#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/89/4108975.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_4108975
loop_
_publ_author_name
'K. C. Nicolaou'
'Scott T. Harrison'
_publ_section_title
;
 Total Synthesis of Abyssomicin C, Atrop-abyssomicin C, and Abyssomicin D:
 Implications for Natural Origins of Atrop-abyssomicin C
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              429
_journal_page_last               440
_journal_paper_doi               10.1021/ja067083p
_journal_volume                  129
_journal_year                    2007
_chemical_absolute_configuration syn
_chemical_formula_moiety         '2(C21 H26 O5 S2), C H Cl2'
_chemical_formula_sum            'C43 H53 Cl2 O10 S4'
_chemical_formula_weight         929.03
_chemical_name_systematic
; 

 ? 

;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 101.35(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   19.187(4)
_cell_length_b                   9.2491(18)
_cell_length_c                   12.923(3)
_cell_measurement_reflns_used    6318
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.00
_cell_measurement_theta_min      2.50
_cell_volume                     2248.5(9)
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_collection       'Bruker SMART'
_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, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8279
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.61
_diffrn_standards_decay_%        1
_exptl_absorpt_coefficient_mu    0.386
_exptl_absorpt_correction_T_max  0.9268
_exptl_absorpt_correction_T_min  0.8865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1999)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       Parallalepiped
_exptl_crystal_F_000             978
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.806
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3950
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0532
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.7000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1481
_refine_ls_wR_factor_ref         0.1511
_reflns_number_gt                3695
_reflns_number_total             3950
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja067083psi20061006_105240.cif
_cod_data_source_block           shar
_cod_original_sg_symbol_Hall     'C 2yb'
_cod_database_code               4108975
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, 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
S1 S 0.49308(5) 0.34968(11) 0.22838(9) 0.0573(3) Uani 1 1 d .
S2 S 0.54990(5) 0.07399(10) 0.16090(9) 0.0597(3) Uani 1 1 d .
O1 O 0.60767(13) 0.5799(3) 0.17202(19) 0.0481(6) Uani 1 1 d .
O2 O 0.73814(14) 0.3274(3) 0.1313(2) 0.0516(6) Uani 1 1 d .
O3 O 0.70481(17) 0.1105(3) 0.1805(2) 0.0595(7) Uani 1 1 d .
O4 O 0.76069(16) 0.8233(3) 0.1755(2) 0.0580(7) Uani 1 1 d .
H4 H 0.7390 0.9001 0.1694 0.070 Uiso 1 1 calc R
O5 O 0.79673(17) 0.3322(4) 0.5171(3) 0.0751(9) Uani 1 1 d .
C1 C 0.6464(2) 0.7035(4) 0.1363(3) 0.0494(9) Uani 1 1 d .
H1 H 0.6195 0.7928 0.1400 0.059 Uiso 1 1 calc R
C2 C 0.6548(2) 0.6781(4) 0.0223(3) 0.0559(9) Uani 1 1 d .
H2 H 0.6811 0.7607 0.0016 0.067 Uiso 1 1 calc R
C3 C 0.7013(3) 0.5419(5) 0.0201(3) 0.0611(11) Uani 1 1 d .
H3A H 0.6780 0.4750 -0.0334 0.073 Uiso 1 1 calc R
H3B H 0.7469 0.5683 0.0041 0.073 Uiso 1 1 calc R
C4 C 0.7115(2) 0.4719(4) 0.1297(3) 0.0442(8) Uani 1 1 d .
C5 C 0.64271(19) 0.4559(4) 0.1640(2) 0.0393(7) Uani 1 1 d .
C6 C 0.63004(17) 0.3189(3) 0.1878(2) 0.0391(7) Uani 1 1 d .
C7 C 0.6916(2) 0.2378(4) 0.1683(3) 0.0458(8) Uani 1 1 d .
C8 C 0.7186(2) 0.7147(4) 0.2114(3) 0.0460(8) Uani 1 1 d .
H8 H 0.7117 0.7384 0.2827 0.055 Uiso 1 1 calc R
C9 C 0.75896(18) 0.5699(4) 0.2133(3) 0.0475(8) Uani 1 1 d .
H9 H 0.8040 0.5878 0.1904 0.057 Uiso 1 1 calc R
C10 C 0.57518(18) 0.2436(4) 0.2381(3) 0.0441(7) Uani 1 1 d .
C11 C 0.6079(2) 0.2160(4) 0.3581(3) 0.0490(8) Uani 1 1 d .
H11 H 0.6574 0.1859 0.3621 0.059 Uiso 1 1 calc R
C12 C 0.6097(2) 0.3552(5) 0.4224(3) 0.0553(9) Uani 1 1 d .
H12A H 0.5661 0.3615 0.4495 0.066 Uiso 1 1 calc R
H12B H 0.6107 0.4369 0.3756 0.066 Uiso 1 1 calc R
C13 C 0.6732(2) 0.3684(5) 0.5157(3) 0.0591(10) Uani 1 1 d .
H13 H 0.6774 0.2782 0.5562 0.071 Uiso 1 1 calc R
C14 C 0.7423(2) 0.3951(4) 0.4796(3) 0.0545(9) Uani 1 1 d .
C15 C 0.7389(2) 0.5041(4) 0.3934(3) 0.0534(9) Uani 1 1 d .
H15 H 0.7105 0.5854 0.3937 0.064 Uiso 1 1 calc R
C16 C 0.7746(2) 0.4893(4) 0.3172(3) 0.0507(8) Uani 1 1 d .
H16 H 0.8123 0.4243 0.3278 0.061 Uiso 1 1 calc R
C17 C 0.5843(4) 0.6676(6) -0.0568(4) 0.0901(17) Uani 1 1 d .
H17A H 0.5935 0.6547 -0.1265 0.108 Uiso 1 1 calc R
H17B H 0.5576 0.7549 -0.0544 0.108 Uiso 1 1 calc R
H17C H 0.5576 0.5868 -0.0390 0.108 Uiso 1 1 calc R
C18 C 0.5713(3) 0.0954(5) 0.4080(4) 0.0698(12) Uani 1 1 d .
H18A H 0.5892 0.0937 0.4828 0.084 Uiso 1 1 calc R
H18B H 0.5806 0.0042 0.3780 0.084 Uiso 1 1 calc R
H18C H 0.5209 0.1126 0.3945 0.084 Uiso 1 1 calc R
C19 C 0.6609(3) 0.4945(7) 0.5891(4) 0.0815(15) Uani 1 1 d .
H19A H 0.7031 0.5095 0.6418 0.098 Uiso 1 1 calc R
H19B H 0.6220 0.4711 0.6228 0.098 Uiso 1 1 calc R
H19C H 0.6500 0.5811 0.5482 0.098 Uiso 1 1 calc R
C20 C 0.4370(2) 0.2469(6) 0.1268(4) 0.0709(12) Uani 1 1 d .
H20A H 0.3873 0.2643 0.1284 0.085 Uiso 1 1 calc R
H20B H 0.4454 0.2748 0.0579 0.085 Uiso 1 1 calc R
C21 C 0.4549(2) 0.0884(6) 0.1475(5) 0.0775(14) Uani 1 1 d .
H21A H 0.4309 0.0294 0.0893 0.093 Uiso 1 1 calc R
H21B H 0.4404 0.0567 0.2116 0.093 Uiso 1 1 calc R
Cl1 Cl 0.4987(2) 0.7021(3) 0.6110(3) 0.1748(12) Uani 1 1 d .
C22 C 0.5000 0.788(3) 0.5000 0.197(7) Uiso 1 2 d S
H22A H 0.4587 0.8461 0.4869 0.237 Uiso 0.50 1 d P
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_3
C20 S1 C10 98.6(2) .
C21 S2 C10 98.1(2) .
C5 O1 C1 110.1(2) .
C7 O2 C4 108.3(3) .
O1 C1 C8 107.5(3) .
O1 C1 C2 109.6(3) .
C8 C1 C2 111.5(3) .
C1 C2 C17 113.9(4) .
C1 C2 C3 108.2(3) .
C17 C2 C3 111.9(4) .
C4 C3 C2 107.2(3) .
O2 C4 C5 103.9(3) .
O2 C4 C3 112.9(3) .
C5 C4 C3 111.0(3) .
O2 C4 C9 112.1(3) .
C5 C4 C9 106.5(3) .
C3 C4 C9 110.2(3) .
C6 C5 O1 132.4(3) .
C6 C5 C4 112.1(3) .
O1 C5 C4 115.3(3) .
C5 C6 C7 104.9(3) .
C5 C6 C10 135.2(3) .
C7 C6 C10 119.5(3) .
O3 C7 O2 120.0(3) .
O3 C7 C6 129.3(3) .
O2 C7 C6 110.7(3) .
O4 C8 C1 110.0(3) .
O4 C8 C9 107.5(3) .
C1 C8 C9 109.9(3) .
C16 C9 C8 116.9(3) .
C16 C9 C4 108.3(3) .
C8 C9 C4 105.7(3) .
C6 C10 C11 108.7(3) .
C6 C10 S1 112.6(2) .
C11 C10 S1 108.9(2) .
C6 C10 S2 106.6(2) .
C11 C10 S2 113.6(2) .
S1 C10 S2 106.39(18) .
C18 C11 C12 110.4(3) .
C18 C11 C10 113.9(3) .
C12 C11 C10 111.1(3) .
C11 C12 C13 114.9(3) .
C14 C13 C12 112.2(3) .
C14 C13 C19 108.3(4) .
C12 C13 C19 110.2(4) .
O5 C14 C15 122.0(4) .
O5 C14 C13 122.6(4) .
C15 C14 C13 115.4(4) .
C16 C15 C14 122.5(4) .
C15 C16 C9 125.0(4) .
C21 C20 S1 107.4(3) .
C20 C21 S2 106.2(3) .
Cl1 C22 Cl1 122.3(15) 2_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C20 1.797(5) .
S1 C10 1.839(3) .
S2 C21 1.802(5) .
S2 C10 1.871(4) .
O1 C5 1.344(4) .
O1 C1 1.486(4) .
O2 C7 1.371(4) .
O2 C4 1.429(4) .
O3 C7 1.209(5) .
O4 C8 1.422(4) .
O5 C14 1.210(5) .
C1 C8 1.530(6) .
C1 C2 1.531(6) .
C2 C17 1.530(7) .
C2 C3 1.547(6) .
C3 C4 1.534(5) .
C4 C5 1.480(5) .
C4 C9 1.559(5) .
C5 C6 1.337(5) .
C6 C7 1.462(5) .
C6 C10 1.512(5) .
C8 C9 1.545(5) .
C9 C16 1.514(5) .
C10 C11 1.575(5) .
C11 C18 1.527(5) .
C11 C12 1.529(6) .
C12 C13 1.540(6) .
C13 C14 1.510(7) .
C13 C19 1.551(7) .
C14 C15 1.494(5) .
C15 C16 1.312(6) .
C20 C21 1.517(8) .
Cl1 C22 1.644(12) .
C22 Cl1 1.644(12) 2_656
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O3 0.82 2.07 2.870(4) 166.3 1_565
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 O1 C1 C8 -63.4(3)
C5 O1 C1 C2 57.9(4)
O1 C1 C2 C17 61.7(4)
C8 C1 C2 C17 -179.4(3)
O1 C1 C2 C3 -63.4(4)
C8 C1 C2 C3 55.5(4)
C1 C2 C3 C4 8.4(4)
C17 C2 C3 C4 -117.9(4)
C7 O2 C4 C5 -3.0(4)
C7 O2 C4 C3 -123.3(3)
C7 O2 C4 C9 111.6(3)
C2 C3 C4 O2 165.4(3)
C2 C3 C4 C5 49.3(4)
C2 C3 C4 C9 -68.5(4)
C1 O1 C5 C6 178.6(4)
C1 O1 C5 C4 3.9(4)
O2 C4 C5 C6 2.3(4)
C3 C4 C5 C6 123.9(3)
C9 C4 C5 C6 -116.2(3)
O2 C4 C5 O1 178.1(3)
C3 C4 C5 O1 -60.4(4)
C9 C4 C5 O1 59.6(4)
O1 C5 C6 C7 -175.5(4)
C4 C5 C6 C7 -0.6(4)
O1 C5 C6 C10 -3.8(7)
C4 C5 C6 C10 171.0(4)
C4 O2 C7 O3 -177.0(4)
C4 O2 C7 C6 2.9(4)
C5 C6 C7 O3 178.5(4)
C10 C6 C7 O3 5.3(6)
C5 C6 C7 O2 -1.4(4)
C10 C6 C7 O2 -174.6(3)
O1 C1 C8 O4 174.8(3)
C2 C1 C8 O4 54.7(4)
O1 C1 C8 C9 56.6(3)
C2 C1 C8 C9 -63.5(4)
O4 C8 C9 C16 123.9(3)
C1 C8 C9 C16 -116.3(3)
O4 C8 C9 C4 -115.5(3)
C1 C8 C9 C4 4.2(3)
O2 C4 C9 C16 -47.1(4)
C5 C4 C9 C16 65.9(3)
C3 C4 C9 C16 -173.6(3)
O2 C4 C9 C8 -173.0(3)
C5 C4 C9 C8 -60.1(3)
C3 C4 C9 C8 60.4(3)
C5 C6 C10 C11 -98.4(5)
C7 C6 C10 C11 72.3(4)
C5 C6 C10 S1 22.4(5)
C7 C6 C10 S1 -166.9(3)
C5 C6 C10 S2 138.7(4)
C7 C6 C10 S2 -50.6(4)
C20 S1 C10 C6 105.2(3)
C20 S1 C10 C11 -134.1(3)
C20 S1 C10 S2 -11.2(2)
C21 S2 C10 C6 -134.2(3)
C21 S2 C10 C11 106.0(3)
C21 S2 C10 S1 -13.8(3)
C6 C10 C11 C18 -158.5(3)
S1 C10 C11 C18 78.5(4)
S2 C10 C11 C18 -39.9(4)
C6 C10 C11 C12 76.0(3)
S1 C10 C11 C12 -47.0(3)
S2 C10 C11 C12 -165.4(3)
C18 C11 C12 C13 85.9(4)
C10 C11 C12 C13 -146.6(3)
C11 C12 C13 C14 71.8(4)
C11 C12 C13 C19 -167.4(3)
C12 C13 C14 O5 -135.7(4)
C19 C13 C14 O5 102.3(5)
C12 C13 C14 C15 43.8(5)
C19 C13 C14 C15 -78.2(4)
O5 C14 C15 C16 37.1(6)
C13 C14 C15 C16 -142.4(4)
C14 C15 C16 C9 162.2(4)
C8 C9 C16 C15 23.2(5)
C4 C9 C16 C15 -96.0(4)
C10 S1 C20 C21 38.9(4)
S1 C20 C21 S2 -52.0(5)
C10 S2 C21 C20 40.0(4)
