The amide bridge in donor–acceptor systems: delocalization depends on push–pull stress
Maldonado-Domínguez, Mauricio; Arcos-Ramos, Rafael; Romero, Margarita; Flores-Pérez, Blas; Farfán, Norberto; Santillan, Rosa; Lacroix, Pascal G.; Malfant, Isabelle; New Journal of Chemistry 38 (2014) 260–; doi:10.1039/c3nj01176c

data_7054002
_publ_section_title
;
 The amide bridge in donor--acceptor systems: delocalization depends on
 push--pull stress
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              260
_journal_paper_doi               10.1039/c3nj01176c
_journal_volume                  38
_journal_year                    2014
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H19 F1 N2 O3'
_chemical_formula_sum            'C20 H19 F N2 O3'
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_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
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_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
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_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
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_audit_creation_date             2012-05-11T18:05:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                104.262(7)
_cell_angle_beta                 91.624(6)
_cell_angle_gamma                100.777(6)
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_cell_length_c                   13.2856(11)
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_cell_measurement_temperature    132(2)
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_cell_measurement_theta_min      3.4889
_cell_measurement_wavelength     0.71073
_cell_volume                     831.83(12)
_computing_cell_refinement
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
        (compiled Apr 28 2010,14:27:37)
;
_computing_data_collection
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
        (compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
        (compiled Apr 28 2010,14:27:37)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
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_diffrn_ambient_temperature      132(2)
_diffrn_detector_area_resol_mean 10.4685
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.829
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0353822
_diffrn_orient_matrix_UB_12      -0.0256437
_diffrn_orient_matrix_UB_13      0.0414121
_diffrn_orient_matrix_UB_21      0.06381
_diffrn_orient_matrix_UB_22      -0.0359856
_diffrn_orient_matrix_UB_23      -0.0333748
_diffrn_orient_matrix_UB_31      0.0744049
_diffrn_orient_matrix_UB_32      0.0651253
_diffrn_orient_matrix_UB_33      0.0149781
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
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_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6150
_diffrn_reflns_theta_full        25
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_diffrn_reflns_theta_min         3.5
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9993
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.933
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0747P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.132
_reflns_number_gt                2363
_reflns_number_total             3838
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c3nj01176c.txt
_cod_data_source_block           far18
_cod_original_cell_volume        831.83(11)
_cod_database_code               7054002