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_4032049
_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         'C21 H18 O2'
_chemical_formula_sum            'C21 H18 O2'
_chemical_formula_weight         302.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-01-15
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                88.457(13)
_cell_angle_beta                 79.0900(10)
_cell_angle_gamma                79.868(12)
_cell_formula_units_Z            2
_cell_length_a                   7.524(3)
_cell_length_b                   8.498(3)
_cell_length_c                   12.116(5)
_cell_measurement_reflns_used    2385
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.1
_cell_measurement_theta_min      3.0
_cell_volume                     748.8(5)
_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, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 8.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: -108.0000
                 XTD: 44.9796
              2theta: -19.9522
scan:
    Number of images: 176
               Slice: -69.0000 - 19.0000
         Image width: 0.5000
            Exp time: 8.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: -180.0000
                 XTD: 44.9796
              2theta: -19.9522
scan:
    Number of images: 160
               Slice: -61.0000 - 19.0000
         Image width: 0.5000
            Exp time: 8.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: 36.0000
                 XTD: 44.9796
              2theta: -19.9522
scan:
    Number of images: 117
               Slice: -73.0000 - -14.5000
         Image width: 0.5000
            Exp time: 8.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: -36.0000
                 XTD: 44.9796
              2theta: -19.9522
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 8.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 0.0000
                 Phi: -36.0000
                 XTD: 44.9796
              2theta: -19.9522
scan:
    Number of images: 189
               Slice: -75.5000 - 19.0000
         Image width: 0.5000
            Exp time: 8.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: -108.0000
                 XTD: 44.9796
              2theta: -19.9522
scan:
    Number of images: 205
               Slice: -58.5000 - 44.0000
         Image width: 0.5000
            Exp time: 8.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 72.0000
                 Phi: 108.0000
                 XTD: 44.9796
              2theta: -19.9522
scan:
    Number of images: 61
               Slice: -25.0000 - 5.5000
         Image width: 0.5000
            Exp time: 8.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: 108.0000
                 XTD: 44.9796
              2theta: -19.9522
;
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       XPlain
_diffrn_orient_matrix_UB_11      0.078517
_diffrn_orient_matrix_UB_12      -0.100864
_diffrn_orient_matrix_UB_13      -0.050533
_diffrn_orient_matrix_UB_21      -0.102240
_diffrn_orient_matrix_UB_22      -0.022277
_diffrn_orient_matrix_UB_23      -0.057809
_diffrn_orient_matrix_UB_31      0.016702
_diffrn_orient_matrix_UB_32      0.061781
_diffrn_orient_matrix_UB_33      -0.054492
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.1192
_diffrn_reflns_av_unetI/netI     0.1107
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11371
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.988
_diffrn_reflns_theta_max         24.988
_diffrn_reflns_theta_min         2.995
_diffrn_source                   MicroMax003_Mo
_diffrn_source_current           0.6
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       irregular
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.840
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2618
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.840
_refine_ls_R_factor_all          0.0680
_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^)+(0.0271P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.1026
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1519
_reflns_number_total             2618
_reflns_shell_number_unique_all  3984
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1b-shelxl.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 4032046--4032049.cif.'
_cod_database_code               4032049
_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:
 C007(H007), C00B(H00B)
2.b Secondary CH2 refined with riding coordinates:
 C00H(H00D,H00G), C00I(H00H,H00I), C00L(H00L,H00M), C00N(H00O,H00P)
2.c Aromatic/amide H refined with riding coordinates:
 C006(H006), C00A(H00A), C00C(H00C), C00E(H00E), C00F(H00F), C00J(H00J),
 C00K(H00K), C00M(H00N)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'