#------------------------------------------------------------------------------
#$Date: 2016-03-05 11:24:19 +0200 (Sat, 05 Mar 2016) $
#$Revision: 177775 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/72/7037244.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_7037244
loop_
_publ_author_name
'Jędrzkiewicz, D'
'Ejfler, J.'
'John, Ł'
'Szafert, S.'
_publ_section_title
;
 Zebra reaction or the recipe for the synthesis of heterodimeric zinc
 complexes.
;
_journal_issue                   7
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2829
_journal_page_last               2838
_journal_paper_doi               10.1039/c5dt03883a
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         'C44 H62 N2 O2 Zn2'
_chemical_formula_sum            'C44 H62 N2 O2 Zn2'
_chemical_formula_weight         781.69
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-10-29 deposited with the CCDC.
2015-11-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.64(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.582(5)
_cell_length_b                   10.542(3)
_cell_length_c                   13.030(4)
_cell_measurement_reflns_used    11513
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.4967
_cell_measurement_theta_min      2.9797
_cell_volume                     1980.3(11)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2013/1 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3359
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.728
_diffrn_measurement_device_type  'Kuma KM-4-CCD κ-geometry'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.728
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14537
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.728
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         32.548
_diffrn_reflns_theta_min         2.984
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.249
_exptl_absorpt_correction_T_max  0.869
_exptl_absorpt_correction_T_min  0.603
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.460
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.707
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         5239
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0341
_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)+(0.0714P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1020
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4552
_reflns_number_total             5239
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5dt03883a2.cif
_cod_data_source_block           RS-Zn
_cod_depositor_comments
'Adding full bibliography for 7037244--7037248.cif.'
_cod_database_code               7037244
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.547
_shelx_estimated_absorpt_t_max   0.854
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Zn1 Zn 0.52641(2) 0.36083(2) 0.51389(2) 0.01369(8) Uani 1 1 d . .
O1 O 0.54362(6) 0.50383(9) 0.41590(8) 0.0144(2) Uani 1 1 d . .
N1 N 0.66151(9) 0.38712(12) 0.60175(10) 0.0133(2) Uani 1 1 d . .
C1 C 0.62764(9) 0.52545(13) 0.38704(11) 0.0138(3) Uani 1 1 d . .
C2 C 0.70894(10) 0.52590(13) 0.46006(11) 0.0146(3) Uani 1 1 d . .
C3 C 0.79398(10) 0.55185(14) 0.42670(11) 0.0158(3) Uani 1 1 d . .
H3 H 0.8486 0.5524 0.4766 0.019 Uiso 1 1 calc R U
C4 C 0.80171(10) 0.57689(14) 0.32300(12) 0.0157(3) Uani 1 1 d . .
C5 C 0.71963(10) 0.57379(14) 0.25212(11) 0.0158(3) Uani 1 1 d . .
H5 H 0.7222 0.5895 0.1808 0.019 Uiso 1 1 calc R U
C6 C 0.63424(10) 0.54827(14) 0.28305(11) 0.0154(3) Uani 1 1 d . .
H6 H 0.5799 0.5464 0.2328 0.018 Uiso 1 1 calc R U
C7 C 0.89406(11) 0.60248(16) 0.28369(12) 0.0188(3) Uani 1 1 d . .
C8 C 0.97430(13) 0.6218(2) 0.37162(16) 0.0343(4) Uani 1 1 d . .
H8A H 0.9592 0.6907 0.4167 0.051 Uiso 1 1 calc R U
H8B H 1.0305 0.6437 0.3426 0.051 Uiso 1 1 calc R U
H8C H 0.9849 0.5435 0.4121 0.051 Uiso 1 1 calc R U
C9 C 0.91670(12) 0.48949(16) 0.21769(15) 0.0276(4) Uani 1 1 d . .
H9A H 0.9243 0.4129 0.2608 0.041 Uiso 1 1 calc R U
H9B H 0.9743 0.5065 0.1899 0.041 Uiso 1 1 calc R U
H9C H 0.8660 0.4768 0.1602 0.041 Uiso 1 1 calc R U
C10 C 0.88664(12) 0.72152(16) 0.21443(15) 0.0259(3) Uani 1 1 d . .
H10A H 0.8368 0.7099 0.1558 0.039 Uiso 1 1 calc R U
H10B H 0.9455 0.7349 0.1883 0.039 Uiso 1 1 calc R U
H10C H 0.8730 0.7955 0.2551 0.039 Uiso 1 1 calc R U
C11 C 0.70296(10) 0.50993(14) 0.57433(11) 0.0150(3) Uani 1 1 d . .
H11A H 0.7662 0.5171 0.6141 0.018 Uiso 1 1 calc R U
H11B H 0.6655 0.5803 0.5965 0.018 Uiso 1 1 calc R U
C12 C 0.71978(10) 0.28070(14) 0.57495(12) 0.0183(3) Uani 1 1 d . .
H12A H 0.6958 0.2007 0.5986 0.027 Uiso 1 1 calc R U
H12B H 0.7838 0.2932 0.6089 0.027 Uiso 1 1 calc R U
H12C H 0.7183 0.2778 0.4995 0.027 Uiso 1 1 calc R U
C13 C 0.64966(11) 0.38865(14) 0.71501(12) 0.0152(3) Uani 1 1 d . .
H13 H 0.6154 0.4685 0.7260 0.018 Uiso 1 1 calc R U
C14 C 0.58793(10) 0.27936(15) 0.73999(12) 0.0199(3) Uani 1 1 d . .
H14A H 0.5266 0.2874 0.6979 0.030 Uiso 1 1 calc R U
H14B H 0.5816 0.2820 0.8138 0.030 Uiso 1 1 calc R U
H14C H 0.6160 0.1985 0.7243 0.030 Uiso 1 1 calc R U
C15 C 0.73939(10) 0.39312(15) 0.79082(12) 0.0160(3) Uani 1 1 d . .
C16 C 0.76908(11) 0.50714(15) 0.83938(13) 0.0201(3) Uani 1 1 d . .
H16 H 0.7358 0.5830 0.8200 0.024 Uiso 1 1 calc R U
C17 C 0.84658(11) 0.51104(16) 0.91562(13) 0.0240(3) Uani 1 1 d . .
H17 H 0.8654 0.5893 0.9483 0.029 Uiso 1 1 calc R U
C18 C 0.89665(11) 0.40182(17) 0.94436(13) 0.0224(3) Uani 1 1 d . .
H18 H 0.9497 0.4047 0.9965 0.027 Uiso 1 1 calc R U
C19 C 0.86846(11) 0.28809(16) 0.89604(12) 0.0204(3) Uani 1 1 d . .
H19 H 0.9029 0.2129 0.9148 0.024 Uiso 1 1 calc R U
C20 C 0.79069(10) 0.28307(15) 0.82077(12) 0.0177(3) Uani 1 1 d . .
H20 H 0.7718 0.2043 0.7890 0.021 Uiso 1 1 calc R U
C21 C 0.46883(11) 0.19447(16) 0.47145(14) 0.0239(3) Uani 1 1 d . .
H21A H 0.4376 0.2019 0.3988 0.029 Uiso 1 1 calc R U
H21B H 0.5191 0.1311 0.4723 0.029 Uiso 1 1 calc R U
C22 C 0.39888(14) 0.14326(15) 0.53662(16) 0.0281(4) Uani 1 1 d . .
H22A H 0.3734 0.0630 0.5070 0.042 Uiso 1 1 calc R U
H22B H 0.3485 0.2048 0.5370 0.042 Uiso 1 1 calc R U
H22C H 0.4296 0.1290 0.6079 0.042 Uiso 1 1 calc R U
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'
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
C21 Zn1 O1 124.86(6) . .
C21 Zn1 O1 121.40(6) . 3_666
O1 Zn1 O1 83.10(5) . 3_666
C21 Zn1 N1 125.39(6) . .
O1 Zn1 N1 92.85(5) . .
O1 Zn1 N1 98.70(5) 3_666 .
C21 Zn1 Zn1 136.85(5) . 3_666
O1 Zn1 Zn1 41.96(3) . 3_666
O1 Zn1 Zn1 41.14(3) 3_666 3_666
N1 Zn1 Zn1 97.75(4) . 3_666
C1 O1 Zn1 120.39(8) . .
C1 O1 Zn1 122.65(9) . 3_666
Zn1 O1 Zn1 96.90(5) . 3_666
C12 N1 C11 109.45(12) . .
C12 N1 C13 113.10(12) . .
C11 N1 C13 109.50(11) . .
C12 N1 Zn1 106.86(9) . .
C11 N1 Zn1 110.89(9) . .
C13 N1 Zn1 106.99(9) . .
O1 C1 C6 119.78(13) . .
O1 C1 C2 121.30(13) . .
C6 C1 C2 118.91(13) . .
C3 C2 C1 119.14(13) . .
C3 C2 C11 120.75(13) . .
C1 C2 C11 119.89(13) . .
C4 C3 C2 122.71(14) . .
C4 C3 H3 118.6 . .
C2 C3 H3 118.6 . .
C3 C4 C5 116.67(13) . .
C3 C4 C7 123.92(13) . .
C5 C4 C7 119.38(13) . .
C6 C5 C4 121.85(13) . .
C6 C5 H5 119.1 . .
C4 C5 H5 119.1 . .
C5 C6 C1 120.70(13) . .
C5 C6 H6 119.6 . .
C1 C6 H6 119.6 . .
C8 C7 C9 108.66(15) . .
C8 C7 C4 112.69(14) . .
C9 C7 C4 108.92(13) . .
C8 C7 C10 108.06(15) . .
C9 C7 C10 107.83(14) . .
C4 C7 C10 110.55(13) . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C7 C9 H9A 109.5 . .
C7 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C7 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C7 C10 H10A 109.5 . .
C7 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C7 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
N1 C11 C2 114.62(12) . .
N1 C11 H11A 108.6 . .
C2 C11 H11A 108.6 . .
N1 C11 H11B 108.6 . .
C2 C11 H11B 108.6 . .
H11A C11 H11B 107.6 . .
N1 C12 H12A 109.5 . .
N1 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
N1 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
N1 C13 C15 114.97(12) . .
N1 C13 C14 110.96(12) . .
C15 C13 C14 111.29(12) . .
N1 C13 H13 106.3 . .
C15 C13 H13 106.3 . .
C14 C13 H13 106.3 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C16 C15 C20 117.99(14) . .
C16 C15 C13 120.01(13) . .
C20 C15 C13 121.79(14) . .
C17 C16 C15 120.88(15) . .
C17 C16 H16 119.6 . .
C15 C16 H16 119.6 . .
C18 C17 C16 120.55(15) . .
C18 C17 H17 119.7 . .
C16 C17 H17 119.7 . .
C17 C18 C19 119.19(15) . .
C17 C18 H18 120.4 . .
C19 C18 H18 120.4 . .
C20 C19 C18 120.65(15) . .
C20 C19 H19 119.7 . .
C18 C19 H19 119.7 . .
C19 C20 C15 120.74(15) . .
C19 C20 H20 119.6 . .
C15 C20 H20 119.6 . .
C22 C21 Zn1 116.66(12) . .
C22 C21 H21A 108.1 . .
Zn1 C21 H21A 108.1 . .
C22 C21 H21B 108.1 . .
Zn1 C21 H21B 108.1 . .
H21A C21 H21B 107.3 . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 C21 1.9866(17) .
Zn1 O1 2.0155(11) .
Zn1 O1 2.0485(11) 3_666
Zn1 N1 2.1426(15) .
Zn1 Zn1 3.0415(9) 3_666
O1 C1 1.3538(17) .
O1 Zn1 2.0485(11) 3_666
N1 C12 1.4804(19) .
N1 C11 1.4947(18) .
N1 C13 1.511(2) .
C1 C6 1.394(2) .
C1 C2 1.404(2) .
C2 C3 1.401(2) .
C2 C11 1.514(2) .
C3 C4 1.398(2) .
C3 H3 0.9500 .
C4 C5 1.398(2) .
C4 C7 1.535(2) .
C5 C6 1.391(2) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 C8 1.523(3) .
C7 C9 1.534(2) .
C7 C10 1.540(2) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C15 1.517(2) .
C13 C14 1.527(2) .
C13 H13 1.0000 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 C16 1.396(2) .
C15 C20 1.404(2) .
C16 C17 1.389(2) .
C16 H16 0.9500 .
C17 C18 1.385(2) .
C17 H17 0.9500 .
C18 C19 1.387(2) .
C18 H18 0.9500 .
C19 C20 1.384(2) .
C19 H19 0.9500 .
C20 H20 0.9500 .
C21 C22 1.521(2) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
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
Zn1 O1 C1 C6 134.76(12) .
Zn1 O1 C1 C6 -102.48(14) 3_666
Zn1 O1 C1 C2 -45.49(16) .
Zn1 O1 C1 C2 77.28(15) 3_666
O1 C1 C2 C3 -178.44(13) .
C6 C1 C2 C3 1.3(2) .
O1 C1 C2 C11 -3.8(2) .
C6 C1 C2 C11 176.00(13) .
C1 C2 C3 C4 -0.3(2) .
C11 C2 C3 C4 -174.98(13) .
C2 C3 C4 C5 -0.6(2) .
C2 C3 C4 C7 -178.48(14) .
C3 C4 C5 C6 0.6(2) .
C7 C4 C5 C6 178.57(14) .
C4 C5 C6 C1 0.4(2) .
O1 C1 C6 C5 178.41(13) .
C2 C1 C6 C5 -1.3(2) .
C3 C4 C7 C8 -10.5(2) .
C5 C4 C7 C8 171.63(15) .
C3 C4 C7 C9 110.11(17) .
C5 C4 C7 C9 -67.72(18) .
C3 C4 C7 C10 -131.59(16) .
C5 C4 C7 C10 50.59(19) .
C12 N1 C11 C2 61.70(15) .
C13 N1 C11 C2 -173.80(12) .
Zn1 N1 C11 C2 -55.96(14) .
C3 C2 C11 N1 -124.16(14) .
C1 C2 C11 N1 61.24(17) .
C12 N1 C13 C15 56.70(17) .
C11 N1 C13 C15 -65.65(15) .
Zn1 N1 C13 C15 174.09(10) .
C12 N1 C13 C14 -70.68(15) .
C11 N1 C13 C14 166.97(12) .
Zn1 N1 C13 C14 46.71(13) .
N1 C13 C15 C16 102.31(16) .
C14 C13 C15 C16 -130.48(15) .
N1 C13 C15 C20 -82.98(17) .
C14 C13 C15 C20 44.23(19) .
C20 C15 C16 C17 -0.6(2) .
C13 C15 C16 C17 174.36(15) .
C15 C16 C17 C18 0.7(2) .
C16 C17 C18 C19 0.0(2) .
C17 C18 C19 C20 -0.7(2) .
C18 C19 C20 C15 0.8(2) .
C16 C15 C20 C19 -0.2(2) .
C13 C15 C20 C19 -174.98(14) .
