#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/64/2206413.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_2206413
loop_
_publ_author_name
'Jun Wan'
'Zheng-Zhong Peng'
'Xue-Mei Li'
'Ping-Kai Ouyang'
'Shu-Sheng Zhang'
_publ_section_title
;
 1-(4-Chlorophenyl)-3-(1H-imidazol-1-yl)propan-1-one
;
_journal_coeditor_code           DN6238
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2659
_journal_page_last               o2660
_journal_paper_doi               10.1107/S160053680502310X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C12 H11 Cl N2 O'
_chemical_formula_moiety         'C12 H11 Cl N2 O'
_chemical_formula_sum            'C12 H11 Cl N2 O'
_chemical_formula_weight         234.68
_chemical_name_systematic
;
1-(4-Chlorophenyl)-3-(1H-imidazol-1-yl)propan-1-one
;
_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                 107.2520(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4902(9)
_cell_length_b                   8.1611(7)
_cell_length_c                   13.8691(12)
_cell_measurement_reflns_used    2278
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.9
_cell_measurement_theta_min      2.9
_cell_volume                     1133.94(17)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Siemens SMART 1000 CCD area-detector'
_diffrn_measurement_method       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  0.0167
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6176
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        0.1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_T_max  0.9813
_exptl_absorpt_correction_T_min  0.8607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       flattened
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2218
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0411
_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)+(0.0533P)²+0.2452P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1118
_reflns_number_gt                1860
_reflns_number_total             2218
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn6238.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2206413
_cod_database_fobs_code          2206413
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
Cl1 0.03977(5) 1.08089(7) 0.36239(4) 0.0733(2) Uani d . 1 Cl
O1 0.59667(14) 0.66317(19) 0.58137(9) 0.0734(4) Uani d . 1 O
N1 0.83076(14) 0.54895(18) 0.39364(10) 0.0508(4) Uani d . 1 N
N2 0.88810(19) 0.4584(2) 0.26214(13) 0.0740(5) Uani d . 1 N
C1 0.36623(18) 0.8551(2) 0.52882(12) 0.0524(4) Uani d . 1 C
H1 0.4077 0.8355 0.5970 0.063 Uiso calc R 1 H
C2 0.24869(19) 0.9413(2) 0.50041(13) 0.0552(4) Uani d . 1 C
H2 0.2105 0.9797 0.5487 0.066 Uiso calc R 1 H
C3 0.18798(17) 0.9703(2) 0.39911(13) 0.0525(4) Uani d . 1 C
C4 0.24348(19) 0.9149(2) 0.32667(13) 0.0609(5) Uani d . 1 C
H4 0.2016 0.9354 0.2587 0.073 Uiso calc R 1 H
C5 0.36164(18) 0.8288(2) 0.35615(12) 0.0555(5) Uani d . 1 C
H5 0.3998 0.7919 0.3076 0.067 Uiso calc R 1 H
C6 0.42471(16) 0.7964(2) 0.45756(12) 0.0462(4) Uani d . 1 C
C7 0.55162(17) 0.7017(2) 0.49302(12) 0.0504(4) Uani d . 1 C
C8 0.62225(17) 0.6537(2) 0.41750(12) 0.0511(4) Uani d . 1 C
H8A 0.6368 0.7508 0.3819 0.061 Uiso calc R 1 H
H8B 0.5657 0.5798 0.3683 0.061 Uiso calc R 1 H
C9 0.75452(18) 0.5715(2) 0.46592(13) 0.0551(4) Uani d . 1 C
H9A 0.8061 0.6377 0.5221 0.066 Uiso calc R 1 H
H9B 0.7392 0.4656 0.4923 0.066 Uiso calc R 1 H
C10 0.93759(18) 0.6373(3) 0.38862(14) 0.0620(5) Uani d . 1 C
H10 0.9793 0.7212 0.4320 0.074 Uiso calc R 1 H
C11 0.9717(2) 0.5804(3) 0.30872(15) 0.0681(6) Uani d . 1 C
H11 1.0429 0.6193 0.2882 0.082 Uiso calc R 1 H
C12 0.8046(2) 0.4441(3) 0.31576(16) 0.0689(5) Uani d . 1 C
H12 0.7346 0.3693 0.3013 0.083 Uiso calc R 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
Cl1 0.0672(3) 0.0889(4) 0.0632(3) 0.0135(3) 0.0182(3) -0.0014(3)
O1 0.0779(9) 0.1047(11) 0.0401(7) 0.0158(8) 0.0214(6) 0.0128(7)
N1 0.0545(8) 0.0555(8) 0.0426(8) 0.0013(6) 0.0148(6) 0.0003(6)
N2 0.0832(12) 0.0851(12) 0.0610(10) 0.0023(10) 0.0326(9) -0.0099(9)
C1 0.0621(10) 0.0627(11) 0.0344(9) -0.0086(9) 0.0176(8) -0.0019(7)
C2 0.0630(11) 0.0628(11) 0.0455(10) -0.0054(8) 0.0250(8) -0.0078(8)
C3 0.0549(10) 0.0558(10) 0.0471(10) -0.0052(8) 0.0157(8) -0.0045(8)
C4 0.0662(12) 0.0767(13) 0.0381(9) 0.0023(10) 0.0130(8) -0.0024(9)
C5 0.0629(11) 0.0703(12) 0.0376(9) -0.0003(9) 0.0213(8) -0.0047(8)
C6 0.0537(9) 0.0501(9) 0.0381(8) -0.0106(7) 0.0185(7) -0.0027(7)
C7 0.0590(10) 0.0553(10) 0.0385(9) -0.0086(8) 0.0171(8) 0.0005(7)
C8 0.0575(10) 0.0578(10) 0.0404(9) -0.0023(8) 0.0181(8) 0.0023(7)
C9 0.0621(11) 0.0624(11) 0.0433(9) -0.0011(8) 0.0197(8) 0.0022(8)
C10 0.0592(11) 0.0705(12) 0.0566(11) -0.0087(9) 0.0179(9) -0.0047(9)
C11 0.0600(11) 0.0892(15) 0.0603(12) 0.0022(10) 0.0259(10) 0.0082(11)
C12 0.0766(13) 0.0722(13) 0.0615(12) -0.0124(10) 0.0262(10) -0.0127(10)
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
C12 N1 C10 105.90(15)
C12 N1 C9 127.39(16)
C10 N1 C9 126.60(15)
C12 N2 C11 103.96(17)
C2 C1 C6 121.32(16)
C2 C1 H1 119.3
C6 C1 H1 119.3
C1 C2 C3 118.96(16)
C1 C2 H2 120.5
C3 C2 H2 120.5
C4 C3 C2 121.25(17)
C4 C3 Cl1 119.42(14)
C2 C3 Cl1 119.33(14)
C5 C4 C3 119.24(16)
C5 C4 H4 120.4
C3 C4 H4 120.4
C4 C5 C6 120.92(16)
C4 C5 H5 119.5
C6 C5 H5 119.5
C5 C6 C1 118.30(16)
C5 C6 C7 122.88(15)
C1 C6 C7 118.82(15)
O1 C7 C6 120.55(15)
O1 C7 C8 120.67(17)
C6 C7 C8 118.79(14)
C7 C8 C9 112.59(14)
C7 C8 H8A 109.1
C9 C8 H8A 109.1
C7 C8 H8B 109.1
C9 C8 H8B 109.1
H8A C8 H8B 107.8
N1 C9 C8 111.56(14)
N1 C9 H9A 109.3
C8 C9 H9A 109.3
N1 C9 H9B 109.3
C8 C9 H9B 109.3
H9A C9 H9B 108.0
C11 C10 N1 106.59(18)
C11 C10 H10 126.7
N1 C10 H10 126.7
C10 C11 N2 110.70(18)
C10 C11 H11 124.7
N2 C11 H11 124.7
N2 C12 N1 112.85(18)
N2 C12 H12 123.6
N1 C12 H12 123.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C3 1.7383(18)
O1 C7 1.2165(19)
N1 C12 1.341(2)
N1 C10 1.352(2)
N1 C9 1.468(2)
N2 C12 1.312(2)
N2 C11 1.357(3)
C1 C2 1.372(3)
C1 C6 1.394(2)
C1 H1 0.9300
C2 C3 1.380(3)
C2 H2 0.9300
C3 C4 1.378(2)
C4 C5 1.377(3)
C4 H4 0.9300
C5 C6 1.391(2)
C5 H5 0.9300
C6 C7 1.491(2)
C7 C8 1.503(2)
C8 C9 1.508(2)
C8 H8A 0.9700
C8 H8B 0.9700
C9 H9A 0.9700
C9 H9B 0.9700
C10 C11 1.344(3)
C10 H10 0.9300
C11 H11 0.9300
C12 H12 0.9300
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
C4 H4 O1 4_575 0.93 2.51 3.353(2) 151
C8 H8A N2 2_655 0.97 2.57 3.499(2) 160
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10255453
