#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/80/2208097.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_2208097
loop_
_publ_author_name
'Shi, Jing-Min'
'Zhang, Xia'
'Xu, Hai-Yan'
'Liu, Lian-Dong'
_publ_section_title
;
 2-Amino-3-(4-hydroxybenzylideneamino)butenedinitrile monohydrate
;
_journal_coeditor_code           IS6177
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o831
_journal_page_last               o832
_journal_paper_doi               10.1107/S1600536806002923
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C11 H10 N4 O2'
_chemical_formula_moiety         'C11 H10 N4 O2'
_chemical_formula_sum            'C11 H10 N4 O2'
_chemical_formula_weight         230.23
_chemical_name_systematic
;
2-Amino-3-(4-hydroxybenzylideneamino)butenedinitrile monohydrate
;
_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                 90.604(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.848(2)
_cell_length_b                   7.0388(15)
_cell_length_c                   16.473(3)
_cell_measurement_reflns_used    2655
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.6225
_cell_measurement_theta_min      2.3985
_cell_volume                     1141.8(4)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL  (Bruker, 2001)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_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  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6301
_diffrn_reflns_theta_full        26.49
_diffrn_reflns_theta_max         26.49
_diffrn_reflns_theta_min         2.40
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9819
_exptl_absorpt_correction_T_min  0.9781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.303
_refine_ls_extinction_coef       0.024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2358
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0884P)²+0.0552P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1374
_reflns_number_gt                1943
_reflns_number_total             2358
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is6177.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_cell_volume        1141.9(4)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2208097
_cod_database_fobs_code          2208097
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_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_type_symbol
N1 0.15384(11) 0.02846(15) 0.45425(6) 0.0334(3) Uani d . 1 N
O1 0.01828(11) 0.41676(15) 0.11294(6) 0.0508(3) Uani d . 1 O
H4 -0.0076 0.3519 0.0744 0.076 Uiso calc R 1 H
C8 0.18530(13) -0.08908(19) 0.51945(7) 0.0328(3) Uani d . 1 C
C7 0.13287(13) -0.03927(19) 0.38325(7) 0.0342(3) Uani d . 1 C
H6 0.1379 -0.1700 0.3758 0.041 Uiso calc R 1 H
C5 0.10147(12) 0.08086(19) 0.31369(7) 0.0331(3) Uani d . 1 C
C4 0.10162(15) 0.2776(2) 0.31899(8) 0.0422(4) Uani d . 1 C
H5 0.1207 0.3359 0.3685 0.051 Uiso calc R 1 H
C6 0.07016(16) -0.0016(2) 0.23923(8) 0.0425(4) Uani d . 1 C
H1 0.0692 -0.1333 0.2347 0.051 Uiso calc R 1 H
C11 0.24004(14) -0.1223(2) 0.66272(8) 0.0399(4) Uani d . 1 C
C2 0.04374(13) 0.3024(2) 0.17805(8) 0.0370(3) Uani d . 1 C
C10 0.20193(13) -0.00669(19) 0.59391(7) 0.0332(3) Uani d . 1 C
C9 0.20000(15) -0.2904(2) 0.51078(8) 0.0406(4) Uani d . 1 C
N3 0.27179(15) -0.2099(2) 0.71749(8) 0.0571(4) Uani d . 1 N
N4 0.18443(13) 0.17866(17) 0.60808(7) 0.0450(3) Uani d . 1 N
H4A 0.1613 0.2534 0.5690 0.054 Uiso calc R 1 H
H4B 0.1963 0.2231 0.6563 0.054 Uiso calc R 1 H
C1 0.04046(15) 0.1075(2) 0.17185(8) 0.0425(4) Uani d . 1 C
H2 0.0184 0.0499 0.1226 0.051 Uiso calc R 1 H
C3 0.07373(16) 0.3871(2) 0.25154(8) 0.0466(4) Uani d . 1 C
H3 0.0751 0.5189 0.2556 0.056 Uiso calc R 1 H
N2 0.21026(18) -0.4505(2) 0.50026(8) 0.0640(4) Uani d . 1 N
O2 0.44395(12) 0.25802(15) 0.47460(6) 0.0527(3) Uani d D 1 O
H8 0.3651 0.3197 0.4772 0.079 Uiso d RD 1 H
H7 0.4335 0.1756 0.4345 0.079 Uiso d RD 1 H
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 0.0427(6) 0.0296(6) 0.0278(6) 0.0011(4) -0.0059(4) 0.0035(4)
O1 0.0699(7) 0.0446(7) 0.0376(6) -0.0057(5) -0.0138(5) 0.0148(5)
C8 0.0397(7) 0.0299(7) 0.0285(6) 0.0011(5) -0.0054(5) 0.0034(5)
C7 0.0430(7) 0.0286(7) 0.0308(7) 0.0014(5) -0.0048(5) 0.0015(5)
C5 0.0382(7) 0.0330(7) 0.0280(6) 0.0013(5) -0.0038(5) 0.0014(5)
C4 0.0595(9) 0.0348(8) 0.0319(7) -0.0053(6) -0.0140(6) -0.0012(5)
C6 0.0653(9) 0.0292(7) 0.0328(7) 0.0045(6) -0.0064(6) -0.0013(5)
C11 0.0483(8) 0.0411(8) 0.0303(7) -0.0008(6) -0.0044(6) 0.0028(6)
C2 0.0402(7) 0.0399(8) 0.0308(7) -0.0018(6) -0.0047(5) 0.0093(5)
C10 0.0391(7) 0.0331(7) 0.0273(6) -0.0017(5) -0.0051(5) 0.0044(5)
C9 0.0552(8) 0.0348(8) 0.0317(7) 0.0019(6) -0.0092(6) 0.0036(5)
N3 0.0724(9) 0.0609(9) 0.0378(7) 0.0062(7) -0.0092(6) 0.0165(6)
N4 0.0724(8) 0.0348(7) 0.0277(6) 0.0026(6) -0.0079(5) -0.0011(5)
C1 0.0624(9) 0.0392(8) 0.0257(6) 0.0048(7) -0.0056(6) -0.0028(5)
C3 0.0671(10) 0.0290(8) 0.0433(8) -0.0075(7) -0.0157(7) 0.0050(6)
N2 0.1055(12) 0.0331(8) 0.0532(8) 0.0077(7) -0.0173(7) 0.0000(6)
O2 0.0683(7) 0.0451(7) 0.0445(6) 0.0015(5) -0.0045(5) -0.0032(4)
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
C7 N1 C8 121.23(11)
C2 O1 H4 109.5
C10 C8 N1 117.76(12)
C10 C8 C9 119.92(11)
N1 C8 C9 122.32(11)
N1 C7 C5 122.35(12)
N1 C7 H6 118.8
C5 C7 H6 118.8
C4 C5 C6 118.22(12)
C4 C5 C7 122.03(11)
C6 C5 C7 119.74(12)
C3 C4 C5 120.50(12)
C3 C4 H5 119.7
C5 C4 H5 119.7
C1 C6 C5 121.44(13)
C1 C6 H1 119.3
C5 C6 H1 119.3
N3 C11 C10 178.44(16)
O1 C2 C1 121.79(12)
O1 C2 C3 118.13(13)
C1 C2 C3 120.07(12)
N4 C10 C8 123.85(11)
N4 C10 C11 116.52(11)
C8 C10 C11 119.63(12)
N2 C9 C8 176.94(14)
C10 N4 H4A 120.0
C10 N4 H4B 120.0
H4A N4 H4B 120.0
C2 C1 C6 119.40(12)
C2 C1 H2 120.3
C6 C1 H2 120.3
C4 C3 C2 120.34(14)
C4 C3 H3 119.8
C2 C3 H3 119.8
H8 O2 H7 105.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C7 1.2778(16)
N1 C8 1.3883(15)
O1 C2 1.3623(15)
O1 H4 0.8200
C8 C10 1.3651(17)
C8 C9 1.432(2)
C7 C5 1.4548(17)
C7 H6 0.9300
C5 C4 1.387(2)
C5 C6 1.3887(17)
C4 C3 1.3779(19)
C4 H5 0.9300
C6 C1 1.3786(18)
C6 H1 0.9300
C11 N3 1.1341(18)
C11 C10 1.4417(17)
C2 C1 1.376(2)
C2 C3 1.3787(19)
C10 N4 1.3368(18)
C9 N2 1.145(2)
N4 H4A 0.8600
N4 H4B 0.8600
C1 H2 0.9300
C3 H3 0.9300
O2 H8 0.8914
O2 H7 0.8848
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
O1 H4 O2 4_565 0.82 1.87 2.6848(16) 169
O2 H7 O1 2_545 0.88 2.04 2.8283(15) 148
O2 H8 N2 1_565 0.89 2.26 3.115(2) 161
N4 H4A N2 1_565 0.86 2.42 3.1691(19) 146
N4 H4B N3 2_556 0.86 2.15 3.0053(18) 171
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
C7 N1 C8 C10 -177.91(12)
C7 N1 C8 C9 1.88(19)
C8 N1 C7 C5 -179.19(11)
N1 C7 C5 C4 4.6(2)
N1 C7 C5 C6 -175.42(13)
C6 C5 C4 C3 -1.1(2)
C7 C5 C4 C3 178.85(13)
C4 C5 C6 C1 0.3(2)
C7 C5 C6 C1 -179.70(13)
N1 C8 C10 N4 2.76(19)
C9 C8 C10 N4 -177.04(13)
N1 C8 C10 C11 -177.51(11)
C9 C8 C10 C11 2.69(19)
O1 C2 C1 C6 178.49(13)
C3 C2 C1 C6 -1.3(2)
C5 C6 C1 C2 0.9(2)
C5 C4 C3 C2 0.8(2)
O1 C2 C3 C4 -179.33(13)
C1 C2 C3 C4 0.5(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654917
