#------------------------------------------------------------------------------
#$Date: 2020-06-05 18:24:39 +0300 (Fri, 05 Jun 2020) $
#$Revision: 252941 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/81/1558190.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_1558190
loop_
_publ_author_name
'Bender, Desiree N.'
'Lough, Alan J.'
'Wylie, R. Stephen'
'Gossage, Robert A.'
'Foucher, Daniel A.'
_publ_section_title
;
 Preparation and DFT Studies of κ2C,N-Hypercoordinated Oxazoline
 Organotins: Monomer Constructs for Stable Polystannanes
;
_journal_issue                   5
_journal_name_full               Inorganics
_journal_page_first              35
_journal_paper_doi               10.3390/inorganics8050035
_journal_volume                  8
_journal_year                    2020
_chemical_formula_moiety         'C18 H19 Br2 N O Sn'
_chemical_formula_sum            'C18 H19 Br2 N O Sn'
_chemical_formula_weight         543.85
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                93.059(2)
_cell_angle_beta                 101.936(2)
_cell_angle_gamma                108.325(2)
_cell_formula_units_Z            2
_cell_length_a                   8.4530(5)
_cell_length_b                   10.2368(5)
_cell_length_c                   11.7987(7)
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.76
_cell_volume                     940.50(9)
_computing_cell_refinement       APEX3
_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015a)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            43074
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         1.779
_diffrn_source
'sealed tube with Bruker Triumph monochromator'
_exptl_absorpt_coefficient_mu    5.610
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.920
_exptl_crystal_description       Shard
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         4285
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0183
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0042P)²+1.1095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0358
_refine_ls_wR_factor_ref         0.0387
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3851
_reflns_number_total             4285
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2046_a_11.cif
_cod_data_source_block           d2046_a
_cod_database_code               1558190
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.334
_shelx_estimated_absorpt_t_max   0.487
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sn1 Sn 0.37496(2) 0.33861(2) 0.31213(2) 0.02113(4) Uani 1 1 d . . . . .
Br1 Br 0.70150(3) 0.43279(2) 0.42350(2) 0.02948(6) Uani 1 1 d . . . . .
Br2 Br 0.42870(3) 0.16421(2) 0.17989(2) 0.02932(6) Uani 1 1 d . . . . .
O1 O -0.1479(2) 0.02708(17) 0.16191(17) 0.0395(4) Uani 1 1 d . . . . .
N1 N 0.0757(2) 0.22388(18) 0.21513(16) 0.0248(4) Uani 1 1 d . . . . .
C1 C 0.2729(3) 0.2462(2) 0.4501(2) 0.0286(5) Uani 1 1 d . . . . .
H1A H 0.364938 0.271759 0.522739 0.034 Uiso 1 1 calc R U . . .
H1B H 0.182493 0.283473 0.463409 0.034 Uiso 1 1 calc R U . . .
C2 C 0.1988(3) 0.0918(2) 0.4245(2) 0.0280(5) Uani 1 1 d . . . . .
C3 C 0.2578(4) 0.0119(3) 0.5034(2) 0.0365(6) Uani 1 1 d . . . . .
H3A H 0.349248 0.056431 0.569315 0.044 Uiso 1 1 calc R U . . .
C4 C 0.1858(4) -0.1314(3) 0.4878(3) 0.0444(7) Uani 1 1 d . . . . .
H4A H 0.228080 -0.183993 0.542877 0.053 Uiso 1 1 calc R U . . .
C5 C 0.0537(4) -0.1975(3) 0.3933(3) 0.0435(7) Uani 1 1 d . . . . .
H5A H 0.003764 -0.295673 0.383641 0.052 Uiso 1 1 calc R U . . .
C6 C -0.0069(3) -0.1221(2) 0.3120(2) 0.0369(6) Uani 1 1 d . . . . .
H6A H -0.098342 -0.168316 0.246496 0.044 Uiso 1 1 calc R U . . .
C7 C 0.0667(3) 0.0234(2) 0.3262(2) 0.0290(5) Uani 1 1 d . . . . .
C8 C 0.0033(3) 0.0992(2) 0.2355(2) 0.0282(5) Uani 1 1 d . . . . .
C9 C -0.0335(3) 0.2529(2) 0.1107(2) 0.0277(5) Uani 1 1 d . . . . .
C10 C -0.1860(3) 0.1158(3) 0.0778(3) 0.0397(6) Uani 1 1 d . . . . .
H10A H -0.294282 0.132091 0.081763 0.048 Uiso 1 1 calc R U . . .
H10B H -0.197320 0.073764 -0.002208 0.048 Uiso 1 1 calc R U . . .
C11 C -0.0918(3) 0.3731(3) 0.1426(3) 0.0434(6) Uani 1 1 d . . . . .
H11A H -0.174859 0.383907 0.075530 0.065 Uiso 1 1 calc R U . . .
H11B H 0.007459 0.458553 0.164220 0.065 Uiso 1 1 calc R U . . .
H11C H -0.145588 0.354363 0.208773 0.065 Uiso 1 1 calc R U . . .
C12 C 0.0607(3) 0.2800(3) 0.0132(2) 0.0429(6) Uani 1 1 d . . . . .
H12A H -0.016582 0.290680 -0.057324 0.064 Uiso 1 1 calc R U . . .
H12B H 0.099414 0.201775 -0.003251 0.064 Uiso 1 1 calc R U . . .
H12C H 0.160194 0.365127 0.037184 0.064 Uiso 1 1 calc R U . . .
C13 C 0.3981(3) 0.5264(2) 0.23693(17) 0.0197(4) Uani 1 1 d . . . . .
C14 C 0.5031(3) 0.5586(2) 0.15840(19) 0.0257(4) Uani 1 1 d . . . . .
H14A H 0.551719 0.493261 0.133809 0.031 Uiso 1 1 calc R U . . .
C15 C 0.5367(3) 0.6859(2) 0.1161(2) 0.0297(5) Uani 1 1 d . . . . .
H15A H 0.607108 0.707133 0.061909 0.036 Uiso 1 1 calc R U . . .
C16 C 0.4677(3) 0.7818(2) 0.1529(2) 0.0287(5) Uani 1 1 d . . . . .
H16A H 0.492284 0.869482 0.124611 0.034 Uiso 1 1 calc R U . . .
C17 C 0.3634(3) 0.7508(2) 0.2304(2) 0.0272(5) Uani 1 1 d . . . . .
H17A H 0.315662 0.816797 0.255116 0.033 Uiso 1 1 calc R U . . .
C18 C 0.3281(3) 0.6229(2) 0.27235(18) 0.0239(4) Uani 1 1 d . . . . .
H18A H 0.255837 0.601463 0.325447 0.029 Uiso 1 1 calc R U . . .
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'
Br Br -0.2901 2.4595 '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
C1 Sn1 C13 136.53(8) . . ?
C1 Sn1 N1 78.24(8) . . ?
C13 Sn1 N1 95.47(7) . . ?
C1 Sn1 Br2 111.35(6) . . ?
C13 Sn1 Br2 110.78(6) . . ?
N1 Sn1 Br2 84.68(4) . . ?
C1 Sn1 Br1 98.03(7) . . ?
C13 Sn1 Br1 91.39(5) . . ?
N1 Sn1 Br1 172.89(4) . . ?
Br2 Sn1 Br1 91.148(9) . . ?
C8 O1 C10 107.31(18) . . ?
C8 N1 C9 108.96(18) . . ?
C8 N1 Sn1 117.61(15) . . ?
C9 N1 Sn1 131.21(13) . . ?
C2 C1 Sn1 112.32(15) . . ?
C2 C1 H1A 109.1 . . ?
Sn1 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
Sn1 C1 H1B 109.1 . . ?
H1A C1 H1B 107.9 . . ?
C3 C2 C7 118.3(2) . . ?
C3 C2 C1 118.9(2) . . ?
C7 C2 C1 122.7(2) . . ?
C4 C3 C2 121.3(3) . . ?
C4 C3 H3A 119.4 . . ?
C2 C3 H3A 119.4 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C5 C6 C7 120.0(3) . . ?
C5 C6 H6A 120.0 . . ?
C7 C6 H6A 120.0 . . ?
C2 C7 C6 119.9(2) . . ?
C2 C7 C8 121.82(19) . . ?
C6 C7 C8 118.3(2) . . ?
N1 C8 O1 116.2(2) . . ?
N1 C8 C7 128.5(2) . . ?
O1 C8 C7 115.29(19) . . ?
N1 C9 C11 110.27(19) . . ?
N1 C9 C12 110.53(18) . . ?
C11 C9 C12 111.9(2) . . ?
N1 C9 C10 101.97(19) . . ?
C11 C9 C10 111.06(19) . . ?
C12 C9 C10 110.7(2) . . ?
O1 C10 C9 105.59(19) . . ?
O1 C10 H10A 110.6 . . ?
C9 C10 H10A 110.6 . . ?
O1 C10 H10B 110.6 . . ?
C9 C10 H10B 110.6 . . ?
H10A C10 H10B 108.8 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 119.37(19) . . ?
C18 C13 Sn1 122.49(15) . . ?
C14 C13 Sn1 117.78(15) . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14A 119.9 . . ?
C13 C14 H14A 119.9 . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15A 120.0 . . ?
C14 C15 H15A 120.0 . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 H16A 119.9 . . ?
C15 C16 H16A 119.9 . . ?
C16 C17 C18 119.9(2) . . ?
C16 C17 H17A 120.0 . . ?
C18 C17 H17A 120.0 . . ?
C13 C18 C17 120.26(19) . . ?
C13 C18 H18A 119.9 . . ?
C17 C18 H18A 119.9 . . ?
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 C1 2.127(2) . ?
Sn1 C13 2.1302(19) . ?
Sn1 N1 2.4245(18) . ?
Sn1 Br2 2.5167(3) . ?
Sn1 Br1 2.6394(3) . ?
O1 C8 1.346(3) . ?
O1 C10 1.436(3) . ?
N1 C8 1.289(3) . ?
N1 C9 1.484(3) . ?
C1 C2 1.494(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.388(3) . ?
C2 C7 1.403(3) . ?
C3 C4 1.386(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.370(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.379(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.408(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.465(3) . ?
C9 C11 1.519(3) . ?
C9 C12 1.520(3) . ?
C9 C10 1.542(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.388(3) . ?
C13 C14 1.394(3) . ?
C14 C15 1.386(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.383(3) . ?
C15 H15A 0.9500 . ?
C16 C17 1.380(3) . ?
C16 H16A 0.9500 . ?
C17 C18 1.390(3) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Sn1 C1 C2 C3 124.64(19) . . . . ?
Sn1 C1 C2 C7 -58.1(3) . . . . ?
C7 C2 C3 C4 -1.6(3) . . . . ?
C1 C2 C3 C4 175.7(2) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C4 C5 C6 C7 -0.1(4) . . . . ?
C3 C2 C7 C6 2.4(3) . . . . ?
C1 C2 C7 C6 -174.9(2) . . . . ?
C3 C2 C7 C8 -176.7(2) . . . . ?
C1 C2 C7 C8 6.1(3) . . . . ?
C5 C6 C7 C2 -1.5(3) . . . . ?
C5 C6 C7 C8 177.5(2) . . . . ?
C9 N1 C8 O1 -0.4(3) . . . . ?
Sn1 N1 C8 O1 -165.38(14) . . . . ?
C9 N1 C8 C7 177.3(2) . . . . ?
Sn1 N1 C8 C7 12.3(3) . . . . ?
C10 O1 C8 N1 -0.2(3) . . . . ?
C10 O1 C8 C7 -178.19(19) . . . . ?
C2 C7 C8 N1 17.4(3) . . . . ?
C6 C7 C8 N1 -161.6(2) . . . . ?
C2 C7 C8 O1 -164.8(2) . . . . ?
C6 C7 C8 O1 16.1(3) . . . . ?
C8 N1 C9 C11 118.8(2) . . . . ?
Sn1 N1 C9 C11 -79.0(2) . . . . ?
C8 N1 C9 C12 -117.0(2) . . . . ?
Sn1 N1 C9 C12 45.2(3) . . . . ?
C8 N1 C9 C10 0.7(2) . . . . ?
Sn1 N1 C9 C10 162.95(15) . . . . ?
C8 O1 C10 C9 0.6(2) . . . . ?
N1 C9 C10 O1 -0.8(2) . . . . ?
C11 C9 C10 O1 -118.3(2) . . . . ?
C12 C9 C10 O1 116.8(2) . . . . ?
C18 C13 C14 C15 -0.1(3) . . . . ?
Sn1 C13 C14 C15 -173.39(17) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 C17 -0.9(3) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C14 C13 C18 C17 -0.4(3) . . . . ?
Sn1 C13 C18 C17 172.53(16) . . . . ?
C16 C17 C18 C13 0.3(3) . . . . ?
