#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/61/2236199.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_2236199
loop_
_publ_author_name
'Centore, Roberto'
'Piccialli, Vincenzo'
_publ_section_title
;
 2-Cyano-5-({4-[N-methyl-N-(2-hydroxyethyl)amino]
 phenyl}diazenyl)pyridine
;
_journal_coeditor_code           FJ2599
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3079
_journal_page_last               o3080
_journal_paper_doi               10.1107/S1600536812041396
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C15 H15 N5 O'
_chemical_formula_moiety         'C15 H15 N5 O'
_chemical_formula_sum            'C15 H15 N5 O'
_chemical_formula_weight         281.32
_chemical_melting_point          439
_chemical_name_systematic
;
2-Cyano-5-({4-[N-methyl-N-(2-hydroxyethyl)amino]
phenyl}diazenyl)pyridine
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.07(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.755(8)
_cell_length_b                   7.240(4)
_cell_length_c                   11.045(8)
_cell_measurement_reflns_used    76
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.147
_cell_measurement_theta_min      5.566
_cell_volume                     1393.4(14)
_computing_cell_refinement       'CELLFITW (Centore, 2004)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction
;
EvalCCD (Duisenberg et al.,  2003)
;
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 2012) and
Mercury (Macrae et al., 2006)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method
;
CCD rotation images, thick slices
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_sigmaI/netI    0.0652
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8528
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9955
_exptl_absorpt_correction_T_min  0.9650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2001)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.211
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0515
_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)+(0.0646P)²+0.0464P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1385
_reflns_number_gt                1336
_reflns_number_total             2403
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fj2599.cif
_cod_data_source_block           I
_cod_database_code               2236199
_cod_database_fobs_code          2236199
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C C1 0.39381(17) 0.5114(4) -0.0089(3) 0.0658(9) Uani d . 1 1
H H1A 0.4101 0.4652 -0.0821 0.079 Uiso calc R 1 1
H H1B 0.3398 0.5431 -0.0314 0.079 Uiso calc R 1 1
C C2 0.40363(16) 0.3604(3) 0.0877(3) 0.0539(7) Uani d . 1 1
H H2A 0.3763 0.2511 0.0523 0.065 Uiso calc R 1 1
H H2B 0.4576 0.3290 0.1102 0.065 Uiso calc R 1 1
C C3 0.43153(16) 0.4817(4) 0.3024(3) 0.0634(8) Uani d . 1 1
H H3A 0.4355 0.3973 0.3704 0.095 Uiso calc R 1 1
H H3B 0.4154 0.6004 0.3266 0.095 Uiso calc R 1 1
H H3C 0.4806 0.4931 0.2788 0.095 Uiso calc R 1 1
C C4 0.29960(14) 0.4002(3) 0.2038(2) 0.0389(6) Uani d . 1 1
C C5 0.27273(14) 0.4488(3) 0.3117(2) 0.0426(7) Uani d . 1 1
H H5 0.3073 0.4906 0.3803 0.051 Uiso calc R 1 1
C C6 0.19600(15) 0.4353(3) 0.3169(2) 0.0416(6) Uani d . 1 1
H H6 0.1799 0.4664 0.3895 0.050 Uiso calc R 1 1
C C7 0.14206(14) 0.3759(3) 0.2154(2) 0.0356(6) Uani d . 1 1
C C8 0.16750(14) 0.3312(3) 0.1079(2) 0.0412(6) Uani d . 1 1
H H8 0.1322 0.2941 0.0388 0.049 Uiso calc R 1 1
C C9 0.24378(14) 0.3407(3) 0.1019(2) 0.0423(7) Uani d . 1 1
H H9 0.2593 0.3072 0.0292 0.051 Uiso calc R 1 1
C C10 -0.03818(14) 0.3687(3) 0.3055(2) 0.0377(6) Uani d . 1 1
C C11 -0.09206(15) 0.4028(3) 0.2005(2) 0.0445(7) Uani d . 1 1
H H11 -0.0770 0.4255 0.1258 0.053 Uiso calc R 1 1
C C12 -0.16836(15) 0.4026(3) 0.2081(2) 0.0479(7) Uani d . 1 1
H H12 -0.2061 0.4250 0.1387 0.058 Uiso calc R 1 1
C C13 -0.18771(15) 0.3687(3) 0.3206(3) 0.0420(6) Uani d . 1 1
C C14 -0.06318(15) 0.3353(3) 0.4146(2) 0.0484(7) Uani d . 1 1
H H14 -0.0264 0.3124 0.4852 0.058 Uiso calc R 1 1
C C15 -0.26695(18) 0.3730(3) 0.3352(3) 0.0519(7) Uani d . 1 1
N N1 0.37562(12) 0.4124(3) 0.1987(2) 0.0459(6) Uani d . 1 1
N N2 0.06251(12) 0.3612(2) 0.21080(19) 0.0417(5) Uani d . 1 1
N N3 0.04319(12) 0.3723(3) 0.3147(2) 0.0455(6) Uani d . 1 1
N N4 -0.13639(13) 0.3339(3) 0.4246(2) 0.0493(6) Uani d . 1 1
N N5 -0.32935(16) 0.3783(3) 0.3473(3) 0.0743(8) Uani d . 1 1
O O1 0.43618(12) 0.6724(3) 0.0323(2) 0.0771(7) Uani d . 1 1
H H1O 0.4068 0.7588 0.0816 0.093 Uiso d R 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'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
O1 C1 C2 112.8(2) no
O1 C1 H1A 109.0 no
C2 C1 H1A 109.0 no
O1 C1 H1B 109.0 no
C2 C1 H1B 109.0 no
H1A C1 H1B 107.8 no
N1 C2 C1 113.2(2) no
N1 C2 H2A 108.9 no
C1 C2 H2A 108.9 no
N1 C2 H2B 108.9 no
C1 C2 H2B 108.9 no
H2A C2 H2B 107.8 no
N1 C3 H3A 109.5 no
N1 C3 H3B 109.5 no
H3A C3 H3B 109.5 no
N1 C3 H3C 109.5 no
H3A C3 H3C 109.5 no
H3B C3 H3C 109.5 no
N1 C4 C5 121.1(2) no
N1 C4 C9 122.2(2) no
C5 C4 C9 116.6(2) no
C6 C5 C4 121.0(2) no
C6 C5 H5 119.5 no
C4 C5 H5 119.5 no
C5 C6 C7 121.3(2) no
C5 C6 H6 119.3 no
C7 C6 H6 119.3 no
C8 C7 C6 118.3(2) no
C8 C7 N2 116.1(2) no
C6 C7 N2 125.6(2) no
C9 C8 C7 121.1(2) no
C9 C8 H8 119.4 no
C7 C8 H8 119.4 no
C8 C9 C4 121.6(2) no
C8 C9 H9 119.2 no
C4 C9 H9 119.2 no
C11 C10 C14 118.5(2) no
C11 C10 N3 125.9(2) no
C14 C10 N3 115.5(2) no
C12 C11 C10 118.9(3) no
C12 C11 H11 120.6 no
C10 C11 H11 120.6 no
C13 C12 C11 118.5(3) no
C13 C12 H12 120.8 no
C11 C12 H12 120.8 no
N4 C13 C12 124.0(3) no
N4 C13 C15 115.0(2) no
C12 C13 C15 121.0(3) no
N4 C14 C10 123.9(3) no
N4 C14 H14 118.1 no
C10 C14 H14 118.1 no
N5 C15 C13 179.3(3) no
C4 N1 C3 121.4(2) no
C4 N1 C2 121.2(2) no
C3 N1 C2 117.4(2) no
N3 N2 C7 114.1(2) no
N2 N3 C10 112.4(2) no
C14 N4 C13 116.2(2) no
C1 O1 H1O 112.1 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.414(3) no
C1 C2 1.514(4) no
C1 H1A 0.9700 no
C1 H1B 0.9700 no
C2 N1 1.458(3) no
C2 H2A 0.9700 no
C2 H2B 0.9700 no
C3 N1 1.454(3) no
C3 H3A 0.9600 no
C3 H3B 0.9600 no
C3 H3C 0.9600 no
C4 N1 1.365(3) no
C4 C5 1.410(3) no
C4 C9 1.416(3) no
C5 C6 1.378(3) no
C5 H5 0.9300 no
C6 C7 1.395(3) no
C6 H6 0.9300 no
C7 C8 1.387(3) no
C7 N2 1.408(3) no
C8 C9 1.370(3) no
C8 H8 0.9300 no
C9 H9 0.9300 no
C10 C11 1.376(4) no
C10 C14 1.383(3) no
C10 N3 1.429(3) no
C11 C12 1.373(3) no
C11 H11 0.9300 no
C12 C13 1.373(3) no
C12 H12 0.9300 no
C13 N4 1.346(3) no
C13 C15 1.447(4) no
C14 N4 1.325(3) no
C14 H14 0.9300 no
C15 N5 1.142(3) no
N2 N3 1.262(3) no
O1 H1O 1.0341 no
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
_geom_hbond_publ_flag
O1 H1O N5 2_555 1.03 1.92 2.925(4) 165 yes
C6 H6 N4 3_566 0.93 2.74 3.637(4) 162 yes
C2 H2B O1 3_665 0.97 2.68 3.369(4) 129 yes
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
_geom_torsion_publ_flag
O1 C1 C2 N1 62.7(3) no
N1 C4 C5 C6 -179.6(2) no
C9 C4 C5 C6 1.1(3) no
C4 C5 C6 C7 -1.0(3) no
C5 C6 C7 C8 -0.3(3) no
C5 C6 C7 N2 -178.6(2) no
C6 C7 C8 C9 1.5(3) no
N2 C7 C8 C9 180.0(2) no
C7 C8 C9 C4 -1.4(3) no
N1 C4 C9 C8 -179.2(2) no
C5 C4 C9 C8 0.1(3) no
C14 C10 C11 C12 0.1(3) no
N3 C10 C11 C12 -176.9(2) no
C10 C11 C12 C13 0.1(3) no
C11 C12 C13 N4 -0.6(4) no
C11 C12 C13 C15 177.8(2) no
C11 C10 C14 N4 0.0(3) no
N3 C10 C14 N4 177.4(2) no
C5 C4 N1 C3 -2.1(3) no
C9 C4 N1 C3 177.2(2) no
C5 C4 N1 C2 179.4(2) no
C9 C4 N1 C2 -1.4(3) no
C1 C2 N1 C4 82.0(3) no
C1 C2 N1 C3 -96.6(3) no
C8 C7 N2 N3 168.65(18) no
C6 C7 N2 N3 -13.0(3) no
C7 N2 N3 C10 176.23(17) no
C11 C10 N3 N2 -18.0(3) no
C14 C10 N3 N2 164.91(19) no
C10 C14 N4 C13 -0.4(3) no
C12 C13 N4 C14 0.7(3) no
C15 C13 N4 C14 -177.8(2) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658056
