# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_116-xd
_database_code_depnum_ccdc_archive 'CCDC 2299096'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2023-10-04 deposited with the CCDC.	2023-12-21 downloaded from the CCDC.
;
_audit_creation_date             2021-10-29
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H15 Br N2 O4'
_chemical_formula_sum            'C13 H15 Br N2 O4'
_chemical_formula_weight         343.18
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.5005(19)
_cell_length_b                   7.9603(6)
_cell_length_c                   18.992(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.951(13)
_cell_angle_gamma                90
_cell_volume                     2753.2(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1969
_cell_measurement_temperature    220.00(10)
_cell_measurement_theta_max      27.5600
_cell_measurement_theta_min      2.5880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.001
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5471
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.237
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      220.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  68.00   1.00    5.00    --   12.05  19.00  60.00   85
  2  ω    -10.00  85.00   1.00    5.00    --   12.05  38.00 120.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0301283500
_diffrn_orient_matrix_UB_12      0.0266198500
_diffrn_orient_matrix_UB_13      -0.0319489000
_diffrn_orient_matrix_UB_21      -0.0242384500
_diffrn_orient_matrix_UB_22      -0.0168076500
_diffrn_orient_matrix_UB_23      0.0194912000
_diffrn_orient_matrix_UB_31      0.0046589500
_diffrn_orient_matrix_UB_32      0.0833552500
_diffrn_orient_matrix_UB_33      0.0140641000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1903
_reflns_number_total             2432
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2432
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0303P)²+4.7930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0853
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C6(H6), C12(H12)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br1 Br 0.51195(2) 0.74678(4) 0.52360(2) 0.03592(14) Uani 1 1 d . . . . .
O1 O 0.58506(19) 0.2017(4) 0.72039(19) 0.0717(10) Uani 1 1 d . . . . .
O2 O 0.66346(13) 0.5281(3) 0.45160(13) 0.0332(6) Uani 1 1 d . . . . .
H2 H 0.667860 0.425622 0.454568 0.050 Uiso 1 1 calc R U . . .
O3 O 0.63095(14) 1.1818(3) 0.43465(15) 0.0421(7) Uani 1 1 d . . . . .
O4 O 0.70604(14) 1.1774(3) 0.55016(16) 0.0422(7) Uani 1 1 d . . . . .
N1 N 0.68502(14) 0.6795(3) 0.56182(15) 0.0275(6) Uani 1 1 d . . . . .
N2 N 0.66332(16) 1.1045(4) 0.49406(19) 0.0334(7) Uani 1 1 d . . . . .
C1 C 0.6170(2) 0.3512(5) 0.7190(2) 0.0484(10) Uani 1 1 d . . . . .
C2 C 0.6078(3) 0.4731(7) 0.7657(2) 0.0632(13) Uani 1 1 d . . . . .
H2A H 0.579790 0.450473 0.795193 0.076 Uiso 1 1 calc R U . . .
C3 C 0.6392(3) 0.6266(7) 0.7693(2) 0.0657(13) Uani 1 1 d . . . . .
H3 H 0.633163 0.708268 0.801631 0.079 Uiso 1 1 calc R U . . .
C4 C 0.6793(2) 0.6602(5) 0.7258(2) 0.0495(11) Uani 1 1 d . . . . .
H4 H 0.700745 0.765556 0.728539 0.059 Uiso 1 1 calc R U . . .
C5 C 0.68888(19) 0.5417(5) 0.67775(19) 0.0346(9) Uani 1 1 d . . . . .
C6 C 0.65806(19) 0.3846(5) 0.67426(19) 0.0372(9) Uani 1 1 d . . . . .
H6 H 0.664729 0.302451 0.642476 0.045 Uiso 1 1 calc R U . . .
C7 C 0.73016(19) 0.5850(5) 0.62758(19) 0.0360(9) Uani 1 1 d . . . . .
H7A H 0.773054 0.650998 0.655667 0.043 Uiso 1 1 calc R U . . .
H7B H 0.746920 0.482545 0.611264 0.043 Uiso 1 1 calc R U . . .
C8 C 0.63101(17) 0.5844(4) 0.50211(18) 0.0263(8) Uani 1 1 d . . . . .
H8 H 0.613644 0.488527 0.523512 0.032 Uiso 1 1 calc R U . . .
C9 C 0.56732(17) 0.6951(4) 0.45865(19) 0.0259(7) Uani 1 1 d . . . . .
H9 H 0.535357 0.632513 0.414734 0.031 Uiso 1 1 calc R U . . .
C10 C 0.59204(18) 0.8538(4) 0.4314(2) 0.0309(8) Uani 1 1 d . . . . .
H10A H 0.610874 0.827545 0.391846 0.037 Uiso 1 1 calc R U . . .
H10B H 0.550911 0.930184 0.411102 0.037 Uiso 1 1 calc R U . . .
C11 C 0.64995(18) 0.9327(4) 0.4956(2) 0.0277(8) Uani 1 1 d . . . . .
C12 C 0.69183(18) 0.8436(4) 0.5556(2) 0.0279(8) Uani 1 1 d . . . . .
H12 H 0.727357 0.900024 0.594656 0.034 Uiso 1 1 calc R U . . .
C13 C 0.6011(2) 0.0729(6) 0.6834(3) 0.0615(13) Uani 1 1 d . . . . .
H13A H 0.582997 0.096518 0.630284 0.092 Uiso 1 1 calc R U . . .
H13B H 0.578363 -0.027662 0.692494 0.092 Uiso 1 1 calc R U . . .
H13C H 0.653337 0.057555 0.700803 0.092 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
Br1 C9 1.952(3) . ?
O1 C1 1.348(5) . ?
O1 C13 1.342(5) . ?
O2 H2 0.8200 . ?
O2 C8 1.398(4) . ?
O3 N2 1.241(4) . ?
O4 N2 1.237(4) . ?
N1 C7 1.454(4) . ?
N1 C8 1.454(4) . ?
N1 C12 1.322(4) . ?
N2 C11 1.394(4) . ?
C1 C2 1.368(6) . ?
C1 C6 1.386(5) . ?
C2 H2A 0.9300 . ?
C2 C3 1.357(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.352(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.371(5) . ?
C5 C6 1.379(5) . ?
C5 C7 1.491(5) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8 0.9800 . ?
C8 C9 1.506(4) . ?
C9 H9 0.9800 . ?
C9 C10 1.508(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.473(5) . ?
C11 C12 1.343(5) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C13 O1 C1 118.0(4) . . ?
C8 O2 H2 109.5 . . ?
C7 N1 C8 116.6(3) . . ?
C12 N1 C7 122.6(3) . . ?
C12 N1 C8 120.8(3) . . ?
O3 N2 C11 117.8(3) . . ?
O4 N2 O3 121.1(3) . . ?
O4 N2 C11 121.1(3) . . ?
O1 C1 C2 116.4(4) . . ?
O1 C1 C6 123.6(4) . . ?
C2 C1 C6 120.0(4) . . ?
C1 C2 H2A 119.6 . . ?
C3 C2 C1 120.7(4) . . ?
C3 C2 H2A 119.6 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.7(4) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.1(4) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 119.7(4) . . ?
C4 C5 C7 120.0(4) . . ?
C6 C5 C7 120.3(3) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 C1 118.8(4) . . ?
C5 C6 H6 120.6 . . ?
N1 C7 C5 111.7(3) . . ?
N1 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
C5 C7 H7A 109.3 . . ?
C5 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
O2 C8 N1 108.8(2) . . ?
O2 C8 H8 110.1 . . ?
O2 C8 C9 107.4(3) . . ?
N1 C8 H8 110.1 . . ?
N1 C8 C9 110.4(3) . . ?
C9 C8 H8 110.1 . . ?
Br1 C9 H9 108.5 . . ?
C8 C9 Br1 108.1(2) . . ?
C8 C9 H9 108.5 . . ?
C8 C9 C10 112.1(3) . . ?
C10 C9 Br1 110.9(2) . . ?
C10 C9 H9 108.5 . . ?
C9 C10 H10A 110.0 . . ?
C9 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
C11 C10 C9 108.6(3) . . ?
C11 C10 H10A 110.0 . . ?
C11 C10 H10B 110.0 . . ?
N2 C11 C10 119.7(3) . . ?
C12 C11 N2 118.3(3) . . ?
C12 C11 C10 122.0(3) . . ?
N1 C12 C11 123.2(3) . . ?
N1 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
Br1 C9 C10 C11 70.7(3) . . . . ?
O1 C1 C2 C3 178.6(4) . . . . ?
O1 C1 C6 C5 -179.4(3) . . . . ?
O2 C8 C9 Br1 171.28(19) . . . . ?
O2 C8 C9 C10 -66.1(3) . . . . ?
O3 N2 C11 C10 -7.7(4) . . . . ?
O3 N2 C11 C12 171.1(3) . . . . ?
O4 N2 C11 C10 172.3(3) . . . . ?
O4 N2 C11 C12 -8.9(5) . . . . ?
N1 C8 C9 Br1 -70.3(3) . . . . ?
N1 C8 C9 C10 52.3(3) . . . . ?
N2 C11 C12 N1 -178.2(3) . . . . ?
C1 C2 C3 C4 0.7(7) . . . . ?
C2 C1 C6 C5 -0.2(6) . . . . ?
C2 C3 C4 C5 0.1(7) . . . . ?
C3 C4 C5 C6 -0.9(6) . . . . ?
C3 C4 C5 C7 176.9(4) . . . . ?
C4 C5 C6 C1 1.0(5) . . . . ?
C4 C5 C7 N1 -79.0(4) . . . . ?
C6 C1 C2 C3 -0.6(7) . . . . ?
C6 C5 C7 N1 98.8(4) . . . . ?
C7 N1 C8 O2 -89.7(3) . . . . ?
C7 N1 C8 C9 152.7(3) . . . . ?
C7 N1 C12 C11 -179.2(3) . . . . ?
C7 C5 C6 C1 -176.8(3) . . . . ?
C8 N1 C7 C5 -76.5(4) . . . . ?
C8 N1 C12 C11 0.7(5) . . . . ?
C8 C9 C10 C11 -50.3(4) . . . . ?
C9 C10 C11 N2 -156.6(3) . . . . ?
C9 C10 C11 C12 24.7(4) . . . . ?
C10 C11 C12 N1 0.5(5) . . . . ?
C12 N1 C7 C5 103.4(4) . . . . ?
C12 N1 C8 O2 90.4(3) . . . . ?
C12 N1 C8 C9 -27.2(4) . . . . ?
C13 O1 C1 C2 -171.1(4) . . . . ?
C13 O1 C1 C6 8.1(6) . . . . ?

_olex2_date_sample_data_collection 2021-10-29
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.322
_oxdiff_exptl_absorpt_empirical_full_min 0.780
####################################################################### 
# 
# 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_37-1
_database_code_depnum_ccdc_archive 'CCDC 2299098'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2023-10-04 deposited with the CCDC.	2023-12-21 downloaded from the CCDC.
;
_audit_creation_date             2023-04-06
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H13 Br N2 O3'
_chemical_formula_sum            'C13 H13 Br N2 O3'
_chemical_formula_weight         325.16
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.5757(3)
_cell_length_b                   12.8565(3)
_cell_length_c                   10.0965(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.417(3)
_cell_angle_gamma                90
_cell_volume                     1277.99(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3966
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.3930
_cell_measurement_theta_min      4.4810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.455
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4547
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.571
_diffrn_reflns_theta_min         4.491
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -91.00 -19.00   1.00    1.00    --  -40.92 -37.00-150.00   72
  2  ω    -91.00  -9.00   1.00    1.00    --  -40.92 -77.00 -30.00   82
  3  ω     59.00  97.00   1.00    1.00    --   40.92-125.00-180.00   38
  4  ω     32.00 102.00   1.00    1.00    --  107.58 -94.00-180.00   70
  5  ω     32.00 118.00   1.00    1.00    --  107.58 -30.00-180.00   86
  6  ω     32.00 136.00   1.00    1.00    --  107.58 -30.00 -90.00  104
  7  ω     34.00  64.00   1.00    1.00    --  107.58 -77.00 120.00   30
  8  ω     30.00 105.00   1.00    1.00    --  107.58 -94.00  90.00   75
  9  ω    106.00 135.00   1.00    1.00    --  107.58 -77.00 120.00   29
 10  ω    123.00 148.00   1.00    1.00    --  107.58 125.00  30.00   25
 11  ω   -112.00 -74.00   1.00    1.00    --  -40.92-151.00 -61.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0593370000
_diffrn_orient_matrix_UB_12      0.0923629000
_diffrn_orient_matrix_UB_13      0.1006372000
_diffrn_orient_matrix_UB_21      0.0915422000
_diffrn_orient_matrix_UB_22      -0.0752483000
_diffrn_orient_matrix_UB_23      0.1133883000
_diffrn_orient_matrix_UB_31      0.1122635000
_diffrn_orient_matrix_UB_32      0.0125640000
_diffrn_orient_matrix_UB_33      -0.0622182000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2399
_reflns_number_total             2498
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.339
_refine_diff_density_min         -1.956
_refine_diff_density_rms         0.304
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2498
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0681
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1738P)²+1.2875P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2046
_refine_ls_wR_factor_ref         0.2098
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br1 Br 0.41256(4) 0.73417(4) 0.33498(4) 0.0222(3) Uani 1 1 d . . . . .
O1 O 0.6671(3) 0.5831(2) 0.1796(3) 0.0170(6) Uani 1 1 d . . . . .
O2 O 0.2847(3) 0.3395(3) 0.2651(4) 0.0292(8) Uani 1 1 d . . . . .
O3 O 0.1676(3) 0.4383(3) 0.0872(4) 0.0328(8) Uani 1 1 d . . . . .
N1 N 0.6079(3) 0.5302(3) 0.3734(3) 0.0131(7) Uani 1 1 d . . . . .
N2 N 0.2750(3) 0.4171(3) 0.1904(4) 0.0205(8) Uani 1 1 d . . . . .
C1 C 0.8557(4) 0.4636(3) 0.3082(4) 0.0173(8) Uani 1 1 d . . . . .
C2 C 0.9390(4) 0.4000(4) 0.2625(5) 0.0238(10) Uani 1 1 d . . . . .
H2 H 0.962318 0.421353 0.184195 0.029 Uiso 1 1 calc R U . . .
C3 C 0.9884(4) 0.3058(4) 0.3300(5) 0.0277(10) Uani 1 1 d . . . . .
H3 H 1.045788 0.263949 0.298280 0.033 Uiso 1 1 calc R U . . .
C4 C 0.9542(5) 0.2734(4) 0.4418(6) 0.0272(11) Uani 1 1 d . . . . .
H4 H 0.988793 0.209468 0.487886 0.033 Uiso 1 1 calc R U . . .
C5 C 0.8691(4) 0.3339(4) 0.4883(4) 0.0206(8) Uani 1 1 d . . . . .
H5 H 0.843159 0.309868 0.563752 0.025 Uiso 1 1 calc R U . . .
C6 C 0.8220(4) 0.4295(3) 0.4243(4) 0.0146(8) Uani 1 1 d . . . . .
C7 C 0.7375(4) 0.4968(3) 0.4827(4) 0.0157(8) Uani 1 1 d . . . . .
H7A H 0.718146 0.457700 0.557578 0.019 Uiso 1 1 calc R U . . .
H7B H 0.790808 0.559228 0.527458 0.019 Uiso 1 1 calc R U . . .
C8 C 0.8128(4) 0.5668(4) 0.2381(4) 0.0205(9) Uani 1 1 d . . . . .
H8A H 0.854726 0.622246 0.308517 0.025 Uiso 1 1 calc R U . . .
H8B H 0.848400 0.573911 0.160458 0.025 Uiso 1 1 calc R U . . .
C9 C 0.6148(4) 0.6161(3) 0.2821(4) 0.0149(8) Uani 1 1 d . . . . .
H9 H 0.674071 0.672171 0.341649 0.018 Uiso 1 1 calc R U . . .
C10 C 0.4748(4) 0.6604(3) 0.1995(4) 0.0168(8) Uani 1 1 d . . . . .
H10 H 0.482845 0.711639 0.128448 0.020 Uiso 1 1 calc R U . . .
C11 C 0.3719(4) 0.5772(4) 0.1207(4) 0.0191(9) Uani 1 1 d . . . . .
H11A H 0.278699 0.605931 0.089952 0.023 Uiso 1 1 calc R U . . .
H11B H 0.388873 0.554384 0.035014 0.023 Uiso 1 1 calc R U . . .
C12 C 0.3854(4) 0.4870(3) 0.2181(4) 0.0172(8) Uani 1 1 d . . . . .
C13 C 0.4994(4) 0.4673(3) 0.3344(4) 0.0134(7) Uani 1 1 d . . . . .
H13 H 0.501891 0.406939 0.389622 0.016 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
Br1 C10 1.965(4) . ?
O1 C8 1.449(5) . ?
O1 C9 1.405(5) . ?
O2 N2 1.233(5) . ?
O3 N2 1.259(5) . ?
N1 C7 1.475(5) . ?
N1 C9 1.457(5) . ?
N1 C13 1.340(5) . ?
N2 C12 1.418(5) . ?
C1 C2 1.399(6) . ?
C1 C6 1.414(5) . ?
C1 C8 1.494(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.395(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.369(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.395(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(6) . ?
C6 C7 1.510(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9 1.0000 . ?
C9 C10 1.520(5) . ?
C10 H10 1.0000 . ?
C10 C11 1.526(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.493(6) . ?
C12 C13 1.365(5) . ?
C13 H13 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C8 112.9(3) . . ?
C9 N1 C7 116.5(3) . . ?
C13 N1 C7 120.4(3) . . ?
C13 N1 C9 120.4(3) . . ?
O2 N2 O3 122.0(4) . . ?
O2 N2 C12 120.9(4) . . ?
O3 N2 C12 117.0(4) . . ?
C2 C1 C6 118.2(4) . . ?
C2 C1 C8 118.8(4) . . ?
C6 C1 C8 123.0(4) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.0(4) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(5) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0(4) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C7 120.6(4) . . ?
C5 C6 C1 120.2(4) . . ?
C5 C6 C7 119.1(3) . . ?
N1 C7 C6 113.3(3) . . ?
N1 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
C6 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
O1 C8 C1 114.5(3) . . ?
O1 C8 H8A 108.6 . . ?
O1 C8 H8B 108.6 . . ?
C1 C8 H8A 108.6 . . ?
C1 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
O1 C9 N1 111.2(3) . . ?
O1 C9 H9 109.3 . . ?
O1 C9 C10 106.0(3) . . ?
N1 C9 H9 109.3 . . ?
N1 C9 C10 111.6(3) . . ?
C10 C9 H9 109.3 . . ?
Br1 C10 H10 108.6 . . ?
C9 C10 Br1 107.8(2) . . ?
C9 C10 H10 108.6 . . ?
C9 C10 C11 112.9(3) . . ?
C11 C10 Br1 110.2(3) . . ?
C11 C10 H10 108.6 . . ?
C10 C11 H11A 109.9 . . ?
C10 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 C10 108.8(3) . . ?
C12 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
N2 C12 C11 119.2(4) . . ?
C13 C12 N2 117.2(4) . . ?
C13 C12 C11 123.6(4) . . ?
N1 C13 C12 122.2(4) . . ?
N1 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?

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
Br1 C10 C11 C12 -75.7(4) . . . . ?
O1 C9 C10 Br1 -168.2(2) . . . . ?
O1 C9 C10 C11 69.9(4) . . . . ?
O2 N2 C12 C11 177.0(4) . . . . ?
O2 N2 C12 C13 -3.1(6) . . . . ?
O3 N2 C12 C11 -3.4(5) . . . . ?
O3 N2 C12 C13 176.5(4) . . . . ?
N1 C9 C10 Br1 70.6(3) . . . . ?
N1 C9 C10 C11 -51.3(4) . . . . ?
N2 C12 C13 N1 -177.7(3) . . . . ?
C1 C2 C3 C4 0.8(6) . . . . ?
C1 C6 C7 N1 53.9(5) . . . . ?
C2 C1 C6 C5 -1.2(5) . . . . ?
C2 C1 C6 C7 177.3(3) . . . . ?
C2 C1 C8 O1 124.7(4) . . . . ?
C2 C3 C4 C5 0.5(7) . . . . ?
C3 C4 C5 C6 -2.2(7) . . . . ?
C4 C5 C6 C1 2.6(6) . . . . ?
C4 C5 C6 C7 -176.0(4) . . . . ?
C5 C6 C7 N1 -127.5(4) . . . . ?
C6 C1 C2 C3 -0.5(6) . . . . ?
C6 C1 C8 O1 -58.8(5) . . . . ?
C7 N1 C9 O1 75.6(4) . . . . ?
C7 N1 C9 C10 -166.2(3) . . . . ?
C7 N1 C13 C12 -168.6(3) . . . . ?
C8 O1 C9 N1 -75.3(4) . . . . ?
C8 O1 C9 C10 163.2(3) . . . . ?
C8 C1 C2 C3 176.2(4) . . . . ?
C8 C1 C6 C5 -177.8(4) . . . . ?
C8 C1 C6 C7 0.8(5) . . . . ?
C9 O1 C8 C1 82.5(4) . . . . ?
C9 N1 C7 C6 -78.6(4) . . . . ?
C9 N1 C13 C12 -7.7(5) . . . . ?
C9 C10 C11 C12 44.9(4) . . . . ?
C10 C11 C12 N2 158.5(3) . . . . ?
C10 C11 C12 C13 -21.4(5) . . . . ?
C11 C12 C13 N1 2.3(6) . . . . ?
C13 N1 C7 C6 83.1(4) . . . . ?
C13 N1 C9 O1 -86.1(4) . . . . ?
C13 N1 C9 C10 32.1(5) . . . . ?

_olex2_date_sample_data_collection 2023-04-04
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 15.524
_oxdiff_exptl_absorpt_empirical_full_min 0.487
####################################################################### 
# 
# 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_zcc-34-2
_database_code_depnum_ccdc_archive 'CCDC 2299099'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2023-10-04 deposited with the CCDC.	2023-12-21 downloaded from the CCDC.
;
_audit_creation_date             2023-03-31
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H15 Br N2 O3 S'
_chemical_formula_sum            'C10 H15 Br N2 O3 S'
_chemical_formula_weight         323.21
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   7.8851(8)
_cell_length_b                   16.802(2)
_cell_length_c                   10.6416(9)
_cell_angle_alpha                90
_cell_angle_beta                 111.647(11)
_cell_angle_gamma                90
_cell_volume                     1310.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2696
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      28.4770
_cell_measurement_theta_min      3.0030
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.295
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6558
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.389
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00  -7.00   1.00    8.80    --  -11.27  77.00   0.00   37
  2  ω      7.00  65.00   1.00    8.80    --  -11.27  77.00   0.00   58
  3  ω     11.00  47.00   1.00    8.80    --   11.90  77.00 -90.00   36
  4  ω    -77.00  -5.00   1.00    6.00    --  -11.43 -57.00-120.00   72
  5  ω    -16.00  34.00   1.00    6.00    --   11.90  77.00 150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0335188000
_diffrn_orient_matrix_UB_12      -0.0396183000
_diffrn_orient_matrix_UB_13      -0.0066344000
_diffrn_orient_matrix_UB_21      -0.0465190000
_diffrn_orient_matrix_UB_22      0.0089024000
_diffrn_orient_matrix_UB_23      0.0439878000
_diffrn_orient_matrix_UB_31      -0.0779661000
_diffrn_orient_matrix_UB_32      0.0115884000
_diffrn_orient_matrix_UB_33      -0.0561770000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1784
_reflns_number_total             2256
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2256
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0282P)²+1.2278P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0762
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C9-C11
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C11) \\sim Ueq: with sigma of 0.0005 and sigma for terminal atoms of 0.001
4. Rigid body (RIGU) restrains
 C7, C11, C9, S1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.003
5. Others
 Sof(H7B)=Sof(C8)=Sof(H8)=Sof(H9BC)=Sof(H9BD)=1-FVAR(1)
 Sof(H7A)=Sof(H9AA)=Sof(H9AB)=Sof(C11)=Sof(H11)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C5(H5), C4(H4)
6.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C6(H6A,H6B), C9(H9BC,H9BD), C9(H9AA,H9AB)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7B), C7(H7A), C8(H8), C11(H11)
6.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
6.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br1 Br 0.75760(4) 0.53356(2) 0.49409(3) 0.03358(14) Uani 1 1 d . . . . .
S1 S 1.25276(14) 0.73156(6) 0.50346(9) 0.0435(3) Uani 1 1 d . . . . .
O1 O 0.1274(3) 0.56268(16) 0.1243(2) 0.0352(6) Uani 1 1 d . . . . .
O3 O 0.7882(3) 0.46338(15) 0.1337(2) 0.0333(6) Uani 1 1 d . . . . .
H3 H 0.890282 0.462452 0.130101 0.050 Uiso 1 1 calc R U . . .
O2 O 0.1641(3) 0.44003(15) 0.1936(2) 0.0344(6) Uani 1 1 d . . . . .
N2 N 0.6571(3) 0.58054(17) 0.1734(2) 0.0239(6) Uani 1 1 d . . . . .
N1 N 0.2283(4) 0.50436(19) 0.1712(2) 0.0258(7) Uani 1 1 d . . . . .
C1 C 0.4810(4) 0.5719(2) 0.1561(3) 0.0234(7) Uani 1 1 d . . . . .
H1 H 0.399582 0.611932 0.111442 0.028 Uiso 1 1 calc R U . . .
C2 C 0.4162(4) 0.5075(2) 0.2006(3) 0.0222(7) Uani 1 1 d . . . . .
C5 C 0.7870(4) 0.5166(2) 0.2354(3) 0.0245(8) Uani 1 1 d . . . . .
H5 H 0.909254 0.538682 0.281802 0.029 Uiso 1 1 calc R U . . .
C4 C 0.7290(4) 0.4691(2) 0.3336(3) 0.0255(7) Uani 1 1 d . . . . .
H4 H 0.809197 0.422645 0.362562 0.031 Uiso 1 1 calc R U . . .
C3 C 0.5338(4) 0.4398(2) 0.2696(3) 0.0273(8) Uani 1 1 d . . . . .
H3A H 0.526163 0.397948 0.204982 0.033 Uiso 1 1 calc R U . . .
H3B H 0.493679 0.418320 0.338622 0.033 Uiso 1 1 calc R U . . .
C6 C 0.7153(4) 0.6426(2) 0.1022(3) 0.0329(9) Uani 1 1 d . . . . .
H6A H 0.607617 0.669961 0.041992 0.039 Uiso 1 1 calc R U . . .
H6B H 0.773583 0.617451 0.046632 0.039 Uiso 1 1 calc R U . . .
C7 C 0.8428(5) 0.7030(2) 0.1895(4) 0.0469(10) Uani 1 1 d . . . . .
H7B H 0.888954 0.738537 0.143117 0.056 Uiso 0.807(7) 1 calc R U P A 2
H7A H 0.770065 0.747390 0.184357 0.056 Uiso 0.193(7) 1 calc R U P A 1
C8 C 0.8988(6) 0.7143(3) 0.3146(4) 0.0358(13) Uani 0.807(7) 1 d . . P A 2
H8 H 0.849449 0.683886 0.365814 0.043 Uiso 0.807(7) 1 calc R U P A 2
C9 C 1.0450(6) 0.7760(2) 0.3867(4) 0.0545(11) Uani 1 1 d D . . . .
H9BC H 0.996772 0.812538 0.435827 0.065 Uiso 0.807(7) 1 calc R U P A 2
H9BD H 1.073510 0.806545 0.319633 0.065 Uiso 0.807(7) 1 calc R U P A 2
H9AA H 0.951893 0.777623 0.425978 0.065 Uiso 0.193(7) 1 calc R U P A 1
H9AB H 1.067734 0.829851 0.363862 0.065 Uiso 0.193(7) 1 calc R U P A 1
C10 C 1.3486(7) 0.6932(3) 0.3885(5) 0.0707(14) Uani 1 1 d . . . . .
H10A H 1.271514 0.651798 0.334991 0.106 Uiso 1 1 calc R U . . .
H10B H 1.467616 0.671867 0.438163 0.106 Uiso 1 1 calc R U . . .
H10C H 1.358525 0.735106 0.330322 0.106 Uiso 1 1 calc R U . . .
C11 C 0.984(3) 0.7219(10) 0.2588(14) 0.0368(19) Uani 0.193(7) 1 d D U P A 1
H11 H 1.078470 0.701843 0.235937 0.044 Uiso 0.193(7) 1 calc R U P A 1


_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
Br1 C4 1.963(3) . ?
S1 C9 1.812(4) . ?
S1 C10 1.780(4) . ?
O1 N1 1.245(4) . ?
O3 H3 0.8200 . ?
O3 C5 1.407(4) . ?
O2 N1 1.253(4) . ?
N2 C1 1.339(4) . ?
N2 C5 1.463(4) . ?
N2 C6 1.459(4) . ?
N1 C2 1.398(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.356(5) . ?
C2 C3 1.480(5) . ?
C5 H5 0.9800 . ?
C5 C4 1.513(4) . ?
C4 H4 0.9800 . ?
C4 C3 1.517(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.487(5) . ?
C7 H7B 0.9300 . ?
C7 H7A 0.9300 . ?
C7 C8 1.254(5) . ?
C7 C11 1.129(17) . ?
C8 H8 0.9300 . ?
C8 C9 1.530(6) . ?
C9 H9BC 0.9700 . ?
C9 H9BD 0.9700 . ?
C9 H9AA 0.9700 . ?
C9 H9AB 0.9700 . ?
C9 C11 1.558(9) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11 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
C10 S1 C9 100.6(2) . . ?
C5 O3 H3 109.5 . . ?
C1 N2 C5 120.0(3) . . ?
C1 N2 C6 121.0(3) . . ?
C6 N2 C5 117.2(2) . . ?
O1 N1 O2 120.8(3) . . ?
O1 N1 C2 121.9(3) . . ?
O2 N1 C2 117.3(3) . . ?
N2 C1 H1 118.5 . . ?
N2 C1 C2 122.9(3) . . ?
C2 C1 H1 118.5 . . ?
N1 C2 C3 120.1(3) . . ?
C1 C2 N1 117.2(3) . . ?
C1 C2 C3 122.6(3) . . ?
O3 C5 N2 108.8(2) . . ?
O3 C5 H5 110.1 . . ?
O3 C5 C4 106.6(3) . . ?
N2 C5 H5 110.1 . . ?
N2 C5 C4 111.1(2) . . ?
C4 C5 H5 110.1 . . ?
Br1 C4 H4 108.2 . . ?
C5 C4 Br1 110.1(2) . . ?
C5 C4 H4 108.2 . . ?
C5 C4 C3 112.1(2) . . ?
C3 C4 Br1 110.0(2) . . ?
C3 C4 H4 108.2 . . ?
C2 C3 C4 108.7(3) . . ?
C2 C3 H3A 110.0 . . ?
C2 C3 H3B 110.0 . . ?
C4 C3 H3A 110.0 . . ?
C4 C3 H3B 110.0 . . ?
H3A C3 H3B 108.3 . . ?
N2 C6 H6A 108.4 . . ?
N2 C6 H6B 108.4 . . ?
N2 C6 C7 115.7(3) . . ?
H6A C6 H6B 107.4 . . ?
C7 C6 H6A 108.4 . . ?
C7 C6 H6B 108.4 . . ?
C6 C7 H7B 114.4 . . ?
C6 C7 H7A 104.5 . . ?
C8 C7 C6 131.2(4) . . ?
C8 C7 H7B 114.4 . . ?
C11 C7 C6 151.0(9) . . ?
C11 C7 H7A 104.5 . . ?
C7 C8 H8 118.7 . . ?
C7 C8 C9 122.7(4) . . ?
C9 C8 H8 118.7 . . ?
S1 C9 H9BC 109.0 . . ?
S1 C9 H9BD 109.0 . . ?
S1 C9 H9AA 110.6 . . ?
S1 C9 H9AB 110.6 . . ?
C8 C9 S1 112.8(3) . . ?
C8 C9 H9BC 109.0 . . ?
C8 C9 H9BD 109.0 . . ?
H9BC C9 H9BD 107.8 . . ?
H9AA C9 H9AB 108.8 . . ?
C11 C9 S1 105.6(8) . . ?
C11 C9 H9AA 110.6 . . ?
C11 C9 H9AB 110.6 . . ?
S1 C10 H10A 109.5 . . ?
S1 C10 H10B 109.5 . . ?
S1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 C9 130.4(15) . . ?
C7 C11 H11 114.8 . . ?
C9 C11 H11 114.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C4 C3 C2 73.6(3) . . . . ?
S1 C9 C11 C7 142.4(18) . . . . ?
O1 N1 C2 C1 -10.4(4) . . . . ?
O1 N1 C2 C3 173.5(3) . . . . ?
O3 C5 C4 Br1 171.61(18) . . . . ?
O3 C5 C4 C3 -65.7(3) . . . . ?
O2 N1 C2 C1 169.4(3) . . . . ?
O2 N1 C2 C3 -6.7(4) . . . . ?
N2 C1 C2 N1 -177.5(3) . . . . ?
N2 C1 C2 C3 -1.6(5) . . . . ?
N2 C5 C4 Br1 -70.0(3) . . . . ?
N2 C5 C4 C3 52.7(4) . . . . ?
N2 C6 C7 C8 -6.8(7) . . . . ?
N2 C6 C7 C11 77(2) . . . . ?
N1 C2 C3 C4 -159.6(3) . . . . ?
C1 N2 C5 O3 87.6(3) . . . . ?
C1 N2 C5 C4 -29.5(4) . . . . ?
C1 N2 C6 C7 118.1(3) . . . . ?
C1 C2 C3 C4 24.6(4) . . . . ?
C5 N2 C1 C2 3.9(4) . . . . ?
C5 N2 C6 C7 -77.2(4) . . . . ?
C5 C4 C3 C2 -49.2(3) . . . . ?
C6 N2 C1 C2 168.2(3) . . . . ?
C6 N2 C5 O3 -77.3(3) . . . . ?
C6 N2 C5 C4 165.7(3) . . . . ?
C6 C7 C8 C9 174.3(4) . . . . ?
C6 C7 C11 C9 -143.6(11) . . . . ?
C7 C8 C9 S1 -115.3(5) . . . . ?
C10 S1 C9 C8 75.4(4) . . . . ?
C10 S1 C9 C11 33.7(8) . . . . ?

_olex2_date_sample_data_collection 2023-03-31
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.503
_oxdiff_exptl_absorpt_empirical_full_min 0.700
####################################################################### 
# 
# 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_1522
_database_code_depnum_ccdc_archive 'CCDC 2299100'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2023-10-04 deposited with the CCDC.	2023-12-21 downloaded from the CCDC.
;
_audit_creation_date             2023-04-05
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H24 N4 O4'
_chemical_formula_sum            'C24 H24 N4 O4'
_chemical_formula_weight         432.47
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.7417(2)
_cell_length_b                   13.7590(2)
_cell_length_c                   9.4773(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.031(2)
_cell_angle_gamma                90
_cell_volume                     1056.67(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3328
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.3830
_cell_measurement_theta_min      5.0210
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.772
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4080
_diffrn_reflns_point_group_measured_fraction_full 0.726
_diffrn_reflns_point_group_measured_fraction_max 0.701
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.520
_diffrn_reflns_theta_min         5.034
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     53.00  80.00   1.00    1.00    --   40.92 -99.00   0.00   27
  2  ω     27.00  67.00   1.00    1.00    --  107.58 -94.00 120.00   40
  3  ω     75.00 101.00   1.00    1.00    --  107.58 -94.00 120.00   26
  4  ω     33.00  98.00   1.00    1.00    --  107.58 -94.00  90.00   65
  5  ω     71.00 125.00   1.00    1.00    --  107.58 -30.00 -60.00   54
  6  ω    103.00 129.00   1.00    1.00    --  107.58 -45.00-150.00   26
  7  ω     83.00 159.00   1.00    1.00    --  107.58  45.00 -30.00   76
  8  ω     79.00 175.00   1.00    1.00    --  107.58  61.00   0.00   96
  9  ω     35.00  89.00   1.00    1.00    --  107.58 -45.00-150.00   54
 10  ω    -99.00 -29.00   1.00    1.00    --  -40.92 -77.00-120.00   70
 11  ω   -113.00 -13.00   1.00    1.00    --  -40.92 -57.00 120.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0473043000
_diffrn_orient_matrix_UB_12      0.0127879000
_diffrn_orient_matrix_UB_13      -0.1400146000
_diffrn_orient_matrix_UB_21      -0.1764687000
_diffrn_orient_matrix_UB_22      0.0350789000
_diffrn_orient_matrix_UB_23      -0.0941810000
_diffrn_orient_matrix_UB_31      0.0528289000
_diffrn_orient_matrix_UB_32      0.1055006000
_diffrn_orient_matrix_UB_33      0.0478991000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.370
_reflns_Friedel_fraction_full    0.426
_reflns_Friedel_fraction_max     0.396
_reflns_number_gt                2926
_reflns_number_total             2982
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 779 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.58(15)
_refine_ls_extinction_coef       0.0074(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         2982
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0542P)²+0.0672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0838
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B), C11(H11A,H11B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C14(H14), C17(H17), C20(H20),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.7206(2) 0.82042(13) 0.82869(18) 0.0381(4) Uani 1 1 d . . . . .
O2 O 0.7709(2) 0.80230(13) 0.6210(2) 0.0410(4) Uani 1 1 d . . . . .
O3 O 0.2861(2) 0.17902(12) 0.73012(18) 0.0373(4) Uani 1 1 d . . . . .
O4 O 0.5510(2) 0.18927(13) 0.85833(19) 0.0419(4) Uani 1 1 d . . . . .
N1 N 0.2247(2) 0.46474(13) 0.77706(18) 0.0262(4) Uani 1 1 d . . . . .
N2 N 0.5059(2) 0.55483(13) 0.52143(18) 0.0255(4) Uani 1 1 d . . . . .
N3 N 0.4111(2) 0.22752(14) 0.80603(19) 0.0304(4) Uani 1 1 d . . . . .
N4 N 0.7089(2) 0.77306(14) 0.7129(2) 0.0302(4) Uani 1 1 d . . . . .
C1 C 0.0201(2) 0.53620(16) 0.8648(2) 0.0285(4) Uani 1 1 d . . . . .
C3 C -0.0114(4) 0.6546(2) 1.0389(3) 0.0536(7) Uani 1 1 d . . . . .
H3 H -0.014937 0.720660 1.066800 0.064 Uiso 1 1 calc R U . . .
C4 C -0.0340(3) 0.5825(3) 1.1280(3) 0.0523(7) Uani 1 1 d . . . . .
H4 H -0.052007 0.598363 1.218077 0.063 Uiso 1 1 calc R U . . .
C5 C -0.0306(4) 0.4864(3) 1.0868(3) 0.0568(8) Uani 1 1 d . . . . .
H5 H -0.045988 0.435887 1.148502 0.068 Uiso 1 1 calc R U . . .
C6 C -0.0048(3) 0.4646(2) 0.9559(3) 0.0444(6) Uani 1 1 d . . . . .
H6 H -0.004030 0.398407 0.927393 0.053 Uiso 1 1 calc R U . . .
C7 C 0.0600(3) 0.50808(17) 0.7281(2) 0.0311(5) Uani 1 1 d . . . . .
H7A H -0.022978 0.460951 0.664745 0.037 Uiso 1 1 calc R U . . .
H7B H 0.055241 0.566414 0.665444 0.037 Uiso 1 1 calc R U . . .
C8 C 0.2473(3) 0.36940(15) 0.7703(2) 0.0265(4) Uani 1 1 d . . . . .
H8 H 0.154071 0.329587 0.719093 0.032 Uiso 1 1 calc R U . . .
C9 C 0.3992(3) 0.32626(15) 0.8340(2) 0.0276(4) Uani 1 1 d . . . . .
C10 C 0.5494(3) 0.37999(17) 0.9321(2) 0.0312(4) Uani 1 1 d . . . . .
H10A H 0.619091 0.395970 0.873639 0.037 Uiso 1 1 calc R U . . .
H10B H 0.614972 0.339461 1.020469 0.037 Uiso 1 1 calc R U . . .
C11 C 0.4936(3) 0.47347(16) 0.9868(2) 0.0298(4) Uani 1 1 d . . . . .
H11A H 0.590523 0.515690 1.037093 0.036 Uiso 1 1 calc R U . . .
H11B H 0.444834 0.456964 1.062676 0.036 Uiso 1 1 calc R U . . .
C12 C 0.3661(2) 0.52881(16) 0.8541(2) 0.0261(4) Uani 1 1 d . . . . .
H12 H 0.325719 0.585086 0.897321 0.031 Uiso 1 1 calc R U . . .
C13 C 0.4412(2) 0.56851(14) 0.7456(2) 0.0231(4) Uani 1 1 d . . . . .
C14 C 0.4243(2) 0.52350(15) 0.6162(2) 0.0242(4) Uani 1 1 d . . . . .
H14 H 0.354446 0.468155 0.586735 0.029 Uiso 1 1 calc R U . . .
C15 C 0.5418(3) 0.65949(16) 0.7988(2) 0.0285(4) Uani 1 1 d . . . . .
H15A H 0.472(4) 0.710(2) 0.807(3) 0.041(7) Uiso 1 1 d . . . . .
H15B H 0.630(3) 0.652(2) 0.902(3) 0.035(7) Uiso 1 1 d . . . . .
C16 C 0.6191(2) 0.68616(16) 0.6873(2) 0.0263(4) Uani 1 1 d . . . . .
C17 C 0.6014(2) 0.63439(15) 0.5601(2) 0.0257(4) Uani 1 1 d . . . . .
H17 H 0.657958 0.654989 0.497027 0.031 Uiso 1 1 calc R U . . .
C18 C 0.5022(3) 0.49377(16) 0.3928(2) 0.0270(4) Uani 1 1 d . . . . .
H18A H 0.518617 0.535570 0.314622 0.032 Uiso 1 1 calc R U . . .
H18B H 0.391944 0.463310 0.346532 0.032 Uiso 1 1 calc R U . . .
C19 C 0.6323(2) 0.41473(16) 0.4379(2) 0.0266(4) Uani 1 1 d . . . . .
C20 C 0.6379(3) 0.34411(17) 0.5450(2) 0.0321(5) Uani 1 1 d . . . . .
H20 H 0.561154 0.346700 0.594206 0.039 Uiso 1 1 calc R U . . .
C21 C 0.7541(3) 0.26995(18) 0.5810(3) 0.0388(5) Uani 1 1 d . . . . .
H21 H 0.757044 0.222517 0.654788 0.047 Uiso 1 1 calc R U . . .
C22 C 0.8659(3) 0.26520(19) 0.5091(3) 0.0406(6) Uani 1 1 d . . . . .
H22 H 0.944208 0.213897 0.532219 0.049 Uiso 1 1 calc R U . . .
C23 C 0.8630(3) 0.3353(2) 0.4039(3) 0.0429(6) Uani 1 1 d . . . . .
H23 H 0.939889 0.332463 0.354956 0.051 Uiso 1 1 calc R U . . .
C24 C 0.7474(3) 0.4103(2) 0.3692(2) 0.0344(5) Uani 1 1 d . . . . .
H24 H 0.747387 0.458899 0.297919 0.041 Uiso 1 1 calc R U . . .
C25 C 0.0168(3) 0.63244(18) 0.9076(3) 0.0413(6) Uani 1 1 d . . . . .
H25 H 0.033964 0.683174 0.847140 0.050 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 N4 1.247(3) . ?
O2 N4 1.252(2) . ?
O3 N3 1.252(2) . ?
O4 N3 1.250(3) . ?
N1 C7 1.464(3) . ?
N1 C8 1.332(3) . ?
N1 C12 1.470(3) . ?
N2 C14 1.409(2) . ?
N2 C17 1.342(3) . ?
N2 C18 1.471(2) . ?
N3 C9 1.395(3) . ?
N4 C16 1.401(3) . ?
C1 C6 1.380(3) . ?
C1 C7 1.513(3) . ?
C1 C25 1.388(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.364(5) . ?
C3 C25 1.390(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.375(4) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8 0.9500 . ?
C8 C9 1.371(3) . ?
C9 C10 1.490(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.533(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.534(3) . ?
C12 H12 1.0000 . ?
C12 C13 1.514(3) . ?
C13 C14 1.332(3) . ?
C13 C15 1.504(3) . ?
C14 H14 0.9500 . ?
C15 H15A 0.94(3) . ?
C15 H15B 1.00(3) . ?
C15 C16 1.498(3) . ?
C16 C17 1.359(3) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.514(3) . ?
C19 C20 1.393(3) . ?
C19 C24 1.390(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.389(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.386(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.381(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.394(4) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C12 117.18(17) . . ?
C8 N1 C7 122.11(18) . . ?
C8 N1 C12 120.19(18) . . ?
C14 N2 C18 119.67(17) . . ?
C17 N2 C14 119.21(16) . . ?
C17 N2 C18 120.68(17) . . ?
O3 N3 C9 121.10(19) . . ?
O4 N3 O3 121.11(19) . . ?
O4 N3 C9 117.79(19) . . ?
O1 N4 O2 122.00(18) . . ?
O1 N4 C16 117.00(17) . . ?
O2 N4 C16 120.99(18) . . ?
C6 C1 C7 119.6(2) . . ?
C6 C1 C25 118.3(2) . . ?
C25 C1 C7 122.0(2) . . ?
C4 C3 H3 119.7 . . ?
C4 C3 C25 120.6(3) . . ?
C25 C3 H3 119.7 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 H6 119.1 . . ?
C5 C6 C1 121.7(3) . . ?
C5 C6 H6 119.1 . . ?
N1 C7 C1 110.38(16) . . ?
N1 C7 H7A 109.6 . . ?
N1 C7 H7B 109.6 . . ?
C1 C7 H7A 109.6 . . ?
C1 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
N1 C8 H8 118.6 . . ?
N1 C8 C9 122.8(2) . . ?
C9 C8 H8 118.6 . . ?
N3 C9 C10 119.36(19) . . ?
C8 C9 N3 117.85(19) . . ?
C8 C9 C10 122.8(2) . . ?
C9 C10 H10A 110.1 . . ?
C9 C10 H10B 110.1 . . ?
C9 C10 C11 108.02(18) . . ?
H10A C10 H10B 108.4 . . ?
C11 C10 H10A 110.1 . . ?
C11 C10 H10B 110.1 . . ?
C10 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
C10 C11 C12 111.42(16) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
N1 C12 C11 109.06(17) . . ?
N1 C12 H12 107.9 . . ?
N1 C12 C13 112.14(15) . . ?
C11 C12 H12 107.9 . . ?
C13 C12 C11 111.65(17) . . ?
C13 C12 H12 107.9 . . ?
C14 C13 C12 122.07(18) . . ?
C14 C13 C15 122.98(18) . . ?
C15 C13 C12 114.89(16) . . ?
N2 C14 H14 118.7 . . ?
C13 C14 N2 122.51(18) . . ?
C13 C14 H14 118.7 . . ?
C13 C15 H15A 109.0(18) . . ?
C13 C15 H15B 112.2(16) . . ?
H15A C15 H15B 106(2) . . ?
C16 C15 C13 109.26(16) . . ?
C16 C15 H15A 110.8(17) . . ?
C16 C15 H15B 109.4(16) . . ?
N4 C16 C15 117.34(17) . . ?
C17 C16 N4 118.07(17) . . ?
C17 C16 C15 124.51(19) . . ?
N2 C17 C16 121.45(17) . . ?
N2 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
N2 C18 H18A 108.9 . . ?
N2 C18 H18B 108.9 . . ?
N2 C18 C19 113.31(16) . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
C20 C19 C18 121.59(18) . . ?
C24 C19 C18 119.88(19) . . ?
C24 C19 C20 118.5(2) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.9(2) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.0(2) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.8(2) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.2(2) . . ?
C24 C23 H23 119.9 . . ?
C19 C24 C23 120.6(2) . . ?
C19 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C1 C25 C3 120.1(3) . . ?
C1 C25 H25 120.0 . . ?
C3 C25 H25 120.0 . . ?

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
O1 N4 C16 C15 1.7(3) . . . . ?
O1 N4 C16 C17 178.55(19) . . . . ?
O2 N4 C16 C15 -176.8(2) . . . . ?
O2 N4 C16 C17 0.1(3) . . . . ?
O3 N3 C9 C8 -2.7(3) . . . . ?
O3 N3 C9 C10 176.56(17) . . . . ?
O4 N3 C9 C8 176.79(17) . . . . ?
O4 N3 C9 C10 -4.0(2) . . . . ?
N1 C8 C9 N3 -173.28(17) . . . . ?
N1 C8 C9 C10 7.5(3) . . . . ?
N1 C12 C13 C14 -23.7(3) . . . . ?
N1 C12 C13 C15 158.92(18) . . . . ?
N2 C18 C19 C20 59.5(3) . . . . ?
N2 C18 C19 C24 -121.9(2) . . . . ?
N3 C9 C10 C11 -161.30(16) . . . . ?
N4 C16 C17 N2 -174.40(18) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C4 C3 C25 C1 0.9(4) . . . . ?
C4 C5 C6 C1 0.8(5) . . . . ?
C6 C1 C7 N1 -68.8(3) . . . . ?
C6 C1 C25 C3 -0.2(4) . . . . ?
C7 N1 C8 C9 -171.05(16) . . . . ?
C7 N1 C12 C11 139.45(17) . . . . ?
C7 N1 C12 C13 -96.36(19) . . . . ?
C7 C1 C6 C5 175.7(2) . . . . ?
C7 C1 C25 C3 -176.4(2) . . . . ?
C8 N1 C7 C1 104.1(2) . . . . ?
C8 N1 C12 C11 -32.5(2) . . . . ?
C8 N1 C12 C13 91.7(2) . . . . ?
C8 C9 C10 C11 17.9(3) . . . . ?
C9 C10 C11 C12 -49.2(2) . . . . ?
C10 C11 C12 N1 57.3(2) . . . . ?
C10 C11 C12 C13 -67.2(2) . . . . ?
C11 C12 C13 C14 99.0(2) . . . . ?
C11 C12 C13 C15 -78.3(2) . . . . ?
C12 N1 C7 C1 -67.7(2) . . . . ?
C12 N1 C8 C9 0.5(3) . . . . ?
C12 C13 C14 N2 -174.04(18) . . . . ?
C12 C13 C15 C16 175.58(17) . . . . ?
C13 C15 C16 N4 175.80(18) . . . . ?
C13 C15 C16 C17 -0.9(3) . . . . ?
C14 N2 C17 C16 -1.0(3) . . . . ?
C14 N2 C18 C19 -83.6(2) . . . . ?
C14 C13 C15 C16 -1.8(3) . . . . ?
C15 C13 C14 N2 3.1(3) . . . . ?
C15 C16 C17 N2 2.3(3) . . . . ?
C17 N2 C14 C13 -1.7(3) . . . . ?
C17 N2 C18 C19 88.7(2) . . . . ?
C18 N2 C14 C13 170.75(19) . . . . ?
C18 N2 C17 C16 -173.36(19) . . . . ?
C18 C19 C20 C21 177.6(2) . . . . ?
C18 C19 C24 C23 -176.9(2) . . . . ?
C19 C20 C21 C22 -0.4(3) . . . . ?
C20 C19 C24 C23 1.7(3) . . . . ?
C20 C21 C22 C23 1.1(3) . . . . ?
C21 C22 C23 C24 -0.4(4) . . . . ?
C22 C23 C24 C19 -1.1(4) . . . . ?
C24 C19 C20 C21 -1.0(3) . . . . ?
C25 C1 C6 C5 -0.6(4) . . . . ?
C25 C1 C7 N1 107.3(2) . . . . ?
C25 C3 C4 C5 -0.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.413
_oxdiff_exptl_absorpt_empirical_full_min 0.509
####################################################################### 
# 
# 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_zcc-15-2
_database_code_depnum_ccdc_archive 'CCDC 2299102'
loop_
_audit_author_name
_audit_author_address
'Qilin Wang'
;Henan University
China
;
_audit_update_record             
;
2023-10-04 deposited with the CCDC.	2023-12-21 downloaded from the CCDC.
;
_audit_creation_date             2023-02-18
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C12 H10 N2 O3)'
_chemical_formula_sum            'C24 H20 N4 O6'
_chemical_formula_weight         460.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N P'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.1802(2)
_cell_length_b                   11.8247(2)
_cell_length_c                   14.6931(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.067(2)
_cell_angle_gamma                90
_cell_volume                     2116.21(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7357
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.3130
_cell_measurement_theta_min      3.6320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.886
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18367
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.906
_diffrn_reflns_theta_min         3.629
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  76.00   0.50    0.80    --   42.30 -82.00 -60.00  190
  2  ω    -46.00  64.00   0.50    0.80    --   42.30 -57.00 -30.00  220
  3  ω     87.00 113.00   0.50    0.80    --   42.30  77.00-120.00   52
  4  ω    104.00 131.00   0.50    0.80    --   42.30  77.00  30.00   54
  5  ω     44.00  90.00   0.50    1.00    --  101.60 -82.00-150.00   92
  6  ω     12.00 145.00   0.50    1.00    --  101.60 -82.00-120.00  266
  7  ω     15.00  41.00   0.50    1.00    --  101.60 -82.00 150.00   52
  8  ω     64.00 189.00   0.50    1.00    --  101.60  25.00-180.00  250
  9  ω     13.00 134.00   0.50    1.00    --  101.60 -63.00-120.00  242
 10  ω     77.00 106.00   0.50    1.00    --  101.60 -82.00-180.00   58
 11  ω     71.00 115.00   0.50    1.00    --  101.60 -82.00 150.00   88
 12  ω     95.00 191.00   0.50    1.00    --  101.60  25.00 -90.00  192
 13  ω     29.00  67.00   0.50    1.00    --  101.60  25.00 -90.00   76
 14  ω     -6.00  44.00   0.50    0.80    --   42.10 -82.00 120.00  100
 15  ω    -12.00  25.00   0.50    0.80    --   42.10 -57.00-150.00   74
 16  ω     93.00 131.00   0.50    0.80    --   42.10  77.00-150.00   76
 17  ω     47.00  74.00   0.50    0.80    --   42.10 -82.00 120.00   54
 18  ω     55.00 109.00   0.50    0.80    --   42.10  57.00  90.00  108
 19  ω    -47.00  68.00   0.50    0.80    --   42.10 -57.00 150.00  230
 20  ω    114.00 156.00   0.50    1.00    --  101.60  38.00-120.00   84
 21  ω     40.00 187.00   0.50    1.00    --  101.60 -12.00-150.00  294
 22  ω     88.00 141.00   0.50    1.00    --  101.60  77.00 -60.00  106
 23  ω     22.00  62.00   0.50    1.00    --  101.60 -77.00  90.00   80
 24  ω     13.00 132.00   0.50    1.00    --  101.60 -63.00  30.00  238
 25  ω     55.00  85.00   0.50    1.00    --  101.60  38.00-120.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0851359000
_diffrn_orient_matrix_UB_12      0.0962749000
_diffrn_orient_matrix_UB_13      0.0034927000
_diffrn_orient_matrix_UB_21      0.0934341000
_diffrn_orient_matrix_UB_22      0.0872826000
_diffrn_orient_matrix_UB_23      0.0071195000
_diffrn_orient_matrix_UB_31      0.0032495000
_diffrn_orient_matrix_UB_32      0.0091450000
_diffrn_orient_matrix_UB_33      -0.1045828000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3401
_reflns_number_total             4023
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4023
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0508P)²+0.6069P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1115
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C14(H14),
 C15(H15), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.89540(8) 0.73654(10) 0.12767(8) 0.0357(3) Uani 1 1 d . . . . .
O2 O 0.47031(8) 0.59330(9) -0.06456(8) 0.0301(3) Uani 1 1 d . . . . .
O3 O 0.58892(9) 0.52240(10) -0.15888(8) 0.0380(3) Uani 1 1 d . . . . .
N1 N 0.71254(9) 0.70760(10) 0.10065(9) 0.0227(3) Uani 1 1 d . . . . .
N2 N 0.56556(10) 0.57372(11) -0.08835(9) 0.0267(3) Uani 1 1 d . . . . .
C1 C 0.67883(11) 0.69860(12) 0.26891(10) 0.0240(3) Uani 1 1 d . . . . .
C2 C 0.57749(11) 0.66517(13) 0.30342(11) 0.0273(3) Uani 1 1 d . . . . .
H2 H 0.512209 0.685154 0.271848 0.033 Uiso 1 1 calc R U . . .
C3 C 0.57061(12) 0.60315(13) 0.38322(12) 0.0304(4) Uani 1 1 d . . . . .
H3 H 0.500868 0.580916 0.405905 0.037 Uiso 1 1 calc R U . . .
C4 C 0.66543(13) 0.57334(13) 0.43020(11) 0.0293(3) Uani 1 1 d . . . . .
H4 H 0.660798 0.531481 0.485253 0.035 Uiso 1 1 calc R U . . .
C5 C 0.76681(12) 0.60526(13) 0.39596(11) 0.0288(3) Uani 1 1 d . . . . .
H5 H 0.831896 0.584292 0.427402 0.035 Uiso 1 1 calc R U . . .
C6 C 0.77406(12) 0.66745(13) 0.31633(11) 0.0271(3) Uani 1 1 d . . . . .
H6 H 0.843992 0.689136 0.293705 0.033 Uiso 1 1 calc R U . . .
C7 C 0.68443(12) 0.77139(12) 0.18439(11) 0.0266(3) Uani 1 1 d . . . . .
H7A H 0.612530 0.808839 0.175459 0.032 Uiso 1 1 calc R U . . .
H7B H 0.740053 0.831290 0.193917 0.032 Uiso 1 1 calc R U . . .
C8 C 0.63058(11) 0.66844(12) 0.04693(10) 0.0232(3) Uani 1 1 d . . . . .
H8 H 0.556218 0.679932 0.064031 0.028 Uiso 1 1 calc R U . . .
C9 C 0.65461(11) 0.61266(12) -0.03152(10) 0.0238(3) Uani 1 1 d . . . . .
C10 C 0.76457(12) 0.59563(13) -0.05922(11) 0.0260(3) Uani 1 1 d . . . . .
H10 H 0.780851 0.556886 -0.114214 0.031 Uiso 1 1 calc R U . . .
C11 C 0.84585(11) 0.63576(13) -0.00561(11) 0.0266(3) Uani 1 1 d . . . . .
H11 H 0.919851 0.623802 -0.023553 0.032 Uiso 1 1 calc R U . . .
C12 C 0.82471(11) 0.69579(13) 0.07744(11) 0.0259(3) Uani 1 1 d . . . . .
O4 O 0.91497(9) 0.44622(10) 0.10073(8) 0.0380(3) Uani 1 1 d . . . . .
O5 O 1.02775(8) 0.37757(10) 0.20105(8) 0.0342(3) Uani 1 1 d . . . . .
O6 O 0.59317(8) 0.28204(10) 0.39584(8) 0.0318(3) Uani 1 1 d . . . . .
N3 N 0.93432(10) 0.40125(10) 0.17497(9) 0.0263(3) Uani 1 1 d . . . . .
N4 N 0.77687(9) 0.28173(10) 0.36293(8) 0.0229(3) Uani 1 1 d . . . . .
C13 C 0.84251(11) 0.37369(12) 0.23225(10) 0.0235(3) Uani 1 1 d . . . . .
C14 C 0.73499(11) 0.40770(12) 0.20793(10) 0.0243(3) Uani 1 1 d . . . . .
H14 H 0.722398 0.450728 0.154322 0.029 Uiso 1 1 calc R U . . .
C15 C 0.65088(11) 0.37786(12) 0.26228(11) 0.0248(3) Uani 1 1 d . . . . .
H15 H 0.578667 0.400875 0.246282 0.030 Uiso 1 1 calc R U . . .
C16 C 0.66666(11) 0.31230(12) 0.34380(11) 0.0248(3) Uani 1 1 d . . . . .
C17 C 0.86147(11) 0.31188(12) 0.30905(11) 0.0235(3) Uani 1 1 d . . . . .
H17 H 0.934199 0.290101 0.324561 0.028 Uiso 1 1 calc R U . . .
C18 C 0.79897(12) 0.21880(12) 0.44796(11) 0.0264(3) Uani 1 1 d . . . . .
H18A H 0.867279 0.174286 0.440921 0.032 Uiso 1 1 calc R U . . .
H18B H 0.738038 0.165330 0.459597 0.032 Uiso 1 1 calc R U . . .
C19 C 0.81078(11) 0.29793(12) 0.52814(10) 0.0245(3) Uani 1 1 d . . . . .
C20 C 0.72219(11) 0.31900(12) 0.58537(11) 0.0257(3) Uani 1 1 d . . . . .
H20 H 0.653813 0.282863 0.574280 0.031 Uiso 1 1 calc R U . . .
C21 C 0.73296(12) 0.39237(13) 0.65853(11) 0.0282(3) Uani 1 1 d . . . . .
H21 H 0.672065 0.406349 0.697278 0.034 Uiso 1 1 calc R U . . .
C22 C 0.83264(13) 0.44535(13) 0.67510(12) 0.0305(4) Uani 1 1 d . . . . .
H22 H 0.840149 0.495395 0.725301 0.037 Uiso 1 1 calc R U . . .
C23 C 0.92110(12) 0.42514(14) 0.61837(12) 0.0331(4) Uani 1 1 d . . . . .
H23 H 0.989236 0.461683 0.629634 0.040 Uiso 1 1 calc R U . . .
C24 C 0.91088(12) 0.35189(13) 0.54521(12) 0.0297(3) Uani 1 1 d . . . . .
H24 H 0.971972 0.338321 0.506593 0.036 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 C12 1.2316(18) . ?
O2 N2 1.2341(16) . ?
O3 N2 1.2345(17) . ?
N1 C7 1.483(2) . ?
N1 C8 1.3536(18) . ?
N1 C12 1.4154(18) . ?
N2 C9 1.4435(18) . ?
C1 C2 1.392(2) . ?
C1 C6 1.402(2) . ?
C1 C7 1.513(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(2) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8 0.9500 . ?
C8 C9 1.360(2) . ?
C9 C10 1.415(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.351(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.435(2) . ?
O4 N3 1.2359(17) . ?
O5 N3 1.2325(16) . ?
O6 C16 1.2310(18) . ?
N3 C13 1.4378(19) . ?
N4 C16 1.4179(17) . ?
N4 C17 1.3482(19) . ?
N4 C18 1.4786(19) . ?
C13 C14 1.4155(19) . ?
C13 C17 1.364(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.347(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.440(2) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.511(2) . ?
C19 C20 1.391(2) . ?
C19 C24 1.399(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.388(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.387(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.384(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.386(2) . ?
C24 H24 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C7 119.13(12) . . ?
C8 N1 C12 122.49(13) . . ?
C12 N1 C7 118.28(12) . . ?
O2 N2 O3 123.21(13) . . ?
O2 N2 C9 118.84(13) . . ?
O3 N2 C9 117.95(12) . . ?
C2 C1 C6 118.55(14) . . ?
C2 C1 C7 120.10(13) . . ?
C6 C1 C7 121.30(13) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.87(14) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.22(14) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.38(15) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.59(14) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.40(14) . . ?
C5 C6 H6 119.8 . . ?
N1 C7 C1 113.72(12) . . ?
N1 C7 H7A 108.8 . . ?
N1 C7 H7B 108.8 . . ?
C1 C7 H7A 108.8 . . ?
C1 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
N1 C8 H8 120.0 . . ?
N1 C8 C9 120.05(13) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 N2 118.86(12) . . ?
C8 C9 C10 121.17(14) . . ?
C10 C9 N2 119.94(14) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 C9 118.41(15) . . ?
C11 C10 H10 120.8 . . ?
C10 C11 H11 118.7 . . ?
C10 C11 C12 122.52(13) . . ?
C12 C11 H11 118.7 . . ?
O1 C12 N1 119.43(14) . . ?
O1 C12 C11 125.24(13) . . ?
N1 C12 C11 115.34(13) . . ?
O4 N3 C13 117.81(12) . . ?
O5 N3 O4 123.17(13) . . ?
O5 N3 C13 119.01(13) . . ?
C16 N4 C18 117.85(12) . . ?
C17 N4 C16 122.70(12) . . ?
C17 N4 C18 119.38(12) . . ?
C14 C13 N3 120.52(13) . . ?
C17 C13 N3 118.34(12) . . ?
C17 C13 C14 121.12(13) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 C13 118.69(14) . . ?
C15 C14 H14 120.7 . . ?
C14 C15 H15 118.9 . . ?
C14 C15 C16 122.25(13) . . ?
C16 C15 H15 118.9 . . ?
O6 C16 N4 119.45(14) . . ?
O6 C16 C15 125.23(13) . . ?
N4 C16 C15 115.32(12) . . ?
N4 C17 C13 119.92(13) . . ?
N4 C17 H17 120.0 . . ?
C13 C17 H17 120.0 . . ?
N4 C18 H18A 109.4 . . ?
N4 C18 H18B 109.4 . . ?
N4 C18 C19 111.35(12) . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 H18A 109.4 . . ?
C19 C18 H18B 109.4 . . ?
C20 C19 C18 120.59(13) . . ?
C20 C19 C24 119.11(14) . . ?
C24 C19 C18 120.30(13) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.51(14) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.01(14) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.88(15) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.38(14) . . ?
C24 C23 H23 119.8 . . ?
C19 C24 H24 119.9 . . ?
C23 C24 C19 120.12(14) . . ?
C23 C24 H24 119.9 . . ?

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
O2 N2 C9 C8 0.8(2) . . . . ?
O2 N2 C9 C10 -177.26(13) . . . . ?
O3 N2 C9 C8 -179.38(13) . . . . ?
O3 N2 C9 C10 2.6(2) . . . . ?
N1 C8 C9 N2 -178.83(12) . . . . ?
N1 C8 C9 C10 -0.8(2) . . . . ?
N2 C9 C10 C11 178.27(13) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
C2 C1 C7 N1 -101.77(16) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
C4 C5 C6 C1 -0.3(2) . . . . ?
C6 C1 C2 C3 0.4(2) . . . . ?
C6 C1 C7 N1 81.03(17) . . . . ?
C7 N1 C8 C9 178.07(13) . . . . ?
C7 N1 C12 O1 1.3(2) . . . . ?
C7 N1 C12 C11 -178.40(12) . . . . ?
C7 C1 C2 C3 -176.84(14) . . . . ?
C7 C1 C6 C5 176.93(14) . . . . ?
C8 N1 C7 C1 93.90(15) . . . . ?
C8 N1 C12 O1 177.59(14) . . . . ?
C8 N1 C12 C11 -2.1(2) . . . . ?
C8 C9 C10 C11 0.3(2) . . . . ?
C9 C10 C11 C12 -0.7(2) . . . . ?
C10 C11 C12 O1 -178.12(15) . . . . ?
C10 C11 C12 N1 1.6(2) . . . . ?
C12 N1 C7 C1 -89.69(15) . . . . ?
C12 N1 C8 C9 1.8(2) . . . . ?
O4 N3 C13 C14 -6.3(2) . . . . ?
O4 N3 C13 C17 172.15(13) . . . . ?
O5 N3 C13 C14 174.90(13) . . . . ?
O5 N3 C13 C17 -6.7(2) . . . . ?
N3 C13 C14 C15 178.41(13) . . . . ?
N3 C13 C17 N4 -178.08(12) . . . . ?
N4 C18 C19 C20 96.78(16) . . . . ?
N4 C18 C19 C24 -82.58(16) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C14 C13 C17 N4 0.3(2) . . . . ?
C14 C15 C16 O6 -179.63(14) . . . . ?
C14 C15 C16 N4 0.2(2) . . . . ?
C16 N4 C17 C13 -0.5(2) . . . . ?
C16 N4 C18 C19 -84.13(15) . . . . ?
C17 N4 C16 O6 -179.98(13) . . . . ?
C17 N4 C16 C15 0.2(2) . . . . ?
C17 N4 C18 C19 93.05(15) . . . . ?
C17 C13 C14 C15 0.0(2) . . . . ?
C18 N4 C16 O6 -2.9(2) . . . . ?
C18 N4 C16 C15 177.26(12) . . . . ?
C18 N4 C17 C13 -177.49(13) . . . . ?
C18 C19 C20 C21 -179.49(13) . . . . ?
C18 C19 C24 C23 179.46(14) . . . . ?
C19 C20 C21 C22 0.0(2) . . . . ?
C20 C19 C24 C23 0.1(2) . . . . ?
C20 C21 C22 C23 0.2(2) . . . . ?
C21 C22 C23 C24 -0.2(2) . . . . ?
C22 C23 C24 C19 0.1(2) . . . . ?
C24 C19 C20 C21 -0.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.467
_oxdiff_exptl_absorpt_empirical_full_min 0.561
