#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/25/8102534.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_8102534
loop_
_publ_author_name
'Hao Hu'
'Shoukai Kang'
'Shaosong Qian'
_publ_section_title
;
 Crystal structure of (E)-ethyl
 3-(dichloro(2-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylimino)methyl)phenoxy)stannyl)propanoate,
 SnCl2(C5H9O2)(C18H16N3O2)
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              621
_journal_volume                  224
_journal_year                    2009
_chemical_formula_sum            'C23 H25 Cl2 N3 O4 Sn'
_chemical_formula_weight         597.05
_chemical_name_systematic
; 
(E)-ethyl 3-(dichloro(2-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylimino)methyl)phenoxy)stannyl)propanoate
C₂₃H₂₅Cl₂N3O4Sn1

;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.698(4)
_cell_angle_beta                 97.556(5)
_cell_angle_gamma                109.116(4)
_cell_formula_units_Z            2
_cell_length_a                   10.371(3)
_cell_length_b                   10.721(3)
_cell_length_c                   12.615(4)
_cell_measurement_reflns_used    2102
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     1200.7(6)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_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  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0516
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7119
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         1.78
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.322
_exptl_absorpt_correction_T_max  0.9369
_exptl_absorpt_correction_T_min  0.8792
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.010
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5211
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1340
_reflns_number_gt                3973
_reflns_number_total             5211
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            1267-2745.cff
_cod_data_source_block           r71015f
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8102534
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn1 Sn 0.22725(4) 0.07111(4) 0.33640(3) 0.04229(14) Uani 1 2 i d . . .
Cl1 Cl 0.21859(18) 0.25437(16) 0.25612(14) 0.0618(4) Uani 1 2 i d . . .
Cl3 Cl 0.28417(18) -0.06819(18) 0.43891(17) 0.0695(4) Uani 1 2 i d . . .
O2 O 0.3717(4) 0.0227(4) 0.2350(3) 0.0500(9) Uani 1 2 i d . . .
O4 O 0.1468(4) 0.1614(4) 0.4662(3) 0.0559(10) Uani 1 2 i d . . .
O6 O 0.1650(7) -0.2450(7) -0.0484(5) 0.110(2) Uani 1 2 i d . . .
O7 O 0.1368(6) -0.2948(6) 0.1061(5) 0.0860(15) Uani 1 2 i d . . .
N1 N 0.4367(4) 0.2481(4) 0.4501(4) 0.0378(9) Uani 1 2 i d . . .
N3 N 0.6145(4) 0.0966(4) 0.2593(4) 0.0471(11) Uani 1 2 i d . . .
N4 N 0.7326(4) 0.2061(4) 0.3474(4) 0.0405(10) Uani 1 2 i d . . .
C1 C 0.6313(9) -0.2593(8) 0.1432(8) 0.086(2) Uani 1 2 i d . . .
H1 H 0.6333 -0.3310 0.1684 0.103 Uiso 1 2 i calc R . .
C3 C 0.6249(8) -0.1349(7) 0.2183(6) 0.0655(17) Uani 1 2 i d . . .
H3 H 0.6218 -0.1223 0.2944 0.079 Uiso 1 2 i calc R . .
C7 C 0.6301(7) -0.0452(7) 0.0700(5) 0.0612(16) Uani 1 2 i d . . .
H7 H 0.6309 0.0277 0.0456 0.073 Uiso 1 2 i calc R . .
C8 C 0.1599(7) 0.4462(7) 0.7248(5) 0.0584(16) Uani 1 2 i d . . .
H8 H 0.0968 0.4677 0.7665 0.070 Uiso 1 2 i calc R . .
C13 C 0.3009(7) 0.5425(6) 0.7624(5) 0.0555(15) Uani 1 2 i d . . .
H13 H 0.3321 0.6290 0.8280 0.067 Uiso 1 2 i calc R . .
C14 C 0.1131(6) 0.3211(7) 0.6279(5) 0.0529(14) Uani 1 2 i d . . .
H14 H 0.0184 0.2578 0.6052 0.063 Uiso 1 2 i calc R . .
C16 C 0.3936(6) 0.5081(6) 0.7015(5) 0.0496(13) Uani 1 2 i d . . .
H16 H 0.4887 0.5709 0.7279 0.060 Uiso 1 2 i calc R . .
C18 C 0.7967(6) 0.4161(6) 0.5338(5) 0.0506(13) Uani 1 2 i d . . .
H18A H 0.8909 0.4270 0.5282 0.076 Uiso 1 2 i calc R . .
H18B H 0.7849 0.4047 0.6046 0.076 Uiso 1 2 i calc R . .
H18C H 0.7822 0.5003 0.5345 0.076 Uiso 1 2 i calc R . .
C19 C 0.4565(5) 0.3576(5) 0.5451(5) 0.0415(11) Uani 1 2 i d . . .
H19 H 0.5484 0.4275 0.5809 0.050 Uiso 1 2 i calc R . .
C22 C 0.3477(6) 0.3794(5) 0.5996(5) 0.0419(12) Uani 1 2 i d . . .
C25 C 0.5447(5) 0.2262(5) 0.3998(4) 0.0368(11) Uani 1 2 i d . . .
C26 C 0.6230(5) -0.0312(5) 0.1805(4) 0.0400(11) Uani 1 2 i d . . .
C27 C 0.0362(6) -0.0863(7) 0.2042(6) 0.0605(16) Uani 1 2 i d . . .
H27A H 0.0062 -0.1724 0.2200 0.073 Uiso 1 2 i calc R . .
H27B H -0.0370 -0.0487 0.2114 0.073 Uiso 1 2 i calc R . .
C31 C 0.6918(5) 0.2867(5) 0.4317(4) 0.0383(11) Uani 1 2 i d . . .
C35 C 0.4972(5) 0.1073(5) 0.2921(5) 0.0397(11) Uani 1 2 i d . . .
C37 C 0.2038(6) 0.2842(6) 0.5605(5) 0.0446(12) Uani 1 2 i d . . .
C42 C 0.2435(14) -0.4219(13) 0.1758(9) 0.137(5) Uani 1 2 i d . . .
H42A H 0.2967 -0.4814 0.1626 0.206 Uiso 1 2 i calc R . .
H42B H 0.1537 -0.4738 0.1848 0.206 Uiso 1 2 i calc R . .
H42C H 0.2954 -0.3354 0.2455 0.206 Uiso 1 2 i calc R . .
C46 C 0.0450(7) -0.1301(8) 0.0785(6) 0.0725(19) Uani 1 2 i d . . .
H46A H -0.0511 -0.1780 0.0279 0.087 Uiso 1 2 i calc R . .
H46B H 0.0902 -0.0424 0.0673 0.087 Uiso 1 2 i calc R . .
C47 C 0.1222(8) -0.2270(8) 0.0363(7) 0.076(2) Uani 1 2 i d . . .
C55 C 0.8734(6) 0.2281(7) 0.3311(6) 0.0611(17) Uani 1 2 i d . . .
H55A H 0.8668 0.1500 0.2619 0.092 Uiso 1 2 i calc R . .
H55B H 0.9330 0.2310 0.3977 0.092 Uiso 1 2 i calc R . .
H55C H 0.9133 0.3177 0.3230 0.092 Uiso 1 2 i calc R . .
C60 C 0.2197(11) -0.3830(10) 0.0736(8) 0.105(3) Uani 1 2 i d . . .
H60A H 0.3089 -0.3281 0.0638 0.126 Uiso 1 2 i calc R . .
H60B H 0.1670 -0.4686 0.0019 0.126 Uiso 1 2 i calc R . .
C54 C 0.6349(8) -0.2757(9) 0.0334(8) 0.088(3) Uani 1 2 i d . . .
H54 H 0.6364 -0.3607 -0.0181 0.105 Uiso 1 2 i calc R . .
C2 C 0.6362(8) -0.1696(10) -0.0041(6) 0.084(2) Uani 1 2 i d . . .
H2 H 0.6412 -0.1817 -0.0798 0.101 Uiso 1 2 i calc R . .
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Sn1 C27 100.9(2) . . ?
O4 Sn1 O2 163.02(14) . . ?
C27 Sn1 O2 96.06(19) . . ?
O4 Sn1 N1 85.24(15) . . ?
C27 Sn1 N1 170.1(2) . . ?
O2 Sn1 N1 77.87(14) . . ?
O4 Sn1 Cl3 89.97(13) . . ?
C27 Sn1 Cl3 102.01(19) . . ?
O2 Sn1 Cl3 87.12(12) . . ?
N1 Sn1 Cl3 85.67(11) . . ?
O4 Sn1 Cl1 89.59(13) . . ?
C27 Sn1 Cl1 89.77(19) . . ?
O2 Sn1 Cl1 89.83(11) . . ?
N1 Sn1 Cl1 82.42(11) . . ?
Cl3 Sn1 Cl1 168.08(6) . . ?
C35 O2 Sn1 109.9(3) . . ?
C37 O4 Sn1 131.8(3) . . ?
C47 O7 C60 113.8(6) . . ?
C19 N1 C25 124.6(4) . . ?
C19 N1 Sn1 126.1(3) . . ?
C25 N1 Sn1 109.3(3) . . ?
C35 N3 N4 107.5(4) . . ?
C35 N3 C26 126.4(4) . . ?
N4 N3 C26 121.3(4) . . ?
C31 N4 N3 110.1(4) . . ?
C31 N4 C55 130.0(4) . . ?
N3 N4 C55 119.4(4) . . ?
C54 C1 C3 119.3(7) . . ?
C54 C1 H1 120.4 . . ?
C3 C1 H1 120.4 . . ?
C26 C3 C1 119.6(7) . . ?
C26 C3 H3 120.2 . . ?
C1 C3 H3 120.2 . . ?
C26 C7 C2 118.3(7) . . ?
C26 C7 H7 120.8 . . ?
C2 C7 H7 120.8 . . ?
C14 C8 C13 120.8(5) . . ?
C14 C8 H8 119.6 . . ?
C13 C8 H8 119.6 . . ?
C16 C13 C8 119.0(5) . . ?
C16 C13 H13 120.5 . . ?
C8 C13 H13 120.5 . . ?
C8 C14 C37 121.9(5) . . ?
C8 C14 H14 119.0 . . ?
C37 C14 H14 119.0 . . ?
C13 C16 C22 121.5(5) . . ?
C13 C16 H16 119.3 . . ?
C22 C16 H16 119.3 . . ?
C31 C18 H18A 109.5 . . ?
C31 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C31 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 C22 125.2(5) . . ?
N1 C19 H19 117.4 . . ?
C22 C19 H19 117.4 . . ?
C37 C22 C16 119.0(5) . . ?
C37 C22 C19 125.7(5) . . ?
C16 C22 C19 115.3(5) . . ?
C31 C25 C35 108.5(4) . . ?
C31 C25 N1 136.8(5) . . ?
C35 C25 N1 114.6(4) . . ?
C3 C26 C7 121.6(5) . . ?
C3 C26 N3 118.8(5) . . ?
C7 C26 N3 119.6(5) . . ?
C46 C27 Sn1 116.3(4) . . ?
C46 C27 H27A 108.2 . . ?
Sn1 C27 H27A 108.2 . . ?
C46 C27 H27B 108.2 . . ?
Sn1 C27 H27B 108.2 . . ?
H27A C27 H27B 107.4 . . ?
N4 C31 C25 106.9(4) . . ?
N4 C31 C18 121.5(4) . . ?
C25 C31 C18 131.6(4) . . ?
O2 C35 N3 124.9(4) . . ?
O2 C35 C25 128.0(4) . . ?
N3 C35 C25 107.0(4) . . ?
O4 C37 C22 125.2(4) . . ?
O4 C37 C14 117.1(5) . . ?
C22 C37 C14 117.7(5) . . ?
C60 C42 H42A 109.5 . . ?
C60 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C60 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C47 C46 C27 118.4(6) . . ?
C47 C46 H46A 107.7 . . ?
C27 C46 H46A 107.7 . . ?
C47 C46 H46B 107.7 . . ?
C27 C46 H46B 107.7 . . ?
H46A C46 H46B 107.1 . . ?
O6 C47 O7 122.4(8) . . ?
O6 C47 C46 126.0(8) . . ?
O7 C47 C46 111.6(6) . . ?
N4 C55 H55A 109.5 . . ?
N4 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
N4 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
O7 C60 C42 102.9(7) . . ?
O7 C60 H60A 111.2 . . ?
C42 C60 H60A 111.2 . . ?
O7 C60 H60B 111.2 . . ?
C42 C60 H60B 111.2 . . ?
H60A C60 H60B 109.1 . . ?
C1 C54 C2 121.1(7) . . ?
C1 C54 H54 119.4 . . ?
C2 C54 H54 119.4 . . ?
C7 C2 C54 120.0(7) . . ?
C7 C2 H2 120.0 . . ?
C54 C2 H2 120.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sn1 O4 2.033(4) . ?
Sn1 C27 2.144(6) . ?
Sn1 O2 2.171(3) . ?
Sn1 N1 2.241(4) . ?
Sn1 Cl3 2.4350(17) . ?
Sn1 Cl1 2.5154(17) . ?
O2 C35 1.255(6) . ?
O4 C37 1.322(6) . ?
O6 C47 1.191(9) . ?
O7 C47 1.340(9) . ?
O7 C60 1.472(9) . ?
N1 C19 1.298(6) . ?
N1 C25 1.404(5) . ?
N3 C35 1.363(6) . ?
N3 N4 1.391(6) . ?
N3 C26 1.434(6) . ?
N4 C31 1.340(6) . ?
N4 C55 1.455(6) . ?
C1 C54 1.343(11) . ?
C1 C3 1.380(9) . ?
C1 H1 0.9300 . ?
C3 C26 1.353(8) . ?
C3 H3 0.9300 . ?
C7 C26 1.365(8) . ?
C7 C2 1.374(9) . ?
C7 H7 0.9300 . ?
C8 C14 1.357(8) . ?
C8 C13 1.388(9) . ?
C8 H8 0.9300 . ?
C13 C16 1.374(7) . ?
C13 H13 0.9300 . ?
C14 C37 1.411(7) . ?
C14 H14 0.9300 . ?
C16 C22 1.412(7) . ?
C16 H16 0.9300 . ?
C18 C31 1.485(7) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C22 1.438(6) . ?
C19 H19 0.9300 . ?
C22 C37 1.408(8) . ?
C25 C31 1.387(7) . ?
C25 C35 1.400(7) . ?
C27 C46 1.519(9) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C42 C60 1.497(12) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C46 C47 1.513(10) . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C55 H55A 0.9600 . ?
C55 H55B 0.9600 . ?
C55 H55C 0.9600 . ?
C60 H60A 0.9700 . ?
C60 H60B 0.9700 . ?
C54 C2 1.368(12) . ?
C54 H54 0.9300 . ?
C2 H2 0.9300 . ?
