#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/70/2217076.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_2217076
loop_
_publ_author_name
'Lin Li'
'Yan-Hong Tian'
'Chu-Yi Yu'
'Li-Ben Wang'
_publ_section_title
;
 (E)-Benzoyl[1-(2-hydroxyethyl)imidazolidin-2-ylidene]acetonitrile
;
_journal_coeditor_code           HB2622
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o62
_journal_page_last               o62
_journal_paper_doi               10.1107/S1600536807055778
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C14 H15 N3 O2'
_chemical_formula_moiety         'C14 H15 N3 O2'
_chemical_formula_sum            'C14 H15 N3 O2'
_chemical_formula_weight         257.29
_chemical_melting_point          .449E-305
_chemical_name_systematic
;
(E)-Benzoyl[1-(2-hydroxyethyl)imidazolidin-2-ylidene]acetonitrile
;
_space_group_IT_number           14
_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                 107.33(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3748(17)
_cell_length_b                   14.633(3)
_cell_length_c                   10.784(2)
_cell_measurement_reflns_used    4329
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      22.5
_cell_measurement_theta_min      2.3
_cell_volume                     1261.6(5)
_computing_cell_refinement       '(CrystalClear; Rigaku, 2005)'
_computing_data_collection       '(CrystalClear; Rigaku, 2005)'
_computing_data_reduction        '(CrystalClear; Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9551
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         2.42
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.179
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2994
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0408
_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)+(0.0503P)²+0.2093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1031
_reflns_number_gt                2534
_reflns_number_total             2994
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            hb2622.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        1261.6(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2217076
_cod_database_fobs_code          2217076
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
O O1 0.30219(13) 0.59907(7) 0.03041(9) 0.0280(2) Uani d . 1
H H1 0.323(2) 0.6459(13) -0.0116(18) 0.044(5) Uiso d . 1
O O2 0.91862(10) 0.56888(6) 0.57744(8) 0.0186(2) Uani d . 1
N N1 0.47423(12) 0.51059(7) 0.28326(10) 0.0171(2) Uani d . 1
N N2 0.72478(13) 0.46439(7) 0.39657(10) 0.0170(2) Uani d . 1
N N3 0.41182(14) 0.73000(8) 0.45144(11) 0.0259(3) Uani d . 1
C C1 0.30005(16) 0.63405(9) 0.15308(12) 0.0195(3) Uani d . 1
H H1A 0.1954 0.6687 0.1432 0.023 Uiso calc R 1
H H1B 0.3957 0.6760 0.1876 0.023 Uiso calc R 1
C C2 0.31137(15) 0.55527(9) 0.24601(11) 0.0169(3) Uani d . 1
H H2A 0.2878 0.5781 0.3252 0.020 Uiso calc R 1
H H2B 0.2244 0.5097 0.2049 0.020 Uiso calc R 1
C C3 0.49585(16) 0.42196(9) 0.22523(12) 0.0201(3) Uani d . 1
H H3A 0.4665 0.4264 0.1295 0.024 Uiso calc R 1
H H3B 0.4264 0.3740 0.2483 0.024 Uiso calc R 1
C C4 0.68186(16) 0.40238(9) 0.28553(12) 0.0210(3) Uani d . 1
H H4A 0.7016 0.3378 0.3135 0.025 Uiso calc R 1
H H4B 0.7461 0.4167 0.2244 0.025 Uiso calc R 1
C C5 0.61006(14) 0.53014(8) 0.38307(11) 0.0150(2) Uani d . 1
C C6 0.63996(14) 0.60969(8) 0.46455(11) 0.0154(2) Uani d . 1
C C7 0.51223(15) 0.67519(9) 0.45570(11) 0.0178(3) Uani d . 1
C C8 0.80273(14) 0.62602(8) 0.55445(11) 0.0151(2) Uani d . 1
C C10 0.79435(15) 0.79899(9) 0.56137(12) 0.0194(3) Uani d . 1
H H10 0.7338 0.7999 0.4716 0.023 Uiso calc R 1
C C11 0.83750(16) 0.88063(9) 0.62852(13) 0.0236(3) Uani d . 1
H H11 0.8066 0.9372 0.5848 0.028 Uiso calc R 1
C C12 0.92588(16) 0.87938(10) 0.75974(13) 0.0238(3) Uani d . 1
H H12 0.9541 0.9352 0.8062 0.029 Uiso calc R 1
C C13 0.97302(16) 0.79694(10) 0.82305(12) 0.0225(3) Uani d . 1
H H13 1.0342 0.7964 0.9127 0.027 Uiso calc R 1
C C9 0.83921(14) 0.71581(8) 0.62480(11) 0.0154(2) Uani d . 1
C C14 0.93138(15) 0.71500(9) 0.75621(12) 0.0194(3) Uani d . 1
H H14 0.9654 0.6586 0.7997 0.023 Uiso calc R 1
H H2 0.827(2) 0.4743(11) 0.4482(16) 0.031(4) 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
C1 O1 H1 105.2(12)
C5 N1 C2 128.69(10)
C5 N1 C3 110.22(10)
C2 N1 C3 120.06(10)
C5 N2 C4 111.39(10)
C5 N2 H2 118.7(11)
C4 N2 H2 125.1(11)
O1 C1 C2 109.04(10)
O1 C1 H1A 109.9
C2 C1 H1A 109.9
O1 C1 H1B 109.9
C2 C1 H1B 109.9
H1A C1 H1B 108.3
N1 C2 C1 113.19(10)
N1 C2 H2A 108.9
C1 C2 H2A 108.9
N1 C2 H2B 108.9
C1 C2 H2B 108.9
H2A C2 H2B 107.8
N1 C3 C4 102.90(10)
N1 C3 H3A 111.2
C4 C3 H3A 111.2
N1 C3 H3B 111.2
C4 C3 H3B 111.2
H3A C3 H3B 109.1
N2 C4 C3 101.74(10)
N2 C4 H4A 111.4
C3 C4 H4A 111.4
N2 C4 H4B 111.4
C3 C4 H4B 111.4
H4A C4 H4B 109.3
N2 C5 N1 110.10(11)
N2 C5 C6 121.91(11)
N1 C5 C6 127.95(11)
C7 C6 C5 121.11(11)
C7 C6 C8 118.52(11)
C5 C6 C8 120.35(11)
N3 C7 C6 177.90(13)
O2 C8 C6 123.17(11)
O2 C8 C9 117.15(10)
C6 C8 C9 119.68(10)
C11 C10 C9 120.40(12)
C11 C10 H10 119.8
C9 C10 H10 119.8
C10 C11 C12 119.83(13)
C10 C11 H11 120.1
C12 C11 H11 120.1
C13 C12 C11 120.10(12)
C13 C12 H12 120.0
C11 C12 H12 120.0
C12 C13 C14 120.37(12)
C12 C13 H13 119.8
C14 C13 H13 119.8
C10 C9 C14 119.50(11)
C10 C9 C8 122.15(11)
C14 C9 C8 118.20(11)
C13 C14 C9 119.77(12)
C13 C14 H14 120.1
C9 C14 H14 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.4235(15) ?
O1 H1 0.87(2) ?
O2 C8 1.2487(14) n
N1 C5 1.3435(16) n
N1 C2 1.4569(16) ?
N1 C3 1.4744(16) ?
N2 C5 1.3366(16) n
N2 C4 1.4595(16) ?
N2 H2 0.881(16) n
N3 C7 1.1530(16) ?
C1 C2 1.5119(17) ?
C1 H1A 0.9900 ?
C1 H1B 0.9900 ?
C2 H2A 0.9900 ?
C2 H2B 0.9900 ?
C3 C4 1.5258(18) ?
C3 H3A 0.9900 ?
C3 H3B 0.9900 ?
C4 H4A 0.9900 ?
C4 H4B 0.9900 ?
C5 C6 1.4348(17) n
C6 C7 1.4182(17) ?
C6 C8 1.4381(17) n
C8 C9 1.5022(16) n
C10 C11 1.3879(18) ?
C10 C9 1.3920(17) ?
C10 H10 0.9500 ?
C11 C12 1.388(2) ?
C11 H11 0.9500 ?
C12 C13 1.384(2) ?
C12 H12 0.9500 ?
C13 C14 1.3889(18) ?
C13 H13 0.9500 ?
C9 C14 1.3974(17) ?
C14 H14 0.9500 ?
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
N2 H2 O2 3_766 0.881(16) 2.318(16) 2.9557(15) 129.3(13)
N2 H2 O2 . 0.881(16) 1.953(16) 2.6252(15) 132.0(14)
O1 H1 N3 4_575 0.87(2) 2.04(2) 2.8794(16) 160.9(17)
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
C5 N1 C2 C1 89.49(14) ?
C3 N1 C2 C1 -103.33(13) ?
O1 C1 C2 N1 69.56(13) ?
C5 N1 C3 C4 -12.82(13) y
C2 N1 C3 C4 177.82(10) ?
C5 N2 C4 C3 -18.34(13) y
N1 C3 C4 N2 17.71(12) y
C4 N2 C5 N1 11.16(14) y
C4 N2 C5 C6 -166.78(11) ?
C2 N1 C5 N2 169.93(11) ?
C3 N1 C5 N2 1.74(14) y
C2 N1 C5 C6 -12.3(2) ?
C3 N1 C5 C6 179.52(11) ?
N2 C5 C6 C7 -174.96(11) ?
N1 C5 C6 C7 7.49(19) ?
N2 C5 C6 C8 7.02(17) ?
N1 C5 C6 C8 -170.52(11) ?
C7 C6 C8 O2 173.51(11) ?
C5 C6 C8 O2 -8.42(18) ?
C7 C6 C8 C9 -6.98(16) ?
C5 C6 C8 C9 171.09(10) ?
C9 C10 C11 C12 -0.02(19) ?
C10 C11 C12 C13 0.94(19) ?
C11 C12 C13 C14 -0.45(19) ?
C11 C10 C9 C14 -1.39(18) ?
C11 C10 C9 C8 -176.84(11) ?
O2 C8 C9 C10 133.69(12) ?
C6 C8 C9 C10 -45.85(16) ?
O2 C8 C9 C14 -41.82(15) ?
C6 C8 C9 C14 138.64(12) ?
C12 C13 C14 C9 -0.96(18) ?
C10 C9 C14 C13 1.87(18) ?
C8 C9 C14 C13 177.50(10) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9024037
