Palladium catalysed [3 + 2]-annulation reaction of vinylcyclopropanes with pentafulvenes: synthesis of polysubstituted spiro[4,4]nona-6,8-dienes
Zhang, Si-Chen; Lei, Xin-Xin; Yang, Yong-jian; Luo, Yong-Chun; Zhang, Huan-Huan; Xu, Peng-Fei; Organic Chemistry Frontiers 6 (2019) 2415–; doi:10.1039/C9QO00467J

data_1554923
_publ_section_title
;
 Palladium catalysed [3 + 2]-annulation reaction of vinylcyclopropanes
 with pentafulvenes: synthesis of polysubstituted
 spiro[4,4]nona-6,8-dienes
;
_journal_issue                   14
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2415
_journal_paper_doi               10.1039/C9QO00467J
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C30 H25 N3 O3'
_chemical_formula_sum            'C30 H25 N3 O3'
_chemical_formula_weight         475.53
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-03-29
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2019-03-30 deposited with the CCDC.	2019-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                97.570(13)
_cell_angle_beta                 90.211(11)
_cell_angle_gamma                115.564(17)
_cell_formula_units_Z            2
_cell_length_a                   8.9859(13)
_cell_length_b                   10.004(2)
_cell_length_c                   15.8029(18)
_cell_measurement_reflns_used    2657
_cell_measurement_temperature    293.00(10)
_cell_measurement_theta_max      68.9480
_cell_measurement_theta_min      9.8000
_cell_volume                     1267.4(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   94.00  128.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   90.0000 17

  2 omega  134.00  176.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   90.0000 21

  3 omega   72.00  122.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   60.0000 25

  4 omega   46.00  178.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -12.0000   60.0000 66

  5 omega   90.00  116.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 13

  6 omega   49.00  127.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   30.0000 39

  7 omega   59.00  107.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 24

  8 omega   99.00  125.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -150.0000 13

  9 omega   65.00  109.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 22

 10 omega   53.00   79.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -150.0000 13

 11 omega   40.00  102.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -120.0000 31

 12 omega   45.00  109.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -180.0000 32

 13 omega   36.00   88.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -90.0000 26

 14 omega   39.00   91.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 26

 15 omega   45.00  111.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 33

 16 omega   49.00  103.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   90.0000 27

 17 omega   49.00   83.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  150.0000 17

 18 omega   46.00   72.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 13

 19 omega   40.00   90.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 25

 20 omega   31.00  125.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000  -30.0000 47

 21 omega   36.00   62.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 13

 22 omega   37.00   83.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 23

 23 omega   31.00   71.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000  -30.0000 20

 24 omega  -13.00   69.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000    0.0000 41

 25 omega  -15.00   59.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -60.0000 37

 26 omega   31.00   67.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 18

 27 omega  -14.00   36.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000   90.0000 25

 28 omega  -15.00   79.00   2.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000  150.0000 47

 29 omega  -71.00  -23.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  149.0000   36.0000 24
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0656288000
_diffrn_orient_matrix_UB_12      -0.1674062000
_diffrn_orient_matrix_UB_13      0.0080761000
_diffrn_orient_matrix_UB_21      -0.1372622000
_diffrn_orient_matrix_UB_22      -0.0383784000
_diffrn_orient_matrix_UB_23      -0.0703599000
_diffrn_orient_matrix_UB_31      0.1146005000
_diffrn_orient_matrix_UB_32      -0.0168554000
_diffrn_orient_matrix_UB_33      -0.0685534000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8173
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         4.955
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.246
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4466
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0550P)^2^+0.1938P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1273
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3530
_reflns_number_total             4466
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00467j2.cif
_cod_data_source_block           zhangsc_0329
_cod_original_cell_volume        1267.5(4)
_cod_database_code               1554923
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.76
_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
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C25(H25), C26(H26), C28(H28), C29(H29)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C)
;
_olex2_date_sample_data_collection 2019-03-29
_olex2_submission_special_instructions 'No special instructions were received'