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_1547521
_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 ad
_chemical_formula_sum            'C22 H28 O4'
_chemical_formula_weight         356.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 93.6410(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.86700(10)
_cell_length_b                   11.4726(2)
_cell_length_c                   10.18150(10)
_cell_measurement_reflns_used    5572
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      69.42
_cell_measurement_theta_min      4.35
_cell_volume                     917.08(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7006
_diffrn_reflns_point_group_measured_fraction_full 0.906
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.496
_diffrn_reflns_theta_min         5.635
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
; 
 Flack x determined using 1252 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.02(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3067
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.1197P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0916
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    0.806
_reflns_Friedel_fraction_max     0.782
_reflns_number_gt                3039
_reflns_number_total             3067
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00435_si_004.cif
_cod_data_source_block           cu_dm14015_0m
_cod_database_code               1547521
_shelx_estimated_absorpt_t_min   0.817
_shelx_estimated_absorpt_t_max   0.914
_shelxl_version_number           2013-4
_shelx_res_checksum              27536
_shelx_hkl_checksum              25590