# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_5_a
_database_code_depnum_ccdc_archive 'CCDC 2150669'
loop_
_audit_author_name
_audit_author_address
'Kento Iwai'
;Kochi University of Technology
Japan
;
_audit_update_record             
;
2022-02-08 deposited with the CCDC.	2022-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
E-1-(2-acetylaminophenyl)-1-bromo-2-(2-bromophenyl)ethene
_chemical_name_common            ?
_chemical_melting_point          388.8-389.5
_chemical_formula_moiety         'C16 H13 Br2 N1 O1'
_chemical_formula_sum            'C16 H13 Br2 N1 O1'
_chemical_formula_weight         395.07

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'
Br Br -0.2901 2.4595 '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                   9.9894(2)
_cell_length_b                   11.4609(3)
_cell_length_c                   14.7673(4)
_cell_angle_alpha                106.052(2)
_cell_angle_beta                 102.529(2)
_cell_angle_gamma                106.772(2)
_cell_volume                     1472.53(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)

_cell_measurement_reflns_used    9984

_cell_measurement_theta_min      2.0200

_cell_measurement_theta_max      29.4400


_exptl_crystal_description       plate

_exptl_crystal_colour            colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.782
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.592

_exptl_crystal_size_mid          0.214

_exptl_crystal_size_min          0.076

_exptl_absorpt_coefficient_mu    5.499
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian

_exptl_absorpt_correction_T_min  0.116

_exptl_absorpt_correction_T_max  1.000

_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.47a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
   a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'

_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 10.0000

_diffrn_reflns_number            16132
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.992
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5481
_reflns_number_gt                4651
_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       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_structure_solution    ?

_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.0486P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5481
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0784
_refine_ls_wR_factor_gt          0.0754
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.002
_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 0.1727(3) 0.0649(3) 0.6607(2) 0.0150(6) Uani 1 1 d . . . . .
C2 C 0.0759(3) -0.0323(3) 0.6819(2) 0.0151(6) Uani 1 1 d . . . . .
C3 C 0.0048(3) -0.1575(3) 0.6084(2) 0.0182(7) Uani 1 1 d . . . . .
H1 H -0.062991 -0.223856 0.620689 0.022 Uiso 1 1 calc R U . . .
C4 C 0.0318(3) -0.1866(3) 0.5175(2) 0.0224(7) Uani 1 1 d . . . . .
H2 H -0.016321 -0.272430 0.468792 0.027 Uiso 1 1 calc R U . . .
C5 C 0.1282(3) -0.0906(3) 0.4987(2) 0.0236(7) Uani 1 1 d . . . . .
H3 H 0.146798 -0.110071 0.436889 0.028 Uiso 1 1 calc R U . . .
C6 C 0.1982(3) 0.0348(3) 0.5698(2) 0.0190(7) Uani 1 1 d . . . . .
H4 H 0.264436 0.100849 0.556258 0.023 Uiso 1 1 calc R U . . .
N1 N 0.2505(3) 0.1950(2) 0.73152(18) 0.0163(5) Uani 1 1 d . . . . .
H5 H 0.347646 0.224471 0.751698 0.020 Uiso 1 1 calc R U . . .
C7 C 0.1848(3) 0.2765(3) 0.7699(2) 0.0170(6) Uani 1 1 d . . . . .
O1 O 0.0508(2) 0.24449(19) 0.74853(15) 0.0212(5) Uani 1 1 d . . . . .
C8 C 0.2927(3) 0.4087(3) 0.8424(2) 0.0235(7) Uani 1 1 d . . . . .
H6 H 0.248294 0.474327 0.840563 0.035 Uiso 1 1 calc R U . . .
H7 H 0.382767 0.431509 0.824056 0.035 Uiso 1 1 calc R U . . .
H8 H 0.317160 0.406513 0.909662 0.035 Uiso 1 1 calc R U . . .
C9 C 0.0567(3) -0.0068(3) 0.7807(2) 0.0157(6) Uani 1 1 d . . . . .
Br1 Br -0.14477(3) -0.04591(3) 0.77811(2) 0.02509(10) Uani 1 1 d . . . . .
C10 C 0.1590(3) 0.0321(3) 0.8690(2) 0.0173(7) Uani 1 1 d . . . . .
H9 H 0.129517 0.050285 0.926694 0.021 Uiso 1 1 calc R U . . .
C13 C 0.5761(4) 0.1618(3) 0.9803(2) 0.0271(8) Uani 1 1 d . . . . .
H10 H 0.652041 0.231311 1.035804 0.033 Uiso 1 1 calc R U . . .
C11 C 0.3154(3) 0.0487(3) 0.8827(2) 0.0161(6) Uani 1 1 d . . . . .
C12 C 0.4303(3) 0.1483(3) 0.9640(2) 0.0186(7) Uani 1 1 d . . . . .
C14 C 0.6095(4) 0.0716(4) 0.9136(3) 0.0297(8) Uani 1 1 d . . . . .
H11 H 0.709620 0.080362 0.923140 0.036 Uiso 1 1 calc R U . . .
C15 C 0.5005(4) -0.0296(3) 0.8346(2) 0.0254(8) Uani 1 1 d . . . . .
H12 H 0.524503 -0.092152 0.790590 0.031 Uiso 1 1 calc R U . . .
C16 C 0.3544(3) -0.0409(3) 0.8187(2) 0.0185(7) Uani 1 1 d . . . . .
H13 H 0.279317 -0.111073 0.763082 0.022 Uiso 1 1 calc R U . . .
Br2 Br 0.38597(4) 0.27011(3) 1.05804(2) 0.02756(10) Uani 1 1 d . . . . .
C17 C 0.8669(3) 0.4775(3) 0.8314(2) 0.0170(7) Uani 1 1 d . . . . .
C18 C 0.9420(3) 0.5717(3) 0.7979(2) 0.0165(6) Uani 1 1 d . . . . .
C19 C 1.0102(3) 0.7016(3) 0.8623(2) 0.0202(7) Uani 1 1 d . . . . .
H14 H 1.064710 0.765386 0.840947 0.024 Uiso 1 1 calc R U . . .
C20 C 0.9993(3) 0.7388(3) 0.9571(2) 0.0244(7) Uani 1 1 d . . . . .
H15 H 1.042868 0.828290 0.999556 0.029 Uiso 1 1 calc R U . . .
C21 C 0.9249(3) 0.6456(3) 0.9897(2) 0.0275(8) Uani 1 1 d . . . . .
H16 H 0.919693 0.670850 1.055398 0.033 Uiso 1 1 calc R U . . .
C22 C 0.8580(3) 0.5158(3) 0.9274(2) 0.0218(7) Uani 1 1 d . . . . .
H17 H 0.805628 0.452483 0.949998 0.026 Uiso 1 1 calc R U . . .
N2 N 0.8026(3) 0.3432(2) 0.76876(18) 0.0178(6) Uani 1 1 d . . . . .
H18 H 0.860237 0.306815 0.745031 0.021 Uiso 1 1 calc R U . . .
C23 C 0.6578(3) 0.2676(3) 0.7431(2) 0.0183(7) Uani 1 1 d . . . . .
O2 O 0.5703(2) 0.3101(2) 0.77438(16) 0.0224(5) Uani 1 1 d . . . . .
C24 C 0.6121(3) 0.1310(3) 0.6718(2) 0.0229(7) Uani 1 1 d . . . . .
H19 H 0.521048 0.075207 0.676788 0.034 Uiso 1 1 calc R U . . .
H20 H 0.690430 0.097457 0.688051 0.034 Uiso 1 1 calc R U . . .
H21 H 0.594806 0.130698 0.603829 0.034 Uiso 1 1 calc R U . . .
C25 C 0.9426(3) 0.5378(3) 0.6933(2) 0.0167(6) Uani 1 1 d . . . . .
C26 C 0.8271(3) 0.4881(3) 0.6101(2) 0.0169(6) Uani 1 1 d . . . . .
H22 H 0.846411 0.468074 0.548551 0.020 Uiso 1 1 calc R U . . .
C27 C 0.6721(3) 0.4617(3) 0.6061(2) 0.0164(6) Uani 1 1 d . . . . .
C28 C 0.5574(3) 0.3546(3) 0.5302(2) 0.0166(6) Uani 1 1 d . . . . .
C29 C 0.4108(3) 0.3297(3) 0.5224(2) 0.0199(7) Uani 1 1 d . . . . .
H23 H 0.334757 0.255914 0.470049 0.024 Uiso 1 1 calc R U . . .
C30 C 0.3767(3) 0.4155(3) 0.5934(2) 0.0184(7) Uani 1 1 d . . . . .
H24 H 0.276536 0.399158 0.589753 0.022 Uiso 1 1 calc R U . . .
C31 C 0.4851(3) 0.5217(3) 0.6673(2) 0.0213(7) Uani 1 1 d . . . . .
H25 H 0.460482 0.579630 0.714687 0.026 Uiso 1 1 calc R U . . .
C32 C 0.6322(3) 0.5462(3) 0.6741(2) 0.0185(7) Uani 1 1 d . . . . .
H26 H 0.707004 0.621611 0.725679 0.022 Uiso 1 1 calc R U . . .
Br3 Br 0.60092(3) 0.23429(3) 0.43440(2) 0.02312(10) Uani 1 1 d . . . . .
Br4 Br 1.13539(3) 0.57968(3) 0.67916(2) 0.02240(10) 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 C6 1.389(4) . ?
C1 C2 1.405(4) . ?
C1 N1 1.427(4) . ?
C2 C3 1.398(4) . ?
C2 C9 1.473(4) . ?
C3 C4 1.396(4) . ?
C4 C5 1.374(5) . ?
C5 C6 1.387(4) . ?
N1 C7 1.358(4) . ?
C7 O1 1.223(3) . ?
C7 C8 1.505(4) . ?
C9 C10 1.335(4) . ?
C9 Br1 1.921(3) . ?
C10 C11 1.479(4) . ?
C13 C12 1.379(4) . ?
C13 C14 1.389(5) . ?
C11 C12 1.396(4) . ?
C11 C16 1.399(4) . ?
C12 Br2 1.904(3) . ?
C14 C15 1.366(5) . ?
C15 C16 1.388(4) . ?
C17 C22 1.394(4) . ?
C17 C18 1.402(4) . ?
C17 N2 1.421(4) . ?
C18 C19 1.391(4) . ?
C18 C25 1.486(4) . ?
C19 C20 1.384(4) . ?
C20 C21 1.382(5) . ?
C21 C22 1.381(5) . ?
N2 C23 1.358(4) . ?
C23 O2 1.230(3) . ?
C23 C24 1.495(4) . ?
C25 C26 1.336(4) . ?
C25 Br4 1.918(3) . ?
C26 C27 1.474(4) . ?
C27 C28 1.395(4) . ?
C27 C32 1.402(4) . ?
C28 C29 1.380(4) . ?
C28 Br3 1.904(3) . ?
C29 C30 1.400(4) . ?
C30 C31 1.356(4) . ?
C31 C32 1.389(4) . ?

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
C6 C1 C2 120.1(3) . . ?
C6 C1 N1 118.0(3) . . ?
C2 C1 N1 121.9(3) . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 C9 120.3(3) . . ?
C1 C2 C9 121.4(3) . . ?
C4 C3 C2 121.2(3) . . ?
C5 C4 C3 119.8(3) . . ?
C4 C5 C6 120.1(3) . . ?
C5 C6 C1 120.7(3) . . ?
C7 N1 C1 124.5(2) . . ?
O1 C7 N1 123.1(3) . . ?
O1 C7 C8 123.3(3) . . ?
N1 C7 C8 113.6(3) . . ?
C10 C9 C2 128.4(3) . . ?
C10 C9 Br1 117.2(2) . . ?
C2 C9 Br1 114.3(2) . . ?
C9 C10 C11 124.2(3) . . ?
C12 C13 C14 118.5(3) . . ?
C12 C11 C16 116.6(3) . . ?
C12 C11 C10 121.9(3) . . ?
C16 C11 C10 121.3(3) . . ?
C13 C12 C11 122.7(3) . . ?
C13 C12 Br2 118.0(2) . . ?
C11 C12 Br2 119.3(2) . . ?
C15 C14 C13 120.9(3) . . ?
C14 C15 C16 119.8(3) . . ?
C15 C16 C11 121.4(3) . . ?
C22 C17 C18 119.6(3) . . ?
C22 C17 N2 120.1(3) . . ?
C18 C17 N2 120.3(3) . . ?
C19 C18 C17 119.2(3) . . ?
C19 C18 C25 119.1(3) . . ?
C17 C18 C25 121.6(3) . . ?
C20 C19 C18 120.7(3) . . ?
C21 C20 C19 119.8(3) . . ?
C22 C21 C20 120.4(3) . . ?
C21 C22 C17 120.2(3) . . ?
C23 N2 C17 124.2(2) . . ?
O2 C23 N2 122.1(3) . . ?
O2 C23 C24 122.7(3) . . ?
N2 C23 C24 115.2(3) . . ?
C26 C25 C18 128.1(3) . . ?
C26 C25 Br4 117.2(2) . . ?
C18 C25 Br4 114.7(2) . . ?
C25 C26 C27 125.3(3) . . ?
C28 C27 C32 116.9(3) . . ?
C28 C27 C26 121.0(3) . . ?
C32 C27 C26 122.0(3) . . ?
C29 C28 C27 122.4(3) . . ?
C29 C28 Br3 117.7(2) . . ?
C27 C28 Br3 119.9(2) . . ?
C28 C29 C30 118.5(3) . . ?
C31 C30 C29 120.7(3) . . ?
C30 C31 C32 120.2(3) . . ?
C31 C32 C27 121.2(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.4(4) . . . . ?
N1 C1 C2 C3 -179.6(2) . . . . ?
C6 C1 C2 C9 174.4(3) . . . . ?
N1 C1 C2 C9 -3.8(4) . . . . ?
C1 C2 C3 C4 1.6(4) . . . . ?
C9 C2 C3 C4 -174.2(3) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
N1 C1 C6 C5 178.7(3) . . . . ?
C6 C1 N1 C7 120.9(3) . . . . ?
C2 C1 N1 C7 -60.9(4) . . . . ?
C1 N1 C7 O1 1.6(4) . . . . ?
C1 N1 C7 C8 -179.4(3) . . . . ?
C3 C2 C9 C10 117.7(3) . . . . ?
C1 C2 C9 C10 -58.0(4) . . . . ?
C3 C2 C9 Br1 -58.2(3) . . . . ?
C1 C2 C9 Br1 126.1(2) . . . . ?
C2 C9 C10 C11 -4.5(5) . . . . ?
Br1 C9 C10 C11 171.3(2) . . . . ?
C9 C10 C11 C12 144.1(3) . . . . ?
C9 C10 C11 C16 -40.9(4) . . . . ?
C14 C13 C12 C11 -0.9(5) . . . . ?
C14 C13 C12 Br2 178.4(2) . . . . ?
C16 C11 C12 C13 1.9(4) . . . . ?
C10 C11 C12 C13 177.2(3) . . . . ?
C16 C11 C12 Br2 -177.4(2) . . . . ?
C10 C11 C12 Br2 -2.1(4) . . . . ?
C12 C13 C14 C15 -1.0(5) . . . . ?
C13 C14 C15 C16 1.8(5) . . . . ?
C14 C15 C16 C11 -0.7(5) . . . . ?
C12 C11 C16 C15 -1.1(4) . . . . ?
C10 C11 C16 C15 -176.4(3) . . . . ?
C22 C17 C18 C19 1.9(4) . . . . ?
N2 C17 C18 C19 -176.9(3) . . . . ?
C22 C17 C18 C25 -174.1(3) . . . . ?
N2 C17 C18 C25 7.0(4) . . . . ?
C17 C18 C19 C20 -2.6(4) . . . . ?
C25 C18 C19 C20 173.5(3) . . . . ?
C18 C19 C20 C21 2.5(5) . . . . ?
C19 C20 C21 C22 -1.7(5) . . . . ?
C20 C21 C22 C17 1.0(5) . . . . ?
C18 C17 C22 C21 -1.1(4) . . . . ?
N2 C17 C22 C21 177.7(3) . . . . ?
C22 C17 N2 C23 57.4(4) . . . . ?
C18 C17 N2 C23 -123.8(3) . . . . ?
C17 N2 C23 O2 -1.3(4) . . . . ?
C17 N2 C23 C24 176.7(3) . . . . ?
C19 C18 C25 C26 -116.1(3) . . . . ?
C17 C18 C25 C26 59.9(4) . . . . ?
C19 C18 C25 Br4 60.6(3) . . . . ?
C17 C18 C25 Br4 -123.4(3) . . . . ?
C18 C25 C26 C27 2.9(5) . . . . ?
Br4 C25 C26 C27 -173.8(2) . . . . ?
C25 C26 C27 C28 -144.9(3) . . . . ?
C25 C26 C27 C32 38.8(4) . . . . ?
C32 C27 C28 C29 -1.3(4) . . . . ?
C26 C27 C28 C29 -177.8(3) . . . . ?
C32 C27 C28 Br3 -180.0(2) . . . . ?
C26 C27 C28 Br3 3.6(4) . . . . ?
C27 C28 C29 C30 0.1(4) . . . . ?
Br3 C28 C29 C30 178.7(2) . . . . ?
C28 C29 C30 C31 0.9(4) . . . . ?
C29 C30 C31 C32 -0.5(4) . . . . ?
C30 C31 C32 C27 -0.8(4) . . . . ?
C28 C27 C32 C31 1.7(4) . . . . ?
C26 C27 C32 C31 178.1(3) . . . . ?

_refine_diff_density_max         0.983
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.099


_symmetry_cell_setting           triclinic
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  mirror
_chemical_absolute_configuration ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane'
####################################################################### 
# 
# 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_9a_a
_database_code_depnum_ccdc_archive 'CCDC 2150670'
loop_
_audit_author_name
_audit_author_address
'Kento Iwai'
;Kochi University of Technology
Japan
;
_audit_update_record             
;
2022-02-08 deposited with the CCDC.	2022-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
Z-1-(2-Acetylaminophenyl)-2-(2-bromophenyl)-1-(4-methylphenyl)ethene
_chemical_name_common            ?
_chemical_melting_point          399.0-400.0
_chemical_formula_moiety         'C23 H20 Br N O'
_chemical_formula_sum            'C23 H20 Br N O'
_chemical_formula_weight         406.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.3390(3)
_cell_length_b                   10.6181(3)
_cell_length_c                   21.0722(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.485(3)
_cell_angle_gamma                90
_cell_volume                     1864.07(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)

_cell_measurement_reflns_used    7331

_cell_measurement_theta_min      1.9770

_cell_measurement_theta_max      29.7010


_exptl_crystal_description       block

_exptl_crystal_colour            colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.660

_exptl_crystal_size_mid          0.489

_exptl_crystal_size_min          0.458

_exptl_absorpt_coefficient_mu    2.216
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian

_exptl_absorpt_correction_T_min  0.402

_exptl_absorpt_correction_T_max  1.000

_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.47a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
   a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'

_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 10.0000

_diffrn_reflns_number            12584
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.445
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3460
_reflns_number_gt                3085
_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       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_structure_solution    ?

_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.0225P)²+1.6201P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3460
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0660
_refine_ls_wR_factor_gt          0.0642
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.002
_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 0.6230(2) 0.7005(2) 0.68215(9) 0.0162(5) Uani 1 1 d . . . . .
C2 C 0.5995(2) 0.8049(2) 0.64239(9) 0.0138(4) Uani 1 1 d . . . . .
C3 C 0.6303(2) 0.9247(2) 0.66681(10) 0.0179(5) Uani 1 1 d . . . . .
H1 H 0.616806 0.995777 0.639713 0.021 Uiso 1 1 calc R U . . .
N1 N 0.6005(2) 0.57870(17) 0.65611(8) 0.0171(4) Uani 1 1 d . . . . .
H2 H 0.543378 0.574944 0.620053 0.021 Uiso 1 1 calc R U . . .
O1 O 0.7290(2) 0.45523(16) 0.73069(8) 0.0298(4) Uani 1 1 d . . . . .
C12 C 0.1896(2) 0.5894(2) 0.58707(9) 0.0149(4) Uani 1 1 d . . . . .
Br1 Br 0.24448(3) 0.48034(2) 0.51942(2) 0.02468(9) Uani 1 1 d . . . . .
C9 C 0.5450(2) 0.79119(19) 0.57388(9) 0.0128(4) Uani 1 1 d . . . . .
C10 C 0.4026(2) 0.74110(19) 0.55592(9) 0.0135(4) Uani 1 1 d . . . . .
H3 H 0.382024 0.729918 0.511590 0.016 Uiso 1 1 calc R U . . .
C11 C 0.2741(2) 0.7014(2) 0.59793(9) 0.0131(4) Uani 1 1 d . . . . .
C13 C 0.0695(2) 0.5492(2) 0.62547(10) 0.0174(5) Uani 1 1 d . . . . .
H4 H 0.014454 0.472386 0.616664 0.021 Uiso 1 1 calc R U . . .
C7 C 0.6558(3) 0.4660(2) 0.67956(11) 0.0201(5) Uani 1 1 d . . . . .
C14 C 0.0306(2) 0.6224(2) 0.67700(10) 0.0183(5) Uani 1 1 d . . . . .
H5 H -0.050623 0.595361 0.704190 0.022 Uiso 1 1 calc R U . . .
C15 C 0.1099(2) 0.7347(2) 0.68882(10) 0.0177(5) Uani 1 1 d . . . . .
H6 H 0.081817 0.785464 0.723782 0.021 Uiso 1 1 calc R U . . .
C4 C 0.6802(3) 0.9427(2) 0.72979(11) 0.0234(5) Uani 1 1 d . . . . .
H7 H 0.700966 1.024955 0.745826 0.028 Uiso 1 1 calc R U . . .
C19 C 0.9340(3) 0.8442(2) 0.49148(10) 0.0178(5) Uani 1 1 d . . . . .
H8 H 1.045834 0.835974 0.501079 0.021 Uiso 1 1 calc R U . . .
C6 C 0.6710(3) 0.7190(2) 0.74609(10) 0.0221(5) Uani 1 1 d . . . . .
H9 H 0.683939 0.648664 0.773698 0.026 Uiso 1 1 calc R U . . .
C20 C 0.8812(3) 0.8809(2) 0.43080(10) 0.0166(5) Uani 1 1 d . . . . .
C5 C 0.6993(3) 0.8383(2) 0.76888(10) 0.0253(5) Uani 1 1 d . . . . .
H10 H 0.732624 0.849609 0.812197 0.030 Uiso 1 1 calc R U . . .
C8 C 0.6244(3) 0.3550(2) 0.63633(11) 0.0257(5) Uani 1 1 d . . . . .
H11 H 0.717525 0.341262 0.610355 0.039 Uiso 1 1 calc R U . . .
H12 H 0.529451 0.371780 0.608595 0.039 Uiso 1 1 calc R U . . .
H13 H 0.605875 0.279720 0.661895 0.039 Uiso 1 1 calc R U . . .
C16 C 0.2302(2) 0.7739(2) 0.64996(9) 0.0151(4) Uani 1 1 d . . . . .
H14 H 0.283773 0.851295 0.658743 0.018 Uiso 1 1 calc R U . . .
C17 C 0.6618(2) 0.82963(19) 0.52590(9) 0.0126(4) Uani 1 1 d . . . . .
C18 C 0.8261(2) 0.8195(2) 0.53843(10) 0.0159(4) Uani 1 1 d . . . . .
H15 H 0.865322 0.795239 0.579631 0.019 Uiso 1 1 calc R U . . .
C21 C 0.7175(3) 0.8961(2) 0.41922(10) 0.0164(5) Uani 1 1 d . . . . .
H16 H 0.678925 0.924057 0.378542 0.020 Uiso 1 1 calc R U . . .
C22 C 0.6088(2) 0.87158(19) 0.46549(9) 0.0142(4) Uani 1 1 d . . . . .
H17 H 0.497271 0.883288 0.456214 0.017 Uiso 1 1 calc R U . . .
C23 C 0.9981(3) 0.9043(2) 0.37915(11) 0.0249(5) Uani 1 1 d . . . . .
H18 H 1.002752 0.829827 0.351795 0.037 Uiso 1 1 calc R U . . .
H19 H 1.104987 0.921060 0.398500 0.037 Uiso 1 1 calc R U . . .
H20 H 0.962453 0.977101 0.353691 0.037 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 C2 1.398(3) . ?
C1 C6 1.403(3) . ?
C1 N1 1.414(3) . ?
C2 C3 1.392(3) . ?
C2 C9 1.502(3) . ?
C3 C4 1.387(3) . ?
N1 C7 1.367(3) . ?
O1 C7 1.220(3) . ?
C12 C13 1.382(3) . ?
C12 C11 1.396(3) . ?
C12 Br1 1.908(2) . ?
C9 C10 1.340(3) . ?
C9 C17 1.491(3) . ?
C10 C11 1.481(3) . ?
C11 C16 1.402(3) . ?
C13 C14 1.386(3) . ?
C7 C8 1.506(3) . ?
C14 C15 1.381(3) . ?
C15 C16 1.386(3) . ?
C4 C5 1.386(4) . ?
C19 C20 1.390(3) . ?
C19 C18 1.391(3) . ?
C6 C5 1.372(3) . ?
C20 C21 1.385(3) . ?
C20 C23 1.513(3) . ?
C17 C18 1.388(3) . ?
C17 C22 1.402(3) . ?
C21 C22 1.384(3) . ?

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 C1 C6 119.4(2) . . ?
C2 C1 N1 118.68(18) . . ?
C6 C1 N1 121.9(2) . . ?
C3 C2 C1 118.96(19) . . ?
C3 C2 C9 119.18(19) . . ?
C1 C2 C9 121.85(19) . . ?
C4 C3 C2 121.5(2) . . ?
C7 N1 C1 128.55(18) . . ?
C13 C12 C11 122.74(19) . . ?
C13 C12 Br1 116.96(16) . . ?
C11 C12 Br1 120.24(15) . . ?
C10 C9 C17 120.92(18) . . ?
C10 C9 C2 122.48(18) . . ?
C17 C9 C2 116.52(17) . . ?
C9 C10 C11 126.83(18) . . ?
C12 C11 C16 116.66(18) . . ?
C12 C11 C10 121.20(18) . . ?
C16 C11 C10 122.13(19) . . ?
C12 C13 C14 119.1(2) . . ?
O1 C7 N1 123.3(2) . . ?
O1 C7 C8 121.9(2) . . ?
N1 C7 C8 114.79(19) . . ?
C15 C14 C13 119.9(2) . . ?
C14 C15 C16 120.4(2) . . ?
C5 C4 C3 118.8(2) . . ?
C20 C19 C18 121.2(2) . . ?
C5 C6 C1 120.2(2) . . ?
C21 C20 C19 117.72(19) . . ?
C21 C20 C23 121.00(19) . . ?
C19 C20 C23 121.29(19) . . ?
C6 C5 C4 121.1(2) . . ?
C15 C16 C11 121.2(2) . . ?
C18 C17 C22 117.84(18) . . ?
C18 C17 C9 121.19(18) . . ?
C22 C17 C9 120.90(18) . . ?
C17 C18 C19 120.90(19) . . ?
C22 C21 C20 121.61(19) . . ?
C21 C22 C17 120.59(19) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 2.4(3) . . . . ?
N1 C1 C2 C3 -176.34(18) . . . . ?
C6 C1 C2 C9 -178.80(18) . . . . ?
N1 C1 C2 C9 2.5(3) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
C9 C2 C3 C4 179.76(19) . . . . ?
C2 C1 N1 C7 160.8(2) . . . . ?
C6 C1 N1 C7 -17.9(3) . . . . ?
C3 C2 C9 C10 -118.6(2) . . . . ?
C1 C2 C9 C10 62.6(3) . . . . ?
C3 C2 C9 C17 64.8(2) . . . . ?
C1 C2 C9 C17 -114.0(2) . . . . ?
C17 C9 C10 C11 -178.57(19) . . . . ?
C2 C9 C10 C11 4.9(3) . . . . ?
C13 C12 C11 C16 -0.8(3) . . . . ?
Br1 C12 C11 C16 -177.76(15) . . . . ?
C13 C12 C11 C10 179.69(19) . . . . ?
Br1 C12 C11 C10 2.8(3) . . . . ?
C9 C10 C11 C12 -138.0(2) . . . . ?
C9 C10 C11 C16 42.6(3) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
Br1 C12 C13 C14 177.03(16) . . . . ?
C1 N1 C7 O1 4.2(3) . . . . ?
C1 N1 C7 C8 -173.91(19) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C13 C14 C15 C16 -1.0(3) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C2 C1 C6 C5 -2.0(3) . . . . ?
N1 C1 C6 C5 176.7(2) . . . . ?
C18 C19 C20 C21 2.2(3) . . . . ?
C18 C19 C20 C23 -178.2(2) . . . . ?
C1 C6 C5 C4 0.5(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C14 C15 C16 C11 0.1(3) . . . . ?
C12 C11 C16 C15 0.8(3) . . . . ?
C10 C11 C16 C15 -179.78(19) . . . . ?
C10 C9 C17 C18 -146.4(2) . . . . ?
C2 C9 C17 C18 30.3(3) . . . . ?
C10 C9 C17 C22 30.5(3) . . . . ?
C2 C9 C17 C22 -152.84(19) . . . . ?
C22 C17 C18 C19 -3.1(3) . . . . ?
C9 C17 C18 C19 173.92(19) . . . . ?
C20 C19 C18 C17 0.5(3) . . . . ?
C19 C20 C21 C22 -2.3(3) . . . . ?
C23 C20 C21 C22 178.1(2) . . . . ?
C20 C21 C22 C17 -0.3(3) . . . . ?
C18 C17 C22 C21 3.0(3) . . . . ?
C9 C17 C22 C21 -174.03(19) . . . . ?

_refine_diff_density_max         0.350
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.058


_symmetry_cell_setting           monoclinic
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  mirror
_chemical_absolute_configuration ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane'
####################################################################### 
# 
# 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. 
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#######################################################################

data_4-Me_a
_database_code_depnum_ccdc_archive 'CCDC 2150671'
loop_
_audit_author_name
_audit_author_address
'Kento Iwai'
;Kochi University of Technology
Japan
;
_audit_update_record             
;
2022-02-08 deposited with the CCDC.	2022-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
5-Ethanoyl-10-(4-methylphenyl)-5H-dibenzo[b,f]azepine
_chemical_name_common            ?
_chemical_melting_point          442.0-442.4
_chemical_formula_moiety         'C23 H19 N O'
_chemical_formula_sum            'C23 H19 N O'
_chemical_formula_weight         325.39

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.5398(5)
_cell_length_b                   8.6572(2)
_cell_length_c                   13.0504(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.779(3)
_cell_angle_gamma                90
_cell_volume                     1730.18(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)

_cell_measurement_reflns_used    7688

_cell_measurement_theta_min      2.6420

_cell_measurement_theta_max      30.1340


_exptl_crystal_description       block

_exptl_crystal_colour            colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211

_exptl_crystal_size_mid          0.121

_exptl_crystal_size_min          0.073

_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian

_exptl_absorpt_correction_T_min  0.802

_exptl_absorpt_correction_T_max  1.000

_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.47a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
   a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'

_diffrn_measurement_method       'ω scans'

_diffrn_detector_area_resol_mean 10.0000

_diffrn_reflns_number            11561
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.660
_diffrn_reflns_theta_max         25.488
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3219
_reflns_number_gt                2766
_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       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_structure_solution    ?

_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.0362P)²+0.7281P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3219
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0909
_refine_ls_wR_factor_gt          0.0867
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_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 0.90058(9) 0.27023(15) 0.79526(10) 0.0201(3) Uani 1 1 d . . . . .
H1 H 0.886833 0.255369 0.862783 0.024 Uiso 1 1 calc R U . . .
C2 C 0.97328(9) 0.19861(15) 0.76895(11) 0.0223(3) Uani 1 1 d . . . . .
H2 H 1.009097 0.135578 0.818431 0.027 Uiso 1 1 calc R U . . .
C3 C 0.99417(9) 0.21846(15) 0.67044(11) 0.0211(3) Uani 1 1 d . . . . .
H3 H 1.044369 0.169640 0.652667 0.025 Uiso 1 1 calc R U . . .
C4 C 0.94145(9) 0.30985(14) 0.59807(10) 0.0183(3) Uani 1 1 d . . . . .
H4 H 0.955724 0.324312 0.530767 0.022 Uiso 1 1 calc R U . . .
N1 N 0.80925(7) 0.46906(12) 0.54938(8) 0.0153(2) Uani 1 1 d . . . . .
C5 C 0.84570(9) 0.73410(15) 0.51040(10) 0.0179(3) Uani 1 1 d . . . . .
H5 H 0.870960 0.696441 0.453897 0.021 Uiso 1 1 calc R U . . .
C6 C 0.84687(9) 0.89090(15) 0.53184(10) 0.0199(3) Uani 1 1 d . . . . .
H6 H 0.872660 0.961099 0.489996 0.024 Uiso 1 1 calc R U . . .
C7 C 0.81009(9) 0.94485(15) 0.61496(10) 0.0208(3) Uani 1 1 d . . . . .
H7 H 0.810817 1.052235 0.630083 0.025 Uiso 1 1 calc R U . . .
C8 C 0.77248(9) 0.84266(15) 0.67562(10) 0.0192(3) Uani 1 1 d . . . . .
H8 H 0.747366 0.881432 0.731930 0.023 Uiso 1 1 calc R U . . .
C9 C 0.73325(8) 0.57439(14) 0.72559(9) 0.0153(3) Uani 1 1 d . . . . .
C10 C 0.76974(9) 0.43597(14) 0.75429(10) 0.0166(3) Uani 1 1 d . . . . .
H10 H 0.741521 0.377263 0.800408 0.020 Uiso 1 1 calc R U . . .
C11 C 0.86770(8) 0.38021(14) 0.62421(10) 0.0153(3) Uani 1 1 d . . . . .
C12 C 0.80740(8) 0.63150(14) 0.57179(10) 0.0153(3) Uani 1 1 d . . . . .
C13 C 0.77035(8) 0.68293(14) 0.65630(10) 0.0156(3) Uani 1 1 d . . . . .
C14 C 0.84673(8) 0.36452(14) 0.72391(10) 0.0161(3) Uani 1 1 d . . . . .
C15 C 0.74622(9) 0.39436(14) 0.48022(9) 0.0159(3) Uani 1 1 d . . . . .
O1 O 0.74861(6) 0.25397(10) 0.46932(7) 0.0213(2) Uani 1 1 d . . . . .
C16 C 0.67537(9) 0.49287(15) 0.42048(11) 0.0226(3) Uani 1 1 d . . . . .
H16 H 0.646263 0.435987 0.359382 0.034 Uiso 1 1 calc R U . . .
H16A H 0.700946 0.587925 0.398030 0.034 Uiso 1 1 calc R U . . .
H16B H 0.632689 0.518995 0.465041 0.034 Uiso 1 1 calc R U . . .
C17 C 0.65482(9) 0.62372(14) 0.76941(10) 0.0166(3) Uani 1 1 d . . . . .
C18 C 0.58821(9) 0.71134(15) 0.71068(10) 0.0205(3) Uani 1 1 d . . . . .
H18 H 0.594227 0.744498 0.642871 0.025 Uiso 1 1 calc R U . . .
C19 C 0.51364(10) 0.75036(16) 0.75007(11) 0.0243(3) Uani 1 1 d . . . . .
H19 H 0.469476 0.809829 0.708619 0.029 Uiso 1 1 calc R U . . .
C20 C 0.50208(9) 0.70424(15) 0.84911(11) 0.0229(3) Uani 1 1 d . . . . .
C21 C 0.56889(9) 0.61824(15) 0.90782(10) 0.0198(3) Uani 1 1 d . . . . .
H21 H 0.562966 0.586204 0.975902 0.024 Uiso 1 1 calc R U . . .
C22 C 0.64356(9) 0.57850(14) 0.86926(10) 0.0174(3) Uani 1 1 d . . . . .
H22 H 0.687775 0.519707 0.911154 0.021 Uiso 1 1 calc R U . . .
C23 C 0.42071(11) 0.7445(2) 0.89163(13) 0.0366(4) Uani 1 1 d . . . . .
H23 H 0.372998 0.676111 0.860852 0.055 Uiso 1 1 calc R U . . .
H23A H 0.404567 0.852002 0.874369 0.055 Uiso 1 1 calc R U . . .
H23B H 0.431583 0.731629 0.967332 0.055 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 C2 1.382(2) . ?
C1 C14 1.4031(18) . ?
C2 C3 1.389(2) . ?
C3 C4 1.3880(19) . ?
C4 C11 1.3906(18) . ?
N1 C15 1.3755(16) . ?
N1 C12 1.4377(16) . ?
N1 C11 1.4384(16) . ?
C5 C6 1.3854(19) . ?
C5 C12 1.3954(18) . ?
C6 C7 1.3901(19) . ?
C7 C8 1.3814(19) . ?
C8 C13 1.4050(18) . ?
C9 C10 1.3511(18) . ?
C9 C13 1.4867(17) . ?
C9 C17 1.4938(18) . ?
C10 C14 1.4603(18) . ?
C11 C14 1.4006(18) . ?
C12 C13 1.4006(18) . ?
C15 O1 1.2250(15) . ?
C15 C16 1.5018(18) . ?
C17 C22 1.3999(18) . ?
C17 C18 1.4017(18) . ?
C18 C19 1.387(2) . ?
C19 C20 1.393(2) . ?
C20 C21 1.3961(19) . ?
C20 C23 1.506(2) . ?
C21 C22 1.3843(19) . ?

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 C1 C14 121.10(12) . . ?
C1 C2 C3 120.25(13) . . ?
C4 C3 C2 119.78(13) . . ?
C3 C4 C11 119.90(12) . . ?
C15 N1 C12 123.83(11) . . ?
C15 N1 C11 119.42(10) . . ?
C12 N1 C11 114.65(10) . . ?
C6 C5 C12 120.00(12) . . ?
C5 C6 C7 119.59(12) . . ?
C8 C7 C6 120.13(12) . . ?
C7 C8 C13 121.80(13) . . ?
C10 C9 C13 122.77(12) . . ?
C10 C9 C17 118.60(11) . . ?
C13 C9 C17 118.56(11) . . ?
C9 C10 C14 128.69(12) . . ?
C4 C11 C14 121.12(12) . . ?
C4 C11 N1 121.29(11) . . ?
C14 C11 N1 117.58(11) . . ?
C5 C12 C13 121.48(11) . . ?
C5 C12 N1 118.73(11) . . ?
C13 C12 N1 119.75(11) . . ?
C12 C13 C8 116.99(12) . . ?
C12 C13 C9 122.13(11) . . ?
C8 C13 C9 120.84(12) . . ?
C11 C14 C1 117.80(12) . . ?
C11 C14 C10 122.80(12) . . ?
C1 C14 C10 119.34(12) . . ?
O1 C15 N1 120.69(12) . . ?
O1 C15 C16 122.49(12) . . ?
N1 C15 C16 116.82(11) . . ?
C22 C17 C18 117.57(12) . . ?
C22 C17 C9 121.03(12) . . ?
C18 C17 C9 121.35(12) . . ?
C19 C18 C17 121.01(13) . . ?
C18 C19 C20 121.43(13) . . ?
C19 C20 C21 117.46(13) . . ?
C19 C20 C23 121.61(13) . . ?
C21 C20 C23 120.93(13) . . ?
C22 C21 C20 121.61(12) . . ?
C21 C22 C17 120.93(12) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C1 C2 C3 -0.3(2) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C2 C3 C4 C11 -0.44(19) . . . . ?
C12 C5 C6 C7 0.3(2) . . . . ?
C5 C6 C7 C8 -0.1(2) . . . . ?
C6 C7 C8 C13 0.3(2) . . . . ?
C13 C9 C10 C14 -1.8(2) . . . . ?
C17 C9 C10 C14 -178.73(12) . . . . ?
C3 C4 C11 C14 1.97(19) . . . . ?
C3 C4 C11 N1 -176.75(11) . . . . ?
C15 N1 C11 C4 82.48(15) . . . . ?
C12 N1 C11 C4 -113.33(13) . . . . ?
C15 N1 C11 C14 -96.29(14) . . . . ?
C12 N1 C11 C14 67.90(15) . . . . ?
C6 C5 C12 C13 -0.7(2) . . . . ?
C6 C5 C12 N1 -178.35(12) . . . . ?
C15 N1 C12 C5 -88.47(16) . . . . ?
C11 N1 C12 C5 108.13(13) . . . . ?
C15 N1 C12 C13 93.80(15) . . . . ?
C11 N1 C12 C13 -69.60(15) . . . . ?
C5 C12 C13 C8 0.81(19) . . . . ?
N1 C12 C13 C8 178.48(11) . . . . ?
C5 C12 C13 C9 -176.91(12) . . . . ?
N1 C12 C13 C9 0.76(19) . . . . ?
C7 C8 C13 C12 -0.64(19) . . . . ?
C7 C8 C13 C9 177.11(12) . . . . ?
C10 C9 C13 C12 38.04(19) . . . . ?
C17 C9 C13 C12 -144.99(12) . . . . ?
C10 C9 C13 C8 -139.59(13) . . . . ?
C17 C9 C13 C8 37.37(17) . . . . ?
C4 C11 C14 C1 -2.59(18) . . . . ?
N1 C11 C14 C1 176.18(11) . . . . ?
C4 C11 C14 C10 -179.73(12) . . . . ?
N1 C11 C14 C10 -0.96(18) . . . . ?
C2 C1 C14 C11 1.75(19) . . . . ?
C2 C1 C14 C10 178.99(12) . . . . ?
C9 C10 C14 C11 -36.2(2) . . . . ?
C9 C10 C14 C1 146.66(14) . . . . ?
C12 N1 C15 O1 -175.39(12) . . . . ?
C11 N1 C15 O1 -12.74(18) . . . . ?
C12 N1 C15 C16 4.25(18) . . . . ?
C11 N1 C15 C16 166.91(11) . . . . ?
C10 C9 C17 C22 31.72(18) . . . . ?
C13 C9 C17 C22 -145.37(12) . . . . ?
C10 C9 C17 C18 -145.59(13) . . . . ?
C13 C9 C17 C18 37.32(17) . . . . ?
C22 C17 C18 C19 -0.55(19) . . . . ?
C9 C17 C18 C19 176.85(12) . . . . ?
C17 C18 C19 C20 0.0(2) . . . . ?
C18 C19 C20 C21 0.6(2) . . . . ?
C18 C19 C20 C23 -179.16(14) . . . . ?
C19 C20 C21 C22 -0.6(2) . . . . ?
C23 C20 C21 C22 179.10(13) . . . . ?
C20 C21 C22 C17 0.1(2) . . . . ?
C18 C17 C22 C21 0.48(19) . . . . ?
C9 C17 C22 C21 -176.93(11) . . . . ?

_refine_diff_density_max         0.189
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.040


_symmetry_cell_setting           monoclinic
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  mirror
_chemical_absolute_configuration ?
