#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/80/2208046.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_2208046
loop_
_publ_author_name
'Ju-Zhen Yuan'
'Ming-Wu Ding'
_publ_section_title
;
 4-Benzylidene-1-phenyl-2-propylamino-1H-imidazol-5(4H)-one
;
_journal_coeditor_code           DN6292
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o647
_journal_page_last               o648
_journal_paper_doi               10.1107/S1600536806000924
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C19 H19 N3 O'
_chemical_formula_moiety         'C19 H19 N3 O'
_chemical_formula_sum            'C19 H19 N3 O'
_chemical_formula_weight         305.37
_chemical_melting_point          456
_chemical_name_systematic
;
4-Benzylidene-1-phenyl-2-propylamino-1H-imidazol-5(4H)-one
;
_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                 99.058(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6442(11)
_cell_length_b                   11.3675(10)
_cell_length_c                   12.8149(12)
_cell_measurement_reflns_used    3773
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      23.84
_cell_measurement_theta_min      2.41
_cell_volume                     1675.1(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'SHELXTL (Bruker 2001) and PLATON (Spek, 2003)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14038
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3784
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0542
_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)+(0.0641P)²+0.168P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1429
_reflns_number_gt                2657
_reflns_number_total             3784
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn6292.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/c'
_cod_database_code               2208046
_cod_database_fobs_code          2208046
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_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
C1 0.57101(16) 0.64388(18) 0.48758(16) 0.0675(5) Uani d . 1 C
H1 0.5794 0.5936 0.5455 0.081 Uiso calc R 1 H
C2 0.51449(17) 0.7491(2) 0.4926(2) 0.0789(6) Uani d . 1 C
H2 0.4844 0.7691 0.5533 0.095 Uiso calc R 1 H
C3 0.50227(16) 0.8246(2) 0.4086(2) 0.0779(6) Uani d . 1 C
H3 0.4650 0.8964 0.4124 0.093 Uiso calc R 1 H
C4 0.54536(18) 0.79380(19) 0.31845(18) 0.0793(6) Uani d . 1 C
H4 0.5363 0.8448 0.2610 0.095 Uiso calc R 1 H
C5 0.60175(17) 0.68828(17) 0.31256(15) 0.0667(5) Uani d . 1 C
H5 0.6306 0.6687 0.2511 0.080 Uiso calc R 1 H
C6 0.61617(14) 0.61059(15) 0.39740(14) 0.0535(4) Uani d . 1 C
C7 0.67356(14) 0.49719(15) 0.39604(13) 0.0516(4) Uani d . 1 C
H7 0.6799 0.4540 0.4583 0.062 Uiso calc R 1 H
C8 0.71876(13) 0.44624(14) 0.31669(12) 0.0458(4) Uani d . 1 C
C9 0.77018(14) 0.32682(14) 0.32689(12) 0.0489(4) Uani d . 1 C
C10 0.77025(13) 0.40570(13) 0.16682(12) 0.0429(4) Uani d . 1 C
C11 0.85257(14) 0.19992(14) 0.19744(12) 0.0494(4) Uani d . 1 C
C12 0.79449(19) 0.09528(16) 0.20022(15) 0.0670(5) Uani d . 1 C
H12 0.7214 0.0930 0.2209 0.080 Uiso calc R 1 H
C13 0.8467(2) -0.00735(18) 0.17165(18) 0.0856(7) Uani d . 1 C
H13 0.8091 -0.0792 0.1744 0.103 Uiso calc R 1 H
C14 0.9531(3) -0.0028(2) 0.13959(18) 0.0902(7) Uani d . 1 C
H14 0.9872 -0.0717 0.1200 0.108 Uiso calc R 1 H
C15 1.0095(2) 0.1013(2) 0.13603(17) 0.0833(7) Uani d . 1 C
H15 1.0814 0.1037 0.1132 0.100 Uiso calc R 1 H
C16 0.96009(16) 0.20362(17) 0.16628(14) 0.0647(5) Uani d . 1 C
H16 0.9994 0.2748 0.1656 0.078 Uiso calc R 1 H
C17 0.74573(16) 0.50487(15) -0.00410(13) 0.0560(4) Uani d . 1 C
H17A 0.6908 0.5512 0.0281 0.067 Uiso calc R 1 H
H17B 0.7044 0.4722 -0.0693 0.067 Uiso calc R 1 H
C18 0.84051(18) 0.58471(17) -0.03000(15) 0.0712(6) Uani d . 1 C
H18A 0.8972 0.5381 -0.0597 0.085 Uiso calc R 1 H
H18B 0.8071 0.6409 -0.0833 0.085 Uiso calc R 1 H
C19 0.9008(2) 0.6501(2) 0.06400(19) 0.0952(7) Uani d . 1 C
H19A 0.8460 0.7001 0.0912 0.143 Uiso calc R 1 H
H19B 0.9621 0.6971 0.0437 0.143 Uiso calc R 1 H
H19C 0.9330 0.5950 0.1175 0.143 Uiso calc R 1 H
N1 0.72326(11) 0.48920(11) 0.21578(10) 0.0464(3) Uani d . 1 N
N2 0.80131(11) 0.30561(11) 0.22856(10) 0.0464(3) Uani d . 1 N
N3 0.78801(12) 0.40849(11) 0.06689(10) 0.0511(4) Uani d D 1 N
H3A 0.8088(14) 0.3436(10) 0.0389(13) 0.061 Uiso d D 1 H
O1 0.78467(12) 0.25914(11) 0.40157(10) 0.0698(4) Uani d . 1 O
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
C2 C1 C6 121.5(2)
C2 C1 H1 119.3
C6 C1 H1 119.3
C3 C2 C1 120.1(2)
C3 C2 H2 120.0
C1 C2 H2 120.0
C2 C3 C4 119.72(19)
C2 C3 H3 120.1
C4 C3 H3 120.1
C5 C4 C3 120.6(2)
C5 C4 H4 119.7
C3 C4 H4 119.7
C4 C5 C6 120.74(18)
C4 C5 H5 119.6
C6 C5 H5 119.6
C5 C6 C1 117.42(17)
C5 C6 C7 123.59(15)
C1 C6 C7 118.98(17)
C8 C7 C6 128.71(16)
C8 C7 H7 115.6
C6 C7 H7 115.6
C7 C8 N1 128.84(15)
C7 C8 C9 121.87(14)
N1 C8 C9 109.26(13)
O1 C9 N2 125.48(15)
O1 C9 C8 130.68(15)
N2 C9 C8 103.84(13)
N1 C10 N3 125.91(14)
N1 C10 N2 114.20(13)
N3 C10 N2 119.88(13)
C12 C11 C16 120.66(16)
C12 C11 N2 119.58(16)
C16 C11 N2 119.76(15)
C11 C12 C13 118.9(2)
C11 C12 H12 120.6
C13 C12 H12 120.6
C14 C13 C12 120.1(2)
C14 C13 H13 119.9
C12 C13 H13 119.9
C15 C14 C13 120.6(2)
C15 C14 H14 119.7
C13 C14 H14 119.7
C14 C15 C16 120.0(2)
C14 C15 H15 120.0
C16 C15 H15 120.0
C11 C16 C15 119.7(2)
C11 C16 H16 120.1
C15 C16 H16 120.1
N3 C17 C18 113.76(14)
N3 C17 H17A 108.8
C18 C17 H17A 108.8
N3 C17 H17B 108.8
C18 C17 H17B 108.8
H17A C17 H17B 107.7
C19 C18 C17 112.94(17)
C19 C18 H18A 109.0
C17 C18 H18A 109.0
C19 C18 H18B 109.0
C17 C18 H18B 109.0
H18A C18 H18B 107.8
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C10 N1 C8 105.77(13)
C9 N2 C10 106.92(12)
C9 N2 C11 125.57(13)
C10 N2 C11 127.50(12)
C10 N3 C17 122.02(13)
C10 N3 H3A 118.1(12)
C17 N3 H3A 117.9(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.372(3)
C1 C6 1.395(2)
C1 H1 0.9300
C2 C3 1.366(3)
C2 H2 0.9300
C3 C4 1.375(3)
C3 H3 0.9300
C4 C5 1.375(3)
C4 H4 0.9300
C5 C6 1.390(3)
C5 H5 0.9300
C6 C7 1.453(2)
C7 C8 1.347(2)
C7 H7 0.9300
C8 N1 1.3909(19)
C8 C9 1.481(2)
C9 O1 1.2188(18)
C9 N2 1.3860(19)
C10 N1 1.3047(19)
C10 N3 1.3292(19)
C10 N2 1.4004(18)
C11 C12 1.372(2)
C11 C16 1.373(2)
C11 N2 1.426(2)
C12 C13 1.391(3)
C12 H12 0.9300
C13 C14 1.367(3)
C13 H13 0.9300
C14 C15 1.358(3)
C14 H14 0.9300
C15 C16 1.380(3)
C15 H15 0.9300
C16 H16 0.9300
C17 N3 1.459(2)
C17 C18 1.506(3)
C17 H17A 0.9700
C17 H17B 0.9700
C18 C19 1.493(3)
C18 H18A 0.9700
C18 H18B 0.9700
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
N3 H3A 0.871(8)
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 O1 4_565 0.871(8) 2.094(13) 2.8452(17) 144.0(16)
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
C6 C1 C2 C3 -0.6(3)
C1 C2 C3 C4 1.0(3)
C2 C3 C4 C5 -0.7(3)
C3 C4 C5 C6 0.1(3)
C4 C5 C6 C1 0.2(3)
C4 C5 C6 C7 179.23(17)
C2 C1 C6 C5 0.0(3)
C2 C1 C6 C7 -179.03(17)
C5 C6 C7 C8 -1.8(3)
C1 C6 C7 C8 177.16(17)
C6 C7 C8 N1 0.6(3)
C6 C7 C8 C9 -177.26(15)
C7 C8 C9 O1 -2.8(3)
N1 C8 C9 O1 178.98(17)
C7 C8 C9 N2 177.54(14)
N1 C8 C9 N2 -0.72(16)
C16 C11 C12 C13 0.5(3)
N2 C11 C12 C13 -178.73(16)
C11 C12 C13 C14 -1.2(3)
C12 C13 C14 C15 0.5(3)
C13 C14 C15 C16 0.9(3)
C12 C11 C16 C15 0.9(3)
N2 C11 C16 C15 -179.90(16)
C14 C15 C16 C11 -1.6(3)
N3 C17 C18 C19 -65.0(2)
N3 C10 N1 C8 177.98(15)
N2 C10 N1 C8 -0.96(17)
C7 C8 N1 C10 -177.09(16)
C9 C8 N1 C10 1.01(16)
O1 C9 N2 C10 -179.56(16)
C8 C9 N2 C10 0.15(16)
O1 C9 N2 C11 1.8(3)
C8 C9 N2 C11 -178.48(14)
N1 C10 N2 C9 0.51(18)
N3 C10 N2 C9 -178.49(14)
N1 C10 N2 C11 179.11(14)
N3 C10 N2 C11 0.1(2)
C12 C11 N2 C9 59.4(2)
C16 C11 N2 C9 -119.82(18)
C12 C11 N2 C10 -118.98(18)
C16 C11 N2 C10 61.8(2)
N1 C10 N3 C17 -5.8(2)
N2 C10 N3 C17 173.10(14)
C18 C17 N3 C10 108.30(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1418013
