#------------------------------------------------------------------------------
#$Date: 2017-01-05 15:42:24 +0200 (Thu, 05 Jan 2017) $
#$Revision: 189894 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/32/35/4323557.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_4323557
loop_
_publ_author_name
'Shwu-Juian Lin'
'Tay-Ning Hong'
'Jo-Yu Tung'
'Jyh-Horung Chen'
_publ_section_title
;
 Molecular Structures of Ge(tpp)(OAc)2and In(tpp)(OAc) and Their
 Implications: Correlations between the 13C NMR Chemical Shift of the
 Acetato Ligand and Different Types of Carboxylate Coordination in
 M(por)(OAc)n {por = tpp (5,10,15,20-Tetraphenylporphyrinate), tmpp
 (5,10,15,20-Tetrakis(4-methoxyphenyl)porphyrinate), tpyp
 (5,10,15,20-Tetrakis(4-pyridyl)porphyrinate); M = Ga, In, Tl, Ge, Sn; n=
 1, 2}
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3886
_journal_page_last               3891
_journal_paper_doi               10.1021/ic961304i
_journal_volume                  36
_journal_year                    1997
_chemical_formula_moiety         C46H31InO4N2
_chemical_formula_sum            'C46 H31 In N2 O4'
_chemical_formula_weight         786.6
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_type_scat_source           'International Table vol IV'
_cell_angle_alpha                90
_cell_angle_beta                 90.28(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.293(1)
_cell_length_b                   16.601(2)
_cell_length_c                   21.054(2)
_cell_measurement_reflns_used    39
_cell_measurement_temperature    293
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     3597.5(7)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens XSCANS'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_structure_solution    'Siemens SHELXTL'
_diffrn_measurement_device       'Siemens R 3m/V diffractometer'
_diffrn_measurement_method       2θ-θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6897
_diffrn_reflns_theta_max         12.5
_diffrn_standards_decay_%        'less than 4.11'
_diffrn_standards_interval_count 197
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.60
_refine_diff_density_min         -0.77
_refine_ls_extinction_coef       None
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_obs   1.14
_refine_ls_hydrogen_treatment    'Riding model, fixed isotropic U'
_refine_ls_number_parameters     478
_refine_ls_number_reflns         4903
_refine_ls_R_factor_obs          0.037
_refine_ls_shift/esd_max         0.039
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     w⁻¹=σ²(F)+0.0010F²
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.049
_reflns_number_observed          4903
_reflns_number_total             6276
_reflns_observed_criterion       F>4.0\s(F)
_cod_data_source_file            ic961304i_2.cif
_cod_data_source_block           (II)_In(tpp)(OAc)2
_cod_depositor_comments
;
 Adding missing minus signs ('-') to the _atom_site_fract_z data item
 values of atoms 'C17' and 'C18'.

 Antanas Vaitkus,
 2017-01-05

 Adding the coordinates and the atom displacement parameter values
 for the hydrogen atoms from the supplementary material of the
 original publication.

 Antanas Vaitkus,
 2017-01-05

 Adding missing minus signs ('-') to the _atom_site_aniso_U_*,
 _atom_site_fract_* data item values.

 Antanas Vaitkus,
 2017-01-05

 Correcting a typo in the _atom_site_aniso_U_22 data item value by changing it
 from '0.031(l)' to '0.031(1)' after consulting the supplementary material of
 the original publication.

 Antanas Vaitkus,
 2017-01-05

 Correcting typos in the _atom_site_label, _atom_site_aniso_label,
 _geom_angle_atom_site_label_*, _geom_bond_atom_site_label_* data item values.

 Antanas Vaitkus,
 2017-01-05

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w^-1^=\s^2^(F)+0.0010F^2^' 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^(F)+0.0010F^2^'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        3597.5(5)
_cod_original_formula_sum        'C46 H31 In O4 N2'
_cod_database_code               4323557
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'1/2-x, 1/2+y, 1/2-z'
'-x, -y, -z'
'1/2+x, 1/2-y, 1/2+z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
In 0.3561(1) 0.1793(1) 0.1528(1) 0.035(1)
N(1) 0.4779(3) 0.2786(2) 0.1209(1) 0.040(1)
N(2) 0.4700(3) 0.1867(2) 0.2397(1) 0.041(1)
N(3) 0.3527(3) 0.0512(2) 0.1735(1) 0.039(1)
N(4) 0.3638(3) 0.1428(2) 0.0540(1) 0.040(1)
C(1) 0.4847(4) 0.3083(2) 0.0595(2) 0.041(1)
C(2) 0.5463(4) 0.3863(2) 0.0622(2) 0.050(1)
C(3) 0.5742(4) 0.4030(2) 0.1234(2) 0.050(1)
C(4) 0.5327(4) 0.3348(2) 0.1610(2) 0.042(1)
C(5) 0.5494(4) 0.3267(2) 0.2267(2) 0.041(1)
C(6) 0.5208(4) 0.2578(2) 0.2628(2) 0.042(1)
C(7) 0.5449(4) 0.2492(3) 0.3301(2) 0.053(1)
C(8) 0.5080(4) 0.1739(2) 0.3464(2) 0.052(1)
C(9) 0.4616(4) 0.1339(2) 0.2903(2) 0.042(1)
C(10) 0.4148(3) 0.0547(2) 0.2872(2) 0.040(1)
C(11) 0.3661(3) 0.0167(2) 0.2323(2) 0.038(1)
C(12) 0.3302(4) -0.0670(2) 0.2275(2) 0.045(1)
C(13) 0.2956(4) -0.0807(2) 0.1670(2) 0.048(1)
C(14) 0.3077(4) -0.0069(2) 0.1325(2) 0.039(1)
C(15) 0.2836(4) 0.0031(2) 0.0675(2) 0.042(1)
C(16) 0.3124(4) 0.0720(2) 0.0311(2) 0.043(1)
C(17) 0.3017(4) 0.0775(3) -0.0367(2) 0.053(1)
C(18) 0.3479(4) 0.1497(3) -0.0538(2) 0.053(1)
C(19) 0.3868(4) 0.1921(2) 0.0026(2) 0.041(1)
C(20) 0.4428(4) 0.2681(2) 0.0053(2) 0.042(1)
C(21) 0.1199(4) 0.2315(2) 0.1772(2) 0.044(1)
C(22) -0.0127(4) 0.2630(3) 0.1943(2) 0.062(2)
O(1) 0.1315(4) 0.1724(3) 0.1443(3) 0.111(2)
O(2) 0.2168(3) 0.2634(2) 0.1975(2) 0.101(2)
C(31) 0.6100(4) 0.3968(2) 0.2608(2) 0.040(1)
C(32) 0.7425(4) 0.4039(3) 0.2652(2) 0.071(2)
C(33) 0.7978(5) 0.4701(4) 0.2948(3) 0.084(2)
C(34) 0.7243(6) 0.5284(3) 0.3201(2) 0.072(2)
C(35) 0.5937(6) 0.5217(3) 0.3171(2) 0.068(2)
C(36) 0.5368(4) 0.4561(3) 0.2874(2) 0.057(2)
C(41) 0.4233(4) 0.0050(2) 0.3463(2) 0.045(1)
C(42) 0.3129(5) -0.0247(3) 0.3755(2) 0.060(2)
C(43) 0.3234(6) -0.0729(3) 0.4283(3) 0.075(2)
C(44) 0.4426(6) -0.0917(3) 0.4536(2) 0.072(2)
C(45) 0.5521(6) -0.0625(3) 0.4261(2) 0.071(2)
C(46) 0.5438(5) -0.0152(3) 0.3720(2) 0.054(1)
C(51) 0.2247(4) -0.0670(2) 0.0325(2) 0.042(1)
C(52) 0.0954(5) -0.0853(3) 0.0403(2) 0.065(2)
C(53) 0.0404(5) -0.1496(3) 0.0077(3) 0.081(2)
C(54) 0.1130(6) -0.1949(3) -0.0324(2) 0.068(2)
C(55) 0.2403(5) -0.1769(3) -0.0416(2) 0.067(2)
C(56) 0.2974(5) -0.1132(3) -0.0093(2) 0.057(2)
C(61) 0.4686(4) 0.3077(2) -0.0578(2) 0.047(1)
C(62) 0.3696(5) 0.3421(3) -0.0938(2) 0.064(2)
C(63) 0.3978(7) 0.3745(3) -0.1525(2) 0.079(2)
C(64) 0.5212(7) 0.3718(3) -0.1764(2) 0.079(2)
C(65) 0.6182(6) 0.3384(4) -0.1414(2) 0.079(2)
C(66) 0.5927(5) 0.3068(3) -0.0829(2) 0.066(2)
H(2A) 0.5641 0.4205 0.0265 0.08
H(3A) 0.6146 0.4511 0.1393 0.08
H(7A) 0.5809 0.2896 0.3577 0.08
H(8A) 0.5114 0.1512 0.3882 0.08
H(12A) 0.3313 -0.1058 0.2613 0.08
H(13A) 0.2670 -0.1312 0.1496 0.08
H(17A) 0.2677 0.0367 -0.0645 0.08
H(18A) 0.3540 0.1701 -0.0964 0.08
H(22A) -0.0750 0.2451 0.1633 0.08
H(22B) -0.0368 0.2434 0.2355 0.08
H(22C) -0.0107 0.3208 0.1949 0.08
H(32A) 0.7964 0.3622 0.2478 0.08
H(33A) 0.8907 0.4741 0.2975 0.08
H(34A) 0.7640 0.5749 0.3391 0.08
H(35A) 0.5404 0.5622 0.3365 0.08
H(36A) 0.4438 0.4520 0.2853 0.08
H(42A) 0.2291 -0.0110 0.3585 0.08
H(43A) 0.2465 -0.0937 0.4481 0.08
H(44A) 0.4488 -0.1252 0.4907 0.08
H(45A) 0.6356 -0.0752 0.4440 0.08
H(46A) 0.6212 0.0040 0.3520 0.08
H(52A) 0.0437 -0.0530 0.0683 0.08
H(53A) -0.0499 -0.1619 0.0133 0.08
H(54A) 0.0749 -0.2400 -0.0541 0.08
H(55A) 0.2906 -0.2082 -0.0710 0.08
H(56A) 0.3875 -0.1007 -0.0153 0.08
H(62A) 0.2827 0.3433 -0.0773 0.08
H(63A) 0.3296 0.3991 -0.1770 0.08
H(64A) 0.5387 0.3937 -0.2177 0.08
H(65A) 0.7047 0.3371 -0.1582 0.08
H(66A) 0.6617 0.2828 -0.0586 0.08
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N(1) In N(2) 84.7(1)
N(2) In N(3) 84.0(1)
N(2) In N(4) 143.3(1)
N(1) In C(21) 110.2(1)
N(3) In C(21) 105.5(1)
N(1) In O(1) 126.0(1)
N(3) In O(1) 87.1(1)
C(21) In O(1) 27.3(1)
N(2) In O(2) 87.3(1)
N(4) In O(2) 127.7(1)
O(1) In O(2) 54.4(2)
In N(1) C(4) 123.9(2)
In N(2) C(6) 123.2(2)
C(6) N(2) C(9) 107.3(3)
In N(3) C(14) 124.5(2)
In N(4) C(16) 124.0(2)
C(16) N(4) C(19) 107.5(3)
N(1) C(1) C(20) 125.4(3)
C(1) C(2) C(3) 108.2(4)
N(1) C(4) C(3) 108.4(3)
C(3) C(4) C(5) 125.5(3)
C(4) C(5) C(31) 116.6(3)
N(2) C(6) C(5) 125.8(3)
C(5) C(6) C(7) 125.2(4)
C(7) C(8) C(9) 108.2(4)
N(2) C(9) C(10) 125.6(3)
C(9) C(10) C(11) 125.5(3)
C(11) C(10) C(41) 117.1(3)
N(3) C(11) C(12) 108.3(3)
C(11) C(12) C(13) 107.3(3)
N(3) C(14) C(13) 108.1(3)
C(13) C(14) C(15) 125.7(3)
C(14) C(15) C(51) 117.2(3)
N(4) C(16) C(15) 125.8(3)
C(15) C(16) C(17) 125.3(4)
C(17) C(18) C(19) 108.3(4)
N(4) C(19) C(20) 125.6(3)
C(1) C(20) C(19) 126.6(3)
C(19) C(20) C(61) 115.9(3)
In C(21) O(1) 61.8(2)
In C(21) O(2) 56.7(3)
O(1) C(21) O(2) 118.5(4)
In O(2) C(21) 96.2(3)
C(5) C(31) C(36) 121.8(4)
C(31) C(32) C(33) 120.4(5)
C(33) C(34) C(35) 119.1(5)
C(31) C(36) C(35) 121.4(4)
C(10) C(41) C(46) 120.4(4)
C(41) C(42) C(43) 120.4(5)
C(43) C(44) C(45) 119.7(5)
C(41) C(46) C(45) 120.6(4)
C(15) C(51) C(56) 121.3(4)
C(51) C(52) C(53) 120.2(4)
C(53) C(54) C(55) 120.1(5)
C(51) C(56) C(55) 120.3(4)
C(20) C(61) C(66) 119.9(4)
N(1) In N(3) 144.4(1)
N(1) In N(4) 83.8(1)
N(3) In N(4) 85.4(1)
N(2) In C(21) 108.1(1)
N(4) In C(21) 108.5(1)
N(2) In O(1) 126.9(2)
N(4) In O(1) 87.3(2)
N(1) In O(2) 91.7(1)
N(3) In O(2) 121.4(1)
C(21) In O(2) 27.1(1)
In N(1) C(1) 126.1(2)
C(1) N(1) C(4) 108.0(3)
In N(2) C(9) 125.3(2)
In N(3) C(11) 126.1(2)
C(11) N(3) C(14) 107.9(3)
In N(4) C(19) 126.4(2)
N(1) C(1) C(2) 107.9(3)
C(2) C(1) C(20) 126.7(4)
C(2) C(3) C(4) 107.5(4)
N(1) C(4) C(5) 126.1(3)
C(4) C(5) C(6) 126.1(3)
C(6) C(5) C(31) 117.3(3)
N(2) C(6) C(7) 109.0(3)
C(6) C(7) C(8) 107.0(4)
N(2) C(9) C(8) 108.5(3)
C(8) C(9) C(10) 125.9(4)
C(9) C(10) C(41) 117.4(3)
N(3) C(11) C(10) 126.1(3)
C(10) C(11) C(12) 125.5(3)
C(12) C(13) C(14) 108.3(3)
N(3) C(14) C(15) 126.2(3)
C(14) C(15) C(16) 126.2(3)
C(16) C(15) C(51) 116.6(3)
N(4) C(16) C(17) 108.8(3)
C(16) C(17) C(18) 107.4(4)
N(4) C(19) C(18) 108.0(3)
C(18) C(19) C(20) 126.3(4)
C(1) C(20) C(61) 117.4(3)
In C(21) C(22) 177.1(3)
C(22) C(21) O(1) 120.8(4)
C(22) C(21) O(2) 120.7(4)
In O(1) C(21) 90.9(3)
C(5) C(31) C(32) 120.7(4)
C(32) C(31) C(36) 117.5(4)
C(32) C(33) C(34) 121.3(5)
C(34) C(35) C(36) 120.3(5)
C(10) C(41) C(42) 121.4(4)
C(42) C(41) C(46) 118.1(4)
C(42) C(43) C(44) 120.9(5)
C(44) C(45) C(46) 120.3(5)
C(15) C(51) C(52) 120.1(4)
C(52) C(51) C(56) 118.5(4)
C(52) C(53) C(54) 120.6(5)
C(54) C(55) C(56) 120.2(5)
C(20) C(61) C(62) 121.8(4)
C(62) C(61) C(66) 118.2(4)
C(61) C(62) C(63) 119.4(5)
C(63) C(64) C(65) 119.7(5)
C(61) C(66) C(65) 121.5(5)
C(62) C(63) C(64) 121.0(5)
C(64) C(65) C(66) 120.2(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
In N(1) 2.178(3)
In N(3) 2.172(3)
In C(21) 2.634(4)
In O(2) 2.215(4)
N(1) C(4) 1.378(5)
N(2) C(9) 1.382(5)
N(3) C(14) 1.373(5)
N(4) C(19) 1.379(5)
C(1) C(20) 1.389(5)
C(3) C(4) 1.447(6)
C(5) C(6) 1.406(5)
C(6) C(7) 1.443(5)
C(8) C(9) 1.435(6)
C(10) C(11) 1.406(5)
C(11) C(12) 1.442(5)
C(13) C(14) 1.432(5)
C(15) C(16) 1.410(5)
C(16) C(17) 1.434(5)
C(18) C(19) 1.437(6)
C(20) C(61) 1.506(5)
C(21) O(1) 1.208(6)
C(31) C(32) 1.371(6)
C(32) C(33) 1.386(8)
C(34) C(35) 1.350(9)
C(41) C(42) 1.385(6)
C(42) C(43) 1.375(7)
C(44) C(45) 1.360(8)
C(51) C(52) 1.376(6)
C(52) C(53) 1.388(8)
C(54) C(55) 1.358(8)
C(61) C(62) 1.390(6)
C(62) C(63) 1.382(7)
C(64) C(65) 1.357(8)
In N(2) 2.174(3)
In N(4) 2.167(3)
In O(1) 2.322(4)
N(1) C(1) 1.385(5)
N(2) C(6) 1.378(5)
N(3) C(11) 1.370(5)
N(4) C(16) 1.374(5)
C(1) C(2) 1.443(5)
C(2) C(3) 1.348(6)
C(4) C(5) 1.398(5)
C(5) C(31) 1.502(5)
C(7) C(8) 1.351(6)
C(9) C(10) 1.401(5)
C(10) C(41) 1.495(5)
C(12) C(13) 1.339(6)
C(14) C(15) 1.398(5)
C(15) C(51) 1.503(5)
C(17) C(18) 1.339(6)
C(19) C(20) 1.388(5)
C(21) C(22) 1.508(6)
C(21) O(2) 1.205(6)
C(31) C(36) 1.363(6)
C(33) C(34) 1.340(8)
C(35) C(36) 1.385(7)
C(41) C(46) 1.392(6)
C(43) C(44) 1.371(8)
C(45) C(46) 1.384(6)
C(51) C(56) 1.389(6)
C(53) C(54) 1.357(8)
C(55) C(56) 1.389(6)
C(61) C(66) 1.385(7)
C(63) C(64) 1.369(9)
C(65) C(66) 1.366(7)
