# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_1211_3_0m
_database_code_depnum_ccdc_archive 'CCDC 1920901'
loop_
_audit_author_name
_audit_author_address
'Zhenhua DING'
;China Pharmaceutical University
China
;
_audit_update_record             
;
2019-06-05 deposited with the CCDC.	2019-09-25 downloaded from the CCDC.
;
_audit_creation_date             2018-12-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H8 Br N O'
_chemical_formula_sum            'C10 H8 Br N O'
_chemical_formula_weight         238.08
_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'
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                   5.6468(5)
_cell_length_b                   12.0159(10)
_cell_length_c                   14.1013(13)
_cell_angle_alpha                81.991(5)
_cell_angle_beta                 89.552(5)
_cell_angle_gamma                82.145(5)
_cell_volume                     938.51(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4539
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   0.723
_shelx_estimated_absorpt_T_min   0.493
_exptl_absorpt_coefficient_mu    4.335
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0951 before and 0.0518 after correction. The Ratio of minimum to maximum transmission is 0.5828. 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    1.685
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12592
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         2.412
_diffrn_ambient_temperature      149.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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                2849
_reflns_number_total             3641
_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         0.870
_refine_diff_density_min         -0.780
_refine_diff_density_rms         0.136
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3641
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0631
_refine_ls_restrained_S_all      1.182
_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)+(0.0064P)²+10.4222P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1577
_refine_ls_wR_factor_ref         0.1658
_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:
 C3(H3), C5(H5), C2(H2), C17(H17), C6(H6), C19(H19), C8(H8), C16(H16),
 C20(H20), C13(H13)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_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 0.50726(17) 0.11569(7) 0.88548(7) 0.0437(3) Uani 1 1 d . . . . .
Br2 Br 1.00908(18) 0.08161(8) 0.60944(7) 0.0458(3) Uani 1 1 d . . . . .
O1 O 0.4462(9) 0.8130(4) 0.8611(4) 0.0308(12) Uani 1 1 d . . . . .
O2 O 0.9604(9) 0.7679(4) 0.6474(4) 0.0328(12) Uani 1 1 d . . . . .
N2 N 0.6876(11) 0.6608(5) 0.6140(4) 0.0271(14) Uani 1 1 d . . . . .
N1 N 0.1720(11) 0.6961(5) 0.8861(4) 0.0274(14) Uani 1 1 d . . . . .
C18 C 0.9795(13) 0.2393(6) 0.6152(5) 0.0228(15) Uani 1 1 d . . . . .
C4 C 0.4237(12) 0.5097(6) 0.8739(5) 0.0212(14) Uani 1 1 d . . . . .
C14 C 0.9102(12) 0.5923(6) 0.6320(5) 0.0225(15) Uani 1 1 d . . . . .
C15 C 0.9381(12) 0.4713(6) 0.6262(5) 0.0225(15) Uani 1 1 d . . . . .
C3 C 0.2408(12) 0.4485(6) 0.9093(5) 0.0251(15) Uani 1 1 d . . . . .
H3 H 0.0962 0.4879 0.9298 0.030 Uiso 1 1 calc R . . . .
C5 C 0.6285(12) 0.4512(6) 0.8399(5) 0.0248(15) Uani 1 1 d . . . . .
H5 H 0.7524 0.4919 0.8138 0.030 Uiso 1 1 calc R . . . .
C2 C 0.2671(13) 0.3308(7) 0.9153(5) 0.0277(16) Uani 1 1 d . . . . .
H2 H 0.1454 0.2895 0.9424 0.033 Uiso 1 1 calc R . . . .
C17 C 1.1663(13) 0.2833(7) 0.6554(5) 0.0296(17) Uani 1 1 d . . . . .
H17 H 1.3065 0.2348 0.6791 0.035 Uiso 1 1 calc R . . . .
C6 C 0.6550(13) 0.3341(7) 0.8434(5) 0.0278(16) Uani 1 1 d . . . . .
H6 H 0.7962 0.2946 0.8203 0.033 Uiso 1 1 calc R . . . .
C7 C 0.3929(12) 0.6324(6) 0.8702(5) 0.0230(15) Uani 1 1 d . . . . .
C9 C 0.2116(14) 0.7998(7) 0.8796(6) 0.0300(17) Uani 1 1 d . . . . .
C19 C 0.7724(13) 0.3087(7) 0.5825(5) 0.0302(17) Uani 1 1 d . . . . .
H19 H 0.6447 0.2779 0.5567 0.036 Uiso 1 1 calc R . . . .
C1 C 0.4726(13) 0.2757(6) 0.8811(5) 0.0248(15) Uani 1 1 d . . . . .
C8 C 0.5595(13) 0.7042(6) 0.8546(6) 0.0289(16) Uani 1 1 d . . . . .
H8 H 0.7238 0.6837 0.8415 0.035 Uiso 1 1 calc R . . . .
C16 C 1.1442(13) 0.3986(7) 0.6602(5) 0.0276(16) Uani 1 1 d . . . . .
H16 H 1.2711 0.4289 0.6869 0.033 Uiso 1 1 calc R . . . .
C12 C 0.7287(13) 0.7611(7) 0.6235(6) 0.0308(17) Uani 1 1 d . . . . .
C20 C 0.7540(13) 0.4235(7) 0.5878(5) 0.0275(16) Uani 1 1 d . . . . .
H20 H 0.6124 0.4714 0.5647 0.033 Uiso 1 1 calc R . . . .
C13 C 1.0743(13) 0.6561(7) 0.6532(6) 0.0304(17) Uani 1 1 d . . . . .
H13 H 1.2376 0.6302 0.6691 0.036 Uiso 1 1 calc R . . . .
C10 C 0.0432(15) 0.9033(6) 0.8865(7) 0.040(2) Uani 1 1 d . . . . .
H10A H 0.0956 0.9417 0.9379 0.060 Uiso 1 1 calc GR . . . .
H10B H -0.1168 0.8829 0.9005 0.060 Uiso 1 1 calc GR . . . .
H10C H 0.0389 0.9541 0.8256 0.060 Uiso 1 1 calc GR . . . .
C11 C 0.5608(16) 0.8682(8) 0.6133(7) 0.046(2) Uani 1 1 d . . . . .
H11A H 0.5518 0.8989 0.6742 0.069 Uiso 1 1 calc GR . . . .
H11B H 0.4019 0.8533 0.5955 0.069 Uiso 1 1 calc GR . . . .
H11C H 0.6178 0.9232 0.5634 0.069 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
Br1 C1 1.898(7) . ?
Br2 C18 1.892(7) . ?
O1 C9 1.374(9) . ?
O1 C8 1.390(9) . ?
O2 C12 1.370(9) . ?
O2 C13 1.400(9) . ?
N2 C14 1.409(9) . ?
N2 C12 1.282(10) . ?
N1 C7 1.405(9) . ?
N1 C9 1.286(10) . ?
C18 C17 1.400(10) . ?
C18 C19 1.382(10) . ?
C4 C3 1.398(10) . ?
C4 C5 1.387(10) . ?
C4 C7 1.455(10) . ?
C14 C15 1.454(10) . ?
C14 C13 1.341(10) . ?
C15 C16 1.401(10) . ?
C15 C20 1.401(10) . ?
C3 H3 0.9500 . ?
C3 C2 1.392(10) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(10) . ?
C2 H2 0.9500 . ?
C2 C1 1.374(10) . ?
C17 H17 0.9500 . ?
C17 C16 1.384(11) . ?
C6 H6 0.9500 . ?
C6 C1 1.386(10) . ?
C7 C8 1.357(10) . ?
C9 C10 1.473(11) . ?
C19 H19 0.9500 . ?
C19 C20 1.382(11) . ?
C8 H8 0.9500 . ?
C16 H16 0.9500 . ?
C12 C11 1.481(11) . ?
C20 H20 0.9500 . ?
C13 H13 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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 C8 104.7(6) . . ?
C12 O2 C13 104.0(6) . . ?
C12 N2 C14 104.7(6) . . ?
C9 N1 C7 105.9(6) . . ?
C17 C18 Br2 119.1(5) . . ?
C19 C18 Br2 119.9(5) . . ?
C19 C18 C17 121.0(7) . . ?
C3 C4 C7 119.8(6) . . ?
C5 C4 C3 118.6(7) . . ?
C5 C4 C7 121.5(6) . . ?
N2 C14 C15 121.3(6) . . ?
C13 C14 N2 109.6(6) . . ?
C13 C14 C15 129.1(7) . . ?
C16 C15 C14 121.9(6) . . ?
C16 C15 C20 117.8(7) . . ?
C20 C15 C14 120.2(6) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 C4 121.1(7) . . ?
C2 C3 H3 119.5 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.9(7) . . ?
C6 C5 H5 119.5 . . ?
C3 C2 H2 120.7 . . ?
C1 C2 C3 118.7(7) . . ?
C1 C2 H2 120.7 . . ?
C18 C17 H17 120.4 . . ?
C16 C17 C18 119.2(7) . . ?
C16 C17 H17 120.4 . . ?
C5 C6 H6 120.5 . . ?
C1 C6 C5 119.0(7) . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C4 122.7(6) . . ?
C8 C7 N1 108.5(6) . . ?
C8 C7 C4 128.8(7) . . ?
O1 C9 C10 117.1(7) . . ?
N1 C9 O1 113.3(7) . . ?
N1 C9 C10 129.5(7) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 C18 118.9(7) . . ?
C20 C19 H19 120.5 . . ?
C2 C1 Br1 119.2(6) . . ?
C2 C1 C6 121.6(7) . . ?
C6 C1 Br1 119.2(6) . . ?
O1 C8 H8 126.2 . . ?
C7 C8 O1 107.6(6) . . ?
C7 C8 H8 126.2 . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.2(7) . . ?
C17 C16 H16 119.4 . . ?
O2 C12 C11 116.6(7) . . ?
N2 C12 O2 114.4(7) . . ?
N2 C12 C11 129.0(7) . . ?
C15 C20 H20 119.0 . . ?
C19 C20 C15 121.9(7) . . ?
C19 C20 H20 119.0 . . ?
O2 C13 H13 126.4 . . ?
C14 C13 O2 107.3(6) . . ?
C14 C13 H13 126.4 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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_22019358xj_0m
_database_code_depnum_ccdc_archive 'CCDC 1920903'
loop_
_audit_author_name
_audit_author_address
'Zhenhua DING'
;China Pharmaceutical University
China
;
_audit_update_record             
;
2019-06-05 deposited with the CCDC.	2019-09-25 downloaded from the CCDC.
;
_audit_creation_date             2019-04-09
_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         'C12 H11 Br N2 O2'
_chemical_formula_sum            'C12 H11 Br N2 O2'
_chemical_formula_weight         295.14
_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'
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      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                   9.930(3)
_cell_length_b                   9.524(3)
_cell_length_c                   24.977(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2362.0(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4532
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.773
_cell_measurement_theta_min      2.620
_shelx_estimated_absorpt_T_max   0.874
_shelx_estimated_absorpt_T_min   0.769
_exptl_absorpt_coefficient_mu    3.471
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1288 before and 0.0799 after correction. The Ratio of minimum to maximum transmission is 0.8124. 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    1.660
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0833
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            17419
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_min         2.621
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1887
_reflns_number_total             2701
_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 (?, 2016)'
_computing_data_collection       ?
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.713
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2701
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.058
_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)+(0.0446P)²+3.3833P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1142
_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. Restrained distances
 N1-H1
 0.87 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C5(H5), C3(H3), C4(H4)
3.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.30511(4) 0.64651(5) 0.50524(2) 0.02717(15) Uani 1 1 d . . . . .
O1 O 0.8823(2) 0.4885(3) 0.60752(11) 0.0234(7) Uani 1 1 d . . . . .
O2 O 1.0320(3) 0.4844(4) 0.67468(13) 0.0380(8) Uani 1 1 d . . . . .
N2 N 0.8395(3) 0.3304(4) 0.73667(13) 0.0201(7) Uani 1 1 d . . . . .
N1 N 0.6192(3) 0.3308(4) 0.72421(13) 0.0210(8) Uani 1 1 d D . . . .
C2 C 0.4154(4) 0.5770(4) 0.56208(15) 0.0202(9) Uani 1 1 d . . . . .
C6 C 0.5826(4) 0.4723(4) 0.64216(16) 0.0182(8) Uani 1 1 d . . . . .
C1 C 0.5296(4) 0.6532(4) 0.57647(16) 0.0195(8) Uani 1 1 d . . . . .
H1A H 0.550895 0.738903 0.558964 0.023 Uiso 1 1 calc R . . . .
C8 C 0.6702(4) 0.4111(4) 0.68340(16) 0.0187(8) Uani 1 1 d . . . . .
C5 C 0.6119(4) 0.6013(4) 0.61696(16) 0.0196(9) Uani 1 1 d . . . . .
H5 H 0.688782 0.653360 0.627781 0.023 Uiso 1 1 calc R . . . .
C7 C 0.8087(4) 0.4090(4) 0.69148(15) 0.0188(8) Uani 1 1 d . . . . .
C3 C 0.3806(4) 0.4531(4) 0.58743(16) 0.0201(9) Uani 1 1 d . . . . .
H3 H 0.300838 0.404137 0.577857 0.024 Uiso 1 1 calc R . . . .
C10 C 0.7226(4) 0.2843(4) 0.75523(16) 0.0201(9) Uani 1 1 d . . . . .
C4 C 0.4653(4) 0.4020(4) 0.62726(16) 0.0209(9) Uani 1 1 d . . . . .
H4 H 0.442547 0.316719 0.644818 0.025 Uiso 1 1 calc R . . . .
C9 C 0.9184(4) 0.4656(4) 0.65862(16) 0.0217(9) Uani 1 1 d . . . . .
C12 C 0.9857(4) 0.5444(5) 0.57313(18) 0.0295(10) Uani 1 1 d . . . . .
H12A H 0.946100 0.571139 0.538670 0.044 Uiso 1 1 calc GR . . . .
H12B H 1.055173 0.472862 0.567320 0.044 Uiso 1 1 calc GR . . . .
H12C H 1.026259 0.627105 0.589997 0.044 Uiso 1 1 calc GR . . . .
C11 C 0.7005(4) 0.1934(5) 0.80289(18) 0.0280(10) Uani 1 1 d . . . . .
H11A H 0.778817 0.132159 0.808004 0.042 Uiso 1 1 calc GR . . . .
H11B H 0.619926 0.135788 0.797370 0.042 Uiso 1 1 calc GR . . . .
H11C H 0.688306 0.252294 0.834691 0.042 Uiso 1 1 calc GR . . . .
H1 H 0.537(2) 0.327(5) 0.7328(17) 0.029(12) Uiso 1 1 d 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 C2 1.911(4) . ?
O1 C9 1.343(5) . ?
O1 C12 1.441(5) . ?
O2 C9 1.211(5) . ?
N2 C7 1.388(5) . ?
N2 C10 1.324(5) . ?
N1 C8 1.371(5) . ?
N1 C10 1.361(5) . ?
N1 H1 0.848(19) . ?
C2 C1 1.393(5) . ?
C2 C3 1.383(6) . ?
C6 C8 1.469(5) . ?
C6 C5 1.410(6) . ?
C6 C4 1.394(5) . ?
C1 H1A 0.9500 . ?
C1 C5 1.391(5) . ?
C8 C7 1.390(5) . ?
C5 H5 0.9500 . ?
C7 C9 1.467(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(5) . ?
C10 C11 1.488(6) . ?
C4 H4 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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 C12 115.8(3) . . ?
C10 N2 C7 105.7(3) . . ?
C8 N1 H1 125(3) . . ?
C10 N1 C8 109.0(3) . . ?
C10 N1 H1 125(3) . . ?
C1 C2 Br1 118.5(3) . . ?
C3 C2 Br1 119.5(3) . . ?
C3 C2 C1 122.0(4) . . ?
C5 C6 C8 122.4(3) . . ?
C4 C6 C8 119.4(4) . . ?
C4 C6 C5 118.1(4) . . ?
C2 C1 H1A 120.6 . . ?
C5 C1 C2 118.7(4) . . ?
C5 C1 H1A 120.6 . . ?
N1 C8 C6 121.6(3) . . ?
N1 C8 C7 104.4(3) . . ?
C7 C8 C6 133.9(4) . . ?
C6 C5 H5 119.6 . . ?
C1 C5 C6 120.9(4) . . ?
C1 C5 H5 119.6 . . ?
N2 C7 C8 110.1(3) . . ?
N2 C7 C9 119.3(3) . . ?
C8 C7 C9 130.4(4) . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.4(4) . . ?
C4 C3 H3 120.8 . . ?
N2 C10 N1 110.7(3) . . ?
N2 C10 C11 127.0(3) . . ?
N1 C10 C11 122.3(3) . . ?
C6 C4 H4 119.1 . . ?
C3 C4 C6 121.8(4) . . ?
C3 C4 H4 119.1 . . ?
O1 C9 C7 113.1(3) . . ?
O2 C9 O1 122.7(4) . . ?
O2 C9 C7 124.1(4) . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
