#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/29/2212907.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_2212907
loop_
_publ_author_name
'Shuja, Shaukat'
'Ali, Saqib'
'Meetsma, Auke'
'Broker, Grant A.'
'Tiekink, Edward R. T.'
_publ_section_title
'[N-Formyl-N'-(2-oxidobenzylidene)hydrazine-κ³O,N,O']diphenyltin(IV)'
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1130
_journal_page_last               m1132
_journal_paper_doi               10.1107/S1600536807012767
_journal_volume                  63
_journal_year                    2007
_chemical_formula_moiety         'C20 H16 N2 O2 Sn'
_chemical_formula_sum            'C20 H16 N2 O2 Sn'
_chemical_formula_weight         435.04
_chemical_name_systematic
;
 ?
;
_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                77.2770(10)
_cell_angle_beta                 74.3240(10)
_cell_angle_gamma                68.8690(10)
_cell_formula_units_Z            2
_cell_length_a                   8.9903(5)
_cell_length_b                   9.0639(5)
_cell_length_c                   11.8622(7)
_cell_measurement_reflns_used    7180
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.6
_cell_measurement_theta_min      2.4
_cell_volume                     859.93(8)
_computing_cell_refinement       'SAINT-Plus  (Bruker, 2006)'
_computing_data_collection       'SMART (Bruker, 2006)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) & DIAMOND (Brandenburg, 2006)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution
'PATTY in DIRDIF92 (Beurskens et al.,  1992)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean '4096x4096 / 62x62 (binned 512)'
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_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  0.030
_diffrn_reflns_av_sigmaI/netI    0.028
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6594
_diffrn_reflns_theta_full        26.0
_diffrn_reflns_theta_max         26.0
_diffrn_reflns_theta_min         2.4
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.501
_exptl_absorpt_correction_T_max  0.557
_exptl_absorpt_correction_T_min  0.459
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.68
_refine_diff_density_min         -0.74
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.12
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3297
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.12
_refine_ls_R_factor_all          0.023
_refine_ls_R_factor_gt           0.022
_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)+(0.0258P)²+0.9175P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.058
_refine_ls_wR_factor_ref         0.058
_reflns_number_gt                3196
_reflns_number_total             3297
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2334.cif
_cod_data_source_block           I
_cod_database_code               2212907
_cod_database_fobs_code          2212907
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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 Sn 0.073101(18) 0.179092(18) 0.246058(13) 0.01552(7) Uani d . 1
O O1 0.2676(2) -0.0444(2) 0.24888(15) 0.0215(4) Uani d . 1
O O2 -0.1012(2) 0.3823(2) 0.30705(15) 0.0201(4) Uani d . 1
N N1 0.2437(3) -0.0236(3) 0.44564(19) 0.0217(4) Uani d . 1
N N2 0.1199(2) 0.1213(2) 0.42263(17) 0.0166(4) Uani d . 1
C C1 0.3058(3) -0.0949(3) 0.3519(2) 0.0195(5) Uani d . 1
H H1 0.3885 -0.1954 0.3595 0.023 Uiso calc R 1
C C2 0.0467(3) 0.2021(3) 0.5111(2) 0.0182(5) Uani d . 1
H H2 0.0854 0.1596 0.5823 0.022 Uiso calc R 1
C C3 -0.0863(3) 0.3487(3) 0.5121(2) 0.0176(5) Uani d . 1
C C4 -0.1546(3) 0.4316(3) 0.4123(2) 0.0169(5) Uani d . 1
C C5 -0.2846(3) 0.5750(3) 0.4244(2) 0.0219(5) Uani d . 1
H H5 -0.3305 0.6324 0.3579 0.026 Uiso calc R 1
C C6 -0.3469(3) 0.6339(3) 0.5313(2) 0.0251(6) Uani d . 1
H H6 -0.4350 0.7310 0.5376 0.030 Uiso calc R 1
C C7 -0.2814(3) 0.5518(3) 0.6308(2) 0.0228(5) Uani d . 1
H H7 -0.3255 0.5921 0.7044 0.027 Uiso calc R 1
C C8 -0.1529(3) 0.4126(3) 0.6205(2) 0.0209(5) Uani d . 1
H H8 -0.1075 0.3578 0.6877 0.025 Uiso calc R 1
C C9 -0.0923(3) 0.0795(3) 0.2184(2) 0.0169(5) Uani d . 1
C C10 -0.2589(3) 0.1418(3) 0.2658(2) 0.0198(5) Uani d . 1
H H10 -0.2980 0.2304 0.3083 0.024 Uiso calc R 1
C C11 -0.3678(3) 0.0742(3) 0.2509(2) 0.0239(5) Uani d . 1
H H11 -0.4807 0.1154 0.2847 0.029 Uiso calc R 1
C C12 -0.3118(3) -0.0530(3) 0.1867(2) 0.0232(5) Uani d . 1
H H12 -0.3867 -0.0980 0.1759 0.028 Uiso calc R 1
C C13 -0.1469(3) -0.1150(3) 0.1383(2) 0.0208(5) Uani d . 1
H H13 -0.1090 -0.2018 0.0940 0.025 Uiso calc R 1
C C14 -0.0366(3) -0.0496(3) 0.1545(2) 0.0190(5) Uani d . 1
H H14 0.0764 -0.0928 0.1222 0.023 Uiso calc R 1
C C15 0.2105(3) 0.3034(3) 0.1105(2) 0.0167(5) Uani d . 1
C C16 0.1485(3) 0.4688(3) 0.0857(2) 0.0219(5) Uani d . 1
H H16 0.0481 0.5254 0.1320 0.026 Uiso calc R 1
C C17 0.2329(3) 0.5521(3) -0.0067(2) 0.0259(6) Uani d . 1
H H17 0.1902 0.6650 -0.0233 0.031 Uiso calc R 1
C C18 0.3795(3) 0.4691(3) -0.0743(2) 0.0265(6) Uani d . 1
H H18 0.4366 0.5255 -0.1378 0.032 Uiso calc R 1
C C19 0.4429(3) 0.3049(3) -0.0498(2) 0.0269(6) Uani d . 1
H H19 0.5438 0.2490 -0.0960 0.032 Uiso calc R 1
C C20 0.3588(3) 0.2211(3) 0.0427(2) 0.0214(5) Uani d . 1
H H20 0.4025 0.1083 0.0595 0.026 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'
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_publ_flag
O2 Sn C9 96.23(8) ?
O2 Sn C15 95.10(8) ?
O1 Sn O2 158.42(7) y
O1 Sn N2 73.94(7) y
O2 Sn N2 84.49(7) y
C9 Sn C15 124.62(9) y
C9 Sn O1 93.72(8) ?
C15 Sn O1 94.91(8) ?
C9 Sn N2 115.22(8) ?
C15 Sn N2 119.75(8) ?
C1 O1 Sn 112.38(15) ?
C4 O2 Sn 132.88(16) ?
C1 N1 N2 110.2(2) ?
C2 N2 N1 115.7(2) ?
C2 N2 Sn 128.20(17) ?
N1 N2 Sn 116.09(14) ?
O1 C1 N1 127.4(2) ?
O1 C1 H1 116.3 ?
N1 C1 H1 116.3 ?
N2 C2 C3 126.6(2) ?
N2 C2 H2 116.7 ?
C3 C2 H2 116.7 ?
C4 C3 C8 118.8(2) ?
C4 C3 C2 124.0(2) ?
C8 C3 C2 117.1(2) ?
O2 C4 C5 117.7(2) ?
O2 C4 C3 123.6(2) ?
C5 C4 C3 118.7(2) ?
C6 C5 C4 121.0(2) ?
C6 C5 H5 119.5 ?
C4 C5 H5 119.5 ?
C5 C6 C7 120.7(2) ?
C5 C6 H6 119.7 ?
C7 C6 H6 119.7 ?
C8 C7 C6 119.2(2) ?
C8 C7 H7 120.4 ?
C6 C7 H7 120.4 ?
C7 C8 C3 121.5(2) ?
C7 C8 H8 119.2 ?
C3 C8 H8 119.2 ?
C10 C9 C14 119.4(2) ?
C10 C9 Sn 119.82(18) ?
C14 C9 Sn 120.82(17) ?
C11 C10 C9 120.2(2) ?
C11 C10 H10 119.9 ?
C9 C10 H10 119.9 ?
C12 C11 C10 120.1(2) ?
C12 C11 H11 119.9 ?
C10 C11 H11 119.9 ?
C13 C12 C11 120.3(2) ?
C13 C12 H12 119.9 ?
C11 C12 H12 119.9 ?
C12 C13 C14 119.9(2) ?
C12 C13 H13 120.0 ?
C14 C13 H13 120.0 ?
C13 C14 C9 120.1(2) ?
C13 C14 H14 119.9 ?
C9 C14 H14 119.9 ?
C16 C15 C20 119.5(2) ?
C16 C15 Sn 119.48(17) ?
C20 C15 Sn 120.95(18) ?
C15 C16 C17 120.4(2) ?
C15 C16 H16 119.8 ?
C17 C16 H16 119.8 ?
C18 C17 C16 119.7(3) ?
C18 C17 H17 120.2 ?
C16 C17 H17 120.2 ?
C19 C18 C17 120.4(2) ?
C19 C18 H18 119.8 ?
C17 C18 H18 119.8 ?
C18 C19 C20 120.1(2) ?
C18 C19 H19 119.9 ?
C20 C19 H19 119.9 ?
C15 C20 C19 119.9(2) ?
C15 C20 H20 120.1 ?
C19 C20 H20 120.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Sn O1 2.1470(18) y
Sn O2 2.0654(17) y
Sn N2 2.162(2) y
Sn C9 2.120(2) y
Sn C15 2.125(2) y
O1 C1 1.299(3) ?
O2 C4 1.325(3) ?
N1 C1 1.299(3) y
N1 N2 1.411(3) y
N2 C2 1.299(3) y
C1 H1 0.9500 ?
C2 C3 1.431(4) ?
C2 H2 0.9500 ?
C3 C4 1.418(3) ?
C3 C8 1.418(3) ?
C4 C5 1.405(3) ?
C5 C6 1.381(4) ?
C5 H5 0.9500 ?
C6 C7 1.402(4) ?
C6 H6 0.9500 ?
C7 C8 1.371(4) ?
C7 H7 0.9500 ?
C8 H8 0.9500 ?
C9 C10 1.397(3) ?
C9 C14 1.399(3) ?
C10 C11 1.392(4) ?
C10 H10 0.9500 ?
C11 C12 1.387(4) ?
C11 H11 0.9500 ?
C12 C13 1.388(4) ?
C12 H12 0.9500 ?
C13 C14 1.396(4) ?
C13 H13 0.9500 ?
C14 H14 0.9500 ?
C15 C16 1.391(4) ?
C15 C20 1.396(3) ?
C16 C17 1.395(4) ?
C16 H16 0.9500 ?
C17 C18 1.387(4) ?
C17 H17 0.9500 ?
C18 C19 1.383(4) ?
C18 H18 0.9500 ?
C19 C20 1.397(4) ?
C19 H19 0.9500 ?
C20 H20 0.9500 ?
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
C2 H2 Cg 2_556 0.95 2.93 3.872(3) 172 y
C19 H19 O1 2_655 0.95 2.67 3.554(3) 154 y
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O2 Sn O1 C1 3.5(3)
C9 Sn O1 C1 -113.83(16)
C15 Sn O1 C1 120.93(16)
N2 Sn O1 C1 1.36(15)
C9 Sn O2 C4 110.4(2)
C15 Sn O2 C4 -123.9(2)
O1 Sn O2 C4 -6.5(3)
N2 Sn O2 C4 -4.4(2)
C1 N1 N2 C2 178.9(2)
C1 N1 N2 Sn -0.2(2)
O2 Sn N2 C2 1.3(2)
C9 Sn N2 C2 -93.0(2)
C15 Sn N2 C2 94.0(2)
O1 Sn N2 C2 -179.5(2)
O2 Sn N2 N1 -179.85(16)
C9 Sn N2 N1 85.85(17)
C15 Sn N2 N1 -87.10(17)
O1 Sn N2 N1 -0.65(14)
Sn O1 C1 N1 -2.3(3)
N2 N1 C1 O1 1.7(3)
N1 N2 C2 C3 -177.4(2)
Sn N2 C2 C3 1.5(3)
N2 C2 C3 C4 -2.6(4)
N2 C2 C3 C8 177.1(2)
Sn O2 C4 C5 -176.08(16)
Sn O2 C4 C3 4.7(3)
C8 C3 C4 O2 179.9(2)
C2 C3 C4 O2 -0.5(4)
C8 C3 C4 C5 0.7(3)
C2 C3 C4 C5 -179.7(2)
O2 C4 C5 C6 179.9(2)
C3 C4 C5 C6 -0.8(4)
C4 C5 C6 C7 0.1(4)
C5 C6 C7 C8 0.8(4)
C6 C7 C8 C3 -0.9(4)
C4 C3 C8 C7 0.2(4)
C2 C3 C8 C7 -179.5(2)
O2 Sn C9 C10 -13.3(2)
C15 Sn C9 C10 -113.89(19)
O1 Sn C9 C10 147.53(19)
N2 Sn C9 C10 73.5(2)
O2 Sn C9 C14 167.59(19)
C15 Sn C9 C14 67.0(2)
O1 Sn C9 C14 -31.6(2)
N2 Sn C9 C14 -105.59(19)
C14 C9 C10 C11 0.9(4)
Sn C9 C10 C11 -178.21(19)
C9 C10 C11 C12 -1.4(4)
C10 C11 C12 C13 0.8(4)
C11 C12 C13 C14 0.3(4)
C12 C13 C14 C9 -0.8(4)
C10 C9 C14 C13 0.1(4)
Sn C9 C14 C13 179.27(18)
O2 Sn C15 C16 -8.3(2)
C9 Sn C15 C16 92.9(2)
O1 Sn C15 C16 -169.15(19)
N2 Sn C15 C16 -94.9(2)
O2 Sn C15 C20 174.43(19)
C9 Sn C15 C20 -84.4(2)
O1 Sn C15 C20 13.6(2)
N2 Sn C15 C20 87.9(2)
C20 C15 C16 C17 0.5(4)
Sn C15 C16 C17 -176.82(19)
C15 C16 C17 C18 0.1(4)
C16 C17 C18 C19 -0.6(4)
C17 C18 C19 C20 0.6(4)
C16 C15 C20 C19 -0.5(4)
Sn C15 C20 C19 176.75(19)
C18 C19 C20 C15 0.0(4)
