Domino enyne metathesis en route to skeletally diverse, privileged scaffolds: synthesis of the tricyclic core of pseudolaric acid F
Lin, Minggui; Cui, Hao; Hua, Yuhui; Zhang, Yandong; Organic Chemistry Frontiers 6 (2019) 2771–; doi:10.1039/C9QO00477G

data_1554929
_publ_section_title
;
 Domino enyne metathesis en route to skeletally diverse, privileged
 scaffolds: synthesis of the tricyclic core of pseudolaric acid F
;
_journal_issue                   15
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2771
_journal_paper_doi               10.1039/C9QO00477G
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C14 H18 O5'
_chemical_formula_sum            'C14 H18 O5'
_chemical_formula_weight         266.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-08-23
_audit_creation_method
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Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
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_audit_update_record
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2019-04-04 deposited with the CCDC.	2019-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                85.681(8)
_cell_angle_beta                 85.985(10)
_cell_angle_gamma                78.332(10)
_cell_formula_units_Z            2
_cell_length_a                   7.3423(10)
_cell_length_b                   8.4321(9)
_cell_length_c                   10.4623(11)
_cell_measurement_reflns_used    1423
_cell_measurement_temperature    185.1(6)
_cell_measurement_theta_max      29.1980
_cell_measurement_theta_min      3.8970
_cell_volume                     631.55(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_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      185.1(6)
_diffrn_detector_area_resol_mean 16.1903
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -91.00    1.00   1.0000    3.9500
omega____ theta____ kappa____ phi______ frames
    -      -23.0060  -57.0000 -120.0000 92

  2 omega  -93.00    8.00   1.0000    3.9500
omega____ theta____ kappa____ phi______ frames
    -      -23.0060  -77.0000 -180.0000 101

  3 omega  -45.00   48.00   1.0000    3.9500
omega____ theta____ kappa____ phi______ frames
    -      -23.0060   57.0000   30.0000 93

  4 omega  -17.00   46.00   1.0000    3.9500
omega____ theta____ kappa____ phi______ frames
    -      -23.0060   38.0000  150.0000 63

  5 omega   -4.00   65.00   1.0000    3.9500
omega____ theta____ kappa____ phi______ frames
    -       24.2560  -99.0000   90.0000 69
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0335180000
_diffrn_orient_matrix_UB_12      -0.0126857000
_diffrn_orient_matrix_UB_13      0.0626563000
_diffrn_orient_matrix_UB_21      0.0897893000
_diffrn_orient_matrix_UB_22      0.0086136000
_diffrn_orient_matrix_UB_23      -0.0255477000
_diffrn_orient_matrix_UB_31      -0.0239938000
_diffrn_orient_matrix_UB_32      0.0846859000
_diffrn_orient_matrix_UB_33      0.0076529000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4909
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         3.054
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
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    1.400
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0443
_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^)+(0.0426P)^2^+0.2299P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1100
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2463
_reflns_number_total             2890
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00477g2.cif
_cod_data_source_block           lmg
_cod_original_cell_volume        631.54(13)
_cod_database_code               1554929
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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
2.a Ternary CH refined with riding coordinates:
 C009(H009)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00D(H00F,H00G), C00E(H00H,H00I), C00F(H00J,H00K), C00G(H00L,
 H00M), C00H(H00N,H00O), C00J(H00P,H00Q)
2.c Idealised Me refined as rotating group:
 C00C(H00C,H00D,H00E)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'