A series of (<i>E</i>)-5-(arylideneamino)-1-<i>tert</i>-butyl-1<i>H</i>-pyrrole-3-carbonitriles and their reduction products to secondary amines: syntheses and X-ray structural studies
Macías, Mario A.; Castillo, Juan-Carlos; Portilla, Jaime; Acta Crystallographica Section C 74 (2018) 82–93; doi:10.1107/S2053229617017260

data_2020991
_publ_section_title
;
 A series of
 (<i>E</i>)-5-(arylideneamino)-1-<i>tert</i>-butyl-1<i>H</i>-pyrrole-3-carbonitriles
 and their reduction products to secondary amines: syntheses and X-ray
 structural studies
;
_journal_coeditor_code           CU3120
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              82
_journal_page_last               93
_journal_paper_doi               10.1107/S2053229617017260
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C16 H15 Cl2 N3'
_chemical_formula_moiety         'C16 H15 Cl2 N3'
_chemical_formula_sum            'C16 H15 Cl2 N3'
_chemical_formula_weight         320.21
_chemical_name_systematic
(<i>E</i>)-1-<i>tert</i>-Butyl-5-[(2,4-dichlorobenzylidene)amino]-1<i>H</i>-pyrrole-3-carbonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 92.987(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5428(7)
_cell_length_b                   7.9586(11)
_cell_length_c                   30.415(5)
_cell_measurement_reflns_used    4572
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.4210
_cell_measurement_theta_min      4.1790
_cell_volume                     1581.6(4)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2014)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>,  2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SUPERFLIP (Palatinus & Chapuis, 2007)
;
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 5.3072
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Agilent SuperNova Dual Source diffractometer with an Atlas detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            16620
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.362
_diffrn_reflns_theta_min         2.890
_exptl_absorpt_coefficient_mu    0.407
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2014)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.287
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.270
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2016 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0692P)^2^+0.5679P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1426
_refine_ls_wR_factor_ref         0.1521
_reflns_number_gt                2577
_reflns_number_total             3206
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cu3120sup1.cif
_cod_data_source_block           7b
_cod_database_code               2020991
_cod_database_fobs_code          2020991
_shelx_estimated_absorpt_t_min   0.892
_shelx_estimated_absorpt_t_max   0.956
_shelx_hkl_checksum              31593
_shelx_res_checksum              54999