#------------------------------------------------------------------------------
#$Date: 2023-12-06 17:50:21 +0200 (Wed, 06 Dec 2023) $
#$Revision: 288091 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/42/4114274.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_4114274
loop_
_publ_author_name
'Janusz Lewiński'
'Wojciech Marciniak'
'Janusz Lipkowski'
'Iwona Justyniak'
_publ_contact_author
;
   Dr. Janusz Lewiński,
   Department of Chemistry
   Warsaw University of Technology
   Noakowskiego 3,
   PL-00-664 Warszawa
   Poland
;
_publ_contact_author_email       lewin@ch.pw.edu.pl
_publ_contact_author_fax         '048 22 6607279'
_publ_contact_author_phone       '048 22 6607315'
_publ_section_title
;
 New Insights into the Reaction of Zinc Alkyls with Dioxygen
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12698
_journal_page_last               12699
_journal_paper_doi               10.1021/ja036020t
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C24 H52 N4 O8 Zn4'
_chemical_formula_weight         786.18
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-97 + manual edition'
_cell_angle_alpha                90.00
_cell_angle_beta                 96.2400(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.6310(2)
_cell_length_b                   9.5120(2)
_cell_length_c                   16.8370(3)
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.02
_cell_measurement_theta_min      2.36
_cell_volume                     3284.55(10)
_computing_cell_refinement       'Denzo & Scalepak (Otwinowski, Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction        'Denzo & Scalepak (Otwinowski, Minor, 1997)'
_computing_molecular_graphics
;
ORTEP III (Burnett, Johnson, 1996) 
;
_computing_publication_material
;
SHELXL-97 (Sheldrick, 1997) 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.473
_diffrn_measured_fraction_theta_max 0.473
_diffrn_measurement_device       'κ-geometry diffractometr'
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       'area detector φ and ω scans'
_diffrn_measurement_specimen_support 'glass capillary'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5686
_diffrn_reflns_theta_full        32.02
_diffrn_reflns_theta_max         32.02
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    2.933
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details   'Scalepak (Otwinowski, Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_description       prism
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.681
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         5686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0342
_refine_ls_shift/su_max          0.329
_refine_ls_shift/su_mean         0.020
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0243P)²+6.6108P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0740
_reflns_number_gt                5108
_reflns_number_total             5686
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja036020tsi20030508_120405_1.cif
_cod_data_source_block           compound1,lewzno2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0243P)^2^+6.6108P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0243P)^2^+6.6108P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 

The following automatic conversions were performed:

data name '_diffrn_crystal_support' was replaced with
'_diffrn_measurement_specimen_support' as specified in the
replacement file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               4114274
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_calc_flag
Zn1 Zn 0.301179(9) 0.67381(2) 0.066607(12) 0.01644(5) Uani 1 d
Zn2 Zn 0.157421(10) 0.72715(2) 0.094332(14) 0.02158(6) Uani 1 d
O1A O 0.29210(6) 0.86037(12) -0.00491(8) 0.0177(2) Uani 1 d
N1A N 0.37763(8) 0.81455(18) 0.12140(11) 0.0251(3) Uani 1 d
C1A C 0.31807(10) 0.98353(19) 0.03320(13) 0.0254(4) Uani 1 d
H1A1 H 0.2850(12) 1.056(3) 0.0313(15) 0.030 Uiso 1 d
H1A2 H 0.3525(13) 1.020(3) 0.0072(16) 0.030 Uiso 1 d
C2A C 0.34493(9) 0.9523(2) 0.11925(13) 0.0255(4) Uani 1 d
H2A1 H 0.3741(12) 1.027(3) 0.1390(16) 0.031 Uiso 1 d
H2A2 H 0.3100(13) 0.944(3) 0.1516(16) 0.031 Uiso 1 d
C3A C 0.42845(13) 0.7914(3) 0.18763(19) 0.0474(7) Uani 1 d
H3A1 H 0.4295(17) 0.697(4) 0.207(2) 0.057 Uiso 1 d
H3A2 H 0.4344(16) 0.866(4) 0.226(2) 0.057 Uiso 1 d
C4A C 0.44618(11) 0.8167(3) 0.1060(2) 0.0449(7) Uani 1 d
H4A1 H 0.4629(15) 0.913(4) 0.0942(19) 0.054 Uiso 1 d
H4A2 H 0.4588(16) 0.740(4) 0.068(2) 0.054 Uiso 1 d
O1B O 0.24439(6) 0.73720(13) 0.15759(8) 0.0208(2) Uani 1 d
N1B N 0.31075(9) 0.48876(17) 0.13765(10) 0.0266(3) Uani 1 d
C1B C 0.25653(13) 0.6453(2) 0.22272(13) 0.0318(4) Uani 1 d
H1B1 H 0.2217(14) 0.649(3) 0.2557(17) 0.038 Uiso 1 d
H1B2 H 0.2979(14) 0.676(3) 0.2562(17) 0.038 Uiso 1 d
C2B C 0.26141(13) 0.4940(2) 0.19507(14) 0.0338(5) Uani 1 d
H2B1 H 0.2746(13) 0.431(3) 0.2397(17) 0.041 Uiso 1 d
H2B2 H 0.2194(15) 0.469(3) 0.1670(18) 0.041 Uiso 1 d
C3B C 0.32223(15) 0.3480(2) 0.10633(16) 0.0406(6) Uani 1 d
H3B1 H 0.2958(15) 0.277(3) 0.1241(19) 0.049 Uiso 1 d
H3B2 H 0.3274(15) 0.349(3) 0.0480(19) 0.049 Uiso 1 d
C4B C 0.37174(15) 0.4145(3) 0.16310(18) 0.0467(6) Uani 1 d
H4B1 H 0.3750(16) 0.384(4) 0.216(2) 0.056 Uiso 1 d
H4B2 H 0.4091(16) 0.457(4) 0.146(2) 0.056 Uiso 1 d
C1E1 C 0.08258(13) 0.6327(3) 0.1369(2) 0.0486(7) Uani 1 d
H1E1 H 0.0786(16) 0.546(4) 0.117(2) 0.058 Uiso 1 d
H1E2 H 0.0907(16) 0.604(4) 0.195(2) 0.058 Uiso 1 d
C2E1 C 0.01888(16) 0.7036(4) 0.1354(3) 0.0719(12) Uani 1 d
H2E1 H 0.025(2) 0.801(5) 0.168(3) 0.108 Uiso 1 d
H2E2 H -0.012(2) 0.645(5) 0.162(3) 0.108 Uiso 1 d
H2E3 H 0.003(2) 0.685(5) 0.073(3) 0.108 Uiso 1 d
O1C O 0.34076(6) 0.59108(14) -0.03199(8) 0.0216(2) Uani 1 d
O2C O 0.40877(7) 0.54191(15) -0.01171(9) 0.0280(3) Uani 1 d
C1E2 C 0.42454(10) 0.4612(2) -0.07822(14) 0.0311(4) Uani 1 d
H1E3 H 0.4738(13) 0.452(3) -0.0686(17) 0.037 Uiso 1 d
H1E4 H 0.4144(13) 0.514(3) -0.1291(17) 0.037 Uiso 1 d
C2E2 C 0.39126(13) 0.3200(3) -0.08538(15) 0.0353(5) Uani 1 d
H2E4 H 0.4045(16) 0.264(3) -0.035(2) 0.053 Uiso 1 d
H2E5 H 0.4031(15) 0.268(3) -0.132(2) 0.053 Uiso 1 d
H2E6 H 0.3441(16) 0.331(4) -0.0919(19) 0.053 Uiso 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'
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'
N N 0.0061 0.0033 '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
O1C Zn1 O1A 88.00(5) . 7_565
O1C Zn1 O1B 168.88(5) . .
O1A Zn1 O1B 81.55(5) 7_565 .
O1C Zn1 N1B 96.62(6) . .
O1A Zn1 N1B 99.99(6) 7_565 .
O1B Zn1 N1B 81.57(6) . .
O1C Zn1 O1A 83.27(5) . .
O1A Zn1 O1A 80.30(5) 7_565 .
O1B Zn1 O1A 98.60(5) . .
N1B Zn1 O1A 179.69(6) . .
O1C Zn1 N1A 103.85(6) . .
O1A Zn1 N1A 151.20(5) 7_565 .
O1B Zn1 N1A 87.19(6) . .
N1B Zn1 N1A 104.49(7) . .
O1A Zn1 N1A 75.27(6) . .
O1C Zn1 Zn2 40.80(4) . 7_565
O1A Zn1 Zn2 86.52(3) 7_565 7_565
O1B Zn1 Zn2 141.21(4) . 7_565
N1B Zn1 Zn2 137.03(5) . 7_565
O1A Zn1 Zn2 42.82(3) . 7_565
N1A Zn1 Zn2 85.86(5) . 7_565
O1C Zn1 Zn2 130.36(4) . .
O1A Zn1 Zn2 42.41(3) 7_565 .
O1B Zn1 Zn2 39.50(4) . .
N1B Zn1 Zn2 94.75(5) . .
O1A Zn1 Zn2 85.54(3) . .
N1A Zn1 Zn2 119.57(4) . .
Zn2 Zn1 Zn2 116.435(7) 7_565 .
O1B Zn2 C1E1 121.35(11) . .
O1B Zn2 O1C 99.80(5) . 7_565
C1E1 Zn2 O1C 129.22(10) . 7_565
O1B Zn2 O1A 85.06(5) . 7_565
C1E1 Zn2 O1A 123.13(10) . 7_565
O1C Zn2 O1A 85.87(5) 7_565 7_565
O1B Zn2 Zn1 97.84(4) . 7_565
C1E1 Zn2 Zn1 139.26(11) . 7_565
O1C Zn2 Zn1 42.22(4) 7_565 7_565
O1A Zn2 Zn1 44.03(3) 7_565 7_565
O1B Zn2 Zn1 42.62(4) . .
C1E1 Zn2 Zn1 140.86(9) . .
O1C Zn2 Zn1 89.41(3) 7_565 .
O1A Zn2 Zn1 42.82(3) 7_565 .
Zn1 Zn2 Zn1 63.565(7) 7_565 .
C1A O1A Zn2 117.55(11) . 7_565
C1A O1A Zn1 129.17(11) . 7_565
Zn2 O1A Zn1 94.76(5) 7_565 7_565
C1A O1A Zn1 115.22(11) . .
Zn2 O1A Zn1 93.15(5) 7_565 .
Zn1 O1A Zn1 99.70(5) 7_565 .
C3A N1A C4A 60.7(2) . .
C3A N1A C2A 116.21(17) . .
C4A N1A C2A 115.57(18) . .
C3A N1A Zn1 130.68(16) . .
C4A N1A Zn1 126.71(14) . .
C2A N1A Zn1 103.07(11) . .
O1A C1A C2A 110.55(15) . .
O1A C1A H1A1 110.1(15) . .
C2A C1A H1A1 110.7(15) . .
O1A C1A H1A2 111.3(16) . .
C2A C1A H1A2 107.4(16) . .
H1A1 C1A H1A2 107(2) . .
N1A C2A C1A 108.39(16) . .
N1A C2A H2A1 112.1(15) . .
C1A C2A H2A1 109.6(16) . .
N1A C2A H2A2 106.7(16) . .
C1A C2A H2A2 109.8(16) . .
H2A1 C2A H2A2 110(2) . .
N1A C3A C4A 59.75(16) . .
N1A C3A H3A1 113(2) . .
C4A C3A H3A1 119(2) . .
N1A C3A H3A2 115(2) . .
C4A C3A H3A2 118(2) . .
H3A1 C3A H3A2 118(3) . .
N1A C4A C3A 59.52(16) . .
N1A C4A H4A1 113.9(18) . .
C3A C4A H4A1 117.2(19) . .
N1A C4A H4A2 114.6(18) . .
C3A C4A H4A2 124.5(19) . .
H4A1 C4A H4A2 114(3) . .
C1B O1B Zn2 117.58(14) . .
C1B O1B Zn1 108.82(11) . .
Zn2 O1B Zn1 97.88(6) . .
C4B N1B C3B 59.89(18) . .
C4B N1B C2B 117.06(19) . .
C3B N1B C2B 114.51(18) . .
C4B N1B Zn1 126.02(17) . .
C3B N1B Zn1 124.21(14) . .
C2B N1B Zn1 108.16(12) . .
O1B C1B C2B 111.26(17) . .
O1B C1B H1B1 110.3(17) . .
C2B C1B H1B1 107.2(17) . .
O1B C1B H1B2 108.8(16) . .
C2B C1B H1B2 111.3(16) . .
H1B1 C1B H1B2 108(2) . .
N1B C2B C1B 107.78(18) . .
N1B C2B H2B1 109.1(17) . .
C1B C2B H2B1 111.7(17) . .
N1B C2B H2B2 108.4(17) . .
C1B C2B H2B2 107.4(18) . .
H2B1 C2B H2B2 112(2) . .
N1B C3B C4B 60.00(16) . .
N1B C3B H3B1 115(2) . .
C4B C3B H3B1 119(2) . .
N1B C3B H3B2 112.4(18) . .
C4B C3B H3B2 119.7(18) . .
H3B1 C3B H3B2 117(3) . .
N1B C4B C3B 60.11(16) . .
N1B C4B H4B1 114(2) . .
C3B C4B H4B1 118(2) . .
N1B C4B H4B2 114(2) . .
C3B C4B H4B2 121(2) . .
H4B1 C4B H4B2 117(3) . .
C2E1 C1E1 Zn2 120.8(2) . .
C2E1 C1E1 H1E1 112(2) . .
Zn2 C1E1 H1E1 109(2) . .
C2E1 C1E1 H1E2 101.2(19) . .
Zn2 C1E1 H1E2 114.8(19) . .
H1E1 C1E1 H1E2 96(3) . .
C1E1 C2E1 H2E1 109(2) . .
C1E1 C2E1 H2E2 111(3) . .
H2E1 C2E1 H2E2 107(4) . .
C1E1 C2E1 H2E3 96(3) . .
H2E1 C2E1 H2E3 130(4) . .
H2E2 C2E1 H2E3 102(4) . .
O2C O1C Zn2 108.55(9) . 7_565
O2C O1C Zn1 112.25(10) . .
Zn2 O1C Zn1 96.98(5) 7_565 .
C1E2 O2C O1C 106.27(14) . .
O2C C1E2 C2E2 113.71(18) . .
O2C C1E2 H1E3 103.3(16) . .
C2E2 C1E2 H1E3 112.2(16) . .
O2C C1E2 H1E4 111.1(16) . .
C2E2 C1E2 H1E4 109.2(16) . .
H1E3 C1E2 H1E4 107(2) . .
C1E2 C2E2 H2E4 108.8(19) . .
C1E2 C2E2 H2E5 111.4(19) . .
H2E4 C2E2 H2E5 110(3) . .
C1E2 C2E2 H2E6 111(2) . .
H2E4 C2E2 H2E6 109(3) . .
H2E5 C2E2 H2E6 107(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O1C 2.0824(13) .
Zn1 O1A 2.1104(12) 7_565
Zn1 O1B 2.1149(13) .
Zn1 N1B 2.1252(16) .
Zn1 O1A 2.1413(12) .
Zn1 N1A 2.1942(16) .
Zn1 Zn2 3.0762(3) 7_565
Zn1 Zn2 3.0940(3) .
Zn2 O1B 1.9868(13) .
Zn2 C1E1 1.987(2) .
Zn2 O1C 2.0251(13) 7_565
Zn2 O1A 2.0940(12) 7_565
Zn2 Zn1 3.0762(3) 7_565
O1A C1A 1.413(2) .
O1A Zn2 2.0940(12) 7_565
O1A Zn1 2.1104(12) 7_565
N1A C3A 1.462(3) .
N1A C4A 1.465(3) .
N1A C2A 1.472(2) .
C1A C2A 1.523(3) .
C1A H1A1 0.97(3) .
C1A H1A2 0.94(3) .
C2A H2A1 0.96(3) .
C2A H2A2 0.95(3) .
C3A C4A 1.480(5) .
C3A H3A1 0.96(3) .
C3A H3A2 0.96(4) .
C4A H4A1 1.00(3) .
C4A H4A2 1.02(3) .
O1B C1B 1.403(2) .
N1B C4B 1.466(3) .
N1B C3B 1.468(3) .
N1B C2B 1.479(3) .
C1B C2B 1.520(3) .
C1B H1B1 0.95(3) .
C1B H1B2 1.01(3) .
C2B H2B1 0.98(3) .
C2B H2B2 0.97(3) .
C3B C4B 1.464(4) .
C3B H3B1 0.94(3) .
C3B H3B2 1.00(3) .
C4B H4B1 0.94(3) .
C4B H4B2 0.94(3) .
C1E1 C2E1 1.475(4) .
C1E1 H1E1 0.89(4) .
C1E1 H1E2 1.01(4) .
C2E1 H2E1 1.08(5) .
C2E1 H2E2 0.99(5) .
C2E1 H2E3 1.08(5) .
O1C O2C 1.4832(18) .
O1C Zn2 2.0251(13) 7_565
O2C C1E2 1.424(3) .
C1E2 C2E2 1.507(3) .
C1E2 H1E3 1.02(3) .
C1E2 H1E4 1.00(3) .
C2E2 H2E4 1.02(3) .
C2E2 H2E5 0.98(3) .
C2E2 H2E6 0.97(3) .
