# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_bisPyTM
_database_code_depnum_ccdc_archive 'CCDC 1559962'
_audit_update_record             
;
2017-07-03 deposited with the CCDC.
2018-01-09 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C17 H6 Cl7 N2'
_chemical_formula_moiety         'C17 H6 Cl7 N2'
_chemical_formula_weight         486.42
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   8.7015(13)
_cell_length_b                   14.840(3)
_cell_length_c                   14.860(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 105.5165(15)
_cell_angle_gamma                90.0000
_cell_volume                     1848.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5228
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      27.48
_cell_measurement_temperature    113
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             964.00
_exptl_absorpt_coefficient_mu    1.077
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.849
_exptl_absorpt_correction_T_max  0.968

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

_diffrn_ambient_temperature      113
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            14405
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# 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).
;
_reflns_number_total             4208
_reflns_number_gt                3601
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0888
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4208
_refine_ls_number_parameters     235
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0484P)²+0.5686P] 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          0.001
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.320
_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 0.0033 0.0016
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.10558(6) 0.26356(3) 0.62941(4) 0.02858(13) Uani 1.0 4 d . . .
Cl2 Cl 0.43120(7) -0.04541(3) 0.75752(4) 0.03016(13) Uani 1.0 4 d . . .
Cl3 Cl 0.54016(6) 0.19701(4) 0.82681(4) 0.03581(15) Uani 1.0 4 d . . .
Cl4 Cl -0.07861(6) 0.18254(4) 0.84981(4) 0.03050(13) Uani 1.0 4 d . . .
Cl5 Cl -0.08477(6) 0.04067(3) 0.61726(3) 0.02722(13) Uani 1.0 4 d . . .
Cl6 Cl 0.30267(6) 0.02878(4) 0.97313(3) 0.03037(13) Uani 1.0 4 d . . .
Cl7 Cl -0.18762(7) -0.19813(4) 0.86298(4) 0.03389(14) Uani 1.0 4 d . . .
N1 N 0.3905(2) 0.10540(11) 0.53476(11) 0.0239(4) Uani 1.0 4 d . . .
N2 N 0.2791(3) 0.34886(12) 0.94394(12) 0.0287(4) Uani 1.0 4 d . . .
C1 C 0.2009(3) 0.10820(13) 0.77445(13) 0.0209(4) Uani 1.0 4 d . . .
C2 C 0.2970(3) 0.17226(13) 0.54861(13) 0.0229(4) Uani 1.0 4 d . . .
C3 C 0.2320(3) 0.17482(12) 0.62412(13) 0.0199(4) Uani 1.0 4 d . . .
C4 C 0.2636(3) 0.10656(12) 0.69170(13) 0.0187(4) Uani 1.0 4 d . . .
C5 C 0.3646(3) 0.03863(12) 0.67585(13) 0.0212(4) Uani 1.0 4 d . . .
C6 C 0.4244(3) 0.04005(13) 0.59806(14) 0.0241(5) Uani 1.0 4 d . . .
C7 C 0.1420(3) 0.30409(13) 0.92568(14) 0.0268(5) Uani 1.0 4 d . . .
C8 C 0.1122(3) 0.22641(13) 0.87205(13) 0.0202(4) Uani 1.0 4 d . . .
C9 C 0.2284(2) 0.18803(12) 0.83394(12) 0.0177(4) Uani 1.0 4 d . . .
C10 C 0.3730(3) 0.23604(13) 0.85717(14) 0.0219(4) Uani 1.0 4 d . . .
C11 C 0.3924(3) 0.31424(14) 0.90896(14) 0.0260(5) Uani 1.0 4 d . . .
C12 C -0.0734(3) -0.11130(13) 0.83703(14) 0.0239(4) Uani 1.0 4 d . . .
C13 C -0.1115(3) -0.07672(13) 0.74729(13) 0.0241(4) Uani 1.0 4 d . . .
C14 C -0.0201(3) -0.00647(13) 0.72767(13) 0.0222(4) Uani 1.0 4 d . . .
C15 C 0.1098(3) 0.03102(12) 0.79512(13) 0.0193(4) Uani 1.0 4 d . . .
C16 C 0.1423(3) -0.00805(13) 0.88462(13) 0.0220(4) Uani 1.0 4 d . . .
C17 C 0.0529(3) -0.07799(13) 0.90614(13) 0.0238(4) Uani 1.0 4 d . . .
H2 H 0.2740 0.2203 0.5048 0.0274 Uiso 1.0 4 calc R . .
H6 H 0.4922 -0.0076 0.5898 0.0290 Uiso 1.0 4 calc R . .
H7 H 0.0599 0.3266 0.9507 0.0321 Uiso 1.0 4 calc R . .
H11 H 0.4914 0.3451 0.9203 0.0312 Uiso 1.0 4 calc R . .
H13 H -0.1983 -0.1005 0.7002 0.0289 Uiso 1.0 4 calc R . .
H17 H 0.0780 -0.1026 0.9674 0.0286 Uiso 1.0 4 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'


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

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Cl1 C3 1.731(2) yes . .
Cl2 C5 1.7285(19) yes . .
Cl3 C10 1.733(3) yes . .
Cl4 C8 1.731(2) yes . .
Cl5 C14 1.7332(19) yes . .
Cl6 C16 1.7302(18) yes . .
Cl7 C12 1.733(3) yes . .
N1 C2 1.333(3) yes . .
N1 C6 1.328(3) yes . .
N2 C7 1.329(3) yes . .
N2 C11 1.334(4) yes . .
C1 C4 1.473(3) yes . .
C1 C9 1.459(3) yes . .
C1 C15 1.471(3) yes . .
C2 C3 1.386(3) yes . .
C3 C4 1.401(3) yes . .
C4 C5 1.398(3) yes . .
C5 C6 1.389(4) yes . .
C7 C8 1.386(3) yes . .
C8 C9 1.405(3) yes . .
C9 C10 1.407(3) yes . .
C10 C11 1.378(3) yes . .
C12 C13 1.384(3) yes . .
C12 C17 1.379(3) yes . .
C13 C14 1.389(3) yes . .
C14 C15 1.409(3) yes . .
C15 C16 1.408(3) yes . .
C16 C17 1.385(3) yes . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C2 N1 C6 117.59(19) yes . . .
C7 N2 C11 116.39(19) yes . . .
C4 C1 C9 118.80(17) yes . . .
C4 C1 C15 120.13(17) yes . . .
C9 C1 C15 121.05(19) yes . . .
N1 C2 C3 122.91(18) yes . . .
Cl1 C3 C2 117.37(14) yes . . .
Cl1 C3 C4 121.51(17) yes . . .
C2 C3 C4 121.09(18) yes . . .
C1 C4 C3 122.75(18) yes . . .
C1 C4 C5 122.86(17) yes . . .
C3 C4 C5 114.34(19) yes . . .
Cl2 C5 C4 120.63(17) yes . . .
Cl2 C5 C6 117.76(16) yes . . .
C4 C5 C6 121.43(17) yes . . .
N1 C6 C5 122.61(19) yes . . .
N2 C7 C8 123.6(3) yes . . .
Cl4 C8 C7 116.41(17) yes . . .
Cl4 C8 C9 121.83(14) yes . . .
C7 C8 C9 121.68(19) yes . . .
C1 C9 C8 123.67(17) yes . . .
C1 C9 C10 123.43(19) yes . . .
C8 C9 C10 112.88(17) yes . . .
Cl3 C10 C9 121.66(16) yes . . .
Cl3 C10 C11 116.18(16) yes . . .
C9 C10 C11 122.1(2) yes . . .
N2 C11 C10 123.3(2) yes . . .
Cl7 C12 C13 119.10(15) yes . . .
Cl7 C12 C17 119.40(16) yes . . .
C13 C12 C17 121.5(2) yes . . .
C12 C13 C14 118.53(17) yes . . .
Cl5 C14 C13 116.28(14) yes . . .
Cl5 C14 C15 120.63(16) yes . . .
C13 C14 C15 122.86(18) yes . . .
C1 C15 C14 122.23(17) yes . . .
C1 C15 C16 122.29(16) yes . . .
C14 C15 C16 115.43(18) yes . . .
Cl6 C16 C15 120.35(15) yes . . .
Cl6 C16 C17 116.74(14) yes . . .
C15 C16 C17 122.89(16) yes . . .
C12 C17 C16 118.78(18) yes . . .



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

#==============================================================================
# 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        
'bis(3,5-dichloro-4-pyridyl)(2,4,6-trichlorophenyl)methyl radical '
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_chemical_properties_physical    ', Light-sensitive'
