Intermolecular Reactions of a Foiled Carbene with Carbonyl Compounds: The Effects of Trishomocyclopropyl Stabilization.
Apeland, Ingrid Malene; Rosenberg, Murray G.; Arion, Vladimir B.; Kählig, Hanspeter; Brinker, Udo H.; The Journal of organic chemistry 80 (2015) 11877–11887; doi:10.1021/acs.joc.5b01988

data_4036444
_publ_section_title
;
 Intermolecular Reactions of a Foiled Carbene with Carbonyl Compounds: The
 Effects of Trishomocyclopropyl Stabilization.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11877
_journal_page_last               11887
_journal_paper_doi               10.1021/acs.joc.5b01988
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H18 O'
_chemical_formula_sum            'C16 H18 O'
_chemical_formula_weight         226.30
_chemical_name_systematic
; 
1-((1R,2R,4S,5S,8r)-8-Phenyltricyclo[3.2.1.0^2,4^]octan-8-yl)
ethan-1-one 
;
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1320(2)
_cell_length_b                   10.6950(3)
_cell_length_c                   18.0264(5)
_cell_measurement_reflns_used    6939
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.46
_cell_measurement_theta_min      2.21
_cell_volume                     1182.20(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            35201
_diffrn_reflns_theta_full        30.12
_diffrn_reflns_theta_max         30.12
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9977
_exptl_absorpt_correction_T_min  0.9810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3489
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0506P)^2^+0.2599P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1099
_reflns_number_gt                2872
_reflns_number_total             3489
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01988_si_002.cif
_cod_data_source_block           ima150
_cod_original_sg_symbol_Hall     'P2ac 2ab'
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               4036444