##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_systematic
;
2,2'-[(2-Nitrophenyl)methylene]bis(3-hydroxy-5,5-dimethylcyclohex-2-enone)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H27 N O6'
_chemical_formula_sum     'C23 H27 N O6'
_chemical_formula_iupac     'C23 H27 N O6'
_chemical_formula_weight     413.45
_chemical_melting_point     ?
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.7024(3)
_cell_length_b     9.8709(4)
_cell_length_c     13.1621(5)
_cell_angle_alpha     90.3822(19)
_cell_angle_beta     108.9608(18)
_cell_angle_gamma     97.3571(18)
_cell_volume     1059.08(7)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     9400
_cell_measurement_theta_min     2.50
_cell_measurement_theta_max     28.75
_cell_measurement_temperature     100(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.387
_exptl_crystal_size_mid     0.251
_exptl_crystal_size_min     0.134
_exptl_crystal_density_diffrn     1.297
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     440
_exptl_absorpt_coefficient_mu     0.094
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     99.99
_diffrn_source     ?
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker SMART BREEZE CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     29458
_diffrn_reflns_av_R_equivalents     0.0314
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_theta_min     2.497
_diffrn_reflns_theta_max     29.045
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.939
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     0
_refine_special_details     ?
_reflns_number_total     5315
_reflns_number_gt     4254
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0689
_refine_ls_R_factor_gt     0.0542
_refine_ls_wR_factor_gt     0.1432
_refine_ls_wR_factor_ref     0.1543
_refine_ls_goodness_of_fit_ref     1.036
_refine_ls_restrained_S_all     1.036
_refine_ls_number_reflns     5315
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0841P)²+0.5356P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.652
_refine_diff_density_min     -0.253
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2013)'
_computing_cell_refinement     'SAINT (Bruker, 2013)'
_computing_data_reduction     'SAINT (Bruker, 2013)'
_computing_structure_solution     'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement     'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics     'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material     'OLEX2 (Dolomanov et al., 2009)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O5 0.04549(13) 0.40295(11) 0.15867(9) 0.0208(2) Uani d 1 . .
    O O3 0.21250(13) 0.20362(12) 0.17985(9) 0.0236(3) Uani d 1 . .
    O O4 0.68127(15) 0.53646(13) 0.29954(11) 0.0320(3) Uani d 1 . .
    O O6 0.50510(15) 0.73583(13) 0.29901(10) 0.0296(3) Uani d 1 . .
    C C9 0.11023(18) 0.52479(16) 0.18099(11) 0.0185(3) Uani d 1 . .
    O O2 0.61739(15) 0.30380(15) 0.47643(10) 0.0346(3) Uani d 1 . .
    O O1 0.50744(18) 0.09861(14) 0.41032(11) 0.0380(3) Uani d 1 . .
    C C16 0.44538(19) 0.37141(16) 0.25549(12) 0.0203(3) Uani d 1 . .
    C C8 0.27365(18) 0.56290(16) 0.25447(11) 0.0183(3) Uani d 1 . .
    C C7 0.37049(18) 0.45661(15) 0.31983(11) 0.0182(3) Uani d 1 . .
    H H7 0.466554 0.510901 0.375098 0.022 Uiso calc 1 . .
    N N1 0.49857(19) 0.21541(16) 0.43905(11) 0.0279(3) Uani d 1 . .
    C C10 0.0114(2) 0.63357(17) 0.12509(13) 0.0235(3) Uani d 1 . .
    H H10A -0.104225 0.606543 0.120725 0.028 Uiso calc 1 . .
    H H10B 0.014314 0.636767 0.050574 0.028 Uiso calc 1 . .
    C C17 0.36806(18) 0.25256(16) 0.19662(12) 0.0209(3) Uani d 1 . .
    C C13 0.34611(19) 0.69472(17) 0.25407(12) 0.0218(3) Uani d 1 . .
    C C6 0.28101(18) 0.36902(16) 0.38462(11) 0.0191(3) Uani d 1 . .
    C C21 0.61154(19) 0.42118(18) 0.26078(13) 0.0237(3) Uani d 1 . .
    C C18 0.4540(2) 0.15999(18) 0.14946(14) 0.0249(3) Uani d 1 . .
    C C12 0.2536(2) 0.80723(17) 0.20066(13) 0.0249(3) Uani d 1 . .
    H H12A 0.273724 0.823572 0.131642 0.030 Uiso calc 1 . .
    H H12B 0.296854 0.892238 0.246928 0.030 Uiso calc 1 . .
    C C11 0.0687(2) 0.77713(16) 0.17870(13) 0.0230(3) Uani d 1 . .
    C C1 0.3365(2) 0.25007(17) 0.43280(12) 0.0238(3) Uani d 1 . .
    C C2 0.2498(2) 0.16111(18) 0.48286(13) 0.0285(4) Uani d 1 . .
    H H2 0.288304 0.078128 0.509312 0.034 Uiso calc 1 . .
    C C4 0.0550(2) 0.31725(19) 0.45528(13) 0.0277(4) Uani d 1 . .
    H H4 -0.039275 0.344284 0.466757 0.033 Uiso calc 1 . .
    C C19 0.6040(2) 0.23166(18) 0.12570(14) 0.0267(4) Uani d 1 . .
    C C14 0.0311(2) 0.78794(18) 0.28423(14) 0.0280(4) Uani d 1 . .
    H H14A -0.086246 0.759417 0.270562 0.042 Uiso calc 1 . .
    H H14B 0.060734 0.882821 0.313448 0.042 Uiso calc 1 . .
    H H14C 0.094698 0.728498 0.336144 0.042 Uiso calc 1 . .
    C C5 0.13841(19) 0.40093(17) 0.40030(12) 0.0220(3) Uani d 1 . .
    H H5 0.097129 0.482417 0.372502 0.026 Uiso calc 1 . .
    C C20 0.7057(2) 0.3260(2) 0.22307(15) 0.0310(4) Uani d 1 . .
    H H20A 0.756393 0.268957 0.283196 0.037 Uiso calc 1 . .
    H H20B 0.795669 0.381263 0.205032 0.037 Uiso calc 1 . .
    C C3 0.1069(2) 0.19581(19) 0.49334(14) 0.0304(4) Uani d 1 . .
    H H3A 0.044832 0.136339 0.526547 0.036 Uiso calc 1 . .
    C C22 0.7073(2) 0.1264(2) 0.10677(18) 0.0361(4) Uani d 1 . .
    H H22A 0.740886 0.071941 0.170262 0.054 Uiso calc 1 . .
    H H22B 0.804872 0.173597 0.093904 0.054 Uiso calc 1 . .
    H H22C 0.642313 0.066101 0.043989 0.054 Uiso calc 1 . .
    C C15 -0.0190(2) 0.87981(19) 0.10242(15) 0.0321(4) Uani d 1 . .
    H H15A 0.001219 0.871620 0.033763 0.048 Uiso calc 1 . .
    H H15B 0.022549 0.972726 0.134428 0.048 Uiso calc 1 . .
    H H15C -0.137191 0.860984 0.090111 0.048 Uiso calc 1 . .
    C C23 0.5504(3) 0.3151(2) 0.02618(16) 0.0377(4) Uani d 1 . .
    H H23A 0.491440 0.253400 -0.036919 0.057 Uiso calc 1 . .
    H H23B 0.647292 0.366841 0.015346 0.057 Uiso calc 1 . .
    H H23C 0.478164 0.378662 0.036190 0.057 Uiso calc 1 . .
    H H3 0.160(4) 0.282(3) 0.187(2) 0.069(9) Uiso d 1 . .
    H H18A 0.377(3) 0.114(2) 0.093(2) 0.042(6) Uiso d 1 . .
    H H18B 0.486(3) 0.084(2) 0.2037(19) 0.042(6) Uiso d 1 . .
    H H6 0.569(5) 0.647(4) 0.307(3) 0.103(12) Uiso d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O5 C9 . 1.2507(19) ?
    O3 C17 . 1.3234(19) ?
    O4 C21 . 1.240(2) ?
    O6 C13 . 1.3228(19) ?
    C9 C8 . 1.437(2) ?
    C9 C10 . 1.507(2) ?
    O2 N1 . 1.227(2) ?
    O1 N1 . 1.231(2) ?
    C16 C7 . 1.529(2) ?
    C16 C17 . 1.370(2) ?
    C16 C21 . 1.445(2) ?
    C8 C7 . 1.523(2) ?
    C8 C13 . 1.372(2) ?
    C7 C6 . 1.533(2) ?
    N1 C1 . 1.470(2) ?
    C10 C11 . 1.527(2) ?
    C17 C18 . 1.499(2) ?
    C13 C12 . 1.499(2) ?
    C6 C1 . 1.404(2) ?
    C6 C5 . 1.395(2) ?
    C21 C20 . 1.502(2) ?
    C18 C19 . 1.528(2) ?
    C12 C11 . 1.528(2) ?
    C11 C14 . 1.533(2) ?
    C11 C15 . 1.527(2) ?
    C1 C2 . 1.391(2) ?
    C2 C3 . 1.380(3) ?
    C4 C5 . 1.389(2) ?
    C4 C3 . 1.375(3) ?
    C19 C20 . 1.526(2) ?
    C19 C22 . 1.526(2) ?
    C19 C23 . 1.526(3) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O5 C9 C8 . . 122.69(14) ?
    O5 C9 C10 . . 117.37(13) ?
    C8 C9 C10 . . 119.93(13) ?
    C17 C16 C7 . . 124.87(14) ?
    C17 C16 C21 . . 119.05(14) ?
    C21 C16 C7 . . 116.07(13) ?
    C9 C8 C7 . . 121.06(13) ?
    C13 C8 C9 . . 117.49(14) ?
    C13 C8 C7 . . 121.00(13) ?
    C16 C7 C6 . . 112.82(12) ?
    C8 C7 C16 . . 113.54(12) ?
    C8 C7 C6 . . 114.51(12) ?
    O2 N1 O1 . . 124.15(16) ?
    O2 N1 C1 . . 117.60(14) ?
    O1 N1 C1 . . 118.19(15) ?
    C9 C10 C11 . . 115.19(13) ?
    O3 C17 C16 . . 123.87(14) ?
    O3 C17 C18 . . 112.79(14) ?
    C16 C17 C18 . . 123.25(14) ?
    O6 C13 C8 . . 123.82(15) ?
    O6 C13 C12 . . 112.72(14) ?
    C8 C13 C12 . . 123.46(14) ?
    C1 C6 C7 . . 122.42(13) ?
    C5 C6 C7 . . 122.82(14) ?
    C5 C6 C1 . . 114.76(14) ?
    O4 C21 C16 . . 122.67(15) ?
    O4 C21 C20 . . 118.99(14) ?
    C16 C21 C20 . . 118.26(15) ?
    C17 C18 C19 . . 114.49(14) ?
    C13 C12 C11 . . 113.81(13) ?
    C10 C11 C12 . . 107.37(13) ?
    C10 C11 C14 . . 111.47(14) ?
    C10 C11 C15 . . 109.11(14) ?
    C12 C11 C14 . . 110.01(14) ?
    C15 C11 C12 . . 110.07(14) ?
    C15 C11 C14 . . 108.80(14) ?
    C6 C1 N1 . . 121.11(15) ?
    C2 C1 N1 . . 114.97(15) ?
    C2 C1 C6 . . 123.83(15) ?
    C3 C2 C1 . . 118.67(16) ?
    C3 C4 C5 . . 120.92(16) ?
    C20 C19 C18 . . 107.98(14) ?
    C20 C19 C22 . . 109.38(15) ?
    C22 C19 C18 . . 110.18(15) ?
    C23 C19 C18 . . 110.18(15) ?
    C23 C19 C20 . . 109.85(16) ?
    C23 C19 C22 . . 109.26(15) ?
    C4 C5 C6 . . 122.05(15) ?
    C21 C20 C19 . . 114.88(14) ?
    C4 C3 C2 . . 119.41(16) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O5 C9 C8 C7 . . . . -7.3(2) ?
    O5 C9 C8 C13 . . . . 165.07(14) ?
    O5 C9 C10 C11 . . . . 161.40(13) ?
    O3 C17 C18 C19 . . . . 156.51(14) ?
    O4 C21 C20 C19 . . . . -146.42(16) ?
    O6 C13 C12 C11 . . . . -162.31(13) ?
    C9 C8 C7 C16 . . . . 78.45(17) ?
    C9 C8 C7 C6 . . . . -53.11(18) ?
    C9 C8 C13 O6 . . . . -164.77(14) ?
    C9 C8 C13 C12 . . . . 14.0(2) ?
    C9 C10 C11 C12 . . . . 49.40(17) ?
    C9 C10 C11 C14 . . . . -71.15(18) ?
    C9 C10 C11 C15 . . . . 168.67(14) ?
    O2 N1 C1 C6 . . . . 51.4(2) ?
    O2 N1 C1 C2 . . . . -125.14(16) ?
    O1 N1 C1 C6 . . . . -131.16(16) ?
    O1 N1 C1 C2 . . . . 52.2(2) ?
    C16 C7 C6 C1 . . . . 35.67(19) ?
    C16 C7 C6 C5 . . . . -144.27(14) ?
    C16 C17 C18 C19 . . . . -26.7(2) ?
    C16 C21 C20 C19 . . . . 36.8(2) ?
    C8 C9 C10 C11 . . . . -20.2(2) ?
    C8 C7 C6 C1 . . . . 167.58(13) ?
    C8 C7 C6 C5 . . . . -12.4(2) ?
    C8 C13 C12 C11 . . . . 18.8(2) ?
    C7 C16 C17 O3 . . . . 6.8(3) ?
    C7 C16 C17 C18 . . . . -169.69(15) ?
    C7 C16 C21 O4 . . . . -11.6(2) ?
    C7 C16 C21 C20 . . . . 165.04(15) ?
    C7 C8 C13 O6 . . . . 7.6(2) ?
    C7 C8 C13 C12 . . . . -173.56(14) ?
    C7 C6 C1 N1 . . . . 10.4(2) ?
    C7 C6 C1 C2 . . . . -173.36(14) ?
    C7 C6 C5 C4 . . . . 177.16(14) ?
    N1 C1 C2 C3 . . . . 171.47(15) ?
    C10 C9 C8 C7 . . . . 174.32(13) ?
    C10 C9 C8 C13 . . . . -13.3(2) ?
    C17 C16 C7 C8 . . . . -88.49(18) ?
    C17 C16 C7 C6 . . . . 43.9(2) ?
    C17 C16 C21 O4 . . . . 169.75(16) ?
    C17 C16 C21 C20 . . . . -13.6(2) ?
    C17 C18 C19 C20 . . . . 45.7(2) ?
    C17 C18 C19 C22 . . . . 165.08(15) ?
    C17 C18 C19 C23 . . . . -74.29(19) ?
    C13 C8 C7 C16 . . . . -93.69(17) ?
    C13 C8 C7 C6 . . . . 134.75(14) ?
    C13 C12 C11 C10 . . . . -48.40(17) ?
    C13 C12 C11 C14 . . . . 73.07(17) ?
    C13 C12 C11 C15 . . . . -167.05(14) ?
    C6 C1 C2 C3 . . . . -5.0(2) ?
    C21 C16 C7 C8 . . . . 92.93(16) ?
    C21 C16 C7 C6 . . . . -134.69(14) ?
    C21 C16 C17 O3 . . . . -174.70(14) ?
    C21 C16 C17 C18 . . . . 8.9(2) ?
    C18 C19 C20 C21 . . . . -51.4(2) ?
    C1 C6 C5 C4 . . . . -2.8(2) ?
    C1 C2 C3 C4 . . . . -0.7(2) ?
    C5 C6 C1 N1 . . . . -169.69(14) ?
    C5 C6 C1 C2 . . . . 6.6(2) ?
    C5 C4 C3 C2 . . . . 4.3(3) ?
    C3 C4 C5 C6 . . . . -2.5(2) ?
    C22 C19 C20 C21 . . . . -171.31(16) ?
    C23 C19 C20 C21 . . . . 68.8(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    O3 H3 O5 . 0.97(3) 1.62(3) 2.5570(16) 162(3) yes
    O6 H6 O4 . 1.08(4) 1.58(4) 2.6437(19) 166(3) yes
    C2 H2 O1 2_656 0.95 2.63 3.538(2) 159.9 yes
    C10 H10B O5 2_565 0.99 2.65 3.6138(19) 165 yes
    C15 H15B O3 1_565 0.98 2.58 3.505(2) 157 yes
    C18 H18B O1 . 1.04(2) 2.67(2) 3.381(2) 125.5(16) yes
    C20 H20B O5 1_655 0.99 2.43 3.332(2) 151.7 yes
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_T_min     0.965
_shelx_estimated_absorpt_T_max     0.988
data_II
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_systematic
;\
Ethyl 4-(4-hydroxy-3,5-dimethoxyphenyl)-2,7,7-trimethyl-5-oxo-\
1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H29 N O6'
_chemical_formula_sum     'C23 H29 N O6'
_chemical_formula_iupac     'C23 H29 N O6'
_chemical_formula_weight     415.47
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 1 21/n 1'
_space_group_name_Hall     '-P 2yn'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     10.8854(4)
_cell_length_b     25.2446(10)
_cell_length_c     15.3665(6)
_cell_angle_alpha     90
_cell_angle_beta     100.7606(19)
_cell_angle_gamma     90
_cell_volume     4148.4(3)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     9684
_cell_measurement_theta_min     2.66
_cell_measurement_theta_max     30.50
_cell_measurement_temperature     100(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.478
_exptl_crystal_size_mid     0.425
_exptl_crystal_size_min     0.306
_exptl_crystal_density_diffrn     1.330
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     1776
_exptl_absorpt_coefficient_mu     0.096
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     100.01
_diffrn_source     ?
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker SMART BREEZE CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     168826
_diffrn_reflns_av_R_equivalents     0.0452
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_theta_min     1.572
_diffrn_reflns_theta_max     30.576
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -36
_diffrn_reflns_limit_k_max     36
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     0
_refine_special_details     ?
_reflns_number_total     12707
_reflns_number_gt     11044
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0456
_refine_ls_R_factor_gt     0.0392
_refine_ls_wR_factor_gt     0.1025
_refine_ls_wR_factor_ref     0.1077
_refine_ls_goodness_of_fit_ref     1.039
_refine_ls_restrained_S_all     1.039
_refine_ls_number_reflns     12707
_refine_ls_number_parameters     569
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0600P)²+1.3541P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.524
_refine_diff_density_min     -0.205
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2013)'
_computing_cell_refinement     'SAINT (Bruker, 2013)'
_computing_data_reduction     'SAINT (Bruker, 2013)'
_computing_structure_solution     'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement     'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics     'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material     'OLEX2 (Dolomanov et al., 2009)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1A 0.09761(6) 0.68726(3) 0.28219(5) 0.01536(13) Uani d 1 . .
    O O2A 0.66193(6) 0.61973(3) 0.32843(5) 0.01652(13) Uani d 1 . .
    O O3A 0.54423(6) 0.69363(3) 0.31163(5) 0.01527(13) Uani d 1 . .
    O O4A 0.40914(7) 0.74895(3) 0.70657(5) 0.01676(14) Uani d 1 . .
    H H4C 0.4593(16) 0.7750(7) 0.7112(11) 0.035(4) Uiso d 1 . .
    O O5A 0.31079(7) 0.65461(3) 0.68643(4) 0.01866(14) Uani d 1 . .
    O O6A 0.47618(6) 0.80349(3) 0.56333(5) 0.01668(14) Uani d 1 . .
    N N1A 0.34484(7) 0.54131(3) 0.39339(5) 0.01093(13) Uani d 1 . .
    H H1A 0.3460(13) 0.5068(6) 0.4013(9) 0.021(3) Uiso d 1 . .
    C C2A 0.45480(8) 0.56515(3) 0.38033(5) 0.01037(15) Uani d 1 . .
    C C3A 0.45444(8) 0.61775(3) 0.36062(6) 0.01007(14) Uani d 1 . .
    C C4A 0.33953(8) 0.65156(3) 0.36544(5) 0.00946(14) Uani d 1 . .
    H H4B 0.332567 0.679421 0.318505 0.011 Uiso calc 1 . .
    C C5A 0.22391(8) 0.61725(3) 0.34576(5) 0.00925(14) Uani d 1 . .
    C C6A 0.10568(8) 0.63990(3) 0.30421(5) 0.00999(14) Uani d 1 . .
    C C7A -0.00768(8) 0.60412(3) 0.28469(6) 0.01162(15) Uani d 1 . .
    H H7C -0.013501 0.588937 0.224662 0.014 Uiso calc 1 . .
    H H7D -0.083739 0.625617 0.284713 0.014 Uiso calc 1 . .
    C C8A -0.00446(8) 0.55865(3) 0.35161(6) 0.01072(15) Uani d 1 . .
    C C9A 0.11952(8) 0.52866(3) 0.35798(6) 0.01071(15) Uani d 1 . .
    H H9C 0.130811 0.504944 0.410176 0.013 Uiso calc 1 . .
    H H9D 0.115282 0.506253 0.304626 0.013 Uiso calc 1 . .
    C C10A 0.23072(8) 0.56462(3) 0.36583(5) 0.00927(14) Uani d 1 . .
    C C11A -0.01825(9) 0.58146(4) 0.44184(6) 0.01572(17) Uani d 1 . .
    H H11D 0.049914 0.606478 0.462131 0.024 Uiso calc 1 . .
    H H11E -0.014841 0.552601 0.484888 0.024 Uiso calc 1 . .
    H H11F -0.098635 0.599854 0.436132 0.024 Uiso calc 1 . .
    C C12A -0.11296(9) 0.52050(4) 0.31995(7) 0.01625(17) Uani d 1 . .
    H H12D -0.192403 0.539584 0.314712 0.024 Uiso calc 1 . .
    H H12E -0.110612 0.491581 0.362771 0.024 Uiso calc 1 . .
    H H12F -0.105306 0.505920 0.262095 0.024 Uiso calc 1 . .
    C C13A 0.56241(8) 0.52727(4) 0.38723(6) 0.01339(16) Uani d 1 . .
    H H13D 0.543503 0.494967 0.417571 0.020 Uiso calc 1 . .
    H H13E 0.638014 0.543801 0.420913 0.020 Uiso calc 1 . .
    H H13F 0.575997 0.518286 0.327703 0.020 Uiso calc 1 . .
    C C14A 0.56421(8) 0.64179(4) 0.33347(6) 0.01162(15) Uani d 1 . .
    C C15A 0.63909(9) 0.71842(4) 0.27011(6) 0.01674(17) Uani d 1 . .
    H H15C 0.723206 0.707623 0.301464 0.020 Uiso calc 1 . .
    H H15D 0.632745 0.757422 0.274256 0.020 Uiso calc 1 . .
    C C16A 0.62173(10) 0.70211(4) 0.17397(7) 0.02087(19) Uani d 1 . .
    H H16D 0.674331 0.724303 0.143533 0.031 Uiso calc 1 . .
    H H16E 0.533831 0.706570 0.145851 0.031 Uiso calc 1 . .
    H H16F 0.645760 0.664893 0.170167 0.031 Uiso calc 1 . .
    C C17A 0.35248(8) 0.67935(3) 0.45549(6) 0.01023(15) Uani d 1 . .
    C C18A 0.32110(8) 0.65290(3) 0.52864(6) 0.01201(15) Uani d 1 . .
    H H18A 0.286818 0.618226 0.521374 0.014 Uiso calc 1 . .
    C C19A 0.33951(8) 0.67677(4) 0.61162(6) 0.01263(16) Uani d 1 . .
    C C20A 0.39194(8) 0.72784(4) 0.62385(6) 0.01266(16) Uani d 1 . .
    C C21A 0.42098(8) 0.75402(3) 0.55069(6) 0.01235(16) Uani d 1 . .
    C C22A 0.40129(8) 0.73027(3) 0.46704(6) 0.01162(15) Uani d 1 . .
    H H22A 0.421364 0.749009 0.417934 0.014 Uiso calc 1 . .
    C C23A 0.25765(10) 0.60304(4) 0.67836(7) 0.02005(19) Uani d 1 . .
    H H23D 0.179341 0.603652 0.634894 0.030 Uiso calc 1 . .
    H H23E 0.240715 0.591604 0.735908 0.030 Uiso calc 1 . .
    H H23F 0.316250 0.578294 0.658694 0.030 Uiso calc 1 . .
    C C24A 0.38733(10) 0.84600(4) 0.54853(7) 0.02017(19) Uani d 1 . .
    H H24D 0.337479 0.843172 0.488624 0.030 Uiso calc 1 . .
    H H24E 0.431736 0.879953 0.554867 0.030 Uiso calc 1 . .
    H H24F 0.332068 0.843913 0.591977 0.030 Uiso calc 1 . .
    O O1B 0.64618(7) 0.56795(3) 0.59302(5) 0.01898(14) Uani d 1 . .
    O O2B 0.42404(7) 0.61173(3) 0.93863(5) 0.02210(15) Uani d 1 . .
    O O3B 0.47350(6) 0.54093(3) 0.86392(5) 0.01724(14) Uani d 1 . .
    O O4B 1.07150(7) 0.47496(3) 0.91945(5) 0.01745(14) Uani d 1 . .
    H H4 1.1277(17) 0.4973(7) 0.9396(12) 0.040(5) Uiso d 1 . .
    O O5B 1.09254(6) 0.57723(3) 0.88846(5) 0.01832(14) Uani d 1 . .
    O O6B 0.85544(7) 0.42479(3) 0.88741(5) 0.01802(14) Uani d 1 . .
    N N1B 0.67195(7) 0.70086(3) 0.81054(5) 0.01272(14) Uani d 1 . .
    H H1 0.6769(13) 0.7356(6) 0.8200(9) 0.022(3) Uiso d 1 . .
    C C2B 0.60016(8) 0.67286(4) 0.86093(6) 0.01315(16) Uani d 1 . .
    C C3B 0.57467(8) 0.62086(4) 0.84315(6) 0.01213(15) Uani d 1 . .
    C C4B 0.63347(8) 0.59179(3) 0.77391(6) 0.01085(15) Uani d 1 . .
    H H4A 0.570391 0.566145 0.742480 0.013 Uiso calc 1 . .
    C C5B 0.66228(8) 0.63135(3) 0.70649(6) 0.01071(15) Uani d 1 . .
    C C6B 0.66639(8) 0.61434(3) 0.61710(6) 0.01161(15) Uani d 1 . .
    C C7B 0.69106(8) 0.65543(3) 0.55138(6) 0.01271(15) Uani d 1 . .
    H H7A 0.610642 0.671873 0.523744 0.015 Uiso calc 1 . .
    H H7B 0.725884 0.637650 0.503929 0.015 Uiso calc 1 . .
    C C8B 0.78141(8) 0.69911(3) 0.59211(6) 0.01258(15) Uani d 1 . .
    C C9B 0.73133(8) 0.72350(3) 0.67009(6) 0.01263(15) Uani d 1 . .
    H H9A 0.798126 0.745108 0.705925 0.015 Uiso calc 1 . .
    H H9B 0.660884 0.747437 0.646616 0.015 Uiso calc 1 . .
    C C10B 0.68745(8) 0.68288(3) 0.72894(6) 0.01098(15) Uani d 1 . .
    C C11B 0.91219(9) 0.67533(4) 0.62358(7) 0.01783(18) Uani d 1 . .
    H H11A 0.906685 0.645916 0.664297 0.027 Uiso calc 1 . .
    H H11B 0.968228 0.702619 0.654158 0.027 Uiso calc 1 . .
    H H11C 0.945007 0.662303 0.572359 0.027 Uiso calc 1 . .
    C C12B 0.78685(10) 0.74186(4) 0.52223(7) 0.01908(18) Uani d 1 . .
    H H12A 0.817987 0.726305 0.472081 0.029 Uiso calc 1 . .
    H H12B 0.843131 0.770322 0.548282 0.029 Uiso calc 1 . .
    H H12C 0.702898 0.756306 0.501600 0.029 Uiso calc 1 . .
    C C13B 0.55601(10) 0.70687(4) 0.92881(7) 0.02043(19) Uani d 1 . .
    H H13A 0.617141 0.735037 0.947664 0.031 Uiso calc 1 . .
    H H13B 0.546865 0.685161 0.980088 0.031 Uiso calc 1 . .
    H H13C 0.475127 0.722665 0.903090 0.031 Uiso calc 1 . .
    C C14B 0.48511(8) 0.59282(4) 0.88766(6) 0.01479(16) Uani d 1 . .
    C C15B 0.37849(9) 0.51189(4) 0.89925(7) 0.01923(18) Uani d 1 . .
    H H15A 0.294455 0.525795 0.873705 0.023 Uiso calc 1 . .
    H H15B 0.392024 0.516062 0.964409 0.023 Uiso calc 1 . .
    C C16B 0.38731(10) 0.45419(4) 0.87558(7) 0.02153(19) Uani d 1 . .
    H H16A 0.376740 0.450555 0.811117 0.032 Uiso calc 1 . .
    H H16B 0.321567 0.434209 0.896828 0.032 Uiso calc 1 . .
    H H16C 0.469351 0.440325 0.903427 0.032 Uiso calc 1 . .
    C C17B 0.75057(8) 0.56042(3) 0.81518(6) 0.01136(15) Uani d 1 . .
    C C18B 0.86636(8) 0.58599(4) 0.83344(6) 0.01318(16) Uani d 1 . .
    H H18 0.871998 0.622799 0.821919 0.016 Uiso calc 1 . .
    C C19B 0.97326(8) 0.55741(4) 0.86850(6) 0.01334(16) Uani d 1 . .
    C C20B 0.96602(8) 0.50345(4) 0.88589(6) 0.01323(16) Uani d 1 . .
    C C21B 0.85061(9) 0.47788(3) 0.86888(6) 0.01301(16) Uani d 1 . .
    C C22B 0.74257(8) 0.50638(4) 0.83344(6) 0.01278(16) Uani d 1 . .
    H H22 0.663772 0.489024 0.821767 0.015 Uiso calc 1 . .
    C C23B 1.10806(9) 0.63320(4) 0.88435(8) 0.02108(19) Uani d 1 . .
    H H23A 1.077197 0.645485 0.823712 0.032 Uiso calc 1 . .
    H H23B 1.196897 0.642070 0.901795 0.032 Uiso calc 1 . .
    H H23C 1.060743 0.650516 0.924718 0.032 Uiso calc 1 . .
    C C24B 0.74049(10) 0.39706(4) 0.88304(7) 0.01957(19) Uani d 1 . .
    H H24A 0.689946 0.400674 0.823490 0.029 Uiso calc 1 . .
    H H24B 0.694746 0.411935 0.926559 0.029 Uiso calc 1 . .
    H H24C 0.757687 0.359498 0.896071 0.029 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1A C6A . 1.2412(10) ?
    O2A C14A . 1.2159(11) ?
    O3A C14A . 1.3583(11) ?
    O3A C15A . 1.4529(11) ?
    O4A C20A . 1.3587(11) ?
    O5A C19A . 1.3661(11) ?
    O5A C23A . 1.4206(12) ?
    O6A C21A . 1.3837(10) ?
    O6A C24A . 1.4341(12) ?
    N1A C2A . 1.3874(11) ?
    N1A C10A . 1.3683(11) ?
    C2A C3A . 1.3617(12) ?
    C2A C13A . 1.5006(12) ?
    C3A C4A . 1.5275(12) ?
    C3A C14A . 1.4684(12) ?
    C4A C5A . 1.5112(11) ?
    C4A C17A . 1.5344(12) ?
    C5A C6A . 1.4437(11) ?
    C5A C10A . 1.3628(11) ?
    C6A C7A . 1.5134(12) ?
    C7A C8A . 1.5371(12) ?
    C8A C9A . 1.5346(12) ?
    C8A C11A . 1.5342(12) ?
    C8A C12A . 1.5313(12) ?
    C9A C10A . 1.4998(11) ?
    C15A C16A . 1.5111(14) ?
    C17A C18A . 1.4034(12) ?
    C17A C22A . 1.3895(11) ?
    C18A C19A . 1.3906(12) ?
    C19A C20A . 1.4082(12) ?
    C20A C21A . 1.3904(13) ?
    C21A C22A . 1.3981(12) ?
    O1B C6B . 1.2355(11) ?
    O2B C14B . 1.2156(12) ?
    O3B C14B . 1.3593(12) ?
    O3B C15B . 1.4530(11) ?
    O4B C20B . 1.3713(11) ?
    O5B C19B . 1.3717(11) ?
    O5B C23B . 1.4257(12) ?
    O6B C21B . 1.3690(11) ?
    O6B C24B . 1.4245(12) ?
    N1B C2B . 1.3913(12) ?
    N1B C10B . 1.3733(11) ?
    C2B C3B . 1.3589(13) ?
    C2B C13B . 1.4979(13) ?
    C3B C4B . 1.5280(12) ?
    C3B C14B . 1.4725(13) ?
    C4B C5B . 1.5134(12) ?
    C4B C17B . 1.5337(12) ?
    C5B C6B . 1.4479(12) ?
    C5B C10B . 1.3604(12) ?
    C6B C7B . 1.5062(12) ?
    C7B C8B . 1.5314(12) ?
    C8B C9B . 1.5350(12) ?
    C8B C11B . 1.5374(13) ?
    C8B C12B . 1.5313(13) ?
    C9B C10B . 1.5027(12) ?
    C15B C16B . 1.5088(15) ?
    C17B C18B . 1.3972(12) ?
    C17B C22B . 1.3987(12) ?
    C18B C19B . 1.3896(12) ?
    C19B C20B . 1.3932(13) ?
    C20B C21B . 1.3931(13) ?
    C21B C22B . 1.3994(12) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C14A O3A C15A . . 115.43(7) ?
    C19A O5A C23A . . 117.08(7) ?
    C21A O6A C24A . . 113.00(7) ?
    C10A N1A C2A . . 121.78(7) ?
    N1A C2A C13A . . 113.36(7) ?
    C3A C2A N1A . . 119.23(8) ?
    C3A C2A C13A . . 127.37(8) ?
    C2A C3A C4A . . 120.17(7) ?
    C2A C3A C14A . . 119.84(8) ?
    C14A C3A C4A . . 119.99(7) ?
    C3A C4A C17A . . 111.17(7) ?
    C5A C4A C3A . . 109.20(7) ?
    C5A C4A C17A . . 112.05(7) ?
    C6A C5A C4A . . 120.12(7) ?
    C10A C5A C4A . . 120.36(7) ?
    C10A C5A C6A . . 119.51(7) ?
    O1A C6A C5A . . 120.93(8) ?
    O1A C6A C7A . . 120.49(8) ?
    C5A C6A C7A . . 118.54(7) ?
    C6A C7A C8A . . 113.41(7) ?
    C9A C8A C7A . . 108.72(7) ?
    C11A C8A C7A . . 109.30(7) ?
    C11A C8A C9A . . 111.15(7) ?
    C12A C8A C7A . . 109.71(7) ?
    C12A C8A C9A . . 109.08(7) ?
    C12A C8A C11A . . 108.87(7) ?
    C10A C9A C8A . . 113.17(7) ?
    N1A C10A C9A . . 115.91(7) ?
    C5A C10A N1A . . 119.81(8) ?
    C5A C10A C9A . . 124.26(7) ?
    O2A C14A O3A . . 121.80(8) ?
    O2A C14A C3A . . 126.64(8) ?
    O3A C14A C3A . . 111.55(7) ?
    O3A C15A C16A . . 110.04(8) ?
    C18A C17A C4A . . 120.65(7) ?
    C22A C17A C4A . . 120.45(8) ?
    C22A C17A C18A . . 118.83(8) ?
    C19A C18A C17A . . 120.88(8) ?
    O5A C19A C18A . . 125.29(8) ?
    O5A C19A C20A . . 114.41(8) ?
    C18A C19A C20A . . 120.30(8) ?
    O4A C20A C19A . . 117.75(8) ?
    O4A C20A C21A . . 123.89(8) ?
    C21A C20A C19A . . 118.35(8) ?
    O6A C21A C20A . . 118.27(8) ?
    O6A C21A C22A . . 120.27(8) ?
    C20A C21A C22A . . 121.37(8) ?
    C17A C22A C21A . . 120.23(8) ?
    C14B O3B C15B . . 115.02(7) ?
    C19B O5B C23B . . 117.82(7) ?
    C21B O6B C24B . . 118.16(7) ?
    C10B N1B C2B . . 121.19(8) ?
    N1B C2B C13B . . 112.51(8) ?
    C3B C2B N1B . . 119.59(8) ?
    C3B C2B C13B . . 127.86(9) ?
    C2B C3B C4B . . 120.50(8) ?
    C2B C3B C14B . . 119.94(8) ?
    C14B C3B C4B . . 119.50(8) ?
    C3B C4B C17B . . 112.57(7) ?
    C5B C4B C3B . . 109.09(7) ?
    C5B C4B C17B . . 111.19(7) ?
    C6B C5B C4B . . 120.05(7) ?
    C10B C5B C4B . . 121.01(8) ?
    C10B C5B C6B . . 118.93(8) ?
    O1B C6B C5B . . 122.00(8) ?
    O1B C6B C7B . . 119.74(8) ?
    C5B C6B C7B . . 118.21(7) ?
    C6B C7B C8B . . 113.78(7) ?
    C7B C8B C9B . . 108.25(7) ?
    C7B C8B C11B . . 109.50(7) ?
    C9B C8B C11B . . 110.73(7) ?
    C12B C8B C7B . . 109.08(7) ?
    C12B C8B C9B . . 109.31(7) ?
    C12B C8B C11B . . 109.94(8) ?
    C10B C9B C8B . . 113.28(7) ?
    N1B C10B C9B . . 115.54(7) ?
    C5B C10B N1B . . 119.61(8) ?
    C5B C10B C9B . . 124.85(8) ?
    O2B C14B O3B . . 121.11(9) ?
    O2B C14B C3B . . 126.85(9) ?
    O3B C14B C3B . . 112.03(8) ?
    O3B C15B C16B . . 108.38(8) ?
    C18B C17B C4B . . 119.57(8) ?
    C18B C17B C22B . . 119.86(8) ?
    C22B C17B C4B . . 120.56(8) ?
    C19B C18B C17B . . 119.78(8) ?
    O5B C19B C18B . . 125.90(8) ?
    O5B C19B C20B . . 113.51(8) ?
    C18B C19B C20B . . 120.59(8) ?
    O4B C20B C19B . . 120.77(8) ?
    O4B C20B C21B . . 119.34(8) ?
    C21B C20B C19B . . 119.89(8) ?
    O6B C21B C20B . . 114.60(8) ?
    O6B C21B C22B . . 125.54(8) ?
    C20B C21B C22B . . 119.85(8) ?
    C17B C22B C21B . . 120.02(8) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1A C6A C7A C8A . . . . -151.01(8) ?
    O4A C20A C21A O6A . . . . 3.22(13) ?
    O4A C20A C21A C22A . . . . 179.97(8) ?
    O5A C19A C20A O4A . . . . 0.60(12) ?
    O5A C19A C20A C21A . . . . -178.29(8) ?
    O6A C21A C22A C17A . . . . 176.30(8) ?
    N1A C2A C3A C4A . . . . 8.37(12) ?
    N1A C2A C3A C14A . . . . -170.77(8) ?
    C2A N1A C10A C5A . . . . -16.97(12) ?
    C2A N1A C10A C9A . . . . 161.69(8) ?
    C2A C3A C4A C5A . . . . -29.30(10) ?
    C2A C3A C4A C17A . . . . 94.83(9) ?
    C2A C3A C14A O2A . . . . -2.27(14) ?
    C2A C3A C14A O3A . . . . 176.45(8) ?
    C3A C4A C5A C6A . . . . -149.71(8) ?
    C3A C4A C5A C10A . . . . 29.31(10) ?
    C3A C4A C17A C18A . . . . -83.76(9) ?
    C3A C4A C17A C22A . . . . 93.08(9) ?
    C4A C3A C14A O2A . . . . 178.59(8) ?
    C4A C3A C14A O3A . . . . -2.69(11) ?
    C4A C5A C6A O1A . . . . 1.72(12) ?
    C4A C5A C6A C7A . . . . 179.35(7) ?
    C4A C5A C10A N1A . . . . -8.32(12) ?
    C4A C5A C10A C9A . . . . 173.14(7) ?
    C4A C17A C18A C19A . . . . 176.22(8) ?
    C4A C17A C22A C21A . . . . -175.56(8) ?
    C5A C4A C17A C18A . . . . 38.74(10) ?
    C5A C4A C17A C22A . . . . -144.43(8) ?
    C5A C6A C7A C8A . . . . 31.35(11) ?
    C6A C5A C10A N1A . . . . 170.71(8) ?
    C6A C5A C10A C9A . . . . -7.84(12) ?
    C6A C7A C8A C9A . . . . -53.22(9) ?
    C6A C7A C8A C11A . . . . 68.27(9) ?
    C6A C7A C8A C12A . . . . -172.43(7) ?
    C7A C8A C9A C10A . . . . 45.78(9) ?
    C8A C9A C10A N1A . . . . 164.48(7) ?
    C8A C9A C10A C5A . . . . -16.93(12) ?
    C10A N1A C2A C3A . . . . 16.82(12) ?
    C10A N1A C2A C13A . . . . -161.19(8) ?
    C10A C5A C6A O1A . . . . -177.31(8) ?
    C10A C5A C6A C7A . . . . 0.32(12) ?
    C11A C8A C9A C10A . . . . -74.57(9) ?
    C12A C8A C9A C10A . . . . 165.38(7) ?
    C13A C2A C3A C4A . . . . -173.92(8) ?
    C13A C2A C3A C14A . . . . 6.94(13) ?
    C14A O3A C15A C16A . . . . 77.56(10) ?
    C14A C3A C4A C5A . . . . 149.84(7) ?
    C14A C3A C4A C17A . . . . -86.04(9) ?
    C15A O3A C14A O2A . . . . 8.56(12) ?
    C15A O3A C14A C3A . . . . -170.22(7) ?
    C17A C4A C5A C6A . . . . 86.68(9) ?
    C17A C4A C5A C10A . . . . -94.30(9) ?
    C17A C18A C19A O5A . . . . 179.24(8) ?
    C17A C18A C19A C20A . . . . -0.95(13) ?
    C18A C17A C22A C21A . . . . 1.33(13) ?
    C18A C19A C20A O4A . . . . -179.24(8) ?
    C18A C19A C20A C21A . . . . 1.87(13) ?
    C19A C20A C21A O6A . . . . -177.97(8) ?
    C19A C20A C21A C22A . . . . -1.22(13) ?
    C20A C21A C22A C17A . . . . -0.39(13) ?
    C22A C17A C18A C19A . . . . -0.67(13) ?
    C23A O5A C19A C18A . . . . -0.11(14) ?
    C23A O5A C19A C20A . . . . -179.94(8) ?
    C24A O6A C21A C20A . . . . -93.57(10) ?
    C24A O6A C21A C22A . . . . 89.64(10) ?
    O1B C6B C7B C8B . . . . -147.46(8) ?
    O4B C20B C21B O6B . . . . -0.68(12) ?
    O4B C20B C21B C22B . . . . -179.08(8) ?
    O5B C19B C20B O4B . . . . -0.23(12) ?
    O5B C19B C20B C21B . . . . 179.96(8) ?
    O6B C21B C22B C17B . . . . -178.23(8) ?
    N1B C2B C3B C4B . . . . 5.35(13) ?
    N1B C2B C3B C14B . . . . -171.69(8) ?
    C2B N1B C10B C5B . . . . -17.81(13) ?
    C2B N1B C10B C9B . . . . 161.71(8) ?
    C2B C3B C4B C5B . . . . -26.83(11) ?
    C2B C3B C4B C17B . . . . 97.09(10) ?
    C2B C3B C14B O2B . . . . 3.16(15) ?
    C2B C3B C14B O3B . . . . -178.35(8) ?
    C3B C4B C5B C6B . . . . -153.27(8) ?
    C3B C4B C5B C10B . . . . 28.25(11) ?
    C3B C4B C17B C18B . . . . -84.89(10) ?
    C3B C4B C17B C22B . . . . 96.04(9) ?
    C4B C3B C14B O2B . . . . -173.92(9) ?
    C4B C3B C14B O3B . . . . 4.58(11) ?
    C4B C5B C6B O1B . . . . 0.45(13) ?
    C4B C5B C6B C7B . . . . 177.94(7) ?
    C4B C5B C10B N1B . . . . -7.91(12) ?
    C4B C5B C10B C9B . . . . 172.62(8) ?
    C4B C17B C18B C19B . . . . -178.18(8) ?
    C4B C17B C22B C21B . . . . 178.27(8) ?
    C5B C4B C17B C18B . . . . 37.86(11) ?
    C5B C4B C17B C22B . . . . -141.21(8) ?
    C5B C6B C7B C8B . . . . 34.99(11) ?
    C6B C5B C10B N1B . . . . 173.59(8) ?
    C6B C5B C10B C9B . . . . -5.88(13) ?
    C6B C7B C8B C9B . . . . -54.30(10) ?
    C6B C7B C8B C11B . . . . 66.51(10) ?
    C6B C7B C8B C12B . . . . -173.14(8) ?
    C7B C8B C9B C10B . . . . 44.60(10) ?
    C8B C9B C10B N1B . . . . 164.10(8) ?
    C8B C9B C10B C5B . . . . -16.41(12) ?
    C10B N1B C2B C3B . . . . 19.06(13) ?
    C10B N1B C2B C13B . . . . -158.87(8) ?
    C10B C5B C6B O1B . . . . 178.96(9) ?
    C10B C5B C6B C7B . . . . -3.55(12) ?
    C11B C8B C9B C10B . . . . -75.44(9) ?
    C12B C8B C9B C10B . . . . 163.30(8) ?
    C13B C2B C3B C4B . . . . -177.07(9) ?
    C13B C2B C3B C14B . . . . 5.89(14) ?
    C14B O3B C15B C16B . . . . -173.74(8) ?
    C14B C3B C4B C5B . . . . 150.23(8) ?
    C14B C3B C4B C17B . . . . -85.86(10) ?
    C15B O3B C14B O2B . . . . 3.78(13) ?
    C15B O3B C14B C3B . . . . -174.82(8) ?
    C17B C4B C5B C6B . . . . 82.01(10) ?
    C17B C4B C5B C10B . . . . -96.48(9) ?
    C17B C18B C19B O5B . . . . 179.14(8) ?
    C17B C18B C19B C20B . . . . -0.19(13) ?
    C18B C17B C22B C21B . . . . -0.80(13) ?
    C18B C19B C20B O4B . . . . 179.18(8) ?
    C18B C19B C20B C21B . . . . -0.63(13) ?
    C19B C20B C21B O6B . . . . 179.13(8) ?
    C19B C20B C21B C22B . . . . 0.72(13) ?
    C20B C21B C22B C17B . . . . -0.02(13) ?
    C22B C17B C18B C19B . . . . 0.89(13) ?
    C23B O5B C19B C18B . . . . 8.86(14) ?
    C23B O5B C19B C20B . . . . -171.77(9) ?
    C24B O6B C21B C20B . . . . 171.90(8) ?
    C24B O6B C21B C22B . . . . -9.80(13) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    O4A H4C O1A 4_676 0.848(17) 1.937(17) 2.6948(9) 148.0(16) yes
    N1A H1A O1B 3_666 0.880(15) 1.890(15) 2.7666(10) 174.1(13) yes
    C7A H7C O6B 3_666 0.99 2.67 3.4510(12) 135.5 yes
    C12A H12D O2A 1_455 0.98 2.60 3.5237(12) 157 yes
    C13A H13D O1B 3_666 0.98 2.59 3.3590(12) 135.8 yes
    C16A H16D O4A 4_675 0.98 2.65 3.3136(13) 125.6 yes
    C24A H24E O4B 2_656 0.98 2.43 3.3105(13) 149 yes
    N1B H1 O1A 4_676 0.888(15) 2.166(15) 2.9479(10) 146.6(12) yes
    C7B H7B O2A . 0.99 2.69 3.4992(11) 138.6 yes
    C9B H9B O6A . 0.99 2.59 3.5751(11) 172 yes
    C15B H15A O5B 1_455 0.99 2.60 3.4993(12) 151.2 yes
    C23B H23B O2B 1_655 0.98 2.55 3.4277(13) 149.2 yes
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_T_min     0.956
_shelx_estimated_absorpt_T_max     0.971
data_III
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_journal_date_recd_electronic     2019-11-01
_journal_date_accepted     2019-12-19
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2020
_journal_volume     76
_journal_issue      2
_journal_page_first     125
_journal_page_last     131
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989019017018
_journal_coeditor_code     DX2021
_chemical_name_systematic
;\
Ethyl 4-(anthracen-9-yl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-\
hexahydroquinoline-3-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C29 H29 N O3'
_chemical_formula_sum     'C29 H29 N O3'
_chemical_formula_iupac     'C29 H29 N O3'
_chemical_formula_weight     439.53
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 1 21/n 1'
_space_group_name_Hall     '-P 2yn'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     11.6527(3)
_cell_length_b     18.1986(4)
_cell_length_c     12.3435(3)
_cell_angle_alpha     90
_cell_angle_beta     114.8758(12)
_cell_angle_gamma     90
_cell_volume     2374.74(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9872
_cell_measurement_theta_min     2.228
_cell_measurement_theta_max     27.642
_cell_measurement_temperature     100(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.453
_exptl_crystal_size_mid     0.122
_exptl_crystal_size_min     0.108
_exptl_crystal_density_diffrn     1.229
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     936
_exptl_absorpt_coefficient_mu     0.079
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     100.0
_diffrn_source     ?
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker SMART BREEZE CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     72579
_diffrn_reflns_av_R_equivalents     0.0547
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_theta_min     2.135
_diffrn_reflns_theta_max     28.301
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -24
_diffrn_reflns_limit_k_max     24
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_refine_special_details     ?
_reflns_number_total     5902
_reflns_number_gt     4515
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0672
_refine_ls_R_factor_gt     0.0484
_refine_ls_wR_factor_gt     0.1218
_refine_ls_wR_factor_ref     0.1346
_refine_ls_goodness_of_fit_ref     1.039
_refine_ls_restrained_S_all     1.039
_refine_ls_number_reflns     5902
_refine_ls_number_parameters     306
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0670P)²+1.0544P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.544
_refine_diff_density_min     -0.224
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2013)'
_computing_cell_refinement     'SAINT (Bruker, 2013)'
_computing_data_reduction     'SAINT (Bruker, 2013)'
_computing_structure_solution     'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement     'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics     'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material     'OLEX2 (Dolomanov et al., 2009)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.34009(10) 0.80683(6) 0.16928(9) 0.0235(2) Uani d 1 . .
    O O2 0.31457(11) 0.54998(7) 0.51900(11) 0.0331(3) Uani d 1 . .
    O O3 0.19449(10) 0.64051(6) 0.40339(10) 0.0256(2) Uani d 1 . .
    N N1 0.61943(12) 0.65569(7) 0.47273(11) 0.0182(3) Uani d 1 . .
    H H1 0.6990(19) 0.6551(11) 0.5295(18) 0.032(5) Uiso d 1 . .
    C C2 0.52536(13) 0.62310(7) 0.49757(12) 0.0177(3) Uani d 1 . .
    C C3 0.40249(13) 0.63374(7) 0.42341(12) 0.0169(3) Uani d 1 . .
    C C4 0.36056(13) 0.68248(7) 0.31263(12) 0.0153(3) Uani d 1 . .
    H H4 0.304711 0.721153 0.322453 0.018 Uiso calc 1 . .
    C C5 0.47314(13) 0.72274(7) 0.30848(12) 0.0152(3) Uani d 1 . .
    C C6 0.44911(13) 0.78495(7) 0.22944(12) 0.0170(3) Uani d 1 . .
    C C7 0.55990(14) 0.82620(8) 0.22492(13) 0.0202(3) Uani d 1 . .
    H H7A 0.575271 0.870831 0.274940 0.024 Uiso calc 1 . .
    H H7B 0.536301 0.842425 0.141710 0.024 Uiso calc 1 . .
    C C8 0.68311(14) 0.78268(8) 0.26676(13) 0.0199(3) Uani d 1 . .
    C C9 0.70717(13) 0.74830(8) 0.38790(13) 0.0188(3) Uani d 1 . .
    H H9A 0.778956 0.713567 0.410903 0.023 Uiso calc 1 . .
    H H9B 0.731471 0.787529 0.449080 0.023 Uiso calc 1 . .
    C C10 0.59379(13) 0.70822(7) 0.38663(12) 0.0158(3) Uani d 1 . .
    C C11 0.67348(15) 0.72310(9) 0.17535(14) 0.0260(3) Uani d 1 . .
    H H11A 0.602860 0.690143 0.164169 0.039 Uiso calc 1 . .
    H H11B 0.752376 0.694870 0.204489 0.039 Uiso calc 1 . .
    H H11C 0.659039 0.746243 0.098998 0.039 Uiso calc 1 . .
    C C12 0.79290(15) 0.83464(9) 0.28370(15) 0.0262(3) Uani d 1 . .
    H H12A 0.872397 0.806942 0.314765 0.039 Uiso calc 1 . .
    H H12B 0.797430 0.873461 0.340391 0.039 Uiso calc 1 . .
    H H12C 0.779071 0.856745 0.206789 0.039 Uiso calc 1 . .
    C C13 0.57721(15) 0.58079(8) 0.61266(13) 0.0240(3) Uani d 1 . .
    H H13A 0.663101 0.597854 0.662873 0.036 Uiso calc 1 . .
    H H13B 0.579314 0.528329 0.595650 0.036 Uiso calc 1 . .
    H H13C 0.523073 0.588557 0.654582 0.036 Uiso calc 1 . .
    C C14 0.30380(14) 0.60270(8) 0.45520(13) 0.0215(3) Uani d 1 . .
    C C15 0.08506(16) 0.61002(11) 0.41441(16) 0.0340(4) Uani d 1 . .
    H H15A 0.023216 0.649703 0.404172 0.041 Uiso calc 1 . .
    H H15B 0.111372 0.589143 0.495409 0.041 Uiso calc 1 . .
    C C16 0.0228(2) 0.55080(12) 0.32261(18) 0.0466(5) Uani d 1 . .
    H H16A 0.080715 0.509048 0.338088 0.070 Uiso calc 1 . .
    H H16B 0.002429 0.570354 0.242627 0.070 Uiso calc 1 . .
    H H16C -0.055015 0.534573 0.327545 0.070 Uiso calc 1 . .
    C C17 0.27883(12) 0.64059(7) 0.19723(12) 0.0149(3) Uani d 1 . .
    C C18 0.33088(13) 0.58220(7) 0.15614(12) 0.0151(3) Uani d 1 . .
    C C19 0.46066(13) 0.55974(8) 0.21467(12) 0.0171(3) Uani d 1 . .
    H H19 0.515995 0.585501 0.283915 0.021 Uiso calc 1 . .
    C C20 0.50692(14) 0.50254(8) 0.17387(13) 0.0199(3) Uani d 1 . .
    H H20 0.593432 0.489206 0.215031 0.024 Uiso calc 1 . .
    C C21 0.42774(15) 0.46271(8) 0.07091(14) 0.0223(3) Uani d 1 . .
    H H21 0.460922 0.422798 0.043432 0.027 Uiso calc 1 . .
    C C22 0.30435(14) 0.48181(8) 0.01176(13) 0.0206(3) Uani d 1 . .
    H H22 0.251852 0.455228 -0.057734 0.025 Uiso calc 1 . .
    C C23 0.25166(13) 0.54115(8) 0.05188(12) 0.0174(3) Uani d 1 . .
    C C24 0.12363(14) 0.55804(8) -0.00657(12) 0.0192(3) Uani d 1 . .
    H H24 0.071627 0.530269 -0.074803 0.023 Uiso calc 1 . .
    C C25 0.06980(13) 0.61454(8) 0.03234(12) 0.0178(3) Uani d 1 . .
    C C26 0.14856(13) 0.65780(7) 0.13450(12) 0.0162(3) Uani d 1 . .
    C C27 0.08637(13) 0.71596(8) 0.16756(13) 0.0191(3) Uani d 1 . .
    H H27 0.135306 0.747691 0.231472 0.023 Uiso calc 1 . .
    C C28 -0.04097(14) 0.72696(8) 0.10984(14) 0.0220(3) Uani d 1 . .
    H H28 -0.078874 0.765462 0.135365 0.026 Uiso calc 1 . .
    C C29 -0.11792(14) 0.68199(8) 0.01238(14) 0.0228(3) Uani d 1 . .
    H H29 -0.206831 0.689377 -0.025495 0.027 Uiso calc 1 . .
    C C30 -0.06317(14) 0.62827(8) -0.02621(13) 0.0210(3) Uani d 1 . .
    H H30 -0.114157 0.599310 -0.093293 0.025 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C6 . 1.2370(17) ?
    O2 C14 . 1.2138(19) ?
    O3 C14 . 1.3489(19) ?
    O3 C15 . 1.4486(19) ?
    N1 C2 . 1.3893(18) ?
    N1 C10 . 1.3658(18) ?
    C2 C3 . 1.350(2) ?
    C2 C13 . 1.5013(19) ?
    C3 C4 . 1.5275(18) ?
    C3 C14 . 1.4749(19) ?
    C4 C5 . 1.5220(18) ?
    C4 C17 . 1.5413(18) ?
    C5 C6 . 1.4430(19) ?
    C5 C10 . 1.3550(19) ?
    C6 C7 . 1.5146(19) ?
    C7 C8 . 1.527(2) ?
    C8 C9 . 1.534(2) ?
    C8 C11 . 1.534(2) ?
    C8 C12 . 1.533(2) ?
    C9 C10 . 1.5036(19) ?
    C15 C16 . 1.510(3) ?
    C17 C18 . 1.4188(19) ?
    C17 C26 . 1.4188(19) ?
    C18 C19 . 1.4342(19) ?
    C18 C23 . 1.4377(19) ?
    C19 C20 . 1.362(2) ?
    C20 C21 . 1.416(2) ?
    C21 C22 . 1.356(2) ?
    C22 C23 . 1.430(2) ?
    C23 C24 . 1.391(2) ?
    C24 C25 . 1.391(2) ?
    C25 C26 . 1.4417(19) ?
    C25 C30 . 1.430(2) ?
    C26 C27 . 1.4356(19) ?
    C27 C28 . 1.364(2) ?
    C28 C29 . 1.419(2) ?
    C29 C30 . 1.358(2) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C14 O3 C15 . . 116.95(13) ?
    C10 N1 C2 . . 122.41(12) ?
    N1 C2 C13 . . 112.76(12) ?
    C3 C2 N1 . . 119.95(12) ?
    C3 C2 C13 . . 127.23(13) ?
    C2 C3 C4 . . 122.61(12) ?
    C2 C3 C14 . . 119.20(13) ?
    C14 C3 C4 . . 117.97(12) ?
    C3 C4 C17 . . 112.38(11) ?
    C5 C4 C3 . . 110.73(11) ?
    C5 C4 C17 . . 114.41(11) ?
    C6 C5 C4 . . 118.40(12) ?
    C10 C5 C4 . . 122.21(12) ?
    C10 C5 C6 . . 118.85(12) ?
    O1 C6 C5 . . 121.10(13) ?
    O1 C6 C7 . . 119.63(12) ?
    C5 C6 C7 . . 119.20(12) ?
    C6 C7 C8 . . 115.17(12) ?
    C7 C8 C9 . . 107.55(11) ?
    C7 C8 C11 . . 110.50(12) ?
    C7 C8 C12 . . 109.77(12) ?
    C9 C8 C11 . . 110.82(12) ?
    C12 C8 C9 . . 108.59(12) ?
    C12 C8 C11 . . 109.57(12) ?
    C10 C9 C8 . . 112.84(11) ?
    N1 C10 C9 . . 115.33(12) ?
    C5 C10 N1 . . 120.82(12) ?
    C5 C10 C9 . . 123.84(12) ?
    O2 C14 O3 . . 122.01(14) ?
    O2 C14 C3 . . 126.59(14) ?
    O3 C14 C3 . . 111.41(12) ?
    O3 C15 C16 . . 111.51(14) ?
    C18 C17 C4 . . 120.66(12) ?
    C18 C17 C26 . . 119.36(12) ?
    C26 C17 C4 . . 119.90(12) ?
    C17 C18 C19 . . 123.51(12) ?
    C17 C18 C23 . . 119.94(12) ?
    C19 C18 C23 . . 116.53(12) ?
    C20 C19 C18 . . 121.93(13) ?
    C19 C20 C21 . . 120.87(14) ?
    C22 C21 C20 . . 119.68(13) ?
    C21 C22 C23 . . 121.31(13) ?
    C22 C23 C18 . . 119.67(13) ?
    C24 C23 C18 . . 119.61(13) ?
    C24 C23 C22 . . 120.69(13) ?
    C25 C24 C23 . . 121.68(13) ?
    C24 C25 C26 . . 119.48(13) ?
    C24 C25 C30 . . 120.32(13) ?
    C30 C25 C26 . . 120.17(13) ?
    C17 C26 C25 . . 119.88(12) ?
    C17 C26 C27 . . 124.04(13) ?
    C27 C26 C25 . . 116.07(12) ?
    C28 C27 C26 . . 121.87(14) ?
    C27 C28 C29 . . 121.26(14) ?
    C30 C29 C28 . . 119.33(13) ?
    C29 C30 C25 . . 121.17(14) ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 C6 C7 C8 . . . . -160.55(13) ?
    N1 C2 C3 C4 . . . . -1.6(2) ?
    N1 C2 C3 C14 . . . . -176.08(12) ?
    C2 N1 C10 C5 . . . . -10.5(2) ?
    C2 N1 C10 C9 . . . . 168.21(12) ?
    C2 C3 C4 C5 . . . . -6.93(18) ?
    C2 C3 C4 C17 . . . . 122.39(14) ?
    C2 C3 C14 O2 . . . . -25.1(2) ?
    C2 C3 C14 O3 . . . . 155.09(13) ?
    C3 C4 C5 C6 . . . . -163.92(11) ?
    C3 C4 C5 C10 . . . . 7.48(18) ?
    C3 C4 C17 C18 . . . . -65.27(16) ?
    C3 C4 C17 C26 . . . . 111.42(14) ?
    C4 C3 C14 O2 . . . . 160.16(14) ?
    C4 C3 C14 O3 . . . . -19.65(17) ?
    C4 C5 C6 O1 . . . . 2.40(19) ?
    C4 C5 C6 C7 . . . . 179.41(12) ?
    C4 C5 C10 N1 . . . . 0.6(2) ?
    C4 C5 C10 C9 . . . . -178.06(12) ?
    C4 C17 C18 C19 . . . . -2.05(19) ?
    C4 C17 C18 C23 . . . . 176.69(12) ?
    C4 C17 C26 C25 . . . . -174.79(12) ?
    C4 C17 C26 C27 . . . . 3.8(2) ?
    C5 C4 C17 C18 . . . . 62.12(16) ?
    C5 C4 C17 C26 . . . . -121.19(13) ?
    C5 C6 C7 C8 . . . . 22.39(18) ?
    C6 C5 C10 N1 . . . . 171.93(12) ?
    C6 C5 C10 C9 . . . . -6.7(2) ?
    C6 C7 C8 C9 . . . . -49.79(16) ?
    C6 C7 C8 C11 . . . . 71.30(15) ?
    C6 C7 C8 C12 . . . . -167.75(12) ?
    C7 C8 C9 C10 . . . . 49.90(15) ?
    C8 C9 C10 N1 . . . . 157.27(12) ?
    C8 C9 C10 C5 . . . . -24.03(19) ?
    C10 N1 C2 C3 . . . . 11.0(2) ?
    C10 N1 C2 C13 . . . . -166.55(13) ?
    C10 C5 C6 O1 . . . . -169.29(13) ?
    C10 C5 C6 C7 . . . . 7.72(19) ?
    C11 C8 C9 C10 . . . . -70.98(15) ?
    C12 C8 C9 C10 . . . . 168.62(12) ?
    C13 C2 C3 C4 . . . . 175.60(13) ?
    C13 C2 C3 C14 . . . . 1.1(2) ?
    C14 O3 C15 C16 . . . . -82.03(19) ?
    C14 C3 C4 C5 . . . . 167.62(12) ?
    C14 C3 C4 C17 . . . . -63.06(16) ?
    C15 O3 C14 O2 . . . . -7.7(2) ?
    C15 O3 C14 C3 . . . . 172.08(12) ?
    C17 C4 C5 C6 . . . . 67.85(16) ?
    C17 C4 C5 C10 . . . . -120.75(14) ?
    C17 C18 C19 C20 . . . . 178.82(13) ?
    C17 C18 C23 C22 . . . . -179.25(12) ?
    C17 C18 C23 C24 . . . . -1.38(19) ?
    C17 C26 C27 C28 . . . . -175.04(13) ?
    C18 C17 C26 C25 . . . . 1.94(19) ?
    C18 C17 C26 C27 . . . . -179.50(12) ?
    C18 C19 C20 C21 . . . . 0.1(2) ?
    C18 C23 C24 C25 . . . . 0.8(2) ?
    C19 C18 C23 C22 . . . . -0.43(18) ?
    C19 C18 C23 C24 . . . . 177.45(12) ?
    C19 C20 C21 C22 . . . . 0.2(2) ?
    C20 C21 C22 C23 . . . . -0.6(2) ?
    C21 C22 C23 C18 . . . . 0.8(2) ?
    C21 C22 C23 C24 . . . . -177.10(13) ?
    C22 C23 C24 C25 . . . . 178.66(13) ?
    C23 C18 C19 C20 . . . . 0.04(19) ?
    C23 C24 C25 C26 . . . . 1.1(2) ?
    C23 C24 C25 C30 . . . . -177.01(13) ?
    C24 C25 C26 C17 . . . . -2.52(19) ?
    C24 C25 C26 C27 . . . . 178.81(12) ?
    C24 C25 C30 C29 . . . . 178.32(13) ?
    C25 C26 C27 C28 . . . . 3.6(2) ?
    C26 C17 C18 C19 . . . . -178.75(12) ?
    C26 C17 C18 C23 . . . . -0.01(19) ?
    C26 C25 C30 C29 . . . . 0.2(2) ?
    C26 C27 C28 C29 . . . . -1.2(2) ?
    C27 C28 C29 C30 . . . . -1.8(2) ?
    C28 C29 C30 C25 . . . . 2.3(2) ?
    C30 C25 C26 C17 . . . . 175.63(12) ?
    C30 C25 C26 C27 . . . . -3.04(19) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N1 H1 O1 4_676 0.90(2) 1.94(2) 2.7776(16) 154.2(18) yes
    C13 H13B O2 3_666 0.98 2.65 3.409(2) 134.2 yes
    C19 H19 N1 . 0.95 2.48 3.4148(19) 167.7 yes
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_T_min     0.965
_shelx_estimated_absorpt_T_max     0.992
data_global
_journal_date_recd_electronic     2019-11-01
_journal_date_accepted     2019-12-19
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2020
_journal_volume     76
_journal_issue      2
_journal_page_first     125
_journal_page_last     131
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989019017018
_journal_coeditor_code     DX2021
_publ_contact_author_name     'Nicholas R. Natale'
_publ_contact_author_address
;
Department of Biomedical and Pharmaceutical Sciences
The University of Montana
32 Campus Drive
Missoula, MT 59812
;
_publ_contact_author_email     'nicholas.natale@mso.umt.edu'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '406-243-4132'
_publ_section_title
;
Synthesis and crystal structures of a bis(3-hydroxy-cyclohex-2-en-1-one) and two
hexahydroquinoline derivatives
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Steiger, Scott A.' .
;
Department of Biomedical and Pharmaceutical Sciences
The University of Montana
32 Campus Drive
Missoula, MT 59812
USA
;
    'Li, Chun' .
;
Department of Chemistry
Ithaca College
953 Danby Road
Ithaca, NY 14850
USA
;
    'Gates, Christina' .
;
Department of Biomedical and Pharmaceutical Sciences
The University of Montana
32 Campus Drive
Missoula, MT 59812
USA
;
    'Natale, Nicholas R.' .
;
Department of Biomedical and Pharmaceutical Sciences
The University of Montana
32 Campus Drive
Missoula, MT 59812
USA
;
_publ_section_synopsis
;\
The syntheses and crystal structures of three compounds,
2,2'-[(2-nitrophenyl)methylene]bis(3-hydroxy-5,5-dimethylcyclohex-2-enone)
(I), ethyl
4-(4-hydroxy-3,5-dimethoxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-\
hexahydroquinoline-3-carboxylate (II), and ethyl
4-(9'-anthryl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-\
carboxylate (III,), are reported.
;
