#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/51/2005199.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_2005199
loop_
_publ_author_name
'Flensburg, C.'
'Jensen, J.'
'Larsen, S.'
'Dehaen, W.'
_publ_section_title
;
 Ethyl 3-(2-Cyano-3-phenylazo-2-butenylidene)carbazoate at 122K
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2093
_journal_page_last               2095
_journal_paper_doi               10.1107/S0108270196003095
_journal_volume                  52
_journal_year                    1996
_chemical_formula_moiety         'C14 H15 N5 O2'
_chemical_formula_sum            'C14 H15 N5 O2'
_chemical_formula_weight         285.31
_chemical_name_systematic
;
2-cyano-3-phenylazo-2-butenal carbazidoethylester-imin
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_audit_creation_method           SHELXL
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.9456(9)
_cell_length_b                   21.011(1)
_cell_length_c                   14.179(1)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    122(1)
_cell_measurement_theta_max      39.8
_cell_measurement_theta_min      32.9
_cell_volume                     2962.9(4)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'DREADD (Blessing, 1989)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-93, local programs'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      122.0(10)
_diffrn_measurement_device       'CAD4 diffractometer'
_diffrn_measurement_method       'Profile data from ω-2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4905
_diffrn_reflns_theta_max         74.86
_diffrn_reflns_theta_min         4.21
_diffrn_standards_decay_%        2.8
_diffrn_standards_interval_time  166.7
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            reddish
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.15(4)
_refine_diff_density_min         -0.20(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.014
_refine_ls_goodness_of_fit_obs   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         2729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_restrained_S_obs      1.051
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_obs          0.0350
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0434P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0829
_refine_ls_wR_factor_obs         0.0763
_reflns_number_observed          2203
_reflns_number_total             2729
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ab1357.cif
_cod_data_source_block           wd77
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0434P)^2^] where P=(Fo^2^+2Fc^2^)/3' was changed
to 'calc'. New tag '_refine_ls_weighting_details' was created. The
value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0434P)^2^]
where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2005199
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_type_symbol
O1 1 .0216(1) .70917(5) .72765(8) .0284(3) Uani d O
O2 1 .1868(1) .63720(5) .70109(8) .0250(2) Uani d O
N1 1 .4335(1) 1.03455(6) .89663(9) .0239(3) Uani d N
N2 1 .3470(1) .99036(5) .89969(9) .0226(3) Uani d N
N3 1 .0627(1) .90326(6) .9282(1) .0309(3) Uani d N
N4 1 .2152(1) .78948(5) .79430(9) .0235(3) Uani d N
N5 1 .2427(1) .73105(5) .7570(1) .0255(3) Uani d N
C1 1 .3921(1) .93349(7) .8575(1) .0223(3) Uani d C
C2 1 .2980(1) .88668(7) .8535(1) .0212(3) Uani d C
C3 1 .1670(1) .89756(7) .8950(1) .0227(3) Uani d C
C4 1 .3188(2) .82450(7) .8108(1) .0238(3) Uani d C
C5 1 .1387(1) .69351(7) .7291(1) .0215(3) Uani d C
C6 1 .5317(2) .92796(8) .8198(1) .0264(3) Uani d C
C7 1 .0860(2) .59193(7) .6675(1) .0255(3) Uani d C
C8 1 .1612(2) .53213(8) .6425(1) .0308(4) Uani d C
C11 1 .3896(2) 1.09292(7) .9371(1) .0231(3) Uani d C
C12 1 .2608(2) 1.10372(7) .9735(1) .0262(3) Uani d C
C13 1 .2312(2) 1.16235(7) 1.0126(1) .0318(4) Uani d C
C14 1 .3280(2) 1.21023(8) 1.0149(1) .0338(4) Uani d C
C15 1 .4545(2) 1.19956(8) .9783(1) .0348(4) Uani d C
C16 1 .4861(2) 1.14088(7) .9390(1) .0293(3) Uani d C
H4 1 .408(2) .8107(8) .795(1) .033(5) Uiso d H
H5 1 .324(2) .7167(8) .757(1) .045(6) Uiso d H
H12 1 .193(2) 1.0707(8) .972(1) .040(5) Uiso d H
H13 1 .140(2) 1.1698(8) 1.039(1) .036(5) Uiso d H
H14 1 .304(2) 1.2513(8) 1.040(1) .037(5) Uiso d H
H15 1 .522(2) 1.2339(8) .978(1) .043(5) Uiso d H
H16 1 .575(2) 1.1324(8) .912(1) .037(5) Uiso d H
H61 1 .541(2) .9592(9) .767(2) .050(6) Uiso d H
H62 1 .551(2) .8851(9) .799(1) .044(5) Uiso d H
H63 1 .598(2) .9401(9) .868(2) .047(6) Uiso d H
H71 1 .019(2) .5843(8) .720(1) .035(5) Uiso d H
H72 1 .042(2) .6111(7) .613(1) .027(4) Uiso d H
H81 1 .208(2) .5153(9) .698(1) .043(5) Uiso d H
H82 1 .230(2) .5402(8) .592(1) .036(5) Uiso d H
H83 1 .098(2) .4991(9) .621(1) .043(5) Uiso d H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
C5 O2 C7 115.28(11) yes
N2 N1 C11 114.18(12) yes
N1 N2 C1 112.98(12) yes
C4 N4 N5 115.05(12) yes
C5 N5 N4 118.82(12) yes
C5 N5 H5 120.5(12) ?
N4 N5 H5 120.3(13) ?
C2 C1 N2 114.36(13) yes
C2 C1 C6 124.68(14) yes
N2 C1 C6 120.95(13) yes
C1 C2 C3 119.22(13) yes
C1 C2 C4 124.75(13) yes
C3 C2 C4 116.03(13) yes
N3 C3 C2 176.9(2) yes
N4 C4 C2 118.33(13) yes
N4 C4 H4 121.7(10) ?
C2 C4 H4 119.9(10) ?
O1 C5 O2 125.49(13) yes
O1 C5 N5 125.38(13) yes
O2 C5 N5 109.11(11) yes
C1 C6 H61 107.8(11) ?
C1 C6 H62 111.4(11) ?
H61 C6 H62 110.9(15) ?
C1 C6 H63 110.6(11) ?
H61 C6 H63 106.8(15) ?
H62 C6 H63 109.2(15) ?
O2 C7 C8 106.22(13) yes
O2 C7 H71 108.2(10) ?
C8 C7 H71 111.6(10) ?
O2 C7 H72 107.2(10) ?
C8 C7 H72 112.5(10) ?
H71 C7 H72 110.9(14) ?
C7 C8 H81 110.6(11) ?
C7 C8 H82 111.4(10) ?
H81 C8 H82 107.8(14) ?
C7 C8 H83 110.0(11) ?
H81 C8 H83 107.7(15) ?
H82 C8 H83 109.3(15) ?
C16 C11 C12 120.44(14) no
C16 C11 N1 114.87(13) yes
C12 C11 N1 124.69(13) yes
C13 C12 C11 119.16(14) no
C13 C12 H12 120.0(11) ?
C11 C12 H12 120.8(11) ?
C12 C13 C14 120.4(2) no
C12 C13 H13 118.9(10) ?
C14 C13 H13 120.7(10) ?
C15 C14 C13 120.3(2) no
C15 C14 H14 120.7(11) ?
C13 C14 H14 119.0(11) ?
C14 C15 C16 120.1(2) no
C14 C15 H15 120.1(11) ?
C16 C15 H15 119.8(11) ?
C15 C16 C11 119.6(2) no
C15 C16 H16 121.6(10) ?
C11 C16 H16 118.8(10) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C5 1.210(2) yes
O2 C5 1.336(2) yes
O2 C7 1.462(2) yes
N1 N2 1.267(2) yes
N1 C11 1.423(2) yes
N2 C1 1.410(2) yes
N3 C3 1.145(2) yes
N4 C4 1.288(2) yes
N4 N5 1.364(2) yes
N5 C5 1.360(2) yes
N5 H5 0.86(2) ?
C1 C2 1.359(2) yes
C1 C6 1.492(2) yes
C2 C3 1.448(2) yes
C2 C4 1.455(2) yes
C4 H4 0.96(2) ?
C6 H61 1.00(2) ?
C6 H62 0.97(2) ?
C6 H63 0.98(2) ?
C7 C8 1.505(2) yes
C7 H71 1.01(2) ?
C7 H72 0.97(2) ?
C8 H81 0.98(2) ?
C8 H82 1.01(2) ?
C8 H83 0.99(2) ?
C11 C16 1.392(2) no
C11 C12 1.400(2) no
C12 C13 1.383(2) no
C12 H12 0.97(2) ?
C13 C14 1.393(2) no
C13 H13 0.99(2) ?
C14 C15 1.380(2) no
C14 H14 0.96(2) ?
C15 C16 1.389(2) no
C15 H15 0.99(2) ?
C16 H16 0.98(2) ?
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
C11 N1 N2 C1 178.86(12) yes
C4 N4 N5 C5 -173.71(14) ?
N1 N2 C1 C2 -175.37(12) yes
N1 N2 C1 C6 3.5(2) ?
N2 C1 C2 C3 -2.8(2) ?
C6 C1 C2 C3 178.41(14) yes
N2 C1 C2 C4 178.02(13) yes
C6 C1 C2 C4 -0.8(2) ?
C1 C2 C3 N3 -157.(3) ?
C4 C2 C3 N3 23.(3) ?
N5 N4 C4 C2 -177.99(13) yes
C1 C2 C4 N4 -166.07(15) yes
C3 C2 C4 N4 14.7(2) yes
C7 O2 C5 O1 -0.7(2) ?
C7 O2 C5 N5 -179.09(12) yes
N4 N5 C5 O1 5.8(2) ?
N4 N5 C5 O2 -175.73(12) yes
C5 O2 C7 C8 -178.56(13) yes
N2 N1 C11 C16 176.61(13) ?
N2 N1 C11 C12 -3.2(2) yes
C16 C11 C12 C13 -1.0(2) ?
N1 C11 C12 C13 178.83(14) ?
C11 C12 C13 C14 0.7(2) ?
C12 C13 C14 C15 -0.2(3) ?
C13 C14 C15 C16 0.0(3) ?
C14 C15 C16 C11 -0.3(3) ?
C12 C11 C16 C15 0.8(2) ?
N1 C11 C16 C15 -179.04(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21186811
