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_2020993
_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 H18 Cl N3'
_chemical_formula_moiety         'C16 H18 Cl N3'
_chemical_formula_sum            'C16 H18 Cl N3'
_chemical_formula_weight         287.78
_chemical_name_systematic
1-<i>tert</i>-Butyl-5-[(4-chlorobenzyl)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   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 98.521(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2422(10)
_cell_length_b                   9.2361(10)
_cell_length_c                   20.623(2)
_cell_measurement_reflns_used    8656
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.0590
_cell_measurement_theta_min      4.0590
_cell_volume                     1552.6(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.928
_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  0.0533
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            36135
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.549
_diffrn_reflns_theta_min         2.976
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2014)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.302
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.131
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.361
_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   1.120
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         4416
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0670
_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^)+(0.0678P)^2^+0.6772P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1724
_refine_ls_wR_factor_ref         0.1975
_reflns_number_gt                2938
_reflns_number_total             4416
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cu3120sup1.cif
_cod_data_source_block           8a
_cod_database_code               2020993
_cod_database_fobs_code          2020993
_shelx_estimated_absorpt_t_min   0.931
_shelx_estimated_absorpt_t_max   0.969
_shelx_hkl_checksum              34142
_shelx_res_checksum              9737