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_4034007
_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            'C16 H17 N O3 S'
_chemical_formula_weight         303.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 103.292(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.8190(5)
_cell_length_b                   6.6125(2)
_cell_length_c                   13.7597(5)
_cell_measurement_reflns_used    4262
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      69.88
_cell_measurement_theta_min      2.87
_cell_volume                     1400.75(8)
_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 0.995
_diffrn_measured_fraction_theta_max 0.987
_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  0.0377
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9113
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.883
_diffrn_reflns_theta_min         2.870
_diffrn_source                   'fine-focused sealed tube'
_exptl_absorpt_coefficient_mu    2.143
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS 2013'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      ?
_exptl_crystal_description       cut
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.304
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.161
_exptl_transmission_factor_max   0.80944
_exptl_transmission_factor_min   0.69783
_refine_diff_density_max         0.710
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2615
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0512
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0879P)^2^+0.8099P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1453
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2342
_reflns_number_total             2615
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00979_si_003.cif
_cod_data_source_block           wiget_RLJMPW_4_0m_2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' 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_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4034007
_shelx_estimated_absorpt_t_min   0.6438
_shelx_estimated_absorpt_t_max   0.8722
_shelxl_version_number           2013-4
_shelx_res_checksum              73502
_shelx_hkl_checksum              47600