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_1554922
_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         'C31 H28 N2 O5'
_chemical_formula_sum            'C31 H28 N2 O5'
_chemical_formula_weight         508.55
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-12-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-24 deposited with the CCDC.	2019-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.4324(12)
_cell_length_b                   13.5256(8)
_cell_length_c                   8.8733(5)
_cell_measurement_reflns_used    1282
_cell_measurement_temperature    292.94(10)
_cell_measurement_theta_max      21.3100
_cell_measurement_theta_min      4.0840
_cell_volume                     2572.2(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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_temperature      292.94(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -89.00  -62.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.4273  178.0000   30.0000 27

  2 omega   -5.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   38.0000    0.0000 96

  3 omega    9.00   44.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000   30.0000 35
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0173680000
_diffrn_orient_matrix_UB_12      0.0444292000
_diffrn_orient_matrix_UB_13      0.0064272000
_diffrn_orient_matrix_UB_21      -0.0189795000
_diffrn_orient_matrix_UB_22      -0.0147968000
_diffrn_orient_matrix_UB_23      -0.0614810000
_diffrn_orient_matrix_UB_31      -0.0208188000
_diffrn_orient_matrix_UB_32      -0.0235895000
_diffrn_orient_matrix_UB_33      0.0506971000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0674
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6449
_diffrn_reflns_point_group_measured_fraction_full 0.765
_diffrn_reflns_point_group_measured_fraction_max 0.760
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.340
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 543 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         3845
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0502
_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^)+(0.0327P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.1086
_reflns_Friedel_coverage         0.427
_reflns_Friedel_fraction_full    0.498
_reflns_Friedel_fraction_max     0.489
_reflns_number_gt                2699
_reflns_number_total             3845
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00467j2.cif
_cod_data_source_block           zhangsch_1213
_cod_database_code               1554922
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.984
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C16(H16), C12(H12), C19(H19), C8(H8), C11(H11), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C24(H24), C20(H20), C27(H27), C28(H28), C14(H14), C2(H2), C13(H13),
 C6(H6), C3(H3), C4(H4), C5(H5)
2.d X=CH2 refined with riding coordinates:
 C21(H21A,H21B)
2.e Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              41709
_shelx_hkl_checksum              27125
_olex2_date_sample_data_collection 2018-12-13
_olex2_submission_special_instructions 'No special instructions were received'