# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_ynum
_database_code_depnum_ccdc_archive 'CCDC 1479193'
_audit_update_record             
;
2016-05-10 deposited with the CCDC.
2016-08-01 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C46 H36 Cl4 N6'
_chemical_formula_moiety         'C34 H24 Cl4 N6, 2(C6 H6)'
_chemical_formula_weight         814.64
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_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                   15.9806(19)
_cell_length_b                   5.8569(7)
_cell_length_c                   22.172(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 109.263(8)
_cell_angle_gamma                90.0000
_cell_volume                     1959.0(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15276
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      68.18
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             844.00
_exptl_absorpt_coefficient_mu    3.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.383
_exptl_absorpt_correction_T_max  0.857

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

_diffrn_ambient_temperature      93
_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            3490
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_theta_max         68.181
_diffrn_reflns_theta_min         2.993
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3490
_reflns_number_gt                2452
_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          0.0708
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1500
_refine_ls_wR_factor_gt          0.1399
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3490
_refine_ls_number_parameters     253
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w = 1/[σ²(Fo²)]'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.45
_refine_diff_density_min         -0.46
_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 0.26540(6) 0.95060(14) 0.11287(4) 0.0323(2) Uani 1 1 d . . . . .
Cl2 Cl 0.90432(5) -0.13925(15) 0.50870(4) 0.0336(2) Uani 1 1 d . . . . .
N1 N 0.51151(17) 0.3922(5) 0.38211(13) 0.0239(6) Uani 1 1 d . . . . .
N2 N 0.55358(17) 0.6190(4) 0.47263(13) 0.0221(6) Uani 1 1 d . . . . .
N3 N 0.62289(19) 1.0653(5) 0.57117(13) 0.0280(6) Uani 1 1 d . . . . .
C1 C 0.3169(2) 0.7619(6) 0.17488(16) 0.0255(7) Uani 1 1 d . . . . .
C2 C 0.3264(2) 0.8269(6) 0.23721(16) 0.0270(8) Uani 1 1 d . . . . .
H2 H 0.3049 0.9704 0.2456 0.032 Uiso 1 1 calc R U . . .
C3 C 0.3681(2) 0.6778(5) 0.28706(16) 0.0250(7) Uani 1 1 d . . . . .
H3 H 0.3750 0.7207 0.3298 0.030 Uiso 1 1 calc R U . . .
C4 C 0.3997(2) 0.4668(6) 0.27519(16) 0.0240(7) Uani 1 1 d . . . . .
C5 C 0.3896(2) 0.4082(6) 0.21180(16) 0.0254(7) Uani 1 1 d . . . . .
H5 H 0.4121 0.2663 0.2031 0.030 Uiso 1 1 calc R U . . .
C6 C 0.3476(2) 0.5535(6) 0.16158(16) 0.0275(7) Uani 1 1 d . . . . .
H6 H 0.3399 0.5106 0.1188 0.033 Uiso 1 1 calc R U . . .
C7 C 0.4386(2) 0.2977(6) 0.32852(15) 0.0259(7) Uani 1 1 d . . . . .
H7A H 0.3911 0.2444 0.3447 0.031 Uiso 1 1 calc R U . . .
H7B H 0.4607 0.1635 0.3112 0.031 Uiso 1 1 calc R U . . .
C8 C 0.8149(2) 0.0341(6) 0.46778(17) 0.0278(7) Uani 1 1 d . . . . .
C9 C 0.8286(2) 0.2407(6) 0.44290(17) 0.0316(8) Uani 1 1 d . . . . .
H9 H 0.8870 0.2894 0.4473 0.038 Uiso 1 1 calc R U . . .
C10 C 0.7565(2) 0.3771(6) 0.41140(17) 0.0275(7) Uani 1 1 d . . . . .
H10 H 0.7660 0.5198 0.3943 0.033 Uiso 1 1 calc R U . . .
C11 C 0.6705(2) 0.3084(5) 0.40443(15) 0.0245(7) Uani 1 1 d . . . . .
C12 C 0.6586(2) 0.0959(6) 0.42948(16) 0.0262(7) Uani 1 1 d . . . . .
H12 H 0.6002 0.0448 0.4244 0.031 Uiso 1 1 calc R U . . .
C13 C 0.7297(2) -0.0408(6) 0.46142(16) 0.0262(7) Uani 1 1 d . . . . .
H13 H 0.7207 -0.1834 0.4788 0.031 Uiso 1 1 calc R U . . .
C14 C 0.5917(2) 0.4554(6) 0.36859(16) 0.0264(7) Uani 1 1 d . . . . .
H14A H 0.6058 0.6173 0.3805 0.032 Uiso 1 1 calc R U . . .
H14B H 0.5807 0.4409 0.3221 0.032 Uiso 1 1 calc R U . . .
C15 C 0.5047(2) 0.4446(5) 0.44087(15) 0.0209(7) Uani 1 1 d . . . . .
C16 C 0.5479(2) 0.6767(5) 0.52998(15) 0.0212(7) Uani 1 1 d . . . . .
C17 C 0.5922(2) 0.8890(6) 0.55468(15) 0.0224(7) Uani 1 1 d . . . . .
C18 C 0.5190(3) -0.0297(8) 0.1554(2) 0.0465(11) Uani 1 1 d . . . . .
H18 H 0.4705 -0.1130 0.1276 0.056 Uiso 1 1 calc R U . . .
C19 C 0.5625(3) -0.1084(7) 0.2157(2) 0.0413(10) Uani 1 1 d . . . . .
H19 H 0.5437 -0.2469 0.2294 0.050 Uiso 1 1 calc R U . . .
C20 C 0.6319(3) 0.0070(8) 0.2562(2) 0.0460(11) Uani 1 1 d . . . . .
H20 H 0.6608 -0.0501 0.2980 0.055 Uiso 1 1 calc R U . . .
C21 C 0.6604(3) 0.2059(8) 0.2368(2) 0.0504(12) Uani 1 1 d . . . . .
H21 H 0.7095 0.2858 0.2651 0.061 Uiso 1 1 calc R U . . .
C22 C 0.6180(4) 0.2897(7) 0.1766(3) 0.0562(13) Uani 1 1 d . . . . .
H22 H 0.6376 0.4276 0.1631 0.067 Uiso 1 1 calc R U . . .
C23 C 0.5459(3) 0.1716(9) 0.1353(2) 0.0555(13) Uani 1 1 d . . . . .
H23 H 0.5158 0.2292 0.0937 0.067 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, 1998)'
_computing_cell_refinement       'RAPID AUTO (Rigaku, 1998)'
_computing_data_reduction        'RAPID AUTO (Rigaku, 1998)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_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 C1 1.744(3) . ?
Cl2 C8 1.744(4) . ?
N1 C15 1.377(4) . ?
N1 C14 1.456(4) . ?
N1 C7 1.471(4) . ?
N2 C15 1.337(4) . ?
N2 C16 1.347(4) . ?
N3 C17 1.150(4) . ?
C1 C6 1.383(5) . ?
C1 C2 1.392(5) . ?
C2 C3 1.393(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.403(5) . ?
C4 C7 1.510(4) . ?
C5 C6 1.386(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.377(5) . ?
C8 C13 1.392(5) . ?
C9 C10 1.386(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.401(5) . ?
C11 C14 1.516(4) . ?
C12 C13 1.379(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.410(4) 3_666 ?
C16 C15 1.410(4) 3_666 ?
C16 C17 1.446(4) . ?
C18 C19 1.366(6) . ?
C18 C23 1.379(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.355(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.370(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.374(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.395(7) . ?
C22 H22 0.9500 . ?
C23 H23 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
C15 N1 C14 119.2(3) . . ?
C15 N1 C7 124.0(3) . . ?
C14 N1 C7 116.5(3) . . ?
C15 N2 C16 118.6(3) . . ?
C6 C1 C2 121.5(3) . . ?
C6 C1 Cl1 120.0(3) . . ?
C2 C1 Cl1 118.5(3) . . ?
C1 C2 C3 118.9(3) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 118.5(3) . . ?
C3 C4 C7 121.0(3) . . ?
C5 C4 C7 120.3(3) . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C1 C6 C5 118.8(3) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
N1 C7 C4 113.4(3) . . ?
N1 C7 H7A 108.9 . . ?
C4 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
C4 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C13 121.0(3) . . ?
C9 C8 Cl2 120.6(3) . . ?
C13 C8 Cl2 118.4(3) . . ?
C8 C9 C10 119.5(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 121.0(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C12 118.1(3) . . ?
C10 C11 C14 120.9(3) . . ?
C12 C11 C14 120.9(3) . . ?
C13 C12 C11 121.5(3) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C8 118.8(3) . . ?
C12 C13 H13 120.6 . . ?
C8 C13 H13 120.6 . . ?
N1 C14 C11 112.5(3) . . ?
N1 C14 H14A 109.1 . . ?
C11 C14 H14A 109.1 . . ?
N1 C14 H14B 109.1 . . ?
C11 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
N2 C15 N1 117.0(3) . . ?
N2 C15 C16 118.5(3) . 3_666 ?
N1 C15 C16 124.5(3) . 3_666 ?
N2 C16 C15 122.8(3) . 3_666 ?
N2 C16 C17 113.4(3) . . ?
C15 C16 C17 123.4(3) 3_666 . ?
N3 C17 C16 175.4(4) . . ?
C19 C18 C23 119.5(4) . . ?
C19 C18 H18 120.3 . . ?
C23 C18 H18 120.3 . . ?
C20 C19 C18 121.4(4) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C21 120.0(4) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 120.0(4) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C23 119.7(4) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C18 C23 C22 119.4(4) . . ?
C18 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?

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
C6 C1 C2 C3 0.2(5) . . . . ?
Cl1 C1 C2 C3 -179.5(2) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
C2 C3 C4 C7 -175.3(3) . . . . ?
C3 C4 C5 C6 -1.4(5) . . . . ?
C7 C4 C5 C6 174.7(3) . . . . ?
C2 C1 C6 C5 -0.9(5) . . . . ?
Cl1 C1 C6 C5 178.9(2) . . . . ?
C4 C5 C6 C1 1.5(5) . . . . ?
C15 N1 C7 C4 107.8(4) . . . . ?
C14 N1 C7 C4 -65.4(4) . . . . ?
C3 C4 C7 N1 -55.0(4) . . . . ?
C5 C4 C7 N1 129.1(3) . . . . ?
C13 C8 C9 C10 0.4(5) . . . . ?
Cl2 C8 C9 C10 -179.0(3) . . . . ?
C8 C9 C10 C11 -0.1(5) . . . . ?
C9 C10 C11 C12 -0.7(5) . . . . ?
C9 C10 C11 C14 -178.5(3) . . . . ?
C10 C11 C12 C13 1.3(5) . . . . ?
C14 C11 C12 C13 179.1(3) . . . . ?
C11 C12 C13 C8 -1.0(5) . . . . ?
C9 C8 C13 C12 0.1(5) . . . . ?
Cl2 C8 C13 C12 179.6(3) . . . . ?
C15 N1 C14 C11 72.3(4) . . . . ?
C7 N1 C14 C11 -114.2(3) . . . . ?
C10 C11 C14 N1 -163.0(3) . . . . ?
C12 C11 C14 N1 19.3(4) . . . . ?
C16 N2 C15 N1 179.3(3) . . . . ?
C16 N2 C15 C16 -2.5(5) . . . 3_666 ?
C14 N1 C15 N2 24.6(4) . . . . ?
C7 N1 C15 N2 -148.4(3) . . . . ?
C14 N1 C15 C16 -153.6(3) . . . 3_666 ?
C7 N1 C15 C16 33.5(5) . . . 3_666 ?
C15 N2 C16 C15 2.6(5) . . . 3_666 ?
C15 N2 C16 C17 -170.4(3) . . . . ?
C23 C18 C19 C20 -0.1(6) . . . . ?
C18 C19 C20 C21 -0.7(6) . . . . ?
C19 C20 C21 C22 0.7(6) . . . . ?
C20 C21 C22 C23 0.0(7) . . . . ?
C19 C18 C23 C22 0.8(6) . . . . ?
C21 C22 C23 C18 -0.8(6) . . . . ?

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




#==============================================================================
#     End of CIF
#==============================================================================
