Controlling the Conformational Energy of a Phenyl Group by Tuning the Strength of a Nonclassical CH···O Hydrogen Bond: The Case of 5-Phenyl-1,3-dioxane.
Bailey, William F.; Lambert, Kyle M.; Stempel, Zachary D.; Wiberg, Kenneth B.; Mercado, Brandon Q.; The Journal of organic chemistry 81 (2016) 12116–12127; doi:10.1021/acs.joc.6b02428

data_4037460
_publ_section_title
;
 Controlling the Conformational Energy of a Phenyl Group by Tuning the
 Strength of a Nonclassical CH&#x00B7;&#x00B7;&#x00B7;O Hydrogen Bond: The
 Case of 5-Phenyl-1,3-dioxane.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12116
_journal_page_last               12127
_journal_paper_doi               10.1021/acs.joc.6b02428
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C13 H19 N O2'
_chemical_formula_sum            'C13 H19 N O2'
_chemical_formula_weight         221.29
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.757(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.1093(13)
_cell_length_b                   5.5821(2)
_cell_length_c                   11.6158(4)
_cell_measurement_reflns_used    17731
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      66.6
_cell_measurement_theta_min      7.0
_cell_volume                     1237.62(10)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_molecular_graphics
; 
Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H.,
OLEX2: A complete structure solution, refinement and analysis program
(2009). J. Appl. Cryst., 42, 339-341.
;
_computing_publication_material  'SHELXL-2013/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 22.2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0755
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            26885
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.580
_diffrn_reflns_theta_max         66.580
_diffrn_reflns_theta_min         6.959
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2179
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0397P)^2^+0.2435P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0895
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1957
_reflns_number_total             2179
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02428_si_002.cif
_cod_data_source_block           007-15080
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037460
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.894
_shelx_estimated_absorpt_t_max   0.975
_shelx_res_checksum              43079
_shelx_hkl_checksum              98382