#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/90/2209054.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_2209054
loop_
_publ_author_name
'Ma, Rong-Ming'
'Ng, Seik Weng'
_publ_section_title
(Z)-4-Benzylidene-1-(4-chlorophenyl)-2-propylamino-1H-imidazol-5(4H)-one
_journal_coeditor_code           XU2034
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2090
_journal_page_last               o2091
_journal_paper_doi               10.1107/S160053680601467X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C19 H18 Cl N3 O'
_chemical_formula_moiety         'C19 H18 Cl N3 O'
_chemical_formula_sum            'C19 H18 Cl N3 O'
_chemical_formula_weight         339.81
_chemical_name_systematic
;
(Z)-4-Benzylidene-1-(4-chlorophenyl)-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                 103.3310(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9150(7)
_cell_length_b                   12.9335(8)
_cell_length_c                   12.8701(8)
_cell_measurement_reflns_used    3657
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      22.4
_cell_measurement_theta_min      2.3
_cell_volume                     1767.90(19)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Bruker SMART APEX 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  0.050
_diffrn_reflns_av_sigmaI/netI    0.042
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16744
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         1.9
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.97
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4038
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.97
_refine_ls_R_factor_all          0.083
_refine_ls_R_factor_gt           0.052
_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)+(0.0731P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.125
_refine_ls_wR_factor_ref         0.139
_reflns_number_gt                2612
_reflns_number_total             4038
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2034.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        1767.9(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2209054
_cod_database_fobs_code          2209054
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.43078(7) 0.61254(4) 0.62306(6) 0.1074(3) Uani d . 1 . .
O O1 0.25522(14) 0.22962(9) 0.90890(10) 0.0717(4) Uani d . 1 . .
N N1 0.27779(14) 0.19827(10) 0.73745(10) 0.0499(4) Uani d . 1 A .
N N2 0.22032(14) 0.02937(10) 0.71804(10) 0.0529(4) Uani d . 1 A .
C C1 0.31669(17) 0.29834(12) 0.71014(12) 0.0501(4) Uani d . 1 . .
C C2 0.42712(18) 0.31034(14) 0.67649(14) 0.0627(5) Uani d . 1 . .
C C3 0.4628(2) 0.40693(15) 0.64944(16) 0.0707(6) Uani d . 1 . .
C C4 0.3883(2) 0.49045(14) 0.65821(15) 0.0670(5) Uani d . 1 . .
C C5 0.2800(2) 0.47964(13) 0.69330(15) 0.0672(5) Uani d . 1 . .
C C6 0.24204(19) 0.38243(12) 0.71860(14) 0.0587(5) Uani d . 1 . .
C C7 0.24914(16) 0.17200(13) 0.83356(13) 0.0515(4) Uani d . 1 . .
C C8 0.21035(16) 0.06162(12) 0.81865(12) 0.0490(4) Uani d . 1 . .
C C9 0.25776(17) 0.10995(11) 0.67258(13) 0.0504(4) Uani d D 1 . .
N N3 0.27496(18) 0.11197(10) 0.57423(11) 0.0679(6) Uani d PD 1 . .
C C10 0.2742(5) 0.0157(3) 0.5131(3) 0.0617(13) Uani d PD 0.612(3) A 1
C C11 0.3783(6) -0.0595(4) 0.5588(4) 0.0669(14) Uani d PD 0.612(3) A 1
C C12 0.3847(4) -0.1467(2) 0.4812(3) 0.0784(11) Uani d PD 0.612(3) A 1
C C10' 0.2100(7) 0.0319(6) 0.4949(5) 0.073(2) Uani d PD 0.388(3) A 2
C C11' 0.3107(6) -0.0366(4) 0.4650(5) 0.085(2) Uani d PD 0.388(3) A 2
C C12' 0.3775(12) -0.1016(7) 0.5578(8) 0.101(4) Uani d PD 0.388(3) A 2
C C13 0.16922(17) 0.00765(13) 0.89299(13) 0.0553(5) Uani d . 1 . .
C C14 0.12379(17) -0.09906(13) 0.88653(14) 0.0549(5) Uani d . 1 . .
C C15 0.12365(19) -0.16436(14) 0.80050(15) 0.0653(5) Uani d . 1 . .
C C16 0.0783(2) -0.26386(15) 0.79929(18) 0.0746(6) Uani d . 1 . .
C C17 0.0332(2) -0.30097(17) 0.8838(2) 0.0783(6) Uani d . 1 . .
C C18 0.0319(2) -0.23816(17) 0.96882(18) 0.0803(6) Uani d . 1 . .
C C19 0.07598(19) -0.13815(16) 0.97019(15) 0.0701(6) Uani d . 1 . .
H H2 0.4774 0.2532 0.6721 0.075 Uiso calc R 1 . .
H H3 0.5363 0.4155 0.6256 0.085 Uiso calc R 1 . .
H H5 0.2318 0.5374 0.7002 0.081 Uiso calc R 1 . .
H H6 0.1674 0.3741 0.7409 0.070 Uiso calc R 1 . .
H H3n 0.2867 0.1702 0.5457 0.081 Uiso calc PR 0.612(3) A 1
H H10a 0.2800 0.0334 0.4411 0.074 Uiso calc PR 0.612(3) A 1
H H10b 0.1941 -0.0187 0.5081 0.074 Uiso calc PR 0.612(3) A 1
H H11a 0.3641 -0.0882 0.6247 0.080 Uiso calc PR 0.612(3) A 1
H H11b 0.4581 -0.0231 0.5755 0.080 Uiso calc PR 0.612(3) A 1
H H12a 0.4507 -0.1938 0.5132 0.118 Uiso calc PR 0.612(3) A 1
H H12b 0.4019 -0.1187 0.4170 0.118 Uiso calc PR 0.612(3) A 1
H H12c 0.3058 -0.1828 0.4645 0.118 Uiso calc PR 0.612(3) A 1
H H3n' 0.3224 0.1582 0.5557 0.081 Uiso calc PR 0.388(3) A 2
H H10c 0.1606 0.0655 0.4317 0.087 Uiso calc PR 0.388(3) A 2
H H10d 0.1540 -0.0098 0.5262 0.087 Uiso calc PR 0.388(3) A 2
H H11c 0.2716 -0.0815 0.4063 0.102 Uiso calc PR 0.388(3) A 2
H H11d 0.3716 0.0065 0.4412 0.102 Uiso calc PR 0.388(3) A 2
H H12d 0.4458 -0.1379 0.5388 0.151 Uiso calc PR 0.388(3) A 2
H H12e 0.3195 -0.1506 0.5757 0.151 Uiso calc PR 0.388(3) A 2
H H12f 0.4097 -0.0579 0.6182 0.151 Uiso calc PR 0.388(3) A 2
H H13 0.1697 0.0424 0.9564 0.066 Uiso calc R 1 . .
H H15 0.1545 -0.1406 0.7433 0.078 Uiso calc R 1 . .
H H16 0.0780 -0.3064 0.7410 0.089 Uiso calc R 1 . .
H H17 0.0039 -0.3685 0.8829 0.094 Uiso calc R 1 . .
H H18 0.0013 -0.2629 1.0258 0.096 Uiso calc R 1 . .
H H19 0.0738 -0.0958 1.0282 0.084 Uiso calc R 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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C7 N1 C9 107.20(10) no
C7 N1 C1 125.60(10) no
C9 N1 C1 127.20(10) no
C9 N2 C8 106.10(10) no
C6 C1 C2 120.7(2) no
C6 C1 N1 118.7(2) no
C2 C1 N1 120.6(2) no
C3 C2 C1 120.0(2) no
C4 C3 C2 119.1(2) no
C5 C4 C3 121.4(2) no
C5 C4 Cl1 118.9(2) no
C3 C4 Cl1 119.7(2) no
C4 C5 C6 119.9(2) no
C1 C6 C5 118.9(2) no
O1 C7 N1 125.5(2) no
O1 C7 C8 130.8(2) no
N1 C7 C8 103.70(10) no
C13 C8 N2 128.3(2) no
C13 C8 C7 122.60(10) no
N2 C8 C7 109.10(10) no
N2 C9 N3 125.0(2) no
N2 C9 N1 113.90(10) no
N3 C9 N1 121.10(10) no
C9 N3 C10 120.7(2) no
N3 C10 C11 115.2(4) no
C10 C11 C12 111.6(4) no
C12' C11' C10' 111.6(6) no
C8 C13 C14 127.9(2) no
C15 C14 C19 117.5(2) no
C15 C14 C13 123.8(2) no
C19 C14 C13 118.7(2) no
C16 C15 C14 120.7(2) no
C15 C16 C17 120.6(2) no
C18 C17 C16 119.8(2) no
C17 C18 C19 120.0(2) no
C18 C19 C14 121.4(2) no
C3 C2 H2 120.0 no
C1 C2 H2 120.0 no
C4 C3 H3 120.5 no
C2 C3 H3 120.5 no
C4 C5 H5 120.0 no
C6 C5 H5 120.0 no
C1 C6 H6 120.6 no
C5 C6 H6 120.6 no
C9 N3 H3n 119.6 no
C10 N3 H3n 119.6 no
N3 C10 H10a 108.5 no
C11 C10 H10a 108.5 no
N3 C10 H10b 108.5 no
C11 C10 H10b 108.5 no
H10a C10 H10b 107.5 no
C10 C11 H11a 109.3 no
C12 C11 H11a 109.3 no
C10 C11 H11b 109.3 no
C12 C11 H11b 109.3 no
H11a C11 H11b 108.0 no
C11 C12 H12a 109.5 no
C11 C12 H12b 109.5 no
H12a C12 H12b 109.5 no
C11 C12 H12c 109.5 no
H12a C12 H12c 109.5 no
H12b C12 H12c 109.5 no
C11' C10' H10c 110.0 no
C11' C10' H10d 110.0 no
H10c C10' H10d 108.4 no
C12' C11' H11c 109.3 no
C10' C11' H11c 109.3 no
C12' C11' H11d 109.3 no
C10' C11' H11d 109.3 no
H11c C11' H11d 108.0 no
C11' C12' H12d 109.5 no
C11' C12' H12e 109.5 no
H12d C12' H12e 109.5 no
C11' C12' H12f 109.5 no
H12d C12' H12f 109.5 no
H12e C12' H12f 109.5 no
C8 C13 H13 116.0 no
C14 C13 H13 116.0 no
C16 C15 H15 119.7 no
C14 C15 H15 119.7 no
C15 C16 H16 119.7 no
C17 C16 H16 119.7 no
C18 C17 H17 120.1 no
C16 C17 H17 120.1 no
C17 C18 H18 120.0 no
C19 C18 H18 120.0 no
C18 C19 H19 119.3 no
C14 C19 H19 119.3 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C4 1.735(2) no
O1 C7 1.213(2) no
N1 C7 1.386(2) no
N1 C9 1.402(2) no
N1 C1 1.431(2) no
N2 C9 1.306(2) no
N2 C8 1.388(2) no
C1 C6 1.378(2) no
C1 C2 1.380(2) no
C2 C3 1.377(2) no
C3 C4 1.372(3) no
C4 C5 1.366(3) no
C5 C6 1.386(2) no
C7 C8 1.489(2) no
C8 C13 1.342(2) no
C9 N3 1.322(2) no
N3 C10 1.472(4) no
C10 C11 1.508(6) no
C11 C12 1.519(5) no
C10' C11' 1.528(7) no
C11' C12' 1.504(8) no
C13 C14 1.462(2) no
C14 C15 1.392(3) no
C14 C19 1.395(2) no
C15 C16 1.378(2) no
C16 C17 1.379(3) no
C17 C18 1.366(3) no
C18 C19 1.379(3) no
C2 H2 0.93 no
C3 H3 0.93 no
C5 H5 0.93 no
C6 H6 0.93 no
N3 H3n 0.86 no
C10 H10a 0.97 no
C10 H10b 0.97 no
C11 H11a 0.97 no
C11 H11b 0.97 no
C12 H12a 0.96 no
C12 H12b 0.96 no
C12 H12c 0.96 no
C10' H10c 0.97 no
C10' H10d 0.97 no
C11' H11c 0.97 no
C11' H11d 0.97 no
C12' H12d 0.96 no
C12' H12e 0.96 no
C12' H12f 0.96 no
C13 H13 0.93 no
C15 H15 0.93 no
C16 H16 0.93 no
C17 H17 0.93 no
C18 H18 0.93 no
C19 H19 0.93 no
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
N3 H3n O1 4_565 0.86 2.15 2.926(2) 150 yes
N3 H3n' O1 4_565 0.86 2.36 2.926(2) 124 yes
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
C7 N1 C1 C6 -54.4(2) no
C9 N1 C1 C6 123.5(2) no
C7 N1 C1 C2 125.3(2) no
C9 N1 C1 C2 -56.8(3) no
C6 C1 C2 C3 -1.0(3) no
N1 C1 C2 C3 179.4(2) no
C1 C2 C3 C4 1.1(3) no
C2 C3 C4 C5 0.1(3) no
C2 C3 C4 Cl1 -179.3(2) no
C3 C4 C5 C6 -1.5(3) no
Cl1 C4 C5 C6 178.00(10) no
C2 C1 C6 C5 -0.4(3) no
N1 C1 C6 C5 179.3(2) no
C4 C5 C6 C1 1.6(3) no
C9 N1 C7 O1 -179.7(2) no
C1 N1 C7 O1 -1.5(3) no
C9 N1 C7 C8 -0.3(2) no
C1 N1 C7 C8 178.0(2) no
C9 N2 C8 C13 176.4(2) no
C9 N2 C8 C7 -1.5(2) no
O1 C7 C8 C13 2.5(3) no
N1 C7 C8 C13 -176.9(2) no
O1 C7 C8 N2 -179.5(2) no
N1 C7 C8 N2 1.1(2) no
C8 N2 C9 N3 -177.9(2) no
C8 N2 C9 N1 1.3(2) no
C7 N1 C9 N2 -0.7(2) no
C1 N1 C9 N2 -178.9(2) no
C7 N1 C9 N3 178.6(2) no
C1 N1 C9 N3 0.4(3) no
N2 C9 N3 C10 -11.0(4) no
N1 C9 N3 C10 169.8(3) no
C9 N3 C10 C11 -63.8(5) no
N3 C10 C11 C12 -169.7(4) no
N2 C8 C13 C14 -0.3(3) no
C7 C8 C13 C14 177.3(2) no
C8 C13 C14 C15 4.0(3) no
C8 C13 C14 C19 -175.1(2) no
C19 C14 C15 C16 -0.3(3) no
C13 C14 C15 C16 -179.4(2) no
C14 C15 C16 C17 -0.6(3) no
C15 C16 C17 C18 0.9(3) no
C16 C17 C18 C19 -0.3(3) no
C17 C18 C19 C14 -0.7(3) no
C15 C14 C19 C18 1.0(3) no
C13 C14 C19 C18 -179.9(2) no
