Quantification of the effects of n-π* interactions on the H-bonding properties of amide groups
Hanna, Fergal E.; Bond, Andrew D.; Hunter, Christopher A.; Chemical Science 16 (2025) 7894–7901; doi:10.1039/D4SC08331H

data_1574308
_publ_section_title
;
 Quantification of the effects of n-\p* interactions on the H-bonding
 properties of amide groups
;
_journal_issue                   18
_journal_name_full               'Chemical Science'
_journal_page_first              7894
_journal_page_last               7901
_journal_paper_doi               10.1039/D4SC08331H
_journal_volume                  16
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H24 N2 O2'
_chemical_formula_sum            'C14 H24 N2 O2'
_chemical_formula_weight         252.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/2
_audit_update_record
;
2024-10-02 deposited with the CCDC.	2025-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7109(2)
_cell_length_b                   14.3218(5)
_cell_length_c                   17.0215(6)
_cell_measurement_reflns_used    4607
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      68.05
_cell_measurement_theta_min      6.05
_cell_volume                     1392.19(8)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX5 (Bruker, 2023)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-III'
_diffrn_measurement_method       '\w and \f-scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9121
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.148
_diffrn_reflns_theta_min         6.048
_diffrn_source                   'Incoatec I\mS Cu microsource'
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
Flack x determined using 941 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0431P)^2^+0.1652P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0843
_reflns_Friedel_coverage         0.688
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                2404
_reflns_number_total             2523
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc08331h2.cif
_cod_data_source_block           5
_cod_depositor_comments
'Adding full bibliography for 1574308--1574310.cif.'
_cod_database_code               1574308
_cambridge_user_name             'Fergal Hanna'
_cambridge_user_crsid            feh27
_cambridge_supervisor_name       'Chris Hunter'
_cambridge_supervisor_crsid      ch664
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             FHBK4-152
_cambridge_data_id               CH_B1_0081
_shelx_estimated_absorpt_t_min   0.856
_shelx_estimated_absorpt_t_max   0.975
_shelx_res_checksum              1389