Meroterpenoids with Protein Tyrosine Phosphatase 1B Inhibitory Activity from a Hyrtios sp. Marine Sponge.
Wang, Jie; Mu, Feng-Rong; Jiao, Wei-Hua; Huang, Jian; Hong, Li-Li; Yang, Fan; Xu, Ying; Wang, Shu-Ping; Sun, Fan; Lin, Hou-Wen; Journal of natural products 80 (2017) 2509–2514; doi:10.1021/acs.jnatprod.7b00435

data_1547522
_publ_section_title
;
 Meroterpenoids with Protein Tyrosine Phosphatase 1B Inhibitory Activity
 from a Hyrtios sp. Marine Sponge.
;
_journal_issue                   9
_journal_name_full               'Journal of natural products'
_journal_page_first              2509
_journal_page_last               2514
_journal_paper_doi               10.1021/acs.jnatprod.7b00435
_journal_volume                  80
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C21 H28 O3'
_chemical_formula_sum            'C21 H28 O3'
_chemical_formula_weight         328.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-04-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.02100(10)
_cell_length_b                   13.4995(2)
_cell_length_c                   26.1852(4)
_cell_measurement_reflns_used    5854
_cell_measurement_temperature    130
_cell_measurement_theta_max      68.428
_cell_measurement_theta_min      3.376
_cell_volume                     3542.29(8)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19062
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.811
_diffrn_reflns_theta_min         3.376
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1019 before and 0.0553 after correction. The Ratio of minimum to maximum transmission is 0.8465. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 2388 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.15(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         6378
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0349
_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/[\s^2^(Fo^2^)+(0.0438P)^2^+0.3016P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0864
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                6006
_reflns_number_total             6378
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00435_si_002.cif
_cod_data_source_block           cu_dm16742_0m
_cod_database_code               1547522
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.928
_shelx_estimated_absorpt_t_min   0.883
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C10A(H10A)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C15(H15A,
 H15B), C1A(H1AA,H1AB), C2A(H2AA,H2AB), C3A(H3AA,H3AB), C6A(H6AA,H6AB),
 C7A(H7AA,H7AB), C15A(H15C,H15D)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C19A(H19A)
2.d X=CH2 refined with riding coordinates:
 C11(H11A,H11B), C11A(H11C,H11D)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C12(H12A,H12B,H12C), C21(H21A,H21B,
 H21C), C13A(H13D,H13E,H13F), C14A(H14D,H14E,H14F), C12A(H12D,H12E,H12F),
 C21A(H21D,H21E,H21F)
;
_shelx_res_checksum              99271
_shelx_hkl_checksum              60768
_olex2_submission_special_instructions 'No special instructions were received'