##############################################################################
#                                                                            #
# 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_global
_audit_creation_method     SHELXL-2018
_journal_date_recd_electronic     2019-08-26
_journal_date_accepted     2019-09-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2019
_journal_volume     75
_journal_issue     10
_journal_page_first     1515
_journal_page_last     1518
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989019012866
_journal_coeditor_code     SU5514
_publ_contact_author_name     'V. Maheshwaran'
_publ_contact_author_address
;
     CAS in Crystallography and Biophysics,
     University of Madras,
     Guindy Campus,
     Chennai 600 025
     India
;
_publ_contact_author_email     mahes1287@gmail.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;\
Crystal structure and Hirshfeld surface analysis of
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-N-(pyridin-2-ylmethyl)\
benzamide
;
loop_
    _publ_author_name
    _publ_author_address
    'G. Artheswari'
;
     CAS in Crystallography and Biophysics,
     University of Madras,
     Guindy Campus,
     Chennai 600 025
     India
;
    'V. Maheshwaran'
;
     CAS in Crystallography and Biophysics,
     University of Madras,
     Guindy Campus,
     Chennai 600 025
     India
;
    'N. Gautham'
;
     CAS in Crystallography and Biophysics,
     University of Madras,
     Guindy Campus,
     Chennai 600 025
     India
;
_publ_section_synopsis
;
The title N-(pyridin-2-ylmethyl)benzamide derivative, crystallizes with
two independent molecules (A and B) in the asymmetric unit,
which differ essentially in the orientation of the pyridine ring with respect
to the benzene ring, with the two rings being inclined to each other by 53.3
(2) and 72.9 (2)° in molecules A and B, respectively.
;
data_I
_audit_creation_method     'SHELXL-2018/3'
_chemical_name_systematic
;
3-(cyclopropylmethoxy)-4-(difluoromethoxy)-N-(pyridin-2-ylmethyl)\
benzamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H18 F2 N2 O3'
_chemical_formula_sum     'C18 H18 F2 N2 O3'
_chemical_formula_iupac     'C18 H18 F2 N2 O3'
_chemical_formula_weight     348.34
_chemical_melting_point     ?
_chemical_absolute_configuration     unk
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P 21 21 21'
_space_group_name_Hall     'P 2ac 2ab'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
_cell_length_a     13.4775(12)
_cell_length_b     28.026(3)
_cell_length_c     9.1085(9)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     3440.5(6)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     8521
_cell_measurement_theta_min     1.453
_cell_measurement_theta_max     28.356
_cell_measurement_temperature     293(2)
_exptl_crystal_description     BLOCK
_exptl_crystal_colour     COLOURLESS
_exptl_crystal_size_max     0.300
_exptl_crystal_size_mid     0.250
_exptl_crystal_size_min     0.200
_exptl_crystal_density_diffrn     1.345
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     1456
_exptl_absorpt_coefficient_mu     0.106
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_absorpt_correction_T_min     0.642
_exptl_absorpt_correction_T_max     0.785
_diffrn_ambient_temperature     293(2)
_diffrn_source     ?
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type
                              'Bruker SMART APEXII area-detector diffractometer'
_diffrn_measurement_method     'ω and φ scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     33263
_diffrn_reflns_av_R_equivalents     0.0371
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_theta_min     1.453
_diffrn_reflns_theta_max     28.356
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -37
_diffrn_reflns_limit_k_max     37
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     12
_refine_special_details     ?
_reflns_number_total     8521
_reflns_number_gt     5868
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0832
_refine_ls_R_factor_gt     0.0529
_refine_ls_wR_factor_gt     0.1444
_refine_ls_wR_factor_ref     0.1671
_refine_ls_goodness_of_fit_ref     1.021
_refine_ls_restrained_S_all     1.021
_refine_ls_number_reflns     8521
_refine_ls_number_parameters     459
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0901P)²+0.6343P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.669
_refine_diff_density_min     -0.241
_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'
    'F' 'F' 0.0171 0.0103
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_structure_solution
;
SHELXS2013/1 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
SHELXL2018/3 (Sheldrick, 2015) and PLATON (Spek, 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
    C C3A 0.6926(5) 0.85621(17) 0.0399(6) 0.0849(15) Uani d 1 . .
    H H3A 0.760513 0.868025 0.052106 0.102 Uiso calc 1 . .
    C C3B 0.8930(3) 0.64609(14) 0.4443(5) 0.0594(10) Uani d 1 . .
    H H3B 0.824697 0.634683 0.432638 0.071 Uiso calc 1 . .
    C C1B 0.9416(4) 0.63426(16) 0.5869(5) 0.0770(14) Uani d 1 . .
    H H1B1 0.988434 0.657112 0.626991 0.092 Uiso calc 1 . .
    H H1B2 0.902904 0.617075 0.659464 0.092 Uiso calc 1 . .
    C C1A 0.6470(6) 0.8684(2) -0.0992(6) 0.0997(19) Uani d 1 . .
    H H1A1 0.686226 0.886135 -0.169794 0.120 Uiso calc 1 . .
    H H1A2 0.600245 0.845892 -0.141389 0.120 Uiso calc 1 . .
    C C2A 0.6200(6) 0.8918(2) 0.0358(7) 0.111(2) Uani d 1 . .
    H H2A1 0.641359 0.924536 0.049262 0.134 Uiso calc 1 . .
    H H2A2 0.555580 0.884387 0.077600 0.134 Uiso calc 1 . .
    C C2B 0.9698(4) 0.60887(18) 0.4527(6) 0.0821(14) Uani d 1 . .
    H H2B1 0.948720 0.575924 0.442855 0.098 Uiso calc 1 . .
    H H2B2 1.034168 0.615922 0.410413 0.098 Uiso calc 1 . .
    C C4B 0.9158(3) 0.69265(12) 0.3746(4) 0.0533(9) Uani d 1 . .
    H H4B1 0.871794 0.717173 0.412054 0.064 Uiso calc 1 . .
    H H4B2 0.983671 0.701907 0.395770 0.064 Uiso calc 1 . .
    C C4A 0.6728(4) 0.80972(14) 0.1111(4) 0.0599(10) Uani d 1 . .
    H H4A1 0.605344 0.799607 0.090866 0.072 Uiso calc 1 . .
    H H4A2 0.717818 0.785685 0.073220 0.072 Uiso calc 1 . .
    C C5A 0.6758(3) 0.77698(11) 0.3535(4) 0.0421(7) Uani d 1 . .
    C C5B 0.9153(3) 0.72633(11) 0.1320(4) 0.0418(7) Uani d 1 . .
    C C10A 0.6486(3) 0.73121(12) 0.3097(4) 0.0423(7) Uani d 1 . .
    H H10A 0.636984 0.725073 0.210853 0.051 Uiso calc 1 . .
    C C10B 0.9444(3) 0.77079(12) 0.1793(4) 0.0425(7) Uani d 1 . .
    H H10B 0.956199 0.775829 0.278668 0.051 Uiso calc 1 . .
    C C9A 0.6385(2) 0.69462(11) 0.4113(3) 0.0398(7) Uani d 1 . .
    C C9B 0.9564(2) 0.80857(11) 0.0804(3) 0.0393(7) Uani d 1 . .
    C C8B 0.9374(3) 0.80117(12) -0.0676(4) 0.0443(7) Uani d 1 . .
    H H8B 0.944975 0.825994 -0.134414 0.053 Uiso calc 1 . .
    C C8A 0.6566(3) 0.70345(12) 0.5597(4) 0.0450(8) Uani d 1 . .
    H H8A 0.649867 0.679050 0.628203 0.054 Uiso calc 1 . .
    C C7A 0.6847(3) 0.74862(12) 0.6046(4) 0.0467(8) Uani d 1 . .
    H H7A 0.696901 0.754677 0.703354 0.056 Uiso calc 1 . .
    C C7B 0.9069(3) 0.75644(12) -0.1152(4) 0.0471(8) Uani d 1 . .
    H H7B 0.894040 0.751332 -0.214280 0.057 Uiso calc 1 . .
    C C6A 0.6947(3) 0.78472(11) 0.5024(4) 0.0428(7) Uani d 1 . .
    C C6B 0.8957(3) 0.71980(11) -0.0171(4) 0.0441(8) Uani d 1 . .
    C C11B 0.7764(3) 0.65960(13) -0.0361(4) 0.0556(9) Uani d 1 . .
    H H11B 0.770549 0.653960 0.069771 0.067 Uiso calc 1 . .
    C C11A 0.8125(3) 0.84507(12) 0.5158(4) 0.0523(9) Uani d 1 . .
    H H11A 0.820805 0.846015 0.408994 0.063 Uiso calc 1 . .
    C C12A 0.6111(3) 0.64577(11) 0.3570(3) 0.0399(7) Uani d 1 . .
    C C12B 0.9851(3) 0.85610(11) 0.1403(3) 0.0394(7) Uani d 1 . .
    C C13B 1.0486(3) 0.93630(12) 0.0893(4) 0.0527(9) Uani d 1 . .
    H H13A 1.112422 0.944908 0.047812 0.063 Uiso calc 1 . .
    H H13B 1.053716 0.938497 0.195349 0.063 Uiso calc 1 . .
    C C13A 0.5474(3) 0.56661(11) 0.4218(4) 0.0504(9) Uani d 1 . .
    H H13C 0.558990 0.560555 0.318366 0.060 Uiso calc 1 . .
    H H13D 0.477237 0.561821 0.440582 0.060 Uiso calc 1 . .
    C C14A 0.6056(3) 0.53127(11) 0.5106(4) 0.0468(8) Uani d 1 . .
    C C14B 0.9714(3) 0.97029(12) 0.0361(5) 0.0574(10) Uani d 1 . .
    C C15A 0.6971(3) 0.54131(14) 0.5656(5) 0.0604(10) Uani d 1 . .
    H H15A 0.726593 0.570913 0.550449 0.072 Uiso calc 1 . .
    C C15B 0.8969(5) 0.9869(2) 0.1237(8) 0.0966(18) Uani d 1 . .
    H H15B 0.893675 0.977774 0.221716 0.116 Uiso calc 1 . .
    C C16A 0.7455(4) 0.50557(19) 0.6458(7) 0.0808(14) Uani d 1 . .
    H H16A 0.808325 0.511136 0.684333 0.097 Uiso calc 1 . .
    C C16B 0.8265(6) 1.0173(3) 0.0664(11) 0.128(3) Uani d 1 . .
    H H16B 0.774980 1.029011 0.124056 0.154 Uiso calc 1 . .
    C C17A 0.7010(5) 0.46329(18) 0.6668(7) 0.0911(17) Uani d 1 . .
    H H17A 0.732284 0.439371 0.720385 0.109 Uiso calc 1 . .
    C C17B 0.8351(6) 1.0297(2) -0.0794(11) 0.122(3) Uani d 1 . .
    H H17B 0.787592 1.048970 -0.124001 0.146 Uiso calc 1 . .
    C C18A 0.6109(5) 0.45618(16) 0.6094(7) 0.0910(17) Uani d 1 . .
    H H18A 0.580764 0.426749 0.624739 0.109 Uiso calc 1 . .
    C C18B 0.9148(6) 1.0132(2) -0.1574(7) 0.108(2) Uani d 1 . .
    H H18B 0.922244 1.023375 -0.253996 0.130 Uiso calc 1 . .
    N N1A 0.5726(3) 0.61610(10) 0.4539(3) 0.0465(7) Uani d 1 . .
    N N1B 1.0244(3) 0.88763(10) 0.0482(4) 0.0473(7) Uani d 1 . .
    N N2B 0.9813(4) 0.98388(15) -0.1035(4) 0.0834(13) Uani d 1 . .
    N N2A 0.5614(3) 0.48899(12) 0.5308(5) 0.0714(10) Uani d 1 . .
    O O1B 0.9022(2) 0.68714(8) 0.2187(3) 0.0538(6) Uani d 1 . .
    O O1A 0.6868(2) 0.81526(8) 0.2653(3) 0.0573(7) Uani d 1 . .
    O O2A 0.7199(2) 0.83023(8) 0.5524(3) 0.0547(7) Uani d 1 . .
    O O2B 0.8688(2) 0.67504(9) -0.0719(3) 0.0547(7) Uani d 1 . .
    O O3A 0.6272(2) 0.63485(8) 0.2278(3) 0.0527(6) Uani d 1 . .
    O O3B 0.9710(2) 0.86563(9) 0.2718(3) 0.0555(7) Uani d 1 . .
    F F2B 0.7076(2) 0.69107(10) -0.0828(3) 0.0810(8) Uani d 1 . .
    F F1A 0.8220(3) 0.88794(10) 0.5731(5) 0.1111(12) Uani d 1 . .
    F F2A 0.8810(2) 0.81731(11) 0.5780(4) 0.0885(9) Uani d 1 . .
    F F1B 0.7623(3) 0.61959(10) -0.1115(4) 0.0974(10) Uani d 1 . .
    H H1A 0.552(3) 0.6261(14) 0.535(5) 0.053(11) Uiso d 1 . .
    H H1B 1.040(3) 0.8804(13) -0.028(4) 0.039(10) 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
    C3A C2A . 1.397(9) ?
    C3A C1A . 1.449(8) ?
    C3A C4A . 1.479(6) ?
    C3A H3A . 0.9800 ?
    C3B C2B . 1.471(6) ?
    C3B C4B . 1.484(5) ?
    C3B C1B . 1.492(6) ?
    C3B H3B . 0.9800 ?
    C1B C2B . 1.465(7) ?
    C1B H1B1 . 0.9700 ?
    C1B H1B2 . 0.9700 ?
    C1A C2A . 1.441(8) ?
    C1A H1A1 . 0.9700 ?
    C1A H1A2 . 0.9700 ?
    C2A H2A1 . 0.9700 ?
    C2A H2A2 . 0.9700 ?
    C2B H2B1 . 0.9700 ?
    C2B H2B2 . 0.9700 ?
    C4B O1B . 1.440(4) ?
    C4B H4B1 . 0.9700 ?
    C4B H4B2 . 0.9700 ?
    C4A O1A . 1.426(5) ?
    C4A H4A1 . 0.9700 ?
    C4A H4A2 . 0.9700 ?
    C5A O1A . 1.349(4) ?
    C5A C10A . 1.392(5) ?
    C5A C6A . 1.397(5) ?
    C5B O1B . 1.365(4) ?
    C5B C10B . 1.375(5) ?
    C5B C6B . 1.395(5) ?
    C10A C9A . 1.388(5) ?
    C10A H10A . 0.9300 ?
    C10B C9B . 1.399(4) ?
    C10B H10B . 0.9300 ?
    C9A C8A . 1.396(5) ?
    C9A C12A . 1.501(4) ?
    C9B C8B . 1.388(5) ?
    C9B C12B . 1.490(4) ?
    C8B C7B . 1.389(5) ?
    C8B H8B . 0.9300 ?
    C8A C7A . 1.383(5) ?
    C8A H8A . 0.9300 ?
    C7A C6A . 1.381(5) ?
    C7A H7A . 0.9300 ?
    C7B C6B . 1.370(5) ?
    C7B H7B . 0.9300 ?
    C6A O2A . 1.396(4) ?
    C6B O2B . 1.398(4) ?
    C11B F1B . 1.329(4) ?
    C11B F2B . 1.348(5) ?
    C11B O2B . 1.359(5) ?
    C11B H11B . 0.9800 ?
    C11A F1A . 1.316(4) ?
    C11A F2A . 1.334(5) ?
    C11A O2A . 1.357(5) ?
    C11A H11A . 0.9800 ?
    C12A O3A . 1.235(4) ?
    C12A N1A . 1.319(4) ?
    C12B O3B . 1.242(4) ?
    C12B N1B . 1.328(4) ?
    C13B N1B . 1.452(4) ?
    C13B C14B . 1.492(6) ?
    C13B H13A . 0.9700 ?
    C13B H13B . 0.9700 ?
    C13A N1A . 1.458(4) ?
    C13A C14A . 1.500(5) ?
    C13A H13C . 0.9700 ?
    C13A H13D . 0.9700 ?
    C14A N2A . 1.339(5) ?
    C14A C15A . 1.361(6) ?
    C14B N2B . 1.333(6) ?
    C14B C15B . 1.365(7) ?
    C15A C16A . 1.400(6) ?
    C15A H15A . 0.9300 ?
    C15B C16B . 1.378(10) ?
    C15B H15B . 0.9300 ?
    C16A C17A . 1.342(8) ?
    C16A H16A . 0.9300 ?
    C16B C17B . 1.378(11) ?
    C16B H16B . 0.9300 ?
    C17A C18A . 1.337(9) ?
    C17A H17A . 0.9300 ?
    C17B C18B . 1.369(11) ?
    C17B H17B . 0.9300 ?
    C18A N2A . 1.343(6) ?
    C18A H18A . 0.9300 ?
    C18B N2B . 1.312(7) ?
    C18B H18B . 0.9300 ?
    N1A H1A . 0.83(4) ?
    N1B H1B . 0.75(4) ?
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
    C2A C3A C1A . . 60.8(4) ?
    C2A C3A C4A . . 120.9(6) ?
    C1A C3A C4A . . 120.9(5) ?
    C2A C3A H3A . . 114.6 ?
    C1A C3A H3A . . 114.6 ?
    C4A C3A H3A . . 114.6 ?
    C2B C3B C4B . . 120.0(4) ?
    C2B C3B C1B . . 59.2(3) ?
    C4B C3B C1B . . 118.5(4) ?
    C2B C3B H3B . . 115.8 ?
    C4B C3B H3B . . 115.8 ?
    C1B C3B H3B . . 115.8 ?
    C2B C1B C3B . . 59.7(3) ?
    C2B C1B H1B1 . . 117.8 ?
    C3B C1B H1B1 . . 117.8 ?
    C2B C1B H1B2 . . 117.8 ?
    C3B C1B H1B2 . . 117.8 ?
    H1B1 C1B H1B2 . . 114.9 ?
    C2A C1A C3A . . 57.8(4) ?
    C2A C1A H1A1 . . 118.0 ?
    C3A C1A H1A1 . . 118.0 ?
    C2A C1A H1A2 . . 118.0 ?
    C3A C1A H1A2 . . 118.0 ?
    H1A1 C1A H1A2 . . 115.2 ?
    C3A C2A C1A . . 61.3(4) ?
    C3A C2A H2A1 . . 117.6 ?
    C1A C2A H2A1 . . 117.6 ?
    C3A C2A H2A2 . . 117.6 ?
    C1A C2A H2A2 . . 117.6 ?
    H2A1 C2A H2A2 . . 114.7 ?
    C1B C2B C3B . . 61.1(3) ?
    C1B C2B H2B1 . . 117.7 ?
    C3B C2B H2B1 . . 117.7 ?
    C1B C2B H2B2 . . 117.7 ?
    C3B C2B H2B2 . . 117.7 ?
    H2B1 C2B H2B2 . . 114.8 ?
    O1B C4B C3B . . 107.5(3) ?
    O1B C4B H4B1 . . 110.2 ?
    C3B C4B H4B1 . . 110.2 ?
    O1B C4B H4B2 . . 110.2 ?
    C3B C4B H4B2 . . 110.2 ?
    H4B1 C4B H4B2 . . 108.5 ?
    O1A C4A C3A . . 108.2(4) ?
    O1A C4A H4A1 . . 110.1 ?
    C3A C4A H4A1 . . 110.1 ?
    O1A C4A H4A2 . . 110.1 ?
    C3A C4A H4A2 . . 110.1 ?
    H4A1 C4A H4A2 . . 108.4 ?
    O1A C5A C10A . . 126.2(3) ?
    O1A C5A C6A . . 115.8(3) ?
    C10A C5A C6A . . 118.0(3) ?
    O1B C5B C10B . . 125.8(3) ?
    O1B C5B C6B . . 115.7(3) ?
    C10B C5B C6B . . 118.5(3) ?
    C9A C10A C5A . . 121.0(3) ?
    C9A C10A H10A . . 119.5 ?
    C5A C10A H10A . . 119.5 ?
    C5B C10B C9B . . 121.1(3) ?
    C5B C10B H10B . . 119.4 ?
    C9B C10B H10B . . 119.4 ?
    C10A C9A C8A . . 119.8(3) ?
    C10A C9A C12A . . 118.6(3) ?
    C8A C9A C12A . . 121.6(3) ?
    C8B C9B C10B . . 119.4(3) ?
    C8B C9B C12B . . 122.5(3) ?
    C10B C9B C12B . . 118.1(3) ?
    C9B C8B C7B . . 119.5(3) ?
    C9B C8B H8B . . 120.2 ?
    C7B C8B H8B . . 120.2 ?
    C7A C8A C9A . . 119.8(3) ?
    C7A C8A H8A . . 120.1 ?
    C9A C8A H8A . . 120.1 ?
    C6A C7A C8A . . 119.9(3) ?
    C6A C7A H7A . . 120.1 ?
    C8A C7A H7A . . 120.1 ?
    C6B C7B C8B . . 120.4(3) ?
    C6B C7B H7B . . 119.8 ?
    C8B C7B H7B . . 119.8 ?
    C7A C6A O2A . . 118.2(3) ?
    C7A C6A C5A . . 121.5(3) ?
    O2A C6A C5A . . 120.2(3) ?
    C7B C6B C5B . . 121.1(3) ?
    C7B C6B O2B . . 117.9(3) ?
    C5B C6B O2B . . 121.0(3) ?
    F1B C11B F2B . . 106.9(3) ?
    F1B C11B O2B . . 106.0(3) ?
    F2B C11B O2B . . 110.3(3) ?
    F1B C11B H11B . . 111.2 ?
    F2B C11B H11B . . 111.2 ?
    O2B C11B H11B . . 111.2 ?
    F1A C11A F2A . . 107.2(4) ?
    F1A C11A O2A . . 105.8(3) ?
    F2A C11A O2A . . 110.7(3) ?
    F1A C11A H11A . . 111.0 ?
    F2A C11A H11A . . 111.0 ?
    O2A C11A H11A . . 111.0 ?
    O3A C12A N1A . . 123.4(3) ?
    O3A C12A C9A . . 119.8(3) ?
    N1A C12A C9A . . 116.8(3) ?
    O3B C12B N1B . . 121.8(3) ?
    O3B C12B C9B . . 120.3(3) ?
    N1B C12B C9B . . 117.8(3) ?
    N1B C13B C14B . . 111.1(3) ?
    N1B C13B H13A . . 109.4 ?
    C14B C13B H13A . . 109.4 ?
    N1B C13B H13B . . 109.4 ?
    C14B C13B H13B . . 109.4 ?
    H13A C13B H13B . . 108.0 ?
    N1A C13A C14A . . 113.4(3) ?
    N1A C13A H13C . . 108.9 ?
    C14A C13A H13C . . 108.9 ?
    N1A C13A H13D . . 108.9 ?
    C14A C13A H13D . . 108.9 ?
    H13C C13A H13D . . 107.7 ?
    N2A C14A C15A . . 122.4(4) ?
    N2A C14A C13A . . 115.2(4) ?
    C15A C14A C13A . . 122.4(3) ?
    N2B C14B C15B . . 122.2(5) ?
    N2B C14B C13B . . 115.0(4) ?
    C15B C14B C13B . . 122.8(4) ?
    C14A C15A C16A . . 117.8(4) ?
    C14A C15A H15A . . 121.1 ?
    C16A C15A H15A . . 121.1 ?
    C14B C15B C16B . . 119.8(6) ?
    C14B C15B H15B . . 120.1 ?
    C16B C15B H15B . . 120.1 ?
    C17A C16A C15A . . 119.9(5) ?
    C17A C16A H16A . . 120.1 ?
    C15A C16A H16A . . 120.1 ?
    C17B C16B C15B . . 117.6(7) ?
    C17B C16B H16B . . 121.2 ?
    C15B C16B H16B . . 121.2 ?
    C18A C17A C16A . . 118.8(5) ?
    C18A C17A H17A . . 120.6 ?
    C16A C17A H17A . . 120.6 ?
    C18B C17B C16B . . 118.7(6) ?
    C18B C17B H17B . . 120.6 ?
    C16B C17B H17B . . 120.6 ?
    C17A C18A N2A . . 123.9(5) ?
    C17A C18A H18A . . 118.0 ?
    N2A C18A H18A . . 118.0 ?
    N2B C18B C17B . . 123.6(6) ?
    N2B C18B H18B . . 118.2 ?
    C17B C18B H18B . . 118.2 ?
    C12A N1A C13A . . 123.9(3) ?
    C12A N1A H1A . . 121(3) ?
    C13A N1A H1A . . 115(3) ?
    C12B N1B C13B . . 123.5(3) ?
    C12B N1B H1B . . 121(3) ?
    C13B N1B H1B . . 115(3) ?
    C18B N2B C14B . . 117.9(5) ?
    C14A N2A C18A . . 117.2(4) ?
    C5B O1B C4B . . 117.9(3) ?
    C5A O1A C4A . . 119.1(3) ?
    C11A O2A C6A . . 115.0(3) ?
    C11B O2B C6B . . 116.0(3) ?
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
    C4B C3B C1B C2B . . . . -109.8(5) ?
    C4A C3A C1A C2A . . . . 110.6(7) ?
    C4A C3A C2A C1A . . . . -110.6(7) ?
    C4B C3B C2B C1B . . . . 107.3(5) ?
    C2B C3B C4B O1B . . . . 84.0(5) ?
    C1B C3B C4B O1B . . . . 153.0(4) ?
    C2A C3A C4A O1A . . . . -81.6(7) ?
    C1A C3A C4A O1A . . . . -153.9(5) ?
    O1A C5A C10A C9A . . . . -179.3(3) ?
    C6A C5A C10A C9A . . . . 1.3(5) ?
    O1B C5B C10B C9B . . . . 179.4(3) ?
    C6B C5B C10B C9B . . . . -1.4(5) ?
    C5A C10A C9A C8A . . . . -0.6(5) ?
    C5A C10A C9A C12A . . . . -178.7(3) ?
    C5B C10B C9B C8B . . . . 0.9(5) ?
    C5B C10B C9B C12B . . . . 178.2(3) ?
    C10B C9B C8B C7B . . . . -0.1(5) ?
    C12B C9B C8B C7B . . . . -177.3(3) ?
    C10A C9A C8A C7A . . . . -0.1(5) ?
    C12A C9A C8A C7A . . . . 177.9(3) ?
    C9A C8A C7A C6A . . . . 0.0(5) ?
    C9B C8B C7B C6B . . . . 0.0(5) ?
    C8A C7A C6A O2A . . . . 177.8(3) ?
    C8A C7A C6A C5A . . . . 0.8(5) ?
    O1A C5A C6A C7A . . . . 179.1(3) ?
    C10A C5A C6A C7A . . . . -1.5(5) ?
    O1A C5A C6A O2A . . . . 2.1(5) ?
    C10A C5A C6A O2A . . . . -178.4(3) ?
    C8B C7B C6B C5B . . . . -0.5(5) ?
    C8B C7B C6B O2B . . . . -177.4(3) ?
    O1B C5B C6B C7B . . . . -179.5(3) ?
    C10B C5B C6B C7B . . . . 1.2(5) ?
    O1B C5B C6B O2B . . . . -2.7(5) ?
    C10B C5B C6B O2B . . . . 178.1(3) ?
    C10A C9A C12A O3A . . . . 21.9(5) ?
    C8A C9A C12A O3A . . . . -156.1(3) ?
    C10A C9A C12A N1A . . . . -159.6(3) ?
    C8A C9A C12A N1A . . . . 22.4(5) ?
    C8B C9B C12B O3B . . . . 156.8(3) ?
    C10B C9B C12B O3B . . . . -20.3(5) ?
    C8B C9B C12B N1B . . . . -22.2(5) ?
    C10B C9B C12B N1B . . . . 160.6(3) ?
    N1A C13A C14A N2A . . . . 154.4(4) ?
    N1A C13A C14A C15A . . . . -26.1(5) ?
    N1B C13B C14B N2B . . . . -82.7(4) ?
    N1B C13B C14B C15B . . . . 98.2(5) ?
    N2A C14A C15A C16A . . . . 0.1(6) ?
    C13A C14A C15A C16A . . . . -179.4(4) ?
    N2B C14B C15B C16B . . . . 2.7(10) ?
    C13B C14B C15B C16B . . . . -178.3(6) ?
    C14A C15A C16A C17A . . . . -0.5(8) ?
    C14B C15B C16B C17B . . . . -0.1(12) ?
    C15A C16A C17A C18A . . . . 0.4(9) ?
    C15B C16B C17B C18B . . . . -3.0(13) ?
    C16A C17A C18A N2A . . . . 0.1(10) ?
    C16B C17B C18B N2B . . . . 3.9(12) ?
    O3A C12A N1A C13A . . . . 2.1(6) ?
    C9A C12A N1A C13A . . . . -176.3(3) ?
    C14A C13A N1A C12A . . . . 117.2(4) ?
    O3B C12B N1B C13B . . . . -3.8(6) ?
    C9B C12B N1B C13B . . . . 175.2(3) ?
    C14B C13B N1B C12B . . . . -101.4(4) ?
    C17B C18B N2B C14B . . . . -1.5(11) ?
    C15B C14B N2B C18B . . . . -1.9(8) ?
    C13B C14B N2B C18B . . . . 179.0(5) ?
    C15A C14A N2A C18A . . . . 0.3(7) ?
    C13A C14A N2A C18A . . . . 179.8(5) ?
    C17A C18A N2A C14A . . . . -0.4(9) ?
    C10B C5B O1B C4B . . . . 2.7(5) ?
    C6B C5B O1B C4B . . . . -176.5(3) ?
    C3B C4B O1B C5B . . . . 177.4(3) ?
    C10A C5A O1A C4A . . . . -2.0(6) ?
    C6A C5A O1A C4A . . . . 177.5(3) ?
    C3A C4A O1A C5A . . . . -178.0(4) ?
    F1A C11A O2A C6A . . . . -179.5(3) ?
    F2A C11A O2A C6A . . . . -63.7(4) ?
    C7A C6A O2A C11A . . . . 110.5(4) ?
    C5A C6A O2A C11A . . . . -72.5(4) ?
    F1B C11B O2B C6B . . . . 173.3(3) ?
    F2B C11B O2B C6B . . . . 58.0(4) ?
    C7B C6B O2B C11B . . . . -111.5(4) ?
    C5B C6B O2B C11B . . . . 71.5(4) ?
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
    C11A H11A O3B . 0.98 2.44 3.136(5) 128
    C11B H11B O3A . 0.98 2.47 3.210(5) 132
    C4B H4B1 Cg3 . 0.97 2.87 3.689(4) 143
    C4A H4A2 Cg6 . 0.97 2.90 3.717(5) 143
    N1A H1A O3B 3_466 0.84(4) 2.08(4) 2.895(4) 163(4)
    N1B H1B O3A 3_565 0.75(4) 2.21(4) 2.939(4) 164(4)
    C13A H13C N2B 3_465 0.97 2.55 3.347(5) 140
    C13A H13D F1A 3_466 0.97 2.52 3.294(6) 136
    C13B H13B Cg2 3_566 0.97 2.73 3.748(4) 137
_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     0.969
_shelx_estimated_absorpt_T_max     0.979
