#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:55:58 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178730 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/41/4084164.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_4084164
loop_
_publ_author_name
'Yasuda, Makoto'
'Nagano, Yoshitaka'
'Yunoki, Hiroshi'
'Tsuruwa, Kensuke'
'Baba, Akio'
_publ_section_title
;
 Chiral Transfer in the Reaction of Aminoallylic Stannanes with Carbonyls
 in Two Different Modes using Tin(II) and Indium(III) Halides for the
 Synthesis of Each Enantiomer
;
_journal_issue                   15
_journal_name_full               Organometallics
_journal_page_first              3924
_journal_paper_doi               10.1021/om500768e
_journal_volume                  33
_journal_year                    2014
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C16 H25 N O2 Sn'
_chemical_formula_sum            'C16 H25 N O2 Sn'
_chemical_formula_weight         382.07
_space_group_IT_number           76
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      76
_symmetry_space_group_name_Hall  'P 4w'
_symmetry_space_group_name_H-M   'P 41'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   10.1368(9)
_cell_length_b                   10.1368(9)
_cell_length_c                   18.0925(15)
_cell_measurement_reflns_used    7426
_cell_measurement_temperature    296
_cell_measurement_theta_max      30.48
_cell_measurement_theta_min      3.02
_cell_volume                     1859.1(3)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1809
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18510
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.376
_exptl_absorpt_correction_T_max  0.871
_exptl_absorpt_correction_T_min  0.461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             776.00
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.770
_refine_diff_density_min         -1.690
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1958 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.433
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     207
_refine_ls_number_reflns         1840
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.016
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/σ²(Fo)'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_ref         0.0261
_reflns_number_gt                1472
_reflns_number_total             4157
_reflns_threshold_expression     F>2.0σ(F)
_cod_data_source_file            om500768e_si_002.cif
_cod_data_source_block           No252-type1
_cod_depositor_comments
'Adding full bibliography for 4084164--4084171.cif.'
_cod_database_code               4084164
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -Y,+X,1/4+Z
3 -X,-Y,1/2+Z
4 +Y,-X,3/4+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_calc_flag
_atom_site_refinement_flags
Sn1 Sn 0.30202(7) 0.19900(7) 0.83555(12) 0.0834(3) Uani 1.0 4 d .
O1 O 0.1571(6) 0.0242(7) 0.9208(3) 0.066(3) Uani 1.0 4 d .
O17 O 0.0607(6) -0.2710(6) 0.8330(5) 0.090(3) Uani 1.0 4 d .
N18 N 0.1153(8) -0.0300(8) 0.8031(5) 0.058(4) Uani 1.0 4 d .
C2 C 0.3984(11) -0.3437(10) 0.9645(8) 0.081(5) Uani 1.0 4 d .
C3 C 0.1212(10) -0.0579(12) 0.8762(7) 0.060(5) Uani 1.0 4 d .
C4 C 0.1845(13) -0.2556(9) 0.9473(7) 0.058(4) Uani 1.0 4 d .
C5 C 0.1553(10) -0.2828(11) 1.0211(7) 0.081(5) Uani 1.0 4 d .
C6 C 0.1499(10) 0.1008(11) 0.7735(5) 0.066(4) Uani 1.0 4 d .
C7 C 0.3049(12) -0.2861(10) 0.9210(5) 0.063(4) Uani 1.0 4 d .
C8 C 0.0318(15) 0.1866(11) 0.7662(6) 0.079(5) Uani 1.0 4 d .
C9 C -0.0112(11) -0.3892(9) 0.8473(7) 0.133(6) Uani 1.0 4 d .
C10 C 0.4565(9) 0.0679(11) 0.8635(6) 0.148(7) Uani 1.0 4 d .
C11 C 0.0811(11) -0.1956(11) 0.8978(5) 0.062(4) Uani 1.0 4 d .
C12 C -0.1894(12) 0.2809(11) 0.7896(8) 0.130(7) Uani 1.0 4 d .
C13 C 0.3685(13) -0.3698(11) 1.0377(8) 0.087(6) Uani 1.0 4 d .
C14 C 0.2343(12) 0.3169(12) 0.9235(5) 0.135(6) Uani 1.0 4 d .
C15 C -0.0799(15) 0.1814(13) 0.7988(6) 0.084(6) Uani 1.0 4 d .
C16 C 0.3820(12) 0.3280(12) 0.7538(6) 0.169(7) Uani 1.0 4 d .
C21 C 0.2472(15) -0.3406(12) 1.0655(6) 0.103(6) Uani 1.0 4 d .
H1 H 0.0839 -0.0943 0.7709 0.0694 Uiso 1.0 4 calc R
H2 H 0.4820 -0.3686 0.9486 0.0970 Uiso 1.0 4 calc R
H3 H 0.0702 -0.2605 1.0356 0.0968 Uiso 1.0 4 calc R
H4 H 0.3288 -0.2675 0.8725 0.0756 Uiso 1.0 4 calc R
H5 H 0.0391 0.2590 0.7349 0.0951 Uiso 1.0 4 calc R
H6 H 0.4284 -0.4036 1.0717 0.1043 Uiso 1.0 4 calc R
H7 H -0.0908 0.1097 0.8303 0.1011 Uiso 1.0 4 calc R
H8 H 0.2188 -0.3578 1.1134 0.1232 Uiso 1.0 4 calc R
H9 H -0.0975 -0.3693 0.8661 0.1599 Uiso 1.0 4 calc R
H10 H -0.0192 -0.4368 0.8016 0.1599 Uiso 1.0 4 calc R
H11 H 0.0357 -0.4422 0.8825 0.1599 Uiso 1.0 4 calc R
H12 H -0.2154 0.2832 0.7386 0.1562 Uiso 1.0 4 calc R
H13 H -0.2636 0.2561 0.8195 0.1562 Uiso 1.0 4 calc R
H14 H -0.1589 0.3666 0.8043 0.1563 Uiso 1.0 4 calc R
H15 H 0.4262 0.0088 0.9013 0.1777 Uiso 1.0 4 calc R
H16 H 0.4808 0.0183 0.8204 0.1777 Uiso 1.0 4 calc R
H17 H 0.5318 0.1159 0.8812 0.1777 Uiso 1.0 4 calc R
H18 H 0.1677 0.3762 0.9057 0.1623 Uiso 1.0 4 calc R
H19 H 0.1978 0.2619 0.9615 0.1622 Uiso 1.0 4 calc R
H20 H 0.3067 0.3667 0.9432 0.1623 Uiso 1.0 4 calc R
H21 H 0.4536 0.3778 0.7744 0.2026 Uiso 1.0 4 calc R
H22 H 0.4136 0.2764 0.7129 0.2025 Uiso 1.0 4 calc R
H23 H 0.3146 0.3872 0.7368 0.2026 Uiso 1.0 4 calc R
H24 H 0.1854 0.0856 0.7238 0.0788 Uiso 1.0 4 calc R
H25 H 0.0004 -0.1931 0.9276 0.0741 Uiso 1.0 4 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 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Sn Sn -0.654 1.425
;
International Tables for Crystallography
(1992, 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
C6 Sn1 C10 111.4(4) yes
C6 Sn1 C14 115.0(4) yes
C6 Sn1 C16 101.2(4) yes
C10 Sn1 C14 114.7(5) yes
C10 Sn1 C16 105.6(5) yes
C14 Sn1 C16 107.5(5) yes
C9 O17 C11 112.2(9) yes
C3 N18 C6 122.2(9) yes
C7 C2 C13 118.8(11) yes
O1 C3 N18 121.3(10) yes
O1 C3 C11 122.9(11) yes
N18 C3 C11 115.8(10) yes
C5 C4 C7 119.0(10) yes
C5 C4 C11 120.1(10) yes
C7 C4 C11 120.9(10) yes
C4 C5 C21 120.3(11) yes
Sn1 C6 N18 113.4(6) yes
Sn1 C6 C8 110.7(7) yes
N18 C6 C8 111.5(9) yes
C2 C7 C4 121.7(10) yes
C6 C8 C15 130.5(11) yes
O17 C11 C3 109.0(8) yes
O17 C11 C4 112.1(9) yes
C3 C11 C4 109.9(9) yes
C2 C13 C21 120.7(12) yes
C8 C15 C12 125.0(11) yes
C5 C21 C13 119.5(11) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Sn1 C6 2.151(10) yes
Sn1 C10 2.115(10) yes
Sn1 C14 2.104(11) yes
Sn1 C16 2.134(11) yes
O1 C3 1.215(14) yes
O17 C9 1.426(12) yes
O17 C11 1.415(13) yes
N18 C3 1.354(16) yes
N18 C6 1.473(13) yes
C2 C7 1.363(16) yes
C2 C13 1.383(19) yes
C3 C11 1.506(16) yes
C4 C5 1.394(17) yes
C4 C7 1.346(17) yes
C4 C11 1.507(16) yes
C5 C21 1.363(18) yes
C6 C8 1.486(17) yes
C8 C15 1.28(2) yes
C12 C15 1.509(18) yes
C13 C21 1.36(2) yes
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_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N18 H1 O1 4_554 2.873(12) 0.930 2.014 152.9 no
N18 H1 O17 . 2.574(12) 0.930 2.133 107.8 no
