#------------------------------------------------------------------------------
#$Date: 2022-09-28 18:08:17 +0300 (Wed, 28 Sep 2022) $
#$Revision: 278247 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/04/2100418.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_2100418
loop_
_publ_author_name
'Somphon, Weenawan'
'Haller, Kenneth J.'
'Ng, Seik Weng'
'Rae, A. David'
_publ_contact_author_address
; School of Chemistry
  Institute of Science
  Suranaree University of Technology
  Nahkon Ratchasima 30000
  Thailand
;
_publ_contact_author_email       haller@sut.ac.th
_publ_contact_author_fax         66(44)224-185
_publ_contact_author_name        'Dr. Kenneth J. Haller'
_publ_contact_author_phone       66(44)224-303
_publ_section_title
;
 Packing and polytypism in 1,10-phenanthrolin-1-ium
 (2-carboxyethyl)(2-carboxylatoethyl)dichlorostannate(IV)
;
_publ_section_title_footnote     ' ?'
_journal_coeditor_code           BS5018
_journal_date_accepted           2006-01-20
_journal_date_recd_electronic    2005-05-05
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              255
_journal_page_last               261
_journal_paper_category          FA
_journal_paper_doi               10.1107/S0108768106002461
_journal_volume                  62
_journal_year                    2006
_chemical_formula_moiety         'C12 H9 N2 1+, C6 H9 Cl2 O4 Sn1 1-'
_chemical_formula_structural
' (Sn Cl2 ((C H2)2 C O2) ((C H2)2 C O2 H)) (C12 H9 N2)''
_chemical_formula_sum            'C18 H18 Cl2 N2 O4 Sn'
_chemical_formula_weight         515.94
_chemical_name_systematic
; 1,10-Phenanthrolin-1-ium
 (2-Carboxyethyl)(2-carboxylatoethyl)dichlorostannate(IV)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_method           'edit of cif form and SHELXTL files'
_cell_angle_alpha                114.4242(11)
_cell_angle_beta                 92.5620(11)
_cell_angle_gamma                104.3542(12)
_cell_formula_units_Z            2
_cell_length_a                   7.12040(10)
_cell_length_b                   12.5017(2)
_cell_length_c                   12.5780(2)
_cell_measurement_reflns_used    25992
_cell_measurement_temperature    200.0(10)
_cell_measurement_theta_max      29.575
_cell_measurement_theta_min      2.910
_cell_volume                     973.78(3)
_computing_cell_refinement       'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP (Burnett & Johnson 1996; Farrugia 1997)'
_computing_structure_refinement  'SHELXTL (Bruker AXS Inc. 1998)'
_computing_structure_solution    'SIR97 (Altomare, et al., 1999)'
_diffrn_ambient_temperature      200.0(10)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ four-circle goniostat'
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD'
_diffrn_measurement_method       'φ scan plus ω scans with κ offsets'
_diffrn_radiation_monochromator  'horizonatlly mounted graphite crystal'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.035
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28062
_diffrn_reflns_theta_full        28.69
_diffrn_reflns_theta_max         28.69
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    1.613
_exptl_absorpt_correction_T_max  0.824
_exptl_absorpt_correction_T_min  0.798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV, (Blessing, 1995)'
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.31
_refine_diff_density_min         -0.68
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.966
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         5019
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.966
_refine_ls_restrained_S_obs      1.001
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0632
_refine_ls_wR_factor_ref         0.0594
_reflns_number_gt                4174
_reflns_number_total             5019
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bs5018.cif
_cod_data_source_block           kh02d
_cod_original_formula_sum        'C18 H18 Cl2 N2 O4 Sn1'
_cod_database_code               2100418
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Sn Sn1 0.40500(2) 0.111904(14) 0.817654(13) 0.02452(6) Uani d . 1
Cl Cl11 0.24231(10) 0.04003(6) 0.94939(6) 0.04213(16) Uani d . 1
Cl Cl12 0.40291(10) 0.32885(5) 0.92664(5) 0.03442(14) Uani d . 1
O O11 0.6070(2) 0.17256(16) 0.68119(14) 0.0326(4) Uani d . 1
C C11 0.7736(3) 0.2339(2) 0.7372(2) 0.0264(5) Uani d . 1
O O12 0.9075(3) 0.29248(17) 0.69688(16) 0.0330(4) Uani d . 1
H H12O 0.870(5) 0.276(3) 0.636(3) 0.049(7) Uiso d . 1
C C12 0.8357(3) 0.2489(2) 0.8595(2) 0.0314(5) Uani d . 1
H H12A 0.8293 0.3297 0.9186 0.038 Uiso calc R 1
H H12B 0.9737 0.2473 0.8683 0.038 Uiso calc R 1
C C13 0.7052(3) 0.1477(2) 0.8840(2) 0.0305(5) Uani d . 1
H H13A 0.7220 0.1730 0.9704 0.037 Uiso calc R 1
H H13B 0.7451 0.0718 0.8458 0.037 Uiso calc R 1
O O13 0.3818(3) -0.08906(15) 0.69251(14) 0.0316(4) Uani d . 1
C C14 0.2685(3) -0.1283(2) 0.5948(2) 0.0254(5) Uani d . 1
O O14 0.2180(2) -0.23959(14) 0.51962(14) 0.0293(4) Uani d . 1
C C15 0.1926(3) -0.0373(2) 0.5686(2) 0.0266(5) Uani d . 1
H H15A 0.0640 -0.0807 0.5153 0.032 Uiso calc R 1
H H15B 0.2853 -0.0018 0.5272 0.032 Uiso calc R 1
C C16 0.1690(3) 0.0657(2) 0.6813(2) 0.0263(5) Uani d . 1
H H16A 0.0418 0.0387 0.7050 0.032 Uiso calc R 1
H H16B 0.1709 0.1384 0.6676 0.032 Uiso calc R 1
C C31 0.8463(4) 0.7657(3) 0.7673(3) 0.0414(7) Uani d . 1
H H31 0.8537 0.8498 0.8105 0.050 Uiso calc R 1
C C32 0.8916(4) 0.7009(3) 0.8249(3) 0.0428(7) Uani d . 1
H H32 0.9292 0.7394 0.9085 0.051 Uiso calc R 1
C C33 0.8819(4) 0.5779(2) 0.7591(2) 0.0353(6) Uani d . 1
H H33 0.9128 0.5342 0.8005 0.042 Uiso calc R 1
N N34 0.8320(3) 0.51821(18) 0.64223(17) 0.0294(4) Uani d . 1
C C35 0.7857(3) 0.5827(2) 0.5861(2) 0.0262(5) Uani d . 1
C C36 0.7889(3) 0.7064(2) 0.6440(2) 0.0333(6) Uani d . 1
C C37 0.7293(4) 0.7645(2) 0.5768(3) 0.0400(7) Uani d . 1
H H37 0.7278 0.8474 0.6168 0.048 Uiso calc R 1
C C38 0.6753(4) 0.7045(2) 0.4584(3) 0.0385(6) Uani d . 1
H H38 0.6358 0.7455 0.4164 0.046 Uiso calc R 1
C C39 0.6767(3) 0.5798(2) 0.3949(2) 0.0317(6) Uani d . 1
C C40 0.7274(3) 0.5197(2) 0.4592(2) 0.0260(5) Uani d . 1
N N41 0.7171(3) 0.39916(19) 0.40163(18) 0.0259(4) Uani d . 1
H H41N 0.735(4) 0.360(3) 0.435(3) 0.049(7) Uiso d . 1
C C42 0.6642(4) 0.3356(2) 0.2841(2) 0.0329(6) Uani d . 1
H H42 0.6577 0.2511 0.2468 0.039 Uiso calc R 1
C C43 0.6189(4) 0.3925(3) 0.2167(2) 0.0390(6) Uani d . 1
H H43 0.5840 0.3477 0.1331 0.047 Uiso calc R 1
C C44 0.6244(4) 0.5134(3) 0.2712(2) 0.0378(6) Uani d . 1
H H44 0.5929 0.5527 0.2253 0.045 Uiso calc R 1
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'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
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_publ_flag
C13 Sn1 C16 153.22(9) y
C13 Sn1 O13 91.47(8) y
C16 Sn1 O13 77.42(7) y
C13 Sn1 Cl11 101.30(7) y
C16 Sn1 Cl11 102.65(7) y
O13 Sn1 Cl11 88.45(5) y
C13 Sn1 Cl12 94.67(7) y
C16 Sn1 Cl12 94.47(6) y
O13 Sn1 Cl12 171.40(4) y
Cl11 Sn1 Cl12 96.24(2) y
C13 Sn1 O11 72.78(7) y
C16 Sn1 O11 82.30(7) y
O13 Sn1 O11 87.19(6) y
Cl11 Sn1 O11 172.54(4) y
Cl12 Sn1 O11 88.87(4) y
C11 O11 Sn1 107.83(14) y
O11 C11 O12 123.2(2) y
O11 C11 C12 121.8(2) y
O12 C11 C12 115.0(2) y
C11 O12 H12O 108.(3) y
C11 C12 C13 111.7(2) y
C12 C13 Sn1 110.5(2) y
C14 O13 Sn1 112.33(14) y
O14 C14 O13 122.4(2) y
O14 C14 C15 119.3(2) y
O13 C14 C15 118.4(2) y
C14 C15 C16 111.6(2) y
C15 C16 Sn1 108.65(14) y
C32 C31 C36 119.3(3) y
C31 C32 C33 119.1(3) y
N34 C33 C32 123.9(2) y
C33 N34 C35 116.5(2) y
N34 C35 C36 124.1(2) y
N34 C35 C40 117.8(2) y
C36 C35 C40 118.1(2) y
C31 C36 C35 117.0(2) y
C31 C36 C37 123.4(2) y
C35 C36 C37 119.6(2) y
C38 C37 C36 121.6(3) y
C37 C38 C39 120.8(2) y
C40 C39 C44 118.2(2) y
C40 C39 C38 118.5(2) y
C44 C39 C38 123.2(2) y
N41 C40 C39 119.5(2) y
N41 C40 C35 119.2(2) y
C39 C40 C35 121.3(2) y
C42 N41 C40 122.1(2) y
C42 N41 H41N 115.(2) y
C40 N41 H41N 123.(2) y
N41 C42 C43 120.2(2) y
C44 C43 C42 119.6(2) y
C43 C44 C39 120.2(2) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Sn1 C13 2.127(2) y
Sn1 C16 2.131(2) y
Sn1 O13 2.3060(17) y
Sn1 Cl11 2.4045(6) y
Sn1 Cl12 2.4864(6) y
Sn1 O11 2.5192(18) y
O11 C11 1.232(3) y
C11 O12 1.307(3) y
C11 C12 1.502(3) y
O12 H12O 0.72(3) y
C12 C13 1.524(3) y
O13 C14 1.272(3) y
C14 O14 1.262(3) y
C14 C15 1.515(3) y
C15 C16 1.521(3) y
C31 C32 1.370(4) y
C31 C36 1.401(4) y
C32 C33 1.395(4) y
C33 N34 1.326(3) y
N34 C35 1.356(3) y
C35 C36 1.404(3) y
C35 C40 1.442(3) y
C36 C37 1.431(4) y
C37 C38 1.346(4) y
C38 C39 1.431(4) y
C39 C40 1.400(3) y
C39 C44 1.405(4) y
C40 N41 1.356(3) y
N41 C42 1.337(3) y
N41 H41N 0.79(3) y
C42 C43 1.384(3) y
C43 C44 1.366(4) y
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O12 H12O O14 2_656 0.72(3) 1.86(3) 2.579(2) 177.(3) y
N41 H41N O14 2_656 0.79(3) 1.91(3) 2.688(2) 166.(3) y
N41 H41N N34 . 0.79(3) 2.46(3) 2.737(3) 102.(2) y
C42 H42 O13 2_656 0.95 2.40 3.154(3) 136.0 y
C43 H43 Cl12 1_554 0.95 2.74 3.578(3) 147.8 y
C44 H44 Cl12 2_666 0.95 2.86 3.785(3) 165.4 y
C37 H37 O13 1_565 0.95 2.86 3.458(3) 122.5 y
C38 H38 O11 2_666 0.95 2.70 3.596(3) 158.4 y
C31 H31 Cl11 2_667 0.95 2.95 3.578(3) 125.1 y
C31 H31 Cl11 1_665 0.95 3.04 3.619(3) 121.2 y
C32 H32 Cl11 2_667 0.95 3.18 3.691(3) 116.4 y
C33 H33 O12 . 0.95 2.74 3.377(3) 125.3 y
