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_7117097
_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_absolute_configuration ad
_chemical_formula_moiety         'C20 H19 Br'
_chemical_formula_sum            'C20 H19 Br'
_chemical_formula_weight         339.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-12-10
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_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                 98.292(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.0119(6)
_cell_length_b                   15.8060(14)
_cell_length_c                   8.3765(8)
_cell_measurement_reflns_used    625
_cell_measurement_temperature    290.92(10)
_cell_measurement_theta_max      21.5290
_cell_measurement_theta_min      3.6560
_cell_volume                     787.65(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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      290.92(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   40.00   94.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       19.9508  178.0000  120.0000 36

  2 omega   65.00   96.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       19.9508 -178.0000 -150.0000 21

  3 omega  -53.00   64.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       19.9508  -19.0000  120.0000 78
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0845764000
_diffrn_orient_matrix_UB_12      0.0290558000
_diffrn_orient_matrix_UB_13      0.0148128000
_diffrn_orient_matrix_UB_21      -0.0317408000
_diffrn_orient_matrix_UB_22      -0.0274136000
_diffrn_orient_matrix_UB_23      0.0598817000
_diffrn_orient_matrix_UB_31      0.0778481000
_diffrn_orient_matrix_UB_32      0.0204209000
_diffrn_orient_matrix_UB_33      0.0592964000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0935
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2904
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         3.56
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.601
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.02119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.017(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2032
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0508
_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^)+(0.0270P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0999
_reflns_number_gt                1624
_reflns_number_total             2032
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc02246k2.cif
_cod_data_source_block           wuxx1210
_cod_database_code               7117097
_reflns_odcompleteness_completeness 99.76
_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
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C13(H13), C14(H14), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20)
;
_olex2_date_sample_data_collection 2014-12-10
_olex2_submission_special_instructions 'No special instructions were received'