# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_10382
_database_code_depnum_ccdc_archive 'CCDC 1944350'
loop_
_audit_author_name
_audit_author_address
'Ji Yanling'
;chengdu uniwersity of TCM
China
;
_audit_update_record             
;
2019-07-31 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H21 Cl N4 O'
_chemical_formula_weight         464.94

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.5705(5)
_cell_length_b                   11.9923(7)
_cell_length_c                   27.772(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2521.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1881
_cell_measurement_theta_min      3.9940
_cell_measurement_theta_max      70.3350

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    1.549
_shelx_estimated_absorpt_T_min   0.824
_shelx_estimated_absorpt_T_max   0.848
_exptl_absorpt_correction_T_min  0.86976
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5868
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.183
_diffrn_reflns_theta_max         67.244
_diffrn_reflns_theta_full        67.244
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_point_group_measured_fraction_full 0.862
_reflns_number_total             3882
_reflns_number_gt                3218
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.501
_reflns_Friedel_fraction_max     0.679
_reflns_Friedel_fraction_full    0.679

_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       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0444P)²+0.2880P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0063(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 862 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(3)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3882
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1235
_refine_ls_wR_factor_gt          0.1120
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
Cl1 Cl 0.3433(4) 0.28901(17) 0.54145(8) 0.1677(12) Uani 1 1 d . . . . .
N1 N 0.5046(6) 0.3643(3) 0.71464(15) 0.0778(11) Uani 1 1 d . . . . .
N2 N 0.5210(5) 0.6569(3) 0.71801(13) 0.0722(11) Uani 1 1 d . . . . .
H2A H 0.549300 0.604503 0.737680 0.087 Uiso 1 1 calc R U . . .
H2B H 0.529844 0.725486 0.726753 0.087 Uiso 1 1 calc R U . . .
N3 N 0.4745(4) 0.9148(3) 0.66604(14) 0.0616(9) Uani 1 1 d . . . . .
N4 N 0.2993(4) 0.8910(2) 0.67921(12) 0.0530(8) Uani 1 1 d . . . . .
O1 O 0.1043(3) 0.7431(2) 0.67231(10) 0.0551(6) Uani 1 1 d . . . . .
C1 C 0.1782(9) 0.3408(4) 0.57898(17) 0.0829(16) Uani 1 1 d . . . . .
C28 C 0.7231(6) 0.8224(5) 0.6279(2) 0.0880(17) Uani 1 1 d . . . . .
H28A H 0.775584 0.895170 0.629511 0.132 Uiso 1 1 calc R U . . .
H28B H 0.721385 0.797470 0.595040 0.132 Uiso 1 1 calc R U . . .
H28C H 0.791089 0.771245 0.646974 0.132 Uiso 1 1 calc R U . . .
C2 C 0.0163(11) 0.2857(5) 0.5798(2) 0.102(2) Uani 1 1 d . . . . .
H2 H -0.001464 0.223133 0.560606 0.122 Uiso 1 1 calc R U . . .
C3 C -0.1159(9) 0.3238(5) 0.6086(3) 0.104(2) Uani 1 1 d . . . . .
H3 H -0.224151 0.287133 0.609342 0.125 Uiso 1 1 calc R U . . .
C4 C -0.0890(7) 0.4157(5) 0.6365(2) 0.0888(16) Uani 1 1 d . . . . .
H4 H -0.179178 0.442210 0.656194 0.107 Uiso 1 1 calc R U . . .
C5 C 0.0721(5) 0.4693(4) 0.63558(19) 0.0653(11) Uani 1 1 d . . . . .
H5 H 0.088545 0.532134 0.654682 0.078 Uiso 1 1 calc R U . . .
C6 C 0.2101(6) 0.4323(3) 0.60699(13) 0.0528(9) Uani 1 1 d . . . . .
C7 C 0.3840(5) 0.4967(3) 0.60692(12) 0.0479(8) Uani 1 1 d . . . . .
H7 H 0.474486 0.449100 0.592274 0.057 Uiso 1 1 calc R U . . .
C8 C 0.3634(5) 0.5978(3) 0.57620(13) 0.0497(8) Uani 1 1 d . . . . .
H8 H 0.344350 0.585925 0.543508 0.060 Uiso 1 1 calc R U . . .
C9 C 0.3695(4) 0.7026(3) 0.59087(12) 0.0442(7) Uani 1 1 d . . . . .
C10 C 0.4098(4) 0.7313(3) 0.64312(13) 0.0443(8) Uani 1 1 d . . . . .
C11 C 0.4626(5) 0.6316(3) 0.67348(13) 0.0483(8) Uani 1 1 d . . . . .
C12 C 0.4447(4) 0.5269(3) 0.65688(13) 0.0468(8) Uani 1 1 d . . . . .
C13 C 0.4791(5) 0.4361(3) 0.68867(14) 0.0536(9) Uani 1 1 d . . . . .
C14 C 0.3383(5) 0.7976(3) 0.55703(14) 0.0534(9) Uani 1 1 d . . . . .
C15 C 0.4353(7) 0.8039(5) 0.51536(19) 0.0845(16) Uani 1 1 d . . . . .
H15 H 0.521795 0.750682 0.509268 0.101 Uiso 1 1 calc R U . . .
C16 C 0.4065(8) 0.8884(6) 0.4822(2) 0.110(2) Uani 1 1 d . . . . .
H16 H 0.472538 0.891359 0.454001 0.132 Uiso 1 1 calc R U . . .
C17 C 0.2805(10) 0.9671(5) 0.4912(3) 0.108(2) Uani 1 1 d . . . . .
H17 H 0.261711 1.024605 0.469346 0.129 Uiso 1 1 calc R U . . .
C18 C 0.1826(10) 0.9616(4) 0.5322(2) 0.099(2) Uani 1 1 d . . . . .
H18 H 0.097845 1.015892 0.538353 0.119 Uiso 1 1 calc R U . . .
C19 C 0.2083(8) 0.8758(4) 0.56472(17) 0.0750(14) Uani 1 1 d . . . . .
H19 H 0.137302 0.871010 0.591966 0.090 Uiso 1 1 calc R U . . .
C20 C 0.2472(5) 0.7858(3) 0.66702(13) 0.0449(8) Uani 1 1 d . . . . .
C21 C 0.5398(5) 0.8274(3) 0.64665(15) 0.0563(10) Uani 1 1 d . . . . .
C22 C 0.1886(6) 0.9807(3) 0.69396(13) 0.0551(9) Uani 1 1 d . . . . .
C23 C 0.2346(6) 1.0886(3) 0.68317(17) 0.0654(11) Uani 1 1 d . . . . .
H23 H 0.340738 1.103454 0.667586 0.078 Uiso 1 1 calc R U . . .
C24 C 0.1224(8) 1.1754(4) 0.69558(19) 0.0778(14) Uani 1 1 d . . . . .
H24 H 0.153832 1.248458 0.688307 0.093 Uiso 1 1 calc R U . . .
C25 C -0.0335(9) 1.1544(4) 0.71835(19) 0.0879(17) Uani 1 1 d . . . . .
H25 H -0.108916 1.212794 0.726227 0.105 Uiso 1 1 calc R U . . .
C26 C -0.0790(9) 1.0466(4) 0.7296(2) 0.0934(18) Uani 1 1 d . . . . .
H26 H -0.185572 1.032427 0.745120 0.112 Uiso 1 1 calc R U . . .
C27 C 0.0322(8) 0.9591(4) 0.71815(18) 0.0800(15) Uani 1 1 d . . . . .
H27 H 0.002385 0.886404 0.726574 0.096 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.742(6) . ?
N1 C13 1.139(5) . ?
N2 C11 1.348(5) . ?
N3 C21 1.277(5) . ?
N3 N4 1.405(5) . ?
N4 C20 1.365(4) . ?
N4 C22 1.425(5) . ?
O1 C20 1.205(4) . ?
C1 C6 1.366(6) . ?
C1 C2 1.393(9) . ?
C28 C21 1.484(6) . ?
C2 C3 1.361(9) . ?
C3 C4 1.363(9) . ?
C4 C5 1.379(6) . ?
C5 C6 1.385(6) . ?
C6 C7 1.526(6) . ?
C7 C8 1.491(5) . ?
C7 C12 1.506(5) . ?
C8 C9 1.323(5) . ?
C9 C14 1.495(5) . ?
C9 C10 1.522(5) . ?
C10 C11 1.517(5) . ?
C10 C21 1.519(5) . ?
C10 C20 1.543(5) . ?
C11 C12 1.345(5) . ?
C12 C13 1.426(5) . ?
C14 C15 1.373(6) . ?
C14 C19 1.377(6) . ?
C15 C16 1.386(7) . ?
C16 C17 1.366(9) . ?
C17 C18 1.359(9) . ?
C18 C19 1.383(7) . ?
C22 C23 1.373(6) . ?
C22 C27 1.386(7) . ?
C23 C24 1.387(6) . ?
C24 C25 1.363(8) . ?
C25 C26 1.373(7) . ?
C26 C27 1.383(7) . ?

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
C21 N3 N4 108.0(3) . . ?
C20 N4 N3 113.3(3) . . ?
C20 N4 C22 126.8(3) . . ?
N3 N4 C22 118.5(3) . . ?
C6 C1 C2 121.8(6) . . ?
C6 C1 Cl1 120.0(4) . . ?
C2 C1 Cl1 118.1(4) . . ?
C3 C2 C1 119.8(5) . . ?
C2 C3 C4 119.8(6) . . ?
C3 C4 C5 119.9(6) . . ?
C4 C5 C6 121.9(5) . . ?
C1 C6 C5 116.8(4) . . ?
C1 C6 C7 123.9(4) . . ?
C5 C6 C7 119.3(3) . . ?
C8 C7 C12 111.3(3) . . ?
C8 C7 C6 108.8(3) . . ?
C12 C7 C6 112.6(3) . . ?
C9 C8 C7 126.4(3) . . ?
C8 C9 C14 121.7(3) . . ?
C8 C9 C10 121.0(3) . . ?
C14 C9 C10 117.3(3) . . ?
C11 C10 C21 113.0(3) . . ?
C11 C10 C9 113.9(3) . . ?
C21 C10 C9 111.3(3) . . ?
C11 C10 C20 107.7(3) . . ?
C21 C10 C20 99.7(3) . . ?
C9 C10 C20 110.2(3) . . ?
C12 C11 N2 123.9(4) . . ?
C12 C11 C10 121.3(3) . . ?
N2 C11 C10 114.8(3) . . ?
C11 C12 C13 118.8(3) . . ?
C11 C12 C7 124.8(3) . . ?
C13 C12 C7 116.3(3) . . ?
N1 C13 C12 178.8(5) . . ?
C15 C14 C19 118.4(4) . . ?
C15 C14 C9 119.2(4) . . ?
C19 C14 C9 122.3(4) . . ?
C14 C15 C16 121.1(5) . . ?
C17 C16 C15 119.6(6) . . ?
C18 C17 C16 120.1(5) . . ?
C17 C18 C19 120.4(6) . . ?
C14 C19 C18 120.4(5) . . ?
O1 C20 N4 128.4(3) . . ?
O1 C20 C10 126.1(3) . . ?
N4 C20 C10 105.5(3) . . ?
N3 C21 C28 122.9(4) . . ?
N3 C21 C10 113.5(3) . . ?
C28 C21 C10 123.6(4) . . ?
C23 C22 C27 120.0(4) . . ?
C23 C22 N4 120.0(4) . . ?
C27 C22 N4 120.0(4) . . ?
C22 C23 C24 119.8(5) . . ?
C25 C24 C23 120.4(5) . . ?
C24 C25 C26 119.8(5) . . ?
C25 C26 C27 120.6(6) . . ?
C26 C27 C22 119.3(5) . . ?

_refine_diff_density_max         0.261
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_10381
_database_code_depnum_ccdc_archive 'CCDC 1944352'
loop_
_audit_author_name
_audit_author_address
'Ji Yanling'
;chengdu university of TCM
China
;
_audit_update_record             
;
2019-07-31 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H21 Cl N4 O'
_chemical_formula_weight         464.94

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.6734(5)
_cell_length_b                   11.9044(8)
_cell_length_c                   27.0141(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2467.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3062
_cell_measurement_theta_min      3.9890
_cell_measurement_theta_max      53.3830

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.583
_shelx_estimated_absorpt_T_min   0.871
_shelx_estimated_absorpt_T_max   0.884
_exptl_absorpt_correction_T_min  0.59358
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16107
_diffrn_reflns_av_unetI/netI     0.0786
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.272
_diffrn_reflns_theta_max         67.232
_diffrn_reflns_theta_full        67.232
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4413
_reflns_number_gt                2282
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1058P)²+0.1181P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0133(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 512 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4413
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1326
_refine_ls_R_factor_gt           0.0785
_refine_ls_wR_factor_ref         0.2507
_refine_ls_wR_factor_gt          0.1863
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
Cl1 Cl 0.2218(4) 0.2192(3) 0.58156(13) 0.1251(12) Uani 1 1 d . . . . .
N1 N 1.0089(14) 0.3265(6) 0.7086(3) 0.103(3) Uani 1 1 d . . . . .
N2 N 1.0146(11) 0.6196(6) 0.7223(3) 0.094(2) Uani 1 1 d . . . . .
H2A H 1.039597 0.563262 0.740893 0.113 Uiso 1 1 calc R U . . .
H2B H 1.021808 0.686814 0.733784 0.113 Uiso 1 1 calc R U . . .
N3 N 0.8014(10) 0.8651(5) 0.6843(3) 0.0756(19) Uani 1 1 d . . . . .
N4 N 0.9773(11) 0.8905(6) 0.6728(3) 0.087(2) Uani 1 1 d . . . . .
O1 O 0.6106(8) 0.7161(4) 0.6750(2) 0.0763(15) Uani 1 1 d . . . . .
C1 C 0.4161(13) 0.2934(7) 0.5877(4) 0.085(3) Uani 1 1 d . . . . .
C2 C 0.4253(14) 0.3819(8) 0.6192(3) 0.089(3) Uani 1 1 d . . . . .
H2 H 0.327797 0.403264 0.637380 0.107 Uiso 1 1 calc R U . . .
C3 C 0.5811(13) 0.4406(7) 0.6244(3) 0.080(2) Uani 1 1 d . . . . .
H3 H 0.587349 0.500855 0.646290 0.097 Uiso 1 1 calc R U . . .
C4 C 0.7260(12) 0.4104(6) 0.5975(3) 0.073(2) Uani 1 1 d . . . . .
C5 C 0.7138(16) 0.3216(7) 0.5659(3) 0.092(3) Uani 1 1 d . . . . .
H5 H 0.811233 0.299369 0.547904 0.111 Uiso 1 1 calc R U . . .
C6 C 0.5572(16) 0.2634(8) 0.5600(4) 0.100(3) Uani 1 1 d . . . . .
H6 H 0.549295 0.204619 0.537481 0.120 Uiso 1 1 calc R U . . .
C7 C 0.8946(12) 0.4770(6) 0.6016(3) 0.068(2) Uani 1 1 d . . . . .
H7 H 0.986870 0.433046 0.585655 0.081 Uiso 1 1 calc R U . . .
C8 C 0.8749(11) 0.5839(6) 0.5733(3) 0.073(2) Uani 1 1 d . . . . .
H8 H 0.859546 0.577804 0.539229 0.087 Uiso 1 1 calc R U . . .
C9 C 0.8773(11) 0.6868(6) 0.5921(3) 0.068(2) Uani 1 1 d . . . . .
C10 C 0.9150(11) 0.7070(6) 0.6468(3) 0.068(2) Uani 1 1 d . . . . .
C11 C 0.9640(11) 0.6025(7) 0.6749(3) 0.073(2) Uani 1 1 d . . . . .
C12 C 0.9501(11) 0.4992(6) 0.6546(3) 0.070(2) Uani 1 1 d . . . . .
C13 C 0.9857(13) 0.4034(7) 0.6841(3) 0.079(2) Uani 1 1 d . . . . .
C14 C 0.8431(13) 0.7884(7) 0.5608(3) 0.079(2) Uani 1 1 d . . . . .
C15 C 0.9506(16) 0.8125(10) 0.5217(4) 0.123(4) Uani 1 1 d . . . . .
H15 H 1.045874 0.766439 0.515351 0.148 Uiso 1 1 calc R U . . .
C16 C 0.920(2) 0.9040(13) 0.4916(5) 0.144(5) Uani 1 1 d . . . . .
H16 H 0.992257 0.918474 0.464843 0.172 Uiso 1 1 calc R U . . .
C17 C 0.780(2) 0.9741(10) 0.5015(6) 0.130(5) Uani 1 1 d . . . . .
H17 H 0.760131 1.037291 0.482073 0.156 Uiso 1 1 calc R U . . .
C18 C 0.6741(17) 0.9496(8) 0.5394(4) 0.110(4) Uani 1 1 d . . . . .
H18 H 0.579791 0.996242 0.546075 0.132 Uiso 1 1 calc R U . . .
C19 C 0.7023(14) 0.8570(7) 0.5685(3) 0.091(3) Uani 1 1 d . . . . .
H19 H 0.624536 0.840470 0.593898 0.109 Uiso 1 1 calc R U . . .
C20 C 0.7544(12) 0.7596(7) 0.6709(3) 0.070(2) Uani 1 1 d . . . . .
C21 C 1.0414(12) 0.8026(8) 0.6534(4) 0.083(2) Uani 1 1 d . . . . .
C22 C 1.2296(12) 0.7963(10) 0.6363(5) 0.117(4) Uani 1 1 d . . . . .
H22A H 1.235532 0.756633 0.605432 0.175 Uiso 1 1 calc R U . . .
H22B H 1.297683 0.757391 0.660712 0.175 Uiso 1 1 calc R U . . .
H22C H 1.274613 0.870917 0.632042 0.175 Uiso 1 1 calc R U . . .
C23 C 0.6888(14) 0.9575(7) 0.6963(3) 0.080(3) Uani 1 1 d . . . . .
C24 C 0.5358(16) 0.9341(8) 0.7227(3) 0.099(3) Uani 1 1 d . . . . .
H24 H 0.510737 0.862507 0.734416 0.119 Uiso 1 1 calc R U . . .
C25 C 0.4228(19) 1.0248(10) 0.7302(4) 0.121(4) Uani 1 1 d . . . . .
H25 H 0.320516 1.012894 0.747938 0.145 Uiso 1 1 calc R U . . .
C26 C 0.457(2) 1.1296(9) 0.7127(4) 0.113(4) Uani 1 1 d . . . . .
H26 H 0.376060 1.187188 0.716766 0.135 Uiso 1 1 calc R U . . .
C27 C 0.6120(19) 1.1491(8) 0.6888(4) 0.101(3) Uani 1 1 d . . . . .
H27 H 0.640866 1.221703 0.679084 0.122 Uiso 1 1 calc R U . . .
C28 C 0.7253(15) 1.0619(7) 0.6791(4) 0.088(3) Uani 1 1 d . . . . .
H28 H 0.826195 1.074628 0.660908 0.106 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
Cl1 C1 1.741(9) . ?
N1 C13 1.143(10) . ?
N2 C11 1.354(10) . ?
N3 C20 1.356(10) . ?
N3 N4 1.417(10) . ?
N3 C23 1.436(11) . ?
N4 C21 1.269(11) . ?
O1 C20 1.224(10) . ?
C1 C2 1.358(12) . ?
C1 C6 1.363(14) . ?
C2 C3 1.392(13) . ?
C3 C4 1.376(12) . ?
C4 C5 1.363(11) . ?
C4 C7 1.521(12) . ?
C5 C6 1.395(15) . ?
C7 C8 1.492(10) . ?
C7 C12 1.517(11) . ?
C8 C9 1.326(10) . ?
C9 C14 1.498(10) . ?
C9 C10 1.527(11) . ?
C10 C11 1.504(10) . ?
C10 C21 1.505(11) . ?
C10 C20 1.527(11) . ?
C11 C12 1.351(10) . ?
C12 C13 1.418(11) . ?
C14 C19 1.370(12) . ?
C14 C15 1.370(13) . ?
C15 C16 1.379(15) . ?
C16 C17 1.383(17) . ?
C17 C18 1.339(16) . ?
C18 C19 1.372(12) . ?
C21 C22 1.518(13) . ?
C23 C28 1.356(12) . ?
C23 C24 1.400(14) . ?
C24 C25 1.400(14) . ?
C25 C26 1.360(15) . ?
C26 C27 1.375(18) . ?
C27 C28 1.379(14) . ?

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
C20 N3 N4 113.1(7) . . ?
C20 N3 C23 127.6(8) . . ?
N4 N3 C23 117.4(7) . . ?
C21 N4 N3 106.5(7) . . ?
C2 C1 C6 120.4(9) . . ?
C2 C1 Cl1 119.9(8) . . ?
C6 C1 Cl1 119.7(8) . . ?
C1 C2 C3 119.9(9) . . ?
C4 C3 C2 120.6(8) . . ?
C5 C4 C3 118.6(9) . . ?
C5 C4 C7 120.5(8) . . ?
C3 C4 C7 120.8(7) . . ?
C4 C5 C6 121.0(10) . . ?
C1 C6 C5 119.5(9) . . ?
C8 C7 C12 111.4(6) . . ?
C8 C7 C4 108.8(7) . . ?
C12 C7 C4 113.4(7) . . ?
C9 C8 C7 126.2(7) . . ?
C8 C9 C14 121.9(7) . . ?
C8 C9 C10 121.3(7) . . ?
C14 C9 C10 116.9(7) . . ?
C11 C10 C21 113.9(7) . . ?
C11 C10 C9 113.9(7) . . ?
C21 C10 C9 110.8(7) . . ?
C11 C10 C20 109.1(7) . . ?
C21 C10 C20 99.2(7) . . ?
C9 C10 C20 108.9(6) . . ?
C12 C11 N2 122.9(7) . . ?
C12 C11 C10 121.9(7) . . ?
N2 C11 C10 115.1(7) . . ?
C11 C12 C13 119.2(7) . . ?
C11 C12 C7 124.3(7) . . ?
C13 C12 C7 116.5(7) . . ?
N1 C13 C12 177.7(11) . . ?
C19 C14 C15 117.8(8) . . ?
C19 C14 C9 122.3(8) . . ?
C15 C14 C9 119.8(9) . . ?
C14 C15 C16 121.0(11) . . ?
C15 C16 C17 119.8(12) . . ?
C18 C17 C16 119.0(10) . . ?
C17 C18 C19 121.2(11) . . ?
C14 C19 C18 121.1(10) . . ?
O1 C20 N3 127.4(8) . . ?
O1 C20 C10 126.3(7) . . ?
N3 C20 C10 106.2(8) . . ?
N4 C21 C10 115.0(8) . . ?
N4 C21 C22 122.3(9) . . ?
C10 C21 C22 122.7(9) . . ?
C28 C23 C24 121.9(9) . . ?
C28 C23 N3 120.0(9) . . ?
C24 C23 N3 117.9(8) . . ?
C25 C24 C23 116.1(10) . . ?
C26 C25 C24 122.6(13) . . ?
C25 C26 C27 119.0(12) . . ?
C26 C27 C28 120.5(10) . . ?
C23 C28 C27 119.7(11) . . ?

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.055

