# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_400k
_database_code_depnum_ccdc_archive 'CCDC 1055101'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2015-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H28 Cl2 N4 Zn'
_chemical_formula_weight         580.83

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pnna

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z'
'-x+1/2, y+1/2, -z+1/2'
'x, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x-1/2, -y-1/2, z-1/2'
'-x, y-1/2, z-1/2'

_cell_length_a                   14.7556(10)
_cell_length_b                   22.5021(14)
_cell_length_c                   10.5208(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3493.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    399(2)
_cell_measurement_reflns_used    2593
_cell_measurement_theta_min      9.279
_cell_measurement_theta_max      122.014

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.104
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    2.539
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6358
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      399(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Microfocus source Incoatec'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'Omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11566
_diffrn_reflns_av_R_equivalents  0.1027
_diffrn_reflns_av_sigmaI/netI    0.0585
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.64
_diffrn_reflns_theta_max         66.11
_reflns_number_total             3008
_reflns_number_gt                1849
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 Software Suite'
_computing_cell_refinement       'Bruker APEX2 Software Suite'
_computing_data_reduction        'Bruker APEX2 Software Suite'
_computing_structure_solution    'SHELXS-1997 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker APEX2 Software Suite'
_computing_publication_material  'Bruker APEX2 Software Suite'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3008
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1278
_refine_ls_R_factor_gt           0.1020
_refine_ls_wR_factor_ref         0.3315
_refine_ls_wR_factor_gt          0.3057
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.81394(8) 0.2500 1.2500 0.0799(5) Uani 1 2 d S . .
Cl2 Cl 0.89049(14) 0.32950(9) 1.1952(2) 0.1164(8) Uani 1 1 d . . .
N1 N 0.7224(3) 0.2258(2) 1.1102(5) 0.0747(13) Uani 1 1 d . . .
C3 C 0.5959(4) 0.1914(3) 0.9311(6) 0.0846(17) Uani 1 1 d . . .
H3 H 0.5535 0.1802 0.8702 0.102 Uiso 1 1 calc R . .
C1 C 0.7059(4) 0.1687(2) 1.0877(6) 0.0739(15) Uani 1 1 d . . .
H1 H 0.7380 0.1406 1.1342 0.089 Uiso 1 1 calc R . .
C9 C 0.6123(4) -0.0400(3) 0.9444(7) 0.0806(17) Uani 1 1 d . . .
C6 C 0.6314(4) 0.0833(3) 0.9806(7) 0.0775(16) Uani 1 1 d . . .
C2 C 0.6432(4) 0.1486(3) 0.9985(6) 0.0762(15) Uani 1 1 d . . .
C8 C 0.6152(5) -0.0005(4) 0.8407(8) 0.106(2) Uani 1 1 d . . .
H8 H 0.6118 -0.0159 0.7588 0.128 Uiso 1 1 calc R . .
C5 C 0.6757(5) 0.2673(3) 1.0431(7) 0.0866(19) Uani 1 1 d . . .
H5 H 0.6872 0.3074 1.0571 0.104 Uiso 1 1 calc R . .
C10 C 0.6181(5) -0.0166(3) 1.0646(7) 0.0903(19) Uani 1 1 d . . .
H10 H 0.6156 -0.0414 1.1353 0.108 Uiso 1 1 calc R . .
C11 C 0.6281(4) 0.0468(3) 1.0803(6) 0.0832(17) Uani 1 1 d . . .
H11 H 0.6323 0.0625 1.1619 0.100 Uiso 1 1 calc R . .
C7 C 0.6230(5) 0.0608(3) 0.8566(7) 0.099(2) Uani 1 1 d . . .
H7 H 0.6226 0.0862 0.7868 0.119 Uiso 1 1 calc R . .
C4 C 0.6122(6) 0.2510(3) 0.9552(9) 0.098(2) Uani 1 1 d . . .
H4 H 0.5798 0.2799 0.9114 0.117 Uiso 1 1 calc R . .
N2 N 0.6021(4) -0.1280(2) 0.8194(6) 0.0944(17) Uani 1 1 d . . .
C12 C 0.6051(4) -0.1022(3) 0.9271(7) 0.0857(18) Uani 1 1 d . . .
H12 H 0.6025 -0.1259 0.9994 0.103 Uiso 1 1 calc R . .
C14 C 0.6832(5) -0.2148(4) 0.7517(8) 0.110(3) Uani 1 1 d . . .
H14A H 0.7366 -0.2006 0.7961 0.132 Uiso 1 1 calc R . .
H14B H 0.6845 -0.1993 0.6657 0.132 Uiso 1 1 calc R . .
C15 C 0.5168(5) -0.2154(3) 0.7520(6) 0.0870(19) Uani 1 1 d . . .
H15A H 0.5153 -0.1999 0.6660 0.104 Uiso 1 1 calc R . .
H15B H 0.4632 -0.2015 0.7962 0.104 Uiso 1 1 calc R . .
C16 C 0.5995(4) -0.1936(3) 0.8184(7) 0.0865(18) Uani 1 1 d . . .
H16 H 0.5996 -0.2083 0.9061 0.104 Uiso 1 1 calc R . .


_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
Zn1 N1 2.070(5) 4_557 ?
Zn1 N1 2.070(5) . ?
Zn1 Cl2 2.193(2) 4_557 ?
Zn1 Cl2 2.193(2) . ?
N1 C1 1.329(6) . ?
N1 C5 1.357(9) . ?
C3 C4 1.385(8) . ?
C3 C2 1.386(9) . ?
C1 C2 1.393(8) . ?
C9 C10 1.373(9) . ?
C9 C8 1.406(10) . ?
C9 C12 1.417(8) . ?
C6 C11 1.334(9) . ?
C6 C7 1.405(9) . ?
C6 C2 1.491(8) . ?
C8 C7 1.395(10) . ?
C5 C4 1.367(11) . ?
C10 C11 1.443(8) . ?
N2 C12 1.274(8) . ?
N2 C16 1.477(8) . ?
C14 C16 1.498(9) . ?
C14 C14 1.584(16) 4_546 ?
C15 C16 1.490(8) . ?
C15 C15 1.556(13) 4_546 ?

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
N1 Zn1 N1 98.5(3) 4_557 . ?
N1 Zn1 Cl2 111.35(16) 4_557 4_557 ?
N1 Zn1 Cl2 107.97(15) . 4_557 ?
N1 Zn1 Cl2 107.97(15) 4_557 . ?
N1 Zn1 Cl2 111.35(16) . . ?
Cl2 Zn1 Cl2 117.98(13) 4_557 . ?
C1 N1 C5 118.6(5) . . ?
C1 N1 Zn1 120.0(4) . . ?
C5 N1 Zn1 121.3(4) . . ?
C4 C3 C2 119.4(6) . . ?
N1 C1 C2 123.8(6) . . ?
C10 C9 C8 118.1(6) . . ?
C10 C9 C12 120.1(7) . . ?
C8 C9 C12 121.7(6) . . ?
C11 C6 C7 120.3(6) . . ?
C11 C6 C2 120.8(6) . . ?
C7 C6 C2 118.9(6) . . ?
C3 C2 C1 117.0(6) . . ?
C3 C2 C6 124.1(6) . . ?
C1 C2 C6 118.9(6) . . ?
C7 C8 C9 122.3(7) . . ?
N1 C5 C4 121.0(6) . . ?
C9 C10 C11 119.3(7) . . ?
C6 C11 C10 121.5(6) . . ?
C8 C7 C6 118.4(7) . . ?
C5 C4 C3 120.2(7) . . ?
C12 N2 C16 117.5(6) . . ?
N2 C12 C9 124.6(7) . . ?
C16 C14 C14 109.2(6) . 4_546 ?
C16 C15 C15 110.0(5) . 4_546 ?
N2 C16 C15 110.7(6) . . ?
N2 C16 C14 107.5(6) . . ?
C15 C16 C14 110.5(5) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        66.11
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         1.067
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.182
# start Validation Reply Form
_vrf_PLAT601_400k                
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of .        471 Ang3  
RESPONSE: This is expected as an avacuated channel upon heating to 400K"
;
# end Validation Reply Form

####################################################################### 
# 
# 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_1_CHCl3
_database_code_depnum_ccdc_archive 'CCDC 1055102'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2015-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H28 Cl5 N4 Zn'
_chemical_formula_weight         699.19

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'

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

_cell_length_a                   14.6608(9)
_cell_length_b                   22.7977(16)
_cell_length_c                   9.9218(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3316.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5766
_cell_measurement_theta_min      7.753
_cell_measurement_theta_max      131.666

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             1428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    4.944
_shelx_estimated_absorpt_T_min   0.349
_shelx_estimated_absorpt_T_max   0.756
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5996
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microfocus source Incoatec'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'Omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10389
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.861
_diffrn_reflns_theta_max         66.183
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.955
_reflns_number_total             2870
_reflns_number_gt                2638
_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       'Bruker APEX2 Software Suite'
_computing_cell_refinement       'Bruker APEX2 Software Suite'
_computing_data_reduction        'Bruker APEX2 Software Suite'
_computing_structure_solution    'SHELXS-1997 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker APEX2 Software Suite'
_computing_publication_material  'Bruker APEX2 Software Suite'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1383P)²+7.4385P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2870
_refine_ls_number_parameters     221
_refine_ls_number_restraints     68
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0760
_refine_ls_wR_factor_ref         0.2268
_refine_ls_wR_factor_gt          0.2231
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.219
_refine_ls_shift/su_max          0.002
_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 0.39633(8) 0.32889(5) 0.31499(12) 0.0436(4) Uani 1 1 d . . . . .
Zn2 Zn 0.31950(5) 0.2500 0.2500 0.0315(3) Uani 1 2 d S T P . .
N2 N 0.0941(3) -0.12873(17) 0.6838(4) 0.0381(9) Uani 1 1 d . . . . .
N1 N 0.2282(2) 0.22422(15) 0.3955(3) 0.0300(7) Uani 1 1 d . . . . .
C1 C 0.1798(3) 0.26420(19) 0.4653(5) 0.0321(9) Uani 1 1 d . . . . .
H1 H 0.1919 0.3047 0.4520 0.039 Uiso 1 1 calc R U . . .
C2 C 0.1129(3) 0.24770(19) 0.5559(5) 0.0356(10) Uani 1 1 d . . . . .
H11 H 0.0787 0.2766 0.6028 0.043 Uiso 1 1 calc R U . . .
C3 C 0.0961(3) 0.1888(2) 0.5779(4) 0.0333(9) Uani 1 1 d . . . . .
H2 H 0.0510 0.1769 0.6411 0.040 Uiso 1 1 calc R U . . .
C6S C 0.1459(3) 0.14673(18) 0.5066(4) 0.0298(9) Uani 1 1 d . . . . .
C6 C 0.1313(3) 0.08282(19) 0.5246(4) 0.0332(9) Uani 1 1 d . . . . .
C7 C 0.1184(4) 0.0588(2) 0.6526(5) 0.0460(12) Uani 1 1 d . . . . .
H9 H 0.1172 0.0838 0.7292 0.055 Uiso 1 1 calc R U . . .
C8 C 0.1073(4) -0.0008(2) 0.6690(5) 0.0472(12) Uani 1 1 d . . . . .
H8 H 0.0987 -0.0163 0.7569 0.057 Uiso 1 1 calc R U . . .
C9 C 0.1084(3) -0.0386(2) 0.5587(5) 0.0340(9) Uani 1 1 d . . . . .
C10 C 0.1209(3) -0.0146(2) 0.4306(5) 0.0356(10) Uani 1 1 d . . . . .
H4 H 0.1214 -0.0397 0.3541 0.043 Uiso 1 1 calc R U . . .
C11 C 0.1324(3) 0.04544(19) 0.4133(4) 0.0348(9) Uani 1 1 d . . . . .
H3 H 0.1411 0.0611 0.3255 0.042 Uiso 1 1 calc R U . . .
C12 C 0.0992(3) -0.10255(19) 0.5726(4) 0.0329(9) Uani 1 1 d . . . . .
H12 H 0.0969 -0.1254 0.4927 0.039 Uiso 1 1 calc R U . . .
C13 C 0.0918(3) -0.1926(2) 0.6798(4) 0.0334(9) Uani 1 1 d . . . . .
H13 H 0.0911 -0.2059 0.5837 0.040 Uiso 1 1 calc R U . . .
C14 C 0.0079(3) -0.2165(2) 0.7512(4) 0.0344(10) Uani 1 1 d . . . . .
H6 H -0.0477 -0.2016 0.7063 0.041 Uiso 1 1 calc R U . . .
H5 H 0.0074 -0.2026 0.8458 0.041 Uiso 1 1 calc R U . . .
C5 C 0.2110(3) 0.16675(18) 0.4162(4) 0.0300(9) Uani 1 1 d . . . . .
H10 H 0.2451 0.1387 0.3664 0.036 Uiso 1 1 calc R U . . .
C15 C 0.1768(3) -0.2167(2) 0.7491(5) 0.0394(12) Uani 1 1 d . . . . .
H15A H 0.2318 -0.2025 0.7010 0.047 Uiso 1 1 calc R U . . .
H15B H 0.1794 -0.2018 0.8427 0.047 Uiso 1 1 calc R U . . .
Cl11 Cl 0.0806(4) 0.0743(2) 0.0270(5) 0.1145(17) Uani 0.5 1 d D U P A .
Cl12 Cl 0.2686(11) 0.0861(6) -0.0965(14) 0.187(9) Uani 0.218(5) 1 d D U P A 1
Cl13 Cl 0.2500 0.0000 0.1290(16) 0.231(8) Uani 0.436(9) 2 d DS TU P A 1
Cl2X Cl 0.2795(8) 0.0753(5) 0.0613(13) 0.149(5) Uani 0.282(5) 1 d D U P A 2
Cl3X Cl 0.1751(9) -0.0381(4) 0.0485(10) 0.122(4) Uani 0.282(5) 1 d D U P A 2
C51S C 0.1858(13) 0.0376(8) -0.001(2) 0.150(8) Uani 0.5 1 d D U P . .


_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 Zn2 2.2179(12) . ?
Zn2 N1 2.054(3) 2 ?
Zn2 N1 2.054(3) . ?
Zn2 Cl1 2.2179(12) 2 ?
N2 C12 1.256(6) . ?
N2 C13 1.458(6) . ?
N1 C1 1.347(6) . ?
N1 C5 1.350(5) . ?
C1 C2 1.382(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.384(6) . ?
C2 H11 0.9500 . ?
C3 C6S 1.398(6) . ?
C3 H2 0.9500 . ?
C6S C5 1.387(6) . ?
C6S C6 1.483(6) . ?
C6 C11 1.395(7) . ?
C6 C7 1.396(6) . ?
C7 C8 1.377(7) . ?
C7 H9 0.9500 . ?
C8 C9 1.393(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.396(6) . ?
C9 C12 1.471(6) . ?
C10 C11 1.390(6) . ?
C10 H4 0.9500 . ?
C11 H3 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.520(6) . ?
C13 C15 1.525(6) . ?
C13 H13 1.0000 . ?
C14 C14 1.529(9) 2_546 ?
C14 H6 0.9900 . ?
C14 H5 0.9900 . ?
C5 H10 0.9500 . ?
C15 C15 1.520(11) 2_546 ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
Cl11 C51S 1.78(2) . ?
Cl12 C51S 1.89(2) . ?
Cl13 C51S 1.815(18) . ?
Cl13 C51S 1.815(18) 4 ?
Cl2X Cl3X 1.085(15) 4 ?
Cl2X C51S 1.74(2) . ?
Cl3X Cl2X 1.085(15) 4 ?
Cl3X C51S 1.802(17) . ?
Cl3X C51S 2.10(2) 4 ?
C51S Cl3X 2.10(2) 4 ?

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
N1 Zn2 N1 98.67(18) 2 . ?
N1 Zn2 Cl1 111.02(10) 2 2 ?
N1 Zn2 Cl1 107.65(10) . 2 ?
N1 Zn2 Cl1 107.65(10) 2 . ?
N1 Zn2 Cl1 111.02(10) . . ?
Cl1 Zn2 Cl1 118.95(7) 2 . ?
C12 N2 C13 116.9(4) . . ?
C1 N1 C5 118.7(4) . . ?
C1 N1 Zn2 120.8(3) . . ?
C5 N1 Zn2 120.4(3) . . ?
N1 C1 C2 121.6(4) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C1 C2 C3 119.6(4) . . ?
C1 C2 H11 120.2 . . ?
C3 C2 H11 120.2 . . ?
C2 C3 C6S 119.5(4) . . ?
C2 C3 H2 120.2 . . ?
C6S C3 H2 120.2 . . ?
C5 C6S C3 117.5(4) . . ?
C5 C6S C6 120.1(4) . . ?
C3 C6S C6 122.5(4) . . ?
C11 C6 C7 118.8(4) . . ?
C11 C6 C6S 120.2(4) . . ?
C7 C6 C6S 121.0(4) . . ?
C8 C7 C6 120.7(5) . . ?
C8 C7 H9 119.7 . . ?
C6 C7 H9 119.7 . . ?
C7 C8 C9 121.1(4) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C10 118.3(4) . . ?
C8 C9 C12 122.6(4) . . ?
C10 C9 C12 119.0(4) . . ?
C11 C10 C9 120.9(4) . . ?
C11 C10 H4 119.5 . . ?
C9 C10 H4 119.5 . . ?
C10 C11 C6 120.2(4) . . ?
C10 C11 H3 119.9 . . ?
C6 C11 H3 119.9 . . ?
N2 C12 C9 124.0(4) . . ?
N2 C12 H12 118.0 . . ?
C9 C12 H12 118.0 . . ?
N2 C13 C14 111.3(4) . . ?
N2 C13 C15 109.1(4) . . ?
C14 C13 C15 108.8(3) . . ?
N2 C13 H13 109.2 . . ?
C14 C13 H13 109.2 . . ?
C15 C13 H13 109.2 . . ?
C13 C14 C14 110.5(3) . 2_546 ?
C13 C14 H6 109.6 . . ?
C14 C14 H6 109.6 2_546 . ?
C13 C14 H5 109.6 . . ?
C14 C14 H5 109.6 2_546 . ?
H6 C14 H5 108.1 . . ?
N1 C5 C6S 123.1(4) . . ?
N1 C5 H10 118.4 . . ?
C6S C5 H10 118.4 . . ?
C15 C15 C13 111.4(4) 2_546 . ?
C15 C15 H15A 109.3 2_546 . ?
C13 C15 H15A 109.3 . . ?
C15 C15 H15B 109.3 2_546 . ?
C13 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C51S Cl13 C51S 89.1(17) . 4 ?
Cl3X Cl2X C51S 93.3(12) 4 . ?
Cl2X Cl3X C51S 136.6(13) 4 . ?
Cl2X Cl3X C51S 55.6(11) 4 4 ?
C51S Cl3X C51S 81.1(11) . 4 ?
Cl2X C51S Cl11 113.4(13) . . ?
Cl2X C51S Cl3X 116.4(10) . . ?
Cl11 C51S Cl3X 109.3(11) . . ?
Cl11 C51S Cl13 124.0(14) . . ?
Cl11 C51S Cl12 111.1(10) . . ?
Cl13 C51S Cl12 107.4(11) . . ?
Cl2X C51S Cl3X 31.1(5) . 4 ?
Cl11 C51S Cl3X 143.5(14) . 4 ?
Cl3X C51S Cl3X 91.5(9) . 4 ?

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
C5 N1 C1 C2 -0.6(6) . . . . ?
Zn2 N1 C1 C2 174.8(3) . . . . ?
N1 C1 C2 C3 1.3(7) . . . . ?
C1 C2 C3 C6S -1.0(7) . . . . ?
C2 C3 C6S C5 0.2(6) . . . . ?
C2 C3 C6S C6 -179.8(4) . . . . ?
C5 C6S C6 C11 -40.3(6) . . . . ?
C3 C6S C6 C11 139.7(4) . . . . ?
C5 C6S C6 C7 138.2(5) . . . . ?
C3 C6S C6 C7 -41.8(6) . . . . ?
C11 C6 C7 C8 0.3(8) . . . . ?
C6S C6 C7 C8 -178.3(5) . . . . ?
C6 C7 C8 C9 -0.1(9) . . . . ?
C7 C8 C9 C10 -0.2(8) . . . . ?
C7 C8 C9 C12 178.4(5) . . . . ?
C8 C9 C10 C11 0.4(7) . . . . ?
C12 C9 C10 C11 -178.2(4) . . . . ?
C9 C10 C11 C6 -0.3(7) . . . . ?
C7 C6 C11 C10 0.0(7) . . . . ?
C6S C6 C11 C10 178.5(4) . . . . ?
C13 N2 C12 C9 -175.7(4) . . . . ?
C8 C9 C12 N2 -3.7(7) . . . . ?
C10 C9 C12 N2 174.9(4) . . . . ?
C12 N2 C13 C14 -123.9(4) . . . . ?
C12 N2 C13 C15 116.0(4) . . . . ?
N2 C13 C14 C14 -178.7(4) . . . 2_546 ?
C15 C13 C14 C14 -58.4(5) . . . 2_546 ?
C1 N1 C5 C6S -0.3(6) . . . . ?
Zn2 N1 C5 C6S -175.7(3) . . . . ?
C3 C6S C5 N1 0.5(6) . . . . ?
C6 C6S C5 N1 -179.6(4) . . . . ?
N2 C13 C15 C15 178.6(4) . . . 2_546 ?
C14 C13 C15 C15 56.9(6) . . . 2_546 ?
Cl3X Cl2X C51S Cl11 167.9(12) 4 . . . ?
Cl3X Cl2X C51S Cl3X 39.8(17) 4 . . . ?
Cl3X Cl2X C51S Cl13 50.0(10) 4 . . . ?
Cl3X Cl2X C51S Cl12 -92.9(12) 4 . . . ?
Cl2X Cl3X C51S Cl2X -41(3) 4 . . . ?
C51S Cl3X C51S Cl2X -45.6(19) 4 . . . ?
Cl2X Cl3X C51S Cl11 -171.2(15) 4 . . . ?
C51S Cl3X C51S Cl11 -175.8(8) 4 . . . ?
Cl2X Cl3X C51S Cl13 -52.6(19) 4 . . . ?
C51S Cl3X C51S Cl13 -57.2(9) 4 . . . ?
Cl2X Cl3X C51S Cl12 20(3) 4 . . . ?
C51S Cl3X C51S Cl12 16(2) 4 . . . ?
Cl2X Cl3X C51S Cl3X -22(2) 4 . . 4 ?
C51S Cl3X C51S Cl3X -26.4(13) 4 . . 4 ?
C51S Cl13 C51S Cl2X -94.6(9) 4 . . . ?
C51S Cl13 C51S Cl11 163.4(18) 4 . . . ?
C51S Cl13 C51S Cl3X 73.9(9) 4 . . . ?
C51S Cl13 C51S Cl12 -64.8(11) 4 . . . ?
C51S Cl13 C51S Cl3X -62.4(7) 4 . . 4 ?

_refine_diff_density_max         1.124
_refine_diff_density_min         -1.361
_refine_diff_density_rms         0.135

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_1_DCM
_database_code_depnum_ccdc_archive 'CCDC 1055103'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2015-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C62 H60 Cl8 N8 Zn2'
_chemical_formula_weight         1331.52

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'

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

_cell_length_a                   14.6639(9)
_cell_length_b                   22.7525(14)
_cell_length_c                   9.8535(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3287.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5142
_cell_measurement_theta_min      9.527
_cell_measurement_theta_max      129.499

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             1368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    4.228
_shelx_estimated_absorpt_T_min   0.364
_shelx_estimated_absorpt_T_max   0.786
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5018
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microphocus source Incoatec'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'Omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32887
_diffrn_reflns_av_unetI/netI     0.0701
_diffrn_reflns_av_R_equivalents  0.1711
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.891
_diffrn_reflns_theta_max         65.999
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             2848
_reflns_number_gt                2672
_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       'Bruker APEX2 Software Suite'
_computing_cell_refinement       'Bruker APEX2 Software Suite'
_computing_data_reduction        'Bruker APEX2 Software Suite'
_computing_structure_solution    'SHELXL-1997 (Sheldrick, 1990'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker APEX2 Software Suite'
_computing_publication_material  'Bruker APEX2 Software Suite'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1179P)²+10.2727P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2848
_refine_ls_number_parameters     240
_refine_ls_number_restraints     144
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.1885
_refine_ls_wR_factor_gt          0.1842
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          1.446
_refine_ls_shift/su_mean         0.036

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
Zn1 Zn 0.67693(4) 0.2500 1.2500 0.0217(3) Uani 1 2 d S T P . .
Cl2 Cl 0.60187(6) 0.17067(4) 1.18161(9) 0.0312(3) Uani 1 1 d . . . . .
N1 N 0.76892(18) 0.27566(13) 1.1038(3) 0.0217(6) Uani 1 1 d . . . . .
C3 C 0.9020(2) 0.31083(17) 0.9218(4) 0.0244(8) Uani 1 1 d . . . . .
H3 H 0.9474 0.3225 0.8585 0.029 Uiso 1 1 calc R U . . .
C5 C 0.7865(2) 0.33306(15) 1.0838(4) 0.0211(7) Uani 1 1 d . . . . .
H5 H 0.7524 0.3612 1.1337 0.025 Uiso 1 1 calc R U . . .
C1 C 0.8174(2) 0.23567(16) 1.0344(4) 0.0237(7) Uani 1 1 d . . . . .
H1 H 0.8052 0.1951 1.0480 0.028 Uiso 1 1 calc R U . . .
C4 C 0.8529(2) 0.35316(15) 0.9929(3) 0.0212(7) Uani 1 1 d . . . . .
C2 C 0.8848(3) 0.25200(16) 0.9434(4) 0.0254(8) Uani 1 1 d . . . . .
H2 H 0.9188 0.2229 0.8962 0.030 Uiso 1 1 calc R U . . .
C12 C 0.9021(2) 0.60247(16) 0.9308(4) 0.0240(8) Uani 1 1 d . . . . .
H12 H 0.9043 0.6255 1.0112 0.029 Uiso 1 1 calc R U . . .
C9 C 0.8919(2) 0.53814(16) 0.9447(4) 0.0245(8) Uani 1 1 d . . . . .
C8 C 0.8922(3) 0.5013(2) 0.8335(4) 0.0415(11) Uani 1 1 d . . . . .
H8 H 0.9002 0.5175 0.7454 0.050 Uiso 1 1 calc R U . . .
C6 C 0.8676(2) 0.41701(16) 0.9765(4) 0.0227(7) Uani 1 1 d . . . . .
C10 C 0.8795(3) 0.51442(16) 1.0725(4) 0.0278(8) Uani 1 1 d . . . . .
H10 H 0.8797 0.5394 1.1498 0.033 Uiso 1 1 calc R U . . .
C11 C 0.8668(3) 0.45418(16) 1.0887(4) 0.0269(8) Uani 1 1 d . . . . .
H11 H 0.8575 0.4384 1.1769 0.032 Uiso 1 1 calc R U . . .
C7 C 0.8809(3) 0.44121(19) 0.8484(4) 0.0381(10) Uani 1 1 d . . . . .
H7 H 0.8824 0.4164 0.7708 0.046 Uiso 1 1 calc R U . . .
N2 N 0.9082(2) 0.62862(14) 0.8182(3) 0.0272(7) Uani 1 1 d . . . . .
C15 C 0.8258(2) 0.71635(19) 0.7508(4) 0.0287(9) Uani 1 1 d . . . . .
H15A H 0.7705 0.7020 0.7981 0.034 Uiso 1 1 calc R U . . .
H15B H 0.8241 0.7014 0.6564 0.034 Uiso 1 1 calc R U . . .
C16 C 0.9950(2) 0.71639(16) 0.7493(3) 0.0235(8) Uani 1 1 d . . . . .
H16A H 0.9955 0.7022 0.6543 0.028 Uiso 1 1 calc R U . . .
H16B H 1.0506 0.7016 0.7948 0.028 Uiso 1 1 calc R U . . .
C14 C 0.9105(2) 0.69285(16) 0.8222(4) 0.0239(8) Uani 1 1 d . . . . .
H14 H 0.9108 0.7064 0.9188 0.029 Uiso 1 1 calc R U . . .
Cl2S Cl 0.9171(5) 0.0738(3) 0.0208(5) 0.0474(14) Uani 0.2031(16) 1 d D U P A 1
Cl1S Cl 0.7139(15) 0.0537(10) 0.038(3) 0.170(9) Uani 0.2031(16) 1 d D U P A 1
C1S C 0.8276(13) 0.0232(11) 0.036(3) 0.081(5) Uani 0.2031(16) 1 d D U P A 1
H1SA H 0.8365 0.0007 0.1209 0.097 Uiso 0.2031(16) 1 calc R U P A 1
H1SB H 0.8318 -0.0050 -0.0403 0.097 Uiso 0.2031(16) 1 calc R U P A 1
Cl2T Cl 0.8490(14) 0.0797(6) 0.0257(9) 0.124(6) Uani 0.1839(15) 1 d D U P B 2
Cl1T Cl 1.0125(15) 0.0245(9) -0.0183(14) 0.175(8) Uani 0.1839(15) 1 d D U P B 2
C1T C 0.895(2) 0.0099(11) 0.035(3) 0.081(5) Uani 0.1839(15) 1 d D U P B 2
H1TA H 0.8635 -0.0176 -0.0270 0.097 Uiso 0.1839(15) 1 calc R U P B 2
H1TB H 0.8922 -0.0058 0.1290 0.097 Uiso 0.1839(15) 1 calc R U P B 2
Cl2Q Cl 0.8348(7) -0.0374(4) 0.0499(9) 0.032(2) Uani 0.1130(15) 1 d D U P C 3
Cl1Q Cl 0.7276(6) 0.0726(4) 0.0642(9) 0.0239(18) Uani 0.1130(15) 1 d D U P C 3
C1Q C 0.822(3) 0.0334(15) -0.012(4) 0.081(5) Uani 0.1130(15) 1 d D U P C 3
H1Q1 H 0.8119 0.0315 -0.1113 0.097 Uiso 0.1130(15) 1 calc R U P C 3
H1Q2 H 0.8785 0.0556 0.0044 0.097 Uiso 0.1130(15) 1 calc R U P C 3


_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
Zn1 N1 2.058(3) 4_557 ?
Zn1 N1 2.058(3) . ?
Zn1 Cl2 2.2188(9) . ?
Zn1 Cl2 2.2189(9) 4_557 ?
N1 C5 1.346(5) . ?
N1 C1 1.343(5) . ?
C3 C2 1.379(5) . ?
C3 C4 1.392(5) . ?
C5 C4 1.400(5) . ?
C1 C2 1.384(5) . ?
C4 C6 1.477(5) . ?
C12 N2 1.262(5) . ?
C12 C9 1.478(5) . ?
C9 C8 1.379(6) . ?
C9 C10 1.382(6) . ?
C8 C7 1.386(6) . ?
C6 C11 1.392(5) . ?
C6 C7 1.391(6) . ?
C10 C11 1.392(5) . ?
N2 C14 1.462(5) . ?
C15 C14 1.525(5) . ?
C15 C15 1.531(9) 4_566 ?
C16 C14 1.530(5) . ?
C16 C16 1.530(7) 4_566 ?
Cl2S C1S 1.753(17) . ?
Cl1S C1S 1.805(16) . ?
Cl1S C1S 1.85(3) 2_655 ?
Cl2T C1T 1.73(2) . ?
Cl1T Cl1T 1.23(4) 5_755 ?
Cl1T C1T 1.58(4) 5_755 ?
Cl1T C1T 1.84(2) . ?
Cl2Q Cl1Q 1.225(16) 2_655 ?
Cl2Q C1Q 1.73(2) . ?
Cl1Q Cl2Q 1.225(16) 2_655 ?
Cl1Q C1Q 1.81(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
N1 Zn1 N1 98.08(15) 4_557 . ?
N1 Zn1 Cl2 107.88(9) 4_557 . ?
N1 Zn1 Cl2 110.09(9) . . ?
N1 Zn1 Cl2 110.08(9) 4_557 4_557 ?
N1 Zn1 Cl2 107.88(9) . 4_557 ?
Cl2 Zn1 Cl2 120.52(6) . 4_557 ?
C5 N1 C1 118.8(3) . . ?
C5 N1 Zn1 120.2(2) . . ?
C1 N1 Zn1 120.8(2) . . ?
C2 C3 C4 119.9(3) . . ?
N1 C5 C4 123.0(3) . . ?
N1 C1 C2 121.8(3) . . ?
C3 C4 C5 117.1(3) . . ?
C3 C4 C6 123.4(3) . . ?
C5 C4 C6 119.5(3) . . ?
C1 C2 C3 119.4(3) . . ?
N2 C12 C9 123.7(3) . . ?
C8 C9 C10 119.2(4) . . ?
C8 C9 C12 121.8(3) . . ?
C10 C9 C12 119.0(3) . . ?
C7 C8 C9 121.0(4) . . ?
C11 C6 C7 118.8(3) . . ?
C11 C6 C4 120.6(3) . . ?
C7 C6 C4 120.6(3) . . ?
C9 C10 C11 120.4(4) . . ?
C6 C11 C10 120.4(3) . . ?
C8 C7 C6 120.2(4) . . ?
C12 N2 C14 116.7(3) . . ?
C14 C15 C15 110.8(3) . 4_566 ?
C14 C16 C16 110.2(3) . 4_566 ?
N2 C14 C15 108.6(3) . . ?
N2 C14 C16 110.8(3) . . ?
C15 C14 C16 108.7(3) . . ?
C1S Cl1S C1S 86.6(13) . 2_655 ?
Cl2S C1S Cl1S 116.1(17) . . ?
Cl1T Cl1T C1T 80.7(18) 5_755 5_755 ?
Cl1T Cl1T C1T 58.0(19) 5_755 . ?
C1T Cl1T C1T 138.7(16) 5_755 . ?
Cl2T C1T Cl1T 100.5(16) . . ?
Cl1Q Cl2Q C1Q 124.4(19) 2_655 . ?
Cl2Q Cl1Q C1Q 101.5(19) 2_655 . ?
Cl2Q C1Q Cl1Q 113.5(18) . . ?

_refine_diff_density_max         0.840
_refine_diff_density_min         -1.449
_refine_diff_density_rms         0.154

_shelxl_version_number           2014-3



# start Validation Reply Form
_vrf_SHFSU01_1_DCM               
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.20
RESPONSE: This is due to the disordered guest.
;
_vrf_PLAT080_1_DCM               
;
PROBLEM: Maximum Shift/Error ............................       1.45 Why ? 
RESPONSE: This is due to the disordered guest.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_1_dce
_database_code_depnum_ccdc_archive 'CCDC 1055104'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2015-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H28 Cl4 N4 Zn'
_chemical_formula_weight         675.75

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'

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

_cell_length_a                   14.7255(9)
_cell_length_b                   22.4827(15)
_cell_length_c                   10.2852(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3405.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4396
_cell_measurement_theta_min      9.456
_cell_measurement_theta_max      129.546

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             1384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    4.092
_shelx_estimated_absorpt_T_min   0.410
_shelx_estimated_absorpt_T_max   0.791
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5772
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microfocus source Incoatec'
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11111
_diffrn_reflns_av_unetI/netI     0.0879
_diffrn_reflns_av_R_equivalents  0.1844
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.728
_diffrn_reflns_theta_max         65.608
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.919
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.919
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.919
_reflns_number_total             2844
_reflns_number_gt                2288
_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       'Bruker APEX2 Software Suite'
_computing_cell_refinement       'Bruker APEX2 Software Suite'
_computing_data_reduction        'Bruker APEX2 Software Suite'
_computing_structure_solution    'SHELXS-1997 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker APEX2 Software Suite'
_computing_publication_material  'Bruker APEX2 Software Suite'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1540P)²+0.9490P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2844
_refine_ls_number_parameters     225
_refine_ls_number_restraints     70
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0765
_refine_ls_wR_factor_ref         0.2187
_refine_ls_wR_factor_gt          0.2036
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.18045(4) 0.2500 1.2500 0.0526(3) Uani 1 2 d S T P . .
Cl2 Cl 0.10575(7) 0.33080(5) 1.19130(14) 0.0765(4) Uani 1 1 d . . . . .
N1 N 0.27250(18) 0.22654(13) 1.1065(3) 0.0508(8) Uani 1 1 d . . . . .
C6 C 0.3686(2) 0.08517(17) 0.9773(4) 0.0520(9) Uani 1 1 d . . . . .
C5 C 0.2902(2) 0.16923(15) 1.0850(4) 0.0487(8) Uani 1 1 d . . . . .
H5 H 0.2573 0.1403 1.1330 0.058 Uiso 1 1 calc R U . . .
C3 C 0.4027(2) 0.19292(19) 0.9281(4) 0.0577(10) Uani 1 1 d . . . . .
H3 H 0.4475 0.1818 0.8663 0.069 Uiso 1 1 calc R U . . .
C1 C 0.3197(2) 0.26740(19) 1.0401(5) 0.0580(10) Uani 1 1 d . . . . .
H1 H 0.3074 0.3083 1.0552 0.070 Uiso 1 1 calc R U . . .
C9 C 0.3895(2) -0.03763(17) 0.9427(4) 0.0550(10) Uani 1 1 d . . . . .
C8 C 0.3809(3) -0.01423(18) 1.0650(4) 0.0569(10) Uani 1 1 d . . . . .
H8 H 0.3823 -0.0398 1.1386 0.068 Uiso 1 1 calc R U . . .
C4 C 0.3550(2) 0.14959(16) 0.9950(4) 0.0490(9) Uani 1 1 d . . . . .
C7 C 0.3702(3) 0.04708(17) 1.0822(4) 0.0571(10) Uani 1 1 d . . . . .
H7 H 0.3639 0.0627 1.1675 0.069 Uiso 1 1 calc R U . . .
C11 C 0.3782(3) 0.0617(2) 0.8530(5) 0.0690(11) Uani 1 1 d . . . . .
H11 H 0.3786 0.0874 0.7796 0.083 Uiso 1 1 calc R U . . .
C10 C 0.3874(4) 0.0002(2) 0.8361(5) 0.0741(13) Uani 1 1 d . . . . .
H10 H 0.3923 -0.0158 0.7509 0.089 Uiso 1 1 calc R U . . .
C2 C 0.3851(3) 0.25226(18) 0.9510(5) 0.0606(10) Uani 1 1 d . . . . .
H2 H 0.4178 0.2822 0.9058 0.073 Uiso 1 1 calc R U . . .
C12 C 0.3980(2) -0.10228(18) 0.9274(5) 0.0577(10) Uani 1 1 d . . . . .
H12 H 0.4005 -0.1261 1.0036 0.069 Uiso 1 1 calc R U . . .
N2 N 0.4021(2) -0.12783(16) 0.8186(4) 0.0639(10) Uani 1 1 d . . . . .
C13 C 0.4046(3) -0.19287(19) 0.8195(5) 0.0605(11) Uani 1 1 d . . . . .
H13 H 0.4047 -0.2074 0.9114 0.073 Uiso 1 1 calc R U . . .
C14 C 0.4887(2) -0.2161(2) 0.7500(4) 0.0593(11) Uani 1 1 d . . . . .
H14A H 0.5439 -0.2012 0.7943 0.071 Uiso 1 1 calc R U . . .
H14B H 0.4895 -0.2013 0.6593 0.071 Uiso 1 1 calc R U . . .
C15 C 0.3206(3) -0.2156(2) 0.7508(5) 0.0756(17) Uani 1 1 d . . . . .
H15A H 0.3193 -0.2004 0.6606 0.091 Uiso 1 1 calc R U . . .
H15B H 0.2656 -0.2011 0.7963 0.091 Uiso 1 1 calc R U . . .
C3S C 0.7469(14) 0.5332(5) 0.983(5) 0.318(14) Uani 0.398(5) 1 d D U P A 1
Cl3 Cl 0.6277(5) 0.5633(2) 0.9728(5) 0.248(3) Uani 0.795(9) 1 d D U P A 1
C3T C 0.732(2) 0.5320(8) 0.910(4) 0.313(14) Uani 0.398(5) 1 d D U P A 1
C4S C 0.7269(17) 0.4703(8) 1.013(15) 0.326(16) Uani 0.102(5) 1 d D U P A 2
Cl4 Cl 0.613(3) 0.4745(15) 0.956(3) 0.340(16) Uani 0.205(9) 1 d D U P A 2
C4T C 0.703(7) 0.488(12) 0.844(8) 0.328(16) Uani 0.102(5) 1 d D U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N1 2.072(3) 4_557 ?
Zn1 N1 2.072(3) . ?
Zn1 Cl2 2.2079(12) . ?
Zn1 Cl2 2.2079(12) 4_557 ?
N1 C5 1.333(5) . ?
N1 C1 1.339(5) . ?
C6 C7 1.378(6) . ?
C6 C11 1.390(6) . ?
C6 C4 1.473(5) . ?
C5 C4 1.400(5) . ?
C3 C2 1.379(6) . ?
C3 C4 1.384(6) . ?
C1 C2 1.372(6) . ?
C9 C8 1.369(6) . ?
C9 C10 1.388(7) . ?
C9 C12 1.467(5) . ?
C8 C7 1.399(6) . ?
C11 C10 1.400(7) . ?
C12 N2 1.259(5) . ?
N2 C13 1.463(6) . ?
C13 C15 1.514(6) . ?
C13 C14 1.522(5) . ?
C14 C14 1.526(9) 4_546 ?
C15 C15 1.545(11) 4_546 ?
C3S C3T 0.78(6) . ?
C3S C3S 1.49(2) 2_665 ?
C3S C3T 1.67(3) 2_665 ?
C3S Cl3 1.885(18) . ?
Cl3 C3T 1.81(2) . ?
C3T C3T 1.53(2) 2_665 ?
C3T C3S 1.67(3) 2_665 ?
C4S C4S 1.50(2) 2_665 ?
C4S C4T 1.8(2) . ?
C4S Cl4 1.78(2) . ?
Cl4 C4T 1.78(2) . ?
C4T C4T 1.49(2) 2_665 ?

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
N1 Zn1 N1 98.29(16) 4_557 . ?
N1 Zn1 Cl2 108.13(9) 4_557 . ?
N1 Zn1 Cl2 109.91(10) . . ?
N1 Zn1 Cl2 109.91(10) 4_557 4_557 ?
N1 Zn1 Cl2 108.13(9) . 4_557 ?
Cl2 Zn1 Cl2 120.24(7) . 4_557 ?
C5 N1 C1 118.5(3) . . ?
C5 N1 Zn1 119.5(3) . . ?
C1 N1 Zn1 121.9(3) . . ?
C7 C6 C11 118.8(4) . . ?
C7 C6 C4 121.1(4) . . ?
C11 C6 C4 120.0(4) . . ?
N1 C5 C4 123.2(4) . . ?
C2 C3 C4 120.0(4) . . ?
N1 C1 C2 122.3(4) . . ?
C8 C9 C10 119.2(4) . . ?
C8 C9 C12 119.1(4) . . ?
C10 C9 C12 121.6(4) . . ?
C9 C8 C7 120.3(4) . . ?
C3 C4 C5 116.9(3) . . ?
C3 C4 C6 124.2(3) . . ?
C5 C4 C6 119.0(3) . . ?
C6 C7 C8 121.1(4) . . ?
C6 C11 C10 119.9(5) . . ?
C9 C10 C11 120.6(4) . . ?
C1 C2 C3 119.1(4) . . ?
N2 C12 C9 123.4(5) . . ?
C12 N2 C13 116.9(4) . . ?
N2 C13 C15 108.3(4) . . ?
N2 C13 C14 111.1(4) . . ?
C15 C13 C14 109.3(3) . . ?
C13 C14 C14 110.0(3) . 4_546 ?
C13 C15 C15 110.1(4) . 4_546 ?
C3T C3S C3S 89.1(15) . 2_665 ?
C3T C3S C3T 66(2) . 2_665 ?
C3S C3S C3T 28(2) 2_665 2_665 ?
C3T C3S Cl3 73(2) . . ?
C3S C3S Cl3 114.5(19) 2_665 . ?
C3T C3S Cl3 117(2) 2_665 . ?
C3T Cl3 C3S 24(2) . . ?
C3S C3T C3T 86.4(11) . 2_665 ?
C3S C3T C3S 63(2) . 2_665 ?
C3T C3T C3S 28(2) 2_665 2_665 ?
C3S C3T Cl3 83(2) . . ?
C3T C3T Cl3 131(3) 2_665 . ?
C3S C3T Cl3 109.7(19) 2_665 . ?
C4S C4S C4T 84(6) 2_665 . ?
C4S C4S Cl4 112(2) 2_665 . ?
C4T C4S Cl4 59(4) . . ?
C4S Cl4 C4T 61(8) . . ?
C4T C4T C4S 84(6) 2_665 . ?
C4T C4T Cl4 139(5) 2_665 . ?
C4S C4T Cl4 59(4) . . ?

_refine_diff_density_max         0.944
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.119

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_jm13_100k_0m
_database_code_depnum_ccdc_archive 'CCDC 1055113'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2015-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H28 N4'
_chemical_formula_weight         444.56

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.5990(4)
_cell_length_b                   7.1074(5)
_cell_length_c                   16.1003(11)
_cell_angle_alpha                92.646(4)
_cell_angle_beta                 98.583(4)
_cell_angle_gamma                112.049(3)
_cell_volume                     583.53(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4403
_cell_measurement_theta_min      13.526
_cell_measurement_theta_max      131.686

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             236
_exptl_absorpt_coefficient_mu    0.584
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5184
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Microfocus source incoatec'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'Omega and phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6525
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         66.17
_reflns_number_total             1997
_reflns_number_gt                1805
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2 Software Suite'
_computing_cell_refinement       'Bruker APEX2 Software Suite'
_computing_data_reduction        'Bruker APEX2 Software Suite'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker APEX2 Software Suite'
_computing_publication_material  'Bruker APEX2 Software Suite'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0700P)²+0.1458P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1997
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1299
_refine_ls_wR_factor_gt          0.1156
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_restrained_S_all      1.173
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1297(2) -0.20748(17) 0.88297(7) 0.0214(3) Uani 1 1 d . . .
N2 N 0.3904(2) 0.72218(17) 0.53701(7) 0.0192(3) Uani 1 1 d . . .
C1 C 0.6445(3) 0.8438(2) 0.54402(9) 0.0191(3) Uani 1 1 d . . .
H1 H 0.6890 0.9570 0.5119 0.023 Uiso 1 1 calc R . .
C2 C 0.8444(3) 0.8135(2) 0.59530(9) 0.0185(3) Uani 1 1 d . . .
H2 H 1.0217 0.9034 0.5982 0.022 Uiso 1 1 calc R . .
C3 C 0.7811(3) 0.64890(19) 0.64250(8) 0.0168(3) Uani 1 1 d . . .
H3 H 0.9151 0.6246 0.6783 0.020 Uiso 1 1 calc R . .
C4 C 0.5195(3) 0.51946(19) 0.63704(8) 0.0157(3) Uani 1 1 d . . .
C5 C 0.4485(3) 0.33986(19) 0.68555(8) 0.0158(3) Uani 1 1 d . . .
C6 C 0.5783(3) 0.20671(19) 0.68151(8) 0.0170(3) Uani 1 1 d . . .
H4 H 0.7030 0.2276 0.6452 0.020 Uiso 1 1 calc R . .
C7 C 0.5265(3) 0.04398(19) 0.73009(9) 0.0175(3) Uani 1 1 d . . .
H12 H 0.6164 -0.0452 0.7267 0.021 Uiso 1 1 calc R . .
C8 C 0.3443(3) 0.01028(19) 0.78357(8) 0.0174(3) Uani 1 1 d . . .
C9 C 0.3004(3) -0.1603(2) 0.83581(9) 0.0194(3) Uani 1 1 d . . .
H13 H 0.4052 -0.2386 0.8340 0.023 Uiso 1 1 calc R . .
C10 C 0.1104(3) -0.3779(2) 0.93281(9) 0.0220(4) Uani 1 1 d . . .
H5 H 0.2207 -0.4486 0.9140 0.026 Uiso 1 1 calc R . .
C11 C -0.1737(3) -0.5284(2) 0.91905(10) 0.0301(4) Uani 1 1 d . . .
H14 H -0.2315 -0.5853 0.8588 0.036 Uiso 1 1 calc R . .
H6 H -0.2854 -0.4555 0.9325 0.036 Uiso 1 1 calc R . .
C12 C 0.2093(3) -0.2967(2) 1.02584(9) 0.0295(4) Uani 1 1 d . . .
H8 H 0.1121 -0.2149 1.0432 0.035 Uiso 1 1 calc R . .
H7 H 0.3971 -0.2062 1.0343 0.035 Uiso 1 1 calc R . .
C13 C 0.3318(3) 0.56380(19) 0.58299(8) 0.0161(3) Uani 1 1 d . . .
H9 H 0.1527 0.4766 0.5787 0.019 Uiso 1 1 calc R . .
C14 C 0.2605(3) 0.3023(2) 0.73784(9) 0.0175(3) Uani 1 1 d . . .
H11 H 0.1665 0.3888 0.7399 0.021 Uiso 1 1 calc R . .
C15 C 0.2097(3) 0.1412(2) 0.78659(9) 0.0183(3) Uani 1 1 d . . .
H10 H 0.0832 0.1191 0.8223 0.022 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C9 1.2658(19) . ?
N1 C10 1.4628(17) . ?
N2 C13 1.3398(16) . ?
N2 C1 1.3433(18) . ?
C1 C2 1.380(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.3864(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3935(19) . ?
C3 H3 0.9500 . ?
C4 C13 1.4011(19) . ?
C4 C5 1.4836(17) . ?
C5 C6 1.3974(19) . ?
C5 C14 1.401(2) . ?
C6 C7 1.3903(18) . ?
C6 H4 0.9500 . ?
C7 C8 1.392(2) . ?
C7 H12 0.9500 . ?
C8 C15 1.403(2) . ?
C8 C9 1.4733(18) . ?
C9 H13 0.9500 . ?
C10 C12 1.522(2) . ?
C10 C11 1.523(2) . ?
C10 H5 1.0000 . ?
C11 C12 1.5298(19) 2_547 ?
C11 H14 0.9900 . ?
C11 H6 0.9900 . ?
C12 C11 1.5297(19) 2_547 ?
C12 H8 0.9900 . ?
C12 H7 0.9900 . ?
C13 H9 0.9500 . ?
C14 C15 1.3831(18) . ?
C14 H11 0.9500 . ?
C15 H10 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
C9 N1 C10 117.40(12) . . ?
C13 N2 C1 117.25(12) . . ?
N2 C1 C2 123.59(12) . . ?
N2 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C1 C2 C3 118.57(12) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 119.52(12) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C13 117.35(12) . . ?
C3 C4 C5 120.29(12) . . ?
C13 C4 C5 122.34(12) . . ?
C6 C5 C14 118.49(12) . . ?
C6 C5 C4 119.36(12) . . ?
C14 C5 C4 122.11(12) . . ?
C7 C6 C5 120.57(13) . . ?
C7 C6 H4 119.7 . . ?
C5 C6 H4 119.7 . . ?
C6 C7 C8 120.72(13) . . ?
C6 C7 H12 119.6 . . ?
C8 C7 H12 119.6 . . ?
C7 C8 C15 118.89(13) . . ?
C7 C8 C9 119.05(13) . . ?
C15 C8 C9 122.05(13) . . ?
N1 C9 C8 123.05(13) . . ?
N1 C9 H13 118.5 . . ?
C8 C9 H13 118.5 . . ?
N1 C10 C12 109.37(11) . . ?
N1 C10 C11 109.34(12) . . ?
C12 C10 C11 110.43(13) . . ?
N1 C10 H5 109.2 . . ?
C12 C10 H5 109.2 . . ?
C11 C10 H5 109.2 . . ?
C10 C11 C12 111.74(13) . 2_547 ?
C10 C11 H14 109.3 . . ?
C12 C11 H14 109.3 2_547 . ?
C10 C11 H6 109.3 . . ?
C12 C11 H6 109.3 2_547 . ?
H14 C11 H6 107.9 . . ?
C10 C12 C11 111.06(12) . 2_547 ?
C10 C12 H8 109.4 . . ?
C11 C12 H8 109.4 2_547 . ?
C10 C12 H7 109.4 . . ?
C11 C12 H7 109.4 2_547 . ?
H8 C12 H7 108.0 . . ?
N2 C13 C4 123.71(12) . . ?
N2 C13 H9 118.1 . . ?
C4 C13 H9 118.1 . . ?
C15 C14 C5 121.00(12) . . ?
C15 C14 H11 119.5 . . ?
C5 C14 H11 119.5 . . ?
C14 C15 C8 120.28(13) . . ?
C14 C15 H10 119.9 . . ?
C8 C15 H10 119.9 . . ?

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
C13 N2 C1 C2 0.17(19) . . . . ?
N2 C1 C2 C3 -0.1(2) . . . . ?
C1 C2 C3 C4 -0.02(19) . . . . ?
C2 C3 C4 C13 0.09(19) . . . . ?
C2 C3 C4 C5 178.59(11) . . . . ?
C3 C4 C5 C6 -49.58(18) . . . . ?
C13 C4 C5 C6 128.86(14) . . . . ?
C3 C4 C5 C14 128.28(14) . . . . ?
C13 C4 C5 C14 -53.29(18) . . . . ?
C14 C5 C6 C7 -1.68(19) . . . . ?
C4 C5 C6 C7 176.26(11) . . . . ?
C5 C6 C7 C8 0.1(2) . . . . ?
C6 C7 C8 C15 1.14(19) . . . . ?
C6 C7 C8 C9 -178.28(11) . . . . ?
C10 N1 C9 C8 -178.80(11) . . . . ?
C7 C8 C9 N1 -176.50(12) . . . . ?
C15 C8 C9 N1 4.1(2) . . . . ?
C9 N1 C10 C12 109.99(15) . . . . ?
C9 N1 C10 C11 -128.98(14) . . . . ?
N1 C10 C11 C12 -176.24(12) . . . 2_547 ?
C12 C10 C11 C12 -55.8(2) . . . 2_547 ?
N1 C10 C12 C11 175.83(12) . . . 2_547 ?
C11 C10 C12 C11 55.5(2) . . . 2_547 ?
C1 N2 C13 C4 -0.10(19) . . . . ?
C3 C4 C13 N2 0.0(2) . . . . ?
C5 C4 C13 N2 -178.51(11) . . . . ?
C6 C5 C14 C15 2.05(19) . . . . ?
C4 C5 C14 C15 -175.82(11) . . . . ?
C5 C14 C15 C8 -0.8(2) . . . . ?
C7 C8 C15 C14 -0.78(19) . . . . ?
C9 C8 C15 C14 178.62(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        66.17
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.058
