Sesquiterpenoids from the Endophytic Fungus Rhinocladiella similis.
Liu, Shuai; Zhao, Yuping; Heering, Christian; Janiak, Christoph; Müller, Werner E G; Akoné, Sergi Hervé; Liu, Zhen; Proksch, Peter; Journal of natural products 82 (2019) 1055–1062; doi:10.1021/acs.jnatprod.8b00938

data_1552627
_publ_section_title
;
 Sesquiterpenoids from the Endophytic Fungus Rhinocladiella similis.
;
_journal_issue                   5
_journal_name_full               'Journal of natural products'
_journal_page_first              1055
_journal_page_last               1062
_journal_paper_doi               10.1021/acs.jnatprod.8b00938
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H25 Cl O6, 1.5(H2 O)'
_chemical_formula_sum            'C16 H28 Cl O7.5'
_chemical_formula_weight         375.83
_chemical_name_common            'rhinomilisin C'
_chemical_name_systematic
;
(1S,2S,5R,6S)-2-(chloromethyl)-2-hydroxy-6-((E)-2-(hydroxymethyl)
-3-methoxy-3-oxoprop-1-en-1-yl)-5-isopropylcyclohexane
-1-carboxylic acid 1.5hydrate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 103.812(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.0154(15)
_cell_length_b                   6.3425(5)
_cell_length_c                   16.3801(13)
_cell_measurement_reflns_used    6899
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.054
_cell_measurement_theta_min      2.913
_cell_volume                     1817.5(3)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'DIAMOND 4.2.2 (Crystal Impact, 2016)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXL2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0136
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7316
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.493
_diffrn_reflns_theta_min         2.328
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(<i>SADABS</i>); Sheldrick, 2012'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       block
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_crystal_size_rad          0.15
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1237 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.040(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3134
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0260
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0328P)^2^+0.9083P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0654
_refine_ls_wR_factor_ref         0.0665
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    0.857
_reflns_Friedel_fraction_max     0.852
_reflns_number_gt                3046
_reflns_number_total             3134
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00938_si_002.cif
_cod_data_source_block           RS_6_3_3
_cod_depositor_comments
;

2022-09-15
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      'C 2'
_cod_original_formula_moiety     '2(C16 H25 Cl O6), 3(H2 O)'
_cod_original_formula_sum        'C32 H56 Cl2 O15'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     751.66
_cod_database_code               1552627
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.846
_shelx_estimated_absorpt_t_max   0.952
_shelx_res_checksum              24303
_shelx_hkl_checksum              23577