# 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_210425_zzc0906_0m
_database_code_depnum_ccdc_archive 'CCDC 2142743'
loop_
_audit_author_name
_audit_author_address
'Zicong Zheng'
; Zhejiang University of Technology
China
;
_audit_update_record             
;
2022-01-18 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;
_audit_creation_date             2021-04-26
_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         'C13 H10 Br N'
_chemical_formula_sum            'C13 H10 Br N'
_chemical_formula_weight         260.13
_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      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                   4.0225(17)
_cell_length_b                   10.358(5)
_cell_length_c                   13.332(6)
_cell_angle_alpha                100.995(15)
_cell_angle_beta                 92.154(15)
_cell_angle_gamma                97.659(14)
_cell_volume                     539.3(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.29
_shelx_estimated_absorpt_T_max   0.895
_shelx_estimated_absorpt_T_min   0.328
_exptl_absorpt_coefficient_mu    3.774
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1627 before and 0.0577 after correction.
The Ratio of minimum to maximum transmission is 0.7874.
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    1.602
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17461
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.181
_diffrn_reflns_theta_min         2.298
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_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                2221
_reflns_number_total             2362
_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         1.577
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.072
_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)+(0.0641P)²+0.1172P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0876
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C12(H12)
2.c X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
;
_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 1.23815(6) 0.83994(2) 0.96070(2) 0.03266(11) Uani 1 1 d . . . . .
N1 N 0.6548(7) 0.3097(3) 0.47294(16) 0.0444(6) Uani 1 1 d . . . . .
C1 C -0.1780(6) -0.0418(2) 0.7272(2) 0.0341(5) Uani 1 1 d . . . . .
H1A H -0.240610 -0.047972 0.794338 0.041 Uiso 1 1 calc R . . . .
H1B H -0.264579 -0.110307 0.670727 0.041 Uiso 1 1 calc R . . . .
C2 C 0.0292(6) 0.0618(2) 0.71248(17) 0.0272(4) Uani 1 1 d . . . . .
C3 C 0.2126(6) 0.1870(2) 0.78258(17) 0.0264(4) Uani 1 1 d . . . . .
H3A H 0.061363 0.246634 0.817480 0.032 Uiso 1 1 calc R . . . .
H3B H 0.383869 0.169697 0.831746 0.032 Uiso 1 1 calc R . . . .
C4 C 0.3560(6) 0.2287(2) 0.68786(16) 0.0241(4) Uani 1 1 d . . . . .
C5 C 0.1813(6) 0.1027(2) 0.61773(17) 0.0279(4) Uani 1 1 d . . . . .
H5A H 0.336895 0.043420 0.584967 0.033 Uiso 1 1 calc R . . . .
H5B H 0.013583 0.118343 0.566750 0.033 Uiso 1 1 calc R . . . .
C6 C 0.5536(6) 0.3332(2) 0.66628(16) 0.0240(4) Uani 1 1 d . . . . .
C7 C 0.7172(5) 0.4539(2) 0.73756(16) 0.0224(4) Uani 1 1 d . . . . .
C8 C 0.6838(6) 0.4726(2) 0.84372(17) 0.0265(4) Uani 1 1 d . . . . .
H8 H 0.553728 0.405445 0.870898 0.032 Uiso 1 1 calc R . . . .
C9 C 0.8355(6) 0.5860(2) 0.90906(17) 0.0272(4) Uani 1 1 d . . . . .
H9 H 0.808301 0.597418 0.980542 0.033 Uiso 1 1 calc R . . . .
C10 C 1.0286(5) 0.6837(2) 0.86979(16) 0.0237(4) Uani 1 1 d . . . . .
C11 C 1.0705(6) 0.6687(2) 0.76585(17) 0.0270(4) Uani 1 1 d . . . . .
H11 H 1.204624 0.735741 0.739638 0.032 Uiso 1 1 calc R . . . .
C12 C 0.9137(6) 0.5543(2) 0.70038(16) 0.0261(4) Uani 1 1 d . . . . .
H12 H 0.940347 0.543945 0.628916 0.031 Uiso 1 1 calc R . . . .
C13 C 0.6121(6) 0.3232(2) 0.55882(17) 0.0304(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C10 1.900(2) . ?
N1 C13 1.149(3) . ?
C1 H1A 0.9500 . ?
C1 H1B 0.9500 . ?
C1 C2 1.319(3) . ?
C2 C3 1.526(3) . ?
C2 C5 1.530(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.520(3) . ?
C4 C5 1.521(3) . ?
C4 C6 1.339(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.477(3) . ?
C6 C13 1.447(3) . ?
C7 C8 1.406(3) . ?
C7 C12 1.399(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.375(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.387(3) . ?
C10 C11 1.384(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(3) . ?
C12 H12 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
H1A C1 H1B 120.0 . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
C1 C2 C3 134.3(2) . . ?
C1 C2 C5 133.8(2) . . ?
C3 C2 C5 91.92(17) . . ?
C2 C3 H3A 114.0 . . ?
C2 C3 H3B 114.0 . . ?
H3A C3 H3B 111.2 . . ?
C4 C3 C2 87.86(17) . . ?
C4 C3 H3A 114.0 . . ?
C4 C3 H3B 114.0 . . ?
C3 C4 C5 92.51(17) . . ?
C6 C4 C3 137.0(2) . . ?
C6 C4 C5 130.5(2) . . ?
C2 C5 H5A 114.0 . . ?
C2 C5 H5B 114.0 . . ?
C4 C5 C2 87.68(17) . . ?
C4 C5 H5A 114.0 . . ?
C4 C5 H5B 114.0 . . ?
H5A C5 H5B 111.2 . . ?
C4 C6 C7 128.4(2) . . ?
C4 C6 C13 114.4(2) . . ?
C13 C6 C7 117.3(2) . . ?
C8 C7 C6 122.0(2) . . ?
C12 C7 C6 120.23(19) . . ?
C12 C7 C8 117.7(2) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.4(2) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.5(2) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 Br1 119.19(17) . . ?
C11 C10 Br1 119.83(17) . . ?
C11 C10 C9 121.0(2) . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 119.1(2) . . ?
C12 C11 H11 120.5 . . ?
C7 C12 H12 119.3 . . ?
C11 C12 C7 121.3(2) . . ?
C11 C12 H12 119.3 . . ?
N1 C13 C6 177.2(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
