#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/58/2215895.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_2215895
loop_
_publ_author_name
'Qingfang Cheng'
'Xingyou Xu'
'Changyong Zong'
'Huiling Feng'
_publ_section_title
;
 2-[1-(3-Aminophenyl)ethylidene]propanedinitrile
;
_journal_coeditor_code           EZ2100
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4316
_journal_page_last               o4316
_journal_paper_doi               10.1107/S1600536807047423
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C11 H9 N3'
_chemical_formula_moiety         'C11 H9 N3'
_chemical_formula_sum            'C11 H9 N3'
_chemical_formula_weight         183.21
_chemical_name_systematic
;
2-[1-(3-Aminophenyl)ethylidene]propanedinitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 99.961(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4654(8)
_cell_length_b                   13.7051(18)
_cell_length_c                   9.5361(17)
_cell_measurement_reflns_used    1277
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.203
_cell_measurement_theta_min      2.455
_cell_volume                     961.0(2)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics
'SHELXTL (Bruker, 2000) and DIAMOND (Brandenburg, 2004)'
_computing_publication_material  'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0527
_diffrn_reflns_av_sigmaI/netI    0.0659
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4744
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9913
_exptl_absorpt_correction_T_min  0.9689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.173
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1687
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0509
_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)+(0.0469P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1239
_reflns_number_gt                944
_reflns_number_total             1687
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ez2100.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2215895
_cod_database_fobs_code          2215895
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
N N1 0.2598(3) 0.98666(15) 0.4529(3) 0.0732(7) Uani d . 1
N N2 0.1402(3) 0.89557(17) 0.0215(3) 0.0784(7) Uani d . 1
N N3 0.2430(3) 0.53195(15) 0.7174(2) 0.0798(7) Uani d . 1
H H3A 0.2525 0.5189 0.8066 0.096 Uiso calc R 1
H H3B 0.2815 0.4908 0.6613 0.096 Uiso calc R 1
C C1 0.2043(3) 0.92393(18) 0.3799(3) 0.0536(7) Uani d . 1
C C2 0.1377(3) 0.84685(16) 0.2806(2) 0.0461(6) Uani d . 1
C C3 0.1375(3) 0.87283(17) 0.1360(3) 0.0553(7) Uani d . 1
C C4 0.0880(3) 0.75772(16) 0.3203(2) 0.0444(6) Uani d . 1
C C5 0.0877(3) 0.73249(16) 0.4696(2) 0.0435(6) Uani d . 1
C C6 0.1566(3) 0.64313(16) 0.5219(3) 0.0499(6) Uani d . 1
H H6 0.1970 0.5988 0.4604 0.060 Uiso calc R 1
C C7 0.1666(3) 0.61835(18) 0.6645(3) 0.0536(7) Uani d . 1
C C8 0.1040(3) 0.68524(19) 0.7545(3) 0.0577(7) Uani d . 1
H H8 0.1115 0.6709 0.8507 0.069 Uiso calc R 1
C C9 0.0308(3) 0.7728(2) 0.7010(3) 0.0592(7) Uani d . 1
H H9 -0.0139 0.8161 0.7616 0.071 Uiso calc R 1
C C10 0.0223(3) 0.79763(17) 0.5605(3) 0.0509(6) Uani d . 1
H H10 -0.0265 0.8573 0.5267 0.061 Uiso calc R 1
C C11 0.0328(3) 0.68186(16) 0.2086(3) 0.0583(7) Uani d . 1
H H11A 0.0460 0.7075 0.1172 0.088 Uiso calc R 1
H H11B -0.0918 0.6640 0.2073 0.088 Uiso calc R 1
H H11C 0.1088 0.6254 0.2294 0.088 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0955(18) 0.0534(14) 0.0705(17) -0.0135(13) 0.0140(14) -0.0121(13)
N2 0.1029(19) 0.0718(16) 0.0607(16) 0.0024(14) 0.0152(14) 0.0081(14)
N3 0.119(2) 0.0599(14) 0.0606(15) 0.0067(14) 0.0162(14) 0.0154(13)
C1 0.0626(18) 0.0447(15) 0.0532(16) 0.0020(13) 0.0090(13) 0.0022(14)
C2 0.0488(15) 0.0424(14) 0.0467(15) 0.0022(11) 0.0072(12) 0.0003(12)
C3 0.0638(17) 0.0450(15) 0.0570(17) -0.0001(12) 0.0107(14) 0.0013(14)
C4 0.0399(13) 0.0436(13) 0.0496(15) 0.0053(11) 0.0073(11) -0.0013(12)
C5 0.0424(14) 0.0403(13) 0.0476(15) -0.0037(11) 0.0074(11) -0.0027(12)
C6 0.0580(16) 0.0438(14) 0.0487(15) -0.0029(12) 0.0115(12) -0.0002(13)
C7 0.0541(16) 0.0506(15) 0.0548(17) -0.0081(13) 0.0062(13) 0.0078(15)
C8 0.0611(17) 0.0674(18) 0.0452(15) -0.0068(15) 0.0113(13) 0.0015(15)
C9 0.0524(16) 0.0719(19) 0.0561(18) -0.0034(14) 0.0175(13) -0.0129(15)
C10 0.0471(15) 0.0494(14) 0.0572(16) -0.0003(12) 0.0119(12) -0.0032(13)
C11 0.0678(17) 0.0506(15) 0.0560(17) -0.0070(13) 0.0089(13) -0.0077(13)
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
C7 N3 H3A 120.0
C7 N3 H3B 120.0
H3A N3 H3B 120.0
N1 C1 C2 176.8(3)
C4 C2 C3 122.9(2)
C4 C2 C1 123.8(2)
C3 C2 C1 113.2(2)
N2 C3 C2 178.2(3)
C2 C4 C5 122.2(2)
C2 C4 C11 119.0(2)
C5 C4 C11 118.8(2)
C6 C5 C10 119.4(2)
C6 C5 C4 119.7(2)
C10 C5 C4 120.9(2)
C5 C6 C7 121.4(2)
C5 C6 H6 119.3
C7 C6 H6 119.3
N3 C7 C8 120.3(2)
N3 C7 C6 121.2(2)
C8 C7 C6 118.4(2)
C9 C8 C7 119.9(2)
C9 C8 H8 120.0
C7 C8 H8 120.0
C10 C9 C8 121.7(2)
C10 C9 H9 119.2
C8 C9 H9 119.2
C9 C10 C5 119.2(2)
C9 C10 H10 120.4
C5 C10 H10 120.4
C4 C11 H11A 109.5
C4 C11 H11B 109.5
H11A C11 H11B 109.5
C4 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.138(3)
N2 C3 1.139(3)
N3 C7 1.372(3)
N3 H3A 0.8600
N3 H3B 0.8600
C1 C2 1.448(3)
C2 C4 1.350(3)
C2 C3 1.424(3)
C4 C5 1.466(3)
C4 C11 1.494(3)
C5 C6 1.387(3)
C5 C10 1.391(3)
C6 C7 1.391(3)
C6 H6 0.9300
C7 C8 1.390(3)
C8 C9 1.379(3)
C8 H8 0.9300
C9 C10 1.373(3)
C9 H9 0.9300
C10 H10 0.9300
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
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
N3 H3A N1 2_546 0.86 2.35 3.209(3) 173.1
N3 H3B N2 2_545 0.86 2.33 3.182(3) 170.3
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
C3 C2 C4 C5 -179.5(2)
C1 C2 C4 C5 3.5(3)
C3 C2 C4 C11 1.0(3)
C1 C2 C4 C11 -176.0(2)
C2 C4 C5 C6 -136.5(2)
C11 C4 C5 C6 43.0(3)
C2 C4 C5 C10 42.3(3)
C11 C4 C5 C10 -138.2(2)
C10 C5 C6 C7 -1.9(3)
C4 C5 C6 C7 177.0(2)
C5 C6 C7 N3 -176.7(2)
C5 C6 C7 C8 0.6(3)
N3 C7 C8 C9 178.6(2)
C6 C7 C8 C9 1.3(4)
C7 C8 C9 C10 -1.9(4)
C8 C9 C10 C5 0.6(4)
C6 C5 C10 C9 1.3(3)
C4 C5 C10 C9 -177.5(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 216522
