Hydrogen bonding to carbonyl oxygen of nitrogen-pyramidalized amide - detection of pyramidalization direction preference by vibrational circular dichroism spectroscopy.
Wang, Siyuan; Taniguchi, Tohru; Monde, Kenji; Kawahata, Masatoshi; Yamaguchi, Kentaro; Otani, Yuko; Ohwada, Tomohiko; Chemical communications (Cambridge, England) 52 (2016) 4018–4021; doi:10.1039/c6cc00284f

data_7118777
_publ_section_title
;
 Hydrogen bonding to carbonyl oxygen of nitrogen-pyramidalized amide -
 detection of pyramidalization direction preference by vibrational
 circular dichroism spectroscopy.
;
_journal_issue                   21
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4018
_journal_page_last               4021
_journal_paper_doi               10.1039/c6cc00284f
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_formula_sum            'C22 H34 N2 O7'
_chemical_formula_weight         438.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-01-04 deposited with the CCDC.
2016-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.787(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.582(4)
_cell_length_b                   10.854(6)
_cell_length_c                   15.521(8)
_cell_measurement_reflns_used    6147
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      2.29
_cell_volume                     1105.0(11)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_molecular_graphics    'ORTEP-3 for Windows'
_computing_publication_material  Yadokari-XG
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9094
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_min         1.317
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       plate
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 1557 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3645
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0267
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0520P)^2^+0.0154P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0811
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_full    0.901
_reflns_Friedel_fraction_max     0.867
_reflns_number_gt                3486
_reflns_number_total             3645
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc00284f2.cif
_cod_data_source_block           wsy-03-119s-Dimer-CH2OH
_cod_depositor_comments          'Adding full bibliography for 7118777.cif.'
_cod_original_cell_volume        1104.9(10)
_cod_database_code               7118777
_shelx_estimated_absorpt_t_min   0.953
_shelx_estimated_absorpt_t_max   0.997
_shelxl_version_number           2013-4
_shelx_res_checksum              67866