# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_222
_database_code_depnum_ccdc_archive 'CCDC 1960411'
loop_
_audit_author_name
_audit_author_address
'Juhua Feng'
;Sichuan Agricultural University
China
;
_audit_update_record             
;
2019-10-21 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;
_audit_creation_date             2019-10-17
_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         'C15 H10 Br N O5'
_chemical_formula_sum            'C15 H10 Br N O5'
_chemical_formula_weight         364.15
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.6910(7)
_cell_length_b                   13.9407(12)
_cell_length_c                   13.4635(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.390(3)
_cell_angle_gamma                90
_cell_volume                     1441.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7800
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.519
_cell_measurement_theta_min      2.922
_shelx_estimated_absorpt_T_max   0.689
_shelx_estimated_absorpt_T_min   0.522
_exptl_absorpt_coefficient_mu    2.876
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0740 before and 0.0481 after correction.
The Ratio of minimum to maximum transmission is 0.8781.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22584
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.627
_diffrn_reflns_theta_min         3.029
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                2272
_reflns_number_total             3330
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.043
_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)+(0.0718P)²+0.5783P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1347
_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 Ternary CH refined with riding coordinates:
 C8(H8), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C14(H14), C5(H5), C2(H2), C3(H3), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.08757(5) 0.57884(3) 0.36571(3) 0.0878(2) Uani 1 1 d . . . . .
O3 O 0.5953(2) 0.56431(13) 0.08983(13) 0.0427(4) Uani 1 1 d . . . . .
O1 O 0.1497(3) 0.5775(2) 0.04239(19) 0.0768(8) Uani 1 1 d . . . . .
N1 N 0.3012(3) 0.59892(17) 0.03909(16) 0.0453(6) Uani 1 1 d . . . . .
O2 O 0.3608(3) 0.65350(18) -0.01973(17) 0.0728(7) Uani 1 1 d . . . . .
C10 C 0.5548(3) 0.65992(17) 0.22528(17) 0.0363(5) Uani 1 1 d . . . . .
O5 O 1.0103(3) 0.8069(2) 0.2146(2) 0.0815(8) Uani 1 1 d . . . . .
C9 C 0.6617(3) 0.63916(19) 0.15019(18) 0.0387(6) Uani 1 1 d . . . . .
O4 O 0.8338(4) 0.84588(17) 0.34172(18) 0.0752(7) Uani 1 1 d . . . . .
C8 C 0.4253(3) 0.54787(19) 0.11551(18) 0.0373(6) Uani 1 1 d . . . . .
H8 H 0.400703 0.478910 0.116301 0.045 Uiso 1 1 calc R . . . .
C6 C 0.4164(4) 0.51652(18) 0.30045(17) 0.0387(6) Uani 1 1 d . . . . .
C1 C 0.2913(4) 0.5013(2) 0.36798(19) 0.0475(7) Uani 1 1 d . . . . .
C7 C 0.4024(3) 0.59221(18) 0.21948(17) 0.0364(5) Uani 1 1 d . . . . .
H7 H 0.292102 0.627247 0.220744 0.044 Uiso 1 1 calc R . . . .
C11 C 0.6019(4) 0.73038(19) 0.29589(19) 0.0456(7) Uani 1 1 d . . . . .
H11 H 0.531400 0.746701 0.347078 0.055 Uiso 1 1 calc R . . . .
C12 C 0.7585(4) 0.7733(2) 0.2842(2) 0.0491(7) Uani 1 1 d . . . . .
C14 C 0.8199(4) 0.6829(2) 0.1369(2) 0.0503(7) Uani 1 1 d . . . . .
H14 H 0.889941 0.668113 0.085088 0.060 Uiso 1 1 calc R . . . .
C13 C 0.8624(4) 0.7503(2) 0.2079(2) 0.0536(8) Uani 1 1 d . . . . .
C5 C 0.5660(5) 0.4586(2) 0.3100(2) 0.0546(8) Uani 1 1 d . . . . .
H5 H 0.655049 0.467888 0.267156 0.066 Uiso 1 1 calc R . . . .
C2 C 0.3092(6) 0.4307(2) 0.4403(2) 0.0641(9) Uani 1 1 d . . . . .
H2 H 0.222551 0.421574 0.484765 0.077 Uiso 1 1 calc R . . . .
C3 C 0.4546(6) 0.3746(2) 0.4459(2) 0.0673(10) Uani 1 1 d . . . . .
H3 H 0.466218 0.326699 0.493857 0.081 Uiso 1 1 calc R . . . .
C4 C 0.5827(5) 0.3881(2) 0.3821(2) 0.0626(9) Uani 1 1 d . . . . .
H4 H 0.681824 0.349798 0.386867 0.075 Uiso 1 1 calc R . . . .
C15 C 1.0032(6) 0.8583(3) 0.3056(3) 0.0887(13) Uani 1 1 d . . . . .
H15A H 1.025620 0.925832 0.294717 0.106 Uiso 1 1 calc R . . . .
H15B H 1.091047 0.834152 0.353961 0.106 Uiso 1 1 calc R . . . .


_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 1.902(3) . ?
O3 C9 1.400(3) . ?
O3 C8 1.391(3) . ?
O1 N1 1.206(3) . ?
N1 O2 1.208(3) . ?
N1 C8 1.536(3) . ?
C10 C9 1.371(4) . ?
C10 C7 1.503(4) . ?
C10 C11 1.400(4) . ?
O5 C13 1.383(4) . ?
O5 C15 1.424(6) . ?
C9 C14 1.382(4) . ?
O4 C12 1.380(3) . ?
O4 C15 1.428(5) . ?
C8 H8 0.9800 . ?
C8 C7 1.550(3) . ?
C6 C1 1.379(4) . ?
C6 C7 1.516(3) . ?
C6 C5 1.405(4) . ?
C1 C2 1.387(4) . ?
C7 H7 0.9800 . ?
C11 H11 0.9300 . ?
C11 C12 1.362(4) . ?
C12 C13 1.377(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.365(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.382(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.362(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.358(5) . ?
C4 H4 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?

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
C8 O3 C9 107.14(19) . . ?
O1 N1 O2 125.8(3) . . ?
O1 N1 C8 115.1(2) . . ?
O2 N1 C8 119.1(2) . . ?
C9 C10 C7 109.2(2) . . ?
C9 C10 C11 120.4(3) . . ?
C11 C10 C7 130.2(2) . . ?
C13 O5 C15 105.7(3) . . ?
C10 C9 O3 111.8(2) . . ?
C10 C9 C14 124.9(3) . . ?
C14 C9 O3 123.2(2) . . ?
C12 O4 C15 105.0(3) . . ?
O3 C8 N1 108.3(2) . . ?
O3 C8 H8 110.4 . . ?
O3 C8 C7 108.5(2) . . ?
N1 C8 H8 110.4 . . ?
N1 C8 C7 108.7(2) . . ?
C7 C8 H8 110.4 . . ?
C1 C6 C7 123.9(2) . . ?
C1 C6 C5 116.8(3) . . ?
C5 C6 C7 119.2(2) . . ?
C6 C1 Br1 120.6(2) . . ?
C6 C1 C2 121.9(3) . . ?
C2 C1 Br1 117.5(3) . . ?
C10 C7 C8 99.7(2) . . ?
C10 C7 C6 112.2(2) . . ?
C10 C7 H7 111.0 . . ?
C8 C7 H7 111.0 . . ?
C6 C7 C8 111.4(2) . . ?
C6 C7 H7 111.0 . . ?
C10 C11 H11 122.4 . . ?
C12 C11 C10 115.2(3) . . ?
C12 C11 H11 122.4 . . ?
C11 C12 O4 127.0(3) . . ?
C11 C12 C13 122.7(3) . . ?
C13 C12 O4 110.3(3) . . ?
C9 C14 H14 123.5 . . ?
C13 C14 C9 112.9(3) . . ?
C13 C14 H14 123.5 . . ?
C12 C13 O5 109.3(3) . . ?
C14 C13 O5 126.9(3) . . ?
C14 C13 C12 123.9(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.7 . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 119.9 . . ?
O5 C15 O4 108.3(3) . . ?
O5 C15 H15A 110.0 . . ?
O5 C15 H15B 110.0 . . ?
O4 C15 H15A 110.0 . . ?
O4 C15 H15B 110.0 . . ?
H15A C15 H15B 108.4 . . ?

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 C1 C2 C3 -178.8(2) . . . . ?
O3 C9 C14 C13 -176.5(2) . . . . ?
O3 C8 C7 C10 18.8(2) . . . . ?
O3 C8 C7 C6 -99.7(2) . . . . ?
O1 N1 C8 O3 168.0(2) . . . . ?
O1 N1 C8 C7 -74.3(3) . . . . ?
N1 C8 C7 C10 -98.7(2) . . . . ?
N1 C8 C7 C6 142.7(2) . . . . ?
O2 N1 C8 O3 -9.9(3) . . . . ?
O2 N1 C8 C7 107.8(3) . . . . ?
C10 C9 C14 C13 0.6(4) . . . . ?
C10 C11 C12 O4 178.5(3) . . . . ?
C10 C11 C12 C13 0.8(4) . . . . ?
C9 O3 C8 N1 99.0(2) . . . . ?
C9 O3 C8 C7 -18.8(3) . . . . ?
C9 C10 C7 C8 -12.1(3) . . . . ?
C9 C10 C7 C6 105.8(2) . . . . ?
C9 C10 C11 C12 -0.9(4) . . . . ?
C9 C14 C13 O5 -179.3(3) . . . . ?
C9 C14 C13 C12 -0.7(4) . . . . ?
O4 C12 C13 O5 0.8(3) . . . . ?
O4 C12 C13 C14 -178.0(3) . . . . ?
C8 O3 C9 C10 11.0(3) . . . . ?
C8 O3 C9 C14 -171.6(2) . . . . ?
C6 C1 C2 C3 0.4(5) . . . . ?
C6 C5 C4 C3 -0.8(5) . . . . ?
C1 C6 C7 C10 123.5(3) . . . . ?
C1 C6 C7 C8 -125.8(3) . . . . ?
C1 C6 C5 C4 1.9(4) . . . . ?
C1 C2 C3 C4 0.8(5) . . . . ?
C7 C10 C9 O3 1.8(3) . . . . ?
C7 C10 C9 C14 -175.6(2) . . . . ?
C7 C10 C11 C12 173.9(3) . . . . ?
C7 C6 C1 Br1 -1.3(4) . . . . ?
C7 C6 C1 C2 179.5(3) . . . . ?
C7 C6 C5 C4 -179.2(3) . . . . ?
C11 C10 C9 O3 177.6(2) . . . . ?
C11 C10 C9 C14 0.3(4) . . . . ?
C11 C10 C7 C8 172.6(3) . . . . ?
C11 C10 C7 C6 -69.4(3) . . . . ?
C11 C12 C13 O5 178.8(3) . . . . ?
C11 C12 C13 C14 0.0(5) . . . . ?
C12 O4 C15 O5 11.9(4) . . . . ?
C13 O5 C15 O4 -11.6(4) . . . . ?
C5 C6 C1 Br1 177.5(2) . . . . ?
C5 C6 C1 C2 -1.7(4) . . . . ?
C5 C6 C7 C10 -55.3(3) . . . . ?
C5 C6 C7 C8 55.4(3) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C15 O5 C13 C12 6.7(4) . . . . ?
C15 O5 C13 C14 -174.5(3) . . . . ?
C15 O4 C12 C11 174.2(3) . . . . ?
C15 O4 C12 C13 -7.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
