#------------------------------------------------------------------------------
#$Date: 2016-03-26 23:06:14 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180529 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/98/7219823.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_7219823
loop_
_publ_author_name
'Rodpun, Kiattipoom'
'Blackman, Allan G.'
'Gardiner, Michael G.'
'Tan, Eng Wui'
'Meledandri, Carla J.'
'Lucas, Nigel T.'
_publ_section_title
;
 Alkyl linker effects on the coordination topology of ditopic
 di(2-pyridylmethyl)amine carboxylate ligands with ZnIIand CuII: polymers
 vs. macrocycles
;
_journal_issue                   15
_journal_name_full               CrystEngComm
_journal_page_first              2974
_journal_paper_doi               10.1039/C5CE00375J
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C20 H28 N3 O3 Zn 1+, Cl O4 1-'
_chemical_formula_sum            'C20 H28 Cl N3 O7 Zn'
_chemical_formula_weight         523.27
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                nl_kr7
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-02-22 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   16.9390(2)
_cell_length_b                   16.9390(2)
_cell_length_c                   33.5981(6)
_cell_measurement_reflns_used    10612
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      74.499
_cell_measurement_theta_min      3.688
_cell_volume                     9640.3(2)
_computing_cell_refinement       'CrysAlisPro (Agilent, V 1.171.36.28)'
_computing_data_collection       'CrysAlisPro (Agilent, V 1.171.36.28)'
_computing_data_reduction        'CrysAlisPro (Agilent, V 1.171.36.28)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'enCIFer (CCDC, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      100(1)
_diffrn_crystal_treatment
; 
Crystal was attached with Paratone N oil to a 0.3 mm CryoLoop supported 
in a copper mounting pin, then quenched in a cold nitrogen gas from a gas
stream from an Oxford Cryosystems Cryostream.
;
_diffrn_detector_area_resol_mean 5.1725
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18903
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         74.85
_diffrn_reflns_theta_min         4.73
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.820
_exptl_absorpt_correction_T_max  0.5509
_exptl_absorpt_correction_T_min  0.4473
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies, Version 1.171.36.28, 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             4352
_exptl_crystal_preparation
;
Crystals were grown by slow diffusion of a methanolic solution of the 
carboxylic acid ligand into an aqueous Zn(II) perchlorate solution 
at room temperature.
;
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol/water'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.819
_refine_diff_density_min         -1.001
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     467
_refine_ls_number_reflns         4814
_refine_ls_number_restraints     575
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0863
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1611P)²+20.8508P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2584
_refine_ls_wR_factor_ref         0.2686
_reflns_number_gt                4197
_reflns_number_total             4814
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ce00375j2.cif
_cod_data_source_block           7_Zn-C7
_cod_depositor_comments
'Adding full bibliography for 7219817--7219825.cif.'
_cod_original_sg_symbol_H-M      I41/a
_cod_database_code               7219823
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+3/4, x+1/4, z+1/4'
'-x, -y+1/2, z'
'y+1/4, -x+1/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'y+3/4, -x+3/4, z+3/4'
'-x, -y, -z'
'y-3/4, -x-1/4, -z-1/4'
'x, y-1/2, -z'
'-y-1/4, x-1/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'x+1/2, y, -z+1/2'
'-y+1/4, x+1/4, -z+1/4'
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 0.19829(5) 0.42719(4) 0.101174(19) 0.0710(3) Uani 1 1 d U . .
Cl1 Cl 0.4311(5) 0.8086(6) 0.0473(3) 0.109(2) Uani 0.25 1 d PDU . 1
Cl2 Cl 0.0000 0.2500 0.03535(5) 0.0776(5) Uani 1 2 d SDU . .
O1 O 0.7780(3) 0.1393(2) 0.05428(11) 0.0850(11) Uani 1 1 d U . .
O2 O 0.7807(2) 0.2276(2) 0.10175(10) 0.0760(10) Uani 1 1 d U . .
O3 O 0.0833(3) 0.3897(3) 0.10924(13) 0.0831(10) Uani 1 1 d DU . .
H31 H 0.078(4) 0.3410(11) 0.105(3) 0.125 Uiso 1 1 d D . .
H32 H 0.044(3) 0.406(4) 0.122(2) 0.125 Uiso 1 1 d D . .
O11 O 0.4639(14) 0.8621(15) 0.0782(7) 0.147(5) Uani 0.25 1 d PDU A 1
O12 O 0.3850(14) 0.8579(13) 0.0215(7) 0.147(6) Uani 0.25 1 d PDU B 1
O13 O 0.3815(10) 0.7567(11) 0.0685(7) 0.112(4) Uani 0.25 1 d PDU C 1
O14 O 0.4940(12) 0.7738(12) 0.0274(6) 0.130(5) Uani 0.25 1 d PDU . 1
O21 O 0.0000 0.2500 0.07670(19) 0.147(3) Uani 1 2 d SDU D 1
O22 O 0.0828(5) 0.2508(11) 0.0282(5) 0.168(5) Uani 0.50 1 d PDU . 1
O23 O -0.0333(11) 0.1849(8) 0.0185(4) 0.156(5) Uani 0.50 1 d PDU . 1
O24 O -0.0280(11) 0.3223(7) 0.0209(4) 0.160(5) Uani 0.50 1 d PDU . 1
N1 N 0.1650(3) 0.5410(3) 0.08365(12) 0.0670(10) Uani 1 1 d U E .
N2 N 0.2327(3) 0.4173(3) 0.15961(14) 0.0787(12) Uani 1 1 d U E .
N3 N 0.3150(3) 0.4880(3) 0.09968(15) 0.0836(13) Uani 1 1 d DU . .
C11 C 0.3061(4) 0.5549(4) 0.0714(2) 0.0919(17) Uani 1 1 d U E .
H11A H 0.3159 0.5361 0.0439 0.110 Uiso 1 1 calc R . .
H11B H 0.3455 0.5962 0.0776 0.110 Uiso 1 1 calc R . .
C12 C 0.2244(4) 0.5894(3) 0.07390(16) 0.0762(13) Uani 1 1 d U . .
C13 C 0.2110(4) 0.6678(4) 0.06320(19) 0.0884(16) Uani 1 1 d U E .
H13 H 0.2536 0.7023 0.0574 0.106 Uiso 1 1 calc R . .
C14 C 0.1344(5) 0.6934(4) 0.0614(2) 0.103(2) Uani 1 1 d U . .
H14 H 0.1232 0.7459 0.0532 0.123 Uiso 1 1 calc R E .
C15 C 0.0739(4) 0.6437(4) 0.07145(19) 0.0896(17) Uani 1 1 d U E .
H15 H 0.0208 0.6616 0.0707 0.108 Uiso 1 1 calc R . .
C16 C 0.0909(3) 0.5679(3) 0.08257(15) 0.0728(13) Uani 1 1 d U . .
H16 H 0.0490 0.5335 0.0897 0.087 Uiso 1 1 calc R E .
C21 C 0.3269(5) 0.5166(5) 0.1409(2) 0.0978(18) Uani 1 1 d DU E .
H21A H 0.2999 0.5680 0.1443 0.117 Uiso 1 1 calc R . .
H21B H 0.3839 0.5248 0.1458 0.117 Uiso 1 1 calc R . .
C22 C 0.2947(4) 0.4580(4) 0.17093(18) 0.0855(15) Uani 1 1 d U . .
C23 C 0.3280(4) 0.4483(5) 0.2089(2) 0.0983(19) Uani 1 1 d U E .
H23 H 0.3724 0.4787 0.2168 0.118 Uiso 1 1 calc R . .
C24 C 0.2959(4) 0.3952(5) 0.2340(2) 0.103(2) Uani 1 1 d U . .
H24 H 0.3186 0.3874 0.2596 0.124 Uiso 1 1 calc R E .
C25 C 0.2294(5) 0.3516(5) 0.22286(19) 0.0980(18) Uani 1 1 d U E .
H25 H 0.2055 0.3143 0.2402 0.118 Uiso 1 1 calc R . .
C26 C 0.2002(4) 0.3660(4) 0.18479(16) 0.0845(15) Uani 1 1 d U . .
H26 H 0.1548 0.3378 0.1763 0.101 Uiso 1 1 calc R E .
C31 C 0.3766(9) 0.4359(10) 0.0827(8) 0.074(3) Uani 0.35 1 d PDU E 1
H31A H 0.3572 0.4143 0.0571 0.089 Uiso 0.35 1 calc PR E 1
H31B H 0.3849 0.3908 0.1010 0.089 Uiso 0.35 1 calc PR E 1
C32 C 0.4544(7) 0.4756(9) 0.0756(5) 0.069(4) Uani 0.35 1 d PDU E 1
H32A H 0.4472 0.5189 0.0561 0.083 Uiso 0.35 1 calc PR E 1
H32B H 0.4734 0.4991 0.1008 0.083 Uiso 0.35 1 calc PR E 1
C33 C 0.5148(6) 0.4192(9) 0.0602(5) 0.066(3) Uani 0.35 1 d PDU E 1
H33A H 0.5284 0.3825 0.0821 0.079 Uiso 0.35 1 calc PR E 1
H33B H 0.4898 0.3874 0.0390 0.079 Uiso 0.35 1 calc PR E 1
C34 C 0.5882(6) 0.4510(8) 0.0444(5) 0.082(4) Uani 0.35 1 d PDU E 1
H34A H 0.6119 0.4845 0.0654 0.099 Uiso 0.35 1 calc PR E 1
H34B H 0.5744 0.4863 0.0220 0.099 Uiso 0.35 1 calc PR E 1
C35 C 0.6498(7) 0.3967(8) 0.0304(4) 0.067(3) Uani 0.35 1 d PDU E 1
H35A H 0.6950 0.4289 0.0211 0.081 Uiso 0.35 1 calc PR E 1
H35B H 0.6289 0.3684 0.0069 0.081 Uiso 0.35 1 calc PR E 1
C36 C 0.6804(13) 0.3370(14) 0.0587(8) 0.064(4) Uani 0.35 1 d PDU E 1
H36A H 0.6350 0.3120 0.0723 0.076 Uiso 0.35 1 calc PR E 1
H36B H 0.7121 0.3645 0.0792 0.076 Uiso 0.35 1 calc PR E 1
C37 C 0.7299(15) 0.2736(16) 0.0406(9) 0.064(4) Uani 0.35 1 d PDU E 1
H37A H 0.7719 0.3003 0.0252 0.076 Uiso 0.35 1 calc PR E 1
H37B H 0.6962 0.2457 0.0211 0.076 Uiso 0.35 1 calc PR E 1
C38 C 0.7708(4) 0.2096(3) 0.06593(16) 0.0763(14) Uani 1 1 d U . .
C41 C 0.3922(10) 0.4496(10) 0.0860(7) 0.074(3) Uani 0.35 1 d PDU E -2
H41A H 0.3865 0.4343 0.0577 0.089 Uiso 0.35 1 calc PR E -2
H41B H 0.4348 0.4895 0.0875 0.089 Uiso 0.35 1 calc PR E -2
C42 C 0.4177(7) 0.3774(8) 0.1095(5) 0.073(3) Uani 0.35 1 d PDU E -2
H42A H 0.4424 0.3953 0.1346 0.087 Uiso 0.35 1 calc PR E -2
H42B H 0.3702 0.3465 0.1165 0.087 Uiso 0.35 1 calc PR E -2
C43 C 0.4749(7) 0.3241(8) 0.0882(5) 0.070(3) Uani 0.35 1 d PDU E -2
H43A H 0.4498 0.3058 0.0632 0.084 Uiso 0.35 1 calc PR E -2
H43B H 0.4842 0.2770 0.1050 0.084 Uiso 0.35 1 calc PR E -2
C44 C 0.5545(7) 0.3603(8) 0.0778(4) 0.062(3) Uani 0.35 1 d PDU E -2
H44A H 0.5763 0.3862 0.1018 0.075 Uiso 0.35 1 calc PR E -2
H44B H 0.5467 0.4014 0.0573 0.075 Uiso 0.35 1 calc PR E -2
C45 C 0.6139(7) 0.3002(8) 0.0626(5) 0.062(3) Uani 0.35 1 d PDU E -2
H45A H 0.6216 0.2595 0.0834 0.074 Uiso 0.35 1 calc PR E -2
H45B H 0.5909 0.2736 0.0390 0.074 Uiso 0.35 1 calc PR E -2
C46 C 0.6936(12) 0.3324(14) 0.0512(9) 0.066(5) Uani 0.35 1 d PDU E -2
H46A H 0.7186 0.3557 0.0751 0.079 Uiso 0.35 1 calc PR E -2
H46B H 0.6862 0.3753 0.0315 0.079 Uiso 0.35 1 calc PR E -2
C47 C 0.7492(15) 0.2713(19) 0.0337(12) 0.064(5) Uani 0.35 1 d PDU E -2
H47A H 0.7977 0.2974 0.0239 0.076 Uiso 0.35 1 calc PR E -2
H47B H 0.7235 0.2446 0.0109 0.076 Uiso 0.35 1 calc PR E -2
C51 C 0.3668(10) 0.4155(10) 0.0929(8) 0.074(3) Uani 0.30 1 d PDU E -3
H51A H 0.3488 0.3872 0.0688 0.089 Uiso 0.30 1 calc PR E -3
H51B H 0.3619 0.3792 0.1158 0.089 Uiso 0.30 1 calc PR E -3
C52 C 0.4534(8) 0.4399(10) 0.0878(6) 0.065(4) Uani 0.30 1 d PDU E -3
H52A H 0.4570 0.4827 0.0678 0.078 Uiso 0.30 1 calc PR E -3
H52B H 0.4738 0.4605 0.1134 0.078 Uiso 0.30 1 calc PR E -3
C53 C 0.5043(7) 0.3705(10) 0.0744(6) 0.063(3) Uani 0.30 1 d PDU E -3
H53A H 0.5038 0.3297 0.0955 0.075 Uiso 0.30 1 calc PR E -3
H53B H 0.4807 0.3470 0.0502 0.075 Uiso 0.30 1 calc PR E -3
C54 C 0.5895(6) 0.3930(8) 0.0656(5) 0.058(3) Uani 0.30 1 d PDU E -3
H54A H 0.6128 0.4182 0.0894 0.070 Uiso 0.30 1 calc PR E -3
H54B H 0.5905 0.4320 0.0436 0.070 Uiso 0.30 1 calc PR E -3
C55 C 0.6397(8) 0.3215(10) 0.0539(6) 0.058(4) Uani 0.30 1 d PDU E -3
H55A H 0.6375 0.2820 0.0756 0.070 Uiso 0.30 1 calc PR E -3
H55B H 0.6168 0.2970 0.0298 0.070 Uiso 0.30 1 calc PR E -3
C56 C 0.7251(9) 0.3420(11) 0.0458(7) 0.058(3) Uani 0.30 1 d PDU E -3
H56A H 0.7484 0.3657 0.0701 0.070 Uiso 0.30 1 calc PR E -3
H56B H 0.7275 0.3820 0.0244 0.070 Uiso 0.30 1 calc PR E -3
C57 C 0.7738(12) 0.2705(16) 0.0337(12) 0.058(4) Uani 0.30 1 d PDU E -3
H57A H 0.7528 0.2481 0.0087 0.070 Uiso 0.30 1 calc PR E -3
H57B H 0.8293 0.2866 0.0290 0.070 Uiso 0.30 1 calc PR E -3
Cl1' Cl 0.4359(5) 0.8525(6) 0.0499(3) 0.115(3) Uani 0.25 1 d PDU F 2
O13' O 0.3758(10) 0.7907(11) 0.0503(7) 0.112(4) Uani 0.25 1 d PDU F 2
O14' O 0.5085(10) 0.8257(13) 0.0335(7) 0.130(5) Uani 0.25 1 d PDU F 2
O12' O 0.4067(14) 0.9203(12) 0.0277(7) 0.147(6) Uani 0.25 1 d PDU F 2
O11' O 0.4470(15) 0.8775(16) 0.0917(5) 0.147(5) Uani 0.25 1 d PDU F 2
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'
O O 0.0492 0.0322 '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'
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
O1 Zn1 N2 131.08(18) 3_655 .
O1 Zn1 O3 96.96(18) 3_655 .
N2 Zn1 O3 96.7(2) . .
O1 Zn1 N1 110.79(16) 3_655 .
N2 Zn1 N1 114.84(18) . .
O3 Zn1 N1 93.79(18) . .
O1 Zn1 N3 93.71(19) 3_655 .
N2 Zn1 N3 78.9(2) . .
O3 Zn1 N3 168.69(17) . .
N1 Zn1 N3 78.86(18) . .
O14 Cl1 O13 115.9(11) . .
O14 Cl1 O12 111.9(11) . .
O13 Cl1 O12 110.1(10) . .
O14 Cl1 O11 108.0(11) . .
O13 Cl1 O11 104.5(10) . .
O12 Cl1 O11 105.7(11) . .
O14 Cl1 O14 19.4(14) . 3_665
O13 Cl1 O14 96.5(12) . 3_665
O12 Cl1 O14 123.3(11) . 3_665
O11 Cl1 O14 115.0(12) . 3_665
O23 Cl2 O23 130.8(13) . 3
O23 Cl2 O21 114.6(6) . .
O23 Cl2 O21 114.6(6) 3 .
O23 Cl2 O24 44.5(7) . 3
O23 Cl2 O24 115.0(7) 3 3
O21 Cl2 O24 110.3(6) . 3
O23 Cl2 O24 115.0(7) . .
O23 Cl2 O24 44.5(7) 3 .
O21 Cl2 O24 110.3(6) . .
O24 Cl2 O24 139.3(13) 3 .
O23 Cl2 O22 110.2(8) . .
O23 Cl2 O22 60.9(8) 3 .
O21 Cl2 O22 99.7(6) . .
O24 Cl2 O22 67.4(8) 3 .
O24 Cl2 O22 105.4(7) . .
O23 Cl2 O22 60.9(8) . 3
O23 Cl2 O22 110.2(8) 3 3
O21 Cl2 O22 99.7(6) . 3
O24 Cl2 O22 105.4(7) 3 3
O24 Cl2 O22 67.4(8) . 3
O22 Cl2 O22 160.6(13) . 3
C38 O1 Zn1 108.1(3) . 3_655
Zn1 O3 H31 113(5) . .
Zn1 O3 H32 136(5) . .
H31 O3 H32 107(3) . .
O14 O14 Cl1 127(3) 3_665 .
O14 O14 Cl1 33.8(18) 3_665 3_665
Cl1 O14 Cl1 128.4(14) . 3_665
O23 O22 Cl2 57.4(5) 3 .
O23 O22 O24 102.7(9) 3 3
Cl2 O22 O24 55.6(5) . 3
O24 O23 Cl2 69.7(6) 3 .
O24 O23 O22 131.3(9) 3 3
Cl2 O23 O22 61.7(5) . 3
O23 O24 Cl2 65.8(6) 3 .
O23 O24 O22 120.5(10) 3 3
Cl2 O24 O22 57.0(5) . 3
C16 N1 C12 119.3(5) . .
C16 N1 Zn1 125.1(4) . .
C12 N1 Zn1 115.5(3) . .
C22 N2 C26 119.3(5) . .
C22 N2 Zn1 117.5(5) . .
C26 N2 Zn1 122.8(4) . .
C21 N3 C31 117.4(12) . .
C21 N3 C11 111.3(6) . .
C31 N3 C11 106.2(11) . .
C21 N3 C51 108.9(11) . .
C31 N3 C51 19.6(13) . .
C11 N3 C51 125.1(11) . .
C21 N3 C41 107.7(11) . .
C31 N3 C41 14.0(13) . .
C11 N3 C41 102.6(9) . .
C51 N3 C41 28.6(9) . .
C21 N3 Zn1 104.5(4) . .
C31 N3 Zn1 110.9(7) . .
C11 N3 Zn1 106.0(4) . .
C51 N3 Zn1 98.1(8) . .
C41 N3 Zn1 124.6(9) . .
N3 C11 C12 110.7(5) . .
N3 C11 H11A 109.5 . .
C12 C11 H11A 109.5 . .
N3 C11 H11B 109.5 . .
C12 C11 H11B 109.5 . .
H11A C11 H11B 108.1 . .
N1 C12 C13 121.6(6) . .
N1 C12 C11 117.8(5) . .
C13 C12 C11 120.4(6) . .
C14 C13 C12 117.9(7) . .
C14 C13 H13 121.0 . .
C12 C13 H13 121.0 . .
C15 C14 C13 120.2(6) . .
C15 C14 H14 119.9 . .
C13 C14 H14 119.9 . .
C14 C15 C16 119.2(6) . .
C14 C15 H15 120.4 . .
C16 C15 H15 120.4 . .
N1 C16 C15 121.7(6) . .
N1 C16 H16 119.2 . .
C15 C16 H16 119.2 . .
N3 C21 C22 111.1(6) . .
N3 C21 H21A 109.4 . .
C22 C21 H21A 109.4 . .
N3 C21 H21B 109.4 . .
C22 C21 H21B 109.4 . .
H21A C21 H21B 108.0 . .
N2 C22 C23 121.5(7) . .
N2 C22 C21 116.0(5) . .
C23 C22 C21 122.5(7) . .
C24 C23 C22 119.0(7) . .
C24 C23 H23 120.5 . .
C22 C23 H23 120.5 . .
C23 C24 C25 120.7(6) . .
C23 C24 H24 119.7 . .
C25 C24 H24 119.7 . .
C26 C25 C24 116.0(8) . .
C26 C25 H25 122.0 . .
C24 C25 H25 122.0 . .
N2 C26 C25 123.5(7) . .
N2 C26 H26 118.3 . .
C25 C26 H26 118.3 . .
N3 C31 C32 114.4(12) . .
N3 C31 H31A 108.7 . .
C32 C31 H31A 108.7 . .
N3 C31 H31B 108.7 . .
C32 C31 H31B 108.7 . .
H31A C31 H31B 107.6 . .
C33 C32 C31 111.7(12) . .
C33 C32 H32A 109.3 . .
C31 C32 H32A 109.3 . .
C33 C32 H32B 109.3 . .
C31 C32 H32B 109.3 . .
H32A C32 H32B 107.9 . .
C34 C33 C32 118.3(12) . .
C34 C33 H33A 107.7 . .
C32 C33 H33A 107.7 . .
C34 C33 H33B 107.7 . .
C32 C33 H33B 107.7 . .
H33A C33 H33B 107.1 . .
C33 C34 C35 119.5(11) . .
C33 C34 H34A 107.4 . .
C35 C34 H34A 107.4 . .
C33 C34 H34B 107.4 . .
C35 C34 H34B 107.4 . .
H34A C34 H34B 107.0 . .
C34 C35 C36 118.0(12) . .
C34 C35 H35A 107.8 . .
C36 C35 H35A 107.8 . .
C34 C35 H35B 107.8 . .
C36 C35 H35B 107.8 . .
H35A C35 H35B 107.1 . .
C35 C36 C37 115.3(17) . .
C35 C36 H36A 108.4 . .
C37 C36 H36A 108.4 . .
C35 C36 H36B 108.4 . .
C37 C36 H36B 108.4 . .
H36A C36 H36B 107.5 . .
C36 C37 C38 122.3(19) . .
C36 C37 H37A 106.8 . .
C38 C37 H37A 106.8 . .
C36 C37 H37B 106.8 . .
C38 C37 H37B 106.8 . .
H37A C37 H37B 106.6 . .
O2 C38 O1 121.1(5) . .
O2 C38 C57 121.4(13) . .
O1 C38 C57 115.1(12) . .
O2 C38 C37 114.7(12) . .
O1 C38 C37 122.5(13) . .
C57 C38 C37 29.7(11) . .
O2 C38 C47 122.6(15) . .
O1 C38 C47 116.3(14) . .
C57 C38 C47 15.6(12) . .
C37 C38 C47 15.0(11) . .
C42 C41 N3 115.4(14) . .
C42 C41 H41A 108.4 . .
N3 C41 H41A 108.4 . .
C42 C41 H41B 108.4 . .
N3 C41 H41B 108.4 . .
H41A C41 H41B 107.5 . .
C43 C42 C41 114.7(12) . .
C43 C42 H42A 108.6 . .
C41 C42 H42A 108.6 . .
C43 C42 H42B 108.6 . .
C41 C42 H42B 108.6 . .
H42A C42 H42B 107.6 . .
C42 C43 C44 115.9(10) . .
C42 C43 H43A 108.3 . .
C44 C43 H43A 108.3 . .
C42 C43 H43B 108.3 . .
C44 C43 H43B 108.3 . .
H43A C43 H43B 107.4 . .
C43 C44 C45 113.2(10) . .
C43 C44 H44A 108.9 . .
C45 C44 H44A 108.9 . .
C43 C44 H44B 108.9 . .
C45 C44 H44B 108.9 . .
H44A C44 H44B 107.7 . .
C46 C45 C44 115.9(13) . .
C46 C45 H45A 108.3 . .
C44 C45 H45A 108.3 . .
C46 C45 H45B 108.3 . .
C44 C45 H45B 108.3 . .
H45A C45 H45B 107.4 . .
C45 C46 C47 114.1(16) . .
C45 C46 H46A 108.7 . .
C47 C46 H46A 108.7 . .
C45 C46 H46B 108.7 . .
C47 C46 H46B 108.7 . .
H46A C46 H46B 107.6 . .
C46 C47 C38 110(2) . .
C46 C47 H47A 109.7 . .
C38 C47 H47A 109.7 . .
C46 C47 H47B 109.7 . .
C38 C47 H47B 109.7 . .
H47A C47 H47B 108.2 . .
N3 C51 C52 110.5(13) . .
N3 C51 H51A 109.6 . .
C52 C51 H51A 109.6 . .
N3 C51 H51B 109.6 . .
C52 C51 H51B 109.6 . .
H51A C51 H51B 108.1 . .
C53 C52 C51 111.5(13) . .
C53 C52 H52A 109.3 . .
C51 C52 H52A 109.3 . .
C53 C52 H52B 109.3 . .
C51 C52 H52B 109.3 . .
H52A C52 H52B 108.0 . .
C54 C53 C52 113.6(13) . .
C54 C53 H53A 108.8 . .
C52 C53 H53A 108.8 . .
C54 C53 H53B 108.8 . .
C52 C53 H53B 108.8 . .
H53A C53 H53B 107.7 . .
C53 C54 C55 112.3(12) . .
C53 C54 H54A 109.1 . .
C55 C54 H54A 109.1 . .
C53 C54 H54B 109.1 . .
C55 C54 H54B 109.1 . .
H54A C54 H54B 107.9 . .
C56 C55 C54 113.3(14) . .
C56 C55 H55A 108.9 . .
C54 C55 H55A 108.9 . .
C56 C55 H55B 108.9 . .
C54 C55 H55B 108.9 . .
H55A C55 H55B 107.7 . .
C55 C56 C57 112.6(14) . .
C55 C56 H56A 109.1 . .
C57 C56 H56A 109.1 . .
C55 C56 H56B 109.1 . .
C57 C56 H56B 109.1 . .
H56A C56 H56B 107.8 . .
C38 C57 C56 110(2) . .
C38 C57 H57A 109.7 . .
C56 C57 H57A 109.7 . .
C38 C57 H57B 109.7 . .
C56 C57 H57B 109.7 . .
H57A C57 H57B 108.2 . .
O14' Cl1' O12' 110.3(11) . .
O14' Cl1' O13' 112.2(10) . .
O12' Cl1' O13' 109.5(10) . .
O14' Cl1' O11' 110.5(11) . .
O12' Cl1' O11' 107.7(11) . .
O13' Cl1' O11' 106.5(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O1 1.978(4) 3_655
Zn1 N2 2.055(4) .
Zn1 O3 2.067(5) .
Zn1 N1 2.093(4) .
Zn1 N3 2.230(6) .
Cl1 O14 1.390(15) .
Cl1 O13 1.409(15) .
Cl1 O12 1.435(15) .
Cl1 O11 1.485(16) .
Cl1 O14 2.00(2) 3_665
Cl2 O23 1.363(8) .
Cl2 O23 1.363(8) 3
Cl2 O21 1.389(6) .
Cl2 O24 1.401(8) 3
Cl2 O24 1.401(8) .
Cl2 O22 1.423(8) .
Cl2 O22 1.423(8) 3
O1 C38 1.259(7) .
O1 Zn1 1.978(4) 3_655
O2 C38 1.253(6) .
O3 H31 0.8399(12) .
O3 H32 0.8400(12) .
O14 O14 0.83(4) 3_665
O14 Cl1 2.00(2) 3_665
O22 O23 1.413(18) 3
O22 O24 1.568(18) 3
O23 O24 1.048(17) 3
O23 O22 1.413(18) 3
O24 O23 1.048(17) 3
O24 O22 1.568(18) 3
N1 C16 1.335(7) .
N1 C12 1.339(8) .
N2 C22 1.312(8) .
N2 C26 1.332(8) .
N3 C21 1.481(8) .
N3 C31 1.482(13) .
N3 C11 1.487(9) .
N3 C51 1.527(14) .
N3 C41 1.532(13) .
C11 C12 1.505(8) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.394(8) .
C13 C14 1.369(10) .
C13 H13 0.9500 .
C14 C15 1.368(10) .
C14 H14 0.9500 .
C15 C16 1.369(8) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C21 C22 1.516(11) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 C23 1.406(9) .
C23 C24 1.347(12) .
C23 H23 0.9500 .
C24 C25 1.398(12) .
C24 H24 0.9500 .
C25 C26 1.393(8) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C31 C32 1.498(15) .
C31 H31A 0.9900 .
C31 H31B 0.9900 .
C32 C33 1.493(13) .
C32 H32A 0.9900 .
C32 H32B 0.9900 .
C33 C34 1.455(13) .
C33 H33A 0.9900 .
C33 H33B 0.9900 .
C34 C35 1.469(12) .
C34 H34A 0.9900 .
C34 H34B 0.9900 .
C35 C36 1.481(16) .
C35 H35A 0.9900 .
C35 H35B 0.9900 .
C36 C37 1.492(16) .
C36 H36A 0.9900 .
C36 H36B 0.9900 .
C37 C38 1.54(3) .
C37 H37A 0.9900 .
C37 H37B 0.9900 .
C38 C57 1.50(4) .
C38 C47 1.55(4) .
C41 C42 1.517(16) .
C41 H41A 0.9900 .
C41 H41B 0.9900 .
C42 C43 1.506(13) .
C42 H42A 0.9900 .
C42 H42B 0.9900 .
C43 C44 1.520(13) .
C43 H43A 0.9900 .
C43 H43B 0.9900 .
C44 C45 1.521(13) .
C44 H44A 0.9900 .
C44 H44B 0.9900 .
C45 C46 1.505(16) .
C45 H45A 0.9900 .
C45 H45B 0.9900 .
C46 C47 1.517(16) .
C46 H46A 0.9900 .
C46 H46B 0.9900 .
C47 H47A 0.9900 .
C47 H47B 0.9900 .
C51 C52 1.534(15) .
C51 H51A 0.9900 .
C51 H51B 0.9900 .
C52 C53 1.525(14) .
C52 H52A 0.9900 .
C52 H52B 0.9900 .
C53 C54 1.521(13) .
C53 H53A 0.9900 .
C53 H53B 0.9900 .
C54 C55 1.531(14) .
C54 H54A 0.9900 .
C54 H54B 0.9900 .
C55 C56 1.512(14) .
C55 H55A 0.9900 .
C55 H55B 0.9900 .
C56 C57 1.520(16) .
C56 H56A 0.9900 .
C56 H56B 0.9900 .
C57 H57A 0.9900 .
C57 H57B 0.9900 .
Cl1' O14' 1.422(15) .
Cl1' O12' 1.456(15) .
Cl1' O13' 1.462(15) .
Cl1' O11' 1.478(15) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H31 O21 0.8399(12) 2.24(5) 2.963(5) 144(8) .
O3 H32 O2 0.8400(12) 1.79(2) 2.597(6) 161(7) 14_565
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_4
O13 Cl1 O14 O14 -2(3) . 3_665
O12 Cl1 O14 O14 -130(3) . 3_665
O11 Cl1 O14 O14 114(3) . 3_665
O13 Cl1 O14 Cl1 -45(2) . 3_665
O12 Cl1 O14 Cl1 -172.6(18) . 3_665
O11 Cl1 O14 Cl1 71(2) . 3_665
O14 Cl1 O14 Cl1 -43.0(15) 3_665 3_665
O23 Cl2 O22 O23 126.2(14) . 3
O21 Cl2 O22 O23 -112.9(8) . 3
O24 Cl2 O22 O23 139.0(11) 3 3
O24 Cl2 O22 O23 1.5(12) . 3
O22 Cl2 O22 O23 67.1(8) 3 3
O23 Cl2 O22 O24 -12.8(12) . 3
O23 Cl2 O22 O24 -139.0(11) 3 3
O21 Cl2 O22 O24 108.1(7) . 3
O24 Cl2 O22 O24 -137.5(14) . 3
O22 Cl2 O22 O24 -71.9(7) 3 3
O23 Cl2 O23 O24 85.4(12) 3 3
O21 Cl2 O23 O24 -94.6(12) . 3
O24 Cl2 O23 O24 135.9(16) . 3
O22 Cl2 O23 O24 16.9(16) . 3
O22 Cl2 O23 O24 177.9(17) 3 3
O23 Cl2 O23 O22 -92.4(8) 3 3
O21 Cl2 O23 O22 87.6(8) . 3
O24 Cl2 O23 O22 -177.9(17) 3 3
O24 Cl2 O23 O22 -41.9(11) . 3
O22 Cl2 O23 O22 -160.9(13) . 3
O23 Cl2 O24 O23 -123.6(17) . 3
O21 Cl2 O24 O23 104.9(12) . 3
O24 Cl2 O24 O23 -75.1(12) 3 3
O22 Cl2 O24 O23 -1.9(16) . 3
O22 Cl2 O24 O23 -162.8(16) 3 3
O23 Cl2 O24 O22 39.2(11) . 3
O23 Cl2 O24 O22 162.8(16) 3 3
O21 Cl2 O24 O22 -92.3(7) . 3
O24 Cl2 O24 O22 87.7(7) 3 3
O22 Cl2 O24 O22 160.9(13) . 3
O1 Zn1 N1 C16 102.0(4) 3_655 .
N2 Zn1 N1 C16 -96.1(4) . .
O3 Zn1 N1 C16 3.1(4) . .
N3 Zn1 N1 C16 -168.2(4) . .
O1 Zn1 N1 C12 -79.6(4) 3_655 .
N2 Zn1 N1 C12 82.2(4) . .
O3 Zn1 N1 C12 -178.6(4) . .
N3 Zn1 N1 C12 10.1(4) . .
O1 Zn1 N2 C22 95.5(4) 3_655 .
O3 Zn1 N2 C22 -159.2(4) . .
N1 Zn1 N2 C22 -61.8(5) . .
N3 Zn1 N2 C22 10.3(4) . .
O1 Zn1 N2 C26 -77.5(5) 3_655 .
O3 Zn1 N2 C26 27.9(5) . .
N1 Zn1 N2 C26 125.3(4) . .
N3 Zn1 N2 C26 -162.6(5) . .
O1 Zn1 N3 C21 -156.7(4) 3_655 .
N2 Zn1 N3 C21 -25.5(4) . .
O3 Zn1 N3 C21 42.7(11) . .
N1 Zn1 N3 C21 92.9(4) . .
O1 Zn1 N3 C31 -29.3(13) 3_655 .
N2 Zn1 N3 C31 101.9(13) . .
O3 Zn1 N3 C31 170.1(14) . .
N1 Zn1 N3 C31 -139.8(13) . .
O1 Zn1 N3 C11 85.6(4) 3_655 .
N2 Zn1 N3 C11 -143.2(4) . .
O3 Zn1 N3 C11 -75.0(11) . .
N1 Zn1 N3 C11 -24.9(4) . .
O1 Zn1 N3 C51 -44.6(11) 3_655 .
N2 Zn1 N3 C51 86.6(11) . .
O3 Zn1 N3 C51 154.8(14) . .
N1 Zn1 N3 C51 -155.1(11) . .
O1 Zn1 N3 C41 -32.7(12) 3_655 .
N2 Zn1 N3 C41 98.5(12) . .
O3 Zn1 N3 C41 166.7(13) . .
N1 Zn1 N3 C41 -143.2(12) . .
C21 N3 C11 C12 -77.8(7) . .
C31 N3 C11 C12 153.3(10) . .
C51 N3 C11 C12 147.7(11) . .
C41 N3 C11 C12 167.3(11) . .
Zn1 N3 C11 C12 35.3(6) . .
C16 N1 C12 C13 1.0(8) . .
Zn1 N1 C12 C13 -177.4(5) . .
C16 N1 C12 C11 -173.8(5) . .
Zn1 N1 C12 C11 7.8(7) . .
N3 C11 C12 N1 -30.7(8) . .
N3 C11 C12 C13 154.4(6) . .
N1 C12 C13 C14 -2.5(9) . .
C11 C12 C13 C14 172.2(6) . .
C12 C13 C14 C15 2.6(11) . .
C13 C14 C15 C16 -1.2(11) . .
C12 N1 C16 C15 0.5(8) . .
Zn1 N1 C16 C15 178.8(4) . .
C14 C15 C16 N1 -0.4(9) . .
C31 N3 C21 C22 -86.8(11) . .
C11 N3 C21 C22 150.5(5) . .
C51 N3 C21 C22 -67.5(10) . .
C41 N3 C21 C22 -97.7(10) . .
Zn1 N3 C21 C22 36.5(6) . .
C26 N2 C22 C23 0.5(8) . .
Zn1 N2 C22 C23 -172.7(4) . .
C26 N2 C22 C21 -178.5(5) . .
Zn1 N2 C22 C21 8.3(7) . .
N3 C21 C22 N2 -32.3(8) . .
N3 C21 C22 C23 148.7(6) . .
N2 C22 C23 C24 0.8(9) . .
C21 C22 C23 C24 179.7(6) . .
C22 C23 C24 C25 -1.4(10) . .
C23 C24 C25 C26 0.7(9) . .
C22 N2 C26 C25 -1.2(9) . .
Zn1 N2 C26 C25 171.6(4) . .
C24 C25 C26 N2 0.6(9) . .
C21 N3 C31 C32 -68(2) . .
C11 N3 C31 C32 58(2) . .
C51 N3 C31 C32 -136(6) . .
C41 N3 C31 C32 -19(6) . .
Zn1 N3 C31 C32 172.3(15) . .
N3 C31 C32 C33 177.4(17) . .
C31 C32 C33 C34 168.0(17) . .
C32 C33 C34 C35 178.0(14) . .
C33 C34 C35 C36 -57(2) . .
C34 C35 C36 C37 167.8(19) . .
C35 C36 C37 C38 176(2) . .
Zn1 O1 C38 O2 1.9(8) 3_655 .
Zn1 O1 C38 C57 164.6(10) 3_655 .
Zn1 O1 C38 C37 -162.4(11) 3_655 .
Zn1 O1 C38 C47 -178.1(11) 3_655 .
C36 C37 C38 O2 -21(3) . .
C36 C37 C38 O1 144(2) . .
C36 C37 C38 C57 -132(5) . .
C36 C37 C38 C47 -147(12) . .
C21 N3 C41 C42 62.9(18) . .
C31 N3 C41 C42 -73(7) . .
C11 N3 C41 C42 -179.6(15) . .
C51 N3 C41 C42 -34(2) . .
Zn1 N3 C41 C42 -60(2) . .
N3 C41 C42 C43 159.3(13) . .
C41 C42 C43 C44 62.8(19) . .
C42 C43 C44 C45 170.6(13) . .
C43 C44 C45 C46 179.1(18) . .
C44 C45 C46 C47 -176(2) . .
C45 C46 C47 C38 -66(3) . .
O2 C38 C47 C46 -37(2) . .
O1 C38 C47 C46 143.2(17) . .
C57 C38 C47 C46 -127(9) . .
C37 C38 C47 C46 25(9) . .
C21 N3 C51 C52 -75.2(19) . .
C31 N3 C51 C52 44(4) . .
C11 N3 C51 C52 60(2) . .
C41 N3 C51 C52 17(2) . .
Zn1 N3 C51 C52 176.4(16) . .
N3 C51 C52 C53 -170.9(17) . .
C51 C52 C53 C54 175.2(17) . .
C52 C53 C54 C55 177.7(16) . .
C53 C54 C55 C56 -178.8(17) . .
C54 C55 C56 C57 -179(2) . .
O2 C38 C57 C56 -46(2) . .
O1 C38 C57 C56 151.0(14) . .
C37 C38 C57 C56 39(3) . .
C47 C38 C57 C56 53(7) . .
C55 C56 C57 C38 -59(3) . .
