Bridgehead vicinal diallylation of norbornene derivatives and extension to propellane derivatives via ring-closing metathesis.
Kotha, Sambasivarao; Gunta, Rama; Beilstein journal of organic chemistry 12 (2016) 1877–1883; doi:10.3762/bjoc.12.177

data_4032048
_publ_section_title
;
 Bridgehead vicinal diallylation of norbornene derivatives and extension
 to propellane derivatives via ring-closing metathesis.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              1877
_journal_page_last               1883
_journal_paper_doi               10.3762/bjoc.12.177
_journal_volume                  12
_journal_year                    2016
_chemical_formula_moiety         'C23 H22 O2'
_chemical_formula_sum            'C23 H22 O2'
_chemical_formula_weight         330.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-01-14
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.10.28 svn.r3245 for OlexSys, GUI svn.r5128)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.630(7)
_cell_length_b                   11.834(6)
_cell_length_c                   10.513(5)
_cell_measurement_reflns_used    2844
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.0
_cell_measurement_theta_min      3.4
_cell_volume                     1820.1(15)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b28 (Rigaku, 2013)
;
_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      150
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
scan:
    Number of images: 192
               Slice: -109.0000 - -13.0000
         Image width: 0.5000
            Exp time: 8.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: 36.0000
                 XTD: 45.0803
              2theta: -19.8999
scan:
    Number of images: 190
               Slice: -78.0000 - 17.0000
         Image width: 0.5000
            Exp time: 8.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: -108.0000
                 XTD: 45.0803
              2theta: -19.8999
scan:
    Number of images: 34
               Slice: -36.0000 - -19.0000
         Image width: 0.5000
            Exp time: 8.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: 108.0000
                 XTD: 45.0803
              2theta: -19.8999
;
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6567
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         3.393
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.784
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_description       Prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1680
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0429
_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^+0.5239P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.1003
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1484
_reflns_number_total             1680
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            2b-shelxl.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 4032046--4032049.cif.'
_cod_database_code               4032048
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: H00C(0.5) H00D(0.5) H00G(0.5) H00H(0.5)
3.a Ternary CH refined with riding coordinates:
 C007(H007)
3.b Secondary CH2 refined with riding coordinates:
 C008(H00A,H00B), C00A(H00C,H00D), C00D(H00G,H00H)
3.c Aromatic/amide H refined with riding coordinates:
 C003(H003), C004(H004), C00B(H00E), C00C(H00F)
3.d X=CH2 refined with riding coordinates:
 C00E(H00I,H00J)
;
_shelx_res_checksum              98914
_shelx_hkl_checksum              52832
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'