Neocucurbins A-G, novel macrocyclic diterpenes and their derivatives from Neocucurbitaria unguis-hominis FS685
Hu, Jinhua; Zhang, Wenge; Tan, Haibo; Li, Saini; Gao, Xiaoxia; Liu, Zhaoming; Wang, Yanlin; Liu, Hong-Xin; Zhang, Weimin; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00585A

data_7158668
_publ_section_title
;
 Neocucurbins A-G, novel macrocyclic diterpenes and their derivatives from
 Neocucurbitaria unguis-hominis FS685
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00585A
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H30 O5'
_chemical_formula_sum            'C20 H30 O5'
_chemical_formula_weight         350.44
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-10-17 deposited with the CCDC.	2022-05-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.675(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9823(4)
_cell_length_b                   7.7311(2)
_cell_length_c                   17.3343(5)
_cell_measurement_reflns_used    6378
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5950
_cell_measurement_theta_min      4.1220
_cell_volume                     1871.77(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -32.00  20.00   0.25    0.40    --    0.00 -82.00 -60.00  208
  2  \w    -32.00  29.00   0.25    0.40    --    0.00 -82.00-120.00  244
  3  \w     -8.00  21.00   0.25    0.40    --    0.00 -77.00 120.00  116
  4  \w    -32.00  26.00   0.25    0.40    --    0.00 -82.00   0.00  232
  5  \w      5.00  89.00   0.25    0.40    --    0.00  57.00   0.00  336
  6  \w     18.00 114.00   0.25    4.10    --   97.10 -45.00   0.00  384
  7  \w     74.00 101.00   0.25    4.10    --   97.10  61.00   0.00  108
  8  \w    156.00 184.00   0.25    4.10    --   97.10  30.00-180.00  112
  9  \w    115.00 149.00   0.25    4.10    --   97.10  15.00 120.00  136
 10  \w     82.00 137.00   0.25    4.10    --   97.10  30.00-150.00  220
 11  \w     10.00 114.00   0.25    4.10    --   97.10 -30.00 120.00  416
 12  \w     75.00 180.00   0.25    4.10    --   97.10  61.00  30.00  420
 13  \w     87.00 182.00   0.25    4.10    --   97.10  30.00 -90.00  380
 14  \w     91.00 132.00   0.25    4.10    --   97.10  82.00 120.00  164
 15  \w     81.00 141.00   0.25    4.10    --   97.10  45.00   0.00  240
 16  \w    134.00 182.00   0.25    4.10    --   97.10  82.00 120.00  192
 17  \w     38.00 113.00   0.25    4.10    --   97.10 -45.00 120.00  300
 18  \w     90.00 181.00   0.25    4.10    --   97.10  30.00-120.00  364
 19  \w    109.00 175.00   0.25    4.10    --   97.10  30.00  60.00  264
 20  \w     96.00 151.00   0.25    4.10    --   97.10  30.00-180.00  220
 21  \w     80.00 136.00   0.25    4.10    --   97.10  45.00  30.00  224
 22  \w     81.00 108.00   0.25    4.10    --   97.10  30.00   0.00  108
 23  \w      8.00  43.00   0.25    4.10    --   97.10   0.00  90.00  140
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0684978000
_diffrn_orient_matrix_UB_12      0.1235029000
_diffrn_orient_matrix_UB_13      0.0399199000
_diffrn_orient_matrix_UB_21      0.0828639000
_diffrn_orient_matrix_UB_22      0.0596604000
_diffrn_orient_matrix_UB_23      0.0553528000
_diffrn_orient_matrix_UB_31      0.0242330000
_diffrn_orient_matrix_UB_32      0.1446115000
_diffrn_orient_matrix_UB_33      -0.0571732000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0861
_diffrn_reflns_av_unetI/netI     0.0832
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19209
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.953
_diffrn_reflns_theta_min         3.164
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details
;
 Flack x determined using 2459 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   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         7440
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0811
_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^)+(0.1482P)^2^+0.2491P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2020
_refine_ls_wR_factor_ref         0.2126
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                6448
_reflns_number_total             7440
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00585a2.cif
_cod_data_source_block           hujinhua_53p-3-34_collect
_cod_database_code               7158668
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C76 H126 N6 O18 '
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.814
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Ternary CH refined with riding coordinates:
 C14A(H14A), C12(H12), C14(H14), C12A(H12A), C20A(H20A), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C13A(H13A,H13B), C3A(H3AA,H3AB), C6A(H6AA,H6AB), C10(H10C,H10D), C13(H13C,
 H13D), C6(H6A,H6B), C10A(H10A,H10B), C9(H9A,H9B), C5(H5B,H5C), C3(H3A,H3B),
 C9A(H9AA,H9AB), C5A(H5AA,H5AB)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C7A(H7A)
2.d Idealised Me refined as rotating group:
 C17A(H17A,H17B,H17C), C17(H17D,H17E,H17F), C19A(H19A,H19B,H19C), C19(H19D,
 H19E,H19F), C16A(H16A,H16B,H16C), C18(H18D,H18E,H18F), C18A(H18A,H18B,H18C),
 C16(H16D,H16E,H16F)
2.e Idealised tetrahedral OH refined as rotating group:
 O4A(H4A), O4(H4), O5(H5), O5A(H5A)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.174
_oxdiff_exptl_absorpt_empirical_full_min 0.487