# 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_CPBRT
_database_code_depnum_ccdc_archive 'CCDC 1583624'
_audit_update_record             
;
2017-11-02 deposited with the CCDC.
2018-06-14 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT375_CPBRT               
;
PROBLEM: Strange C-O-H Geometry (C-O  &gt;   1.45 Ang) .....        O1B Check
RESPONSE: This is due to thermal motion and dynamic disorder
;
_vrf_PLAT084_CPBRT               
;
PROBLEM: High wR2 Value (i.e. &gt; 0.25) ...................       0.39 Report
RESPONSE: This is due to thermal motion and dynamic disorder
;
_vrf_PLAT910_CPBRT               
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         12 Note
RESPONSE: This is due to thermal motion and dynamic disorder
;
_vrf_PLAT934_CPBRT               
;
PROBLEM: Number of (Iobs-Icalc)/SigmaW &gt; 10 Outliers ....         10 Check
RESPONSE: This is due to thermal motion and dynamic disorder
;
# Added during the CSD deposition process: Thursday 02 November 2017 10:33 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            Clozapine
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H23 Cl N4 O'
_chemical_formula_weight         358.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   20.275(2)
_cell_length_b                   10.7573(11)
_cell_length_c                   17.3839(17)
_cell_angle_alpha                90
_cell_angle_beta                 95.541(2)
_cell_angle_gamma                90
_cell_volume                     3773.7(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    234
_cell_measurement_theta_min      2
_cell_measurement_theta_max      20

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.217
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6997
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32387
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.852
_diffrn_reflns_theta_max         27.588
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             4284
_reflns_number_gt                3549
_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.
 
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.2000P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4284
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0979
_refine_ls_wR_factor_ref         0.3919
_refine_ls_wR_factor_gt          0.3693
_refine_ls_goodness_of_fit_ref   1.842
_refine_ls_restrained_S_all      1.842
_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
N1 N 0.27685(10) 0.6717(2) 0.66060(11) 0.0508(6) Uani 1 1 d . . . . .
C2 C 0.29596(11) 0.6252(2) 0.59816(14) 0.0450(6) Uani 1 1 d . . . . .
C3 C 0.25673(11) 0.5444(2) 0.54269(13) 0.0472(6) Uani 1 1 d . . . . .
C4 C 0.25766(14) 0.5609(3) 0.46267(15) 0.0574(7) Uani 1 1 d . . . . .
H4 H 0.2799 0.6287 0.4443 0.069 Uiso 1 1 calc R U . . .
C5 C 0.22616(16) 0.4783(4) 0.41099(18) 0.0722(9) Uani 1 1 d . . . . .
H5 H 0.2263 0.4913 0.3581 0.087 Uiso 1 1 calc R U . . .
C6 C 0.19432(19) 0.3760(4) 0.4381(2) 0.0773(10) Uani 1 1 d . . . . .
H6 H 0.1758 0.3167 0.4035 0.093 Uiso 1 1 calc R U . . .
C7 C 0.18997(16) 0.3616(3) 0.5157(2) 0.0661(8) Uani 1 1 d . . . . .
H7 H 0.1669 0.2940 0.5330 0.079 Uiso 1 1 calc R U . . .
C8 C 0.21914(12) 0.4453(2) 0.56876(15) 0.0511(6) Uani 1 1 d . . . . .
N9 N 0.21120(12) 0.4323(2) 0.64756(14) 0.0612(7) Uani 1 1 d . . . . .
H9 H 0.2232 0.3664 0.6731 0.073 Uiso 1 1 calc R U . . .
C10 C 0.18219(12) 0.5346(3) 0.68206(14) 0.0533(7) Uani 1 1 d . . . . .
C11 C 0.12283(14) 0.5209(3) 0.71679(17) 0.0657(8) Uani 1 1 d . . . . .
H11 H 0.1018 0.4439 0.7153 0.079 Uiso 1 1 calc R U . . .
C12 C 0.09492(14) 0.6196(4) 0.75326(19) 0.0740(10) Uani 1 1 d . . . . .
H12 H 0.0563 0.6088 0.7774 0.089 Uiso 1 1 calc R U . . .
C13 C 0.12523(15) 0.7333(4) 0.75308(16) 0.0662(9) Uani 1 1 d . . . . .
C14 C 0.18457(13) 0.7498(3) 0.71972(14) 0.0572(7) Uani 1 1 d . . . . .
H14 H 0.2049 0.8274 0.7214 0.069 Uiso 1 1 calc R U . . .
C15 C 0.21308(12) 0.6516(3) 0.68427(13) 0.0497(6) Uani 1 1 d . . . . .
Cl16 Cl 0.09174(6) 0.85758(12) 0.80000(6) 0.0956(5) Uani 1 1 d . . . . .
N17 N 0.35683(10) 0.6604(2) 0.57700(13) 0.0500(6) Uani 1 1 d . . . . .
C18 C 0.39435(14) 0.7595(3) 0.61840(16) 0.0596(7) Uani 1 1 d . . . . .
H18A H 0.4254 0.7243 0.6585 0.072 Uiso 1 1 calc R U . . .
H18B H 0.3645 0.8143 0.6426 0.072 Uiso 1 1 calc R U . . .
C19 C 0.43148(14) 0.8320(3) 0.56175(19) 0.0605(7) Uani 1 1 d . . . . .
H19A H 0.4000 0.8725 0.5243 0.073 Uiso 1 1 calc R U . . .
H19B H 0.4579 0.8961 0.5893 0.073 Uiso 1 1 calc R U . . .
N20 N 0.47461(11) 0.7513(2) 0.52143(13) 0.0583(7) Uani 1 1 d . . . . .
C21 C 0.43668(14) 0.6534(3) 0.48200(16) 0.0566(7) Uani 1 1 d . . . . .
H21A H 0.4661 0.5990 0.4568 0.068 Uiso 1 1 calc R U . . .
H21B H 0.4052 0.6890 0.4425 0.068 Uiso 1 1 calc R U . . .
C22 C 0.39978(13) 0.5785(3) 0.53806(16) 0.0554(7) Uani 1 1 d . . . . .
H22A H 0.3735 0.5144 0.5103 0.067 Uiso 1 1 calc R U . . .
H22B H 0.4312 0.5384 0.5758 0.067 Uiso 1 1 calc R U . . .
C23 C 0.51034(19) 0.8241(4) 0.4669(2) 0.0811(10) Uani 1 1 d . . . . .
H23A H 0.5398 0.7705 0.4423 0.122 Uiso 1 1 calc R U . . .
H23B H 0.5354 0.8885 0.4944 0.122 Uiso 1 1 calc R U . . .
H23C H 0.4791 0.8607 0.4285 0.122 Uiso 1 1 calc R U . . .
O1A O 0.3537(3) 0.7133(4) 0.8019(3) 0.1468(18) Uani 0.541(11) 1 d . . P A 1
H1A H 0.3367 0.6931 0.7590 0.176 Uiso 0.541(11) 1 calc R U P A 1
C1A C 0.3989(3) 0.6168(5) 0.8319(3) 0.0643(19) Uani 0.541(11) 1 d . . P A 1
H1A1 H 0.4351 0.6111 0.8004 0.097 Uiso 0.541(11) 1 calc R U P A 1
H1A2 H 0.3759 0.5388 0.8312 0.097 Uiso 0.541(11) 1 calc R U P A 1
H1A3 H 0.4156 0.6368 0.8840 0.097 Uiso 0.541(11) 1 calc R U P A 1
O1B O 0.3537(3) 0.7133(4) 0.8019(3) 0.1468(18) Uani 0.459(11) 1 d . . P A 2
H1B H 0.3646 0.7482 0.7631 0.176 Uiso 0.459(11) 1 calc R U P A 2
C1B C 0.4111(4) 0.7224(9) 0.8678(6) 0.101(4) Uani 0.459(11) 1 d . . P A 2
H1B1 H 0.4065 0.7975 0.8966 0.151 Uiso 0.459(11) 1 calc R U P A 2
H1B2 H 0.4528 0.7232 0.8458 0.151 Uiso 0.459(11) 1 calc R U P A 2
H1B3 H 0.4095 0.6520 0.9015 0.151 Uiso 0.459(11) 1 calc R U P A 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
N1 C2 1.289(3) . ?
N1 C15 1.411(3) . ?
C2 N17 1.375(3) . ?
C2 C3 1.473(3) . ?
C3 C4 1.404(3) . ?
C3 C8 1.410(3) . ?
C4 C5 1.376(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.369(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.381(4) . ?
C7 H7 0.9300 . ?
C8 N9 1.401(4) . ?
N9 C10 1.409(4) . ?
N9 H9 0.8600 . ?
C10 C15 1.405(4) . ?
C10 C11 1.406(4) . ?
C11 C12 1.385(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.397(4) . ?
C13 Cl16 1.738(4) . ?
C14 C15 1.378(4) . ?
C14 H14 0.9300 . ?
N17 C22 1.452(3) . ?
N17 C18 1.458(4) . ?
C18 C19 1.513(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 N20 1.459(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
N20 C21 1.438(4) . ?
N20 C23 1.473(4) . ?
C21 C22 1.517(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O1A C1A 1.448(7) . ?
O1A H1A 0.8200 . ?
C1A H1A1 0.9600 . ?
C1A H1A2 0.9600 . ?
C1A H1A3 0.9600 . ?
O1B C1B 1.556(8) . ?
O1B H1B 0.8200 . ?
C1B H1B1 0.9600 . ?
C1B H1B2 0.9600 . ?
C1B H1B3 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 C15 123.0(2) . . ?
N1 C2 N17 118.0(2) . . ?
N1 C2 C3 126.4(2) . . ?
N17 C2 C3 115.4(2) . . ?
C4 C3 C8 118.2(2) . . ?
C4 C3 C2 121.1(2) . . ?
C8 C3 C2 120.7(2) . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 121.4(3) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C7 C8 N9 120.4(3) . . ?
C7 C8 C3 119.2(3) . . ?
N9 C8 C3 120.4(2) . . ?
C8 N9 C10 115.5(2) . . ?
C8 N9 H9 122.2 . . ?
C10 N9 H9 122.2 . . ?
C15 C10 C11 118.7(3) . . ?
C15 C10 N9 120.5(2) . . ?
C11 C10 N9 120.7(3) . . ?
C12 C11 C10 121.4(3) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C11 118.7(3) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C14 121.3(3) . . ?
C12 C13 Cl16 119.4(2) . . ?
C14 C13 Cl16 119.2(3) . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C10 119.6(2) . . ?
C14 C15 N1 116.7(2) . . ?
C10 C15 N1 123.2(3) . . ?
C2 N17 C22 123.5(2) . . ?
C2 N17 C18 120.6(2) . . ?
C22 N17 C18 111.5(2) . . ?
N17 C18 C19 108.9(2) . . ?
N17 C18 H18A 109.9 . . ?
C19 C18 H18A 109.9 . . ?
N17 C18 H18B 109.9 . . ?
C19 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
N20 C19 C18 111.4(2) . . ?
N20 C19 H19A 109.3 . . ?
C18 C19 H19A 109.3 . . ?
N20 C19 H19B 109.3 . . ?
C18 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
C21 N20 C19 110.3(2) . . ?
C21 N20 C23 110.9(3) . . ?
C19 N20 C23 110.3(3) . . ?
N20 C21 C22 110.9(2) . . ?
N20 C21 H21A 109.5 . . ?
C22 C21 H21A 109.5 . . ?
N20 C21 H21B 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 108.0 . . ?
N17 C22 C21 109.4(2) . . ?
N17 C22 H22A 109.8 . . ?
C21 C22 H22A 109.8 . . ?
N17 C22 H22B 109.8 . . ?
C21 C22 H22B 109.8 . . ?
H22A C22 H22B 108.2 . . ?
N20 C23 H23A 109.5 . . ?
N20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1A O1A H1A 109.5 . . ?
O1A C1A H1A1 109.5 . . ?
O1A C1A H1A2 109.5 . . ?
H1A1 C1A H1A2 109.5 . . ?
O1A C1A H1A3 109.5 . . ?
H1A1 C1A H1A3 109.5 . . ?
H1A2 C1A H1A3 109.5 . . ?
C1B O1B H1B 109.5 . . ?
O1B C1B H1B1 109.5 . . ?
O1B C1B H1B2 109.5 . . ?
H1B1 C1B H1B2 109.5 . . ?
O1B C1B H1B3 109.5 . . ?
H1B1 C1B H1B3 109.5 . . ?
H1B2 C1B H1B3 109.5 . . ?

_refine_diff_density_max         0.933
_refine_diff_density_min         -0.888
_refine_diff_density_rms         0.079

####################################################################### 
# 
# 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_CPBLT
_database_code_depnum_ccdc_archive 'CCDC 1583625'
_audit_update_record             
;
2017-11-02 deposited with the CCDC.
2018-06-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            Clozapine
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H23 Cl N4 O'
_chemical_formula_weight         358.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   20.0103(8)
_cell_length_b                   10.5732(5)
_cell_length_c                   17.3750(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.1720(10)
_cell_angle_gamma                90
_cell_volume                     3654.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    234
_cell_measurement_theta_min      2
_cell_measurement_theta_max      20

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.224
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6995
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27247
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.427
_diffrn_reflns_theta_max         30.315
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5045
_reflns_number_gt                3463
_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.
 
 _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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0703P)²+7.8185P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5045
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1061
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.1720
_refine_ls_wR_factor_gt          0.1434
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
N1 N 0.27715(9) 0.67243(19) 0.66160(11) 0.0233(4) Uani 1 1 d . . . . .
C2 C 0.29617(10) 0.6248(2) 0.59922(12) 0.0188(4) Uani 1 1 d . . . . .
C3 C 0.25577(10) 0.5422(2) 0.54256(12) 0.0191(4) Uani 1 1 d . . . . .
C4 C 0.25734(11) 0.5604(2) 0.46305(13) 0.0226(5) Uani 1 1 d . . . . .
H4 H 0.2797 0.6302 0.4457 0.027 Uiso 1 1 calc R U . . .
C5 C 0.22611(12) 0.4758(3) 0.40972(14) 0.0287(5) Uani 1 1 d . . . . .
H5 H 0.2272 0.4888 0.3569 0.034 Uiso 1 1 calc R U . . .
C6 C 0.19316(13) 0.3714(3) 0.43622(16) 0.0329(6) Uani 1 1 d . . . . .
H6 H 0.1744 0.3115 0.4011 0.040 Uiso 1 1 calc R U . . .
C7 C 0.18812(12) 0.3560(2) 0.51390(15) 0.0286(5) Uani 1 1 d . . . . .
H7 H 0.1646 0.2873 0.5307 0.034 Uiso 1 1 calc R U . . .
C8 C 0.21778(11) 0.4419(2) 0.56773(13) 0.0225(5) Uani 1 1 d . . . . .
N9 N 0.20943(10) 0.4281(2) 0.64704(12) 0.0278(5) Uani 1 1 d . . . . .
H9 H 0.2210 0.3603 0.6724 0.033 Uiso 1 1 calc R U . . .
C10 C 0.18089(11) 0.5326(2) 0.68183(13) 0.0245(5) Uani 1 1 d . . . . .
C11 C 0.12135(12) 0.5176(3) 0.71651(13) 0.0306(6) Uani 1 1 d . . . . .
H11 H 0.1002 0.4392 0.7148 0.037 Uiso 1 1 calc R U . . .
C12 C 0.09361(12) 0.6177(3) 0.75335(14) 0.0328(6) Uani 1 1 d . . . . .
H12 H 0.0548 0.6064 0.7775 0.039 Uiso 1 1 calc R U . . .
C13 C 0.12421(12) 0.7342(3) 0.75369(13) 0.0289(5) Uani 1 1 d . . . . .
C14 C 0.18352(12) 0.7519(3) 0.72046(12) 0.0264(5) Uani 1 1 d . . . . .
H14 H 0.2038 0.8311 0.7222 0.032 Uiso 1 1 calc R U . . .
C15 C 0.21268(11) 0.6514(2) 0.68451(12) 0.0231(5) Uani 1 1 d . . . . .
Cl16 Cl 0.09057(3) 0.86124(7) 0.80141(4) 0.0401(2) Uani 1 1 d . . . . .
N17 N 0.35804(9) 0.65958(17) 0.57859(10) 0.0195(4) Uani 1 1 d . . . . .
C18 C 0.39678(11) 0.7598(2) 0.62057(13) 0.0233(5) Uani 1 1 d . . . . .
H18A H 0.4289 0.7232 0.6602 0.028 Uiso 1 1 calc R U . . .
H18B H 0.3669 0.8149 0.6456 0.028 Uiso 1 1 calc R U . . .
C19 C 0.43348(11) 0.8349(2) 0.56382(13) 0.0224(5) Uani 1 1 d . . . . .
H19A H 0.4009 0.8764 0.5268 0.027 Uiso 1 1 calc R U . . .
H19B H 0.4605 0.8999 0.5916 0.027 Uiso 1 1 calc R U . . .
N20 N 0.47696(9) 0.75353(18) 0.52233(11) 0.0210(4) Uani 1 1 d . . . . .
C21 C 0.43716(11) 0.6527(2) 0.48193(13) 0.0218(5) Uani 1 1 d . . . . .
H21A H 0.4664 0.5977 0.4560 0.026 Uiso 1 1 calc R U . . .
H21B H 0.4045 0.6893 0.4430 0.026 Uiso 1 1 calc R U . . .
C22 C 0.40120(11) 0.5762(2) 0.53864(13) 0.0217(5) Uani 1 1 d . . . . .
H22A H 0.3743 0.5108 0.5112 0.026 Uiso 1 1 calc R U . . .
H22B H 0.4338 0.5357 0.5760 0.026 Uiso 1 1 calc R U . . .
C23 C 0.51039(12) 0.8285(2) 0.46693(14) 0.0283(5) Uani 1 1 d . . . . .
H23A H 0.5373 0.7739 0.4386 0.043 Uiso 1 1 calc R U . . .
H23B H 0.5386 0.8909 0.4942 0.043 Uiso 1 1 calc R U . . .
H23C H 0.4772 0.8698 0.4316 0.043 Uiso 1 1 calc R U . . .
O1A O 0.09285(17) 0.2199(4) 0.6326(2) 0.0532(13) Uani 0.606(5) 1 d . . P A 1
H1A H 0.0607 0.2166 0.5991 0.064 Uiso 0.606(5) 1 calc R U P A 1
C1A C 0.09916(14) 0.1090(3) 0.67002(17) 0.0385(6) Uani 0.394(5) 1 d . . P A 1
H1A1 H 0.1346 0.1149 0.7117 0.058 Uiso 0.394(5) 1 calc R U P A 1
H1A2 H 0.1096 0.0439 0.6347 0.058 Uiso 0.394(5) 1 calc R U P A 1
H1A3 H 0.0577 0.0889 0.6904 0.058 Uiso 0.394(5) 1 calc R U P A 1
O1B O 0.1403(2) 0.2137(4) 0.6988(2) 0.0275(12) Uani 0.394(5) 1 d . . P A 2
H1B H 0.1630 0.1929 0.7390 0.033 Uiso 0.394(5) 1 calc R U P A 2
C1B C 0.09916(14) 0.1090(3) 0.67002(17) 0.0385(6) Uani 0.606(5) 1 d . . P A 2
H1B1 H 0.1086 0.0371 0.7031 0.058 Uiso 0.606(5) 1 calc R U P A 2
H1B2 H 0.1087 0.0886 0.6185 0.058 Uiso 0.606(5) 1 calc R U P A 2
H1B3 H 0.0526 0.1315 0.6692 0.058 Uiso 0.606(5) 1 calc R U P A 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
N1 C2 1.289(3) . ?
N1 C15 1.408(3) . ?
C2 N17 1.375(3) . ?
C2 C3 1.488(3) . ?
C3 C4 1.398(3) . ?
C3 C8 1.402(3) . ?
C4 C5 1.387(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.374(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.390(3) . ?
C7 H7 0.9300 . ?
C8 N9 1.413(3) . ?
N9 C10 1.410(3) . ?
N9 H9 0.8600 . ?
C10 C11 1.401(3) . ?
C10 C15 1.407(3) . ?
C11 C12 1.384(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(3) . ?
C13 Cl16 1.751(3) . ?
C14 C15 1.392(3) . ?
C14 H14 0.9300 . ?
N17 C18 1.461(3) . ?
N17 C22 1.461(3) . ?
C18 C19 1.516(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 N20 1.467(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
N20 C23 1.463(3) . ?
N20 C21 1.464(3) . ?
C21 C22 1.515(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O1A C1A 1.339(4) . ?
O1A H1A 0.8200 . ?
C1A H1A1 0.9600 . ?
C1A H1A2 0.9600 . ?
C1A H1A3 0.9600 . ?
O1B C1B 1.437(5) . ?
O1B H1B 0.8200 . ?
C1B H1B1 0.9600 . ?
C1B H1B2 0.9600 . ?
C1B H1B3 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 C15 122.58(19) . . ?
N1 C2 N17 118.0(2) . . ?
N1 C2 C3 126.64(19) . . ?
N17 C2 C3 115.14(19) . . ?
C4 C3 C8 118.8(2) . . ?
C4 C3 C2 120.32(19) . . ?
C8 C3 C2 120.79(19) . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.1(2) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.8(2) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C3 119.4(2) . . ?
C7 C8 N9 120.1(2) . . ?
C3 C8 N9 120.5(2) . . ?
C10 N9 C8 115.64(19) . . ?
C10 N9 H9 122.2 . . ?
C8 N9 H9 122.2 . . ?
C11 C10 C15 119.3(2) . . ?
C11 C10 N9 119.9(2) . . ?
C15 C10 N9 120.8(2) . . ?
C12 C11 C10 121.0(2) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C13 C12 C11 119.1(2) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 121.3(2) . . ?
C12 C13 Cl16 119.70(19) . . ?
C14 C13 Cl16 118.9(2) . . ?
C13 C14 C15 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 119.1(2) . . ?
C14 C15 N1 116.6(2) . . ?
C10 C15 N1 123.8(2) . . ?
C2 N17 C18 120.53(18) . . ?
C2 N17 C22 123.85(19) . . ?
C18 N17 C22 111.47(17) . . ?
N17 C18 C19 108.88(18) . . ?
N17 C18 H18A 109.9 . . ?
C19 C18 H18A 109.9 . . ?
N17 C18 H18B 109.9 . . ?
C19 C18 H18B 109.9 . . ?
H18A C18 H18B 108.3 . . ?
N20 C19 C18 111.49(19) . . ?
N20 C19 H19A 109.3 . . ?
C18 C19 H19A 109.3 . . ?
N20 C19 H19B 109.3 . . ?
C18 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
C23 N20 C21 110.04(18) . . ?
C23 N20 C19 110.05(18) . . ?
C21 N20 C19 110.01(17) . . ?
N20 C21 C22 110.42(18) . . ?
N20 C21 H21A 109.6 . . ?
C22 C21 H21A 109.6 . . ?
N20 C21 H21B 109.6 . . ?
C22 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
N17 C22 C21 109.46(18) . . ?
N17 C22 H22A 109.8 . . ?
C21 C22 H22A 109.8 . . ?
N17 C22 H22B 109.8 . . ?
C21 C22 H22B 109.8 . . ?
H22A C22 H22B 108.2 . . ?
N20 C23 H23A 109.5 . . ?
N20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1A O1A H1A 109.5 . . ?
O1A C1A H1A1 109.5 . . ?
O1A C1A H1A2 109.5 . . ?
H1A1 C1A H1A2 109.5 . . ?
O1A C1A H1A3 109.5 . . ?
H1A1 C1A H1A3 109.5 . . ?
H1A2 C1A H1A3 109.5 . . ?
C1B O1B H1B 109.5 . . ?
O1B C1B H1B1 109.5 . . ?
O1B C1B H1B2 109.5 . . ?
H1B1 C1B H1B2 109.5 . . ?
O1B C1B H1B3 109.5 . . ?
H1B1 C1B H1B3 109.5 . . ?
H1B2 C1B H1B3 109.5 . . ?

_refine_diff_density_max         0.968
_refine_diff_density_min         -0.985
_refine_diff_density_rms         0.085

