# 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 2018

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1447218'
_audit_update_record             
;
2018-08-09 deposited with the CCDC.
2018-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H9 Br2 Cd N O3'
_chemical_formula_weight         403.35

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'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.8799(6)
_cell_length_b                   7.4837(5)
_cell_length_c                   8.0522(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.935(3)
_cell_angle_gamma                90
_cell_volume                     462.80(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2490
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      30.61

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.895
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    10.960
_shelx_estimated_absorpt_T_min   0.138
_shelx_estimated_absorpt_T_max   0.170
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.138
_exptl_absorpt_correction_T_max  0.170
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6547
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.595
_diffrn_reflns_theta_max         30.615
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.900
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2490
_reflns_number_gt                2320
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_max     0.835
_reflns_Friedel_fraction_full    0.992

_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.
;

_computing_data_collection       'APEXII (Bruker, 2012)'
_computing_cell_refinement       'APEXII/SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2012)'
_computing_structure_solution    'SHELXS-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2016/6 (Sheldrick, 2016)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0674P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.132(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 971 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.037(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2490
_refine_ls_number_parameters     111
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0209
_refine_ls_R_factor_gt           0.0187
_refine_ls_wR_factor_ref         0.0569
_refine_ls_wR_factor_gt          0.0549
_refine_ls_goodness_of_fit_ref   0.616
_refine_ls_restrained_S_all      0.616
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.1742(4) 0.8000(10) 0.0333(4) 0.0176(6) Uani 1 1 d . . . . .
C2 C 0.0494(4) 0.8112(8) 0.1541(4) 0.0208(7) Uani 1 1 d . . . . .
H2 H -0.071212 0.816177 0.088213 0.025 Uiso 1 1 calc R U . . .
C3 C 0.0826(6) 0.9616(7) 0.2839(6) 0.0256(10) Uani 1 1 d . . . . .
H3A H -0.026038 1.002342 0.308474 0.031 Uiso 1 1 calc R U . . .
H3B H 0.138351 1.061662 0.241085 0.031 Uiso 1 1 calc R U . . .
C4 C 0.2027(6) 0.8837(7) 0.4453(6) 0.0242(10) Uani 1 1 d . . . . .
H4 H 0.316009 0.943829 0.468077 0.029 Uiso 1 1 calc R U . . .
C5 C 0.2236(7) 0.6879(7) 0.4078(7) 0.0272(10) Uani 1 1 d . . . . .
H5A H 0.334291 0.666488 0.377632 0.033 Uiso 1 1 calc R U . . .
H5B H 0.217488 0.615104 0.506001 0.033 Uiso 1 1 calc R U . . .
N1 N 0.0764(6) 0.6466(6) 0.2621(6) 0.0297(10) Uani 1 1 d . . . . .
H1A H -0.019197 0.620799 0.298872 0.036 Uiso 1 1 calc R U . . .
H1B H 0.102345 0.553898 0.203135 0.036 Uiso 1 1 calc R U . . .
O1 O 0.2076(4) 0.9448(5) -0.0330(4) 0.0244(8) Uani 1 1 d . . . . .
O2 O 0.2266(4) 0.6484(5) 0.0055(5) 0.0244(7) Uani 1 1 d . . . . .
O3 O 0.1210(5) 0.9085(5) 0.5843(4) 0.0373(8) Uani 1 1 d . . . . .
H3 H 0.183883 0.868685 0.671562 0.056 Uiso 1 1 calc R U . . .
Br1 Br 0.37973(4) 1.30200(7) -0.24923(4) 0.02303(12) Uani 1 1 d . . . . .
Br2 Br 0.43647(4) 1.29943(7) 0.22554(4) 0.02496(12) Uani 1 1 d . . . . .
Cd1 Cd 0.49692(5) 1.05022(6) 0.00188(6) 0.02155(11) 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
C1 O2 1.244(8) . ?
C1 O1 1.261(7) . ?
C1 C2 1.533(5) . ?
C2 N1 1.495(7) . ?
C2 C3 1.518(7) . ?
C2 H2 0.9800 . ?
C3 C4 1.540(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O3 1.423(6) . ?
C4 C5 1.513(6) . ?
C4 H4 0.9800 . ?
C5 N1 1.486(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
O1 Cd1 2.369(3) . ?
O2 Cd1 2.313(3) 2_645 ?
O3 H3 0.8200 . ?
Br1 Cd1 2.7378(6) 2_655 ?
Br1 Cd1 2.7669(6) . ?
Br2 Cd1 2.7079(7) . ?
Br2 Cd1 2.7535(7) 2_655 ?

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
O2 C1 O1 126.8(3) . . ?
O2 C1 C2 116.7(6) . . ?
O1 C1 C2 116.5(6) . . ?
N1 C2 C3 103.3(3) . . ?
N1 C2 C1 107.2(5) . . ?
C3 C2 C1 116.2(4) . . ?
N1 C2 H2 109.9 . . ?
C3 C2 H2 109.9 . . ?
C1 C2 H2 109.9 . . ?
C2 C3 C4 106.2(4) . . ?
C2 C3 H3A 110.5 . . ?
C4 C3 H3A 110.5 . . ?
C2 C3 H3B 110.5 . . ?
C4 C3 H3B 110.5 . . ?
H3A C3 H3B 108.7 . . ?
O3 C4 C5 111.8(4) . . ?
O3 C4 C3 108.3(4) . . ?
C5 C4 C3 105.8(5) . . ?
O3 C4 H4 110.3 . . ?
C5 C4 H4 110.3 . . ?
C3 C4 H4 110.3 . . ?
N1 C5 C4 105.0(4) . . ?
N1 C5 H5A 110.8 . . ?
C4 C5 H5A 110.8 . . ?
N1 C5 H5B 110.8 . . ?
C4 C5 H5B 110.8 . . ?
H5A C5 H5B 108.8 . . ?
C5 N1 C2 105.8(3) . . ?
C5 N1 H1A 110.6 . . ?
C2 N1 H1A 110.6 . . ?
C5 N1 H1B 110.6 . . ?
C2 N1 H1B 110.6 . . ?
H1A N1 H1B 108.7 . . ?
C1 O1 Cd1 121.5(2) . . ?
C1 O2 Cd1 130.3(3) . 2_645 ?
C4 O3 H3 109.5 . . ?
Cd1 Br1 Cd1 85.662(10) 2_655 . ?
Cd1 Br2 Cd1 86.505(11) . 2_655 ?
O2 Cd1 O1 171.88(14) 2_655 . ?
O2 Cd1 Br2 96.04(10) 2_655 . ?
O1 Cd1 Br2 90.01(9) . . ?
O2 Cd1 Br1 92.93(9) 2_655 2_645 ?
O1 Cd1 Br1 92.04(9) . 2_645 ?
Br2 Cd1 Br1 94.019(19) . 2_645 ?
O2 Cd1 Br2 83.03(10) 2_655 2_645 ?
O1 Cd1 Br2 90.91(10) . 2_645 ?
Br2 Cd1 Br2 179.06(2) . 2_645 ?
Br1 Cd1 Br2 86.094(19) 2_645 2_645 ?
O2 Cd1 Br1 85.82(9) 2_655 . ?
O1 Cd1 Br1 89.16(9) . . ?
Br2 Cd1 Br1 86.410(19) . . ?
Br1 Cd1 Br1 178.716(15) 2_645 . ?
Br2 Cd1 Br1 93.458(19) 2_645 . ?

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
O2 C1 C2 N1 22.3(4) . . . . ?
O1 C1 C2 N1 -160.4(3) . . . . ?
O2 C1 C2 C3 137.2(4) . . . . ?
O1 C1 C2 C3 -45.5(4) . . . . ?
N1 C2 C3 C4 25.0(4) . . . . ?
C1 C2 C3 C4 -92.1(5) . . . . ?
C2 C3 C4 O3 -124.2(4) . . . . ?
C2 C3 C4 C5 -4.1(5) . . . . ?
O3 C4 C5 N1 99.1(4) . . . . ?
C3 C4 C5 N1 -18.6(5) . . . . ?
C4 C5 N1 C2 35.2(5) . . . . ?
C3 C2 N1 C5 -37.4(4) . . . . ?
C1 C2 N1 C5 85.9(4) . . . . ?
O2 C1 O1 Cd1 -60.5(5) . . . . ?
C2 C1 O1 Cd1 122.6(3) . . . . ?
O1 C1 O2 Cd1 47.7(5) . . . 2_645 ?
C2 C1 O2 Cd1 -135.4(3) . . . 2_645 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 Br1 0.98 3.00 3.631(3) 123.1 2_545
C3 H3A Br1 0.97 3.11 3.784(5) 128.3 2_545
C3 H3B Br2 0.97 2.97 3.870(5) 154.5 .
C5 H5A Br1 0.97 2.87 3.731(6) 148.8 2_645
N1 H1A O3 0.89 2.09 2.825(6) 138.7 2_546
N1 H1A Br1 0.89 3.09 3.757(5) 133.1 2_545
O3 H3 O1 0.82 2.41 3.016(5) 131.1 1_556
O3 H3 Br2 0.82 2.97 3.575(3) 133.0 2_646
C2 H2 Br1 0.98 3.00 3.631(3) 123.1 2_545
C3 H3A Br1 0.97 3.11 3.784(5) 128.3 2_545
C3 H3B Br2 0.97 2.97 3.870(5) 154.5 .
C4 H4 Br2 0.98 2.98 3.484(5) 112.9 2_646
C5 H5A Br1 0.97 2.87 3.731(6) 148.8 2_645
N1 H1A O3 0.89 2.09 2.825(6) 138.7 2_546
N1 H1A Br1 0.89 3.09 3.757(5) 133.1 2_545
O3 H3 O1 0.82 2.41 3.016(5) 131.1 1_556
O3 H3 Br2 0.82 2.97 3.575(3) 133.0 2_646

_refine_diff_density_max         0.692
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.109

