#------------------------------------------------------------------------------
#$Date: 2019-11-23 17:31:14 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234217 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/33/1553390.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_1553390
loop_
_publ_author_name
'Huang, Hongbo'
'Song, Yongxiang'
'Li, Xin'
'Wang, Xin'
'Ling, Chunyao'
'Qin, Xiangjing'
'Zhou, Zhenbin'
'Li, Qinglian'
'Wei, Xiaoyi'
'Ju, Jianhua'
_publ_section_title
;
 Abyssomicin Monomers and Dimers from the Marine-Derived Streptomyces
 koyangensis SCSIO 5802.
;
_journal_issue                   8
_journal_name_full               'Journal of natural products'
_journal_page_first              1892
_journal_page_last               1898
_journal_paper_doi               10.1021/acs.jnatprod.8b00448
_journal_volume                  81
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C38 H46 O12 S, 2(H2 O)'
_chemical_formula_sum            'C38 H50 O14 S'
_chemical_formula_weight         762.84
_space_group_crystal_system      hexagonal
_space_group_IT_number           171
_space_group_name_Hall           'P 62'
_space_group_name_H-M_alt        'P 62'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   13.4030(8)
_cell_length_b                   13.4030(8)
_cell_length_c                   17.8604(10)
_cell_measurement_reflns_used    4374
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.0480
_cell_measurement_theta_min      3.8330
_cell_volume                     2778.6(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SMART'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  graphite
_diffrn_measurement_method       'CCD area detector'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9136
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.604
_diffrn_reflns_theta_min         3.808
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.368
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   saddas
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       diamond
_exptl_crystal_F_000             1218
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3407
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0856P)²+0.1637P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1211
_refine_ls_wR_factor_ref         0.1229
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    0.948
_reflns_Friedel_fraction_max     0.916
_reflns_number_gt                3234
_reflns_number_total             3407
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np8b00448_si_004.cif
_cod_data_source_block           1
_cod_original_cell_volume        2778.6(4)
_cod_database_code               1553390
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.875
_shelx_estimated_absorpt_t_max   0.960
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z'
'y, -x+y, z+2/3'
'x-y, x, z+1/3'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C1 C 0.7837(4) 0.6148(3) 0.3973(2) 0.0396(8) Uani 1 1 d . . .
C2 C 0.8416(3) 0.5878(3) 0.4575(2) 0.0359(8) Uani 1 1 d . . .
C3 C 0.7817(3) 0.4878(3) 0.4959(2) 0.0349(7) Uani 1 1 d . . .
C4 C 0.8214(3) 0.4578(3) 0.5666(2) 0.0356(7) Uani 1 1 d . . .
H4A H 0.8772 0.4345 0.5539 0.043 Uiso 1 1 calc R U .
H4B H 0.7561 0.3925 0.5900 0.043 Uiso 1 1 calc R U .
C5 C 0.8759(3) 0.5571(3) 0.6228(2) 0.0345(7) Uani 1 1 d . . .
H5A H 0.9512 0.6143 0.6043 0.041 Uiso 1 1 calc R U .
H5B H 0.8872 0.5278 0.6698 0.041 Uiso 1 1 calc R U .
C6 C 0.8045(3) 0.6164(3) 0.6379(2) 0.0358(8) Uani 1 1 d . . .
C7 C 0.8124(3) 0.6990(3) 0.57596(19) 0.0354(7) Uani 1 1 d . . .
C8 C 0.9291(3) 0.7704(3) 0.53835(19) 0.0335(7) Uani 1 1 d . . .
C9 C 0.9460(3) 0.8789(3) 0.49681(19) 0.0342(7) Uani 1 1 d . . .
C10 C 1.0269(4) 0.8893(3) 0.43260(19) 0.0359(8) Uani 1 1 d . . .
C11 C 1.1436(3) 0.9081(3) 0.4629(2) 0.0350(8) Uani 1 1 d . . .
C12 C 1.1544(3) 0.7976(3) 0.45440(19) 0.0344(7) Uani 1 1 d . . .
C13 C 1.1516(4) 0.7714(3) 0.3703(2) 0.0372(8) Uani 1 1 d . . .
C14 C 1.0326(4) 0.7441(3) 0.3418(2) 0.0400(8) Uani 1 1 d . . .
H14A H 1.0417 0.7909 0.2982 0.048 Uiso 1 1 calc R U .
H14B H 0.9891 0.6638 0.3270 0.048 Uiso 1 1 calc R U .
C15 C 0.9665(3) 0.7675(3) 0.40212(19) 0.0351(7) Uani 1 1 d . . .
C16 C 0.9494(3) 0.6989(3) 0.47500(19) 0.0322(7) Uani 1 1 d . . .
C17 C 0.6793(4) 0.5324(3) 0.6587(2) 0.0426(9) Uani 1 1 d . . .
H17A H 0.6421 0.5749 0.6731 0.064 Uiso 1 1 calc R U .
H17B H 0.6770 0.4850 0.6997 0.064 Uiso 1 1 calc R U .
H17C H 0.6401 0.4846 0.6164 0.064 Uiso 1 1 calc R U .
C18 C 1.2600(4) 0.8145(3) 0.4958(2) 0.0381(8) Uani 1 1 d . . .
H18A H 1.2517 0.8243 0.5482 0.057 Uiso 1 1 calc R U .
H18B H 1.3269 0.8817 0.4768 0.057 Uiso 1 1 calc R U .
H18C H 1.2687 0.7483 0.4886 0.057 Uiso 1 1 calc R U .
C19 C 1.1737(4) 0.6717(4) 0.3535(2) 0.0443(9) Uani 1 1 d . . .
H19A H 1.1223 0.6056 0.3828 0.066 Uiso 1 1 calc R U .
H19B H 1.2519 0.6944 0.3659 0.066 Uiso 1 1 calc R U .
H19C H 1.1607 0.6526 0.3012 0.066 Uiso 1 1 calc R U .
H6 H 0.839(3) 0.676(3) 0.679(2) 0.026(9) Uiso 1 1 d . . .
H8 H 0.985(3) 0.788(3) 0.574(2) 0.018(8) Uiso 1 1 d . . .
H9 H 0.869(4) 0.862(4) 0.476(3) 0.038(11) Uiso 1 1 d . . .
H10 H 1.038(3) 0.943(3) 0.397(3) 0.025(8) Uiso 1 1 d . . .
H11 H 1.149(3) 0.922(3) 0.516(3) 0.030(10) Uiso 1 1 d . . .
H13 H 1.209(4) 0.837(4) 0.346(3) 0.038(11) Uiso 1 1 d . . .
O1 O 0.8499(3) 0.7262(2) 0.37424(14) 0.0394(6) Uani 1 1 d . . .
O2 O 0.6885(3) 0.5523(2) 0.37152(16) 0.0466(7) Uani 1 1 d . . .
O3 O 0.6749(2) 0.4072(2) 0.47416(15) 0.0406(6) Uani 1 1 d . . .
H3 H 0.6564 0.4297 0.4368 0.061 Uiso 1 1 calc R U .
O4 O 0.7302(2) 0.7097(2) 0.55939(17) 0.0439(6) Uani 1 1 d . . .
O5 O 1.0543(2) 0.6982(2) 0.48921(13) 0.0328(5) Uani 1 1 d . . .
O6 O 1.2350(3) 1.0010(2) 0.42382(15) 0.0430(6) Uani 1 1 d . . .
H6A H 1.2968 1.0113 0.4398 0.065 Uiso 1 1 calc R U .
O7 O 0.6022(4) 0.8083(3) 0.5059(2) 0.0624(9) Uani 1 1 d G . .
H7A H 0.6568 0.8051 0.5277 0.11(3) Uiso 1 1 d G . .
H7B H 0.5394 0.7457 0.5130 0.017(8) Uiso 1 1 d G . .
S1 S 1.0000 1.0000 0.56182(7) 0.0343(3) Uani 1 2 d S T P
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
S S 0.3331 0.5567 '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
O2 C1 O1 121.6(3) .
O2 C1 C2 127.5(4) .
O1 C1 C2 110.8(3) .
C3 C2 C1 119.2(3) .
C3 C2 C16 132.6(3) .
C1 C2 C16 105.8(3) .
O3 C3 C2 120.9(3) .
O3 C3 C4 113.8(3) .
C2 C3 C4 125.2(3) .
C3 C4 C5 113.4(3) .
C3 C4 H4A 108.9 .
C5 C4 H4A 108.9 .
C3 C4 H4B 108.9 .
C5 C4 H4B 108.9 .
H4A C4 H4B 107.7 .
C4 C5 C6 114.5(3) .
C4 C5 H5A 108.6 .
C6 C5 H5A 108.6 .
C4 C5 H5B 108.6 .
C6 C5 H5B 108.6 .
H5A C5 H5B 107.6 .
C17 C6 C7 111.2(3) .
C17 C6 C5 113.5(3) .
C7 C6 C5 114.2(3) .
C17 C6 H6 108(2) .
C7 C6 H6 96(2) .
C5 C6 H6 112(2) .
O4 C7 C8 121.7(3) .
O4 C7 C6 121.5(4) .
C8 C7 C6 116.8(3) .
C7 C8 C9 115.2(3) .
C7 C8 C16 111.5(3) .
C9 C8 C16 103.7(3) .
C7 C8 H8 108(2) .
C9 C8 H8 112(2) .
C16 C8 H8 107(2) .
C10 C9 C8 102.0(3) .
C10 C9 S1 116.5(3) .
C8 C9 S1 109.8(2) .
C10 C9 H9 110(3) .
C8 C9 H9 108(3) .
S1 C9 H9 110(3) .
C15 C10 C9 101.4(3) .
C15 C10 C11 104.6(3) .
C9 C10 C11 111.3(3) .
C15 C10 H10 113(2) .
C9 C10 H10 114(2) .
C11 C10 H10 111(2) .
O6 C11 C10 109.2(3) .
O6 C11 C12 109.6(3) .
C10 C11 C12 112.0(3) .
O6 C11 H11 112(2) .
C10 C11 H11 110(2) .
C12 C11 H11 104(2) .
O5 C12 C18 106.9(3) .
O5 C12 C13 107.4(3) .
C18 C12 C13 115.2(3) .
O5 C12 C11 110.0(3) .
C18 C12 C11 109.5(3) .
C13 C12 C11 107.9(3) .
C14 C13 C19 110.9(3) .
C14 C13 C12 106.4(3) .
C19 C13 C12 113.3(3) .
C14 C13 H13 110(3) .
C19 C13 H13 107(3) .
C12 C13 H13 109(3) .
C15 C14 C13 111.0(3) .
C15 C14 H14A 109.4 .
C13 C14 H14A 109.4 .
C15 C14 H14B 109.4 .
C13 C14 H14B 109.4 .
H14A C14 H14B 108.0 .
O1 C15 C10 115.1(3) .
O1 C15 C14 107.7(3) .
C10 C15 C14 115.1(3) .
O1 C15 C16 104.5(3) .
C10 C15 C16 100.3(3) .
C14 C15 C16 113.7(3) .
O5 C16 C2 119.5(3) .
O5 C16 C15 107.4(3) .
C2 C16 C15 101.4(3) .
O5 C16 C8 110.0(3) .
C2 C16 C8 112.0(3) .
C15 C16 C8 105.0(3) .
C6 C17 H17A 109.5 .
C6 C17 H17B 109.5 .
H17A C17 H17B 109.5 .
C6 C17 H17C 109.5 .
H17A C17 H17C 109.5 .
H17B C17 H17C 109.5 .
C12 C18 H18A 109.5 .
C12 C18 H18B 109.5 .
H18A C18 H18B 109.5 .
C12 C18 H18C 109.5 .
H18A C18 H18C 109.5 .
H18B C18 H18C 109.5 .
C13 C19 H19A 109.5 .
C13 C19 H19B 109.5 .
H19A C19 H19B 109.5 .
C13 C19 H19C 109.5 .
H19A C19 H19C 109.5 .
H19B C19 H19C 109.5 .
C1 O1 C15 107.4(3) .
C3 O3 H3 109.5 .
C16 O5 C12 111.8(2) .
C11 O6 H6A 109.5 .
H7A O7 H7B 109.5 .
C9 S1 C9 101.0(2) 4_775
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O2 1.214(5) .
C1 O1 1.365(5) .
C1 C2 1.473(5) .
C2 C3 1.355(6) .
C2 C16 1.500(5) .
C3 O3 1.349(5) .
C3 C4 1.501(5) .
C4 C5 1.530(5) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C6 1.543(5) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C17 1.528(6) .
C6 C7 1.531(5) .
C6 H6 1.01(4) .
C7 O4 1.217(5) .
C7 C8 1.522(5) .
C8 C9 1.545(4) .
C8 C16 1.592(5) .
C8 H8 0.93(4) .
C9 C10 1.536(5) .
C9 S1 1.825(3) .
C9 H9 1.01(5) .
C10 C15 1.515(5) .
C10 C11 1.552(6) .
C10 H10 0.91(4) .
C11 O6 1.419(4) .
C11 C12 1.566(5) .
C11 H11 0.97(5) .
C12 O5 1.474(4) .
C12 C18 1.511(6) .
C12 C13 1.538(5) .
C13 C14 1.533(6) .
C13 C19 1.537(5) .
C13 H13 0.94(5) .
C14 C15 1.524(5) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 O1 1.460(5) .
C15 C16 1.543(4) .
C16 O5 1.433(4) .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
O3 H3 0.8200 .
O6 H6A 0.8200 .
O7 H7A 0.8494 .
O7 H7B 0.8498 .
S1 C9 1.825(3) 4_775
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
_geom_torsion_site_symmetry_4
O2 C1 C2 C3 -7.7(6) .
O1 C1 C2 C3 169.3(3) .
O2 C1 C2 C16 -172.4(4) .
O1 C1 C2 C16 4.7(4) .
C1 C2 C3 O3 7.9(5) .
C16 C2 C3 O3 167.6(4) .
C1 C2 C3 C4 -168.7(3) .
C16 C2 C3 C4 -9.0(6) .
O3 C3 C4 C5 -133.6(3) .
C2 C3 C4 C5 43.2(5) .
C3 C4 C5 C6 48.8(4) .
C4 C5 C6 C17 51.8(4) .
C4 C5 C6 C7 -77.1(4) .
C17 C6 C7 O4 14.8(5) .
C5 C6 C7 O4 144.8(3) .
C17 C6 C7 C8 -167.6(3) .
C5 C6 C7 C8 -37.6(4) .
O4 C7 C8 C9 17.3(5) .
C6 C7 C8 C9 -160.3(3) .
O4 C7 C8 C16 -100.5(4) .
C6 C7 C8 C16 81.9(4) .
C7 C8 C9 C10 -148.5(3) .
C16 C8 C9 C10 -26.4(4) .
C7 C8 C9 S1 87.3(3) .
C16 C8 C9 S1 -150.6(2) .
C8 C9 C10 C15 48.8(3) .
S1 C9 C10 C15 168.3(2) .
C8 C9 C10 C11 -62.0(4) .
S1 C9 C10 C11 57.5(3) .
C15 C10 C11 O6 119.3(3) .
C9 C10 C11 O6 -131.9(3) .
C15 C10 C11 C12 -2.2(4) .
C9 C10 C11 C12 106.5(3) .
O6 C11 C12 O5 -175.1(3) .
C10 C11 C12 O5 -53.7(4) .
O6 C11 C12 C18 67.7(4) .
C10 C11 C12 C18 -170.9(3) .
O6 C11 C12 C13 -58.3(4) .
C10 C11 C12 C13 63.1(4) .
O5 C12 C13 C14 54.8(3) .
C18 C12 C13 C14 173.7(3) .
C11 C12 C13 C14 -63.7(4) .
O5 C12 C13 C19 -67.3(4) .
C18 C12 C13 C19 51.6(5) .
C11 C12 C13 C19 174.2(3) .
C19 C13 C14 C15 131.2(3) .
C12 C13 C14 C15 7.6(4) .
C9 C10 C15 O1 60.5(3) .
C11 C10 C15 O1 176.3(3) .
C9 C10 C15 C14 -173.4(3) .
C11 C10 C15 C14 -57.6(4) .
C9 C10 C15 C16 -51.0(3) .
C11 C10 C15 C16 64.8(3) .
C13 C14 C15 O1 -173.1(3) .
C13 C14 C15 C10 57.0(4) .
C13 C14 C15 C16 -57.9(4) .
C3 C2 C16 O5 58.9(6) .
C1 C2 C16 O5 -139.4(3) .
C3 C2 C16 C15 176.7(4) .
C1 C2 C16 C15 -21.7(4) .
C3 C2 C16 C8 -71.8(5) .
C1 C2 C16 C8 89.9(3) .
O1 C15 C16 O5 157.1(2) .
C10 C15 C16 O5 -83.4(3) .
C14 C15 C16 O5 40.0(4) .
O1 C15 C16 C2 30.9(3) .
C10 C15 C16 C2 150.5(3) .
C14 C15 C16 C2 -86.2(4) .
O1 C15 C16 C8 -85.8(3) .
C10 C15 C16 C8 33.7(3) .
C14 C15 C16 C8 157.1(3) .
C7 C8 C16 O5 -124.5(3) .
C9 C8 C16 O5 111.0(3) .
C7 C8 C16 C2 10.9(4) .
C9 C8 C16 C2 -113.6(3) .
C7 C8 C16 C15 120.2(3) .
C9 C8 C16 C15 -4.3(4) .
O2 C1 O1 C15 -166.8(4) .
C2 C1 O1 C15 16.0(4) .
C10 C15 O1 C1 -138.6(3) .
C14 C15 O1 C1 91.5(3) .
C16 C15 O1 C1 -29.6(3) .
C2 C16 O5 C12 139.6(3) .
C15 C16 O5 C12 25.1(3) .
C8 C16 O5 C12 -88.7(3) .
C18 C12 O5 C16 158.5(3) .
C13 C12 O5 C16 -77.3(3) .
C11 C12 O5 C16 39.8(4) .
C10 C9 S1 C9 47.9(2) 4_775
C8 C9 S1 C9 163.2(3) 4_775
