# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_200916_ljm_3_61_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2243493'
loop_
_audit_author_name
_audit_author_address
'Jiaming Li'
;Zhejiang University
China
;
_audit_update_record             
;
2023-02-21 deposited with the CCDC.	2024-03-04 downloaded from the CCDC.
;
_audit_creation_date             2020-09-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H17 Cl N2 O'
_chemical_formula_sum            'C14 H17 Cl N2 O'
_chemical_formula_weight         264.74
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.9523(2)
_cell_length_b                   9.0139(4)
_cell_length_c                   14.5673(7)
_cell_angle_alpha                100.404(2)
_cell_angle_beta                 92.408(2)
_cell_angle_gamma                94.706(2)
_cell_volume                     636.36(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4929
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.12
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.874
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7025
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1206 before and 0.0609 after correction.
The Ratio of minimum to maximum transmission is 0.9423.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8009
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.124
_diffrn_reflns_theta_min         2.307
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2592
_reflns_number_total             2817
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'Bruker Instrument Service vV6.2.10'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2817
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0433P)²+0.2061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0900
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C10(H10a,H10b), C11(H11a,H11b), C12(H12a,H12b), C13(H13a,H13b)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Cl01 Cl 0.13836(8) 0.69011(4) 0.57856(3) 0.04221(13) Uani 1 1 d . . . . .
O1 O 0.2754(2) 0.52154(10) 0.91819(6) 0.0307(2) Uani 1 1 d . . . . .
N1 N 0.2999(2) 0.27092(11) 0.83414(7) 0.0231(2) Uani 1 1 d . . . . .
N2 N 0.1027(2) 0.54695(11) 0.76277(7) 0.0236(2) Uani 1 1 d . . . . .
C1 C 0.6103(3) 0.10674(14) 0.90451(9) 0.0301(3) Uani 1 1 d . . . . .
H1 H 0.584489 0.146553 0.968175 0.036 Uiso 1 1 calc R . . . .
C2 C 0.7816(3) -0.00670(15) 0.87959(10) 0.0334(3) Uani 1 1 d . . . . .
H2 H 0.873994 -0.045375 0.927374 0.040 Uiso 1 1 calc R . . . .
C3 C 0.8217(3) -0.06569(14) 0.78569(10) 0.0311(3) Uani 1 1 d . . . . .
H3 H 0.943933 -0.141309 0.771065 0.037 Uiso 1 1 calc R . . . .
C4 C 0.6855(3) -0.01504(13) 0.71435(9) 0.0264(3) Uani 1 1 d . . . . .
H4 H 0.711794 -0.055939 0.650878 0.032 Uiso 1 1 calc R . . . .
C5 C 0.5079(2) 0.09772(12) 0.73704(8) 0.0216(2) Uani 1 1 d . . . . .
C6 C 0.4777(2) 0.15974(12) 0.83199(8) 0.0228(2) Uani 1 1 d . . . . .
C7 C 0.2140(2) 0.27666(12) 0.74258(8) 0.0208(2) Uani 1 1 d . . . . .
C8 C 0.3385(2) 0.17363(12) 0.68174(8) 0.0219(2) Uani 1 1 d . . . . .
C9 C 0.2107(3) 0.36523(14) 0.91659(8) 0.0276(3) Uani 1 1 d . . . . .
H9A H 0.011768 0.345226 0.918879 0.033 Uiso 1 1 calc R . . . .
H9B H 0.296828 0.337555 0.972947 0.033 Uiso 1 1 calc R . . . .
C10 C 0.0846(3) 0.58574(15) 0.86199(9) 0.0309(3) Uani 1 1 d . . . . .
H10A H -0.101312 0.553123 0.877266 0.037 Uiso 1 1 calc R . . . .
H10B H 0.110634 0.697414 0.880379 0.037 Uiso 1 1 calc R . . . .
C11 C 0.0159(2) 0.38677(13) 0.72486(8) 0.0224(2) Uani 1 1 d . . . . .
H11A H -0.020615 0.375269 0.656481 0.027 Uiso 1 1 calc R . . . .
H11B H -0.157085 0.359495 0.752019 0.027 Uiso 1 1 calc R . . . .
C12 C 0.3650(3) 0.60067(15) 0.73261(10) 0.0307(3) Uani 1 1 d . . . . .
H12A H 0.506770 0.543391 0.756142 0.037 Uiso 1 1 calc R . . . .
H12B H 0.406665 0.708637 0.761707 0.037 Uiso 1 1 calc R . . . .
C13 C 0.3802(3) 0.58555(16) 0.62856(11) 0.0361(3) Uani 1 1 d . . . . .
H13A H 0.347504 0.477218 0.599205 0.043 Uiso 1 1 calc R . . . .
H13B H 0.565189 0.622081 0.614513 0.043 Uiso 1 1 calc R . . . .
C14 C 0.3048(3) 0.14034(15) 0.57722(9) 0.0322(3) Uani 1 1 d . . . . .
H14A H 0.159814 0.196708 0.556613 0.048 Uiso 1 1 calc GR . . . .
H14B H 0.257351 0.031537 0.555634 0.048 Uiso 1 1 calc GR . . . .
H14C H 0.475053 0.170969 0.550987 0.048 Uiso 1 1 calc GR . . . .


_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
Cl01 C13 1.7926(15) . ?
O1 C9 1.4149(15) . ?
O1 C10 1.4471(15) . ?
N1 C6 1.3844(15) . ?
N1 C7 1.3942(14) . ?
N1 C9 1.4485(15) . ?
N2 C10 1.4327(16) . ?
N2 C11 1.4712(14) . ?
N2 C12 1.4620(16) . ?
C1 H1 0.9500 . ?
C1 C2 1.3896(19) . ?
C1 C6 1.3968(17) . ?
C2 H2 0.9500 . ?
C2 C3 1.404(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.3807(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.4023(16) . ?
C5 C6 1.4141(16) . ?
C5 C8 1.4342(16) . ?
C7 C8 1.3678(16) . ?
C7 C11 1.4982(16) . ?
C8 C14 1.4973(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.503(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
C9 O1 C10 113.16(10) . . ?
C6 N1 C7 108.61(9) . . ?
C6 N1 C9 126.73(10) . . ?
C7 N1 C9 124.65(10) . . ?
C10 N2 C11 113.11(10) . . ?
C10 N2 C12 112.30(10) . . ?
C12 N2 C11 114.37(10) . . ?
C2 C1 H1 121.4 . . ?
C2 C1 C6 117.17(12) . . ?
C6 C1 H1 121.4 . . ?
C1 C2 H2 119.1 . . ?
C1 C2 C3 121.76(12) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.75(12) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 118.96(12) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 C6 119.46(11) . . ?
C4 C5 C8 133.15(11) . . ?
C6 C5 C8 107.37(10) . . ?
N1 C6 C1 130.76(11) . . ?
N1 C6 C5 107.40(10) . . ?
C1 C6 C5 121.82(11) . . ?
N1 C7 C11 119.67(10) . . ?
C8 C7 N1 109.60(10) . . ?
C8 C7 C11 130.73(11) . . ?
C5 C8 C14 125.11(10) . . ?
C7 C8 C5 107.00(10) . . ?
C7 C8 C14 127.88(11) . . ?
O1 C9 N1 112.61(10) . . ?
O1 C9 H9A 109.1 . . ?
O1 C9 H9B 109.1 . . ?
N1 C9 H9A 109.1 . . ?
N1 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
O1 C10 H10A 108.3 . . ?
O1 C10 H10B 108.3 . . ?
N2 C10 O1 116.04(10) . . ?
N2 C10 H10A 108.3 . . ?
N2 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
N2 C11 C7 115.42(9) . . ?
N2 C11 H11A 108.4 . . ?
N2 C11 H11B 108.4 . . ?
C7 C11 H11A 108.4 . . ?
C7 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
N2 C12 H12A 108.6 . . ?
N2 C12 H12B 108.6 . . ?
N2 C12 C13 114.62(11) . . ?
H12A C12 H12B 107.6 . . ?
C13 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
Cl01 C13 H13A 109.1 . . ?
Cl01 C13 H13B 109.1 . . ?
C12 C13 Cl01 112.54(10) . . ?
C12 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C8 C14 H14A 109.5 . . ?
C8 C14 H14B 109.5 . . ?
C8 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_230307_ljm_8_3_3_0m
_database_code_depnum_ccdc_archive 'CCDC 2249556'
loop_
_audit_author_name
_audit_author_address
'Jiaming Li'
;Zhejiang University
China
;
_audit_update_record             
;
2023-03-17 deposited with the CCDC.	2024-03-04 downloaded from the CCDC.
;
_audit_creation_date             2023-03-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H17 Cl N2 S'
_chemical_formula_sum            'C14 H17 Cl N2 S'
_chemical_formula_weight         280.80
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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'
Cl Cl 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0074(4)
_cell_length_b                   9.0205(7)
_cell_length_c                   15.1568(13)
_cell_angle_alpha                80.365(3)
_cell_angle_beta                 89.851(3)
_cell_angle_gamma                84.042(3)
_cell_volume                     671.24(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5035
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.576
_cell_measurement_theta_min      2.573
_shelx_estimated_absorpt_T_max   0.928
_shelx_estimated_absorpt_T_min   0.632
_exptl_absorpt_coefficient_mu    2.528
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0676 before and 0.0576 after correction.
The Ratio of minimum to maximum transmission is 0.8985.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11083
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.576
_diffrn_reflns_theta_min         2.573
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.24957869999999996
_diffrn_source_voltage           69.91
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2657
_reflns_number_total             3025
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3025
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      1.140
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0634P)²+0.2526P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1273
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Cl1 Cl 0.87832(12) 0.69011(7) 0.42754(4) 0.04258(19) Uani 1 1 d . . . . .
S1 S 0.69366(9) 0.53684(5) 0.08020(3) 0.02607(16) Uani 1 1 d . . . . .
N1 N 0.7393(3) 0.24864(17) 0.17352(10) 0.0223(3) Uani 1 1 d . . . . .
N2 N 0.9064(3) 0.53699(17) 0.25215(10) 0.0218(3) Uani 1 1 d . . . . .
C1 C 0.3387(4) -0.0215(2) 0.29285(14) 0.0271(4) Uani 1 1 d . . . . .
H1 H 0.305539 -0.058099 0.353952 0.033 Uiso 1 1 calc R U . . .
C2 C 0.2100(4) -0.0746(2) 0.22579(15) 0.0325(5) Uani 1 1 d . . . . .
H2 H 0.087335 -0.148055 0.241118 0.039 Uiso 1 1 calc R U . . .
C3 C 0.2579(4) -0.0217(2) 0.13566(15) 0.0337(5) Uani 1 1 d . . . . .
H3 H 0.168179 -0.061160 0.090980 0.040 Uiso 1 1 calc R U . . .
C4 C 0.4324(4) 0.0867(2) 0.10962(14) 0.0290(4) Uani 1 1 d . . . . .
H4 H 0.464196 0.122228 0.048289 0.035 Uiso 1 1 calc R U . . .
C5 C 0.5598(4) 0.1412(2) 0.17800(12) 0.0224(4) Uani 1 1 d . . . . .
C6 C 0.5187(4) 0.0873(2) 0.26956(12) 0.0219(4) Uani 1 1 d . . . . .
C7 C 0.6781(4) 0.1666(2) 0.32049(12) 0.0220(4) Uani 1 1 d . . . . .
C8 C 0.8082(3) 0.2645(2) 0.26048(12) 0.0205(4) Uani 1 1 d . . . . .
C9 C 0.8258(4) 0.3391(2) 0.09323(12) 0.0253(4) Uani 1 1 d . . . . .
H9A H 0.768804 0.297062 0.040852 0.030 Uiso 1 1 calc R U . . .
H9B H 1.024418 0.332052 0.093811 0.030 Uiso 1 1 calc R U . . .
C10 C 0.9258(4) 0.5966(2) 0.15880(13) 0.0273(4) Uani 1 1 d . . . . .
H10A H 1.111531 0.569108 0.140199 0.033 Uiso 1 1 calc R U . . .
H10B H 0.898503 0.708282 0.151717 0.033 Uiso 1 1 calc R U . . .
C11 C 1.0002(4) 0.3749(2) 0.27672(12) 0.0230(4) Uani 1 1 d . . . . .
H11A H 1.049477 0.354625 0.341142 0.028 Uiso 1 1 calc R U . . .
H11B H 1.165951 0.354178 0.243176 0.028 Uiso 1 1 calc R U . . .
C12 C 0.7004(5) 0.1392(2) 0.42024(13) 0.0335(5) Uani 1 1 d . . . . .
H12A H 0.847866 0.191112 0.438776 0.050 Uiso 1 1 calc R U . . .
H12B H 0.736118 0.030389 0.442156 0.050 Uiso 1 1 calc R U . . .
H12C H 0.531874 0.178085 0.445263 0.050 Uiso 1 1 calc R U . . .
C13 C 0.6495(4) 0.5837(2) 0.28994(13) 0.0272(4) Uani 1 1 d . . . . .
H13A H 0.513375 0.521224 0.272761 0.033 Uiso 1 1 calc R U . . .
H13B H 0.592725 0.690185 0.263263 0.033 Uiso 1 1 calc R U . . .
C14 C 0.6538(4) 0.5707(3) 0.38999(15) 0.0337(5) Uani 1 1 d . . . . .
H14A H 0.709321 0.464321 0.417175 0.040 Uiso 1 1 calc R U . . .
H14B H 0.470245 0.598232 0.410523 0.040 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
Cl1 C14 1.792(2) . ?
S1 C9 1.815(2) . ?
S1 C10 1.848(2) . ?
N1 C5 1.382(2) . ?
N1 C8 1.397(2) . ?
N1 C9 1.440(2) . ?
N2 C10 1.434(2) . ?
N2 C11 1.474(2) . ?
N2 C13 1.458(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.382(3) . ?
C1 C6 1.402(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.398(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.401(3) . ?
C5 C6 1.414(2) . ?
C6 C7 1.432(3) . ?
C7 C8 1.371(2) . ?
C7 C12 1.493(3) . ?
C8 C11 1.502(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.501(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 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
C9 S1 C10 98.07(9) . . ?
C5 N1 C8 108.82(15) . . ?
C5 N1 C9 126.12(15) . . ?
C8 N1 C9 124.88(15) . . ?
C10 N2 C11 114.54(15) . . ?
C10 N2 C13 113.08(15) . . ?
C13 N2 C11 114.93(14) . . ?
C2 C1 H1 120.4 . . ?
C2 C1 C6 119.13(19) . . ?
C6 C1 H1 120.4 . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.88(18) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 121.90(19) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 121.6 . . ?
C3 C4 C5 116.88(19) . . ?
C5 C4 H4 121.6 . . ?
N1 C5 C4 130.40(17) . . ?
N1 C5 C6 107.36(15) . . ?
C4 C5 C6 122.24(17) . . ?
C1 C6 C5 118.95(17) . . ?
C1 C6 C7 133.51(18) . . ?
C5 C6 C7 107.51(15) . . ?
C6 C7 C12 124.77(16) . . ?
C8 C7 C6 107.06(16) . . ?
C8 C7 C12 128.13(17) . . ?
N1 C8 C11 120.89(15) . . ?
C7 C8 N1 109.24(16) . . ?
C7 C8 C11 129.86(16) . . ?
S1 C9 H9A 108.9 . . ?
S1 C9 H9B 108.9 . . ?
N1 C9 S1 113.57(13) . . ?
N1 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
S1 C10 H10A 107.8 . . ?
S1 C10 H10B 107.8 . . ?
N2 C10 S1 117.83(12) . . ?
N2 C10 H10A 107.8 . . ?
N2 C10 H10B 107.8 . . ?
H10A C10 H10B 107.2 . . ?
N2 C11 C8 117.04(15) . . ?
N2 C11 H11A 108.0 . . ?
N2 C11 H11B 108.0 . . ?
C8 C11 H11A 108.0 . . ?
C8 C11 H11B 108.0 . . ?
H11A C11 H11B 107.3 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 108.7 . . ?
N2 C13 H13B 108.7 . . ?
N2 C13 C14 114.24(16) . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
Cl1 C14 H14A 109.2 . . ?
Cl1 C14 H14B 109.2 . . ?
C13 C14 Cl1 112.18(14) . . ?
C13 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C5 C6 C1 178.60(16) . . . . ?
N1 C5 C6 C7 0.5(2) . . . . ?
N1 C8 C11 N2 68.9(2) . . . . ?
N2 C13 C14 Cl1 62.4(2) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C1 C6 C7 C8 -177.6(2) . . . . ?
C1 C6 C7 C12 4.7(3) . . . . ?
C2 C1 C6 C5 1.1(3) . . . . ?
C2 C1 C6 C7 178.63(19) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 N1 -179.29(19) . . . . ?
C3 C4 C5 C6 1.3(3) . . . . ?
C4 C5 C6 C1 -1.9(3) . . . . ?
C4 C5 C6 C7 180.00(17) . . . . ?
C5 N1 C8 C7 1.0(2) . . . . ?
C5 N1 C8 C11 -179.60(15) . . . . ?
C5 N1 C9 S1 108.93(18) . . . . ?
C5 C6 C7 C8 0.1(2) . . . . ?
C5 C6 C7 C12 -177.59(18) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
C6 C7 C8 N1 -0.7(2) . . . . ?
C6 C7 C8 C11 179.98(17) . . . . ?
C7 C8 C11 N2 -111.8(2) . . . . ?
C8 N1 C5 C4 179.64(19) . . . . ?
C8 N1 C5 C6 -0.9(2) . . . . ?
C8 N1 C9 S1 -65.6(2) . . . . ?
C9 S1 C10 N2 -67.06(16) . . . . ?
C9 N1 C5 C4 4.4(3) . . . . ?
C9 N1 C5 C6 -176.15(17) . . . . ?
C9 N1 C8 C7 176.33(17) . . . . ?
C9 N1 C8 C11 -4.3(3) . . . . ?
C10 S1 C9 N1 78.48(15) . . . . ?
C10 N2 C11 C8 -80.78(19) . . . . ?
C10 N2 C13 C14 -159.90(16) . . . . ?
C11 N2 C10 S1 70.47(19) . . . . ?
C11 N2 C13 C14 66.0(2) . . . . ?
C12 C7 C8 N1 176.94(18) . . . . ?
C12 C7 C8 C11 -2.4(3) . . . . ?
C13 N2 C10 S1 -63.83(19) . . . . ?
C13 N2 C11 C8 52.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_210125_ljm_4_60_1_0ma
_database_code_depnum_ccdc_archive 'CCDC 2243505'
loop_
_audit_author_name
_audit_author_address
'Jiaming Li'
;Zhejiang University
China
;
_audit_update_record             
;
2023-02-21 deposited with the CCDC.	2024-03-04 downloaded from the CCDC.
;
_audit_creation_date             2021-01-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H15 Br Cl N2 O'
_chemical_formula_sum            'C14 H15 Br Cl N2 O'
_chemical_formula_weight         342.64
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.4362(6)
_cell_length_b                   11.6969(6)
_cell_length_c                   10.4292(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.360(2)
_cell_angle_gamma                90
_cell_volume                     1386.51(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      25.33
_cell_measurement_theta_min      2.50
_shelx_estimated_absorpt_T_max   0.586
_shelx_estimated_absorpt_T_min   0.381
_exptl_absorpt_coefficient_mu    3.150
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1179 before and 0.0573 after correction.
The Ratio of minimum to maximum transmission is 0.7695.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            28315
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.341
_diffrn_reflns_theta_min         2.499
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2354
_reflns_number_total             2541
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.821
_refine_diff_density_min         -0.647
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2541
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0281
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0264P)²+1.9143P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0722
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C9(H9)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br1 Br 0.29463(2) 0.49839(2) 0.89369(3) 0.03999(11) Uani 1 1 d . . . . .
Cl1 Cl 1.09073(5) 0.21507(5) 0.48603(6) 0.03616(16) Uani 1 1 d . . . . .
O1 O 0.86517(14) 0.49067(13) 0.78717(16) 0.0295(4) Uani 1 1 d . . . . .
N1 N 0.68340(16) 0.48063(15) 0.65329(18) 0.0230(4) Uani 1 1 d . . . . .
N2 N 0.92904(16) 0.39648(16) 0.59737(18) 0.0262(4) Uani 1 1 d . . . . .
C1 C 0.4143(2) 0.32561(19) 0.5867(2) 0.0288(5) Uani 1 1 d . . . . .
H1 H 0.384212 0.269970 0.525374 0.035 Uiso 1 1 calc R . . . .
C2 C 0.3465(2) 0.3632(2) 0.6794(2) 0.0304(5) Uani 1 1 d . . . . .
H2 H 0.269609 0.333462 0.682754 0.036 Uiso 1 1 calc R . . . .
C3 C 0.39204(19) 0.4457(2) 0.7688(2) 0.0278(5) Uani 1 1 d . . . . .
C4 C 0.5034(2) 0.49152(18) 0.7710(2) 0.0244(5) Uani 1 1 d . . . . .
H4 H 0.532319 0.547145 0.832870 0.029 Uiso 1 1 calc R . . . .
C5 C 0.57075(18) 0.45164(18) 0.6774(2) 0.0226(4) Uani 1 1 d . . . . .
C6 C 0.52814(19) 0.36987(18) 0.5832(2) 0.0244(5) Uani 1 1 d . . . . .
C7 C 0.6193(2) 0.34969(18) 0.5019(2) 0.0255(5) Uani 1 1 d . . . . .
C8 C 0.71159(19) 0.41869(18) 0.5463(2) 0.0239(4) Uani 1 1 d . . . . .
C9 C 0.76570(19) 0.55245(19) 0.7322(2) 0.0266(5) Uani 1 1 d . . . . .
H9 H 0.754208 0.631820 0.745538 0.032 Uiso 1 1 calc R . . . .
C10 C 0.9541(2) 0.4770(2) 0.6995(2) 0.0307(5) Uani 1 1 d . . . . .
H10A H 0.967780 0.552435 0.660841 0.037 Uiso 1 1 calc R . . . .
H10B H 1.028509 0.453885 0.750639 0.037 Uiso 1 1 calc R . . . .
C11 C 0.8307(2) 0.43116(19) 0.5019(2) 0.0266(5) Uani 1 1 d . . . . .
H11A H 0.833495 0.384756 0.422879 0.032 Uiso 1 1 calc R . . . .
H11B H 0.842059 0.512111 0.478433 0.032 Uiso 1 1 calc R . . . .
C12 C 0.6124(2) 0.2682(2) 0.3904(2) 0.0338(5) Uani 1 1 d . . . . .
H12A H 0.679342 0.280883 0.341101 0.051 Uiso 1 1 calc GR . . . .
H12B H 0.538869 0.280910 0.334512 0.051 Uiso 1 1 calc GR . . . .
H12C H 0.614382 0.189475 0.422788 0.051 Uiso 1 1 calc GR . . . .
C13 C 0.9233(2) 0.27783(19) 0.6402(2) 0.0285(5) Uani 1 1 d . . . . .
H13A H 0.844025 0.262803 0.666144 0.034 Uiso 1 1 calc R . . . .
H13B H 0.981205 0.266438 0.716913 0.034 Uiso 1 1 calc R . . . .
C14 C 0.9478(2) 0.1930(2) 0.5371(2) 0.0302(5) Uani 1 1 d . . . . .
H14A H 0.887351 0.200956 0.462063 0.036 Uiso 1 1 calc R . . . .
H14B H 0.942853 0.114365 0.571263 0.036 Uiso 1 1 calc R . . . .


_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
Br1 C3 1.907(2) . ?
Cl1 C14 1.793(2) . ?
O1 C9 1.414(3) . ?
O1 C10 1.450(3) . ?
N1 C5 1.382(3) . ?
N1 C8 1.398(3) . ?
N1 C9 1.448(3) . ?
N2 C10 1.427(3) . ?
N2 C11 1.474(3) . ?
N2 C13 1.462(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.376(4) . ?
C1 C6 1.405(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.402(3) . ?
C3 C4 1.379(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(3) . ?
C5 C6 1.419(3) . ?
C6 C7 1.435(3) . ?
C7 C8 1.368(3) . ?
C7 C12 1.499(3) . ?
C8 C11 1.494(3) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.512(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 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
C9 O1 C10 112.96(18) . . ?
C5 N1 C8 108.68(18) . . ?
C5 N1 C9 126.80(19) . . ?
C8 N1 C9 124.16(19) . . ?
C10 N2 C11 113.47(18) . . ?
C10 N2 C13 114.25(19) . . ?
C13 N2 C11 114.25(18) . . ?
C2 C1 H1 120.1 . . ?
C2 C1 C6 119.8(2) . . ?
C6 C1 H1 120.1 . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.4(2) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 Br1 118.33(17) . . ?
C4 C3 Br1 118.14(18) . . ?
C4 C3 C2 123.5(2) . . ?
C3 C4 H4 121.9 . . ?
C3 C4 C5 116.2(2) . . ?
C5 C4 H4 121.9 . . ?
N1 C5 C4 130.3(2) . . ?
N1 C5 C6 107.16(19) . . ?
C4 C5 C6 122.6(2) . . ?
C1 C6 C5 118.6(2) . . ?
C1 C6 C7 133.7(2) . . ?
C5 C6 C7 107.69(19) . . ?
C6 C7 C12 125.7(2) . . ?
C8 C7 C6 106.67(19) . . ?
C8 C7 C12 127.6(2) . . ?
N1 C8 C11 119.73(19) . . ?
C7 C8 N1 109.8(2) . . ?
C7 C8 C11 130.4(2) . . ?
O1 C9 N1 112.14(18) . . ?
O1 C9 H9 123.9 . . ?
N1 C9 H9 123.9 . . ?
O1 C10 H10A 108.2 . . ?
O1 C10 H10B 108.2 . . ?
N2 C10 O1 116.51(19) . . ?
N2 C10 H10A 108.2 . . ?
N2 C10 H10B 108.2 . . ?
H10A C10 H10B 107.3 . . ?
N2 C11 C8 114.66(18) . . ?
N2 C11 H11A 108.6 . . ?
N2 C11 H11B 108.6 . . ?
C8 C11 H11A 108.6 . . ?
C8 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 109.0 . . ?
N2 C13 H13B 109.0 . . ?
N2 C13 C14 112.84(19) . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
Cl1 C14 H14A 109.4 . . ?
Cl1 C14 H14B 109.4 . . ?
C13 C14 Cl1 111.35(16) . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_210125_ljm_4_51_3_0m
_database_code_depnum_ccdc_archive 'CCDC 2243494'
loop_
_audit_author_name
_audit_author_address
'Jiaming Li'
;Zhejiang University
China
;
_audit_update_record             
;
2023-02-21 deposited with the CCDC.	2024-03-04 downloaded from the CCDC.
;
_audit_creation_date             2021-01-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H22 N2 O'
_chemical_formula_sum            'C20 H22 N2 O'
_chemical_formula_weight         306.39
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.3944(8)
_cell_length_b                   9.3978(8)
_cell_length_c                   20.419(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1610.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9013
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      68.29
_cell_measurement_theta_min      4.33
_shelx_estimated_absorpt_T_max   0.838
_shelx_estimated_absorpt_T_min   0.770
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1302 before and 0.0369 after correction.
The Ratio of minimum to maximum transmission is 0.8723.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18171
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.177
_diffrn_reflns_theta_min         4.330
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2940
_reflns_number_total             2945
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.133
_refine_ls_abs_structure_details 
;
 Flack x determined using 1218 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2945
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0431
_refine_ls_restrained_S_all      1.187
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0714P)²+0.1584P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1052
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O1 O 0.99426(16) 0.52338(16) 0.61286(7) 0.0335(4) Uani 1 1 d . . . . .
N1 N 0.76637(19) 0.42796(17) 0.55807(8) 0.0266(4) Uani 1 1 d . . . . .
N2 N 0.89709(19) 0.34708(17) 0.69125(7) 0.0272(4) Uani 1 1 d . . . . .
C1 C 0.3606(3) 0.4346(2) 0.50534(9) 0.0326(4) Uani 1 1 d . . . . .
H1 H 0.267267 0.381253 0.514757 0.039 Uiso 1 1 calc R . . . .
C2 C 0.3549(3) 0.5469(3) 0.46188(10) 0.0412(5) Uani 1 1 d . . . . .
H2 H 0.256743 0.571660 0.441725 0.049 Uiso 1 1 calc R . . . .
C3 C 0.4930(3) 0.6249(2) 0.44722(10) 0.0423(5) Uani 1 1 d . . . . .
H3 H 0.486320 0.701551 0.417026 0.051 Uiso 1 1 calc R . . . .
C4 C 0.6388(3) 0.5932(2) 0.47553(9) 0.0364(5) Uani 1 1 d . . . . .
H4 H 0.732015 0.645825 0.465011 0.044 Uiso 1 1 calc R . . . .
C5 C 0.6430(2) 0.4807(2) 0.52016(8) 0.0262(4) Uani 1 1 d . . . . .
C6 C 0.5058(2) 0.4001(2) 0.53549(8) 0.0251(4) Uani 1 1 d . . . . .
C7 C 0.5500(2) 0.29746(19) 0.58405(9) 0.0252(4) Uani 1 1 d . . . . .
C8 C 0.7079(2) 0.31752(18) 0.59680(8) 0.0235(4) Uani 1 1 d . . . . .
C9 C 0.9329(2) 0.4676(2) 0.55372(10) 0.0327(4) Uani 1 1 d . . . . .
H9A H 0.995953 0.382874 0.541181 0.039 Uiso 1 1 calc R . . . .
H9B H 0.945696 0.539587 0.518701 0.039 Uiso 1 1 calc R . . . .
C10 C 1.0308(2) 0.4146(2) 0.66058(10) 0.0336(5) Uani 1 1 d . . . . .
H10A H 1.095465 0.340266 0.638813 0.040 Uiso 1 1 calc R . . . .
H10B H 1.097713 0.457701 0.695230 0.040 Uiso 1 1 calc R . . . .
C11 C 0.8137(2) 0.24838(19) 0.64690(9) 0.0275(4) Uani 1 1 d . . . . .
H11A H 0.748160 0.182840 0.673652 0.033 Uiso 1 1 calc R . . . .
H11B H 0.894242 0.190288 0.623696 0.033 Uiso 1 1 calc R . . . .
C12 C 0.4394(3) 0.1930(2) 0.61555(10) 0.0360(5) Uani 1 1 d . . . . .
H12A H 0.501431 0.116146 0.635631 0.054 Uiso 1 1 calc GR . . . .
H12B H 0.367917 0.153094 0.582334 0.054 Uiso 1 1 calc GR . . . .
H12C H 0.376408 0.241223 0.649305 0.054 Uiso 1 1 calc GR . . . .
C13 C 0.7880(2) 0.44505(19) 0.72570(9) 0.0269(4) Uani 1 1 d . . . . .
H13 H 0.728605 0.501875 0.692262 0.032 Uiso 1 1 calc R . . . .
C14 C 0.8795(3) 0.5473(2) 0.76969(12) 0.0435(5) Uani 1 1 d . . . . .
H14A H 0.951994 0.493358 0.797926 0.065 Uiso 1 1 calc GR . . . .
H14B H 0.804221 0.600923 0.796866 0.065 Uiso 1 1 calc GR . . . .
H14C H 0.941017 0.613546 0.742587 0.065 Uiso 1 1 calc GR . . . .
C15 C 0.6681(2) 0.36410(19) 0.76711(8) 0.0259(4) Uani 1 1 d . . . . .
C16 C 0.7177(3) 0.2644(2) 0.81339(10) 0.0346(5) Uani 1 1 d . . . . .
H16 H 0.827040 0.238965 0.816169 0.042 Uiso 1 1 calc R . . . .
C17 C 0.6079(3) 0.2020(2) 0.85547(10) 0.0440(6) Uani 1 1 d . . . . .
H17 H 0.642828 0.134346 0.886910 0.053 Uiso 1 1 calc R . . . .
C18 C 0.4480(3) 0.2376(2) 0.85201(11) 0.0440(6) Uani 1 1 d . . . . .
H18 H 0.373686 0.195676 0.881317 0.053 Uiso 1 1 calc R . . . .
C19 C 0.3975(3) 0.3348(3) 0.80541(11) 0.0416(5) Uani 1 1 d . . . . .
H19 H 0.287823 0.358779 0.802312 0.050 Uiso 1 1 calc R . . . .
C20 C 0.5068(3) 0.3971(2) 0.76322(10) 0.0318(4) Uani 1 1 d . . . . .
H20 H 0.471039 0.463252 0.731259 0.038 Uiso 1 1 calc R . . . .


_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
O1 C9 1.413(3) . ?
O1 C10 1.445(3) . ?
N1 C5 1.385(3) . ?
N1 C8 1.394(2) . ?
N1 C9 1.450(2) . ?
N2 C10 1.434(3) . ?
N2 C11 1.473(2) . ?
N2 C13 1.477(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.380(3) . ?
C1 C6 1.403(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.404(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.396(3) . ?
C5 C6 1.414(3) . ?
C6 C7 1.432(3) . ?
C7 C8 1.363(3) . ?
C7 C12 1.497(3) . ?
C8 C11 1.502(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 1.0000 . ?
C13 C14 1.523(3) . ?
C13 C15 1.519(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.395(3) . ?
C15 C20 1.391(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.390(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(3) . ?
C20 H20 0.9500 . ?

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
C9 O1 C10 113.03(16) . . ?
C5 N1 C8 108.69(15) . . ?
C5 N1 C9 126.49(16) . . ?
C8 N1 C9 124.46(16) . . ?
C10 N2 C11 112.48(15) . . ?
C10 N2 C13 114.68(15) . . ?
C11 N2 C13 112.99(14) . . ?
C2 C1 H1 120.4 . . ?
C2 C1 C6 119.3(2) . . ?
C6 C1 H1 120.4 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.5(2) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.89(19) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 121.4 . . ?
C3 C4 C5 117.2(2) . . ?
C5 C4 H4 121.4 . . ?
N1 C5 C4 130.92(19) . . ?
N1 C5 C6 107.05(16) . . ?
C4 C5 C6 121.99(19) . . ?
C1 C6 C5 119.09(18) . . ?
C1 C6 C7 133.21(18) . . ?
C5 C6 C7 107.63(16) . . ?
C6 C7 C12 125.33(18) . . ?
C8 C7 C6 106.93(17) . . ?
C8 C7 C12 127.71(19) . . ?
N1 C8 C11 120.00(16) . . ?
C7 C8 N1 109.68(17) . . ?
C7 C8 C11 130.14(18) . . ?
O1 C9 N1 113.23(16) . . ?
O1 C9 H9A 108.9 . . ?
O1 C9 H9B 108.9 . . ?
N1 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
O1 C10 H10A 108.2 . . ?
O1 C10 H10B 108.2 . . ?
N2 C10 O1 116.20(15) . . ?
N2 C10 H10A 108.2 . . ?
N2 C10 H10B 108.2 . . ?
H10A C10 H10B 107.4 . . ?
N2 C11 C8 115.29(15) . . ?
N2 C11 H11A 108.5 . . ?
N2 C11 H11B 108.5 . . ?
C8 C11 H11A 108.5 . . ?
C8 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13 108.5 . . ?
N2 C13 C14 111.21(16) . . ?
N2 C13 C15 111.34(15) . . ?
C14 C13 H13 108.5 . . ?
C15 C13 H13 108.5 . . ?
C15 C13 C14 108.78(16) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C13 121.04(18) . . ?
C20 C15 C13 120.10(17) . . ?
C20 C15 C16 118.65(19) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.3(2) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.6(2) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.4(2) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.1(2) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 119.5 . . ?
C19 C20 C15 120.9(2) . . ?
C19 C20 H20 119.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
