#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/21/2222100.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_2222100
loop_
_publ_author_name
'Tamilvendan, Dhanapal'
'Venkatesa Prabhu, Ganesan'
'Fronczek, Frank R.'
'Vembu, Nagarajan'
_publ_section_title
;
 N,N'-(Phenyliminodimethylene)diprop-2-enamide
 hemihydrate
;
_journal_coeditor_code           LH2820
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1343
_journal_paper_doi               10.1107/S1600536809017784
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H17 N3 O2, 0.5H2 O1'
_chemical_formula_moiety         'C14 H17 N3 O2, 0.5(H2 O1)'
_chemical_formula_sum            'C14 H18 N3 O2.5'
_chemical_formula_weight         268.31
_chemical_melting_point          398
_chemical_name_systematic
;
N,N'-(Phenyliminodimethylene)diprop-2-enamide hemihydrate
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.074(2)
_cell_length_b                   9.8366(15)
_cell_length_c                   16.316(2)
_cell_measurement_reflns_used    34434
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      33.0
_cell_measurement_theta_min      2.5
_cell_volume                     2740.3(6)
_computing_cell_refinement
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type
'Nonius KappaCCD diffractometer with an Oxford Cryosystems Cryostream cooler'
_diffrn_measurement_method       'ω and φ'
_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  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9467
_diffrn_reflns_theta_full        32.96
_diffrn_reflns_theta_max         32.96
_diffrn_reflns_theta_min         2.70
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.283
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         5065
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0597P)²+0.7128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1195
_reflns_number_gt                3885
_reflns_number_total             5065
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2820.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C14 H18 N3 O2.50'
_cod_database_code               2222100
_cod_database_fobs_code          2222100
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, 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_disorder_assembly
_atom_site_disorder_group
N N1 0.80007(5) 0.89440(8) 0.13232(5) 0.01594(16) Uani d . 1 . .
C C2 0.88056(6) 0.84769(10) 0.12071(6) 0.01569(17) Uani d . 1 . .
N N3 0.89921(5) 0.80690(8) 0.03825(5) 0.01545(16) Uani d . 1 . .
C C4 0.91579(6) 0.66584(10) 0.02225(6) 0.01665(18) Uani d . 1 . .
N N5 0.85082(5) 0.59623(8) -0.01804(5) 0.01671(16) Uani d . 1 . .
C C6 0.85921(6) 0.52348(9) -0.08750(6) 0.01635(18) Uani d . 1 . .
O O7 0.92364(4) 0.50903(8) -0.12139(5) 0.02232(17) Uani d . 1 . .
C C8 0.78566(6) 0.46251(11) -0.11941(6) 0.0210(2) Uani d . 1 . .
C C9 0.78569(7) 0.37886(13) -0.18250(7) 0.0267(2) Uani d . 1 . .
C C10 0.73876(5) 0.80842(9) 0.13486(5) 0.01421(17) Uani d . 1 . .
O O11 0.74626(4) 0.68455(7) 0.12367(4) 0.01761(15) Uani d . 1 . .
C C12 0.66234(6) 0.87457(10) 0.15303(6) 0.01837(19) Uani d . 1 . .
C C13 0.59676(6) 0.80534(12) 0.16321(7) 0.0247(2) Uani d . 1 . .
C C14 0.90493(5) 0.90267(10) -0.02424(6) 0.01502(17) Uani d . 1 . .
C C15 0.91823(5) 0.86297(11) -0.10565(6) 0.01785(19) Uani d . 1 . .
C C16 0.92620(6) 0.96063(12) -0.16649(6) 0.0226(2) Uani d . 1 . .
C C17 0.92139(6) 1.09817(12) -0.14964(7) 0.0249(2) Uani d . 1 . .
C C18 0.90668(6) 1.13762(11) -0.06939(7) 0.0229(2) Uani d . 1 . .
C C19 0.89752(6) 1.04206(10) -0.00757(7) 0.01868(19) Uani d . 1 . .
O OW 1.0000 0.37093(12) -0.2500 0.0356(3) Uani d S 1 . .
H H1 0.7899(9) 0.9829(15) 0.1371(9) 0.028(4) Uiso d . 1 . .
H H2A 0.8901(7) 0.7705(14) 0.1559(8) 0.018(3) Uiso d . 1 . .
H H2B 0.9140(7) 0.9206(14) 0.1393(8) 0.015(3) Uiso d . 1 . .
H H4A 0.9616(8) 0.6566(13) -0.0140(8) 0.018(3) Uiso d . 1 . .
H H4B 0.9274(7) 0.6225(13) 0.0743(8) 0.017(3) Uiso d . 1 . .
H H5 0.8046(9) 0.6058(14) 0.0045(9) 0.027(3) Uiso d . 1 . .
H H8 0.7378(9) 0.4864(15) -0.0914(10) 0.035(4) Uiso d . 1 . .
H H9A 0.7377(8) 0.3357(15) -0.2005(9) 0.029(4) Uiso d . 1 . .
H H9B 0.8348(9) 0.3542(15) -0.2119(10) 0.036(4) Uiso d . 1 . .
H H12 0.6636(9) 0.9714(16) 0.1589(10) 0.034(4) Uiso d . 1 . .
H H13A 0.5471(8) 0.8504(15) 0.1751(8) 0.027(3) Uiso d . 1 . .
H H13B 0.5952(10) 0.7040(19) 0.1577(11) 0.045(5) Uiso d . 1 . .
H H15 0.9212(7) 0.7696(15) -0.1208(8) 0.018(3) Uiso d . 1 . .
H H16 0.9353(9) 0.9338(15) -0.2219(9) 0.031(4) Uiso d . 1 . .
H H17 0.9294(9) 1.1688(16) -0.1936(10) 0.038(4) Uiso d . 1 . .
H H18 0.9027(8) 1.2309(16) -0.0557(9) 0.029(4) Uiso d . 1 . .
H H19 0.8871(8) 1.0736(14) 0.0458(9) 0.022(3) Uiso d . 1 . .
H HW 1.0232(10) 0.4232(17) -0.2832(11) 0.048(5) Uiso d . 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 N1 C2 . . 122.52(8) ?
C10 N1 H1 . . 117.3(10) ?
C2 N1 H1 . . 120.2(10) ?
N3 C2 N1 . . 114.64(8) ?
N3 C2 H2A . . 107.4(8) ?
N1 C2 H2A . . 109.2(8) ?
N3 C2 H2B . . 111.7(8) ?
N1 C2 H2B . . 106.4(8) ?
H2A C2 H2B . . 107.3(11) ?
C14 N3 C2 . . 120.77(8) ?
C14 N3 C4 . . 120.38(8) ?
C2 N3 C4 . . 118.78(8) ?
N3 C4 N5 . . 112.59(8) ?
N3 C4 H4A . . 110.7(7) ?
N5 C4 H4A . . 106.8(7) ?
N3 C4 H4B . . 107.8(8) ?
N5 C4 H4B . . 110.0(8) ?
H4A C4 H4B . . 108.8(11) ?
C6 N5 C4 . . 123.15(8) ?
C6 N5 H5 . . 120.4(10) ?
C4 N5 H5 . . 116.4(9) ?
O7 C6 N5 . . 122.03(9) ?
O7 C6 C8 . . 123.19(9) ?
N5 C6 C8 . . 114.78(8) ?
C9 C8 C6 . . 121.70(9) ?
C9 C8 H8 . . 121.4(9) ?
C6 C8 H8 . . 116.9(9) ?
C8 C9 H9A . . 120.7(9) ?
C8 C9 H9B . . 121.9(9) ?
H9A C9 H9B . . 117.4(12) ?
O11 C10 N1 . . 122.20(9) ?
O11 C10 C12 . . 123.38(9) ?
N1 C10 C12 . . 114.41(8) ?
C13 C12 C10 . . 122.88(9) ?
C13 C12 H12 . . 121.3(9) ?
C10 C12 H12 . . 115.8(9) ?
C12 C13 H13A . . 121.8(9) ?
C12 C13 H13B . . 121.6(10) ?
H13A C13 H13B . . 116.6(13) ?
N3 C14 C15 . . 121.10(9) ?
N3 C14 C19 . . 120.87(9) ?
C15 C14 C19 . . 118.03(9) ?
C16 C15 C14 . . 120.02(10) ?
C16 C15 H15 . . 118.5(8) ?
C14 C15 H15 . . 121.5(8) ?
C17 C16 C15 . . 121.95(10) ?
C17 C16 H16 . . 118.0(9) ?
C15 C16 H16 . . 120.1(9) ?
C16 C17 C18 . . 118.13(10) ?
C16 C17 H17 . . 121.7(9) ?
C18 C17 H17 . . 120.2(9) ?
C19 C18 C17 . . 121.10(10) ?
C19 C18 H18 . . 118.4(9) ?
C17 C18 H18 . . 120.5(9) ?
C18 C19 C14 . . 120.72(10) ?
C18 C19 H19 . . 118.1(8) ?
C14 C19 H19 . . 121.2(8) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C10 . 1.3465(12) ?
N1 C2 . 1.4613(13) ?
N1 H1 . 0.891(15) ?
C2 N3 . 1.4397(12) ?
C2 H2A . 0.966(13) ?
C2 H2B . 0.966(13) ?
N3 C14 . 1.3915(12) ?
N3 C4 . 1.4400(12) ?
C4 N5 . 1.4599(12) ?
C4 H4A . 0.984(13) ?
C4 H4B . 0.970(13) ?
N5 C6 . 1.3480(12) ?
N5 H5 . 0.876(15) ?
C6 O7 . 1.2394(12) ?
C6 C8 . 1.4859(14) ?
C8 C9 . 1.3178(15) ?
C8 H8 . 0.966(16) ?
C9 H9A . 0.969(14) ?
C9 H9B . 0.996(16) ?
C10 O11 . 1.2387(11) ?
C10 C12 . 1.4878(14) ?
C12 C13 . 1.3210(15) ?
C12 H12 . 0.957(16) ?
C13 H13A . 0.976(14) ?
C13 H13B . 1.001(19) ?
C14 C15 . 1.4030(14) ?
C14 C19 . 1.4036(14) ?
C15 C16 . 1.3880(14) ?
C15 H15 . 0.953(14) ?
C16 C17 . 1.3830(17) ?
C16 H16 . 0.954(15) ?
C17 C18 . 1.3886(17) ?
C17 H17 . 1.008(16) ?
C18 C19 . 1.3876(15) ?
C18 H18 . 0.947(16) ?
C19 H19 . 0.942(14) ?
OW HW . 0.845(17) ?
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
N5 H5 O11 . 0.876(15) 2.318(15) 3.0476(11) 140.8(12) y
C4 H4A O7 . 0.984(13) 2.366(13) 2.8089(12) 106.5(9) y
C15 H15 O7 . 0.953(14) 2.563(14) 3.4922(14) 165.1(10) y
OW HW O7 4_754 0.845(17) 1.990(17) 2.8193(9) 166.7(16) y
N1 H1 O11 7_765 0.891(15) 2.089(15) 2.9651(11) 167.4(14) y
C2 H2B Cg1 5_775 0.966(13) 3.178 3.874 130.40 y
C8 H8 Cg1 7_645 0.966(16) 2.571 3.444 150.57 y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 N1 C2 N3 . . . . 75.00(12) ?
N1 C2 N3 C14 . . . . 70.15(11) ?
N1 C2 N3 C4 . . . . -112.95(9) ?
C14 N3 C4 N5 . . . . -78.90(10) ?
C2 N3 C4 N5 . . . . 104.19(10) ?
N3 C4 N5 C6 . . . . 127.89(10) ?
C4 N5 C6 O7 . . . . 1.15(15) ?
C4 N5 C6 C8 . . . . -179.03(9) ?
O7 C6 C8 C9 . . . . 5.99(17) ?
N5 C6 C8 C9 . . . . -173.83(11) ?
C2 N1 C10 O11 . . . . -3.45(14) ?
C2 N1 C10 C12 . . . . 175.89(8) ?
O11 C10 C12 C13 . . . . 3.88(16) ?
N1 C10 C12 C13 . . . . -175.46(10) ?
C2 N3 C14 C15 . . . . -175.96(8) ?
C4 N3 C14 C15 . . . . 7.19(13) ?
C2 N3 C14 C19 . . . . 4.02(13) ?
C4 N3 C14 C19 . . . . -172.83(8) ?
N3 C14 C15 C16 . . . . -177.94(9) ?
C19 C14 C15 C16 . . . . 2.09(13) ?
C14 C15 C16 C17 . . . . -0.07(15) ?
C15 C16 C17 C18 . . . . -1.19(16) ?
C16 C17 C18 C19 . . . . 0.39(15) ?
C17 C18 C19 C14 . . . . 1.67(15) ?
N3 C14 C19 C18 . . . . 177.14(9) ?
C15 C14 C19 C18 . . . . -2.88(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26000925
