# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1874277'
loop_
_audit_author_name
_audit_author_address
'Peigang Ding'
;??The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2018-10-20 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 N4 O3 S'
_chemical_formula_weight         328.35

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   6.4901(2)
_cell_length_b                   13.5853(4)
_cell_length_c                   17.2054(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1517.00(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7004
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9205
_exptl_absorpt_correction_T_max  0.9591
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17672
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2673
_reflns_number_gt                2510
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0534P)²+0.2743P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2673
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.97202(10) 0.40728(6) 0.99903(4) 0.0688(2) Uani 1 1 d . . .
O1 O 1.1846(4) 0.24230(15) 1.18721(17) 0.1035(8) Uani 1 1 d . . .
O2 O 1.4873(4) 0.27082(17) 1.22721(14) 0.1084(9) Uani 1 1 d . . .
O3 O 0.7033(2) 0.53418(12) 1.11922(10) 0.0519(4) Uani 1 1 d . . .
N1 N 1.3182(4) 0.29690(16) 1.20652(11) 0.0605(5) Uani 1 1 d . . .
N2 N 1.0029(3) 0.55486(13) 1.25598(10) 0.0478(4) Uani 1 1 d . . .
N3 N 0.8274(3) 0.52993(12) 1.27574(10) 0.0465(4) Uani 1 1 d . . .
N4 N 0.6732(4) 0.51170(16) 1.30216(13) 0.0683(6) Uani 1 1 d . . .
C1 C 0.8972(3) 0.68474(14) 1.10727(10) 0.0383(4) Uani 1 1 d . . .
C2 C 0.7593(3) 0.75361(16) 1.07788(12) 0.0477(5) Uani 1 1 d . . .
H2A H 0.6241 0.7363 1.0662 0.057 Uiso 1 1 calc R . .
C3 C 0.8295(4) 0.84857(17) 1.06651(14) 0.0558(6) Uani 1 1 d . . .
H3A H 0.7409 0.8963 1.0469 0.067 Uiso 1 1 calc R . .
C4 C 1.0305(4) 0.87281(17) 1.08409(13) 0.0565(6) Uani 1 1 d . . .
H4A H 1.0753 0.9370 1.0758 0.068 Uiso 1 1 calc R . .
C5 C 1.1672(4) 0.80450(15) 1.11361(12) 0.0485(5) Uani 1 1 d . . .
H5A H 1.3019 0.8223 1.1256 0.058 Uiso 1 1 calc R . .
C6 C 1.0999(3) 0.70934(14) 1.12496(11) 0.0379(4) Uani 1 1 d . . .
C7 C 1.2184(3) 0.62102(14) 1.15456(13) 0.0412(5) Uani 1 1 d . . .
H7A H 1.2941 0.6372 1.2015 0.049 Uiso 1 1 calc R . .
H7B H 1.3144 0.5973 1.1156 0.049 Uiso 1 1 calc R . .
C8 C 1.0520(3) 0.54428(14) 1.17121(11) 0.0361(4) Uani 1 1 d . . .
C9 C 0.8588(3) 0.58190(15) 1.12773(11) 0.0381(4) Uani 1 1 d . . .
C10 C 1.2805(3) 0.40535(15) 1.20699(12) 0.0455(5) Uani 1 1 d . . .
H10A H 1.4053 0.4390 1.1911 0.055 Uiso 1 1 calc R . .
H10B H 1.2483 0.4261 1.2596 0.055 Uiso 1 1 calc R . .
C11 C 1.1057(3) 0.43541(13) 1.15351(11) 0.0361(4) Uani 1 1 d . . .
H11A H 0.9853 0.3953 1.1668 0.043 Uiso 1 1 calc R . .
C12 C 1.1585(3) 0.41569(13) 1.06952(11) 0.0382(4) Uani 1 1 d . . .
C13 C 1.3477(3) 0.39592(16) 1.03731(12) 0.0471(5) Uani 1 1 d . . .
H13A H 1.4703 0.3975 1.0653 0.057 Uiso 1 1 calc R . .
C14 C 1.3370(5) 0.37279(18) 0.95708(14) 0.0614(6) Uani 1 1 d . . .
H14A H 1.4511 0.3569 0.9269 0.074 Uiso 1 1 calc R . .
C15 C 1.1456(5) 0.3763(2) 0.92983(14) 0.0705(8) Uani 1 1 d . . .
H15B H 1.1109 0.3633 0.8784 0.085 Uiso 1 1 calc R . .


_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
S1 C15 1.692(3) . ?
S1 C12 1.7173(19) . ?
O1 N1 1.189(3) . ?
O2 N1 1.207(3) . ?
O3 C9 1.208(2) . ?
N1 C10 1.494(3) . ?
N2 N3 1.236(3) . ?
N2 C8 1.500(3) . ?
N3 N4 1.127(3) . ?
C1 C2 1.390(3) . ?
C1 C6 1.391(3) . ?
C1 C9 1.462(3) . ?
C2 C3 1.382(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.379(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.378(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.513(3) . ?
C7 C8 1.528(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.547(3) . ?
C8 C11 1.550(3) . ?
C10 C11 1.516(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.509(3) . ?
C11 H11A 0.9800 . ?
C12 C13 1.374(3) . ?
C13 C14 1.417(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.329(4) . ?
C14 H14A 0.9300 . ?
C15 H15B 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
C15 S1 C12 92.53(12) . . ?
O1 N1 O2 124.2(2) . . ?
O1 N1 C10 119.8(2) . . ?
O2 N1 C10 115.9(2) . . ?
N3 N2 C8 115.90(17) . . ?
N4 N3 N2 171.8(2) . . ?
C2 C1 C6 121.80(19) . . ?
C2 C1 C9 128.37(19) . . ?
C6 C1 C9 109.77(17) . . ?
C3 C2 C1 117.9(2) . . ?
C3 C2 H2A 121.1 . . ?
C1 C2 H2A 121.1 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C5 121.9(2) . . ?
C3 C4 H4A 119.1 . . ?
C5 C4 H4A 119.1 . . ?
C6 C5 C4 118.6(2) . . ?
C6 C5 H5A 120.7 . . ?
C4 C5 H5A 120.7 . . ?
C5 C6 C1 119.61(19) . . ?
C5 C6 C7 129.06(19) . . ?
C1 C6 C7 111.33(17) . . ?
C6 C7 C8 104.17(15) . . ?
C6 C7 H7A 110.9 . . ?
C8 C7 H7A 110.9 . . ?
C6 C7 H7B 110.9 . . ?
C8 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
N2 C8 C7 105.49(16) . . ?
N2 C8 C9 105.47(15) . . ?
C7 C8 C9 104.88(15) . . ?
N2 C8 C11 109.29(15) . . ?
C7 C8 C11 117.06(16) . . ?
C9 C8 C11 113.75(15) . . ?
O3 C9 C1 128.75(18) . . ?
O3 C9 C8 123.93(18) . . ?
C1 C9 C8 107.09(15) . . ?
N1 C10 C11 112.65(18) . . ?
N1 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
N1 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C10 111.31(16) . . ?
C12 C11 C8 114.13(15) . . ?
C10 C11 C8 107.83(15) . . ?
C12 C11 H11A 107.8 . . ?
C10 C11 H11A 107.8 . . ?
C8 C11 H11A 107.8 . . ?
C13 C12 C11 128.60(18) . . ?
C13 C12 S1 109.40(15) . . ?
C11 C12 S1 121.87(15) . . ?
C12 C13 C14 113.1(2) . . ?
C12 C13 H13A 123.5 . . ?
C14 C13 H13A 123.5 . . ?
C15 C14 C13 112.4(2) . . ?
C15 C14 H14A 123.8 . . ?
C13 C14 H14A 123.8 . . ?
C14 C15 S1 112.53(19) . . ?
C14 C15 H15B 123.7 . . ?
S1 C15 H15B 123.7 . . ?

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 N2 N3 N4 -172.6(15) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C9 C1 C2 C3 176.86(19) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C4 C5 C6 C7 178.6(2) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C9 C1 C6 C5 -177.08(17) . . . . ?
C2 C1 C6 C7 -178.99(18) . . . . ?
C9 C1 C6 C7 3.6(2) . . . . ?
C5 C6 C7 C8 167.9(2) . . . . ?
C1 C6 C7 C8 -12.9(2) . . . . ?
N3 N2 C8 C7 153.11(17) . . . . ?
N3 N2 C8 C9 42.4(2) . . . . ?
N3 N2 C8 C11 -80.2(2) . . . . ?
C6 C7 C8 N2 -94.79(17) . . . . ?
C6 C7 C8 C9 16.3(2) . . . . ?
C6 C7 C8 C11 143.44(16) . . . . ?
C2 C1 C9 O3 4.7(3) . . . . ?
C6 C1 C9 O3 -178.1(2) . . . . ?
C2 C1 C9 C8 -169.93(19) . . . . ?
C6 C1 C9 C8 7.2(2) . . . . ?
N2 C8 C9 O3 -78.7(2) . . . . ?
C7 C8 C9 O3 170.21(18) . . . . ?
C11 C8 C9 O3 41.1(3) . . . . ?
N2 C8 C9 C1 96.26(17) . . . . ?
C7 C8 C9 C1 -14.9(2) . . . . ?
C11 C8 C9 C1 -143.99(16) . . . . ?
O1 N1 C10 C11 -22.7(3) . . . . ?
O2 N1 C10 C11 158.0(2) . . . . ?
N1 C10 C11 C12 -65.4(2) . . . . ?
N1 C10 C11 C8 168.68(18) . . . . ?
N2 C8 C11 C12 -179.89(16) . . . . ?
C7 C8 C11 C12 -60.1(2) . . . . ?
C9 C8 C11 C12 62.5(2) . . . . ?
N2 C8 C11 C10 -55.7(2) . . . . ?
C7 C8 C11 C10 64.1(2) . . . . ?
C9 C8 C11 C10 -173.24(16) . . . . ?
C10 C11 C12 C13 -15.0(3) . . . . ?
C8 C11 C12 C13 107.3(2) . . . . ?
C10 C11 C12 S1 160.51(14) . . . . ?
C8 C11 C12 S1 -77.2(2) . . . . ?
C15 S1 C12 C13 0.88(18) . . . . ?
C15 S1 C12 C11 -175.42(17) . . . . ?
C11 C12 C13 C14 174.90(19) . . . . ?
S1 C12 C13 C14 -1.1(2) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C13 C14 C15 S1 -0.1(3) . . . . ?
C12 S1 C15 C14 -0.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_z_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1874278'
loop_
_audit_author_name
_audit_author_address
'Peigang Ding'
;??The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2018-10-20 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H21 Cl N2 O3'
_chemical_formula_weight         432.89

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   6.2023(2)
_cell_length_b                   15.1707(4)
_cell_length_c                   23.3424(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2196.36(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6102
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      23.02

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9323
_exptl_absorpt_correction_T_max  0.9663
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25874
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3885
_reflns_number_gt                3249
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0595P)²+0.3348P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3885
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1092
_refine_ls_wR_factor_gt          0.1005
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.99399(15) 0.84045(5) 0.88806(4) 0.0884(3) Uani 1 1 d . . .
O1 O 0.5563(3) 0.44383(12) 0.96452(7) 0.0575(5) Uani 1 1 d . . .
O2 O 1.2797(4) 0.46267(16) 1.10066(10) 0.0837(7) Uani 1 1 d . . .
O3 O 1.0281(6) 0.52055(16) 1.15196(9) 0.1088(10) Uani 1 1 d . . .
N2 N 0.9200(3) 0.33860(12) 1.01176(8) 0.0446(5) Uani 1 1 d . . .
H2B H 0.9551 0.2840 1.0086 0.054 Uiso 1 1 calc R . .
N1 N 1.0947(5) 0.48829(14) 1.10798(9) 0.0623(6) Uani 1 1 d . . .
C1 C 0.7688(4) 0.44995(15) 0.87850(10) 0.0444(6) Uani 1 1 d . . .
C2 C 0.6349(5) 0.48852(17) 0.83734(11) 0.0577(7) Uani 1 1 d . . .
H2A H 0.4971 0.5076 0.8469 0.069 Uiso 1 1 calc R . .
C3 C 0.7116(6) 0.4975(2) 0.78261(12) 0.0729(9) Uani 1 1 d . . .
H3A H 0.6264 0.5234 0.7545 0.087 Uiso 1 1 calc R . .
C4 C 0.9184(6) 0.4675(2) 0.76943(12) 0.0746(9) Uani 1 1 d . . .
H4A H 0.9695 0.4744 0.7322 0.089 Uiso 1 1 calc R . .
C5 C 1.0491(5) 0.42816(18) 0.80935(11) 0.0605(7) Uani 1 1 d . . .
H5A H 1.1854 0.4077 0.7993 0.073 Uiso 1 1 calc R . .
C6 C 0.9732(4) 0.41947(15) 0.86521(10) 0.0451(6) Uani 1 1 d . . .
C7 C 1.0778(4) 0.37739(16) 0.91631(10) 0.0461(6) Uani 1 1 d . . .
H7A H 1.2248 0.3980 0.9208 0.055 Uiso 1 1 calc R . .
H7B H 1.0792 0.3137 0.9125 0.055 Uiso 1 1 calc R . .
C8 C 0.9394(3) 0.40544(13) 0.96724(9) 0.0373(5) Uani 1 1 d . . .
C9 C 0.7257(4) 0.43446(14) 0.93896(10) 0.0411(5) Uani 1 1 d . . .
C10 C 1.0195(4) 0.57463(13) 0.97449(9) 0.0377(5) Uani 1 1 d . . .
C11 C 0.8365(4) 0.62672(15) 0.97750(10) 0.0467(6) Uani 1 1 d . . .
H11A H 0.7172 0.6068 0.9978 0.056 Uiso 1 1 calc R . .
C12 C 0.8285(4) 0.70787(15) 0.95073(11) 0.0521(6) Uani 1 1 d . . .
H12A H 0.7047 0.7423 0.9531 0.062 Uiso 1 1 calc R . .
C13 C 1.0034(4) 0.73711(15) 0.92087(11) 0.0528(6) Uani 1 1 d . . .
C14 C 1.1869(4) 0.68744(18) 0.91659(12) 0.0605(7) Uani 1 1 d . . .
H14A H 1.3046 0.7077 0.8957 0.073 Uiso 1 1 calc R . .
C15 C 1.1939(4) 0.60659(16) 0.94387(10) 0.0499(6) Uani 1 1 d . . .
H15A H 1.3188 0.5729 0.9416 0.060 Uiso 1 1 calc R . .
C16 C 0.8298(4) 0.38104(14) 1.06299(10) 0.0436(5) Uani 1 1 d . . .
H16A H 0.6739 0.3870 1.0573 0.052 Uiso 1 1 calc R . .
C17 C 0.9302(4) 0.47505(14) 1.06074(9) 0.0446(6) Uani 1 1 d . . .
H17A H 0.8156 0.5191 1.0646 0.054 Uiso 1 1 calc R . .
C18 C 1.0347(4) 0.48402(13) 1.00202(9) 0.0374(5) Uani 1 1 d . . .
H18A H 1.1885 0.4716 1.0072 0.045 Uiso 1 1 calc R . .
C19 C 0.8652(4) 0.33125(14) 1.11840(10) 0.0423(5) Uani 1 1 d . . .
C20 C 1.0554(5) 0.28714(16) 1.12985(11) 0.0529(6) Uani 1 1 d . . .
H20A H 1.1611 0.2825 1.1018 0.063 Uiso 1 1 calc R . .
C21 C 1.0878(5) 0.24993(17) 1.18334(12) 0.0618(7) Uani 1 1 d . . .
H21A H 1.2160 0.2202 1.1906 0.074 Uiso 1 1 calc R . .
C22 C 0.9358(6) 0.25576(17) 1.22586(11) 0.0628(8) Uani 1 1 d . . .
C23 C 0.7470(5) 0.29759(18) 1.21361(12) 0.0612(7) Uani 1 1 d . . .
H23A H 0.6404 0.3011 1.2415 0.073 Uiso 1 1 calc R . .
C24 C 0.7108(4) 0.33507(16) 1.16028(11) 0.0535(6) Uani 1 1 d . . .
H24A H 0.5803 0.3631 1.1529 0.064 Uiso 1 1 calc R . .
C25 C 0.9764(7) 0.2168(2) 1.28472(13) 0.1019(13) Uani 1 1 d . . .
H25A H 0.8527 0.2266 1.3086 0.153 Uiso 1 1 calc R . .
H25B H 1.1002 0.2445 1.3016 0.153 Uiso 1 1 calc R . .
H25C H 1.0019 0.1546 1.2812 0.153 Uiso 1 1 calc R . .


_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
Cl1 C13 1.746(2) . ?
O1 C9 1.217(3) . ?
O2 N1 1.224(3) . ?
O3 N1 1.210(3) . ?
N2 C8 1.457(3) . ?
N2 C16 1.469(3) . ?
N2 H2B 0.8600 . ?
N1 C17 1.515(4) . ?
C1 C6 1.385(3) . ?
C1 C2 1.398(3) . ?
C1 C9 1.455(3) . ?
C2 C3 1.370(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.396(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.372(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.392(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.500(3) . ?
C7 C8 1.527(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.545(3) . ?
C8 C18 1.559(3) . ?
C10 C15 1.384(3) . ?
C10 C11 1.385(3) . ?
C10 C18 1.520(3) . ?
C11 C12 1.381(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.364(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.368(4) . ?
C14 C15 1.383(4) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C19 1.514(3) . ?
C16 C17 1.557(3) . ?
C16 H16A 0.9800 . ?
C17 C18 1.522(3) . ?
C17 H17A 0.9800 . ?
C18 H18A 0.9800 . ?
C19 C24 1.370(3) . ?
C19 C20 1.382(4) . ?
C20 C21 1.385(4) . ?
C20 H20A 0.9300 . ?
C21 C22 1.372(4) . ?
C21 H21A 0.9300 . ?
C22 C23 1.362(4) . ?
C22 C25 1.517(4) . ?
C23 C24 1.387(4) . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
C8 N2 C16 107.89(16) . . ?
C8 N2 H2B 126.1 . . ?
C16 N2 H2B 126.1 . . ?
O3 N1 O2 124.5(3) . . ?
O3 N1 C17 116.2(3) . . ?
O2 N1 C17 119.2(2) . . ?
C6 C1 C2 122.0(2) . . ?
C6 C1 C9 109.3(2) . . ?
C2 C1 C9 128.7(2) . . ?
C3 C2 C1 118.5(3) . . ?
C3 C2 H2A 120.8 . . ?
C1 C2 H2A 120.8 . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C5 C4 C3 122.4(3) . . ?
C5 C4 H4A 118.8 . . ?
C3 C4 H4A 118.8 . . ?
C4 C5 C6 118.5(3) . . ?
C4 C5 H5A 120.7 . . ?
C6 C5 H5A 120.7 . . ?
C1 C6 C5 119.2(2) . . ?
C1 C6 C7 111.1(2) . . ?
C5 C6 C7 129.7(2) . . ?
C6 C7 C8 104.94(18) . . ?
C6 C7 H7A 110.8 . . ?
C8 C7 H7A 110.8 . . ?
C6 C7 H7B 110.8 . . ?
C8 C7 H7B 110.8 . . ?
H7A C7 H7B 108.8 . . ?
N2 C8 C7 114.09(18) . . ?
N2 C8 C9 115.59(18) . . ?
C7 C8 C9 103.23(17) . . ?
N2 C8 C18 101.09(16) . . ?
C7 C8 C18 113.94(19) . . ?
C9 C8 C18 109.26(17) . . ?
O1 C9 C1 128.0(2) . . ?
O1 C9 C8 124.4(2) . . ?
C1 C9 C8 107.64(19) . . ?
C15 C10 C11 117.8(2) . . ?
C15 C10 C18 119.13(19) . . ?
C11 C10 C18 123.0(2) . . ?
C12 C11 C10 121.0(2) . . ?
C12 C11 H11A 119.5 . . ?
C10 C11 H11A 119.5 . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 H12A 120.3 . . ?
C11 C12 H12A 120.3 . . ?
C12 C13 C14 121.3(2) . . ?
C12 C13 Cl1 119.3(2) . . ?
C14 C13 Cl1 119.4(2) . . ?
C13 C14 C15 118.7(2) . . ?
C13 C14 H14A 120.6 . . ?
C15 C14 H14A 120.6 . . ?
C14 C15 C10 121.6(2) . . ?
C14 C15 H15A 119.2 . . ?
C10 C15 H15A 119.2 . . ?
N2 C16 C19 114.94(18) . . ?
N2 C16 C17 102.80(18) . . ?
C19 C16 C17 115.32(19) . . ?
N2 C16 H16A 107.8 . . ?
C19 C16 H16A 107.8 . . ?
C17 C16 H16A 107.8 . . ?
N1 C17 C18 110.9(2) . . ?
N1 C17 C16 111.48(18) . . ?
C18 C17 C16 106.40(17) . . ?
N1 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17A 109.3 . . ?
C10 C18 C17 115.79(17) . . ?
C10 C18 C8 116.63(17) . . ?
C17 C18 C8 103.85(18) . . ?
C10 C18 H18A 106.6 . . ?
C17 C18 H18A 106.6 . . ?
C8 C18 H18A 106.6 . . ?
C24 C19 C20 118.6(2) . . ?
C24 C19 C16 119.2(2) . . ?
C20 C19 C16 122.1(2) . . ?
C19 C20 C21 119.7(3) . . ?
C19 C20 H20A 120.1 . . ?
C21 C20 H20A 120.1 . . ?
C22 C21 C20 121.8(3) . . ?
C22 C21 H21A 119.1 . . ?
C20 C21 H21A 119.1 . . ?
C23 C22 C21 118.0(2) . . ?
C23 C22 C25 121.0(3) . . ?
C21 C22 C25 121.1(3) . . ?
C22 C23 C24 121.2(3) . . ?
C22 C23 H23A 119.4 . . ?
C24 C23 H23A 119.4 . . ?
C19 C24 C23 120.7(3) . . ?
C19 C24 H24A 119.7 . . ?
C23 C24 H24A 119.7 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C6 C1 C2 C3 -1.2(4) . . . . ?
C9 C1 C2 C3 179.1(3) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C3 C4 C5 C6 -1.2(4) . . . . ?
C2 C1 C6 C5 0.6(4) . . . . ?
C9 C1 C6 C5 -179.6(2) . . . . ?
C2 C1 C6 C7 -177.3(2) . . . . ?
C9 C1 C6 C7 2.5(3) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
C4 C5 C6 C7 178.0(3) . . . . ?
C1 C6 C7 C8 -14.0(3) . . . . ?
C5 C6 C7 C8 168.4(2) . . . . ?
C16 N2 C8 C7 166.53(19) . . . . ?
C16 N2 C8 C9 -74.0(2) . . . . ?
C16 N2 C8 C18 43.8(2) . . . . ?
C6 C7 C8 N2 144.96(19) . . . . ?
C6 C7 C8 C9 18.7(2) . . . . ?
C6 C7 C8 C18 -99.6(2) . . . . ?
C6 C1 C9 O1 -171.5(2) . . . . ?
C2 C1 C9 O1 8.2(4) . . . . ?
C6 C1 C9 C8 10.0(2) . . . . ?
C2 C1 C9 C8 -170.2(2) . . . . ?
N2 C8 C9 O1 38.3(3) . . . . ?
C7 C8 C9 O1 163.6(2) . . . . ?
C18 C8 C9 O1 -74.8(3) . . . . ?
N2 C8 C9 C1 -143.21(18) . . . . ?
C7 C8 C9 C1 -17.9(2) . . . . ?
C18 C8 C9 C1 103.6(2) . . . . ?
C15 C10 C11 C12 0.0(4) . . . . ?
C18 C10 C11 C12 -178.6(2) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C11 C12 C13 Cl1 -179.0(2) . . . . ?
C12 C13 C14 C15 -0.8(4) . . . . ?
Cl1 C13 C14 C15 178.6(2) . . . . ?
C13 C14 C15 C10 0.9(4) . . . . ?
C11 C10 C15 C14 -0.5(4) . . . . ?
C18 C10 C15 C14 178.1(2) . . . . ?
C8 N2 C16 C19 -160.83(18) . . . . ?
C8 N2 C16 C17 -34.7(2) . . . . ?
O3 N1 C17 C18 148.6(2) . . . . ?
O2 N1 C17 C18 -34.7(3) . . . . ?
O3 N1 C17 C16 -93.0(2) . . . . ?
O2 N1 C17 C16 83.7(3) . . . . ?
N2 C16 C17 N1 -110.2(2) . . . . ?
C19 C16 C17 N1 15.7(3) . . . . ?
N2 C16 C17 C18 10.9(2) . . . . ?
C19 C16 C17 C18 136.7(2) . . . . ?
C15 C10 C18 C17 141.7(2) . . . . ?
C11 C10 C18 C17 -39.7(3) . . . . ?
C15 C10 C18 C8 -95.7(2) . . . . ?
C11 C10 C18 C8 82.9(3) . . . . ?
N1 C17 C18 C10 -95.0(2) . . . . ?
C16 C17 C18 C10 143.55(19) . . . . ?
N1 C17 C18 C8 135.78(18) . . . . ?
C16 C17 C18 C8 14.4(2) . . . . ?
N2 C8 C18 C10 -163.10(18) . . . . ?
C7 C8 C18 C10 74.1(2) . . . . ?
C9 C8 C18 C10 -40.8(2) . . . . ?
N2 C8 C18 C17 -34.4(2) . . . . ?
C7 C8 C18 C17 -157.26(18) . . . . ?
C9 C8 C18 C17 87.9(2) . . . . ?
N2 C16 C19 C24 -146.5(2) . . . . ?
C17 C16 C19 C24 94.1(3) . . . . ?
N2 C16 C19 C20 38.3(3) . . . . ?
C17 C16 C19 C20 -81.1(3) . . . . ?
C24 C19 C20 C21 -1.5(4) . . . . ?
C16 C19 C20 C21 173.7(2) . . . . ?
C19 C20 C21 C22 -0.2(4) . . . . ?
C20 C21 C22 C23 1.7(4) . . . . ?
C20 C21 C22 C25 -178.3(3) . . . . ?
C21 C22 C23 C24 -1.5(4) . . . . ?
C25 C22 C23 C24 178.6(3) . . . . ?
C20 C19 C24 C23 1.8(4) . . . . ?
C16 C19 C24 C23 -173.6(2) . . . . ?
C22 C23 C24 C19 -0.3(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.031
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_517
_database_code_depnum_ccdc_archive 'CCDC 1874283'
loop_
_audit_author_name
_audit_author_address
'Peigang Ding'
;??The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2018-10-20 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;
_audit_creation_date             2018-10-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H14 Br2 N4 O3'
_chemical_formula_sum            'C18 H14 Br2 N4 O3'
_chemical_formula_weight         494.15
_chemical_absolute_configuration ad
_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           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                   7.63640(10)
_cell_length_b                   11.6851(2)
_cell_length_c                   11.5473(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.259(2)
_cell_angle_gamma                90
_cell_volume                     998.65(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12619
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.9920
_cell_measurement_theta_min      5.4150
_shelx_estimated_absorpt_T_max   0.445
_shelx_estimated_absorpt_T_min   0.278
_exptl_absorpt_coefficient_mu    5.374
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.32a (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_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21816
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.458
_diffrn_reflns_theta_min         3.950
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00 -14.00   1.00    2.00    --    0.00 -52.00 -80.00   26
  2  ω    -22.00  45.00   1.00    2.00    --    0.00  52.00  65.00   67
  3  ω     42.00  67.00   1.00    2.00    --   95.80 -52.00 -80.00   25
  4  ω     76.00 172.00   1.00    2.00    --   95.80  52.00  65.00   96
  5  ω    -21.00  23.00   1.00    2.00    --    0.00 -57.00  60.00   44
  6  ω     39.00  84.00   1.00    2.00    --    0.00  38.00   0.00   45
  7  ω    -19.00  33.00   1.00    2.00    --    0.00  38.00   0.00   52
  8  ω      7.00  62.00   1.00    2.00    --    0.00  77.00  60.00   55
  9  ω    -89.00 -51.00   1.00    2.00    --    0.00 -38.00 -60.00   38
 10  ω    -89.00 -30.00   1.00    2.00    --    0.00 -57.00  60.00   59
 11  ω    -11.00  24.00   1.00    2.00    --    0.00 -19.00-150.00   35
 12  ω    -43.00  17.00   1.00    2.00    --    0.00 -38.00 -60.00   60
 13  ω    -22.00  54.00   1.00    2.00    --    0.00  57.00 -60.00   76
 14  ω     39.00  75.00   1.00    2.00    --    0.00  19.00-120.00   36
 15  ω    -19.00  31.00   1.00    2.00    --    0.00  38.00 150.00   50
 16  ω    -50.00 -24.00   1.00    2.00    --    0.00 -19.00-150.00   26
 17  ω    -19.00  33.00   1.00    2.00    --    0.00  19.00-120.00   52
 18  ω     65.00 118.00   1.00    2.00    --   95.80  79.00 161.77   53
 19  ω     72.00 107.00   1.00    2.00    --   95.80  58.00  41.77   35
 20  ω     41.00 126.00   1.00    2.00    --   95.80 -82.00 150.00   85
 21  ω     73.00 128.00   1.00    2.00    --   95.80 -82.00 -60.00   55
 22  ω     79.00 128.00   1.00    2.00    --   95.80 -82.00-150.00   49
 23  ω     11.00  37.00   1.00    2.00    --   95.80 -82.00 150.00   26
 24  ω    145.00 172.00   1.00    2.00    --   95.80  77.00-150.00   27
 25  ω    129.00 159.00   1.00    2.00    --   95.80  45.00  30.00   30
 26  ω    114.00 173.00   1.00    2.00    --   95.80  79.00 -77.07   59
 27  ω     75.00 119.00   1.00    2.00    --   95.80  45.00  30.00   44
 28  ω     71.00  96.00   1.00    2.00    --   95.80  61.00-150.00   25
 29  ω     65.00  99.00   1.00    2.00    --   95.80  77.00 120.00   34
 30  ω     75.00 114.00   1.00    2.00    --   95.80  45.00   0.00   39
 31  ω    116.00 141.00   1.00    2.00    --   95.80  45.00   0.00   25
 32  ω    149.00 185.00   1.00    2.00    --   95.80  45.00   0.00   36
 33  ω     64.00  89.00   1.00    2.00    --   95.80  80.00 100.76   25
 34  ω     67.00  93.00   1.00    2.00    --   95.80  73.00  78.89   26
 35  ω     75.00 121.00   1.00    2.00    --   95.80  45.00 -90.00   46
 36  ω     65.00 178.00   1.00    2.00    --   95.80  77.00  90.00  113
 37  ω     65.00  90.00   1.00    2.00    --   95.80  77.00 -30.00   25
 38  ω    146.00 171.00   1.00    2.00    --   95.80  77.00   0.00   25
 39  ω     75.00 185.00   1.00    2.00    --   95.80  45.00 -30.00  110
 40  ω     63.00 185.00   1.00    2.00    --   95.80  82.00 130.09  122
 41  ω     80.00 184.00   1.00    2.00    --   95.80  45.00-120.00  104
 42  ω    111.00 156.00   1.00    2.00    --   95.80  82.00 150.00   45
 43  ω     71.00 175.00   1.00    2.00    --   95.80  59.00  76.40  104
 44  ω     65.00  90.00   1.00    2.00    --   95.80  77.00  60.00   25
 45  ω    152.00 178.00   1.00    2.00    --   95.80  77.00  60.00   26
 46  ω     64.00  98.00   1.00    2.00    --   95.80  79.00 -77.07   34
 47  ω    116.00 185.00   1.00    2.00    --   95.80  82.00-120.00   69
 48  ω     69.00  95.00   1.00    2.00    --   95.80  82.00 -30.00   26
 49  ω    139.00 168.00   1.00    2.00    --   95.80  82.00 -30.00   29
 50  ω     64.00  89.00   1.00    2.00    --   95.80  82.00   0.00   25
 51  ω     63.00  99.00   1.00    2.00    --   95.80  82.00 150.00   36
 52  ω     68.00 123.00   1.00    2.00    --   95.80 -77.00 -90.00   55
 53  ω     12.00  49.00   1.00    2.00    --   95.80 -77.00 -90.00   37
 54  ω     65.00  91.00   1.00    2.00    --   95.80  77.00  30.00   26
 55  ω     76.00 102.00   1.00    2.00    --   95.80  61.00  60.00   26
 56  ω     66.00  92.00   1.00    2.00    --   95.80  77.00 -90.00   26
 57  ω     63.00  88.00   1.00    2.00    --   95.80  82.00 120.00   25
 58  ω     78.00 122.00   1.00    2.00    --   95.80 -82.00   0.00   44
 59  ω     71.00  96.00   1.00    2.00    --   95.80  61.00-120.00   25
 60  ω     65.00  91.00   1.00    2.00    --   95.80  77.00-180.00   26
 61  ω    139.00 169.00   1.00    2.00    --   95.80  77.00-180.00   30
 62  ω     61.00 105.00   1.00    2.00    --   95.80 -82.00  90.00   44
 63  ω    130.00 167.00   1.00    2.00    --   95.80  79.00 161.77   37
 64  ω     89.00 115.00   1.00    2.00    --   95.80  30.00 -60.00   26
 65  ω     63.00  88.00   1.00    2.00    --   95.80  82.00-120.00   25
 66  ω     65.00  91.00   1.00    2.00    --   95.80  77.00   0.00   26
 67  ω     65.00  90.00   1.00    2.00    --   95.80  77.00-150.00   25
 68  ω     65.00  90.00   1.00    2.00    --   95.80  77.00 -60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1207180000
_diffrn_orient_matrix_UB_12      0.0873431000
_diffrn_orient_matrix_UB_13      0.0436225000
_diffrn_orient_matrix_UB_21      -0.1357054000
_diffrn_orient_matrix_UB_22      -0.0037369000
_diffrn_orient_matrix_UB_23      -0.1231976000
_diffrn_orient_matrix_UB_31      -0.1017326000
_diffrn_orient_matrix_UB_32      -0.0986824000
_diffrn_orient_matrix_UB_33      0.0431811000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.885
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                3735
_reflns_number_total             4011
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 1583 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.015(12)
_refine_ls_extinction_coef       0.0081(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4011
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      1.059
_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)+(0.0605P)²+0.2211P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1061
_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:
 C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17)
;
_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 0.14195(9) 0.23183(8) -0.03048(4) 0.0872(3) Uani 1 1 d . . . . .
Br2 Br 0.37674(17) 0.96481(8) 0.90308(9) 0.1152(4) Uani 1 1 d . . . . .
O1 O 0.1169(6) 0.0340(3) 0.5204(4) 0.0720(10) Uani 1 1 d . . . . .
O2 O 0.6661(6) 0.3077(4) 0.6254(4) 0.0764(11) Uani 1 1 d . . . . .
O3 O 0.6852(7) 0.2949(6) 0.8130(5) 0.0976(16) Uani 1 1 d . . . . .
N1 N 0.6083(6) 0.2766(4) 0.7092(4) 0.0629(11) Uani 1 1 d . . . . .
N2 N 0.0683(6) 0.1893(5) 0.6852(4) 0.0642(11) Uani 1 1 d . . . . .
N3 N -0.0588(6) 0.1218(4) 0.6746(4) 0.0625(10) Uani 1 1 d . . . . .
N4 N -0.1720(8) 0.0608(5) 0.6796(6) 0.0847(15) Uani 1 1 d . . . . .
C1 C 0.1556(6) 0.0717(5) 0.2900(4) 0.0579(11) Uani 1 1 d . . . . .
H1 H 0.170450 -0.002474 0.319985 0.069 Uiso 1 1 calc R . . . .
C2 C 0.1646(7) 0.0933(6) 0.1743(5) 0.0645(13) Uani 1 1 d . . . . .
H2 H 0.187173 0.034001 0.126153 0.077 Uiso 1 1 calc R . . . .
C3 C 0.1401(6) 0.2031(6) 0.1304(4) 0.0630(13) Uani 1 1 d . . . . .
C4 C 0.1066(7) 0.2925(5) 0.2005(5) 0.0614(12) Uani 1 1 d . . . . .
H4 H 0.089716 0.366487 0.170016 0.074 Uiso 1 1 calc R . . . .
C5 C 0.0986(7) 0.2703(5) 0.3162(4) 0.0583(12) Uani 1 1 d . . . . .
H5 H 0.075597 0.329612 0.364028 0.070 Uiso 1 1 calc R . . . .
C6 C 0.1244(6) 0.1609(4) 0.3618(4) 0.0513(10) Uani 1 1 d . . . . .
C7 C 0.1144(6) 0.1313(5) 0.4864(4) 0.0530(10) Uani 1 1 d . . . . .
C8 C 0.1056(5) 0.2304(5) 0.5727(3) 0.0508(9) Uani 1 1 d . . . . .
H8 H 0.010332 0.283890 0.533784 0.061 Uiso 1 1 calc R . . . .
C9 C 0.2863(6) 0.2949(4) 0.6092(4) 0.0492(9) Uani 1 1 d . . . . .
H9 H 0.322271 0.315005 0.535899 0.059 Uiso 1 1 calc R . . . .
C10 C 0.2773(6) 0.4031(4) 0.6764(4) 0.0507(10) Uani 1 1 d . . . . .
H10 H 0.225688 0.400587 0.741396 0.061 Uiso 1 1 calc R . . . .
C11 C 0.3391(6) 0.5017(4) 0.6481(4) 0.0512(10) Uani 1 1 d . . . . .
H11 H 0.382653 0.501961 0.579670 0.061 Uiso 1 1 calc R . . . .
C12 C 0.3476(6) 0.6111(4) 0.7111(4) 0.0497(9) Uani 1 1 d . . . . .
C13 C 0.3778(7) 0.7108(5) 0.6544(4) 0.0604(11) Uani 1 1 d . . . . .
H13 H 0.392595 0.706634 0.576966 0.073 Uiso 1 1 calc R . . . .
C14 C 0.3869(9) 0.8171(5) 0.7099(6) 0.0708(15) Uani 1 1 d . . . . .
H14 H 0.404554 0.883579 0.669984 0.085 Uiso 1 1 calc R . . . .
C15 C 0.3691(9) 0.8212(5) 0.8246(6) 0.0678(14) Uani 1 1 d . . . . .
C16 C 0.3406(7) 0.7234(5) 0.8850(4) 0.0628(11) Uani 1 1 d . . . . .
H16 H 0.329132 0.728246 0.963166 0.075 Uiso 1 1 calc R . . . .
C17 C 0.3294(7) 0.6198(4) 0.8288(4) 0.0557(11) Uani 1 1 d . . . . .
H17 H 0.309571 0.554057 0.869197 0.067 Uiso 1 1 calc R . . . .
C18 C 0.4330(6) 0.2161(5) 0.6834(5) 0.0607(11) Uani 1 1 d . . . . .
H18A H 0.402746 0.195751 0.757577 0.073 Uiso 1 1 calc R . . . .
H18B H 0.440540 0.146341 0.639405 0.073 Uiso 1 1 calc R . . . .


_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 C3 1.892(5) . ?
Br2 C15 1.902(6) . ?
O1 C7 1.201(7) . ?
O2 N1 1.214(7) . ?
O3 N1 1.217(6) . ?
N1 C18 1.478(7) . ?
N2 N3 1.234(7) . ?
N2 C8 1.477(6) . ?
N3 N4 1.132(7) . ?
C1 H1 0.9300 . ?
C1 C2 1.379(8) . ?
C1 C6 1.388(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(9) . ?
C3 C4 1.384(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(7) . ?
C6 C7 1.500(6) . ?
C7 C8 1.540(7) . ?
C8 H8 0.9800 . ?
C8 C9 1.537(6) . ?
C9 H9 0.9800 . ?
C9 C10 1.494(6) . ?
C9 C18 1.537(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.317(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.464(7) . ?
C12 C13 1.383(8) . ?
C12 C17 1.404(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.392(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.364(10) . ?
C15 C16 1.383(9) . ?
C16 H16 0.9300 . ?
C16 C17 1.367(8) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 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
O2 N1 O3 123.4(5) . . ?
O2 N1 C18 118.1(4) . . ?
O3 N1 C18 118.4(5) . . ?
N3 N2 C8 116.0(4) . . ?
N4 N3 N2 171.6(6) . . ?
C2 C1 H1 120.0 . . ?
C2 C1 C6 119.9(5) . . ?
C6 C1 H1 120.0 . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.5(5) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 Br1 119.6(4) . . ?
C2 C3 C4 121.2(5) . . ?
C4 C3 Br1 119.2(5) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 118.9(5) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.7(5) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C7 117.2(5) . . ?
C5 C6 C1 119.8(4) . . ?
C5 C6 C7 123.0(4) . . ?
O1 C7 C6 122.1(5) . . ?
O1 C7 C8 120.0(4) . . ?
C6 C7 C8 117.9(4) . . ?
N2 C8 C7 111.9(4) . . ?
N2 C8 H8 109.2 . . ?
N2 C8 C9 105.8(3) . . ?
C7 C8 H8 109.2 . . ?
C9 C8 C7 111.5(3) . . ?
C9 C8 H8 109.2 . . ?
C8 C9 H9 107.7 . . ?
C8 C9 C18 109.9(4) . . ?
C10 C9 C8 113.8(4) . . ?
C10 C9 H9 107.7 . . ?
C10 C9 C18 109.7(4) . . ?
C18 C9 H9 107.7 . . ?
C9 C10 H10 118.4 . . ?
C11 C10 C9 123.1(4) . . ?
C11 C10 H10 118.4 . . ?
C10 C11 H11 116.0 . . ?
C10 C11 C12 128.0(4) . . ?
C12 C11 H11 116.0 . . ?
C13 C12 C11 119.5(4) . . ?
C13 C12 C17 117.7(4) . . ?
C17 C12 C11 122.8(4) . . ?
C12 C13 H13 119.0 . . ?
C12 C13 C14 121.9(5) . . ?
C14 C13 H13 119.0 . . ?
C13 C14 H14 120.9 . . ?
C15 C14 C13 118.2(5) . . ?
C15 C14 H14 120.9 . . ?
C14 C15 Br2 119.6(5) . . ?
C14 C15 C16 121.8(5) . . ?
C16 C15 Br2 118.6(5) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.4(5) . . ?
C17 C16 H16 120.3 . . ?
C12 C17 H17 119.5 . . ?
C16 C17 C12 120.9(5) . . ?
C16 C17 H17 119.5 . . ?
N1 C18 C9 109.0(4) . . ?
N1 C18 H18A 109.9 . . ?
N1 C18 H18B 109.9 . . ?
C9 C18 H18A 109.9 . . ?
C9 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?

_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 4.897
_oxdiff_exptl_absorpt_empirical_full_min 0.287
####################################################################### 
# 
# 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_cu_dm16503_0m
_database_code_depnum_ccdc_archive 'CCDC 1874281'
loop_
_audit_author_name
_audit_author_address
'Peigang Ding'
;??The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2018-10-20 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;
_audit_creation_date             2016-08-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 F N4 O3'
_chemical_formula_sum            'C19 H15 F N4 O3'
_chemical_formula_weight         366.35
_chemical_absolute_configuration rmad
_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'
F F 0.0727 0.0534 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.3148(2)
_cell_length_b                   11.9114(3)
_cell_length_c                   14.6673(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1802.08(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3485
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      61.889
_cell_measurement_theta_min      3.711
_shelx_estimated_absorpt_T_max   0.883
_shelx_estimated_absorpt_T_min   0.816
_exptl_absorpt_coefficient_mu    0.848
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1052 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.8816.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12680
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.605
_diffrn_reflns_theta_min         4.782
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                2819
_reflns_number_total             3229
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.846
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 1071 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(11)
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0691
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1729P)²+0.1627P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2196
_refine_ls_wR_factor_ref         0.2314
_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:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C16(H16), C17(H17),
 C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_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
F1 F 0.8690(5) 0.2750(4) 0.4148(4) 0.1503(19) Uani 1 1 d . . . . .
O1 O 0.3852(4) 0.6665(3) 0.2589(3) 0.0965(11) Uani 1 1 d . . . . .
O2 O 0.7432(5) 0.5702(5) 0.1188(3) 0.1203(16) Uani 1 1 d . . . . .
O3 O 0.7578(5) 0.3984(5) 0.0854(4) 0.1327(19) Uani 1 1 d . . . . .
N1 N 0.4770(5) 0.5284(5) 0.4185(3) 0.0891(12) Uani 1 1 d . . . . .
N2 N 0.5193(6) 0.6254(5) 0.4263(3) 0.1017(16) Uani 1 1 d . . . . .
N3 N 0.5593(10) 0.7108(6) 0.4442(5) 0.154(3) Uani 1 1 d . . . . .
N4 N 0.7063(4) 0.4748(5) 0.1240(3) 0.0891(13) Uani 1 1 d . . . . .
C1 C 0.4662(4) 0.4901(4) 0.3232(3) 0.0682(10) Uani 1 1 d . . . . .
C2 C 0.3682(4) 0.5672(4) 0.2724(3) 0.0719(11) Uani 1 1 d . . . . .
C3 C 0.2580(4) 0.4984(4) 0.2443(3) 0.0705(10) Uani 1 1 d . . . . .
C4 C 0.1475(5) 0.5299(5) 0.1951(3) 0.0890(15) Uani 1 1 d . . . . .
H4 H 0.1366 0.6040 0.1766 0.107 Uiso 1 1 calc R . . . .
C5 C 0.0579(5) 0.4527(7) 0.1749(4) 0.1056(19) Uani 1 1 d . . . . .
H5 H -0.0152 0.4725 0.1414 0.127 Uiso 1 1 calc R . . . .
C6 C 0.0747(6) 0.3427(7) 0.2043(4) 0.111(2) Uani 1 1 d . . . . .
H6 H 0.0109 0.2899 0.1914 0.134 Uiso 1 1 calc R . . . .
C7 C 0.1829(6) 0.3103(5) 0.2518(5) 0.0989(16) Uani 1 1 d . . . . .
H7 H 0.1930 0.2360 0.2700 0.119 Uiso 1 1 calc R . . . .
C8 C 0.2767(4) 0.3892(4) 0.2721(3) 0.0740(11) Uani 1 1 d . . . . .
C9 C 0.4001(4) 0.3745(4) 0.3244(4) 0.0805(12) Uani 1 1 d . . . . .
H9A H 0.4549 0.3185 0.2957 0.097 Uiso 1 1 calc R . . . .
H9B H 0.3822 0.3511 0.3865 0.097 Uiso 1 1 calc R . . . .
C10 C 0.5986(4) 0.4978(4) 0.2744(2) 0.0647(9) Uani 1 1 d . . . . .
H10 H 0.6207 0.5775 0.2685 0.078 Uiso 1 1 calc R . . . .
C11 C 0.5864(4) 0.4494(5) 0.1784(3) 0.0776(12) Uani 1 1 d . . . . .
H11A H 0.5740 0.3688 0.1819 0.093 Uiso 1 1 calc R . . . .
H11B H 0.5114 0.4817 0.1484 0.093 Uiso 1 1 calc R . . . .
C12 C 0.7059(4) 0.4419(4) 0.3259(3) 0.0664(9) Uani 1 1 d . . . . .
H12 H 0.7025 0.3646 0.3344 0.080 Uiso 1 1 calc R . . . .
C13 C 0.8051(4) 0.4980(4) 0.3597(3) 0.0683(10) Uani 1 1 d . . . . .
H13 H 0.8018 0.5752 0.3503 0.082 Uiso 1 1 calc R . . . .
C14 C 0.9205(4) 0.4585(4) 0.4101(3) 0.0707(11) Uani 1 1 d . . . . .
C15 C 0.9491(6) 0.3530(5) 0.4349(3) 0.0870(14) Uani 1 1 d . . . . .
C16 C 1.0604(8) 0.3202(7) 0.4809(4) 0.111(2) Uani 1 1 d . . . . .
H16 H 1.0756 0.2456 0.4963 0.133 Uiso 1 1 calc R . . . .
C17 C 1.1471(6) 0.4039(9) 0.5027(4) 0.112(2) Uani 1 1 d . . . . .
H17 H 1.2223 0.3854 0.5342 0.134 Uiso 1 1 calc R . . . .
C18 C 1.1264(6) 0.5091(8) 0.4802(4) 0.110(2) Uani 1 1 d . . . . .
H18 H 1.1883 0.5624 0.4961 0.132 Uiso 1 1 calc R . . . .
C19 C 1.0144(5) 0.5449(9) 0.4329(4) 0.118(3) Uani 1 1 d . . . . .
H19 H 1.0015 0.6198 0.4174 0.141 Uiso 1 1 calc R . . . .


_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
F1 C15 1.277(7) . ?
O1 C2 1.211(6) . ?
O2 N4 1.201(7) . ?
O3 N4 1.196(7) . ?
N1 N2 1.240(8) . ?
N1 C1 1.475(6) . ?
N2 N3 1.128(9) . ?
N4 C11 1.503(6) . ?
C1 C2 1.556(6) . ?
C1 C9 1.537(6) . ?
C1 C10 1.545(6) . ?
C2 C3 1.461(6) . ?
C3 C4 1.401(6) . ?
C3 C8 1.376(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.337(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.390(10) . ?
C6 H6 0.9300 . ?
C6 C7 1.371(10) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(7) . ?
C8 C9 1.497(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10 0.9800 . ?
C10 C11 1.526(6) . ?
C10 C12 1.496(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12 0.9300 . ?
C12 C13 1.318(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.478(6) . ?
C14 C15 1.341(7) . ?
C14 C19 1.453(9) . ?
C15 C16 1.388(9) . ?
C16 H16 0.9300 . ?
C16 C17 1.377(11) . ?
C17 H17 0.9300 . ?
C17 C18 1.313(11) . ?
C18 H18 0.9300 . ?
C18 C19 1.414(9) . ?
C19 H19 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
N2 N1 C1 113.7(4) . . ?
N3 N2 N1 171.7(7) . . ?
O2 N4 C11 119.0(5) . . ?
O3 N4 O2 123.3(6) . . ?
O3 N4 C11 117.7(6) . . ?
N1 C1 C2 108.7(4) . . ?
N1 C1 C9 107.4(4) . . ?
N1 C1 C10 110.8(3) . . ?
C9 C1 C2 104.3(3) . . ?
C9 C1 C10 116.8(4) . . ?
C10 C1 C2 108.5(3) . . ?
O1 C2 C1 124.1(4) . . ?
O1 C2 C3 127.9(4) . . ?
C3 C2 C1 108.0(4) . . ?
C4 C3 C2 128.9(5) . . ?
C8 C3 C2 109.8(4) . . ?
C8 C3 C4 121.3(5) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.5(6) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.6(6) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.6(6) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 120.4 . . ?
C6 C7 C8 119.2(6) . . ?
C8 C7 H7 120.4 . . ?
C3 C8 C7 118.8(5) . . ?
C3 C8 C9 112.4(4) . . ?
C7 C8 C9 128.8(5) . . ?
C1 C9 H9A 110.7 . . ?
C1 C9 H9B 110.7 . . ?
C8 C9 C1 105.4(4) . . ?
C8 C9 H9A 110.7 . . ?
C8 C9 H9B 110.7 . . ?
H9A C9 H9B 108.8 . . ?
C1 C10 H10 107.7 . . ?
C11 C10 C1 109.4(3) . . ?
C11 C10 H10 107.7 . . ?
C12 C10 C1 113.2(3) . . ?
C12 C10 H10 107.7 . . ?
C12 C10 C11 111.0(4) . . ?
N4 C11 C10 110.2(3) . . ?
N4 C11 H11A 109.6 . . ?
N4 C11 H11B 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C10 C12 H12 118.7 . . ?
C13 C12 C10 122.5(4) . . ?
C13 C12 H12 118.7 . . ?
C12 C13 H13 114.7 . . ?
C12 C13 C14 130.6(4) . . ?
C14 C13 H13 114.7 . . ?
C15 C14 C13 127.7(5) . . ?
C15 C14 C19 117.0(5) . . ?
C19 C14 C13 115.3(5) . . ?
F1 C15 C14 118.5(5) . . ?
F1 C15 C16 116.2(6) . . ?
C14 C15 C16 125.3(6) . . ?
C15 C16 H16 121.8 . . ?
C17 C16 C15 116.5(6) . . ?
C17 C16 H16 121.8 . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.9(6) . . ?
C18 C17 H17 119.1 . . ?
C17 C18 H18 118.5 . . ?
C17 C18 C19 122.9(8) . . ?
C19 C18 H18 118.5 . . ?
C14 C19 H19 121.8 . . ?
C18 C19 C14 116.4(8) . . ?
C18 C19 H19 121.8 . . ?

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
F1 C15 C16 C17 180.0(6) . . . . ?
O1 C2 C3 C4 0.6(8) . . . . ?
O1 C2 C3 C8 179.3(5) . . . . ?
O2 N4 C11 C10 -53.1(6) . . . . ?
O3 N4 C11 C10 129.3(5) . . . . ?
N1 C1 C2 O1 64.5(6) . . . . ?
N1 C1 C2 C3 -116.3(4) . . . . ?
N1 C1 C9 C8 118.1(4) . . . . ?
N1 C1 C10 C11 175.8(4) . . . . ?
N1 C1 C10 C12 51.4(5) . . . . ?
N2 N1 C1 C2 -62.2(6) . . . . ?
N2 N1 C1 C9 -174.4(4) . . . . ?
N2 N1 C1 C10 57.0(6) . . . . ?
C1 C2 C3 C4 -178.5(4) . . . . ?
C1 C2 C3 C8 0.2(5) . . . . ?
C1 C10 C11 N4 169.7(4) . . . . ?
C1 C10 C12 C13 -115.2(5) . . . . ?
C2 C1 C9 C8 2.9(5) . . . . ?
C2 C1 C10 C11 -65.0(5) . . . . ?
C2 C1 C10 C12 170.6(3) . . . . ?
C2 C3 C4 C5 178.9(5) . . . . ?
C2 C3 C8 C7 -179.8(4) . . . . ?
C2 C3 C8 C9 1.8(5) . . . . ?
C3 C4 C5 C6 1.0(9) . . . . ?
C3 C8 C9 C1 -3.0(5) . . . . ?
C4 C3 C8 C7 -1.0(7) . . . . ?
C4 C3 C8 C9 -179.4(4) . . . . ?
C4 C5 C6 C7 -1.7(10) . . . . ?
C5 C6 C7 C8 1.0(9) . . . . ?
C6 C7 C8 C3 0.3(8) . . . . ?
C6 C7 C8 C9 178.5(5) . . . . ?
C7 C8 C9 C1 178.7(5) . . . . ?
C8 C3 C4 C5 0.3(7) . . . . ?
C9 C1 C2 O1 178.8(5) . . . . ?
C9 C1 C2 C3 -2.0(5) . . . . ?
C9 C1 C10 C11 52.4(5) . . . . ?
C9 C1 C10 C12 -72.0(5) . . . . ?
C10 C1 C2 O1 -56.1(6) . . . . ?
C10 C1 C2 C3 123.1(4) . . . . ?
C10 C1 C9 C8 -116.8(4) . . . . ?
C10 C12 C13 C14 -178.4(4) . . . . ?
C11 C10 C12 C13 121.3(5) . . . . ?
C12 C10 C11 N4 -64.6(5) . . . . ?
C12 C13 C14 C15 -1.5(8) . . . . ?
C12 C13 C14 C19 176.9(5) . . . . ?
C13 C14 C15 F1 -0.8(8) . . . . ?
C13 C14 C15 C16 178.8(5) . . . . ?
C13 C14 C19 C18 -179.3(4) . . . . ?
C14 C15 C16 C17 0.3(9) . . . . ?
C15 C14 C19 C18 -0.7(7) . . . . ?
C15 C16 C17 C18 -0.8(10) . . . . ?
C16 C17 C18 C19 0.5(10) . . . . ?
C17 C18 C19 C14 0.2(9) . . . . ?
C19 C14 C15 F1 -179.3(6) . . . . ?
C19 C14 C15 C16 0.4(8) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_z_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1874279'
loop_
_audit_author_name
_audit_author_address
'Peigang Ding'
;??The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2018-10-20 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H21 Cl N2 O3'
_chemical_formula_weight         432.89

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   6.6447(5)
_cell_length_b                   14.3101(11)
_cell_length_c                   22.5008(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2139.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3602
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      20.86

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9047
_exptl_absorpt_correction_T_max  0.9615
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24886
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3762
_reflns_number_gt                2822
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0445P)²+0.7313P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.14(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3762
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1084
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.3049(2) 0.83315(7) 0.88362(5) 0.0994(4) Uani 1 1 d . . .
O1 O 0.8832(3) 0.40382(15) 0.97765(9) 0.0544(5) Uani 1 1 d . . .
O2 O 0.3883(5) 0.5440(2) 1.12833(12) 0.0980(10) Uani 1 1 d . . .
O3 O 0.1074(4) 0.4738(2) 1.13565(11) 0.0860(8) Uani 1 1 d . . .
N1 N 0.5146(4) 0.31366(15) 1.02005(10) 0.0483(6) Uani 1 1 d . . .
H1A H 0.5833 0.2630 1.0166 0.058 Uiso 1 1 calc R . .
N2 N 0.2650(4) 0.49011(18) 1.11048(11) 0.0538(6) Uani 1 1 d . . .
C1 C 0.7260(4) 0.40552(18) 0.94982(12) 0.0396(6) Uani 1 1 d . . .
C2 C 0.7007(4) 0.42537(18) 0.88646(12) 0.0429(7) Uani 1 1 d . . .
C3 C 0.8442(5) 0.4543(2) 0.84553(14) 0.0584(8) Uani 1 1 d . . .
H3A H 0.9763 0.4657 0.8571 0.070 Uiso 1 1 calc R . .
C4 C 0.7850(7) 0.4656(3) 0.78744(15) 0.0747(11) Uani 1 1 d . . .
H4A H 0.8780 0.4844 0.7590 0.090 Uiso 1 1 calc R . .
C5 C 0.5875(7) 0.4491(3) 0.77124(15) 0.0756(12) Uani 1 1 d . . .
H5A H 0.5498 0.4576 0.7318 0.091 Uiso 1 1 calc R . .
C6 C 0.4450(6) 0.4204(2) 0.81176(14) 0.0641(9) Uani 1 1 d . . .
H6A H 0.3131 0.4092 0.7999 0.077 Uiso 1 1 calc R . .
C7 C 0.5016(4) 0.40842(19) 0.87074(12) 0.0450(7) Uani 1 1 d . . .
C8 C 0.3808(4) 0.3754(2) 0.92227(12) 0.0462(7) Uani 1 1 d . . .
H8A H 0.3451 0.3101 0.9176 0.055 Uiso 1 1 calc R . .
H8B H 0.2584 0.4118 0.9262 0.055 Uiso 1 1 calc R . .
C9 C 0.5180(4) 0.38916(18) 0.97682(12) 0.0374(6) Uani 1 1 d . . .
C10 C 0.4653(4) 0.47567(18) 1.01602(11) 0.0370(6) Uani 1 1 d . . .
H10A H 0.5826 0.4880 1.0412 0.044 Uiso 1 1 calc R . .
C11 C 0.3040(4) 0.43481(17) 1.05561(11) 0.0401(6) Uani 1 1 d . . .
H11A H 0.1787 0.4300 1.0329 0.048 Uiso 1 1 calc R . .
C12 C 0.3799(4) 0.33396(19) 1.07062(12) 0.0420(7) Uani 1 1 d . . .
H12A H 0.2650 0.2912 1.0687 0.050 Uiso 1 1 calc R . .
C13 C 0.4801(4) 0.32213(19) 1.12991(13) 0.0437(7) Uani 1 1 d . . .
C14 C 0.3735(5) 0.2860(2) 1.17734(14) 0.0583(9) Uani 1 1 d . . .
H14A H 0.2390 0.2700 1.1722 0.070 Uiso 1 1 calc R . .
C15 C 0.4617(6) 0.2732(2) 1.23209(15) 0.0699(10) Uani 1 1 d . . .
H15A H 0.3860 0.2494 1.2634 0.084 Uiso 1 1 calc R . .
C16 C 0.6622(6) 0.2955(2) 1.24108(15) 0.0649(10) Uani 1 1 d . . .
C17 C 0.7673(5) 0.3329(2) 1.19425(15) 0.0618(9) Uani 1 1 d . . .
H17A H 0.9011 0.3500 1.1997 0.074 Uiso 1 1 calc R . .
C18 C 0.6793(5) 0.3459(2) 1.13912(13) 0.0526(8) Uani 1 1 d . . .
H18A H 0.7546 0.3708 1.1081 0.063 Uiso 1 1 calc R . .
C19 C 0.7602(7) 0.2789(3) 1.30031(16) 0.0996(15) Uani 1 1 d . . .
H19A H 0.8989 0.2975 1.2985 0.149 Uiso 1 1 calc R . .
H19B H 0.7521 0.2137 1.3101 0.149 Uiso 1 1 calc R . .
H19C H 0.6923 0.3148 1.3302 0.149 Uiso 1 1 calc R . .
C20 C 0.4188(4) 0.56501(18) 0.98338(12) 0.0393(6) Uani 1 1 d . . .
C21 C 0.5712(5) 0.62860(19) 0.97320(13) 0.0489(7) Uani 1 1 d . . .
H21A H 0.6996 0.6158 0.9875 0.059 Uiso 1 1 calc R . .
C22 C 0.5384(6) 0.7107(2) 0.94239(14) 0.0581(9) Uani 1 1 d . . .
H22A H 0.6430 0.7527 0.9360 0.070 Uiso 1 1 calc R . .
C23 C 0.3484(6) 0.7292(2) 0.92147(14) 0.0618(9) Uani 1 1 d . . .
C24 C 0.1946(6) 0.6687(2) 0.93117(15) 0.0673(9) Uani 1 1 d . . .
H24A H 0.0666 0.6821 0.9167 0.081 Uiso 1 1 calc R . .
C25 C 0.2286(5) 0.5869(2) 0.96264(13) 0.0545(8) Uani 1 1 d . . .
H25A H 0.1222 0.5463 0.9699 0.065 Uiso 1 1 calc R . .


_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
Cl1 C23 1.738(3) . ?
O1 C1 1.218(3) . ?
O2 N2 1.195(3) . ?
O3 N2 1.213(3) . ?
N1 C9 1.454(3) . ?
N1 C12 1.476(3) . ?
N1 H1A 0.8600 . ?
N2 C11 1.489(3) . ?
C1 C2 1.463(4) . ?
C1 C9 1.528(4) . ?
C2 C3 1.389(4) . ?
C2 C7 1.391(4) . ?
C3 C4 1.375(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.382(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.377(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.390(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.487(4) . ?
C8 C9 1.542(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.560(4) . ?
C10 C20 1.506(4) . ?
C10 C11 1.511(4) . ?
C10 H10A 0.9800 . ?
C11 C12 1.566(4) . ?
C11 H11A 0.9800 . ?
C12 C13 1.501(4) . ?
C12 H12A 0.9800 . ?
C13 C14 1.381(4) . ?
C13 C18 1.382(4) . ?
C14 C15 1.377(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.385(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.373(5) . ?
C16 C19 1.502(5) . ?
C17 C18 1.384(4) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.381(4) . ?
C20 C25 1.383(4) . ?
C21 C22 1.382(4) . ?
C21 H21A 0.9300 . ?
C22 C23 1.373(5) . ?
C22 H22A 0.9300 . ?
C23 C24 1.358(5) . ?
C24 C25 1.386(4) . ?
C24 H24A 0.9300 . ?
C25 H25A 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
C9 N1 C12 112.3(2) . . ?
C9 N1 H1A 123.9 . . ?
C12 N1 H1A 123.9 . . ?
O2 N2 O3 124.0(3) . . ?
O2 N2 C11 120.2(3) . . ?
O3 N2 C11 115.8(3) . . ?
O1 C1 C2 127.1(3) . . ?
O1 C1 C9 124.6(2) . . ?
C2 C1 C9 108.3(2) . . ?
C3 C2 C7 122.4(3) . . ?
C3 C2 C1 128.7(3) . . ?
C7 C2 C1 108.8(3) . . ?
C4 C3 C2 118.0(3) . . ?
C4 C3 H3A 121.0 . . ?
C2 C3 H3A 121.0 . . ?
C3 C4 C5 120.2(3) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C6 C5 C4 122.0(3) . . ?
C6 C5 H5A 119.0 . . ?
C4 C5 H5A 119.0 . . ?
C5 C6 C7 118.9(3) . . ?
C5 C6 H6A 120.6 . . ?
C7 C6 H6A 120.6 . . ?
C6 C7 C2 118.6(3) . . ?
C6 C7 C8 129.6(3) . . ?
C2 C7 C8 111.8(2) . . ?
C7 C8 C9 105.1(2) . . ?
C7 C8 H8A 110.7 . . ?
C9 C8 H8A 110.7 . . ?
C7 C8 H8B 110.7 . . ?
C9 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
N1 C9 C1 113.2(2) . . ?
N1 C9 C8 115.4(2) . . ?
C1 C9 C8 103.8(2) . . ?
N1 C9 C10 102.0(2) . . ?
C1 C9 C10 107.8(2) . . ?
C8 C9 C10 114.8(2) . . ?
C20 C10 C11 118.1(2) . . ?
C20 C10 C9 116.4(2) . . ?
C11 C10 C9 100.7(2) . . ?
C20 C10 H10A 107.0 . . ?
C11 C10 H10A 107.0 . . ?
C9 C10 H10A 107.0 . . ?
N2 C11 C10 114.0(2) . . ?
N2 C11 C12 111.5(2) . . ?
C10 C11 C12 104.8(2) . . ?
N2 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
N1 C12 C13 113.2(2) . . ?
N1 C12 C11 102.1(2) . . ?
C13 C12 C11 116.0(2) . . ?
N1 C12 H12A 108.4 . . ?
C13 C12 H12A 108.4 . . ?
C11 C12 H12A 108.4 . . ?
C14 C13 C18 117.9(3) . . ?
C14 C13 C12 120.1(3) . . ?
C18 C13 C12 122.0(3) . . ?
C15 C14 C13 121.5(3) . . ?
C15 C14 H14A 119.2 . . ?
C13 C14 H14A 119.2 . . ?
C14 C15 C16 120.7(3) . . ?
C14 C15 H15A 119.7 . . ?
C16 C15 H15A 119.7 . . ?
C17 C16 C15 117.8(3) . . ?
C17 C16 C19 121.5(4) . . ?
C15 C16 C19 120.7(4) . . ?
C16 C17 C18 121.7(3) . . ?
C16 C17 H17A 119.2 . . ?
C18 C17 H17A 119.2 . . ?
C13 C18 C17 120.4(3) . . ?
C13 C18 H18A 119.8 . . ?
C17 C18 H18A 119.8 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C25 117.7(3) . . ?
C21 C20 C10 119.3(2) . . ?
C25 C20 C10 123.0(2) . . ?
C20 C21 C22 121.9(3) . . ?
C20 C21 H21A 119.1 . . ?
C22 C21 H21A 119.1 . . ?
C23 C22 C21 118.8(3) . . ?
C23 C22 H22A 120.6 . . ?
C21 C22 H22A 120.6 . . ?
C24 C23 C22 121.0(3) . . ?
C24 C23 Cl1 120.0(3) . . ?
C22 C23 Cl1 119.1(3) . . ?
C23 C24 C25 119.9(3) . . ?
C23 C24 H24A 120.1 . . ?
C25 C24 H24A 120.1 . . ?
C20 C25 C24 120.8(3) . . ?
C20 C25 H25A 119.6 . . ?
C24 C25 H25A 119.6 . . ?

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 C1 C2 C3 -6.2(5) . . . . ?
C9 C1 C2 C3 172.3(3) . . . . ?
O1 C1 C2 C7 172.3(3) . . . . ?
C9 C1 C2 C7 -9.1(3) . . . . ?
C7 C2 C3 C4 -0.5(5) . . . . ?
C1 C2 C3 C4 177.9(3) . . . . ?
C2 C3 C4 C5 0.5(5) . . . . ?
C3 C4 C5 C6 -0.6(6) . . . . ?
C4 C5 C6 C7 0.5(6) . . . . ?
C5 C6 C7 C2 -0.4(5) . . . . ?
C5 C6 C7 C8 -177.7(3) . . . . ?
C3 C2 C7 C6 0.4(4) . . . . ?
C1 C2 C7 C6 -178.3(3) . . . . ?
C3 C2 C7 C8 178.2(3) . . . . ?
C1 C2 C7 C8 -0.5(3) . . . . ?
C6 C7 C8 C9 -172.9(3) . . . . ?
C2 C7 C8 C9 9.6(3) . . . . ?
C12 N1 C9 C1 142.6(2) . . . . ?
C12 N1 C9 C8 -98.1(3) . . . . ?
C12 N1 C9 C10 27.0(3) . . . . ?
O1 C1 C9 N1 -41.2(4) . . . . ?
C2 C1 C9 N1 140.2(2) . . . . ?
O1 C1 C9 C8 -167.0(3) . . . . ?
C2 C1 C9 C8 14.4(3) . . . . ?
O1 C1 C9 C10 70.9(3) . . . . ?
C2 C1 C9 C10 -107.7(2) . . . . ?
C7 C8 C9 N1 -138.6(2) . . . . ?
C7 C8 C9 C1 -14.2(3) . . . . ?
C7 C8 C9 C10 103.2(3) . . . . ?
N1 C9 C10 C20 -169.3(2) . . . . ?
C1 C9 C10 C20 71.3(3) . . . . ?
C8 C9 C10 C20 -43.8(3) . . . . ?
N1 C9 C10 C11 -40.5(2) . . . . ?
C1 C9 C10 C11 -159.9(2) . . . . ?
C8 C9 C10 C11 85.0(3) . . . . ?
O2 N2 C11 C10 -20.0(4) . . . . ?
O3 N2 C11 C10 162.5(3) . . . . ?
O2 N2 C11 C12 98.4(3) . . . . ?
O3 N2 C11 C12 -79.0(3) . . . . ?
C20 C10 C11 N2 -70.2(3) . . . . ?
C9 C10 C11 N2 162.1(2) . . . . ?
C20 C10 C11 C12 167.6(2) . . . . ?
C9 C10 C11 C12 39.9(2) . . . . ?
C9 N1 C12 C13 -127.9(3) . . . . ?
C9 N1 C12 C11 -2.4(3) . . . . ?
N2 C11 C12 N1 -148.1(2) . . . . ?
C10 C11 C12 N1 -24.3(2) . . . . ?
N2 C11 C12 C13 -24.4(3) . . . . ?
C10 C11 C12 C13 99.4(3) . . . . ?
N1 C12 C13 C14 -143.0(3) . . . . ?
C11 C12 C13 C14 99.3(3) . . . . ?
N1 C12 C13 C18 36.6(4) . . . . ?
C11 C12 C13 C18 -81.0(3) . . . . ?
C18 C13 C14 C15 -0.5(5) . . . . ?
C12 C13 C14 C15 179.2(3) . . . . ?
C13 C14 C15 C16 -0.7(5) . . . . ?
C14 C15 C16 C17 1.8(5) . . . . ?
C14 C15 C16 C19 -178.2(3) . . . . ?
C15 C16 C17 C18 -1.8(5) . . . . ?
C19 C16 C17 C18 178.2(3) . . . . ?
C14 C13 C18 C17 0.5(4) . . . . ?
C12 C13 C18 C17 -179.2(3) . . . . ?
C16 C17 C18 C13 0.7(5) . . . . ?
C11 C10 C20 C21 146.6(3) . . . . ?
C9 C10 C20 C21 -93.5(3) . . . . ?
C11 C10 C20 C25 -33.5(4) . . . . ?
C9 C10 C20 C25 86.4(3) . . . . ?
C25 C20 C21 C22 -1.3(4) . . . . ?
C10 C20 C21 C22 178.6(3) . . . . ?
C20 C21 C22 C23 0.0(4) . . . . ?
C21 C22 C23 C24 0.6(5) . . . . ?
C21 C22 C23 Cl1 179.1(2) . . . . ?
C22 C23 C24 C25 0.0(5) . . . . ?
Cl1 C23 C24 C25 -178.4(2) . . . . ?
C21 C20 C25 C24 1.9(4) . . . . ?
C10 C20 C25 C24 -177.9(3) . . . . ?
C23 C24 C25 C20 -1.3(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.034
