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_1547520
_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         'C22 H29 N O3'
_chemical_formula_sum            'C22 H29 N O3'
_chemical_formula_weight         355.46
_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
_atom_sites_solution_primary     direct
_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                 102.887(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6578(11)
_cell_length_b                   9.9005(7)
_cell_length_c                   12.3571(8)
_cell_measurement_reflns_used    5020
_cell_measurement_temperature    296
_cell_measurement_theta_max      69.172
_cell_measurement_theta_min      5.036
_cell_volume                     1986.6(2)
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.949
_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  0.0348
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13940
_diffrn_reflns_point_group_measured_fraction_full 0.813
_diffrn_reflns_point_group_measured_fraction_max 0.793
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.642
_diffrn_reflns_theta_min         5.036
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.621
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1189 before and 0.0562 after correction. The Ratio of minimum to maximum transmission is 0.7250. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 1583 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     479
_refine_ls_number_reflns         5934
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0652
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1078P)^2^+0.9375P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1823
_refine_ls_wR_factor_ref         0.1920
_reflns_Friedel_coverage         0.572
_reflns_Friedel_fraction_full    0.638
_reflns_Friedel_fraction_max     0.615
_reflns_number_gt                5190
_reflns_number_total             5934
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00435_si_003.cif
_cod_data_source_block           cu_dm17150_0m
_cod_database_code               1547520
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.929
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C1A \\sim C2A \\sim C3A \\sim C4A \\sim C5A: within 2A with sigma of 0.005 and
sigma for terminal atoms of 0.01
C5A \\sim C6A \\sim C7A \\sim C8A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
C4A \\sim C11A: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02
3.a Ternary CH refined with riding coordinates:
 C8(H8), C10(H10), C8A(H8A), C10A(H10A)
3.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)
3.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C19(H19), C22A(H22A), C19A(H19A)
3.d X=CH2 refined with riding coordinates:
 C11(H11A,H11B), C11A(H11C,H11D)
3.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C12A(H12D,H12E,
 H12F), C13A(H13D,H13E,H13F), C14A(H14D,H14E,H14F)
3.f Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O5(H5), O6(H6)
;
_shelx_res_checksum              59105
_shelx_hkl_checksum              11805
_olex2_submission_special_instructions 'No special instructions were received'