#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/81/1508164.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_1508164
loop_
_publ_author_name
'Mendoza, Abraham'
'Ishihara, Yoshihiro'
'Baran, Phil S.'
_publ_section_title
;
 Scalable enantioselective total synthesis of taxanes.
;
_journal_issue                   1
_journal_name_full               'Nature chemistry'
_journal_page_first              21
_journal_page_last               25
_journal_paper_doi               10.1038/nchem.1196
_journal_volume                  4
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H30 O'
_chemical_formula_weight         286.44
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8261(2)
_cell_length_b                   11.6102(2)
_cell_length_c                   14.6754(3)
_cell_measurement_reflns_used    6438
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.18
_cell_measurement_theta_min      3.81
_cell_volume                     1674.21(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0859
_diffrn_reflns_av_sigmaI/netI    0.0632
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7309
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         68.18
_diffrn_reflns_theta_min         4.86
_exptl_absorpt_coefficient_mu    0.507
_exptl_absorpt_correction_T_max  0.8628
_exptl_absorpt_correction_T_min  0.8386
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2891
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0750P)²+0.1800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1127
_reflns_number_gt                2842
_reflns_number_total             2891
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            nchem.1196-s3.cif
_cod_data_source_block           baran215
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1508164
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
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
O1 O 0.21685(11) 0.21582(9) 1.00567(8) 0.0372(3) Uani 1 1 d .
C1 C 0.37066(19) -0.22797(16) 0.84307(14) 0.0495(5) Uani 1 1 d .
H1A H 0.3194 -0.2840 0.8793 0.074 Uiso 1 1 calc R
H1B H 0.4530 -0.2645 0.8189 0.074 Uiso 1 1 calc R
H1C H 0.3141 -0.2007 0.7925 0.074 Uiso 1 1 calc R
C2 C 0.41006(16) -0.12727(13) 0.90250(12) 0.0372(4) Uani 1 1 d .
C3 C 0.35651(16) -0.10451(12) 0.98459(11) 0.0334(3) Uani 1 1 d .
C4 C 0.41734(17) -0.00551(12) 1.04021(12) 0.0377(4) Uani 1 1 d .
C5 C 0.41190(14) 0.10204(12) 0.97710(11) 0.0328(3) Uani 1 1 d .
H5 H 0.4565 0.1668 1.0107 0.039 Uiso 1 1 calc R
C6 C 0.26293(14) 0.13587(11) 0.96237(9) 0.0268(3) Uani 1 1 d .
C7 C 0.17041(13) 0.07480(11) 0.89229(9) 0.0238(3) Uani 1 1 d .
H7 H 0.2298 0.0243 0.8540 0.029 Uiso 1 1 calc R
C8 C 0.11483(15) 0.17027(12) 0.83036(10) 0.0297(3) Uani 1 1 d .
C9 C 0.21881(18) 0.25091(15) 0.79061(12) 0.0425(4) Uani 1 1 d .
H9A H 0.1738 0.3051 0.7492 0.064 Uiso 1 1 calc R
H9B H 0.2871 0.2065 0.7569 0.064 Uiso 1 1 calc R
H9C H 0.2634 0.2937 0.8398 0.064 Uiso 1 1 calc R
C10 C 0.51083(17) -0.04574(17) 0.85932(14) 0.0480(4) Uani 1 1 d .
H10A H 0.5003 -0.0495 0.7923 0.058 Uiso 1 1 calc R
H10B H 0.6040 -0.0721 0.8742 0.058 Uiso 1 1 calc R
C11 C 0.49548(16) 0.08096(15) 0.88991(14) 0.0437(4) Uani 1 1 d .
H11A H 0.5876 0.1133 0.8993 0.052 Uiso 1 1 calc R
H11B H 0.4527 0.1246 0.8396 0.052 Uiso 1 1 calc R
C12 C -0.01591(17) 0.17942(15) 0.80756(11) 0.0380(4) Uani 1 1 d .
H12 H -0.0423 0.2426 0.7704 0.046 Uiso 1 1 calc R
C13 C -0.12289(15) 0.09715(17) 0.83658(12) 0.0432(4) Uani 1 1 d .
H13A H -0.1872 0.0837 0.7858 0.052 Uiso 1 1 calc R
H13B H -0.1745 0.1298 0.8884 0.052 Uiso 1 1 calc R
C14 C -0.05778(14) -0.01626(14) 0.86479(11) 0.0359(4) Uani 1 1 d .
H14A H -0.0202 -0.0542 0.8098 0.043 Uiso 1 1 calc R
H14B H -0.1293 -0.0672 0.8899 0.043 Uiso 1 1 calc R
C15 C 0.05687(14) -0.00426(12) 0.93608(10) 0.0286(3) Uani 1 1 d .
C16 C 0.10498(16) -0.13037(12) 0.95210(11) 0.0346(4) Uani 1 1 d .
H16A H 0.0252 -0.1737 0.9749 0.042 Uiso 1 1 calc R
H16B H 0.1273 -0.1627 0.8915 0.042 Uiso 1 1 calc R
C17 C 0.22456(18) -0.15972(13) 1.01528(12) 0.0397(4) Uani 1 1 d .
H17A H 0.2030 -0.1333 1.0778 0.048 Uiso 1 1 calc R
H17B H 0.2364 -0.2444 1.0172 0.048 Uiso 1 1 calc R
C18 C 0.5675(2) -0.03077(17) 1.06645(17) 0.0579(6) Uani 1 1 d .
H18A H 0.6055 0.0358 1.0987 0.087 Uiso 1 1 calc R
H18B H 0.6206 -0.0454 1.0111 0.087 Uiso 1 1 calc R
H18C H 0.5711 -0.0986 1.1061 0.087 Uiso 1 1 calc R
C19 C 0.3450(2) 0.02055(15) 1.13008(12) 0.0488(4) Uani 1 1 d .
H19A H 0.2494 0.0391 1.1180 0.073 Uiso 1 1 calc R
H19B H 0.3891 0.0862 1.1599 0.073 Uiso 1 1 calc R
H19C H 0.3502 -0.0470 1.1700 0.073 Uiso 1 1 calc R
C20 C -0.00694(17) 0.04611(14) 1.02317(10) 0.0371(3) Uani 1 1 d .
H20A H -0.0332 0.1264 1.0123 0.056 Uiso 1 1 calc R
H20B H 0.0594 0.0428 1.0730 0.056 Uiso 1 1 calc R
H20C H -0.0877 0.0012 1.0397 0.056 Uiso 1 1 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 0.0181 0.0091 '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'
O O 0.0492 0.0322 '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
C3 C2 C10 120.73(15)
C3 C2 C1 124.84(16)
C10 C2 C1 114.30(16)
C2 C3 C17 121.31(14)
C2 C3 C4 118.27(15)
C17 C3 C4 119.56(14)
C19 C4 C3 115.28(15)
C19 C4 C18 105.37(16)
C3 C4 C18 111.18(14)
C19 C4 C5 109.81(13)
C3 C4 C5 105.77(12)
C18 C4 C5 109.39(14)
C6 C5 C11 115.68(13)
C6 C5 C4 108.84(12)
C11 C5 C4 110.41(13)
O1 C6 C5 118.64(13)
O1 C6 C7 118.72(12)
C5 C6 C7 122.61(12)
C8 C7 C6 105.80(11)
C8 C7 C15 114.15(11)
C6 C7 C15 114.27(11)
C12 C8 C9 120.55(15)
C12 C8 C7 123.36(14)
C9 C8 C7 115.97(12)
C2 C10 C11 114.27(15)
C5 C11 C10 116.40(14)
C8 C12 C13 124.08(16)
C12 C13 C14 109.73(12)
C13 C14 C15 114.40(13)
C20 C15 C14 107.45(12)
C20 C15 C16 110.84(13)
C14 C15 C16 103.83(12)
C20 C15 C7 113.85(11)
C14 C15 C7 106.96(12)
C16 C15 C7 113.15(11)
C17 C16 C15 122.17(12)
C3 C17 C16 112.43(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C6 1.2127(18)
C1 C2 1.509(2)
C2 C3 1.341(2)
C2 C10 1.509(2)
C3 C17 1.515(2)
C3 C4 1.531(2)
C4 C19 1.528(3)
C4 C18 1.553(2)
C4 C5 1.556(2)
C5 C6 1.5309(19)
C5 C11 1.540(2)
C6 C7 1.5449(18)
C7 C8 1.5338(19)
C7 C15 1.5813(18)
C8 C12 1.332(2)
C8 C9 1.504(2)
C10 C11 1.545(3)
C12 C13 1.483(3)
C13 C14 1.521(3)
C14 C15 1.544(2)
C15 C20 1.5390(19)
C15 C16 1.556(2)
C16 C17 1.535(2)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 30651956 ChemSpider
