# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cs140
_database_code_depnum_ccdc_archive 'CCDC 1900621'
loop_
_audit_author_name
_audit_author_address
'Shiva shivakeshava'
;Tunghai university
Taiwan
;
_audit_update_record             
;
2019-03-02 deposited with the CCDC.	2021-01-18 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_CS509
_database_code_depnum_ccdc_archive 'CCDC 2012685'
loop_
_audit_author_name
_audit_author_address
'Shiva shivakeshava'
;Tunghai university
Taiwan
;
_audit_update_record             
;
2020-06-29 deposited with the CCDC.	2021-01-18 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         'C21 H14 Br N O3'
_chemical_formula_sum            'C21 H14 Br N O3'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         408.24

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                   8.4713(4)
_cell_length_b                   10.0832(5)
_cell_length_c                   10.7844(5)
_cell_angle_alpha                94.9324(17)
_cell_angle_beta                 105.5420(17)
_cell_angle_gamma                108.9946(16)
_cell_volume                     823.87(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9899
_cell_measurement_theta_min      3.156
_cell_measurement_theta_max      27.901
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_F_000             412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.330
_exptl_absorpt_coefficient_mu    2.517
_shelx_estimated_absorpt_T_min   0.366
_shelx_estimated_absorpt_T_max   0.491
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8156
_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            17024
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.658
_diffrn_reflns_theta_max         27.949
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3911
_reflns_number_gt                3679
_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)+(0.0231P)²+0.3953P] 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         3911
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0210
_refine_ls_wR_factor_ref         0.0546
_refine_ls_wR_factor_gt          0.0535
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.003
_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 1.41541(2) 0.51117(2) 0.16624(2) 0.02274(6) Uani 1 1 d . . . . .
O1 O 0.67617(13) 0.16768(11) -0.17234(9) 0.0205(2) Uani 1 1 d . . . . .
O2 O 0.39039(14) 0.08889(13) -0.21666(10) 0.0284(2) Uani 1 1 d . . . . .
O3 O 0.25369(13) 0.07141(12) -0.01166(10) 0.0234(2) Uani 1 1 d . . . . .
N N 0.44749(15) 0.18082(12) 0.19158(11) 0.0151(2) Uani 1 1 d . . . . .
C1 C 0.61513(17) 0.25008(15) 0.27528(13) 0.0164(3) Uani 1 1 d . . . . .
C2 C 0.75560(18) 0.28950(15) 0.23086(13) 0.0180(3) Uani 1 1 d . . . . .
H2A H 0.870604 0.339408 0.290096 0.022 Uiso 1 1 calc R U . . .
C3 C 0.72861(17) 0.25530(14) 0.09503(13) 0.0154(2) Uani 1 1 d . . . . .
C4 C 0.87576(18) 0.29258(14) 0.04240(13) 0.0163(3) Uani 1 1 d . . . . .
C5 C 1.04962(18) 0.37397(15) 0.11814(13) 0.0178(3) Uani 1 1 d . . . . .
H5A H 1.076338 0.411028 0.208390 0.021 Uiso 1 1 calc R U . . .
C6 C 1.18166(18) 0.40014(14) 0.06148(14) 0.0180(3) Uani 1 1 d . . . . .
C7 C 1.1478(2) 0.34573(16) -0.07005(15) 0.0227(3) Uani 1 1 d . . . . .
H7A H 1.241133 0.362771 -0.106811 0.027 Uiso 1 1 calc R U . . .
C8 C 0.9777(2) 0.26711(16) -0.14582(14) 0.0225(3) Uani 1 1 d . . . . .
H8A H 0.952178 0.229419 -0.235754 0.027 Uiso 1 1 calc R U . . .
C9 C 0.84302(18) 0.24303(15) -0.08989(14) 0.0180(3) Uani 1 1 d . . . . .
C10 C 0.52861(19) 0.14278(15) -0.13146(13) 0.0183(3) Uani 1 1 d . . . . .
C11 C 0.55944(18) 0.18236(14) 0.00901(13) 0.0157(3) Uani 1 1 d . . . . .
C12 C 0.40567(18) 0.13882(14) 0.05466(13) 0.0160(3) Uani 1 1 d . . . . .
C13 C 0.32358(18) 0.15738(14) 0.26288(13) 0.0159(3) Uani 1 1 d . . . . .
C14 C 0.14180(18) 0.09589(15) 0.21746(14) 0.0194(3) Uani 1 1 d . . . . .
H14A H 0.079457 0.060308 0.126844 0.023 Uiso 1 1 calc R U . . .
C15 C 0.05429(19) 0.08861(16) 0.31116(15) 0.0229(3) Uani 1 1 d . . . . .
H15A H -0.070465 0.047359 0.283731 0.028 Uiso 1 1 calc R U . . .
C16 C 0.1462(2) 0.14051(16) 0.44362(15) 0.0234(3) Uani 1 1 d . . . . .
H16A H 0.083497 0.134419 0.505243 0.028 Uiso 1 1 calc R U . . .
C17 C 0.32952(19) 0.20150(16) 0.48723(14) 0.0212(3) Uani 1 1 d . . . . .
H17A H 0.392320 0.236148 0.577887 0.025 Uiso 1 1 calc R U . . .
C18 C 0.41755(18) 0.21033(15) 0.39554(13) 0.0172(3) Uani 1 1 d . . . . .
C19 C 0.61292(18) 0.26827(16) 0.41587(13) 0.0189(3) Uani 1 1 d . . . . .
C20 C 0.7016(2) 0.1739(2) 0.48869(15) 0.0295(4) Uani 1 1 d . . . . .
H20A H 0.828106 0.212930 0.501031 0.044 Uiso 1 1 calc R U . . .
H20B H 0.682656 0.171968 0.574354 0.044 Uiso 1 1 calc R U . . .
H20C H 0.650707 0.076566 0.437083 0.044 Uiso 1 1 calc R U . . .
C21 C 0.7017(2) 0.42513(18) 0.48616(16) 0.0303(4) Uani 1 1 d . . . . .
H21A H 0.827788 0.457546 0.496952 0.046 Uiso 1 1 calc R U . . .
H21B H 0.649276 0.483894 0.433944 0.046 Uiso 1 1 calc R U . . .
H21C H 0.684828 0.434087 0.572469 0.046 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 C6 1.8951(14) . ?
O1 C9 1.3700(17) . ?
O1 C10 1.3893(17) . ?
O2 C10 1.1975(17) . ?
O3 C12 1.2184(17) . ?
N C1 1.3705(17) . ?
N C12 1.4142(17) . ?
N C13 1.4322(17) . ?
C1 C2 1.3542(19) . ?
C1 C19 1.5173(18) . ?
C2 C3 1.4140(18) . ?
C2 H2A 0.9500 . ?
C3 C11 1.3927(18) . ?
C3 C4 1.4588(18) . ?
C4 C9 1.3918(19) . ?
C4 C5 1.4011(19) . ?
C5 C6 1.3769(19) . ?
C5 H5A 0.9500 . ?
C6 C7 1.393(2) . ?
C7 C8 1.374(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.392(2) . ?
C8 H8A 0.9500 . ?
C10 C11 1.4623(18) . ?
C11 C12 1.4630(19) . ?
C13 C14 1.3848(19) . ?
C13 C18 1.3954(19) . ?
C14 C15 1.398(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.390(2) . ?
C15 H15A 0.9500 . ?
C16 C17 1.396(2) . ?
C16 H16A 0.9500 . ?
C17 C18 1.3817(19) . ?
C17 H17A 0.9500 . ?
C18 C19 1.5108(19) . ?
C19 C20 1.538(2) . ?
C19 C21 1.535(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C9 O1 C10 122.39(11) . . ?
C1 N C12 124.09(11) . . ?
C1 N C13 110.28(11) . . ?
C12 N C13 125.63(11) . . ?
C2 C1 N 121.63(12) . . ?
C2 C1 C19 128.33(12) . . ?
N C1 C19 110.02(11) . . ?
C1 C2 C3 119.03(12) . . ?
C1 C2 H2A 120.5 . . ?
C3 C2 H2A 120.5 . . ?
C11 C3 C2 120.02(12) . . ?
C11 C3 C4 118.73(12) . . ?
C2 C3 C4 121.24(12) . . ?
C9 C4 C5 117.85(12) . . ?
C9 C4 C3 118.50(12) . . ?
C5 C4 C3 123.64(12) . . ?
C6 C5 C4 119.86(13) . . ?
C6 C5 H5A 120.1 . . ?
C4 C5 H5A 120.1 . . ?
C5 C6 C7 121.68(13) . . ?
C5 C6 Br 118.90(11) . . ?
C7 C6 Br 119.42(11) . . ?
C8 C7 C6 119.07(13) . . ?
C8 C7 H7A 120.5 . . ?
C6 C7 H7A 120.5 . . ?
C7 C8 C9 119.54(13) . . ?
C7 C8 H8A 120.2 . . ?
C9 C8 H8A 120.2 . . ?
O1 C9 C4 121.77(12) . . ?
O1 C9 C8 116.28(12) . . ?
C4 C9 C8 121.95(13) . . ?
O2 C10 O1 115.24(12) . . ?
O2 C10 C11 127.85(13) . . ?
O1 C10 C11 116.90(12) . . ?
C3 C11 C12 121.94(12) . . ?
C3 C11 C10 121.04(12) . . ?
C12 C11 C10 117.01(12) . . ?
O3 C12 N 119.73(12) . . ?
O3 C12 C11 127.02(12) . . ?
N C12 C11 113.24(11) . . ?
C14 C13 C18 122.42(13) . . ?
C14 C13 N 129.69(13) . . ?
C18 C13 N 107.89(11) . . ?
C13 C14 C15 116.91(13) . . ?
C13 C14 H14A 121.5 . . ?
C15 C14 H14A 121.5 . . ?
C16 C15 C14 121.29(14) . . ?
C16 C15 H15A 119.4 . . ?
C14 C15 H15A 119.4 . . ?
C15 C16 C17 120.80(14) . . ?
C15 C16 H16A 119.6 . . ?
C17 C16 H16A 119.6 . . ?
C18 C17 C16 118.48(14) . . ?
C18 C17 H17A 120.8 . . ?
C16 C17 H17A 120.8 . . ?
C17 C18 C13 120.09(13) . . ?
C17 C18 C19 129.31(13) . . ?
C13 C18 C19 110.58(12) . . ?
C18 C19 C1 101.00(11) . . ?
C18 C19 C20 110.55(12) . . ?
C1 C19 C20 109.05(12) . . ?
C18 C19 C21 112.63(12) . . ?
C1 C19 C21 111.94(12) . . ?
C20 C19 C21 111.21(13) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C12 N C1 C2 2.9(2) . . . . ?
C13 N C1 C2 -177.39(13) . . . . ?
C12 N C1 C19 -175.55(12) . . . . ?
C13 N C1 C19 4.19(15) . . . . ?
N C1 C2 C3 -1.5(2) . . . . ?
C19 C1 C2 C3 176.64(13) . . . . ?
C1 C2 C3 C11 0.1(2) . . . . ?
C1 C2 C3 C4 -178.67(13) . . . . ?
C11 C3 C4 C9 -5.47(19) . . . . ?
C2 C3 C4 C9 173.34(13) . . . . ?
C11 C3 C4 C5 175.57(13) . . . . ?
C2 C3 C4 C5 -5.6(2) . . . . ?
C9 C4 C5 C6 -1.2(2) . . . . ?
C3 C4 C5 C6 177.77(13) . . . . ?
C4 C5 C6 C7 -1.0(2) . . . . ?
C4 C5 C6 Br 179.77(10) . . . . ?
C5 C6 C7 C8 1.7(2) . . . . ?
Br C6 C7 C8 -179.06(11) . . . . ?
C6 C7 C8 C9 -0.2(2) . . . . ?
C10 O1 C9 C4 3.7(2) . . . . ?
C10 O1 C9 C8 -176.35(13) . . . . ?
C5 C4 C9 O1 -177.30(12) . . . . ?
C3 C4 C9 O1 3.7(2) . . . . ?
C5 C4 C9 C8 2.7(2) . . . . ?
C3 C4 C9 C8 -176.28(13) . . . . ?
C7 C8 C9 O1 177.97(13) . . . . ?
C7 C8 C9 C4 -2.1(2) . . . . ?
C9 O1 C10 O2 172.40(13) . . . . ?
C9 O1 C10 C11 -8.70(19) . . . . ?
C2 C3 C11 C12 -0.1(2) . . . . ?
C4 C3 C11 C12 178.77(12) . . . . ?
C2 C3 C11 C10 -178.53(13) . . . . ?
C4 C3 C11 C10 0.3(2) . . . . ?
O2 C10 C11 C3 -174.65(15) . . . . ?
O1 C10 C11 C3 6.61(19) . . . . ?
O2 C10 C11 C12 6.8(2) . . . . ?
O1 C10 C11 C12 -171.93(12) . . . . ?
C1 N C12 O3 176.40(13) . . . . ?
C13 N C12 O3 -3.3(2) . . . . ?
C1 N C12 C11 -2.60(18) . . . . ?
C13 N C12 C11 177.71(12) . . . . ?
C3 C11 C12 O3 -177.71(14) . . . . ?
C10 C11 C12 O3 0.8(2) . . . . ?
C3 C11 C12 N 1.20(19) . . . . ?
C10 C11 C12 N 179.72(11) . . . . ?
C1 N C13 C14 177.77(14) . . . . ?
C12 N C13 C14 -2.5(2) . . . . ?
C1 N C13 C18 -1.61(15) . . . . ?
C12 N C13 C18 178.11(12) . . . . ?
C18 C13 C14 C15 0.0(2) . . . . ?
N C13 C14 C15 -179.34(13) . . . . ?
C13 C14 C15 C16 -0.2(2) . . . . ?
C14 C15 C16 C17 -0.1(2) . . . . ?
C15 C16 C17 C18 0.6(2) . . . . ?
C16 C17 C18 C13 -0.8(2) . . . . ?
C16 C17 C18 C19 -178.87(14) . . . . ?
C14 C13 C18 C17 0.5(2) . . . . ?
N C13 C18 C17 179.95(13) . . . . ?
C14 C13 C18 C19 178.94(13) . . . . ?
N C13 C18 C19 -1.63(15) . . . . ?
C17 C18 C19 C1 -177.96(15) . . . . ?
C13 C18 C19 C1 3.81(15) . . . . ?
C17 C18 C19 C20 66.71(19) . . . . ?
C13 C18 C19 C20 -111.53(13) . . . . ?
C17 C18 C19 C21 -58.4(2) . . . . ?
C13 C18 C19 C21 123.38(13) . . . . ?
C2 C1 C19 C18 176.92(14) . . . . ?
N C1 C19 C18 -4.78(15) . . . . ?
C2 C1 C19 C20 -66.62(19) . . . . ?
N C1 C19 C20 111.67(13) . . . . ?
C2 C1 C19 C21 56.9(2) . . . . ?
N C1 C19 C21 -124.84(13) . . . . ?

_refine_diff_density_max         0.331
_refine_diff_density_min         -0.285
_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 ?

####################################################################### 
# 
# 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_CS565
_database_code_depnum_ccdc_archive 'CCDC 2036791'
loop_
_audit_author_name
_audit_author_address
'Shiva shivakeshava'
;Tunghai university
Taiwan
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2021-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C21 H17 N3 O3'
_chemical_formula_sum            'C21 H17 N3 O3'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         359.38

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                   12.4264(5)
_cell_length_b                   14.8397(5)
_cell_length_c                   9.9773(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.5859(14)
_cell_angle_gamma                90
_cell_volume                     1710.82(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7875
_cell_measurement_theta_min      2.639
_cell_measurement_theta_max      27.874
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8662
_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            21544
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.263
_diffrn_reflns_theta_max         27.905
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4076
_reflns_number_gt                3479
_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)+(0.0620P)²+0.6809P] 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         4076
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1177
_refine_ls_wR_factor_gt          0.1114
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_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 0.25457(9) 1.04366(6) 0.53877(11) 0.0257(2) Uani 1 1 d . . . . .
O2 O 0.39114(8) 0.93113(6) 0.48384(11) 0.0228(2) Uani 1 1 d . . . . .
O3 O 0.01242(9) 0.53113(7) 0.71313(12) 0.0303(3) Uani 1 1 d . . . . .
N1 N 0.12176(9) 0.64533(7) 0.67384(12) 0.0183(2) Uani 1 1 d . . . . .
N2 N 0.48693(10) 0.34362(8) 0.49826(13) 0.0240(3) Uani 1 1 d . . . . .
N3 N 0.15289(12) 0.32155(8) 0.69903(16) 0.0328(3) Uani 1 1 d . . . . .
C1 C 0.03368(11) 0.70981(9) 0.68338(16) 0.0230(3) Uani 1 1 d . . . . .
H1A H -0.003818 0.684636 0.747183 0.028 Uiso 1 1 calc R U . . .
H1B H -0.026733 0.718215 0.586460 0.028 Uiso 1 1 calc R U . . .
C2 C 0.08687(11) 0.79992(9) 0.74143(14) 0.0201(3) Uani 1 1 d . . . . .
H2B H 0.024679 0.843929 0.732262 0.024 Uiso 1 1 calc R U . . .
H2C H 0.135195 0.793882 0.845015 0.024 Uiso 1 1 calc R U . . .
C3 C 0.15988(10) 0.83410(8) 0.66158(13) 0.0173(2) Uani 1 1 d . . . . .
C4 C 0.16628(11) 0.92601(8) 0.63394(14) 0.0191(3) Uani 1 1 d . . . . .
H4A H 0.119038 0.967771 0.659357 0.023 Uiso 1 1 calc R U . . .
C5 C 0.24119(11) 0.95639(8) 0.56967(14) 0.0188(3) Uani 1 1 d . . . . .
C6 C 0.31403(11) 0.89424(8) 0.53613(14) 0.0180(3) Uani 1 1 d . . . . .
C7 C 0.30494(11) 0.80360(8) 0.55881(13) 0.0173(2) Uani 1 1 d . . . . .
H7A H 0.351932 0.761892 0.532847 0.021 Uiso 1 1 calc R U . . .
C8 C 0.22624(10) 0.77208(8) 0.62040(13) 0.0163(2) Uani 1 1 d . . . . .
C9 C 0.21420(10) 0.67486(8) 0.64087(13) 0.0160(2) Uani 1 1 d . . . . .
C10 C 0.28931(11) 0.61269(8) 0.62073(14) 0.0175(3) Uani 1 1 d . . . . .
H10A H 0.354715 0.632862 0.601405 0.021 Uiso 1 1 calc R U . . .
C11 C 0.27033(11) 0.52039(8) 0.62841(13) 0.0173(3) Uani 1 1 d . . . . .
C12 C 0.17933(11) 0.49131(8) 0.66506(14) 0.0192(3) Uani 1 1 d . . . . .
C13 C 0.09790(11) 0.55374(9) 0.68708(14) 0.0202(3) Uani 1 1 d . . . . .
C14 C 0.17539(14) 1.10762(9) 0.55738(17) 0.0290(3) Uani 1 1 d . . . . .
H14A H 0.193893 1.167853 0.531754 0.043 Uiso 1 1 calc R U . . .
H14B H 0.096296 1.091523 0.494972 0.043 Uiso 1 1 calc R U . . .
H14C H 0.181610 1.107402 0.658190 0.043 Uiso 1 1 calc R U . . .
C15 C 0.48260(12) 0.87340(9) 0.48045(17) 0.0247(3) Uani 1 1 d . . . . .
H15A H 0.532564 0.906595 0.441201 0.037 Uiso 1 1 calc R U . . .
H15B H 0.528292 0.853123 0.578447 0.037 Uiso 1 1 calc R U . . .
H15C H 0.449471 0.821014 0.419392 0.037 Uiso 1 1 calc R U . . .
C16 C 0.34594(11) 0.45627(8) 0.58956(13) 0.0174(2) Uani 1 1 d . . . . .
C17 C 0.46576(11) 0.45976(9) 0.65492(14) 0.0199(3) Uani 1 1 d . . . . .
H17A H 0.501963 0.500678 0.731550 0.024 Uiso 1 1 calc R U . . .
C18 C 0.53145(12) 0.40230(9) 0.60604(14) 0.0219(3) Uani 1 1 d . . . . .
H18A H 0.613263 0.404858 0.652149 0.026 Uiso 1 1 calc R U . . .
C19 C 0.37148(13) 0.34015(9) 0.43744(17) 0.0270(3) Uani 1 1 d . . . . .
H19A H 0.337833 0.298059 0.361786 0.032 Uiso 1 1 calc R U . . .
C20 C 0.29800(12) 0.39445(9) 0.47840(16) 0.0239(3) Uani 1 1 d . . . . .
H20A H 0.216444 0.389562 0.431467 0.029 Uiso 1 1 calc R U . . .
C21 C 0.16253(12) 0.39726(9) 0.68361(15) 0.0232(3) 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
O1 C5 1.3556(15) . ?
O1 C14 1.4276(16) . ?
O2 C6 1.3630(15) . ?
O2 C15 1.4335(16) . ?
O3 C13 1.2294(16) . ?
N1 C9 1.3775(15) . ?
N1 C13 1.4077(16) . ?
N1 C1 1.4830(16) . ?
N2 C18 1.3353(18) . ?
N2 C19 1.3374(19) . ?
N3 C21 1.1462(18) . ?
C1 C2 1.5095(19) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.4989(17) . ?
C2 H2B 0.9900 . ?
C2 H2C 0.9900 . ?
C3 C8 1.3948(17) . ?
C3 C4 1.3996(18) . ?
C4 C5 1.3857(18) . ?
C4 H4A 0.9500 . ?
C5 C6 1.4159(17) . ?
C6 C7 1.3755(17) . ?
C7 C8 1.4124(17) . ?
C7 H7A 0.9500 . ?
C8 C9 1.4723(17) . ?
C9 C10 1.3787(17) . ?
C10 C11 1.3968(17) . ?
C10 H10A 0.9500 . ?
C11 C12 1.3795(17) . ?
C11 C16 1.4855(17) . ?
C12 C21 1.4333(18) . ?
C12 C13 1.4470(18) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.3893(18) . ?
C16 C20 1.3930(18) . ?
C17 C18 1.3872(18) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 C20 1.3873(19) . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9500 . ?

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
C5 O1 C14 117.23(11) . . ?
C6 O2 C15 116.36(10) . . ?
C9 N1 C13 123.54(10) . . ?
C9 N1 C1 120.67(10) . . ?
C13 N1 C1 115.53(10) . . ?
C18 N2 C19 116.61(12) . . ?
N1 C1 C2 111.52(10) . . ?
N1 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
C3 C2 C1 111.16(10) . . ?
C3 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2C 109.4 . . ?
C1 C2 H2C 109.4 . . ?
H2B C2 H2C 108.0 . . ?
C8 C3 C4 120.16(11) . . ?
C8 C3 C2 118.19(11) . . ?
C4 C3 C2 121.59(11) . . ?
C5 C4 C3 120.32(11) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
O1 C5 C4 125.14(11) . . ?
O1 C5 C6 115.21(12) . . ?
C4 C5 C6 119.61(11) . . ?
O2 C6 C7 124.58(11) . . ?
O2 C6 C5 115.43(11) . . ?
C7 C6 C5 119.98(12) . . ?
C6 C7 C8 120.49(11) . . ?
C6 C7 H7A 119.8 . . ?
C8 C7 H7A 119.8 . . ?
C3 C8 C7 119.25(11) . . ?
C3 C8 C9 120.29(11) . . ?
C7 C8 C9 120.46(11) . . ?
C10 C9 N1 119.39(11) . . ?
C10 C9 C8 121.77(11) . . ?
N1 C9 C8 118.76(11) . . ?
C9 C10 C11 120.74(11) . . ?
C9 C10 H10A 119.6 . . ?
C11 C10 H10A 119.6 . . ?
C12 C11 C10 119.52(11) . . ?
C12 C11 C16 121.85(11) . . ?
C10 C11 C16 118.56(11) . . ?
C11 C12 C21 120.76(12) . . ?
C11 C12 C13 121.81(11) . . ?
C21 C12 C13 117.43(11) . . ?
O3 C13 N1 120.77(12) . . ?
O3 C13 C12 124.34(12) . . ?
N1 C13 C12 114.88(11) . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C20 117.96(12) . . ?
C17 C16 C11 121.67(11) . . ?
C20 C16 C11 120.22(12) . . ?
C18 C17 C16 118.66(12) . . ?
C18 C17 H17A 120.7 . . ?
C16 C17 H17A 120.7 . . ?
N2 C18 C17 124.12(12) . . ?
N2 C18 H18A 117.9 . . ?
C17 C18 H18A 117.9 . . ?
N2 C19 C20 123.81(13) . . ?
N2 C19 H19A 118.1 . . ?
C20 C19 H19A 118.1 . . ?
C19 C20 C16 118.82(13) . . ?
C19 C20 H20A 120.6 . . ?
C16 C20 H20A 120.6 . . ?
N3 C21 C12 177.70(14) . . ?

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
C9 N1 C1 C2 -34.03(17) . . . . ?
C13 N1 C1 C2 151.66(11) . . . . ?
N1 C1 C2 C3 50.35(15) . . . . ?
C1 C2 C3 C8 -38.28(16) . . . . ?
C1 C2 C3 C4 144.55(12) . . . . ?
C8 C3 C4 C5 -2.05(19) . . . . ?
C2 C3 C4 C5 175.06(11) . . . . ?
C14 O1 C5 C4 -8.20(19) . . . . ?
C14 O1 C5 C6 174.00(12) . . . . ?
C3 C4 C5 O1 -179.69(12) . . . . ?
C3 C4 C5 C6 -1.98(19) . . . . ?
C15 O2 C6 C7 -13.01(18) . . . . ?
C15 O2 C6 C5 166.09(11) . . . . ?
O1 C5 C6 O2 2.95(17) . . . . ?
C4 C5 C6 O2 -174.98(11) . . . . ?
O1 C5 C6 C7 -177.90(11) . . . . ?
C4 C5 C6 C7 4.17(19) . . . . ?
O2 C6 C7 C8 176.73(12) . . . . ?
C5 C6 C7 C8 -2.34(19) . . . . ?
C4 C3 C8 C7 3.87(18) . . . . ?
C2 C3 C8 C7 -173.33(11) . . . . ?
C4 C3 C8 C9 -176.07(11) . . . . ?
C2 C3 C8 C9 6.73(17) . . . . ?
C6 C7 C8 C3 -1.67(18) . . . . ?
C6 C7 C8 C9 178.27(11) . . . . ?
C13 N1 C9 C10 -0.70(18) . . . . ?
C1 N1 C9 C10 -174.54(12) . . . . ?
C13 N1 C9 C8 176.02(11) . . . . ?
C1 N1 C9 C8 2.17(17) . . . . ?
C3 C8 C9 C10 -170.65(12) . . . . ?
C7 C8 C9 C10 9.41(18) . . . . ?
C3 C8 C9 N1 12.72(17) . . . . ?
C7 C8 C9 N1 -167.22(11) . . . . ?
N1 C9 C10 C11 2.26(19) . . . . ?
C8 C9 C10 C11 -174.36(11) . . . . ?
C9 C10 C11 C12 -3.90(19) . . . . ?
C9 C10 C11 C16 173.13(11) . . . . ?
C10 C11 C12 C21 -175.62(12) . . . . ?
C16 C11 C12 C21 7.44(19) . . . . ?
C10 C11 C12 C13 4.01(19) . . . . ?
C16 C11 C12 C13 -172.92(12) . . . . ?
C9 N1 C13 O3 -178.14(13) . . . . ?
C1 N1 C13 O3 -4.01(18) . . . . ?
C9 N1 C13 C12 0.73(18) . . . . ?
C1 N1 C13 C12 174.86(11) . . . . ?
C11 C12 C13 O3 176.42(13) . . . . ?
C21 C12 C13 O3 -3.9(2) . . . . ?
C11 C12 C13 N1 -2.41(18) . . . . ?
C21 C12 C13 N1 177.24(12) . . . . ?
C12 C11 C16 C17 -128.66(14) . . . . ?
C10 C11 C16 C17 54.38(17) . . . . ?
C12 C11 C16 C20 55.79(18) . . . . ?
C10 C11 C16 C20 -121.18(14) . . . . ?
C20 C16 C17 C18 0.40(18) . . . . ?
C11 C16 C17 C18 -175.25(12) . . . . ?
C19 N2 C18 C17 -1.4(2) . . . . ?
C16 C17 C18 N2 0.6(2) . . . . ?
C18 N2 C19 C20 1.2(2) . . . . ?
N2 C19 C20 C16 -0.3(2) . . . . ?
C17 C16 C20 C19 -0.56(19) . . . . ?
C11 C16 C20 C19 175.16(12) . . . . ?

_refine_diff_density_max         0.344
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.046

_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
_database_code_depnum_ccdc_archive 'CCDC 2012710'
loop_
_audit_author_name
_audit_author_address
'Shiva shivakeshava'
;Tunghai university
Taiwan
;
_audit_update_record             
;
2020-06-29 deposited with the CCDC.	2021-01-18 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_CS506A
_database_code_depnum_ccdc_archive 'CCDC 2012684'
loop_
_audit_author_name
_audit_author_address
'Shiva shivakeshava'
;Tunghai university
Taiwan
;
_audit_update_record             
;
2020-06-29 deposited with the CCDC.	2021-01-18 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         'C21 H17 N O3'
_chemical_formula_sum            'C21 H17 N O3'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         331.36

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                   8.9048(2)
_cell_length_b                   19.0917(5)
_cell_length_c                   10.2276(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.2045(12)
_cell_angle_gamma                90
_cell_volume                     1669.69(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9986
_cell_measurement_theta_min      2.891
_cell_measurement_theta_max      27.830
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8741
_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            28812
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0356
_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       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.198
_diffrn_reflns_theta_max         27.881
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3965
_reflns_number_gt                3377
_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)+(0.0637P)²+0.5083P] 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         3965
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1126
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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
O1 O 1.00426(9) 0.59857(5) 0.77362(9) 0.0286(2) Uani 1 1 d . . . . .
O2 O 0.81726(10) 0.67570(4) 0.69177(9) 0.0303(2) Uani 1 1 d . . . . .
O3 O 0.48610(10) 0.56693(5) 0.74121(9) 0.0328(2) Uani 1 1 d . . . . .
N N 0.50421(10) 0.60473(5) 0.53585(9) 0.0201(2) Uani 1 1 d . . . . .
C1 C 0.84863(13) 0.61539(6) 0.72118(11) 0.0227(2) Uani 1 1 d . . . . .
C2 C 1.05269(13) 0.53289(7) 0.82349(11) 0.0267(3) Uani 1 1 d . . . . .
C3 C 1.21218(15) 0.52381(9) 0.88302(13) 0.0365(3) Uani 1 1 d . . . . .
H3A H 1.283651 0.561141 0.886193 0.044 Uiso 1 1 calc R U . . .
C4 C 1.26371(16) 0.45908(9) 0.93732(13) 0.0429(4) Uani 1 1 d . . . . .
H4A H 1.372069 0.451996 0.979288 0.051 Uiso 1 1 calc R U . . .
C5 C 1.16000(19) 0.40414(9) 0.93171(14) 0.0428(4) Uani 1 1 d . . . . .
H5A H 1.197818 0.359908 0.969387 0.051 Uiso 1 1 calc R U . . .
C6 C 1.00181(17) 0.41359(7) 0.87146(13) 0.0362(3) Uani 1 1 d . . . . .
H6A H 0.931139 0.375852 0.867501 0.043 Uiso 1 1 calc R U . . .
C7 C 0.94580(14) 0.47890(7) 0.81623(11) 0.0266(3) Uani 1 1 d . . . . .
C8 C 0.78297(14) 0.49420(6) 0.75633(11) 0.0246(2) Uani 1 1 d . . . . .
H8A H 0.707444 0.458349 0.750741 0.030 Uiso 1 1 calc R U . . .
C9 C 0.73597(12) 0.55836(6) 0.70818(10) 0.0207(2) Uani 1 1 d . . . . .
C10 C 0.56510(13) 0.57656(6) 0.66289(11) 0.0211(2) Uani 1 1 d . . . . .
C11 C 0.35789(12) 0.64114(6) 0.49763(10) 0.0204(2) Uani 1 1 d . . . . .
C12 C 0.23174(13) 0.63565(6) 0.55155(11) 0.0245(2) Uani 1 1 d . . . . .
H12A H 0.233278 0.604018 0.623613 0.029 Uiso 1 1 calc R U . . .
C13 C 0.10258(14) 0.67830(7) 0.49607(13) 0.0306(3) Uani 1 1 d . . . . .
H13A H 0.014008 0.675418 0.530363 0.037 Uiso 1 1 calc R U . . .
C14 C 0.10120(16) 0.72488(7) 0.39159(14) 0.0353(3) Uani 1 1 d . . . . .
H14A H 0.012740 0.754059 0.356242 0.042 Uiso 1 1 calc R U . . .
C15 C 0.22851(16) 0.72912(7) 0.33832(13) 0.0325(3) Uani 1 1 d . . . . .
H15A H 0.227337 0.760941 0.266636 0.039 Uiso 1 1 calc R U . . .
C16 C 0.35687(14) 0.68654(6) 0.39073(11) 0.0238(2) Uani 1 1 d . . . . .
C17 C 0.50863(14) 0.68158(6) 0.35181(11) 0.0249(2) Uani 1 1 d . . . . .
C18 C 0.58273(13) 0.61684(6) 0.43225(11) 0.0218(2) Uani 1 1 d . . . . .
C19 C 0.69041(15) 0.57570(7) 0.40689(12) 0.0297(3) Uani 1 1 d . . . . .
H19A H 0.7362(19) 0.5888(9) 0.3343(17) 0.040(4) Uiso 1 1 d . . . . .
H19B H 0.7272(18) 0.5326(8) 0.4578(16) 0.034(4) Uiso 1 1 d . . . . .
C20 C 0.48255(18) 0.67328(8) 0.19805(13) 0.0366(3) Uani 1 1 d . . . . .
H20A H 0.583891 0.670324 0.178261 0.055 Uiso 1 1 calc R U . . .
H20B H 0.422669 0.630437 0.166844 0.055 Uiso 1 1 calc R U . . .
H20C H 0.424424 0.713786 0.150714 0.055 Uiso 1 1 calc R U . . .
C21 C 0.61033(16) 0.74673(7) 0.40274(14) 0.0338(3) Uani 1 1 d . . . . .
H21A H 0.708153 0.743007 0.377072 0.051 Uiso 1 1 calc R U . . .
H21B H 0.553678 0.788846 0.361475 0.051 Uiso 1 1 calc R U . . .
H21C H 0.633833 0.749758 0.502065 0.051 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
O1 C2 1.3767(15) . ?
O1 C1 1.3772(13) . ?
O2 C1 1.2030(15) . ?
O3 C10 1.2185(14) . ?
N C10 1.3705(14) . ?
N C11 1.4315(14) . ?
N C18 1.4416(14) . ?
C1 C9 1.4613(15) . ?
C2 C3 1.3911(16) . ?
C2 C7 1.3909(18) . ?
C3 C4 1.380(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.388(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.383(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.4019(18) . ?
C6 H6A 0.9500 . ?
C7 C8 1.4378(16) . ?
C8 C9 1.3428(16) . ?
C8 H8A 0.9500 . ?
C9 C10 1.5023(15) . ?
C11 C12 1.3867(15) . ?
C11 C16 1.3933(15) . ?
C12 C13 1.3941(17) . ?
C12 H12A 0.9500 . ?
C13 C14 1.3877(18) . ?
C13 H13A 0.9500 . ?
C14 C15 1.3904(19) . ?
C14 H14A 0.9500 . ?
C15 C16 1.3830(17) . ?
C15 H15A 0.9500 . ?
C16 C17 1.5146(16) . ?
C17 C18 1.5287(16) . ?
C17 C20 1.5324(16) . ?
C17 C21 1.5412(17) . ?
C18 C19 1.3200(17) . ?
C19 H19A 0.974(17) . ?
C19 H19B 0.980(16) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C2 O1 C1 122.26(9) . . ?
C10 N C11 122.59(9) . . ?
C10 N C18 127.95(9) . . ?
C11 N C18 108.22(9) . . ?
O2 C1 O1 117.31(10) . . ?
O2 C1 C9 125.79(10) . . ?
O1 C1 C9 116.89(10) . . ?
O1 C2 C3 116.85(12) . . ?
O1 C2 C7 121.08(10) . . ?
C3 C2 C7 122.06(13) . . ?
C4 C3 C2 118.16(14) . . ?
C4 C3 H3A 120.9 . . ?
C2 C3 H3A 120.9 . . ?
C3 C4 C5 121.17(13) . . ?
C3 C4 H4A 119.4 . . ?
C5 C4 H4A 119.4 . . ?
C6 C5 C4 120.20(14) . . ?
C6 C5 H5A 119.9 . . ?
C4 C5 H5A 119.9 . . ?
C5 C6 C7 119.95(15) . . ?
C5 C6 H6A 120.0 . . ?
C7 C6 H6A 120.0 . . ?
C2 C7 C6 118.45(12) . . ?
C2 C7 C8 117.77(11) . . ?
C6 C7 C8 123.74(12) . . ?
C9 C8 C7 121.04(11) . . ?
C9 C8 H8A 119.5 . . ?
C7 C8 H8A 119.5 . . ?
C8 C9 C1 120.70(10) . . ?
C8 C9 C10 120.62(10) . . ?
C1 C9 C10 117.79(10) . . ?
O3 C10 N 122.29(10) . . ?
O3 C10 C9 118.90(10) . . ?
N C10 C9 118.80(9) . . ?
C12 C11 C16 122.04(10) . . ?
C12 C11 N 129.15(10) . . ?
C16 C11 N 108.81(9) . . ?
C11 C12 C13 117.51(11) . . ?
C11 C12 H12A 121.2 . . ?
C13 C12 H12A 121.2 . . ?
C14 C13 C12 121.11(12) . . ?
C14 C13 H13A 119.4 . . ?
C12 C13 H13A 119.4 . . ?
C15 C14 C13 120.40(12) . . ?
C15 C14 H14A 119.8 . . ?
C13 C14 H14A 119.8 . . ?
C16 C15 C14 119.34(11) . . ?
C16 C15 H15A 120.3 . . ?
C14 C15 H15A 120.3 . . ?
C15 C16 C11 119.57(11) . . ?
C15 C16 C17 129.53(11) . . ?
C11 C16 C17 110.88(10) . . ?
C16 C17 C18 101.06(9) . . ?
C16 C17 C20 112.66(10) . . ?
C18 C17 C20 112.82(10) . . ?
C16 C17 C21 110.12(10) . . ?
C18 C17 C21 110.24(10) . . ?
C20 C17 C21 109.68(10) . . ?
C19 C18 N 125.24(11) . . ?
C19 C18 C17 127.11(11) . . ?
N C18 C17 107.47(9) . . ?
C18 C19 H19A 118.6(10) . . ?
C18 C19 H19B 123.2(9) . . ?
H19A C19 H19B 118.2(14) . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C2 O1 C1 O2 173.28(10) . . . . ?
C2 O1 C1 C9 -5.81(15) . . . . ?
C1 O1 C2 C3 -175.33(10) . . . . ?
C1 O1 C2 C7 3.60(16) . . . . ?
O1 C2 C3 C4 178.23(11) . . . . ?
C7 C2 C3 C4 -0.70(18) . . . . ?
C2 C3 C4 C5 0.68(19) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C4 C5 C6 C7 -0.2(2) . . . . ?
O1 C2 C7 C6 -178.61(10) . . . . ?
C3 C2 C7 C6 0.27(17) . . . . ?
O1 C2 C7 C8 -0.70(16) . . . . ?
C3 C2 C7 C8 178.18(11) . . . . ?
C5 C6 C7 C2 0.19(18) . . . . ?
C5 C6 C7 C8 -177.58(12) . . . . ?
C2 C7 C8 C9 0.47(16) . . . . ?
C6 C7 C8 C9 178.26(11) . . . . ?
C7 C8 C9 C1 -2.91(16) . . . . ?
C7 C8 C9 C10 -171.85(10) . . . . ?
O2 C1 C9 C8 -173.52(11) . . . . ?
O1 C1 C9 C8 5.48(15) . . . . ?
O2 C1 C9 C10 -4.28(17) . . . . ?
O1 C1 C9 C10 174.73(9) . . . . ?
C11 N C10 O3 16.37(17) . . . . ?
C18 N C10 O3 -177.92(11) . . . . ?
C11 N C10 C9 -162.29(10) . . . . ?
C18 N C10 C9 3.42(16) . . . . ?
C8 C9 C10 O3 53.63(15) . . . . ?
C1 C9 C10 O3 -115.62(12) . . . . ?
C8 C9 C10 N -127.66(11) . . . . ?
C1 C9 C10 N 63.09(14) . . . . ?
C10 N C11 C12 -24.06(17) . . . . ?
C18 N C11 C12 167.77(11) . . . . ?
C10 N C11 C16 156.01(10) . . . . ?
C18 N C11 C16 -12.16(12) . . . . ?
C16 C11 C12 C13 -0.89(17) . . . . ?
N C11 C12 C13 179.18(11) . . . . ?
C11 C12 C13 C14 -0.55(19) . . . . ?
C12 C13 C14 C15 1.1(2) . . . . ?
C13 C14 C15 C16 -0.2(2) . . . . ?
C14 C15 C16 C11 -1.24(19) . . . . ?
C14 C15 C16 C17 -179.44(12) . . . . ?
C12 C11 C16 C15 1.80(17) . . . . ?
N C11 C16 C15 -178.26(11) . . . . ?
C12 C11 C16 C17 -179.68(10) . . . . ?
N C11 C16 C17 0.26(12) . . . . ?
C15 C16 C17 C18 -170.98(12) . . . . ?
C11 C16 C17 C18 10.70(12) . . . . ?
C15 C16 C17 C20 -50.32(17) . . . . ?
C11 C16 C17 C20 131.35(11) . . . . ?
C15 C16 C17 C21 72.47(16) . . . . ?
C11 C16 C17 C21 -105.86(11) . . . . ?
C10 N C18 C19 36.32(17) . . . . ?
C11 N C18 C19 -156.33(12) . . . . ?
C10 N C18 C17 -148.32(11) . . . . ?
C11 N C18 C17 19.03(11) . . . . ?
C16 C17 C18 C19 157.58(12) . . . . ?
C20 C17 C18 C19 37.03(17) . . . . ?
C21 C17 C18 C19 -85.96(14) . . . . ?
C16 C17 C18 N -17.67(11) . . . . ?
C20 C17 C18 N -138.21(10) . . . . ?
C21 C17 C18 N 98.80(11) . . . . ?

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.036

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

