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_7158667
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-23
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.17520(10)
_cell_length_b                   10.18530(10)
_cell_length_c                   22.0750(2)
_cell_measurement_reflns_used    14883
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.9620
_cell_measurement_theta_min      4.0080
_cell_volume                     1838.12(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_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    -33.00  31.00   0.50    0.50    --    0.00 -82.00  90.00  128
  2  \w    -46.00  29.00   0.50    0.50    --    0.00 -77.00 -90.00  150
  3  \w    -46.00  29.00   0.50    0.50    --    0.00 -77.00-180.00  150
  4  \w     87.00 185.00   0.50    0.67    --   95.80  82.00 -90.00  196
  5  \w      6.00 125.00   0.50    0.67    --   95.80 -77.00 -30.00  238
  6  \w      6.00 119.00   0.50    0.67    --   95.80 -15.00   0.00  226
  7  \w      6.00 112.00   0.50    0.67    --   95.80 -30.00 -30.00  212
  8  \w      6.00 119.00   0.50    0.67    --   95.80 -61.00 -30.00  226
  9  \w      6.00 185.00   0.50    0.67    --   95.80   0.00 -90.00  358
 10  \w    -33.00  31.00   0.50    0.50    --    0.00 -82.00   0.00  128
 11  \w    -89.00  22.00   0.50    0.50    --    0.00 -57.00 -60.00  222
 12  \w     72.00 185.00   0.50    0.67    --   95.80  61.00  30.00  226
 13  \w     72.00 152.00   0.50    0.67    --   95.80  61.00   0.00  160
;
_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      -0.0713082000
_diffrn_orient_matrix_UB_12      -0.0713468000
_diffrn_orient_matrix_UB_13      -0.0555732000
_diffrn_orient_matrix_UB_21      -0.0226575000
_diffrn_orient_matrix_UB_22      -0.1252860000
_diffrn_orient_matrix_UB_23      0.0382194000
_diffrn_orient_matrix_UB_31      -0.1729090000
_diffrn_orient_matrix_UB_32      0.0458227000
_diffrn_orient_matrix_UB_33      0.0179280000
_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  0.0221
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17927
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.387
_diffrn_reflns_theta_min         4.005
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.726
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
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    1.266
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1521 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3702
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0287
_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^)+(0.0358P)^2^+0.4500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0714
_refine_ls_wR_factor_ref         0.0716
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                3646
_reflns_number_total             3702
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00585a2.cif
_cod_data_source_block           53p-3-8_collect
_cod_database_code               7158667
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C76 H120 N4 O20 '
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.931
_reflns_odcompleteness_completeness 99.95
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O4A-C3
 1.43 with sigma of 0.001
 O4-C3 \\sim O4A-C3
 with sigma of 0.02
3. Rigid bond restraints
 O4A, C3
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 O2, C2
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Others
 Sof(H3BC)=Sof(H3BD)=Sof(O4A)=Sof(H4A)=1-FVAR(1)
 Sof(O4)=Sof(H4)=Sof(H3AA)=Sof(H3AB)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C12(H12), C14(H14), C6(H6)
5.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C10(H10A,H10B), C9(H9A,H9B), C5(H5A,H5B), C20(H20A,H20B),
 C3(H3AA,H3AB), C3(H3BC,H3BD)
5.c Aromatic/amide H refined with riding coordinates:
 C7(H7)
5.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C16(H16A,H16B,
 H16C)
5.e Idealised tetrahedral OH refined as rotating group:
 O5(H5), O4(H4), O4A(H4A)
;
_shelx_res_checksum              82436
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.136
_oxdiff_exptl_absorpt_empirical_full_min 0.894