Hyperconjugation Involving Strained Carbon-Carbon Bonds. Structural Analysis of Ester and Ether Derivatives and One-Bond 13C-13C Coupling Constants of α- and β-Nopinol
Shinn Dee Yeoh; Colin E. Skene; Jonathan M. White; Journal of Organic Chemistry 78 (2013) 311–319; doi:10.1021/jo3020243

data_4027843
_publ_section_title
;
 Hyperconjugation Involving Strained Carbon-Carbon Bonds. Structural
 Analysis of Ester and Ether Derivatives and One-Bond 13C-13C Coupling
 Constants of \a- and \b-Nopinol
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              311
_journal_page_last               319
_journal_paper_doi               10.1021/jo3020243
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C16 H18 N2 O6'
_chemical_formula_weight         334.32
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 113.621(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0798(2)
_cell_length_b                   32.9160(6)
_cell_length_c                   7.4809(2)
_cell_measurement_reflns_used    4708
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      72.2548
_cell_measurement_theta_min      4.0285
_cell_volume                     1597.28(8)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 16.0711
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.948
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7512
_diffrn_reflns_theta_full        72.61
_diffrn_reflns_theta_max         72.61
_diffrn_reflns_theta_min         5.38
_exptl_absorpt_coefficient_mu    0.907
_exptl_absorpt_correction_T_max  0.896
_exptl_absorpt_correction_T_min  0.602
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET)
(compiled May  8 2007,13:10:02)
numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.608
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         4231
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0738P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.0957
_reflns_number_gt                3834
_reflns_number_total             4231
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3020243_si_005.cif
_cod_data_source_block           jmwsdy40
_cod_original_cell_volume        1597.27(7)
_cod_database_code               4027843