# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_exp_12479_tw
_database_code_depnum_ccdc_archive 'CCDC 2183638'
loop_
_audit_author_name
_audit_author_address
'Wenzeng Duan'
;Liaocheng University
China
;
_audit_update_record             
;
2022-07-04 deposited with the CCDC.	2022-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H19 N O4'
_chemical_formula_weight         397.41

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.1268(8)
_cell_length_b                   8.0238(7)
_cell_length_c                   26.1099(14)
_cell_angle_alpha                90
_cell_angle_beta                 89.960(6)
_cell_angle_gamma                90
_cell_volume                     1912.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2788
_cell_measurement_theta_min      5.1190
_cell_measurement_theta_max      70.2600

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.763
_shelx_estimated_absorpt_T_min   0.914
_shelx_estimated_absorpt_T_max   0.921
_exptl_absorpt_correction_T_min  0.90755
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3424
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.385
_diffrn_reflns_theta_max         67.317
_diffrn_reflns_theta_full        67.317
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3424
_reflns_number_gt                2469
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] 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         3424
_refine_ls_number_parameters     272
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0622
_refine_ls_wR_factor_ref         0.1964
_refine_ls_wR_factor_gt          0.1746
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.146
_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
N1 N 0.6170(7) 0.0452(6) -0.08327(19) 0.1165(17) Uani 1 1 d . U . . .
O1 O 0.1516(3) 0.4469(3) 0.07246(9) 0.0786(7) Uani 1 1 d . . . . .
O2 O -0.2170(4) 0.3382(5) 0.05101(13) 0.1035(10) Uani 1 1 d . . . . .
O3 O 0.7329(6) 0.0963(6) -0.06655(18) 0.1311(16) Uani 1 1 d . U . . .
O4 O 0.6052(6) -0.0559(7) -0.11957(18) 0.161(2) Uani 1 1 d . . . . .
C1 C 0.2977(5) 0.6057(6) 0.15950(18) 0.0946(14) Uani 1 1 d . . . . .
H1A H 0.337604 0.701931 0.177102 0.114 Uiso 1 1 calc R U . . .
H1B H 0.356946 0.585894 0.129253 0.114 Uiso 1 1 calc R U . . .
C2 C 0.3076(6) 0.4492(8) 0.1958(2) 0.1085(16) Uani 1 1 d . . . . .
H2A H 0.364400 0.363065 0.178911 0.130 Uiso 1 1 calc R U . . .
H2B H 0.359242 0.480464 0.226836 0.130 Uiso 1 1 calc R U . . .
C3 C 0.1605(5) 0.3793(6) 0.21011(15) 0.0825(11) Uani 1 1 d . . . . .
C4 C 0.0732(7) 0.4552(6) 0.24646(15) 0.0884(13) Uani 1 1 d . . . . .
H4A H 0.115848 0.519882 0.271968 0.106 Uiso 1 1 calc R U . . .
C5 C -0.0762(6) 0.4356(6) 0.24516(15) 0.0873(13) Uani 1 1 d . . . . .
H5 H -0.133420 0.487750 0.269921 0.105 Uiso 1 1 calc R U . . .
C6 C -0.1439(5) 0.3397(5) 0.20772(15) 0.0826(11) Uani 1 1 d . . . . .
C7 C -0.0533(5) 0.2348(5) 0.17956(14) 0.0797(12) Uani 1 1 d . . . . .
H7 H -0.094046 0.150033 0.159887 0.096 Uiso 1 1 calc R U . . .
C8 C 0.0956(6) 0.2554(5) 0.18062(15) 0.0825(12) Uani 1 1 d . . . . .
H8 H 0.154607 0.185101 0.161198 0.099 Uiso 1 1 calc R U . . .
C9 C -0.2997(5) 0.3748(8) 0.1910(2) 0.1095(16) Uani 1 1 d . . . . .
H9A H -0.359919 0.394174 0.221017 0.131 Uiso 1 1 calc R U . . .
H9B H -0.338185 0.277720 0.173388 0.131 Uiso 1 1 calc R U . . .
C10 C -0.3106(5) 0.5316(7) 0.15416(19) 0.0990(14) Uani 1 1 d . . . . .
H10A H -0.361515 0.498943 0.123143 0.119 Uiso 1 1 calc R U . . .
H10B H -0.368790 0.616926 0.170862 0.119 Uiso 1 1 calc R U . . .
C11 C -0.1656(5) 0.6041(6) 0.13989(15) 0.0822(11) Uani 1 1 d . . . . .
C12 C -0.0999(6) 0.7280(6) 0.16868(15) 0.0852(13) Uani 1 1 d . . . . .
H12 H -0.158317 0.800744 0.187431 0.102 Uiso 1 1 calc R U . . .
C13 C 0.0498(6) 0.7461(5) 0.17021(15) 0.0871(14) Uani 1 1 d . . . . .
H13 H 0.089427 0.831079 0.190056 0.104 Uiso 1 1 calc R U . . .
C14 C 0.1437(5) 0.6428(5) 0.14342(14) 0.0782(11) Uani 1 1 d . . . . .
C15 C 0.0730(5) 0.5497(4) 0.10627(12) 0.0659(9) Uani 1 1 d . . . . .
C16 C -0.0736(5) 0.5263(5) 0.10359(12) 0.0705(10) Uani 1 1 d . . . . .
C17 C -0.0965(5) 0.3976(5) 0.06499(14) 0.0776(10) Uani 1 1 d . . . . .
C18 C 0.0474(5) 0.3573(5) 0.04604(13) 0.0769(11) Uani 1 1 d . . . . .
C19 C 0.0812(5) 0.2492(5) 0.00732(13) 0.0820(11) Uani 1 1 d . . . . .
H19 H 0.001003 0.194848 -0.006984 0.098 Uiso 1 1 calc R U . . .
C20 C 0.2208(5) 0.2053(5) -0.01505(13) 0.0791(11) Uani 1 1 d . . . . .
C21 C 0.3549(5) 0.2751(6) -0.00123(16) 0.0870(11) Uani 1 1 d . . . . .
H21 H 0.357292 0.357378 0.023841 0.104 Uiso 1 1 calc R U . . .
C22 C 0.4830(6) 0.2252(5) -0.02375(15) 0.0934(13) Uani 1 1 d . . . . .
H22 H 0.571733 0.273061 -0.014288 0.112 Uiso 1 1 calc R U . . .
C23 C 0.4780(7) 0.1021(6) -0.06091(15) 0.0911(13) Uani 1 1 d . . . . .
C24 C 0.3475(8) 0.0320(6) -0.07628(18) 0.1027(16) Uani 1 1 d . . . . .
H24 H 0.346294 -0.047729 -0.102128 0.123 Uiso 1 1 calc R U . . .
C25 C 0.2182(7) 0.0810(6) -0.05301(16) 0.1000(16) Uani 1 1 d . . . . .
H25 H 0.129986 0.031874 -0.062434 0.120 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
N1 O3 1.215(7) . ?
N1 O4 1.252(7) . ?
N1 C23 1.469(7) . ?
O1 C18 1.377(5) . ?
O1 C15 1.405(4) . ?
O2 C17 1.254(5) . ?
C1 C14 1.497(7) . ?
C1 C2 1.576(7) . ?
C2 C3 1.502(7) . ?
C3 C4 1.380(7) . ?
C3 C8 1.390(6) . ?
C4 C5 1.373(7) . ?
C5 C6 1.389(7) . ?
C6 C7 1.390(6) . ?
C6 C9 1.515(7) . ?
C7 C8 1.370(6) . ?
C9 C10 1.586(7) . ?
C10 C11 1.493(7) . ?
C11 C12 1.383(7) . ?
C11 C16 1.412(6) . ?
C12 C13 1.374(7) . ?
C13 C14 1.382(6) . ?
C14 C15 1.384(6) . ?
C15 C16 1.353(6) . ?
C16 C17 1.458(5) . ?
C17 C18 1.440(6) . ?
C18 C19 1.367(5) . ?
C19 C20 1.445(6) . ?
C20 C21 1.393(7) . ?
C20 C25 1.406(6) . ?
C21 C22 1.368(7) . ?
C22 C23 1.385(6) . ?
C23 C24 1.377(8) . ?
C24 C25 1.384(8) . ?

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
O3 N1 O4 124.5(6) . . ?
O3 N1 C23 120.3(5) . . ?
O4 N1 C23 115.3(6) . . ?
C18 O1 C15 105.6(3) . . ?
C14 C1 C2 112.5(4) . . ?
C3 C2 C1 113.3(4) . . ?
C4 C3 C8 116.8(4) . . ?
C4 C3 C2 121.4(5) . . ?
C8 C3 C2 120.7(4) . . ?
C5 C4 C3 120.4(5) . . ?
C4 C5 C6 121.5(4) . . ?
C5 C6 C7 116.3(4) . . ?
C5 C6 C9 121.2(5) . . ?
C7 C6 C9 121.2(4) . . ?
C8 C7 C6 120.4(4) . . ?
C7 C8 C3 121.4(4) . . ?
C6 C9 C10 112.4(4) . . ?
C11 C10 C9 113.9(4) . . ?
C12 C11 C16 115.1(4) . . ?
C12 C11 C10 122.0(4) . . ?
C16 C11 C10 121.5(4) . . ?
C13 C12 C11 121.5(4) . . ?
C12 C13 C14 122.6(4) . . ?
C13 C14 C15 112.9(4) . . ?
C13 C14 C1 124.0(4) . . ?
C15 C14 C1 121.8(4) . . ?
C16 C15 C14 124.9(4) . . ?
C16 C15 O1 113.0(4) . . ?
C14 C15 O1 121.3(4) . . ?
C15 C16 C11 119.4(4) . . ?
C15 C16 C17 106.0(4) . . ?
C11 C16 C17 133.8(4) . . ?
O2 C17 C18 127.9(4) . . ?
O2 C17 C16 126.7(4) . . ?
C18 C17 C16 105.4(4) . . ?
C19 C18 O1 123.1(4) . . ?
C19 C18 C17 127.0(4) . . ?
O1 C18 C17 109.9(3) . . ?
C18 C19 C20 130.7(4) . . ?
C21 C20 C25 118.9(5) . . ?
C21 C20 C19 124.9(4) . . ?
C25 C20 C19 116.3(5) . . ?
C22 C21 C20 121.4(4) . . ?
C21 C22 C23 118.8(5) . . ?
C24 C23 C22 121.6(5) . . ?
C24 C23 N1 120.3(5) . . ?
C22 C23 N1 118.1(6) . . ?
C23 C24 C25 119.6(5) . . ?
C24 C25 C20 119.7(6) . . ?

_refine_diff_density_max         0.281
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.040



####################################################################### 
# 
# 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_220728b
_database_code_depnum_ccdc_archive 'CCDC 2202112'
loop_
_audit_author_name
_audit_author_address
'Wenzeng Duan'
;Liaocheng University
China
;
_audit_update_record             
;
2022-08-18 deposited with the CCDC.	2022-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H9 N O4'
_chemical_formula_weight         267.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   3.8550(4)
_cell_length_b                   6.9039(7)
_cell_length_c                   11.2145(11)
_cell_angle_alpha                91.025(2)
_cell_angle_beta                 93.364(3)
_cell_angle_gamma                96.825(4)
_cell_volume                     295.75(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3797
_cell_measurement_theta_min      5.943
_cell_measurement_theta_max      49.724

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_F_000             138
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.992
_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     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1492
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.447
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.594
_diffrn_reflns_point_group_measured_fraction_full 0.594
_reflns_number_total             1242
_reflns_number_gt                1040
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.203
_reflns_Friedel_fraction_max     0.201
_reflns_Friedel_fraction_full    0.201

_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    ?
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.1743P)²] 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_abs_structure_details 
;
 Flack x determined using 169 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -4.0(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         1242
_refine_ls_number_parameters     170
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0885
_refine_ls_wR_factor_ref         0.2301
_refine_ls_wR_factor_gt          0.2224
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.080
_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
N1 N -0.1043(16) -0.1062(11) -0.2664(7) 0.0565(19) Uani 1 1 d . . . . .
O1 O 0.8677(13) 0.2965(7) 0.1939(5) 0.0469(14) Uani 1 1 d . . . . .
O2 O 0.9775(18) 0.8044(9) 0.1938(7) 0.079(2) Uani 1 1 d . . . . .
O3 O -0.140(2) -0.2727(10) -0.2345(7) 0.091(3) Uani 1 1 d . . . . .
O4 O -0.231(2) -0.0588(11) -0.3616(7) 0.088(3) Uani 1 1 d . . . . .
C1 C 1.1379(19) 0.5450(12) 0.3197(7) 0.0471(19) Uani 1 1 d . . . . .
C2 C 1.318(2) 0.6130(14) 0.4209(8) 0.057(2) Uani 1 1 d . . . . .
H2 H 1.364046 0.746812 0.435970 0.068 Uiso 1 1 calc R U . . .
C3 C 1.433(2) 0.4852(14) 0.5021(8) 0.061(2) Uani 1 1 d . . . . .
H3 H 1.558954 0.530299 0.572456 0.074 Uiso 1 1 calc R U . . .
C4 C 1.356(2) 0.2860(15) 0.4765(9) 0.058(2) Uani 1 1 d . . . . .
H4 H 1.433547 0.199011 0.531613 0.070 Uiso 1 1 calc R U . . .
C5 C 1.177(2) 0.2136(14) 0.3761(8) 0.056(2) Uani 1 1 d . . . . .
H5 H 1.132054 0.080009 0.360229 0.068 Uiso 1 1 calc R U . . .
C6 C 1.0627(18) 0.3463(12) 0.2984(7) 0.0453(19) Uani 1 1 d . . . . .
C7 C 0.8095(19) 0.4704(12) 0.1410(7) 0.0439(18) Uani 1 1 d . . . . .
C8 C 0.976(2) 0.6332(12) 0.2167(7) 0.052(2) Uani 1 1 d . . . . .
C9 C 0.622(2) 0.4759(12) 0.0382(7) 0.047(2) Uani 1 1 d . . . . .
H9 H 0.603644 0.600675 0.010426 0.056 Uiso 1 1 calc R U . . .
C10 C 0.4425(11) 0.3214(6) -0.0366(4) 0.0395(17) Uani 1 1 d G . . . .
C11 C 0.4008(12) 0.1274(7) -0.0044(4) 0.049(2) Uani 1 1 d G . . . .
H11 H 0.499065 0.091624 0.068431 0.059 Uiso 1 1 calc R U . . .
C12 C 0.2178(14) -0.0102(7) -0.0784(5) 0.0460(19) Uani 1 1 d G . . . .
H12 H 0.181862 -0.139326 -0.055082 0.055 Uiso 1 1 calc R U . . .
C13 C 0.0854(14) 0.0419(7) -0.1881(5) 0.0433(18) Uani 1 1 d G . . . .
C14 C 0.1179(13) 0.2323(7) -0.2214(5) 0.049(2) Uani 1 1 d G . . . .
H14 H 0.018056 0.267330 -0.294119 0.058 Uiso 1 1 calc R U . . .
C15 C 0.2988(11) 0.3692(6) -0.1461(4) 0.0462(19) Uani 1 1 d G . . . .
H15 H 0.326682 0.498691 -0.168825 0.055 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
N1 O3 1.205(10) . ?
N1 O4 1.214(10) . ?
N1 C13 1.437(9) . ?
O1 C6 1.371(9) . ?
O1 C7 1.385(10) . ?
O2 C8 1.214(10) . ?
C1 C2 1.342(12) . ?
C1 C6 1.381(11) . ?
C1 C8 1.459(11) . ?
C2 C3 1.371(13) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(14) . ?
C3 H3 0.9300 . ?
C4 C5 1.343(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.368(11) . ?
C5 H5 0.9300 . ?
C7 C9 1.328(10) . ?
C7 C8 1.458(12) . ?
C9 C10 1.430(9) . ?
C9 H9 0.9300 . ?
C10 C15 1.378(3) . ?
C10 C11 1.387(3) . ?
C11 C12 1.353(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.366(3) . ?
C14 C15 1.356(3) . ?
C14 H14 0.9300 . ?
C15 H15 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
O3 N1 O4 122.0(8) . . ?
O3 N1 C13 119.1(7) . . ?
O4 N1 C13 118.9(7) . . ?
C6 O1 C7 106.2(6) . . ?
C2 C1 C6 120.1(7) . . ?
C2 C1 C8 135.1(8) . . ?
C6 C1 C8 104.8(7) . . ?
C1 C2 C3 119.9(8) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 118.2(8) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 123.2(9) . . ?
C5 C4 H4 118.4 . . ?
C3 C4 H4 118.4 . . ?
C4 C5 C6 116.6(9) . . ?
C4 C5 H5 121.7 . . ?
C6 C5 H5 121.7 . . ?
C5 C6 O1 123.9(7) . . ?
C5 C6 C1 121.9(7) . . ?
O1 C6 C1 114.2(6) . . ?
C9 C7 O1 122.2(7) . . ?
C9 C7 C8 128.5(7) . . ?
O1 C7 C8 109.3(7) . . ?
O2 C8 C7 125.2(8) . . ?
O2 C8 C1 129.2(8) . . ?
C7 C8 C1 105.6(7) . . ?
C7 C9 C10 130.5(7) . . ?
C7 C9 H9 114.7 . . ?
C10 C9 H9 114.7 . . ?
C15 C10 C11 118.4 . . ?
C15 C10 C9 117.9(4) . . ?
C11 C10 C9 123.7(4) . . ?
C12 C11 C10 120.4 . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 119.6 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 121.1 . . ?
C14 C13 N1 119.8(4) . . ?
C12 C13 N1 119.0(4) . . ?
C15 C14 C13 118.6 . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C10 121.7 . . ?
C14 C15 H15 119.1 . . ?
C10 C15 H15 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.3(11) . . . . ?
C8 C1 C2 C3 179.2(8) . . . . ?
C1 C2 C3 C4 -0.3(12) . . . . ?
C2 C3 C4 C5 0.3(13) . . . . ?
C3 C4 C5 C6 -1.1(13) . . . . ?
C4 C5 C6 O1 -178.1(7) . . . . ?
C4 C5 C6 C1 2.1(11) . . . . ?
C7 O1 C6 C5 -179.4(7) . . . . ?
C7 O1 C6 C1 0.4(7) . . . . ?
C2 C1 C6 C5 -2.3(10) . . . . ?
C8 C1 C6 C5 179.3(7) . . . . ?
C2 C1 C6 O1 177.9(8) . . . . ?
C8 C1 C6 O1 -0.6(8) . . . . ?
C6 O1 C7 C9 -178.7(7) . . . . ?
C6 O1 C7 C8 -0.1(8) . . . . ?
C9 C7 C8 O2 -3.0(14) . . . . ?
O1 C7 C8 O2 178.5(8) . . . . ?
C9 C7 C8 C1 178.3(7) . . . . ?
O1 C7 C8 C1 -0.2(9) . . . . ?
C2 C1 C8 O2 3.7(16) . . . . ?
C6 C1 C8 O2 -178.2(9) . . . . ?
C2 C1 C8 C7 -177.7(9) . . . . ?
C6 C1 C8 C7 0.4(8) . . . . ?
O1 C7 C9 C10 1.2(12) . . . . ?
C8 C7 C9 C10 -177.2(8) . . . . ?
C7 C9 C10 C15 -172.9(7) . . . . ?
C7 C9 C10 C11 8.2(10) . . . . ?
C15 C10 C11 C12 -1.1 . . . . ?
C9 C10 C11 C12 177.8(5) . . . . ?
C10 C11 C12 C13 2.7 . . . . ?
C11 C12 C13 C14 -3.8 . . . . ?
C11 C12 C13 N1 179.2(5) . . . . ?
O3 N1 C13 C14 -177.8(6) . . . . ?
O4 N1 C13 C14 0.5(9) . . . . ?
O3 N1 C13 C12 -0.7(9) . . . . ?
O4 N1 C13 C12 177.6(6) . . . . ?
C12 C13 C14 C15 3.1 . . . . ?
N1 C13 C14 C15 -179.9(5) . . . . ?
C13 C14 C15 C10 -1.5 . . . . ?
C11 C10 C15 C14 0.5 . . . . ?
C9 C10 C15 C14 -178.5(5) . . . . ?

_refine_diff_density_max         0.359
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.098



