#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/35/1503599.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_1503599
loop_
_publ_author_name
'Niu, Dawen'
'Hoye, Thomas R.'
_publ_section_title
;
 A concise total synthesis of (+-)- and (-)-okilactomycin d.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              828
_journal_page_last               831
_journal_paper_doi               10.1021/ol203355g
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C24 H34 O4'
_chemical_formula_sum            'C24 H34 O4'
_chemical_formula_weight         386.51
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 103.8120(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1195(5)
_cell_length_b                   13.0223(6)
_cell_length_c                   16.5396(7)
_cell_measurement_reflns_used    9964
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.77
_cell_measurement_theta_min      2.60
_cell_volume                     2116.55(17)
_computing_cell_refinement       'Bruker APEX2'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX 2 Platform CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0135
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23828
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4842
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0579P)²+0.6126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1078
_reflns_number_gt                4268
_reflns_number_total             4842
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol203355g_si_002.cif
_cod_data_source_block           11084
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1503599
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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 0.27458(9) 0.53463(6) 0.15433(5) 0.03120(19) Uani 1 1 d .
O2 O 0.46726(7) 0.46033(6) 0.14015(5) 0.02241(17) Uani 1 1 d .
O3 O 0.45918(8) 0.19969(6) 0.19836(5) 0.02737(18) Uani 1 1 d .
O4 O 0.15343(9) 0.36653(7) 0.26786(5) 0.0347(2) Uani 1 1 d .
C1 C 0.34392(10) 0.45864(8) 0.16047(6) 0.0225(2) Uani 1 1 d .
C2 C 0.31604(10) 0.35463(8) 0.18612(6) 0.0218(2) Uani 1 1 d .
C3 C 0.42446(10) 0.29687(8) 0.18137(6) 0.0213(2) Uani 1 1 d .
C4 C 0.37244(12) 0.13537(9) 0.23528(8) 0.0299(3) Uani 1 1 d .
H4A H 0.4214 0.0747 0.2581 0.045 Uiso 1 1 calc R
H4B H 0.2931 0.1162 0.1934 0.045 Uiso 1 1 calc R
H4C H 0.3455 0.1726 0.2788 0.045 Uiso 1 1 calc R
C5 C 0.52927(10) 0.35936(8) 0.15186(6) 0.0208(2) Uani 1 1 d .
C6 C 0.66412(11) 0.36389(9) 0.21764(7) 0.0255(2) Uani 1 1 d .
H6A H 0.7026 0.2953 0.2257 0.031 Uiso 1 1 calc R
H6B H 0.6464 0.3860 0.2700 0.031 Uiso 1 1 calc R
C7 C 0.76901(11) 0.43650(9) 0.19486(7) 0.0257(2) Uani 1 1 d .
H7A H 0.8590 0.4122 0.2249 0.031 Uiso 1 1 calc R
C8 C 0.75408(12) 0.54659(10) 0.22468(8) 0.0335(3) Uani 1 1 d .
H8A H 0.8230 0.5893 0.2111 0.050 Uiso 1 1 calc R
H8B H 0.7640 0.5466 0.2839 0.050 Uiso 1 1 calc R
H8C H 0.6658 0.5727 0.1977 0.050 Uiso 1 1 calc R
C9 C 0.76553(10) 0.43129(8) 0.10279(7) 0.0243(2) Uani 1 1 d .
C10 C 0.87425(12) 0.49022(10) 0.07413(8) 0.0313(3) Uani 1 1 d .
H10A H 0.8672 0.4766 0.0162 0.047 Uiso 1 1 calc R
H10B H 0.9623 0.4692 0.1060 0.047 Uiso 1 1 calc R
H10C H 0.8625 0.5624 0.0819 0.047 Uiso 1 1 calc R
C11 C 0.67195(11) 0.37788(8) 0.04896(7) 0.0237(2) Uani 1 1 d .
H11A H 0.6799 0.3757 -0.0059 0.028 Uiso 1 1 calc R
C12 C 0.55384(10) 0.32035(8) 0.06884(6) 0.0214(2) Uani 1 1 d .
H12A H 0.5795 0.2478 0.0761 0.026 Uiso 1 1 calc R
C13 C 0.42725(11) 0.32798(8) -0.00433(7) 0.0240(2) Uani 1 1 d .
H13A H 0.3466 0.3243 0.0176 0.029 Uiso 1 1 calc R
H13B H 0.4274 0.3946 -0.0305 0.029 Uiso 1 1 calc R
C14 C 0.41745(12) 0.24463(9) -0.07102(7) 0.0300(2) Uani 1 1 d .
H14A H 0.5016 0.2447 -0.0894 0.036 Uiso 1 1 calc R
H14B H 0.3448 0.2631 -0.1185 0.036 Uiso 1 1 calc R
C15 C 0.39141(12) 0.13496(9) -0.04452(8) 0.0315(3) Uani 1 1 d .
H15A H 0.4743 0.1101 -0.0073 0.038 Uiso 1 1 calc R
H15B H 0.3736 0.0917 -0.0937 0.038 Uiso 1 1 calc R
C16 C 0.27410(11) 0.12061(9) -0.00117(7) 0.0275(2) Uani 1 1 d .
H16A H 0.2973 0.1607 0.0504 0.033 Uiso 1 1 calc R
C17 C 0.26503(14) 0.00834(10) 0.02391(10) 0.0411(3) Uani 1 1 d .
H17A H 0.3490 -0.0117 0.0612 0.062 Uiso 1 1 calc R
H17B H 0.2486 -0.0342 -0.0249 0.062 Uiso 1 1 calc R
H17C H 0.1918 0.0004 0.0511 0.062 Uiso 1 1 calc R
C18 C 0.13562(12) 0.15971(9) -0.05118(7) 0.0281(2) Uani 1 1 d .
H18A H 0.0968 0.1091 -0.0931 0.034 Uiso 1 1 calc R
H18B H 0.1495 0.2223 -0.0798 0.034 Uiso 1 1 calc R
C19 C 0.03303(11) 0.18145(9) 0.00234(7) 0.0256(2) Uani 1 1 d .
H19A H 0.0111 0.1168 0.0265 0.031 Uiso 1 1 calc R
C20 C -0.09814(12) 0.22848(10) -0.05020(8) 0.0348(3) Uani 1 1 d .
H20A H -0.1635 0.2351 -0.0169 0.052 Uiso 1 1 calc R
H20B H -0.1344 0.1848 -0.0970 0.052 Uiso 1 1 calc R
H20C H -0.0789 0.2950 -0.0696 0.052 Uiso 1 1 calc R
C21 C 0.10061(10) 0.25247(8) 0.07151(7) 0.0232(2) Uani 1 1 d .
H21A H 0.1561 0.3024 0.0567 0.028 Uiso 1 1 calc R
C22 C 0.09307(10) 0.25477(8) 0.15119(7) 0.0236(2) Uani 1 1 d .
C23 C -0.00069(12) 0.19084(10) 0.18858(8) 0.0332(3) Uani 1 1 d .
H23A H -0.0454 0.1408 0.1487 0.050 Uiso 1 1 calc R
H23B H -0.0675 0.2344 0.2037 0.050 Uiso 1 1 calc R
H23C H 0.0509 0.1565 0.2373 0.050 Uiso 1 1 calc R
C24 C 0.18324(11) 0.32857(9) 0.20744(6) 0.0236(2) 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
C1 O2 C5 110.11(8)
C3 O3 C4 118.98(9)
O1 C1 O2 120.93(10)
O1 C1 C2 129.44(10)
O2 C1 C2 109.61(9)
C3 C2 C1 106.44(9)
C3 C2 C24 132.19(10)
C1 C2 C24 121.29(9)
O3 C3 C2 134.32(10)
O3 C3 C5 114.37(9)
C2 C3 C5 111.29(9)
O3 C4 H4A 109.5
O3 C4 H4B 109.5
H4A C4 H4B 109.5
O3 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
O2 C5 C3 102.55(8)
O2 C5 C6 110.13(8)
C3 C5 C6 111.57(8)
O2 C5 C12 109.70(8)
C3 C5 C12 112.75(9)
C6 C5 C12 109.91(8)
C5 C6 C7 113.64(9)
C5 C6 H6A 108.8
C7 C6 H6A 108.8
C5 C6 H6B 108.8
C7 C6 H6B 108.8
H6A C6 H6B 107.7
C9 C7 C6 111.56(9)
C9 C7 C8 112.58(10)
C6 C7 C8 111.70(9)
C9 C7 H7A 106.9
C6 C7 H7A 106.9
C8 C7 H7A 106.9
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C11 C9 C10 120.79(10)
C11 C9 C7 122.52(10)
C10 C9 C7 116.69(10)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C9 C11 C12 125.93(10)
C9 C11 H11A 117.0
C12 C11 H11A 117.0
C11 C12 C5 109.58(8)
C11 C12 C13 110.45(8)
C5 C12 C13 113.47(8)
C11 C12 H12A 107.7
C5 C12 H12A 107.7
C13 C12 H12A 107.7
C14 C13 C12 114.71(9)
C14 C13 H13A 108.6
C12 C13 H13A 108.6
C14 C13 H13B 108.6
C12 C13 H13B 108.6
H13A C13 H13B 107.6
C13 C14 C15 116.05(9)
C13 C14 H14A 108.3
C15 C14 H14A 108.3
C13 C14 H14B 108.3
C15 C14 H14B 108.3
H14A C14 H14B 107.4
C14 C15 C16 116.77(10)
C14 C15 H15A 108.1
C16 C15 H15A 108.1
C14 C15 H15B 108.1
C16 C15 H15B 108.1
H15A C15 H15B 107.3
C17 C16 C18 110.94(10)
C17 C16 C15 110.23(10)
C18 C16 C15 114.57(10)
C17 C16 H16A 106.9
C18 C16 H16A 106.9
C15 C16 H16A 106.9
C16 C17 H17A 109.5
C16 C17 H17B 109.5
H17A C17 H17B 109.5
C16 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C16 C18 C19 113.88(9)
C16 C18 H18A 108.8
C19 C18 H18A 108.8
C16 C18 H18B 108.8
C19 C18 H18B 108.8
H18A C18 H18B 107.7
C21 C19 C20 111.18(9)
C21 C19 C18 107.67(9)
C20 C19 C18 111.04(9)
C21 C19 H19A 109.0
C20 C19 H19A 109.0
C18 C19 H19A 109.0
C19 C20 H20A 109.5
C19 C20 H20B 109.5
H20A C20 H20B 109.5
C19 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C22 C21 C19 129.85(10)
C22 C21 H21A 115.1
C19 C21 H21A 115.1
C21 C22 C24 117.34(10)
C21 C22 C23 125.67(10)
C24 C22 C23 116.97(10)
C22 C23 H23A 109.5
C22 C23 H23B 109.5
H23A C23 H23B 109.5
C22 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
O4 C24 C22 122.75(10)
O4 C24 C2 120.72(10)
C22 C24 C2 116.53(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2032(13)
O2 C1 1.3681(12)
O2 C5 1.4499(12)
O3 C3 1.3254(13)
O3 C4 1.4495(13)
O4 C24 1.2157(13)
C1 C2 1.4668(15)
C2 C3 1.3480(15)
C2 C24 1.5072(14)
C3 C5 1.5075(14)
C4 H4A 0.9600
C4 H4B 0.9600
C4 H4C 0.9600
C5 C6 1.5298(14)
C5 C12 1.5389(14)
C6 C7 1.5343(15)
C6 H6A 0.9700
C6 H6B 0.9700
C7 C9 1.5163(15)
C7 C8 1.5353(17)
C7 H7A 0.9800
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 C11 1.3306(16)
C9 C10 1.5076(15)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 C12 1.5118(14)
C11 H11A 0.9300
C12 C13 1.5412(14)
C12 H12A 0.9800
C13 C14 1.5337(15)
C13 H13A 0.9700
C13 H13B 0.9700
C14 C15 1.5350(17)
C14 H14A 0.9700
C14 H14B 0.9700
C15 C16 1.5376(16)
C15 H15A 0.9700
C15 H15B 0.9700
C16 C17 1.5285(17)
C16 C18 1.5342(16)
C16 H16A 0.9800
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 C19 1.5427(15)
C18 H18A 0.9700
C18 H18B 0.9700
C19 C21 1.5028(15)
C19 C20 1.5302(16)
C19 H19A 0.9800
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
C21 C22 1.3384(15)
C21 H21A 0.9300
C22 C24 1.4888(15)
C22 C23 1.5020(15)
C23 H23A 0.9600
C23 H23B 0.9600
C23 H23C 0.9600
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
C5 O2 C1 O1 -179.21(10)
C5 O2 C1 C2 -0.75(11)
O1 C1 C2 C3 178.97(11)
O2 C1 C2 C3 0.68(11)
O1 C1 C2 C24 1.79(17)
O2 C1 C2 C24 -176.50(9)
C4 O3 C3 C2 -4.53(18)
C4 O3 C3 C5 173.73(9)
C1 C2 C3 O3 177.96(11)
C24 C2 C3 O3 -5.3(2)
C1 C2 C3 C5 -0.34(12)
C24 C2 C3 C5 176.41(10)
C1 O2 C5 C3 0.51(10)
C1 O2 C5 C6 -118.36(9)
C1 O2 C5 C12 120.54(9)
O3 C3 C5 O2 -178.74(8)
C2 C3 C5 O2 -0.08(11)
O3 C3 C5 C6 -60.89(12)
C2 C3 C5 C6 117.77(10)
O3 C3 C5 C12 63.36(11)
C2 C3 C5 C12 -117.97(10)
O2 C5 C6 C7 -60.23(11)
C3 C5 C6 C7 -173.42(9)
C12 C5 C6 C7 60.74(12)
C5 C6 C7 C9 -38.55(13)
C5 C6 C7 C8 88.43(11)
C6 C7 C9 C11 6.63(15)
C8 C7 C9 C11 -119.87(12)
C6 C7 C9 C10 -173.43(9)
C8 C7 C9 C10 60.07(13)
C10 C9 C11 C12 -176.62(10)
C7 C9 C11 C12 3.31(17)
C9 C11 C12 C5 18.06(15)
C9 C11 C12 C13 143.77(11)
O2 C5 C12 C11 73.50(10)
C3 C5 C12 C11 -172.90(8)
C6 C5 C12 C11 -47.73(11)
O2 C5 C12 C13 -50.46(11)
C3 C5 C12 C13 63.14(11)
C6 C5 C12 C13 -171.70(9)
C11 C12 C13 C14 87.78(11)
C5 C12 C13 C14 -148.74(9)
C12 C13 C14 C15 68.39(13)
C13 C14 C15 C16 49.35(15)
C14 C15 C16 C17 -177.94(11)
C14 C15 C16 C18 56.09(14)
C17 C16 C18 C19 75.27(13)
C15 C16 C18 C19 -159.12(10)
C16 C18 C19 C21 53.35(12)
C16 C18 C19 C20 175.28(10)
C20 C19 C21 C22 95.85(14)
C18 C19 C21 C22 -142.31(12)
C19 C21 C22 C24 174.12(10)
C19 C21 C22 C23 -7.25(19)
C21 C22 C24 O4 151.03(11)
C23 C22 C24 O4 -27.72(16)
C21 C22 C24 C2 -29.15(14)
C23 C22 C24 C2 152.10(10)
C3 C2 C24 O4 117.79(14)
C1 C2 C24 O4 -65.86(14)
C3 C2 C24 C22 -62.04(15)
C1 C2 C24 C22 114.32(11)
