#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/28/2232875.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_2232875
loop_
_publ_author_name
'Letessier, Julien'
'Schollmeyer, Dieter'
'Detert, Heiner'
'Opatz, Till'
_publ_section_title
;
 rac-4-{(E)-[1-Cyano-1-cyclohexyl-2-(1H-indol-3-yl)ethyl]iminomethyl}benzonitrile
;
_journal_coeditor_code           NC2256
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3435
_journal_paper_doi               10.1107/S1600536811049841
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C25 H24 N4'
_chemical_formula_moiety         'C25 H24 N4'
_chemical_formula_sum            'C25 H24 N4'
_chemical_formula_weight         380.48
_chemical_melting_point_gt       438
_chemical_melting_point_lt       439
_chemical_name_systematic
;
rac-4-{(E)-[1-Cyano-1-cyclohexyl-2-(1H-indol-
3-yl)ethyl]iminomethyl}benzonitrile
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.958(6)
_cell_angle_beta                 105.995(5)
_cell_angle_gamma                99.505(6)
_cell_formula_units_Z            2
_cell_length_a                   9.0755(6)
_cell_length_b                   10.4546(8)
_cell_length_c                   11.8246(8)
_cell_measurement_reflns_used    7492
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      29.66
_cell_measurement_theta_min      3.37
_cell_volume                     1058.09(13)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2001)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11005
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         3.37
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.232
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         5089
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0520P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0968
_refine_ls_wR_factor_ref         0.1066
_reflns_number_gt                3183
_reflns_number_total             5089
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc2256.cif
_cod_data_source_block           I
_cod_database_code               2232875
_cod_database_fobs_code          2232875
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
N N1 0.58172(14) 0.16501(12) 0.34742(10) 0.0446(3) Uani d . 1 1
H H1 0.6422 0.1093 0.3401 0.053 Uiso calc R 1 1
C C2 0.51776(15) 0.23949(13) 0.26196(11) 0.0388(3) Uani d . 1 1
C C3 0.52832(18) 0.24696(15) 0.14670(12) 0.0486(4) Uani d . 1 1
H H3 0.5864 0.1944 0.1151 0.058 Uiso calc R 1 1
C C4 0.45124(19) 0.33346(17) 0.08059(12) 0.0545(4) Uani d . 1 1
H H4 0.4560 0.3403 0.0018 0.065 Uiso calc R 1 1
C C5 0.36656(18) 0.41101(16) 0.12666(13) 0.0523(4) Uani d . 1 1
H H5 0.3155 0.4703 0.0791 0.063 Uiso calc R 1 1
C C6 0.35547(16) 0.40333(14) 0.24005(12) 0.0434(3) Uani d . 1 1
H H6 0.2973 0.4567 0.2706 0.052 Uiso calc R 1 1
C C7 0.43120(15) 0.31584(13) 0.30950(11) 0.0356(3) Uani d . 1 1
C C8 0.44490(15) 0.28356(12) 0.42828(11) 0.0359(3) Uani d . 1 1
C C9 0.53641(16) 0.19104(14) 0.44635(12) 0.0419(3) Uani d . 1 1
H H9 0.5647 0.1505 0.5172 0.050 Uiso calc R 1 1
C C10 0.37533(15) 0.34143(13) 0.51440(11) 0.0391(3) Uani d . 1 1
H H10A 0.3701 0.4330 0.4990 0.047 Uiso calc R 1 1
H H10B 0.4461 0.3428 0.5950 0.047 Uiso calc R 1 1
C C11 0.20943(15) 0.26983(12) 0.51160(10) 0.0339(3) Uani d . 1 1
C C12 0.22302(15) 0.14187(13) 0.55972(11) 0.0369(3) Uani d . 1 1
N N13 0.23057(15) 0.04430(12) 0.59751(10) 0.0487(3) Uani d . 1 1
C C14 0.13740(15) 0.35027(12) 0.58881(10) 0.0346(3) Uani d . 1 1
H H14 0.1336 0.4365 0.5564 0.042 Uiso calc R 1 1
C C15 -0.03045(16) 0.28806(14) 0.58034(12) 0.0417(3) Uani d . 1 1
H H15A -0.0947 0.2791 0.4968 0.050 Uiso calc R 1 1
H H15B -0.0323 0.1996 0.6067 0.050 Uiso calc R 1 1
C C16 -0.10125(17) 0.36810(15) 0.65522(12) 0.0450(3) Uani d . 1 1
H H16A -0.1117 0.4526 0.6227 0.054 Uiso calc R 1 1
H H16B -0.2069 0.3213 0.6516 0.054 Uiso calc R 1 1
C C17 -0.00124(18) 0.39252(14) 0.78303(12) 0.0453(3) Uani d . 1 1
H H17A 0.0015 0.3086 0.8180 0.054 Uiso calc R 1 1
H H17B -0.0472 0.4484 0.8288 0.054 Uiso calc R 1 1
C C18 0.16384(18) 0.45897(15) 0.79033(12) 0.0488(4) Uani d . 1 1
H H18A 0.1614 0.5456 0.7606 0.059 Uiso calc R 1 1
H H18B 0.2283 0.4723 0.8740 0.059 Uiso calc R 1 1
C C19 0.23735(17) 0.37809(15) 0.71819(11) 0.0446(3) Uani d . 1 1
H H19A 0.2488 0.2946 0.7525 0.054 Uiso calc R 1 1
H H19B 0.3427 0.4255 0.7219 0.054 Uiso calc R 1 1
N N20 0.11173(12) 0.25599(10) 0.38904(8) 0.0344(2) Uani d . 1 1
C C21 0.06207(15) 0.14545(12) 0.33013(10) 0.0365(3) Uani d . 1 1
H H21 0.0836 0.0694 0.3671 0.044 Uiso calc R 1 1
C C22 -0.02917(15) 0.13329(13) 0.20417(10) 0.0379(3) Uani d . 1 1
C C23 -0.1016(2) 0.01174(15) 0.14411(12) 0.0529(4) Uani d . 1 1
H H23 -0.0948 -0.0640 0.1849 0.064 Uiso calc R 1 1
C C24 -0.1835(2) -0.00046(17) 0.02578(13) 0.0644(5) Uani d . 1 1
H H24 -0.2321 -0.0841 -0.0149 0.077 Uiso calc R 1 1
C C25 -0.19417(19) 0.10979(17) -0.03294(12) 0.0561(4) Uani d . 1 1
C C26 -0.12354(17) 0.23217(15) 0.02625(12) 0.0478(4) Uani d . 1 1
H H26 -0.1322 0.3079 -0.0144 0.057 Uiso calc R 1 1
C C27 -0.04120(16) 0.24334(13) 0.14366(11) 0.0408(3) Uani d . 1 1
H H27 0.0080 0.3270 0.1839 0.049 Uiso calc R 1 1
C C28 -0.2738(3) 0.1007(2) -0.15794(14) 0.0846(7) Uani d . 1 1
N N29 -0.3312(3) 0.0976(2) -0.25669(14) 0.1323(11) Uani d . 1 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N1 C9 109.06(12)
C2 N1 H1 125.5
C9 N1 H1 125.5
N1 C2 C3 130.63(14)
N1 C2 C7 107.47(11)
C3 C2 C7 121.90(13)
C4 C3 C2 117.47(15)
C4 C3 H3 121.3
C2 C3 H3 121.3
C3 C4 C5 121.45(13)
C3 C4 H4 119.3
C5 C4 H4 119.3
C6 C5 C4 121.14(14)
C6 C5 H5 119.4
C4 C5 H5 119.4
C5 C6 C7 119.02(15)
C5 C6 H6 120.5
C7 C6 H6 120.5
C6 C7 C2 119.01(12)
C6 C7 C8 133.73(13)
C2 C7 C8 107.25(11)
C9 C8 C7 106.01(12)
C9 C8 C10 127.18(11)
C7 C8 C10 126.80(12)
C8 C9 N1 110.21(12)
C8 C9 H9 124.9
N1 C9 H9 124.9
C8 C10 C11 115.35(10)
C8 C10 H10A 108.4
C11 C10 H10A 108.4
C8 C10 H10B 108.4
C11 C10 H10B 108.4
H10A C10 H10B 107.5
N20 C11 C12 112.70(10)
N20 C11 C14 108.71(10)
C12 C11 C14 108.63(9)
N20 C11 C10 107.39(9)
C12 C11 C10 108.49(11)
C14 C11 C10 110.94(10)
N13 C12 C11 178.41(14)
C15 C14 C19 110.85(10)
C15 C14 C11 112.32(10)
C19 C14 C11 112.82(11)
C15 C14 H14 106.8
C19 C14 H14 106.8
C11 C14 H14 106.8
C16 C15 C14 112.13(11)
C16 C15 H15A 109.2
C14 C15 H15A 109.2
C16 C15 H15B 109.2
C14 C15 H15B 109.2
H15A C15 H15B 107.9
C17 C16 C15 111.34(12)
C17 C16 H16A 109.4
C15 C16 H16A 109.4
C17 C16 H16B 109.4
C15 C16 H16B 109.4
H16A C16 H16B 108.0
C16 C17 C18 110.28(11)
C16 C17 H17A 109.6
C18 C17 H17A 109.6
C16 C17 H17B 109.6
C18 C17 H17B 109.6
H17A C17 H17B 108.1
C19 C18 C17 111.34(12)
C19 C18 H18A 109.4
C17 C18 H18A 109.4
C19 C18 H18B 109.4
C17 C18 H18B 109.4
H18A C18 H18B 108.0
C18 C19 C14 111.10(12)
C18 C19 H19A 109.4
C14 C19 H19A 109.4
C18 C19 H19B 109.4
C14 C19 H19B 109.4
H19A C19 H19B 108.0
C21 N20 C11 121.14(11)
N20 C21 C22 120.67(12)
N20 C21 H21 119.7
C22 C21 H21 119.7
C23 C22 C27 119.03(12)
C23 C22 C21 120.53(12)
C27 C22 C21 120.42(12)
C24 C23 C22 120.77(14)
C24 C23 H23 119.6
C22 C23 H23 119.6
C25 C24 C23 119.43(14)
C25 C24 H24 120.3
C23 C24 H24 120.3
C24 C25 C26 120.46(13)
C24 C25 C28 121.09(15)
C26 C25 C28 118.41(15)
C27 C26 C25 119.74(13)
C27 C26 H26 120.1
C25 C26 H26 120.1
C26 C27 C22 120.56(13)
C26 C27 H27 119.7
C22 C27 H27 119.7
N29 C28 C25 176.98(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.3681(17)
N1 C9 1.3715(18)
N1 H1 0.8800
C2 C3 1.3976(18)
C2 C7 1.4051(19)
C3 C4 1.378(2)
C3 H3 0.9500
C4 C5 1.391(2)
C4 H4 0.9500
C5 C6 1.3773(19)
C5 H5 0.9500
C6 C7 1.3992(19)
C6 H6 0.9500
C7 C8 1.4382(16)
C8 C9 1.364(2)
C8 C10 1.4895(19)
C9 H9 0.9500
C10 C11 1.5576(17)
C10 H10A 0.9900
C10 H10B 0.9900
C11 N20 1.4612(15)
C11 C12 1.4910(17)
C11 C14 1.5489(18)
C12 N13 1.1394(16)
C14 C15 1.5282(18)
C14 C19 1.5330(17)
C14 H14 1.0000
C15 C16 1.520(2)
C15 H15A 0.9900
C15 H15B 0.9900
C16 C17 1.517(2)
C16 H16A 0.9900
C16 H16B 0.9900
C17 C18 1.521(2)
C17 H17A 0.9900
C17 H17B 0.9900
C18 C19 1.521(2)
C18 H18A 0.9900
C18 H18B 0.9900
C19 H19A 0.9900
C19 H19B 0.9900
N20 C21 1.2633(16)
C21 C22 1.4786(17)
C21 H21 0.9500
C22 C23 1.3875(19)
C22 C27 1.3897(18)
C23 C24 1.380(2)
C23 H23 0.9500
C24 C25 1.379(2)
C24 H24 0.9500
C25 C26 1.388(2)
C25 C28 1.446(2)
C26 C27 1.3719(18)
C26 H26 0.9500
C27 H27 0.9500
C28 N29 1.136(2)
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
N1 H1 N13 2_656 0.88 2.17 2.9801(18) 152
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
C9 N1 C2 C3 -179.37(14)
C9 N1 C2 C7 0.76(14)
N1 C2 C3 C4 -179.33(13)
C7 C2 C3 C4 0.5(2)
C2 C3 C4 C5 0.3(2)
C3 C4 C5 C6 -0.6(2)
C4 C5 C6 C7 0.1(2)
C5 C6 C7 C2 0.72(19)
C5 C6 C7 C8 179.62(13)
N1 C2 C7 C6 178.85(11)
C3 C2 C7 C6 -1.03(19)
N1 C2 C7 C8 -0.32(14)
C3 C2 C7 C8 179.79(12)
C6 C7 C8 C9 -179.23(14)
C2 C7 C8 C9 -0.23(14)
C6 C7 C8 C10 -0.2(2)
C2 C7 C8 C10 178.80(12)
C7 C8 C9 N1 0.71(14)
C10 C8 C9 N1 -178.32(12)
C2 N1 C9 C8 -0.93(15)
C9 C8 C10 C11 -90.70(16)
C7 C8 C10 C11 90.47(15)
C8 C10 C11 N20 -51.87(14)
C8 C10 C11 C12 70.21(13)
C8 C10 C11 C14 -170.53(10)
N20 C11 C12 N13 -93(5)
C14 C11 C12 N13 27(5)
C10 C11 C12 N13 148(5)
N20 C11 C14 C15 57.61(12)
C12 C11 C14 C15 -65.36(13)
C10 C11 C14 C15 175.47(10)
N20 C11 C14 C19 -176.23(10)
C12 C11 C14 C19 60.80(13)
C10 C11 C14 C19 -58.36(13)
C19 C14 C15 C16 53.39(15)
C11 C14 C15 C16 -179.38(10)
C14 C15 C16 C17 -55.08(15)
C15 C16 C17 C18 56.49(16)
C16 C17 C18 C19 -57.64(16)
C17 C18 C19 C14 56.67(15)
C15 C14 C19 C18 -53.95(15)
C11 C14 C19 C18 179.09(11)
C12 C11 N20 C21 -7.59(17)
C14 C11 N20 C21 -128.07(12)
C10 C11 N20 C21 111.83(13)
C11 N20 C21 C22 -176.49(11)
N20 C21 C22 C23 -171.10(14)
N20 C21 C22 C27 10.1(2)
C27 C22 C23 C24 0.6(2)
C21 C22 C23 C24 -178.30(15)
C22 C23 C24 C25 -0.5(3)
C23 C24 C25 C26 -0.1(3)
C23 C24 C25 C28 177.63(18)
C24 C25 C26 C27 0.7(3)
C28 C25 C26 C27 -177.12(16)
C25 C26 C27 C22 -0.6(2)
C23 C22 C27 C26 0.0(2)
C21 C22 C27 C26 178.88(13)
C24 C25 C28 N29 -137(6)
C26 C25 C28 N29 41(6)
