# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_mo_wcm141013_0m-auto
_database_code_depnum_ccdc_archive 'CCDC 2205053'
loop_
_audit_author_name
_audit_author_address
' Chu'
;China West Normal University
China
;
_audit_update_record             
;
2022-09-03 deposited with the CCDC.	2022-10-30 downloaded from the CCDC.
;
_audit_creation_date             2022-03-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H18 Br N O'
_chemical_formula_sum            'C15 H18 Br N O'
_chemical_formula_weight         308.220
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   6.034(3)
_cell_length_b                   23.507(11)
_cell_length_c                   9.961(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.291(13)
_cell_angle_gamma                90
_cell_volume                     1410.6(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7779
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.98
_cell_measurement_theta_min      2.22
_exptl_absorpt_coefficient_mu    2.902
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4452
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0960 before and 0.0499 after correction.
The Ratio of minimum to maximum transmission is 0.5972.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_description       block
_exptl_crystal_F_000             631.419
_exptl_crystal_preparation       block
_exptl_crystal_recrystallization_method block
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.9988
_diffrn_reflns_Laue_measured_fraction_max 0.9966
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20844
_diffrn_reflns_point_group_measured_fraction_full 0.9988
_diffrn_reflns_point_group_measured_fraction_max 0.9966
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.22
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.9988
_diffrn_measured_fraction_theta_max 0.9966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -7
_reflns_limit_k_max              30
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              -5
_reflns_number_gt                2568
_reflns_number_total             3225
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.8520
_refine_diff_density_min         -0.8230
_refine_diff_density_rms         0.1200
_refine_ls_d_res_high            0.7701
_refine_ls_d_res_low             9.1589
_refine_ls_goodness_of_fit_ref   1.0325
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    29
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.0325
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0761P)²+1.7496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1466
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C4(H4a,H4b), C5(H5a,H5b)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C8(H8), C9(H9), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c), C12(H12a,H12b,H12c)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
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_refinement_flags_posn
Br1 Br 0.81002(8) 0.438313(18) 0.15690(4) 0.06097(19) Uani 1.000000 .
N1 N 0.2759(4) 0.61712(11) 0.4293(3) 0.0385(6) Uani 1.000000 .
O1 O 0.4966(9) 0.8038(2) 0.7696(6) 0.137(2) Uani 1.000000 .
C2 C 0.2621(8) 0.80783(18) 0.7429(4) 0.0682(13) Uani 1.000000 .
C3 C 0.2082(6) 0.80278(14) 0.5941(4) 0.0432(8) Uani 1.000000 .
C4 C 0.3120(6) 0.74930(14) 0.5378(4) 0.0469(8) Uani 1.000000 .
C5 C 0.2318(6) 0.69255(14) 0.5909(4) 0.0466(8) Uani 1.000000 .
C6 C 0.3626(5) 0.64442(13) 0.5350(3) 0.0398(7) Uani 1.000000 .
C7 C 0.4002(5) 0.57559(12) 0.3730(3) 0.0331(6) Uani 1.000000 .
C8 C 0.3106(6) 0.54710(14) 0.2573(4) 0.0421(7) Uani 1.000000 .
C9 C 0.4294(6) 0.50682(15) 0.1950(4) 0.0451(8) Uani 1.000000 .
C10 C 0.6439(6) 0.49337(13) 0.2470(3) 0.0397(7) Uani 1.000000 .
C11 C 0.3061(10) 0.85510(19) 0.5252(6) 0.0829(15) Uani 1.000000 .
C12 C -0.0387(8) 0.8034(2) 0.5649(7) 0.0851(18) Uani 1.000000 .
C13 C 0.5768(6) 0.63167(15) 0.5929(4) 0.0465(8) Uani 1.000000 .
C14 C 0.7009(6) 0.59075(14) 0.5388(3) 0.0430(7) Uani 1.000000 .
C15 C 0.6153(5) 0.56125(12) 0.4244(3) 0.0338(6) Uani 1.000000 .
C16 C 0.7365(5) 0.51941(14) 0.3589(3) 0.0385(7) Uani 1.000000 .
H16 H 0.8788(5) 0.50962(14) 0.3917(3) 0.0462(8) Uiso 1.000000 R
H8 H 0.1681(6) 0.55605(14) 0.2234(4) 0.0505(9) Uiso 1.000000 R
H9 H 0.3692(6) 0.48840(15) 0.1187(4) 0.0542(9) Uiso 1.000000 R
H13 H 0.6321(6) 0.65154(15) 0.6683(4) 0.0558(10) Uiso 1.000000 R
H14 H 0.8414(6) 0.58218(14) 0.5767(3) 0.0516(9) Uiso 1.000000 R
H2a H 0.1885(8) 0.77771(18) 0.7898(4) 0.0818(15) Uiso 1.000000 R
H2b H 0.2092(8) 0.84404(18) 0.7751(4) 0.0818(15) Uiso 1.000000 R
H4a H 0.2847(6) 0.74954(14) 0.4409(4) 0.0562(10) Uiso 1.000000 R
H4b H 0.4714(6) 0.75144(14) 0.5562(4) 0.0562(10) Uiso 1.000000 R
H5a H 0.2491(6) 0.69223(14) 0.6883(4) 0.0559(10) Uiso 1.000000 R
H5b H 0.0755(6) 0.68764(14) 0.5651(4) 0.0559(10) Uiso 1.000000 R
H11a H 0.242(5) 0.8891(2) 0.559(3) 0.124(2) Uiso 1.000000 GR
H11b H 0.4640(14) 0.8560(10) 0.543(4) 0.124(2) Uiso 1.000000 GR
H11c H 0.273(6) 0.8528(9) 0.4299(8) 0.124(2) Uiso 1.000000 GR
H12a H -0.1047(11) 0.7725(12) 0.611(4) 0.128(3) Uiso 1.000000 GR
H12b H -0.0981(13) 0.8388(8) 0.595(4) 0.128(3) Uiso 1.000000 GR
H12c H -0.0710(8) 0.7993(19) 0.4699(8) 0.128(3) Uiso 1.000000 GR
H1 H 0.539(3) 0.830(3) 0.818(9) 0.205(3) Uiso 1.000000 GR


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 C10 1.894(3) . ?
N1 C6 1.316(4) . ?
N1 C7 1.371(4) . ?
O1 C2 1.428(7) . ?
O1 H1 0.8200 . ?
C2 C3 1.504(6) . ?
C2 H2a 0.9700 . ?
C2 H2b 0.9700 . ?
C3 C4 1.525(4) . ?
C3 C11 1.542(6) . ?
C3 C12 1.502(6) . ?
C4 C5 1.524(5) . ?
C4 H4a 0.9700 . ?
C4 H4b 0.9700 . ?
C5 C6 1.504(5) . ?
C5 H5a 0.9700 . ?
C5 H5b 0.9700 . ?
C6 C13 1.417(5) . ?
C7 C8 1.413(5) . ?
C7 C15 1.409(4) . ?
C8 C9 1.359(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.402(5) . ?
C9 H9 0.9300 . ?
C10 C16 1.363(5) . ?
C11 H11a 0.9600 . ?
C11 H11b 0.9600 . ?
C11 H11c 0.9600 . ?
C12 H12a 0.9600 . ?
C12 H12b 0.9600 . ?
C12 H12c 0.9600 . ?
C13 C14 1.350(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.406(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.408(5) . ?
C16 H16 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C6 118.3(3) . . ?
H1 O1 C2 109.5 . . ?
C3 C2 O1 109.5(4) . . ?
H2a C2 O1 109.8(3) . . ?
H2a C2 C3 109.8(2) . . ?
H2b C2 O1 109.8(3) . . ?
H2b C2 C3 109.8(2) . . ?
H2b C2 H2a 108.2 . . ?
C4 C3 C2 110.9(3) . . ?
C11 C3 C2 108.0(4) . . ?
C11 C3 C4 108.5(3) . . ?
C12 C3 C2 110.2(4) . . ?
C12 C3 C4 111.2(3) . . ?
C12 C3 C11 107.8(4) . . ?
C5 C4 C3 116.7(3) . . ?
H4a C4 C3 108.1(2) . . ?
H4a C4 C5 108.1(2) . . ?
H4b C4 C3 108.13(19) . . ?
H4b C4 C5 108.1(2) . . ?
H4b C4 H4a 107.3 . . ?
C6 C5 C4 110.3(3) . . ?
H5a C5 C4 109.6(2) . . ?
H5a C5 C6 109.6(2) . . ?
H5b C5 C4 109.6(2) . . ?
H5b C5 C6 109.60(19) . . ?
H5b C5 H5a 108.1 . . ?
C5 C6 N1 118.0(3) . . ?
C13 C6 N1 122.2(3) . . ?
C13 C6 C5 119.6(3) . . ?
C8 C7 N1 118.6(3) . . ?
C15 C7 N1 122.4(3) . . ?
C15 C7 C8 119.0(3) . . ?
C9 C8 C7 121.0(3) . . ?
H8 C8 C7 119.48(19) . . ?
H8 C8 C9 119.5(2) . . ?
C10 C9 C8 119.2(3) . . ?
H9 C9 C8 120.4(2) . . ?
H9 C9 C10 120.40(19) . . ?
C9 C10 Br1 118.7(3) . . ?
C16 C10 Br1 119.4(3) . . ?
C16 C10 C9 121.8(3) . . ?
H11a C11 C3 109.5 . . ?
H11b C11 C3 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 C3 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
H12a C12 C3 109.5 . . ?
H12b C12 C3 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 C3 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
C14 C13 C6 120.2(3) . . ?
H13 C13 C6 119.9(2) . . ?
H13 C13 C14 119.9(2) . . ?
C15 C14 C13 119.2(3) . . ?
H14 C14 C13 120.4(2) . . ?
H14 C14 C15 120.39(19) . . ?
C14 C15 C7 117.7(3) . . ?
C16 C15 C7 119.4(3) . . ?
C16 C15 C14 122.9(3) . . ?
C15 C16 C10 119.6(3) . . ?
H16 C16 C10 120.22(19) . . ?
H16 C16 C15 120.22(18) . . ?

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
Br1 C10 C9 C8 -178.7(3) . . . . ?
Br1 C10 C16 C15 178.6(2) . . . . ?
N1 C6 C5 C4 -97.4(3) . . . . ?
N1 C6 C13 C14 0.8(4) . . . . ?
N1 C7 C8 C9 177.9(3) . . . . ?
N1 C7 C15 C14 0.8(3) . . . . ?
N1 C7 C15 C16 -177.9(3) . . . . ?
O1 C2 C3 C4 53.1(4) . . . . ?
O1 C2 C3 C11 -65.8(4) . . . . ?
O1 C2 C3 C12 176.6(4) . . . . ?
C2 C3 C4 C5 63.1(4) . . . . ?
C3 C4 C5 C6 -175.2(3) . . . . ?
C4 C5 C6 C13 79.7(4) . . . . ?
C5 C6 C13 C14 -176.2(3) . . . . ?
C6 C13 C14 C15 0.2(4) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
C7 C15 C14 C13 -0.9(3) . . . . ?
C7 C15 C16 C10 -0.1(3) . . . . ?
C8 C9 C10 C16 0.3(4) . . . . ?
C9 C10 C16 C15 -0.3(4) . . . . ?
C10 C16 C15 C14 -178.8(3) . . . . ?
C13 C14 C15 C16 177.7(3) . . . . ?


_olex2_exptl_crystal_mounting_method 
;
block
;
_olex2_submission_special_instructions 'No special instructions were received'
