#------------------------------------------------------------------------------
#$Date: 2016-03-21 19:06:25 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178835 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/89/4108974.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_4108974
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         'C19 H22 O6'
_chemical_formula_sum            'C19 H22 O6'
_chemical_formula_weight         346.37
_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                 93.88(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.934(4)
_cell_length_b                   6.8950(14)
_cell_length_c                   12.745(3)
_cell_measurement_reflns_used    3499
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      5.00
_cell_volume                     1835.4(7)
_computing_cell_refinement       'Bruker SMART'
_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  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0434
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6578
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        1
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9819
_exptl_absorpt_correction_T_min  0.9789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1999)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3192
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0600P)²+0.1200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1169
_reflns_number_gt                2572
_reflns_number_total             3192
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja067083psi20061006_105220.cif
_cod_data_source_block           stha
_cod_database_code               4108974
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
O1 O 0.27260(8) 0.6018(2) 0.13143(13) 0.0634(5) Uani 1 1 d .
O2 O 0.26507(10) 0.1588(3) 0.27500(15) 0.0747(5) Uani 1 1 d .
O3 O 0.16544(12) 0.0386(3) 0.24232(19) 0.0993(7) Uani 1 1 d .
O4 O 0.39584(9) 0.7217(4) 0.33871(18) 0.0976(7) Uani 1 1 d .
H4 H 0.3933 0.7976 0.3878 0.117 Uiso 1 1 calc R
O5 O 0.12308(9) 0.4856(3) 0.03234(13) 0.0801(6) Uani 1 1 d .
O6 O 0.13088(12) 0.4946(5) 0.50838(16) 0.1277(11) Uani 1 1 d .
C1 C 0.33795(12) 0.6482(4) 0.17589(19) 0.0630(6) Uani 1 1 d .
H1 H 0.3520 0.7705 0.1458 0.076 Uiso 1 1 calc R
C2 C 0.38533(13) 0.4859(4) 0.1512(2) 0.0682(7) Uani 1 1 d .
H2 H 0.4272 0.5185 0.1858 0.082 Uiso 1 1 calc R
C3 C 0.36199(14) 0.2921(4) 0.2002(2) 0.0730(7) Uani 1 1 d .
H3A H 0.3561 0.1932 0.1462 0.088 Uiso 1 1 calc R
H3B H 0.3935 0.2460 0.2538 0.088 Uiso 1 1 calc R
C4 C 0.29894(13) 0.3331(3) 0.24816(19) 0.0624(6) Uani 1 1 d .
C5 C 0.25296(12) 0.4331(3) 0.17048(16) 0.0553(6) Uani 1 1 d .
C6 C 0.19524(13) 0.3433(4) 0.16254(18) 0.0587(6) Uani 1 1 d .
C7 C 0.20363(15) 0.1672(4) 0.2283(2) 0.0715(7) Uani 1 1 d .
C8 C 0.33301(12) 0.6735(4) 0.2962(2) 0.0682(7) Uani 1 1 d .
H8 H 0.3034 0.7794 0.3095 0.082 Uiso 1 1 calc R
C9 C 0.30830(12) 0.4797(4) 0.34328(19) 0.0694(7) Uani 1 1 d .
H9 H 0.3422 0.4287 0.3924 0.083 Uiso 1 1 calc R
C10 C 0.13179(12) 0.4196(3) 0.12162(18) 0.0599(6) Uani 1 1 d .
C11 C 0.07989(13) 0.4281(4) 0.2008(2) 0.0718(7) Uani 1 1 d .
H11 H 0.0933 0.3433 0.2599 0.086 Uiso 1 1 calc R
C12 C 0.07644(13) 0.6397(4) 0.24385(19) 0.0695(7) Uani 1 1 d .
H12A H 0.1134 0.7110 0.2227 0.083 Uiso 1 1 calc R
H12B H 0.0385 0.7020 0.2114 0.083 Uiso 1 1 calc R
C13 C 0.07441(13) 0.6543(5) 0.3655(2) 0.0768(8) Uani 1 1 d .
H13 H 0.0385 0.5751 0.3862 0.092 Uiso 1 1 calc R
C14 C 0.13450(14) 0.5803(5) 0.42458(19) 0.0751(8) Uani 1 1 d .
C15 C 0.19795(13) 0.6091(4) 0.38028(17) 0.0647(7) Uani 1 1 d .
H15 H 0.2032 0.7148 0.3364 0.078 Uiso 1 1 calc R
C16 C 0.24735(14) 0.4905(4) 0.40074(18) 0.0729(7) Uani 1 1 d .
H16 H 0.2441 0.4047 0.4564 0.087 Uiso 1 1 calc R
C17 C 0.39326(18) 0.4659(5) 0.0327(2) 0.0943(9) Uani 1 1 d .
H17A H 0.3527 0.4337 -0.0028 0.113 Uiso 1 1 calc R
H17B H 0.4236 0.3651 0.0211 0.113 Uiso 1 1 calc R
H17C H 0.4084 0.5863 0.0058 0.113 Uiso 1 1 calc R
C18 C 0.01491(16) 0.3570(7) 0.1550(3) 0.1205(15) Uani 1 1 d .
H18A H 0.0008 0.4368 0.0961 0.145 Uiso 1 1 calc R
H18B H -0.0156 0.3644 0.2078 0.145 Uiso 1 1 calc R
H18C H 0.0186 0.2250 0.1321 0.145 Uiso 1 1 calc R
C19 C 0.06204(17) 0.8669(6) 0.3993(2) 0.0981(11) Uani 1 1 d .
H19A H 0.0592 0.8722 0.4741 0.118 Uiso 1 1 calc R
H19B H 0.0227 0.9122 0.3647 0.118 Uiso 1 1 calc R
H19C H 0.0967 0.9478 0.3798 0.118 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 0.0033 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
C5 O1 C1 110.12(17)
C7 O2 C4 108.67(18)
O1 C1 C2 110.85(19)
O1 C1 C8 106.31(19)
C2 C1 C8 111.7(2)
C17 C2 C1 112.3(2)
C17 C2 C3 111.9(2)
C1 C2 C3 108.4(2)
C4 C3 C2 107.7(2)
O2 C4 C5 103.58(19)
O2 C4 C3 113.2(2)
C5 C4 C3 110.9(2)
O2 C4 C9 112.8(2)
C5 C4 C9 104.6(2)
C3 C4 C9 111.2(2)
O1 C5 C6 131.5(2)
O1 C5 C4 116.4(2)
C6 C5 C4 111.6(2)
C5 C6 C7 105.2(2)
C5 C6 C10 129.3(2)
C7 C6 C10 123.9(2)
O3 C7 O2 120.6(2)
O3 C7 C6 128.9(3)
O2 C7 C6 110.5(2)
O4 C8 C1 106.2(2)
O4 C8 C9 111.9(2)
C1 C8 C9 109.1(2)
C16 C9 C8 117.0(2)
C16 C9 C4 109.7(2)
C8 C9 C4 106.20(19)
O5 C10 C6 121.9(2)
O5 C10 C11 121.9(2)
C6 C10 C11 116.0(2)
C18 C11 C10 112.9(2)
C18 C11 C12 111.9(3)
C10 C11 C12 108.6(2)
C13 C12 C11 114.5(2)
C14 C13 C19 109.2(2)
C14 C13 C12 113.4(2)
C19 C13 C12 110.7(3)
O6 C14 C15 120.2(3)
O6 C14 C13 119.9(3)
C15 C14 C13 119.9(2)
C16 C15 C14 123.0(2)
C15 C16 C9 127.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.340(3)
O1 C1 1.480(3)
O2 C7 1.381(3)
O2 C4 1.448(3)
O3 C7 1.215(3)
O4 C8 1.427(3)
O5 C10 1.228(3)
O6 C14 1.227(3)
C1 C2 1.542(4)
C1 C8 1.554(4)
C2 C17 1.537(4)
C2 C3 1.567(4)
C3 C4 1.518(4)
C4 C5 1.501(3)
C4 C9 1.581(4)
C5 C6 1.356(3)
C6 C7 1.479(4)
C6 C10 1.490(4)
C8 C9 1.567(4)
C9 C16 1.515(4)
C10 C11 1.533(4)
C11 C18 1.525(4)
C11 C12 1.562(4)
C12 C13 1.557(4)
C13 C14 1.511(4)
C13 C19 1.555(5)
C14 C15 1.491(4)
C15 C16 1.330(4)
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 O6 0.82 1.99 2.793(3) 167.7 4_556
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 C2 58.5(2)
C5 O1 C1 C8 -63.1(2)
O1 C1 C2 C17 64.5(3)
C8 C1 C2 C17 -177.2(2)
O1 C1 C2 C3 -59.6(3)
C8 C1 C2 C3 58.8(3)
C17 C2 C3 C4 -120.9(3)
C1 C2 C3 C4 3.5(3)
C7 O2 C4 C5 -6.4(2)
C7 O2 C4 C3 -126.5(2)
C7 O2 C4 C9 106.2(2)
C2 C3 C4 O2 166.9(2)
C2 C3 C4 C5 51.0(3)
C2 C3 C4 C9 -64.9(3)
C1 O1 C5 C6 171.7(3)
C1 O1 C5 C4 0.6(3)
O2 C4 C5 O1 -179.74(19)
C3 C4 C5 O1 -58.0(3)
C9 C4 C5 O1 61.9(3)
O2 C4 C5 C6 7.5(3)
C3 C4 C5 C6 129.2(2)
C9 C4 C5 C6 -110.9(2)
O1 C5 C6 C7 -176.8(2)
C4 C5 C6 C7 -5.4(3)
O1 C5 C6 C10 -11.2(4)
C4 C5 C6 C10 160.2(2)
C4 O2 C7 O3 -177.9(3)
C4 O2 C7 C6 3.5(3)
C5 C6 C7 O3 -177.2(3)
C10 C6 C7 O3 16.2(4)
C5 C6 C7 O2 1.2(3)
C10 C6 C7 O2 -165.4(2)
O1 C1 C8 O4 -179.0(2)
C2 C1 C8 O4 60.0(3)
O1 C1 C8 C9 60.2(2)
C2 C1 C8 C9 -60.8(3)
O4 C8 C9 C16 120.6(2)
C1 C8 C9 C16 -122.2(2)
O4 C8 C9 C4 -116.6(2)
C1 C8 C9 C4 0.7(3)
O2 C4 C9 C16 -41.9(3)
C5 C4 C9 C16 70.0(2)
C3 C4 C9 C16 -170.3(2)
O2 C4 C9 C8 -169.23(19)
C5 C4 C9 C8 -57.3(2)
C3 C4 C9 C8 62.4(3)
C5 C6 C10 O5 56.8(4)
C7 C6 C10 O5 -140.0(2)
C5 C6 C10 C11 -117.7(3)
C7 C6 C10 C11 45.5(3)
O5 C10 C11 C18 48.9(4)
C6 C10 C11 C18 -136.6(3)
O5 C10 C11 C12 -75.9(3)
C6 C10 C11 C12 98.7(2)
C18 C11 C12 C13 101.1(3)
C10 C11 C12 C13 -133.5(2)
C11 C12 C13 C14 64.3(3)
C11 C12 C13 C19 -172.6(2)
C19 C13 C14 O6 91.9(4)
C12 C13 C14 O6 -144.2(3)
C19 C13 C14 C15 -88.9(3)
C12 C13 C14 C15 35.0(4)
O6 C14 C15 C16 26.9(5)
C13 C14 C15 C16 -152.3(3)
C14 C15 C16 C9 165.9(3)
C8 C9 C16 C15 32.2(4)
C4 C9 C16 C15 -88.8(3)
