#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/64/2006428.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2006428
loop_
_publ_author_name
'Ng, Seik Weng'
'Kumar Das, V.G.'
_publ_contact_author
;
      Assoc. Prof. Seik Weng Ng
      Institute of Advanced Studies
      University of Malaya
      50603 Kuala Lumpur
      Malaysia
;
_publ_section_title
;
 Tetramethylammonium Bis(coumarin-3-carboxylato)triphenylstannate
 Ethanol Solvate
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1034
_journal_page_last               1036
_journal_paper_doi               10.1107/S0108270197004307
_journal_volume                  53
_journal_year                    1997
_chemical_formula_iupac
'(C4 H12 N) [Sn (C6 H5)3 (C10 H5 O4)2] , C2 H6 O'
_chemical_formula_moiety
'[(CH~3~)~4~N][Sn(C~6~H~5~)~3~(C~10~H~5~O~4~)~2~] , C~2~H~5~OH'
_chemical_formula_sum            'C44 H43 N O9 Sn'
_chemical_formula_weight         848.48
_chemical_name_systematic
;
 Tetramethylammonium Bis(coumarin-3-carboxylato)triphenylstannate
 Ethanol Solvate
;
_space_group_IT_number           64
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-C 2ac 2'
_symmetry_space_group_name_H-M   'C m c a'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   29.608(2)
_cell_length_b                   23.6935(9)
_cell_length_c                   11.8195(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      12
_cell_volume                     8291.6(7)
_computing_cell_refinement       'CAD-4 VAX/PC (Enraf-Nonius Delft, 1988)'
_computing_data_collection       'CAD-4 VAX/PC (Enraf-Nonius Delft, 1988)'
_computing_data_reduction
'NRCVAX (Gabe, Le Page, Charland, Lee & White, 1989)'
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) in SHELXTL/PC (Sheldrick, 1990b)'
_computing_publication_material  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       'ω 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  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5631
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         1.38
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  0.791
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_type   '\y scans (North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_description       'Irregular block'
_exptl_crystal_F_000             3488
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.507
_refine_diff_density_min         -0.330
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.997
_refine_ls_goodness_of_fit_obs   1.125
_refine_ls_hydrogen_treatment
'H-atom treatment: riding model, U(H) = 1.5U~eq~(C,O).'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_restrained_S_obs      1.125
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_obs          .0355
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0546P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0991
_refine_ls_wR_factor_obs         .0890
_reflns_number_observed          2449
_reflns_number_total             3725
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            sk1052.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

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 'calc w =
1/[\s^2^(Fo^2^)+(0.0546P)^2^] 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^)+(0.0546P)^2^]
where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        8291.5(7)
_cod_original_sg_symbol_Hall     '-C 2bc 2'
_cod_database_code               2006428
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'x+1/2, -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
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
Sn1 .156410(10) .0000 .0000 .04190(10) Uani d S 1 . Sn
O1 .16450(10) .07290(10) -.1177(2) .0560(10) Uani d . 1 . O
O2 .09330(10) .10250(10) -.1268(3) .0870(10) Uani d . 1 . O
O3 .09030(10) .21270(10) -.2210(2) .0820(10) Uani d . 1 . O
O4 .13100(10) .22180(10) -.3744(2) .0640(10) Uani d . 1 . O
N1 .0000 .1828(3) .0379(6) .101(2) Uani d S 1 . N
C1 .12730(10) .0498(2) .1297(3) .0510(10) Uani d . 1 . C
C2 .1442(2) .1043(2) .1479(4) .0700(10) Uani d . 1 . C
H2 .1655(2) .1189(2) .0981(4) .104 Uiso calc R 1 . H
C3 .1299(2) .1366(2) .2377(5) .095(2) Uani d . 1 . C
H3 .1418(2) .1725(2) .2482(5) .142 Uiso calc R 1 . H
C4 .0986(2) .1166(3) .3110(5) .107(2) Uani d . 1 . C
H4 .0891(2) .1388(3) .3714(5) .161 Uiso calc R 1 . H
C5 .0809(2) .0639(3) .2963(4) .099(2) Uani d . 1 . C
H5 .0596(2) .0500(3) .3468(4) .148 Uiso calc R 1 . H
C6 .0950(2) .0311(2) .2053(4) .0770(10) Uani d . 1 . C
H6 .0823(2) -.0044(2) .1951(4) .116 Uiso calc R 1 . H
C7 .22850(10) .0000 .0000 .0430(10) Uani d S 1 . C
C8 .25250(10) .0127(2) .0953(3) .0630(10) Uani d . 1 . C
H8 .23700(10) .0212(2) .1615(3) .094 Uiso calc R 1 . H
C9 .29940(10) .0132(2) .0962(4) .0740(10) Uani d . 1 . C
H9 .31500(10) .0225(2) .1619(4) .112 Uiso calc R 1 . H
C10 .3224(2) .0000 .0000 .078(2) Uani d S 1 . C
H10 .3538(2) .0000 .0000 .117 Uiso calc SR 1 . H
C11 .13280(10) .1042(2) -.1569(3) .0540(10) Uani d . 1 . C
C12 .14710(10) .14290(10) -.2518(3) .0450(10) Uani d . 1 . C
C13 .18320(10) .13100(10) -.3160(3) .0510(10) Uani d . 1 . C
H13 .20160(10) .10090(10) -.2954(3) .077 Uiso calc R 1 . H
C14 .19460(10) .16280(10) -.4154(3) .0510(10) Uani d . 1 . C
C15 .23060(10) .1509(2) -.4863(3) .0670(10) Uani d . 1 . C
H15 .25030(10) .1217(2) -.4685(3) .100 Uiso calc R 1 . H
C16 .2373(2) .1820(2) -.5824(4) .0780(10) Uani d . 1 . C
H16 .2608(2) .1728(2) -.6313(4) .117 Uiso calc R 1 . H
C17 .2095(2) .2271(2) -.6071(3) .0750(10) Uani d . 1 . C
H17 .2149(2) .2488(2) -.6711(3) .112 Uiso calc R 1 . H
C18 .1738(2) .2399(2) -.5378(3) .0670(10) Uani d . 1 . C
H18 .1546(2) .2697(2) -.5553(3) .100 Uiso calc R 1 . H
C19 .16690(10) .2083(2) -.4425(3) .0530(10) Uani d . 1 . C
C20 .12040(10) .1928(2) -.2776(3) .0550(10) Uani d . 1 . C
C21 .0000 .1199(6) .0480(10) .197(5) Uani d S 1 . C
H21A .0000 .1096(6) .1270(10) .295 Uiso calc SR 1 . H
H21B .0265 .1049(6) .0120(10) .295 Uiso calc R 1 . H
C22 .0000 .1930(10) -.0740(10) .300(10) Uani d S 1 . C
H22A .0000 .2327 -.0869 .436 Uiso d S 1 . H
H22B .0240 .1722 -.1086 .436 Uiso d . 1 . H
C23 .0410(3) .2009(5) .0800(10) .254(6) Uani d . 1 . C
H23A .0421(3) .1944(5) .1600(10) .381 Uiso calc R 1 . H
H23B .0444(3) .2406(5) .0650(10) .381 Uiso calc R 1 . H
H23C .0649(3) .1805(5) .0430(10) .381 Uiso calc R 1 . H
O1' -.0290(10) .4130(10) .081(3) .41(2) Uiso d P .50 -1 O
H1' -.0400(10) .3820(10) .086(3) .619 Uiso calc PR .50 -1 H
C2' .010(3) .419(2) .172(3) .39(2) Uiso d P .50 -1 C
H2'1 .027(3) .454(2) .167(3) .582 Uiso calc PR .50 -1 H
H2'2 -.001(3) .413(2) .249(3) .582 Uiso calc SR 1 -1 H
C3' .0330(10) .3750(10) .131(3) .30(2) Uiso d P .50 -1 C
H3'1 .0590(10) .3690(10) .176(3) .452 Uiso calc PR .50 -1 H
H3'2 .0420(10) .3820(10) .054(3) .452 Uiso calc PR .50 -1 H
H3'3 .0140(10) .3420(10) .134(3) .452 Uiso calc PR .50 -1 H
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'
Sn Sn -0.6537 1.4246 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 Sn1 C1 . 4 131.9(2) yes
C1 Sn1 C7 . . 114.00(10) yes
C1 Sn1 O1 . . 93.70(10) yes
C1 Sn1 O1 . 4 91.30(10) yes
C1 Sn1 C7 4 . 114.00(10) yes
C1 Sn1 O1 4 . 91.30(10) yes
C1 Sn1 O1 4 4 93.70(10) yes
C7 Sn1 O1 . . 83.84(6) yes
C7 Sn1 O1 . 4 83.84(6) yes
O1 Sn1 O1 . 4 167.70(10) yes
C11 O1 Sn1 . . 126.4(2) no
C20 O4 C19 . . 123.4(3) no
C22 N1 C23 . . 107.1(8) no
C22 N1 C23 . 12 107.1(8) no
C23 N1 C23 . 12 123.0(10) no
C22 N1 C21 . . 105.0(10) no
C23 N1 C21 . . 106.3(6) no
C23 N1 C21 12 . 106.3(6) no
C6 C1 C2 . . 116.3(4) no
C6 C1 Sn1 . . 124.9(3) no
C2 C1 Sn1 . . 118.6(3) no
C3 C2 C1 . . 121.4(5) no
C4 C3 C2 . . 120.7(5) no
C3 C4 C5 . . 120.0(5) no
C4 C5 C6 . . 119.7(5) no
C1 C6 C5 . . 121.9(5) no
C8 C7 C8 4 . 117.4(5) no
C8 C7 Sn1 4 . 121.3(2) no
C8 C7 Sn1 . . 121.3(2) no
C7 C8 C9 . . 121.9(4) no
C10 C9 C8 . . 119.4(4) no
C9 C10 C9 4 . 120.1(5) no
O2 C11 O1 . . 125.1(4) no
O2 C11 C12 . . 120.4(3) no
O1 C11 C12 . . 114.4(3) no
C13 C12 C20 . . 119.0(3) no
C13 C12 C11 . . 121.2(3) no
C20 C12 C11 . . 119.7(3) no
C12 C13 C14 . . 122.8(3) no
C15 C14 C19 . . 118.1(3) no
C15 C14 C13 . . 124.8(3) no
C19 C14 C13 . . 117.1(3) no
C16 C15 C14 . . 120.3(4) no
C15 C16 C17 . . 120.3(4) no
C18 C17 C16 . . 120.4(4) no
C17 C18 C19 . . 119.0(4) no
O4 C19 C18 . . 118.1(3) no
O4 C19 C14 . . 120.2(3) no
C18 C19 C14 . . 121.7(4) no
O3 C20 O4 . . 115.7(3) no
O3 C20 C12 . . 127.0(3) no
O4 C20 C12 . . 117.2(3) no
C3' C2' O1' . . 93(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Sn1 C1 . 2.117(4) yes
Sn1 C1 4 2.117(4) yes
Sn1 C7 . 2.135(4) yes
Sn1 O1 . 2.232(2) yes
Sn1 O1 4 2.232(2) no
O1 C11 . 1.283(4) no
O2 C11 . 1.222(4) no
O3 C20 . 1.211(4) no
O4 C20 . 1.372(4) no
O4 C19 . 1.370(4) no
N1 C21 . 1.500(10) no
N1 C22 . 1.34(2) no
N1 C23 . 1.379(7) no
N1 C23 12 1.379(7) no
C1 C6 . 1.382(5) no
C1 C2 . 1.402(5) no
C2 C3 . 1.376(6) no
C3 C4 . 1.353(7) no
C4 C5 . 1.366(8) no
C5 C6 . 1.390(6) no
C7 C8 4 1.365(4) no
C7 C8 . 1.365(4) no
C8 C9 . 1.389(6) no
C9 C10 . 1.361(5) no
C10 C9 4 1.361(5) no
C11 C12 . 1.509(5) no
C12 C13 . 1.339(5) no
C12 C20 . 1.455(4) no
C13 C14 . 1.435(5) no
C14 C15 . 1.386(5) no
C14 C19 . 1.392(5) no
C15 C16 . 1.368(5) no
C16 C17 . 1.380(6) no
C17 C18 . 1.370(6) no
C18 C19 . 1.368(5) no
O1' C2' . 1.58(6) no
C2' C3' . 1.33(5) no
