#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/97/2239718.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_2239718
loop_
_publ_author_name
'Cheng, Miao'
'Zhao, Yuhong'
'Dong, Tiantian'
'Cui, Jichun'
_publ_section_title
;
 {4-Amino-N'-[(2-oxidonaphthalen-1-yl)methylidene]benzohydrazidato}dimethyltin(IV)
;
_journal_coeditor_code           CV5466
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m283
_journal_paper_doi               10.1107/S1600536814014652
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          '[Sn (C H3)2 (C18 H13 N3 O2)]'
_chemical_formula_moiety         'C20 H19 N3 O2 Sn'
_chemical_formula_sum            'C20 H19 N3 O2 Sn'
_chemical_formula_weight         452.07
_chemical_name_systematic
{4-Amino-N'-[(2-oxidonaphthalen-1-yl)methylidene]benzohydrazidato}dimethyltin(IV)
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.3545(7)
_cell_length_b                   12.9503(11)
_cell_length_c                   34.291(2)
_cell_measurement_reflns_used    1667
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.3661
_cell_measurement_theta_min      2.7065
_cell_volume                     3710.1(5)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       'phi and omega 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  0.0552
_diffrn_reflns_av_sigmaI/netI    0.0694
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            8234
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    1.396
_exptl_absorpt_correction_T_max  0.8179
_exptl_absorpt_correction_T_min  0.6407
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.489
_refine_diff_density_min         -1.274
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3265
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0515
_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)+(0.0340P)²+1.7722P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1210
_reflns_number_gt                2382
_reflns_number_total             3265
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv5466sup1.cf
_cod_data_source_block           I
_cod_database_code               2239718
_cod_database_fobs_code          2239718
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
_atom_site_symmetry_multiplicity
Sn Sn1 0.22653(5) 0.82846(3) 0.350360(13) 0.03635(18) Uani d . 1 1
C C1 0.6096(7) 1.0398(4) 0.31885(17) 0.0282(13) Uani d . 1 1
C C2 0.6565(7) 1.1338(4) 0.33421(18) 0.0333(14) Uani d . 1 1
H H2 0.6144 1.1553 0.3580 0.040 Uiso calc R 1 1
C C3 0.7651(7) 1.1966(5) 0.3149(2) 0.0357(16) Uani d . 1 1
H H3 0.7940 1.2599 0.3256 0.043 Uiso calc R 1 1
C C4 0.8311(7) 1.1654(5) 0.27934(19) 0.0346(14) Uani d . 1 1
C C5 0.7822(7) 1.0706(5) 0.26347(19) 0.0361(15) Uani d . 1 1
H H5 0.8241 1.0488 0.2397 0.043 Uiso calc R 1 1
C C6 0.6718(7) 1.0092(4) 0.28297(18) 0.0326(14) Uani d . 1 1
H H6 0.6391 0.9471 0.2720 0.039 Uiso calc R 1 1
C C7 0.4895(7) 0.9742(5) 0.33911(19) 0.0337(15) Uani d . 1 1
C C8 0.3081(8) 0.9472(4) 0.4283(2) 0.0358(15) Uani d . 1 1
H H8 0.3624 1.0011 0.4404 0.043 Uiso calc R 1 1
C C9 0.1988(7) 0.8916(5) 0.45182(18) 0.0331(15) Uani d . 1 1
C C10 0.1039(7) 0.8101(4) 0.43669(19) 0.0365(15) Uani d . 1 1
C C18 0.1849(7) 0.9175(5) 0.4931(2) 0.0366(15) Uani d . 1 1
C C11 0.0086(9) 0.7509(5) 0.4619(2) 0.052(2) Uani d . 1 1
H H11 -0.0513 0.6962 0.4521 0.062 Uiso calc R 1 1
C C12 0.0036(9) 0.7732(6) 0.5005(2) 0.057(2) Uani d . 1 1
H H12 -0.0591 0.7321 0.5167 0.069 Uiso calc R 1 1
C C13 0.0892(8) 0.8557(5) 0.5173(2) 0.0456(18) Uani d . 1 1
C C14 0.0800(10) 0.8798(7) 0.5574(2) 0.065(2) Uani d . 1 1
H H14 0.0174 0.8382 0.5734 0.078 Uiso calc R 1 1
C C15 0.1576(10) 0.9600(7) 0.5734(2) 0.067(2) Uani d . 1 1
H H15 0.1495 0.9737 0.5999 0.081 Uiso calc R 1 1
C C16 0.2504(9) 1.0222(7) 0.5491(2) 0.058(2) Uani d . 1 1
H H16 0.3037 1.0788 0.5596 0.070 Uiso calc R 1 1
C C17 0.2644(8) 1.0012(6) 0.5102(2) 0.0485(19) Uani d . 1 1
H H17 0.3282 1.0435 0.4948 0.058 Uiso calc R 1 1
C C19 0.0383(9) 0.9080(5) 0.3224(2) 0.057(2) Uani d . 1 1
H H19A -0.0545 0.9080 0.3389 0.085 Uiso calc R 1 1
H H19B 0.0132 0.8742 0.2982 0.085 Uiso calc R 1 1
H H19C 0.0705 0.9778 0.3173 0.085 Uiso calc R 1 1
C C20 0.3138(9) 0.6763(5) 0.3414(2) 0.056(2) Uani d . 1 1
H H20A 0.2512 0.6286 0.3564 0.084 Uiso calc R 1 1
H H20B 0.4237 0.6726 0.3495 0.084 Uiso calc R 1 1
H H20C 0.3059 0.6590 0.3142 0.084 Uiso calc R 1 1
N N1 0.4605(6) 0.9964(3) 0.37632(14) 0.0331(12) Uani d . 1 1
N N2 0.3417(6) 0.9318(3) 0.39137(15) 0.0323(12) Uani d . 1 1
N N3 0.9344(7) 1.2295(4) 0.25953(17) 0.0493(15) Uani d . 1 1
H H3A 0.9585 1.2890 0.2690 0.059 Uiso calc R 1 1
H H3B 0.9749 1.2101 0.2377 0.059 Uiso calc R 1 1
O O1 0.4219(5) 0.9000(3) 0.31939(12) 0.0393(11) Uani d . 1 1
O O2 0.0996(6) 0.7846(4) 0.39985(14) 0.0609(15) Uani d . 1 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'
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'
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
O2 Sn1 C19 97.1(3)
O2 Sn1 C20 92.3(3)
C19 Sn1 C20 130.0(3)
O2 Sn1 O1 154.81(18)
C19 Sn1 O1 97.5(2)
C20 Sn1 O1 93.9(2)
O2 Sn1 N2 82.28(18)
C19 Sn1 N2 108.9(2)
C20 Sn1 N2 121.0(2)
O1 Sn1 N2 73.63(17)
C2 C1 C6 118.8(5)
C2 C1 C7 121.0(5)
C6 C1 C7 120.1(5)
C1 C2 C3 121.3(6)
C1 C2 H2 119.4
C3 C2 H2 119.4
C2 C3 C4 120.3(6)
C2 C3 H3 119.8
C4 C3 H3 119.8
N3 C4 C3 120.2(6)
N3 C4 C5 121.2(6)
C3 C4 C5 118.5(6)
C6 C5 C4 120.4(6)
C6 C5 H5 119.8
C4 C5 H5 119.8
C5 C6 C1 120.7(6)
C5 C6 H6 119.7
C1 C6 H6 119.7
O1 C7 N1 125.3(5)
O1 C7 C1 118.1(5)
N1 C7 C1 116.6(5)
N2 C8 C9 127.7(6)
N2 C8 H8 116.2
C9 C8 H8 116.2
C8 C9 C10 122.0(6)
C8 C9 C18 119.2(6)
C10 C9 C18 118.8(6)
O2 C10 C11 116.2(6)
O2 C10 C9 123.9(6)
C11 C10 C9 119.9(6)
C17 C18 C13 117.6(7)
C17 C18 C9 123.2(6)
C13 C18 C9 119.2(6)
C12 C11 C10 120.2(7)
C12 C11 H11 119.9
C10 C11 H11 119.9
C11 C12 C13 122.9(7)
C11 C12 H12 118.5
C13 C12 H12 118.5
C18 C13 C12 118.8(7)
C18 C13 C14 118.8(7)
C12 C13 C14 122.5(7)
C15 C14 C13 122.9(8)
C15 C14 H14 118.5
C13 C14 H14 118.5
C14 C15 C16 118.1(7)
C14 C15 H15 120.9
C16 C15 H15 120.9
C17 C16 C15 121.0(8)
C17 C16 H16 119.5
C15 C16 H16 119.5
C16 C17 C18 121.6(8)
C16 C17 H17 119.2
C18 C17 H17 119.2
Sn1 C19 H19A 109.5
Sn1 C19 H19B 109.5
H19A C19 H19B 109.5
Sn1 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
Sn1 C20 H20A 109.5
Sn1 C20 H20B 109.5
H20A C20 H20B 109.5
Sn1 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C7 N1 N2 110.8(5)
C8 N2 N1 114.7(5)
C8 N2 Sn1 128.7(4)
N1 N2 Sn1 116.5(4)
C4 N3 H3A 120.0
C4 N3 H3B 120.0
H3A N3 H3B 120.0
C7 O1 Sn1 112.9(4)
C10 O2 Sn1 134.9(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Sn1 O2 2.080(5)
Sn1 C19 2.110(7)
Sn1 C20 2.123(6)
Sn1 O1 2.157(4)
Sn1 N2 2.167(5)
C1 C2 1.383(8)
C1 C6 1.393(8)
C1 C7 1.487(8)
C2 C3 1.388(8)
C2 H2 0.9300
C3 C4 1.397(9)
C3 H3 0.9300
C4 N3 1.377(8)
C4 C5 1.403(8)
C5 C6 1.389(8)
C5 H5 0.9300
C6 H6 0.9300
C7 O1 1.304(7)
C7 N1 1.330(8)
C8 N2 1.311(8)
C8 C9 1.416(8)
C8 H8 0.9300
C9 C10 1.418(8)
C9 C18 1.458(9)
C10 O2 1.306(7)
C10 C11 1.403(9)
C18 C17 1.401(9)
C18 C13 1.402(9)
C11 C12 1.356(10)
C11 H11 0.9300
C12 C13 1.409(10)
C12 H12 0.9300
C13 C14 1.412(10)
C14 C15 1.342(11)
C14 H14 0.9300
C15 C16 1.394(11)
C15 H15 0.9300
C16 C17 1.366(10)
C16 H16 0.9300
C17 H17 0.9300
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
N1 N2 1.397(6)
N3 H3A 0.8600
N3 H3B 0.8600
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
N3 H3A O1 8_765 0.86 2.46 3.245(7) 152
