Palladium-catalyzed ring opening of norbornene: efficient synthesis of methylenecyclopentane derivatives
Xin-Xing Wu; Yi Shen; Wen-Long Chen; Si Chen; Xin-Hua Hao; Yu Xia; Peng-Fei Xu; Yong-Min Liang; Chem.Commun. 51 (2015) 8031–; doi:10.1039/C5cc02246K

data_7117098
_publ_section_title
;
 Palladium-catalyzed ring opening of norbornene: efficient synthesis of
 methylenecyclopentane derivatives
;
_journal_name_full               Chem.Commun.
_journal_page_first              8031
_journal_paper_doi               10.1039/C5cc02246K
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C21 H22 O'
_chemical_formula_sum            'C21 H22 O'
_chemical_formula_weight         290.39
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-11-19
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2014-12-23 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.114(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.7810(8)
_cell_length_b                   15.3478(9)
_cell_length_c                   6.0728(2)
_cell_measurement_reflns_used    1166
_cell_measurement_temperature    294.68(10)
_cell_measurement_theta_max      23.5940
_cell_measurement_theta_min      3.9810
_cell_volume                     1636.34(13)
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      294.68(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -45.00  -12.60   1.2000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -57.0000 -180.0000 27

  2 omega   45.00   93.00   1.2000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  178.0000  150.0000 40

  3 omega   -1.00   67.40   1.2000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   77.0000  120.0000 57

  4 omega  -40.00   44.00   1.2000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -38.0000  -90.0000 70
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0303938000
_diffrn_orient_matrix_UB_12      -0.0002032000
_diffrn_orient_matrix_UB_13      -0.0628828000
_diffrn_orient_matrix_UB_21      0.0097265000
_diffrn_orient_matrix_UB_22      0.0430935000
_diffrn_orient_matrix_UB_23      0.0358989000
_diffrn_orient_matrix_UB_31      0.0248024000
_diffrn_orient_matrix_UB_32      -0.0166654000
_diffrn_orient_matrix_UB_33      0.0935201000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6904
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.48
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85728
_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_density_diffrn    1.179
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3215
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.1235
_refine_ls_R_factor_gt           0.0705
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0487P)^2^+0.6679P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1524
_refine_ls_wR_factor_ref         0.1875
_reflns_number_gt                1792
_reflns_number_total             3215
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc02246k2.cif
_cod_data_source_block           wuxx1118
_cod_original_cell_volume        1636.33(14)
_cod_database_code               7117098
_reflns_odcompleteness_completeness 99.74
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C9') \\sim Ueq, Uanis(C9) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Fixed Sof: H8A(0.65) H8B(0.35) H10A(0.65) H10B(0.65) H10C(0.35) H10D(0.35)
 H13A(0.65) H13B(0.65) H13C(0.35) H13D(0.35) C9(0.65) H9(0.65) C9'(0.35)
 H9'(0.35)
4.a Ternary CH refined with riding coordinates:
 C9(H9), C9'(H9')
4.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10(H10C,H10D), C12(H12A,H12B), C13(H13A,H13B), C13(H13C,H13D)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8A), C8(H8B), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20)
4.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_olex2_submission_special_instructions 'No special instructions were received'