#------------------------------------------------------------------------------
#$Date: 2019-11-25 03:14:35 +0200 (Mon, 25 Nov 2019) $
#$Revision: 239999 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/92/4129217.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_4129217
loop_
_publ_author_name
'Ni, Jun'
'Yan, He'
'Wang, Anchuang'
'Yang, Yu'
'Stern, Charlotte L.'
'Metz, Andrew W.'
'Jin, Shu'
'Wang, Lian'
'Marks, Tobin J.'
'Ireland, John R.'
'Kannewurf, Carl R.'
_publ_section_title
;
 MOCVD-derived highly transparent, conductive zinc- and tin-doped indium
 oxide thin films: precursor synthesis, metastable phase film growth and
 characterization, and application as anodes in polymer light-emitting
 diodes.
;
_journal_issue                   15
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5613
_journal_page_last               5624
_journal_paper_doi               10.1021/ja044643g
_journal_volume                  127
_journal_year                    2005
_chemical_formula_sum            'C16 H18 F12 N2 O4 Zn'
_chemical_formula_weight         595.69
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 105.617(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.216(6)
_cell_length_b                   10.448(2)
_cell_length_c                   13.242(4)
_cell_measurement_temperature    280(2)
_cell_volume                     2427.2(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.924
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11152
_diffrn_reflns_theta_full        28.97
_diffrn_reflns_theta_max         28.97
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    1.128
_exptl_absorpt_correction_T_max  0.9886
_exptl_absorpt_correction_T_min  0.7544
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2977
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0799P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1454
_reflns_number_gt                1500
_reflns_number_total             2977
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja044643gsi20040903_022244.cif
_cod_data_source_block           s75m1m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        2427.2(11)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4129217
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Zn1 Zn 0.5000 0.53494(4) 0.7500 0.0755(2) Uani 1 2 d S .
F1A F 0.6711(3) 0.1402(4) 0.9506(4) 0.1457(18) Uani 0.744(5) 1 d P .
F1B F 0.6129(9) 0.1030(13) 0.8773(12) 0.1457(18) Uani 0.256(5) 1 d P .
F2A F 0.5479(4) 0.1268(8) 0.9037(8) 0.193(3) Uani 0.726(15) 1 d P .
F2B F 0.5517(14) 0.1772(18) 0.946(3) 0.193(3) Uani 0.274(15) 1 d P .
F3A F 0.665(2) 0.191(2) 0.9981(19) 0.174(2) Uani 0.161(6) 1 d P .
F3B F 0.6059(3) 0.2372(4) 1.0307(3) 0.174(2) Uani 0.839(6) 1 d P .
F4A F 0.7773(2) 0.3738(4) 0.7313(5) 0.1387(17) Uani 0.808(8) 1 d P .
F4B F 0.7924(11) 0.437(2) 0.790(2) 0.1387(17) Uani 0.192(8) 1 d P .
F5A F 0.7157(2) 0.5051(6) 0.6210(3) 0.1388(17) Uani 0.876(9) 1 d P .
F5B F 0.7385(19) 0.417(5) 0.652(2) 0.1388(17) Uani 0.124(9) 1 d P .
F6A F 0.7682(2) 0.5730(4) 0.7700(4) 0.1540(17) Uani 0.895(7) 1 d P .
F6B F 0.733(2) 0.586(4) 0.691(4) 0.1540(17) Uani 0.105(7) 1 d P .
O1 O 0.54058(12) 0.38618(19) 0.85851(18) 0.0823(6) Uani 1 1 d . .
O2 O 0.60756(12) 0.52949(18) 0.7212(2) 0.0818(6) Uani 1 1 d . .
N1 N 0.52882(16) 0.6853(2) 0.8617(2) 0.0814(8) Uani 1 1 d . .
C1 C 0.59986(18) 0.3245(3) 0.8666(2) 0.0732(8) Uani 1 1 d . .
C2 C 0.65939(18) 0.3489(3) 0.8225(3) 0.0779(8) Uani 1 1 d . .
H2 H 0.7012 0.2940 0.8382 0.093 Uiso 1 1 calc R .
C3 C 0.65944(16) 0.4508(3) 0.7562(3) 0.0684(7) Uani 1 1 d . .
C4 C 0.6072(3) 0.2068(4) 0.9355(4) 0.1049(13) Uani 1 1 d . .
C5 C 0.7312(2) 0.4767(4) 0.7227(4) 0.0907(10) Uani 1 1 d . .
C6A C 0.5380(11) 0.8003(13) 0.7899(13) 0.0965(19) Uani 0.340(10) 1 d P 1
H6A H 0.5470 0.8800 0.8289 0.116 Uiso 0.340(10) 1 calc PR 1
H6B H 0.5792 0.7856 0.7577 0.116 Uiso 0.340(10) 1 calc PR 1
C6B C 0.4954(6) 0.8031(6) 0.8059(6) 0.0965(19) Uani 0.660(10) 1 d P 2
H6C H 0.5206 0.8775 0.8435 0.116 Uiso 0.660(10) 1 calc PR 2
H6D H 0.4417 0.8078 0.8032 0.116 Uiso 0.660(10) 1 calc PR 2
C7 C 0.6065(2) 0.6871(4) 0.9314(3) 0.1171(14) Uani 1 1 d . .
H7A H 0.6416 0.7009 0.8888 0.140 Uiso 1 1 calc R .
H7B H 0.6173 0.6031 0.9631 0.140 Uiso 1 1 calc R .
C8 C 0.6231(3) 0.7826(4) 1.0159(4) 0.1340(16) Uani 1 1 d . .
H8A H 0.6208 0.8668 0.9861 0.201 Uiso 1 1 calc R .
H8B H 0.6732 0.7678 1.0612 0.201 Uiso 1 1 calc R .
H8C H 0.5862 0.7756 1.0554 0.201 Uiso 1 1 calc R .
H3 H 0.500(2) 0.665(3) 0.901(3) 0.103(13) Uiso 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'
F F 0.0171 0.0103 '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
O2 Zn1 O2 176.89(11) . 2_656
O2 Zn1 O1 91.69(8) . 2_656
O2 Zn1 O1 86.02(8) 2_656 2_656
O2 Zn1 O1 86.02(8) . .
O2 Zn1 O1 91.69(8) 2_656 .
O1 Zn1 O1 85.15(12) 2_656 .
O2 Zn1 N1 94.52(10) . .
O2 Zn1 N1 87.79(10) 2_656 .
O1 Zn1 N1 173.79(10) 2_656 .
O1 Zn1 N1 95.46(11) . .
O2 Zn1 N1 87.79(10) . 2_656
O2 Zn1 N1 94.52(10) 2_656 2_656
O1 Zn1 N1 95.46(10) 2_656 2_656
O1 Zn1 N1 173.79(10) . 2_656
N1 Zn1 N1 84.60(16) . 2_656
F3A F1A F1B 120(3) . .
F3A F1A C4 60(3) . .
F1B F1A C4 62.2(6) . .
F1A F1B F2A 110.6(12) . .
F1A F1B C4 60.2(9) . .
F2A F1B C4 59.6(7) . .
F2B F2A C4 55(2) . .
F2B F2A F1B 114(3) . .
C4 F2A F1B 60.4(9) . .
F2A F2B C4 90(4) . .
F2A F2B F3B 142(3) . .
C4 F2B F3B 60.8(12) . .
F1A F3A C4 81(3) . .
F1A F3A F3B 137(4) . .
C4 F3A F3B 62.0(19) . .
C4 F3B F3A 51.8(13) . .
C4 F3B F2B 47.4(13) . .
F3A F3B F2B 92.0(19) . .
F4B F4A F5B 114(3) . .
F4B F4A C5 64.7(11) . .
F5B F4A C5 54(2) . .
F4A F4B C5 71.0(17) . .
F4A F4B F6A 119(2) . .
C5 F4B F6A 54.2(7) . .
F5B F5A F6B 108(3) . .
F5B F5A C5 56.5(17) . .
F6B F5A C5 56(2) . .
F5A F5B C5 74(3) . .
F5A F5B F4A 140(4) . .
C5 F5B F4A 70.5(18) . .
F6B F6A C5 61.4(18) . .
F6B F6A F4B 111(2) . .
C5 F6A F4B 55.1(10) . .
F6A F6B C5 67(3) . .
F6A F6B F5A 128(4) . .
C5 F6B F5A 66.2(16) . .
C1 O1 Zn1 125.5(2) . .
C3 O2 Zn1 127.1(2) . .
C7 N1 C6B 120.1(4) . .
C7 N1 C6A 97.4(7) . .
C6B N1 C6A 32.6(5) . .
C7 N1 Zn1 117.6(2) . .
C6B N1 Zn1 106.0(3) . .
C6A N1 Zn1 101.1(6) . .
C7 N1 H3 105(3) . .
C6B N1 H3 106(3) . .
C6A N1 H3 138(3) . .
Zn1 N1 H3 99(2) . .
O1 C1 C2 129.1(3) . .
O1 C1 C4 114.1(3) . .
C2 C1 C4 116.8(3) . .
C3 C2 C1 122.9(3) . .
C3 C2 H2 118.5 . .
C1 C2 H2 118.5 . .
O2 C3 C2 128.1(3) . .
O2 C3 C5 113.7(3) . .
C2 C3 C5 118.2(3) . .
F2B C4 F3A 124(2) . .
F2B C4 F3B 71.8(19) . .
F3A C4 F3B 66.1(13) . .
F2B C4 F1A 129.3(11) . .
F3A C4 F1A 39.4(12) . .
F3B C4 F1A 103.1(5) . .
F2B C4 F2A 34.6(18) . .
F3A C4 F2A 129.4(15) . .
F3B C4 F2A 103.5(6) . .
F1A C4 F2A 108.8(6) . .
F2B C4 F1B 93.6(18) . .
F3A C4 F1B 95.7(14) . .
F3B C4 F1B 140.4(6) . .
F1A C4 F1B 57.7(6) . .
F2A C4 F1B 60.0(8) . .
F2B C4 C1 111.8(12) . .
F3A C4 C1 117.4(14) . .
F3B C4 C1 111.2(4) . .
F1A C4 C1 116.6(4) . .
F2A C4 C1 112.6(5) . .
F1B C4 C1 108.4(5) . .
F5B C5 F6B 102(3) . .
F5B C5 F6A 131.1(15) . .
F6B C5 F6A 51(2) . .
F5B C5 F4B 97(2) . .
F6B C5 F4B 116(2) . .
F6A C5 F4B 70.7(11) . .
F5B C5 F5A 49(2) . .
F6B C5 F5A 57(2) . .
F6A C5 F5A 105.1(4) . .
F4B C5 F5A 132.3(9) . .
F5B C5 F4A 56(2) . .
F6B C5 F4A 134.8(14) . .
F6A C5 F4A 110.6(4) . .
F4B C5 F4A 44.4(10) . .
F5A C5 F4A 102.7(4) . .
F5B C5 C3 115.9(14) . .
F6B C5 C3 111.6(14) . .
F6A C5 C3 112.3(3) . .
F4B C5 C3 113.4(8) . .
F5A C5 C3 111.8(3) . .
F4A C5 C3 113.5(3) . .
C6A C6A N1 101.4(12) 2_656 .
C6A C6A H6A 111.5 2_656 .
N1 C6A H6A 111.5 . .
C6A C6A H6B 111.5 2_656 .
N1 C6A H6B 111.5 . .
H6A C6A H6B 109.3 . .
N1 C6B C6B 110.2(6) . 2_656
N1 C6B H6C 109.6 . .
C6B C6B H6C 109.6 2_656 .
N1 C6B H6D 109.6 . .
C6B C6B H6D 109.6 2_656 .
H6C C6B H6D 108.1 . .
N1 C7 C8 117.0(3) . .
N1 C7 H7A 108.0 . .
C8 C7 H7A 108.0 . .
N1 C7 H7B 108.0 . .
C8 C7 H7B 108.0 . .
H7A C7 H7B 107.3 . .
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 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O2 2.095(2) .
Zn1 O2 2.095(2) 2_656
Zn1 O1 2.111(2) 2_656
Zn1 O1 2.111(2) .
Zn1 N1 2.125(3) .
Zn1 N1 2.125(3) 2_656
F1A F3A 0.85(2) .
F1A F1B 1.290(17) .
F1A C4 1.325(6) .
F1B F2A 1.345(14) .
F1B C4 1.351(15) .
F2A F2B 0.76(3) .
F2A C4 1.340(10) .
F2B C4 1.10(2) .
F2B F3B 1.42(3) .
F3A C4 1.16(4) .
F3A F3B 1.35(3) .
F3B C4 1.307(6) .
F4A F4B 1.00(2) .
F4A F5B 1.18(4) .
F4A C5 1.350(5) .
F4B C5 1.29(2) .
F4B F6A 1.487(18) .
F5A F5B 1.05(5) .
F5A F6B 1.23(3) .
F5A C5 1.334(6) .
F5B C5 1.15(3) .
F6A F6B 1.08(5) .
F6A C5 1.277(6) .
F6B C5 1.22(4) .
O1 C1 1.237(3) .
O2 C3 1.244(3) .
N1 C7 1.467(4) .
N1 C6B 1.479(7) .
N1 C6A 1.568(15) .
N1 H3 0.86(4) .
C1 C2 1.387(4) .
C1 C4 1.516(5) .
C2 C3 1.379(4) .
C2 H2 0.9300 .
C3 C5 1.514(4) .
C6A C6A 1.50(4) 2_656
C6A H6A 0.9700 .
C6A H6B 0.9700 .
C6B C6B 1.534(17) 2_656
C6B H6C 0.9700 .
C6B H6D 0.9700 .
C7 C8 1.468(6) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
