# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_v830_0m
_database_code_depnum_ccdc_archive 'CCDC 1965257'
loop_
_audit_author_name
_audit_author_address
'P. Deschamps'
;University of Paris
France
;
_audit_update_record             
;
2019-11-12 deposited with the CCDC.	2020-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H27 N O6'
_chemical_formula_weight         533.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0096 '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 0.0311 0.0189 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.6327(6)
_cell_length_b                   15.2434(7)
_cell_length_c                   15.9800(7)
_cell_angle_alpha                102.027(2)
_cell_angle_beta                 105.432(2)
_cell_angle_gamma                112.595(2)
_cell_volume                     2566.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9064
_cell_measurement_theta_min      3.4
_cell_measurement_theta_max      66.0

_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.745
_shelx_estimated_absorpt_T_min   0.824
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  1.000
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS (Siemens,1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            77250
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.061
_diffrn_reflns_theta_max         66.744
_diffrn_reflns_theta_full        66.744
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             9064
_reflns_number_gt                7943
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       'SAINT v8.34 A (Bruker,2013)'
_computing_data_reduction        'SAINT v8.34 A (Bruker,2013)'
_computing_structure_solution    'SHELXS-2016/6 (Sheldrick,2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0568P)²+0.8441P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9064
_refine_ls_number_parameters     743
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.0998
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.14813(11) 0.53030(9) 0.30643(8) 0.0173(2) Uani 1 1 d . . . . .
C2 C 0.23688(11) 0.50878(9) 0.36018(8) 0.0177(2) Uani 1 1 d . . . . .
C3 C 0.35067(11) 0.58439(9) 0.42631(8) 0.0190(3) Uani 1 1 d . . . . .
C4 C 0.37927(11) 0.68540(9) 0.44197(8) 0.0190(3) Uani 1 1 d . . . . .
C4A C 0.29410(11) 0.71116(9) 0.38843(8) 0.0179(2) Uani 1 1 d . . . . .
C5 C 0.32932(11) 0.81813(9) 0.40908(8) 0.0178(2) Uani 1 1 d . . . . .
C6 C 0.24471(11) 0.85674(9) 0.35520(8) 0.0188(3) Uani 1 1 d . . . . .
C7 C 0.11829(11) 0.81426(9) 0.36347(8) 0.0205(3) Uani 1 1 d . . . . .
C8 C 0.04334(11) 0.71688(9) 0.31482(8) 0.0206(3) Uani 1 1 d . . . . .
H8 H -0.037488 0.684521 0.315118 0.031 Uiso 1 1 calc R U . . .
C9 C 0.08972(11) 0.65847(9) 0.25874(8) 0.0185(2) Uani 1 1 d . . . . .
H9 H 0.016742 0.594332 0.212031 0.028 Uiso 1 1 calc R U . . .
C9A C 0.17854(11) 0.63110(9) 0.31936(8) 0.0171(2) Uani 1 1 d . . . . .
C10 C 0.15544(11) 0.71997(9) 0.20742(8) 0.0182(2) Uani 1 1 d . . . . .
C12 C 0.02117(11) 0.44137(9) 0.24293(8) 0.0196(3) Uani 1 1 d . . . . .
H12A H -0.008793 0.452412 0.184125 0.029 Uiso 1 1 calc R U . . .
H12B H 0.028472 0.378073 0.228265 0.029 Uiso 1 1 calc R U . . .
C13 C -0.07139(11) 0.43081(9) 0.28929(8) 0.0206(3) Uani 1 1 d . . . . .
C14 C -0.06124(12) 0.39839(10) 0.36494(9) 0.0274(3) Uani 1 1 d . . . . .
H14 H 0.000315 0.377743 0.384729 0.041 Uiso 1 1 calc R U . . .
C15 C -0.13978(13) 0.39580(11) 0.41190(10) 0.0328(3) Uani 1 1 d . . . . .
H15 H -0.131887 0.373028 0.463139 0.049 Uiso 1 1 calc R U . . .
C16 C -0.22970(13) 0.42626(11) 0.38441(10) 0.0322(3) Uani 1 1 d . . . . .
H16 H -0.282811 0.425310 0.416965 0.048 Uiso 1 1 calc R U . . .
C17 C -0.24102(12) 0.45805(11) 0.30892(10) 0.0310(3) Uani 1 1 d . . . . .
H17 H -0.302078 0.479355 0.289758 0.047 Uiso 1 1 calc R U . . .
C18 C -0.16392(12) 0.45906(10) 0.26100(9) 0.0259(3) Uani 1 1 d . . . . .
H18 H -0.174321 0.479262 0.208263 0.039 Uiso 1 1 calc R U . . .
C19 C 0.09442(12) 0.88618(10) 0.42660(9) 0.0241(3) Uani 1 1 d . . . . .
H19A H 0.089262 0.937605 0.399062 0.036 Uiso 1 1 calc R U . . .
H19B H 0.166482 0.922156 0.486531 0.036 Uiso 1 1 calc R U . . .
C20 C -0.02211(12) 0.83771(10) 0.44534(8) 0.0242(3) Uani 1 1 d . . . . .
C21 C -0.04754(14) 0.75511(11) 0.47516(10) 0.0310(3) Uani 1 1 d . . . . .
H21 H 0.009595 0.728406 0.484402 0.046 Uiso 1 1 calc R U . . .
C22 C -0.15525(15) 0.71100(12) 0.49165(10) 0.0348(3) Uani 1 1 d . . . . .
H22 H -0.172487 0.653221 0.509951 0.052 Uiso 1 1 calc R U . . .
C23 C -0.23722(14) 0.75104(11) 0.48148(9) 0.0326(3) Uani 1 1 d . . . . .
H23 H -0.311122 0.720676 0.492266 0.049 Uiso 1 1 calc R U . . .
C24 C -0.21098(13) 0.83556(11) 0.45549(10) 0.0317(3) Uani 1 1 d . . . . .
H24 H -0.265158 0.865188 0.451043 0.047 Uiso 1 1 calc R U . . .
C25 C -0.10535(12) 0.87742(10) 0.43580(9) 0.0265(3) Uani 1 1 d . . . . .
H25 H -0.089893 0.933848 0.415593 0.040 Uiso 1 1 calc R U . . .
C26 C 0.28923(12) 0.88914(9) 0.21309(9) 0.0217(3) Uani 1 1 d . . . . .
H26A H 0.257011 0.939008 0.213884 0.033 Uiso 1 1 calc R U . . .
H26B H 0.265988 0.850317 0.147467 0.033 Uiso 1 1 calc R U . . .
C27 C 0.42858(12) 0.94586(10) 0.25914(9) 0.0257(3) Uani 1 1 d . . . . .
C28 C 0.49925(15) 0.89524(14) 0.27108(11) 0.0389(4) Uani 1 1 d . . . . .
H28 H 0.457616 0.823275 0.250584 0.058 Uiso 1 1 calc R U . A 1
C29A C 0.6264(6) 0.9445(7) 0.3111(4) 0.0643(17) Uani 0.756(17) 1 d D . P B 1
H29A H 0.671799 0.907885 0.321571 0.096 Uiso 0.756(17) 1 calc R U P B 1
C30A C 0.6862(8) 1.0478(7) 0.3356(6) 0.070(2) Uani 0.756(17) 1 d D . P B 1
H30A H 0.774267 1.083110 0.359179 0.105 Uiso 0.756(17) 1 calc R U P B 1
C31A C 0.6191(8) 1.1007(5) 0.3263(6) 0.063(2) Uani 0.756(17) 1 d D . P B 1
H31A H 0.662373 1.172677 0.347116 0.095 Uiso 0.756(17) 1 calc R U P B 1
C29B C 0.6312(16) 0.9623(10) 0.3072(10) 0.022(3) Uiso 0.244(17) 1 d D . P B 2
H29B H 0.684195 0.931716 0.308312 0.033 Uiso 0.244(17) 1 calc R U P B 2
C30B C 0.687(2) 1.0676(13) 0.3405(17) 0.025(3) Uiso 0.244(17) 1 d D . P B 2
H30B H 0.774333 1.106153 0.373948 0.037 Uiso 0.244(17) 1 calc R U P B 2
C31B C 0.6143(17) 1.1160(13) 0.3245(14) 0.020(3) Uiso 0.244(17) 1 d D . P B 2
H31B H 0.648192 1.187228 0.338340 0.030 Uiso 0.244(17) 1 calc R U P B 2
C32 C 0.48805(14) 1.05127(11) 0.28660(10) 0.0364(4) Uani 1 1 d . . . . .
H32 H 0.442498 1.088180 0.278996 0.055 Uiso 1 1 calc R U . B 1
C33 C 0.64918(11) 0.53471(9) 0.81124(8) 0.0176(2) Uani 1 1 d . . . . .
C34 C 0.73782(11) 0.51124(9) 0.86278(8) 0.0179(2) Uani 1 1 d . . . . .
C35 C 0.85524(11) 0.58566(9) 0.92460(8) 0.0190(3) Uani 1 1 d . . . . .
C36 C 0.88778(11) 0.68679(9) 0.93727(8) 0.0193(3) Uani 1 1 d . . . . .
C36A C 0.80251(11) 0.71428(9) 0.88682(8) 0.0178(2) Uani 1 1 d . . . . .
C37 C 0.84140(11) 0.82160(9) 0.90615(8) 0.0182(3) Uani 1 1 d . . . . .
C38 C 0.75750(11) 0.86192(9) 0.85467(8) 0.0178(2) Uani 1 1 d . . . . .
C39 C 0.63650(11) 0.82605(9) 0.87100(8) 0.0197(3) Uani 1 1 d . . . . .
C40 C 0.55609(11) 0.72910(9) 0.82548(8) 0.0197(3) Uani 1 1 d . . . . .
H40 H 0.477683 0.700756 0.830539 0.030 Uiso 1 1 calc R U . . .
C41 C 0.59211(11) 0.66465(9) 0.76529(8) 0.0182(2) Uani 1 1 d . . . . .
H41 H 0.515352 0.601196 0.721704 0.027 Uiso 1 1 calc R U . . .
C41A C 0.68246(11) 0.63554(9) 0.82220(8) 0.0172(2) Uani 1 1 d . . . . .
C42 C 0.65292(11) 0.72065(9) 0.70871(8) 0.0174(2) Uani 1 1 d . . . . .
C44 C 0.52138(11) 0.44723(9) 0.75214(8) 0.0194(3) Uani 1 1 d . . . . .
H44A H 0.529619 0.385496 0.729612 0.029 Uiso 1 1 calc R U . . .
H44B H 0.484861 0.462171 0.697344 0.029 Uiso 1 1 calc R U . . .
C45 C 0.43276(11) 0.42575(9) 0.80281(8) 0.0210(3) Uani 1 1 d . . . . .
C46 C 0.33340(13) 0.32911(11) 0.77138(10) 0.0302(3) Uani 1 1 d . . . . .
H46 H 0.325459 0.277104 0.721723 0.045 Uiso 1 1 calc R U . . .
C47 C 0.24561(13) 0.30719(12) 0.81122(11) 0.0363(3) Uani 1 1 d . . . . .
H47 H 0.177671 0.240936 0.787926 0.054 Uiso 1 1 calc R U . . .
C48 C 0.25643(14) 0.38102(13) 0.88439(10) 0.0358(3) Uani 1 1 d . . . . .
H48 H 0.196321 0.366056 0.911633 0.054 Uiso 1 1 calc R U . . .
C49 C 0.35555(14) 0.47684(12) 0.91754(10) 0.0336(3) Uani 1 1 d . . . . .
H49 H 0.364142 0.528028 0.968274 0.050 Uiso 1 1 calc R U . . .
C50 C 0.44316(13) 0.49908(10) 0.87714(9) 0.0271(3) Uani 1 1 d . . . . .
H50 H 0.511046 0.565403 0.900783 0.041 Uiso 1 1 calc R U . . .
C51 C 0.62153(12) 0.90209(10) 0.93720(9) 0.0239(3) Uani 1 1 d . . . . .
H51A H 0.614226 0.953007 0.909671 0.036 Uiso 1 1 calc R U . . .
H51B H 0.696558 0.937942 0.995236 0.036 Uiso 1 1 calc R U . . .
C52 C 0.50883(13) 0.85323(10) 0.95959(9) 0.0250(3) Uani 1 1 d . . . . .
C53 C 0.50732(14) 0.79294(11) 1.01416(10) 0.0316(3) Uani 1 1 d . . . . .
H53 H 0.578861 0.785161 1.039527 0.047 Uiso 1 1 calc R U . . .
C54 C 0.40177(15) 0.74385(12) 1.03193(10) 0.0389(4) Uani 1 1 d . . . . .
H54 H 0.401632 0.703050 1.069496 0.058 Uiso 1 1 calc R U . . .
C55 C 0.29725(15) 0.75458(13) 0.99483(11) 0.0420(4) Uani 1 1 d . . . . .
H55 H 0.224635 0.720200 1.005876 0.063 Uiso 1 1 calc R U . . .
C56 C 0.29881(16) 0.81509(14) 0.94199(12) 0.0452(4) Uani 1 1 d . . . . .
H56 H 0.227467 0.823366 0.917333 0.068 Uiso 1 1 calc R U . . .
C57 C 0.40416(15) 0.86440(12) 0.92426(11) 0.0359(3) Uani 1 1 d . . . . .
H57 H 0.404156 0.906092 0.887590 0.054 Uiso 1 1 calc R U . . .
C58 C 0.79714(12) 0.88337(9) 0.70883(8) 0.0211(3) Uani 1 1 d . . . . .
H58A H 0.784896 0.944512 0.717607 0.032 Uiso 1 1 calc R U . . .
H58B H 0.761739 0.845288 0.641451 0.032 Uiso 1 1 calc R U . . .
C59 C 0.93424(12) 0.91587(10) 0.74626(8) 0.0217(3) Uani 1 1 d . . . . .
C60 C 0.97661(13) 0.84402(10) 0.73834(9) 0.0277(3) Uani 1 1 d . . . . .
H60 H 0.918566 0.774037 0.709344 0.042 Uiso 1 1 calc R U . . .
C61 C 1.10239(13) 0.87328(12) 0.77223(10) 0.0335(3) Uani 1 1 d . . . . .
H61 H 1.130254 0.823475 0.766050 0.050 Uiso 1 1 calc R U . . .
C62 C 1.18782(13) 0.97515(12) 0.81519(10) 0.0330(3) Uani 1 1 d . . . . .
H62 H 1.274213 0.995371 0.839047 0.049 Uiso 1 1 calc R U . . .
C63 C 1.14656(14) 1.04692(11) 0.82307(10) 0.0351(3) Uani 1 1 d . . . . .
H63 H 1.204849 1.116829 0.852315 0.053 Uiso 1 1 calc R U . . .
C64 C 1.02058(13) 1.01778(10) 0.78861(10) 0.0290(3) Uani 1 1 d . . . . .
H64 H 0.993128 1.067867 0.793999 0.044 Uiso 1 1 calc R U . . .
N11 N 0.22801(9) 0.81868(7) 0.25586(7) 0.0189(2) Uani 1 1 d . . . . .
N43 N 0.72922(9) 0.81954(7) 0.75364(7) 0.0179(2) Uani 1 1 d . . . . .
O1 O 0.30369(8) 0.96154(6) 0.38824(6) 0.02094(19) Uani 1 1 d . . . . .
H1 H 0.376616 0.983244 0.425620 0.046(2) Uiso 1 1 calc R U . . .
O2 O 0.42913(8) 0.88612(6) 0.47064(6) 0.02218(19) Uani 1 1 d . . . . .
O3 O 0.49028(8) 0.75423(7) 0.50943(6) 0.0250(2) Uani 1 1 d . . . . .
H3 H 0.498007 0.812819 0.516282 0.046(2) Uiso 1 1 calc R U . . .
O4 O 0.42723(8) 0.55284(7) 0.47304(6) 0.0251(2) Uani 1 1 d . . . . .
H4 H 0.488048 0.602783 0.517168 0.046(2) Uiso 1 1 calc R U . . .
O5 O 0.20917(8) 0.41083(6) 0.34746(6) 0.02086(19) Uani 1 1 d . . . . .
H5 H 0.273939 0.407467 0.373577 0.046(2) Uiso 1 1 calc R U . . .
O6 O 0.14137(8) 0.67874(6) 0.12688(6) 0.02062(19) Uani 1 1 d . . . . .
O7 O 0.82117(8) 0.96668(6) 0.88440(6) 0.01961(19) Uani 1 1 d . . . . .
H7 H 0.893617 0.987196 0.922014 0.046(2) Uiso 1 1 calc R U . . .
O8 O 0.94366(8) 0.88821(6) 0.96550(6) 0.0237(2) Uani 1 1 d . . . . .
O9 O 1.00308(8) 0.75424(7) 0.99974(6) 0.0265(2) Uani 1 1 d . . . . .
H9A H 1.013510 0.813402 1.005770 0.046(2) Uiso 1 1 calc R U . . .
O10 O 0.93237(8) 0.55343(7) 0.96949(6) 0.0252(2) Uani 1 1 d . . . . .
H10 H 0.994144 0.603139 1.013161 0.046(2) Uiso 1 1 calc R U . . .
O11 O 0.70525(8) 0.41283(6) 0.85138(6) 0.02167(19) Uani 1 1 d . . . . .
H11 H 0.768547 0.407323 0.876990 0.046(2) Uiso 1 1 calc R U . . .
O12 O 0.63351(8) 0.67519(6) 0.62789(6) 0.02012(19) Uani 1 1 d . . . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C9A 1.3867(17) . ?
C1 C2 1.4107(17) . ?
C1 C12 1.5263(16) . ?
C2 O5 1.3518(15) . ?
C2 C3 1.3865(17) . ?
C3 O4 1.3591(15) . ?
C3 C4 1.3884(18) . ?
C4 O3 1.3501(15) . ?
C4 C4A 1.4208(17) . ?
C4A C9A 1.4321(17) . ?
C4A C5 1.4511(17) . ?
C5 O2 1.2420(15) . ?
C5 C6 1.5605(17) . ?
C6 O1 1.3822(14) . ?
C6 N11 1.4982(15) . ?
C6 C7 1.5299(17) . ?
C7 C8 1.3235(18) . ?
C7 C19 1.5053(18) . ?
C8 C9 1.5123(17) . ?
C8 H8 0.9500 . ?
C9 C9A 1.5234(17) . ?
C9 C10 1.5249(17) . ?
C9 H9 1.0000 . ?
C10 O6 1.2403(15) . ?
C10 N11 1.3345(16) . ?
C12 C13 1.5193(17) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.3918(19) . ?
C13 C18 1.3939(18) . ?
C14 C15 1.388(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.5145(18) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.391(2) . ?
C20 C25 1.3920(19) . ?
C21 C22 1.391(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.381(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.393(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 N11 1.4724(16) . ?
C26 C27 1.5046(18) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.389(2) . ?
C27 C32 1.394(2) . ?
C28 C29B 1.445(17) . ?
C28 C29A 1.370(7) . ?
C28 H28 0.9500 . ?
C29A C30A 1.369(7) . ?
C29A H29A 0.9500 . ?
C30A C31A 1.378(7) . ?
C30A H30A 0.9500 . ?
C31A C32 1.412(9) . ?
C31A H31A 0.9500 . ?
C29B C30B 1.391(13) . ?
C29B H29B 0.9500 . ?
C30B C31B 1.390(12) . ?
C30B H30B 0.9500 . ?
C31B C32 1.383(19) . ?
C31B H31B 0.9500 . ?
C32 H32 0.9500 . ?
C33 C41A 1.3865(17) . ?
C33 C34 1.4141(17) . ?
C33 C44 1.5120(16) . ?
C34 O11 1.3509(15) . ?
C34 C35 1.3868(18) . ?
C35 O10 1.3594(15) . ?
C35 C36 1.3874(18) . ?
C36 O9 1.3502(15) . ?
C36 C36A 1.4183(17) . ?
C36A C41A 1.4346(17) . ?
C36A C37 1.4505(17) . ?
C37 O8 1.2402(15) . ?
C37 C38 1.5572(17) . ?
C38 O7 1.3843(14) . ?
C38 N43 1.4941(15) . ?
C38 C39 1.5274(17) . ?
C39 C40 1.3230(18) . ?
C39 C51 1.5040(17) . ?
C40 C41 1.5100(17) . ?
C40 H40 0.9500 . ?
C41 C42 1.5245(17) . ?
C41 C41A 1.5268(17) . ?
C41 H41 1.0000 . ?
C42 O12 1.2394(15) . ?
C42 N43 1.3345(16) . ?
C44 C45 1.5255(18) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C50 1.3886(19) . ?
C45 C46 1.3904(18) . ?
C46 C47 1.388(2) . ?
C46 H46 0.9500 . ?
C47 C48 1.379(2) . ?
C47 H47 0.9500 . ?
C48 C49 1.379(2) . ?
C48 H48 0.9500 . ?
C49 C50 1.393(2) . ?
C49 H49 0.9500 . ?
C50 H50 0.9500 . ?
C51 C52 1.5091(18) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C52 C57 1.383(2) . ?
C52 C53 1.391(2) . ?
C53 C54 1.394(2) . ?
C53 H53 0.9500 . ?
C54 C55 1.382(3) . ?
C54 H54 0.9500 . ?
C55 C56 1.373(3) . ?
C55 H55 0.9500 . ?
C56 C57 1.392(2) . ?
C56 H56 0.9500 . ?
C57 H57 0.9500 . ?
C58 N43 1.4736(16) . ?
C58 C59 1.5062(18) . ?
C58 H58A 0.9900 . ?
C58 H58B 0.9900 . ?
C59 C64 1.3885(19) . ?
C59 C60 1.3895(19) . ?
C60 C61 1.383(2) . ?
C60 H60 0.9500 . ?
C61 C62 1.386(2) . ?
C61 H61 0.9500 . ?
C62 C63 1.379(2) . ?
C62 H62 0.9500 . ?
C63 C64 1.386(2) . ?
C63 H63 0.9500 . ?
C64 H64 0.9500 . ?
O1 H1 0.8400 . ?
O3 H3 0.8400 . ?
O4 H4 0.8400 . ?
O5 H5 0.8400 . ?
O7 H7 0.8400 . ?
O9 H9A 0.8400 . ?
O10 H10 0.8400 . ?
O11 H11 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9A C1 C2 118.05(11) . . ?
C9A C1 C12 124.10(11) . . ?
C2 C1 C12 117.69(10) . . ?
O5 C2 C3 118.89(11) . . ?
O5 C2 C1 118.71(10) . . ?
C3 C2 C1 122.39(11) . . ?
O4 C3 C2 116.17(11) . . ?
O4 C3 C4 124.19(11) . . ?
C2 C3 C4 119.63(11) . . ?
O3 C4 C3 115.91(11) . . ?
O3 C4 C4A 123.91(11) . . ?
C3 C4 C4A 120.18(11) . . ?
C4 C4A C9A 118.66(11) . . ?
C4 C4A C5 117.30(11) . . ?
C9A C4A C5 124.02(11) . . ?
O2 C5 C4A 122.78(11) . . ?
O2 C5 C6 114.71(10) . . ?
C4A C5 C6 122.51(10) . . ?
O1 C6 N11 109.47(9) . . ?
O1 C6 C7 111.17(10) . . ?
N11 C6 C7 109.66(10) . . ?
O1 C6 C5 109.49(9) . . ?
N11 C6 C5 106.16(9) . . ?
C7 C6 C5 110.76(10) . . ?
C8 C7 C19 127.69(12) . . ?
C8 C7 C6 115.23(11) . . ?
C19 C7 C6 117.07(10) . . ?
C7 C8 C9 118.27(11) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C8 C9 C9A 111.84(10) . . ?
C8 C9 C10 110.52(10) . . ?
C9A C9 C10 108.96(10) . . ?
C8 C9 H9 108.5 . . ?
C9A C9 H9 108.5 . . ?
C10 C9 H9 108.5 . . ?
C1 C9A C4A 121.01(11) . . ?
C1 C9A C9 120.23(10) . . ?
C4A C9A C9 118.76(10) . . ?
O6 C10 N11 123.99(11) . . ?
O6 C10 C9 120.96(11) . . ?
N11 C10 C9 115.05(10) . . ?
C13 C12 C1 110.42(10) . . ?
C13 C12 H12A 109.6 . . ?
C1 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C1 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C18 118.17(12) . . ?
C14 C13 C12 120.68(11) . . ?
C18 C13 C12 121.03(11) . . ?
C15 C14 C13 120.95(13) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C14 120.37(13) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 119.12(13) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C18 120.55(13) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 120.80(13) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
C7 C19 C20 115.36(11) . . ?
C7 C19 H19A 108.4 . . ?
C20 C19 H19A 108.4 . . ?
C7 C19 H19B 108.4 . . ?
C20 C19 H19B 108.4 . . ?
H19A C19 H19B 107.5 . . ?
C21 C20 C25 118.05(13) . . ?
C21 C20 C19 121.68(12) . . ?
C25 C20 C19 120.24(12) . . ?
C22 C21 C20 121.07(14) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C23 C22 C21 120.14(14) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 119.56(13) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C23 C24 C25 120.20(14) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C20 C25 C24 120.89(13) . . ?
C20 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
N11 C26 C27 114.84(10) . . ?
N11 C26 H26A 108.6 . . ?
C27 C26 H26A 108.6 . . ?
N11 C26 H26B 108.6 . . ?
C27 C26 H26B 108.6 . . ?
H26A C26 H26B 107.5 . . ?
C28 C27 C32 119.38(14) . . ?
C28 C27 C26 121.44(13) . . ?
C32 C27 C26 119.11(13) . . ?
C27 C28 C29B 113.0(5) . . ?
C27 C28 C29A 122.9(4) . . ?
C27 C28 H28 118.5 . . ?
C29A C28 H28 118.5 . . ?
C30A C29A C28 118.3(6) . . ?
C30A C29A H29A 120.9 . . ?
C28 C29A H29A 120.9 . . ?
C31A C30A C29A 120.3(7) . . ?
C31A C30A H30A 119.8 . . ?
C29A C30A H30A 119.8 . . ?
C30A C31A C32 122.0(6) . . ?
C30A C31A H31A 119.0 . . ?
C32 C31A H31A 119.0 . . ?
C30B C29B C28 125.6(14) . . ?
C30B C29B H29B 117.2 . . ?
C28 C29B H29B 117.2 . . ?
C31B C30B C29B 119.4(18) . . ?
C31B C30B H30B 120.3 . . ?
C29B C30B H30B 120.3 . . ?
C30B C31B C32 114.0(16) . . ?
C30B C31B H31B 123.0 . . ?
C32 C31B H31B 123.0 . . ?
C31B C32 C27 127.8(6) . . ?
C31A C32 C27 117.0(4) . . ?
C31A C32 H32 121.5 . . ?
C27 C32 H32 121.5 . . ?
C41A C33 C34 118.43(11) . . ?
C41A C33 C44 124.68(11) . . ?
C34 C33 C44 116.78(11) . . ?
O11 C34 C35 119.62(11) . . ?
O11 C34 C33 118.21(11) . . ?
C35 C34 C33 122.17(11) . . ?
O10 C35 C34 116.60(11) . . ?
O10 C35 C36 123.89(11) . . ?
C34 C35 C36 119.51(11) . . ?
O9 C36 C35 115.59(11) . . ?
O9 C36 C36A 123.89(11) . . ?
C35 C36 C36A 120.52(11) . . ?
C36 C36A C41A 118.73(11) . . ?
C36 C36A C37 117.41(11) . . ?
C41A C36A C37 123.84(11) . . ?
O8 C37 C36A 122.48(11) . . ?
O8 C37 C38 114.93(10) . . ?
C36A C37 C38 122.58(10) . . ?
O7 C38 N43 109.05(9) . . ?
O7 C38 C39 111.27(10) . . ?
N43 C38 C39 109.37(9) . . ?
O7 C38 C37 109.55(9) . . ?
N43 C38 C37 107.35(9) . . ?
C39 C38 C37 110.15(10) . . ?
C40 C39 C51 126.89(12) . . ?
C40 C39 C38 115.24(11) . . ?
C51 C39 C38 117.85(10) . . ?
C39 C40 C41 118.30(11) . . ?
C39 C40 H40 120.8 . . ?
C41 C40 H40 120.8 . . ?
C40 C41 C42 110.69(10) . . ?
C40 C41 C41A 112.13(10) . . ?
C42 C41 C41A 108.13(10) . . ?
C40 C41 H41 108.6 . . ?
C42 C41 H41 108.6 . . ?
C41A C41 H41 108.6 . . ?
C33 C41A C36A 120.61(11) . . ?
C33 C41A C41 120.53(10) . . ?
C36A C41A C41 118.86(10) . . ?
O12 C42 N43 123.88(11) . . ?
O12 C42 C41 121.13(11) . . ?
N43 C42 C41 114.96(10) . . ?
C33 C44 C45 113.77(10) . . ?
C33 C44 H44A 108.8 . . ?
C45 C44 H44A 108.8 . . ?
C33 C44 H44B 108.8 . . ?
C45 C44 H44B 108.8 . . ?
H44A C44 H44B 107.7 . . ?
C50 C45 C46 117.74(12) . . ?
C50 C45 C44 123.33(11) . . ?
C46 C45 C44 118.88(12) . . ?
C47 C46 C45 121.23(14) . . ?
C47 C46 H46 119.4 . . ?
C45 C46 H46 119.4 . . ?
C48 C47 C46 120.39(13) . . ?
C48 C47 H47 119.8 . . ?
C46 C47 H47 119.8 . . ?
C47 C48 C49 119.20(13) . . ?
C47 C48 H48 120.4 . . ?
C49 C48 H48 120.4 . . ?
C48 C49 C50 120.44(14) . . ?
C48 C49 H49 119.8 . . ?
C50 C49 H49 119.8 . . ?
C45 C50 C49 120.99(13) . . ?
C45 C50 H50 119.5 . . ?
C49 C50 H50 119.5 . . ?
C39 C51 C52 112.29(11) . . ?
C39 C51 H51A 109.1 . . ?
C52 C51 H51A 109.1 . . ?
C39 C51 H51B 109.1 . . ?
C52 C51 H51B 109.1 . . ?
H51A C51 H51B 107.9 . . ?
C57 C52 C53 118.73(13) . . ?
C57 C52 C51 121.17(13) . . ?
C53 C52 C51 120.07(13) . . ?
C52 C53 C54 120.56(15) . . ?
C52 C53 H53 119.7 . . ?
C54 C53 H53 119.7 . . ?
C55 C54 C53 119.94(15) . . ?
C55 C54 H54 120.0 . . ?
C53 C54 H54 120.0 . . ?
C56 C55 C54 119.74(14) . . ?
C56 C55 H55 120.1 . . ?
C54 C55 H55 120.1 . . ?
C55 C56 C57 120.47(16) . . ?
C55 C56 H56 119.8 . . ?
C57 C56 H56 119.8 . . ?
C52 C57 C56 120.55(15) . . ?
C52 C57 H57 119.7 . . ?
C56 C57 H57 119.7 . . ?
N43 C58 C59 113.23(10) . . ?
N43 C58 H58A 108.9 . . ?
C59 C58 H58A 108.9 . . ?
N43 C58 H58B 108.9 . . ?
C59 C58 H58B 108.9 . . ?
H58A C58 H58B 107.7 . . ?
C64 C59 C60 118.75(12) . . ?
C64 C59 C58 120.86(12) . . ?
C60 C59 C58 120.38(11) . . ?
C61 C60 C59 120.73(13) . . ?
C61 C60 H60 119.6 . . ?
C59 C60 H60 119.6 . . ?
C60 C61 C62 120.09(14) . . ?
C60 C61 H61 120.0 . . ?
C62 C61 H61 120.0 . . ?
C63 C62 C61 119.54(13) . . ?
C63 C62 H62 120.2 . . ?
C61 C62 H62 120.2 . . ?
C62 C63 C64 120.45(13) . . ?
C62 C63 H63 119.8 . . ?
C64 C63 H63 119.8 . . ?
C63 C64 C59 120.44(13) . . ?
C63 C64 H64 119.8 . . ?
C59 C64 H64 119.8 . . ?
C10 N11 C26 121.24(10) . . ?
C10 N11 C6 118.27(10) . . ?
C26 N11 C6 120.48(9) . . ?
C42 N43 C58 121.29(10) . . ?
C42 N43 C38 118.29(10) . . ?
C58 N43 C38 119.94(9) . . ?
C6 O1 H1 109.5 . . ?
C4 O3 H3 109.5 . . ?
C3 O4 H4 109.5 . . ?
C2 O5 H5 109.5 . . ?
C38 O7 H7 109.5 . . ?
C36 O9 H9A 109.5 . . ?
C35 O10 H10 109.5 . . ?
C34 O11 H11 109.5 . . ?

_refine_diff_density_max         0.237
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.046

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_24j
_database_code_depnum_ccdc_archive 'CCDC 1981805'
loop_
_audit_author_name
_audit_author_address
'Patrick Deschamps and Regis Guillot'
;University of Paris
France
;
_audit_update_record             
;
2020-02-04 deposited with the CCDC.	2020-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            
(E)-N-(2,3-dihydro-1H-inden-2-yl)-1(p-tolyl)methanimine
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 N'
_chemical_formula_sum            'C17 H17 N'
_chemical_formula_weight         235.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6742(2)
_cell_length_b                   8.7921(4)
_cell_length_c                   13.5713(5)
_cell_angle_alpha                103.2590(10)
_cell_angle_beta                 95.0990(10)
_cell_angle_gamma                95.6240(10)
_cell_volume                     651.48(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9977
_cell_measurement_theta_min      3.37
_cell_measurement_theta_max      63.8

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_F_000             252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.526
_shelx_estimated_absorpt_T_min   0.889
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8641
_exptl_absorpt_correction_T_max  0.9524
_exptl_absorpt_process_details   'Bruker APEX3'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS ICMMO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21496
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.368
_diffrn_reflns_theta_max         63.997
_diffrn_reflns_theta_full        63.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2166
_reflns_number_gt                1995
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ORTEP(III)
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0631P)²+0.2041P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.036(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2166
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1122
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7763(2) 0.30884(14) 0.64462(9) 0.0198(3) Uani 1 1 d . . . . .
H1 H 0.892630 0.253848 0.667926 0.024 Uiso 1 1 calc R U . . .
N2 N 0.72673(19) 0.29012(12) 0.54939(8) 0.0247(3) Uani 1 1 d . . . . .
C3 C 0.8528(2) 0.17918(14) 0.48290(9) 0.0219(3) Uani 1 1 d . . . . .
H3 H 0.945772 0.122907 0.524033 0.026 Uiso 1 1 calc R U . . .
C4 C 1.0205(2) 0.26094(15) 0.42226(9) 0.0253(3) Uani 1 1 d . . . . .
H4A H 0.966840 0.359034 0.413716 0.033 Uiso 1 1 calc R U . . .
H4B H 1.182258 0.282333 0.456130 0.033 Uiso 1 1 calc R U . . .
C4A C 1.0056(2) 0.14313(14) 0.32093(9) 0.0204(3) Uani 1 1 d . . . . .
C5 C 1.1535(2) 0.13928(15) 0.24440(10) 0.0280(3) Uani 1 1 d . . . . .
H5 H 1.284697 0.215076 0.252644 0.034 Uiso 1 1 calc R U . . .
C6 C 1.1029(2) 0.02092(16) 0.15547(10) 0.0272(3) Uani 1 1 d . . . . .
H6 H 1.201262 0.017184 0.103883 0.033 Uiso 1 1 calc R U . . .
C7 C 0.9071(2) -0.09167(15) 0.14303(9) 0.0246(3) Uani 1 1 d . . . . .
H7 H 0.874484 -0.170206 0.082996 0.030 Uiso 1 1 calc R U . . .
C8 C 0.7592(2) -0.08824(15) 0.21941(10) 0.0255(3) Uani 1 1 d . . . . .
H8 H 0.627356 -0.163698 0.210875 0.031 Uiso 1 1 calc R U . . .
C8A C 0.8107(2) 0.02953(14) 0.30887(9) 0.0204(3) Uani 1 1 d . . . . .
C9 C 0.6784(2) 0.05919(16) 0.40174(10) 0.0284(3) Uani 1 1 d . . . . .
H9A H 0.641437 -0.037182 0.423562 0.037 Uiso 1 1 calc R U . . .
H9B H 0.531270 0.102238 0.388052 0.037 Uiso 1 1 calc R U . . .
C10 C 0.6573(2) 0.41412(14) 0.71988(9) 0.0189(3) Uani 1 1 d . . . . .
C11 C 0.4527(2) 0.47808(15) 0.69208(9) 0.0229(3) Uani 1 1 d . . . . .
H11 H 0.388868 0.454972 0.624044 0.027 Uiso 1 1 calc R U . . .
C12 C 0.3447(2) 0.57530(15) 0.76487(10) 0.0234(3) Uani 1 1 d . . . . .
H12 H 0.206881 0.615162 0.745185 0.028 Uiso 1 1 calc R U . . .
C13 C 0.4382(2) 0.61520(14) 0.86784(9) 0.0203(3) Uani 1 1 d . . . . .
C14 C 0.3258(2) 0.72953(16) 0.94451(10) 0.0271(3) Uani 1 1 d . . . . .
H14A H 0.398268 0.733620 1.011886 0.069(4) Uiso 1 1 calc R U . . .
H14B H 0.158159 0.695673 0.939389 0.069(4) Uiso 1 1 calc R U . . .
H14C H 0.349266 0.832237 0.931176 0.069(4) Uiso 1 1 calc R U . . .
C15 C 0.6395(2) 0.54951(14) 0.89500(9) 0.0209(3) Uani 1 1 d . . . . .
H15 H 0.703511 0.572854 0.963008 0.025 Uiso 1 1 calc R U . . .
C16 C 0.7471(2) 0.44947(14) 0.82242(9) 0.0206(3) Uani 1 1 d . . . . .
H16 H 0.880536 0.405691 0.842583 0.025 Uiso 1 1 calc R U . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.2670(16) . ?
C1 C10 1.4724(17) . ?
C1 H1 0.9300 . ?
N2 C3 1.4576(15) . ?
C3 C9 1.5409(18) . ?
C3 C4 1.5414(18) . ?
C3 H3 0.9800 . ?
C4 C4A 1.5101(16) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4A C8A 1.3871(18) . ?
C4A C5 1.3885(18) . ?
C5 C6 1.3877(19) . ?
C5 H5 0.9300 . ?
C6 C7 1.3847(19) . ?
C6 H6 0.9300 . ?
C7 C8 1.3877(18) . ?
C7 H7 0.9300 . ?
C8 C8A 1.3901(18) . ?
C8 H8 0.9300 . ?
C8A C9 1.5086(17) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C16 1.3920(17) . ?
C10 C11 1.3978(18) . ?
C11 C12 1.3803(17) . ?
C11 H11 0.9300 . ?
C12 C13 1.4016(18) . ?
C12 H12 0.9300 . ?
C13 C15 1.3876(18) . ?
C13 C14 1.5047(16) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.3897(17) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C10 122.66(11) . . ?
N2 C1 H1 118.7 . . ?
C10 C1 H1 118.7 . . ?
C1 N2 C3 117.28(11) . . ?
N2 C3 C9 111.42(10) . . ?
N2 C3 C4 112.39(10) . . ?
C9 C3 C4 105.19(10) . . ?
N2 C3 H3 109.2 . . ?
C9 C3 H3 109.2 . . ?
C4 C3 H3 109.2 . . ?
C4A C4 C3 103.69(10) . . ?
C4A C4 H4A 111.0 . . ?
C3 C4 H4A 111.0 . . ?
C4A C4 H4B 111.0 . . ?
C3 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
C8A C4A C5 120.41(11) . . ?
C8A C4A C4 110.75(11) . . ?
C5 C4A C4 128.84(12) . . ?
C6 C5 C4A 119.17(12) . . ?
C6 C5 H5 120.4 . . ?
C4A C5 H5 120.4 . . ?
C7 C6 C5 120.44(12) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.53(12) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C8A 119.08(12) . . ?
C7 C8 H8 120.5 . . ?
C8A C8 H8 120.5 . . ?
C4A C8A C8 120.36(12) . . ?
C4A C8A C9 110.41(11) . . ?
C8 C8A C9 129.21(12) . . ?
C8A C9 C3 104.06(10) . . ?
C8A C9 H9A 110.9 . . ?
C3 C9 H9A 110.9 . . ?
C8A C9 H9B 110.9 . . ?
C3 C9 H9B 110.9 . . ?
H9A C9 H9B 109.0 . . ?
C16 C10 C11 118.44(11) . . ?
C16 C10 C1 119.47(11) . . ?
C11 C10 C1 122.08(11) . . ?
C12 C11 C10 120.47(11) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 121.39(11) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C15 C13 C12 117.76(11) . . ?
C15 C13 C14 121.98(11) . . ?
C12 C13 C14 120.23(11) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 C16 121.20(11) . . ?
C13 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C10 120.70(11) . . ?
C15 C16 H16 119.7 . . ?
C10 C16 H16 119.7 . . ?

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.130

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_25d
_database_code_depnum_ccdc_archive 'CCDC 1981802'
loop_
_audit_author_name
_audit_author_address
'Deschamps Patrick and Regis Guillot'
;University of Paris
France
;
_audit_update_record             
;
2020-02-04 deposited with the CCDC.	2020-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        2-cyclopropyl-1-phenyl-1H-benzoimidazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 N2'
_chemical_formula_sum            'C16 H14 N2'
_chemical_formula_weight         234.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.3880(4)
_cell_length_b                   10.8621(4)
_cell_length_c                   11.9356(4)
_cell_angle_alpha                103.3680(10)
_cell_angle_beta                 111.3160(10)
_cell_angle_gamma                90.2670(10)
_cell_volume                     1214.77(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9875
_cell_measurement_theta_min      4.11
_cell_measurement_theta_max      59.0

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.591
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8840
_exptl_absorpt_correction_T_max  0.9516
_exptl_absorpt_process_details   'Bruker APEX3'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS ICMMO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29618
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.106
_diffrn_reflns_theta_max         59.042
_diffrn_reflns_theta_full        59.042
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3491
_reflns_number_gt                3328
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0380P)²+0.4114P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3491
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0784
_refine_ls_wR_factor_gt          0.0776
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.61439(10) 0.85980(9) 0.27240(9) 0.0148(2) Uani 1 1 d . . . . .
C2 C 0.71118(12) 0.80988(11) 0.36103(11) 0.0151(3) Uani 1 1 d . . . . .
N3 N 0.83975(10) 0.84198(9) 0.37617(9) 0.0163(2) Uani 1 1 d . . . . .
C3A C 0.82883(12) 0.91664(11) 0.29338(11) 0.0150(3) Uani 1 1 d . . . . .
C4 C 0.93141(13) 0.97648(11) 0.26943(12) 0.0181(3) Uani 1 1 d . . . . .
H4 H 1.026919 0.969273 0.312295 0.022 Uiso 1 1 calc R U . . .
C5 C 0.89015(13) 1.04690(11) 0.18121(11) 0.0188(3) Uani 1 1 d . . . . .
H5 H 0.958853 1.088180 0.163733 0.023 Uiso 1 1 calc R U . . .
C6 C 0.74996(13) 1.05869(11) 0.11731(11) 0.0179(3) Uani 1 1 d . . . . .
H6 H 0.725217 1.107351 0.057206 0.021 Uiso 1 1 calc R U . . .
C7 C 0.64682(13) 1.00032(11) 0.14058(11) 0.0164(3) Uani 1 1 d . . . . .
H7 H 0.551388 1.008425 0.098394 0.020 Uiso 1 1 calc R U . . .
C7A C 0.68936(12) 0.92949(11) 0.22835(11) 0.0145(3) Uani 1 1 d . . . . .
C8 C 0.46626(12) 0.84989(11) 0.23241(11) 0.0148(3) Uani 1 1 d . . . . .
C9 C 0.40151(12) 0.95968(12) 0.25360(11) 0.0173(3) Uani 1 1 d . . . . .
H9 H 0.455194 1.039004 0.297585 0.021 Uiso 1 1 calc R U . . .
C10 C 0.25818(13) 0.95229(12) 0.21001(11) 0.0188(3) Uani 1 1 d . . . . .
H10 H 0.213014 1.026987 0.223536 0.023 Uiso 1 1 calc R U . . .
C11 C 0.18001(13) 0.83615(12) 0.14657(11) 0.0177(3) Uani 1 1 d . . . . .
H11 H 0.081535 0.831354 0.117324 0.021 Uiso 1 1 calc R U . . .
C12 C 0.24549(13) 0.72723(12) 0.12587(11) 0.0185(3) Uani 1 1 d . . . . .
H12 H 0.191855 0.647798 0.082396 0.022 Uiso 1 1 calc R U . . .
C13 C 0.38893(12) 0.73392(12) 0.16842(11) 0.0173(3) Uani 1 1 d . . . . .
H13 H 0.434012 0.659405 0.153796 0.021 Uiso 1 1 calc R U . . .
C14 C 0.67062(13) 0.73308(11) 0.43119(11) 0.0177(3) Uani 1 1 d . . . . .
H14 H 0.568834 0.712424 0.407678 0.021 Uiso 1 1 calc R U . . .
C15 C 0.76464(13) 0.63463(12) 0.47690(12) 0.0214(3) Uani 1 1 d . . . . .
H15A H 0.720648 0.554727 0.479280 0.028 Uiso 1 1 calc R U . . .
H15B H 0.848333 0.624967 0.455650 0.028 Uiso 1 1 calc R U . . .
C16 C 0.76154(14) 0.75327(12) 0.56716(12) 0.0226(3) Uani 1 1 d . . . . .
H16A H 0.843275 0.817158 0.601818 0.029 Uiso 1 1 calc R U . . .
H16B H 0.715579 0.746912 0.625450 0.029 Uiso 1 1 calc R U . . .
N17 N 0.10832(10) 0.52280(9) 0.26459(9) 0.0147(2) Uani 1 1 d . . . . .
C18 C 0.20530(12) 0.61631(11) 0.35626(11) 0.0150(3) Uani 1 1 d . . . . .
N19 N 0.33385(10) 0.59166(9) 0.37286(9) 0.0161(2) Uani 1 1 d . . . . .
C19A C 0.32274(12) 0.47630(11) 0.28823(11) 0.0153(3) Uani 1 1 d . . . . .
C20 C 0.42556(13) 0.40468(12) 0.26537(12) 0.0188(3) Uani 1 1 d . . . . .
H20 H 0.521133 0.433286 0.310198 0.023 Uiso 1 1 calc R U . . .
C21 C 0.38438(13) 0.29062(12) 0.17543(12) 0.0202(3) Uani 1 1 d . . . . .
H21 H 0.453174 0.240509 0.158878 0.024 Uiso 1 1 calc R U . . .
C22 C 0.24413(13) 0.24720(12) 0.10826(11) 0.0193(3) Uani 1 1 d . . . . .
H22 H 0.219506 0.168592 0.046998 0.023 Uiso 1 1 calc R U . . .
C23 C 0.14071(13) 0.31724(11) 0.12985(11) 0.0170(3) Uani 1 1 d . . . . .
H23 H 0.045203 0.288462 0.084904 0.020 Uiso 1 1 calc R U . . .
C23A C 0.18298(12) 0.43126(11) 0.22004(11) 0.0144(3) Uani 1 1 d . . . . .
C24 C -0.04004(12) 0.51290(11) 0.22355(11) 0.0148(3) Uani 1 1 d . . . . .
C25 C -0.11537(13) 0.59776(11) 0.16099(11) 0.0180(3) Uani 1 1 d . . . . .
H25 H -0.068740 0.665054 0.147520 0.022 Uiso 1 1 calc R U . . .
C26 C -0.25894(13) 0.58398(12) 0.11823(11) 0.0195(3) Uani 1 1 d . . . . .
H26 H -0.310989 0.642590 0.076243 0.023 Uiso 1 1 calc R U . . .
C27 C -0.32679(13) 0.48487(12) 0.13659(11) 0.0188(3) Uani 1 1 d . . . . .
H27 H -0.425339 0.475023 0.106626 0.023 Uiso 1 1 calc R U . . .
C28 C -0.25046(13) 0.39992(12) 0.19887(11) 0.0195(3) Uani 1 1 d . . . . .
H28 H -0.297125 0.331873 0.211264 0.023 Uiso 1 1 calc R U . . .
C29 C -0.10730(13) 0.41370(11) 0.24288(11) 0.0179(3) Uani 1 1 d . . . . .
H29 H -0.055239 0.355859 0.286009 0.021 Uiso 1 1 calc R U . . .
C30 C 0.16500(13) 0.72747(11) 0.42770(11) 0.0176(3) Uani 1 1 d . . . . .
H30 H 0.063374 0.737005 0.402292 0.021 Uiso 1 1 calc R U . . .
C31 C 0.25275(14) 0.77265(12) 0.56498(12) 0.0230(3) Uani 1 1 d . . . . .
H31A H 0.204972 0.807168 0.622036 0.030 Uiso 1 1 calc R U . . .
H31B H 0.332572 0.724997 0.599603 0.030 Uiso 1 1 calc R U . . .
C32 C 0.26163(13) 0.84861(12) 0.47880(11) 0.0206(3) Uani 1 1 d . . . . .
H32A H 0.347034 0.848104 0.460123 0.027 Uiso 1 1 calc R U . . .
H32B H 0.219458 0.930260 0.482551 0.027 Uiso 1 1 calc R U . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.3860(15) . ?
N1 C7A 1.3900(15) . ?
N1 C8 1.4310(15) . ?
C2 N3 1.3149(16) . ?
C2 C14 1.4667(17) . ?
N3 C3A 1.3917(16) . ?
C3A C7A 1.3983(17) . ?
C3A C4 1.3931(17) . ?
C4 C5 1.3873(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3994(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.3851(18) . ?
C6 H6 0.9500 . ?
C7 C7A 1.3871(17) . ?
C7 H7 0.9500 . ?
C8 C13 1.3839(17) . ?
C8 C9 1.3893(17) . ?
C9 C10 1.3822(17) . ?
C9 H9 0.9500 . ?
C10 C11 1.3878(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.3848(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.3840(17) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.5123(17) . ?
C14 C16 1.5142(18) . ?
C14 H14 1.0000 . ?
C15 C16 1.4852(18) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
N17 C18 1.3852(16) . ?
N17 C23A 1.3912(15) . ?
N17 C24 1.4325(15) . ?
C18 N19 1.3152(15) . ?
C18 C30 1.4657(17) . ?
N19 C19A 1.3901(16) . ?
C19A C23A 1.3999(17) . ?
C19A C20 1.3936(17) . ?
C20 C21 1.3843(18) . ?
C20 H20 0.9500 . ?
C21 C22 1.3991(18) . ?
C21 H21 0.9500 . ?
C22 C23 1.3847(18) . ?
C22 H22 0.9500 . ?
C23 C23A 1.3857(17) . ?
C23 H23 0.9500 . ?
C24 C25 1.3855(17) . ?
C24 C29 1.3884(17) . ?
C25 C26 1.3843(17) . ?
C25 H25 0.9500 . ?
C26 C27 1.3849(18) . ?
C26 H26 0.9500 . ?
C27 C28 1.3886(18) . ?
C27 H27 0.9500 . ?
C28 C29 1.3797(17) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 C32 1.5107(17) . ?
C30 C31 1.5148(18) . ?
C30 H30 1.0000 . ?
C31 C32 1.4858(18) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C7A 106.38(9) . . ?
C2 N1 C8 129.61(10) . . ?
C7A N1 C8 123.98(10) . . ?
N3 C2 N1 112.74(10) . . ?
N3 C2 C14 125.06(11) . . ?
N1 C2 C14 122.17(10) . . ?
C2 N3 C3A 105.23(10) . . ?
N3 C3A C7A 110.30(10) . . ?
N3 C3A C4 130.46(11) . . ?
C7A C3A C4 119.24(11) . . ?
C5 C4 C3A 118.13(11) . . ?
C5 C4 H4 120.9 . . ?
C3A C4 H4 120.9 . . ?
C4 C5 C6 121.71(11) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C7 C6 C5 120.83(11) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C7A C7 C6 116.90(11) . . ?
C7A C7 H7 121.6 . . ?
C6 C7 H7 121.6 . . ?
C7 C7A N1 131.47(11) . . ?
C7 C7A C3A 123.19(11) . . ?
N1 C7A C3A 105.35(10) . . ?
C13 C8 C9 120.76(11) . . ?
C13 C8 N1 120.40(10) . . ?
C9 C8 N1 118.77(10) . . ?
C8 C9 C10 119.31(11) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 120.24(11) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.03(11) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 120.11(11) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C8 C13 C12 119.55(11) . . ?
C8 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C2 C14 C15 117.89(11) . . ?
C2 C14 C16 117.16(10) . . ?
C15 C14 C16 58.77(8) . . ?
C2 C14 H14 116.8 . . ?
C15 C14 H14 116.8 . . ?
C16 C14 H14 116.8 . . ?
C16 C15 C14 60.68(8) . . ?
C16 C15 H15A 117.7 . . ?
C14 C15 H15A 117.7 . . ?
C16 C15 H15B 117.7 . . ?
C14 C15 H15B 117.7 . . ?
H15A C15 H15B 114.8 . . ?
C15 C16 C14 60.55(8) . . ?
C15 C16 H16A 117.7 . . ?
C14 C16 H16A 117.7 . . ?
C15 C16 H16B 117.7 . . ?
C14 C16 H16B 117.7 . . ?
H16A C16 H16B 114.8 . . ?
C18 N17 C23A 106.48(9) . . ?
C18 N17 C24 129.25(10) . . ?
C23A N17 C24 124.20(10) . . ?
N19 C18 N17 112.68(10) . . ?
N19 C18 C30 125.07(11) . . ?
N17 C18 C30 122.22(10) . . ?
C18 N19 C19A 105.30(10) . . ?
N19 C19A C23A 110.35(10) . . ?
N19 C19A C20 130.30(11) . . ?
C23A C19A C20 119.35(11) . . ?
C21 C20 C19A 118.06(12) . . ?
C21 C20 H20 121.0 . . ?
C19A C20 H20 121.0 . . ?
C20 C21 C22 121.74(11) . . ?
C20 C21 H21 119.1 . . ?
C22 C21 H21 119.1 . . ?
C23 C22 C21 120.91(12) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C23A C23 C22 116.92(11) . . ?
C23A C23 H23 121.5 . . ?
C22 C23 H23 121.5 . . ?
C23 C23A N17 131.79(11) . . ?
C23 C23A C19A 123.03(11) . . ?
N17 C23A C19A 105.19(10) . . ?
C25 C24 C29 120.59(11) . . ?
C25 C24 N17 120.50(10) . . ?
C29 C24 N17 118.86(10) . . ?
C24 C25 C26 119.66(11) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C27 C26 C25 120.08(11) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C28 119.86(11) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C27 C28 C29 120.43(11) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C24 C29 C28 119.37(11) . . ?
C24 C29 H29 120.3 . . ?
C28 C29 H29 120.3 . . ?
C18 C30 C32 117.94(10) . . ?
C18 C30 C31 117.25(10) . . ?
C32 C30 C31 58.83(8) . . ?
C18 C30 H30 116.8 . . ?
C32 C30 H30 116.8 . . ?
C31 C30 H30 116.8 . . ?
C32 C31 C30 60.45(8) . . ?
C32 C31 H31A 117.7 . . ?
C30 C31 H31A 117.7 . . ?
C32 C31 H31B 117.7 . . ?
C30 C31 H31B 117.7 . . ?
H31A C31 H31B 114.8 . . ?
C31 C32 C30 60.72(8) . . ?
C31 C32 H32A 117.7 . . ?
C30 C32 H32A 117.7 . . ?
C31 C32 H32B 117.7 . . ?
C30 C32 H32B 117.7 . . ?
H32A C32 H32B 114.8 . . ?

_refine_diff_density_max         0.121
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.039

