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_4037461
_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         'C14 H19 Cl O2'
_chemical_formula_sum            'C14 H19 Cl O2'
_chemical_formula_weight         254.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 95.208(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.2073(8)
_cell_length_b                   11.4382(8)
_cell_length_c                   20.9983(15)
_cell_measurement_reflns_used    1014
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.8
_cell_volume                     2680.7(3)
_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 6.8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Mercury275R CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            45954
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.627
_diffrn_reflns_theta_min         1.989
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         6225
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0476P)^2^+1.4536P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.1026
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4980
_reflns_number_total             6225
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02428_si_003.cif
_cod_data_source_block           mini-15050
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4037461
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.942
_shelx_estimated_absorpt_t_max   0.978
_shelx_res_checksum              7946
_shelx_hkl_checksum              66705