# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1916377'
loop_
_audit_author_name
_audit_author_address
'Lei Jia'
;YNU
China
;
_audit_update_record             
;
2019-11-09 deposited with the CCDC.	2019-11-29 downloaded from the CCDC.
;
_audit_creation_date             2019-11-09
_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         'C18 H11 Br Cd N3 O4, H2 O, 0.5(C3 H7 N O)'
_chemical_formula_sum            'C19.50 H16.50 Br Cd N3.50 O5.50'
_chemical_formula_weight         580.17
_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'
Cd Cd -0.8075 1.2024 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.661(4)
_cell_length_b                   13.297(3)
_cell_length_c                   23.290(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.660(3)
_cell_angle_gamma                90
_cell_volume                     4595.0(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3755
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.595
_cell_measurement_theta_min      2.428
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.727
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2280
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            15141
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.237
_diffrn_reflns_theta_min         1.846
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.934
_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                3775
_reflns_number_total             5324
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.779
_refine_diff_density_min         -0.847
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5324
_refine_ls_number_restraints     246
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.038
_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)+(0.0683P)²+3.7742P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1299
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 N3-C11
 1.46 with sigma of 0.02
 N4A-C19A = N4A-C20A = N4A-C21A
 1.48 with sigma of 0.01
 C19A-C21A
 2.5 with sigma of 0.02
 C21A-C20A
 2.5 with sigma of 0.02
 C20A-C19A
 2.5 with sigma of 0.02
 O6A-C21A
 1.2 with sigma of 0.02
 N4A-O6A
 2.2 with sigma of 0.02
 O6A-C19A
 3 with sigma of 0.02
 O6-C21
 1.2 with sigma of 0.01
 N0AA-C19 = N0AA-C20 = C21-N0AA
 1.48 with sigma of 0.01
3. Restrained planarity
 N4A, C21A, O6A, C19A, C20A
 with sigma of 0.01
 N0AA, O6, C21, C19, C20
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C21 \\sim O6 \\sim N0AA \\sim C19 \\sim C20: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
C20 \\sim O6 \\sim C21 \\sim N0AA \\sim C19 \\sim C21A \\sim O6A \\sim N4A
\\sim C19A \\sim C20A: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(O6) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(N0AA) \\sim Ueq, Uanis(C19)
\\sim Ueq, Uanis(C20) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C21) \\sim Ueq, Uanis(O6) \\sim Ueq, Uanis(N0AA) \\sim Ueq, Uanis(C19)
\\sim Ueq, Uanis(C20) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C21A) \\sim Ueq, Uanis(O6A) \\sim Ueq, Uanis(N4A) \\sim Ueq, Uanis(C19A)
\\sim Ueq, Uanis(C20A) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(O6) \\sim Ueq,
Uanis(C21) \\sim Ueq, Uanis(N0AA) \\sim Ueq, Uanis(C19) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(O5) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C21, O6, N0AA, C19, C20
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C21A, O6A, N4A, C19A, C20A, C20, O6, C21, N0AA, C19
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
6. Others
 Sof(O6A)=Sof(C21A)=Sof(H21A)=Sof(N4A)=Sof(C19A)=Sof(H19d)=Sof(H19e)=Sof(H19f)=
 Sof(C20A)=Sof(H20d)=Sof(H20e)=Sof(H20f)=0.5*(1-FVAR(2))
 Sof(O6)=Sof(C19)=Sof(H19a)=Sof(H19b)=Sof(H19c)=Sof(C20)=Sof(H20a)=Sof(H20b)=
 Sof(H20c)=Sof(N0AA)=Sof(C21)=Sof(H21)=0.5*FVAR(2)
7.a Riding coordinates:
 O5(H5a,H5b), C19(H19a,H19b,H19c), C20(H20a,H20b,H20c), C19A(H19d,H19e,H19f),
 C20A(H20d,H20e,H20f)
7.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C10(H10), C5(H5), C12(H12), N3(H3a), C13(H13), C17(H17),
 C18(H18), C15(H15), C16(H16), C21(H21), C21A(H21A)
;
_atom_sites_solution_hydrogens   mixed
_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
Cd1 Cd 0.15164(2) 0.25771(2) 0.03554(2) 0.03277(12) Uani 1 1 d . . . . .
Br1 Br -0.29913(5) 0.19943(5) 0.10718(4) 0.0705(2) Uani 1 1 d . . . . .
O4 O -0.2103(2) 0.6362(3) 0.02093(16) 0.0484(9) Uani 1 1 d . . . . .
C1 C -0.2428(3) 0.5751(3) 0.0495(2) 0.0334(10) Uani 1 1 d . . . . .
O3 O -0.3029(2) 0.5976(2) 0.07119(15) 0.0422(8) Uani 1 1 d . . . . .
N2 N 0.0680(2) 0.1836(3) -0.05445(16) 0.0373(9) Uani 1 1 d . . . . .
C2 C -0.2086(3) 0.4684(3) 0.0572(2) 0.0376(11) Uani 1 1 d . . . . .
C3 C -0.2597(3) 0.3956(4) 0.0745(2) 0.0427(12) Uani 1 1 d . . . . .
H3 H -0.3142 0.4131 0.0797 0.051 Uiso 1 1 calc R . . . .
N1 N -0.2542(3) 0.1694(3) -0.37798(18) 0.0440(10) Uani 1 1 d . . . . .
C7 C -0.1288(3) 0.4409(4) 0.0474(2) 0.0371(10) Uani 1 1 d . . . . .
H7 H -0.0963 0.4881 0.0333 0.045 Uiso 1 1 calc R . . . .
O1 O 0.0265(3) 0.2296(3) 0.07438(18) 0.0571(10) Uani 1 1 d . . . . .
O2 O 0.0302(2) 0.3699(3) 0.02586(19) 0.0553(10) Uani 1 1 d . . . . .
C9 C 0.0448(3) 0.2340(4) -0.1072(2) 0.0431(11) Uani 1 1 d . . . . .
C10 C -0.0091(3) 0.1919(4) -0.1603(2) 0.0434(12) Uani 1 1 d . . . . .
H10 H -0.0234 0.2287 -0.1961 0.052 Uiso 1 1 calc R . . . .
C8 C -0.0074(3) 0.3127(4) 0.0522(2) 0.0445(12) Uani 1 1 d . . . . .
C11 C -0.0424(3) 0.0953(4) -0.1610(2) 0.0417(11) Uani 1 1 d D . . . .
C5 C -0.1472(4) 0.2708(4) 0.0766(3) 0.0501(13) Uani 1 1 d . . . . .
H5 H -0.1262 0.2051 0.0839 0.060 Uiso 1 1 calc R . . . .
C6 C -0.0974(3) 0.3419(4) 0.0586(2) 0.0405(11) Uani 1 1 d . . . . .
C12 C -0.0171(3) 0.0429(4) -0.1060(2) 0.0448(12) Uani 1 1 d . . . . .
H12 H -0.0366 -0.0228 -0.1042 0.054 Uiso 1 1 calc R . . . .
N3 N -0.0938(3) 0.0456(4) -0.21363(18) 0.0568(13) Uani 1 1 d D . . . .
H3A H -0.0934 -0.0190 -0.2125 0.068 Uiso 1 1 calc R . . . .
C4 C -0.2292(4) 0.2973(4) 0.0839(3) 0.0492(13) Uani 1 1 d . . . . .
C13 C 0.0366(3) 0.0895(4) -0.0551(2) 0.0448(12) Uani 1 1 d . . . . .
H13 H 0.0524 0.0541 -0.0188 0.054 Uiso 1 1 calc R . . . .
C14 C -0.1455(3) 0.0900(4) -0.2677(2) 0.0444(12) Uani 1 1 d . . . . .
C17 C -0.2203(4) 0.0763(4) -0.3742(2) 0.0491(13) Uani 1 1 d . . . . .
H17 H -0.2330 0.0382 -0.4095 0.059 Uiso 1 1 calc R . . . .
C18 C -0.1674(4) 0.0341(4) -0.3204(2) 0.0524(14) Uani 1 1 d . . . . .
H18 H -0.1467 -0.0316 -0.3197 0.063 Uiso 1 1 calc R . . . .
C15 C -0.1834(4) 0.1837(4) -0.2706(2) 0.0538(14) Uani 1 1 d . . . . .
H15 H -0.1741 0.2213 -0.2355 0.065 Uiso 1 1 calc R . . . .
C16 C -0.2355(4) 0.2223(4) -0.3262(3) 0.0510(13) Uani 1 1 d . . . . .
H16 H -0.2584 0.2871 -0.3276 0.061 Uiso 1 1 calc R . . . .
O5 O 0.0622(5) 0.1619(4) 0.1941(2) 0.115(2) Uani 1 1 d . U . . .
H5A H 0.0576 0.1765 0.1577 0.172 Uiso 1 1 d R . . . .
H5B H 0.0410 0.2097 0.2097 0.172 Uiso 1 1 d R . . . .
O6 O 0.0321(9) 0.3139(10) 0.2559(8) 0.086(5) Uani 0.338(5) 1 d D U P A -2
C19 C 0.0804(15) 0.4521(18) 0.1754(7) 0.080(5) Uani 0.338(5) 1 d D U P A -2
H19A H 0.0585 0.5171 0.1593 0.119 Uiso 0.338(5) 1 d R . P A -2
H19B H 0.0315 0.4049 0.1651 0.119 Uiso 0.338(5) 1 d R . P A -2
H19C H 0.1257 0.4301 0.1586 0.119 Uiso 0.338(5) 1 d R . P A -2
C20 C 0.1801(12) 0.5353(15) 0.2740(11) 0.094(5) Uani 0.338(5) 1 d D U P A -2
H20A H 0.2147 0.5620 0.2502 0.141 Uiso 0.338(5) 1 d R . P A -2
H20B H 0.2199 0.5040 0.3098 0.141 Uiso 0.338(5) 1 d R . P A -2
H20C H 0.1477 0.5888 0.2855 0.141 Uiso 0.338(5) 1 d R . P A -2
N0AA N 0.1161(9) 0.4583(11) 0.2415(7) 0.087(4) Uani 0.338(5) 1 d D U P A -2
C21 C 0.0838(9) 0.3815(10) 0.2748(10) 0.094(4) Uani 0.338(5) 1 d D U P A -2
H21 H 0.1069 0.3861 0.3168 0.113 Uiso 0.338(5) 1 calc R . P A -2
O6A O 0.0229(15) 0.6314(15) 0.2592(14) 0.073(7) Uani 0.162(5) 1 d D U P A -1
C21A C 0.0665(16) 0.5633(18) 0.2792(13) 0.089(5) Uani 0.162(5) 1 d D U P A -1
H21A H 0.0809 0.5513 0.3205 0.106 Uiso 0.162(5) 1 calc R . P A -1
N4A N 0.1008(16) 0.4944(18) 0.2434(12) 0.089(4) Uani 0.162(5) 1 d D U P A -1
C19A C 0.085(3) 0.501(3) 0.1782(12) 0.090(7) Uani 0.162(5) 1 d D U P A -1
H19D H 0.0902 0.5724 0.1738 0.135 Uiso 0.162(5) 1 d R . P A -1
H19E H 0.0258 0.4794 0.1549 0.135 Uiso 0.162(5) 1 d R . P A -1
H19F H 0.1288 0.4674 0.1639 0.135 Uiso 0.162(5) 1 d R . P A -1
C20A C 0.156(3) 0.410(2) 0.2760(18) 0.092(6) Uani 0.162(5) 1 d D U P A -1
H20D H 0.1617 0.3677 0.2437 0.137 Uiso 0.162(5) 1 d R . P A -1
H20E H 0.1317 0.3709 0.3018 0.137 Uiso 0.162(5) 1 d R . P A -1
H20F H 0.2147 0.4344 0.2991 0.137 Uiso 0.162(5) 1 d R . P A -1


_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
Cd1 O4 2.311(4) 5_565 ?
Cd1 O3 2.313(3) 3_545 ?
Cd1 N2 2.307(4) . ?
Cd1 N1 2.295(4) 8_556 ?
Cd1 O1 2.436(4) . ?
Cd1 O2 2.370(3) . ?
Br1 C4 1.889(5) . ?
O4 Cd1 2.311(3) 5_565 ?
O4 C1 1.256(5) . ?
C1 O3 1.239(5) . ?
C1 C2 1.508(6) . ?
O3 Cd1 2.313(3) 3_455 ?
N2 C9 1.343(6) . ?
N2 C13 1.343(6) . ?
C2 C3 1.394(7) . ?
C2 C7 1.390(6) . ?
C3 C4 1.384(7) . ?
N1 Cd1 2.296(4) 8_455 ?
N1 C17 1.340(7) . ?
N1 C16 1.345(7) . ?
C7 C6 1.400(6) . ?
O1 C8 1.262(6) . ?
O2 C8 1.238(6) . ?
C9 C10 1.374(7) . ?
C10 C11 1.385(7) . ?
C8 C6 1.514(6) . ?
C11 C12 1.399(7) . ?
C11 N3 1.398(6) . ?
C5 C6 1.374(7) . ?
C5 C4 1.394(7) . ?
C12 C13 1.363(7) . ?
N3 C14 1.392(6) . ?
C14 C18 1.381(7) . ?
C14 C15 1.372(7) . ?
C17 C18 1.381(7) . ?
C15 C16 1.388(7) . ?
O6 C21 1.196(9) . ?
C19 N0AA 1.462(10) . ?
C20 N0AA 1.463(10) . ?
N0AA C21 1.468(10) . ?
O6A C21A 1.140(18) . ?
C21A N4A 1.452(9) . ?
N4A C19A 1.463(9) . ?
N4A C20A 1.477(9) . ?

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
O4 Cd1 O3 129.32(11) 5_565 3_545 ?
O4 Cd1 O1 144.96(12) 5_565 . ?
O4 Cd1 O2 90.83(13) 5_565 . ?
O3 Cd1 O1 85.26(11) 3_545 . ?
O3 Cd1 O2 139.36(12) 3_545 . ?
N2 Cd1 O4 87.56(13) . 5_565 ?
N2 Cd1 O3 87.31(13) . 3_545 ?
N2 Cd1 O1 88.94(14) . . ?
N2 Cd1 O2 88.71(14) . . ?
N1 Cd1 O4 88.89(14) 8_556 5_565 ?
N1 Cd1 O3 92.06(14) 8_556 3_545 ?
N1 Cd1 N2 174.84(14) 8_556 . ?
N1 Cd1 O1 96.11(15) 8_556 . ?
N1 Cd1 O2 95.08(14) 8_556 . ?
O2 Cd1 O1 54.23(12) . . ?
C1 O4 Cd1 177.0(3) . 5_565 ?
O4 C1 C2 118.9(4) . . ?
O3 C1 O4 123.3(4) . . ?
O3 C1 C2 117.8(4) . . ?
C1 O3 Cd1 105.2(3) . 3_455 ?
C9 N2 Cd1 121.8(3) . . ?
C13 N2 Cd1 120.5(3) . . ?
C13 N2 C9 117.6(4) . . ?
C3 C2 C1 118.2(4) . . ?
C7 C2 C1 122.1(4) . . ?
C7 C2 C3 119.7(4) . . ?
C4 C3 C2 120.0(4) . . ?
C17 N1 Cd1 125.3(3) . 8_455 ?
C17 N1 C16 117.2(4) . . ?
C16 N1 Cd1 117.4(4) . 8_455 ?
C2 C7 C6 119.8(5) . . ?
C8 O1 Cd1 89.8(3) . . ?
C8 O2 Cd1 93.5(3) . . ?
N2 C9 C10 121.9(5) . . ?
C9 C10 C11 120.6(4) . . ?
O1 C8 C6 117.8(5) . . ?
O2 C8 O1 122.4(4) . . ?
O2 C8 C6 119.8(4) . . ?
C10 C11 C12 117.1(4) . . ?
C10 C11 N3 123.9(4) . . ?
N3 C11 C12 118.8(5) . . ?
C6 C5 C4 119.9(5) . . ?
C7 C6 C8 120.3(5) . . ?
C5 C6 C7 120.3(4) . . ?
C5 C6 C8 119.4(4) . . ?
C13 C12 C11 119.0(5) . . ?
C14 N3 C11 126.7(5) . . ?
C3 C4 Br1 119.6(4) . . ?
C3 C4 C5 120.3(5) . . ?
C5 C4 Br1 120.1(4) . . ?
N2 C13 C12 123.8(5) . . ?
C18 C14 N3 118.9(5) . . ?
C15 C14 N3 123.1(5) . . ?
C15 C14 C18 117.7(5) . . ?
N1 C17 C18 123.0(5) . . ?
C17 C18 C14 119.6(5) . . ?
C14 C15 C16 119.8(5) . . ?
N1 C16 C15 122.5(5) . . ?
C19 N0AA C20 123.5(17) . . ?
C19 N0AA C21 115.9(17) . . ?
C20 N0AA C21 120.5(16) . . ?
O6 C21 N0AA 129(2) . . ?
O6A C21A N4A 123.4(17) . . ?
C21A N4A C19A 126.0(12) . . ?
C21A N4A C20A 116.9(13) . . ?
C19A N4A C20A 117.1(12) . . ?

_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_2
_database_code_depnum_ccdc_archive 'CCDC 1916379'
loop_
_audit_author_name
_audit_author_address
'Lei Jia'
;Yunnan University
China
;
_audit_update_record             
;
2019-09-12 deposited with the CCDC.	2019-11-29 downloaded from the CCDC.
;
_audit_creation_date             2019-07-23
_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         'C21 H19 Br Cd N2 O5'
_chemical_formula_sum            'C21 H19 Br Cd N2 O5'
_chemical_formula_weight         571.69
_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'
Cd Cd -0.8075 1.2024 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.340(2)
_cell_length_b                   18.918(3)
_cell_length_c                   16.582(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.615(2)
_cell_angle_gamma                90
_cell_volume                     4421.3(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5158
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.266
_cell_measurement_theta_min      0.023
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.829
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.742315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.0666 before and 0.0298 after correction.
The Ratio of minimum to maximum transmission is 0.7423.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2256
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14786
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.266
_diffrn_reflns_theta_min         1.802
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.939
_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                3613
_reflns_number_total             5158
_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 v7.23A (Bruker, 2003)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.23A (Bruker, 2003)'
_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    'SIR2004 (Burla et al.,  2007)'
_refine_diff_density_max         0.718
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         5158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0350
_refine_ls_restrained_S_all      1.025
_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)+(0.0323P)²+3.3226P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0821
_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:
 C8(H8A,H8B), C7(H7A,H7B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C17(H17), C19(H19), C5(H5), C4(H4), C2(H2), C1(H1), C12(H12),
 C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Cd1 Cd 0.37315(2) 0.08362(2) 0.03979(2) 0.04230(9) Uani 1 1 d . . . . .
Br1 Br 0.36525(5) 0.34107(2) -0.34460(4) 0.1232(3) Uani 1 1 d . . . . .
O1 O 0.39311(18) 0.07847(13) -0.09114(14) 0.0566(6) Uani 1 1 d . . . . .
O2 O 0.3833(2) 0.19117(14) -0.05953(15) 0.0707(8) Uani 1 1 d . . . . .
O3 O 0.3655(2) -0.00234(14) 0.12916(16) 0.0724(8) Uani 1 1 d . . . . .
O4 O 0.3485(2) -0.07654(16) 0.02468(15) 0.0731(8) Uani 1 1 d . . . . .
O5 O 0.5359(2) 0.06359(19) 0.08427(19) 0.0568(7) Uani 1 1 d . . . . .
N1 N 0.20694(19) 0.07863(14) -0.00844(16) 0.0463(7) Uani 1 1 d . . . . .
N2 N 0.36465(19) 0.16592(14) 0.13903(15) 0.0443(6) Uani 1 1 d . . . . .
C14 C 0.3879(2) 0.1437(2) -0.1096(2) 0.0480(8) Uani 1 1 d . . . . .
C20 C 0.3827(2) 0.16168(16) -0.19948(19) 0.0405(7) Uani 1 1 d . . . . .
C15 C 0.3791(2) 0.23147(18) -0.2255(2) 0.0521(9) Uani 1 1 d . . . . .
H15 H 0.3824 0.2682 -0.1878 0.063 Uiso 1 1 calc R . . . .
C16 C 0.3704(3) 0.24572(18) -0.3078(2) 0.0565(9) Uani 1 1 d . . . . .
C17 C 0.3648(2) 0.19233(19) -0.3662(2) 0.0514(9) Uani 1 1 d . . . . .
H17 H 0.3590 0.2031 -0.4216 0.062 Uiso 1 1 calc R . . . .
C18 C 0.3679(2) 0.12288(17) -0.33993(18) 0.0389(7) Uani 1 1 d . . . . .
C19 C 0.3776(2) 0.10855(17) -0.25706(19) 0.0398(7) Uani 1 1 d . . . . .
H19 H 0.3806 0.0617 -0.2396 0.048 Uiso 1 1 calc R . . . .
C21 C 0.3604(2) -0.0631(2) 0.0994(2) 0.0515(9) Uani 1 1 d . . . . .
C5 C 0.1722(3) 0.03321(18) -0.0683(2) 0.0535(9) Uani 1 1 d . . . . .
H5 H 0.2145 0.0051 -0.0902 0.064 Uiso 1 1 calc R . . . .
C4 C 0.0770(3) 0.02621(18) -0.0989(2) 0.0564(9) Uani 1 1 d . . . . .
H4 H 0.0563 -0.0058 -0.1410 0.068 Uiso 1 1 calc R . . . .
C3 C 0.0117(3) 0.06662(19) -0.0675(2) 0.0562(10) Uani 1 1 d . . . . .
C2 C 0.0473(3) 0.1127(2) -0.0056(2) 0.0578(10) Uani 1 1 d . . . . .
H2 H 0.0061 0.1407 0.0179 0.069 Uiso 1 1 calc R . . . .
C1 C 0.1443(3) 0.11778(19) 0.0220(2) 0.0524(9) Uani 1 1 d . . . . .
H1 H 0.1667 0.1499 0.0636 0.063 Uiso 1 1 calc R . . . .
C12 C 0.3766(3) 0.14585(18) 0.2170(2) 0.0563(9) Uani 1 1 d . . . . .
H12 H 0.3818 0.0978 0.2288 0.068 Uiso 1 1 calc R . . . .
C13 C 0.3818(3) 0.19260(19) 0.2814(2) 0.0554(9) Uani 1 1 d . . . . .
C9 C 0.3747(2) 0.26423(18) 0.26593(19) 0.0428(8) Uani 1 1 d . . . . .
C10 C 0.3607(2) 0.28479(17) 0.1853(2) 0.0498(8) Uani 1 1 d . . . . .
H10 H 0.3543 0.3325 0.1720 0.060 Uiso 1 1 calc R . . . .
C11 C 0.3560(2) 0.23503(17) 0.1238(2) 0.0483(8) Uani 1 1 d . . . . .
H11 H 0.3464 0.2503 0.0696 0.058 Uiso 1 1 calc R . . . .
C8 C 0.3862(2) 0.31471(19) 0.3374(2) 0.0551(9) Uani 1 1 d . . . . .
H8A H 0.4466 0.3048 0.3727 0.066 Uiso 1 1 calc R . . . .
H8B H 0.3370 0.3044 0.3687 0.066 Uiso 1 1 calc R . . . .
C7 C 0.3826(2) 0.39271(19) 0.3182(2) 0.0563(10) Uani 1 1 d . . . . .
H7A H 0.3194 0.4049 0.2895 0.068 Uiso 1 1 calc R . . . .
H7B H 0.4269 0.4032 0.2821 0.068 Uiso 1 1 calc R . . . .
C6 C 0.4073(3) 0.4382(2) 0.3961(3) 0.0711(12) Uani 1 1 d . . . . .
H6A H 0.3907 0.4871 0.3827 0.085 Uiso 1 1 calc R . . . .
H6B H 0.3704 0.4224 0.4362 0.085 Uiso 1 1 calc R . . . .
H5A H 0.568(3) 0.070(2) 0.048(3) 0.074(15) Uiso 1 1 d . . . . .
H13 H 0.391(2) 0.1777(19) 0.336(2) 0.066(11) Uiso 1 1 d . . . . .
H5B H 0.542(3) 0.026(2) 0.093(3) 0.075(18) Uiso 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
Cd1 O1 2.244(2) . ?
Cd1 O2 2.638(3) . ?
Cd1 O3 2.216(2) . ?
Cd1 O5 2.346(3) . ?
Cd1 N1 2.372(3) . ?
Cd1 N2 2.285(2) . ?
Br1 C16 1.901(3) . ?
O1 C14 1.270(4) . ?
O2 C14 1.234(4) . ?
O3 C21 1.247(4) . ?
O4 C21 1.246(4) . ?
N1 C5 1.338(4) . ?
N1 C1 1.333(4) . ?
N2 C12 1.328(4) . ?
N2 C11 1.333(4) . ?
C14 C20 1.517(4) . ?
C20 C15 1.387(5) . ?
C20 C19 1.379(4) . ?
C15 C16 1.374(5) . ?
C16 C17 1.391(5) . ?
C17 C18 1.382(5) . ?
C18 C19 1.382(4) . ?
C18 C21 1.504(5) 6 ?
C21 C18 1.504(5) 6_556 ?
C5 C4 1.372(5) . ?
C4 C3 1.383(5) . ?
C3 C2 1.372(5) . ?
C3 C6 1.511(5) 8_455 ?
C2 C1 1.385(5) . ?
C12 C13 1.378(5) . ?
C13 C9 1.379(5) . ?
C9 C10 1.371(5) . ?
C9 C8 1.508(4) . ?
C10 C11 1.381(4) . ?
C8 C7 1.508(5) . ?
C7 C6 1.538(5) . ?
C6 C3 1.511(5) 8_556 ?

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
O1 Cd1 O2 52.98(8) . . ?
O1 Cd1 O5 90.02(10) . . ?
O1 Cd1 N1 88.36(9) . . ?
O1 Cd1 N2 139.43(9) . . ?
O3 Cd1 O1 130.24(10) . . ?
O3 Cd1 O2 176.70(9) . . ?
O3 Cd1 O5 80.82(12) . . ?
O3 Cd1 N1 91.47(10) . . ?
O3 Cd1 N2 90.15(10) . . ?
O5 Cd1 O2 98.91(11) . . ?
O5 Cd1 N1 168.37(11) . . ?
N1 Cd1 O2 89.29(9) . . ?
N2 Cd1 O2 86.58(9) . . ?
N2 Cd1 O5 93.76(10) . . ?
N2 Cd1 N1 94.96(9) . . ?
C14 O1 Cd1 100.3(2) . . ?
C14 O2 Cd1 82.8(2) . . ?
C21 O3 Cd1 114.7(2) . . ?
C5 N1 Cd1 119.3(2) . . ?
C1 N1 Cd1 123.8(2) . . ?
C1 N1 C5 116.9(3) . . ?
C12 N2 Cd1 119.5(2) . . ?
C12 N2 C11 117.1(3) . . ?
C11 N2 Cd1 123.2(2) . . ?
O1 C14 C20 116.4(3) . . ?
O2 C14 O1 123.6(3) . . ?
O2 C14 C20 119.9(3) . . ?
C15 C20 C14 120.8(3) . . ?
C19 C20 C14 120.2(3) . . ?
C19 C20 C15 119.0(3) . . ?
C16 C15 C20 119.2(3) . . ?
C15 C16 Br1 119.7(3) . . ?
C15 C16 C17 122.1(3) . . ?
C17 C16 Br1 118.2(3) . . ?
C18 C17 C16 118.5(3) . . ?
C17 C18 C19 119.4(3) . . ?
C17 C18 C21 120.7(3) . 6 ?
C19 C18 C21 119.9(3) . 6 ?
C20 C19 C18 121.9(3) . . ?
O3 C21 C18 115.9(3) . 6_556 ?
O4 C21 O3 124.7(3) . . ?
O4 C21 C18 119.4(4) . 6_556 ?
N1 C5 C4 123.1(3) . . ?
C5 C4 C3 120.2(4) . . ?
C4 C3 C6 120.4(4) . 8_455 ?
C2 C3 C4 116.7(3) . . ?
C2 C3 C6 122.8(4) . 8_455 ?
C3 C2 C1 120.2(3) . . ?
N1 C1 C2 122.9(3) . . ?
N2 C12 C13 123.4(3) . . ?
C12 C13 C9 119.7(3) . . ?
C13 C9 C8 118.8(3) . . ?
C10 C9 C13 116.9(3) . . ?
C10 C9 C8 124.2(3) . . ?
C9 C10 C11 120.4(3) . . ?
N2 C11 C10 122.6(3) . . ?
C9 C8 C7 117.3(3) . . ?
C8 C7 C6 112.1(3) . . ?
C3 C6 C7 111.0(3) 8_556 . ?

_olex2_submission_special_instructions 'No special instructions were received'
