Enol-imino-Keto-enamine Tautomerism in a Diazepine Derivative: How Decisive Are the Intermolecular Interactions in the Equilibrium?
Rocha, Mariana; Gil, Diego M.; Echeverría, Gustavo A; Piro, Oscar E.; Jios, Jorge L.; Ulic, Sonia E.; The Journal of organic chemistry 84 (2019) 11042–11053; doi:10.1021/acs.joc.9b01533

data_4033817
_publ_section_title
;
 Enol-imino-Keto-enamine Tautomerism in a Diazepine Derivative: How
 Decisive Are the Intermolecular Interactions in the Equilibrium?
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11042
_journal_page_last               11053
_journal_paper_doi               10.1021/acs.joc.9b01533
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C12 H11 F3 N2 O'
_chemical_formula_weight         256.23
_chemical_name_systematic
5-(2-hydroxyphenyl)-7-trifluoromethyl-2,3-dihydro-1H-1,4-diazepine
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.6241(5)
_cell_length_b                   17.7725(7)
_cell_length_c                   8.3960(5)
_cell_measurement_reflns_used    1645
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.8660
_cell_measurement_theta_min      3.7390
_cell_volume                     2331.40(18)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0604
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.823
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.823
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            8087
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.082
_diffrn_reflns_theta_min         2.983
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.225
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.131
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         2581
_refine_ls_number_restraints     73
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0488P)^2^+0.2237P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1219
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1555
_reflns_number_total             2581
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01533_si_002.cif
_cod_data_source_block           shelx
_cod_database_code               4033817
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.984
_oxdiff_exptl_absorpt_empirical_full_min 0.869
_oxdiff_exptl_absorpt_empirical_full_max 1.129
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelx_res_checksum              35745
_shelx_hkl_checksum              52643