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_4037713
_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_absolute_configuration unk
_chemical_formula_moiety         'C21 H24 O'
_chemical_formula_sum            'C21 H24 O'
_chemical_formula_weight         292.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-13
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2966(13)
_cell_length_b                   6.8639(5)
_cell_length_c                   18.5829(15)
_cell_measurement_reflns_used    3247
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.0870
_cell_measurement_theta_min      2.9610
_cell_volume                     1568.4(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -59.00  70.00   0.50    8.00    --  -20.00  72.00 -36.00  258
  2  \w    -59.00  43.50   0.50    8.00    --  -20.00  72.00-108.00  205
  3  \w    -67.50 -21.00   0.50    8.00    --  -20.00 -72.00  36.00   93
  4  \w    -78.00   0.50   0.50    8.00    --  -20.00 -72.00-108.00  157
;
_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      -0.0193966000
_diffrn_orient_matrix_UB_12      -0.0566944000
_diffrn_orient_matrix_UB_13      0.0000310000
_diffrn_orient_matrix_UB_21      0.0125467000
_diffrn_orient_matrix_UB_22      -0.0013100000
_diffrn_orient_matrix_UB_23      0.0378802000
_diffrn_orient_matrix_UB_31      -0.1006632000
_diffrn_orient_matrix_UB_32      0.0107243000
_diffrn_orient_matrix_UB_33      0.0046920000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1221
_diffrn_reflns_av_unetI/netI     0.0939
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9883
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        24.987
_diffrn_reflns_theta_max         24.987
_diffrn_reflns_theta_min         2.968
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61516
_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    1.238
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Flack x determined using 595 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.9(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2711
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0954
_refine_ls_R_factor_gt           0.0645
_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^)+(0.0680P)^2^+0.0256P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1683
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_full    0.967
_reflns_Friedel_fraction_max     0.967
_reflns_number_gt                1864
_reflns_number_total             2711
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02829_si_004.cif
_cod_data_source_block           srk-rk-101-1_mo
_cod_database_code               4037713
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.982
_reflns_odcompleteness_completeness 95.09
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C003(H003), C005(H005), C00C(H00K), C00F(H00N), C00L(H00R), C00M(H00S)
2.b Secondary CH2 refined with riding coordinates:
 C004(H00C,H00D), C009(H00E,H00F), C00A(H00G,H00H), C00B(H00I,H00J)
2.c Aromatic/amide H refined with riding coordinates:
 C006(H006), C007(H007), C008(H008), C00D(H00L), C00E(H00M), C00H(H00O)
2.d X=CH2 refined with riding coordinates:
 C002(H00A,H00B), C00J(H00P,H00Q)
;
_shelx_res_checksum              95944
_shelx_hkl_checksum              36574
_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 1.462
_oxdiff_exptl_absorpt_empirical_full_min 0.525