# 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 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_cs140
_audit_block_doi                 10.5517/ccdc.csd.cc21srcz
_database_code_depnum_ccdc_archive 'CCDC 1900621'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0OB02376K 2021
loop_
_audit_author_name
_audit_author_address
'Shiva shivakeshava'
;Tunghai university
Taiwan
;
_audit_update_record             
;
2019-03-02 deposited with the CCDC.	2021-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C22 H17 N O5, H2 O'
_chemical_formula_sum            'C22 H19 N O6'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         393.38

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.0475(10)
_cell_length_b                   20.289(3)
_cell_length_c                   9.7241(13)
_cell_angle_alpha                90
_cell_angle_beta                 101.000(5)
_cell_angle_gamma                90
_cell_volume                     1752.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9082
_cell_measurement_theta_min      2.992
_cell_measurement_theta_max      26.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8106
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29436
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.930
_diffrn_reflns_theta_max         26.411
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3569
_reflns_number_gt                2774
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0553P)²+1.1122P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3569
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.1007
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.002
_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
O1 O 1.07493(13) 0.66369(6) 0.44110(12) 0.0246(3) Uani 1 1 d . . . . .
O2 O 0.52625(14) 0.31365(7) 0.73277(13) 0.0298(3) Uani 1 1 d . . . . .
O3 O 0.35664(14) 0.25732(7) 0.52401(14) 0.0310(3) Uani 1 1 d . . . . .
O4 O 0.82091(16) 0.54510(7) 0.12528(13) 0.0322(3) Uani 1 1 d . . . . .
O5 O 1.02647(14) 0.64013(6) 0.21745(13) 0.0278(3) Uani 1 1 d . . . . .
N N 0.70715(15) 0.49321(7) 0.28540(13) 0.0181(3) Uani 1 1 d . . . . .
C1 C 1.05486(19) 0.65562(8) 0.57698(18) 0.0209(4) Uani 1 1 d . . . . .
C2 C 1.1393(2) 0.69743(9) 0.6753(2) 0.0264(4) Uani 1 1 d . . . . .
H2A H 1.2079 0.7280 0.6482 0.032 Uiso 1 1 calc R U . . .
C3 C 1.1217(2) 0.69362(9) 0.81286(19) 0.0273(4) Uani 1 1 d . . . . .
H3A H 1.1773 0.7223 0.8809 0.033 Uiso 1 1 calc R U . . .
C4 C 1.0227(2) 0.64796(9) 0.85277(19) 0.0261(4) Uani 1 1 d . . . . .
H4A H 1.0107 0.6458 0.9476 0.031 Uiso 1 1 calc R U . . .
C5 C 0.94176(19) 0.60575(9) 0.75435(17) 0.0218(4) Uani 1 1 d . . . . .
H5A H 0.8760 0.5742 0.7827 0.026 Uiso 1 1 calc R U . . .
C6 C 0.95571(17) 0.60904(8) 0.61276(17) 0.0181(3) Uani 1 1 d . . . . .
C7 C 0.87055(17) 0.56807(8) 0.50096(16) 0.0167(3) Uani 1 1 d . . . . .
C8 C 0.77253(17) 0.51800(8) 0.52866(16) 0.0177(3) Uani 1 1 d . . . . .
H8A H 0.7608 0.5103 0.6224 0.021 Uiso 1 1 calc R U . . .
C9 C 0.69313(17) 0.47990(8) 0.42194(16) 0.0165(3) Uani 1 1 d . . . . .
C10 C 0.59838(17) 0.42379(8) 0.44741(17) 0.0180(3) Uani 1 1 d . . . . .
C11 C 0.60748(18) 0.39777(8) 0.58349(17) 0.0197(3) Uani 1 1 d . . . . .
H11A H 0.6716 0.4181 0.6606 0.024 Uiso 1 1 calc R U . . .
C12 C 0.52429(18) 0.34321(9) 0.60544(17) 0.0215(4) Uani 1 1 d . . . . .
C13 C 0.42981(18) 0.31203(9) 0.49100(18) 0.0220(4) Uani 1 1 d . . . . .
C14 C 0.41889(18) 0.33812(9) 0.35778(18) 0.0225(4) Uani 1 1 d . . . . .
H14A H 0.3551 0.3177 0.2807 0.027 Uiso 1 1 calc R U . . .
C15 C 0.50071(17) 0.39419(9) 0.33579(17) 0.0199(4) Uani 1 1 d . . . . .
C16 C 0.48174(19) 0.42614(9) 0.19326(18) 0.0255(4) Uani 1 1 d . . . . .
H16A H 0.4409 0.3935 0.1201 0.031 Uiso 1 1 calc R U . . .
H16B H 0.4090 0.4630 0.1875 0.031 Uiso 1 1 calc R U . . .
C17 C 0.63043(19) 0.45183(9) 0.16755(17) 0.0233(4) Uani 1 1 d . . . . .
H17A H 0.6961 0.4142 0.1547 0.028 Uiso 1 1 calc R U . . .
H17B H 0.6133 0.4782 0.0803 0.028 Uiso 1 1 calc R U . . .
C18 C 0.80754(19) 0.54017(8) 0.24912(17) 0.0207(4) Uani 1 1 d . . . . .
C19 C 0.88949(18) 0.57904(8) 0.36353(17) 0.0182(3) Uani 1 1 d . . . . .
C20 C 0.99631(18) 0.62775(8) 0.33060(17) 0.0205(4) Uani 1 1 d . . . . .
C21 C 0.6011(2) 0.34828(10) 0.85415(19) 0.0309(4) Uani 1 1 d . . . . .
H21A H 0.5951 0.3225 0.9381 0.046 Uiso 1 1 calc R U . . .
H21B H 0.7070 0.3549 0.8481 0.046 Uiso 1 1 calc R U . . .
H21C H 0.5526 0.3912 0.8594 0.046 Uiso 1 1 calc R U . . .
C22 C 0.2540(2) 0.22557(9) 0.4127(2) 0.0286(4) Uani 1 1 d . . . . .
H22A H 0.2090 0.1871 0.4499 0.043 Uiso 1 1 calc R U . . .
H22B H 0.1744 0.2566 0.3724 0.043 Uiso 1 1 calc R U . . .
H22C H 0.3085 0.2113 0.3400 0.043 Uiso 1 1 calc R U . . .
O6 O 0.83018(15) 0.47132(7) 0.88448(14) 0.0294(3) Uani 1 1 d . . . . .
H6A H 0.843(3) 0.4909(14) 0.980(3) 0.065(8) Uiso 1 1 d . . . . .
H6B H 0.924(4) 0.4487(16) 0.885(3) 0.085(10) 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
O1 C20 1.379(2) . ?
O1 C1 1.377(2) . ?
O2 C12 1.373(2) . ?
O2 C21 1.428(2) . ?
O3 C13 1.362(2) . ?
O3 C22 1.437(2) . ?
O4 C18 1.237(2) . ?
O5 C20 1.209(2) . ?
N C9 1.384(2) . ?
N C18 1.407(2) . ?
N C17 1.482(2) . ?
C1 C2 1.393(2) . ?
C1 C6 1.392(2) . ?
C2 C3 1.379(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.394(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.385(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.408(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.465(2) . ?
C7 C19 1.397(2) . ?
C7 C8 1.408(2) . ?
C8 C9 1.381(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.474(2) . ?
C10 C15 1.398(2) . ?
C10 C11 1.412(2) . ?
C11 C12 1.378(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.416(2) . ?
C13 C14 1.385(2) . ?
C14 C15 1.396(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.510(2) . ?
C16 C17 1.507(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.447(2) . ?
C19 C20 1.460(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O6 H6A 1.00(3) . ?
O6 H6B 0.96(3) . ?

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
C20 O1 C1 122.82(13) . . ?
C12 O2 C21 116.93(14) . . ?
C13 O3 C22 117.48(14) . . ?
C9 N C18 123.66(14) . . ?
C9 N C17 121.07(13) . . ?
C18 N C17 114.79(13) . . ?
O1 C1 C2 115.52(15) . . ?
O1 C1 C6 121.98(15) . . ?
C2 C1 C6 122.50(16) . . ?
C3 C2 C1 118.82(17) . . ?
C3 C2 H2A 120.6 . . ?
C1 C2 H2A 120.6 . . ?
C2 C3 C4 120.44(17) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C5 C4 C3 120.11(17) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C6 120.82(16) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C1 C6 C5 117.31(15) . . ?
C1 C6 C7 118.19(15) . . ?
C5 C6 C7 124.48(15) . . ?
C19 C7 C8 119.65(15) . . ?
C19 C7 C6 118.43(15) . . ?
C8 C7 C6 121.92(14) . . ?
C9 C8 C7 121.11(14) . . ?
C9 C8 H8A 119.4 . . ?
C7 C8 H8A 119.4 . . ?
N C9 C8 118.82(14) . . ?
N C9 C10 118.32(14) . . ?
C8 C9 C10 122.82(14) . . ?
C15 C10 C11 118.83(15) . . ?
C15 C10 C9 120.20(15) . . ?
C11 C10 C9 120.94(14) . . ?
C12 C11 C10 120.63(15) . . ?
C12 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
C11 C12 O2 125.25(15) . . ?
C11 C12 C13 120.18(15) . . ?
O2 C12 C13 114.55(15) . . ?
O3 C13 C14 125.50(16) . . ?
O3 C13 C12 115.25(15) . . ?
C14 C13 C12 119.25(15) . . ?
C13 C14 C15 120.62(16) . . ?
C13 C14 H14A 119.7 . . ?
C15 C14 H14A 119.7 . . ?
C10 C15 C14 120.42(15) . . ?
C10 C15 C16 118.21(15) . . ?
C14 C15 C16 121.32(15) . . ?
C17 C16 C15 110.60(14) . . ?
C17 C16 H16A 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
N C17 C16 111.64(13) . . ?
N C17 H17A 109.3 . . ?
C16 C17 H17A 109.3 . . ?
N C17 H17B 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
O4 C18 N 119.12(15) . . ?
O4 C18 C19 124.98(16) . . ?
N C18 C19 115.90(14) . . ?
C7 C19 C18 120.67(15) . . ?
C7 C19 C20 121.66(15) . . ?
C18 C19 C20 117.63(14) . . ?
O5 C20 O1 115.27(15) . . ?
O5 C20 C19 127.87(16) . . ?
O1 C20 C19 116.86(14) . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
H6A O6 H6B 103(2) . . ?

_refine_diff_density_max         0.231
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.050


_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/c
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_cs465
_audit_block_doi                 10.5517/ccdc.csd.cc25kd49
_database_code_depnum_ccdc_archive 'CCDC 2012710'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0OB02376K 2021
loop_
_audit_author_name
_audit_author_address
'Shiva shivakeshava'
;Tunghai university
Taiwan
;
_audit_update_record             
;
2020-06-29 deposited with the CCDC.	2021-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C22 H16 Br N O5, C H2 Cl2'
_chemical_formula_sum            'C23 H18 Br Cl2 N O5'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         539.19

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.9528(6)
_cell_length_b                   9.8435(4)
_cell_length_c                   14.8269(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.3485(16)
_cell_angle_gamma                90
_cell_volume                     2182.99(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9829
_cell_measurement_theta_min      3.234
_cell_measurement_theta_max      27.846
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.290
_exptl_absorpt_coefficient_mu    2.165
_shelx_estimated_absorpt_T_min   0.423
_shelx_estimated_absorpt_T_max   0.573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7973
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39472
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.931
_diffrn_reflns_theta_max         27.880
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             5168
_reflns_number_gt                4523
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0404P)²+2.5564P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5168
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0879
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.002
_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
Br Br 1.10909(2) 0.20409(3) 0.16505(2) 0.03667(9) Uani 1 1 d . . . . .
O1 O 0.93095(9) 0.35999(14) 0.44561(9) 0.0192(3) Uani 1 1 d . . . . .
O2 O 0.61667(9) -0.13490(14) -0.11530(9) 0.0204(3) Uani 1 1 d . . . . .
O3 O 0.49202(9) -0.27665(15) -0.08983(10) 0.0235(3) Uani 1 1 d . . . . .
O4 O 0.67167(9) 0.22017(15) 0.41382(10) 0.0235(3) Uani 1 1 d . . . . .
O5 O 0.82837(9) 0.34955(14) 0.51162(9) 0.0200(3) Uani 1 1 d . . . . .
N N 0.66625(9) 0.09635(15) 0.28250(10) 0.0146(3) Uani 1 1 d . . . . .
C1 C 0.96719(12) 0.32242(18) 0.37800(12) 0.0157(3) Uani 1 1 d . . . . .
C2 C 1.05372(12) 0.36820(19) 0.39421(14) 0.0203(4) Uani 1 1 d . . . . .
H2A H 1.0834 0.4240 0.4481 0.024 Uiso 1 1 calc R U . . .
C3 C 1.09576(12) 0.3313(2) 0.33085(14) 0.0207(4) Uani 1 1 d . . . . .
H3A H 1.1554 0.3597 0.3414 0.025 Uiso 1 1 calc R U . . .
C4 C 1.04991(12) 0.2521(2) 0.25125(13) 0.0197(4) Uani 1 1 d . . . . .
C5 C 0.96358(12) 0.20781(19) 0.23393(13) 0.0180(3) Uani 1 1 d . . . . .
H5A H 0.9336 0.1545 0.1787 0.022 Uiso 1 1 calc R U . . .
C6 C 0.92051(11) 0.24240(18) 0.29882(12) 0.0143(3) Uani 1 1 d . . . . .
C7 C 0.83085(11) 0.19665(17) 0.28991(12) 0.0133(3) Uani 1 1 d . . . . .
C8 C 0.77915(11) 0.11594(17) 0.21266(12) 0.0142(3) Uani 1 1 d . . . . .
H8A H 0.8004 0.0962 0.1617 0.017 Uiso 1 1 calc R U . . .
C9 C 0.69781(11) 0.06492(17) 0.20979(12) 0.0137(3) Uani 1 1 d . . . . .
C10 C 0.64282(11) -0.02398(17) 0.13166(12) 0.0135(3) Uani 1 1 d . . . . .
C11 C 0.65841(11) -0.03164(18) 0.04367(12) 0.0143(3) Uani 1 1 d . . . . .
H11A H 0.7034 0.0229 0.0335 0.017 Uiso 1 1 calc R U . . .
C12 C 0.60791(11) -0.11870(18) -0.02748(12) 0.0156(3) Uani 1 1 d . . . . .
C13 C 0.53930(12) -0.19766(18) -0.01373(13) 0.0161(3) Uani 1 1 d . . . . .
C14 C 0.52400(12) -0.18956(18) 0.07234(13) 0.0167(3) Uani 1 1 d . . . . .
H14A H 0.4781 -0.2428 0.0819 0.020 Uiso 1 1 calc R U . . .
C15 C 0.57576(12) -0.10331(18) 0.14523(12) 0.0154(3) Uani 1 1 d . . . . .
C16 C 0.56143(13) -0.0961(2) 0.24012(13) 0.0200(4) Uani 1 1 d . . . . .
H16A H 0.6028 -0.1597 0.2863 0.024 Uiso 1 1 calc R U . . .
H16B H 0.4994 -0.1238 0.2314 0.024 Uiso 1 1 calc R U . . .
C17 C 0.57773(12) 0.0465(2) 0.27969(13) 0.0187(4) Uani 1 1 d . . . . .
H17A H 0.5303 0.1075 0.2388 0.022 Uiso 1 1 calc R U . . .
H17B H 0.5751 0.0478 0.3454 0.022 Uiso 1 1 calc R U . . .
C18 C 0.70956(12) 0.18665(18) 0.35789(12) 0.0153(3) Uani 1 1 d . . . . .
C19 C 0.79733(11) 0.23249(17) 0.36205(12) 0.0139(3) Uani 1 1 d . . . . .
C20 C 0.84906(11) 0.31458(17) 0.44409(12) 0.0151(3) Uani 1 1 d . . . . .
C21 C 0.68883(14) -0.0666(2) -0.13110(14) 0.0268(4) Uani 1 1 d . . . . .
H21A H 0.6878 -0.0861 -0.1963 0.040 Uiso 1 1 calc R U . . .
H21B H 0.6829 0.0315 -0.1238 0.040 Uiso 1 1 calc R U . . .
H21C H 0.7455 -0.0980 -0.0841 0.040 Uiso 1 1 calc R U . . .
C22 C 0.41894(13) -0.3523(2) -0.08062(15) 0.0252(4) Uani 1 1 d . . . . .
H22A H 0.3903 -0.4048 -0.1395 0.038 Uiso 1 1 calc R U . . .
H22B H 0.4411 -0.4143 -0.0257 0.038 Uiso 1 1 calc R U . . .
H22C H 0.3753 -0.2896 -0.0704 0.038 Uiso 1 1 calc R U . . .
Cl1 Cl 0.91088(5) 0.49565(8) 0.04795(6) 0.0566(2) Uani 1 1 d . . . . .
Cl2 Cl 0.73514(5) 0.59476(8) 0.03784(10) 0.0935(4) Uani 1 1 d . . . . .
C23 C 0.82009(17) 0.4758(3) 0.0876(2) 0.0400(6) Uani 1 1 d . . . . .
H23A H 0.8417 0.4842 0.1586 0.048 Uiso 1 1 calc R U . . .
H23B H 0.7951 0.3834 0.0708 0.048 Uiso 1 1 calc R U . . .


_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
Br C4 1.8941(18) . ?
O1 C20 1.373(2) . ?
O1 C1 1.371(2) . ?
O2 C12 1.366(2) . ?
O2 C21 1.421(2) . ?
O3 C13 1.362(2) . ?
O3 C22 1.429(2) . ?
O4 C18 1.229(2) . ?
O5 C20 1.208(2) . ?
N C9 1.374(2) . ?
N C18 1.407(2) . ?
N C17 1.482(2) . ?
C1 C2 1.391(2) . ?
C1 C6 1.395(2) . ?
C2 C3 1.379(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.391(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.381(2) . ?
C5 C6 1.405(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.461(2) . ?
C7 C8 1.402(2) . ?
C7 C19 1.397(2) . ?
C8 C9 1.378(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.473(2) . ?
C10 C15 1.394(2) . ?
C10 C11 1.413(2) . ?
C11 C12 1.380(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.414(2) . ?
C13 C14 1.382(2) . ?
C14 C15 1.397(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.503(2) . ?
C16 C17 1.509(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.452(2) . ?
C19 C20 1.455(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
Cl1 C23 1.753(3) . ?
Cl2 C23 1.748(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?

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
C20 O1 C1 122.74(14) . . ?
C12 O2 C21 117.32(14) . . ?
C13 O3 C22 116.97(14) . . ?
C9 N C18 123.55(14) . . ?
C9 N C17 120.60(14) . . ?
C18 N C17 115.55(14) . . ?
O1 C1 C2 115.58(15) . . ?
O1 C1 C6 122.03(15) . . ?
C2 C1 C6 122.39(16) . . ?
C3 C2 C1 119.04(17) . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 H2A 120.5 . . ?
C2 C3 C4 119.24(17) . . ?
C2 C3 H3A 120.4 . . ?
C4 C3 H3A 120.4 . . ?
C5 C4 C3 122.07(17) . . ?
C5 C4 Br 119.64(14) . . ?
C3 C4 Br 118.29(14) . . ?
C4 C5 C6 119.32(16) . . ?
C4 C5 H5A 120.3 . . ?
C6 C5 H5A 120.3 . . ?
C1 C6 C5 117.92(16) . . ?
C1 C6 C7 118.01(15) . . ?
C5 C6 C7 124.05(16) . . ?
C8 C7 C19 119.69(15) . . ?
C8 C7 C6 121.86(15) . . ?
C19 C7 C6 118.43(15) . . ?
C9 C8 C7 120.78(15) . . ?
C9 C8 H8A 119.6 . . ?
C7 C8 H8A 119.6 . . ?
C8 C9 N 119.45(15) . . ?
C8 C9 C10 122.52(15) . . ?
N C9 C10 118.04(15) . . ?
C15 C10 C11 119.58(15) . . ?
C15 C10 C9 119.75(15) . . ?
C11 C10 C9 120.66(15) . . ?
C12 C11 C10 119.71(15) . . ?
C12 C11 H11A 120.1 . . ?
C10 C11 H11A 120.1 . . ?
O2 C12 C11 125.09(15) . . ?
O2 C12 C13 114.47(15) . . ?
C11 C12 C13 120.43(15) . . ?
O3 C13 C14 124.96(16) . . ?
O3 C13 C12 115.33(15) . . ?
C14 C13 C12 119.70(16) . . ?
C13 C14 C15 120.19(16) . . ?
C13 C14 H14A 119.9 . . ?
C15 C14 H14A 119.9 . . ?
C10 C15 C14 120.37(15) . . ?
C10 C15 C16 118.86(15) . . ?
C14 C15 C16 120.76(15) . . ?
C15 C16 C17 110.22(15) . . ?
C15 C16 H16A 109.6 . . ?
C17 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
N C17 C16 110.64(14) . . ?
N C17 H17A 109.5 . . ?
C16 C17 H17A 109.5 . . ?
N C17 H17B 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
O4 C18 N 119.00(16) . . ?
O4 C18 C19 125.53(16) . . ?
N C18 C19 115.47(14) . . ?
C7 C19 C20 121.57(15) . . ?
C7 C19 C18 120.61(15) . . ?
C20 C19 C18 117.82(15) . . ?
O5 C20 O1 115.22(15) . . ?
O5 C20 C19 127.75(16) . . ?
O1 C20 C19 117.03(15) . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
Cl1 C23 Cl2 113.17(16) . . ?
Cl1 C23 H23A 108.9 . . ?
Cl2 C23 H23A 108.9 . . ?
Cl1 C23 H23B 108.9 . . ?
Cl2 C23 H23B 108.9 . . ?
H23A C23 H23B 107.8 . . ?

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
C20 O1 C1 C2 -174.88(16) . . . . ?
C20 O1 C1 C6 4.5(3) . . . . ?
O1 C1 C2 C3 178.14(17) . . . . ?
C6 C1 C2 C3 -1.2(3) . . . . ?
C1 C2 C3 C4 1.5(3) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C2 C3 C4 Br 179.59(15) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
Br C4 C5 C6 179.21(14) . . . . ?
O1 C1 C6 C5 -179.29(16) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
O1 C1 C6 C7 -0.9(3) . . . . ?
C2 C1 C6 C7 178.37(17) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
C4 C5 C6 C7 -177.40(17) . . . . ?
C1 C6 C7 C8 179.99(16) . . . . ?
C5 C6 C7 C8 -1.8(3) . . . . ?
C1 C6 C7 C19 -1.5(2) . . . . ?
C5 C6 C7 C19 176.74(17) . . . . ?
C19 C7 C8 C9 -3.8(3) . . . . ?
C6 C7 C8 C9 174.71(16) . . . . ?
C7 C8 C9 N 1.5(3) . . . . ?
C7 C8 C9 C10 -177.90(16) . . . . ?
C18 N C9 C8 4.6(3) . . . . ?
C17 N C9 C8 178.03(16) . . . . ?
C18 N C9 C10 -175.92(15) . . . . ?
C17 N C9 C10 -2.5(2) . . . . ?
C8 C9 C10 C15 161.49(17) . . . . ?
N C9 C10 C15 -18.0(2) . . . . ?
C8 C9 C10 C11 -17.3(3) . . . . ?
N C9 C10 C11 163.23(16) . . . . ?
C15 C10 C11 C12 -0.8(3) . . . . ?
C9 C10 C11 C12 178.02(16) . . . . ?
C21 O2 C12 C11 6.3(3) . . . . ?
C21 O2 C12 C13 -175.23(17) . . . . ?
C10 C11 C12 O2 179.94(16) . . . . ?
C10 C11 C12 C13 1.6(3) . . . . ?
C22 O3 C13 C14 2.6(3) . . . . ?
C22 O3 C13 C12 -176.67(17) . . . . ?
O2 C12 C13 O3 -0.5(2) . . . . ?
C11 C12 C13 O3 178.01(16) . . . . ?
O2 C12 C13 C14 -179.87(16) . . . . ?
C11 C12 C13 C14 -1.3(3) . . . . ?
O3 C13 C14 C15 -178.96(17) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C11 C10 C15 C14 -0.2(3) . . . . ?
C9 C10 C15 C14 -179.04(16) . . . . ?
C11 C10 C15 C16 178.68(16) . . . . ?
C9 C10 C15 C16 -0.1(2) . . . . ?
C13 C14 C15 C10 0.4(3) . . . . ?
C13 C14 C15 C16 -178.42(17) . . . . ?
C10 C15 C16 C17 35.5(2) . . . . ?
C14 C15 C16 C17 -145.61(17) . . . . ?
C9 N C17 C16 38.2(2) . . . . ?
C18 N C17 C16 -147.90(15) . . . . ?
C15 C16 C17 N -52.6(2) . . . . ?
C9 N C18 O4 172.12(16) . . . . ?
C17 N C18 O4 -1.6(2) . . . . ?
C9 N C18 C19 -7.9(2) . . . . ?
C17 N C18 C19 178.42(15) . . . . ?
C8 C7 C19 C20 179.22(16) . . . . ?
C6 C7 C19 C20 0.7(2) . . . . ?
C8 C7 C19 C18 0.2(3) . . . . ?
C6 C7 C19 C18 -178.39(15) . . . . ?
O4 C18 C19 C7 -174.64(18) . . . . ?
N C18 C19 C7 5.3(2) . . . . ?
O4 C18 C19 C20 6.3(3) . . . . ?
N C18 C19 C20 -173.75(15) . . . . ?
C1 O1 C20 O5 175.59(16) . . . . ?
C1 O1 C20 C19 -5.1(2) . . . . ?
C7 C19 C20 O5 -178.29(18) . . . . ?
C18 C19 C20 O5 0.8(3) . . . . ?
C7 C19 C20 O1 2.5(2) . . . . ?
C18 C19 C20 O1 -178.37(15) . . . . ?

_refine_diff_density_max         1.274
_refine_diff_density_min         -0.989
_refine_diff_density_rms         0.065


_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/c
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_cs479
_database_code_depnum_ccdc_archive 'CCDC 2003732'
loop_
_audit_author_name
_audit_author_address
'Shiva shivakeshava'
;Tunghai university
Taiwan
;
_audit_update_record             
;
2020-05-13 deposited with the CCDC.	2021-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C22 H16 Br N O5'
_chemical_formula_sum            'C22 H16 Br N O5'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            green
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         454.27

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.3236(3)
_cell_length_b                   10.0313(3)
_cell_length_c                   11.2021(5)
_cell_angle_alpha                74.6908(16)
_cell_angle_beta                 65.4310(11)
_cell_angle_gamma                70.1382(11)
_cell_volume                     886.89(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9974
_cell_measurement_theta_min      3.716
_cell_measurement_theta_max      27.876
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    2.355
_shelx_estimated_absorpt_T_min   0.476
_shelx_estimated_absorpt_T_max   0.638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7477
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18511
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.179
_diffrn_reflns_theta_max         27.905
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4204
_reflns_number_gt                3830
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_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)+(0.0286P)²+0.3065P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4204
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0218
_refine_ls_wR_factor_ref         0.0575
_refine_ls_wR_factor_gt          0.0560
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
Br Br 0.27662(2) 1.47827(2) 0.38737(2) 0.02611(6) Uani 1 1 d . . . . .
O1 O 0.83137(12) 0.97192(10) 0.44420(10) 0.0183(2) Uani 1 1 d . . . . .
O2 O 0.46735(13) 1.02542(11) 0.19032(11) 0.0228(2) Uani 1 1 d . . . . .
O3 O 0.90012(12) 0.15786(10) 0.03762(10) 0.0194(2) Uani 1 1 d . . . . .
O4 O 1.01662(13) 0.16817(10) 0.20490(10) 0.0200(2) Uani 1 1 d . . . . .
O5 O 1.01934(13) 0.77388(11) 0.38507(11) 0.0252(2) Uani 1 1 d . . . . .
N N 0.63105(14) 0.79848(12) 0.17703(11) 0.0153(2) Uani 1 1 d . . . . .
C1 C 0.70024(17) 1.08245(14) 0.42889(13) 0.0165(3) Uani 1 1 d . . . . .
C2 C 0.65507(18) 1.19394(15) 0.49961(14) 0.0184(3) Uani 1 1 d . . . . .
H2A H 0.711236 1.189726 0.555012 0.022 Uiso 1 1 calc R U . . .
C3 C 0.52717(18) 1.31138(15) 0.48846(14) 0.0199(3) Uani 1 1 d . . . . .
H3A H 0.493148 1.388161 0.537091 0.024 Uiso 1 1 calc R U . . .
C4 C 0.44943(17) 1.31500(14) 0.40493(14) 0.0190(3) Uani 1 1 d . . . . .
C5 C 0.49180(17) 1.20309(15) 0.33627(14) 0.0184(3) Uani 1 1 d . . . . .
H5A H 0.434994 1.208097 0.281110 0.022 Uiso 1 1 calc R U . . .
C6 C 0.61981(16) 1.08133(14) 0.34844(13) 0.0156(3) Uani 1 1 d . . . . .
C7 C 0.67036(16) 0.95284(14) 0.28828(13) 0.0153(3) Uani 1 1 d . . . . .
C8 C 0.58146(17) 0.93360(14) 0.21590(13) 0.0164(3) Uani 1 1 d . . . . .
C9 C 0.52846(17) 0.77408(15) 0.11773(15) 0.0193(3) Uani 1 1 d . . . . .
H9A H 0.471449 0.867022 0.079152 0.023 Uiso 1 1 calc R U . . .
H9B H 0.444788 0.727965 0.187433 0.023 Uiso 1 1 calc R U . . .
C10 C 0.63292(18) 0.67951(15) 0.01091(14) 0.0201(3) Uani 1 1 d . . . . .
H10A H 0.562301 0.657368 -0.023073 0.024 Uiso 1 1 calc R U . . .
H10B H 0.707808 0.730467 -0.063817 0.024 Uiso 1 1 calc R U . . .
C11 C 0.73032(16) 0.54296(14) 0.06565(13) 0.0156(3) Uani 1 1 d . . . . .
C12 C 0.76448(17) 0.41279(15) 0.02360(13) 0.0170(3) Uani 1 1 d . . . . .
H12A H 0.721711 0.408837 -0.038595 0.020 Uiso 1 1 calc R U . . .
C13 C 0.86007(16) 0.28943(14) 0.07164(13) 0.0156(3) Uani 1 1 d . . . . .
C14 C 0.92286(16) 0.29560(14) 0.16487(13) 0.0155(3) Uani 1 1 d . . . . .
C15 C 0.88634(16) 0.42345(14) 0.20853(13) 0.0163(3) Uani 1 1 d . . . . .
H15A H 0.925997 0.426851 0.272967 0.020 Uiso 1 1 calc R U . . .
C16 C 0.79042(16) 0.54941(14) 0.15816(13) 0.0147(3) Uani 1 1 d . . . . .
C17 C 0.75799(16) 0.68728(14) 0.19985(13) 0.0149(3) Uani 1 1 d . . . . .
C18 C 0.84635(17) 0.71083(14) 0.26026(13) 0.0164(3) Uani 1 1 d . . . . .
H18A H 0.938855 0.638378 0.271271 0.020 Uiso 1 1 calc R U . . .
C19 C 0.80009(16) 0.84220(14) 0.30593(13) 0.0156(3) Uani 1 1 d . . . . .
C20 C 0.89405(17) 0.85676(15) 0.37829(14) 0.0176(3) Uani 1 1 d . . . . .
C21 C 0.81788(18) 0.14162(15) -0.03878(15) 0.0210(3) Uani 1 1 d . . . . .
H21A H 0.856759 0.042653 -0.057116 0.031 Uiso 1 1 calc R U . . .
H21B H 0.699883 0.164191 0.011154 0.031 Uiso 1 1 calc R U . . .
H21C H 0.840732 0.206899 -0.122648 0.031 Uiso 1 1 calc R U . . .
C22 C 1.07426(18) 0.16635(16) 0.30558(14) 0.0214(3) Uani 1 1 d . . . . .
H22A H 1.139676 0.069709 0.325823 0.032 Uiso 1 1 calc R U . . .
H22B H 1.141749 0.234022 0.274049 0.032 Uiso 1 1 calc R U . . .
H22C H 0.980817 0.194067 0.385819 0.032 Uiso 1 1 calc R U . . .


_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
Br C4 1.9019(14) . ?
O1 C20 1.3616(16) . ?
O1 C1 1.3807(16) . ?
O2 C8 1.2291(17) . ?
O3 C13 1.3561(16) . ?
O3 C21 1.4322(16) . ?
O4 C14 1.3650(16) . ?
O4 C22 1.4310(16) . ?
O5 C20 1.2009(17) . ?
N C17 1.3836(17) . ?
N C8 1.3996(17) . ?
N C9 1.4797(17) . ?
C1 C2 1.3878(19) . ?
C1 C6 1.3956(19) . ?
C2 C3 1.385(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.389(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.382(2) . ?
C5 C6 1.4113(19) . ?
C5 H5A 0.9500 . ?
C6 C7 1.4558(18) . ?
C7 C19 1.3801(19) . ?
C7 C8 1.4601(19) . ?
C9 C10 1.511(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5004(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.3949(19) . ?
C11 C16 1.3910(18) . ?
C12 C13 1.3831(19) . ?
C12 H12A 0.9500 . ?
C13 C14 1.4157(19) . ?
C14 C15 1.3769(19) . ?
C15 C16 1.4107(18) . ?
C15 H15A 0.9500 . ?
C16 C17 1.4703(18) . ?
C17 C18 1.3684(19) . ?
C18 C19 1.4038(19) . ?
C18 H18A 0.9500 . ?
C19 C20 1.4785(18) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C20 O1 C1 122.10(11) . . ?
C13 O3 C21 116.98(10) . . ?
C14 O4 C22 117.02(11) . . ?
C17 N C8 124.59(11) . . ?
C17 N C9 119.69(11) . . ?
C8 N C9 115.52(11) . . ?
O1 C1 C2 114.82(12) . . ?
O1 C1 C6 122.29(12) . . ?
C2 C1 C6 122.89(12) . . ?
C1 C2 C3 119.21(13) . . ?
C1 C2 H2A 120.4 . . ?
C3 C2 H2A 120.4 . . ?
C2 C3 C4 118.86(13) . . ?
C2 C3 H3A 120.6 . . ?
C4 C3 H3A 120.6 . . ?
C5 C4 C3 122.16(13) . . ?
C5 C4 Br 119.16(11) . . ?
C3 C4 Br 118.67(10) . . ?
C4 C5 C6 119.72(13) . . ?
C4 C5 H5A 120.1 . . ?
C6 C5 H5A 120.1 . . ?
C1 C6 C5 117.09(12) . . ?
C1 C6 C7 117.47(12) . . ?
C5 C6 C7 125.39(13) . . ?
C19 C7 C6 119.52(12) . . ?
C19 C7 C8 118.57(12) . . ?
C6 C7 C8 121.80(12) . . ?
O2 C8 N 119.49(12) . . ?
O2 C8 C7 124.70(13) . . ?
N C8 C7 115.80(11) . . ?
N C9 C10 110.24(11) . . ?
N C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
N C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C9 110.12(11) . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.2 . . ?
C12 C11 C16 120.11(12) . . ?
C12 C11 C10 121.71(12) . . ?
C16 C11 C10 118.16(12) . . ?
C13 C12 C11 120.60(12) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
O3 C13 C12 125.29(12) . . ?
O3 C13 C14 115.17(11) . . ?
C12 C13 C14 119.54(12) . . ?
O4 C14 C15 125.36(12) . . ?
O4 C14 C13 114.74(12) . . ?
C15 C14 C13 119.89(12) . . ?
C14 C15 C16 120.41(12) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C11 C16 C15 119.42(12) . . ?
C11 C16 C17 120.09(12) . . ?
C15 C16 C17 120.46(12) . . ?
C18 C17 N 118.54(12) . . ?
C18 C17 C16 123.40(12) . . ?
N C17 C16 118.06(12) . . ?
C17 C18 C19 119.90(12) . . ?
C17 C18 H18A 120.0 . . ?
C19 C18 H18A 120.0 . . ?
C7 C19 C18 122.40(13) . . ?
C7 C19 C20 120.55(12) . . ?
C18 C19 C20 117.02(12) . . ?
O5 C20 O1 117.79(12) . . ?
O5 C20 C19 125.07(13) . . ?
O1 C20 C19 117.13(12) . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
C20 O1 C1 C2 -177.88(12) . . . . ?
C20 O1 C1 C6 2.2(2) . . . . ?
O1 C1 C2 C3 178.56(12) . . . . ?
C6 C1 C2 C3 -1.5(2) . . . . ?
C1 C2 C3 C4 -1.0(2) . . . . ?
C2 C3 C4 C5 2.3(2) . . . . ?
C2 C3 C4 Br -178.79(10) . . . . ?
C3 C4 C5 C6 -1.1(2) . . . . ?
Br C4 C5 C6 180.00(10) . . . . ?
O1 C1 C6 C5 -177.42(12) . . . . ?
C2 C1 C6 C5 2.7(2) . . . . ?
O1 C1 C6 C7 4.9(2) . . . . ?
C2 C1 C6 C7 -175.01(12) . . . . ?
C4 C5 C6 C1 -1.3(2) . . . . ?
C4 C5 C6 C7 176.14(13) . . . . ?
C1 C6 C7 C19 -3.85(19) . . . . ?
C5 C6 C7 C19 178.70(13) . . . . ?
C1 C6 C7 C8 172.43(12) . . . . ?
C5 C6 C7 C8 -5.0(2) . . . . ?
C17 N C8 O2 179.71(13) . . . . ?
C9 N C8 O2 -5.49(19) . . . . ?
C17 N C8 C7 -1.63(19) . . . . ?
C9 N C8 C7 173.16(12) . . . . ?
C19 C7 C8 O2 -177.69(13) . . . . ?
C6 C7 C8 O2 6.0(2) . . . . ?
C19 C7 C8 N 3.73(18) . . . . ?
C6 C7 C8 N -172.58(12) . . . . ?
C17 N C9 C10 -39.45(17) . . . . ?
C8 N C9 C10 145.48(12) . . . . ?
N C9 C10 C11 54.73(15) . . . . ?
C9 C10 C11 C12 144.94(13) . . . . ?
C9 C10 C11 C16 -36.70(17) . . . . ?
C16 C11 C12 C13 -0.9(2) . . . . ?
C10 C11 C12 C13 177.38(13) . . . . ?
C21 O3 C13 C12 -9.6(2) . . . . ?
C21 O3 C13 C14 169.94(12) . . . . ?
C11 C12 C13 O3 179.81(13) . . . . ?
C11 C12 C13 C14 0.3(2) . . . . ?
C22 O4 C14 C15 3.5(2) . . . . ?
C22 O4 C14 C13 -176.00(12) . . . . ?
O3 C13 C14 O4 0.99(17) . . . . ?
C12 C13 C14 O4 -179.49(12) . . . . ?
O3 C13 C14 C15 -178.50(12) . . . . ?
C12 C13 C14 C15 1.0(2) . . . . ?
O4 C14 C15 C16 178.79(13) . . . . ?
C13 C14 C15 C16 -1.8(2) . . . . ?
C12 C11 C16 C15 0.2(2) . . . . ?
C10 C11 C16 C15 -178.20(12) . . . . ?
C12 C11 C16 C17 178.40(12) . . . . ?
C10 C11 C16 C17 0.02(19) . . . . ?
C14 C15 C16 C11 1.2(2) . . . . ?
C14 C15 C16 C17 -177.02(12) . . . . ?
C8 N C17 C18 -2.5(2) . . . . ?
C9 N C17 C18 -177.09(12) . . . . ?
C8 N C17 C16 177.27(12) . . . . ?
C9 N C17 C16 2.68(18) . . . . ?
C11 C16 C17 C18 -161.59(13) . . . . ?
C15 C16 C17 C18 16.6(2) . . . . ?
C11 C16 C17 N 18.65(19) . . . . ?
C15 C16 C17 N -163.16(12) . . . . ?
N C17 C18 C19 4.5(2) . . . . ?
C16 C17 C18 C19 -175.28(12) . . . . ?
C6 C7 C19 C18 174.50(12) . . . . ?
C8 C7 C19 C18 -1.9(2) . . . . ?
C6 C7 C19 C20 -3.7(2) . . . . ?
C8 C7 C19 C20 179.87(12) . . . . ?
C17 C18 C19 C7 -2.3(2) . . . . ?
C17 C18 C19 C20 175.95(12) . . . . ?
C1 O1 C20 O5 171.49(13) . . . . ?
C1 O1 C20 C19 -9.71(19) . . . . ?
C7 C19 C20 O5 -170.80(14) . . . . ?
C18 C19 C20 O5 10.9(2) . . . . ?
C7 C19 C20 O1 10.49(19) . . . . ?
C18 C19 C20 O1 -167.83(12) . . . . ?

_refine_diff_density_max         0.384
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.051


_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_h-m   P-1
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

