#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006348.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_2006348
loop_
_publ_author_name
'Shanmuga Sundara Raj, S.'
'Ponnuswamy, M. N.'
'Shanmugam, G.'
'Nanjundan, S.'
_publ_contact_author
;
      Dr. M.N.Ponnuswamy
      Reader
      Department of Crystallography and Biophysics
      University of Madras
      Guindy Campus
      Madras 600 025
      India
;
_publ_section_title
;
 3-(4-Chlorophenyl)-1-(2-naphthyl)prop-2-enone
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              917
_journal_page_last               918
_journal_volume                  53
_journal_year                    1997
_chemical_formula_sum            'C19 H13 Cl O'
_chemical_formula_weight         292.74
_chemical_melting_point          163
_chemical_name_systematic
;
1-[2-(napthylenyl)]-3-(4-chlorophenyl)-2-propen-1-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                100.55(3)
_cell_angle_beta                 91.90(3)
_cell_angle_gamma                91.62(4)
_cell_formula_units_Z            2
_cell_length_a                   5.911(4)
_cell_length_b                   7.474(3)
_cell_length_c                   16.366(3)
_cell_measurement_reflns_used    18
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23
_cell_measurement_theta_min      16
_cell_volume                     710.0(6)
_computing_cell_refinement       SDP
_computing_data_collection       'SDP (Frenz, 1978)'
_computing_data_reduction        SDP
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL-93
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0850
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            2533
_diffrn_reflns_theta_max         65
_diffrn_reflns_theta_min         2.75
_diffrn_standards_decay_%        <1.5
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  3600
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.327
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            transparent
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.244
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.066
_refine_ls_goodness_of_fit_obs   1.108
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2351
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_restrained_S_obs      1.108
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_obs          0.0563
_refine_ls_shift/esd_max         -0.065
_refine_ls_shift/esd_mean        0.017
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.1189P)^2^+0.1410P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1730
_refine_ls_wR_factor_obs         0.1652
_reflns_number_observed          2017
_reflns_number_total             2351
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    vj1049.cif
_[local]_cod_data_source_block   ketone
_cod_database_code               2006348
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 0.0440(13) 0.0447(11) 0.0561(13) -0.0011(9) -0.0011(9) 0.0113(9)
C2 0.0499(13) 0.0463(11) 0.0566(13) -0.0035(9) 0.0045(10) 0.0085(9)
C3 0.0515(14) 0.0527(13) 0.0658(15) 0.0024(10) 0.0091(11) 0.0076(11)
C4 0.0464(14) 0.0495(12) 0.078(2) 0.0054(10) -0.0004(11) 0.0170(11)
C5 0.0484(13) 0.0395(11) 0.0645(13) -0.0059(9) -0.0043(10) 0.0153(9)
C6 0.059(2) 0.0530(13) 0.075(2) -0.0061(11) -0.0130(13) 0.0241(12)
C7 0.082(2) 0.066(2) 0.0574(15) -0.0095(14) -0.0103(13) 0.0205(12)
C8 0.077(2) 0.0602(14) 0.0569(14) -0.0081(13) 0.0051(13) 0.0105(11)
C9 0.0564(15) 0.0504(12) 0.0568(13) -0.0007(10) 0.0042(11) 0.0124(10)
C10 0.0499(13) 0.0380(10) 0.0555(12) -0.0063(9) 0.0016(9) 0.0115(9)
C11 0.058(2) 0.0578(13) 0.0550(13) 0.0008(11) 0.0029(11) 0.0048(10)
C12 0.054(2) 0.0622(14) 0.0578(14) -0.0042(11) 0.0003(11) 0.0107(10)
C13 0.0498(14) 0.0520(12) 0.0567(13) -0.0002(10) 0.0023(10) 0.0114(10)
C14 0.0508(13) 0.0432(11) 0.0545(12) 0.0037(9) 0.0032(10) 0.0115(9)
C15 0.0526(14) 0.0491(12) 0.0537(13) 0.0016(10) -0.0034(10) 0.0076(10)
C16 0.0456(14) 0.0477(12) 0.0673(14) -0.0019(10) 0.0030(10) 0.0119(10)
C17 0.0541(14) 0.0482(12) 0.0581(13) 0.0023(10) 0.0098(10) 0.0137(10)
C18 0.0593(15) 0.0503(12) 0.0500(12) -0.0008(10) 0.0010(10) 0.0055(9)
C19 0.0468(14) 0.0484(12) 0.0577(13) -0.0027(10) 0.0004(10) 0.0100(9)
O20 0.0541(12) 0.119(2) 0.0565(10) 0.0073(10) 0.0001(8) 0.0114(10)
Cl 0.0812(6) 0.0848(5) 0.0660(5) -0.0109(4) 0.0224(3) 0.0146(3)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_type_symbol
C1 -0.5469(4) 0.3104(3) 0.65314(14) 0.0481(5) Uani d 1 C
C2 -0.4074(4) 0.2511(3) 0.58915(14) 0.0511(5) Uani d 1 C
C3 -0.1958(4) 0.1801(3) 0.6074(2) 0.0569(6) Uani d 1 C
C4 -0.1324(4) 0.1681(3) 0.6868(2) 0.0572(6) Uani d 1 C
C5 -0.2723(4) 0.2296(3) 0.7536(2) 0.0504(6) Uani d 1 C
C6 -0.2098(5) 0.2236(3) 0.8372(2) 0.0614(7) Uani d 1 C
C7 -0.3492(5) 0.2877(4) 0.9000(2) 0.0677(7) Uani d 1 C
C8 -0.5565(5) 0.3612(4) 0.8830(2) 0.0648(7) Uani d 1 C
C9 -0.6233(5) 0.3692(3) 0.80335(15) 0.0542(6) Uani d 1 C
C10 -0.4835(4) 0.3034(3) 0.73624(14) 0.0476(5) Uani d 1 C
C11 -0.4875(5) 0.2608(3) 0.5025(2) 0.0576(6) Uani d 1 C
C12 -0.3169(5) 0.2602(4) 0.4381(2) 0.0583(6) Uani d 1 C
C13 -0.3775(4) 0.2157(3) 0.35844(15) 0.0527(6) Uani d 1 C
C14 -0.2372(4) 0.2172(3) 0.28660(14) 0.0491(5) Uani d 1 C
C15 -0.0189(4) 0.2974(3) 0.29289(15) 0.0522(6) Uani d 1 C
C16 0.1038(4) 0.3005(3) 0.2234(2) 0.0534(6) Uani d 1 C
C17 0.0102(4) 0.2224(3) 0.14657(15) 0.0528(6) Uani d 1 C
C18 -0.2039(4) 0.1422(3) 0.13744(15) 0.0538(6) Uani d 1 C
C19 -0.3252(4) 0.1405(3) 0.20786(15) 0.0511(6) Uani d 1 C
O20 -0.6879(3) 0.2714(3) 0.48621(11) 0.0772(6) Uani d 1 O
Cl 0.16685(13) 0.22475(10) 0.05804(4) 0.0771(3) Uani d 1 Cl
H1 -0.686(5) 0.351(3) 0.6389(14) 0.045(6) Uiso d 1 H
H3 -0.109(6) 0.133(5) 0.565(2) 0.083(9) Uiso d 1 H
H4 0.008(5) 0.115(4) 0.6978(16) 0.058(7) Uiso d 1 H
H6 -0.068(5) 0.171(4) 0.8463(16) 0.059(7) Uiso d 1 H
H7 -0.297(5) 0.283(4) 0.9578(19) 0.072(8) Uiso d 1 H
H8 -0.661(6) 0.406(4) 0.922(2) 0.082(9) Uiso d 1 H
H9 -0.758(5) 0.420(3) 0.7890(14) 0.047(6) Uiso d 1 H
H12 -0.176(5) 0.290(4) 0.4553(16) 0.058(7) Uiso d 1 H
H13 -0.529(5) 0.181(3) 0.3439(15) 0.053(7) Uiso d 1 H
H15 0.047(4) 0.356(3) 0.3440(15) 0.044(6) Uiso d 1 H
H16 0.242(5) 0.353(4) 0.2270(16) 0.057(7) Uiso d 1 H
H18 -0.266(4) 0.099(3) 0.0848(16) 0.053(6) Uiso d 1 H
H19 -0.474(5) 0.090(3) 0.2008(14) 0.048(6) Uiso d 1 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C2 C1 C10 121.5(2) ?
C2 C1 H1 116.8(15) ?
C10 C1 H1 121.7(15) ?
C1 C2 C3 118.9(2) ?
C1 C2 C11 118.4(2) ?
C3 C2 C11 122.6(2) yes
C4 C3 C2 120.8(2) ?
C4 C3 H3 120.(2) ?
C2 C3 H3 119.(2) ?
C3 C4 C5 121.2(2) ?
C3 C4 H4 119.8(15) ?
C5 C4 H4 118.9(15) ?
C4 C5 C6 122.9(2) ?
C4 C5 C10 118.4(2) ?
C6 C5 C10 118.6(2) ?
C7 C6 C5 120.7(3) ?
C7 C6 H6 123.1(16) ?
C5 C6 H6 116.2(16) ?
C6 C7 C8 120.7(2) ?
C6 C7 H7 117.8(17) ?
C8 C7 H7 121.5(17) ?
C9 C8 C7 120.5(3) ?
C9 C8 H8 114.(2) ?
C7 C8 H8 126.(2) ?
C8 C9 C10 120.6(3) ?
C8 C9 H9 123.6(14) ?
C10 C9 H9 115.7(14) ?
C1 C10 C9 122.1(2) ?
C1 C10 C5 119.0(2) ?
C9 C10 C5 118.8(2) ?
O20 C11 C12 121.2(2) yes
O20 C11 C2 120.2(2) yes
C12 C11 C2 118.5(2) yes
C13 C12 C11 120.4(3) yes
C13 C12 H12 122.2(17) ?
C11 C12 H12 117.4(17) ?
C12 C13 C14 128.2(3) yes
C12 C13 H13 118.4(16) ?
C14 C13 H13 113.4(16) ?
C19 C14 C15 117.9(2) ?
C19 C14 C13 119.0(2) ?
C15 C14 C13 123.1(2) ?
C16 C15 C14 121.0(2) ?
C16 C15 H15 117.1(15) ?
C14 C15 H15 121.8(15) ?
C15 C16 C17 119.1(2) ?
C15 C16 H16 121.3(17) ?
C17 C16 H16 119.5(17) ?
C18 C17 C16 121.8(2) ?
C18 C17 Cl 119.0(2) ?
C16 C17 Cl 119.2(2) ?
C17 C18 C19 118.3(2) ?
C17 C18 H18 119.7(16) ?
C19 C18 H18 121.8(16) ?
C18 C19 C14 121.8(2) ?
C18 C19 H19 117.7(14) ?
C14 C19 H19 120.4(14) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.371(3) ?
C1 C10 1.409(3) ?
C1 H1 0.92(3) ?
C2 C3 1.416(4) ?
C2 C11 1.495(3) yes
C3 C4 1.360(4) ?
C3 H3 0.91(4) ?
C4 C5 1.411(4) ?
C4 H4 0.95(3) ?
C5 C6 1.414(4) ?
C5 C10 1.421(3) ?
C6 C7 1.364(4) ?
C6 H6 0.95(3) ?
C7 C8 1.397(4) ?
C7 H7 0.99(3) ?
C8 C9 1.362(4) ?
C8 H8 0.93(3) ?
C9 C10 1.420(3) ?
C9 H9 0.94(3) ?
C11 O20 1.213(3) yes
C11 C12 1.483(4) yes
C12 C13 1.319(4) yes
C12 H12 0.88(3) ?
C13 C14 1.463(3) yes
C13 H13 0.94(3) ?
C14 C19 1.389(3) ?
C14 C15 1.400(4) ?
C15 C16 1.373(4) ?
C15 H15 0.94(2) ?
C16 C17 1.376(4) ?
C16 H16 0.89(3) ?
C17 C18 1.376(4) ?
C17 Cl 1.748(2) yes
C18 C19 1.379(3) ?
C18 H18 0.92(3) ?
C19 H19 0.94(3) ?
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
C10 C1 C2 C3 0.5(3) ?
C10 C1 C2 C11 179.3(2) yes
C1 C2 C3 C4 1.0(4) ?
C11 C2 C3 C4 -177.8(2) ?
C2 C3 C4 C5 -1.5(4) ?
C3 C4 C5 C6 -178.4(2) ?
C3 C4 C5 C10 0.6(3) ?
C4 C5 C6 C7 178.8(2) ?
C10 C5 C6 C7 -0.1(4) ?
C5 C6 C7 C8 -0.2(4) ?
C6 C7 C8 C9 0.3(4) ?
C7 C8 C9 C10 -0.1(4) ?
C2 C1 C10 C9 178.1(2) ?
C2 C1 C10 C5 -1.4(3) ?
C8 C9 C10 C1 -179.7(2) ?
C8 C9 C10 C5 -0.2(3) ?
C4 C5 C10 C1 0.8(3) ?
C6 C5 C10 C1 179.8(2) ?
C4 C5 C10 C9 -178.7(2) ?
C6 C5 C10 C9 0.3(3) ?
C1 C2 C11 O20 -20.1(4) ?
C3 C2 C11 O20 158.7(3) ?
C1 C2 C11 C12 158.9(2) ?
C3 C2 C11 C12 -22.3(3) ?
O20 C11 C12 C13 -20.8(4) yes
C2 C11 C12 C13 160.2(2) yes
C11 C12 C13 C14 176.3(2) yes
C12 C13 C14 C19 170.8(2) yes
C12 C13 C14 C15 -11.1(4) ?
C19 C14 C15 C16 0.2(3) ?
C13 C14 C15 C16 -177.9(2) ?
C14 C15 C16 C17 -0.4(4) ?
C15 C16 C17 C18 0.5(4) ?
C15 C16 C17 Cl -179.5(2) ?
C16 C17 C18 C19 -0.4(4) ?
Cl C17 C18 C19 179.6(2) ?
C17 C18 C19 C14 0.2(4) ?
C15 C14 C19 C18 -0.1(3) ?
C13 C14 C19 C18 178.1(2) ?