#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/61/4116134.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_4116134
loop_
_publ_author_name
'Eiji Shirakawa'
'Yoshiaki Nakao'
'Hiroto Yoshida'
'Tamejiro Hiyama'
_publ_contact_author_address
;
Graduate School of Materials Science, Japan Advanced Institute of Science and 
Technology, Asahidai, Tatsunokuchi, Ishikawa 923-1292, Japan
;
_publ_contact_author_email       ' shira@jaist.ac.jp '
_publ_contact_author_fax         ' +81-761-51-1635 '
_publ_contact_author_name        ' Eiji  Shirakawa'
_publ_contact_author_phone       ' +81-761-51-1631 '
_publ_section_title
;
 Nickel-Catalyzed Acylstannylation of 1,3-Dienes: Synthesis and Reaction
 of ε-Oxoallylstannanes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9030
_journal_page_last               9031
_journal_paper_doi               10.1021/ja0020409
_journal_volume                  122
_journal_year                    2000
_chemical_formula_moiety         'C21 H24 O2 '
_chemical_formula_sum            'C21 H24 O2'
_chemical_formula_weight         308.42
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.807(5)
_cell_length_b                   13.334(4)
_cell_length_c                   11.354(6)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      10.8
_cell_measurement_theta_min      9.4
_cell_volume                     3604(2)
_diffrn_ambient_temperature      296.2
_diffrn_measurement_device       AFC7R
_diffrn_measurement_method       ω-2θ
_diffrn_orient_matrix_UB_11      0.03442
_diffrn_orient_matrix_UB_12      -0.01693
_diffrn_orient_matrix_UB_13      0.04639
_diffrn_orient_matrix_UB_21      0.02406
_diffrn_orient_matrix_UB_22      0.02208
_diffrn_orient_matrix_UB_23      -0.06738
_diffrn_orient_matrix_UB_31      0.00074
_diffrn_orient_matrix_UB_32      0.06964
_diffrn_orient_matrix_UB_33      0.03264
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.00000
_diffrn_reflns_av_sigmaI/netI    0.198
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4635
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.51
_diffrn_standards_decay_%        0.11
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.071
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1328.00
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.14
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.780
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     304
_refine_ls_number_reflns         1183
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.2300
_refine_ls_shift/su_mean         0.0117
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00000|Fo|²]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_ref         0.0260
_reflns_number_gt                1183
_reflns_number_total             4635
_reflns_threshold_expression     I>3.00σ(I)
_cod_data_source_file            ja0020409.cif
_cod_data_source_block           global
_cod_original_sg_symbol_H-M      'P b c a '
_cod_original_formula_sum        'C21 H24 O2 '
_cod_database_code               4116134
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'1/2+x,1/2-y,   -z'
'   -x,1/2+y,1/2-z'
'1/2-x,   -y,1/2+z'
'   -x,   -y,   -z'
'1/2-x,1/2+y,   +z'
'   +x,1/2-y,1/2+z'
'1/2+x,   +y,1/2-z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_calc_flag
O(1) 0.44934(8) 0.5016(2) -0.1722(2) 0.0659(8) 1.000 Uani d
O(2) 0.46414(8) 0.2505(2) 0.1388(2) 0.0788(8) 1.000 Uani d
C(1) 0.4753(1) 0.3310(3) -0.0478(4) 0.053(1) 1.000 Uani d
C(2) 0.4138(1) 0.3684(2) -0.0503(3) 0.046(1) 1.000 Uani d
C(3) 0.4077(1) 0.4244(2) -0.1714(3) 0.053(1) 1.000 Uani d
C(4) 0.3501(1) 0.4663(3) -0.1985(3) 0.053(1) 1.000 Uani d
C(5) 0.3137(2) 0.4109(3) -0.2674(3) 0.074(1) 1.000 Uani d
C(6) 0.2610(2) 0.4496(4) -0.2940(4) 0.094(2) 1.000 Uani d
C(7) 0.2447(2) 0.5407(4) -0.2545(4) 0.091(2) 1.000 Uani d
C(8) 0.2801(2) 0.5969(3) -0.1882(4) 0.084(2) 1.000 Uani d
C(9) 0.3333(2) 0.5597(3) -0.1602(3) 0.068(1) 1.000 Uani d
C(10) 0.4939(1) 0.2674(2) 0.0552(3) 0.055(1) 1.000 Uani d
C(11) 0.5524(1) 0.2255(2) 0.0507(3) 0.053(1) 1.000 Uani d
C(12) 0.5680(2) 0.1591(3) 0.1377(4) 0.075(1) 1.000 Uani d
C(13) 0.6211(2) 0.1172(3) 0.1371(4) 0.096(2) 1.000 Uani d
C(14) 0.6588(2) 0.1403(3) 0.0508(5) 0.092(2) 1.000 Uani d
C(15) 0.6445(2) 0.2060(3) -0.0363(4) 0.080(2) 1.000 Uani d
C(16) 0.5910(1) 0.2494(3) -0.0358(3) 0.063(1) 1.000 Uani d
C(17) 0.3723(1) 0.2814(2) -0.0472(3) 0.052(1) 1.000 Uani d
C(18) 0.3876(2) 0.1881(3) -0.1103(4) 0.089(2) 1.000 Uani d
C(19) 0.3218(2) 0.2904(3) 0.0047(4) 0.077(2) 1.000 Uani d
C(20) 0.4045(2) 0.4423(3) 0.0509(4) 0.061(1) 1.000 Uani d
C(21) 0.4591(2) 0.5420(4) -0.2861(5) 0.095(2) 1.000 Uani d
H(1) 0.4835(9) 0.295(2) -0.119(2) 0.038(9) 1.000 Uiso d
H(2) 0.4979(9) 0.388(2) -0.044(2) 0.032(8) 1.000 Uiso d
H(3) 0.4167(8) 0.377(1) -0.237(2) 0.020(7) 1.000 Uiso d
H(4) 0.327(1) 0.340(2) -0.298(2) 0.09(1) 1.000 Uiso d
H(5) 0.239(1) 0.405(2) -0.347(2) 0.10(1) 1.000 Uiso d
H(6) 0.206(1) 0.570(2) -0.277(3) 0.13(1) 1.000 Uiso d
H(7) 0.273(1) 0.665(2) -0.159(3) 0.09(1) 1.000 Uiso d
H(8) 0.360(1) 0.601(2) -0.114(2) 0.08(1) 1.000 Uiso d
H(9) 0.538(1) 0.139(2) 0.201(2) 0.08(1) 1.000 Uiso d
H(10) 0.628(1) 0.071(2) 0.198(2) 0.09(1) 1.000 Uiso d
H(11) 0.697(1) 0.111(2) 0.041(3) 0.11(1) 1.000 Uiso d
H(12) 0.667(1) 0.226(2) -0.102(2) 0.10(1) 1.000 Uiso d
H(13) 0.5807(9) 0.296(2) -0.102(2) 0.046(9) 1.000 Uiso d
H(14) 0.416(1) 0.151(3) -0.068(3) 0.13(1) 1.000 Uiso d
H(15) 0.359(1) 0.145(2) -0.104(3) 0.09(1) 1.000 Uiso d
H(16) 0.402(2) 0.201(3) -0.209(4) 0.25(1) 1.000 Uiso d
H(17) 0.307(1) 0.349(2) 0.030(3) 0.10(1) 1.000 Uiso d
H(18) 0.2969(9) 0.235(2) -0.000(2) 0.054(9) 1.000 Uiso d
H(19) 0.4085(9) 0.411(2) 0.122(2) 0.029(8) 1.000 Uiso d
H(20) 0.434(1) 0.497(2) 0.049(3) 0.08(1) 1.000 Uiso d
H(21) 0.368(1) 0.479(2) 0.046(2) 0.07(1) 1.000 Uiso d
H(22) 0.492(1) 0.583(3) -0.280(3) 0.15(1) 1.000 Uiso d
H(23) 0.467(2) 0.485(2) -0.348(3) 0.14(1) 1.000 Uiso d
H(24) 0.432(1) 0.572(3) -0.317(3) 0.13(1) 1.000 Uiso d
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0 168 0.002 0.002
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
H 0 192 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O 0 16 0.008 0.006
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
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(3) O(1) C(21) 113.1(4) no
C(2) C(1) C(10) 118.2(4) no
C(2) C(1) H(1) 110(2) no
C(2) C(1) H(2) 107(2) no
C(10) C(1) H(1) 108(2) no
C(10) C(1) H(2) 105(2) no
H(1) C(1) H(2) 109(3) no
C(1) C(2) C(3) 104.9(3) no
C(1) C(2) C(17) 111.6(3) no
C(1) C(2) C(20) 109.3(4) no
C(3) C(2) C(17) 108.8(3) no
C(3) C(2) C(20) 109.7(4) no
C(17) C(2) C(20) 112.3(4) no
O(1) C(3) C(2) 106.5(3) no
O(1) C(3) C(4) 111.3(3) no
O(1) C(3) H(3) 108(2) no
C(2) C(3) C(4) 115.9(3) no
C(2) C(3) H(3) 109(2) no
C(4) C(3) H(3) 106(2) no
C(3) C(4) C(5) 119.1(5) no
C(3) C(4) C(9) 122.1(5) no
C(5) C(4) C(9) 118.7(5) no
C(4) C(5) C(6) 119.4(5) no
C(4) C(5) H(4) 118(2) no
C(6) C(5) H(4) 123(2) no
C(5) C(6) C(7) 121.3(6) no
C(5) C(6) H(5) 113(3) no
C(7) C(6) H(5) 126(3) no
C(6) C(7) C(8) 120.2(6) no
C(6) C(7) H(6) 121(3) no
C(8) C(7) H(6) 119(3) no
C(7) C(8) C(9) 119.6(6) no
C(7) C(8) H(7) 126(3) no
C(9) C(8) H(7) 114(3) no
C(4) C(9) C(8) 120.7(5) no
C(4) C(9) H(8) 119(2) no
C(8) C(9) H(8) 120(2) no
O(2) C(10) C(1) 122.8(4) no
O(2) C(10) C(11) 120.1(4) no
C(1) C(10) C(11) 117.1(4) no
C(10) C(11) C(12) 117.8(4) no
C(10) C(11) C(16) 123.7(4) no
C(12) C(11) C(16) 118.6(4) no
C(11) C(12) C(13) 120.3(5) no
C(11) C(12) H(9) 118(2) no
C(13) C(12) H(9) 122(2) no
C(12) C(13) C(14) 120.9(6) no
C(12) C(13) H(10) 115(3) no
C(14) C(13) H(10) 124(3) no
C(13) C(14) C(15) 120.1(5) no
C(13) C(14) H(11) 126(3) no
C(15) C(14) H(11) 114(3) no
C(14) C(15) C(16) 119.3(5) no
C(14) C(15) H(12) 127(3) no
C(16) C(15) H(12) 114(3) no
C(11) C(16) C(15) 120.8(5) no
C(11) C(16) H(13) 121(2) no
C(15) C(16) H(13) 118(2) no
C(2) C(17) C(18) 118.0(4) no
C(2) C(17) C(19) 121.5(4) no
C(18) C(17) C(19) 120.5(4) no
C(17) C(18) H(14) 111(3) no
C(17) C(18) H(15) 108(3) no
C(17) C(18) H(16) 114(3) no
H(14) C(18) H(15) 99(4) no
H(14) C(18) H(16) 110(4) no
H(15) C(18) H(16) 113(4) no
C(17) C(19) H(17) 125(3) no
C(17) C(19) H(18) 118(2) no
H(17) C(19) H(18) 116(3) no
C(2) C(20) H(19) 110(2) no
C(2) C(20) H(20) 110(2) no
C(2) C(20) H(21) 114(2) no
H(19) C(20) H(20) 106(3) no
H(19) C(20) H(21) 111(3) no
H(20) C(20) H(21) 104(3) no
O(1) C(21) H(22) 106(3) no
O(1) C(21) H(23) 111(3) no
O(1) C(21) H(24) 116(4) no
H(22) C(21) H(23) 108(4) no
H(22) C(21) H(24) 113(4) no
H(23) C(21) H(24) 102(5) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(3) 1.428(4) no
O(1) C(21) 1.421(6) no
O(2) C(10) 1.206(4) no
C(1) C(2) 1.546(5) no
C(1) C(10) 1.511(5) no
C(1) H(1) 0.96(3) no
C(1) H(2) 0.93(3) no
C(2) C(3) 1.571(5) no
C(2) C(17) 1.524(5) no
C(2) C(20) 1.530(6) no
C(3) C(4) 1.513(5) no
C(3) H(3) 1.00(3) no
C(4) C(5) 1.381(5) no
C(4) C(9) 1.378(5) no
C(5) C(6) 1.390(7) no
C(5) H(4) 1.06(3) no
C(6) C(7) 1.353(7) no
C(6) H(5) 0.99(4) no
C(7) C(8) 1.355(7) no
C(7) H(6) 1.03(4) no
C(8) C(9) 1.399(6) no
C(8) H(7) 0.98(3) no
C(9) H(8) 0.99(3) no
C(10) C(11) 1.502(5) no
C(11) C(12) 1.378(5) no
C(11) C(16) 1.382(5) no
C(12) C(13) 1.381(6) no
C(12) H(9) 1.04(3) no
C(13) C(14) 1.365(7) no
C(13) H(10) 0.94(3) no
C(14) C(15) 1.363(7) no
C(14) H(11) 1.00(4) no
C(15) C(16) 1.400(6) no
C(15) H(12) 0.96(3) no
C(16) H(13) 1.00(3) no
C(17) C(18) 1.481(6) no
C(17) C(19) 1.344(5) no
C(18) H(14) 0.97(4) no
C(18) H(15) 0.90(3) no
C(18) H(16) 1.18(6) no
C(19) H(17) 0.90(4) no
C(19) H(18) 0.95(3) no
C(20) H(19) 0.91(3) no
C(20) H(20) 1.01(3) no
C(20) H(21) 0.99(3) no
C(21) H(22) 0.96(4) no
C(21) H(23) 1.05(4) no
C(21) H(24) 0.84(4) no
