#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:30:38 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178902 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/31/4113129.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_4113129
loop_
_publ_author_name
'Masaharu Nakamura'
'Takuji Hatakeyama'
'Kenji Hara'
'Hiroki Fukudome'
'Eiichi Nakamura'
_publ_contact_author             'Nakamura, E.'
_publ_contact_author_email       nakamura@chem.s.u-tokyo.ac.jp
_publ_section_title
;
 Sequential Coupling of Zincated Hydrazone, Alkenylboronate, and
 Electrophile That Creates Several Contiguous Stereogenic Centers
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14344
_journal_page_last               14345
_journal_paper_doi               10.1021/ja044878s
_journal_volume                  126
_journal_year                    2004
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H35 B1 O3'
_chemical_formula_structural     'C18 H35 B1 O3'
_chemical_formula_sum            'C18 H35 B O3'
_chemical_formula_weight         310.27
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2003-07-02T18:57:01-00:00
_cell_angle_alpha                79.600(5)
_cell_angle_beta                 67.790(5)
_cell_angle_gamma                71.001(5)
_cell_formula_units_Z            2
_cell_length_a                   9.725(5)
_cell_length_b                   10.608(5)
_cell_length_c                   11.225(5)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_measurement_wavelength     0.71073
_cell_volume                     1011.5(8)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.915
_diffrn_measured_fraction_theta_max 0.915
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3544
_diffrn_reflns_theta_full        25.75
_diffrn_reflns_theta_max         25.75
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.019
_exptl_crystal_description       prism
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.819
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.217
_refine_ls_extinction_coef       2.9(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.816
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3544
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.816
_refine_ls_R_factor_all          0.2049
_refine_ls_R_factor_gt           0.1816
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.441
_refine_ls_wR_factor_ref         0.5057
_reflns_number_gt                2099
_reflns_number_total             3544
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja044878ssi20040825_120049.cif
_cod_data_source_block           hydrogenation
_cod_database_code               4113129
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.9465(10) -0.1064(8) 0.7917(10) 0.192(3) Uani 1 1 d .
H1A H 0.8413 -0.0576 0.835 0.287 Uiso 1 1 calc R
H1B H 0.9969 -0.1456 0.8539 0.287 Uiso 1 1 calc R
H1C H 0.9479 -0.1757 0.7464 0.287 Uiso 1 1 calc R
C2 C 1.0305(8) -0.0128(7) 0.6971(7) 0.149(2) Uani 1 1 d .
H2 H 0.9795 0.0224 0.6328 0.178 Uiso 1 1 calc R
C3 C 1.0128(6) 0.1031(6) 0.7668(6) 0.1334(17) Uani 1 1 d .
C4 C 0.8591(6) 0.2066(6) 0.8146(6) 0.1327(17) Uani 1 1 d .
H4 H 0.7812 0.1787 0.7988 0.159 Uiso 1 1 calc R
C5 C 0.8693(6) 0.3432(5) 0.7390(5) 0.1229(15) Uani 1 1 d .
H5 H 0.9462 0.3709 0.7565 0.148 Uiso 1 1 calc R
C6 C 0.7138(5) 0.4551(5) 0.7789(5) 0.1214(14) Uani 1 1 d .
H6 H 0.6915 0.4654 0.87 0.146 Uiso 1 1 calc R
C7 C 0.7268(6) 0.5879(5) 0.7131(5) 0.1287(16) Uani 1 1 d .
H7A H 0.8141 0.605 0.7226 0.154 Uiso 1 1 calc R
H7B H 0.7499 0.5834 0.6218 0.154 Uiso 1 1 calc R
C8 C 0.5883(7) 0.7032(6) 0.7598(6) 0.1403(18) Uani 1 1 d .
H8A H 0.565 0.7072 0.8513 0.168 Uiso 1 1 calc R
H8B H 0.5012 0.686 0.7502 0.168 Uiso 1 1 calc R
C9 C 0.6001(9) 0.8373(7) 0.6949(9) 0.174(3) Uani 1 1 d .
H9A H 0.505 0.904 0.7326 0.261 Uiso 1 1 calc R
H9B H 0.619 0.8365 0.6046 0.261 Uiso 1 1 calc R
H9C H 0.6838 0.8575 0.7057 0.261 Uiso 1 1 calc R
C10 C 1.1943(10) -0.0835(9) 0.6281(11) 0.211(4) Uani 1 1 d .
H10A H 1.1984 -0.156 0.5854 0.317 Uiso 1 1 calc R
H10B H 1.2478 -0.1179 0.6888 0.317 Uiso 1 1 calc R
H10C H 1.2428 -0.0224 0.5655 0.317 Uiso 1 1 calc R
C11 C 0.8105(9) 0.2177(8) 0.9605(6) 0.174(3) Uani 1 1 d .
H11A H 0.7126 0.2842 0.9897 0.261 Uiso 1 1 calc R
H11B H 0.8873 0.2428 0.9777 0.261 Uiso 1 1 calc R
H11C H 0.8014 0.133 1.0052 0.261 Uiso 1 1 calc R
C12 C 0.9281(6) 0.3237(6) 0.5921(5) 0.144(2) Uani 1 1 d .
H12A H 0.9356 0.4074 0.5443 0.215 Uiso 1 1 calc R
H12B H 0.8569 0.2923 0.5733 0.215 Uiso 1 1 calc R
H12C H 1.0283 0.2594 0.5681 0.215 Uiso 1 1 calc R
C13 C 0.3629(5) 0.3329(6) 0.8487(5) 0.1238(16) Uani 1 1 d .
C14 C 0.3985(6) 0.3802(7) 0.7073(5) 0.1385(19) Uani 1 1 d .
C15 C 0.2039(7) 0.3784(8) 0.9384(7) 0.162(2) Uani 1 1 d .
H15A H 0.199 0.3398 1.0236 0.243 Uiso 1 1 calc R
H15B H 0.1357 0.3512 0.9115 0.243 Uiso 1 1 calc R
H15C H 0.1729 0.474 0.9387 0.243 Uiso 1 1 calc R
C16 C 0.4195(9) 0.1789(6) 0.8657(8) 0.168(3) Uani 1 1 d .
H16A H 0.5224 0.1474 0.8056 0.252 Uiso 1 1 calc R
H16B H 0.3514 0.1409 0.8499 0.252 Uiso 1 1 calc R
H16C H 0.4199 0.1527 0.952 0.252 Uiso 1 1 calc R
C17 C 0.2817(8) 0.5245(8) 0.6935(9) 0.190(3) Uani 1 1 d .
H17A H 0.2785 0.5822 0.7518 0.284 Uiso 1 1 calc R
H17B H 0.18 0.5156 0.7137 0.284 Uiso 1 1 calc R
H17C H 0.3167 0.5619 0.6066 0.284 Uiso 1 1 calc R
C18 C 0.4022(9) 0.2939(9) 0.6161(7) 0.182(3) Uani 1 1 d .
H18A H 0.4253 0.3375 0.531 0.273 Uiso 1 1 calc R
H18B H 0.3032 0.2774 0.6421 0.273 Uiso 1 1 calc R
H18C H 0.4805 0.2106 0.6157 0.273 Uiso 1 1 calc R
B B 0.5764(6) 0.4148(5) 0.7780(5) 0.1108(13) Uani 1 1 d .
O1 O 1.1230(5) 0.1125(5) 0.7873(6) 0.1744(19) Uani 1 1 d .
O2 O 0.4624(4) 0.3844(4) 0.8867(3) 0.1307(13) Uani 1 1 d .
O3 O 0.5510(4) 0.4030(4) 0.6695(3) 0.1352(14) Uani 1 1 d .
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C10 C2 C3 113.2(6)
C10 C2 C1 111.6(7)
C3 C2 C1 109.0(7)
O1 C3 C2 119.8(5)
O1 C3 C4 119.2(6)
C2 C3 C4 121.0(5)
C3 C4 C11 110.3(5)
C3 C4 C5 109.7(4)
C11 C4 C5 111.1(5)
C6 C5 C4 113.3(4)
C6 C5 C12 110.8(4)
C4 C5 C12 108.7(5)
C7 C6 B 115.1(4)
C7 C6 C5 113.1(4)
B C6 C5 113.4(4)
C8 C7 C6 116.0(5)
C7 C8 C9 116.5(5)
C15 C13 O2 108.2(4)
C15 C13 C14 119.0(5)
O2 C13 C14 102.7(3)
C15 C13 C16 108.5(5)
O2 C13 C16 106.5(4)
C14 C13 C16 111.1(5)
O3 C14 C18 109.6(5)
O3 C14 C13 103.6(4)
C18 C14 C13 119.3(6)
O3 C14 C17 105.5(5)
C18 C14 C17 108.4(6)
C13 C14 C17 109.6(5)
O3 B O2 110.6(4)
O3 B C6 124.8(4)
O2 B C6 124.6(5)
B O2 C13 109.2(4)
B O3 C14 108.8(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.507(10)
C2 C10 1.483(10)
C2 C3 1.503(9)
C3 O1 1.215(6)
C3 C4 1.505(7)
C4 C11 1.539(9)
C4 C5 1.554(7)
C5 C6 1.552(7)
C5 C12 1.556(8)
C6 C7 1.488(7)
C6 B 1.534(6)
C7 C8 1.487(7)
C8 C9 1.496(9)
C13 C15 1.466(7)
C13 O2 1.468(5)
C13 C14 1.517(7)
C13 C16 1.546(8)
C14 O3 1.469(6)
C14 C18 1.476(8)
C14 C17 1.604(10)
B O3 1.365(6)
B O2 1.375(6)
