The Stabilizing Role of the Intramolecular C-H···O Hydrogen Bond in Cyclic Amides Derived From α-Methylbenzylamine.
Sandoval-Lira, Jacinto; Fuentes, Lilia; Quintero, Leticia; Höpfl, Herbert; Hernández-Pérez, Julio M; Terán, Joel L; Sartillo-Piscil, Fernando; The Journal of organic chemistry 80 (2015) 4481–4490; doi:10.1021/acs.joc.5b00286

data_4036157
_publ_section_title
;
 The Stabilizing Role of the Intramolecular C-H&#x00B7;&#x00B7;&#x00B7;O
 Hydrogen Bond in Cyclic Amides Derived From \a-Methylbenzylamine.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4481
_journal_page_last               4490
_journal_paper_doi               10.1021/acs.joc.5b00286
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C13 H15 N O2'
_chemical_formula_weight         217.26
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.084(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5642(6)
_cell_length_b                   9.0929(3)
_cell_length_c                   11.2620(4)
_cell_measurement_temperature    293(2)
_cell_volume                     1131.97(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            49008
_diffrn_reflns_theta_full        29.65
_diffrn_reflns_theta_max         29.65
_diffrn_reflns_theta_min         2.90
_exptl_absorpt_coefficient_mu    0.086
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         3087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0448P)^2^+0.2809P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1276
_reflns_number_gt                1801
_reflns_number_total             3087
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b00286_si_002.cif
_cod_data_source_block           12_mo
_cod_original_cell_volume        1131.98(8)
_cod_database_code               4036157