#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/52/4115276.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_4115276
loop_
_publ_author_name
'Makoto Yasuda'
'Kay Hirata'
'Mitsuyoshi Nishino'
'Akihiro Yamamoto'
'Akio Baba'
_publ_contact_author_address
;
    Department of Molecular Chemistry
    Graduate School of Engineering
    Osaka University
    2-1 Yamadaoka
    Suita Osaka 565-0871
    Japan
;
_publ_contact_author_email       ' baba@ap.chem.eng.osaka-u.ac.jp'
_publ_contact_author_fax         ' 81(6)68797387 '
_publ_contact_author_name        ' Dr Akio Baba'
_publ_contact_author_phone       ' 81(6)68797386 '
_publ_section_title
;
 Diastereoselective Addition of γ-Substituted Allylic Nucleophiles to
 Ketones: Highly Stereoselective Synthesis of Tertiary Homoallylic
 Alcohols Using an Allylic Tributylstannane/Stannous Chloride System
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13442
_journal_page_last               13447
_journal_paper_doi               10.1021/ja0274047
_journal_volume                  124
_journal_year                    2002
_chemical_formula_moiety         'C17 H18 O2 '
_chemical_formula_sum            'C17 H18 O2'
_chemical_formula_weight         254.33
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      88
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   23.703(2)
_cell_length_b                   23.703(2)
_cell_length_c                   10.2725(7)
_cell_measurement_reflns_used    25365
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.7
_cell_volume                     5771.4(8)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9994
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15500
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.658
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     244
_refine_ls_number_reflns         1191
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.1929
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.05000(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0783
_reflns_number_gt                830
_reflns_number_total             3314
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja0274047-4_s2_6.cif
_cod_data_source_block           17e
_cod_original_cell_volume        5771.2(7)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_original_formula_sum        'C17 H18 O2 '
_cod_database_code               4115276
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2-y,z
3/4-y,1/4+x,1/4+z
1/4+y,1/4-x,1/4+z
-x,-y,-z
x,1/2+y,-z
3/4+y,1/4-x,1/4-z
1/4-y,1/4+x,1/4-z
1/2+x,1/2+y,1/2+z
1/2-x,-y,1/2+z
1/4-y,3/4+x,3/4+z
3/4+y,3/4-x,3/4+z
1/2-x,1/2-y,1/2-z
1/2+x,y,1/2-z
1/4+y,3/4-x,3/4-z
3/4-y,3/4+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_calc_flag
O(1) O 0.44883(9) 0.18867(9) 0.4300(2) 0.0626(8) Uani 1.00 d
O(2) O 0.36301(9) 0.21782(9) 0.2384(2) 0.0636(8) Uani 1.00 d
C(1) C 0.3982(1) 0.1569(1) 0.4066(4) 0.058(1) Uani 1.00 d
C(2) C 0.3799(1) 0.1614(1) 0.2652(3) 0.050(1) Uani 1.00 d
C(3) C 0.3264(1) 0.1249(1) 0.2408(4) 0.061(1) Uani 1.00 d
C(4) C 0.3041(2) 0.1365(2) 0.1049(5) 0.088(2) Uani 1.00 d
C(5) C 0.2887(2) 0.0997(3) 0.0231(6) 0.117(2) Uani 1.00 d
C(6) C 0.4276(1) 0.1425(1) 0.1762(3) 0.052(1) Uani 1.00 d
C(7) C 0.4520(2) 0.0896(2) 0.1916(4) 0.067(1) Uani 1.00 d
C(8) C 0.4954(2) 0.0719(2) 0.1098(5) 0.086(2) Uani 1.00 d
C(9) C 0.5161(2) 0.1075(2) 0.0156(5) 0.095(2) Uani 1.00 d
C(10) C 0.4928(2) 0.1592(2) 0.0016(5) 0.103(2) Uani 1.00 d
C(11) C 0.4492(2) 0.1770(2) 0.0793(4) 0.078(1) Uani 1.00 d
C(12) C 0.2815(1) 0.1316(1) 0.3442(4) 0.061(1) Uani 1.00 d
C(13) C 0.2797(2) 0.0941(2) 0.4467(5) 0.085(2) Uani 1.00 d
C(14) C 0.2398(2) 0.0997(2) 0.5431(5) 0.106(2) Uani 1.00 d
C(15) C 0.2008(2) 0.1423(2) 0.5394(5) 0.094(2) Uani 1.00 d
C(16) C 0.2018(2) 0.1797(2) 0.4395(5) 0.081(2) Uani 1.00 d
C(17) C 0.2417(2) 0.1748(2) 0.3417(5) 0.070(1) Uani 1.00 d
H(1) H 0.407(1) 0.118(1) 0.444(4) 0.096(5) Uiso 1.00 calc
H(2) H 0.369(1) 0.172(1) 0.467(3) 0.045(6) Uiso 1.00 calc
H(3) H 0.342(1) 0.086(1) 0.249(3) 0.050(6) Uiso 1.00 calc
H(4) H 0.304(2) 0.174(2) 0.057(5) 0.169(3) Uiso 1.00 calc
H(5) H 0.300(3) 0.064(2) 0.038(7) 0.218(2) Uiso 1.00 calc
H(6) H 0.275(2) 0.110(2) -0.055(5) 0.159(3) Uiso 1.00 calc
H(7) H 0.437(1) 0.063(1) 0.256(3) 0.074(5) Uiso 1.00 calc
H(8) H 0.509(2) 0.037(1) 0.122(4) 0.105(4) Uiso 1.00 calc
H(9) H 0.549(2) 0.092(2) -0.033(4) 0.124(4) Uiso 1.00 calc
H(10) H 0.509(2) 0.187(2) -0.060(4) 0.123(4) Uiso 1.00 calc
H(11) H 0.431(1) 0.214(1) 0.066(3) 0.094(5) Uiso 1.00 calc
H(12) H 0.306(1) 0.063(2) 0.460(4) 0.112(5) Uiso 1.00 calc
H(13) H 0.242(2) 0.074(2) 0.611(4) 0.117(4) Uiso 1.00 calc
H(14) H 0.172(2) 0.146(2) 0.613(4) 0.146(3) Uiso 1.00 calc
H(15) H 0.175(1) 0.212(1) 0.446(4) 0.099(5) Uiso 1.00 calc
H(16) H 0.244(1) 0.200(1) 0.267(3) 0.062(6) Uiso 1.00 calc
H(17) H 0.441(2) 0.224(2) 0.446(5) 0.157(3) Uiso 1.00 calc
H(18) H 0.389(1) 0.240(1) 0.258(3) 0.057(5) Uiso 1.00 calc
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 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
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
C(4) C(1) C(9) 122.0(3) yes
C(4) C(1) C(11) 120.5(3) yes
C(9) C(1) C(11) 117.5(3) yes
O(2) C(2) C(4) 111.1(3) yes
C(4) C(3) C(5) 113.7(3) yes
C(4) C(3) C(8) 109.3(3) yes
C(5) C(3) C(8) 112.5(3) yes
O(1) C(4) C(1) 111.8(3) yes
O(1) C(4) C(2) 109.4(3) yes
O(1) C(4) C(3) 105.1(3) yes
C(1) C(4) C(2) 110.0(3) yes
C(1) C(4) C(3) 110.2(3) yes
C(2) C(4) C(3) 110.3(3) yes
C(3) C(5) C(6) 119.4(4) yes
C(3) C(5) C(7) 122.7(4) yes
C(6) C(5) C(7) 117.9(4) yes
C(5) C(6) C(13) 120.6(4) yes
C(5) C(7) C(12) 120.8(4) yes
C(3) C(8) C(16) 125.9(5) yes
C(1) C(9) C(17) 120.9(4) yes
C(11) C(10) C(14) 120.2(4) yes
C(1) C(11) C(10) 120.7(4) yes
C(7) C(12) C(15) 120.4(4) yes
C(6) C(13) C(15) 121.1(4) yes
C(10) C(14) C(17) 119.0(5) yes
C(12) C(15) C(13) 119.3(4) yes
C(9) C(17) C(14) 121.7(5) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(4) 1.422(3) yes
O(2) C(2) 1.438(4) yes
C(1) C(4) 1.522(4) yes
C(1) C(9) 1.386(4) yes
C(1) C(11) 1.389(4) yes
C(2) C(4) 1.518(5) yes
C(3) C(4) 1.557(4) yes
C(3) C(5) 1.511(5) yes
C(3) C(8) 1.517(6) yes
C(5) C(6) 1.378(5) yes
C(5) C(7) 1.391(4) yes
C(6) C(13) 1.376(6) yes
C(7) C(12) 1.385(5) yes
C(8) C(16) 1.266(6) yes
C(9) C(17) 1.373(6) yes
C(10) C(11) 1.393(5) yes
C(10) C(14) 1.375(6) yes
C(12) C(15) 1.356(6) yes
C(13) C(15) 1.369(5) yes
C(14) C(17) 1.352(6) yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O(1) O(2) 2.797(3) 15_555
O(1) C(12) 3.406(5) 13_555
O(1) C(2) 3.512(4) 15_555
O(2) O(2) 2.906(4) 15_555
O(2) O(2) 2.906(4) 16_545
C(13) C(16) 3.489(7) 11_545
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
O(2) H(18) O(1) . 0.84(2) 2.57(3) 2.913(3) 106(2) no
O(1) H(17) O(1) 15_555 0.87(4) 2.24(4) 2.906(3) 132(3) no
O(2) H(18) O(1) 15_555 0.84(2) 1.97(2) 2.797(3) 168(2) no
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_publ_flag
O(1) C(4) C(1) C(9) -2.0(4) yes
O(1) C(4) C(1) C(11) 176.7(3) yes
O(1) C(4) C(2) O(2) -67.0(3) yes
O(1) C(4) C(3) C(5) -72.5(4) yes
O(1) C(4) C(3) C(8) 54.2(4) yes
O(2) C(2) C(4) C(1) 56.2(3) yes
O(2) C(2) C(4) C(3) 177.9(3) yes
C(1) C(4) C(3) C(5) 166.9(3) yes
C(1) C(4) C(3) C(8) -66.3(4) yes
C(1) C(9) C(17) C(14) 0.5(7) yes
C(1) C(11) C(10) C(14) 2.4(6) yes
C(2) C(4) C(1) C(9) -123.7(4) yes
C(2) C(4) C(1) C(11) 55.0(4) yes
C(2) C(4) C(3) C(5) 45.3(4) yes
C(2) C(4) C(3) C(8) 172.0(3) yes
C(3) C(4) C(1) C(9) 114.5(4) yes
C(3) C(4) C(1) C(11) -66.8(4) yes
C(3) C(5) C(6) C(13) 179.1(4) yes
C(3) C(5) C(7) C(12) -179.2(4) yes
C(4) C(1) C(9) C(17) 179.0(4) yes
C(4) C(1) C(11) C(10) 179.6(3) yes
C(4) C(3) C(5) C(6) -94.5(4) yes
C(4) C(3) C(5) C(7) 84.8(4) yes
C(4) C(3) C(8) C(16) 134.0(5) yes
C(5) C(3) C(8) C(16) -98.5(5) yes
C(5) C(6) C(13) C(15) 0.3(8) yes
C(5) C(7) C(12) C(15) -0.2(6) yes
C(6) C(5) C(3) C(8) 140.5(4) yes
C(6) C(5) C(7) C(12) 0.1(5) yes
C(6) C(13) C(15) C(12) -0.4(8) yes
C(7) C(5) C(3) C(8) -40.3(5) yes
C(7) C(5) C(6) C(13) -0.2(6) yes
C(7) C(12) C(15) C(13) 0.3(7) yes
C(9) C(1) C(11) C(10) -1.7(6) yes
C(9) C(17) C(14) C(10) 0.2(8) yes
C(11) C(1) C(9) C(17) 0.2(6) yes
C(11) C(10) C(14) C(17) -1.7(7) yes
C(11) C(10) C(14) C(17) -1.7(7) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4404562
