# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_532_0ma
_database_code_depnum_ccdc_archive 'CCDC 2043179'
loop_
_audit_author_name
_audit_author_address
'Lei. X'
;donghua university
China
;
_audit_update_record             
;
2020-11-09 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;
_audit_creation_date             2020-04-30
_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         'C18 H17 Br N2'
_chemical_formula_sum            'C18 H17 Br N2'
_chemical_formula_weight         341.24
_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'
N N 0.0061 0.0033 '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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   12.3914(12)
_cell_length_b                   11.5252(9)
_cell_length_c                   22.193(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3169.4(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6567
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.46
_shelx_estimated_absorpt_T_max   0.782
_shelx_estimated_absorpt_T_min   0.626
_exptl_absorpt_coefficient_mu    2.589
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0808 before and 0.0661 after correction.
The Ratio of minimum to maximum transmission is 0.4022.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_colour_primary    ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0945
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            37056
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.395
_diffrn_reflns_theta_min         2.464
_diffrn_ambient_temperature      150.2
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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                2235
_reflns_number_total             3224
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.721
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.032
_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)+(0.0452P)²+5.0964P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1135
_refine_special_details          ?
_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:
 C005(H005), C006(H006), C009(H009), C00A(H00A), C00C(H00C), C00E(H00E),
 C00G(H00G), C00J(H00J)
2.b Idealised Me refined as rotating group:
 C00H(H00B,H00D,H00F), C00K(H00H,H00I,H00K), C00L(H00L,H00M,H00N)
;
_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
Br01 Br 0.40626(3) 0.20339(3) 0.57741(2) 0.04305(15) Uani 1 1 d . . . . .
N002 N 0.4775(3) 0.7066(3) 0.74477(14) 0.0394(7) Uani 1 1 d . . . . .
N003 N 0.2851(3) 0.9061(3) 0.71383(17) 0.0572(10) Uani 1 1 d . . . . .
C004 C 0.2325(3) 0.5561(3) 0.45333(17) 0.0349(9) Uani 1 1 d . . . . .
C005 C 0.3826(3) 0.5705(3) 0.52245(17) 0.0346(9) Uani 1 1 d . . . . .
H005 H 0.447801 0.608073 0.533762 0.041 Uiso 1 1 calc R . . . .
C006 C 0.2482(3) 0.4263(3) 0.53921(17) 0.0356(9) Uani 1 1 d . . . . .
H006 H 0.219360 0.363935 0.562135 0.043 Uiso 1 1 calc R . . . .
C007 C 0.3444(3) 0.4787(3) 0.55739(17) 0.0342(8) Uani 1 1 d . . . . .
C008 C 0.4030(3) 0.4425(3) 0.61307(17) 0.0337(8) Uani 1 1 d . . . . .
C009 C 0.1940(3) 0.4641(3) 0.48802(18) 0.0380(9) Uani 1 1 d . . . . .
H009 H 0.129177 0.426285 0.476356 0.046 Uiso 1 1 calc R . . . .
C00A C 0.3662(3) 0.6328(3) 0.66357(17) 0.0359(8) Uani 1 1 d . . . . .
H00A H 0.304801 0.643801 0.638599 0.043 Uiso 1 1 calc R . . . .
C00B C 0.4301(3) 0.5337(3) 0.65760(17) 0.0347(9) Uani 1 1 d . . . . .
C00C C 0.3280(3) 0.6082(3) 0.47167(17) 0.0365(9) Uani 1 1 d . . . . .
H00C H 0.356411 0.671019 0.448938 0.044 Uiso 1 1 calc R . . . .
C00D C 0.3938(3) 0.7146(3) 0.70646(17) 0.0366(8) Uani 1 1 d . . . . .
C00E C 0.4291(3) 0.3337(3) 0.62746(18) 0.0373(9) Uani 1 1 d . . . . .
H00E H 0.461476 0.320750 0.665678 0.045 Uiso 1 1 calc R . . . .
C00F C 0.3313(4) 0.8200(4) 0.71130(19) 0.0440(10) Uani 1 1 d . . . . .
C00G C 0.5180(3) 0.5252(3) 0.69654(18) 0.0399(9) Uani 1 1 d . . . . .
H00G H 0.564563 0.459887 0.694416 0.048 Uiso 1 1 calc R . . . .
C00H C 0.1674(4) 0.4974(4) 0.35026(18) 0.0443(10) Uani 1 1 d . . . . .
H00B H 0.241625 0.476657 0.339405 0.067 Uiso 1 1 calc GR . . . .
H00D H 0.128724 0.523486 0.314213 0.067 Uiso 1 1 calc GR . . . .
H00F H 0.130886 0.429516 0.367289 0.067 Uiso 1 1 calc GR . . . .
C00I C 0.1691(3) 0.5956(3) 0.39711(18) 0.0410(9) Uani 1 1 d . . . . .
C00J C 0.5375(3) 0.6118(3) 0.73826(19) 0.0436(10) Uani 1 1 d . . . . .
H00J H 0.597973 0.602838 0.764132 0.052 Uiso 1 1 calc R . . . .
C00K C 0.2197(4) 0.7035(4) 0.3681(2) 0.0525(11) Uani 1 1 d . . . . .
H00H H 0.220878 0.767130 0.397363 0.079 Uiso 1 1 calc GR . . . .
H00I H 0.176923 0.726607 0.332905 0.079 Uiso 1 1 calc GR . . . .
H00K H 0.293636 0.685786 0.355350 0.079 Uiso 1 1 calc GR . . . .
C00L C 0.0518(4) 0.6233(4) 0.4142(2) 0.0553(12) Uani 1 1 d . . . . .
H00L H 0.019335 0.555758 0.433953 0.083 Uiso 1 1 calc GR . . . .
H00M H 0.010763 0.642116 0.377688 0.083 Uiso 1 1 calc GR . . . .
H00N H 0.050329 0.689722 0.441725 0.083 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
Br01 C00E 1.889(4) . ?
N002 C00D 1.344(5) . ?
N002 C00J 1.330(5) . ?
N003 C00F 1.147(5) . ?
C004 C009 1.395(5) . ?
C004 C00C 1.388(5) . ?
C004 C00I 1.542(5) . ?
C005 C007 1.395(5) . ?
C005 C00C 1.385(5) . ?
C006 C007 1.396(5) . ?
C006 C009 1.390(5) . ?
C007 C008 1.493(5) . ?
C008 C00B 1.481(5) . ?
C008 C00E 1.334(5) . ?
C00A C00B 1.396(5) . ?
C00A C00D 1.382(5) . ?
C00B C00G 1.393(5) . ?
C00D C00F 1.445(6) . ?
C00G C00J 1.382(6) . ?
C00H C00I 1.537(6) . ?
C00I C00K 1.535(6) . ?
C00I C00L 1.536(6) . ?

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
C00J N002 C00D 114.7(3) . . ?
C009 C004 C00I 119.8(3) . . ?
C00C C004 C009 117.3(4) . . ?
C00C C004 C00I 122.9(3) . . ?
C00C C005 C007 121.6(4) . . ?
C009 C006 C007 120.9(4) . . ?
C005 C007 C006 117.2(3) . . ?
C005 C007 C008 120.4(3) . . ?
C006 C007 C008 122.3(3) . . ?
C00B C008 C007 117.7(3) . . ?
C00E C008 C007 125.4(3) . . ?
C00E C008 C00B 116.9(3) . . ?
C006 C009 C004 121.7(4) . . ?
C00D C00A C00B 118.9(4) . . ?
C00A C00B C008 121.0(3) . . ?
C00G C00B C008 122.8(3) . . ?
C00G C00B C00A 116.2(4) . . ?
C005 C00C C004 121.3(4) . . ?
N002 C00D C00A 125.5(4) . . ?
N002 C00D C00F 115.1(3) . . ?
C00A C00D C00F 119.5(4) . . ?
C008 C00E Br01 124.8(3) . . ?
N003 C00F C00D 177.0(5) . . ?
C00J C00G C00B 120.1(4) . . ?
C00H C00I C004 109.7(3) . . ?
C00K C00I C004 111.8(3) . . ?
C00K C00I C00H 108.5(3) . . ?
C00K C00I C00L 108.8(4) . . ?
C00L C00I C004 110.1(3) . . ?
C00L C00I C00H 107.9(4) . . ?
N002 C00J C00G 124.6(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
