# 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_mo_d8v23188_0m
_database_code_depnum_ccdc_archive 'CCDC 2268376'
loop_
_audit_author_name
_audit_author_address
'Qiongwen Kang'
;East China Normal University
China
;
_audit_update_record             
;
2023-06-08 deposited with the CCDC.	2024-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 N2 O2'
_chemical_formula_weight         266.29

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

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

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

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

_cell_length_a                   8.0941(4)
_cell_length_b                   16.8363(7)
_cell_length_c                   10.3616(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.720(2)
_cell_angle_gamma                90
_cell_volume                     1311.77(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    5700
_cell_measurement_theta_min      4.875
_cell_measurement_theta_max      54.494

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4830
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            13345
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.709
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2562
_reflns_number_gt                1986
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0569P)²+0.6689P] 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     SHELXL
_refine_ls_extinction_coef       0.021(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2562
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1463
_refine_ls_wR_factor_gt          0.1331
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.003

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6636(2) 0.45247(9) 0.25185(16) 0.0472(5) Uani 1 1 d . . . . .
H1 H 0.7233 0.4231 0.3167 0.071 Uiso 1 1 calc R U . . .
O2 O 0.8330(2) 0.42346(9) 0.51554(16) 0.0437(4) Uani 1 1 d . . . . .
N1 N 0.5847(2) 0.60999(10) 0.44936(17) 0.0352(4) Uani 1 1 d . . . . .
H1A H 0.5956 0.6350 0.5255 0.042 Uiso 1 1 calc R U . . .
N2 N 0.8631(2) 0.51322(10) 0.68486(17) 0.0349(4) Uani 1 1 d . . . . .
C1 C 0.4823(3) 0.63395(12) 0.3175(2) 0.0336(5) Uani 1 1 d . . . . .
C2 C 0.3793(3) 0.70223(13) 0.2726(2) 0.0438(6) Uani 1 1 d . . . . .
H2 H 0.3691 0.7398 0.3364 0.053 Uiso 1 1 calc R U . . .
C3 C 0.2933(3) 0.71269(14) 0.1322(2) 0.0452(6) Uani 1 1 d . . . . .
H3 H 0.2248 0.7587 0.0996 0.054 Uiso 1 1 calc R U . . .
C4 C 0.3050(3) 0.65653(14) 0.0364(2) 0.0441(6) Uani 1 1 d . . . . .
H4 H 0.2419 0.6648 -0.0590 0.053 Uiso 1 1 calc R U . . .
C5 C 0.4072(3) 0.58975(13) 0.0798(2) 0.0404(5) Uani 1 1 d . . . . .
H5 H 0.4157 0.5524 0.0150 0.049 Uiso 1 1 calc R U . . .
C6 C 0.4990(3) 0.57805(12) 0.2226(2) 0.0328(5) Uani 1 1 d . . . . .
C7 C 0.6155(3) 0.51816(12) 0.3037(2) 0.0324(5) Uani 1 1 d . . . . .
C8 C 0.6690(3) 0.53865(12) 0.4412(2) 0.0326(5) Uani 1 1 d . . . . .
C9 C 0.7940(3) 0.48971(12) 0.5508(2) 0.0325(5) Uani 1 1 d . . . . .
C10 C 0.8543(3) 0.59278(12) 0.7311(2) 0.0313(5) Uani 1 1 d . . . . .
C11 C 0.7758(3) 0.60686(14) 0.8270(2) 0.0419(6) Uani 1 1 d . . . . .
H11 H 0.7263 0.5647 0.8602 0.050 Uiso 1 1 calc R U . . .
C12 C 0.7708(3) 0.68352(15) 0.8737(3) 0.0506(6) Uani 1 1 d . . . . .
H12 H 0.7189 0.6933 0.9397 0.061 Uiso 1 1 calc R U . . .
C13 C 0.8414(3) 0.74557(14) 0.8244(3) 0.0487(6) Uani 1 1 d . . . . .
H13 H 0.8367 0.7975 0.8560 0.058 Uiso 1 1 calc R U . . .
C14 C 0.9183(3) 0.73142(13) 0.7289(2) 0.0425(6) Uani 1 1 d . . . . .
H14 H 0.9657 0.7739 0.6947 0.051 Uiso 1 1 calc R U . . .
C15 C 0.9268(3) 0.65494(12) 0.6827(2) 0.0346(5) Uani 1 1 d . . . . .
H15 H 0.9816 0.6453 0.6186 0.042 Uiso 1 1 calc R U . . .
C16 C 0.9759(3) 0.45725(13) 0.7890(2) 0.0447(6) Uani 1 1 d . . . . .
H16A H 1.0837 0.4840 0.8477 0.067 Uiso 1 1 calc R U . . .
H16B H 1.0065 0.4128 0.7425 0.067 Uiso 1 1 calc R U . . .
H16C H 0.9120 0.4380 0.8456 0.067 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.348(2) . ?
O1 H1 0.8300 . ?
O2 C9 1.250(2) . ?
N1 C1 1.370(3) . ?
N1 C8 1.399(3) . ?
N1 H1A 0.8700 . ?
N2 C9 1.351(3) . ?
N2 C10 1.433(2) . ?
N2 C16 1.469(3) . ?
C1 C2 1.395(3) . ?
C1 C6 1.404(3) . ?
C2 C3 1.372(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.400(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.369(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.402(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.423(3) . ?
C7 C8 1.371(3) . ?
C8 C9 1.464(3) . ?
C10 C15 1.381(3) . ?
C10 C11 1.384(3) . ?
C11 C12 1.384(3) . ?
C11 H11 0.9400 . ?
C12 C13 1.377(4) . ?
C12 H12 0.9400 . ?
C13 C14 1.371(3) . ?
C13 H13 0.9400 . ?
C14 C15 1.384(3) . ?
C14 H14 0.9400 . ?
C15 H15 0.9400 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?

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
C7 O1 H1 109.5 . . ?
C1 N1 C8 108.73(16) . . ?
C1 N1 H1A 125.6 . . ?
C8 N1 H1A 125.6 . . ?
C9 N2 C10 124.39(16) . . ?
C9 N2 C16 118.42(17) . . ?
C10 N2 C16 116.63(16) . . ?
N1 C1 C2 129.9(2) . . ?
N1 C1 C6 108.75(17) . . ?
C2 C1 C6 121.30(19) . . ?
C3 C2 C1 117.7(2) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 121.6(2) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 118.8(2) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 119.64(19) . . ?
C5 C6 C7 134.34(19) . . ?
C1 C6 C7 106.02(17) . . ?
O1 C7 C8 126.42(18) . . ?
O1 C7 C6 124.87(18) . . ?
C8 C7 C6 108.71(17) . . ?
C7 C8 N1 107.78(17) . . ?
C7 C8 C9 121.77(18) . . ?
N1 C8 C9 130.45(18) . . ?
O2 C9 N2 120.59(18) . . ?
O2 C9 C8 116.89(18) . . ?
N2 C9 C8 122.51(18) . . ?
C15 C10 C11 120.0(2) . . ?
C15 C10 N2 120.44(18) . . ?
C11 C10 N2 119.53(19) . . ?
C12 C11 C10 119.4(2) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 119.9(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.3(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 119.8(2) . . ?
C10 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 -177.5(2) . . . . ?
C8 N1 C1 C6 0.2(2) . . . . ?
N1 C1 C2 C3 178.0(2) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C2 C3 C4 C5 -1.7(4) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C1 0.9(3) . . . . ?
C4 C5 C6 C7 -179.3(2) . . . . ?
N1 C1 C6 C5 -179.48(18) . . . . ?
C2 C1 C6 C5 -1.6(3) . . . . ?
N1 C1 C6 C7 0.7(2) . . . . ?
C2 C1 C6 C7 178.6(2) . . . . ?
C5 C6 C7 O1 -1.2(4) . . . . ?
C1 C6 C7 O1 178.65(19) . . . . ?
C5 C6 C7 C8 178.9(2) . . . . ?
C1 C6 C7 C8 -1.3(2) . . . . ?
O1 C7 C8 N1 -178.53(19) . . . . ?
C6 C7 C8 N1 1.4(2) . . . . ?
O1 C7 C8 C9 1.8(3) . . . . ?
C6 C7 C8 C9 -178.29(18) . . . . ?
C1 N1 C8 C7 -1.0(2) . . . . ?
C1 N1 C8 C9 178.7(2) . . . . ?
C10 N2 C9 O2 167.44(19) . . . . ?
C16 N2 C9 O2 -3.7(3) . . . . ?
C10 N2 C9 C8 -13.8(3) . . . . ?
C16 N2 C9 C8 175.04(19) . . . . ?
C7 C8 C9 O2 -8.6(3) . . . . ?
N1 C8 C9 O2 171.7(2) . . . . ?
C7 C8 C9 N2 172.57(19) . . . . ?
N1 C8 C9 N2 -7.1(3) . . . . ?
C9 N2 C10 C15 -58.9(3) . . . . ?
C16 N2 C10 C15 112.4(2) . . . . ?
C9 N2 C10 C11 122.4(2) . . . . ?
C16 N2 C10 C11 -66.3(3) . . . . ?
C15 C10 C11 C12 -0.1(3) . . . . ?
N2 C10 C11 C12 178.65(19) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
C11 C12 C13 C14 -0.5(4) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C11 C10 C15 C14 -0.9(3) . . . . ?
N2 C10 C15 C14 -179.59(18) . . . . ?
C13 C14 C15 C10 1.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C15 H15 O2 0.94 2.66 3.564(3) 161.9 3_766
O1 H1 O2 0.83 1.92 2.610(2) 140.1 .

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_mo_d8v23354_0m
_database_code_depnum_ccdc_archive 'CCDC 2280227'
loop_
_audit_author_name
_audit_author_address
'Qiongwen Kang'
;East China Normal University
China
;
_audit_update_record             
;
2023-07-08 deposited with the CCDC.	2024-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 N2 O4'
_chemical_formula_weight         322.31

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   5.5407(4)
_cell_length_b                   13.5218(9)
_cell_length_c                   10.3493(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.771(2)
_cell_angle_gamma                90
_cell_volume                     764.12(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    4902
_cell_measurement_theta_min      5.003
_cell_measurement_theta_max      54.970

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5754
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            8348
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.013
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2955
_reflns_number_gt                2651
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.905
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    0.983

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+0.1051P] 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     SHELXL
_refine_ls_extinction_coef       0.114(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1122 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.1(8)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2955
_refine_ls_number_parameters     220
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1040
_refine_ls_wR_factor_gt          0.0986
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.1975(4) 0.4120(2) 0.1206(2) 0.0437(6) Uani 1 1 d . . . . .
O2 O -0.1563(4) 0.42755(18) 0.4600(2) 0.0377(6) Uani 1 1 d . . . . .
O3 O 0.7431(6) 0.7953(2) 0.3219(3) 0.0788(12) Uani 1 1 d . . . . .
O4 O 0.6067(6) 0.8289(2) 0.1135(2) 0.0545(8) Uani 1 1 d . . . . .
N1 N 0.3237(4) 0.45575(18) 0.3628(2) 0.0281(6) Uani 1 1 d . . . . .
H1 H 0.4256 0.4476 0.4358 0.034 Uiso 1 1 calc R U . . .
N2 N -0.0698(4) 0.26534(19) 0.4150(2) 0.0297(6) Uani 1 1 d . . . . .
C1 C 0.3231(5) 0.5355(2) 0.2808(3) 0.0250(6) Uani 1 1 d . . . . .
C2 C 0.4896(5) 0.6131(2) 0.2917(3) 0.0267(7) Uani 1 1 d . . . . .
H2 H 0.6283 0.6138 0.3580 0.032 Uiso 1 1 calc R U . . .
C3 C 0.4443(5) 0.6896(2) 0.2013(3) 0.0281(7) Uani 1 1 d . . . . .
C4 C 0.2404(6) 0.6893(2) 0.0999(3) 0.0317(7) Uani 1 1 d . . . . .
H4 H 0.2157 0.7418 0.0396 0.038 Uiso 1 1 calc R U . . .
C5 C 0.0774(6) 0.6120(2) 0.0891(3) 0.0318(7) Uani 1 1 d . . . . .
H5 H -0.0600 0.6111 0.0219 0.038 Uiso 1 1 calc R U . . .
C6 C 0.1190(5) 0.5350(2) 0.1794(3) 0.0266(7) Uani 1 1 d . . . . .
C7 C -0.0139(5) 0.4434(2) 0.1892(3) 0.0294(7) Uani 1 1 d . . . . .
C8 C 0.1302(5) 0.3866(2) 0.3105(3) 0.0266(7) Uani 1 1 d . . . . .
C9 C -0.0485(5) 0.3652(2) 0.4061(3) 0.0284(7) Uani 1 1 d . . . . .
C10 C 0.0871(5) 0.2162(2) 0.3431(3) 0.0288(7) Uani 1 1 d . . . . .
C11 C 0.2116(5) 0.2848(2) 0.2786(3) 0.0270(6) Uani 1 1 d . . . . .
C12 C 0.3794(6) 0.2534(2) 0.2027(3) 0.0321(7) Uani 1 1 d . . . . .
H12 H 0.4637 0.2992 0.1585 0.039 Uiso 1 1 calc R U . . .
C13 C 0.4204(6) 0.1530(3) 0.1935(3) 0.0392(8) Uani 1 1 d . . . . .
H13 H 0.5336 0.1301 0.1421 0.047 Uiso 1 1 calc R U . . .
C14 C 0.2959(6) 0.0853(3) 0.2594(3) 0.0394(8) Uani 1 1 d . . . . .
H14 H 0.3279 0.0174 0.2522 0.047 Uiso 1 1 calc R U . . .
C15 C 0.1258(6) 0.1154(3) 0.3353(3) 0.0358(8) Uani 1 1 d . . . . .
H15 H 0.0411 0.0697 0.3794 0.043 Uiso 1 1 calc R U . . .
C16 C -0.2124(6) 0.2172(3) 0.5027(3) 0.0385(8) Uani 1 1 d . . . . .
H16A H -0.1039 0.1798 0.5684 0.058 Uiso 1 1 calc R U . . .
H16B H -0.3305 0.1728 0.4527 0.058 Uiso 1 1 calc R U . . .
H16C H -0.2979 0.2668 0.5454 0.058 Uiso 1 1 calc R U . . .
C17 C 0.6160(6) 0.7754(2) 0.2207(3) 0.0347(8) Uani 1 1 d . . . . .
C18 C 0.7635(9) 0.9151(3) 0.1226(5) 0.0639(12) Uani 1 1 d . . . . .
H18A H 0.7091 0.9585 0.0488 0.096 Uiso 1 1 calc R U . . .
H18B H 0.9308 0.8945 0.1214 0.096 Uiso 1 1 calc R U . . .
H18C H 0.7557 0.9500 0.2037 0.096 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.214(4) . ?
O2 C9 1.222(4) . ?
O3 C17 1.189(4) . ?
O4 C17 1.319(4) . ?
O4 C18 1.446(4) . ?
N1 C1 1.372(4) . ?
N1 C8 1.456(4) . ?
N1 H1 0.8700 . ?
N2 C9 1.360(4) . ?
N2 C10 1.404(4) . ?
N2 C16 1.454(4) . ?
C1 C2 1.389(4) . ?
C1 C6 1.406(4) . ?
C2 C3 1.389(4) . ?
C2 H2 0.9400 . ?
C3 C4 1.406(4) . ?
C3 C17 1.491(4) . ?
C4 C5 1.373(4) . ?
C4 H4 0.9400 . ?
C5 C6 1.392(4) . ?
C5 H5 0.9400 . ?
C6 C7 1.453(4) . ?
C7 C8 1.569(4) . ?
C8 C11 1.503(4) . ?
C8 C9 1.541(4) . ?
C10 C15 1.384(5) . ?
C10 C11 1.392(4) . ?
C11 C12 1.382(4) . ?
C12 C13 1.383(5) . ?
C12 H12 0.9400 . ?
C13 C14 1.392(5) . ?
C13 H13 0.9400 . ?
C14 C15 1.387(5) . ?
C14 H14 0.9400 . ?
C15 H15 0.9400 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?

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
C17 O4 C18 116.8(3) . . ?
C1 N1 C8 110.5(2) . . ?
C1 N1 H1 124.8 . . ?
C8 N1 H1 124.8 . . ?
C9 N2 C10 111.4(3) . . ?
C9 N2 C16 123.3(3) . . ?
C10 N2 C16 124.8(3) . . ?
N1 C1 C2 127.7(3) . . ?
N1 C1 C6 112.1(3) . . ?
C2 C1 C6 120.2(3) . . ?
C3 C2 C1 117.8(3) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 122.1(3) . . ?
C2 C3 C17 116.8(3) . . ?
C4 C3 C17 121.1(3) . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 118.9(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 121.2(3) . . ?
C5 C6 C7 131.0(3) . . ?
C1 C6 C7 107.7(3) . . ?
O1 C7 C6 130.0(3) . . ?
O1 C7 C8 123.9(3) . . ?
C6 C7 C8 106.1(2) . . ?
N1 C8 C11 116.1(2) . . ?
N1 C8 C9 113.3(2) . . ?
C11 C8 C9 102.6(2) . . ?
N1 C8 C7 103.0(2) . . ?
C11 C8 C7 113.8(2) . . ?
C9 C8 C7 108.1(2) . . ?
O2 C9 N2 126.9(3) . . ?
O2 C9 C8 125.5(3) . . ?
N2 C9 C8 107.6(3) . . ?
C15 C10 C11 122.3(3) . . ?
C15 C10 N2 127.8(3) . . ?
C11 C10 N2 109.9(3) . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 C8 131.5(3) . . ?
C10 C11 C8 108.3(3) . . ?
C13 C12 C11 118.4(3) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C12 C13 C14 120.7(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 121.7(3) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C10 C15 C14 116.7(3) . . ?
C10 C15 H15 121.7 . . ?
C14 C15 H15 121.7 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 O4 123.3(3) . . ?
O3 C17 C3 124.3(3) . . ?
O4 C17 C3 112.4(3) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 -174.9(3) . . . . ?
C8 N1 C1 C6 7.8(3) . . . . ?
N1 C1 C2 C3 -176.0(3) . . . . ?
C6 C1 C2 C3 1.1(4) . . . . ?
C1 C2 C3 C4 -1.1(4) . . . . ?
C1 C2 C3 C17 175.8(3) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
C17 C3 C4 C5 -176.1(3) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C4 C5 C6 C7 -177.2(3) . . . . ?
N1 C1 C6 C5 176.9(3) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
N1 C1 C6 C7 -5.1(3) . . . . ?
C2 C1 C6 C7 177.3(3) . . . . ?
C5 C6 C7 O1 -0.8(6) . . . . ?
C1 C6 C7 O1 -178.6(3) . . . . ?
C5 C6 C7 C8 178.4(3) . . . . ?
C1 C6 C7 C8 0.6(3) . . . . ?
C1 N1 C8 C11 118.4(3) . . . . ?
C1 N1 C8 C9 -123.3(3) . . . . ?
C1 N1 C8 C7 -6.7(3) . . . . ?
O1 C7 C8 N1 -177.1(3) . . . . ?
C6 C7 C8 N1 3.6(3) . . . . ?
O1 C7 C8 C11 56.3(4) . . . . ?
C6 C7 C8 C11 -123.0(3) . . . . ?
O1 C7 C8 C9 -57.0(4) . . . . ?
C6 C7 C8 C9 123.7(3) . . . . ?
C10 N2 C9 O2 -178.2(3) . . . . ?
C16 N2 C9 O2 -6.0(5) . . . . ?
C10 N2 C9 C8 4.0(3) . . . . ?
C16 N2 C9 C8 176.2(2) . . . . ?
N1 C8 C9 O2 52.5(4) . . . . ?
C11 C8 C9 O2 178.4(3) . . . . ?
C7 C8 C9 O2 -61.1(4) . . . . ?
N1 C8 C9 N2 -129.7(3) . . . . ?
C11 C8 C9 N2 -3.8(3) . . . . ?
C7 C8 C9 N2 116.8(3) . . . . ?
C9 N2 C10 C15 176.0(3) . . . . ?
C16 N2 C10 C15 3.9(5) . . . . ?
C9 N2 C10 C11 -2.6(3) . . . . ?
C16 N2 C10 C11 -174.6(3) . . . . ?
C15 C10 C11 C12 0.5(4) . . . . ?
N2 C10 C11 C12 179.1(2) . . . . ?
C15 C10 C11 C8 -178.7(3) . . . . ?
N2 C10 C11 C8 -0.1(3) . . . . ?
N1 C8 C11 C12 -52.7(4) . . . . ?
C9 C8 C11 C12 -176.8(3) . . . . ?
C7 C8 C11 C12 66.7(4) . . . . ?
N1 C8 C11 C10 126.3(3) . . . . ?
C9 C8 C11 C10 2.3(3) . . . . ?
C7 C8 C11 C10 -114.3(3) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C8 C11 C12 C13 178.6(3) . . . . ?
C11 C12 C13 C14 -0.2(5) . . . . ?
C12 C13 C14 C15 0.5(5) . . . . ?
C11 C10 C15 C14 -0.1(5) . . . . ?
N2 C10 C15 C14 -178.5(3) . . . . ?
C13 C14 C15 C10 -0.4(5) . . . . ?
C18 O4 C17 O3 0.7(6) . . . . ?
C18 O4 C17 C3 179.0(3) . . . . ?
C2 C3 C17 O3 -20.6(5) . . . . ?
C4 C3 C17 O3 156.3(4) . . . . ?
C2 C3 C17 O4 161.1(3) . . . . ?
C4 C3 C17 O4 -21.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C15 H15 O2 0.94 2.55 3.293(4) 136.2 2_546
N1 H1 O2 0.87 2.30 2.911(3) 127.0 1_655

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_d8v23376
_database_code_depnum_ccdc_archive 'CCDC 2280225'
loop_
_audit_author_name
_audit_author_address
'Qiongwen Kang'
;East China Normal University
China
;
_audit_update_record             
;
2023-07-08 deposited with the CCDC.	2024-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H26 N4 O4'
_chemical_formula_weight         530.57

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

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

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

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

_cell_length_a                   12.3359(8)
_cell_length_b                   19.7652(13)
_cell_length_c                   12.0310(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.454(2)
_cell_angle_gamma                90
_cell_volume                     2765.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5251
_cell_measurement_theta_min      4.586
_cell_measurement_theta_max      50.676

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6255
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            20565
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.074
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5121
_reflns_number_gt                3298
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0702P)²+1.1244P] 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     SHELXL
_refine_ls_extinction_coef       0.016(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5121
_refine_ls_number_parameters     364
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.1792
_refine_ls_wR_factor_gt          0.1508
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.54420(18) 0.70626(11) 0.36471(17) 0.0552(6) Uani 1 1 d . . . . .
O2 O 0.62132(18) 0.60993(11) 0.72313(18) 0.0578(6) Uani 1 1 d . . . . .
O3 O 0.76047(19) 0.80921(11) 0.5396(2) 0.0668(7) Uani 1 1 d . . . . .
O4 O 0.76893(18) 0.76866(12) 0.78269(19) 0.0615(6) Uani 1 1 d . . . . .
N1 N 0.54105(18) 0.74903(11) 0.64629(19) 0.0409(6) Uani 1 1 d . . . . .
H1 H 0.5649 0.7661 0.7160 0.049 Uiso 1 1 calc R U . . .
N2 N 0.76325(19) 0.67256(12) 0.5341(2) 0.0451(6) Uani 1 1 d . . . . .
H2 H 0.8089 0.6985 0.5131 0.054 Uiso 1 1 calc R U . . .
N3 N 0.6095(2) 0.86911(12) 0.5479(2) 0.0497(6) Uani 1 1 d . . . . .
N4 N 0.8939(2) 0.68456(15) 0.7940(2) 0.0631(8) Uani 1 1 d . . . . .
C1 C 0.4332(2) 0.72486(14) 0.5935(2) 0.0398(7) Uani 1 1 d . . . . .
C2 C 0.3411(2) 0.72240(15) 0.6370(3) 0.0486(7) Uani 1 1 d . . . . .
H2A H 0.3496 0.7365 0.7132 0.058 Uiso 1 1 calc R U . . .
C3 C 0.2377(3) 0.69840(17) 0.5630(3) 0.0597(9) Uani 1 1 d . . . . .
H3 H 0.1754 0.6970 0.5902 0.072 Uiso 1 1 calc R U . . .
C4 C 0.2223(3) 0.67603(18) 0.4489(3) 0.0624(9) Uani 1 1 d . . . . .
H4 H 0.1511 0.6597 0.4019 0.075 Uiso 1 1 calc R U . . .
C5 C 0.3117(3) 0.67808(16) 0.4060(3) 0.0529(8) Uani 1 1 d . . . . .
H5 H 0.3022 0.6635 0.3299 0.063 Uiso 1 1 calc R U . . .
C6 C 0.4174(2) 0.70247(14) 0.4788(2) 0.0416(7) Uani 1 1 d . . . . .
C7 C 0.5232(2) 0.71480(14) 0.4561(2) 0.0405(7) Uani 1 1 d . . . . .
C8 C 0.6108(2) 0.74290(14) 0.5724(2) 0.0390(7) Uani 1 1 d . . . . .
C9 C 0.6653(3) 0.81014(15) 0.5511(3) 0.0462(7) Uani 1 1 d . . . . .
C10 C 0.4886(3) 0.87691(15) 0.5298(3) 0.0490(8) Uani 1 1 d . . . . .
C11 C 0.4109(3) 0.86815(17) 0.4182(3) 0.0667(10) Uani 1 1 d . . . . .
H11 H 0.4360 0.8549 0.3566 0.080 Uiso 1 1 calc R U . . .
C12 C 0.2961(3) 0.8791(2) 0.3986(4) 0.0858(13) Uani 1 1 d . . . . .
H12 H 0.2433 0.8722 0.3236 0.103 Uiso 1 1 calc R U . . .
C13 C 0.2584(3) 0.8998(2) 0.4869(5) 0.0862(13) Uani 1 1 d . . . . .
H13 H 0.1804 0.9072 0.4726 0.103 Uiso 1 1 calc R U . . .
C14 C 0.3375(3) 0.90989(19) 0.5990(4) 0.0768(11) Uani 1 1 d . . . . .
H14 H 0.3123 0.9246 0.6596 0.092 Uiso 1 1 calc R U . . .
C15 C 0.4526(3) 0.89819(16) 0.6207(3) 0.0573(8) Uani 1 1 d . . . . .
H15 H 0.5054 0.9046 0.6958 0.069 Uiso 1 1 calc R U . . .
C16 C 0.6677(3) 0.93094(16) 0.5294(3) 0.0696(10) Uani 1 1 d . . . . .
H16A H 0.6582 0.9354 0.4472 0.104 Uiso 1 1 calc R U . . .
H16B H 0.7482 0.9282 0.5742 0.104 Uiso 1 1 calc R U . . .
H16C H 0.6348 0.9696 0.5546 0.104 Uiso 1 1 calc R U . . .
C17 C 0.7290(2) 0.60921(15) 0.4889(2) 0.0444(7) Uani 1 1 d . . . . .
C18 C 0.7451(3) 0.57914(17) 0.3905(3) 0.0556(8) Uani 1 1 d . . . . .
H18 H 0.7811 0.6022 0.3451 0.067 Uiso 1 1 calc R U . . .
C19 C 0.7054(3) 0.51401(18) 0.3634(3) 0.0667(10) Uani 1 1 d . . . . .
H19 H 0.7142 0.4932 0.2976 0.080 Uiso 1 1 calc R U . . .
C20 C 0.6530(3) 0.47853(18) 0.4304(3) 0.0697(10) Uani 1 1 d . . . . .
H20 H 0.6277 0.4345 0.4094 0.084 Uiso 1 1 calc R U . . .
C21 C 0.6379(3) 0.50763(16) 0.5277(3) 0.0579(8) Uani 1 1 d . . . . .
H21 H 0.6049 0.4834 0.5746 0.069 Uiso 1 1 calc R U . . .
C22 C 0.6732(2) 0.57444(15) 0.5546(2) 0.0457(7) Uani 1 1 d . . . . .
C23 C 0.6612(2) 0.61998(15) 0.6444(2) 0.0440(7) Uani 1 1 d . . . . .
C24 C 0.7114(2) 0.68929(14) 0.6223(2) 0.0406(7) Uani 1 1 d . . . . .
C25 C 0.7948(2) 0.71784(16) 0.7394(3) 0.0477(7) Uani 1 1 d . . . . .
C26 C 0.9253(3) 0.61869(19) 0.7634(3) 0.0612(9) Uani 1 1 d . . . . .
C27 C 0.9003(3) 0.5622(2) 0.8165(4) 0.0953(14) Uani 1 1 d . . . . .
H27 H 0.8597 0.5659 0.8690 0.114 Uiso 1 1 calc R U . . .
C28 C 0.9367(5) 0.4990(3) 0.7908(7) 0.136(2) Uani 1 1 d . . . . .
H28 H 0.9204 0.4601 0.8259 0.163 Uiso 1 1 calc R U . . .
C29 C 0.9962(5) 0.4947(4) 0.7141(8) 0.143(3) Uani 1 1 d . . . . .
H29 H 1.0206 0.4526 0.6974 0.172 Uiso 1 1 calc R U . . .
C30 C 1.0205(4) 0.5501(4) 0.6617(5) 0.117(2) Uani 1 1 d . . . . .
H30 H 1.0600 0.5461 0.6083 0.141 Uiso 1 1 calc R U . . .
C31 C 0.9866(3) 0.6126(2) 0.6878(3) 0.0793(12) Uani 1 1 d . . . . .
H31 H 1.0055 0.6511 0.6538 0.095 Uiso 1 1 calc R U . . .
C32 C 0.9684(3) 0.7116(2) 0.9080(4) 0.0944(14) Uani 1 1 d . . . . .
H32A H 0.9608 0.7599 0.9084 0.142 Uiso 1 1 calc R U . . .
H32B H 1.0469 0.6999 0.9195 0.142 Uiso 1 1 calc R U . . .
H32C H 0.9459 0.6925 0.9705 0.142 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.222(3) . ?
O2 C23 1.220(3) . ?
O3 C9 1.228(3) . ?
O4 C25 1.222(3) . ?
N1 C1 1.356(3) . ?
N1 C8 1.433(3) . ?
N1 H1 0.8600 . ?
N2 C17 1.375(4) . ?
N2 C24 1.448(3) . ?
N2 H2 0.8600 . ?
N3 C9 1.347(4) . ?
N3 C10 1.442(4) . ?
N3 C16 1.472(4) . ?
N4 C25 1.350(4) . ?
N4 C26 1.441(4) . ?
N4 C32 1.474(4) . ?
C1 C6 1.399(4) . ?
C1 C2 1.401(4) . ?
C2 C3 1.374(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.394(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.441(4) . ?
C7 C8 1.558(4) . ?
C8 C9 1.549(4) . ?
C8 C24 1.590(4) . ?
C10 C11 1.376(4) . ?
C10 C15 1.376(4) . ?
C11 C12 1.374(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.357(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.390(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C22 1.391(4) . ?
C17 C18 1.396(4) . ?
C18 C19 1.377(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.381(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.372(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.394(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.451(4) . ?
C23 C24 1.563(4) . ?
C24 C25 1.548(4) . ?
C26 C31 1.368(5) . ?
C26 C27 1.372(5) . ?
C27 C28 1.396(7) . ?
C27 H27 0.9300 . ?
C28 C29 1.360(9) . ?
C28 H28 0.9300 . ?
C29 C30 1.346(8) . ?
C29 H29 0.9300 . ?
C30 C31 1.373(6) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 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
C1 N1 C8 112.2(2) . . ?
C1 N1 H1 123.9 . . ?
C8 N1 H1 123.9 . . ?
C17 N2 C24 110.2(2) . . ?
C17 N2 H2 124.9 . . ?
C24 N2 H2 124.9 . . ?
C9 N3 C10 126.1(2) . . ?
C9 N3 C16 116.9(2) . . ?
C10 N3 C16 114.9(2) . . ?
C25 N4 C26 126.4(3) . . ?
C25 N4 C32 117.3(3) . . ?
C26 N4 C32 115.3(3) . . ?
N1 C1 C6 111.5(2) . . ?
N1 C1 C2 128.9(3) . . ?
C6 C1 C2 119.6(3) . . ?
C3 C2 C1 117.6(3) . . ?
C3 C2 H2A 121.2 . . ?
C1 C2 H2A 121.2 . . ?
C2 C3 C4 122.7(3) . . ?
C2 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 118.5(3) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C5 C6 C1 121.6(3) . . ?
C5 C6 C7 131.1(3) . . ?
C1 C6 C7 107.2(2) . . ?
O1 C7 C6 128.6(3) . . ?
O1 C7 C8 124.5(2) . . ?
C6 C7 C8 106.9(2) . . ?
N1 C8 C9 114.4(2) . . ?
N1 C8 C7 102.0(2) . . ?
C9 C8 C7 111.5(2) . . ?
N1 C8 C24 112.1(2) . . ?
C9 C8 C24 107.9(2) . . ?
C7 C8 C24 108.8(2) . . ?
O3 C9 N3 120.5(3) . . ?
O3 C9 C8 119.4(3) . . ?
N3 C9 C8 120.1(2) . . ?
C11 C10 C15 120.6(3) . . ?
C11 C10 N3 118.9(3) . . ?
C15 C10 N3 120.2(3) . . ?
C12 C11 C10 119.4(4) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C13 C12 C11 121.1(4) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 119.3(4) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 120.5(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C10 119.1(3) . . ?
C14 C15 H15 120.5 . . ?
C10 C15 H15 120.5 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 C22 111.7(2) . . ?
N2 C17 C18 127.7(3) . . ?
C22 C17 C18 120.6(3) . . ?
C19 C18 C17 117.3(3) . . ?
C19 C18 H18 121.3 . . ?
C17 C18 H18 121.3 . . ?
C18 C19 C20 122.3(3) . . ?
C18 C19 H19 118.8 . . ?
C20 C19 H19 118.8 . . ?
C21 C20 C19 120.6(3) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 118.3(3) . . ?
C20 C21 H21 120.8 . . ?
C22 C21 H21 120.8 . . ?
C17 C22 C21 120.8(3) . . ?
C17 C22 C23 108.0(3) . . ?
C21 C22 C23 131.2(3) . . ?
O2 C23 C22 130.1(3) . . ?
O2 C23 C24 124.1(3) . . ?
C22 C23 C24 105.8(2) . . ?
N2 C24 C25 115.3(2) . . ?
N2 C24 C23 102.8(2) . . ?
C25 C24 C23 110.2(2) . . ?
N2 C24 C8 110.8(2) . . ?
C25 C24 C8 107.4(2) . . ?
C23 C24 C8 110.1(2) . . ?
O4 C25 N4 121.1(3) . . ?
O4 C25 C24 119.9(3) . . ?
N4 C25 C24 119.0(3) . . ?
C31 C26 C27 119.8(4) . . ?
C31 C26 N4 120.3(4) . . ?
C27 C26 N4 119.7(4) . . ?
C26 C27 C28 119.1(5) . . ?
C26 C27 H27 120.4 . . ?
C28 C27 H27 120.4 . . ?
C29 C28 C27 119.5(6) . . ?
C29 C28 H28 120.3 . . ?
C27 C28 H28 120.3 . . ?
C30 C29 C28 121.5(6) . . ?
C30 C29 H29 119.3 . . ?
C28 C29 H29 119.3 . . ?
C29 C30 C31 119.5(6) . . ?
C29 C30 H30 120.3 . . ?
C31 C30 H30 120.3 . . ?
C26 C31 C30 120.6(5) . . ?
C26 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
N4 C32 H32A 109.5 . . ?
N4 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
N4 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C6 -2.1(3) . . . . ?
C8 N1 C1 C2 -179.7(3) . . . . ?
N1 C1 C2 C3 176.7(3) . . . . ?
C6 C1 C2 C3 -0.7(4) . . . . ?
C1 C2 C3 C4 0.9(5) . . . . ?
C2 C3 C4 C5 -0.7(5) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C4 C5 C6 C7 -175.3(3) . . . . ?
N1 C1 C6 C5 -177.4(3) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
N1 C1 C6 C7 -1.3(3) . . . . ?
C2 C1 C6 C7 176.5(2) . . . . ?
C5 C6 C7 O1 0.0(5) . . . . ?
C1 C6 C7 O1 -175.5(3) . . . . ?
C5 C6 C7 C8 179.4(3) . . . . ?
C1 C6 C7 C8 3.9(3) . . . . ?
C1 N1 C8 C9 124.8(2) . . . . ?
C1 N1 C8 C7 4.3(3) . . . . ?
C1 N1 C8 C24 -112.0(2) . . . . ?
O1 C7 C8 N1 174.6(3) . . . . ?
C6 C7 C8 N1 -4.9(3) . . . . ?
O1 C7 C8 C9 52.1(4) . . . . ?
C6 C7 C8 C9 -127.4(2) . . . . ?
O1 C7 C8 C24 -66.8(3) . . . . ?
C6 C7 C8 C24 113.8(2) . . . . ?
C10 N3 C9 O3 162.9(3) . . . . ?
C16 N3 C9 O3 0.4(4) . . . . ?
C10 N3 C9 C8 -18.5(4) . . . . ?
C16 N3 C9 C8 179.0(3) . . . . ?
N1 C8 C9 O3 146.7(3) . . . . ?
C7 C8 C9 O3 -98.2(3) . . . . ?
C24 C8 C9 O3 21.1(4) . . . . ?
N1 C8 C9 N3 -31.9(4) . . . . ?
C7 C8 C9 N3 83.2(3) . . . . ?
C24 C8 C9 N3 -157.4(2) . . . . ?
C9 N3 C10 C11 -75.0(4) . . . . ?
C16 N3 C10 C11 87.8(4) . . . . ?
C9 N3 C10 C15 110.3(3) . . . . ?
C16 N3 C10 C15 -86.9(4) . . . . ?
C15 C10 C11 C12 -1.8(5) . . . . ?
N3 C10 C11 C12 -176.4(3) . . . . ?
C10 C11 C12 C13 1.5(6) . . . . ?
C11 C12 C13 C14 -0.2(6) . . . . ?
C12 C13 C14 C15 -0.8(6) . . . . ?
C13 C14 C15 C10 0.5(5) . . . . ?
C11 C10 C15 C14 0.8(5) . . . . ?
N3 C10 C15 C14 175.4(3) . . . . ?
C24 N2 C17 C22 -11.3(3) . . . . ?
C24 N2 C17 C18 169.1(3) . . . . ?
N2 C17 C18 C19 178.5(3) . . . . ?
C22 C17 C18 C19 -1.1(4) . . . . ?
C17 C18 C19 C20 -0.9(5) . . . . ?
C18 C19 C20 C21 0.3(5) . . . . ?
C19 C20 C21 C22 2.1(5) . . . . ?
N2 C17 C22 C21 -176.0(3) . . . . ?
C18 C17 C22 C21 3.6(4) . . . . ?
N2 C17 C22 C23 4.9(3) . . . . ?
C18 C17 C22 C23 -175.4(3) . . . . ?
C20 C21 C22 C17 -4.1(4) . . . . ?
C20 C21 C22 C23 174.7(3) . . . . ?
C17 C22 C23 O2 -177.2(3) . . . . ?
C21 C22 C23 O2 3.9(5) . . . . ?
C17 C22 C23 C24 2.8(3) . . . . ?
C21 C22 C23 C24 -176.1(3) . . . . ?
C17 N2 C24 C25 132.0(3) . . . . ?
C17 N2 C24 C23 12.0(3) . . . . ?
C17 N2 C24 C8 -105.6(2) . . . . ?
O2 C23 C24 N2 171.2(3) . . . . ?
C22 C23 C24 N2 -8.8(3) . . . . ?
O2 C23 C24 C25 47.7(3) . . . . ?
C22 C23 C24 C25 -132.3(2) . . . . ?
O2 C23 C24 C8 -70.7(3) . . . . ?
C22 C23 C24 C8 109.3(2) . . . . ?
N1 C8 C24 N2 166.7(2) . . . . ?
C9 C8 C24 N2 -66.4(3) . . . . ?
C7 C8 C24 N2 54.7(3) . . . . ?
N1 C8 C24 C25 -66.4(3) . . . . ?
C9 C8 C24 C25 60.4(3) . . . . ?
C7 C8 C24 C25 -178.5(2) . . . . ?
N1 C8 C24 C23 53.7(3) . . . . ?
C9 C8 C24 C23 -179.5(2) . . . . ?
C7 C8 C24 C23 -58.4(3) . . . . ?
C26 N4 C25 O4 168.7(3) . . . . ?
C32 N4 C25 O4 0.7(5) . . . . ?
C26 N4 C25 C24 -9.1(5) . . . . ?
C32 N4 C25 C24 -177.2(3) . . . . ?
N2 C24 C25 O4 132.5(3) . . . . ?
C23 C24 C25 O4 -111.7(3) . . . . ?
C8 C24 C25 O4 8.3(4) . . . . ?
N2 C24 C25 N4 -49.7(4) . . . . ?
C23 C24 C25 N4 66.2(3) . . . . ?
C8 C24 C25 N4 -173.8(3) . . . . ?
C25 N4 C26 C31 92.6(4) . . . . ?
C32 N4 C26 C31 -99.1(4) . . . . ?
C25 N4 C26 C27 -91.8(4) . . . . ?
C32 N4 C26 C27 76.5(4) . . . . ?
C31 C26 C27 C28 -1.0(6) . . . . ?
N4 C26 C27 C28 -176.6(4) . . . . ?
C26 C27 C28 C29 0.1(8) . . . . ?
C27 C28 C29 C30 -0.3(9) . . . . ?
C28 C29 C30 C31 1.3(9) . . . . ?
C27 C26 C31 C30 1.9(5) . . . . ?
N4 C26 C31 C30 177.6(3) . . . . ?
C29 C30 C31 C26 -2.1(7) . . . . ?

_refine_diff_density_max         0.565
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.042

_shelxl_version_number           2013-4



