Elongation of Phenoxide C-O Bonds Due to Formation of Multifold Hydrogen Bonds: Statistical, Experimental, and Theoretical Studies
Naoto Hayashi; Kazuhito Sato; Yuka Sato; Masayuki Iwagami; Naoki Nishimura; Junro Yoshino; Hiroyuki Higuchi; Tohru Sato; Journal of Organic Chemistry 76 (2011) 5747–5758; doi:10.1021/jo200852r

data_4026460
_publ_section_title
;
 Elongation of Phenoxide C-O Bonds Due to Formation of Multifold Hydrogen
 Bonds: Statistical, Experimental, and Theoretical Studies
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5747
_journal_page_last               5758
_journal_paper_doi               10.1021/jo200852r
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C28 H35 N O5'
_chemical_formula_weight         465.57
_chemical_name_systematic
;
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.96(5)
_cell_angle_beta                 104.70(4)
_cell_angle_gamma                64.61(4)
_cell_formula_units_Z            2
_cell_length_a                   13.307(7)
_cell_length_b                   14.665(9)
_cell_length_c                   7.756(3)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      10
_cell_volume                     1314.2(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'RIGAKU AFC-7S'
_diffrn_measurement_method       w/2q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_sigmaI/netI    0.0614
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6404
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.73
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9881
_exptl_absorpt_correction_T_min  0.9687
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_description       prism
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1435
_refine_ls_R_factor_gt           0.0654
_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^)+(0.1298P)^2^+0.4599P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1940
_refine_ls_wR_factor_ref         0.2370
_reflns_number_gt                3352
_reflns_number_total             6036
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200852r_si_002_3.cif
_cod_data_source_block           shelxl_3
_cod_original_cell_volume        1314.2(12)
_cod_database_code               4026460