#------------------------------------------------------------------------------
#$Date: 2016-06-02 09:36:27 +0200 (jue 02 de jun de 2016) $
#$Revision: 183259 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/90/7119013.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7119013
loop_
_publ_author_name
'Helena Isla'
'Monika Srebro-Hooper'
'Marion Jean'
'Nicolas Vanthuyne'
'Thierry Roisnel'
'Jamie L. Lunkley'
'Gilles Muller'
'J. A. Gareth Williams'
'Jochen Autschbach'
'Jeanne Crassous'
_publ_section_title
;
 Conformational changes and chiroptical switching of enantiopure
 bis-helicenic terpyridine upon Zn²⁺ binding
;
_journal_name_full               Chem.Commun.
_journal_page_first              5932
_journal_volume                  52
_journal_year                    2016
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C59 H37 N3 O4 Zn, 2(C H2 Cl2)'
_chemical_formula_sum            'C61 H41 Cl4 N3 O4 Zn'
_chemical_formula_weight         1087.14
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2016-01-21 deposited with the CCDC.
2016-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.356(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3452(6)
_cell_length_b                   16.8828(7)
_cell_length_c                   18.9071(7)
_cell_measurement_reflns_used    9782
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.47
_cell_measurement_wavelength     0.71073
_cell_volume                     4884.1(3)
_computing_cell_refinement       'APEX2 (Bruker, 2014); SAINT (Bruker, 2014)'
_computing_data_collection
'SAINT (Bruker, 2014); XPREP (Sheldrick, 2014)'
_computing_data_reduction
'SAINT (Bruker, 2014); XPREP (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'CRYSCALc (T. Roisnel, local program, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            58468
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_min         2.923
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_T_max  0.876
_exptl_absorpt_correction_T_min  0.728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_description       prism
_exptl_crystal_F_000             2232
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.170
_refine_diff_density_max         1.599
_refine_diff_density_min         -1.371
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     660
_refine_ls_number_reflns         11188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0591P)²+10.9478P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1431
_reflns_number_gt                8884
_reflns_number_total             11188
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc01748g2.cif
_cod_data_source_block           HI103ZN
_cod_database_code               7119013
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.34011(2) 0.14616(2) 0.01555(2) 0.01835(9) Uani 1 1 d . . .
C1 C 0.39272(18) -0.12257(16) 0.08942(14) 0.0219(5) Uani 1 1 d . . .
H1 H 0.4000 -0.1763 0.1037 0.026 Uiso 1 1 calc R U .
N2 N 0.37322(13) 0.03321(12) 0.04840(11) 0.0170(4) Uani 1 1 d . . .
O3 O 0.22008(13) 0.17924(12) -0.01420(11) 0.0265(4) Uani 1 1 d . . .
C4 C 0.16647(19) 0.12184(18) -0.01245(16) 0.0276(6) Uani 1 1 d . . .
O5 O 0.18889(15) 0.05232(13) -0.00120(15) 0.0419(6) Uani 1 1 d . . .
C6 C 0.0704(2) 0.1423(2) -0.0247(3) 0.0499(10) Uani 1 1 d . . .
H6A H 0.0581 0.1611 -0.0735 0.075 Uiso 1 1 calc R U .
H6B H 0.0557 0.1839 0.0085 0.075 Uiso 1 1 calc R U .
H6C H 0.0352 0.0950 -0.0170 0.075 Uiso 1 1 calc R U .
O7 O 0.40477(14) 0.24608(12) 0.00767(10) 0.0265(4) Uani 1 1 d . . .
C8 C 0.47269(18) 0.25942(16) 0.04833(15) 0.0237(5) Uani 1 1 d . . .
O9 O 0.50694(14) 0.21145(13) 0.09142(12) 0.0335(5) Uani 1 1 d . . .
C10 C 0.5122(3) 0.3412(2) 0.0421(2) 0.0511(10) Uani 1 1 d . . .
H10A H 0.4731 0.3808 0.0606 0.077 Uiso 1 1 calc R U .
H10B H 0.5202 0.3526 -0.0078 0.077 Uiso 1 1 calc R U .
H10C H 0.5690 0.3431 0.0696 0.077 Uiso 1 1 calc R U .
C11 C 0.38087(17) -0.06437(16) 0.13958(13) 0.0198(5) Uani 1 1 d . . .
H11 H 0.3801 -0.0775 0.1884 0.024 Uiso 1 1 calc R U .
C12 C 0.37014(16) 0.01397(15) 0.11684(13) 0.0174(5) Uani 1 1 d . . .
C13 C 0.35262(16) 0.08133(15) 0.16462(13) 0.0182(5) Uani 1 1 d . . .
N14 N 0.32615(14) 0.14818(12) 0.13273(11) 0.0175(4) Uani 1 1 d . . .
C15 C 0.30900(17) 0.21268(15) 0.17249(14) 0.0192(5) Uani 1 1 d . . .
C16 C 0.28748(17) 0.28551(16) 0.13567(14) 0.0225(5) Uani 1 1 d . . .
H16 H 0.2755 0.2859 0.0856 0.027 Uiso 1 1 calc R U .
C17 C 0.28464(18) 0.35322(16) 0.17316(15) 0.0247(6) Uani 1 1 d . . .
H17 H 0.2746 0.4017 0.1484 0.030 Uiso 1 1 calc R U .
C18 C 0.29618(18) 0.35460(16) 0.24884(15) 0.0234(5) Uani 1 1 d . . .
C19 C 0.30904(19) 0.42859(17) 0.28533(17) 0.0280(6) Uani 1 1 d . . .
H19 H 0.3025 0.4770 0.2598 0.034 Uiso 1 1 calc R U .
C20 C 0.33052(19) 0.42950(17) 0.35600(17) 0.0287(6) Uani 1 1 d . . .
H20 H 0.3480 0.4778 0.3787 0.034 Uiso 1 1 calc R U .
C21 C 0.32716(18) 0.35861(17) 0.39689(15) 0.0256(6) Uani 1 1 d . . .
C22 C 0.35003(19) 0.36126(19) 0.47121(17) 0.0307(6) Uani 1 1 d . . .
H22 H 0.3683 0.4099 0.4929 0.037 Uiso 1 1 calc R U .
C23 C 0.3460(2) 0.2952(2) 0.51130(16) 0.0319(7) Uani 1 1 d . . .
H23 H 0.3704 0.2953 0.5590 0.038 Uiso 1 1 calc R U .
C24 C 0.30539(19) 0.22530(18) 0.48224(15) 0.0268(6) Uani 1 1 d . . .
C25 C 0.2924(2) 0.1591(2) 0.52763(15) 0.0310(7) Uani 1 1 d . . .
H25 H 0.3175 0.1600 0.5751 0.037 Uiso 1 1 calc R U .
C26 C 0.2451(2) 0.09549(19) 0.50429(15) 0.0305(6) Uani 1 1 d . . .
H26 H 0.2416 0.0504 0.5340 0.037 Uiso 1 1 calc R U .
C27 C 0.20036(19) 0.09579(17) 0.43491(14) 0.0250(6) Uani 1 1 d . . .
C28 C 0.1406(2) 0.03459(17) 0.41500(16) 0.0297(6) Uani 1 1 d . . .
H28 H 0.1352 -0.0093 0.4458 0.036 Uiso 1 1 calc R U .
C29 C 0.0905(2) 0.03751(18) 0.35211(17) 0.0303(6) Uani 1 1 d . . .
H29 H 0.0513 -0.0044 0.3388 0.036 Uiso 1 1 calc R U .
C30 C 0.09772(19) 0.10337(17) 0.30737(16) 0.0267(6) Uani 1 1 d . . .
H30 H 0.0613 0.1068 0.2646 0.032 Uiso 1 1 calc R U .
C31 C 0.15681(18) 0.16292(16) 0.32469(15) 0.0235(5) Uani 1 1 d . . .
H31 H 0.1605 0.2067 0.2935 0.028 Uiso 1 1 calc R U .
C32 C 0.21237(17) 0.16010(16) 0.38823(14) 0.0211(5) Uani 1 1 d . . .
C33 C 0.27475(17) 0.22247(16) 0.40964(14) 0.0217(5) Uani 1 1 d . . .
C34 C 0.29997(17) 0.28611(16) 0.36425(14) 0.0209(5) Uani 1 1 d . . .
C35 C 0.30034(16) 0.28287(15) 0.28748(14) 0.0199(5) Uani 1 1 d . . .
C36 C 0.31609(16) 0.21112(15) 0.24771(13) 0.0189(5) Uani 1 1 d . . .
C37 C 0.34819(17) 0.14028(16) 0.27962(13) 0.0208(5) Uani 1 1 d . . .
H37 H 0.3576 0.1372 0.3298 0.025 Uiso 1 1 calc R U .
C38 C 0.36602(17) 0.07573(16) 0.23885(14) 0.0210(5) Uani 1 1 d . . .
H38 H 0.3871 0.0280 0.2605 0.025 Uiso 1 1 calc R U .
C51 C 0.39393(17) -0.10216(16) 0.01830(14) 0.0213(5) Uani 1 1 d . . .
H51 H 0.4008 -0.1415 -0.0168 0.026 Uiso 1 1 calc R U .
C52 C 0.38482(16) -0.02244(15) -0.00031(13) 0.0175(5) Uani 1 1 d . . .
C53 C 0.38941(16) 0.00730(15) -0.07431(13) 0.0180(5) Uani 1 1 d . . .
N54 N 0.37936(14) 0.08506(13) -0.08343(11) 0.0190(4) Uani 1 1 d . . .
C55 C 0.39308(17) 0.11720(15) -0.14805(13) 0.0194(5) Uani 1 1 d . . .
C56 C 0.3944(2) 0.20141(16) -0.15301(14) 0.0258(6) Uani 1 1 d . . .
H56 H 0.3727 0.2327 -0.1165 0.031 Uiso 1 1 calc R U .
C57 C 0.4266(2) 0.23676(16) -0.20980(14) 0.0265(6) Uani 1 1 d . . .
H57 H 0.4294 0.2929 -0.2117 0.032 Uiso 1 1 calc R U .
C58 C 0.45661(19) 0.19132(16) -0.26692(14) 0.0234(5) Uani 1 1 d . . .
C59 C 0.5084(2) 0.22828(17) -0.31705(15) 0.0284(6) Uani 1 1 d . . .
H59 H 0.5126 0.2844 -0.3188 0.034 Uiso 1 1 calc R U .
C60 C 0.55165(19) 0.18283(18) -0.36233(15) 0.0277(6) Uani 1 1 d . . .
H60 H 0.5942 0.2063 -0.3897 0.033 Uiso 1 1 calc R U .
C61 C 0.53373(18) 0.10035(17) -0.36911(14) 0.0231(5) Uani 1 1 d . . .
C62 C 0.58207(19) 0.05124(19) -0.41343(15) 0.0286(6) Uani 1 1 d . . .
H62 H 0.6301 0.0728 -0.4358 0.034 Uiso 1 1 calc R U .
C63 C 0.56022(19) -0.02569(19) -0.42386(15) 0.0290(6) Uani 1 1 d . . .
H63 H 0.5981 -0.0599 -0.4470 0.035 Uiso 1 1 calc R U .
C64 C 0.48071(19) -0.05575(17) -0.40030(14) 0.0245(6) Uani 1 1 d . . .
C65 C 0.4498(2) -0.13184(17) -0.42450(15) 0.0310(6) Uani 1 1 d . . .
H65 H 0.4887 -0.1671 -0.4455 0.037 Uiso 1 1 calc R U .
C66 C 0.3663(2) -0.15426(18) -0.41793(16) 0.0353(7) Uani 1 1 d . . .
H66 H 0.3470 -0.2052 -0.4337 0.042 Uiso 1 1 calc R U .
C67 C 0.3073(2) -0.10160(17) -0.38738(15) 0.0296(6) Uani 1 1 d . . .
C68 C 0.2167(2) -0.1190(2) -0.39359(17) 0.0391(8) Uani 1 1 d . . .
H68 H 0.1969 -0.1667 -0.4161 0.047 Uiso 1 1 calc R U .
C69 C 0.1571(2) -0.0681(2) -0.36760(18) 0.0394(8) Uani 1 1 d . . .
H69 H 0.0965 -0.0804 -0.3722 0.047 Uiso 1 1 calc R U .
C70 C 0.1863(2) 0.0024(2) -0.33408(16) 0.0316(7) Uani 1 1 d . . .
H70 H 0.1454 0.0376 -0.3156 0.038 Uiso 1 1 calc R U .
C71 C 0.27413(18) 0.02069(17) -0.32797(14) 0.0239(5) Uani 1 1 d . . .
H71 H 0.2927 0.0685 -0.3050 0.029 Uiso 1 1 calc R U .
C72 C 0.33743(18) -0.02963(16) -0.35488(13) 0.0218(5) Uani 1 1 d . . .
C73 C 0.42868(17) -0.00799(16) -0.35898(13) 0.0201(5) Uani 1 1 d . . .
C74 C 0.46596(17) 0.06601(16) -0.33204(13) 0.0200(5) Uani 1 1 d . . .
C75 C 0.44091(16) 0.10893(15) -0.27047(13) 0.0184(5) Uani 1 1 d . . .
C76 C 0.41378(16) 0.07024(15) -0.20684(13) 0.0178(5) Uani 1 1 d . . .
C77 C 0.41856(17) -0.01225(15) -0.19568(13) 0.0192(5) Uani 1 1 d . . .
H77 H 0.4290 -0.0464 -0.2341 0.023 Uiso 1 1 calc R U .
C78 C 0.40824(17) -0.04376(15) -0.12981(13) 0.0199(5) Uani 1 1 d . . .
H78 H 0.4138 -0.0992 -0.1219 0.024 Uiso 1 1 calc R U .
C101 C 0.1688(4) 0.9614(3) 0.8508(2) 0.0748(16) Uani 1 1 d . . .
H101 H 0.1868 1.0055 0.8207 0.090 Uiso 1 1 calc R U .
H102 H 0.1951 0.9704 0.8996 0.090 Uiso 1 1 calc R U .
Cl1 Cl 0.05436(10) 0.96024(9) 0.85123(9) 0.0897(5) Uani 1 1 d . . .
Cl2 Cl 0.20759(9) 0.87218(8) 0.81860(6) 0.0714(4) Uani 1 1 d . . .
C111 C 0.0873(3) 0.2390(2) 0.7457(2) 0.0493(9) Uani 1 1 d . . .
H111 H 0.0775 0.2567 0.6958 0.059 Uiso 1 1 calc R U .
H112 H 0.0750 0.2842 0.7768 0.059 Uiso 1 1 calc R U .
Cl11 Cl 0.01721(8) 0.15983(9) 0.76123(8) 0.0764(4) Uani 1 1 d . . .
Cl12 Cl 0.19585(8) 0.20866(10) 0.76279(11) 0.1014(6) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O3 Zn1 O7 101.63(9) . .
O3 Zn1 N2 123.66(8) . .
O7 Zn1 N2 134.66(9) . .
O3 Zn1 N14 96.93(8) . .
O7 Zn1 N14 98.53(8) . .
N2 Zn1 N14 75.86(8) . .
O3 Zn1 N54 101.29(8) . .
O7 Zn1 N54 99.27(8) . .
N2 Zn1 N54 75.61(8) . .
N14 Zn1 N54 151.31(8) . .
C11 C1 C51 119.9(2) . .
C11 C1 H1 120.1 . .
C51 C1 H1 120.1 . .
C52 N2 C12 120.8(2) . .
C52 N2 Zn1 119.09(16) . .
C12 N2 Zn1 119.39(17) . .
C4 O3 Zn1 111.68(18) . .
O5 C4 O3 123.7(3) . .
O5 C4 C6 119.8(3) . .
O3 C4 C6 116.5(3) . .
C4 C6 H6A 109.5 . .
C4 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C4 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C8 O7 Zn1 120.16(18) . .
O9 C8 O7 124.9(3) . .
O9 C8 C10 119.6(3) . .
O7 C8 C10 115.5(3) . .
C8 C10 H10A 109.5 . .
C8 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C8 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C1 C11 C12 118.6(2) . .
C1 C11 H11 120.7 . .
C12 C11 H11 120.7 . .
N2 C12 C11 121.0(2) . .
N2 C12 C13 115.0(2) . .
C11 C12 C13 124.0(2) . .
N14 C13 C38 121.8(2) . .
N14 C13 C12 115.9(2) . .
C38 C13 C12 122.3(2) . .
C13 N14 C15 119.6(2) . .
C13 N14 Zn1 112.74(16) . .
C15 N14 Zn1 126.53(16) . .
N14 C15 C36 122.4(2) . .
N14 C15 C16 117.6(2) . .
C36 C15 C16 119.9(2) . .
C17 C16 C15 119.1(2) . .
C17 C16 H16 120.5 . .
C15 C16 H16 120.5 . .
C16 C17 C18 122.3(2) . .
C16 C17 H17 118.9 . .
C18 C17 H17 118.9 . .
C35 C18 C17 120.1(2) . .
C35 C18 C19 119.9(3) . .
C17 C18 C19 119.9(3) . .
C20 C19 C18 120.0(3) . .
C20 C19 H19 120.0 . .
C18 C19 H19 120.0 . .
C19 C20 C21 120.6(3) . .
C19 C20 H20 119.7 . .
C21 C20 H20 119.7 . .
C34 C21 C22 119.9(3) . .
C34 C21 C20 120.6(3) . .
C22 C21 C20 119.5(3) . .
C23 C22 C21 120.6(3) . .
C23 C22 H22 119.7 . .
C21 C22 H22 119.7 . .
C22 C23 C24 120.3(3) . .
C22 C23 H23 119.9 . .
C24 C23 H23 119.9 . .
C33 C24 C23 120.3(3) . .
C33 C24 C25 120.2(3) . .
C23 C24 C25 119.4(3) . .
C26 C25 C24 121.4(3) . .
C26 C25 H25 119.3 . .
C24 C25 H25 119.3 . .
C25 C26 C27 120.3(3) . .
C25 C26 H26 119.9 . .
C27 C26 H26 119.9 . .
C28 C27 C32 120.4(3) . .
C28 C27 C26 119.8(3) . .
C32 C27 C26 119.7(3) . .
C29 C28 C27 121.1(3) . .
C29 C28 H28 119.5 . .
C27 C28 H28 119.5 . .
C28 C29 C30 119.1(3) . .
C28 C29 H29 120.4 . .
C30 C29 H29 120.4 . .
C31 C30 C29 121.0(3) . .
C31 C30 H30 119.5 . .
C29 C30 H30 119.5 . .
C30 C31 C32 121.3(3) . .
C30 C31 H31 119.4 . .
C32 C31 H31 119.4 . .
C27 C32 C31 117.0(3) . .
C27 C32 C33 119.5(2) . .
C31 C32 C33 123.3(2) . .
C24 C33 C34 117.7(3) . .
C24 C33 C32 117.1(2) . .
C34 C33 C32 124.8(2) . .
C21 C34 C33 117.8(2) . .
C21 C34 C35 116.3(2) . .
C33 C34 C35 125.9(2) . .
C18 C35 C34 118.7(2) . .
C18 C35 C36 116.7(2) . .
C34 C35 C36 124.1(2) . .
C37 C36 C15 116.2(2) . .
C37 C36 C35 123.4(2) . .
C15 C36 C35 120.0(2) . .
C38 C37 C36 120.7(2) . .
C38 C37 H37 119.7 . .
C36 C37 H37 119.7 . .
C37 C38 C13 119.1(2) . .
C37 C38 H38 120.5 . .
C13 C38 H38 120.5 . .
C1 C51 C52 118.3(2) . .
C1 C51 H51 120.8 . .
C52 C51 H51 120.8 . .
N2 C52 C51 121.3(2) . .
N2 C52 C53 115.3(2) . .
C51 C52 C53 123.3(2) . .
N54 C53 C78 122.5(2) . .
N54 C53 C52 116.1(2) . .
C78 C53 C52 121.4(2) . .
C53 N54 C55 118.9(2) . .
C53 N54 Zn1 112.25(16) . .
C55 N54 Zn1 128.89(17) . .
N54 C55 C76 122.4(2) . .
N54 C55 C56 117.3(2) . .
C76 C55 C56 120.0(2) . .
C57 C56 C55 120.0(3) . .
C57 C56 H56 120.0 . .
C55 C56 H56 120.0 . .
C56 C57 C58 121.4(3) . .
C56 C57 H57 119.3 . .
C58 C57 H57 119.3 . .
C75 C58 C59 120.1(3) . .
C75 C58 C57 120.1(2) . .
C59 C58 C57 119.7(3) . .
C60 C59 C58 119.7(3) . .
C60 C59 H59 120.2 . .
C58 C59 H59 120.2 . .
C59 C60 C61 120.6(3) . .
C59 C60 H60 119.7 . .
C61 C60 H60 119.7 . .
C74 C61 C60 119.9(3) . .
C74 C61 C62 119.0(3) . .
C60 C61 C62 121.1(3) . .
C63 C62 C61 120.6(3) . .
C63 C62 H62 119.7 . .
C61 C62 H62 119.7 . .
C62 C63 C64 120.4(3) . .
C62 C63 H63 119.8 . .
C64 C63 H63 119.8 . .
C73 C64 C63 120.2(3) . .
C73 C64 C65 120.1(3) . .
C63 C64 C65 119.4(3) . .
C66 C65 C64 121.0(3) . .
C66 C65 H65 119.5 . .
C64 C65 H65 119.5 . .
C65 C66 C67 120.0(3) . .
C65 C66 H66 120.0 . .
C67 C66 H66 120.0 . .
C68 C67 C66 119.2(3) . .
C68 C67 C72 119.9(3) . .
C66 C67 C72 120.8(3) . .
C69 C68 C67 121.1(3) . .
C69 C68 H68 119.5 . .
C67 C68 H68 119.5 . .
C68 C69 C70 119.6(3) . .
C68 C69 H69 120.2 . .
C70 C69 H69 120.2 . .
C71 C70 C69 120.2(3) . .
C71 C70 H70 119.9 . .
C69 C70 H70 119.9 . .
C70 C71 C72 121.9(3) . .
C70 C71 H71 119.0 . .
C72 C71 H71 119.0 . .
C71 C72 C67 117.3(3) . .
C71 C72 C73 124.0(2) . .
C67 C72 C73 118.3(3) . .
C64 C73 C74 117.5(2) . .
C64 C73 C72 118.2(2) . .
C74 C73 C72 123.6(2) . .
C61 C74 C75 116.2(2) . .
C61 C74 C73 117.5(2) . .
C75 C74 C73 126.3(2) . .
C58 C75 C74 118.5(2) . .
C58 C75 C76 117.4(2) . .
C74 C75 C76 123.3(2) . .
C77 C76 C55 116.5(2) . .
C77 C76 C75 123.5(2) . .
C55 C76 C75 119.4(2) . .
C78 C77 C76 120.6(2) . .
C78 C77 H77 119.7 . .
C76 C77 H77 119.7 . .
C77 C78 C53 118.9(2) . .
C77 C78 H78 120.5 . .
C53 C78 H78 120.5 . .
Cl2 C101 Cl1 111.1(2) . .
Cl2 C101 H101 109.4 . .
Cl1 C101 H101 109.4 . .
Cl2 C101 H102 109.4 . .
Cl1 C101 H102 109.4 . .
H101 C101 H102 108.0 . .
Cl12 C111 Cl11 109.4(2) . .
Cl12 C111 H111 109.8 . .
Cl11 C111 H111 109.8 . .
Cl12 C111 H112 109.8 . .
Cl11 C111 H112 109.8 . .
H111 C111 H112 108.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O3 1.9657(19) .
Zn1 O7 1.9684(19) .
Zn1 N2 2.057(2) .
Zn1 N14 2.242(2) .
Zn1 N54 2.258(2) .
C1 C11 1.387(4) .
C1 C51 1.390(4) .
C1 H1 0.9500 .
N2 C52 1.337(3) .
N2 C12 1.339(3) .
O3 C4 1.273(4) .
C4 O5 1.237(4) .
C4 C6 1.515(4) .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
O7 C8 1.267(3) .
C8 O9 1.237(3) .
C8 C10 1.516(4) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 C12 1.397(4) .
C11 H11 0.9500 .
C12 C13 1.489(3) .
C13 N14 1.328(3) .
C13 C38 1.406(3) .
N14 C15 1.360(3) .
C15 C36 1.418(3) .
C15 C16 1.439(3) .
C16 C17 1.347(4) .
C16 H16 0.9500 .
C17 C18 1.429(4) .
C17 H17 0.9500 .
C18 C35 1.413(4) .
C18 C19 1.433(4) .
C19 C20 1.352(4) .
C19 H19 0.9500 .
C20 C21 1.428(4) .
C20 H20 0.9500 .
C21 C34 1.419(4) .
C21 C22 1.423(4) .
C22 C23 1.353(5) .
C22 H22 0.9500 .
C23 C24 1.425(4) .
C23 H23 0.9500 .
C24 C33 1.417(4) .
C24 C25 1.432(4) .
C25 C26 1.351(5) .
C25 H25 0.9500 .
C26 C27 1.434(4) .
C26 H26 0.9500 .
C27 C28 1.413(4) .
C27 C32 1.420(4) .
C28 C29 1.367(5) .
C28 H28 0.9500 .
C29 C30 1.407(4) .
C29 H29 0.9500 .
C30 C31 1.377(4) .
C30 H30 0.9500 .
C31 C32 1.420(4) .
C31 H31 0.9500 .
C32 C33 1.459(4) .
C33 C34 1.446(4) .
C34 C35 1.453(4) .
C35 C36 1.456(4) .
C36 C37 1.411(4) .
C37 C38 1.374(4) .
C37 H37 0.9500 .
C38 H38 0.9500 .
C51 C52 1.395(4) .
C51 H51 0.9500 .
C52 C53 1.493(3) .
C53 N54 1.331(3) .
C53 C78 1.405(4) .
N54 C55 1.368(3) .
C55 C76 1.421(4) .
C55 C56 1.425(4) .
C56 C57 1.354(4) .
C56 H56 0.9500 .
C57 C58 1.429(4) .
C57 H57 0.9500 .
C58 C75 1.412(4) .
C58 C59 1.426(4) .
C59 C60 1.360(4) .
C59 H59 0.9500 .
C60 C61 1.423(4) .
C60 H60 0.9500 .
C61 C74 1.421(4) .
C61 C62 1.426(4) .
C62 C63 1.352(5) .
C62 H62 0.9500 .
C63 C64 1.424(4) .
C63 H63 0.9500 .
C64 C73 1.411(4) .
C64 C65 1.432(4) .
C65 C66 1.351(5) .
C65 H65 0.9500 .
C66 C67 1.423(5) .
C66 H66 0.9500 .
C67 C68 1.417(5) .
C67 C72 1.423(4) .
C68 C69 1.373(5) .
C68 H68 0.9500 .
C69 C70 1.406(5) .
C69 H69 0.9500 .
C70 C71 1.379(4) .
C70 H70 0.9500 .
C71 C72 1.414(4) .
C71 H71 0.9500 .
C72 C73 1.455(4) .
C73 C74 1.450(4) .
C74 C75 1.448(4) .
C75 C76 1.457(3) .
C76 C77 1.410(4) .
C77 C78 1.374(4) .
C77 H77 0.9500 .
C78 H78 0.9500 .
C101 Cl2 1.745(6) .
C101 Cl1 1.758(6) .
C101 H101 0.9900 .
C101 H102 0.9900 .
C111 Cl12 1.749(4) .
C111 Cl11 1.755(4) .
C111 H111 0.9900 .
C111 H112 0.9900 .
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
Zn1 O3 C4 O5 -7.6(4) . . . .
Zn1 O3 C4 C6 172.0(3) . . . .
Zn1 O7 C8 O9 5.0(4) . . . .
Zn1 O7 C8 C10 -174.6(2) . . . .
C51 C1 C11 C12 0.2(4) . . . .
C52 N2 C12 C11 1.4(4) . . . .
Zn1 N2 C12 C11 171.50(18) . . . .
C52 N2 C12 C13 -177.2(2) . . . .
Zn1 N2 C12 C13 -7.1(3) . . . .
C1 C11 C12 N2 -1.6(4) . . . .
C1 C11 C12 C13 176.9(2) . . . .
N2 C12 C13 N14 12.2(3) . . . .
C11 C12 C13 N14 -166.4(2) . . . .
N2 C12 C13 C38 -165.7(2) . . . .
C11 C12 C13 C38 15.7(4) . . . .
C38 C13 N14 C15 -1.9(4) . . . .
C12 C13 N14 C15 -179.8(2) . . . .
C38 C13 N14 Zn1 167.0(2) . . . .
C12 C13 N14 Zn1 -10.9(3) . . . .
C13 N14 C15 C36 -1.7(4) . . . .
Zn1 N14 C15 C36 -168.88(18) . . . .
C13 N14 C15 C16 175.0(2) . . . .
Zn1 N14 C15 C16 7.8(3) . . . .
N14 C15 C16 C17 -168.9(2) . . . .
C36 C15 C16 C17 7.9(4) . . . .
C15 C16 C17 C18 -4.5(4) . . . .
C16 C17 C18 C35 -7.9(4) . . . .
C16 C17 C18 C19 168.2(3) . . . .
C35 C18 C19 C20 4.1(4) . . . .
C17 C18 C19 C20 -171.9(3) . . . .
C18 C19 C20 C21 -10.0(4) . . . .
C19 C20 C21 C34 -0.9(4) . . . .
C19 C20 C21 C22 -179.9(3) . . . .
C34 C21 C22 C23 -0.1(4) . . . .
C20 C21 C22 C23 178.9(3) . . . .
C21 C22 C23 C24 -10.4(4) . . . .
C22 C23 C24 C33 4.8(4) . . . .
C22 C23 C24 C25 -172.5(3) . . . .
C33 C24 C25 C26 -5.2(4) . . . .
C23 C24 C25 C26 172.1(3) . . . .
C24 C25 C26 C27 -5.5(4) . . . .
C25 C26 C27 C28 -170.3(3) . . . .
C25 C26 C27 C32 5.9(4) . . . .
C32 C27 C28 C29 -2.9(4) . . . .
C26 C27 C28 C29 173.3(3) . . . .
C27 C28 C29 C30 -1.1(4) . . . .
C28 C29 C30 C31 2.6(4) . . . .
C29 C30 C31 C32 -0.1(4) . . . .
C28 C27 C32 C31 5.2(4) . . . .
C26 C27 C32 C31 -170.9(2) . . . .
C28 C27 C32 C33 -179.7(2) . . . .
C26 C27 C32 C33 4.2(4) . . . .
C30 C31 C32 C27 -3.8(4) . . . .
C30 C31 C32 C33 -178.7(3) . . . .
C23 C24 C33 C34 10.9(4) . . . .
C25 C24 C33 C34 -171.7(2) . . . .
C23 C24 C33 C32 -162.5(3) . . . .
C25 C24 C33 C32 14.8(4) . . . .
C27 C32 C33 C24 -14.2(4) . . . .
C31 C32 C33 C24 160.6(3) . . . .
C27 C32 C33 C34 172.8(2) . . . .
C31 C32 C33 C34 -12.4(4) . . . .
C22 C21 C34 C33 15.8(4) . . . .
C20 C21 C34 C33 -163.2(2) . . . .
C22 C21 C34 C35 -164.1(2) . . . .
C20 C21 C34 C35 16.9(4) . . . .
C24 C33 C34 C21 -20.8(4) . . . .
C32 C33 C34 C21 152.1(3) . . . .
C24 C33 C34 C35 159.0(3) . . . .
C32 C33 C34 C35 -28.1(4) . . . .
C17 C18 C35 C34 -171.6(2) . . . .
C19 C18 C35 C34 12.3(4) . . . .
C17 C18 C35 C36 16.1(4) . . . .
C19 C18 C35 C36 -160.0(2) . . . .
C21 C34 C35 C18 -22.3(4) . . . .
C33 C34 C35 C18 157.9(3) . . . .
C21 C34 C35 C36 149.4(3) . . . .
C33 C34 C35 C36 -30.4(4) . . . .
N14 C15 C36 C37 4.4(4) . . . .
C16 C15 C36 C37 -172.2(2) . . . .
N14 C15 C36 C35 177.5(2) . . . .
C16 C15 C36 C35 0.9(4) . . . .
C18 C35 C36 C37 159.9(3) . . . .
C34 C35 C36 C37 -11.9(4) . . . .
C18 C35 C36 C15 -12.6(4) . . . .
C34 C35 C36 C15 175.5(2) . . . .
C15 C36 C37 C38 -3.8(4) . . . .
C35 C36 C37 C38 -176.6(2) . . . .
C36 C37 C38 C13 0.6(4) . . . .
N14 C13 C38 C37 2.4(4) . . . .
C12 C13 C38 C37 -179.8(2) . . . .
C11 C1 C51 C52 1.3(4) . . . .
C12 N2 C52 C51 0.1(4) . . . .
Zn1 N2 C52 C51 -169.98(19) . . . .
C12 N2 C52 C53 -178.4(2) . . . .
Zn1 N2 C52 C53 11.5(3) . . . .
C1 C51 C52 N2 -1.5(4) . . . .
C1 C51 C52 C53 176.9(2) . . . .
N2 C52 C53 N54 -1.6(3) . . . .
C51 C52 C53 N54 179.9(2) . . . .
N2 C52 C53 C78 174.9(2) . . . .
C51 C52 C53 C78 -3.6(4) . . . .
C78 C53 N54 C55 -4.1(4) . . . .
C52 C53 N54 C55 172.4(2) . . . .
C78 C53 N54 Zn1 175.85(19) . . . .
C52 C53 N54 Zn1 -7.7(3) . . . .
C53 N54 C55 C76 2.9(4) . . . .
Zn1 N54 C55 C76 -176.97(18) . . . .
C53 N54 C55 C56 -171.0(2) . . . .
Zn1 N54 C55 C56 9.1(3) . . . .
N54 C55 C56 C57 165.2(3) . . . .
C76 C55 C56 C57 -8.9(4) . . . .
C55 C56 C57 C58 2.5(4) . . . .
C56 C57 C58 C75 9.7(4) . . . .
C56 C57 C58 C59 -165.3(3) . . . .
C75 C58 C59 C60 -8.4(4) . . . .
C57 C58 C59 C60 166.6(3) . . . .
C58 C59 C60 C61 11.4(4) . . . .
C59 C60 C61 C74 4.3(4) . . . .
C59 C60 C61 C62 -176.5(3) . . . .
C74 C61 C62 C63 4.3(4) . . . .
C60 C61 C62 C63 -174.9(3) . . . .
C61 C62 C63 C64 10.1(4) . . . .
C62 C63 C64 C73 -7.0(4) . . . .
C62 C63 C64 C65 167.0(3) . . . .
C73 C64 C65 C66 10.2(4) . . . .
C63 C64 C65 C66 -163.8(3) . . . .
C64 C65 C66 C67 0.8(5) . . . .
C65 C66 C67 C68 167.5(3) . . . .
C65 C66 C67 C72 -8.5(4) . . . .
C66 C67 C68 C69 -177.1(3) . . . .
C72 C67 C68 C69 -1.1(5) . . . .
C67 C68 C69 C70 -0.2(5) . . . .
C68 C69 C70 C71 0.7(5) . . . .
C69 C70 C71 C72 0.2(4) . . . .
C70 C71 C72 C67 -1.5(4) . . . .
C70 C71 C72 C73 170.8(3) . . . .
C68 C67 C72 C71 1.9(4) . . . .
C66 C67 C72 C71 177.9(3) . . . .
C68 C67 C72 C73 -170.8(3) . . . .
C66 C67 C72 C73 5.2(4) . . . .
C63 C64 C73 C74 -10.1(4) . . . .
C65 C64 C73 C74 175.9(2) . . . .
C63 C64 C73 C72 160.9(2) . . . .
C65 C64 C73 C72 -13.1(4) . . . .
C71 C72 C73 C64 -166.6(2) . . . .
C67 C72 C73 C64 5.5(4) . . . .
C71 C72 C73 C74 3.7(4) . . . .
C67 C72 C73 C74 175.9(2) . . . .
C60 C61 C74 C75 -22.1(4) . . . .
C62 C61 C74 C75 158.7(2) . . . .
C60 C61 C74 C73 157.9(2) . . . .
C62 C61 C74 C73 -21.3(4) . . . .
C64 C73 C74 C61 23.9(3) . . . .
C72 C73 C74 C61 -146.5(3) . . . .
C64 C73 C74 C75 -156.1(3) . . . .
C72 C73 C74 C75 33.5(4) . . . .
C59 C58 C75 C74 -9.9(4) . . . .
C57 C58 C75 C74 175.1(2) . . . .
C59 C58 C75 C76 160.2(2) . . . .
C57 C58 C75 C76 -14.8(4) . . . .
C61 C74 C75 C58 24.6(3) . . . .
C73 C74 C75 C58 -155.4(3) . . . .
C61 C74 C75 C76 -144.9(2) . . . .
C73 C74 C75 C76 35.1(4) . . . .
N54 C55 C76 C77 0.8(4) . . . .
C56 C55 C76 C77 174.6(2) . . . .
N54 C55 C76 C75 -170.4(2) . . . .
C56 C55 C76 C75 3.3(4) . . . .
C58 C75 C76 C77 -162.2(2) . . . .
C74 C75 C76 C77 7.4(4) . . . .
C58 C75 C76 C55 8.3(4) . . . .
C74 C75 C76 C55 177.9(2) . . . .
C55 C76 C77 C78 -3.5(4) . . . .
C75 C76 C77 C78 167.4(2) . . . .
C76 C77 C78 C53 2.5(4) . . . .
N54 C53 C78 C77 1.4(4) . . . .
C52 C53 C78 C77 -174.9(2) . . . .
