# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_210309c_0m
_database_code_depnum_ccdc_archive 'CCDC 2070218'
loop_
_audit_author_name
_audit_author_address
'Meng Xiang-Gao'
;College of Chemistry , Central China Normal University
China
;
_audit_update_record             
;
2021-03-14 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;
_audit_creation_date             2021-03-11
_audit_creation_method           
; 
Olex2 1.3 
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) 
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 Br N O4'
_chemical_formula_sum            'C15 H16 Br N O4'
_chemical_formula_weight         354.20
_chemical_absolute_configuration ad
_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 0.0137 0.0067 '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 -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.6884(10)
_cell_length_b                   13.820(2)
_cell_length_c                   8.5300(13)
_cell_angle_alpha                90
_cell_angle_beta                 92.210(2)
_cell_angle_gamma                90
_cell_volume                     787.9(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      72.33
_cell_measurement_theta_min      2.78
_shelx_estimated_absorpt_T_max   0.793
_shelx_estimated_absorpt_T_min   0.642
_exptl_absorpt_coefficient_mu    2.434
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_unetI/netI     0.0782
_diffrn_reflns_Laue_measured_fraction_full 0.655
_diffrn_reflns_Laue_measured_fraction_max 0.790
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11510
_diffrn_reflns_point_group_measured_fraction_full 0.596
_diffrn_reflns_point_group_measured_fraction_max 0.754
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         72.333
_diffrn_reflns_theta_min         7.463
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.655
_diffrn_measured_fraction_theta_max 0.790
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.837
_reflns_Friedel_fraction_full    0.531
_reflns_Friedel_fraction_max     0.714
_reflns_number_gt                3558
_reflns_number_total             3566
_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 (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XM  (Sheldrick, 2008)'
_refine_diff_density_max         0.840
_refine_diff_density_min         -0.888
_refine_diff_density_rms         0.201
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1582 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.008(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3566
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0638
_refine_ls_restrained_S_all      1.202
_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)+(0.1122P)²+0.0264P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1662
_refine_ls_wR_factor_ref         0.1663
_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 
2.a Ternary CH refined with riding coordinates: 
 C7(H7) 
2.b Secondary CH2 refined with riding coordinates: 
 C10(H10A,H10B), C13(H13A,H13B) 
2.c Aromatic/amide H refined with riding coordinates: 
 C2(H2), C3(H3), C5(H5), C6(H6) 
2.d Idealised Me refined as rotating group: 
 C12(H12A,H12B,H12C), C16(H16A,H16B,H16C) 
2.e : 
 C9(H9) 
;
_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 -0.11242(6) 0.23279(4) 0.66167(6) 0.0646(2) Uani 1 1 d . . . . .
C1 C 0.4342(5) 0.4307(2) 0.5616(4) 0.0419(5) Uani 1 1 d . . . . .
C2 C 0.4239(6) 0.3820(3) 0.7034(4) 0.0506(7) Uani 1 1 d . . . . .
H2 H 0.527173 0.388935 0.778718 0.061 Uiso 1 1 calc R U . . .
C3 C 0.2621(7) 0.3230(3) 0.7347(4) 0.0533(7) Uani 1 1 d . . . . .
H3 H 0.256389 0.290740 0.830114 0.064 Uiso 1 1 calc R U . . .
C4 C 0.1086(5) 0.3130(3) 0.6208(4) 0.0467(6) Uani 1 1 d . . . . .
C5 C 0.1167(6) 0.3596(3) 0.4790(5) 0.0546(8) Uani 1 1 d . . . . .
H5 H 0.013883 0.352225 0.403457 0.065 Uiso 1 1 calc R U . . .
C6 C 0.2814(6) 0.4182(3) 0.4495(4) 0.0516(7) Uani 1 1 d . . . . .
H6 H 0.288280 0.449318 0.353159 0.062 Uiso 1 1 calc R U . . .
C7 C 0.6220(5) 0.4909(3) 0.5376(4) 0.0464(6) Uani 1 1 d . . . . .
H7 H 0.736366 0.447171 0.553834 0.056 Uiso 1 1 calc R U . . .
C8 C 0.6337(7) 0.5301(3) 0.3762(5) 0.0537(7) Uani 1 1 d . . . . .
C9 C 0.6503(11) 0.5654(5) 0.2520(5) 0.0700(13) Uani 1 1 d . . . . .
H9 H 0.663343 0.593276 0.153770 0.084 Uiso 1 1 calc R U . . .
C10 C 0.5050(6) 0.6470(2) 0.6329(3) 0.0456(6) Uani 1 1 d . . . . .
H10A H 0.377423 0.622469 0.592183 0.055 Uiso 1 1 calc R U . . .
H10B H 0.557440 0.690363 0.555029 0.055 Uiso 1 1 calc R U . . .
C11 C 0.4732(7) 0.7025(3) 0.7816(4) 0.0524(8) Uani 1 1 d . . . . .
C12 C 0.2713(17) 0.8225(5) 0.8927(6) 0.091(2) Uani 1 1 d . . . . .
H12A H 0.371729 0.870920 0.913725 0.136 Uiso 1 1 calc R U . . .
H12B H 0.261654 0.781205 0.982576 0.136 Uiso 1 1 calc R U . . .
H12C H 0.144682 0.853261 0.870654 0.136 Uiso 1 1 calc R U . . .
C13 C 0.8504(6) 0.5940(3) 0.6907(4) 0.0518(8) Uani 1 1 d . . . . .
H13A H 0.857442 0.662806 0.712710 0.062 Uiso 1 1 calc R U . . .
H13B H 0.928103 0.581271 0.599229 0.062 Uiso 1 1 calc R U . . .
C14 C 0.9377(5) 0.5384(3) 0.8291(3) 0.0448(6) Uani 1 1 d . . . . .
C16 C 1.2090(12) 0.5295(7) 1.0101(10) 0.087(2) Uani 1 1 d . . . A 2
H16A H 1.213773 0.460737 0.995099 0.131 Uiso 1 1 calc R U . A 2
H16B H 1.134084 0.543862 1.101040 0.131 Uiso 1 1 calc R U . A 2
H16C H 1.342604 0.554176 1.024857 0.131 Uiso 1 1 calc R U . A 2
N1 N 0.6431(4) 0.5664(2) 0.6578(3) 0.0453(5) Uani 1 1 d . . . . .
O1 O 0.5660(9) 0.6928(4) 0.9048(4) 0.0772(12) Uani 1 1 d . . . . .
O2 O 0.3253(8) 0.7656(3) 0.7594(3) 0.0666(9) Uani 1 1 d . . . . .
O3 O 0.8620(7) 0.4709(4) 0.8909(5) 0.0775(13) Uani 1 1 d . . . . .
O4 O 1.1144(6) 0.5740(4) 0.8751(6) 0.0735(12) 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 C4 1.891(4) . ?
C1 C2 1.389(5) . ?
C1 C6 1.383(4) . ?
C1 C7 1.527(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(5) . ?
C4 C5 1.373(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.398(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C7 C8 1.485(6) . ?
C7 N1 1.465(5) . ?
C8 C9 1.175(7) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.505(4) . ?
C10 N1 1.457(4) . ?
C11 O1 1.207(5) . ?
C11 O2 1.327(6) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 O2 1.440(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.508(4) . ?
C13 N1 1.455(4) . ?
C14 O3 1.193(5) . ?
C14 O4 1.326(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 O4 1.431(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
C2 C1 C7 116.7(3) . . ?
C6 C1 C2 118.8(3) . . ?
C6 C1 C7 124.4(3) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.1(3) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.9(3) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 Br1 119.3(3) . . ?
C5 C4 Br1 119.7(3) . . ?
C5 C4 C3 121.0(3) . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.3(3) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C5 120.9(3) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C1 C7 H7 106.7 . . ?
C8 C7 C1 113.3(3) . . ?
C8 C7 H7 106.7 . . ?
N1 C7 C1 110.6(3) . . ?
N1 C7 H7 106.7 . . ?
N1 C7 C8 112.4(3) . . ?
C9 C8 C7 176.0(5) . . ?
C8 C9 H9 180.0 . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
N1 C10 H10A 109.2 . . ?
N1 C10 H10B 109.2 . . ?
N1 C10 C11 112.1(3) . . ?
O1 C11 C10 126.4(5) . . ?
O1 C11 O2 123.5(4) . . ?
O2 C11 C10 110.1(3) . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 C14 110.8(3) . . ?
O3 C14 C13 125.9(3) . . ?
O3 C14 O4 123.2(3) . . ?
O4 C14 C13 110.9(3) . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
C10 N1 C7 113.5(2) . . ?
C13 N1 C7 112.7(3) . . ?
C13 N1 C10 114.9(3) . . ?
C11 O2 C12 117.0(5) . . ?
C14 O4 C16 116.1(5) . . ?

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 C4 C5 C6 -179.6(3) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C1 C7 N1 C10 -74.9(4) . . . . ?
C1 C7 N1 C13 152.3(3) . . . . ?
C2 C1 C6 C5 1.5(6) . . . . ?
C2 C1 C7 C8 172.5(3) . . . . ?
C2 C1 C7 N1 -60.2(4) . . . . ?
C2 C3 C4 Br1 179.9(3) . . . . ?
C2 C3 C4 C5 0.7(6) . . . . ?
C3 C4 C5 C6 -0.4(6) . . . . ?
C4 C5 C6 C1 -0.8(7) . . . . ?
C6 C1 C2 C3 -1.2(6) . . . . ?
C6 C1 C7 C8 -4.2(5) . . . . ?
C6 C1 C7 N1 123.1(4) . . . . ?
C7 C1 C2 C3 -178.1(4) . . . . ?
C7 C1 C6 C5 178.1(4) . . . . ?
C8 C7 N1 C10 52.9(4) . . . . ?
C8 C7 N1 C13 -80.0(4) . . . . ?
C10 C11 O2 C12 177.9(6) . . . . ?
C11 C10 N1 C7 158.3(3) . . . . ?
C11 C10 N1 C13 -69.8(4) . . . . ?
C13 C14 O4 C16 177.5(6) . . . . ?
C14 C13 N1 C7 -94.7(4) . . . . ?
C14 C13 N1 C10 133.1(3) . . . . ?
N1 C10 C11 O1 9.3(7) . . . . ?
N1 C10 C11 O2 -170.7(4) . . . . ?
N1 C13 C14 O3 10.3(7) . . . . ?
N1 C13 C14 O4 -170.0(4) . . . . ?
O1 C11 O2 C12 -2.1(9) . . . . ?
O3 C14 O4 C16 -2.8(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
