#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007183.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_2007183
loop_
_publ_author_name
'Shanmuga Sundara Raj, S.'
'Ponnuswamy, M. N.'
'Shanmugam, G.'
'Nanjundan, S.'
_publ_section_title
;
 1-(2-Naphthalenyl)-3-(3-nitrophenyl)-2-propen-1-one
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              541
_journal_page_last               542
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C19 H13 N O3'
_chemical_formula_sum            'C19 H13 N O3'
_chemical_formula_weight         303.30
_chemical_melting_point          148.5
_chemical_name_systematic
;
1-[2-(napthalenyl)]-3-(3-nitrophenyl)-2-propen-1-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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 100.15(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.317(2)
_cell_length_b                   5.864(4)
_cell_length_c                   24.5820(10)
_cell_measurement_reflns_used    23
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24
_cell_measurement_theta_min      13
_cell_volume                     1463.9(10)
_computing_cell_refinement       SDP
_computing_data_collection       'SDP (Frenz,1978)'
_computing_data_reduction        SDP
_computing_molecular_graphics    'ORTEPII, (Johnson, 1976)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_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     1.54180
_diffrn_reflns_av_R_equivalents  0.072
_diffrn_reflns_av_sigmaI/netI    0.0079
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            2924
_diffrn_reflns_theta_max         70
_diffrn_reflns_theta_min         3.65
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.13
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.079
_refine_ls_goodness_of_fit_obs   0.925
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         2763
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_restrained_S_obs      0.925
_refine_ls_R_factor_all          0.029
_refine_ls_R_factor_obs          0.028
_refine_ls_shift/esd_max         0.012
_refine_ls_shift/esd_mean        0.089
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.1P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.118
_refine_ls_wR_factor_obs         0.097
_reflns_number_observed          2537
_reflns_number_total             2763
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    mu1335.cif
_[local]_cod_data_source_block   ketone
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_database_code               2007183
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_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 0.0414(8) 0.0420(8) 0.0419(8) -0.0004(6) 0.0074(6) 0.0005(5)
C2 0.0417(8) 0.0407(8) 0.0403(7) -0.0007(5) 0.0074(6) 0.0002(5)
C3 0.0497(9) 0.0500(9) 0.0493(9) 0.0002(7) 0.0086(7) -0.0005(6)
C4 0.0529(9) 0.0526(10) 0.0519(10) -0.0005(7) 0.0094(7) 0.0007(6)
C5 0.0461(8) 0.0459(9) 0.0463(8) 0.0001(6) 0.0085(6) 0.0011(6)
C6 0.0567(10) 0.0551(10) 0.0554(10) -0.0011(7) 0.0100(7) 0.0003(7)
C7 0.0591(10) 0.0596(10) 0.0590(10) 0.0000(8) 0.0111(7) 0.0008(7)
C8 0.0644(11) 0.0659(12) 0.0639(11) 0.0005(9) 0.0113(9) 0.0005(8)
C9 0.0566(10) 0.0554(10) 0.0574(10) 0.0002(7) 0.0106(8) 0.0000(7)
C10 0.0434(8) 0.0438(9) 0.0432(8) 0.0005(6) 0.0077(6) 0.0010(5)
C11 0.0460(8) 0.0467(9) 0.0456(8) 0.0001(6) 0.0081(6) 0.0002(6)
C12 0.0555(10) 0.0548(10) 0.0544(10) -0.0003(8) 0.0098(7) -0.0002(7)
C13 0.0441(8) 0.0427(8) 0.0435(8) 0.0003(6) 0.0074(6) -0.0001(5)
C14 0.0411(8) 0.0420(8) 0.0412(8) 0.0001(5) 0.0076(6) 0.0004(5)
C15 0.0432(8) 0.0420(8) 0.0430(8) -0.0003(6) 0.0074(6) 0.0001(5)
C16 0.0422(8) 0.0428(8) 0.0423(8) 0.0002(6) 0.0077(6) 0.0006(5)
C17 0.0507(9) 0.0502(9) 0.0509(8) -0.0003(6) 0.0092(7) 0.0003(6)
C18 0.0535(10) 0.0542(10) 0.0544(10) 0.0006(7) 0.0086(7) 0.0001(7)
C19 0.0482(9) 0.0496(9) 0.0480(8) -0.0008(6) 0.0099(6) 0.0001(6)
O20 0.0446(6) 0.0440(7) 0.0441(6) -0.0001(4) 0.0075(4) 0.0006(4)
N21 0.0554(9) 0.0553(9) 0.0557(9) 0.0000(6) 0.0099(7) 0.0001(6)
O22 0.0867(11) 0.0877(11) 0.0883(11) 0.0003(9) 0.0156(9) 0.0007(8)
O23 0.0897(12) 0.0881(12) 0.0899(11) 0.0008(9) 0.0163(8) 0.0007(8)
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 0.67211(14) 0.3852(3) 0.33109(6) 0.0418(4) Uani d 1 C
C2 0.58488(13) 0.2390(2) 0.34899(5) 0.0409(4) Uani d 1 C
C3 0.5566(2) 0.0257(3) 0.32178(7) 0.0497(5) Uani d 1 C
C4 0.6116(2) -0.0263(3) 0.27590(7) 0.0524(5) Uani d 1 C
C5 0.7011(2) 0.1241(3) 0.25651(7) 0.0461(4) Uani d 1 C
C6 0.7592(2) 0.0757(3) 0.20952(7) 0.0557(5) Uani d 1 C
C7 0.8449(2) 0.2235(3) 0.19243(7) 0.0591(5) Uani d 1 C
C8 0.8773(2) 0.4274(4) 0.22064(8) 0.0648(5) Uani d 1 C
C9 0.8223(2) 0.4840(3) 0.26583(8) 0.0564(5) Uani d 1 C
C10 0.73225(14) 0.3324(3) 0.28540(6) 0.0435(4) Uani d 1 C
C11 0.52214(15) 0.3087(3) 0.39653(6) 0.0461(4) Uani d 1 C
C12 0.4253(2) 0.1524(3) 0.41465(8) 0.0549(5) Uani d 1 C
C13 0.38422(14) 0.1737(2) 0.46252(6) 0.0435(4) Uani d 1 C
C14 0.29343(15) 0.0154(3) 0.48329(6) 0.0414(4) Uani d 1 C
C15 0.23687(15) 0.0789(2) 0.52888(6) 0.0428(4) Uani d 1 C
C16 0.15188(15) -0.0717(2) 0.54762(6) 0.0424(4) Uani d 1 C
C17 0.1205(2) -0.2807(3) 0.52378(7) 0.0506(4) Uani d 1 C
C18 0.1779(2) -0.3431(3) 0.47894(7) 0.0541(5) Uani d 1 C
C19 0.2621(2) -0.1974(3) 0.45893(6) 0.0484(4) Uani d 1 C
O20 0.54923(10) 0.4930(2) 0.41998(4) 0.0443(4) Uani d 1 O
N21 0.08679(15) -0.0019(3) 0.59412(6) 0.0554(5) Uani d 1 N
O22 0.0112(2) -0.1358(3) 0.60976(8) 0.0875(5) Uani d 1 O
O23 0.1109(2) 0.1869(3) 0.61404(8) 0.0892(5) Uani d 1 O
H1 0.700(3) 0.553(4) 0.3499(11) 0.080(7) Uiso d 1 H
H3 0.486(3) -0.066(5) 0.3411(11) 0.122(8) Uiso d 1 H
H4 0.6007(19) -0.174(3) 0.2497(8) 0.071(4) Uiso d 1 H
H6 0.7279(17) -0.080(3) 0.1871(7) 0.078(4) Uiso d 1 H
H7 0.899(3) 0.229(5) 0.1623(11) 0.110(9) Uiso d 1 H
H8 0.953(4) 0.502(6) 0.2059(16) 0.133(11) Uiso d 1 H
H9 0.8494(14) 0.641(3) 0.2921(6) 0.063(3) Uiso d 1 H
H12 0.390(3) 0.060(5) 0.3867(12) 0.094(7) Uiso d 1 H
H13 0.451(2) 0.278(4) 0.4961(8) 0.096(5) Uiso d 1 H
H15 0.240(3) 0.213(5) 0.5548(11) 0.123(8) Uiso d 1 H
H17 0.067(3) -0.381(5) 0.5437(11) 0.124(7) Uiso d 1 H
H18 0.1616(17) -0.488(3) 0.4605(7) 0.086(4) Uiso d 1 H
H19 0.3015(15) -0.199(2) 0.4258(6) 0.065(3) 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'
N N 0.0311 0.0180 '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 121.65(14) ?
C2 C1 H1 124.2(14) ?
C10 C1 H1 114.2(14) ?
C1 C2 C3 119.37(13) ?
C1 C2 C11 118.76(13) ?
C3 C2 C11 121.87(13) yes
C4 C3 C2 119.8(2) ?
C4 C3 H3 130.8(15) ?
C2 C3 H3 109.3(15) ?
C3 C4 C5 121.5(2) ?
C3 C4 H4 130.8(10) ?
C5 C4 H4 107.8(10) ?
C4 C5 C10 118.01(14) ?
C4 C5 C6 122.8(2) ?
C10 C5 C6 119.17(14) ?
C7 C6 C5 121.1(2) ?
C7 C6 H6 122.1(9) ?
C5 C6 H6 116.7(9) ?
C6 C7 C8 120.4(2) ?
C6 C7 H7 136.6(16) ?
C8 C7 H7 103.0(16) ?
C9 C8 C7 120.8(2) ?
C9 C8 H8 130.(2) ?
C7 C8 H8 109.(2) ?
C8 C9 C10 120.5(2) ?
C8 C9 H9 124.2(7) ?
C10 C9 H9 115.1(7) ?
C1 C10 C5 119.63(14) ?
C1 C10 C9 122.34(14) ?
C5 C10 C9 118.01(14) ?
O20 C11 C12 120.72(14) yes
O20 C11 C2 120.88(13) yes
C12 C11 C2 118.40(14) yes
C13 C12 C11 123.2(2) yes
C13 C12 H12 125.8(19) ?
C11 C12 H12 110.2(19) ?
C12 C13 C14 124.83(15) yes
C12 C13 H13 116.4(10) ?
C14 C13 H13 114.9(10) ?
C19 C14 C15 118.85(14) ?
C19 C14 C13 121.83(13) ?
C15 C14 C13 119.32(13) ?
C16 C15 C14 118.39(13) ?
C16 C15 H15 103.8(14) ?
C14 C15 H15 137.8(15) ?
C17 C16 C15 123.03(13) ?
C17 C16 N21 118.11(13) ?
C15 C16 N21 118.81(13) ?
C16 C17 C18 118.21(15) ?
C16 C17 H17 115.4(16) ?
C18 C17 H17 125.9(16) ?
C19 C18 C17 120.4(2) ?
C19 C18 H18 116.8(11) ?
C17 C18 H18 122.8(11) ?
C18 C19 C14 121.10(15) ?
C18 C19 H19 132.7(9) ?
C14 C19 H19 105.7(9) ?
O23 N21 O22 123.8(2) ?
O23 N21 C16 118.2(2) ?
O22 N21 C16 117.96(15) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.370(2) ?
C1 C10 1.410(2) ?
C1 H1 1.10(2) ?
C2 C3 1.424(2) ?
C2 C11 1.489(2) ?
C3 C4 1.383(2) ?
C3 H3 1.08(3) ?
C4 C5 1.419(2) ?
C4 H4 1.07(2) ?
C5 C10 1.421(2) ?
C5 C6 1.421(2) ?
C6 C7 1.356(3) ?
C6 H6 1.09(2) ?
C7 C8 1.393(3) ?
C7 H7 1.00(3) ?
C8 C9 1.374(3) ?
C8 H8 1.02(4) ?
C9 C10 1.429(2) ?
C9 H9 1.130(15) ?
C11 O20 1.233(2) yes
C11 C12 1.481(2) yes
C12 C13 1.325(2) yes
C12 H12 0.90(3) ?
C13 C14 1.472(2) yes
C13 H13 1.15(2) ?
C14 C19 1.397(2) ?
C14 C15 1.402(2) ?
C15 C16 1.380(2) ?
C15 H15 1.01(3) ?
C16 C17 1.373(2) ?
C16 N21 1.482(2) ?
C17 C18 1.389(2) ?
C17 H17 1.00(3) ?
C18 C19 1.371(2) ?
C18 H18 0.96(2) ?
C19 H19 0.973(15) ?
N21 O23 1.218(2) yes
N21 O22 1.216(2) 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
C10 C1 C2 C3 1.6(2) ?
C10 C1 C2 C11 -178.27(12) ?
C1 C2 C3 C4 -3.5(2) ?
C11 C2 C3 C4 176.44(15) ?
C2 C3 C4 C5 2.9(3) ?
C3 C4 C5 C10 -0.5(3) ?
C3 C4 C5 C6 -179.9(2) ?
C4 C5 C6 C7 -179.7(2) ?
C10 C5 C6 C7 0.9(3) ?
C5 C6 C7 C8 -0.4(3) ?
C6 C7 C8 C9 -0.7(3) ?
C7 C8 C9 C10 1.1(3) ?
C2 C1 C10 C5 0.8(2) ?
C2 C1 C10 C9 179.28(13) ?
C4 C5 C10 C1 -1.3(2) ?
C6 C5 C10 C1 178.11(14) ?
C4 C5 C10 C9 -179.92(14) ?
C6 C5 C10 C9 -0.5(2) ?
C8 C9 C10 C1 -179.1(2) ?
C8 C9 C10 C5 -0.5(3) ?
C1 C2 C11 O20 -1.0(2) yes
C3 C2 C11 O20 179.10(10) yes
C1 C2 C11 C12 178.40(10) yes
C3 C2 C11 C12 -1.5(2) yes
O20 C11 C12 C13 -14.9(3) yes
C2 C11 C12 C13 165.7(2) yes
C11 C12 C13 C14 -176.70(10) yes
C12 C13 C14 C19 12.8(2) yes
C12 C13 C14 C15 -167.4(2) ?
C19 C14 C15 C16 -0.3(2) ?
C13 C14 C15 C16 179.88(13) ?
C14 C15 C16 C17 0.2(2) ?
C14 C15 C16 N21 -177.19(13) ?
C15 C16 C17 C18 0.4(3) ?
N21 C16 C17 C18 177.79(14) ?
C16 C17 C18 C19 -0.8(3) ?
C17 C18 C19 C14 0.7(3) ?
C15 C14 C19 C18 -0.1(2) ?
C13 C14 C19 C18 179.69(14) ?
C17 C16 N21 O23 -177.4(2) ?
C15 C16 N21 O23 0.1(2) ?
C17 C16 N21 O22 1.8(2) ?
C15 C16 N21 O22 179.29(15) ?