# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_k10187
_database_code_depnum_ccdc_archive 'CCDC 1545272'
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2016). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2017-06-27 deposited with the CCDC.
2017-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6

_shelx_SHELXL_version_number     2016/6

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 Cl N O2'
_chemical_formula_sum            'C13 H10 Cl N O2'
_chemical_formula_weight         247.67

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   9.8504(1)
_cell_length_b                   7.4915(2)
_cell_length_c                   31.4272(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2319.15(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    3056
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.317
_shelx_estimated_absorpt_T_min   0.884
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.884
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 2006)'
_exptl_absorpt_special_details   
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by x-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the x-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;

_exptl_special_details           
; 
The crystal was mounted using polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
Diffraction data were collected with the crystal at 90K, which is standard 
practice in this laboratory for the majority of flash-cooled crystals. 
;

_diffrn_ambient_temperature      90.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed-tube'
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'φ and ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 9.1
_diffrn_reflns_number            4917
_diffrn_reflns_av_unetI/netI     0.0713
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.440
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_full        25.242
_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             2655
_reflns_number_gt                1420
_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       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 2006)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 2006)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015b)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'

_refine_special_details          
; 
Refinement progress was checked using Platon (Spek, 2009) and by 
an R-tensor (Parkin, 2000). The final model was further checked 
with the IUCr utility checkCIF. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0846P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2655
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1190
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1573
_refine_ls_wR_factor_gt          0.1269
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_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
Cl1 Cl 1.15122(7) 0.33957(12) 0.62450(2) 0.0438(3) Uani 1 1 d . . . . .
C1 C 0.7640(3) 0.2122(4) 0.59897(8) 0.0277(6) Uani 1 1 d . . . . .
C2 C 0.7753(3) 0.1372(4) 0.55767(8) 0.0273(6) Uani 1 1 d . . . . .
C3 C 0.9047(3) 0.1162(4) 0.53968(8) 0.0324(7) Uani 1 1 d . . . . .
H3 H 0.912162 0.060754 0.512592 0.039 Uiso 1 1 calc R U . . .
C4 C 1.0209(3) 0.1726(4) 0.55970(9) 0.0335(7) Uani 1 1 d . . . . .
H4 H 1.107694 0.155971 0.547161 0.040 Uiso 1 1 calc R U . . .
C5 C 1.0064(3) 0.2544(4) 0.59873(9) 0.0346(7) Uani 1 1 d . . . . .
C6 C 0.8828(3) 0.2767(4) 0.61834(8) 0.0295(7) Uani 1 1 d . . . . .
H6 H 0.877748 0.335696 0.645049 0.035 Uiso 1 1 calc R U . . .
N7 N 0.6396(2) 0.2269(3) 0.61871(7) 0.0295(6) Uani 1 1 d . . . . .
H7 H 0.567(3) 0.211(4) 0.6007(9) 0.035 Uiso 1 1 d . U . . .
C8 C 0.6125(3) 0.2884(4) 0.66013(8) 0.0285(7) Uani 1 1 d . . . . .
C9 C 0.6935(3) 0.2441(4) 0.69507(9) 0.0319(7) Uani 1 1 d . . . . .
H9 H 0.769896 0.168091 0.691621 0.038 Uiso 1 1 calc R U . . .
C10 C 0.6613(3) 0.3124(4) 0.73484(9) 0.0367(8) Uani 1 1 d . . . . .
H10 H 0.718164 0.286439 0.758468 0.044 Uiso 1 1 calc R U . . .
C11 C 0.5475(3) 0.4178(4) 0.74050(9) 0.0413(8) Uani 1 1 d . . . . .
H11 H 0.526782 0.464726 0.767819 0.050 Uiso 1 1 calc R U . . .
C12 C 0.4641(3) 0.4546(4) 0.70629(9) 0.0387(8) Uani 1 1 d . . . . .
H12 H 0.384405 0.524088 0.710253 0.046 Uiso 1 1 calc R U . . .
C13 C 0.4962(3) 0.3905(4) 0.66635(9) 0.0316(7) Uani 1 1 d . . . . .
H13 H 0.438500 0.416337 0.642927 0.038 Uiso 1 1 calc R U . . .
C14 C 0.6561(3) 0.0818(4) 0.53294(9) 0.0293(7) Uani 1 1 d . . . . .
O15 O 0.53744(18) 0.1102(3) 0.54382(6) 0.0334(5) Uani 1 1 d . . . . .
O16 O 0.6844(2) 0.0018(3) 0.49629(6) 0.0328(5) Uani 1 1 d . . . . .
H16 H 0.609(3) -0.034(4) 0.4828(9) 0.049 Uiso 1 1 d . 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 C5 1.760(3) . ?
C1 N7 1.378(3) . ?
C1 C6 1.405(4) . ?
C1 C2 1.419(4) . ?
C2 C3 1.403(3) . ?
C2 C14 1.469(4) . ?
C3 C4 1.373(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.375(4) . ?
C6 H6 0.9500 . ?
N7 C8 1.406(3) . ?
N7 H7 0.92(3) . ?
C8 C13 1.391(4) . ?
C8 C9 1.398(4) . ?
C9 C10 1.387(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O15 1.236(3) . ?
C14 O16 1.328(3) . ?
O16 H16 0.90(3) . ?

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
N7 C1 C6 121.2(2) . . ?
N7 C1 C2 120.9(2) . . ?
C6 C1 C2 117.9(2) . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 C14 118.8(2) . . ?
C1 C2 C14 122.2(2) . . ?
C4 C3 C2 122.5(3) . . ?
C4 C3 H3 118.7 . . ?
C2 C3 H3 118.7 . . ?
C3 C4 C5 117.3(3) . . ?
C3 C4 H4 121.3 . . ?
C5 C4 H4 121.3 . . ?
C6 C5 C4 123.0(3) . . ?
C6 C5 Cl1 117.9(2) . . ?
C4 C5 Cl1 119.2(2) . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C1 N7 C8 127.7(2) . . ?
C1 N7 H7 113.7(17) . . ?
C8 N7 H7 117.8(17) . . ?
C13 C8 C9 119.4(3) . . ?
C13 C8 N7 117.8(2) . . ?
C9 C8 N7 122.8(3) . . ?
C10 C9 C8 119.3(3) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.1(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 120.5(3) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
O15 C14 O16 121.1(3) . . ?
O15 C14 C2 124.1(3) . . ?
O16 C14 C2 114.7(2) . . ?
C14 O16 H16 112(2) . . ?

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
N7 C1 C2 C3 -176.7(3) . . . . ?
C6 C1 C2 C3 5.6(4) . . . . ?
N7 C1 C2 C14 3.7(4) . . . . ?
C6 C1 C2 C14 -174.0(3) . . . . ?
C1 C2 C3 C4 -2.9(4) . . . . ?
C14 C2 C3 C4 176.7(3) . . . . ?
C2 C3 C4 C5 -0.7(5) . . . . ?
C3 C4 C5 C6 1.7(5) . . . . ?
C3 C4 C5 Cl1 -176.8(2) . . . . ?
C4 C5 C6 C1 1.1(5) . . . . ?
Cl1 C5 C6 C1 179.6(2) . . . . ?
N7 C1 C6 C5 177.5(3) . . . . ?
C2 C1 C6 C5 -4.7(4) . . . . ?
C6 C1 N7 C8 -6.2(4) . . . . ?
C2 C1 N7 C8 176.2(3) . . . . ?
C1 N7 C8 C13 142.3(3) . . . . ?
C1 N7 C8 C9 -40.7(4) . . . . ?
C13 C8 C9 C10 -4.1(4) . . . . ?
N7 C8 C9 C10 178.9(3) . . . . ?
C8 C9 C10 C11 2.4(4) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
C10 C11 C12 C13 -1.8(4) . . . . ?
C11 C12 C13 C8 0.1(4) . . . . ?
C9 C8 C13 C12 2.9(4) . . . . ?
N7 C8 C13 C12 180.0(3) . . . . ?
C3 C2 C14 O15 -172.6(3) . . . . ?
C1 C2 C14 O15 7.0(4) . . . . ?
C3 C2 C14 O16 5.3(4) . . . . ?
C1 C2 C14 O16 -175.1(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N7 H7 O15 0.92(3) 1.96(3) 2.705(3) 137(2) .
C13 H13 Cl1 0.95 2.95 3.664(3) 133.4 1_455
O16 H16 O15 0.90(3) 1.76(3) 2.659(3) 178(3) 5_656

_refine_diff_density_max         0.498
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_k10157
_database_code_depnum_ccdc_archive 'CCDC 1545271'
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2016). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2017-06-27 deposited with the CCDC.
2017-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6

_shelx_SHELXL_version_number     2016/6

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 Cl N O2'
_chemical_formula_sum            'C13 H10 Cl N O2'
_chemical_formula_weight         247.67

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.2249(2)
_cell_length_b                   10.1269(3)
_cell_length_c                   13.7993(4)
_cell_angle_alpha                88.2266(11)
_cell_angle_beta                 85.9540(11)
_cell_angle_gamma                81.4168(11)
_cell_volume                     1133.43(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    5159
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.324
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 2006)'
_exptl_absorpt_special_details   
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by x-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the x-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;

_exptl_special_details           
; 
The crystal was mounted using polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
Diffraction data were collected with the crystal at 90K, which is standard 
practice in this laboratory for the majority of flash-cooled crystals. 
;

_diffrn_ambient_temperature      90.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed-tube'
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'φ and ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 9.1
_diffrn_reflns_number            10310
_diffrn_reflns_av_unetI/netI     0.0784
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.480
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000

_reflns_number_total             5202
_reflns_number_gt                3263
_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       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 2006)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 2006)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015b)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'

_refine_special_details          
; 
Refinement progress was checked using Platon (Spek, 2009) and by 
an R-tensor (Parkin, 2000). The final model was further checked 
with the IUCr utility checkCIF. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0427P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5202
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.0993
_refine_ls_wR_factor_gt          0.0853
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_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
Cl1A Cl 0.95907(6) -0.35528(5) 0.24016(3) 0.02806(15) Uani 1 1 d . . . . .
C1A C 0.5970(2) -0.05393(19) 0.19182(13) 0.0221(4) Uani 1 1 d . . . . .
C2A C 0.6603(2) 0.00391(19) 0.10428(13) 0.0202(4) Uani 1 1 d . . . . .
C3A C 0.8136(2) -0.05318(19) 0.06216(13) 0.0231(5) Uani 1 1 d . . . . .
H3A H 0.854696 -0.014603 0.003552 0.028 Uiso 1 1 calc R U . . .
C4A C 0.9066(2) -0.16209(19) 0.10179(13) 0.0243(5) Uani 1 1 d . . . . .
H4A H 1.010745 -0.198597 0.072188 0.029 Uiso 1 1 calc R U . . .
C5A C 0.8428(2) -0.21723(19) 0.18706(13) 0.0231(5) Uani 1 1 d . . . . .
C6A C 0.6932(2) -0.16701(18) 0.23200(13) 0.0223(4) Uani 1 1 d . . . . .
H6A H 0.654310 -0.208249 0.290094 0.027 Uiso 1 1 calc R U . . .
N7A N 0.45047(19) -0.00074(17) 0.23790(12) 0.0267(4) Uani 1 1 d . . . . .
H7A H 0.401(2) 0.074(2) 0.2116(14) 0.032 Uiso 1 1 d . U . . .
C8A C 0.3727(2) -0.05801(19) 0.32117(14) 0.0227(5) Uani 1 1 d . . . . .
C9A C 0.3252(2) -0.1837(2) 0.31749(14) 0.0267(5) Uani 1 1 d . . . . .
H9A H 0.349419 -0.234337 0.260089 0.032 Uiso 1 1 calc R U . . .
C10A C 0.2423(2) -0.2353(2) 0.39773(14) 0.0274(5) Uani 1 1 d . . . . .
H10A H 0.211561 -0.321907 0.395725 0.033 Uiso 1 1 calc R U . . .
C11A C 0.2044(2) -0.1602(2) 0.48078(14) 0.0270(5) Uani 1 1 d . . . . .
H11A H 0.145639 -0.194352 0.535335 0.032 Uiso 1 1 calc R U . . .
C12A C 0.2525(2) -0.0352(2) 0.48394(14) 0.0285(5) Uani 1 1 d . . . . .
H12A H 0.226628 0.016199 0.540921 0.034 Uiso 1 1 calc R U . . .
C13A C 0.3377(2) 0.0156(2) 0.40488(13) 0.0265(5) Uani 1 1 d . . . . .
H13A H 0.372230 0.100732 0.408009 0.032 Uiso 1 1 calc R U . . .
C14A C 0.5727(2) 0.12385(19) 0.05916(13) 0.0215(4) Uani 1 1 d . . . . .
O15A O 0.43798(15) 0.18531(13) 0.09151(9) 0.0245(3) Uani 1 1 d . . . . .
O16A O 0.64971(16) 0.16435(14) -0.02144(9) 0.0268(3) Uani 1 1 d . . . . .
H16A H 0.591(2) 0.253(2) -0.0455(14) 0.040 Uiso 1 1 d . U . . .
Cl1B Cl 0.98489(6) 0.07709(5) 0.27343(3) 0.02514(14) Uani 1 1 d . . . . .
C1B C 0.6390(2) 0.38135(18) 0.20481(13) 0.0200(4) Uani 1 1 d . . . . .
C2B C 0.7170(2) 0.43747(19) 0.12100(13) 0.0210(4) Uani 1 1 d . . . . .
C3B C 0.8765(2) 0.37981(19) 0.08881(13) 0.0222(4) Uani 1 1 d . . . . .
H3B H 0.928101 0.417124 0.032873 0.027 Uiso 1 1 calc R U . . .
C4B C 0.9608(2) 0.27165(19) 0.13496(13) 0.0231(5) Uani 1 1 d . . . . .
H4B H 1.069556 0.235174 0.112478 0.028 Uiso 1 1 calc R U . . .
C5B C 0.8820(2) 0.21687(18) 0.21583(13) 0.0203(4) Uani 1 1 d . . . . .
C6B C 0.7252(2) 0.26901(18) 0.25042(13) 0.0203(4) Uani 1 1 d . . . . .
H6B H 0.674991 0.228686 0.305529 0.024 Uiso 1 1 calc R U . . .
N7B N 0.48209(19) 0.43356(16) 0.23697(11) 0.0230(4) Uani 1 1 d . . . . .
H7B H 0.432(2) 0.4952(18) 0.1992(13) 0.028 Uiso 1 1 d . U . . .
C8B C 0.3885(2) 0.39811(18) 0.32124(13) 0.0206(4) Uani 1 1 d . . . . .
C9B C 0.4530(2) 0.38246(18) 0.41227(13) 0.0240(5) Uani 1 1 d . . . . .
H9B H 0.565913 0.388176 0.418768 0.029 Uiso 1 1 calc R U . . .
C10B C 0.3512(2) 0.35849(19) 0.49329(14) 0.0260(5) Uani 1 1 d . . . . .
H10B H 0.395746 0.345902 0.555157 0.031 Uiso 1 1 calc R U . . .
C11B C 0.1861(2) 0.35264(19) 0.48533(14) 0.0277(5) Uani 1 1 d . . . . .
H11B H 0.116812 0.337964 0.541474 0.033 Uiso 1 1 calc R U . . .
C12B C 0.1223(2) 0.36835(19) 0.39491(14) 0.0263(5) Uani 1 1 d . . . . .
H12B H 0.008690 0.364825 0.389024 0.032 Uiso 1 1 calc R U . . .
C13B C 0.2233(2) 0.38923(18) 0.31267(14) 0.0232(5) Uani 1 1 d . . . . .
H13B H 0.179454 0.397452 0.250548 0.028 Uiso 1 1 calc R U . . .
C14B C 0.6360(2) 0.55419(19) 0.06901(13) 0.0211(4) Uani 1 1 d . . . . .
O15B O 0.49311(15) 0.60846(13) 0.09054(9) 0.0254(3) Uani 1 1 d . . . . .
O16B O 0.72624(16) 0.60020(14) -0.00461(9) 0.0267(3) Uani 1 1 d . . . . .
H16B H 0.663(2) 0.677(2) -0.0321(14) 0.040 Uiso 1 1 d . 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
Cl1A C5A 1.7442(19) . ?
C1A N7A 1.366(2) . ?
C1A C6A 1.413(3) . ?
C1A C2A 1.425(2) . ?
C2A C3A 1.401(2) . ?
C2A C14A 1.462(3) . ?
C3A C4A 1.368(3) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.390(3) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.372(2) . ?
C6A H6A 0.9500 . ?
N7A C8A 1.425(2) . ?
N7A H7A 0.884(19) . ?
C8A C13A 1.384(2) . ?
C8A C9A 1.390(3) . ?
C9A C10A 1.388(3) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.387(3) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.384(3) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.383(3) . ?
C12A H12A 0.9500 . ?
C13A H13A 0.9500 . ?
C14A O15A 1.247(2) . ?
C14A O16A 1.325(2) . ?
O16A H16A 1.01(2) . ?
Cl1B C5B 1.7376(19) . ?
C1B N7B 1.368(2) . ?
C1B C6B 1.404(2) . ?
C1B C2B 1.427(3) . ?
C2B C3B 1.402(2) . ?
C2B C14B 1.461(3) . ?
C3B C4B 1.371(3) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.393(2) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.377(2) . ?
C6B H6B 0.9500 . ?
N7B C8B 1.416(2) . ?
N7B H7B 0.876(18) . ?
C8B C13B 1.388(2) . ?
C8B C9B 1.393(3) . ?
C9B C10B 1.386(2) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.381(3) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.383(3) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.388(2) . ?
C12B H12B 0.9500 . ?
C13B H13B 0.9500 . ?
C14B O15B 1.240(2) . ?
C14B O16B 1.330(2) . ?
O16B H16B 0.95(2) . ?

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
N7A C1A C6A 120.28(17) . . ?
N7A C1A C2A 121.78(17) . . ?
C6A C1A C2A 117.92(16) . . ?
C3A C2A C1A 118.97(17) . . ?
C3A C2A C14A 119.05(16) . . ?
C1A C2A C14A 121.94(16) . . ?
C4A C3A C2A 122.83(18) . . ?
C4A C3A H3A 118.6 . . ?
C2A C3A H3A 118.6 . . ?
C3A C4A C5A 117.37(17) . . ?
C3A C4A H4A 121.3 . . ?
C5A C4A H4A 121.3 . . ?
C6A C5A C4A 122.94(18) . . ?
C6A C5A Cl1A 118.47(15) . . ?
C4A C5A Cl1A 118.58(14) . . ?
C5A C6A C1A 119.97(17) . . ?
C5A C6A H6A 120.0 . . ?
C1A C6A H6A 120.0 . . ?
C1A N7A C8A 125.23(17) . . ?
C1A N7A H7A 115.7(13) . . ?
C8A N7A H7A 119.1(13) . . ?
C13A C8A C9A 120.00(18) . . ?
C13A C8A N7A 119.22(18) . . ?
C9A C8A N7A 120.71(17) . . ?
C10A C9A C8A 119.99(18) . . ?
C10A C9A H9A 120.0 . . ?
C8A C9A H9A 120.0 . . ?
C11A C10A C9A 119.87(19) . . ?
C11A C10A H10A 120.1 . . ?
C9A C10A H10A 120.1 . . ?
C12A C11A C10A 119.77(18) . . ?
C12A C11A H11A 120.1 . . ?
C10A C11A H11A 120.1 . . ?
C13A C12A C11A 120.56(18) . . ?
C13A C12A H12A 119.7 . . ?
C11A C12A H12A 119.7 . . ?
C12A C13A C8A 119.78(19) . . ?
C12A C13A H13A 120.1 . . ?
C8A C13A H13A 120.1 . . ?
O15A C14A O16A 121.38(17) . . ?
O15A C14A C2A 124.73(17) . . ?
O16A C14A C2A 113.88(16) . . ?
C14A O16A H16A 110.9(11) . . ?
N7B C1B C6B 121.46(16) . . ?
N7B C1B C2B 120.30(17) . . ?
C6B C1B C2B 118.19(16) . . ?
C3B C2B C1B 118.84(17) . . ?
C3B C2B C14B 119.38(17) . . ?
C1B C2B C14B 121.77(16) . . ?
C4B C3B C2B 122.50(18) . . ?
C4B C3B H3B 118.8 . . ?
C2B C3B H3B 118.8 . . ?
C3B C4B C5B 117.93(17) . . ?
C3B C4B H4B 121.0 . . ?
C5B C4B H4B 121.0 . . ?
C6B C5B C4B 122.06(17) . . ?
C6B C5B Cl1B 119.34(14) . . ?
C4B C5B Cl1B 118.60(14) . . ?
C5B C6B C1B 120.46(17) . . ?
C5B C6B H6B 119.8 . . ?
C1B C6B H6B 119.8 . . ?
C1B N7B C8B 128.73(16) . . ?
C1B N7B H7B 115.5(12) . . ?
C8B N7B H7B 115.7(12) . . ?
C13B C8B C9B 119.66(18) . . ?
C13B C8B N7B 117.79(17) . . ?
C9B C8B N7B 122.36(17) . . ?
C10B C9B C8B 119.57(18) . . ?
C10B C9B H9B 120.2 . . ?
C8B C9B H9B 120.2 . . ?
C11B C10B C9B 120.91(19) . . ?
C11B C10B H10B 119.5 . . ?
C9B C10B H10B 119.5 . . ?
C10B C11B C12B 119.40(18) . . ?
C10B C11B H11B 120.3 . . ?
C12B C11B H11B 120.3 . . ?
C11B C12B C13B 120.44(18) . . ?
C11B C12B H12B 119.8 . . ?
C13B C12B H12B 119.8 . . ?
C12B C13B C8B 119.99(18) . . ?
C12B C13B H13B 120.0 . . ?
C8B C13B H13B 120.0 . . ?
O15B C14B O16B 121.11(17) . . ?
O15B C14B C2B 123.54(16) . . ?
O16B C14B C2B 115.35(16) . . ?
C14B O16B H16B 108.5(12) . . ?

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
N7A C1A C2A C3A 178.15(17) . . . . ?
C6A C1A C2A C3A 0.0(3) . . . . ?
N7A C1A C2A C14A 0.4(3) . . . . ?
C6A C1A C2A C14A -177.71(17) . . . . ?
C1A C2A C3A C4A -0.5(3) . . . . ?
C14A C2A C3A C4A 177.30(17) . . . . ?
C2A C3A C4A C5A 0.6(3) . . . . ?
C3A C4A C5A C6A -0.2(3) . . . . ?
C3A C4A C5A Cl1A -179.43(14) . . . . ?
C4A C5A C6A C1A -0.3(3) . . . . ?
Cl1A C5A C6A C1A 178.98(14) . . . . ?
N7A C1A C6A C5A -177.83(17) . . . . ?
C2A C1A C6A C5A 0.4(3) . . . . ?
C6A C1A N7A C8A -7.0(3) . . . . ?
C2A C1A N7A C8A 174.89(17) . . . . ?
C1A N7A C8A C13A 122.1(2) . . . . ?
C1A N7A C8A C9A -60.9(3) . . . . ?
C13A C8A C9A C10A 0.2(3) . . . . ?
N7A C8A C9A C10A -176.82(17) . . . . ?
C8A C9A C10A C11A 1.2(3) . . . . ?
C9A C10A C11A C12A -1.3(3) . . . . ?
C10A C11A C12A C13A 0.1(3) . . . . ?
C11A C12A C13A C8A 1.2(3) . . . . ?
C9A C8A C13A C12A -1.4(3) . . . . ?
N7A C8A C13A C12A 175.66(17) . . . . ?
C3A C2A C14A O15A -177.97(17) . . . . ?
C1A C2A C14A O15A -0.3(3) . . . . ?
C3A C2A C14A O16A 1.9(2) . . . . ?
C1A C2A C14A O16A 179.57(16) . . . . ?
N7B C1B C2B C3B -178.66(16) . . . . ?
C6B C1B C2B C3B -1.0(3) . . . . ?
N7B C1B C2B C14B 2.3(3) . . . . ?
C6B C1B C2B C14B 179.88(16) . . . . ?
C1B C2B C3B C4B -0.2(3) . . . . ?
C14B C2B C3B C4B 178.93(16) . . . . ?
C2B C3B C4B C5B 1.1(3) . . . . ?
C3B C4B C5B C6B -0.8(3) . . . . ?
C3B C4B C5B Cl1B 178.37(14) . . . . ?
C4B C5B C6B C1B -0.4(3) . . . . ?
Cl1B C5B C6B C1B -179.59(13) . . . . ?
N7B C1B C6B C5B 178.93(17) . . . . ?
C2B C1B C6B C5B 1.3(3) . . . . ?
C6B C1B N7B C8B 7.0(3) . . . . ?
C2B C1B N7B C8B -175.47(17) . . . . ?
C1B N7B C8B C13B -138.02(19) . . . . ?
C1B N7B C8B C9B 47.0(3) . . . . ?
C13B C8B C9B C10B -0.1(3) . . . . ?
N7B C8B C9B C10B 174.71(17) . . . . ?
C8B C9B C10B C11B -1.4(3) . . . . ?
C9B C10B C11B C12B 1.3(3) . . . . ?
C10B C11B C12B C13B 0.3(3) . . . . ?
C11B C12B C13B C8B -1.8(3) . . . . ?
C9B C8B C13B C12B 1.7(3) . . . . ?
N7B C8B C13B C12B -173.40(17) . . . . ?
C3B C2B C14B O15B 177.42(17) . . . . ?
C1B C2B C14B O15B -3.5(3) . . . . ?
C3B C2B C14B O16B -2.6(3) . . . . ?
C1B C2B C14B O16B 176.52(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N7B H7B O15B 0.876(18) 1.944(19) 2.651(2) 136.8(16) .
O16B H16B O15A 0.95(2) 1.73(2) 2.6781(18) 174.6(19) 2_665
N7A H7A O15A 0.884(19) 2.01(2) 2.716(2) 136.2(17) .
O16A H16A O15B 1.01(2) 1.60(2) 2.6073(18) 176.0(18) 2_665

_refine_diff_density_max         0.266
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_k10138
_database_code_depnum_ccdc_archive 'CCDC 1545269'
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2016). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2017-06-27 deposited with the CCDC.
2017-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6

_shelx_SHELXL_version_number     2016/6

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 Cl N O2'
_chemical_formula_sum            'C13 H10 Cl N O2'
_chemical_formula_weight         247.67

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.9015(2)
_cell_length_b                   10.7701(2)
_cell_length_c                   11.3935(2)
_cell_angle_alpha                90.2523(8)
_cell_angle_beta                 103.8986(8)
_cell_angle_gamma                102.7160(8)
_cell_volume                     1148.40(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    5219
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       lath
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.320
_shelx_estimated_absorpt_T_min   0.856
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.856
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 2006)'
_exptl_absorpt_special_details   
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by x-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the x-ray beam cross section, absorption by the crystal 
mount etc.  These account, by and large, for much of the difference between 
estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;

_exptl_special_details           
; 
The crystal was mounted using polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
Diffraction data were collected with the crystal at 90K, which is standard 
practice in this laboratory for the majority of flash-cooled crystals. 
;

_diffrn_ambient_temperature      90.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed-tube'
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'φ and ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 9.1
_diffrn_reflns_number            10432
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.845
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000

_reflns_number_total             5257
_reflns_number_gt                3683
_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       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 2006)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 2006)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015b)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'

_refine_special_details          
; 
Refinement progress was checked using Platon (Spek, 2009) and by 
an R-tensor (Parkin, 2000). The final model was further checked 
with the IUCr utility checkCIF. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0604P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5257
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1148
_refine_ls_wR_factor_gt          0.1015
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
Cl1A Cl 0.35111(4) 0.49259(4) 0.68818(4) 0.02279(12) Uani 1 1 d . . . . .
C1A C 0.59133(16) 0.23552(14) 0.71121(13) 0.0160(3) Uani 1 1 d . . . . .
C2A C 0.57784(17) 0.20411(14) 0.58667(13) 0.0155(3) Uani 1 1 d . . . . .
C3A C 0.49208(17) 0.26179(14) 0.49756(14) 0.0185(4) Uani 1 1 d . . . . .
H3A H 0.482483 0.239147 0.414790 0.022 Uiso 1 1 calc R U . . .
C4A C 0.42114(17) 0.35009(15) 0.52538(14) 0.0194(4) Uani 1 1 d . . . . .
H4A H 0.363992 0.388927 0.463872 0.023 Uiso 1 1 calc R U . . .
C5A C 0.43695(17) 0.37993(14) 0.64792(14) 0.0180(4) Uani 1 1 d . . . . .
C6A C 0.51768(17) 0.32500(14) 0.73903(14) 0.0180(4) Uani 1 1 d . . . . .
H6A H 0.523882 0.347468 0.821188 0.022 Uiso 1 1 calc R U . . .
N7A N 0.67284(15) 0.17967(13) 0.80096(12) 0.0207(3) Uani 1 1 d . . . . .
H7A H 0.7038(19) 0.1129(17) 0.7774(15) 0.025 Uiso 1 1 d . U . . .
C8A C 0.69404(17) 0.20321(15) 0.92757(14) 0.0189(4) Uani 1 1 d . . . . .
C9A C 0.66548(18) 0.10117(16) 0.99768(14) 0.0248(4) Uani 1 1 d . . . . .
H9A H 0.631963 0.017091 0.960993 0.030 Uiso 1 1 calc R U . . .
C10A C 0.68571(19) 0.12129(17) 1.12196(15) 0.0292(4) Uani 1 1 d . . . . .
H10A H 0.665877 0.050797 1.169867 0.035 Uiso 1 1 calc R U . . .
C11A C 0.73441(19) 0.24305(17) 1.17609(15) 0.0277(4) Uani 1 1 d . . . . .
H11A H 0.746421 0.256775 1.260763 0.033 Uiso 1 1 calc R U . . .
C12A C 0.76559(18) 0.34491(17) 1.10608(15) 0.0269(4) Uani 1 1 d . . . . .
H12A H 0.800415 0.428715 1.143260 0.032 Uiso 1 1 calc R U . . .
C13A C 0.74660(18) 0.32606(16) 0.98236(14) 0.0244(4) Uani 1 1 d . . . . .
H13A H 0.769249 0.396442 0.935036 0.029 Uiso 1 1 calc R U . . .
C14A C 0.65099(16) 0.11188(14) 0.54928(13) 0.0161(3) Uani 1 1 d . . . . .
O15A O 0.72668(11) 0.05395(10) 0.62057(9) 0.0182(3) Uani 1 1 d . . . . .
O16A O 0.62916(12) 0.09435(11) 0.43031(9) 0.0198(3) Uani 1 1 d . . . . .
H16A H 0.6770(19) 0.0358(18) 0.4137(16) 0.030 Uiso 1 1 d . U . . .
Cl1B Cl 0.86075(4) 0.50414(4) 0.70774(3) 0.02074(12) Uani 1 1 d . . . . .
C1B C 1.08577(17) 0.23494(14) 0.72380(14) 0.0171(4) Uani 1 1 d . . . . .
C2B C 1.07278(17) 0.20666(14) 0.59897(13) 0.0158(3) Uani 1 1 d . . . . .
C3B C 0.98960(17) 0.26797(14) 0.51105(14) 0.0182(4) Uani 1 1 d . . . . .
H3B H 0.980263 0.247549 0.427858 0.022 Uiso 1 1 calc R U . . .
C4B C 0.92109(17) 0.35684(15) 0.54167(14) 0.0189(4) Uani 1 1 d . . . . .
H4B H 0.864735 0.397493 0.481262 0.023 Uiso 1 1 calc R U . . .
C5B C 0.93745(17) 0.38520(14) 0.66516(14) 0.0170(3) Uani 1 1 d . . . . .
C6B C 1.01493(16) 0.32570(14) 0.75457(14) 0.0175(4) Uani 1 1 d . . . . .
H6B H 1.020821 0.345675 0.837209 0.021 Uiso 1 1 calc R U . . .
N7B N 1.16865(16) 0.17904(14) 0.81239(12) 0.0222(3) Uani 1 1 d . . . . .
H7B H 1.2189(19) 0.1294(17) 0.7864(15) 0.027 Uiso 1 1 d . U . . .
C8B C 1.18406(18) 0.19514(15) 0.93917(14) 0.0187(4) Uani 1 1 d . . . . .
C9B C 1.31909(19) 0.23539(16) 1.01504(14) 0.0271(4) Uani 1 1 d . . . . .
H9B H 1.400150 0.256404 0.982043 0.033 Uiso 1 1 calc R U . . .
C10B C 1.3362(2) 0.24509(18) 1.13967(15) 0.0310(4) Uani 1 1 d . . . . .
H10B H 1.429305 0.271085 1.191791 0.037 Uiso 1 1 calc R U . . .
C11B C 1.21869(19) 0.21717(16) 1.18816(15) 0.0261(4) Uani 1 1 d . . . . .
H11B H 1.230711 0.225239 1.273327 0.031 Uiso 1 1 calc R U . . .
C12B C 1.08364(19) 0.17748(17) 1.11247(15) 0.0303(4) Uani 1 1 d . . . . .
H12B H 1.002457 0.158402 1.145435 0.036 Uiso 1 1 calc R U . . .
C13B C 1.06662(19) 0.16547(17) 0.98797(14) 0.0272(4) Uani 1 1 d . . . . .
H13B H 0.973774 0.136709 0.936091 0.033 Uiso 1 1 calc R U . . .
C14B C 1.14724(17) 0.11694(14) 0.55956(13) 0.0163(3) Uani 1 1 d . . . . .
O15B O 1.23165(11) 0.06527(10) 0.63000(9) 0.0188(3) Uani 1 1 d . . . . .
O16B O 1.11782(12) 0.09409(10) 0.44042(9) 0.0185(3) Uani 1 1 d . . . . .
H16B H 1.1759(19) 0.0386(17) 0.4218(16) 0.028 Uiso 1 1 d . 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
Cl1A C5A 1.7439(16) . ?
C1A N7A 1.372(2) . ?
C1A C6A 1.407(2) . ?
C1A C2A 1.425(2) . ?
C2A C3A 1.400(2) . ?
C2A C14A 1.468(2) . ?
C3A C4A 1.377(2) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.395(2) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.372(2) . ?
C6A H6A 0.9500 . ?
N7A C8A 1.4203(19) . ?
N7A H7A 0.905(18) . ?
C8A C9A 1.380(2) . ?
C8A C13A 1.394(2) . ?
C9A C10A 1.391(2) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.380(2) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.383(2) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.385(2) . ?
C12A H12A 0.9500 . ?
C13A H13A 0.9500 . ?
C14A O15A 1.2363(18) . ?
C14A O16A 1.3262(17) . ?
O16A H16A 0.912(19) . ?
Cl1B C5B 1.7473(16) . ?
C1B N7B 1.371(2) . ?
C1B C6B 1.410(2) . ?
C1B C2B 1.422(2) . ?
C2B C3B 1.402(2) . ?
C2B C14B 1.466(2) . ?
C3B C4B 1.376(2) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.401(2) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.372(2) . ?
C6B H6B 0.9500 . ?
N7B C8B 1.4212(19) . ?
N7B H7B 0.898(19) . ?
C8B C9B 1.382(2) . ?
C8B C13B 1.383(2) . ?
C9B C10B 1.390(2) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.381(3) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.380(2) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.390(2) . ?
C12B H12B 0.9500 . ?
C13B H13B 0.9500 . ?
C14B O15B 1.2405(18) . ?
C14B O16B 1.3280(17) . ?
O16B H16B 0.970(19) . ?

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
N7A C1A C6A 121.14(14) . . ?
N7A C1A C2A 121.02(14) . . ?
C6A C1A C2A 117.84(14) . . ?
C3A C2A C1A 119.39(14) . . ?
C3A C2A C14A 119.04(14) . . ?
C1A C2A C14A 121.57(14) . . ?
C4A C3A C2A 122.49(14) . . ?
C4A C3A H3A 118.8 . . ?
C2A C3A H3A 118.8 . . ?
C3A C4A C5A 117.01(15) . . ?
C3A C4A H4A 121.5 . . ?
C5A C4A H4A 121.5 . . ?
C6A C5A C4A 123.04(15) . . ?
C6A C5A Cl1A 118.07(12) . . ?
C4A C5A Cl1A 118.89(12) . . ?
C5A C6A C1A 120.22(14) . . ?
C5A C6A H6A 119.9 . . ?
C1A C6A H6A 119.9 . . ?
C1A N7A C8A 126.04(14) . . ?
C1A N7A H7A 116.5(11) . . ?
C8A N7A H7A 116.7(11) . . ?
C9A C8A C13A 119.69(14) . . ?
C9A C8A N7A 118.81(14) . . ?
C13A C8A N7A 121.47(15) . . ?
C8A C9A C10A 120.07(15) . . ?
C8A C9A H9A 120.0 . . ?
C10A C9A H9A 120.0 . . ?
C11A C10A C9A 120.40(16) . . ?
C11A C10A H10A 119.8 . . ?
C9A C10A H10A 119.8 . . ?
C10A C11A C12A 119.45(15) . . ?
C10A C11A H11A 120.3 . . ?
C12A C11A H11A 120.3 . . ?
C11A C12A C13A 120.70(16) . . ?
C11A C12A H12A 119.6 . . ?
C13A C12A H12A 119.6 . . ?
C12A C13A C8A 119.65(16) . . ?
C12A C13A H13A 120.2 . . ?
C8A C13A H13A 120.2 . . ?
O15A C14A O16A 121.66(14) . . ?
O15A C14A C2A 124.11(14) . . ?
O16A C14A C2A 114.23(13) . . ?
C14A O16A H16A 109.5(11) . . ?
N7B C1B C6B 120.54(14) . . ?
N7B C1B C2B 121.21(14) . . ?
C6B C1B C2B 118.21(14) . . ?
C3B C2B C1B 119.54(15) . . ?
C3B C2B C14B 118.86(13) . . ?
C1B C2B C14B 121.58(14) . . ?
C4B C3B C2B 121.98(14) . . ?
C4B C3B H3B 119.0 . . ?
C2B C3B H3B 119.0 . . ?
C3B C4B C5B 117.61(15) . . ?
C3B C4B H4B 121.2 . . ?
C5B C4B H4B 121.2 . . ?
C6B C5B C4B 122.62(15) . . ?
C6B C5B Cl1B 118.40(12) . . ?
C4B C5B Cl1B 118.95(12) . . ?
C5B C6B C1B 120.01(14) . . ?
C5B C6B H6B 120.0 . . ?
C1B C6B H6B 120.0 . . ?
C1B N7B C8B 126.13(14) . . ?
C1B N7B H7B 115.6(11) . . ?
C8B N7B H7B 118.2(11) . . ?
C9B C8B C13B 119.63(15) . . ?
C9B C8B N7B 119.37(15) . . ?
C13B C8B N7B 120.93(15) . . ?
C8B C9B C10B 119.94(17) . . ?
C8B C9B H9B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C11B C10B C9B 120.36(16) . . ?
C11B C10B H10B 119.8 . . ?
C9B C10B H10B 119.8 . . ?
C12B C11B C10B 119.78(16) . . ?
C12B C11B H11B 120.1 . . ?
C10B C11B H11B 120.1 . . ?
C11B C12B C13B 119.90(17) . . ?
C11B C12B H12B 120.0 . . ?
C13B C12B H12B 120.0 . . ?
C8B C13B C12B 120.38(16) . . ?
C8B C13B H13B 119.8 . . ?
C12B C13B H13B 119.8 . . ?
O15B C14B O16B 121.47(14) . . ?
O15B C14B C2B 123.83(13) . . ?
O16B C14B C2B 114.70(13) . . ?
C14B O16B H16B 109.4(10) . . ?

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
N7A C1A C2A C3A 179.12(15) . . . . ?
C6A C1A C2A C3A -0.5(2) . . . . ?
N7A C1A C2A C14A -0.4(2) . . . . ?
C6A C1A C2A C14A 179.93(13) . . . . ?
C1A C2A C3A C4A 1.0(2) . . . . ?
C14A C2A C3A C4A -179.37(14) . . . . ?
C2A C3A C4A C5A -0.5(2) . . . . ?
C3A C4A C5A C6A -0.5(2) . . . . ?
C3A C4A C5A Cl1A 179.25(11) . . . . ?
C4A C5A C6A C1A 1.0(2) . . . . ?
Cl1A C5A C6A C1A -178.72(11) . . . . ?
N7A C1A C6A C5A 179.87(14) . . . . ?
C2A C1A C6A C5A -0.5(2) . . . . ?
C6A C1A N7A C8A -0.3(3) . . . . ?
C2A C1A N7A C8A -179.94(15) . . . . ?
C1A N7A C8A C9A 126.20(18) . . . . ?
C1A N7A C8A C13A -55.6(2) . . . . ?
C13A C8A C9A C10A 1.6(3) . . . . ?
N7A C8A C9A C10A 179.78(15) . . . . ?
C8A C9A C10A C11A 0.0(3) . . . . ?
C9A C10A C11A C12A -1.2(3) . . . . ?
C10A C11A C12A C13A 0.9(3) . . . . ?
C11A C12A C13A C8A 0.7(3) . . . . ?
C9A C8A C13A C12A -1.9(3) . . . . ?
N7A C8A C13A C12A 179.95(16) . . . . ?
C3A C2A C14A O15A -178.53(15) . . . . ?
C1A C2A C14A O15A 1.0(2) . . . . ?
C3A C2A C14A O16A 1.3(2) . . . . ?
C1A C2A C14A O16A -179.15(13) . . . . ?
N7B C1B C2B C3B -178.55(15) . . . . ?
C6B C1B C2B C3B -0.7(2) . . . . ?
N7B C1B C2B C14B -0.1(2) . . . . ?
C6B C1B C2B C14B 177.76(13) . . . . ?
C1B C2B C3B C4B 1.0(2) . . . . ?
C14B C2B C3B C4B -177.54(14) . . . . ?
C2B C3B C4B C5B 0.2(2) . . . . ?
C3B C4B C5B C6B -1.8(2) . . . . ?
C3B C4B C5B Cl1B 176.32(11) . . . . ?
C4B C5B C6B C1B 2.1(2) . . . . ?
Cl1B C5B C6B C1B -176.06(11) . . . . ?
N7B C1B C6B C5B 177.09(14) . . . . ?
C2B C1B C6B C5B -0.8(2) . . . . ?
C6B C1B N7B C8B 5.5(3) . . . . ?
C2B C1B N7B C8B -176.73(15) . . . . ?
C1B N7B C8B C9B -125.05(18) . . . . ?
C1B N7B C8B C13B 58.0(2) . . . . ?
C13B C8B C9B C10B 0.4(3) . . . . ?
N7B C8B C9B C10B -176.63(16) . . . . ?
C8B C9B C10B C11B -1.3(3) . . . . ?
C9B C10B C11B C12B 1.0(3) . . . . ?
C10B C11B C12B C13B 0.2(3) . . . . ?
C9B C8B C13B C12B 0.8(3) . . . . ?
N7B C8B C13B C12B 177.78(16) . . . . ?
C11B C12B C13B C8B -1.1(3) . . . . ?
C3B C2B C14B O15B 174.39(15) . . . . ?
C1B C2B C14B O15B -4.1(2) . . . . ?
C3B C2B C14B O16B -5.5(2) . . . . ?
C1B C2B C14B O16B 175.97(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N7A H7A O15A 0.905(18) 1.973(18) 2.6760(17) 133.3(15) .
O16A H16A O15B 0.912(19) 1.70(2) 2.6104(16) 174.2(18) 2_756
C4B H4B Cl1A 0.95 2.97 3.9145(17) 170.4 2_666
C4A H4A Cl1B 0.95 3.03 3.9641(17) 169.4 2_666
N7B H7B O15B 0.898(19) 1.951(18) 2.6732(17) 136.3(15) .
O16B H16B O15A 0.970(19) 1.674(19) 2.6422(16) 175.9(17) 2_756
C12A H12A Cl1A 0.95 2.93 3.4712(17) 117.4 2_667

_refine_diff_density_max         0.488
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.062

