Synthetic Strategies to Diverse Polyquinanes via Olefin Metathesis: Access to the Basic Core of Crinipellin, Presilphiperfolanol and Cucumin.
Kotha, Sambasivarao; Keesari, Ramakrishna Reddy; Fatma, Ambareen; Gunta, Rama; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02829

data_4037715
_publ_section_title
;
 Synthetic Strategies to Diverse Polyquinanes via Olefin Metathesis:
 Access to the Basic Core of Crinipellin, Presilphiperfolanol and Cucumin.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02829
_journal_year                    2019
_chemical_formula_moiety         'C20 H26 O2'
_chemical_formula_sum            'C20 H26 O2'
_chemical_formula_weight         298.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-21
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.763(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4293(16)
_cell_length_b                   10.2165(15)
_cell_length_c                   17.616(2)
_cell_measurement_reflns_used    2111
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.4980
_cell_measurement_theta_min      2.3560
_cell_volume                     1667.2(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -110.00  70.00   0.50    8.00    --  -20.00   0.00 108.00  360
  2  \w    -17.50  69.00   0.50    8.00    --  -20.00  72.00-180.00  173
  3  \w    -20.00  10.00   0.50    8.00    --  -20.00  72.00 -36.00   60
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0248915000
_diffrn_orient_matrix_UB_12      -0.0473240000
_diffrn_orient_matrix_UB_13      -0.0288716000
_diffrn_orient_matrix_UB_21      -0.0695677000
_diffrn_orient_matrix_UB_22      0.0023595000
_diffrn_orient_matrix_UB_23      0.0098123000
_diffrn_orient_matrix_UB_31      -0.0199768000
_diffrn_orient_matrix_UB_32      0.0507545000
_diffrn_orient_matrix_UB_33      -0.0273940000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1344
_diffrn_reflns_av_unetI/netI     0.1491
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9182
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.315
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.027
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2938
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1545
_refine_ls_R_factor_gt           0.0755
_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^)+(0.0665P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.2022
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1499
_reflns_number_total             2938
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02829_si_005.cif
_cod_data_source_block           srk-af-196_mo
_cod_original_cell_volume        1667.1(4)
_cod_database_code               4037715
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.988
_reflns_odcompleteness_completeness 90.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.16
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C16(H16), C14(H14), C12(H12), C8(H8), C6(H6), C13(H13), C4(H4),
 C3(H3), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C15(H15A,H15B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C19(H19), C17(H17)
2.d X=CH2 refined with riding coordinates:
 C11(H11A,H11B), C20(H20A,H20B), C18(H18A,H18B)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              75365
_shelx_hkl_checksum              575
_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 1.626
_oxdiff_exptl_absorpt_empirical_full_min 0.694