#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/85/2218537.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_2218537
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Chantrapromma, Suchada'
'Patil, P. S.'
'Dharmaprakash, S. M.'
_publ_section_title
;
 (E)-3-(2-Chlorophenyl)-1-(4-nitrophenyl)prop-2-en-1-one
;
_journal_coeditor_code           SJ2489
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o958
_journal_page_last               o959
_journal_paper_doi               10.1107/S160053680801218X
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C15 H10 Cl N O3'
_chemical_formula_moiety         'C15 H10 Cl N O3'
_chemical_formula_sum            'C15 H10 Cl N O3'
_chemical_formula_weight         287.69
_chemical_name_systematic
;
(E)-3-(2-Chlorophenyl)-1-(4-nitrophenyl)prop-2-en-1-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 102.2900(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.7003(2)
_cell_length_b                   7.36590(10)
_cell_length_c                   25.9954(4)
_cell_measurement_reflns_used    3736
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      1.60
_cell_volume                     2563.21(7)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
;
Bruker SMART APEX2 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  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            27534
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.60
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_T_max  0.9573
_exptl_absorpt_correction_T_min  0.8992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.255
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3736
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0392
_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)+(0.0472P)²+1.7337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1026
_reflns_number_gt                3008
_reflns_number_total             3736
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2489.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      'C 2/c'
_cod_database_code               2218537
_cod_database_fobs_code          2218537
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
Cl Cl1 0.51146(3) 1.13027(5) 0.327931(14) 0.02471(10) Uani d . 1
O O1 0.26191(7) 0.90593(14) 0.17879(4) 0.0253(2) Uani d . 1
O O2 0.07873(8) 0.27115(15) -0.01091(4) 0.0305(3) Uani d . 1
O O3 0.18728(9) 0.07688(15) 0.02905(4) 0.0321(3) Uani d . 1
N N1 0.14644(9) 0.22581(17) 0.02587(4) 0.0224(2) Uani d . 1
C C1 0.51251(10) 0.91188(19) 0.35378(5) 0.0193(3) Uani d . 1
C C2 0.57265(10) 0.8810(2) 0.40322(5) 0.0227(3) Uani d . 1
H H2 0.6106 0.9747 0.4213 0.027 Uiso calc R 1
C C3 0.57562(10) 0.7097(2) 0.42526(5) 0.0235(3) Uani d . 1
H H3 0.6157 0.6881 0.4583 0.028 Uiso calc R 1
C C4 0.51884(10) 0.5699(2) 0.39809(6) 0.0228(3) Uani d . 1
H H4 0.5207 0.4548 0.4130 0.027 Uiso calc R 1
C C5 0.45951(10) 0.60253(19) 0.34883(5) 0.0210(3) Uani d . 1
H H5 0.4218 0.5080 0.3310 0.025 Uiso calc R 1
C C6 0.45467(9) 0.77387(18) 0.32502(5) 0.0181(3) Uani d . 1
C C7 0.39252(9) 0.80876(19) 0.27284(5) 0.0191(3) Uani d . 1
H H7 0.3918 0.9272 0.2604 0.023 Uiso calc R 1
C C8 0.33667(10) 0.68819(19) 0.24123(5) 0.0211(3) Uani d . 1
H H8 0.3334 0.5685 0.2521 0.025 Uiso calc R 1
C C9 0.28008(9) 0.74551(18) 0.18885(5) 0.0183(3) Uani d . 1
C C10 0.24532(9) 0.60468(18) 0.14738(5) 0.0173(3) Uani d . 1
C C11 0.27549(9) 0.42431(19) 0.15364(5) 0.0192(3) Uani d . 1
H H11 0.3174 0.3876 0.1849 0.023 Uiso calc R 1
C C12 0.24381(10) 0.29833(19) 0.11385(5) 0.0198(3) Uani d . 1
H H12 0.2642 0.1778 0.1178 0.024 Uiso calc R 1
C C13 0.18098(9) 0.35820(18) 0.06821(5) 0.0181(3) Uani d . 1
C C14 0.14839(10) 0.53630(19) 0.06062(5) 0.0206(3) Uani d . 1
H H14 0.1051 0.5715 0.0296 0.025 Uiso calc R 1
C C15 0.18190(10) 0.65985(19) 0.10033(5) 0.0203(3) Uani d . 1
H H15 0.1622 0.7807 0.0958 0.024 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
O3 N1 O2 123.63(12)
O3 N1 C13 118.24(11)
O2 N1 C13 118.13(12)
C2 C1 C6 122.04(13)
C2 C1 Cl1 117.55(11)
C6 C1 Cl1 120.41(10)
C3 C2 C1 119.48(13)
C3 C2 H2 120.3
C1 C2 H2 120.3
C2 C3 C4 120.10(13)
C2 C3 H3 119.9
C4 C3 H3 119.9
C5 C4 C3 119.79(14)
C5 C4 H4 120.1
C3 C4 H4 120.1
C4 C5 C6 121.89(13)
C4 C5 H5 119.1
C6 C5 H5 119.1
C5 C6 C1 116.69(12)
C5 C6 C7 122.10(12)
C1 C6 C7 121.21(12)
C8 C7 C6 126.75(13)
C8 C7 H7 116.6
C6 C7 H7 116.6
C7 C8 C9 119.78(13)
C7 C8 H8 120.1
C9 C8 H8 120.1
O1 C9 C8 121.04(12)
O1 C9 C10 119.69(12)
C8 C9 C10 119.28(12)
C11 C10 C15 119.53(12)
C11 C10 C9 122.41(11)
C15 C10 C9 118.04(12)
C12 C11 C10 120.88(12)
C12 C11 H11 119.6
C10 C11 H11 119.6
C13 C12 C11 117.72(13)
C13 C12 H12 121.1
C11 C12 H12 121.1
C12 C13 C14 123.19(13)
C12 C13 N1 118.25(12)
C14 C13 N1 118.56(12)
C15 C14 C13 118.16(12)
C15 C14 H14 120.9
C13 C14 H14 120.9
C14 C15 C10 120.51(13)
C14 C15 H15 119.7
C10 C15 H15 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7422(14)
O1 C9 1.2243(16)
O2 N1 1.2283(15)
O3 N1 1.2263(16)
N1 C13 1.4712(17)
C1 C2 1.3898(19)
C1 C6 1.4029(18)
C2 C3 1.382(2)
C2 H2 0.9300
C3 C4 1.389(2)
C3 H3 0.9300
C4 C5 1.3839(19)
C4 H4 0.9300
C5 C6 1.4010(19)
C5 H5 0.9300
C6 C7 1.4627(18)
C7 C8 1.3348(19)
C7 H7 0.9300
C8 C9 1.4777(18)
C8 H8 0.9300
C9 C10 1.4989(18)
C10 C11 1.3906(19)
C10 C15 1.4012(18)
C11 C12 1.3886(19)
C11 H11 0.9300
C12 C13 1.3814(18)
C12 H12 0.9300
C13 C14 1.3863(19)
C14 C15 1.3795(19)
C14 H14 0.9300
C15 H15 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
_geom_hbond_publ_flag
C4 H4 O2 8_556 0.93 2.58 3.4284(18) 152 y
C5 H5 O1 4_545 0.93 2.59 3.2996(17) 134 y
C7 H7 Cl1 1_555 0.93 2.60 3.0531(14) 110 y
C7 H7 O1 1_555 0.93 2.47 2.7981(16) 101 y
C12 H12 O1 1_545 0.93 2.56 3.3298(17) 141 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
C6 C1 C2 C3 -0.4(2)
Cl1 C1 C2 C3 179.90(10)
C1 C2 C3 C4 0.0(2)
C2 C3 C4 C5 0.2(2)
C3 C4 C5 C6 0.1(2)
C4 C5 C6 C1 -0.5(2)
C4 C5 C6 C7 179.65(13)
C2 C1 C6 C5 0.67(19)
Cl1 C1 C6 C5 -179.69(10)
C2 C1 C6 C7 -179.46(12)
Cl1 C1 C6 C7 0.19(18)
C5 C6 C7 C8 -2.1(2)
C1 C6 C7 C8 178.04(13)
C6 C7 C8 C9 -178.41(12)
C7 C8 C9 O1 -19.1(2)
C7 C8 C9 C10 160.38(12)
O1 C9 C10 C11 170.56(13)
C8 C9 C10 C11 -8.89(19)
O1 C9 C10 C15 -7.99(19)
C8 C9 C10 C15 172.55(12)
C15 C10 C11 C12 0.2(2)
C9 C10 C11 C12 -178.36(12)
C10 C11 C12 C13 -0.5(2)
C11 C12 C13 C14 -0.2(2)
C11 C12 C13 N1 -179.66(12)
O3 N1 C13 C12 -11.92(19)
O2 N1 C13 C12 168.59(12)
O3 N1 C13 C14 168.59(13)
O2 N1 C13 C14 -10.89(19)
C12 C13 C14 C15 1.1(2)
N1 C13 C14 C15 -179.41(12)
C13 C14 C15 C10 -1.4(2)
C11 C10 C15 C14 0.8(2)
C9 C10 C15 C14 179.38(12)
