# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_20211222HB_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2253535'
loop_
_audit_author_name
_audit_author_address
'weifang Zuo'
;ChengDu University of TCM
China
;
_audit_update_record             
;
2023-04-03 deposited with the CCDC.	2024-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H22 N2 O3'
_chemical_formula_weight         422.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   13.7242(3)
_cell_length_b                   14.7245(4)
_cell_length_c                   11.2636(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.7090(10)
_cell_angle_gamma                90
_cell_volume                     2180.06(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9948
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      68.23

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.679
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_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            33977
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.362
_diffrn_reflns_theta_max         68.736
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4018
_reflns_number_gt                3221
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0885P)²+0.2984P] 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         4018
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1457
_refine_ls_wR_factor_gt          0.1308
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
O001 O 0.92017(8) 0.51851(9) 0.80362(13) 0.0662(4) Uani 1 1 d . . . . .
O1 O 0.89340(11) 0.30086(10) 1.05899(16) 0.0846(5) Uani 1 1 d . . . . .
O002 O 0.76022(10) 0.35038(9) 0.90352(15) 0.0833(5) Uani 1 1 d . . . . .
N003 N 0.83043(10) 0.52009(10) 0.94658(13) 0.0554(4) Uani 1 1 d . . . . .
N005 N 0.87864(11) 0.44725(10) 1.01680(15) 0.0679(5) Uani 1 1 d . . . . .
H005 H 0.932402 0.454600 1.078073 0.082 Uiso 1 1 calc R U . . .
C006 C 0.69352(10) 0.60828(10) 0.85459(14) 0.0444(3) Uani 1 1 d . . . . .
C007 C 0.59709(11) 0.64830(10) 0.84140(14) 0.0455(3) Uani 1 1 d . . . . .
C008 C 0.70584(10) 0.56888(10) 0.64161(14) 0.0455(4) Uani 1 1 d . . . . .
C009 C 0.76187(10) 0.60955(10) 0.76879(14) 0.0454(3) Uani 1 1 d . . . . .
C00A C 0.81261(11) 0.70176(11) 0.76206(15) 0.0476(4) Uani 1 1 d . . . . .
C00B C 0.54526(12) 0.70412(11) 0.74070(15) 0.0509(4) Uani 1 1 d . . . . .
H00B H 0.576157 0.718701 0.679733 0.061 Uiso 1 1 calc R U . . .
C00C C 0.73656(11) 0.55469(11) 0.95527(15) 0.0504(4) Uani 1 1 d . . . . .
C00D C 0.54904(12) 0.62970(12) 0.93590(15) 0.0528(4) Uani 1 1 d . . . . .
C00E C 0.84810(11) 0.54405(11) 0.83717(15) 0.0506(4) Uani 1 1 d . . . . .
C00F C 0.80034(13) 0.77430(11) 0.83378(17) 0.0562(4) Uani 1 1 d . . . . .
H00F H 0.759093 0.767981 0.885907 0.067 Uiso 1 1 calc R U . . .
C00G C 0.67120(12) 0.62181(12) 0.53644(15) 0.0538(4) Uani 1 1 d . . . . .
H00G H 0.683707 0.683979 0.541230 0.065 Uiso 1 1 calc R U . . .
C00H C 0.68333(12) 0.47641(11) 0.63200(16) 0.0558(4) Uani 1 1 d . . . . .
H00H H 0.704459 0.439633 0.701838 0.067 Uiso 1 1 calc R U . . .
C00I C 0.44974(13) 0.73699(13) 0.73210(18) 0.0596(4) Uani 1 1 d . . . . .
H00I H 0.416761 0.773467 0.665213 0.071 Uiso 1 1 calc R U . . .
C00J C 0.44948(13) 0.66512(13) 0.92129(19) 0.0635(5) Uani 1 1 d . . . . .
H00J H 0.416814 0.652639 0.981248 0.076 Uiso 1 1 calc R U . . .
C00K C 0.69185(14) 0.53769(13) 1.05042(16) 0.0631(5) Uani 1 1 d . . . . .
H00K H 0.724135 0.502059 1.118543 0.076 Uiso 1 1 calc R U . . .
C00L C 0.59881(14) 0.57577(14) 1.03868(17) 0.0630(5) Uani 1 1 d . . . . .
H00L H 0.567359 0.565763 1.100460 0.076 Uiso 1 1 calc R U . . .
C00M C 0.62985(14) 0.43874(12) 0.51958(18) 0.0631(5) Uani 1 1 d . . . . .
H00M H 0.615177 0.376951 0.514589 0.076 Uiso 1 1 calc R U . . .
C00N C 0.61819(14) 0.58363(13) 0.42420(17) 0.0628(4) Uani 1 1 d . . . . .
H00N H 0.595887 0.620208 0.354308 0.075 Uiso 1 1 calc R U . . .
C00O C 0.40161(13) 0.71647(13) 0.82207(19) 0.0645(5) Uani 1 1 d . . . . .
H00O H 0.336355 0.738140 0.813919 0.077 Uiso 1 1 calc R U . . .
C00P C 0.84841(14) 0.85648(13) 0.8295(2) 0.0675(5) Uani 1 1 d . . . . .
H00P H 0.839231 0.904640 0.878638 0.081 Uiso 1 1 calc R U . . .
C00Q C 0.59826(13) 0.49188(13) 0.41532(17) 0.0618(4) Uani 1 1 d . . . . .
H00Q H 0.563748 0.466123 0.339500 0.074 Uiso 1 1 calc R U . . .
C00R C 0.87559(13) 0.71297(14) 0.68552(18) 0.0621(5) Uani 1 1 d . . . . .
H00R H 0.885985 0.664815 0.637129 0.075 Uiso 1 1 calc R U . . .
C00S C 0.83751(13) 0.36338(13) 0.98496(19) 0.0659(5) Uani 1 1 d . . . . .
C00T C 0.92268(14) 0.79564(15) 0.6814(2) 0.0721(5) Uani 1 1 d . . . . .
H00T H 0.963781 0.802729 0.629242 0.087 Uiso 1 1 calc R U . . .
C00U C 0.90950(14) 0.86707(14) 0.7531(2) 0.0706(5) Uani 1 1 d . . . . .
H00U H 0.941668 0.922245 0.750057 0.085 Uiso 1 1 calc R U . . .
C00V C 0.85010(18) 0.20911(16) 1.0445(3) 0.0928(8) Uani 1 1 d . . . . .
H00A H 0.776538 0.213107 1.023149 0.111 Uiso 1 1 calc R U . . .
H00C H 0.873835 0.176795 1.122558 0.111 Uiso 1 1 calc R U . . .
C00W C 0.8792(3) 0.1582(2) 0.9473(4) 0.1213(11) Uani 1 1 d . . . . .
H00D H 0.851684 0.187820 0.868912 0.182 Uiso 1 1 calc R U . . .
H00E H 0.852755 0.097492 0.942948 0.182 Uiso 1 1 calc R U . . .
H00S H 0.951968 0.155988 0.966836 0.182 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
O001 C00E 1.215(2) . ?
O1 C00S 1.328(2) . ?
O1 C00V 1.466(3) . ?
O002 C00S 1.202(2) . ?
N003 C00E 1.369(2) . ?
N003 N005 1.3830(19) . ?
N003 C00C 1.415(2) . ?
N005 C00S 1.362(2) . ?
N005 H005 0.8600 . ?
C006 C00C 1.368(2) . ?
C006 C007 1.417(2) . ?
C006 C009 1.528(2) . ?
C007 C00B 1.416(2) . ?
C007 C00D 1.431(2) . ?
C008 C00G 1.383(2) . ?
C008 C00H 1.394(2) . ?
C008 C009 1.539(2) . ?
C009 C00A 1.538(2) . ?
C009 C00E 1.549(2) . ?
C00A C00F 1.378(2) . ?
C00A C00R 1.395(2) . ?
C00B C00I 1.374(2) . ?
C00B H00B 0.9300 . ?
C00C C00K 1.402(2) . ?
C00D C00L 1.408(3) . ?
C00D C00J 1.427(2) . ?
C00F C00P 1.386(2) . ?
C00F H00F 0.9300 . ?
C00G C00N 1.384(2) . ?
C00G H00G 0.9300 . ?
C00H C00M 1.384(2) . ?
C00H H00H 0.9300 . ?
C00I C00O 1.393(3) . ?
C00I H00I 0.9300 . ?
C00J C00O 1.353(3) . ?
C00J H00J 0.9300 . ?
C00K C00L 1.366(3) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00M C00Q 1.373(3) . ?
C00M H00M 0.9300 . ?
C00N C00Q 1.376(3) . ?
C00N H00N 0.9300 . ?
C00O H00O 0.9300 . ?
C00P C00U 1.372(3) . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00R C00T 1.385(3) . ?
C00R H00R 0.9300 . ?
C00T C00U 1.369(3) . ?
C00T H00T 0.9300 . ?
C00U H00U 0.9300 . ?
C00V C00W 1.473(5) . ?
C00V H00A 0.9700 . ?
C00V H00C 0.9700 . ?
C00W H00D 0.9600 . ?
C00W H00E 0.9600 . ?
C00W H00S 0.9600 . ?

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
C00S O1 C00V 115.24(16) . . ?
C00E N003 N005 122.36(15) . . ?
C00E N003 C00C 111.71(13) . . ?
N005 N003 C00C 122.36(15) . . ?
C00S N005 N003 117.29(13) . . ?
C00S N005 H005 121.4 . . ?
N003 N005 H005 121.4 . . ?
C00C C006 C007 119.63(14) . . ?
C00C C006 C009 109.50(13) . . ?
C007 C006 C009 130.79(13) . . ?
C00B C007 C006 124.37(14) . . ?
C00B C007 C00D 118.32(14) . . ?
C006 C007 C00D 117.31(14) . . ?
C00G C008 C00H 118.04(15) . . ?
C00G C008 C009 122.32(14) . . ?
C00H C008 C009 119.52(14) . . ?
C006 C009 C00A 114.27(12) . . ?
C006 C009 C008 110.52(11) . . ?
C00A C009 C008 114.19(13) . . ?
C006 C009 C00E 101.42(12) . . ?
C00A C009 C00E 106.39(11) . . ?
C008 C009 C00E 109.05(12) . . ?
C00F C00A C00R 118.18(15) . . ?
C00F C00A C009 121.47(14) . . ?
C00R C00A C009 120.32(15) . . ?
C00I C00B C007 120.68(16) . . ?
C00I C00B H00B 119.7 . . ?
C007 C00B H00B 119.7 . . ?
C006 C00C C00K 123.84(15) . . ?
C006 C00C N003 109.58(14) . . ?
C00K C00C N003 126.58(15) . . ?
C00L C00D C00J 121.53(16) . . ?
C00L C00D C007 120.08(15) . . ?
C00J C00D C007 118.37(16) . . ?
O001 C00E N003 124.81(15) . . ?
O001 C00E C009 127.71(16) . . ?
N003 C00E C009 107.48(13) . . ?
C00A C00F C00P 121.12(17) . . ?
C00A C00F H00F 119.4 . . ?
C00P C00F H00F 119.4 . . ?
C008 C00G C00N 120.97(16) . . ?
C008 C00G H00G 119.5 . . ?
C00N C00G H00G 119.5 . . ?
C00M C00H C008 120.67(16) . . ?
C00M C00H H00H 119.7 . . ?
C008 C00H H00H 119.7 . . ?
C00B C00I C00O 120.98(18) . . ?
C00B C00I H00I 119.5 . . ?
C00O C00I H00I 119.5 . . ?
C00O C00J C00D 121.40(16) . . ?
C00O C00J H00J 119.3 . . ?
C00D C00J H00J 119.3 . . ?
C00L C00K C00C 117.08(16) . . ?
C00L C00K H00K 121.5 . . ?
C00C C00K H00K 121.5 . . ?
C00K C00L C00D 122.02(16) . . ?
C00K C00L H00L 119.0 . . ?
C00D C00L H00L 119.0 . . ?
C00Q C00M C00H 120.53(17) . . ?
C00Q C00M H00M 119.7 . . ?
C00H C00M H00M 119.7 . . ?
C00Q C00N C00G 120.43(17) . . ?
C00Q C00N H00N 119.8 . . ?
C00G C00N H00N 119.8 . . ?
C00J C00O C00I 120.20(16) . . ?
C00J C00O H00O 119.9 . . ?
C00I C00O H00O 119.9 . . ?
C00U C00P C00F 120.25(19) . . ?
C00U C00P H00P 119.9 . . ?
C00F C00P H00P 119.9 . . ?
C00M C00Q C00N 119.33(16) . . ?
C00M C00Q H00Q 120.3 . . ?
C00N C00Q H00Q 120.3 . . ?
C00T C00R C00A 120.17(18) . . ?
C00T C00R H00R 119.9 . . ?
C00A C00R H00R 119.9 . . ?
O002 C00S O1 126.35(18) . . ?
O002 C00S N005 123.60(16) . . ?
O1 C00S N005 110.02(15) . . ?
C00U C00T C00R 120.88(18) . . ?
C00U C00T H00T 119.6 . . ?
C00R C00T H00T 119.6 . . ?
C00T C00U C00P 119.39(17) . . ?
C00T C00U H00U 120.3 . . ?
C00P C00U H00U 120.3 . . ?
O1 C00V C00W 111.4(2) . . ?
O1 C00V H00A 109.4 . . ?
C00W C00V H00A 109.4 . . ?
O1 C00V H00C 109.4 . . ?
C00W C00V H00C 109.4 . . ?
H00A C00V H00C 108.0 . . ?
C00V C00W H00D 109.5 . . ?
C00V C00W H00E 109.5 . . ?
H00D C00W H00E 109.5 . . ?
C00V C00W H00S 109.5 . . ?
H00D C00W H00S 109.5 . . ?
H00E C00W H00S 109.5 . . ?

_refine_diff_density_max         0.147
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.048



####################################################################### 
# 
# 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_20230517ZWF_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2267724'
loop_
_audit_author_name
_audit_author_address
'weifang Zuo'
;ChengDu University of Traditional Chinese Medicine
China
;
_audit_update_record             
;
2023-06-06 deposited with the CCDC.	2024-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 Br N2 O3'
_chemical_formula_weight         437.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   12.1826(4)
_cell_length_b                   7.4970(2)
_cell_length_c                   21.2926(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.662(2)
_cell_angle_gamma                90
_cell_volume                     1942.62(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9852
_cell_measurement_theta_min      3.63
_cell_measurement_theta_max      68.33

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    3.098
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_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            24905
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.632
_diffrn_reflns_theta_max         68.553
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3561
_reflns_number_gt                3129
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0424P)²+0.8764P] 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         3561
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0899
_refine_ls_wR_factor_gt          0.0858
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
Br01 Br 0.17337(2) 0.71251(3) 0.59687(2) 0.05326(12) Uani 1 1 d . . . . .
O002 O 0.35574(13) -0.0475(2) 0.50178(8) 0.0522(4) Uani 1 1 d . . . . .
O003 O 0.38299(14) -0.0105(2) 0.64201(8) 0.0538(4) Uani 1 1 d . . . . .
O004 O 0.24354(14) 0.1639(3) 0.45849(8) 0.0529(4) Uani 1 1 d . . . . .
N005 N 0.24057(14) 0.3240(2) 0.57896(8) 0.0337(4) Uani 1 1 d . . . . .
N006 N 0.27352(14) 0.1422(2) 0.56464(8) 0.0367(4) Uani 1 1 d . . . . .
C007 C 0.12321(16) 0.3441(3) 0.57922(9) 0.0325(4) Uani 1 1 d . . . . .
C008 C 0.23948(17) 0.3273(3) 0.70084(10) 0.0384(5) Uani 1 1 d . . . . .
C009 C 0.28837(16) 0.0908(3) 0.50256(11) 0.0386(5) Uani 1 1 d . . . . .
C00A C 0.07911(17) 0.5136(3) 0.58525(10) 0.0383(5) Uani 1 1 d . . . . .
C00B C 0.33145(16) 0.1136(3) 0.62203(10) 0.0379(5) Uani 1 1 d . . . . .
C00C C 0.30588(17) 0.3047(3) 0.64346(10) 0.0353(4) Uani 1 1 d . . . . .
C00D C 0.41327(17) 0.4084(3) 0.64329(10) 0.0391(5) Uani 1 1 d . . . . .
C00E C 0.05092(18) 0.2022(3) 0.56950(11) 0.0391(5) Uani 1 1 d . . . . .
H00E H 0.078473 0.087469 0.565034 0.047 Uiso 1 1 calc R U . . .
C00F C -0.03323(19) 0.5419(3) 0.58148(11) 0.0473(5) Uani 1 1 d . . . . .
H00F H -0.061166 0.656650 0.585253 0.057 Uiso 1 1 calc R U . . .
C00G C 0.1672(2) 0.1963(4) 0.71866(11) 0.0479(6) Uani 1 1 d . . . . .
H00G H 0.163665 0.088877 0.696825 0.057 Uiso 1 1 calc R U . . .
C00H C -0.06153(19) 0.2297(4) 0.56639(12) 0.0474(6) Uani 1 1 d . . . . .
H00H H -0.108859 0.133226 0.560418 0.057 Uiso 1 1 calc R U . . .
C00I C 0.2447(2) 0.4860(3) 0.73511(11) 0.0490(6) Uani 1 1 d . . . . .
H00I H 0.293946 0.574767 0.724602 0.059 Uiso 1 1 calc R U . . .
C00J C 0.44027(19) 0.5172(4) 0.59383(12) 0.0492(6) Uani 1 1 d . . . . .
H00J H 0.390550 0.533728 0.559848 0.059 Uiso 1 1 calc R U . . .
C00K C -0.10380(19) 0.3990(4) 0.57207(12) 0.0517(6) Uani 1 1 d . . . . .
H00K H -0.179400 0.417127 0.569597 0.062 Uiso 1 1 calc R U . . .
C00L C 0.4897(2) 0.3819(4) 0.69302(12) 0.0549(6) Uani 1 1 d . . . . .
H00L H 0.472921 0.307383 0.726169 0.066 Uiso 1 1 calc R U . . .
C00M C 0.5416(2) 0.6015(4) 0.59506(15) 0.0617(7) Uani 1 1 d . . . . .
H00M H 0.559102 0.675508 0.561922 0.074 Uiso 1 1 calc R U . . .
C00N C 0.1001(2) 0.2228(4) 0.76851(13) 0.0610(7) Uani 1 1 d . . . . .
H00N H 0.051680 0.133805 0.779897 0.073 Uiso 1 1 calc R U . . .
C00O C 0.1769(2) 0.5115(4) 0.78469(13) 0.0626(7) Uani 1 1 d . . . . .
H00O H 0.180322 0.618230 0.806962 0.075 Uiso 1 1 calc R U . . .
C00P C 0.6165(2) 0.5773(4) 0.64460(15) 0.0643(8) Uani 1 1 d . . . . .
H00P H 0.683953 0.635477 0.645222 0.077 Uiso 1 1 calc R U . . .
C00Q C 0.5910(2) 0.4669(5) 0.69307(15) 0.0665(8) Uani 1 1 d . . . . .
H00Q H 0.641988 0.448640 0.726312 0.080 Uiso 1 1 calc R U . . .
C00R C 0.1051(2) 0.3818(5) 0.80133(13) 0.0644(8) Uani 1 1 d . . . . .
H00R H 0.059661 0.400494 0.834632 0.077 Uiso 1 1 calc R U . . .
C00S C 0.3781(2) -0.1159(4) 0.43999(15) 0.0664(8) Uani 1 1 d . . . . .
H00A H 0.309939 -0.141717 0.417336 0.100 Uiso 1 1 calc R U . . .
H00B H 0.420962 -0.222939 0.444297 0.100 Uiso 1 1 calc R U . . .
H00C H 0.418032 -0.028245 0.417411 0.100 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
Br01 C00A 1.891(2) . ?
O002 C009 1.323(3) . ?
O002 C00S 1.450(3) . ?
O003 C00B 1.190(3) . ?
O004 C009 1.196(3) . ?
N005 C007 1.438(3) . ?
N005 N006 1.457(2) . ?
N005 C00C 1.562(3) . ?
N006 C009 1.397(3) . ?
N006 C00B 1.399(3) . ?
C007 C00A 1.388(3) . ?
C007 C00E 1.390(3) . ?
C008 C00G 1.384(3) . ?
C008 C00I 1.395(3) . ?
C008 C00C 1.506(3) . ?
C00A C00F 1.384(3) . ?
C00B C00C 1.540(3) . ?
C00C C00D 1.522(3) . ?
C00D C00J 1.384(3) . ?
C00D C00L 1.391(3) . ?
C00E C00H 1.384(3) . ?
C00E H00E 0.9300 . ?
C00F C00K 1.382(4) . ?
C00F H00F 0.9300 . ?
C00G C00N 1.384(4) . ?
C00G H00G 0.9300 . ?
C00H C00K 1.377(4) . ?
C00H H00H 0.9300 . ?
C00I C00O 1.384(4) . ?
C00I H00I 0.9300 . ?
C00J C00M 1.386(3) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00L C00Q 1.389(4) . ?
C00L H00L 0.9300 . ?
C00M C00P 1.375(4) . ?
C00M H00M 0.9300 . ?
C00N C00R 1.382(5) . ?
C00N H00N 0.9300 . ?
C00O C00R 1.366(4) . ?
C00O H00O 0.9300 . ?
C00P C00Q 1.370(5) . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00S H00A 0.9600 . ?
C00S H00B 0.9600 . ?
C00S H00C 0.9600 . ?

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
C009 O002 C00S 115.5(2) . . ?
C007 N005 N006 112.50(15) . . ?
C007 N005 C00C 118.19(15) . . ?
N006 N005 C00C 87.92(14) . . ?
C009 N006 C00B 134.61(18) . . ?
C009 N006 N005 120.34(17) . . ?
C00B N006 N005 95.33(15) . . ?
C00A C007 C00E 117.97(19) . . ?
C00A C007 N005 119.06(18) . . ?
C00E C007 N005 122.83(19) . . ?
C00G C008 C00I 118.4(2) . . ?
C00G C008 C00C 121.0(2) . . ?
C00I C008 C00C 120.5(2) . . ?
O004 C009 O002 127.6(2) . . ?
O004 C009 N006 122.8(2) . . ?
O002 C009 N006 109.61(19) . . ?
C00F C00A C007 121.4(2) . . ?
C00F C00A Br01 118.67(18) . . ?
C007 C00A Br01 119.91(16) . . ?
O003 C00B N006 131.9(2) . . ?
O003 C00B C00C 137.1(2) . . ?
N006 C00B C00C 90.91(16) . . ?
C008 C00C C00D 116.02(18) . . ?
C008 C00C C00B 117.96(18) . . ?
C00D C00C C00B 106.78(16) . . ?
C008 C00C N005 115.61(16) . . ?
C00D C00C N005 110.72(17) . . ?
C00B C00C N005 85.82(15) . . ?
C00J C00D C00L 119.3(2) . . ?
C00J C00D C00C 122.5(2) . . ?
C00L C00D C00C 118.0(2) . . ?
C00H C00E C007 120.8(2) . . ?
C00H C00E H00E 119.6 . . ?
C007 C00E H00E 119.6 . . ?
C00K C00F C00A 119.8(2) . . ?
C00K C00F H00F 120.1 . . ?
C00A C00F H00F 120.1 . . ?
C00N C00G C008 121.0(3) . . ?
C00N C00G H00G 119.5 . . ?
C008 C00G H00G 119.5 . . ?
C00K C00H C00E 120.4(2) . . ?
C00K C00H H00H 119.8 . . ?
C00E C00H H00H 119.8 . . ?
C00O C00I C008 120.2(3) . . ?
C00O C00I H00I 119.9 . . ?
C008 C00I H00I 119.9 . . ?
C00D C00J C00M 119.8(2) . . ?
C00D C00J H00J 120.1 . . ?
C00M C00J H00J 120.1 . . ?
C00H C00K C00F 119.6(2) . . ?
C00H C00K H00K 120.2 . . ?
C00F C00K H00K 120.2 . . ?
C00Q C00L C00D 119.9(3) . . ?
C00Q C00L H00L 120.1 . . ?
C00D C00L H00L 120.1 . . ?
C00P C00M C00J 120.9(3) . . ?
C00P C00M H00M 119.6 . . ?
C00J C00M H00M 119.6 . . ?
C00R C00N C00G 119.9(3) . . ?
C00R C00N H00N 120.1 . . ?
C00G C00N H00N 120.1 . . ?
C00R C00O C00I 120.8(3) . . ?
C00R C00O H00O 119.6 . . ?
C00I C00O H00O 119.6 . . ?
C00Q C00P C00M 119.5(2) . . ?
C00Q C00P H00P 120.3 . . ?
C00M C00P H00P 120.3 . . ?
C00P C00Q C00L 120.6(3) . . ?
C00P C00Q H00Q 119.7 . . ?
C00L C00Q H00Q 119.7 . . ?
C00O C00R C00N 119.8(2) . . ?
C00O C00R H00R 120.1 . . ?
C00N C00R H00R 120.1 . . ?
O002 C00S H00A 109.5 . . ?
O002 C00S H00B 109.5 . . ?
H00A C00S H00B 109.5 . . ?
O002 C00S H00C 109.5 . . ?
H00A C00S H00C 109.5 . . ?
H00B C00S H00C 109.5 . . ?

_refine_diff_density_max         0.476
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.051



####################################################################### 
# 
# 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_20240103ZWF_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2325419'
loop_
_audit_author_name
_audit_author_address
'weifang Zuo'
;ChengDu University of TCM
China
;
_audit_update_record             
;
2024-01-15 deposited with the CCDC.	2024-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 N2 O4'
_chemical_formula_weight         388.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   10.4537(3)
_cell_length_b                   14.6776(4)
_cell_length_c                   13.2849(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.6830(10)
_cell_angle_gamma                90
_cell_volume                     1930.96(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9115
_cell_measurement_theta_min      4.46
_cell_measurement_theta_max      68.18

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.755
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_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            27665
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.465
_diffrn_reflns_theta_max         68.576
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3547
_reflns_number_gt                2832
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0953P)²+0.3648P] 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         3547
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.1614
_refine_ls_wR_factor_gt          0.1469
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
O001 O 0.57662(14) 0.40111(10) 0.14302(10) 0.0496(4) Uani 1 1 d . . . . .
O1 O 0.23410(15) 0.59604(12) 0.01748(13) 0.0636(4) Uani 1 1 d . . . . .
O2 O 0.82887(17) 0.76520(11) 0.51325(13) 0.0635(5) Uani 1 1 d . . . . .
N004 N 0.56937(16) 0.55579(11) 0.16451(12) 0.0425(4) Uani 1 1 d . . . . .
O005 O 0.32440(17) 0.55704(15) 0.19032(14) 0.0737(5) Uani 1 1 d . . . . .
N006 N 0.45179(17) 0.57155(13) 0.08150(13) 0.0511(4) Uani 1 1 d . . . . .
H006 H 0.452965 0.579600 0.017684 0.061 Uiso 1 1 calc R U . . .
C007 C 0.72193(18) 0.57833(12) 0.32922(14) 0.0370(4) Uani 1 1 d . . . . .
C008 C 0.72840(18) 0.47731(12) 0.30461(14) 0.0369(4) Uani 1 1 d . . . . .
C009 C 0.62516(18) 0.62072(13) 0.24581(14) 0.0394(4) Uani 1 1 d . . . . .
C00A C 0.61660(18) 0.46962(13) 0.19495(14) 0.0394(4) Uani 1 1 d . . . . .
C00B C 0.78862(19) 0.62768(13) 0.41886(15) 0.0410(4) Uani 1 1 d . . . . .
H00B H 0.853139 0.600173 0.475916 0.049 Uiso 1 1 calc R U . . .
C00C C 0.86238(19) 0.44701(14) 0.29192(14) 0.0433(4) Uani 1 1 d . . . . .
C00D C 0.6848(2) 0.42102(12) 0.38617(14) 0.0407(4) Uani 1 1 d . . . . .
C00E C 0.5911(2) 0.71087(14) 0.24778(17) 0.0485(5) Uani 1 1 d . . . . .
H00E H 0.524996 0.737509 0.191038 0.058 Uiso 1 1 calc R U . . .
C00F C 0.7572(2) 0.72018(13) 0.42227(16) 0.0448(5) Uani 1 1 d . . . . .
C00G C 0.3344(2) 0.57383(14) 0.10467(16) 0.0493(5) Uani 1 1 d . . . . .
C00H C 0.5536(2) 0.42900(15) 0.38839(17) 0.0512(5) Uani 1 1 d . . . . .
H00H H 0.492384 0.465754 0.338800 0.061 Uiso 1 1 calc R U . . .
C00I C 0.6593(2) 0.76073(13) 0.33787(18) 0.0493(5) Uani 1 1 d . . . . .
H00I H 0.638992 0.822074 0.341651 0.059 Uiso 1 1 calc R U . . .
C00J C 0.9701(2) 0.50626(17) 0.30662(18) 0.0538(5) Uani 1 1 d . . . . .
H00J H 0.961341 0.566734 0.324259 0.065 Uiso 1 1 calc R U . . .
C00K C 0.7740(3) 0.36616(17) 0.46083(18) 0.0617(6) Uani 1 1 d . . . . .
H00K H 0.862670 0.360207 0.460974 0.074 Uiso 1 1 calc R U . . .
C00L C 0.8781(2) 0.35721(17) 0.26395(18) 0.0598(6) Uani 1 1 d . . . . .
H00L H 0.806800 0.316371 0.252065 0.072 Uiso 1 1 calc R U . . .
C00M C 0.5129(3) 0.38266(17) 0.4639(2) 0.0639(6) Uani 1 1 d . . . . .
H00M H 0.424640 0.388665 0.464695 0.077 Uiso 1 1 calc R U . . .
C00N C 0.6019(3) 0.32806(17) 0.5374(2) 0.0715(7) Uani 1 1 d . . . . .
H00N H 0.574542 0.296899 0.587968 0.086 Uiso 1 1 calc R U . . .
C00O C 1.0912(2) 0.4765(2) 0.2953(2) 0.0696(7) Uani 1 1 d . . . . .
H00O H 1.162542 0.517063 0.305670 0.084 Uiso 1 1 calc R U . . .
C00P C 1.1057(3) 0.3884(2) 0.2693(2) 0.0785(8) Uani 1 1 d . . . . .
H00P H 1.186817 0.368633 0.261937 0.094 Uiso 1 1 calc R U . . .
C00Q C 0.9997(3) 0.3285(2) 0.2538(2) 0.0769(8) Uani 1 1 d . . . . .
H00Q H 1.009845 0.268193 0.236314 0.092 Uiso 1 1 calc R U . . .
C00R C 0.7316(3) 0.3200(2) 0.5356(2) 0.0804(8) Uani 1 1 d . . . . .
H00R H 0.792217 0.282883 0.585184 0.096 Uiso 1 1 calc R U . . .
C00S C 0.7794(3) 0.8495(2) 0.5340(3) 0.0887(10) Uani 1 1 d . . . . .
H00A H 0.786105 0.893291 0.482278 0.133 Uiso 1 1 calc R U . . .
H00C H 0.831649 0.869887 0.603775 0.133 Uiso 1 1 calc R U . . .
H00D H 0.686618 0.843083 0.530333 0.133 Uiso 1 1 calc R U . . .
C00T C 0.1054(3) 0.6113(3) 0.0332(3) 0.0892(9) Uani 1 1 d . . . . .
H00F H 0.036536 0.617342 -0.034597 0.134 Uiso 1 1 calc R U . . .
H00G H 0.109620 0.665981 0.073654 0.134 Uiso 1 1 calc R U . . .
H00S H 0.084578 0.560566 0.070828 0.134 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
O001 C00A 1.215(2) . ?
O1 C00G 1.330(3) . ?
O1 C00T 1.443(3) . ?
O2 C00F 1.371(2) . ?
O2 C00S 1.402(3) . ?
N004 C00A 1.371(2) . ?
N004 N006 1.383(2) . ?
N004 C009 1.418(2) . ?
O005 C00G 1.201(3) . ?
N006 C00G 1.357(3) . ?
N006 H006 0.8600 . ?
C007 C00B 1.377(3) . ?
C007 C009 1.386(3) . ?
C007 C008 1.525(2) . ?
C008 C00C 1.529(3) . ?
C008 C00D 1.543(2) . ?
C008 C00A 1.552(2) . ?
C009 C00E 1.373(3) . ?
C00B C00F 1.401(3) . ?
C00B H00B 0.9300 . ?
C00C C00J 1.386(3) . ?
C00C C00L 1.393(3) . ?
C00D C00K 1.382(3) . ?
C00D C00H 1.386(3) . ?
C00E C00I 1.389(3) . ?
C00E H00E 0.9300 . ?
C00F C00I 1.387(3) . ?
C00H C00M 1.387(3) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00J C00O 1.392(3) . ?
C00J H00J 0.9300 . ?
C00K C00R 1.387(3) . ?
C00K H00K 0.9300 . ?
C00L C00Q 1.386(3) . ?
C00L H00L 0.9300 . ?
C00M C00N 1.371(4) . ?
C00M H00M 0.9300 . ?
C00N C00R 1.369(4) . ?
C00N H00N 0.9300 . ?
C00O C00P 1.360(4) . ?
C00O H00O 0.9300 . ?
C00P C00Q 1.377(4) . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00S H00A 0.9600 . ?
C00S H00C 0.9600 . ?
C00S H00D 0.9600 . ?
C00T H00F 0.9600 . ?
C00T H00G 0.9600 . ?
C00T H00S 0.9600 . ?

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
C00G O1 C00T 115.1(2) . . ?
C00F O2 C00S 117.9(2) . . ?
C00A N004 N006 122.26(16) . . ?
C00A N004 C009 111.95(15) . . ?
N006 N004 C009 122.59(16) . . ?
C00G N006 N004 117.41(16) . . ?
C00G N006 H006 121.3 . . ?
N004 N006 H006 121.3 . . ?
C00B C007 C009 119.54(17) . . ?
C00B C007 C008 130.69(16) . . ?
C009 C007 C008 109.65(15) . . ?
C007 C008 C00C 114.30(15) . . ?
C007 C008 C00D 109.07(14) . . ?
C00C C008 C00D 114.13(15) . . ?
C007 C008 C00A 101.54(14) . . ?
C00C C008 C00A 108.43(14) . . ?
C00D C008 C00A 108.49(14) . . ?
C00E C009 C007 123.02(18) . . ?
C00E C009 N004 128.04(18) . . ?
C007 C009 N004 108.91(16) . . ?
O001 C00A N004 124.75(17) . . ?
O001 C00A C008 127.69(17) . . ?
N004 C00A C008 107.55(15) . . ?
C007 C00B C00F 118.60(18) . . ?
C007 C00B H00B 120.7 . . ?
C00F C00B H00B 120.7 . . ?
C00J C00C C00L 118.1(2) . . ?
C00J C00C C008 122.23(18) . . ?
C00L C00C C008 119.68(19) . . ?
C00K C00D C00H 118.63(19) . . ?
C00K C00D C008 122.17(19) . . ?
C00H C00D C008 119.12(17) . . ?
C009 C00E C00I 117.36(19) . . ?
C009 C00E H00E 121.3 . . ?
C00I C00E H00E 121.3 . . ?
O2 C00F C00I 124.01(18) . . ?
O2 C00F C00B 115.36(18) . . ?
C00I C00F C00B 120.64(18) . . ?
O005 C00G O1 126.3(2) . . ?
O005 C00G N006 124.69(19) . . ?
O1 C00G N006 109.05(18) . . ?
C00D C00H C00M 120.6(2) . . ?
C00D C00H H00H 119.7 . . ?
C00M C00H H00H 119.7 . . ?
C00F C00I C00E 120.83(18) . . ?
C00F C00I H00I 119.6 . . ?
C00E C00I H00I 119.6 . . ?
C00C C00J C00O 120.9(2) . . ?
C00C C00J H00J 119.6 . . ?
C00O C00J H00J 119.6 . . ?
C00D C00K C00R 120.1(2) . . ?
C00D C00K H00K 120.0 . . ?
C00R C00K H00K 120.0 . . ?
C00Q C00L C00C 120.2(2) . . ?
C00Q C00L H00L 119.9 . . ?
C00C C00L H00L 119.9 . . ?
C00N C00M C00H 120.4(2) . . ?
C00N C00M H00M 119.8 . . ?
C00H C00M H00M 119.8 . . ?
C00R C00N C00M 119.2(2) . . ?
C00R C00N H00N 120.4 . . ?
C00M C00N H00N 120.4 . . ?
C00P C00O C00J 120.4(3) . . ?
C00P C00O H00O 119.8 . . ?
C00J C00O H00O 119.8 . . ?
C00O C00P C00Q 119.6(2) . . ?
C00O C00P H00P 120.2 . . ?
C00Q C00P H00P 120.2 . . ?
C00P C00Q C00L 120.7(3) . . ?
C00P C00Q H00Q 119.6 . . ?
C00L C00Q H00Q 119.6 . . ?
C00N C00R C00K 121.1(3) . . ?
C00N C00R H00R 119.5 . . ?
C00K C00R H00R 119.5 . . ?
O2 C00S H00A 109.5 . . ?
O2 C00S H00C 109.5 . . ?
H00A C00S H00C 109.5 . . ?
O2 C00S H00D 109.5 . . ?
H00A C00S H00D 109.5 . . ?
H00C C00S H00D 109.5 . . ?
O1 C00T H00F 109.5 . . ?
O1 C00T H00G 109.5 . . ?
H00F C00T H00G 109.5 . . ?
O1 C00T H00S 109.5 . . ?
H00F C00T H00S 109.5 . . ?
H00G C00T H00S 109.5 . . ?

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.102



