# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_xcalibur
_database_code_depnum_ccdc_archive 'CCDC 1828027'
_audit_update_record             
;
2018-03-07 deposited with the CCDC.
2018-07-13 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C24 H22 Cl2 N2 O2'
_chemical_formula_moiety         'C24 H22 Cl2 N2 O2'
_chemical_formula_weight         441.36
_chemical_melting_point          506

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21/c
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   11.31549(16)
_cell_length_b                   9.66903(15)
_cell_length_c                   9.86401(15)
_cell_angle_alpha                90.0000
_cell_angle_beta                 96.4687(13)
_cell_angle_gamma                90.0000
_cell_volume                     1072.35(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3815
_cell_measurement_theta_min      4.51
_cell_measurement_theta_max      73.77
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.649
_exptl_crystal_size_mid          0.358
_exptl_crystal_size_min          0.197
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460.00
_exptl_absorpt_coefficient_mu    2.911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.174
_exptl_absorpt_correction_T_max  0.564

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            5661
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_theta_max         66.480
_diffrn_reflns_theta_min         3.932
_diffrn_reflns_theta_full        66.480
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1868
_reflns_number_gt                1672
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1424
_refine_ls_wR_factor_gt          0.1383
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1868
_refine_ls_number_parameters     136
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0937P)²+0.1234P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.42
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 -0.11591(5) 0.79323(7) 0.38728(7) 0.0810(3) Uani 1 1 d . . . . .
O1 O 0.62151(13) 0.49758(16) 0.78062(13) 0.0581(4) Uani 1 1 d . . . . .
N1 N 0.43453(13) 0.56925(15) 0.68258(13) 0.0432(4) Uani 1 1 d . . . . .
C2 C 0.37133(15) 0.57013(16) 0.55333(16) 0.0395(4) Uani 1 1 d . . . . .
C4 C 0.24995(15) 0.62306(17) 0.52107(16) 0.0396(4) Uani 1 1 d . . . . .
C1 C 0.44423(15) 0.51767(18) 0.46365(17) 0.0427(4) Uani 1 1 d . . . . .
C9 C 0.17252(17) 0.5539(2) 0.42397(18) 0.0473(4) Uani 1 1 d . . . . .
H9 H 0.1973 0.4725 0.3855 0.057 Uiso 1 1 calc R U . . .
C3 C 0.55029(16) 0.51243(18) 0.67912(18) 0.0442(4) Uani 1 1 d . . . . .
C5 C 0.21170(18) 0.7454(2) 0.5761(2) 0.0509(5) Uani 1 1 d . . . . .
H5 H 0.2623 0.7931 0.6407 0.061 Uiso 1 1 calc R U . . .
C10 C 0.38714(19) 0.5921(2) 0.81363(17) 0.0504(5) Uani 1 1 d . . . . .
H10A H 0.3453 0.6798 0.8101 0.061 Uiso 1 1 calc R U . . .
H10B H 0.4530 0.5981 0.8854 0.061 Uiso 1 1 calc R U . . .
C8 C 0.05964(18) 0.6039(2) 0.3838(2) 0.0540(5) Uani 1 1 d . . . . .
H8 H 0.0082 0.5561 0.3202 0.065 Uiso 1 1 calc R U . . .
C7 C 0.02444(18) 0.7261(2) 0.4397(2) 0.0520(5) Uani 1 1 d . . . . .
C6 C 0.0993(2) 0.7968(2) 0.5355(2) 0.0565(5) Uani 1 1 d . . . . .
H6 H 0.0743 0.8786 0.5728 0.068 Uiso 1 1 calc R U . . .
C11 C 0.3036(2) 0.4793(2) 0.8490(2) 0.0618(6) Uani 1 1 d . . . . .
H11A H 0.2793 0.4984 0.9384 0.074 Uiso 1 1 calc R U . . .
H11B H 0.2329 0.4816 0.7836 0.074 Uiso 1 1 calc R U . . .
C12 C 0.3562(3) 0.3366(3) 0.8500(3) 0.0740(7) Uani 1 1 d . . . . .
H12A H 0.2984 0.2705 0.8732 0.089 Uiso 1 1 calc R U . . .
H12B H 0.3786 0.3156 0.7613 0.089 Uiso 1 1 calc R U . . .
H12C H 0.4251 0.3325 0.9162 0.089 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C7 1.740(2) . ?
O1 C3 1.221(2) . ?
N1 C2 1.390(2) . ?
N1 C3 1.424(2) . ?
N1 C10 1.471(2) . ?
C2 C1 1.373(2) . ?
C2 C4 1.467(2) . ?
C4 C5 1.390(3) . ?
C4 C9 1.394(3) . ?
C1 C1 1.421(3) 3_666 ?
C1 C3 1.446(3) 3_666 ?
C9 C8 1.381(3) . ?
C9 H9 0.9300 . ?
C3 C1 1.446(3) 3_666 ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C10 C11 1.509(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C8 C7 1.381(3) . ?
C8 H8 0.9300 . ?
C7 C6 1.377(3) . ?
C6 H6 0.9300 . ?
C11 C12 1.503(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C3 111.10(13) . . ?
C2 N1 C10 127.19(15) . . ?
C3 N1 C10 120.41(14) . . ?
C1 C2 N1 107.72(15) . . ?
C1 C2 C4 127.24(15) . . ?
N1 C2 C4 125.01(15) . . ?
C5 C4 C9 118.49(17) . . ?
C5 C4 C2 122.50(16) . . ?
C9 C4 C2 118.83(16) . . ?
C2 C1 C1 109.12(18) . 3_666 ?
C2 C1 C3 142.80(16) . 3_666 ?
C1 C1 C3 108.06(19) 3_666 3_666 ?
C8 C9 C4 121.21(17) . . ?
C8 C9 H9 119.4 . . ?
C4 C9 H9 119.4 . . ?
O1 C3 N1 123.33(16) . . ?
O1 C3 C1 132.70(18) . 3_666 ?
N1 C3 C1 103.96(14) . 3_666 ?
C6 C5 C4 120.65(18) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
N1 C10 C11 113.24(15) . . ?
N1 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
N1 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C7 C8 C9 118.95(18) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C6 C7 C8 121.05(19) . . ?
C6 C7 Cl1 119.25(16) . . ?
C8 C7 Cl1 119.70(16) . . ?
C7 C6 C5 119.64(18) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C12 C11 C10 114.0(2) . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C10 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C2 C1 -1.33(19) . . . . ?
C10 N1 C2 C1 -168.19(17) . . . . ?
C3 N1 C2 C4 -179.32(16) . . . . ?
C10 N1 C2 C4 13.8(3) . . . . ?
C1 C2 C4 C5 -135.22(19) . . . . ?
N1 C2 C4 C5 42.4(3) . . . . ?
C1 C2 C4 C9 39.9(3) . . . . ?
N1 C2 C4 C9 -142.50(18) . . . . ?
N1 C2 C1 C1 0.1(2) . . . 3_666 ?
C4 C2 C1 C1 178.05(18) . . . 3_666 ?
N1 C2 C1 C3 -178.2(2) . . . 3_666 ?
C4 C2 C1 C3 -0.2(4) . . . 3_666 ?
C5 C4 C9 C8 -0.8(3) . . . . ?
C2 C4 C9 C8 -176.10(17) . . . . ?
C2 N1 C3 O1 -178.16(18) . . . . ?
C10 N1 C3 O1 -10.3(3) . . . . ?
C2 N1 C3 C1 1.93(19) . . . 3_666 ?
C10 N1 C3 C1 169.81(15) . . . 3_666 ?
C9 C4 C5 C6 0.2(3) . . . . ?
C2 C4 C5 C6 175.34(18) . . . . ?
C2 N1 C10 C11 66.4(2) . . . . ?
C3 N1 C10 C11 -99.3(2) . . . . ?
C4 C9 C8 C7 1.2(3) . . . . ?
C9 C8 C7 C6 -1.0(3) . . . . ?
C9 C8 C7 Cl1 178.33(15) . . . . ?
C8 C7 C6 C5 0.4(3) . . . . ?
Cl1 C7 C6 C5 -178.89(16) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
N1 C10 C11 C12 55.4(2) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
3,6-bis(4-chlorophenyl)-2,5-dipropyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione
_exptl_crystal_recrystallization_method 'liquid-liquid diffusion method'
####################################################################### 
# 
# 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_pr3_1_2(-50)_0707
_database_code_depnum_ccdc_archive 'CCDC 1828028'
_audit_update_record             
;
2018-07-10 deposited with the CCDC.
2018-07-13 downloaded from the CCDC.
;
_audit_creation_date             2018-07-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H22 Cl2 N2 O2'
_chemical_formula_sum            'C24 H22 Cl2 N2 O2'
_chemical_formula_weight         441.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         C24H22Cl2N2O2
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7334(2)
_cell_length_b                   9.9244(2)
_cell_length_c                   12.4910(3)
_cell_angle_alpha                89.585(2)
_cell_angle_beta                 69.561(2)
_cell_angle_gamma                67.774(2)
_cell_volume                     1035.74(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5949
_cell_measurement_temperature    223
_cell_measurement_theta_max      73.8730
_cell_measurement_theta_min      3.8030
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.014
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             460
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 6 0 0.0936
4 5 -3 0.1472
2 -4 -2 0.0441
-4 -3 3 0.1173
-2 4 2 0.0786
3 4 -5 0.1498
6 1 5 0.0251
-4 -3 4 0.1137
-5 -1 -6 0.0148
-4 -4 4 0.1258

_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.055
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.8015 6.2144 -0.2906 0.7268 -0.5676 0.3867
4.1159 4.7017 -2.8644 0.1617 -0.1269 0.9786
1.8508 -4.3244 -1.6126 -0.7722 0.6025 0.2017
-4.4756 -3.2952 3.2063 0.0626 -0.0482 -0.9969
-2.1462 3.9717 1.8174 0.7586 -0.5919 -0.2725
2.5667 3.5405 -5.3886 -0.1531 -0.3123 0.9376
5.8015 1.1671 5.4503 0.4085 0.8395 0.3583
-3.9908 -2.7498 4.0588 0.1899 -0.0063 -0.9818
-5.4615 -0.7371 -6.0616 -0.4244 -0.8719 -0.2443
-3.6383 -3.6896 4.2177 0.0710 0.1426 -0.9872

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9651
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        66.480
_diffrn_reflns_theta_max         66.480
_diffrn_reflns_theta_min         3.816
_diffrn_ambient_temperature      223
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  22.00   0.50    0.50    --  -12.20  68.00  93.00   52
  2  ω    -64.00 -39.00   0.50    0.50    --  -12.20 -68.00 -39.00   50
  3  ω    -35.00   0.00   0.50    0.50    --   12.20 -68.00 -39.00   70
  4  ω     74.00 109.00   0.50    1.25    --  103.70  68.00  93.00   70
  5  ω    118.00 144.00   0.50    1.25    --  103.70  68.00  93.00   52
  6  ω     40.00 114.00   0.50    1.25    --  103.70 -68.00 -39.00  148
  7  ω    -96.00  14.00   0.50    0.50    --  -12.20 -57.00-180.00  220
  8  ω    -97.00  16.00   0.50    0.50    --  -12.20 -57.00  30.00  226
  9  ω    -51.00  77.00   0.50    0.50    --  -12.20  77.00 -60.00  256
 10  ω     63.00  88.00   0.50    0.50    --   12.20  57.00  60.00   50
 11  ω     51.00  84.00   0.50    0.50    --   12.20  77.00 -90.00   66
 12  ω     -2.00  38.00   0.50    0.50    --   12.20  68.00  93.00   80
 13  ω    -10.00  27.00   0.50    0.50    --   12.20  77.00 -90.00   74
 14  ω     14.00 192.00   0.50    1.25    --  103.70 -15.00-180.00  356
 15  ω     97.00 123.00   0.50    1.25    --  103.70 -82.00   0.00   52
 16  ω     92.00 118.00   0.50    1.25    --  103.70 -61.00 120.00   52
 17  ω     95.00 193.00   0.50    1.25    --  103.70  45.00  60.00  196
 18  ω     31.00 145.00   0.50    1.25    --  103.70 -82.00 -30.00  228
 19  ω     80.00 143.00   0.50    1.25    --  103.70 -82.00 120.00  126
 20  ω     35.00 145.00   0.50    1.25    --  103.70 -82.00 -90.00  220
 21  ω     19.00 140.00   0.50    1.25    --  103.70 -82.00-180.00  242
 22  ω     18.00 142.00   0.50    1.25    --  103.70 -82.00  60.00  248
 23  ω     15.00  73.00   0.50    1.25    --  103.70 -82.00 120.00  116
 24  ω    166.00 192.00   0.50    1.25    --  103.70  61.00 -90.00   52
 25  ω     99.00 137.00   0.50    1.25    --  103.70  61.00 -90.00   76
 26  ω     73.00  98.00   0.50    1.25    --  103.70 -61.00-180.00   50
 27  ω     58.00 152.00   0.50    1.25    --  103.70  30.00  30.00  188
 28  ω     17.00  42.00   0.50    1.25    --  103.70 -61.00 120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0413690000
_diffrn_orient_matrix_UB_12      0.1265930000
_diffrn_orient_matrix_UB_13      0.0918857000
_diffrn_orient_matrix_UB_21      0.1216129000
_diffrn_orient_matrix_UB_22      -0.1048179000
_diffrn_orient_matrix_UB_23      0.0470161000
_diffrn_orient_matrix_UB_31      0.1322708000
_diffrn_orient_matrix_UB_32      0.0412498000
_diffrn_orient_matrix_UB_33      -0.0838849000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3182
_reflns_number_total             3580
_reflns_odcompleteness_completeness 99.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3580
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0690P)²+0.3150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1215
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C11B)=Sof(H11C)=Sof(H11D)=Sof(C12B)=Sof(H12D)=Sof(H12E)=Sof(H12F)=1-FVAR(1)
 Sof(C11A)=Sof(H11A)=Sof(H11B)=Sof(C12A)=Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(1)
 Fixed Sof: H10A(0.75) H10B(0.75) H10C(0.25) H10D(0.25)
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10(H10C,H10D), C22(H22A,H22B), C23(H23A,H23B), C11A(H11A,
 H11B), C11B(H11C,H11D)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C17(H17), C6(H6), C21(H21), C18(H18), C9(H9), C8(H8), C20(H20)
3.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C12A(H12A,H12B,H12C), C12B(H12D,H12E,H12F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.83086(6) 1.06102(6) -0.13226(4) 0.04966(18) Uani 1 1 d . . . . .
Cl2 Cl -0.03523(7) 0.32359(6) 0.73943(5) 0.05276(18) Uani 1 1 d . . . . .
O1 O 0.45838(17) 0.38451(14) 0.23031(12) 0.0419(3) Uani 1 1 d . . . . .
O2 O 0.31155(17) 1.00741(14) 0.36281(11) 0.0406(3) Uani 1 1 d . . . . .
N1 N 0.55166(17) 0.55608(16) 0.13987(12) 0.0300(3) Uani 1 1 d . . . . .
N2 N 0.22597(18) 0.83330(16) 0.45739(12) 0.0311(3) Uani 1 1 d . . . . .
C15 C 0.3229(2) 0.88086(19) 0.36371(15) 0.0312(4) Uani 1 1 d . . . . .
C13 C 0.3807(2) 0.63125(19) 0.32688(15) 0.0309(4) Uani 1 1 d . . . . .
C14 C 0.2612(2) 0.68494(19) 0.43438(15) 0.0301(4) Uani 1 1 d . . . . .
C1 C 0.4249(2) 0.74759(19) 0.28058(15) 0.0306(4) Uani 1 1 d . . . . .
C3 C 0.4605(2) 0.50652(19) 0.23497(15) 0.0311(4) Uani 1 1 d . . . . .
C2 C 0.5300(2) 0.69980(19) 0.16786(15) 0.0293(4) Uani 1 1 d . . . . .
C4 C 0.6076(2) 0.78227(19) 0.08926(15) 0.0294(4) Uani 1 1 d . . . . .
C16 C 0.1826(2) 0.6033(2) 0.51309(15) 0.0311(4) Uani 1 1 d . . . . .
C5 C 0.6207(2) 0.78317(19) -0.02613(15) 0.0315(4) Uani 1 1 d . . . . .
H5 H 0.5835 0.7256 -0.0571 0.038 Uiso 1 1 calc R . . . .
C17 C 0.0178(2) 0.6590(2) 0.57766(15) 0.0330(4) Uani 1 1 d . . . . .
H17 H -0.0467 0.7546 0.5741 0.040 Uiso 1 1 calc R . . . .
C6 C 0.6887(2) 0.86911(19) -0.09414(15) 0.0327(4) Uani 1 1 d . . . . .
H6 H 0.6958 0.8712 -0.1703 0.039 Uiso 1 1 calc R . . . .
C10 C 0.6813(2) 0.4499(2) 0.04083(15) 0.0331(4) Uani 1 1 d . . . . .
H10A H 0.7268 0.5028 -0.0170 0.040 Uiso 0.75 1 calc R . P A 1
H10B H 0.6373 0.3970 0.0068 0.040 Uiso 0.75 1 calc R . P A 1
H10C H 0.6742 0.4869 -0.0300 0.040 Uiso 0.25 1 calc R . P B 2
H10D H 0.6678 0.3578 0.0420 0.040 Uiso 0.25 1 calc R . P B 2
C22 C 0.1401(2) 0.9237(2) 0.57141(15) 0.0345(4) Uani 1 1 d . . . . .
H22A H 0.0383 0.9154 0.6077 0.041 Uiso 1 1 calc R . . . .
H22B H 0.1182 1.0259 0.5621 0.041 Uiso 1 1 calc R . . . .
C21 C 0.2767(2) 0.4593(2) 0.51958(17) 0.0391(4) Uani 1 1 d . . . . .
H21 H 0.3861 0.4202 0.4762 0.047 Uiso 1 1 calc R . . . .
C7 C 0.7462(2) 0.9519(2) -0.04736(16) 0.0342(4) Uani 1 1 d . . . . .
C18 C -0.0502(2) 0.5737(2) 0.64668(16) 0.0362(4) Uani 1 1 d . . . . .
H18 H -0.1599 0.6107 0.6887 0.043 Uiso 1 1 calc R . . . .
C9 C 0.6662(2) 0.8676(2) 0.13343(16) 0.0374(4) Uani 1 1 d . . . . .
H9 H 0.6582 0.8676 0.2098 0.045 Uiso 1 1 calc R . . . .
C19 C 0.0476(2) 0.4328(2) 0.65209(16) 0.0363(4) Uani 1 1 d . . . . .
C8 C 0.7359(2) 0.9521(2) 0.06564(17) 0.0404(4) Uani 1 1 d . . . . .
H8 H 0.7754 1.0083 0.0956 0.048 Uiso 1 1 calc R . . . .
C20 C 0.2105(2) 0.3741(2) 0.58903(18) 0.0426(5) Uani 1 1 d . . . . .
H20 H 0.2744 0.2786 0.5935 0.051 Uiso 1 1 calc R . . . .
C24 C 0.3885(3) 0.8985(3) 0.6070(2) 0.0518(5) Uani 1 1 d . . . . .
H24A H 0.4548 0.8429 0.5316 0.078 Uiso 1 1 calc GR . . . .
H24B H 0.4431 0.8650 0.6591 0.078 Uiso 1 1 calc GR . . . .
H24C H 0.3662 1.0009 0.6030 0.078 Uiso 1 1 calc GR . . . .
C23 C 0.2346(3) 0.8778(3) 0.64944(17) 0.0453(5) Uani 1 1 d . . . . .
H23A H 0.1686 0.9344 0.7256 0.054 Uiso 1 1 calc R . . . .
H23B H 0.2581 0.7749 0.6571 0.054 Uiso 1 1 calc R . . . .
C11A C 0.8150(3) 0.3386(4) 0.0741(2) 0.0398(10) Uani 0.740(8) 1 d . . P C 1
H11A H 0.7736 0.2748 0.1221 0.048 Uiso 0.740(8) 1 calc R . P C 1
H11B H 0.9017 0.2777 0.0046 0.048 Uiso 0.740(8) 1 calc R . P C 1
C12A C 0.8800(12) 0.4114(10) 0.1382(9) 0.077(3) Uani 0.740(8) 1 d . . P C 1
H12A H 0.9157 0.4789 0.0931 0.116 Uiso 0.740(8) 1 calc GR . P C 1
H12B H 0.9682 0.3378 0.1515 0.116 Uiso 0.740(8) 1 calc GR . P C 1
H12C H 0.7974 0.4638 0.2108 0.116 Uiso 0.740(8) 1 calc GR . P C 1
C11B C 0.8414(9) 0.4221(10) 0.0412(8) 0.044(3) Uani 0.260(8) 1 d . . P C 2
H11C H 0.9219 0.3538 -0.0271 0.052 Uiso 0.260(8) 1 calc R . P C 2
H11D H 0.8561 0.5137 0.0365 0.052 Uiso 0.260(8) 1 calc R . P C 2
C12B C 0.867(3) 0.363(3) 0.1419(15) 0.075(8) Uani 0.260(8) 1 d . . P C 2
H12D H 0.9784 0.3315 0.1303 0.113 Uiso 0.260(8) 1 calc GR . P C 2
H12E H 0.8377 0.2805 0.1541 0.113 Uiso 0.260(8) 1 calc GR . P C 2
H12F H 0.8033 0.4374 0.2083 0.113 Uiso 0.260(8) 1 calc GR . P C 2


_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 C7 1.7393(18) . ?
Cl2 C19 1.7453(19) . ?
O1 C3 1.221(2) . ?
O2 C15 1.219(2) . ?
N1 C3 1.423(2) . ?
N1 C2 1.389(2) . ?
N1 C10 1.468(2) . ?
N2 C15 1.428(2) . ?
N2 C14 1.387(2) . ?
N2 C22 1.467(2) . ?
C15 C1 1.456(2) . ?
C13 C14 1.375(2) . ?
C13 C1 1.430(3) . ?
C13 C3 1.457(2) . ?
C14 C16 1.463(2) . ?
C1 C2 1.375(2) . ?
C2 C4 1.464(2) . ?
C4 C5 1.402(2) . ?
C4 C9 1.393(3) . ?
C16 C17 1.401(3) . ?
C16 C21 1.396(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.383(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C10 H10D 0.9700 . ?
C10 C11A 1.540(3) . ?
C10 C11B 1.478(8) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.519(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.376(3) . ?
C7 C8 1.380(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.379(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.377(3) . ?
C19 C20 1.382(3) . ?
C8 H8 0.9300 . ?
C20 H20 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C24 C23 1.498(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C11A H11A 0.9700 . ?
C11A H11B 0.9700 . ?
C11A C12A 1.507(9) . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
C11B H11C 0.9700 . ?
C11B H11D 0.9700 . ?
C11B C12B 1.45(3) . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C10 120.15(14) . . ?
C2 N1 C3 111.46(14) . . ?
C2 N1 C10 126.29(15) . . ?
C15 N2 C22 120.18(15) . . ?
C14 N2 C15 111.39(14) . . ?
C14 N2 C22 126.05(15) . . ?
O2 C15 N2 123.50(16) . . ?
O2 C15 C1 132.80(17) . . ?
N2 C15 C1 103.70(14) . . ?
C14 C13 C1 108.92(16) . . ?
C14 C13 C3 142.47(17) . . ?
C1 C13 C3 107.51(16) . . ?
N2 C14 C16 124.70(15) . . ?
C13 C14 N2 108.04(15) . . ?
C13 C14 C16 127.27(16) . . ?
C13 C1 C15 107.92(16) . . ?
C2 C1 C15 141.80(17) . . ?
C2 C1 C13 109.25(16) . . ?
O1 C3 N1 123.31(16) . . ?
O1 C3 C13 132.70(17) . . ?
N1 C3 C13 104.00(14) . . ?
N1 C2 C4 124.91(15) . . ?
C1 C2 N1 107.75(15) . . ?
C1 C2 C4 127.34(16) . . ?
C5 C4 C2 123.36(16) . . ?
C9 C4 C2 117.73(16) . . ?
C9 C4 C5 118.88(17) . . ?
C17 C16 C14 123.68(16) . . ?
C21 C16 C14 117.80(16) . . ?
C21 C16 C17 118.45(17) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.37(17) . . ?
C6 C5 H5 119.8 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.85(17) . . ?
C18 C17 H17 119.6 . . ?
C5 C6 H6 120.5 . . ?
C5 C6 C7 119.06(16) . . ?
C7 C6 H6 120.5 . . ?
N1 C10 H10A 109.0 . . ?
N1 C10 H10B 109.0 . . ?
N1 C10 H10C 109.1 . . ?
N1 C10 H10D 109.1 . . ?
N1 C10 C11A 112.73(16) . . ?
N1 C10 C11B 112.5(3) . . ?
H10A C10 H10B 107.8 . . ?
H10C C10 H10D 107.8 . . ?
C11A C10 H10A 109.0 . . ?
C11A C10 H10B 109.0 . . ?
C11B C10 H10C 109.1 . . ?
C11B C10 H10D 109.1 . . ?
N2 C22 H22A 109.2 . . ?
N2 C22 H22B 109.2 . . ?
N2 C22 C23 112.19(15) . . ?
H22A C22 H22B 107.9 . . ?
C23 C22 H22A 109.2 . . ?
C23 C22 H22B 109.2 . . ?
C16 C21 H21 119.4 . . ?
C20 C21 C16 121.15(17) . . ?
C20 C21 H21 119.4 . . ?
C6 C7 Cl1 119.26(14) . . ?
C8 C7 Cl1 119.02(15) . . ?
C8 C7 C6 121.71(17) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 C17 118.79(17) . . ?
C19 C18 H18 120.6 . . ?
C4 C9 H9 119.5 . . ?
C8 C9 C4 120.99(17) . . ?
C8 C9 H9 119.5 . . ?
C18 C19 Cl2 119.63(15) . . ?
C18 C19 C20 121.87(17) . . ?
C20 C19 Cl2 118.50(15) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 118.98(18) . . ?
C9 C8 H8 120.5 . . ?
C21 C20 C19 118.88(18) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
C22 C23 H23A 108.8 . . ?
C22 C23 H23B 108.8 . . ?
C24 C23 C22 113.96(18) . . ?
C24 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C10 C11A H11A 109.0 . . ?
C10 C11A H11B 109.0 . . ?
H11A C11A H11B 107.8 . . ?
C12A C11A C10 112.8(5) . . ?
C12A C11A H11A 109.0 . . ?
C12A C11A H11B 109.0 . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12B 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C10 C11B H11C 108.7 . . ?
C10 C11B H11D 108.7 . . ?
H11C C11B H11D 107.6 . . ?
C12B C11B C10 114.1(13) . . ?
C12B C11B H11C 108.7 . . ?
C12B C11B H11D 108.7 . . ?
C11B C12B H12D 109.5 . . ?
C11B C12B H12E 109.5 . . ?
C11B C12B H12F 109.5 . . ?
H12D C12B H12E 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.441
_oxdiff_exptl_absorpt_empirical_full_min 0.790
