# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_20210910a
_audit_block_doi                 10.5517/ccdc.csd.cc29hwk8
_database_code_depnum_ccdc_archive 'CCDC 2130430'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1002/ajoc.202200031 2022
loop_
_audit_author_name
_audit_author_address
'Wen Wan'
;Shanghai University
China
;
_audit_update_record             
;
2021-12-22 deposited with the CCDC.	2024-02-05 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 F2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         314.32
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   7.534(2)
_cell_length_b                   12.716(3)
_cell_length_c                   15.945(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1527.6(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6113
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      66.32
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656

_exptl_absorpt_coefficient_mu    0.870
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   
;
;
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.95

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150.(2)

_diffrn_source                   'Microfocus sealed tube'
_diffrn_source_type              'Incoatec Ius 3.0'
_diffrn_source_power             ?
_diffrn_source_current           ?
_diffrn_source_voltage           ?

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helios MX Multilayer Optic'

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE DUO PHOTON III'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            10659
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_theta_min         3.48
_diffrn_reflns_theta_max         66.74
_diffrn_reflns_theta_full        66.74
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             2445
_reflns_number_gt                2276
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_max     0.826
_reflns_Friedel_fraction_full    0.826

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0946
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_restrained_S_all      1.168
_refine_ls_number_reflns         2445
_refine_ls_number_parameters     211
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0347P)²+0.6455P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.215
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 913 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(8)

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1260)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.6454(3) 0.13962(15) 0.39603(15) 0.0431(6) Uani d . . . 1 . .
F F2 0.8857(3) 0.17976(15) 0.46044(15) 0.0406(6) Uani d . . . 1 . .
O O1 0.7432(3) 0.33224(16) 0.36040(15) 0.0277(5) Uani d . . . 1 . .
O O2 0.5471(4) 0.56591(18) 0.50993(18) 0.0401(6) Uani d . . . 1 . .
C C1 0.6243(4) 0.1644(2) 0.5437(2) 0.0236(7) Uani d . . . 1 . .
C C2 0.4518(4) 0.1218(2) 0.5454(2) 0.0256(7) Uani d . . . 1 . .
C C3 0.3812(4) 0.0918(2) 0.6225(2) 0.0265(7) Uani d . . . 1 . .
H H3 0.266681 0.060614 0.623964 0.032000 Uiso calc U . R 1 . .
C C4 0.4718(5) 0.1059(2) 0.6972(2) 0.0259(7) Uani d . . . 1 . .
C C5 0.6381(5) 0.1517(2) 0.6940(2) 0.0275(8) Uani d . . . 1 . .
H H5 0.700011 0.163749 0.744977 0.033000 Uiso calc U . R 1 . .
C C6 0.7186(4) 0.1807(2) 0.6187(2) 0.0261(7) Uani d . . . 1 . .
C C7 0.7067(4) 0.1985(2) 0.4613(2) 0.0281(7) Uani d . . . 1 . .
C C8 0.6797(4) 0.3130(2) 0.4391(2) 0.0243(7) Uani d . . . 1 . .
C C9 0.6100(4) 0.3863(2) 0.4891(2) 0.0264(7) Uani d . . . 1 . .
H H9 0.562073 0.366147 0.541796 0.032000 Uiso calc U . R 1 . .
C C10 0.6058(4) 0.4964(2) 0.4645(2) 0.0281(7) Uani d . . . 1 . .
C C11 0.6792(4) 0.5169(2) 0.3805(2) 0.0259(7) Uani d . . . 1 . .
C C12 0.6863(5) 0.6188(3) 0.3466(3) 0.0322(8) Uani d . . . 1 . .
H H12 0.645660 0.676869 0.378774 0.039000 Uiso calc U . R 1 . .
C C13 0.7518(5) 0.6348(3) 0.2671(2) 0.0356(9) Uani d . . . 1 . .
H H13 0.757292 0.703985 0.244773 0.043000 Uiso calc U . R 1 . .
C C14 0.8097(5) 0.5506(3) 0.2194(3) 0.0354(8) Uani d . . . 1 . .
H H14 0.853847 0.562701 0.164441 0.042000 Uiso calc U . R 1 . .
C C15 0.8045(5) 0.4494(3) 0.2503(2) 0.0305(8) Uani d . . . 1 . .
H H15 0.843402 0.391595 0.217289 0.037000 Uiso calc U . R 1 . .
C C16 0.7401(5) 0.4344(2) 0.3317(2) 0.0263(7) Uani d . . . 1 . .
C C17 0.3332(5) 0.1085(3) 0.4697(3) 0.0395(9) Uani d . . . 1 . .
H H17A 0.210966 0.096032 0.488203 0.059000 Uiso calc U . R 1 . .
H H17B 0.374220 0.048469 0.436391 0.059000 Uiso calc U . R 1 . .
H H17C 0.337520 0.172426 0.435420 0.059000 Uiso calc U . R 1 . .
C C18 0.3915(6) 0.0737(3) 0.7799(2) 0.0395(9) Uani d . . . 1 . .
H H18A 0.435155 0.120333 0.824298 0.059000 Uiso calc U . R 1 . .
H H18B 0.425269 0.001047 0.792640 0.059000 Uiso calc U . R 1 . .
H H18C 0.261917 0.078918 0.776524 0.059000 Uiso calc U . R 1 . .
C C19 0.9021(4) 0.2288(3) 0.6244(3) 0.0381(9) Uani d . . . 1 . .
H H19A 0.925562 0.250180 0.682407 0.057000 Uiso calc U . R 1 . .
H H19B 0.908746 0.290438 0.587649 0.057000 Uiso calc U . R 1 . .
H H19C 0.990767 0.176873 0.606868 0.057000 Uiso calc U . R 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C7 . 1.363(4) ?
F2 C7 . 1.369(4) ?
O1 C8 . 1.366(4) ?
O1 C16 . 1.378(4) ?
O2 C10 . 1.225(4) ?
C1 C6 . 1.406(5) ?
C1 C2 . 1.408(4) ?
C1 C7 . 1.517(5) ?
C2 C3 . 1.394(5) ?
C2 C17 . 1.510(5) ?
C3 C4 . 1.383(5) ?
C3 H3 . 0.950000 ?
C4 C5 . 1.383(5) ?
C4 C18 . 1.508(5) ?
C5 C6 . 1.394(5) ?
C5 H5 . 0.950000 ?
C6 C19 . 1.514(4) ?
C7 C8 . 1.512(4) ?
C8 C9 . 1.334(5) ?
C9 C10 . 1.455(5) ?
C9 H9 . 0.950000 ?
C10 C11 . 1.473(5) ?
C11 C16 . 1.384(5) ?
C11 C12 . 1.404(5) ?
C12 C13 . 1.376(6) ?
C12 H12 . 0.950000 ?
C13 C14 . 1.384(6) ?
C13 H13 . 0.950000 ?
C14 C15 . 1.378(5) ?
C14 H14 . 0.950000 ?
C15 C16 . 1.398(5) ?
C15 H15 . 0.950000 ?
C17 H17A . 0.980000 ?
C17 H17B . 0.980000 ?
C17 H17C . 0.980000 ?
C18 H18A . 0.980000 ?
C18 H18B . 0.980000 ?
C18 H18C . 0.980000 ?
C19 H19A . 0.980000 ?
C19 H19B . 0.980000 ?
C19 H19C . 0.980000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 O1 C16 . . 118.0(3) ?
C6 C1 C2 . . 120.5(3) ?
C6 C1 C7 . . 119.2(3) ?
C2 C1 C7 . . 120.3(3) ?
C3 C2 C1 . . 118.3(3) ?
C3 C2 C17 . . 116.7(3) ?
C1 C2 C17 . . 125.0(3) ?
C4 C3 C2 . . 122.4(3) ?
C4 C3 H3 . . 118.800000 ?
C2 C3 H3 . . 118.800000 ?
C5 C4 C3 . . 118.0(3) ?
C5 C4 C18 . . 120.7(3) ?
C3 C4 C18 . . 121.3(3) ?
C4 C5 C6 . . 122.5(3) ?
C4 C5 H5 . . 118.700000 ?
C6 C5 H5 . . 118.700000 ?
C5 C6 C1 . . 118.2(3) ?
C5 C6 C19 . . 116.9(3) ?
C1 C6 C19 . . 124.9(3) ?
F1 C7 F2 . . 103.3(3) ?
F1 C7 C8 . . 107.7(3) ?
F2 C7 C8 . . 107.3(3) ?
F1 C7 C1 . . 111.4(3) ?
F2 C7 C1 . . 111.2(3) ?
C8 C7 C1 . . 115.0(3) ?
C9 C8 O1 . . 124.1(3) ?
C9 C8 C7 . . 125.9(3) ?
O1 C8 C7 . . 109.9(3) ?
C8 C9 C10 . . 121.4(3) ?
C8 C9 H9 . . 119.300000 ?
C10 C9 H9 . . 119.300000 ?
O2 C10 C9 . . 122.9(3) ?
O2 C10 C11 . . 123.1(3) ?
C9 C10 C11 . . 114.0(3) ?
C16 C11 C12 . . 118.0(3) ?
C16 C11 C10 . . 120.1(3) ?
C12 C11 C10 . . 121.8(3) ?
C13 C12 C11 . . 120.3(3) ?
C13 C12 H12 . . 119.900000 ?
C11 C12 H12 . . 119.900000 ?
C12 C13 C14 . . 120.3(3) ?
C12 C13 H13 . . 119.800000 ?
C14 C13 H13 . . 119.800000 ?
C15 C14 C13 . . 121.2(4) ?
C15 C14 H14 . . 119.400000 ?
C13 C14 H14 . . 119.400000 ?
C14 C15 C16 . . 117.9(3) ?
C14 C15 H15 . . 121.000000 ?
C16 C15 H15 . . 121.000000 ?
O1 C16 C11 . . 122.2(3) ?
O1 C16 C15 . . 115.5(3) ?
C11 C16 C15 . . 122.3(3) ?
C2 C17 H17A . . 109.500000 ?
C2 C17 H17B . . 109.500000 ?
H17A C17 H17B . . 109.500000 ?
C2 C17 H17C . . 109.500000 ?
H17A C17 H17C . . 109.500000 ?
H17B C17 H17C . . 109.500000 ?
C4 C18 H18A . . 109.500000 ?
C4 C18 H18B . . 109.500000 ?
H18A C18 H18B . . 109.500000 ?
C4 C18 H18C . . 109.500000 ?
H18A C18 H18C . . 109.500000 ?
H18B C18 H18C . . 109.500000 ?
C6 C19 H19A . . 109.500000 ?
C6 C19 H19B . . 109.500000 ?
H19A C19 H19B . . 109.500000 ?
C6 C19 H19C . . 109.500000 ?
H19A C19 H19C . . 109.500000 ?
H19B C19 H19C . . 109.500000 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -3.0(4) ?
C7 C1 C2 C3 . . . . -179.8(3) ?
C6 C1 C2 C17 . . . . 175.1(3) ?
C7 C1 C2 C17 . . . . -1.7(5) ?
C1 C2 C3 C4 . . . . 2.3(4) ?
C17 C2 C3 C4 . . . . -176.0(3) ?
C2 C3 C4 C5 . . . . 0.1(4) ?
C2 C3 C4 C18 . . . . 179.4(3) ?
C3 C4 C5 C6 . . . . -1.9(5) ?
C18 C4 C5 C6 . . . . 178.8(3) ?
C4 C5 C6 C1 . . . . 1.2(4) ?
C4 C5 C6 C19 . . . . -179.2(3) ?
C2 C1 C6 C5 . . . . 1.3(4) ?
C7 C1 C6 C5 . . . . 178.1(3) ?
C2 C1 C6 C19 . . . . -178.2(3) ?
C7 C1 C6 C19 . . . . -1.4(4) ?
C6 C1 C7 F1 . . . . 153.0(3) ?
C2 C1 C7 F1 . . . . -30.3(4) ?
C6 C1 C7 F2 . . . . 38.2(4) ?
C2 C1 C7 F2 . . . . -145.0(3) ?
C6 C1 C7 C8 . . . . -84.1(4) ?
C2 C1 C7 C8 . . . . 92.7(3) ?
C16 O1 C8 C9 . . . . 2.1(5) ?
C16 O1 C8 C7 . . . . -175.9(3) ?
F1 C7 C8 C9 . . . . 133.1(3) ?
F2 C7 C8 C9 . . . . -116.2(4) ?
C1 C7 C8 C9 . . . . 8.2(5) ?
F1 C7 C8 O1 . . . . -48.9(4) ?
F2 C7 C8 O1 . . . . 61.8(3) ?
C1 C7 C8 O1 . . . . -173.8(3) ?
O1 C8 C9 C10 . . . . -3.8(5) ?
C7 C8 C9 C10 . . . . 173.9(3) ?
C8 C9 C10 O2 . . . . -178.0(3) ?
C8 C9 C10 C11 . . . . 1.8(5) ?
O2 C10 C11 C16 . . . . -178.7(3) ?
C9 C10 C11 C16 . . . . 1.6(4) ?
O2 C10 C11 C12 . . . . -0.1(5) ?
C9 C10 C11 C12 . . . . -179.8(3) ?
C16 C11 C12 C13 . . . . 0.2(5) ?
C10 C11 C12 C13 . . . . -178.5(3) ?
C11 C12 C13 C14 . . . . 0.6(6) ?
C12 C13 C14 C15 . . . . -0.4(6) ?
C13 C14 C15 C16 . . . . -0.5(5) ?
C8 O1 C16 C11 . . . . 1.5(5) ?
C8 O1 C16 C15 . . . . -179.2(3) ?
C12 C11 C16 O1 . . . . 178.1(3) ?
C10 C11 C16 O1 . . . . -3.2(5) ?
C12 C11 C16 C15 . . . . -1.2(5) ?
C10 C11 C16 C15 . . . . 177.5(3) ?
C14 C15 C16 O1 . . . . -178.0(3) ?
C14 C15 C16 C11 . . . . 1.4(5) ?



####################################################################### 
# 
# 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_xlh014
_database_code_depnum_ccdc_archive 'CCDC 2150401'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2022-02-07 deposited with the CCDC.	2024-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H24 N4 O'
_chemical_formula_sum            'C27 H24 N4 O'
_chemical_formula_weight         420.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   24.3936(8)
_cell_length_b                   24.3936(8)
_cell_length_c                   16.9622(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     10093.3(8)
_cell_formula_units_Z            16
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9986
_cell_measurement_theta_min      4.82
_cell_measurement_theta_max      68.36

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_F_000             3552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.363
_exptl_crystal_size_min          0.356
_exptl_absorpt_coefficient_mu    0.545
_shelx_estimated_absorpt_T_min   0.812
_shelx_estimated_absorpt_T_max   0.830
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7231
_exptl_absorpt_correction_T_max  0.8932
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36996
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.173
_diffrn_reflns_theta_max         68.356
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             4529
_reflns_number_gt                3814
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 Structure factors included contributions from the .fab file. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0767P)²+14.5582P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4529
_refine_ls_number_parameters     301
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0664
_refine_ls_wR_factor_ref         0.1736
_refine_ls_wR_factor_gt          0.1629
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.17696(7) 0.51984(7) 0.61174(8) 0.0467(4) Uani 1 1 d . . . . .
N1X N -0.0332(15) 0.440(3) 0.857(4) 0.0997(17) Uani 0.073(10) 1 d D . P A 1
N1Y N -0.02082(16) 0.4176(2) 0.8866(3) 0.0997(17) Uani 0.927(10) 1 d D . P A 2
N2 N 0.16809(7) 0.36556(8) 0.68994(10) 0.0386(4) Uani 1 1 d . . . . .
N3 N 0.23606(7) 0.42825(7) 0.64745(9) 0.0342(4) Uani 1 1 d . . . . .
N4 N 0.21888(7) 0.46736(7) 0.70371(9) 0.0370(4) Uani 1 1 d D . . . .
H4N H 0.2254(12) 0.4615(12) 0.7549(11) 0.060(8) Uiso 1 1 d D . . . .
C1X C -0.061(2) 0.470(3) 0.891(5) 0.150(4) Uani 0.073(10) 1 d D . P A 1
C1Y C -0.0476(2) 0.4177(4) 0.9425(4) 0.150(4) Uani 0.927(10) 1 d D . P A 2
C2 C 0.01471(13) 0.41575(16) 0.8185(2) 0.0799(10) Uani 1 1 d D . . . .
H2A H 0.044828 0.439822 0.836709 0.096 Uiso 0.073(10) 1 calc R U P A 1
H2B H 0.009056 0.425682 0.762479 0.096 Uiso 0.073(10) 1 calc R U P A 1
H2C H 0.042823 0.444871 0.822744 0.096 Uiso 0.927(10) 1 calc R U P A 2
H2D H -0.007026 0.422566 0.770178 0.096 Uiso 0.927(10) 1 calc R U P A 2
C3 C 0.04258(11) 0.36017(14) 0.81260(17) 0.0653(8) Uani 1 1 d . . . . .
H3A H 0.059610 0.350858 0.863859 0.078 Uiso 1 1 calc R U . . .
H3B H 0.014943 0.331716 0.800250 0.078 Uiso 1 1 calc R U . . .
C11 C 0.08578(10) 0.36091(10) 0.74940(14) 0.0469(5) Uani 1 1 d . . . . .
C12 C 0.14075(9) 0.36371(10) 0.76171(13) 0.0437(5) Uani 1 1 d . . . . .
H12 H 0.157936 0.364311 0.811958 0.052 Uiso 1 1 calc R U . . .
C13 C 0.12998(8) 0.36398(8) 0.63022(13) 0.0374(5) Uani 1 1 d . . . . .
C14 C 0.13689(9) 0.36488(9) 0.54961(13) 0.0429(5) Uani 1 1 d . . . . .
H14 H 0.172285 0.367962 0.526654 0.051 Uiso 1 1 calc R U . . .
C15 C 0.09015(10) 0.36111(11) 0.50320(15) 0.0509(6) Uani 1 1 d . . . . .
H15 H 0.093579 0.361989 0.447423 0.061 Uiso 1 1 calc R U . . .
C16 C 0.03813(10) 0.35604(11) 0.53704(16) 0.0551(6) Uani 1 1 d . . . . .
H16 H 0.006950 0.352558 0.503862 0.066 Uiso 1 1 calc R U . . .
C17 C 0.03134(10) 0.35602(11) 0.61738(16) 0.0525(6) Uani 1 1 d . . . . .
H17 H -0.004255 0.353215 0.639739 0.063 Uiso 1 1 calc R U . . .
C18 C 0.07762(9) 0.36019(9) 0.66599(14) 0.0410(5) Uani 1 1 d . . . . .
C21 C 0.22655(8) 0.37330(9) 0.68092(11) 0.0351(4) Uani 1 1 d . . . . .
H21 H 0.243577 0.372174 0.734526 0.042 Uiso 1 1 calc R U . . .
C22 C 0.25282(8) 0.32885(9) 0.63129(12) 0.0372(5) Uani 1 1 d . . . . .
C23 C 0.23975(10) 0.27451(10) 0.64780(14) 0.0464(5) Uani 1 1 d . . . . .
H23 H 0.213958 0.266388 0.688101 0.056 Uiso 1 1 calc R U . . .
C24 C 0.26400(12) 0.23216(11) 0.60601(17) 0.0603(7) Uani 1 1 d . . . . .
H24 H 0.254690 0.195190 0.617470 0.072 Uiso 1 1 calc R U . . .
C25 C 0.30165(13) 0.24377(13) 0.54778(19) 0.0682(8) Uani 1 1 d . . . . .
H25 H 0.318325 0.214888 0.518862 0.082 Uiso 1 1 calc R U . . .
C26 C 0.31502(12) 0.29776(12) 0.53167(17) 0.0628(7) Uani 1 1 d . . . . .
H26 H 0.341219 0.305502 0.491754 0.075 Uiso 1 1 calc R U . . .
C27 C 0.29093(9) 0.34103(10) 0.57265(13) 0.0452(5) Uani 1 1 d . . . . .
C28 C 0.30547(10) 0.39990(11) 0.55484(14) 0.0494(6) Uani 1 1 d . . . . .
H28A H 0.284223 0.412520 0.508539 0.059 Uiso 1 1 calc R U . . .
H28B H 0.344904 0.402361 0.541531 0.059 Uiso 1 1 calc R U . . .
C29 C 0.29330(9) 0.43695(10) 0.62470(13) 0.0417(5) Uani 1 1 d . . . . .
H29A H 0.317902 0.427895 0.669257 0.050 Uiso 1 1 calc R U . . .
H29B H 0.299241 0.475775 0.610025 0.050 Uiso 1 1 calc R U . . .
C31 C 0.18724(9) 0.50911(9) 0.68130(11) 0.0357(5) Uani 1 1 d . . . . .
C32 C 0.16430(9) 0.54361(9) 0.74643(12) 0.0403(5) Uani 1 1 d . . . . .
C33 C 0.14280(10) 0.52026(11) 0.81412(13) 0.0465(5) Uani 1 1 d . . . . .
H33 H 0.144807 0.481701 0.821458 0.056 Uiso 1 1 calc R U . . .
C34 C 0.11840(12) 0.55271(13) 0.87122(14) 0.0586(7) Uani 1 1 d . . . . .
H34 H 0.103093 0.536318 0.917007 0.070 Uiso 1 1 calc R U . . .
C35 C 0.11633(13) 0.60840(13) 0.86167(16) 0.0661(8) Uani 1 1 d . . . . .
H35 H 0.099900 0.630611 0.901135 0.079 Uiso 1 1 calc R U . . .
C36 C 0.13809(15) 0.63245(13) 0.79473(18) 0.0719(9) Uani 1 1 d . . . . .
H36 H 0.137071 0.671143 0.788595 0.086 Uiso 1 1 calc R U . . .
C37 C 0.16140(13) 0.59993(11) 0.73659(16) 0.0588(7) Uani 1 1 d . . . . .
H37 H 0.175411 0.616311 0.689940 0.071 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 C31 1.234(2) . ?
N1X C1X 1.160(19) . ?
N1X C2 1.460(17) . ?
N1Y C1Y 1.152(5) . ?
N1Y C2 1.445(4) . ?
N2 C13 1.375(3) . ?
N2 C12 1.389(3) . ?
N2 C21 1.446(3) . ?
N3 N4 1.413(2) . ?
N3 C29 1.464(3) . ?
N3 C21 1.474(3) . ?
N4 C31 1.333(3) . ?
N4 H4N 0.895(17) . ?
C2 C3 1.520(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 H2C 0.9900 . ?
C2 H2D 0.9900 . ?
C3 C11 1.503(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C11 C12 1.359(3) . ?
C11 C18 1.429(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(3) . ?
C13 C18 1.417(3) . ?
C14 C15 1.389(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.398(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.373(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.402(3) . ?
C17 H17 0.9500 . ?
C21 C22 1.515(3) . ?
C21 H21 1.0000 . ?
C22 C23 1.392(3) . ?
C22 C27 1.393(3) . ?
C23 C24 1.386(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.378(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.384(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.394(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.510(4) . ?
C28 C29 1.519(3) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C31 C32 1.497(3) . ?
C32 C33 1.385(3) . ?
C32 C37 1.386(3) . ?
C33 C34 1.385(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.369(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.384(4) . ?
C35 H35 0.9500 . ?
C36 C37 1.387(4) . ?
C36 H36 0.9500 . ?
C37 H37 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
C1X N1X C2 161(6) . . ?
C1Y N1Y C2 177.2(7) . . ?
C13 N2 C12 108.67(17) . . ?
C13 N2 C21 126.31(17) . . ?
C12 N2 C21 124.77(18) . . ?
N4 N3 C29 111.28(16) . . ?
N4 N3 C21 107.89(15) . . ?
C29 N3 C21 112.55(16) . . ?
C31 N4 N3 119.66(16) . . ?
C31 N4 H4N 120.1(19) . . ?
N3 N4 H4N 119.7(19) . . ?
N1Y C2 C3 110.4(4) . . ?
N1X C2 C3 138(3) . . ?
N1X C2 H2A 102.6 . . ?
C3 C2 H2A 102.6 . . ?
N1X C2 H2B 102.6 . . ?
C3 C2 H2B 102.6 . . ?
H2A C2 H2B 104.9 . . ?
N1Y C2 H2C 109.6 . . ?
C3 C2 H2C 109.6 . . ?
N1Y C2 H2D 109.6 . . ?
C3 C2 H2D 109.6 . . ?
H2C C2 H2D 108.1 . . ?
C11 C3 C2 110.5(3) . . ?
C11 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
C11 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C12 C11 C18 106.87(19) . . ?
C12 C11 C3 125.6(2) . . ?
C18 C11 C3 127.5(2) . . ?
C11 C12 N2 109.9(2) . . ?
C11 C12 H12 125.0 . . ?
N2 C12 H12 125.0 . . ?
N2 C13 C14 130.4(2) . . ?
N2 C13 C18 107.20(18) . . ?
C14 C13 C18 122.4(2) . . ?
C13 C14 C15 117.4(2) . . ?
C13 C14 H14 121.3 . . ?
C15 C14 H14 121.3 . . ?
C14 C15 C16 121.2(2) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 121.1(2) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 119.1(2) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C17 C18 C13 118.6(2) . . ?
C17 C18 C11 134.1(2) . . ?
C13 C18 C11 107.31(19) . . ?
N2 C21 N3 108.34(16) . . ?
N2 C21 C22 112.48(17) . . ?
N3 C21 C22 111.73(16) . . ?
N2 C21 H21 108.0 . . ?
N3 C21 H21 108.0 . . ?
C22 C21 H21 108.0 . . ?
C23 C22 C27 120.0(2) . . ?
C23 C22 C21 118.22(19) . . ?
C27 C22 C21 121.75(19) . . ?
C24 C23 C22 120.6(2) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 119.9(3) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 119.6(3) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C25 C26 C27 121.5(3) . . ?
C25 C26 H26 119.2 . . ?
C27 C26 H26 119.2 . . ?
C22 C27 C26 118.4(2) . . ?
C22 C27 C28 120.2(2) . . ?
C26 C27 C28 121.4(2) . . ?
C27 C28 C29 111.33(18) . . ?
C27 C28 H28A 109.4 . . ?
C29 C28 H28A 109.4 . . ?
C27 C28 H28B 109.4 . . ?
C29 C28 H28B 109.4 . . ?
H28A C28 H28B 108.0 . . ?
N3 C29 C28 107.79(18) . . ?
N3 C29 H29A 110.1 . . ?
C28 C29 H29A 110.1 . . ?
N3 C29 H29B 110.1 . . ?
C28 C29 H29B 110.1 . . ?
H29A C29 H29B 108.5 . . ?
O1 C31 N4 123.52(19) . . ?
O1 C31 C32 120.7(2) . . ?
N4 C31 C32 115.81(17) . . ?
C33 C32 C37 119.2(2) . . ?
C33 C32 C31 121.5(2) . . ?
C37 C32 C31 119.2(2) . . ?
C32 C33 C34 120.5(2) . . ?
C32 C33 H33 119.8 . . ?
C34 C33 H33 119.8 . . ?
C35 C34 C33 120.0(3) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C34 C35 C36 120.2(2) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C35 C36 C37 119.9(3) . . ?
C35 C36 H36 120.1 . . ?
C37 C36 H36 120.1 . . ?
C32 C37 C36 120.1(3) . . ?
C32 C37 H37 119.9 . . ?
C36 C37 H37 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
C29 N3 N4 C31 103.3(2) . . . . ?
C21 N3 N4 C31 -132.75(19) . . . . ?
C1X N1X C2 C3 138(21) . . . . ?
N1Y C2 C3 C11 -171.5(3) . . . . ?
N1X C2 C3 C11 169(4) . . . . ?
C2 C3 C11 C12 103.9(3) . . . . ?
C2 C3 C11 C18 -74.5(3) . . . . ?
C18 C11 C12 N2 0.8(3) . . . . ?
C3 C11 C12 N2 -177.9(2) . . . . ?
C13 N2 C12 C11 0.1(3) . . . . ?
C21 N2 C12 C11 174.5(2) . . . . ?
C12 N2 C13 C14 179.9(2) . . . . ?
C21 N2 C13 C14 5.6(4) . . . . ?
C12 N2 C13 C18 -0.9(2) . . . . ?
C21 N2 C13 C18 -175.29(19) . . . . ?
N2 C13 C14 C15 178.1(2) . . . . ?
C18 C13 C14 C15 -0.9(3) . . . . ?
C13 C14 C15 C16 -0.6(4) . . . . ?
C14 C15 C16 C17 1.7(4) . . . . ?
C15 C16 C17 C18 -1.1(4) . . . . ?
C16 C17 C18 C13 -0.3(4) . . . . ?
C16 C17 C18 C11 -179.3(3) . . . . ?
N2 C13 C18 C17 -177.8(2) . . . . ?
C14 C13 C18 C17 1.4(3) . . . . ?
N2 C13 C18 C11 1.4(2) . . . . ?
C14 C13 C18 C11 -179.4(2) . . . . ?
C12 C11 C18 C17 177.7(3) . . . . ?
C3 C11 C18 C17 -3.7(5) . . . . ?
C12 C11 C18 C13 -1.4(3) . . . . ?
C3 C11 C18 C13 177.3(2) . . . . ?
C13 N2 C21 N3 63.8(3) . . . . ?
C12 N2 C21 N3 -109.7(2) . . . . ?
C13 N2 C21 C22 -60.2(3) . . . . ?
C12 N2 C21 C22 126.3(2) . . . . ?
N4 N3 C21 N2 65.67(19) . . . . ?
C29 N3 C21 N2 -171.17(16) . . . . ?
N4 N3 C21 C22 -169.88(16) . . . . ?
C29 N3 C21 C22 -46.7(2) . . . . ?
N2 C21 C22 C23 -47.3(3) . . . . ?
N3 C21 C22 C23 -169.38(18) . . . . ?
N2 C21 C22 C27 135.4(2) . . . . ?
N3 C21 C22 C27 13.3(3) . . . . ?
C27 C22 C23 C24 -0.5(3) . . . . ?
C21 C22 C23 C24 -177.8(2) . . . . ?
C22 C23 C24 C25 0.3(4) . . . . ?
C23 C24 C25 C26 0.2(5) . . . . ?
C24 C25 C26 C27 -0.5(5) . . . . ?
C23 C22 C27 C26 0.1(3) . . . . ?
C21 C22 C27 C26 177.4(2) . . . . ?
C23 C22 C27 C28 -179.7(2) . . . . ?
C21 C22 C27 C28 -2.4(3) . . . . ?
C25 C26 C27 C22 0.4(4) . . . . ?
C25 C26 C27 C28 -179.8(3) . . . . ?
C22 C27 C28 C29 22.7(3) . . . . ?
C26 C27 C28 C29 -157.1(2) . . . . ?
N4 N3 C29 C28 -170.58(17) . . . . ?
C21 N3 C29 C28 68.2(2) . . . . ?
C27 C28 C29 N3 -53.6(3) . . . . ?
N3 N4 C31 O1 -9.1(3) . . . . ?
N3 N4 C31 C32 171.26(17) . . . . ?
O1 C31 C32 C33 137.0(2) . . . . ?
N4 C31 C32 C33 -43.3(3) . . . . ?
O1 C31 C32 C37 -38.9(3) . . . . ?
N4 C31 C32 C37 140.8(2) . . . . ?
C37 C32 C33 C34 0.4(4) . . . . ?
C31 C32 C33 C34 -175.6(2) . . . . ?
C32 C33 C34 C35 -1.3(4) . . . . ?
C33 C34 C35 C36 0.6(5) . . . . ?
C34 C35 C36 C37 0.9(5) . . . . ?
C33 C32 C37 C36 1.2(4) . . . . ?
C31 C32 C37 C36 177.2(3) . . . . ?
C35 C36 C37 C32 -1.8(5) . . . . ?

_refine_diff_density_max         0.360
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.049




_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_20210331_s1_lgg_m
_database_code_depnum_ccdc_archive 'CCDC 2111851'
loop_
_audit_author_name
_audit_author_address
ZJF
;Southwest Jiaotong University
China
;
_audit_update_record             
;
2021-09-25 deposited with the CCDC.	2024-02-05 downloaded from the CCDC.
;
_audit_creation_date             2021-04-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C27 H24 N4 O'
_chemical_formula_sum            'C27 H24 N4 O'
_chemical_formula_weight         420.50
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
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'

_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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   26.264(2)
_cell_length_b                   9.4519(8)
_cell_length_c                   18.6059(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4618.8(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2030
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.5050
_cell_measurement_theta_min      3.3490
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            4710
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.102
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -15.00   16.60   0.4000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.3211  -99.0000  -90.0000 79

#__ type_ start__ end____ width___ exp.time_
  2 omega    8.00   78.00   0.4000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       17.5086   57.0000    0.0000 175

#__ type_ start__ end____ width___ exp.time_
  3 omega  -15.00   29.00   0.4000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       17.5086  -19.0000  150.0000 110
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0077266000
_diffrn_orient_matrix_UB_12      0.0490059000
_diffrn_orient_matrix_UB_13      -0.0266773000
_diffrn_orient_matrix_UB_21      -0.0049422000
_diffrn_orient_matrix_UB_22      0.0509963000
_diffrn_orient_matrix_UB_23      0.0270691000
_diffrn_orient_matrix_UB_31      0.0254383000
_diffrn_orient_matrix_UB_32      0.0248648000
_diffrn_orient_matrix_UB_33      -0.0028428000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2783
_reflns_number_total             4710
_reflns_odcompleteness_completeness 99.68
_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, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4710
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0606
_refine_ls_restrained_S_all      1.006
_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)+(0.0709P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1528
_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:
 C23(H23A,H23B), C5(H5A,H5B), C22(H22A,H22B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C8(H8), C9(H9), C20(H20), C25(H25), C16(H16), C31(H31),
 C28(H28), C19(H19), C18(H18), C30(H30), C17(H17), C29(H29)
;
_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
O14 O 0.58223(5) 0.79109(16) 0.12215(7) 0.0468(4) Uani 1 1 d . . . . .
N21 N 0.65389(7) 0.85416(18) 0.18528(9) 0.0403(4) Uani 1 1 d . . . . .
N3 N 0.61537(7) 0.95843(19) 0.01515(9) 0.0438(5) Uani 1 1 d . . . . .
N2 N 0.57071(6) 0.8779(2) 0.00510(9) 0.0431(5) Uani 1 1 d . . . . .
C11 C 0.67560(7) 0.7558(2) 0.01521(11) 0.0356(5) Uani 1 1 d . . . . .
C13 C 0.63114(7) 0.8427(2) 0.12649(11) 0.0362(5) Uani 1 1 d . . . . .
C6 C 0.67659(7) 0.7593(2) -0.05992(11) 0.0401(5) Uani 1 1 d . . . . .
C12 C 0.65401(8) 0.8817(2) 0.05615(11) 0.0378(5) Uani 1 1 d . . . . .
H12 H 0.682133 0.947238 0.065610 0.045 Uiso 1 1 calc R . . . .
C7 C 0.69830(8) 0.6457(3) -0.09623(12) 0.0482(6) Uani 1 1 d . . . . .
H7 H 0.699887 0.647573 -0.146152 0.058 Uiso 1 1 calc R . . . .
C1 C 0.55656(8) 0.8019(2) 0.05728(11) 0.0398(5) Uani 1 1 d . . . . .
C26 C 0.68385(9) 0.5964(2) 0.26052(11) 0.0437(5) Uani 1 1 d . . . . .
C10 C 0.69488(8) 0.6390(2) 0.05127(12) 0.0438(6) Uani 1 1 d . . . . .
H10 H 0.694011 0.636345 0.101217 0.053 Uiso 1 1 calc R . . . .
C32 C 0.68833(10) 0.3879(3) 0.19872(12) 0.0494(6) Uani 1 1 d . . . . .
C27 C 0.65404(9) 0.4815(2) 0.23228(11) 0.0433(6) Uani 1 1 d . . . . .
C23 C 0.66420(9) 0.7252(2) 0.29848(12) 0.0488(6) Uani 1 1 d . . . . .
H23A H 0.692800 0.783566 0.312925 0.059 Uiso 1 1 calc R . . . .
H23B H 0.646391 0.696011 0.341684 0.059 Uiso 1 1 calc R . . . .
C5 C 0.65147(9) 0.8778(3) -0.10068(12) 0.0533(6) Uani 1 1 d . . . . .
H5A H 0.621542 0.840884 -0.124789 0.064 Uiso 1 1 calc R . . . .
H5B H 0.674775 0.911199 -0.137397 0.064 Uiso 1 1 calc R . . . .
C15 C 0.50981(8) 0.7164(2) 0.05663(12) 0.0412(5) Uani 1 1 d . . . . .
C22 C 0.62867(9) 0.8122(3) 0.25258(11) 0.0485(6) Uani 1 1 d . . . . .
H22A H 0.598400 0.757442 0.241667 0.058 Uiso 1 1 calc R . . . .
H22B H 0.618274 0.896049 0.278810 0.058 Uiso 1 1 calc R . . . .
N24 N 0.73606(9) 0.4415(2) 0.20673(12) 0.0578(6) Uani 1 1 d . . . . .
C4 C 0.63577(9) 1.0017(3) -0.05452(12) 0.0528(6) Uani 1 1 d . . . . .
H4A H 0.665043 1.062397 -0.046861 0.063 Uiso 1 1 calc R . . . .
H4B H 0.610170 1.056315 -0.079848 0.063 Uiso 1 1 calc R . . . .
C8 C 0.71736(8) 0.5312(3) -0.06021(13) 0.0525(6) Uani 1 1 d . . . . .
H8 H 0.731692 0.456492 -0.085679 0.063 Uiso 1 1 calc R . . . .
C9 C 0.71536(8) 0.5264(3) 0.01363(13) 0.0510(6) Uani 1 1 d . . . . .
H9 H 0.727734 0.447848 0.038121 0.061 Uiso 1 1 calc R . . . .
C20 C 0.46896(8) 0.7546(3) 0.01386(13) 0.0545(6) Uani 1 1 d . . . . .
H20 H 0.470430 0.837291 -0.013110 0.065 Uiso 1 1 calc R . . . .
C25 C 0.73257(9) 0.5662(3) 0.24408(13) 0.0513(6) Uani 1 1 d . . . . .
H25 H 0.760249 0.622519 0.256449 0.062 Uiso 1 1 calc R . . . .
C16 C 0.50704(9) 0.5936(3) 0.09650(13) 0.0534(6) Uani 1 1 d . . . . .
H16 H 0.534059 0.567384 0.125925 0.064 Uiso 1 1 calc R . . . .
C31 C 0.67162(13) 0.2651(3) 0.16531(14) 0.0689(8) Uani 1 1 d . . . . .
H31 H 0.694394 0.205062 0.142169 0.083 Uiso 1 1 calc R . . . .
C28 C 0.60261(9) 0.4469(3) 0.23365(13) 0.0564(7) Uani 1 1 d . . . . .
H28 H 0.579349 0.506109 0.256323 0.068 Uiso 1 1 calc R . . . .
C19 C 0.42634(9) 0.6711(3) 0.01104(15) 0.0653(8) Uani 1 1 d . . . . .
H19 H 0.398916 0.697984 -0.017475 0.078 Uiso 1 1 calc R . . . .
C18 C 0.42392(9) 0.5483(3) 0.04996(15) 0.0648(8) Uani 1 1 d . . . . .
H18 H 0.395124 0.491298 0.047438 0.078 Uiso 1 1 calc R . . . .
C30 C 0.62077(14) 0.2348(3) 0.16740(17) 0.0817(9) Uani 1 1 d . . . . .
H30 H 0.608917 0.152529 0.145702 0.098 Uiso 1 1 calc R . . . .
C17 C 0.46414(10) 0.5098(3) 0.09268(14) 0.0638(7) Uani 1 1 d . . . . .
H17 H 0.462479 0.426633 0.119262 0.077 Uiso 1 1 calc R . . . .
C29 C 0.58649(12) 0.3243(3) 0.20121(17) 0.0762(8) Uani 1 1 d . . . . .
H29 H 0.552087 0.301051 0.201926 0.091 Uiso 1 1 calc R . . . .
H24 H 0.7649(11) 0.402(3) 0.1992(16) 0.086(10) Uiso 1 1 d . . . . .


_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
O14 C13 1.377(2) . ?
O14 C1 1.386(2) . ?
N21 C13 1.251(2) . ?
N21 C22 1.471(3) . ?
N3 N2 1.411(2) . ?
N3 C12 1.462(3) . ?
N3 C4 1.461(3) . ?
N2 C1 1.263(3) . ?
C11 C6 1.399(3) . ?
C11 C12 1.522(3) . ?
C11 C10 1.388(3) . ?
C13 C12 1.486(3) . ?
C6 C7 1.391(3) . ?
C6 C5 1.505(3) . ?
C7 C8 1.367(3) . ?
C1 C15 1.470(3) . ?
C26 C27 1.439(3) . ?
C26 C23 1.499(3) . ?
C26 C25 1.346(3) . ?
C10 C9 1.382(3) . ?
C32 C27 1.408(3) . ?
C32 N24 1.360(3) . ?
C32 C31 1.388(3) . ?
C27 C28 1.390(3) . ?
C23 C22 1.509(3) . ?
C5 C4 1.510(3) . ?
C15 C20 1.384(3) . ?
C15 C16 1.379(3) . ?
N24 C25 1.371(3) . ?
C8 C9 1.376(3) . ?
C20 C19 1.370(3) . ?
C16 C17 1.379(3) . ?
C31 C30 1.366(4) . ?
C28 C29 1.373(4) . ?
C19 C18 1.369(4) . ?
C18 C17 1.371(3) . ?
C30 C29 1.387(4) . ?

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 O14 C1 118.59(16) . . ?
C13 N21 C22 120.40(18) . . ?
N2 N3 C12 112.24(16) . . ?
N2 N3 C4 109.77(17) . . ?
C4 N3 C12 110.32(16) . . ?
C1 N2 N3 116.70(17) . . ?
C6 C11 C12 119.26(19) . . ?
C10 C11 C6 119.7(2) . . ?
C10 C11 C12 121.06(18) . . ?
O14 C13 C12 114.42(18) . . ?
N21 C13 O14 121.84(19) . . ?
N21 C13 C12 123.75(18) . . ?
C11 C6 C5 120.9(2) . . ?
C7 C6 C11 118.3(2) . . ?
C7 C6 C5 120.6(2) . . ?
N3 C12 C11 112.65(17) . . ?
N3 C12 C13 107.57(16) . . ?
C13 C12 C11 113.43(17) . . ?
C8 C7 C6 121.5(2) . . ?
O14 C1 C15 111.87(18) . . ?
N2 C1 O14 124.62(19) . . ?
N2 C1 C15 123.50(19) . . ?
C27 C26 C23 126.7(2) . . ?
C25 C26 C27 105.9(2) . . ?
C25 C26 C23 127.4(2) . . ?
C9 C10 C11 120.6(2) . . ?
N24 C32 C27 107.9(2) . . ?
N24 C32 C31 130.7(3) . . ?
C31 C32 C27 121.4(3) . . ?
C32 C27 C26 106.8(2) . . ?
C28 C27 C26 134.4(2) . . ?
C28 C27 C32 118.8(2) . . ?
C26 C23 C22 112.88(18) . . ?
C6 C5 C4 114.22(18) . . ?
C20 C15 C1 120.6(2) . . ?
C16 C15 C1 120.17(19) . . ?
C16 C15 C20 119.2(2) . . ?
N21 C22 C23 110.50(18) . . ?
C32 N24 C25 108.3(2) . . ?
N3 C4 C5 112.83(18) . . ?
C7 C8 C9 120.1(2) . . ?
C8 C9 C10 119.7(2) . . ?
C19 C20 C15 120.4(2) . . ?
C26 C25 N24 111.2(2) . . ?
C15 C16 C17 119.9(2) . . ?
C30 C31 C32 118.1(3) . . ?
C29 C28 C27 119.4(3) . . ?
C18 C19 C20 120.4(2) . . ?
C19 C18 C17 119.7(2) . . ?
C31 C30 C29 121.3(3) . . ?
C18 C17 C16 120.5(3) . . ?
C28 C29 C30 120.9(3) . . ?

_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_zjf020
_database_code_depnum_ccdc_archive 'CCDC 2271212'
loop_
_audit_author_name
_audit_author_address
'Jianfeng Zheng'
;Southwest Jiaotong University
China
;
_audit_update_record             
;
2023-06-21 deposited with the CCDC.	2024-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H22 Cl2 N4 O'
_chemical_formula_sum            'C27 H22 Cl2 N4 O'
_chemical_formula_weight         489.38

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.1692(2)
_cell_length_b                   9.7507(2)
_cell_length_c                   23.6934(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.6860(10)
_cell_angle_gamma                90
_cell_volume                     2300.67(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9779
_cell_measurement_theta_min      3.81
_cell_measurement_theta_max      68.25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.549
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.101
_exptl_absorpt_coefficient_mu    2.767
_shelx_estimated_absorpt_T_min   0.312
_shelx_estimated_absorpt_T_max   0.767
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.4124
_exptl_absorpt_correction_T_max  0.9310
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42371
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.810
_diffrn_reflns_theta_max         68.248
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             8210
_reflns_number_gt                7704
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_max     0.951
_reflns_Friedel_fraction_full    0.953

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0345P)²+0.4919P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 3256 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.048(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         8210
_refine_ls_number_parameters     621
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0783
_refine_ls_wR_factor_gt          0.0759
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.34858(18) 0.3229(2) 0.40919(8) 0.0252(4) Uani 1 1 d . . . . .
N1A N -0.0773(3) 0.5756(3) 0.45708(11) 0.0371(7) Uani 1 1 d D . . . .
H1NA H -0.119(5) 0.627(5) 0.479(2) 0.072(16) Uiso 1 1 d D . . . .
N2A N 0.2121(2) 0.1823(3) 0.44960(9) 0.0227(5) Uani 1 1 d . . . . .
N3A N 0.5600(2) 0.2172(2) 0.48285(9) 0.0215(4) Uani 1 1 d . . . . .
N4A N 0.5814(2) 0.3232(3) 0.44633(9) 0.0221(5) Uani 1 1 d . . . . .
C1A C 0.1140(3) 0.1829(3) 0.39463(11) 0.0265(6) Uani 1 1 d . . . . .
H1AA H 0.107704 0.089634 0.377760 0.032 Uiso 1 1 calc R U . . .
H1AB H 0.145354 0.245781 0.367318 0.032 Uiso 1 1 calc R U . . .
C2A C -0.0244(3) 0.2281(4) 0.40264(12) 0.0309(7) Uani 1 1 d . . . . .
H2AA H -0.090965 0.204822 0.367336 0.037 Uiso 1 1 calc R U . . .
H2AB H -0.047904 0.175266 0.434885 0.037 Uiso 1 1 calc R U . . .
C3A C -0.0356(3) 0.3775(4) 0.41473(12) 0.0279(6) Uani 1 1 d . . . . .
C4A C -0.0689(3) 0.4358(4) 0.46229(13) 0.0352(8) Uani 1 1 d . . . . .
H4A H -0.084351 0.385924 0.494773 0.042 Uiso 1 1 calc R U . . .
C5A C -0.0253(3) 0.4895(3) 0.37631(11) 0.0250(6) Uani 1 1 d . . . . .
C6A C -0.0523(3) 0.6119(4) 0.40387(12) 0.0291(6) Uani 1 1 d . . . . .
C7A C -0.0543(3) 0.7403(4) 0.37781(13) 0.0334(7) Uani 1 1 d . . . . .
H7A H -0.071477 0.821888 0.396978 0.040 Uiso 1 1 calc R U . . .
C8A C -0.0300(3) 0.7421(3) 0.32259(14) 0.0315(6) Uani 1 1 d . . . . .
C9A C -0.0053(3) 0.6237(3) 0.29331(12) 0.0294(6) Uani 1 1 d . . . . .
H9A H 0.009163 0.629953 0.255018 0.035 Uiso 1 1 calc R U . . .
Cl1A Cl -0.03230(10) 0.89901(10) 0.28706(4) 0.0498(2) Uani 1 1 d . . . . .
Cl2A Cl 0.52030(10) 0.80768(9) 0.24050(3) 0.0458(2) Uani 1 1 d . . . . .
C10A C -0.0020(3) 0.4972(3) 0.32005(12) 0.0262(6) Uani 1 1 d . . . . .
H10A H 0.015839 0.416458 0.300485 0.031 Uiso 1 1 calc R U . . .
C11A C 0.3225(3) 0.2429(3) 0.45334(11) 0.0202(5) Uani 1 1 d . . . . .
C12A C 0.4360(3) 0.2312(3) 0.50524(11) 0.0217(5) Uani 1 1 d . . . . .
H12A H 0.422938 0.143095 0.525003 0.026 Uiso 1 1 calc R U . . .
C13A C 0.4435(3) 0.3453(3) 0.54993(11) 0.0210(5) Uani 1 1 d . . . . .
C14A C 0.3271(3) 0.4024(3) 0.56292(12) 0.0270(6) Uani 1 1 d . . . . .
H14A H 0.241801 0.377016 0.540919 0.032 Uiso 1 1 calc R U . . .
C15A C 0.3349(3) 0.4957(4) 0.60757(13) 0.0334(7) Uani 1 1 d . . . . .
H15A H 0.255244 0.533922 0.616107 0.040 Uiso 1 1 calc R U . . .
C16A C 0.4590(3) 0.5333(3) 0.63975(13) 0.0319(6) Uani 1 1 d . . . . .
H16A H 0.464595 0.596493 0.670669 0.038 Uiso 1 1 calc R U . . .
C17A C 0.5744(3) 0.4786(3) 0.62671(12) 0.0284(6) Uani 1 1 d . . . . .
H17A H 0.659284 0.505798 0.648598 0.034 Uiso 1 1 calc R U . . .
C18A C 0.5691(3) 0.3843(3) 0.58211(11) 0.0236(5) Uani 1 1 d . . . . .
C19A C 0.6981(3) 0.3280(3) 0.56856(12) 0.0270(6) Uani 1 1 d . . . . .
H19A H 0.759894 0.303816 0.605127 0.032 Uiso 1 1 calc R U . . .
H19B H 0.741761 0.400591 0.549598 0.032 Uiso 1 1 calc R U . . .
C20A C 0.6769(3) 0.2024(3) 0.52981(11) 0.0243(5) Uani 1 1 d . . . . .
H20A H 0.757858 0.187272 0.513418 0.029 Uiso 1 1 calc R U . . .
H20B H 0.664673 0.120834 0.553107 0.029 Uiso 1 1 calc R U . . .
C21A C 0.4789(3) 0.3691(3) 0.41179(11) 0.0212(5) Uani 1 1 d . . . . .
C22A C 0.4872(3) 0.4746(3) 0.36846(11) 0.0212(5) Uani 1 1 d . . . . .
C23A C 0.3737(3) 0.5476(3) 0.34153(11) 0.0239(6) Uani 1 1 d . . . . .
H23A H 0.288444 0.525450 0.349609 0.029 Uiso 1 1 calc R U . . .
C24A C 0.3844(3) 0.6521(3) 0.30315(11) 0.0268(6) Uani 1 1 d . . . . .
H24A H 0.307589 0.704010 0.286020 0.032 Uiso 1 1 calc R U . . .
C25A C 0.5081(3) 0.6798(3) 0.29007(11) 0.0299(6) Uani 1 1 d . . . . .
C26A C 0.6214(3) 0.6068(4) 0.31520(12) 0.0347(7) Uani 1 1 d . . . . .
H26A H 0.705461 0.626563 0.305393 0.042 Uiso 1 1 calc R U . . .
C27A C 0.6115(3) 0.5048(3) 0.35473(12) 0.0302(6) Uani 1 1 d . . . . .
H27A H 0.689303 0.455289 0.372591 0.036 Uiso 1 1 calc R U . . .
O1B O 0.43491(18) 0.6914(2) 0.09225(7) 0.0242(4) Uani 1 1 d . . . . .
N1B N -0.0356(3) 0.4293(4) 0.04218(11) 0.0384(7) Uani 1 1 d D . . . .
H1NB H -0.095(4) 0.377(4) 0.0194(16) 0.051(12) Uiso 1 1 d D . . . .
N2B N 0.2563(2) 0.8275(2) 0.05190(9) 0.0221(4) Uani 1 1 d . . . . .
N3B N 0.6297(2) 0.6876(2) 0.05306(9) 0.0213(4) Uani 1 1 d . . . . .
N4B N 0.5733(2) 0.7946(2) 0.01732(9) 0.0210(4) Uani 1 1 d . . . . .
C1B C 0.2113(3) 0.8234(3) 0.10728(11) 0.0271(6) Uani 1 1 d . . . . .
H1BA H 0.219803 0.916011 0.124742 0.032 Uiso 1 1 calc R U . . .
H1BB H 0.269891 0.760409 0.133992 0.032 Uiso 1 1 calc R U . . .
C2B C 0.0659(3) 0.7755(3) 0.09954(13) 0.0312(7) Uani 1 1 d . . . . .
H2BA H 0.033593 0.795502 0.135374 0.037 Uiso 1 1 calc R U . . .
H2BB H 0.010399 0.829511 0.068132 0.037 Uiso 1 1 calc R U . . .
C3B C 0.0449(3) 0.6277(4) 0.08599(12) 0.0293(7) Uani 1 1 d . . . . .
C4B C -0.0333(3) 0.5694(4) 0.03816(13) 0.0365(8) Uani 1 1 d . . . . .
H4B H -0.080163 0.619935 0.006043 0.044 Uiso 1 1 calc R U . . .
C5B C 0.0934(3) 0.5139(3) 0.12290(12) 0.0261(6) Uani 1 1 d . . . . .
C6B C 0.0404(3) 0.3912(4) 0.09468(12) 0.0302(7) Uani 1 1 d . . . . .
C7B C 0.0646(3) 0.2630(4) 0.12024(14) 0.0336(7) Uani 1 1 d . . . . .
H7B H 0.029847 0.181585 0.100754 0.040 Uiso 1 1 calc R U . . .
C8B C 0.1416(3) 0.2597(3) 0.17521(13) 0.0321(7) Uani 1 1 d . . . . .
C9B C 0.1954(3) 0.3780(4) 0.20491(12) 0.0298(6) Uani 1 1 d . . . . .
H9B H 0.247616 0.370994 0.242874 0.036 Uiso 1 1 calc R U . . .
Cl1B Cl 0.17246(11) 0.10256(10) 0.21073(4) 0.0536(2) Uani 1 1 d . . . . .
Cl2B Cl 0.75425(9) 0.19838(9) 0.25847(3) 0.04161(19) Uani 1 1 d . . . . .
C10B C 0.1721(3) 0.5040(3) 0.17882(12) 0.0278(6) Uani 1 1 d . . . . .
H10B H 0.209144 0.584263 0.198563 0.033 Uiso 1 1 calc R U . . .
C11B C 0.3650(3) 0.7698(3) 0.04791(11) 0.0192(5) Uani 1 1 d . . . . .
C12B C 0.4275(2) 0.7819(3) -0.00412(11) 0.0196(5) Uani 1 1 d . . . . .
H12B H 0.395633 0.870257 -0.023623 0.023 Uiso 1 1 calc R U . . .
C13B C 0.3905(3) 0.6679(3) -0.04871(11) 0.0200(5) Uani 1 1 d . . . . .
C14B C 0.2624(3) 0.6108(3) -0.06029(11) 0.0248(6) Uani 1 1 d . . . . .
H14B H 0.199532 0.636228 -0.037464 0.030 Uiso 1 1 calc R U . . .
C15B C 0.2255(3) 0.5172(3) -0.10482(13) 0.0297(6) Uani 1 1 d . . . . .
H15B H 0.137777 0.478835 -0.112389 0.036 Uiso 1 1 calc R U . . .
C16B C 0.3167(3) 0.4800(3) -0.13814(12) 0.0301(6) Uani 1 1 d . . . . .
H16B H 0.291478 0.416863 -0.168982 0.036 Uiso 1 1 calc R U . . .
C17B C 0.4448(3) 0.5349(3) -0.12644(12) 0.0270(6) Uani 1 1 d . . . . .
H17B H 0.507343 0.507665 -0.149120 0.032 Uiso 1 1 calc R U . . .
C18B C 0.4839(3) 0.6293(3) -0.08200(11) 0.0215(5) Uani 1 1 d . . . . .
C19B C 0.6262(3) 0.6844(3) -0.06975(12) 0.0266(6) Uani 1 1 d . . . . .
H19C H 0.651632 0.708604 -0.106691 0.032 Uiso 1 1 calc R U . . .
H19D H 0.687951 0.611355 -0.051349 0.032 Uiso 1 1 calc R U . . .
C20B C 0.6437(3) 0.8099(3) -0.03076(11) 0.0248(5) Uani 1 1 d . . . . .
H20C H 0.740533 0.824813 -0.015170 0.030 Uiso 1 1 calc R U . . .
H20D H 0.608582 0.891670 -0.053715 0.030 Uiso 1 1 calc R U . . .
C21B C 0.5612(3) 0.6431(3) 0.08866(11) 0.0201(5) Uani 1 1 d . . . . .
C22B C 0.6089(3) 0.5368(3) 0.13161(11) 0.0206(5) Uani 1 1 d . . . . .
C23B C 0.5228(3) 0.4769(3) 0.16338(12) 0.0259(6) Uani 1 1 d . . . . .
H23B H 0.432631 0.507884 0.158288 0.031 Uiso 1 1 calc R U . . .
C24B C 0.5674(3) 0.3728(3) 0.20233(12) 0.0289(6) Uani 1 1 d . . . . .
H24B H 0.507888 0.331419 0.223485 0.035 Uiso 1 1 calc R U . . .
C25B C 0.6988(3) 0.3300(3) 0.21003(11) 0.0278(6) Uani 1 1 d . . . . .
C26B C 0.7867(3) 0.3883(4) 0.17959(12) 0.0314(7) Uani 1 1 d . . . . .
H26B H 0.877087 0.357534 0.185434 0.038 Uiso 1 1 calc R U . . .
C27B C 0.7421(3) 0.4923(3) 0.14033(12) 0.0280(6) Uani 1 1 d . . . . .
H27B H 0.802183 0.533296 0.119387 0.034 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
O1A C11A 1.373(3) . ?
O1A C21A 1.389(3) . ?
N1A C4A 1.370(5) . ?
N1A C6A 1.382(4) . ?
N2A C11A 1.256(4) . ?
N2A C1A 1.472(3) . ?
N3A N4A 1.393(3) . ?
N3A C20A 1.462(3) . ?
N3A C12A 1.470(3) . ?
N4A C21A 1.269(4) . ?
C1A C2A 1.523(4) . ?
C2A C3A 1.494(5) . ?
C3A C4A 1.365(4) . ?
C3A C5A 1.439(4) . ?
C5A C10A 1.402(4) . ?
C5A C6A 1.414(5) . ?
C6A C7A 1.394(5) . ?
C7A C8A 1.380(5) . ?
C8A C9A 1.395(5) . ?
C8A Cl1A 1.744(3) . ?
C9A C10A 1.384(5) . ?
Cl2A C25A 1.734(3) . ?
C11A C12A 1.511(4) . ?
C12A C13A 1.527(4) . ?
C13A C14A 1.397(4) . ?
C13A C18A 1.401(4) . ?
C14A C15A 1.385(4) . ?
C15A C16A 1.385(5) . ?
C16A C17A 1.380(5) . ?
C17A C18A 1.393(4) . ?
C18A C19A 1.516(4) . ?
C19A C20A 1.520(4) . ?
C21A C22A 1.468(4) . ?
C22A C23A 1.396(4) . ?
C22A C27A 1.399(4) . ?
C23A C24A 1.384(4) . ?
C24A C25A 1.382(4) . ?
C25A C26A 1.383(5) . ?
C26A C27A 1.384(4) . ?
O1B C11B 1.375(3) . ?
O1B C21B 1.386(3) . ?
N1B C4B 1.370(5) . ?
N1B C6B 1.376(4) . ?
N2B C11B 1.261(4) . ?
N2B C1B 1.475(3) . ?
N3B C21B 1.274(4) . ?
N3B N4B 1.392(3) . ?
N4B C20B 1.470(3) . ?
N4B C12B 1.472(3) . ?
C1B C2B 1.525(4) . ?
C2B C3B 1.482(5) . ?
C3B C4B 1.369(4) . ?
C3B C5B 1.438(4) . ?
C5B C10B 1.406(4) . ?
C5B C6B 1.423(4) . ?
C6B C7B 1.389(5) . ?
C7B C8B 1.377(5) . ?
C8B C9B 1.403(5) . ?
C8B Cl1B 1.746(3) . ?
C9B C10B 1.374(5) . ?
Cl2B C25B 1.737(3) . ?
C11B C12B 1.501(3) . ?
C12B C13B 1.527(4) . ?
C13B C14B 1.392(4) . ?
C13B C18B 1.403(4) . ?
C14B C15B 1.388(4) . ?
C15B C16B 1.383(4) . ?
C16B C17B 1.383(4) . ?
C17B C18B 1.395(4) . ?
C18B C19B 1.516(4) . ?
C19B C20B 1.522(4) . ?
C21B C22B 1.465(4) . ?
C22B C23B 1.392(4) . ?
C22B C27B 1.397(4) . ?
C23B C24B 1.385(4) . ?
C24B C25B 1.377(4) . ?
C25B C26B 1.380(4) . ?
C26B C27B 1.389(4) . ?

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
C11A O1A C21A 118.7(2) . . ?
C4A N1A C6A 108.5(3) . . ?
C11A N2A C1A 119.8(2) . . ?
N4A N3A C20A 109.9(2) . . ?
N4A N3A C12A 114.1(2) . . ?
C20A N3A C12A 111.1(2) . . ?
C21A N4A N3A 116.8(2) . . ?
N2A C1A C2A 111.7(2) . . ?
C3A C2A C1A 114.5(2) . . ?
C4A C3A C5A 105.6(3) . . ?
C4A C3A C2A 127.3(3) . . ?
C5A C3A C2A 126.9(3) . . ?
C3A C4A N1A 111.2(3) . . ?
C10A C5A C6A 118.6(3) . . ?
C10A C5A C3A 133.7(3) . . ?
C6A C5A C3A 107.6(2) . . ?
N1A C6A C7A 130.2(3) . . ?
N1A C6A C5A 107.1(3) . . ?
C7A C6A C5A 122.7(2) . . ?
C8A C7A C6A 116.2(3) . . ?
C7A C8A C9A 123.1(3) . . ?
C7A C8A Cl1A 118.8(3) . . ?
C9A C8A Cl1A 118.2(2) . . ?
C10A C9A C8A 120.0(3) . . ?
C9A C10A C5A 119.4(3) . . ?
N2A C11A O1A 121.4(2) . . ?
N2A C11A C12A 123.1(2) . . ?
O1A C11A C12A 115.5(2) . . ?
N3A C12A C11A 106.4(2) . . ?
N3A C12A C13A 113.1(2) . . ?
C11A C12A C13A 115.6(2) . . ?
C14A C13A C18A 119.4(3) . . ?
C14A C13A C12A 121.2(2) . . ?
C18A C13A C12A 119.1(2) . . ?
C15A C14A C13A 120.6(3) . . ?
C16A C15A C14A 120.0(3) . . ?
C17A C16A C15A 119.7(3) . . ?
C16A C17A C18A 121.4(3) . . ?
C17A C18A C13A 118.9(3) . . ?
C17A C18A C19A 119.8(3) . . ?
C13A C18A C19A 121.3(3) . . ?
C18A C19A C20A 113.4(2) . . ?
N3A C20A C19A 112.0(2) . . ?
N4A C21A O1A 124.5(2) . . ?
N4A C21A C22A 122.8(2) . . ?
O1A C21A C22A 112.7(2) . . ?
C23A C22A C27A 119.2(3) . . ?
C23A C22A C21A 121.2(2) . . ?
C27A C22A C21A 119.5(2) . . ?
C24A C23A C22A 120.6(3) . . ?
C25A C24A C23A 119.2(3) . . ?
C24A C25A C26A 121.3(3) . . ?
C24A C25A Cl2A 119.1(2) . . ?
C26A C25A Cl2A 119.6(2) . . ?
C25A C26A C27A 119.6(3) . . ?
C26A C27A C22A 120.1(3) . . ?
C11B O1B C21B 118.9(2) . . ?
C4B N1B C6B 108.5(3) . . ?
C11B N2B C1B 119.3(2) . . ?
C21B N3B N4B 116.4(2) . . ?
N3B N4B C20B 110.0(2) . . ?
N3B N4B C12B 114.1(2) . . ?
C20B N4B C12B 110.83(19) . . ?
N2B C1B C2B 111.7(2) . . ?
C3B C2B C1B 114.7(2) . . ?
C4B C3B C5B 104.6(3) . . ?
C4B C3B C2B 128.1(3) . . ?
C5B C3B C2B 127.0(3) . . ?
C3B C4B N1B 111.9(3) . . ?
C10B C5B C6B 118.3(3) . . ?
C10B C5B C3B 133.4(3) . . ?
C6B C5B C3B 108.2(2) . . ?
N1B C6B C7B 130.9(3) . . ?
N1B C6B C5B 106.7(3) . . ?
C7B C6B C5B 122.3(3) . . ?
C8B C7B C6B 116.7(3) . . ?
C7B C8B C9B 123.0(3) . . ?
C7B C8B Cl1B 119.2(3) . . ?
C9B C8B Cl1B 117.8(2) . . ?
C10B C9B C8B 119.7(3) . . ?
C9B C10B C5B 119.9(3) . . ?
N2B C11B O1B 121.1(2) . . ?
N2B C11B C12B 123.3(2) . . ?
O1B C11B C12B 115.6(2) . . ?
N4B C12B C11B 106.7(2) . . ?
N4B C12B C13B 112.9(2) . . ?
C11B C12B C13B 115.1(2) . . ?
C14B C13B C18B 119.7(3) . . ?
C14B C13B C12B 121.1(2) . . ?
C18B C13B C12B 119.0(2) . . ?
C15B C14B C13B 120.7(3) . . ?
C16B C15B C14B 119.8(3) . . ?
C15B C16B C17B 119.8(3) . . ?
C16B C17B C18B 121.3(3) . . ?
C17B C18B C13B 118.7(2) . . ?
C17B C18B C19B 119.6(2) . . ?
C13B C18B C19B 121.8(2) . . ?
C18B C19B C20B 113.0(2) . . ?
N4B C20B C19B 111.9(2) . . ?
N3B C21B O1B 124.2(2) . . ?
N3B C21B C22B 123.5(2) . . ?
O1B C21B C22B 112.2(2) . . ?
C23B C22B C27B 119.1(3) . . ?
C23B C22B C21B 121.1(2) . . ?
C27B C22B C21B 119.8(2) . . ?
C24B C23B C22B 120.7(3) . . ?
C25B C24B C23B 119.2(3) . . ?
C24B C25B C26B 121.3(3) . . ?
C24B C25B Cl2B 119.2(2) . . ?
C26B C25B Cl2B 119.5(2) . . ?
C25B C26B C27B 119.5(3) . . ?
C26B C27B C22B 120.1(3) . . ?

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
C20A N3A N4A C21A -164.2(2) . . . . ?
C12A N3A N4A C21A -38.6(3) . . . . ?
C11A N2A C1A C2A -128.9(3) . . . . ?
N2A C1A C2A C3A 72.5(3) . . . . ?
C1A C2A C3A C4A -120.0(3) . . . . ?
C1A C2A C3A C5A 66.0(4) . . . . ?
C5A C3A C4A N1A -1.3(3) . . . . ?
C2A C3A C4A N1A -176.3(3) . . . . ?
C6A N1A C4A C3A 1.6(4) . . . . ?
C4A C3A C5A C10A -175.7(3) . . . . ?
C2A C3A C5A C10A -0.7(5) . . . . ?
C4A C3A C5A C6A 0.6(3) . . . . ?
C2A C3A C5A C6A 175.6(3) . . . . ?
C4A N1A C6A C7A 177.2(3) . . . . ?
C4A N1A C6A C5A -1.1(3) . . . . ?
C10A C5A C6A N1A 177.3(3) . . . . ?
C3A C5A C6A N1A 0.3(3) . . . . ?
C10A C5A C6A C7A -1.2(4) . . . . ?
C3A C5A C6A C7A -178.2(3) . . . . ?
N1A C6A C7A C8A -177.3(3) . . . . ?
C5A C6A C7A C8A 0.8(4) . . . . ?
C6A C7A C8A C9A 0.4(4) . . . . ?
C6A C7A C8A Cl1A 179.5(2) . . . . ?
C7A C8A C9A C10A -1.2(4) . . . . ?
Cl1A C8A C9A C10A 179.7(2) . . . . ?
C8A C9A C10A C5A 0.8(4) . . . . ?
C6A C5A C10A C9A 0.4(4) . . . . ?
C3A C5A C10A C9A 176.4(3) . . . . ?
C1A N2A C11A O1A 7.3(4) . . . . ?
C1A N2A C11A C12A -171.3(3) . . . . ?
C21A O1A C11A N2A -169.7(3) . . . . ?
C21A O1A C11A C12A 9.0(3) . . . . ?
N4A N3A C12A C11A 56.2(3) . . . . ?
C20A N3A C12A C11A -178.9(2) . . . . ?
N4A N3A C12A C13A -71.8(3) . . . . ?
C20A N3A C12A C13A 53.1(3) . . . . ?
N2A C11A C12A N3A 137.9(3) . . . . ?
O1A C11A C12A N3A -40.8(3) . . . . ?
N2A C11A C12A C13A -95.6(3) . . . . ?
O1A C11A C12A C13A 85.7(3) . . . . ?
N3A C12A C13A C14A 160.1(2) . . . . ?
C11A C12A C13A C14A 37.1(3) . . . . ?
N3A C12A C13A C18A -25.8(3) . . . . ?
C11A C12A C13A C18A -148.8(2) . . . . ?
C18A C13A C14A C15A -0.7(4) . . . . ?
C12A C13A C14A C15A 173.4(3) . . . . ?
C13A C14A C15A C16A 0.1(5) . . . . ?
C14A C15A C16A C17A 0.7(5) . . . . ?
C15A C16A C17A C18A -0.9(5) . . . . ?
C16A C17A C18A C13A 0.3(4) . . . . ?
C16A C17A C18A C19A 179.2(3) . . . . ?
C14A C13A C18A C17A 0.5(4) . . . . ?
C12A C13A C18A C17A -173.7(2) . . . . ?
C14A C13A C18A C19A -178.3(3) . . . . ?
C12A C13A C18A C19A 7.5(4) . . . . ?
C17A C18A C19A C20A 165.7(3) . . . . ?
C13A C18A C19A C20A -15.5(4) . . . . ?
N4A N3A C20A C19A 64.8(3) . . . . ?
C12A N3A C20A C19A -62.5(3) . . . . ?
C18A C19A C20A N3A 42.4(3) . . . . ?
N3A N4A C21A O1A 1.6(4) . . . . ?
N3A N4A C21A C22A -176.2(2) . . . . ?
C11A O1A C21A N4A 13.6(4) . . . . ?
C11A O1A C21A C22A -168.5(2) . . . . ?
N4A C21A C22A C23A -163.4(3) . . . . ?
O1A C21A C22A C23A 18.6(4) . . . . ?
N4A C21A C22A C27A 15.2(4) . . . . ?
O1A C21A C22A C27A -162.8(3) . . . . ?
C27A C22A C23A C24A -2.2(4) . . . . ?
C21A C22A C23A C24A 176.4(3) . . . . ?
C22A C23A C24A C25A 2.5(4) . . . . ?
C23A C24A C25A C26A -1.0(4) . . . . ?
C23A C24A C25A Cl2A 178.3(2) . . . . ?
C24A C25A C26A C27A -0.7(5) . . . . ?
Cl2A C25A C26A C27A -180.0(2) . . . . ?
C25A C26A C27A C22A 1.0(5) . . . . ?
C23A C22A C27A C26A 0.5(4) . . . . ?
C21A C22A C27A C26A -178.1(3) . . . . ?
C21B N3B N4B C20B -164.9(2) . . . . ?
C21B N3B N4B C12B -39.6(3) . . . . ?
C11B N2B C1B C2B -129.6(3) . . . . ?
N2B C1B C2B C3B 71.8(3) . . . . ?
C1B C2B C3B C4B -119.7(3) . . . . ?
C1B C2B C3B C5B 66.2(4) . . . . ?
C5B C3B C4B N1B -0.7(3) . . . . ?
C2B C3B C4B N1B -175.9(3) . . . . ?
C6B N1B C4B C3B 1.4(4) . . . . ?
C4B C3B C5B C10B -176.5(3) . . . . ?
C2B C3B C5B C10B -1.2(5) . . . . ?
C4B C3B C5B C6B -0.2(3) . . . . ?
C2B C3B C5B C6B 175.1(3) . . . . ?
C4B N1B C6B C7B 176.8(3) . . . . ?
C4B N1B C6B C5B -1.4(3) . . . . ?
C10B C5B C6B N1B 177.9(2) . . . . ?
C3B C5B C6B N1B 0.9(3) . . . . ?
C10B C5B C6B C7B -0.5(4) . . . . ?
C3B C5B C6B C7B -177.5(3) . . . . ?
N1B C6B C7B C8B -177.0(3) . . . . ?
C5B C6B C7B C8B 1.0(4) . . . . ?
C6B C7B C8B C9B -0.6(4) . . . . ?
C6B C7B C8B Cl1B 178.3(2) . . . . ?
C7B C8B C9B C10B -0.3(4) . . . . ?
Cl1B C8B C9B C10B -179.2(2) . . . . ?
C8B C9B C10B C5B 0.7(4) . . . . ?
C6B C5B C10B C9B -0.4(4) . . . . ?
C3B C5B C10B C9B 175.7(3) . . . . ?
C1B N2B C11B O1B 6.8(4) . . . . ?
C1B N2B C11B C12B -172.6(2) . . . . ?
C21B O1B C11B N2B -172.6(2) . . . . ?
C21B O1B C11B C12B 6.8(3) . . . . ?
N3B N4B C12B C11B 56.3(3) . . . . ?
C20B N4B C12B C11B -178.9(2) . . . . ?
N3B N4B C12B C13B -71.2(3) . . . . ?
C20B N4B C12B C13B 53.6(3) . . . . ?
N2B C11B C12B N4B 140.3(3) . . . . ?
O1B C11B C12B N4B -39.2(3) . . . . ?
N2B C11B C12B C13B -93.5(3) . . . . ?
O1B C11B C12B C13B 87.0(3) . . . . ?
N4B C12B C13B C14B 159.3(2) . . . . ?
C11B C12B C13B C14B 36.4(3) . . . . ?
N4B C12B C13B C18B -26.5(3) . . . . ?
C11B C12B C13B C18B -149.4(2) . . . . ?
C18B C13B C14B C15B -0.7(4) . . . . ?
C12B C13B C14B C15B 173.5(3) . . . . ?
C13B C14B C15B C16B 0.0(5) . . . . ?
C14B C15B C16B C17B 0.8(5) . . . . ?
C15B C16B C17B C18B -1.0(5) . . . . ?
C16B C17B C18B C13B 0.3(4) . . . . ?
C16B C17B C18B C19B 178.6(3) . . . . ?
C14B C13B C18B C17B 0.5(4) . . . . ?
C12B C13B C18B C17B -173.8(2) . . . . ?
C14B C13B C18B C19B -177.7(3) . . . . ?
C12B C13B C18B C19B 8.0(4) . . . . ?
C17B C18B C19B C20B 166.0(2) . . . . ?
C13B C18B C19B C20B -15.8(4) . . . . ?
N3B N4B C20B C19B 64.3(3) . . . . ?
C12B N4B C20B C19B -62.9(3) . . . . ?
C18B C19B C20B N4B 42.6(3) . . . . ?
N4B N3B C21B O1B 2.1(4) . . . . ?
N4B N3B C21B C22B -176.3(2) . . . . ?
C11B O1B C21B N3B 14.7(4) . . . . ?
C11B O1B C21B C22B -166.7(2) . . . . ?
N3B C21B C22B C23B -170.0(3) . . . . ?
O1B C21B C22B C23B 11.4(4) . . . . ?
N3B C21B C22B C27B 8.8(4) . . . . ?
O1B C21B C22B C27B -169.8(2) . . . . ?
C27B C22B C23B C24B -1.3(4) . . . . ?
C21B C22B C23B C24B 177.5(3) . . . . ?
C22B C23B C24B C25B 0.9(4) . . . . ?
C23B C24B C25B C26B -0.3(5) . . . . ?
C23B C24B C25B Cl2B -179.5(2) . . . . ?
C24B C25B C26B C27B 0.0(5) . . . . ?
Cl2B C25B C26B C27B 179.2(2) . . . . ?
C25B C26B C27B C22B -0.4(5) . . . . ?
C23B C22B C27B C26B 1.0(4) . . . . ?
C21B C22B C27B C26B -177.8(3) . . . . ?

_refine_diff_density_max         0.145
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.043



