#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:30:38 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178785 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/39/4103914.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_4103914
loop_
_publ_author_name
'Amos B. Smith III'
'Todd Bosanac'
'Kallol Basu'
_publ_section_title
;
 Evolution of the Total Synthesis of (-)-Okilactomycin Exploiting a Tandem
 Oxy-Cope Rearrangement/Oxidation, a Petasis-Ferrier Union/Rearrangement,
 and Ring-Closing Metathesis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2348
_journal_page_last               2358
_journal_paper_doi               10.1021/ja8084669
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C22 H34 O4'
_chemical_formula_weight         362.49
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.581(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.291(12)
_cell_length_b                   7.147(5)
_cell_length_c                   14.561(12)
_cell_measurement_temperature    143(1)
_cell_volume                     1015.1(16)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0132
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4785
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8165
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.2(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3063
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0502P)²+0.1541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0876
_reflns_number_gt                2911
_reflns_number_total             3063
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja8084669_si_004.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21 '
_cod_database_code               4103914
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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 0.58564(17) 0.7276(3) 0.15180(12) 0.0231(4) Uani 1 1 d .
H1 H 0.5940 0.5999 0.1299 0.031 Uiso 1 1 calc R
C2 C 0.64818(18) 0.8613(3) 0.09474(12) 0.0311(4) Uani 1 1 d .
H2A H 0.6113 0.8315 0.0263 0.041 Uiso 1 1 calc R
H2B H 0.6211 0.9884 0.1034 0.041 Uiso 1 1 calc R
C3 C 0.80161(18) 0.8516(3) 0.12516(13) 0.0260(4) Uani 1 1 d .
C4 C 0.87347(17) 0.8354(3) 0.23246(12) 0.0261(4) Uani 1 1 d .
H4 H 0.9680 0.7950 0.2424 0.035 Uiso 1 1 calc R
C5 C 0.80127(17) 0.6827(3) 0.27259(12) 0.0241(4) Uani 1 1 d .
H5 H 0.8022 0.5673 0.2364 0.032 Uiso 1 1 calc R
C6 C 0.86955(18) 0.6405(3) 0.37999(13) 0.0263(4) Uani 1 1 d .
H6 H 0.8681 0.7540 0.4174 0.035 Uiso 1 1 calc R
C7 C 0.79637(19) 0.4832(3) 0.41561(13) 0.0285(4) Uani 1 1 d .
H7A H 0.8629 0.4212 0.4696 0.038 Uiso 1 1 calc R
H7B H 0.7643 0.3919 0.3640 0.038 Uiso 1 1 calc R
C8 C 0.67381(18) 0.5430(3) 0.44795(12) 0.0284(4) Uani 1 1 d .
H8 H 0.6406 0.6641 0.4181 0.038 Uiso 1 1 calc R
C9 C 0.5570(2) 0.4020(3) 0.41399(13) 0.0343(5) Uani 1 1 d .
H9A H 0.4893 0.4288 0.4457 0.046 Uiso 1 1 calc R
H9B H 0.5926 0.2774 0.4332 0.046 Uiso 1 1 calc R
C10 C 0.48758(19) 0.4059(3) 0.30423(13) 0.0299(4) Uani 1 1 d .
H10A H 0.5574 0.4115 0.2726 0.040 Uiso 1 1 calc R
H10B H 0.4363 0.2909 0.2842 0.040 Uiso 1 1 calc R
C11 C 0.39106(18) 0.5717(3) 0.27149(13) 0.0283(4) Uani 1 1 d .
H11A H 0.4355 0.6820 0.3065 0.038 Uiso 1 1 calc R
H11B H 0.3095 0.5485 0.2895 0.038 Uiso 1 1 calc R
C12 C 0.34676(17) 0.6146(3) 0.16213(12) 0.0238(4) Uani 1 1 d .
H12 H 0.3558 0.4990 0.1285 0.032 Uiso 1 1 calc R
C13 C 0.19449(18) 0.6782(3) 0.12235(13) 0.0290(4) Uani 1 1 d .
H13A H 0.1388 0.5754 0.0874 0.039 Uiso 1 1 calc R
H13B H 0.1624 0.7108 0.1761 0.039 Uiso 1 1 calc R
C14 C 0.17730(17) 0.8468(3) 0.05471(12) 0.0262(4) Uani 1 1 d .
H14 H 0.0801 0.8734 0.0221 0.035 Uiso 1 1 calc R
C15 C 0.25074(18) 1.0191(3) 0.11192(13) 0.0265(4) Uani 1 1 d .
H15 H 0.2545 1.1151 0.0647 0.035 Uiso 1 1 calc R
C16 C 0.40034(17) 0.9603(3) 0.16770(12) 0.0236(4) Uani 1 1 d .
H16A H 0.4633 1.0530 0.1576 0.031 Uiso 1 1 calc R
H16B H 0.4128 0.9546 0.2365 0.031 Uiso 1 1 calc R
C17 C 0.43237(17) 0.7684(3) 0.13256(11) 0.0221(4) Uani 1 1 d .
C18 C 0.24960(17) 0.8090(3) -0.01723(13) 0.0275(4) Uani 1 1 d .
C19 C 0.8779(2) 1.0247(3) 0.28318(14) 0.0339(5) Uani 1 1 d .
H19A H 0.9134 1.1184 0.2504 0.051 Uiso 1 1 calc R
H19B H 0.9360 1.0152 0.3493 0.051 Uiso 1 1 calc R
H19C H 0.7870 1.0589 0.2816 0.051 Uiso 1 1 calc R
C20 C 1.01921(19) 0.5835(3) 0.39681(15) 0.0371(5) Uani 1 1 d .
H20A H 1.0219 0.4777 0.3568 0.056 Uiso 1 1 calc R
H20B H 1.0615 0.5510 0.4637 0.056 Uiso 1 1 calc R
H20C H 1.0678 0.6862 0.3804 0.056 Uiso 1 1 calc R
C21 C 0.7189(2) 0.5668(3) 0.55805(13) 0.0397(5) Uani 1 1 d .
H21A H 0.6433 0.6125 0.5768 0.060 Uiso 1 1 calc R
H21B H 0.7932 0.6546 0.5778 0.060 Uiso 1 1 calc R
H21C H 0.7484 0.4483 0.5886 0.060 Uiso 1 1 calc R
C22 C 0.17256(19) 1.1016(3) 0.17552(14) 0.0365(5) Uani 1 1 d .
H22A H 0.0806 1.1309 0.1363 0.055 Uiso 1 1 calc R
H22B H 0.2176 1.2136 0.2061 0.055 Uiso 1 1 calc R
H22C H 0.1703 1.0123 0.2242 0.055 Uiso 1 1 calc R
O1 O 0.65885(11) 0.73710(17) 0.25345(8) 0.0221(3) Uani 1 1 d .
O2 O 0.86240(13) 0.8567(2) 0.06617(9) 0.0348(3) Uani 1 1 d .
O3 O 0.20450(13) 0.8170(2) -0.10455(8) 0.0344(3) Uani 1 1 d .
O4 O 0.38384(12) 0.76940(18) 0.02545(8) 0.0257(3) 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
O1 C1 C2 110.89(15)
O1 C1 C17 110.49(13)
C2 C1 C17 111.44(15)
C3 C2 C1 113.26(16)
O2 C3 C2 121.42(17)
O2 C3 C4 122.91(17)
C2 C3 C4 115.67(14)
C3 C4 C19 111.14(16)
C3 C4 C5 108.21(14)
C19 C4 C5 112.75(15)
O1 C5 C6 110.85(13)
O1 C5 C4 108.49(14)
C6 C5 C4 114.17(14)
C5 C6 C7 112.10(15)
C5 C6 C20 109.07(14)
C7 C6 C20 109.14(16)
C6 C7 C8 116.01(17)
C9 C8 C21 110.97(16)
C9 C8 C7 110.79(17)
C21 C8 C7 110.29(16)
C8 C9 C10 112.61(15)
C11 C10 C9 112.50(16)
C10 C11 C12 115.28(15)
C11 C12 C17 114.83(14)
C11 C12 C13 111.97(14)
C17 C12 C13 106.44(16)
C14 C13 C12 111.46(15)
C18 C14 C13 109.18(17)
C18 C14 C15 104.82(15)
C13 C14 C15 110.17(14)
C22 C15 C14 111.95(16)
C22 C15 C16 114.46(16)
C14 C15 C16 107.45(15)
C17 C16 C15 110.48(14)
O4 C17 C16 108.13(13)
O4 C17 C1 100.07(12)
C16 C17 C1 115.13(14)
O4 C17 C12 105.36(13)
C16 C17 C12 109.81(14)
C1 C17 C12 117.02(16)
O3 C18 O4 119.16(16)
O3 C18 C14 128.38(17)
O4 C18 C14 112.38(15)
C1 O1 C5 110.57(12)
C18 O4 C17 115.98(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.433(2)
C1 C2 1.536(3)
C1 C17 1.539(3)
C2 C3 1.499(3)
C3 O2 1.214(2)
C3 C4 1.505(3)
C4 C19 1.535(3)
C4 C5 1.536(3)
C5 O1 1.455(3)
C5 C6 1.527(3)
C6 C7 1.532(3)
C6 C20 1.535(3)
C7 C8 1.541(3)
C8 C9 1.525(3)
C8 C21 1.530(3)
C9 C10 1.529(3)
C10 C11 1.522(3)
C11 C12 1.541(3)
C12 C17 1.553(3)
C12 C13 1.555(3)
C13 C14 1.531(3)
C14 C18 1.490(3)
C14 C15 1.543(3)
C15 C22 1.526(3)
C15 C16 1.552(3)
C16 C17 1.536(3)
C17 O4 1.478(2)
C18 O3 1.208(2)
C18 O4 1.352(3)
