# 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_pClo_160427_3
_database_code_depnum_ccdc_archive 'CCDC 1525754'
_audit_update_record             
;
2017-01-05 deposited with the CCDC.
2017-03-08 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C34 H24 Cl4 N6'
_chemical_formula_moiety         'C34 H24 Cl4 N6'
_chemical_formula_weight         658.42
_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                   14.6554(5)
_cell_length_b                   6.00711(18)
_cell_length_c                   17.9996(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.1994(14)
_cell_angle_gamma                90.0000
_cell_volume                     1584.62(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7645
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      68.03
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.140
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             676.00
_exptl_absorpt_coefficient_mu    3.669
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6276
_exptl_absorpt_correction_T_max  0.7514

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

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            13776
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_theta_max         67.00
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_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             2751
_reflns_number_gt                1151
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0762
_refine_ls_wR_factor_ref         0.2408
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2750
_refine_ls_number_parameters     200
_refine_ls_goodness_of_fit_ref   1.606
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0550P)²+0.3000P] 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         -0.260
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0073(10)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(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)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
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 0.57728(12) 0.0494(4) 0.90963(10) 0.1427(9) Uani 1.0 4 d . . .
Cl2 Cl 1.16440(15) -0.1220(4) 0.54608(10) 0.1544(10) Uani 1.0 4 d . . .
N1 N 1.0066(3) 0.4045(7) 0.8510(3) 0.0859(13) Uani 1.0 4 d . . .
N2 N 0.9500(3) 0.6276(7) 0.9483(3) 0.0861(13) Uani 1.0 4 d . . .
N18 N 1.1261(4) -0.0388(10) 0.9382(3) 0.1215(19) Uani 1.0 4 d . . .
C1 C 1.0025(4) 0.4544(9) 0.9260(3) 0.0826(15) Uani 1.0 4 d . . .
C2 C 0.8385(4) 0.3662(9) 0.8320(3) 0.0826(15) Uani 1.0 4 d . . .
C3 C 0.8386(5) 0.1547(10) 0.8647(3) 0.0940(17) Uani 1.0 4 d . . .
C4 C 0.7558(5) 0.4743(10) 0.8228(3) 0.0980(18) Uani 1.0 4 d . . .
C5 C 1.0498(4) 0.3309(9) 0.9796(3) 0.0815(15) Uani 1.0 4 d . . .
C6 C 0.9272(4) 0.4739(9) 0.8064(3) 0.0932(17) Uani 1.0 4 d . . .
C7 C 0.6751(5) 0.3771(12) 0.8461(3) 0.1038(19) Uani 1.0 4 d . . .
C8 C 0.7581(5) 0.0616(10) 0.8881(3) 0.1002(18) Uani 1.0 4 d . . .
C9 C 0.6765(5) 0.1683(11) 0.8796(3) 0.0976(17) Uani 1.0 4 d . . .
C10 C 1.0962(4) 0.4399(10) 0.8162(3) 0.0982(18) Uani 1.0 4 d . . .
C11 C 1.1122(4) 0.2963(10) 0.7481(3) 0.0933(17) Uani 1.0 4 d . . .
C12 C 1.0892(5) -0.0417(10) 0.6780(4) 0.1060(19) Uani 1.0 4 d . . .
C13 C 1.1430(5) 0.0396(12) 0.6232(4) 0.1022(18) Uani 1.0 4 d . . .
C14 C 1.0722(4) 0.0857(10) 0.7404(3) 0.0996(18) Uani 1.0 4 d . . .
C15 C 1.0966(4) 0.1285(10) 0.9561(3) 0.0917(17) Uani 1.0 4 d . . .
C16 C 1.1671(5) 0.3732(10) 0.6912(4) 0.1072(19) Uani 1.0 4 d . . .
C17 C 1.1833(5) 0.2408(13) 0.6292(4) 0.123(3) Uani 1.0 4 d . . .
H3 H 0.8931 0.0774 0.8706 0.1128 Uiso 1.0 4 calc R . .
H4 H 0.7544 0.6142 0.8008 0.1176 Uiso 1.0 4 calc R . .
H6A H 0.9377 0.4351 0.7548 0.1118 Uiso 1.0 4 calc R . .
H6B H 0.9210 0.6344 0.8093 0.1118 Uiso 1.0 4 calc R . .
H7 H 0.6200 0.4514 0.8394 0.1245 Uiso 1.0 4 calc R . .
H8 H 0.7592 -0.0781 0.9104 0.1203 Uiso 1.0 4 calc R . .
H10A H 1.1436 0.4088 0.8525 0.1179 Uiso 1.0 4 calc R . .
H10B H 1.1015 0.5952 0.8021 0.1179 Uiso 1.0 4 calc R . .
H12 H 1.0638 -0.1830 0.6736 0.1271 Uiso 1.0 4 calc R . .
H14 H 1.0341 0.0313 0.7774 0.1195 Uiso 1.0 4 calc R . .
H16 H 1.1933 0.5139 0.6945 0.1286 Uiso 1.0 4 calc R . .
H17 H 1.2219 0.2910 0.5919 0.1478 Uiso 1.0 4 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_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 C9 1.709(7) yes . .
Cl2 C13 1.723(7) yes . .
N1 C1 1.385(7) yes . .
N1 C6 1.471(7) yes . .
N1 C10 1.472(7) yes . .
N2 C1 1.356(7) yes . .
N2 C5 1.321(7) yes . 3_767
N18 C15 1.141(9) yes . .
C1 C5 1.399(8) yes . .
C2 C3 1.401(8) yes . .
C2 C4 1.384(9) yes . .
C2 C6 1.525(8) yes . .
C3 C8 1.373(9) yes . .
C4 C7 1.385(10) yes . .
C5 C15 1.459(8) yes . .
C7 C9 1.391(9) yes . .
C8 C9 1.366(10) yes . .
C10 C11 1.518(8) yes . .
C11 C14 1.401(8) yes . .
C11 C16 1.384(9) yes . .
C12 C13 1.356(9) yes . .
C12 C14 1.383(9) yes . .
C13 C17 1.349(10) yes . .
C16 C17 1.391(10) yes . .
C3 H3 0.930 no . .
C4 H4 0.930 no . .
C6 H6A 0.970 no . .
C6 H6B 0.970 no . .
C7 H7 0.930 no . .
C8 H8 0.930 no . .
C10 H10A 0.970 no . .
C10 H10B 0.970 no . .
C12 H12 0.930 no . .
C14 H14 0.930 no . .
C16 H16 0.930 no . .
C17 H17 0.930 no . .

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
C1 N1 C6 115.7(5) yes . . .
C1 N1 C10 115.2(5) yes . . .
C6 N1 C10 115.6(4) yes . . .
C1 N2 C5 115.8(5) yes . . 3_767
N1 C1 N2 118.7(5) yes . . .
N1 C1 C5 122.3(5) yes . . .
N2 C1 C5 118.9(5) yes . . .
C3 C2 C4 118.4(6) yes . . .
C3 C2 C6 120.8(6) yes . . .
C4 C2 C6 120.8(5) yes . . .
C2 C3 C8 119.9(6) yes . . .
C2 C4 C7 121.0(6) yes . . .
N2 C5 C1 125.3(5) yes 3_767 . .
N2 C5 C15 116.2(5) yes 3_767 . .
C1 C5 C15 118.3(5) yes . . .
N1 C6 C2 112.9(5) yes . . .
C4 C7 C9 120.0(6) yes . . .
C3 C8 C9 121.9(6) yes . . .
Cl1 C9 C7 120.2(5) yes . . .
Cl1 C9 C8 120.9(5) yes . . .
C7 C9 C8 118.9(6) yes . . .
N1 C10 C11 113.7(5) yes . . .
C10 C11 C14 121.9(5) yes . . .
C10 C11 C16 120.0(6) yes . . .
C14 C11 C16 118.2(6) yes . . .
C13 C12 C14 119.9(6) yes . . .
Cl2 C13 C12 119.4(6) yes . . .
Cl2 C13 C17 119.3(5) yes . . .
C12 C13 C17 121.2(6) yes . . .
C11 C14 C12 120.2(6) yes . . .
N18 C15 C5 174.1(7) yes . . .
C11 C16 C17 120.2(6) yes . . .
C13 C17 C16 120.1(6) yes . . .
C2 C3 H3 120.042 no . . .
C8 C3 H3 120.038 no . . .
C2 C4 H4 119.513 no . . .
C7 C4 H4 119.516 no . . .
N1 C6 H6A 109.012 no . . .
N1 C6 H6B 109.018 no . . .
C2 C6 H6A 109.005 no . . .
C2 C6 H6B 109.007 no . . .
H6A C6 H6B 107.785 no . . .
C4 C7 H7 120.004 no . . .
C9 C7 H7 119.998 no . . .
C3 C8 H8 119.072 no . . .
C9 C8 H8 119.067 no . . .
N1 C10 H10A 108.834 no . . .
N1 C10 H10B 108.832 no . . .
C11 C10 H10A 108.823 no . . .
C11 C10 H10B 108.826 no . . .
H10A C10 H10B 107.690 no . . .
C13 C12 H12 120.035 no . . .
C14 C12 H12 120.046 no . . .
C11 C14 H14 119.879 no . . .
C12 C14 H14 119.875 no . . .
C11 C16 H16 119.898 no . . .
C17 C16 H16 119.883 no . . .
C13 C17 H17 119.939 no . . .
C16 C17 H17 119.942 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N1 C6 C2 -60.3(6) no . . . .
C6 N1 C1 N2 -25.4(7) no . . . .
C6 N1 C1 C5 153.8(5) no . . . .
C1 N1 C10 C11 154.3(4) no . . . .
C10 N1 C1 N2 113.7(5) no . . . .
C10 N1 C1 C5 -67.1(6) no . . . .
C6 N1 C10 C11 -66.5(6) no . . . .
C10 N1 C6 C2 160.8(4) no . . . .
C1 N2 C5 C1 -2.1(7) no . . 3_767 3_767
C1 N2 C5 C15 172.5(4) no . . 3_767 3_767
C5 N2 C1 N1 -178.8(4) no 3_767 . . .
C5 N2 C1 C5 1.9(7) no 3_767 . . .
N1 C1 C5 N2 178.7(5) no . . . 3_767
N1 C1 C5 C15 -6.9(8) no . . . .
N2 C1 C5 N2 -2.1(8) no . . . 3_767
N2 C1 C5 C15 172.3(4) no . . . .
C3 C2 C4 C7 0.6(8) no . . . .
C4 C2 C3 C8 -1.2(8) no . . . .
C3 C2 C6 N1 -30.0(7) no . . . .
C6 C2 C3 C8 179.3(4) no . . . .
C4 C2 C6 N1 150.5(5) no . . . .
C6 C2 C4 C7 -179.9(4) no . . . .
C2 C3 C8 C9 0.9(8) no . . . .
C2 C4 C7 C9 0.3(8) no . . . .
C4 C7 C9 Cl1 179.0(5) no . . . .
C4 C7 C9 C8 -0.7(8) no . . . .
C3 C8 C9 Cl1 -179.6(5) no . . . .
C3 C8 C9 C7 0.1(9) no . . . .
N1 C10 C11 C14 -30.0(7) no . . . .
N1 C10 C11 C16 149.6(5) no . . . .
C10 C11 C14 C12 -179.2(5) no . . . .
C10 C11 C16 C17 178.9(5) no . . . .
C14 C11 C16 C17 -1.5(9) no . . . .
C16 C11 C14 C12 1.2(9) no . . . .
C13 C12 C14 C11 -1.6(9) no . . . .
C14 C12 C13 Cl2 179.5(5) no . . . .
C14 C12 C13 C17 2.3(10) no . . . .
Cl2 C13 C17 C16 -179.7(5) no . . . .
C12 C13 C17 C16 -2.6(10) no . . . .
C11 C16 C17 C13 2.2(10) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
N1 N18 3.550(7) no . .
N1 C3 2.895(8) no . .
N1 C5 3.539(7) no . 3_767
N1 C14 2.927(7) no . .
N1 C15 2.838(7) no . .
N2 N2 2.819(6) no . 3_767
N2 N18 3.396(7) no . 3_767
N2 C2 3.081(7) no . .
N2 C6 2.735(7) no . .
N2 C10 3.398(7) no . .
N18 C1 3.479(8) no . .
C1 C1 2.720(8) no . 3_767
C1 C2 2.982(8) no . .
C1 C3 3.195(8) no . .
C1 C15 3.593(8) no . 3_767
C2 C9 2.793(9) no . .
C3 C7 2.763(9) no . .
C4 C8 2.743(9) no . .
C5 C5 2.608(7) no . 3_767
C5 C10 3.091(8) no . .
C6 C11 3.099(9) no . .
C6 C14 3.374(8) no . .
C10 C15 3.137(8) no . .
C11 C13 2.765(9) no . .
C12 C16 2.752(9) no . .
C14 C17 2.747(9) no . .
N2 N18 3.273(7) no . 1_565
N18 N2 3.273(7) no . 1_545
N18 C1 3.549(8) no . 1_545
N18 C5 3.454(8) no . 3_757
N18 C8 3.555(8) no . 3_757
N18 C17 3.325(9) no . 2_746
C1 N18 3.549(8) no . 1_565
C5 N18 3.454(8) no . 3_757
C8 N18 3.555(8) no . 3_757
C15 C15 3.595(9) no . 3_757
C17 N18 3.325(9) no . 2_756
Cl1 H7 2.7976 no . .
Cl1 H8 2.7741 no . .
Cl2 H12 2.7562 no . .
Cl2 H17 2.7465 no . .
N1 H3 2.5995 no . .
N1 H14 2.6357 no . .
N2 H6B 2.5358 no . .
N2 H10A 3.5750 no . .
N2 H10B 3.4541 no . .
N18 H10A 3.1104 no . .
N18 H14 3.2167 no . .
C1 H3 2.9465 no . .
C1 H6A 3.2231 no . .
C1 H6B 2.6438 no . .
C1 H10A 2.4732 no . .
C1 H10B 2.7958 no . .
C2 H7 3.2456 no . .
C2 H8 3.2366 no . .
C3 H4 3.2338 no . .
C3 H6A 2.9802 no . .
C3 H6B 3.2813 no . .
C3 H14 3.3554 no . .
C4 H3 3.2345 no . .
C4 H6A 2.9473 no . .
C4 H6B 2.6178 no . .
C5 H3 3.3771 no . .
C5 H10A 2.7135 no . .
C6 H3 2.6949 no . .
C6 H4 2.6708 no . .
C6 H10A 3.2980 no . .
C6 H10B 2.6578 no . .
C6 H14 3.1305 no . .
C7 H8 3.2127 no . .
C8 H7 3.2145 no . .
C9 H3 3.2265 no . .
C9 H4 3.2407 no . .
C10 H6A 2.5683 no . .
C10 H6B 2.8227 no . .
C10 H14 2.7089 no . .
C10 H16 2.6549 no . .
C11 H6A 2.6919 no . .
C11 H12 3.2536 no . .
C11 H17 3.2433 no . .
C12 H17 3.1929 no . .
C13 H14 3.2077 no . .
C13 H16 3.2098 no . .
C14 H3 3.5252 no . .
C14 H6A 2.8915 no . .
C14 H10A 2.9869 no . .
C14 H10B 3.2843 no . .
C14 H16 3.2346 no . .
C15 H3 3.3644 no . .
C15 H10A 2.6066 no . .
C15 H14 3.3926 no . .
C16 H6A 3.5744 no . .
C16 H10A 2.9328 no . .
C16 H10B 2.5886 no . .
C16 H14 3.2320 no . .
C17 H12 3.1926 no . .
H3 H6A 3.0659 no . .
H3 H6B 3.5475 no . .
H3 H8 2.2904 no . .
H3 H14 2.6804 no . .
H4 H6A 3.0126 no . .
H4 H6B 2.4494 no . .
H4 H7 2.3082 no . .
H6A H10A 3.4898 no . .
H6A H10B 2.7196 no . .
H6A H14 2.8353 no . .
H6B H10B 2.6591 no . .
H10A H14 3.0871 no . .
H10A H16 3.0068 no . .
H10B H14 3.5564 no . .
H10B H16 2.4132 no . .
H12 H14 2.3119 no . .
H16 H17 2.3191 no . .
Cl1 H6A 3.0460 no . 2_646
Cl1 H12 3.0132 no . 2_656
Cl2 H8 3.3417 no . 4_544
Cl2 H10A 3.3540 no . 2_746
Cl2 H16 3.4770 no . 1_545
N2 H3 3.1526 no . 1_565
N2 H8 3.3756 no . 1_565
N18 H3 3.4609 no . 3_757
N18 H8 3.2735 no . 3_757
N18 H10B 3.3102 no . 1_545
N18 H16 3.5850 no . 2_746
N18 H17 2.5125 no . 2_746
C2 H4 3.1356 no . 2_646
C3 H4 3.2806 no . 2_646
C3 H6B 3.4971 no . 1_545
C4 H4 3.1064 no . 2_646
C4 H8 3.1168 no . 1_565
C7 H4 3.2511 no . 2_646
C7 H6B 3.4513 no . 2_646
C7 H12 3.5364 no . 2_656
C8 H4 3.1137 no . 1_545
C8 H4 3.4184 no . 2_646
C9 H4 3.4189 no . 2_646
C9 H6A 3.2536 no . 2_646
C10 H12 3.4557 no . 1_565
C11 H12 3.4757 no . 1_565
C11 H16 3.4713 no . 2_746
C12 H7 3.0819 no . 2_646
C12 H10B 3.1274 no . 1_545
C12 H16 3.0887 no . 1_545
C13 H10A 3.2527 no . 2_746
C13 H16 3.4866 no . 1_545
C14 H7 3.2593 no . 2_646
C14 H10B 3.1773 no . 1_545
C15 H3 3.3574 no . 3_757
C15 H8 3.2092 no . 3_757
C15 H17 3.4572 no . 2_746
C16 H12 3.0821 no . 1_565
C17 H10A 3.2432 no . 2_746
C17 H10B 3.4941 no . 2_746
H3 N2 3.1526 no . 1_545
H3 N18 3.4609 no . 3_757
H3 C15 3.3574 no . 3_757
H3 H6B 2.9101 no . 1_545
H4 C2 3.1356 no . 2_656
H4 C3 3.2806 no . 2_656
H4 C4 3.1064 no . 2_656
H4 C7 3.2511 no . 2_656
H4 C8 3.1137 no . 1_565
H4 C8 3.4184 no . 2_656
H4 C9 3.4189 no . 2_656
H4 H4 3.5181 no . 2_646
H4 H4 3.5181 no . 2_656
H4 H6A 3.5538 no . 2_656
H4 H8 2.7041 no . 1_565
H6A Cl1 3.0460 no . 2_656
H6A C9 3.2536 no . 2_656
H6A H4 3.5538 no . 2_646
H6A H7 3.4683 no . 2_646
H6A H12 3.2914 no . 1_565
H6B C3 3.4971 no . 1_565
H6B C7 3.4513 no . 2_656
H6B H3 2.9101 no . 1_565
H6B H7 3.3382 no . 2_656
H6B H8 3.4562 no . 1_565
H6B H12 3.4040 no . 1_565
H6B H14 2.9608 no . 1_565
H7 C12 3.0819 no . 2_656
H7 C14 3.2593 no . 2_656
H7 H6A 3.4683 no . 2_656
H7 H6B 3.3382 no . 2_646
H7 H12 2.8213 no . 2_656
H7 H14 3.1176 no . 2_656
H8 Cl2 3.3417 no . 4_445
H8 N2 3.3756 no . 1_545
H8 N18 3.2735 no . 3_757
H8 C4 3.1168 no . 1_545
H8 C15 3.2092 no . 3_757
H8 H4 2.7041 no . 1_545
H8 H6B 3.4562 no . 1_545
H10A Cl2 3.3540 no . 2_756
H10A C13 3.2527 no . 2_756
H10A C17 3.2432 no . 2_756
H10A H16 3.4742 no . 2_746
H10A H17 3.1850 no . 2_756
H10B N18 3.3102 no . 1_565
H10B C12 3.1274 no . 1_565
H10B C14 3.1773 no . 1_565
H10B C17 3.4941 no . 2_756
H10B H12 2.7253 no . 1_565
H10B H14 2.8343 no . 1_565
H10B H17 3.4176 no . 2_756
H12 Cl1 3.0132 no . 2_646
H12 C7 3.5364 no . 2_646
H12 C10 3.4557 no . 1_545
H12 C11 3.4757 no . 1_545
H12 C16 3.0821 no . 1_545
H12 H6A 3.2914 no . 1_545
H12 H6B 3.4040 no . 1_545
H12 H7 2.8213 no . 2_646
H12 H10B 2.7253 no . 1_545
H12 H16 2.6567 no . 1_545
H14 H6B 2.9608 no . 1_545
H14 H7 3.1176 no . 2_646
H14 H10B 2.8343 no . 1_545
H16 Cl2 3.4770 no . 1_565
H16 N18 3.5850 no . 2_756
H16 C11 3.4713 no . 2_756
H16 C12 3.0887 no . 1_565
H16 C13 3.4866 no . 1_565
H16 H10A 3.4742 no . 2_756
H16 H12 2.6567 no . 1_565
H17 N18 2.5125 no . 2_756
H17 C15 3.4572 no . 2_756
H17 H10A 3.1850 no . 2_746
H17 H10B 3.4176 no . 2_746

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

#==============================================================================
# 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
#==============================================================================
####################################################################### 
# 
# 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_AI
_database_code_depnum_ccdc_archive 'CCDC 1525752'
_audit_update_record             
;
2017-01-05 deposited with the CCDC.
2017-03-08 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C34 H24 Cl4 N6'
_chemical_formula_moiety         'C34 H24 Cl4 N6'
_chemical_formula_weight         658.42
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   4.70709(16)
_cell_length_b                   26.1213(12)
_cell_length_c                   12.1528(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.267(3)
_cell_angle_gamma                90.0000
_cell_volume                     1491.82(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3660
_cell_measurement_theta_min      3.37
_cell_measurement_theta_max      74.36
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.017
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             676.00
_exptl_absorpt_coefficient_mu    3.897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.392
_exptl_absorpt_correction_T_max  0.936

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

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            8347
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_theta_max         74.625
_diffrn_reflns_theta_min         3.384
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2970
_reflns_number_gt                2405
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1793
_refine_ls_wR_factor_gt          0.1651
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2970
_refine_ls_number_parameters     199
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1250P)²+0.0928P] 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         0.40
_refine_diff_density_min         -0.43
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.33286(13) 0.75738(3) 0.29993(6) 0.0447(3) Uani 1 1 d . . . . .
Cl2 Cl 0.32808(17) 0.60507(4) 1.13734(6) 0.0585(3) Uani 1 1 d . . . . .
N1 N 0.3825(4) 0.54729(8) 0.47903(17) 0.0301(5) Uani 1 1 d . . . . .
N2 N -0.1275(5) 0.53148(9) 0.2847(2) 0.0394(5) Uani 1 1 d . . . . .
N3 N 0.6751(4) 0.58841(8) 0.60982(18) 0.0294(5) Uani 1 1 d . . . . .
C1 C 0.2904(5) 0.50614(10) 0.4238(2) 0.0296(5) Uani 1 1 d . . . . .
C2 C 0.5956(5) 0.54359(9) 0.5575(2) 0.0282(5) Uani 1 1 d . . . . .
C3 C 0.0576(5) 0.51863(9) 0.3444(2) 0.0309(5) Uani 1 1 d . . . . .
C4 C 0.5417(5) 0.63727(9) 0.5765(2) 0.0296(5) Uani 1 1 d . . . . .
H4A H 0.4976 0.6569 0.6430 0.036 Uiso 1 1 calc R U . . .
H4B H 0.3606 0.6305 0.5335 0.036 Uiso 1 1 calc R U . . .
C5 C 0.7357(5) 0.66873(9) 0.5073(2) 0.0300(5) Uani 1 1 d . . . . .
C6 C 0.7818(5) 0.65337(10) 0.4000(2) 0.0335(5) Uani 1 1 d . . . . .
H6 H 0.6861 0.6240 0.3703 0.040 Uiso 1 1 calc R U . . .
C7 C 0.9645(5) 0.68014(11) 0.3361(2) 0.0363(6) Uani 1 1 d . . . . .
H7 H 0.9949 0.6694 0.2631 0.044 Uiso 1 1 calc R U . . .
C8 C 1.1032(5) 0.72310(10) 0.3804(2) 0.0353(6) Uani 1 1 d . . . . .
C9 C 1.0628(6) 0.73929(10) 0.4864(2) 0.0351(6) Uani 1 1 d . . . . .
H9 H 1.1601 0.7685 0.5160 0.042 Uiso 1 1 calc R U . . .
C10 C 0.8756(5) 0.71179(10) 0.5492(2) 0.0326(5) Uani 1 1 d . . . . .
H10 H 0.8436 0.7228 0.6220 0.039 Uiso 1 1 calc R U . . .
C11 C 0.8852(5) 0.59285(10) 0.7035(2) 0.0312(5) Uani 1 1 d . . . . .
H11A H 1.0003 0.6241 0.6945 0.037 Uiso 1 1 calc R U . . .
H11B H 1.0152 0.5631 0.7037 0.037 Uiso 1 1 calc R U . . .
C12 C 0.7473(5) 0.59528(9) 0.8128(2) 0.0314(5) Uani 1 1 d . . . . .
C13 C 0.8006(6) 0.63628(11) 0.8840(2) 0.0383(6) Uani 1 1 d . . . . .
H13 H 0.9257 0.6627 0.8635 0.046 Uiso 1 1 calc R U . . .
C14 C 0.6748(6) 0.63934(12) 0.9841(2) 0.0438(7) Uani 1 1 d . . . . .
H14 H 0.7156 0.6672 1.0326 0.053 Uiso 1 1 calc R U . . .
C15 C 0.4891(6) 0.60118(12) 1.0123(2) 0.0417(7) Uani 1 1 d . . . . .
C16 C 0.4279(6) 0.56033(11) 0.9427(2) 0.0406(6) Uani 1 1 d . . . . .
H16 H 0.2976 0.5346 0.9626 0.049 Uiso 1 1 calc R U . . .
C17 C 0.5580(5) 0.55719(10) 0.8439(2) 0.0362(6) Uani 1 1 d . . . . .
H17 H 0.5187 0.5289 0.7964 0.043 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

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

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C8 1.745(3) . ?
Cl2 C15 1.740(3) . ?
N1 C1 1.327(3) . ?
N1 C2 1.348(3) . ?
N2 C3 1.151(3) . ?
N3 C2 1.374(3) . ?
N3 C4 1.469(3) . ?
N3 C11 1.470(3) . ?
C1 C2 1.419(3) 3_666 ?
C1 C3 1.455(3) . ?
C2 C1 1.419(3) 3_666 ?
C4 C5 1.518(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.386(4) . ?
C5 C6 1.393(4) . ?
C6 C7 1.381(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.380(4) . ?
C9 C10 1.397(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.512(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.390(4) . ?
C12 C17 1.402(4) . ?
C13 C14 1.386(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(4) . ?
C16 C17 1.381(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

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
C1 N1 C2 120.6(2) . . ?
C2 N3 C4 120.78(19) . . ?
C2 N3 C11 125.4(2) . . ?
C4 N3 C11 113.79(19) . . ?
N1 C1 C2 123.4(2) . 3_666 ?
N1 C1 C3 111.4(2) . . ?
C2 C1 C3 125.1(2) 3_666 . ?
N1 C2 N3 116.0(2) . . ?
N1 C2 C1 116.0(2) . 3_666 ?
N3 C2 C1 128.0(2) . 3_666 ?
N2 C3 C1 175.7(3) . . ?
N3 C4 C5 111.22(19) . . ?
N3 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
N3 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C10 C5 C6 118.8(2) . . ?
C10 C5 C4 121.6(2) . . ?
C6 C5 C4 119.6(2) . . ?
C7 C6 C5 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 119.0(2) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C9 C8 C7 121.4(2) . . ?
C9 C8 Cl1 119.3(2) . . ?
C7 C8 Cl1 119.3(2) . . ?
C8 C9 C10 118.5(2) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
C5 C10 C9 121.2(2) . . ?
C5 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
N3 C11 C12 112.35(19) . . ?
N3 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
N3 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C17 118.3(3) . . ?
C13 C12 C11 120.5(2) . . ?
C17 C12 C11 121.2(2) . . ?
C14 C13 C12 121.3(3) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C15 C14 C13 118.9(3) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C16 C15 C14 121.2(3) . . ?
C16 C15 Cl2 119.6(2) . . ?
C14 C15 Cl2 119.2(2) . . ?
C17 C16 C15 119.4(3) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C12 120.8(3) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?

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
C2 N1 C1 C2 0.2(4) . . . 3_666 ?
C2 N1 C1 C3 179.2(2) . . . . ?
C1 N1 C2 N3 180.0(2) . . . . ?
C1 N1 C2 C1 -0.1(4) . . . 3_666 ?
C4 N3 C2 N1 -2.9(3) . . . . ?
C11 N3 C2 N1 174.8(2) . . . . ?
C4 N3 C2 C1 177.2(2) . . . 3_666 ?
C11 N3 C2 C1 -5.0(4) . . . 3_666 ?
C2 N3 C4 C5 -102.8(2) . . . . ?
C11 N3 C4 C5 79.3(3) . . . . ?
N3 C4 C5 C10 -106.6(2) . . . . ?
N3 C4 C5 C6 71.5(3) . . . . ?
C10 C5 C6 C7 0.4(4) . . . . ?
C4 C5 C6 C7 -177.8(2) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C6 C7 C8 C9 0.2(4) . . . . ?
C6 C7 C8 Cl1 -179.62(19) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
Cl1 C8 C9 C10 179.22(18) . . . . ?
C6 C5 C10 C9 -0.8(4) . . . . ?
C4 C5 C10 C9 177.3(2) . . . . ?
C8 C9 C10 C5 0.9(4) . . . . ?
C2 N3 C11 C12 -97.8(3) . . . . ?
C4 N3 C11 C12 80.1(3) . . . . ?
N3 C11 C12 C13 -123.5(2) . . . . ?
N3 C11 C12 C17 55.0(3) . . . . ?
C17 C12 C13 C14 1.1(4) . . . . ?
C11 C12 C13 C14 179.6(2) . . . . ?
C12 C13 C14 C15 -1.2(4) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C13 C14 C15 Cl2 -179.5(2) . . . . ?
C14 C15 C16 C17 0.9(4) . . . . ?
Cl2 C15 C16 C17 -179.5(2) . . . . ?
C15 C16 C17 C12 -1.0(4) . . . . ?
C13 C12 C17 C16 0.0(4) . . . . ?
C11 C12 C17 C16 -178.5(2) . . . . ?

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

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


