##############################################################################
#                                                                            #
# 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.                                        #
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##############################################################################
data_1
_audit_creation_method     'SHELXL-2017/1'
_chemical_name_systematic
;
1,4-Dihydroxy-2-propoxyanthraquinone acetonitrile monosolvate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H14 O5, C2 H3 N'
_chemical_formula_sum     'C19 H17 N O5'
_chemical_formula_iupac     'C17 H14 O5, C2 H3 N'
_chemical_formula_weight     339.33
_chemical_melting_point     ?
_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.
;
_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     8.2160(11)
_cell_length_b     9.8605(13)
_cell_length_c     10.7410(14)
_cell_angle_alpha     95.999(2)
_cell_angle_beta     90.181(2)
_cell_angle_gamma     113.774(2)
_cell_volume     790.99(18)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3016
_cell_measurement_theta_min     2.71
_cell_measurement_theta_max     27.18
_cell_measurement_temperature     100(2)
_exptl_crystal_description     'cut irregular block'
_exptl_crystal_colour     'orange'
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.09
_exptl_crystal_density_diffrn     1.425
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     356
_exptl_absorpt_coefficient_mu     0.104
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_shelx_estimated_absorpt_T_min     0.955
_shelx_estimated_absorpt_T_max     0.991
_exptl_absorpt_correction_T_min     0.8689
_exptl_absorpt_correction_T_max     1.0000
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     8.3660
_diffrn_reflns_number     10216
_diffrn_reflns_av_R_equivalents     0.0215
_diffrn_reflns_theta_min     1.909
_diffrn_reflns_theta_max     27.253
_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     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_refine_special_details     ?
_reflns_number_total     3548
_reflns_number_gt     2718
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0649
_refine_ls_R_factor_gt     0.0517
_refine_ls_wR_factor_gt     0.1400
_refine_ls_wR_factor_ref     0.1530
_refine_ls_goodness_of_fit_ref     1.058
_refine_ls_restrained_S_all     1.059
_refine_ls_number_reflns     3548
_refine_ls_number_parameters     234
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0962P)²+0.0684P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.710
_refine_diff_density_min     -0.265
_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
;
SMART (Bruker, 2014)
;
_computing_cell_refinement
;
SMART (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
XSeed (Barbour, 2001)
;
_computing_publication_material
;
XSeed (Barbour, 2001)
;
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 0.93351(13) 0.54640(11) 0.31245(9) 0.0224(2) Uani d 1 . .
    H H1O 0.943(2) 0.6376(15) 0.3329(15) 0.027 Uiso d 1 . .
    N N1 0.69308(19) 1.25060(16) 0.93564(13) 0.0376(4) Uani d 1 . .
    C C1 0.83016(17) 0.46925(15) 0.39909(12) 0.0179(3) Uani d 1 . .
    O O2 0.85708(12) 0.26110(10) 0.29025(9) 0.0216(2) Uani d 1 . .
    C C2 0.78580(17) 0.31187(15) 0.38774(12) 0.0186(3) Uani d 1 . .
    O O3 0.50110(13) 0.19718(10) 0.64607(9) 0.0231(3) Uani d 1 . .
    H H3O 0.471(2) 0.2555(17) 0.6993(14) 0.028 Uiso d 1 . .
    C C3 0.67840(17) 0.22550(15) 0.47188(12) 0.0190(3) Uani d 1 . .
    H H3 0.650425 0.121543 0.464073 0.023 Uiso calc 1 . .
    O O4 0.48044(13) 0.42907(11) 0.76272(9) 0.0236(2) Uani d 1 . .
    C C4 0.60915(17) 0.28978(15) 0.56995(12) 0.0184(3) Uani d 1 . .
    O O5 0.90743(13) 0.77360(10) 0.43289(9) 0.0237(3) Uani d 1 . .
    C C5 0.65148(17) 0.44303(14) 0.58446(12) 0.0168(3) Uani d 1 . .
    C C6 0.58069(17) 0.50732(15) 0.68671(12) 0.0186(3) Uani d 1 . .
    C C7 0.63155(17) 0.67078(15) 0.70039(12) 0.0182(3) Uani d 1 . .
    C C8 0.57026(18) 0.73660(16) 0.80017(12) 0.0215(3) Uani d 1 . .
    H H8 0.496307 0.676508 0.858499 0.026 Uiso calc 1 . .
    C C9 0.61668(18) 0.88946(16) 0.81480(13) 0.0230(3) Uani d 1 . .
    H H9 0.577257 0.934122 0.884204 0.028 Uiso calc 1 . .
    C C10 0.72114(18) 0.97713(15) 0.72752(13) 0.0232(3) Uani d 1 . .
    H H10 0.750414 1.081320 0.736488 0.028 Uiso calc 1 . .
    C C11 0.78274(18) 0.91324(15) 0.62752(13) 0.0211(3) Uani d 1 . .
    H H11 0.854261 0.973685 0.568420 0.025 Uiso calc 1 . .
    C C12 0.73939(17) 0.75953(14) 0.61376(12) 0.0175(3) Uani d 1 . .
    C C13 0.80994(17) 0.69324(15) 0.50858(12) 0.0185(3) Uani d 1 . .
    C C14 0.76399(17) 0.53320(14) 0.49710(12) 0.0171(3) Uani d 1 . .
    C C15 0.80376(18) 0.10079(14) 0.26995(12) 0.0197(3) Uani d 1 . .
    H H15A 0.672284 0.048972 0.262662 0.024 Uiso calc 1 . .
    H H15B 0.847744 0.066928 0.341400 0.024 Uiso calc 1 . .
    C C16 0.88231(18) 0.06548(15) 0.15066(12) 0.0216(3) Uani d 1 . .
    H H16A 1.013724 0.117694 0.158502 0.026 Uiso calc 1 . .
    H H16B 0.839009 0.100713 0.079785 0.026 Uiso calc 1 . .
    C C17 0.8285(2) -0.10258(15) 0.12525(13) 0.0259(3) Uani d 1 . .
    H H17A 0.864454 -0.138135 0.198037 0.039 Uiso calc 1 . .
    H H17B 0.887518 -0.124293 0.051405 0.039 Uiso calc 1 . .
    H H17C 0.699127 -0.153202 0.110002 0.039 Uiso calc 1 . .
    C C18 0.7439(2) 1.37684(18) 0.95263(14) 0.0300(3) Uani d 1 . .
    C C19 0.8085(2) 1.53842(19) 0.97699(19) 0.0451(5) Uani d 1 . .
    H H19A 0.707605 1.567300 0.974361 0.068 Uiso calc 1 . .
    H H19B 0.891236 1.584642 0.913041 0.068 Uiso calc 1 . .
    H H19C 0.870055 1.572114 1.059963 0.068 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 C1 . 1.3410(15) ?
    O1 H1O . 0.875(13) ?
    N1 C18 . 1.136(2) ?
    C1 C14 . 1.3938(19) ?
    C1 C2 . 1.4353(19) ?
    O2 C2 . 1.3493(16) ?
    O2 C15 . 1.4516(15) ?
    C2 C3 . 1.3714(19) ?
    O3 C4 . 1.3407(15) ?
    O3 H3O . 0.874(14) ?
    C3 C4 . 1.4106(18) ?
    C3 H3 . 0.9500 ?
    O4 C6 . 1.2505(16) ?
    C4 C5 . 1.3983(18) ?
    O5 C13 . 1.2480(16) ?
    C5 C14 . 1.4292(19) ?
    C5 C6 . 1.4498(18) ?
    C6 C7 . 1.4836(18) ?
    C7 C8 . 1.3947(18) ?
    C7 C12 . 1.4025(18) ?
    C8 C9 . 1.3887(19) ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.392(2) ?
    C9 H9 . 0.9500 ?
    C10 C11 . 1.3877(19) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.4013(18) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.4814(19) ?
    C13 C14 . 1.4584(19) ?
    C15 C16 . 1.5075(18) ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C16 C17 . 1.5265(18) ?
    C16 H16A . 0.9900 ?
    C16 H16B . 0.9900 ?
    C17 H17A . 0.9800 ?
    C17 H17B . 0.9800 ?
    C17 H17C . 0.9800 ?
    C18 C19 . 1.456(2) ?
    C19 H19A . 0.9800 ?
    C19 H19B . 0.9800 ?
    C19 H19C . 0.9800 ?
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
    C1 O1 H1O . . 104.0(11) ?
    O1 C1 C14 . . 123.72(12) ?
    O1 C1 C2 . . 117.06(11) ?
    C14 C1 C2 . . 119.22(12) ?
    C2 O2 C15 . . 116.12(10) ?
    O2 C2 C3 . . 125.11(12) ?
    O2 C2 C1 . . 114.62(12) ?
    C3 C2 C1 . . 120.27(12) ?
    C4 O3 H3O . . 104.0(11) ?
    C2 C3 C4 . . 120.53(12) ?
    C2 C3 H3 . . 119.7 ?
    C4 C3 H3 . . 119.7 ?
    O3 C4 C5 . . 122.48(11) ?
    O3 C4 C3 . . 116.90(12) ?
    C5 C4 C3 . . 120.61(12) ?
    C4 C5 C14 . . 118.88(12) ?
    C4 C5 C6 . . 119.80(12) ?
    C14 C5 C6 . . 121.32(12) ?
    O4 C6 C5 . . 121.78(12) ?
    O4 C6 C7 . . 120.05(11) ?
    C5 C6 C7 . . 118.17(12) ?
    C8 C7 C12 . . 119.70(12) ?
    C8 C7 C6 . . 119.52(12) ?
    C12 C7 C6 . . 120.79(12) ?
    C9 C8 C7 . . 120.41(13) ?
    C9 C8 H8 . . 119.8 ?
    C7 C8 H8 . . 119.8 ?
    C8 C9 C10 . . 119.86(12) ?
    C8 C9 H9 . . 120.1 ?
    C10 C9 H9 . . 120.1 ?
    C11 C10 C9 . . 120.40(12) ?
    C11 C10 H10 . . 119.8 ?
    C9 C10 H10 . . 119.8 ?
    C10 C11 C12 . . 119.97(13) ?
    C10 C11 H11 . . 120.0 ?
    C12 C11 H11 . . 120.0 ?
    C11 C12 C7 . . 119.64(12) ?
    C11 C12 C13 . . 119.48(12) ?
    C7 C12 C13 . . 120.88(12) ?
    O5 C13 C14 . . 121.35(12) ?
    O5 C13 C12 . . 120.31(12) ?
    C14 C13 C12 . . 118.33(12) ?
    C1 C14 C5 . . 120.48(12) ?
    C1 C14 C13 . . 119.04(12) ?
    C5 C14 C13 . . 120.47(12) ?
    O2 C15 C16 . . 107.99(10) ?
    O2 C15 H15A . . 110.1 ?
    C16 C15 H15A . . 110.1 ?
    O2 C15 H15B . . 110.1 ?
    C16 C15 H15B . . 110.1 ?
    H15A C15 H15B . . 108.4 ?
    C15 C16 C17 . . 109.75(11) ?
    C15 C16 H16A . . 109.7 ?
    C17 C16 H16A . . 109.7 ?
    C15 C16 H16B . . 109.7 ?
    C17 C16 H16B . . 109.7 ?
    H16A C16 H16B . . 108.2 ?
    C16 C17 H17A . . 109.5 ?
    C16 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C16 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    N1 C18 C19 . . 178.89(17) ?
    C18 C19 H19A . . 109.5 ?
    C18 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C18 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
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
    C15 O2 C2 C3 . . . . 4.50(19) ?
    C15 O2 C2 C1 . . . . -175.30(10) ?
    O1 C1 C2 O2 . . . . 0.80(18) ?
    C14 C1 C2 O2 . . . . -179.69(11) ?
    O1 C1 C2 C3 . . . . -179.01(11) ?
    C14 C1 C2 C3 . . . . 0.5(2) ?
    O2 C2 C3 C4 . . . . -179.31(12) ?
    C1 C2 C3 C4 . . . . 0.5(2) ?
    C2 C3 C4 O3 . . . . 178.11(11) ?
    C2 C3 C4 C5 . . . . -1.2(2) ?
    O3 C4 C5 C14 . . . . -178.34(11) ?
    C3 C4 C5 C14 . . . . 0.9(2) ?
    O3 C4 C5 C6 . . . . 1.4(2) ?
    C3 C4 C5 C6 . . . . -179.28(11) ?
    C4 C5 C6 O4 . . . . -0.6(2) ?
    C14 C5 C6 O4 . . . . 179.13(11) ?
    C4 C5 C6 C7 . . . . 178.82(11) ?
    C14 C5 C6 C7 . . . . -1.4(2) ?
    O4 C6 C7 C8 . . . . 1.5(2) ?
    C5 C6 C7 C8 . . . . -177.94(11) ?
    O4 C6 C7 C12 . . . . -178.03(11) ?
    C5 C6 C7 C12 . . . . 2.49(19) ?
    C12 C7 C8 C9 . . . . -0.6(2) ?
    C6 C7 C8 C9 . . . . 179.85(11) ?
    C7 C8 C9 C10 . . . . 1.7(2) ?
    C8 C9 C10 C11 . . . . -1.5(2) ?
    C9 C10 C11 C12 . . . . 0.2(2) ?
    C10 C11 C12 C7 . . . . 0.9(2) ?
    C10 C11 C12 C13 . . . . -178.36(11) ?
    C8 C7 C12 C11 . . . . -0.8(2) ?
    C6 C7 C12 C11 . . . . 178.81(11) ?
    C8 C7 C12 C13 . . . . 178.54(11) ?
    C6 C7 C12 C13 . . . . -1.9(2) ?
    C11 C12 C13 O5 . . . . 0.1(2) ?
    C7 C12 C13 O5 . . . . -179.19(11) ?
    C11 C12 C13 C14 . . . . 179.48(11) ?
    C7 C12 C13 C14 . . . . 0.19(19) ?
    O1 C1 C14 C5 . . . . 178.71(11) ?
    C2 C1 C14 C5 . . . . -0.8(2) ?
    O1 C1 C14 C13 . . . . -0.8(2) ?
    C2 C1 C14 C13 . . . . 179.77(11) ?
    C4 C5 C14 C1 . . . . 0.1(2) ?
    C6 C5 C14 C1 . . . . -179.73(11) ?
    C4 C5 C14 C13 . . . . 179.51(11) ?
    C6 C5 C14 C13 . . . . -0.3(2) ?
    O5 C13 C14 C1 . . . . -0.3(2) ?
    C12 C13 C14 C1 . . . . -179.62(11) ?
    O5 C13 C14 C5 . . . . -179.72(11) ?
    C12 C13 C14 C5 . . . . 0.91(19) ?
    C2 O2 C15 C16 . . . . 174.51(10) ?
    O2 C15 C16 C17 . . . . -179.69(10) ?
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
    O1 H1O O5 . 0.875(13) 1.747(14) 2.5537(13) 152.1(15) yes
    O3 H3O O4 . 0.874(14) 1.747(14) 2.5578(13) 153.3(15) yes
    C10 H10 N1 . 0.95 2.73 3.4009(19) 127.8 yes
    C15 H15A O3 2_656 0.99 2.57 3.2179(16) 123.1 yes
    C11 H11 O5 2_776 0.95 2.47 3.2446(17) 138.3 yes
data_2
_audit_creation_method     'SHELXL-2017/1'
_chemical_name_systematic
;
2-Butoxy-1,4-dihydroxyanthraquinone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H16 O5'
_chemical_formula_sum     'C18 H16 O5'
_chemical_formula_weight     312.31
_chemical_melting_point     ?
_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.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/n'
_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     4.7730(9)
_cell_length_b     44.272(8)
_cell_length_c     13.807(3)
_cell_angle_alpha     90
_cell_angle_beta     95.164(2)
_cell_angle_gamma     90
_cell_volume     2905.8(9)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     2921
_cell_measurement_theta_min     2.36
_cell_measurement_theta_max     23.75
_cell_measurement_temperature     100(2)
_exptl_crystal_description     'cut irregular block'
_exptl_crystal_colour     'orange-red'
_exptl_crystal_size_max     0.480
_exptl_crystal_size_mid     0.100
_exptl_crystal_size_min     0.030
_exptl_crystal_density_diffrn     1.428
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     1312
_exptl_absorpt_coefficient_mu     0.104
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_shelx_estimated_absorpt_T_min     0.952
_shelx_estimated_absorpt_T_max     0.997
_exptl_absorpt_correction_T_min     0.854
_exptl_absorpt_correction_T_max     1.000
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_detector_area_resol_mean     8.3660
_diffrn_reflns_number     36901
_diffrn_reflns_av_R_equivalents     0.1043
_diffrn_reflns_theta_min     1.551
_diffrn_reflns_theta_max     27.209
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -56
_diffrn_reflns_limit_k_max     56
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_refine_special_details     ?
_reflns_number_total     6456
_reflns_number_gt     3747
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1202
_refine_ls_R_factor_gt     0.0626
_refine_ls_wR_factor_gt     0.1419
_refine_ls_wR_factor_ref     0.1657
_refine_ls_goodness_of_fit_ref     1.040
_refine_ls_restrained_S_all     1.040
_refine_ls_number_reflns     6456
_refine_ls_number_parameters     429
_refine_ls_number_restraints     4
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0470P)²+2.0816P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.258
_refine_diff_density_min     -0.270
_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'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
SMART (Bruker, 2014)
;
_computing_cell_refinement
;
SMART (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
XSeed (Barbour, 2001)
;
_computing_publication_material
;
XSeed (Barbour, 2001)
;
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 -0.3186(4) 0.27290(4) 0.38526(14) 0.0341(5) Uani d 1 . .
    H H1O -0.448(5) 0.2616(6) 0.359(2) 0.041 Uiso d 1 . .
    C C1 -0.3234(6) 0.29688(6) 0.32535(19) 0.0272(6) Uani d 1 . .
    O O2 0.0428(4) 0.31529(4) 0.43337(13) 0.0312(5) Uani d 1 . .
    C C2 -0.1245(6) 0.32043(6) 0.3504(2) 0.0275(6) Uani d 1 . .
    O O3 -0.2823(4) 0.37359(4) 0.15477(15) 0.0350(5) Uani d 1 . .
    H H3O -0.399(6) 0.3708(7) 0.1034(17) 0.042 Uiso d 1 . .
    C C3 -0.1160(6) 0.34561(6) 0.2928(2) 0.0287(6) Uani d 1 . .
    H H3 0.017152 0.361103 0.309821 0.034 Uiso calc 1 . .
    O O4 -0.6827(4) 0.35220(4) 0.04208(14) 0.0367(5) Uani d 1 . .
    C C4 -0.3032(6) 0.34858(6) 0.2089(2) 0.0286(6) Uani d 1 . .
    O O5 -0.7188(4) 0.25237(4) 0.26716(15) 0.0375(5) Uani d 1 . .
    C C5 -0.5023(5) 0.32611(6) 0.18344(19) 0.0254(6) Uani d 1 . .
    O O6 0.7609(4) 0.39771(4) 0.48700(15) 0.0355(5) Uani d 1 . .
    H H6O 0.636(6) 0.3937(7) 0.4395(17) 0.043 Uiso d 1 . .
    C C6 -0.6920(6) 0.32954(6) 0.0958(2) 0.0293(6) Uani d 1 . .
    O O7 1.1866(4) 0.42067(4) 0.59154(14) 0.0367(5) Uani d 1 . .
    C C7 -0.9003(5) 0.30521(6) 0.07061(19) 0.0266(6) Uani d 1 . .
    O O8 1.2269(4) 0.50371(4) 0.37289(15) 0.0341(5) Uani d 1 . .
    H H8O 1.123(6) 0.5094(7) 0.3208(16) 0.041 Uiso d 1 . .
    C C8 -1.0870(6) 0.30801(6) -0.0124(2) 0.0328(7) Uani d 1 . .
    H H8 -1.081236 0.325412 -0.052455 0.039 Uiso calc 1 . .
    O O9 0.8632(4) 0.50517(4) 0.22553(14) 0.0359(5) Uani d 1 . .
    C C9 -1.2818(6) 0.28529(7) -0.0366(2) 0.0349(7) Uani d 1 . .
    H H9 -1.410599 0.287331 -0.092840 0.042 Uiso calc 1 . .
    O O10 0.4078(4) 0.40025(4) 0.33801(14) 0.0346(5) Uani d 1 . .
    C C10 -1.2893(6) 0.25958(6) 0.0210(2) 0.0340(7) Uani d 1 . .
    H H10 -1.419875 0.243897 0.003368 0.041 Uiso calc 1 . .
    C C11 -1.1065(6) 0.25689(6) 0.1040(2) 0.0321(7) Uani d 1 . .
    H H11 -1.114821 0.239564 0.144244 0.038 Uiso calc 1 . .
    C C12 -0.9090(6) 0.27958(6) 0.12909(19) 0.0274(6) Uani d 1 . .
    C C13 -0.7114(6) 0.27581(6) 0.2171(2) 0.0286(6) Uani d 1 . .
    C C14 -0.5100(5) 0.29996(6) 0.2427(2) 0.0264(6) Uani d 1 . .
    C C15 0.2386(6) 0.33909(6) 0.4653(2) 0.0313(6) Uani d 1 . .
    H H15B 0.136313 0.358244 0.473426 0.038 Uiso calc 1 . .
    H H15A 0.375876 0.342303 0.416602 0.038 Uiso calc 1 . .
    C C16 0.3885(6) 0.32930(6) 0.5611(2) 0.0339(7) Uani d 1 . .
    H H16A 0.538850 0.344065 0.580570 0.041 Uiso calc 1 . .
    H H16B 0.479215 0.309504 0.552161 0.041 Uiso calc 1 . .
    C C17 0.1962(7) 0.32659(7) 0.6425(2) 0.0402(7) Uani d 1 . .
    H H17A 0.060155 0.310046 0.626768 0.048 Uiso calc 1 . .
    H H17B 0.088094 0.345572 0.646233 0.048 Uiso calc 1 . .
    C C18 0.3532(8) 0.32039(7) 0.7413(2) 0.0488(9) Uani d 1 . .
    H H18A 0.475930 0.302797 0.736548 0.073 Uiso calc 1 . .
    H H18B 0.217716 0.316330 0.788912 0.073 Uiso calc 1 . .
    H H18C 0.467288 0.338036 0.761934 0.073 Uiso calc 1 . .
    C C19 0.8649(6) 0.42371(6) 0.4540(2) 0.0296(6) Uani d 1 . .
    C C20 1.0975(6) 0.43683(6) 0.5119(2) 0.0301(6) Uani d 1 . .
    C C21 1.2100(6) 0.46359(6) 0.4840(2) 0.0302(6) Uani d 1 . .
    H H21 1.362242 0.472501 0.522992 0.036 Uiso calc 1 . .
    C C22 1.1009(6) 0.47784(6) 0.3981(2) 0.0300(6) Uani d 1 . .
    C C23 0.8739(6) 0.46552(6) 0.3399(2) 0.0278(6) Uani d 1 . .
    C C24 0.7634(6) 0.48070(6) 0.2524(2) 0.0293(6) Uani d 1 . .
    C C25 0.5272(6) 0.46627(6) 0.1918(2) 0.0300(6) Uani d 1 . .
    C C26 0.4175(6) 0.48005(7) 0.1061(2) 0.0365(7) Uani d 1 . .
    H H26 0.489850 0.498971 0.087551 0.044 Uiso calc 1 . .
    C C27 0.2030(7) 0.46627(7) 0.0475(2) 0.0413(8) Uani d 1 . .
    H H27 0.132225 0.475545 -0.011761 0.050 Uiso calc 1 . .
    C C28 0.0917(6) 0.43906(7) 0.0752(2) 0.0394(7) Uani d 1 . .
    H H28 -0.057104 0.429841 0.035422 0.047 Uiso calc 1 . .
    C C29 0.1970(6) 0.42527(6) 0.1608(2) 0.0354(7) Uani d 1 . .
    H H29 0.120415 0.406580 0.179632 0.042 Uiso calc 1 . .
    C C30 0.4146(6) 0.43869(6) 0.2195(2) 0.0305(6) Uani d 1 . .
    C C31 0.5203(6) 0.42406(6) 0.3111(2) 0.0296(6) Uani d 1 . .
    C C32 0.7571(6) 0.43774(6) 0.3698(2) 0.0290(6) Uani d 1 . .
    C C33 1.4201(6) 0.43232(6) 0.6555(2) 0.0354(7) Uani d 1 . .
    H H33A 1.359002 0.449853 0.692861 0.042 Uiso calc 1 . .
    H H33B 1.575349 0.438816 0.617335 0.042 Uiso calc 1 . .
    C C34 1.5157(7) 0.40682(7) 0.7235(2) 0.0392(7) Uani d 1 . .
    H H34A 1.589349 0.390176 0.685154 0.047 Uiso calc 1 . .
    H H34B 1.351732 0.398995 0.754780 0.047 Uiso calc 1 . .
    C C35 1.7415(7) 0.41641(7) 0.8018(2) 0.0449(8) Uani d 1 . .
    H H35A 1.663659 0.431719 0.844235 0.054 Uiso calc 1 . .
    H H35B 1.900044 0.425732 0.771114 0.054 Uiso calc 1 . .
    C C36 1.8488(8) 0.38931(8) 0.8632(2) 0.0525(9) Uani d 1 . .
    H H36A 1.695632 0.381183 0.898166 0.079 Uiso calc 1 . .
    H H36B 2.003713 0.395739 0.910094 0.079 Uiso calc 1 . .
    H H36C 1.915812 0.373660 0.820721 0.079 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 C1 . 1.345(3) ?
    O1 H1O . 0.848(18) ?
    C1 C14 . 1.390(4) ?
    C1 C2 . 1.431(4) ?
    O2 C2 . 1.356(3) ?
    O2 C15 . 1.450(3) ?
    C2 C3 . 1.372(4) ?
    O3 C4 . 1.344(3) ?
    O3 H3O . 0.870(17) ?
    C3 C4 . 1.404(4) ?
    C3 H3 . 0.9500 ?
    O4 C6 . 1.251(3) ?
    C4 C5 . 1.399(4) ?
    O5 C13 . 1.249(3) ?
    C5 C14 . 1.420(4) ?
    C5 C6 . 1.453(4) ?
    O6 C19 . 1.349(3) ?
    O6 H6O . 0.863(18) ?
    C6 C7 . 1.485(4) ?
    O7 C20 . 1.348(3) ?
    O7 C33 . 1.453(3) ?
    C7 C8 . 1.393(4) ?
    C7 C12 . 1.396(4) ?
    O8 C22 . 1.354(3) ?
    O8 H8O . 0.874(17) ?
    C8 C9 . 1.390(4) ?
    C8 H8 . 0.9500 ?
    O9 C24 . 1.253(3) ?
    C9 C10 . 1.391(4) ?
    C9 H9 . 0.9500 ?
    O10 C31 . 1.254(3) ?
    C10 C11 . 1.381(4) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.399(4) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.479(4) ?
    C13 C14 . 1.460(4) ?
    C15 C16 . 1.510(4) ?
    C15 H15B . 0.9900 ?
    C15 H15A . 0.9900 ?
    C16 C17 . 1.518(4) ?
    C16 H16A . 0.9900 ?
    C16 H16B . 0.9900 ?
    C17 C18 . 1.520(4) ?
    C17 H17A . 0.9900 ?
    C17 H17B . 0.9900 ?
    C18 H18A . 0.9800 ?
    C18 H18B . 0.9800 ?
    C18 H18C . 0.9800 ?
    C19 C32 . 1.377(4) ?
    C19 C20 . 1.432(4) ?
    C20 C21 . 1.370(4) ?
    C21 C22 . 1.402(4) ?
    C21 H21 . 0.9500 ?
    C22 C23 . 1.400(4) ?
    C23 C32 . 1.426(4) ?
    C23 C24 . 1.441(4) ?
    C24 C25 . 1.486(4) ?
    C25 C26 . 1.392(4) ?
    C25 C30 . 1.401(4) ?
    C26 C27 . 1.388(4) ?
    C26 H26 . 0.9500 ?
    C27 C28 . 1.384(4) ?
    C27 H27 . 0.9500 ?
    C28 C29 . 1.384(4) ?
    C28 H28 . 0.9500 ?
    C29 C30 . 1.392(4) ?
    C29 H29 . 0.9500 ?
    C30 C31 . 1.469(4) ?
    C31 C32 . 1.462(4) ?
    C33 C34 . 1.512(4) ?
    C33 H33A . 0.9900 ?
    C33 H33B . 0.9900 ?
    C34 C35 . 1.517(4) ?
    C34 H34A . 0.9900 ?
    C34 H34B . 0.9900 ?
    C35 C36 . 1.531(4) ?
    C35 H35A . 0.9900 ?
    C35 H35B . 0.9900 ?
    C36 H36A . 0.9800 ?
    C36 H36B . 0.9800 ?
    C36 H36C . 0.9800 ?
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
    C1 O1 H1O . . 103(2) ?
    O1 C1 C14 . . 123.8(2) ?
    O1 C1 C2 . . 116.9(2) ?
    C14 C1 C2 . . 119.3(2) ?
    C2 O2 C15 . . 116.7(2) ?
    O2 C2 C3 . . 125.4(2) ?
    O2 C2 C1 . . 114.2(2) ?
    C3 C2 C1 . . 120.4(2) ?
    C4 O3 H3O . . 105(2) ?
    C2 C3 C4 . . 120.3(2) ?
    C2 C3 H3 . . 119.9 ?
    C4 C3 H3 . . 119.9 ?
    O3 C4 C5 . . 121.9(2) ?
    O3 C4 C3 . . 117.5(2) ?
    C5 C4 C3 . . 120.5(2) ?
    C4 C5 C14 . . 119.2(2) ?
    C4 C5 C6 . . 119.6(2) ?
    C14 C5 C6 . . 121.2(2) ?
    C19 O6 H6O . . 100(2) ?
    O4 C6 C5 . . 121.7(2) ?
    O4 C6 C7 . . 120.1(2) ?
    C5 C6 C7 . . 118.2(2) ?
    C20 O7 C33 . . 118.4(2) ?
    C8 C7 C12 . . 119.9(3) ?
    C8 C7 C6 . . 119.6(2) ?
    C12 C7 C6 . . 120.6(2) ?
    C22 O8 H8O . . 103(2) ?
    C9 C8 C7 . . 119.9(3) ?
    C9 C8 H8 . . 120.1 ?
    C7 C8 H8 . . 120.1 ?
    C8 C9 C10 . . 120.4(3) ?
    C8 C9 H9 . . 119.8 ?
    C10 C9 H9 . . 119.8 ?
    C11 C10 C9 . . 119.9(3) ?
    C11 C10 H10 . . 120.1 ?
    C9 C10 H10 . . 120.1 ?
    C10 C11 C12 . . 120.3(3) ?
    C10 C11 H11 . . 119.9 ?
    C12 C11 H11 . . 119.9 ?
    C7 C12 C11 . . 119.7(2) ?
    C7 C12 C13 . . 121.1(2) ?
    C11 C12 C13 . . 119.2(2) ?
    O5 C13 C14 . . 121.7(2) ?
    O5 C13 C12 . . 120.0(2) ?
    C14 C13 C12 . . 118.2(2) ?
    C1 C14 C5 . . 120.3(2) ?
    C1 C14 C13 . . 119.1(2) ?
    C5 C14 C13 . . 120.6(2) ?
    O2 C15 C16 . . 107.4(2) ?
    O2 C15 H15B . . 110.2 ?
    C16 C15 H15B . . 110.2 ?
    O2 C15 H15A . . 110.2 ?
    C16 C15 H15A . . 110.2 ?
    H15B C15 H15A . . 108.5 ?
    C15 C16 C17 . . 113.7(2) ?
    C15 C16 H16A . . 108.8 ?
    C17 C16 H16A . . 108.8 ?
    C15 C16 H16B . . 108.8 ?
    C17 C16 H16B . . 108.8 ?
    H16A C16 H16B . . 107.7 ?
    C16 C17 C18 . . 113.3(3) ?
    C16 C17 H17A . . 108.9 ?
    C18 C17 H17A . . 108.9 ?
    C16 C17 H17B . . 108.9 ?
    C18 C17 H17B . . 108.9 ?
    H17A C17 H17B . . 107.7 ?
    C17 C18 H18A . . 109.5 ?
    C17 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    C17 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    O6 C19 C32 . . 123.3(2) ?
    O6 C19 C20 . . 116.6(2) ?
    C32 C19 C20 . . 120.1(2) ?
    O7 C20 C21 . . 125.8(3) ?
    O7 C20 C19 . . 114.4(2) ?
    C21 C20 C19 . . 119.9(3) ?
    C20 C21 C22 . . 120.1(3) ?
    C20 C21 H21 . . 120.0 ?
    C22 C21 H21 . . 120.0 ?
    O8 C22 C23 . . 121.4(3) ?
    O8 C22 C21 . . 117.3(2) ?
    C23 C22 C21 . . 121.3(2) ?
    C22 C23 C32 . . 118.2(2) ?
    C22 C23 C24 . . 120.4(2) ?
    C32 C23 C24 . . 121.4(2) ?
    O9 C24 C23 . . 122.1(3) ?
    O9 C24 C25 . . 119.7(3) ?
    C23 C24 C25 . . 118.2(2) ?
    C26 C25 C30 . . 119.3(3) ?
    C26 C25 C24 . . 119.9(3) ?
    C30 C25 C24 . . 120.8(3) ?
    C27 C26 C25 . . 120.3(3) ?
    C27 C26 H26 . . 119.8 ?
    C25 C26 H26 . . 119.8 ?
    C28 C27 C26 . . 120.2(3) ?
    C28 C27 H27 . . 119.9 ?
    C26 C27 H27 . . 119.9 ?
    C27 C28 C29 . . 120.1(3) ?
    C27 C28 H28 . . 120.0 ?
    C29 C28 H28 . . 120.0 ?
    C28 C29 C30 . . 120.2(3) ?
    C28 C29 H29 . . 119.9 ?
    C30 C29 H29 . . 119.9 ?
    C29 C30 C25 . . 119.9(3) ?
    C29 C30 C31 . . 119.5(3) ?
    C25 C30 C31 . . 120.6(3) ?
    O10 C31 C32 . . 121.0(3) ?
    O10 C31 C30 . . 120.2(2) ?
    C32 C31 C30 . . 118.9(2) ?
    C19 C32 C23 . . 120.5(2) ?
    C19 C32 C31 . . 119.5(2) ?
    C23 C32 C31 . . 120.0(2) ?
    O7 C33 C34 . . 106.5(2) ?
    O7 C33 H33A . . 110.4 ?
    C34 C33 H33A . . 110.4 ?
    O7 C33 H33B . . 110.4 ?
    C34 C33 H33B . . 110.4 ?
    H33A C33 H33B . . 108.6 ?
    C33 C34 C35 . . 112.9(2) ?
    C33 C34 H34A . . 109.0 ?
    C35 C34 H34A . . 109.0 ?
    C33 C34 H34B . . 109.0 ?
    C35 C34 H34B . . 109.0 ?
    H34A C34 H34B . . 107.8 ?
    C34 C35 C36 . . 110.9(3) ?
    C34 C35 H35A . . 109.5 ?
    C36 C35 H35A . . 109.5 ?
    C34 C35 H35B . . 109.5 ?
    C36 C35 H35B . . 109.5 ?
    H35A C35 H35B . . 108.1 ?
    C35 C36 H36A . . 109.5 ?
    C35 C36 H36B . . 109.5 ?
    H36A C36 H36B . . 109.5 ?
    C35 C36 H36C . . 109.5 ?
    H36A C36 H36C . . 109.5 ?
    H36B C36 H36C . . 109.5 ?
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
    C15 O2 C2 C3 . . . . 2.6(4) ?
    C15 O2 C2 C1 . . . . -176.8(2) ?
    O1 C1 C2 O2 . . . . -0.6(3) ?
    C14 C1 C2 O2 . . . . 178.7(2) ?
    O1 C1 C2 C3 . . . . 179.9(2) ?
    C14 C1 C2 C3 . . . . -0.7(4) ?
    O2 C2 C3 C4 . . . . -179.2(2) ?
    C1 C2 C3 C4 . . . . 0.2(4) ?
    C2 C3 C4 O3 . . . . -179.2(2) ?
    C2 C3 C4 C5 . . . . 0.6(4) ?
    O3 C4 C5 C14 . . . . 178.8(2) ?
    C3 C4 C5 C14 . . . . -1.0(4) ?
    O3 C4 C5 C6 . . . . 0.4(4) ?
    C3 C4 C5 C6 . . . . -179.4(2) ?
    C4 C5 C6 O4 . . . . -0.1(4) ?
    C14 C5 C6 O4 . . . . -178.5(3) ?
    C4 C5 C6 C7 . . . . 179.8(2) ?
    C14 C5 C6 C7 . . . . 1.4(4) ?
    O4 C6 C7 C8 . . . . -0.8(4) ?
    C5 C6 C7 C8 . . . . 179.3(2) ?
    O4 C6 C7 C12 . . . . 178.8(3) ?
    C5 C6 C7 C12 . . . . -1.0(4) ?
    C12 C7 C8 C9 . . . . 0.1(4) ?
    C6 C7 C8 C9 . . . . 179.8(3) ?
    C7 C8 C9 C10 . . . . -0.8(4) ?
    C8 C9 C10 C11 . . . . 1.5(4) ?
    C9 C10 C11 C12 . . . . -1.6(4) ?
    C8 C7 C12 C11 . . . . -0.2(4) ?
    C6 C7 C12 C11 . . . . -179.9(2) ?
    C8 C7 C12 C13 . . . . 179.3(2) ?
    C6 C7 C12 C13 . . . . -0.3(4) ?
    C10 C11 C12 C7 . . . . 1.0(4) ?
    C10 C11 C12 C13 . . . . -178.6(2) ?
    C7 C12 C13 O5 . . . . -178.4(3) ?
    C11 C12 C13 O5 . . . . 1.2(4) ?
    C7 C12 C13 C14 . . . . 1.3(4) ?
    C11 C12 C13 C14 . . . . -179.1(2) ?
    O1 C1 C14 C5 . . . . 179.7(2) ?
    C2 C1 C14 C5 . . . . 0.4(4) ?
    O1 C1 C14 C13 . . . . -1.0(4) ?
    C2 C1 C14 C13 . . . . 179.6(2) ?
    C4 C5 C14 C1 . . . . 0.5(4) ?
    C6 C5 C14 C1 . . . . 178.9(2) ?
    C4 C5 C14 C13 . . . . -178.8(2) ?
    C6 C5 C14 C13 . . . . -0.4(4) ?
    O5 C13 C14 C1 . . . . -0.6(4) ?
    C12 C13 C14 C1 . . . . 179.7(2) ?
    O5 C13 C14 C5 . . . . 178.7(3) ?
    C12 C13 C14 C5 . . . . -1.0(4) ?
    C2 O2 C15 C16 . . . . 176.7(2) ?
    O2 C15 C16 C17 . . . . -65.1(3) ?
    C15 C16 C17 C18 . . . . -173.1(2) ?
    C33 O7 C20 C21 . . . . 0.9(4) ?
    C33 O7 C20 C19 . . . . -179.4(2) ?
    O6 C19 C20 O7 . . . . 1.7(4) ?
    C32 C19 C20 O7 . . . . -178.9(2) ?
    O6 C19 C20 C21 . . . . -178.5(2) ?
    C32 C19 C20 C21 . . . . 0.8(4) ?
    O7 C20 C21 C22 . . . . 178.6(3) ?
    C19 C20 C21 C22 . . . . -1.1(4) ?
    C20 C21 C22 O8 . . . . -177.9(2) ?
    C20 C21 C22 C23 . . . . 1.0(4) ?
    O8 C22 C23 C32 . . . . 178.2(2) ?
    C21 C22 C23 C32 . . . . -0.7(4) ?
    O8 C22 C23 C24 . . . . -1.7(4) ?
    C21 C22 C23 C24 . . . . 179.4(3) ?
    C22 C23 C24 O9 . . . . -0.4(4) ?
    C32 C23 C24 O9 . . . . 179.7(3) ?
    C22 C23 C24 C25 . . . . 178.4(3) ?
    C32 C23 C24 C25 . . . . -1.5(4) ?
    O9 C24 C25 C26 . . . . -0.3(4) ?
    C23 C24 C25 C26 . . . . -179.1(3) ?
    O9 C24 C25 C30 . . . . 179.0(3) ?
    C23 C24 C25 C30 . . . . 0.2(4) ?
    C30 C25 C26 C27 . . . . -1.4(4) ?
    C24 C25 C26 C27 . . . . 178.0(3) ?
    C25 C26 C27 C28 . . . . 1.6(5) ?
    C26 C27 C28 C29 . . . . -0.9(5) ?
    C27 C28 C29 C30 . . . . 0.1(4) ?
    C28 C29 C30 C25 . . . . 0.1(4) ?
    C28 C29 C30 C31 . . . . 178.8(3) ?
    C26 C25 C30 C29 . . . . 0.6(4) ?
    C24 C25 C30 C29 . . . . -178.8(3) ?
    C26 C25 C30 C31 . . . . -178.2(3) ?
    C24 C25 C30 C31 . . . . 2.5(4) ?
    C29 C30 C31 O10 . . . . -2.8(4) ?
    C25 C30 C31 O10 . . . . 176.0(2) ?
    C29 C30 C31 C32 . . . . 177.3(3) ?
    C25 C30 C31 C32 . . . . -3.9(4) ?
    O6 C19 C32 C23 . . . . 178.8(2) ?
    C20 C19 C32 C23 . . . . -0.5(4) ?
    O6 C19 C32 C31 . . . . -0.9(4) ?
    C20 C19 C32 C31 . . . . 179.8(2) ?
    C22 C23 C32 C19 . . . . 0.5(4) ?
    C24 C23 C32 C19 . . . . -179.6(3) ?
    C22 C23 C32 C31 . . . . -179.9(2) ?
    C24 C23 C32 C31 . . . . 0.0(4) ?
    O10 C31 C32 C19 . . . . 2.4(4) ?
    C30 C31 C32 C19 . . . . -177.7(2) ?
    O10 C31 C32 C23 . . . . -177.2(2) ?
    C30 C31 C32 C23 . . . . 2.7(4) ?
    C20 O7 C33 C34 . . . . -167.3(2) ?
    O7 C33 C34 C35 . . . . -174.3(3) ?
    C33 C34 C35 C36 . . . . -175.2(3) ?
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
    O1 H1O O5 . 0.848(18) 1.78(2) 2.564(3) 153(3) yes
    O3 H3O O4 . 0.870(17) 1.74(2) 2.536(3) 151(3) yes
    O6 H6O O10 . 0.863(18) 1.72(2) 2.542(3) 158(3) yes
    O8 H8O O9 . 0.874(17) 1.73(2) 2.554(3) 155(3) yes
    C3 H3 O10 . 0.95 2.55 3.494(3) 172.8 yes
    C29 H29 O3 . 0.95 2.41 3.231(4) 144.0 yes
    C15 H15B O6 1_455 0.99 2.52 3.485(3) 164.4 yes
    C21 H21 O8 3_866 0.95 2.55 3.502(3) 179.7 yes
    C33 H33A O9 3_766 0.99 2.56 3.547(4) 172.1 yes
data_global
_journal_date_recd_electronic     2017-08-11
_journal_date_accepted     2017-10-11
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2017
_journal_volume     73
_journal_issue     11
_journal_page_first     1687
_journal_page_last     1691
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989017014724
_journal_coeditor_code     PK2605
_publ_contact_author_name     'Professor E. Bosch'
_publ_contact_author_address
;
Department of Chemistry,
Missouri State University,
Springfield, MO 65897, USA
;
_publ_contact_author_email     'ericbosch@missouristate.edu'
_publ_contact_author_fax     '417 8365507'
_publ_contact_author_phone     '417 8364277'
_publ_section_title
;
Synthesis and crystal structures of two purpurin derivatives:
1,4-dihydroxy-2-propoxyanthraquinone and 2-butoxy-1,4-dihydroxyanthraquinone
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Bosch, Eric' .
;
Department of Chemistry,
Missouri State University,
Springfield, MO 65897, USA
;
    'McClain, Emily N.' .
;
Department of Chemistry,
Missouri State University,
Springfield, MO 65897, USA
;
_publ_section_synopsis
;
The title compounds were obtained by deprotonation of
1,2,4-trihydroxyanthraquinone (purpurin) using sodium hydride followed by
reaction with either 1-bromopropane or 1-bromobutane. The compounds were
characterized by ¹H and ¹³C NMR and the structures determined using
single-crystal X-ray diffraction.
;
