##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# 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 data    # 
# article from which it was obtained.                                        #
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##############################################################################
data_global
_audit_creation_method     'APEX3 v2015.9-0'
_journal_date_recd_electronic     2016-12-23
_journal_date_accepted     2017-01-23
_journal_name_full     'IUCrData'
_journal_year     2017
_journal_volume     2
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314617001201
_journal_coeditor_code     BV4007
_publ_contact_author_name     'Essaghouani, Abdelhanine'
_publ_contact_author_address
;
Laboratoire de Chimie Organique Hétérocyclique
URAC 21
Pôle de Compétence Pharmacochimie
Av Ibn Battouta, BP 1014
Faculté des Sciences
Université Mohammed V
Rabat
Morocco
;
_publ_contact_author_email     essaghouani.hanine@gmail.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     '+212670503002'
_publ_section_title
;
2-(2-Oxo-4-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-1-yl)acetic acid
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Essaghouani, Abdelhanine' .
;
Laboratoire de Chimie Organique Hétérocyclique
URAC 21
Pôle de Compétence Pharmacochimie
Av Ibn Battouta, BP 1014
Faculté des Sciences
Université Mohammed V
Rabat
Morocco
;
    'Boulhaoua, Mohammed' .
;
Laboratoire de Chimie Organique Hétérocyclique
URAC 21
Pôle de Compétence Pharmacochimie
Av Ibn Battouta, BP 1014
Faculté des Sciences
Université Mohammed V
Rabat
Morocco
;
    'El Hafi, Mohamed' .
;
Laboratoire de Chimie Organique Hétérocyclique
URAC 21
Pôle de Compétence Pharmacochimie
Av Ibn Battouta, BP 1014
Faculté des Sciences
Université Mohammed V
Rabat
Morocco
;
    'Benchidmi, Mohammed' .
;
Laboratoire de Chimie Organique Hétérocyclique
URAC 21
Pôle de Compétence Pharmacochimie
Av Ibn Battouta, BP 1014
Faculté des Sciences
Université Mohammed V
Rabat
Morocco
;
    'Essassi, El Mokhtar' .
;
Laboratoire de Chimie Organique Hétérocyclique
URAC 21
Pôle de Compétence Pharmacochimie
Av Ibn Battouta, BP 1014
Faculté des Sciences
Université Mohammed V
Rabat
Morocco
;
    'Mague, Joel T.' .
;
Department of Chemistry
Tulane University
New Orleans, LA 70118
USA
;
_publ_section_synopsis
;
The asymmetric unit of the title compound consists of two independent molecules
having distinctly different conformations. The components of the asymmetric
unit are connected by an O---H...N hydrogen bond, with additional O---H...N
hydrogen bonds connecting this assemblage into chains running parallel to the
b axis. Intermolecular C---H...π(ring) interactions are also present.
;
data_I
_audit_creation_method     'SHELXL-2014/7'
_chemical_name_systematic
;
2-(2-Oxo-4-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-1-yl)acetic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H14 N2 O3'
_chemical_formula_sum     'C17 H14 N2 O3'
_chemical_formula_iupac     'C17 H14 N2 O3'
_chemical_formula_weight     294.30
_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/c'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     17.9752(8)
_cell_length_b     17.4403(8)
_cell_length_c     9.2472(4)
_cell_angle_alpha     90
_cell_angle_beta     102.8920(10)
_cell_angle_gamma     90
_cell_volume     2825.9(2)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     9857
_cell_measurement_theta_min     2.2594
_cell_measurement_theta_max     28.7470
_cell_measurement_temperature     298.(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.320
_exptl_crystal_size_mid     0.290
_exptl_crystal_size_min     0.280
_exptl_crystal_density_diffrn     1.384
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1232
_exptl_absorpt_coefficient_mu     0.097
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_shelx_estimated_absorpt_T_min     0.970
_shelx_estimated_absorpt_T_max     0.973
_exptl_absorpt_correction_T_min     0.89
_exptl_absorpt_correction_T_max     0.97
_exptl_special_details
;
The diffraction data were obtained from 3 sets of 400 frames,
each of width 0.5° in ω, collected at φ = 0.00,
90.00 and 180.00° and 2 sets of 800 frames, each of
width 0.45° in φ, collected at ω = --30.00 and 210.00°.
The scan time was 15 sec/frame.
;
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     8.3333
_diffrn_reflns_number     54166
_diffrn_reflns_av_R_equivalents     0.0331
_diffrn_reflns_theta_min     1.647
_diffrn_reflns_theta_max     29.215
_diffrn_reflns_theta_full     29.200
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -24
_diffrn_reflns_limit_h_max     24
_diffrn_reflns_limit_k_min     -23
_diffrn_reflns_limit_k_max     23
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_refine_special_details
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. Hydrogens attached to oxygen
were placed in calculated positions and included as riding contributions.
;
_reflns_number_total     7627
_reflns_number_gt     5791
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0624
_refine_ls_R_factor_gt     0.0478
_refine_ls_wR_factor_gt     0.1353
_refine_ls_wR_factor_ref     0.1455
_refine_ls_goodness_of_fit_ref     1.109
_refine_ls_restrained_S_all     1.109
_refine_ls_number_reflns     7627
_refine_ls_number_parameters     503
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0941P)²+0.0156P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.364
_refine_diff_density_min     -0.212
_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
;
APEX3 (Bruker, 2016)
;
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
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 0.60331(5) 0.13791(5) 0.27570(13) 0.0536(3) Uani d 1 . .
    O O2 0.70218(5) 0.30973(5) 0.14443(10) 0.0448(2) Uani d 1 . .
    H H2A 0.7194 0.3483 0.1907 0.067 Uiso calc 1 . .
    O O3 0.76238(7) 0.24959(5) 0.34987(10) 0.0523(3) Uani d 1 . .
    N N1 0.71781(5) 0.10783(5) 0.22680(11) 0.0335(2) Uani d 1 . .
    N N2 0.72769(5) -0.06012(5) 0.28503(11) 0.0338(2) Uani d 1 . .
    C C1 0.78810(6) 0.06741(6) 0.26215(12) 0.0325(2) Uani d 1 . .
    C C2 0.85619(7) 0.10630(7) 0.26274(15) 0.0429(3) Uani d 1 . .
    H H2 0.8576(8) 0.1607(10) 0.2436(17) 0.054(4) Uiso d 1 . .
    C C3 0.92572(8) 0.06889(9) 0.29592(17) 0.0498(3) Uani d 1 . .
    H H3 0.9738(9) 0.0964(10) 0.3011(19) 0.061(4) Uiso d 1 . .
    C C4 0.92926(7) -0.00864(9) 0.32758(16) 0.0488(3) Uani d 1 . .
    H H4 0.9792(9) -0.0350(9) 0.3519(17) 0.054(4) Uiso d 1 . .
    C C5 0.86265(7) -0.04874(8) 0.32415(15) 0.0428(3) Uani d 1 . .
    H H5 0.8635(8) -0.1047(9) 0.3472(16) 0.049(4) Uiso d 1 . .
    C C6 0.79178(6) -0.01189(6) 0.29224(13) 0.0337(2) Uani d 1 . .
    C C7 0.67194(6) -0.03881(6) 0.34201(12) 0.0306(2) Uani d 1 . .
    C C8 0.67410(7) 0.03717(6) 0.41964(13) 0.0351(2) Uani d 1 . .
    H H8A 0.6343(7) 0.0428(7) 0.4751(15) 0.038(3) Uiso d 1 . .
    H H8B 0.7249(8) 0.0453(8) 0.4914(15) 0.043(4) Uiso d 1 . .
    C C9 0.66091(6) 0.09902(6) 0.30295(13) 0.0349(2) Uani d 1 . .
    C C10 0.70987(8) 0.17555(6) 0.13187(14) 0.0371(3) Uani d 1 . .
    H H10A 0.7430(8) 0.1719(8) 0.0700(16) 0.042(4) Uiso d 1 . .
    H H10B 0.6579(9) 0.1776(9) 0.0709(17) 0.053(4) Uiso d 1 . .
    C C11 0.72781(7) 0.24848(6) 0.22292(13) 0.0351(2) Uani d 1 . .
    C C12 0.60495(6) -0.08991(6) 0.33007(13) 0.0336(2) Uani d 1 . .
    C C13 0.58545(8) -0.14086(8) 0.21200(16) 0.0478(3) Uani d 1 . .
    H H13 0.6142(9) -0.1415(9) 0.1355(18) 0.058(4) Uiso d 1 . .
    C C14 0.52507(9) -0.19148(9) 0.2063(2) 0.0638(4) Uani d 1 . .
    H H14 0.5166(13) -0.2278(14) 0.127(3) 0.103(7) Uiso d 1 . .
    C C15 0.48451(9) -0.19212(9) 0.3147(2) 0.0627(4) Uani d 1 . .
    H H15 0.4416(10) -0.2285(10) 0.3082(19) 0.068(5) Uiso d 1 . .
    C C16 0.50222(8) -0.14105(8) 0.43070(19) 0.0527(4) Uani d 1 . .
    H H16 0.4772(11) -0.1397(11) 0.505(2) 0.075(5) Uiso d 1 . .
    C C17 0.56172(7) -0.08953(7) 0.43804(15) 0.0410(3) Uani d 1 . .
    H H17 0.5723(8) -0.0524(10) 0.5231(18) 0.056(4) Uiso d 1 . .
    O O4 0.90968(5) 0.61482(6) 0.27642(12) 0.0522(3) Uani d 1 . .
    O O5 0.81149(7) 0.75579(5) 0.35900(11) 0.0582(3) Uani d 1 . .
    O O6 0.74537(7) 0.80350(5) 0.14535(11) 0.0572(3) Uani d 1 . .
    H H6 0.7438 0.8422 0.1948 0.086 Uiso calc 1 . .
    N N3 0.78152(5) 0.60652(5) 0.25031(11) 0.0330(2) Uani d 1 . .
    N N4 0.76233(5) 0.43981(5) 0.28495(10) 0.0323(2) Uani d 1 . .
    C C18 0.71694(6) 0.57473(6) 0.29305(12) 0.0308(2) Uani d 1 . .
    C C19 0.65708(7) 0.62319(7) 0.30917(14) 0.0408(3) Uani d 1 . .
    H H19 0.6625(8) 0.6793(9) 0.3044(16) 0.050(4) Uiso d 1 . .
    C C20 0.59079(7) 0.59410(8) 0.33805(16) 0.0477(3) Uani d 1 . .
    H H20 0.5497(10) 0.6274(10) 0.3508(18) 0.064(5) Uiso d 1 . .
    C C21 0.58232(7) 0.51563(9) 0.35311(16) 0.0492(3) Uani d 1 . .
    H H21 0.5326(8) 0.4907(9) 0.3709(16) 0.047(4) Uiso d 1 . .
    C C22 0.64072(7) 0.46703(7) 0.33788(14) 0.0417(3) Uani d 1 . .
    H H22 0.6367(7) 0.4087(8) 0.3431(15) 0.044(4) Uiso d 1 . .
    C C23 0.70850(6) 0.49519(6) 0.30834(12) 0.0319(2) Uani d 1 . .
    C C24 0.83437(6) 0.45013(6) 0.33622(12) 0.0320(2) Uani d 1 . .
    C C25 0.86337(7) 0.52106(6) 0.42453(13) 0.0361(2) Uani d 1 . .
    H H25A 0.9180(8) 0.5147(8) 0.4696(16) 0.044(4) Uiso d 1 . .
    H H25B 0.8342(8) 0.5321(8) 0.4972(16) 0.043(4) Uiso d 1 . .
    C C26 0.85536(6) 0.58557(6) 0.31257(14) 0.0352(2) Uani d 1 . .
    C C27 0.77099(8) 0.67215(6) 0.15010(14) 0.0374(3) Uani d 1 . .
    H H27A 0.8080(8) 0.6687(8) 0.0928(16) 0.045(4) Uiso d 1 . .
    H H27B 0.7230(8) 0.6712(8) 0.0886(15) 0.040(4) Uiso d 1 . .
    C C28 0.77890(7) 0.74808(6) 0.23226(14) 0.0370(3) Uani d 1 . .
    C C29 0.88927(6) 0.39373(6) 0.30039(13) 0.0343(2) Uani d 1 . .
    C C30 0.95522(7) 0.37419(7) 0.40601(14) 0.0399(3) Uani d 1 . .
    H H30 0.9649(8) 0.3990(9) 0.5045(18) 0.053(4) Uiso d 1 . .
    C C31 1.00541(8) 0.32027(8) 0.37314(17) 0.0473(3) Uani d 1 . .
    H H31 1.0518(9) 0.3082(9) 0.4463(16) 0.049(4) Uiso d 1 . .
    C C32 0.99114(8) 0.28555(8) 0.23510(18) 0.0522(3) Uani d 1 . .
    H H32 1.0269(10) 0.2474(10) 0.214(2) 0.070(5) Uiso d 1 . .
    C C33 0.92654(8) 0.30505(8) 0.12984(17) 0.0506(3) Uani d 1 . .
    H H33 0.9169(9) 0.2840(11) 0.035(2) 0.062(5) Uiso d 1 . .
    C C34 0.87589(7) 0.35883(7) 0.16167(14) 0.0422(3) Uani d 1 . .
    H H34 0.8301(9) 0.3742(9) 0.0780(17) 0.058(4) 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
    O1 C9 . 1.2162(14) ?
    O2 C11 . 1.3157(14) ?
    O2 H2A . 0.8200 ?
    O3 C11 . 1.1996(15) ?
    N1 C9 . 1.3737(14) ?
    N1 C1 . 1.4197(14) ?
    N1 C10 . 1.4593(14) ?
    N2 C7 . 1.2868(14) ?
    N2 C6 . 1.4159(14) ?
    C1 C2 . 1.3983(16) ?
    C1 C6 . 1.4094(15) ?
    C2 C3 . 1.382(2) ?
    C2 H2 . 0.967(17) ?
    C3 C4 . 1.382(2) ?
    C3 H3 . 0.980(16) ?
    C4 C5 . 1.3808(19) ?
    C4 H4 . 0.989(16) ?
    C5 C6 . 1.3984(16) ?
    C5 H5 . 0.999(15) ?
    C7 C12 . 1.4823(15) ?
    C7 C8 . 1.5034(15) ?
    C8 C9 . 1.5066(16) ?
    C8 H8A . 0.975(14) ?
    C8 H8B . 1.012(14) ?
    C10 C11 . 1.5198(15) ?
    C10 H10A . 0.916(14) ?
    C10 H10B . 0.978(15) ?
    C12 C13 . 1.3906(17) ?
    C12 C17 . 1.3952(17) ?
    C13 C14 . 1.391(2) ?
    C13 H13 . 0.964(16) ?
    C14 C15 . 1.365(3) ?
    C14 H14 . 0.96(3) ?
    C15 C16 . 1.376(2) ?
    C15 H15 . 0.991(18) ?
    C16 C17 . 1.3870(18) ?
    C16 H16 . 0.901(19) ?
    C17 H17 . 1.004(17) ?
    O4 C26 . 1.2127(14) ?
    O5 C28 . 1.1952(16) ?
    O6 C28 . 1.3141(15) ?
    O6 H6 . 0.8200 ?
    N3 C26 . 1.3732(14) ?
    N3 C18 . 1.4197(14) ?
    N3 C27 . 1.4582(14) ?
    N4 C24 . 1.2885(14) ?
    N4 C23 . 1.4175(14) ?
    C18 C19 . 1.4022(16) ?
    C18 C23 . 1.4060(15) ?
    C19 C20 . 1.3750(19) ?
    C19 H19 . 0.986(16) ?
    C20 C21 . 1.387(2) ?
    C20 H20 . 0.967(17) ?
    C21 C22 . 1.3807(19) ?
    C21 H21 . 1.039(15) ?
    C22 C23 . 1.3959(16) ?
    C22 H22 . 1.021(15) ?
    C24 C29 . 1.4822(15) ?
    C24 C25 . 1.5097(15) ?
    C25 C26 . 1.5139(17) ?
    C25 H25A . 0.983(14) ?
    C25 H25B . 0.959(15) ?
    C27 C28 . 1.5176(15) ?
    C27 H27A . 0.941(15) ?
    C27 H27B . 0.921(14) ?
    C29 C34 . 1.3915(17) ?
    C29 C30 . 1.3995(16) ?
    C30 C31 . 1.3832(18) ?
    C30 H30 . 0.988(16) ?
    C31 C32 . 1.384(2) ?
    C31 H31 . 0.972(15) ?
    C32 C33 . 1.381(2) ?
    C32 H32 . 0.974(19) ?
    C33 C34 . 1.3838(18) ?
    C33 H33 . 0.933(18) ?
    C34 H34 . 1.031(16) ?
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
    C11 O2 H2A . . 109.5 ?
    C9 N1 C1 . . 123.54(9) ?
    C9 N1 C10 . . 114.51(9) ?
    C1 N1 C10 . . 120.19(9) ?
    C7 N2 C6 . . 120.58(9) ?
    C2 C1 C6 . . 118.21(10) ?
    C2 C1 N1 . . 119.56(10) ?
    C6 C1 N1 . . 122.20(9) ?
    C3 C2 C1 . . 121.29(12) ?
    C3 C2 H2 . . 116.4(9) ?
    C1 C2 H2 . . 122.3(9) ?
    C4 C3 C2 . . 120.36(12) ?
    C4 C3 H3 . . 118.0(10) ?
    C2 C3 H3 . . 121.6(10) ?
    C5 C4 C3 . . 119.48(12) ?
    C5 C4 H4 . . 120.6(9) ?
    C3 C4 H4 . . 120.0(9) ?
    C4 C5 C6 . . 121.10(12) ?
    C4 C5 H5 . . 121.2(8) ?
    C6 C5 H5 . . 117.7(8) ?
    C5 C6 C1 . . 119.55(10) ?
    C5 C6 N2 . . 115.48(10) ?
    C1 C6 N2 . . 124.88(10) ?
    N2 C7 C12 . . 119.32(10) ?
    N2 C7 C8 . . 120.71(10) ?
    C12 C7 C8 . . 119.97(10) ?
    C7 C8 C9 . . 107.81(9) ?
    C7 C8 H8A . . 113.3(8) ?
    C9 C8 H8A . . 106.8(8) ?
    C7 C8 H8B . . 111.1(8) ?
    C9 C8 H8B . . 110.1(8) ?
    H8A C8 H8B . . 107.6(11) ?
    O1 C9 N1 . . 121.89(11) ?
    O1 C9 C8 . . 122.57(11) ?
    N1 C9 C8 . . 115.54(10) ?
    N1 C10 C11 . . 111.34(10) ?
    N1 C10 H10A . . 109.3(9) ?
    C11 C10 H10A . . 108.5(9) ?
    N1 C10 H10B . . 109.2(9) ?
    C11 C10 H10B . . 110.3(9) ?
    H10A C10 H10B . . 108.2(13) ?
    O3 C11 O2 . . 124.60(10) ?
    O3 C11 C10 . . 123.72(10) ?
    O2 C11 C10 . . 111.66(10) ?
    C13 C12 C17 . . 118.80(11) ?
    C13 C12 C7 . . 120.07(11) ?
    C17 C12 C7 . . 121.11(11) ?
    C12 C13 C14 . . 119.55(14) ?
    C12 C13 H13 . . 120.0(10) ?
    C14 C13 H13 . . 120.4(10) ?
    C15 C14 C13 . . 121.18(15) ?
    C15 C14 H14 . . 122.6(14) ?
    C13 C14 H14 . . 116.1(14) ?
    C14 C15 C16 . . 119.92(13) ?
    C14 C15 H15 . . 119.8(10) ?
    C16 C15 H15 . . 120.3(10) ?
    C15 C16 C17 . . 119.95(15) ?
    C15 C16 H16 . . 122.8(12) ?
    C17 C16 H16 . . 117.2(12) ?
    C16 C17 C12 . . 120.56(13) ?
    C16 C17 H17 . . 117.7(9) ?
    C12 C17 H17 . . 121.7(9) ?
    C28 O6 H6 . . 109.5 ?
    C26 N3 C18 . . 123.59(9) ?
    C26 N3 C27 . . 116.85(10) ?
    C18 N3 C27 . . 119.02(9) ?
    C24 N4 C23 . . 120.87(9) ?
    C19 C18 C23 . . 118.77(10) ?
    C19 C18 N3 . . 119.26(10) ?
    C23 C18 N3 . . 121.78(9) ?
    C20 C19 C18 . . 121.14(12) ?
    C20 C19 H19 . . 118.2(9) ?
    C18 C19 H19 . . 120.6(9) ?
    C19 C20 C21 . . 120.18(12) ?
    C19 C20 H20 . . 121.4(10) ?
    C21 C20 H20 . . 118.4(10) ?
    C22 C21 C20 . . 119.50(12) ?
    C22 C21 H21 . . 117.3(8) ?
    C20 C21 H21 . . 123.1(8) ?
    C21 C22 C23 . . 121.36(12) ?
    C21 C22 H22 . . 122.9(8) ?
    C23 C22 H22 . . 115.7(8) ?
    C22 C23 C18 . . 119.04(10) ?
    C22 C23 N4 . . 116.45(10) ?
    C18 C23 N4 . . 124.34(9) ?
    N4 C24 C29 . . 119.33(10) ?
    N4 C24 C25 . . 120.72(10) ?
    C29 C24 C25 . . 119.86(10) ?
    C24 C25 C26 . . 105.68(9) ?
    C24 C25 H25A . . 109.1(8) ?
    C26 C25 H25A . . 107.9(8) ?
    C24 C25 H25B . . 111.6(9) ?
    C26 C25 H25B . . 110.2(9) ?
    H25A C25 H25B . . 112.1(12) ?
    O4 C26 N3 . . 122.33(11) ?
    O4 C26 C25 . . 122.79(11) ?
    N3 C26 C25 . . 114.83(10) ?
    N3 C27 C28 . . 112.49(10) ?
    N3 C27 H27A . . 107.5(9) ?
    C28 C27 H27A . . 109.8(9) ?
    N3 C27 H27B . . 110.5(9) ?
    C28 C27 H27B . . 107.1(9) ?
    H27A C27 H27B . . 109.5(12) ?
    O5 C28 O6 . . 125.06(11) ?
    O5 C28 C27 . . 124.04(11) ?
    O6 C28 C27 . . 110.90(10) ?
    C34 C29 C30 . . 118.83(11) ?
    C34 C29 C24 . . 120.63(10) ?
    C30 C29 C24 . . 120.54(10) ?
    C31 C30 C29 . . 120.31(12) ?
    C31 C30 H30 . . 120.7(9) ?
    C29 C30 H30 . . 119.0(9) ?
    C30 C31 C32 . . 120.29(12) ?
    C30 C31 H31 . . 119.6(9) ?
    C32 C31 H31 . . 120.1(9) ?
    C33 C32 C31 . . 119.74(13) ?
    C33 C32 H32 . . 121.2(11) ?
    C31 C32 H32 . . 119.1(11) ?
    C32 C33 C34 . . 120.44(13) ?
    C32 C33 H33 . . 121.2(10) ?
    C34 C33 H33 . . 118.4(10) ?
    C33 C34 C29 . . 120.39(12) ?
    C33 C34 H34 . . 118.0(9) ?
    C29 C34 H34 . . 121.5(9) ?
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
    C9 N1 C1 C2 . . . . -137.08(12) ?
    C10 N1 C1 C2 . . . . 26.96(16) ?
    C9 N1 C1 C6 . . . . 45.09(16) ?
    C10 N1 C1 C6 . . . . -150.87(11) ?
    C6 C1 C2 C3 . . . . -1.79(18) ?
    N1 C1 C2 C3 . . . . -179.70(12) ?
    C1 C2 C3 C4 . . . . 0.9(2) ?
    C2 C3 C4 C5 . . . . 0.7(2) ?
    C3 C4 C5 C6 . . . . -1.4(2) ?
    C4 C5 C6 C1 . . . . 0.39(19) ?
    C4 C5 C6 N2 . . . . 177.02(12) ?
    C2 C1 C6 C5 . . . . 1.16(17) ?
    N1 C1 C6 C5 . . . . 179.02(11) ?
    C2 C1 C6 N2 . . . . -175.12(11) ?
    N1 C1 C6 N2 . . . . 2.73(18) ?
    C7 N2 C6 C5 . . . . 138.67(11) ?
    C7 N2 C6 C1 . . . . -44.91(17) ?
    C6 N2 C7 C12 . . . . 178.79(9) ?
    C6 N2 C7 C8 . . . . -0.99(16) ?
    N2 C7 C8 C9 . . . . 73.67(13) ?
    C12 C7 C8 C9 . . . . -106.11(11) ?
    C1 N1 C9 O1 . . . . 175.41(11) ?
    C10 N1 C9 O1 . . . . 10.55(16) ?
    C1 N1 C9 C8 . . . . -5.74(15) ?
    C10 N1 C9 C8 . . . . -170.60(9) ?
    C7 C8 C9 O1 . . . . 111.79(13) ?
    C7 C8 C9 N1 . . . . -67.04(12) ?
    C9 N1 C10 C11 . . . . 72.77(13) ?
    C1 N1 C10 C11 . . . . -92.65(13) ?
    N1 C10 C11 O3 . . . . 17.87(18) ?
    N1 C10 C11 O2 . . . . -163.44(10) ?
    N2 C7 C12 C13 . . . . -27.62(16) ?
    C8 C7 C12 C13 . . . . 152.16(11) ?
    N2 C7 C12 C17 . . . . 150.59(11) ?
    C8 C7 C12 C17 . . . . -29.63(15) ?
    C17 C12 C13 C14 . . . . -1.80(19) ?
    C7 C12 C13 C14 . . . . 176.45(13) ?
    C12 C13 C14 C15 . . . . 0.0(2) ?
    C13 C14 C15 C16 . . . . 1.3(3) ?
    C14 C15 C16 C17 . . . . -0.6(2) ?
    C15 C16 C17 C12 . . . . -1.2(2) ?
    C13 C12 C17 C16 . . . . 2.43(18) ?
    C7 C12 C17 C16 . . . . -175.80(11) ?
    C26 N3 C18 C19 . . . . 137.80(11) ?
    C27 N3 C18 C19 . . . . -33.44(15) ?
    C26 N3 C18 C23 . . . . -47.32(16) ?
    C27 N3 C18 C23 . . . . 141.44(11) ?
    C23 C18 C19 C20 . . . . -0.59(18) ?
    N3 C18 C19 C20 . . . . 174.44(11) ?
    C18 C19 C20 C21 . . . . 0.6(2) ?
    C19 C20 C21 C22 . . . . -0.4(2) ?
    C20 C21 C22 C23 . . . . 0.3(2) ?
    C21 C22 C23 C18 . . . . -0.37(18) ?
    C21 C22 C23 N4 . . . . -175.85(12) ?
    C19 C18 C23 C22 . . . . 0.49(16) ?
    N3 C18 C23 C22 . . . . -174.42(10) ?
    C19 C18 C23 N4 . . . . 175.58(10) ?
    N3 C18 C23 N4 . . . . 0.67(17) ?
    C24 N4 C23 C22 . . . . -141.09(11) ?
    C24 N4 C23 C18 . . . . 43.70(16) ?
    C23 N4 C24 C29 . . . . -175.62(10) ?
    C23 N4 C24 C25 . . . . 0.86(16) ?
    N4 C24 C25 C26 . . . . -74.56(13) ?
    C29 C24 C25 C26 . . . . 101.89(11) ?
    C18 N3 C26 O4 . . . . -178.32(11) ?
    C27 N3 C26 O4 . . . . -6.90(16) ?
    C18 N3 C26 C25 . . . . 4.16(15) ?
    C27 N3 C26 C25 . . . . 175.58(9) ?
    C24 C25 C26 O4 . . . . -108.08(13) ?
    C24 C25 C26 N3 . . . . 69.43(12) ?
    C26 N3 C27 C28 . . . . -81.33(13) ?
    C18 N3 C27 C28 . . . . 90.50(13) ?
    N3 C27 C28 O5 . . . . 21.02(18) ?
    N3 C27 C28 O6 . . . . -159.08(11) ?
    N4 C24 C29 C34 . . . . 36.54(16) ?
    C25 C24 C29 C34 . . . . -139.96(12) ?
    N4 C24 C29 C30 . . . . -142.93(11) ?
    C25 C24 C29 C30 . . . . 40.57(15) ?
    C34 C29 C30 C31 . . . . -0.92(18) ?
    C24 C29 C30 C31 . . . . 178.56(11) ?
    C29 C30 C31 C32 . . . . 0.5(2) ?
    C30 C31 C32 C33 . . . . 0.1(2) ?
    C31 C32 C33 C34 . . . . -0.2(2) ?
    C32 C33 C34 C29 . . . . -0.2(2) ?
    C30 C29 C34 C33 . . . . 0.81(19) ?
    C24 C29 C34 C33 . . . . -178.67(12) ?
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
    O2 H2A N4 . 0.82 1.90 2.7161(12) 176
    O6 H6 N2 1_565 0.82 1.95 2.7585(13) 171
    C4 H4 Cg2 2_745 0.989(16) 2.97(2) 3.7650(16) 139.0(10)
    C17 H17 Cg1 4_566 1.004(17) 2.82(2) 3.6431(14) 140.0(10)
