#------------------------------------------------------------------------------
#$Date: 2018-01-26 10:18:46 +0200 (Fri, 26 Jan 2018) $
#$Revision: 205711 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/09/2020990.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2020990
loop_
_publ_author_name
'Macías, Mario A.'
'Castillo, Juan-Carlos'
'Portilla, Jaime'
_publ_section_title
;
 A series of
 (E)-5-(arylideneamino)-1-tert-butyl-1H-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 H16 Cl N3'
_chemical_formula_moiety         'C16 H16 Cl N3'
_chemical_formula_sum            'C16 H16 Cl N3'
_chemical_formula_weight         285.77
_chemical_name_systematic
(E)-1-tert-butyl-5-[(4-chlorobenzylidene)amino]-1H-pyrrole-3-carbonitrile
_space_group_crystal_system      orthorhombic
_space_group_IT_number           57
_space_group_name_Hall           '-P 2c 2b'
_space_group_name_H-M_alt        'P b c m'
_symmetry_space_group_name_Hall  '-P 2c 2b'
_symmetry_space_group_name_H-M   'P b c m'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8317(14)
_cell_length_b                   24.261(3)
_cell_length_c                   6.9706(14)
_cell_measurement_reflns_used    8043
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.0310
_cell_measurement_theta_min      4.0190
_cell_volume                     1493.6(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 et al.,  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 0.995
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Agilent SuperNova Dual Source diffractometer with an Atlas detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            29057
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.393
_diffrn_reflns_theta_min         2.853
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2014)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.191
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.109
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.289
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1658
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0490
_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/[σ²(Fo²)+(0.0667P)²+0.5084P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1393
_reflns_number_gt                1417
_reflns_number_total             1658
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cu3120sup1.cif
_cod_data_source_block           7a
_cod_database_code               2020990
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.954
_shelx_estimated_absorpt_t_max   0.973
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y+1/2, z+1/2'
'-x, -y, z+1/2'
'x, -y+1/2, -z'
'-x, -y, -z'
'-x, y-1/2, -z-1/2'
'x, y, -z-1/2'
'-x, y-1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Cl Cl4 0.86106(9) 0.04937(3) 0.750000 0.0877(4) Uani d 1
C C524 0.8268(3) 0.11940(10) 0.750000 0.0526(6) Uani d 1
C C525 0.9478(3) 0.15465(10) 0.750000 0.0564(6) Uani d 1
H H525 1.046360 0.141182 0.750000 0.068 Uiso calc 1
C C526 0.9201(3) 0.21091(10) 0.750000 0.0565(7) Uani d 1
H H526 1.001353 0.235280 0.750000 0.068 Uiso calc 1
C C521 0.7739(3) 0.23155(9) 0.750000 0.0417(5) Uani d 1
C C522 0.6541(3) 0.19449(10) 0.750000 0.0507(6) Uani d 1
H H522 0.555139 0.207616 0.750000 0.061 Uiso calc 1
C C523 0.6800(3) 0.13859(10) 0.750000 0.0585(7) Uani d 1
H H523 0.599257 0.113988 0.750000 0.070 Uiso calc 1
C C52 0.7474(3) 0.29093(9) 0.750000 0.0472(6) Uani d 1
H H52 0.830509 0.314479 0.750000 0.057 Uiso calc 1
N N51 0.6172(2) 0.31146(8) 0.750000 0.0479(5) Uani d 1
C C5 0.5981(3) 0.36838(9) 0.750000 0.0455(5) Uani d 1
N N1 0.4523(2) 0.39007(7) 0.750000 0.0472(5) Uani d 1
C C11 0.3066(3) 0.35837(9) 0.750000 0.0534(6) Uani d 1
C C12 0.1732(3) 0.39860(12) 0.750000 0.0702(9) Uani d 1
H H12B 0.172(3) 0.4216(12) 0.624(4) 0.105 Uiso d 1
H H12A 0.083(4) 0.3774(17) 0.750000 0.105 Uiso d 1
C C13 0.3003(2) 0.32337(7) 0.5675(3) 0.0663(6) Uani d 1
H H13A 0.309936 0.346819 0.457270 0.100 Uiso calc 1
H H13B 0.205339 0.304180 0.562117 0.100 Uiso calc 1
H H13C 0.381713 0.297150 0.568733 0.100 Uiso calc 1
C C2 0.4636(3) 0.44565(9) 0.750000 0.0536(6) Uani d 1
H H2 0.382738 0.470218 0.750000 0.064 Uiso calc 1
C C3 0.6145(3) 0.45988(10) 0.750000 0.0519(6) Uani d 1
C C4 0.6996(3) 0.41106(10) 0.750000 0.0522(6) Uani d 1
H H4 0.804606 0.408227 0.750000 0.063 Uiso calc 1
C C31 0.6689(3) 0.51488(11) 0.750000 0.0616(7) Uani d 1
N N32 0.7127(4) 0.55906(10) 0.750000 0.0859(9) Uani d 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
C525 C524 C523 . 121.6(2)
C525 C524 Cl4 . 118.60(19)
C523 C524 Cl4 . 119.84(19)
C524 C525 C526 . 118.5(2)
C524 C525 H525 . 120.7
C526 C525 H525 . 120.7
C521 C526 C525 . 121.4(2)
C521 C526 H526 . 119.3
C525 C526 H526 . 119.3
C526 C521 C522 . 118.4(2)
C526 C521 C52 . 120.4(2)
C522 C521 C52 . 121.1(2)
C523 C522 C521 . 120.8(2)
C523 C522 H522 . 119.6
C521 C522 H522 . 119.6
C522 C523 C524 . 119.3(2)
C522 C523 H523 . 120.3
C524 C523 H523 . 120.3
N51 C52 C521 . 122.7(2)
N51 C52 H52 . 118.7
C521 C52 H52 . 118.7
C52 N51 C5 . 120.4(2)
C4 C5 N51 . 132.2(2)
C4 C5 N1 . 108.65(19)
N51 C5 N1 . 119.17(19)
C2 N1 C5 . 108.00(18)
C2 N1 C11 . 125.08(19)
C5 N1 C11 . 126.92(18)
N1 C11 C12 . 109.50(19)
N1 C11 C13 . 108.40(13)
C12 C11 C13 . 109.04(13)
N1 C11 C13 7_557 108.40(13)
C12 C11 C13 7_557 109.04(13)
C13 C11 C13 7_557 112.4(2)
C11 C12 H12B . 110.5(15)
C11 C12 H12A . 107(2)
H12B C12 H12A . 106.6(18)
C11 C13 H13A . 109.5
C11 C13 H13B . 109.5
H13A C13 H13B . 109.5
C11 C13 H13C . 109.5
H13A C13 H13C . 109.5
H13B C13 H13C . 109.5
N1 C2 C3 . 108.7(2)
N1 C2 H2 . 125.6
C3 C2 H2 . 125.6
C2 C3 C4 . 107.9(2)
C2 C3 C31 . 124.3(2)
C4 C3 C31 . 127.8(2)
C5 C4 C3 . 106.7(2)
C5 C4 H4 . 126.6
C3 C4 H4 . 126.6
N32 C31 C3 . 179.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cl4 C524 . 1.726(2)
C524 C525 . 1.368(4)
C524 C523 . 1.378(4)
C525 C526 . 1.387(3)
C525 H525 . 0.9300
C526 C521 . 1.384(3)
C526 H526 . 0.9300
C521 C522 . 1.389(3)
C521 C52 . 1.459(3)
C522 C523 . 1.375(3)
C522 H522 . 0.9300
C523 H523 . 0.9300
C52 N51 . 1.254(3)
C52 H52 . 0.9300
N51 C5 . 1.391(3)
C5 C4 . 1.369(3)
C5 N1 . 1.391(3)
N1 C2 . 1.352(3)
N1 C11 . 1.499(3)
C11 C12 . 1.530(4)
C11 C13 . 1.530(2)
C11 C13 7_557 1.530(2)
C12 H12B . 1.04(3)
C12 H12A . 0.95(4)
C13 H13A . 0.9600
C13 H13B . 0.9600
C13 H13C . 0.9600
C2 C3 . 1.377(4)
C2 H2 . 0.9300
C3 C4 . 1.403(3)
C3 C31 . 1.418(3)
C4 H4 . 0.9300
C31 N32 . 1.140(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C13 H13C N51 . 0.96 2.46 3.088(3) 123.0
C13 H13A N32 5_666 0.96 2.71 3.612(3) 156.9
C2 H2 Cl4 8_665 0.93 2.89 3.815(3) 178.1
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_4
_geom_torsion
C523 C524 C525 C526 . 0.0
Cl4 C524 C525 C526 . 180.0
C524 C525 C526 C521 . 0.0
C525 C526 C521 C522 . 0.0
C525 C526 C521 C52 . 180.0
C526 C521 C522 C523 . 0.0
C52 C521 C522 C523 . 180.0
C521 C522 C523 C524 . 0.0
C525 C524 C523 C522 . 0.0
Cl4 C524 C523 C522 . 180.0
C526 C521 C52 N51 . 180.0
C522 C521 C52 N51 . 0.0
C521 C52 N51 C5 . 180.0
C52 N51 C5 C4 . 0.0
C52 N51 C5 N1 . 180.0
C4 C5 N1 C2 . 0.0
N51 C5 N1 C2 . 180.0
C4 C5 N1 C11 . 180.0
N51 C5 N1 C11 . 0.0
C2 N1 C11 C12 . 0.0
C5 N1 C11 C12 . 180.0
C2 N1 C11 C13 . 118.85(13)
C5 N1 C11 C13 . -61.15(13)
C2 N1 C11 C13 7_557 -118.85(13)
C5 N1 C11 C13 7_557 61.15(13)
C5 N1 C2 C3 . 0.0
C11 N1 C2 C3 . 180.0
N1 C2 C3 C4 . 0.0
N1 C2 C3 C31 . 180.0
N51 C5 C4 C3 . 180.0
N1 C5 C4 C3 . 0.0
C2 C3 C4 C5 . 0.0
C31 C3 C4 C5 . 180.0

_cod_database_fobs_code 2020990
