# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_a14854
_database_code_depnum_ccdc_archive 'CCDC 2110327'
loop_
_audit_author_name
_audit_author_address
'Shaik Anwar'
;Vignans Foundation for Science Technology and research
India
;
_audit_update_record             
;
2021-09-17 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H17 F O4'
_chemical_formula_sum            'C22 H17 F O4'
_chemical_formula_weight         364.36

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   18.116(7)
_cell_length_b                   5.561(2)
_cell_length_c                   18.910(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.394(10)
_cell_angle_gamma                90.00
_cell_volume                     1761.2(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1538
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      20.58

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9588
_exptl_absorpt_correction_T_max  0.9990
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11711
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_reflns_av_sigmaI/netI    0.1234
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3101
_reflns_number_gt                1576
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0477P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3101
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1469
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1191
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_restrained_S_all      0.959
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.14569(17) 1.2446(6) 0.35089(16) 0.0262(8) Uani 1 1 d . . .
C2 C 0.21835(16) 1.1001(6) 0.36383(15) 0.0244(8) Uani 1 1 d . . .
C3 C 0.27656(18) 1.1227(6) 0.33335(16) 0.0342(9) Uani 1 1 d . . .
H3 H 0.2740 1.2472 0.2981 0.041 Uiso 1 1 calc R . .
C4 C 0.33841(18) 0.9579(7) 0.35602(17) 0.0391(9) Uani 1 1 d . . .
H4 H 0.3784 0.9678 0.3352 0.047 Uiso 1 1 calc R . .
C5 C 0.34319(18) 0.7786(6) 0.40852(18) 0.0388(9) Uani 1 1 d . . .
H5 H 0.3863 0.6678 0.4230 0.047 Uiso 1 1 calc R . .
C6 C 0.28629(18) 0.7591(6) 0.43982(16) 0.0338(9) Uani 1 1 d . . .
H6 H 0.2902 0.6388 0.4768 0.041 Uiso 1 1 calc R . .
C7 C 0.22345(16) 0.9190(6) 0.41607(15) 0.0246(8) Uani 1 1 d . . .
C8 C 0.15364(16) 0.9307(6) 0.43844(16) 0.0255(8) Uani 1 1 d . . .
C9 C 0.09520(16) 1.1154(6) 0.38709(15) 0.0227(8) Uani 1 1 d . . .
C10 C 0.05548(16) 1.2722(6) 0.42947(15) 0.0292(8) Uani 1 1 d . . .
H10A H 0.0869 1.2704 0.4853 0.035 Uiso 1 1 calc R . .
H10B H 0.0500 1.4405 0.4111 0.035 Uiso 1 1 calc R . .
C11 C -0.02438(16) 1.1594(6) 0.41106(15) 0.0270(8) Uani 1 1 d . . .
H11 H -0.0598 1.2020 0.4353 0.032 Uiso 1 1 calc R . .
C12 C -0.04038(16) 0.9938(6) 0.35728(15) 0.0232(8) Uani 1 1 d . . .
C13 C -0.11293(17) 0.8434(6) 0.32545(18) 0.0277(8) Uani 1 1 d . . .
C14 C -0.24335(17) 0.7772(6) 0.32466(17) 0.0385(9) Uani 1 1 d . . .
H14A H -0.2553 0.7229 0.2716 0.046 Uiso 1 1 calc R . .
H14B H -0.2872 0.8843 0.3241 0.046 Uiso 1 1 calc R . .
C15 C -0.23938(18) 0.5639(7) 0.37399(18) 0.0492(10) Uani 1 1 d . . .
H15A H -0.2398 0.6568 0.4238 0.059 Uiso 1 1 d R . .
H15B H -0.2990 0.4917 0.3555 0.059 Uiso 1 1 d R . .
H15C H -0.1843 0.4393 0.3726 0.059 Uiso 1 1 d R . .
C16 C 0.02495(15) 0.9633(5) 0.32649(14) 0.0217(7) Uani 1 1 d . . .
H16 H 0.0412 0.7903 0.3311 0.026 Uiso 1 1 calc R . .
C17 C -0.00048(15) 1.0384(6) 0.24392(15) 0.0230(8) Uani 1 1 d . . .
C18 C -0.04223(16) 1.2488(6) 0.21649(17) 0.0280(8) Uani 1 1 d . . .
H18 H -0.0545 1.3523 0.2505 0.034 Uiso 1 1 calc R . .
C19 C -0.06637(17) 1.3107(6) 0.14017(17) 0.0337(9) Uani 1 1 d . . .
H19 H -0.0951 1.4553 0.1215 0.040 Uiso 1 1 calc R . .
C20 C -0.04830(18) 1.1609(7) 0.09258(17) 0.0350(9) Uani 1 1 d . . .
C21 C -0.00723(18) 0.9505(7) 0.11689(17) 0.0380(9) Uani 1 1 d . . .
H21 H 0.0044 0.8485 0.0822 0.046 Uiso 1 1 calc R . .
C22 C 0.01691(17) 0.8905(6) 0.19340(16) 0.0297(8) Uani 1 1 d . . .
H22 H 0.0458 0.7459 0.2115 0.036 Uiso 1 1 calc R . .
F1 F -0.07248(11) 1.2194(3) 0.01715(9) 0.0575(6) Uani 1 1 d . . .
O1 O 0.13031(11) 1.4375(4) 0.31787(11) 0.0364(6) Uani 1 1 d . . .
O2 O 0.14311(11) 0.8098(4) 0.48719(11) 0.0381(6) Uani 1 1 d . . .
O3 O -0.12125(12) 0.6845(4) 0.28071(13) 0.0477(7) Uani 1 1 d . . .
O4 O -0.16860(11) 0.9107(4) 0.35209(10) 0.0364(6) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.219(3) . ?
C1 C2 1.481(4) . ?
C1 C9 1.516(4) . ?
C2 C7 1.389(4) . ?
C2 C3 1.387(4) . ?
C3 C4 1.383(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.375(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.378(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.480(4) . ?
C8 O2 1.213(3) . ?
C8 C9 1.528(4) . ?
C9 C10 1.536(4) . ?
C9 C16 1.593(4) . ?
C10 C11 1.491(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.320(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.479(4) . ?
C12 C16 1.514(3) . ?
C13 O3 1.192(3) . ?
C13 O4 1.341(3) . ?
C14 O4 1.456(3) . ?
C14 C15 1.494(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 1.0776 . ?
C15 H15B 1.0777 . ?
C15 H15C 1.2232 . ?
C16 C17 1.509(3) . ?
C16 H16 1.0000 . ?
C17 C18 1.383(4) . ?
C17 C22 1.385(4) . ?
C18 C19 1.383(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.355(4) . ?
C19 H19 0.9500 . ?
C20 F1 1.362(3) . ?
C20 C21 1.368(4) . ?
C21 C22 1.383(4) . ?
C21 H21 0.9500 . ?
C22 H22 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
O1 C1 C2 125.3(3) . . ?
O1 C1 C9 126.1(3) . . ?
C2 C1 C9 108.6(3) . . ?
C7 C2 C3 120.4(3) . . ?
C7 C2 C1 109.0(3) . . ?
C3 C2 C1 130.6(3) . . ?
C4 C3 C2 117.8(3) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 118.1(3) . . ?
C5 C6 H6 121.0 . . ?
C7 C6 H6 121.0 . . ?
C6 C7 C2 121.5(3) . . ?
C6 C7 C8 128.7(3) . . ?
C2 C7 C8 109.8(3) . . ?
O2 C8 C7 126.3(3) . . ?
O2 C8 C9 125.7(3) . . ?
C7 C8 C9 108.0(3) . . ?
C1 C9 C8 102.4(2) . . ?
C1 C9 C10 116.7(2) . . ?
C8 C9 C10 113.5(2) . . ?
C1 C9 C16 112.4(2) . . ?
C8 C9 C16 105.7(2) . . ?
C10 C9 C16 105.8(2) . . ?
C11 C10 C9 104.2(2) . . ?
C11 C10 H10A 110.9 . . ?
C9 C10 H10A 110.9 . . ?
C11 C10 H10B 110.9 . . ?
C9 C10 H10B 110.9 . . ?
H10A C10 H10B 108.9 . . ?
C12 C11 C10 112.5(3) . . ?
C12 C11 H11 123.8 . . ?
C10 C11 H11 123.8 . . ?
C11 C12 C13 127.5(3) . . ?
C11 C12 C16 113.6(3) . . ?
C13 C12 C16 118.9(3) . . ?
O3 C13 O4 124.3(3) . . ?
O3 C13 C12 124.1(3) . . ?
O4 C13 C12 111.6(3) . . ?
O4 C14 C15 111.4(2) . . ?
O4 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
O4 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 H15A 98.7 . . ?
C14 C15 H15B 106.8 . . ?
H15A C15 H15B 97.0 . . ?
C14 C15 H15C 106.4 . . ?
H15A C15 H15C 124.6 . . ?
H15B C15 H15C 120.5 . . ?
C17 C16 C12 113.1(2) . . ?
C17 C16 C9 116.3(2) . . ?
C12 C16 C9 101.0(2) . . ?
C17 C16 H16 108.7 . . ?
C12 C16 H16 108.7 . . ?
C9 C16 H16 108.7 . . ?
C18 C17 C22 118.6(3) . . ?
C18 C17 C16 122.0(3) . . ?
C22 C17 C16 119.3(3) . . ?
C19 C18 C17 120.8(3) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C18 118.7(3) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C19 C20 F1 119.1(3) . . ?
C19 C20 C21 122.7(3) . . ?
F1 C20 C21 118.2(3) . . ?
C20 C21 C22 118.2(3) . . ?
C20 C21 H21 120.9 . . ?
C22 C21 H21 120.9 . . ?
C21 C22 C17 120.9(3) . . ?
C21 C22 H22 119.5 . . ?
C17 C22 H22 119.5 . . ?
C13 O4 C14 117.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_a14859
_database_code_depnum_ccdc_archive 'CCDC 2110328'
loop_
_audit_author_name
_audit_author_address
'Shaik Anwar'
;Vignans Foundation for Science Technology and research
India
;
_audit_update_record             
;
2021-09-17 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H17 Cl O4'
_chemical_formula_sum            'C22 H17 Cl O4'
_chemical_formula_weight         380.81

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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   18.038(4)
_cell_length_b                   5.5757(14)
_cell_length_c                   19.590(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.044(6)
_cell_angle_gamma                90.00
_cell_volume                     1838.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1728
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      24.73

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8690
_exptl_absorpt_correction_T_max  0.9977
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11954
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_sigmaI/netI    0.1073
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.32
_diffrn_reflns_theta_max         25.09
_reflns_number_total             3221
_reflns_number_gt                1833
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0653P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3221
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1282
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1409
_refine_ls_wR_factor_gt          0.1182
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_restrained_S_all      0.978
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.65415(18) 0.5857(6) 0.43614(17) 0.0249(8) Uani 1 1 d . . .
C2 C 0.72243(18) 0.5975(6) 0.41098(16) 0.0233(8) Uani 1 1 d . . .
C3 C 0.78429(18) 0.7593(7) 0.42998(17) 0.0314(9) Uani 1 1 d . . .
H3 H 0.7885 0.8828 0.4646 0.038 Uiso 1 1 calc R . .
C4 C 0.8396(2) 0.7358(7) 0.39711(19) 0.0371(10) Uani 1 1 d . . .
H4 H 0.8821 0.8476 0.4083 0.045 Uiso 1 1 calc R . .
C5 C 0.8347(2) 0.5513(7) 0.34775(18) 0.0373(10) Uani 1 1 d . . .
H5 H 0.8737 0.5391 0.3258 0.045 Uiso 1 1 calc R . .
C6 C 0.77359(19) 0.3852(7) 0.33022(17) 0.0324(9) Uani 1 1 d . . .
H6 H 0.7705 0.2575 0.2972 0.039 Uiso 1 1 calc R . .
C7 C 0.71720(18) 0.4114(6) 0.36231(16) 0.0231(8) Uani 1 1 d . . .
C8 C 0.64578(18) 0.2644(7) 0.35318(16) 0.0248(8) Uani 1 1 d . . .
C9 C 0.59597(17) 0.3981(6) 0.38954(16) 0.0233(8) Uani 1 1 d . . .
C10 C 0.52553(17) 0.5475(6) 0.33184(15) 0.0219(8) Uani 1 1 d . . .
H10 H 0.5410 0.7205 0.3349 0.026 Uiso 1 1 calc R . .
C11 C 0.50159(17) 0.4644(6) 0.25317(16) 0.0210(8) Uani 1 1 d . . .
C12 C 0.51772(18) 0.6062(6) 0.20244(17) 0.0274(9) Uani 1 1 d . . .
H12 H 0.5461 0.7519 0.2178 0.033 Uiso 1 1 calc R . .
C13 C 0.4933(2) 0.5400(7) 0.12966(18) 0.0348(10) Uani 1 1 d . . .
H13 H 0.5028 0.6413 0.0947 0.042 Uiso 1 1 calc R . .
C14 C 0.45469(19) 0.3235(7) 0.10895(17) 0.0298(9) Uani 1 1 d . . .
C15 C 0.43793(18) 0.1791(7) 0.15830(17) 0.0289(9) Uani 1 1 d . . .
H15 H 0.4105 0.0319 0.1429 0.035 Uiso 1 1 calc R . .
C16 C 0.46135(17) 0.2498(6) 0.23056(17) 0.0266(9) Uani 1 1 d . . .
H16 H 0.4498 0.1509 0.2650 0.032 Uiso 1 1 calc R . .
C17 C 0.46036(18) 0.5171(6) 0.36220(16) 0.0232(8) Uani 1 1 d . . .
C18 C 0.47666(18) 0.3556(6) 0.41473(17) 0.0268(9) Uani 1 1 d . . .
H18 H 0.4411 0.3135 0.4387 0.032 Uiso 1 1 calc R . .
C19 C 0.55658(17) 0.2466(6) 0.43244(17) 0.0289(9) Uani 1 1 d . . .
H19A H 0.5522 0.0768 0.4167 0.035 Uiso 1 1 calc R . .
H19B H 0.5873 0.2548 0.4856 0.035 Uiso 1 1 calc R . .
C20 C 0.38683(19) 0.6600(7) 0.33060(19) 0.0281(9) Uani 1 1 d . . .
C21 C 0.25602(19) 0.7233(7) 0.3292(2) 0.0421(11) Uani 1 1 d . . .
H21A H 0.2129 0.6143 0.3296 0.051 Uiso 1 1 calc R . .
H21B H 0.2452 0.7718 0.2779 0.051 Uiso 1 1 calc R . .
C22 C 0.2564(2) 0.9380(9) 0.3733(2) 0.0713(15) Uani 1 1 d . . .
H22A H 0.2049 1.0192 0.3530 0.107 Uiso 1 1 calc R . .
H22B H 0.2985 1.0474 0.3723 0.107 Uiso 1 1 calc R . .
H22C H 0.2660 0.8901 0.4239 0.107 Uiso 1 1 calc R . .
O1 O 0.64494(12) 0.7058(5) 0.48388(12) 0.0359(7) Uani 1 1 d . . .
O2 O 0.63038(13) 0.0712(5) 0.32325(12) 0.0340(6) Uani 1 1 d . . .
O3 O 0.37816(13) 0.8117(5) 0.28470(14) 0.0475(8) Uani 1 1 d . . .
O4 O 0.33136(13) 0.5966(5) 0.35699(12) 0.0416(7) Uani 1 1 d . . .
Cl1 Cl 0.42360(6) 0.2318(2) 0.01781(4) 0.0481(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
C1 O1 1.209(4) . ?
C1 C2 1.483(4) . ?
C1 C9 1.530(4) . ?
C2 C3 1.378(4) . ?
C2 C7 1.390(4) . ?
C3 C4 1.375(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.482(4) . ?
C8 O2 1.210(4) . ?
C8 C9 1.526(4) . ?
C9 C19 1.534(4) . ?
C9 C10 1.599(4) . ?
C10 C17 1.506(4) . ?
C10 C11 1.516(4) . ?
C10 H10 1.0000 . ?
C11 C12 1.380(4) . ?
C11 C16 1.387(4) . ?
C12 C13 1.383(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.373(5) . ?
C14 Cl1 1.745(3) . ?
C15 C16 1.381(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.318(4) . ?
C17 C20 1.479(4) . ?
C18 C19 1.486(4) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 O3 1.203(4) . ?
C20 O4 1.329(4) . ?
C21 O4 1.453(4) . ?
C21 C22 1.476(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
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
O1 C1 C2 126.4(3) . . ?
O1 C1 C9 125.8(3) . . ?
C2 C1 C9 107.8(3) . . ?
C3 C2 C7 121.5(3) . . ?
C3 C2 C1 128.9(3) . . ?
C7 C2 C1 109.6(3) . . ?
C4 C3 C2 117.7(3) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C3 C4 C5 121.3(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C7 C6 C5 117.8(3) . . ?
C7 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C6 C7 C2 120.7(3) . . ?
C6 C7 C8 129.5(3) . . ?
C2 C7 C8 109.7(3) . . ?
O2 C8 C7 126.1(3) . . ?
O2 C8 C9 126.1(3) . . ?
C7 C8 C9 107.8(3) . . ?
C8 C9 C1 102.7(3) . . ?
C8 C9 C19 116.9(3) . . ?
C1 C9 C19 113.8(2) . . ?
C8 C9 C10 112.1(2) . . ?
C1 C9 C10 105.4(3) . . ?
C19 C9 C10 105.5(2) . . ?
C17 C10 C11 112.9(2) . . ?
C17 C10 C9 101.4(2) . . ?
C11 C10 C9 115.1(3) . . ?
C17 C10 H10 109.1 . . ?
C11 C10 H10 109.1 . . ?
C9 C10 H10 109.1 . . ?
C12 C11 C16 119.0(3) . . ?
C12 C11 C10 120.0(3) . . ?
C16 C11 C10 120.9(3) . . ?
C11 C12 C13 121.2(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 118.5(3) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
C15 C14 C13 121.4(3) . . ?
C15 C14 Cl1 118.5(3) . . ?
C13 C14 Cl1 120.0(3) . . ?
C14 C15 C16 119.4(3) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C11 120.4(3) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C18 C17 C20 127.6(3) . . ?
C18 C17 C10 113.5(3) . . ?
C20 C17 C10 118.9(3) . . ?
C17 C18 C19 112.8(3) . . ?
C17 C18 H18 123.6 . . ?
C19 C18 H18 123.6 . . ?
C18 C19 C9 104.4(3) . . ?
C18 C19 H19A 110.9 . . ?
C9 C19 H19A 110.9 . . ?
C18 C19 H19B 110.9 . . ?
C9 C19 H19B 110.9 . . ?
H19A C19 H19B 108.9 . . ?
O3 C20 O4 124.3(3) . . ?
O3 C20 C17 123.2(3) . . ?
O4 C20 C17 112.4(3) . . ?
O4 C21 C22 111.6(3) . . ?
O4 C21 H21A 109.3 . . ?
C22 C21 H21A 109.3 . . ?
O4 C21 H21B 109.3 . . ?
C22 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 O4 C21 117.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.09
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.061
####################################################################### 
# 
# 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_a14909
_database_code_depnum_ccdc_archive 'CCDC 2110329'
loop_
_audit_author_name
_audit_author_address
'Shaik Anwar'
;Vignans Foundation for Science Technology and research
India
;
_audit_update_record             
;
2021-09-17 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H17 Br O4'
_chemical_formula_sum            'C22 H17 Br O4'
_chemical_formula_weight         425.27

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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   18.073(5)
_cell_length_b                   5.5804(17)
_cell_length_c                   19.888(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.898(8)
_cell_angle_gamma                90.00
_cell_volume                     1886.1(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    850
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      20.07

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    2.204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6795
_exptl_absorpt_correction_T_max  0.8978
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9089
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_av_sigmaI/netI    0.0994
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         25.07
_reflns_number_total             3338
_reflns_number_gt                2000
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0344P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3338
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1052
_refine_ls_wR_factor_gt          0.0878
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4551(2) 1.1785(9) 0.1153(2) 0.0287(11) Uani 1 1 d . . .
C2 C 0.4936(3) 0.9637(9) 0.1341(2) 0.0326(12) Uani 1 1 d . . .
H2 H 0.5037 0.8655 0.0991 0.039 Uiso 1 1 calc R . .
C3 C 0.5176(2) 0.8931(8) 0.2052(2) 0.0254(11) Uani 1 1 d . . .
H3 H 0.5455 0.7469 0.2190 0.030 Uiso 1 1 calc R . .
C4 C 0.5015(2) 1.0313(7) 0.2562(2) 0.0224(10) Uani 1 1 d . . .
C5 C 0.4622(2) 1.2483(8) 0.2351(2) 0.0253(10) Uani 1 1 d . . .
H5 H 0.4514 1.3466 0.2697 0.030 Uiso 1 1 calc R . .
C6 C 0.4386(2) 1.3230(8) 0.1644(2) 0.0307(11) Uani 1 1 d . . .
H6 H 0.4117 1.4707 0.1502 0.037 Uiso 1 1 calc R . .
C7 C 0.5255(2) 0.9482(8) 0.3326(2) 0.0234(10) Uani 1 1 d . . .
H7 H 0.5410 0.7756 0.3348 0.028 Uiso 1 1 calc R . .
C8 C 0.4605(2) 0.9749(7) 0.3643(2) 0.0230(10) Uani 1 1 d . . .
C9 C 0.3871(3) 0.8363(8) 0.3330(2) 0.0305(11) Uani 1 1 d . . .
C10 C 0.2573(3) 0.7716(9) 0.3331(3) 0.0537(15) Uani 1 1 d . . .
H10A H 0.2469 0.7305 0.2823 0.064 Uiso 1 1 calc R . .
H10B H 0.2151 0.8807 0.3355 0.064 Uiso 1 1 calc R . .
C11 C 0.2561(3) 0.5526(11) 0.3733(3) 0.089(2) Uani 1 1 d . . .
H11A H 0.2046 0.4749 0.3531 0.134 Uiso 1 1 calc R . .
H11B H 0.2655 0.5933 0.4235 0.134 Uiso 1 1 calc R . .
H11C H 0.2972 0.4432 0.3703 0.134 Uiso 1 1 calc R . .
C12 C 0.4763(2) 1.1359(8) 0.4159(2) 0.0282(11) Uani 1 1 d . . .
H12 H 0.4409 1.1771 0.4401 0.034 Uiso 1 1 calc R . .
C13 C 0.5552(2) 1.2456(7) 0.4319(2) 0.0295(11) Uani 1 1 d . . .
H13A H 0.5857 1.2366 0.4837 0.035 Uiso 1 1 calc R . .
H13B H 0.5507 1.4155 0.4167 0.035 Uiso 1 1 calc R . .
C14 C 0.5946(2) 1.0942(7) 0.3883(2) 0.0224(10) Uani 1 1 d . . .
C15 C 0.6444(2) 1.2314(8) 0.3526(2) 0.0242(10) Uani 1 1 d . . .
C16 C 0.7155(2) 1.0839(8) 0.3600(2) 0.0239(10) Uani 1 1 d . . .
C17 C 0.7726(2) 1.1108(8) 0.3283(2) 0.0300(12) Uani 1 1 d . . .
H17 H 0.7700 1.2385 0.2960 0.036 Uiso 1 1 calc R . .
C18 C 0.8332(3) 0.9464(9) 0.3451(2) 0.0366(13) Uani 1 1 d . . .
H18 H 0.8726 0.9611 0.3237 0.044 Uiso 1 1 calc R . .
C19 C 0.8378(3) 0.7596(8) 0.3925(2) 0.0364(12) Uani 1 1 d . . .
H19 H 0.8799 0.6481 0.4026 0.044 Uiso 1 1 calc R . .
C20 C 0.7818(2) 0.7339(7) 0.4253(2) 0.0324(11) Uani 1 1 d . . .
H20 H 0.7853 0.6087 0.4586 0.039 Uiso 1 1 calc R . .
C21 C 0.7208(2) 0.8966(8) 0.4078(2) 0.0248(11) Uani 1 1 d . . .
C22 C 0.6522(2) 0.9075(8) 0.4335(2) 0.0254(11) Uani 1 1 d . . .
O1 O 0.37744(18) 0.6903(6) 0.28611(19) 0.0494(10) Uani 1 1 d . . .
O2 O 0.33268(18) 0.8926(6) 0.36152(17) 0.0507(10) Uani 1 1 d . . .
O3 O 0.62894(17) 1.4241(6) 0.32372(16) 0.0341(8) Uani 1 1 d . . .
O4 O 0.64310(16) 0.7856(5) 0.48044(15) 0.0362(8) Uani 1 1 d . . .
Br1 Br 0.42112(3) 1.28379(10) 0.01844(2) 0.0484(2) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.374(5) . ?
C1 C2 1.373(6) . ?
C1 Br1 1.905(4) . ?
C2 C3 1.388(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(5) . ?
C4 C7 1.504(5) . ?
C5 C6 1.388(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.517(5) . ?
C7 C14 1.584(5) . ?
C7 H7 1.0000 . ?
C8 C12 1.319(5) . ?
C8 C9 1.479(6) . ?
C9 O1 1.206(5) . ?
C9 O2 1.329(4) . ?
C10 O2 1.452(5) . ?
C10 C11 1.465(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.483(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.548(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.528(5) . ?
C14 C22 1.530(6) . ?
C15 O3 1.206(4) . ?
C15 C16 1.491(6) . ?
C16 C17 1.389(5) . ?
C16 C21 1.394(5) . ?
C17 C18 1.379(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.384(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.379(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.494(5) . ?
C22 O4 1.211(4) . ?

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
C6 C1 C2 122.2(4) . . ?
C6 C1 Br1 117.6(4) . . ?
C2 C1 Br1 120.2(3) . . ?
C1 C2 C3 118.6(4) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 121.3(4) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 118.4(4) . . ?
C3 C4 C7 120.6(4) . . ?
C5 C4 C7 121.0(4) . . ?
C6 C5 C4 121.0(4) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C1 C6 C5 118.5(4) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C4 C7 C8 113.1(3) . . ?
C4 C7 C14 115.8(3) . . ?
C8 C7 C14 101.3(3) . . ?
C4 C7 H7 108.8 . . ?
C8 C7 H7 108.8 . . ?
C14 C7 H7 108.8 . . ?
C12 C8 C9 127.5(4) . . ?
C12 C8 C7 113.4(4) . . ?
C9 C8 C7 119.0(4) . . ?
O1 C9 O2 123.8(4) . . ?
O1 C9 C8 123.5(4) . . ?
O2 C9 C8 112.6(4) . . ?
O2 C10 C11 111.2(4) . . ?
O2 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
O2 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 C13 112.7(4) . . ?
C8 C12 H12 123.7 . . ?
C13 C12 H12 123.7 . . ?
C12 C13 C14 104.2(3) . . ?
C12 C13 H13A 110.9 . . ?
C14 C13 H13A 110.9 . . ?
C12 C13 H13B 110.9 . . ?
C14 C13 H13B 110.9 . . ?
H13A C13 H13B 108.9 . . ?
C15 C14 C22 102.9(3) . . ?
C15 C14 C13 116.3(3) . . ?
C22 C14 C13 113.1(3) . . ?
C15 C14 C7 112.5(3) . . ?
C22 C14 C7 106.1(3) . . ?
C13 C14 C7 105.6(3) . . ?
O3 C15 C16 126.3(4) . . ?
O3 C15 C14 126.2(4) . . ?
C16 C15 C14 107.5(4) . . ?
C17 C16 C21 120.2(4) . . ?
C17 C16 C15 130.1(4) . . ?
C21 C16 C15 109.7(3) . . ?
C18 C17 C16 117.9(4) . . ?
C18 C17 H17 121.0 . . ?
C16 C17 H17 121.0 . . ?
C17 C18 C19 121.5(4) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C20 C19 C18 120.8(4) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C21 C20 C19 117.6(4) . . ?
C21 C20 H20 121.2 . . ?
C19 C20 H20 121.2 . . ?
C20 C21 C16 121.9(4) . . ?
C20 C21 C22 128.8(4) . . ?
C16 C21 C22 109.3(4) . . ?
O4 C22 C21 125.9(4) . . ?
O4 C22 C14 126.3(4) . . ?
C21 C22 C14 107.7(3) . . ?
C9 O2 C10 117.1(4) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.07
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.082
####################################################################### 
# 
# 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_a14321
_database_code_depnum_ccdc_archive 'CCDC 921839'
loop_
_audit_author_name
_audit_author_address
'Shaik Anwar'
;Vignans Foundation for Science Technology and research
India
;
_audit_update_record             
;
2021-09-24 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H17 N O4'
_chemical_formula_sum            'C23 H17 N O4'
_chemical_formula_weight         371.38

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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

_cell_length_a                   31.098(4)
_cell_length_b                   8.4741(11)
_cell_length_c                   14.651(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.962(4)
_cell_angle_gamma                90.00
_cell_volume                     3823.7(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1552
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9721
_exptl_absorpt_correction_T_max  0.9833
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11967
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3276
_reflns_number_gt                2194
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0639P)²+13.2466P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3276
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1196
_refine_ls_R_factor_gt           0.0741
_refine_ls_wR_factor_ref         0.1901
_refine_ls_wR_factor_gt          0.1662
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.005
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.36878(12) 0.4663(5) 0.2286(3) 0.0377(9) Uani 1 1 d . . .
C2 C 0.33021(11) 0.5441(4) 0.2564(2) 0.0309(8) Uani 1 1 d . . .
C3 C 0.31361(12) 0.5348(5) 0.3398(2) 0.0388(10) Uani 1 1 d . . .
H3 H 0.3276 0.4737 0.3896 0.047 Uiso 1 1 calc R . .
C4 C 0.27611(13) 0.6174(5) 0.3473(3) 0.0437(10) Uani 1 1 d . . .
H4 H 0.2642 0.6138 0.4035 0.052 Uiso 1 1 calc R . .
C5 C 0.25551(13) 0.7053(5) 0.2749(3) 0.0511(12) Uani 1 1 d . . .
H5 H 0.2299 0.7621 0.2826 0.061 Uiso 1 1 calc R . .
C6 C 0.27124(13) 0.7122(5) 0.1920(3) 0.0499(11) Uani 1 1 d . . .
H6 H 0.2567 0.7712 0.1419 0.060 Uiso 1 1 calc R . .
C7 C 0.30909(12) 0.6303(4) 0.1839(2) 0.0339(9) Uani 1 1 d . . .
C8 C 0.33230(13) 0.6152(4) 0.1026(3) 0.0402(10) Uani 1 1 d . . .
C9 C 0.37328(11) 0.5182(4) 0.1304(3) 0.0371(9) Uani 1 1 d . . .
C10 C 0.38002(11) 0.3826(4) 0.0682(2) 0.0311(8) Uani 1 1 d . . .
C11 C 0.34598(11) 0.2639(4) 0.0449(2) 0.0312(8) Uani 1 1 d . . .
C12 C 0.32543(13) 0.0340(4) -0.0443(3) 0.0419(10) Uani 1 1 d . . .
H12A H 0.2969 0.0814 -0.0674 0.050 Uiso 1 1 calc R . .
H12B H 0.3218 -0.0375 0.0076 0.050 Uiso 1 1 calc R . .
C13 C 0.34274(15) -0.0542(6) -0.1193(3) 0.0624(13) Uani 1 1 d . . .
H13A H 0.3224 -0.1384 -0.1420 0.094 Uiso 1 1 calc R . .
H13B H 0.3709 -0.1005 -0.0953 0.094 Uiso 1 1 calc R . .
H13C H 0.3463 0.0181 -0.1699 0.094 Uiso 1 1 calc R . .
C14 C 0.41946(14) 0.3824(5) 0.0465(3) 0.0565(13) Uani 1 1 d . . .
H14 H 0.4301 0.3044 0.0088 0.068 Uiso 1 1 calc R . .
C15 C 0.44584(14) 0.5186(5) 0.0879(4) 0.0625(14) Uani 1 1 d . . .
H15A H 0.4673 0.4841 0.1405 0.075 Uiso 1 1 calc R . .
H15B H 0.4614 0.5708 0.0416 0.075 Uiso 1 1 calc R . .
C16 C 0.41384(15) 0.6225(6) 0.1181(4) 0.0681(15) Uani 1 1 d . . .
H16 H 0.4036 0.6857 0.0616 0.082 Uiso 1 1 calc R . .
C17 C 0.42728(12) 0.7467(5) 0.1896(3) 0.0398(10) Uani 1 1 d . . .
C18 C 0.44787(12) 0.7154(5) 0.2775(3) 0.0460(11) Uani 1 1 d . . .
H18 H 0.4531 0.6088 0.2958 0.055 Uiso 1 1 calc R . .
C19 C 0.46099(12) 0.8343(5) 0.3392(3) 0.0437(10) Uani 1 1 d . . .
H19 H 0.4750 0.8096 0.3992 0.052 Uiso 1 1 calc R . .
C20 C 0.45363(11) 0.9893(5) 0.3132(3) 0.0389(10) Uani 1 1 d . . .
C21 C 0.43253(13) 1.0236(5) 0.2257(3) 0.0456(10) Uani 1 1 d . . .
H21 H 0.4270 1.1301 0.2074 0.055 Uiso 1 1 calc R . .
C22 C 0.41985(13) 0.9037(5) 0.1660(3) 0.0462(11) Uani 1 1 d . . .
H22 H 0.4054 0.9286 0.1063 0.055 Uiso 1 1 calc R . .
C23 C 0.46843(14) 1.1127(6) 0.3765(3) 0.0609(13) Uani 1 1 d . . .
N1 N 0.48086(15) 1.2076(6) 0.4290(4) 0.0934(16) Uani 1 1 d . . .
O1 O 0.39318(10) 0.3782(4) 0.2743(2) 0.0608(9) Uani 1 1 d . . .
O2 O 0.32054(11) 0.6704(3) 0.0267(2) 0.0617(9) Uani 1 1 d . . .
O3 O 0.31188(8) 0.2655(3) 0.07527(19) 0.0482(8) Uani 1 1 d . . .
O4 O 0.35689(8) 0.1564(3) -0.01427(17) 0.0391(7) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.200(5) . ?
C1 C2 1.475(5) . ?
C1 C9 1.530(5) . ?
C2 C7 1.378(5) . ?
C2 C3 1.393(5) . ?
C3 C4 1.378(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.372(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.482(5) . ?
C8 O2 1.215(5) . ?
C8 C9 1.524(5) . ?
C9 C10 1.499(5) . ?
C9 C16 1.570(5) . ?
C10 C14 1.309(5) . ?
C10 C11 1.466(5) . ?
C11 O3 1.206(4) . ?
C11 O4 1.333(4) . ?
C12 O4 1.451(4) . ?
C12 C13 1.491(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.495(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.443(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.503(6) . ?
C16 H16 1.0000 . ?
C17 C18 1.382(6) . ?
C17 C22 1.386(6) . ?
C18 C19 1.377(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.378(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(6) . ?
C20 C23 1.431(6) . ?
C21 C22 1.362(6) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 N1 1.142(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 126.9(4) . . ?
O1 C1 C9 124.8(3) . . ?
C2 C1 C9 108.3(3) . . ?
C7 C2 C3 120.7(3) . . ?
C7 C2 C1 110.1(3) . . ?
C3 C2 C1 129.1(4) . . ?
C4 C3 C2 117.5(4) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 121.3(4) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 117.7(4) . . ?
C5 C6 H6 121.1 . . ?
C7 C6 H6 121.1 . . ?
C2 C7 C6 121.3(3) . . ?
C2 C7 C8 109.9(3) . . ?
C6 C7 C8 128.8(4) . . ?
O2 C8 C7 125.7(4) . . ?
O2 C8 C9 125.9(3) . . ?
C7 C8 C9 108.3(3) . . ?
C10 C9 C8 115.7(3) . . ?
C10 C9 C1 113.0(3) . . ?
C8 C9 C1 103.0(3) . . ?
C10 C9 C16 100.3(3) . . ?
C8 C9 C16 108.7(3) . . ?
C1 C9 C16 116.7(3) . . ?
C14 C10 C11 127.8(3) . . ?
C14 C10 C9 111.3(3) . . ?
C11 C10 C9 120.7(3) . . ?
O3 C11 O4 124.3(3) . . ?
O3 C11 C10 123.4(3) . . ?
O4 C11 C10 112.3(3) . . ?
O4 C12 C13 106.5(3) . . ?
O4 C12 H12A 110.4 . . ?
C13 C12 H12A 110.4 . . ?
O4 C12 H12B 110.4 . . ?
C13 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 C15 112.4(4) . . ?
C10 C14 H14 123.8 . . ?
C15 C14 H14 123.8 . . ?
C16 C15 C14 103.4(3) . . ?
C16 C15 H15A 111.1 . . ?
C14 C15 H15A 111.1 . . ?
C16 C15 H15B 111.1 . . ?
C14 C15 H15B 111.1 . . ?
H15A C15 H15B 109.0 . . ?
C15 C16 C17 120.2(4) . . ?
C15 C16 C9 106.9(4) . . ?
C17 C16 C9 117.6(3) . . ?
C15 C16 H16 103.2 . . ?
C17 C16 H16 103.2 . . ?
C9 C16 H16 103.2 . . ?
C18 C17 C22 117.1(4) . . ?
C18 C17 C16 124.3(4) . . ?
C22 C17 C16 118.5(4) . . ?
C19 C18 C17 121.9(4) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C18 C19 C20 119.6(4) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C19 C20 C21 119.6(4) . . ?
C19 C20 C23 119.4(4) . . ?
C21 C20 C23 121.0(4) . . ?
C22 C21 C20 119.6(4) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C17 122.2(4) . . ?
C21 C22 H22 118.9 . . ?
C17 C22 H22 118.9 . . ?
N1 C23 C20 177.8(6) . . ?
C11 O4 C12 117.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.706
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_a14972
_database_code_depnum_ccdc_archive 'CCDC 2110330'
loop_
_audit_author_name
_audit_author_address
'Shaik Anwar'
;Vignans Foundation for Science Technology and research
India
;
_audit_update_record             
;
2021-09-17 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 O4 S'
_chemical_formula_sum            'C20 H16 O4 S'
_chemical_formula_weight         352.39

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'

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

_cell_length_a                   8.833(13)
_cell_length_b                   6.042(11)
_cell_length_c                   16.23(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.32(3)
_cell_angle_gamma                90.00
_cell_volume                     843(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    368
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      19.02

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8787
_exptl_absorpt_correction_T_max  0.9979
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6003
_diffrn_reflns_av_R_equivalents  0.1321
_diffrn_reflns_av_sigmaI/netI    0.2185
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2445
_reflns_number_gt                1348
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0292P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(2)
_refine_ls_number_reflns         2445
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1624
_refine_ls_R_factor_gt           0.0822
_refine_ls_wR_factor_ref         0.1726
_refine_ls_wR_factor_gt          0.1383
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3777(9) 0.1565(15) 0.5725(5) 0.030(2) Uani 1 1 d . . .
H1 H 0.4445 0.1940 0.6253 0.036 Uiso 1 1 calc R . .
C2 C 0.3906(9) -0.0302(15) 0.5299(5) 0.030(2) Uani 1 1 d . . .
H2 H 0.4695 -0.1378 0.5484 0.036 Uiso 1 1 calc R . .
C3 C 0.2702(9) -0.0495(15) 0.4521(4) 0.029(2) Uani 1 1 d . . .
H3 H 0.2589 -0.1730 0.4150 0.035 Uiso 1 1 calc R . .
C4 C 0.1761(10) 0.1311(15) 0.4393(4) 0.028(2) Uani 1 1 d . . .
C5 C 0.0390(9) 0.1722(15) 0.3648(4) 0.028(2) Uani 1 1 d . . .
H5 H -0.0275 0.0364 0.3568 0.034 Uiso 1 1 calc R . .
C6 C 0.0879(9) 0.2199(12) 0.2779(4) 0.023(2) Uani 1 1 d . . .
C7 C 0.1031(9) 0.0057(14) 0.2294(4) 0.026(2) Uani 1 1 d . . .
C8 C 0.2648(9) -0.0168(14) 0.2211(4) 0.0227(19) Uani 1 1 d . . .
C9 C 0.3309(9) -0.1836(16) 0.1833(4) 0.032(2) Uani 1 1 d . . .
H9 H 0.2704 -0.3055 0.1573 0.038 Uiso 1 1 calc R . .
C10 C 0.4873(9) -0.1695(17) 0.1840(5) 0.037(2) Uani 1 1 d . . .
H10 H 0.5348 -0.2842 0.1588 0.045 Uiso 1 1 calc R . .
C11 C 0.5763(10) 0.0093(17) 0.2209(5) 0.039(2) Uani 1 1 d . . .
H11 H 0.6837 0.0166 0.2206 0.047 Uiso 1 1 calc R . .
C12 C 0.5077(10) 0.1791(14) 0.2585(5) 0.036(2) Uani 1 1 d . . .
H12 H 0.5682 0.3005 0.2850 0.044 Uiso 1 1 calc R . .
C13 C 0.3496(9) 0.1673(14) 0.2564(5) 0.027(2) Uani 1 1 d . . .
C14 C 0.2505(9) 0.3267(16) 0.2908(4) 0.0261(18) Uani 1 1 d . . .
C15 C -0.0416(9) 0.3702(13) 0.2334(4) 0.024(2) Uani 1 1 d . . .
C16 C -0.0512(10) 0.4275(12) 0.1448(5) 0.024(2) Uani 1 1 d . . .
C17 C -0.1900(10) 0.6152(16) 0.0230(5) 0.047(3) Uani 1 1 d . . .
H17A H -0.1943 0.4930 -0.0181 0.057 Uiso 1 1 calc R . .
H17B H -0.0950 0.7033 0.0242 0.057 Uiso 1 1 calc R . .
C18 C -0.3290(10) 0.7561(18) -0.0024(5) 0.059(3) Uani 1 1 d . . .
H18A H -0.3337 0.8175 -0.0589 0.089 Uiso 1 1 calc R . .
H18B H -0.3234 0.8771 0.0384 0.089 Uiso 1 1 calc R . .
H18C H -0.4224 0.6674 -0.0037 0.089 Uiso 1 1 calc R . .
C19 C -0.1220(9) 0.4549(16) 0.2858(5) 0.031(2) Uani 1 1 d . . .
H19 H -0.2054 0.5566 0.2691 0.037 Uiso 1 1 calc R . .
C20 C -0.0649(9) 0.3701(14) 0.3743(4) 0.034(2) Uani 1 1 d . . .
H20A H -0.1528 0.3229 0.3985 0.041 Uiso 1 1 calc R . .
H20B H -0.0045 0.4851 0.4113 0.041 Uiso 1 1 calc R . .
O1 O -0.0065(6) -0.1166(9) 0.2010(3) 0.0397(17) Uani 1 1 d . . .
O2 O 0.2886(6) 0.5016(10) 0.3212(3) 0.0328(15) Uani 1 1 d . . .
O3 O 0.0553(6) 0.3912(9) 0.1107(3) 0.0387(17) Uani 1 1 d . . .
O4 O -0.1864(6) 0.5258(9) 0.1072(3) 0.0305(15) Uani 1 1 d . . .
S1 S 0.2278(3) 0.3187(4) 0.52084(12) 0.0360(6) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.341(11) . ?
C1 S1 1.704(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.456(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.359(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.522(10) . ?
C4 S1 1.722(8) . ?
C5 C20 1.536(10) . ?
C5 C6 1.593(10) . ?
C5 H5 1.0000 . ?
C6 C15 1.508(10) . ?
C6 C7 1.537(11) . ?
C6 C14 1.544(11) . ?
C7 O1 1.220(9) . ?
C7 C8 1.472(10) . ?
C8 C9 1.378(11) . ?
C8 C13 1.389(11) . ?
C9 C10 1.382(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(12) . ?
C10 H10 0.9500 . ?
C11 C12 1.401(11) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(11) . ?
C12 H12 0.9500 . ?
C13 C14 1.494(11) . ?
C14 O2 1.182(10) . ?
C15 C19 1.329(10) . ?
C15 C16 1.463(10) . ?
C16 O3 1.217(9) . ?
C16 O4 1.347(8) . ?
C17 O4 1.463(8) . ?
C17 C18 1.473(11) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.498(9) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 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
C2 C1 S1 112.3(6) . . ?
C2 C1 H1 123.9 . . ?
S1 C1 H1 123.9 . . ?
C1 C2 C3 112.5(8) . . ?
C1 C2 H2 123.8 . . ?
C3 C2 H2 123.8 . . ?
C4 C3 C2 111.5(7) . . ?
C4 C3 H3 124.2 . . ?
C2 C3 H3 124.2 . . ?
C3 C4 C5 126.9(7) . . ?
C3 C4 S1 111.5(6) . . ?
C5 C4 S1 121.7(7) . . ?
C4 C5 C20 115.6(7) . . ?
C4 C5 C6 113.8(6) . . ?
C20 C5 C6 103.8(6) . . ?
C4 C5 H5 107.8 . . ?
C20 C5 H5 107.8 . . ?
C6 C5 H5 107.8 . . ?
C15 C6 C7 114.0(6) . . ?
C15 C6 C14 113.1(6) . . ?
C7 C6 C14 103.5(6) . . ?
C15 C6 C5 101.7(6) . . ?
C7 C6 C5 112.0(6) . . ?
C14 C6 C5 113.0(6) . . ?
O1 C7 C8 127.7(8) . . ?
O1 C7 C6 123.2(7) . . ?
C8 C7 C6 109.0(7) . . ?
C9 C8 C13 121.7(7) . . ?
C9 C8 C7 128.9(8) . . ?
C13 C8 C7 109.3(7) . . ?
C8 C9 C10 118.5(8) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C9 C10 C11 121.2(9) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C12 119.9(8) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 119.0(8) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C8 C13 C12 119.6(8) . . ?
C8 C13 C14 111.3(7) . . ?
C12 C13 C14 129.0(8) . . ?
O2 C14 C13 126.7(8) . . ?
O2 C14 C6 126.6(7) . . ?
C13 C14 C6 106.7(7) . . ?
C19 C15 C16 128.2(7) . . ?
C19 C15 C6 112.6(7) . . ?
C16 C15 C6 118.7(7) . . ?
O3 C16 O4 124.8(7) . . ?
O3 C16 C15 121.9(7) . . ?
O4 C16 C15 113.3(7) . . ?
O4 C17 C18 108.2(7) . . ?
O4 C17 H17A 110.1 . . ?
C18 C17 H17A 110.1 . . ?
O4 C17 H17B 110.1 . . ?
C18 C17 H17B 110.1 . . ?
H17A C17 H17B 108.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 C20 111.7(7) . . ?
C15 C19 H19 124.2 . . ?
C20 C19 H19 124.2 . . ?
C19 C20 C5 104.3(6) . . ?
C19 C20 H20A 110.9 . . ?
C5 C20 H20A 110.9 . . ?
C19 C20 H20B 110.9 . . ?
C5 C20 H20B 110.9 . . ?
H20A C20 H20B 108.9 . . ?
C16 O4 C17 114.4(6) . . ?
C1 S1 C4 92.2(4) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.078
####################################################################### 
# 
# 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_a14348
_database_code_depnum_ccdc_archive 'CCDC 921702'
loop_
_audit_author_name
_audit_author_address
'Shaik Anwar'
;Vignans Foundation for Science Technology and research
India
;
_audit_update_record             
;
2021-09-24 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H17 N O4'
_chemical_formula_sum            'C23 H17 N O4'
_chemical_formula_weight         371.38

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'

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

_cell_length_a                   11.4044(13)
_cell_length_b                   5.5305(7)
_cell_length_c                   15.6417(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.178(7)
_cell_angle_gamma                90.00
_cell_volume                     982.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.73
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9396
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7031
_diffrn_reflns_av_R_equivalents  0.0912
_diffrn_reflns_av_sigmaI/netI    0.1530
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         25.10
_reflns_number_total             2840
_reflns_number_gt                1596
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0475P)²+0.0046P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_number_reflns         2840
_refine_ls_number_parameters     253
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1724
_refine_ls_R_factor_gt           0.0882
_refine_ls_wR_factor_ref         0.1488
_refine_ls_wR_factor_gt          0.1266
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9862(4) 0.2833(12) 0.7831(3) 0.0441(14) Uani 1 1 d . . .
C2 C 1.0645(4) 0.1430(12) 0.8468(3) 0.0487(16) Uani 1 1 d . . .
C3 C 1.0912(4) 0.1890(12) 0.9337(3) 0.061(2) Uani 1 1 d . . .
H3 H 1.0571 0.3172 0.9609 0.073 Uiso 1 1 calc R . .
C4 C 1.1708(5) 0.0356(16) 0.9780(4) 0.080(2) Uani 1 1 d . . .
H4 H 1.1903 0.0593 1.0364 0.097 Uiso 1 1 calc R . .
C5 C 1.2228(5) -0.1562(14) 0.9359(4) 0.079(2) Uani 1 1 d . . .
H5 H 1.2760 -0.2577 0.9668 0.095 Uiso 1 1 calc R . .
C6 C 1.1962(4) -0.1952(14) 0.8505(4) 0.0670(19) Uani 1 1 d . . .
H6 H 1.2310 -0.3216 0.8228 0.080 Uiso 1 1 calc R . .
C7 C 1.1158(4) -0.0421(12) 0.8056(3) 0.0509(16) Uani 1 1 d . . .
C8 C 1.0721(4) -0.0477(12) 0.7137(3) 0.0529(16) Uani 1 1 d . . .
C9 C 0.9733(4) 0.1386(11) 0.7002(3) 0.0426(15) Uani 1 1 d . . .
C10 C 0.9787(4) 0.2888(12) 0.6168(3) 0.0579(17) Uani 1 1 d . . .
H10A H 0.9605 0.4574 0.6264 0.069 Uiso 1 1 calc R . .
H10B H 1.0560 0.2780 0.5957 0.069 Uiso 1 1 calc R . .
C11 C 0.8865(4) 0.1736(12) 0.5551(3) 0.0613(19) Uani 1 1 d . . .
H11 H 0.8777 0.2074 0.4966 0.074 Uiso 1 1 calc R . .
C12 C 0.8205(4) 0.0218(12) 0.5921(3) 0.0451(15) Uani 1 1 d . . .
C13 C 0.7213(5) -0.1223(14) 0.5512(4) 0.065(2) Uani 1 1 d . . .
C14 C 0.5993(6) -0.201(2) 0.4208(4) 0.126(4) Uani 1 1 d . . .
H14A H 0.5501 -0.2715 0.4617 0.151 Uiso 1 1 calc R . .
H14B H 0.5522 -0.0855 0.3861 0.151 Uiso 1 1 calc R . .
C15 C 0.6348(7) -0.373(3) 0.3708(8) 0.259(10) Uani 1 1 d . . .
H15A H 0.5676 -0.4472 0.3398 0.388 Uiso 1 1 calc R . .
H15B H 0.6778 -0.4930 0.4052 0.388 Uiso 1 1 calc R . .
H15C H 0.6848 -0.3049 0.3309 0.388 Uiso 1 1 calc R . .
C16 C 0.8530(3) -0.0078(11) 0.6877(2) 0.0418(14) Uani 1 1 d . . .
H16 H 0.8683 -0.1789 0.7006 0.050 Uiso 1 1 calc R . .
C17 C 0.7585(4) 0.0824(10) 0.7409(3) 0.0437(16) Uani 1 1 d . . .
C18 C 0.7323(4) -0.0498(11) 0.8124(3) 0.0525(17) Uani 1 1 d . . .
H18 H 0.7728 -0.1921 0.8268 0.063 Uiso 1 1 calc R . .
C19 C 0.6454(5) 0.0312(14) 0.8622(3) 0.065(2) Uani 1 1 d . . .
H19 H 0.6287 -0.0562 0.9104 0.078 Uiso 1 1 calc R . .
C20 C 0.5839(4) 0.2393(13) 0.8408(4) 0.0581(18) Uani 1 1 d . . .
C21 C 0.4938(5) 0.3205(15) 0.8920(4) 0.080(2) Uani 1 1 d . . .
C22 C 0.6103(4) 0.3718(12) 0.7705(3) 0.0611(18) Uani 1 1 d . . .
H22 H 0.5704 0.5152 0.7566 0.073 Uiso 1 1 calc R . .
C23 C 0.6967(4) 0.2904(13) 0.7205(3) 0.0549(16) Uani 1 1 d . . .
H23 H 0.7130 0.3784 0.6723 0.066 Uiso 1 1 calc R . .
N1 N 0.4197(5) 0.3849(14) 0.9307(3) 0.117(3) Uani 1 1 d . . .
O1 O 0.9406(3) 0.4750(9) 0.7956(2) 0.0650(12) Uani 1 1 d . . .
O2 O 1.1072(3) -0.1772(9) 0.6588(2) 0.0674(13) Uani 1 1 d . . .
O3 O 0.6612(4) -0.2506(10) 0.5886(3) 0.0878(16) Uani 1 1 d . . .
O4 O 0.7003(3) -0.0743(11) 0.4679(2) 0.109(2) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.205(6) . ?
C1 C2 1.493(8) . ?
C1 C9 1.521(7) . ?
C2 C7 1.369(7) . ?
C2 C3 1.391(6) . ?
C3 C4 1.382(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.407(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.359(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.392(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.479(6) . ?
C8 O2 1.214(6) . ?
C8 C9 1.527(7) . ?
C9 C10 1.552(7) . ?
C9 C16 1.590(7) . ?
C10 C11 1.503(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.299(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.481(8) . ?
C12 C16 1.517(5) . ?
C13 O3 1.178(7) . ?
C13 O4 1.330(6) . ?
C14 C15 1.317(12) . ?
C14 O4 1.487(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.505(6) . ?
C16 H16 0.9800 . ?
C17 C23 1.372(7) . ?
C17 C18 1.391(6) . ?
C18 C19 1.388(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.374(8) . ?
C19 H19 0.9300 . ?
C20 C22 1.377(7) . ?
C20 C21 1.430(8) . ?
C21 N1 1.140(6) . ?
C22 C23 1.387(6) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 126.2(5) . . ?
O1 C1 C9 126.3(5) . . ?
C2 C1 C9 107.5(5) . . ?
C7 C2 C3 122.1(5) . . ?
C7 C2 C1 109.3(5) . . ?
C3 C2 C1 128.5(6) . . ?
C4 C3 C2 117.0(6) . . ?
C4 C3 H3 121.5 . . ?
C2 C3 H3 121.5 . . ?
C3 C4 C5 120.9(6) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 120.9(6) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 118.6(6) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C2 C7 C6 120.5(5) . . ?
C2 C7 C8 110.6(5) . . ?
C6 C7 C8 128.9(6) . . ?
O2 C8 C7 126.6(5) . . ?
O2 C8 C9 125.9(5) . . ?
C7 C8 C9 107.5(4) . . ?
C1 C9 C8 102.9(4) . . ?
C1 C9 C10 115.3(5) . . ?
C8 C9 C10 113.1(4) . . ?
C1 C9 C16 112.9(3) . . ?
C8 C9 C16 107.0(5) . . ?
C10 C9 C16 105.6(4) . . ?
C11 C10 C9 103.5(5) . . ?
C11 C10 H10A 111.1 . . ?
C9 C10 H10A 111.1 . . ?
C11 C10 H10B 111.1 . . ?
C9 C10 H10B 111.1 . . ?
H10A C10 H10B 109.0 . . ?
C12 C11 C10 112.8(5) . . ?
C12 C11 H11 123.6 . . ?
C10 C11 H11 123.6 . . ?
C11 C12 C13 127.3(5) . . ?
C11 C12 C16 114.2(5) . . ?
C13 C12 C16 118.5(5) . . ?
O3 C13 O4 123.1(6) . . ?
O3 C13 C12 124.4(5) . . ?
O4 C13 C12 112.3(6) . . ?
C15 C14 O4 111.7(8) . . ?
C15 C14 H14A 109.3 . . ?
O4 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
O4 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C12 112.7(4) . . ?
C17 C16 C9 114.6(4) . . ?
C12 C16 C9 101.4(4) . . ?
C17 C16 H16 109.3 . . ?
C12 C16 H16 109.3 . . ?
C9 C16 H16 109.3 . . ?
C23 C17 C18 119.0(5) . . ?
C23 C17 C16 121.8(5) . . ?
C18 C17 C16 119.1(5) . . ?
C19 C18 C17 119.8(5) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C20 C19 C18 120.6(5) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C22 119.8(5) . . ?
C19 C20 C21 120.2(6) . . ?
C22 C20 C21 120.0(6) . . ?
N1 C21 C20 178.0(6) . . ?
C20 C22 C23 119.7(6) . . ?
C20 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C17 C23 C22 121.1(5) . . ?
C17 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C13 O4 C14 117.0(6) . . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.041
