Electronic Donation or Steric Contraction: A Spectroscopic and Structural Analysis of Medium-Sized Constrained Rings for Potential Long-Range Hyperconjugation.
Lee, Robert; Bashrum, Bryan; Cagle, Ethan C.; Walters, Jillian; Massey, Jake; Zanghi, Monica; Birchfield, Carolyn; French, David; Joy, Jessica; Dos Passos Gomes, Gabriel; Wiget, Paul A.; The Journal of organic chemistry 84 (2019) 9897–9906; doi:10.1021/acs.joc.9b00979

data_4034010
_publ_section_title
;
 Electronic Donation or Steric Contraction: A Spectroscopic and Structural
 Analysis of Medium-Sized Constrained Rings for Potential Long-Range
 Hyperconjugation.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9897
_journal_page_last               9906
_journal_paper_doi               10.1021/acs.joc.9b00979
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C11 H14 O'
_chemical_formula_weight         162.22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.0831(9)
_cell_length_b                   7.6632(3)
_cell_length_c                   10.9517(5)
_cell_measurement_reflns_used    8174
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      70.049
_cell_measurement_theta_min      4.028
_cell_volume                     1685.48(13)
_computing_cell_refinement       'SAINT (Bruker AXS, 2012)'
_computing_data_collection       'APEX2 (Version 2012.10-0)'
_computing_data_reduction        'SADABS V2012/1 (Bruker AXS)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXTL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART BREEZE CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12917
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.041
_diffrn_reflns_theta_min         4.403
_diffrn_source                   'fine-focused sealed tube'
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  0.89393
_exptl_absorpt_correction_T_min  0.84727
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS 2013'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_description       cut
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.387
_exptl_crystal_size_mid          0.345
_exptl_crystal_size_min          0.242
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1589
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0520
_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^)+(0.0778P)^2^+0.6382P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1321
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1564
_reflns_number_total             1589
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00979_si_004.cif
_cod_data_source_block           PWJW_CP
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measure' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4034010
_shelx_estimated_absorpt_t_min   0.796
_shelx_estimated_absorpt_t_max   0.865
_shelxl_version_number           2013-4
_shelx_res_checksum              9677
_shelx_hkl_checksum              53926