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

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

data_final2_a
_database_code_depnum_ccdc_archive 'CCDC 1963872'
loop_
_audit_author_name
_audit_author_address
'Douglas Stephan'
;University of Toronto
Canada
;
_audit_update_record             
;
2019-11-05 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;
_audit_creation_date             2019-10-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C42 H58 N4'
_chemical_formula_sum            'C42 H58 N4'
_chemical_formula_weight         618.96
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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   6.449(3)
_cell_length_b                   10.347(6)
_cell_length_c                   13.623(8)
_cell_angle_alpha                85.979(13)
_cell_angle_beta                 84.125(13)
_cell_angle_gamma                82.722(16)
_cell_volume                     895.6(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1458
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.05
_cell_measurement_theta_min      2.42
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1083 before and 0.0508 after correction.
The Ratio of minimum to maximum transmission is 0.9265.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.1476
_exptl_crystal_description       block
_exptl_crystal_F_000             338.1138
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.1470
_diffrn_reflns_av_unetI/netI     0.1464
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11757
_diffrn_reflns_theta_full        25.4038
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         1.99
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.9961
_diffrn_measured_fraction_theta_max 0.9961
_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_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                1772
_reflns_number_total             3290
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.3664
_refine_diff_density_min         -0.3911
_refine_diff_density_rms         0.1012
_refine_ls_d_res_high            0.8284
_refine_ls_d_res_low             10.2467
_refine_ls_goodness_of_fit_ref   0.8225
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    44
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      0.8225
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0097P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0977
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C04(H04), C05(H05), C101(H101), C102(H102), C104(H104), C201(H201),
 C202(H202), C204(H204)
2.b Idealised Me refined as rotating group:
 C02(H02a,H02b,H02c), C12(H12a,H12b,H12c), C13(H13a,H13b,H13c), C14(H14a,H14b,
 H14c), C22(H22a,H22b,H22c), C23(H23a,H23b,H23c), C24(H24a,H24b,H24c)
;
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
N01 N 0.2836(2) 0.63672(17) 0.59592(13) 0.0201(4) Uani 1.000000 .
N02 N 0.5193(2) 0.08527(17) 0.82342(13) 0.0203(4) Uani 1.000000 .
C01 C 0.3278(3) 0.4398(2) 0.83432(15) 0.0169(5) Uani 1.000000 .
C02 C 0.5279(3) 0.4858(2) 0.86573(16) 0.0229(6) Uani 1.000000 .
H02a H 0.5658(11) 0.4381(8) 0.9255(5) 0.0343(8) Uiso 1.000000 GR
H02b H 0.6404(6) 0.4708(11) 0.8144(4) 0.0343(8) Uiso 1.000000 GR
H02c H 0.5023(6) 0.5773(3) 0.8768(9) 0.0343(8) Uiso 1.000000 GR
C03 C 0.1511(3) 0.4691(2) 0.91889(15) 0.0158(5) Uani 1.000000 .
C04 C 0.0793(3) 0.3729(2) 0.98483(16) 0.0207(5) Uani 1.000000 .
H04 H 0.1306(3) 0.2860(2) 0.97564(16) 0.0248(6) Uiso 1.000000 R
C05 C -0.0678(3) 0.4030(2) 1.06448(16) 0.0211(5) Uani 1.000000 .
H05 H -0.1113(3) 0.3359(2) 1.10763(16) 0.0253(7) Uiso 1.000000 R
C11 C 0.3477(3) 0.7319(2) 0.51549(16) 0.0214(5) Uani 1.000000 .
C12 C 0.2624(3) 0.7041(2) 0.42056(17) 0.0349(7) Uani 1.000000 .
H12a H 0.3046(17) 0.6144(4) 0.4064(5) 0.0523(10) Uiso 1.000000 GR
H12b H 0.1119(3) 0.7204(12) 0.4279(4) 0.0523(10) Uiso 1.000000 GR
H12c H 0.3167(16) 0.7597(9) 0.3672(2) 0.0523(10) Uiso 1.000000 GR
C13 C 0.2637(3) 0.8701(2) 0.54519(18) 0.0368(7) Uani 1.000000 .
H13a H 0.1130(3) 0.8795(5) 0.5526(9) 0.0551(10) Uiso 1.000000 GR
H13b H 0.3144(16) 0.8852(5) 0.6067(5) 0.0551(10) Uiso 1.000000 GR
H13c H 0.3110(17) 0.9324(2) 0.4949(5) 0.0551(10) Uiso 1.000000 GR
C14 C 0.5883(3) 0.7181(2) 0.49842(18) 0.0364(7) Uani 1.000000 .
H14a H 0.6447(3) 0.7395(14) 0.5570(4) 0.0546(10) Uiso 1.000000 GR
H14b H 0.6405(3) 0.6299(4) 0.4835(10) 0.0546(10) Uiso 1.000000 GR
H14c H 0.6300(3) 0.7764(11) 0.4441(7) 0.0546(10) Uiso 1.000000 GR
C21 C 0.6805(3) -0.0309(2) 0.82987(16) 0.0203(5) Uani 1.000000 .
C22 C 0.8145(3) -0.0411(2) 0.73055(16) 0.0340(7) Uani 1.000000 .
H22a H 0.7260(4) -0.0488(13) 0.6792(2) 0.0510(10) Uiso 1.000000 GR
H22b H 0.8841(16) 0.0358(6) 0.7166(5) 0.0510(10) Uiso 1.000000 GR
H22c H 0.9173(14) -0.1166(7) 0.7336(4) 0.0510(10) Uiso 1.000000 GR
C23 C 0.8179(3) -0.0177(2) 0.91177(17) 0.0303(6) Uani 1.000000 .
H23a H 0.8845(15) 0.0604(7) 0.8987(5) 0.0454(9) Uiso 1.000000 GR
H23b H 0.7329(4) -0.0132(13) 0.9738(2) 0.0454(9) Uiso 1.000000 GR
H23c H 0.9231(13) -0.0919(6) 0.9146(6) 0.0454(9) Uiso 1.000000 GR
C24 C 0.5712(3) -0.1535(2) 0.85175(19) 0.0345(7) Uani 1.000000 .
H24a H 0.4832(16) -0.1462(6) 0.9128(5) 0.0518(10) Uiso 1.000000 GR
H24b H 0.4870(16) -0.1630(7) 0.7992(5) 0.0518(10) Uiso 1.000000 GR
H24c H 0.6747(3) -0.2283(3) 0.8571(10) 0.0518(10) Uiso 1.000000 GR
C100 C 0.2681(3) 0.5149(2) 0.73944(16) 0.0164(5) Uani 1.000000 .
C101 C 0.0783(3) 0.5166(2) 0.69484(17) 0.0267(6) Uani 1.000000 .
H101 H -0.0359(3) 0.4743(2) 0.72058(17) 0.0321(7) Uiso 1.000000 R
C102 C 0.0909(3) 0.5901(2) 0.60855(17) 0.0278(6) Uani 1.000000 .
H102 H -0.0130(3) 0.6064(2) 0.56516(17) 0.0334(7) Uiso 1.000000 R
C104 C 0.3877(3) 0.5924(2) 0.67628(15) 0.0202(5) Uani 1.000000 .
H104 H 0.5204(3) 0.6116(2) 0.68694(15) 0.0243(6) Uiso 1.000000 R
C200 C 0.3702(3) 0.2943(2) 0.81884(15) 0.0163(5) Uani 1.000000 .
C201 C 0.2390(3) 0.2152(2) 0.77825(17) 0.0267(6) Uani 1.000000 .
H201 H 0.1108(3) 0.2442(2) 0.75370(17) 0.0320(7) Uiso 1.000000 R
C202 C 0.3342(3) 0.0889(2) 0.78161(16) 0.0262(6) Uani 1.000000 .
H202 H 0.2819(3) 0.0177(2) 0.75925(16) 0.0315(7) Uiso 1.000000 R
C204 C 0.5410(3) 0.2104(2) 0.84517(15) 0.0195(5) Uani 1.000000 .
H204 H 0.6544(3) 0.2347(2) 0.87348(15) 0.0234(6) Uiso 1.000000 R


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
N01 C11 1.484(3) . ?
N01 C102 1.380(2) . ?
N01 C104 1.365(2) . ?
N02 C21 1.491(2) . ?
N02 C202 1.369(2) . ?
N02 C204 1.376(3) . ?
C01 C02 1.540(3) . ?
C01 C03 1.553(3) . ?
C01 C100 1.519(3) . ?
C01 C200 1.522(3) . ?
C03 C04 1.385(3) . ?
C03 C05 1.389(3) 2_567 ?
C04 C05 1.392(3) . ?
C11 C12 1.515(3) . ?
C11 C13 1.530(3) . ?
C11 C14 1.535(3) . ?
C21 C22 1.532(3) . ?
C21 C23 1.517(3) . ?
C21 C24 1.525(3) . ?
C100 C101 1.419(3) . ?
C100 C104 1.379(3) . ?
C101 C102 1.356(3) . ?
C200 C201 1.423(3) . ?
C200 C204 1.375(3) . ?
C201 C202 1.372(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
C102 N01 C11 124.58(17) . . ?
C104 N01 C11 127.52(17) . . ?
C104 N01 C102 107.42(17) . . ?
C202 N02 C21 125.08(18) . . ?
C204 N02 C21 126.52(16) . . ?
C204 N02 C202 107.84(17) . . ?
C03 C01 C02 107.10(17) . . ?
C100 C01 C02 109.57(16) . . ?
C100 C01 C03 109.85(15) . . ?
C200 C01 C02 108.74(15) . . ?
C200 C01 C03 111.13(16) . . ?
C200 C01 C100 110.37(18) . . ?
C04 C03 C01 122.84(18) . . ?
C05 C03 C01 120.20(18) 2_567 . ?
C05 C03 C04 116.81(18) 2_567 . ?
C05 C04 C03 121.59(19) . . ?
C04 C05 C03 121.60(19) . 2_567 ?
C12 C11 N01 109.81(18) . . ?
C13 C11 N01 109.15(17) . . ?
C13 C11 C12 110.35(17) . . ?
C14 C11 N01 109.29(16) . . ?
C14 C11 C12 108.37(18) . . ?
C14 C11 C13 109.85(18) . . ?
C22 C21 N02 108.85(17) . . ?
C23 C21 N02 109.94(18) . . ?
C23 C21 C22 110.15(16) . . ?
C24 C21 N02 109.28(15) . . ?
C24 C21 C22 109.16(19) . . ?
C24 C21 C23 109.43(18) . . ?
C101 C100 C01 127.12(18) . . ?
C104 C100 C01 127.89(18) . . ?
C104 C100 C101 104.96(18) . . ?
C102 C101 C100 108.79(18) . . ?
C101 C102 N01 108.53(18) . . ?
C100 C104 N01 110.27(18) . . ?
C201 C200 C01 127.67(17) . . ?
C204 C200 C01 126.78(19) . . ?
C204 C200 C201 105.50(18) . . ?
C202 C201 C200 108.19(18) . . ?
C201 C202 N02 108.5(2) . . ?
C200 C204 N02 109.92(18) . . ?

_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_FINAL_a
_database_code_depnum_ccdc_archive 'CCDC 1963873'
loop_
_audit_author_name
_audit_author_address
'Douglas Stephan'
;University of Toronto
Canada
;
_audit_update_record             
;
2019-11-05 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;
_audit_creation_date             2019-11-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         '2(C24 H31 Br N2)'
_chemical_formula_sum            'C48 H62 Br2 N4'
_chemical_formula_weight         854.86
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'
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                   10.782(5)
_cell_length_b                   13.431(6)
_cell_length_c                   15.604(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.24(3)
_cell_angle_gamma                90
_cell_volume                     2241.6(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8686
_cell_measurement_theta_max      22.33
_cell_measurement_theta_min      2.45
_exptl_absorpt_coefficient_mu    1.844
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1082 before and 0.0720 after correction.
The Ratio of minimum to maximum transmission is 0.7729.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2665
_exptl_crystal_description       Shard
_exptl_crystal_F_000             895.1588
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            38958
_diffrn_reflns_theta_full        26.3716
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.17
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.9976
_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_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -13
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              -9
_reflns_number_gt                3104
_reflns_number_total             4575
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.7676
_refine_diff_density_min         -0.8208
_refine_diff_density_rms         0.1060
_refine_ls_d_res_high            0.8000
_refine_ls_d_res_low             9.3688
_refine_ls_goodness_of_fit_ref   1.0363
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     251
_refine_ls_number_reflns         4575
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0477
_refine_ls_restrained_S_all      1.0363
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0719P)²+1.3542P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1429
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C20(H20), C12(H12), C9(H9), C11(H11), C24(H24), C21(H21), C3(H3),
 C4(H4), C23(H23)
2.b Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c), C15(H15a,H15b,H15c), C7(H7a,H7b,H7c), C8(H8a,H8b,H8c),
 C6(H6a,H6b,H6c), C14(H14a,H14b,H14c), C16(H16a,H16b,H16c)
;
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 0.25910(4) 0.84139(3) 0.51409(3) 0.06569(19) Uani 1.000000 .
N1 N 0.3309(2) 0.25899(17) 0.56587(15) 0.0337(6) Uani 1.000000 .
N2 N 0.8134(2) 0.45652(18) 0.71621(17) 0.0391(6) Uani 1.000000 .
C17 C 0.4682(3) 0.4612(2) 0.71378(18) 0.0301(6) Uani 1.000000 .
C2 C 0.4272(3) 0.3673(2) 0.66198(18) 0.0296(6) Uani 1.000000 .
C19 C 0.4105(3) 0.5539(2) 0.66520(17) 0.0283(6) Uani 1.000000 .
C1 C 0.3423(3) 0.3578(2) 0.58826(18) 0.0313(6) Uani 1.000000 .
H1 H 0.2998(3) 0.4100(2) 0.55852(18) 0.0376(8) Uiso 1.000000 R
C10 C 0.6096(3) 0.47345(19) 0.72529(18) 0.0308(6) Uani 1.000000 .
C20 C 0.4550(3) 0.5848(2) 0.58932(19) 0.0349(7) Uani 1.000000 .
H20 H 0.5177(3) 0.5477(2) 0.56860(19) 0.0419(8) Uiso 1.000000 R
C12 C 0.8003(3) 0.5351(2) 0.7697(2) 0.0400(8) Uani 1.000000 .
H12 H 0.8650(3) 0.5740(2) 0.7968(2) 0.0479(9) Uiso 1.000000 R
C9 C 0.6960(3) 0.4192(2) 0.6891(2) 0.0401(7) Uani 1.000000 .
H9 H 0.6785(3) 0.3654(2) 0.6520(2) 0.0481(9) Uiso 1.000000 R
C11 C 0.6773(3) 0.5469(2) 0.7769(2) 0.0398(7) Uani 1.000000 .
H11 H 0.6432(3) 0.5950(2) 0.8100(2) 0.0478(9) Uiso 1.000000 R
C24 C 0.3174(3) 0.6113(2) 0.6938(2) 0.0374(7) Uani 1.000000 .
H24 H 0.2847(3) 0.5927(2) 0.7438(2) 0.0449(8) Uiso 1.000000 R
C21 C 0.4099(3) 0.6684(2) 0.5435(2) 0.0400(7) Uani 1.000000 .
H21 H 0.4409(3) 0.6867(2) 0.4928(2) 0.0480(9) Uiso 1.000000 R
C22 C 0.3179(3) 0.7238(2) 0.5751(2) 0.0394(7) Uani 1.000000 .
C3 C 0.4675(3) 0.2691(2) 0.6851(2) 0.0426(8) Uani 1.000000 .
H3 H 0.5244(3) 0.2514(2) 0.7325(2) 0.0511(9) Uiso 1.000000 R
C5 C 0.2465(3) 0.2138(3) 0.4913(2) 0.0443(8) Uani 1.000000 .
C18 C 0.4260(3) 0.4510(2) 0.80415(19) 0.0399(7) Uani 1.000000 .
H18a H 0.3368(4) 0.4438(16) 0.7985(2) 0.0598(11) Uiso 1.000000 GR
H18b H 0.4648(16) 0.3935(9) 0.8326(6) 0.0598(11) Uiso 1.000000 GR
H18c H 0.4502(18) 0.5094(7) 0.8376(5) 0.0598(11) Uiso 1.000000 GR
C4 C 0.4077(3) 0.2054(2) 0.6253(2) 0.0430(8) Uani 1.000000 .
H4 H 0.4176(3) 0.1366(2) 0.6251(2) 0.0516(9) Uiso 1.000000 R
C23 C 0.2713(3) 0.6964(2) 0.6493(2) 0.0424(8) Uani 1.000000 .
H23 H 0.2092(3) 0.7342(2) 0.6700(2) 0.0509(9) Uiso 1.000000 R
C13 C 0.9304(3) 0.4160(3) 0.6894(2) 0.0489(9) Uani 1.000000 .
C15 C 0.9360(4) 0.3056(3) 0.7048(3) 0.0761(13) Uani 1.000000 .
H15a H 0.935(3) 0.2925(3) 0.7652(4) 0.114(2) Uiso 1.000000 GR
H15b H 0.8652(17) 0.2743(4) 0.6721(17) 0.114(2) Uiso 1.000000 GR
H15c H 1.0116(16) 0.2794(5) 0.687(2) 0.114(2) Uiso 1.000000 GR
C7 C 0.1494(5) 0.1538(5) 0.5277(3) 0.109(2) Uani 1.000000 .
H7a H 0.1888(6) 0.111(2) 0.572(2) 0.163(3) Uiso 1.000000 GR
H7b H 0.093(2) 0.1975(5) 0.552(3) 0.163(3) Uiso 1.000000 GR
H7c H 0.104(3) 0.115(3) 0.4826(7) 0.163(3) Uiso 1.000000 GR
C8 C 0.3230(6) 0.1443(4) 0.4437(4) 0.111(2) Uani 1.000000 .
H8a H 0.388(3) 0.1811(7) 0.421(3) 0.167(3) Uiso 1.000000 GR
H8b H 0.360(4) 0.094(2) 0.4826(8) 0.167(3) Uiso 1.000000 GR
H8c H 0.2703(10) 0.113(3) 0.3970(19) 0.167(3) Uiso 1.000000 GR
C6 C 0.1945(7) 0.2928(4) 0.4309(4) 0.142(3) Uani 1.000000 .
H6a H 0.156(5) 0.343(2) 0.4624(8) 0.213(5) Uiso 1.000000 GR
H6b H 0.2606(13) 0.322(3) 0.403(3) 0.213(5) Uiso 1.000000 GR
H6c H 0.133(4) 0.2646(10) 0.388(2) 0.213(5) Uiso 1.000000 GR
C14 C 0.9286(6) 0.4355(5) 0.5929(4) 0.126(3) Uani 1.000000 .
H14a H 0.854(3) 0.408(3) 0.5621(5) 0.189(4) Uiso 1.000000 GR
H14b H 0.931(5) 0.5060(5) 0.5828(5) 0.189(4) Uiso 1.000000 GR
H14c H 1.000(3) 0.405(3) 0.5730(9) 0.189(4) Uiso 1.000000 GR
C16 C 1.0417(4) 0.4625(5) 0.7426(6) 0.153(3) Uani 1.000000 .
H16a H 1.047(3) 0.5316(13) 0.728(3) 0.230(5) Uiso 1.000000 GR
H16b H 1.033(3) 0.457(4) 0.8028(5) 0.230(5) Uiso 1.000000 GR
H16c H 1.1165(7) 0.429(3) 0.731(3) 0.230(5) 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 C22 1.911(3) . ?
N1 C1 1.374(3) . ?
N1 C5 1.511(4) . ?
N1 C4 1.368(4) . ?
N2 C12 1.364(4) . ?
N2 C9 1.378(4) . ?
N2 C13 1.482(4) . ?
C17 C2 1.533(4) . ?
C17 C19 1.547(4) . ?
C17 C10 1.521(4) . ?
C17 C18 1.541(4) . ?
C2 C1 1.382(4) . ?
C2 C3 1.420(4) . ?
C19 C20 1.396(4) . ?
C19 C24 1.383(4) . ?
C1 H1 0.9300 . ?
C10 C9 1.360(4) . ?
C10 C11 1.417(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.386(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.354(4) . ?
C9 H9 0.9300 . ?
C11 H11 0.9300 . ?
C24 H24 0.9300 . ?
C24 C23 1.395(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.380(4) . ?
C22 C23 1.370(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.367(4) . ?
C5 C7 1.489(6) . ?
C5 C8 1.503(6) . ?
C5 C6 1.482(6) . ?
C18 H18a 0.9600 . ?
C18 H18b 0.9600 . ?
C18 H18c 0.9600 . ?
C4 H4 0.9300 . ?
C23 H23 0.9300 . ?
C13 C15 1.503(5) . ?
C13 C14 1.526(7) . ?
C13 C16 1.506(6) . ?
C15 H15a 0.9600 . ?
C15 H15b 0.9600 . ?
C15 H15c 0.9600 . ?
C7 H7a 0.9600 . ?
C7 H7b 0.9600 . ?
C7 H7c 0.9600 . ?
C8 H8a 0.9600 . ?
C8 H8b 0.9600 . ?
C8 H8c 0.9600 . ?
C6 H6a 0.9600 . ?
C6 H6b 0.9600 . ?
C6 H6c 0.9600 . ?
C14 H14a 0.9600 . ?
C14 H14b 0.9600 . ?
C14 H14c 0.9600 . ?
C16 H16a 0.9600 . ?
C16 H16b 0.9600 . ?
C16 H16c 0.9600 . ?

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
C5 N1 C1 127.6(2) . . ?
C4 N1 C1 108.0(2) . . ?
C4 N1 C5 124.4(2) . . ?
C9 N2 C12 107.9(3) . . ?
C13 N2 C12 127.9(3) . . ?
C13 N2 C9 124.2(3) . . ?
C19 C17 C2 109.4(2) . . ?
C10 C17 C2 111.7(2) . . ?
C10 C17 C19 107.8(2) . . ?
C18 C17 C2 108.1(2) . . ?
C18 C17 C19 111.9(2) . . ?
C18 C17 C10 108.0(2) . . ?
C1 C2 C17 129.1(2) . . ?
C3 C2 C17 124.8(2) . . ?
C3 C2 C1 106.0(2) . . ?
C20 C19 C17 119.7(2) . . ?
C24 C19 C17 123.7(3) . . ?
C24 C19 C20 116.7(3) . . ?
C2 C1 N1 109.2(2) . . ?
H1 C1 N1 125.39(16) . . ?
H1 C1 C2 125.39(16) . . ?
C9 C10 C17 128.4(2) . . ?
C11 C10 C17 125.4(3) . . ?
C11 C10 C9 106.2(3) . . ?
H20 C20 C19 118.55(17) . . ?
C21 C20 C19 122.9(3) . . ?
C21 C20 H20 118.55(18) . . ?
H12 C12 N2 125.67(17) . . ?
C11 C12 N2 108.7(3) . . ?
C11 C12 H12 125.67(17) . . ?
C10 C9 N2 109.2(3) . . ?
H9 C9 N2 125.42(16) . . ?
H9 C9 C10 125.42(17) . . ?
C12 C11 C10 108.1(3) . . ?
H11 C11 C10 125.97(18) . . ?
H11 C11 C12 125.97(17) . . ?
H24 C24 C19 119.21(17) . . ?
C23 C24 C19 121.6(3) . . ?
C23 C24 H24 119.21(18) . . ?
H21 C21 C20 120.88(18) . . ?
C22 C21 C20 118.2(3) . . ?
C22 C21 H21 120.88(18) . . ?
C21 C22 Br1 118.4(2) . . ?
C23 C22 Br1 120.6(2) . . ?
C23 C22 C21 120.9(3) . . ?
H3 C3 C2 126.13(17) . . ?
C4 C3 C2 107.7(3) . . ?
C4 C3 H3 126.13(18) . . ?
C7 C5 N1 107.9(3) . . ?
C8 C5 N1 108.4(3) . . ?
C8 C5 C7 108.0(4) . . ?
C6 C5 N1 110.1(3) . . ?
C6 C5 C7 113.7(5) . . ?
C6 C5 C8 108.6(5) . . ?
H18a C18 C17 109.5 . . ?
H18b C18 C17 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 C17 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
C3 C4 N1 109.0(3) . . ?
H4 C4 N1 125.48(16) . . ?
H4 C4 C3 125.48(18) . . ?
C22 C23 C24 119.7(3) . . ?
H23 C23 C24 120.17(18) . . ?
H23 C23 C22 120.17(18) . . ?
C15 C13 N2 109.6(3) . . ?
C14 C13 N2 108.1(3) . . ?
C14 C13 C15 108.8(4) . . ?
C16 C13 N2 109.8(3) . . ?
C16 C13 C15 107.9(4) . . ?
C16 C13 C14 112.5(5) . . ?
H15a C15 C13 109.5 . . ?
H15b C15 C13 109.5 . . ?
H15b C15 H15a 109.5 . . ?
H15c C15 C13 109.5 . . ?
H15c C15 H15a 109.5 . . ?
H15c C15 H15b 109.5 . . ?
H7a C7 C5 109.5 . . ?
H7b C7 C5 109.5 . . ?
H7b C7 H7a 109.5 . . ?
H7c C7 C5 109.5 . . ?
H7c C7 H7a 109.5 . . ?
H7c C7 H7b 109.5 . . ?
H8a C8 C5 109.5 . . ?
H8b C8 C5 109.5 . . ?
H8b C8 H8a 109.5 . . ?
H8c C8 C5 109.5 . . ?
H8c C8 H8a 109.5 . . ?
H8c C8 H8b 109.5 . . ?
H6a C6 C5 109.5 . . ?
H6b C6 C5 109.5 . . ?
H6b C6 H6a 109.5 . . ?
H6c C6 C5 109.5 . . ?
H6c C6 H6a 109.5 . . ?
H6c C6 H6b 109.5 . . ?
H14a C14 C13 109.5 . . ?
H14b C14 C13 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 C13 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?
H16a C16 C13 109.5 . . ?
H16b C16 C13 109.5 . . ?
H16b C16 H16a 109.5 . . ?
H16c C16 C13 109.5 . . ?
H16c C16 H16a 109.5 . . ?
H16c C16 H16b 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
