#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007370.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_2007370
loop_
_publ_author_name
'\"Ozt\"urk, S.'
'Fun, H.-K.'
'Akkurt, M.'
'S\"onmez, M.'
'Chinnakali, K.'
_publ_section_title
;
 2-Benzoyl-3-hydroxy-1-naphthylamino-3-phenyl-2-propen-1-one
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              IUC9800023
_journal_volume                  54
_journal_year                    1998
_chemical_formula_sum            'C26 H19 N O3'
_chemical_formula_weight         393.42
_chemical_name_systematic
;
1-naphthylamino-2-benzoyl-3-phenyl-3-hydroxy-2-propene-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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 92.777(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9862(5)
_cell_length_b                   12.3722(5)
_cell_length_c                   16.0829(7)
_cell_measurement_reflns_used    2604
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      33
_cell_measurement_theta_min      1.5
_cell_volume                     1984.73(15)
_computing_cell_refinement       'SAINT (Siemens, 1996b)'
_computing_data_collection       'SMART (Siemens, 1996a)'
_computing_data_reduction        'SAINT (Siemens, 1996b)'
_computing_publication_material
; SHELXTL (Sheldrick, 1996)
  PARST (Nardelli, 1995)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 1996)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1996)'
_diffrn_ambient_temperature      173(2)
_diffrn_measurement_device
;
Siemens SMART CCD area detector diffractometer
;
_diffrn_measurement_method       '\w scans'
_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  0.0995
_diffrn_reflns_av_sigmaI/netI    0.1319
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            9219
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.267
_refine_ls_extinction_coef       0.0103(15)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.033
_refine_ls_goodness_of_fit_obs   1.143
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         3455
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_restrained_S_obs      1.143
_refine_ls_R_factor_all          0.1538
_refine_ls_R_factor_obs          0.0667
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w=1/[\s^2^(Fo^2^)+(0.0536P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1555
_refine_ls_wR_factor_obs         0.1192
_reflns_number_observed          1823
_reflns_number_total             3455
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    qa0039.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_cod_original_cell_volume        1984.7(2)
_cod_database_code               2007370
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_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
N1 0.024(2) 0.019(2) 0.027(2) 0.0025(15) 0.000(2) -0.0050(14)
O1 0.027(2) 0.030(2) 0.035(2) 0.0054(13) -0.0016(13) -0.0091(13)
O2 0.021(2) 0.030(2) 0.052(2) 0.0023(12) -0.0051(14) -0.0104(13)
O3 0.034(2) 0.029(2) 0.038(2) 0.0096(14) -0.0107(14) -0.0061(14)
C1 0.017(2) 0.021(2) 0.028(2) -0.001(2) 0.001(2) -0.001(2)
C2 0.029(2) 0.028(2) 0.026(2) 0.001(2) -0.002(2) 0.000(2)
C3 0.030(3) 0.024(2) 0.039(3) 0.008(2) 0.002(2) 0.000(2)
C4 0.031(3) 0.026(2) 0.032(2) 0.001(2) 0.001(2) -0.006(2)
C5 0.030(3) 0.034(3) 0.031(3) -0.003(2) 0.000(2) -0.009(2)
C6 0.037(3) 0.041(3) 0.023(2) -0.004(2) -0.001(2) -0.001(2)
C7 0.042(3) 0.031(3) 0.030(3) -0.002(2) 0.001(2) 0.010(2)
C8 0.029(2) 0.027(2) 0.025(2) -0.004(2) 0.007(2) -0.004(2)
C9 0.020(2) 0.022(2) 0.028(2) -0.001(2) 0.004(2) -0.002(2)
C10 0.021(2) 0.033(2) 0.025(2) -0.003(2) 0.003(2) -0.004(2)
C11 0.022(2) 0.025(2) 0.022(2) 0.001(2) 0.005(2) 0.006(2)
C12 0.024(2) 0.018(2) 0.021(2) 0.000(2) 0.004(2) -0.001(2)
C13 0.028(2) 0.024(2) 0.021(2) 0.000(2) 0.003(2) -0.002(2)
C14 0.026(2) 0.021(2) 0.024(2) 0.004(2) 0.003(2) -0.003(2)
C15 0.029(2) 0.028(2) 0.020(2) 0.001(2) 0.006(2) 0.000(2)
C16 0.033(3) 0.025(2) 0.033(2) -0.005(2) 0.004(2) 0.002(2)
C17 0.045(3) 0.020(2) 0.043(3) -0.002(2) -0.001(2) 0.002(2)
C18 0.043(3) 0.024(2) 0.057(3) 0.010(2) 0.004(2) -0.001(2)
C19 0.024(2) 0.029(2) 0.046(3) 0.001(2) 0.006(2) -0.005(2)
C20 0.026(2) 0.021(2) 0.027(2) 0.000(2) 0.004(2) 0.004(2)
C21 0.029(2) 0.025(2) 0.022(2) -0.005(2) 0.004(2) -0.002(2)
C22 0.025(3) 0.041(3) 0.033(2) -0.002(2) 0.006(2) -0.009(2)
C23 0.037(3) 0.056(3) 0.037(3) -0.012(2) 0.004(2) -0.019(2)
C24 0.046(3) 0.059(3) 0.037(3) -0.010(3) 0.012(2) -0.023(2)
C25 0.033(3) 0.051(3) 0.035(3) -0.003(2) 0.010(2) -0.011(2)
C26 0.027(3) 0.041(3) 0.023(2) -0.008(2) 0.007(2) -0.003(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_thermal_displace_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_type_symbol
N1 0.7101(3) 0.9182(2) -0.0231(2) 0.0235(8) Uani d 1 N
O1 0.9180(3) 0.8860(2) 0.0331(2) 0.0308(7) Uani d 1 O
O2 0.5939(3) 1.0995(2) 0.0226(2) 0.0349(7) Uani d 1 O
O3 1.0069(3) 0.9902(2) 0.1502(2) 0.0341(7) Uani d 1 O
C1 0.7040(3) 0.8297(3) -0.0796(2) 0.0221(9) Uani d 1 C
C2 0.7463(4) 0.7287(3) -0.0555(3) 0.0277(10) Uani d 1 C
C3 0.7337(4) 0.6418(3) -0.1121(3) 0.0310(10) Uani d 1 C
C4 0.6827(4) 0.6572(3) -0.1916(2) 0.0298(10) Uani d 1 C
C5 0.5930(4) 0.7805(3) -0.3010(2) 0.0315(10) Uani d 1 C
C6 0.5548(4) 0.8810(3) -0.3261(3) 0.0337(11) Uani d 1 C
C7 0.5587(4) 0.9679(3) -0.2693(2) 0.0342(11) Uani d 1 C
C8 0.6052(4) 0.9520(3) -0.1887(2) 0.0269(10) Uani d 1 C
C9 0.6489(4) 0.8492(3) -0.1612(2) 0.0231(9) Uani d 1 C
C10 0.6418(4) 0.7611(3) -0.2175(2) 0.0260(9) Uani d 1 C
C11 0.8139(4) 0.9453(3) 0.0279(2) 0.0230(9) Uani d 1 C
C12 0.8073(4) 1.0450(3) 0.0785(2) 0.0209(9) Uani d 1 C
C13 0.7042(4) 1.1261(3) 0.0549(2) 0.0242(9) Uani d 1 C
C14 0.7355(4) 1.2440(3) 0.0624(2) 0.0237(9) Uani d 1 C
C15 0.8639(4) 1.2849(3) 0.0548(2) 0.0255(9) Uani d 1 C
C16 0.8854(4) 1.3962(3) 0.0603(2) 0.0302(10) Uani d 1 C
C17 0.7799(4) 1.4649(3) 0.0745(3) 0.0361(11) Uani d 1 C
C18 0.6514(5) 1.4249(3) 0.0819(3) 0.0413(12) Uani d 1 C
C19 0.6290(4) 1.3149(3) 0.0740(3) 0.0328(10) Uani d 1 C
C20 0.9038(4) 1.0563(3) 0.1434(2) 0.0248(9) Uani d 1 C
C21 0.9003(4) 1.1340(3) 0.2126(2) 0.0252(9) Uani d 1 C
C22 1.0220(4) 1.1662(3) 0.2516(2) 0.0325(10) Uani d 1 C
C23 1.0254(5) 1.2374(4) 0.3179(3) 0.0431(12) Uani d 1 C
C24 0.9074(5) 1.2750(4) 0.3478(3) 0.0469(13) Uani d 1 C
C25 0.7856(5) 1.2425(4) 0.3109(3) 0.0396(11) Uani d 1 C
C26 0.7808(4) 1.1710(3) 0.2446(2) 0.0299(10) Uani d 1 C
H2 0.779(4) 0.716(3) -0.002(2) 0.031(11) Uiso d 1 H
H3 0.762(3) 0.573(3) -0.090(2) 0.029(10) Uiso d 1 H
H4 0.673(3) 0.598(3) -0.231(2) 0.020(9) Uiso d 1 H
H5 0.592(3) 0.717(3) -0.339(2) 0.028(10) Uiso d 1 H
H6 0.518(4) 0.899(3) -0.385(2) 0.042(11) Uiso d 1 H
H7 0.529(3) 1.039(3) -0.289(2) 0.026(10) Uiso d 1 H
H8 0.607(3) 1.014(3) -0.1493(19) 0.022(9) Uiso d 1 H
H1N 0.636(4) 0.961(3) -0.021(2) 0.040(12) Uiso d 1 H
H3O 0.986(5) 0.932(4) 0.098(3) 0.089(17) Uiso d 1 H
H15 0.943(4) 1.234(3) 0.046(2) 0.043(11) Uiso d 1 H
H16 0.984(4) 1.424(3) 0.057(2) 0.042(11) Uiso d 1 H
H17 0.802(4) 1.545(3) 0.082(2) 0.052(12) Uiso d 1 H
H18 0.579(4) 1.472(3) 0.089(2) 0.047(12) Uiso d 1 H
H19 0.539(4) 1.287(3) 0.081(2) 0.045(12) Uiso d 1 H
H22 1.100(3) 1.142(3) 0.230(2) 0.022(10) Uiso d 1 H
H23 1.113(4) 1.257(3) 0.347(3) 0.058(14) Uiso d 1 H
H24 0.908(4) 1.326(3) 0.394(3) 0.054(13) Uiso d 1 H
H25 0.696(4) 1.266(3) 0.333(2) 0.053(13) Uiso d 1 H
H26 0.699(4) 1.144(3) 0.220(2) 0.033(11) 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 0.0033 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'
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
C11 N1 C1 126.4(3) yes
C2 C1 C9 121.1(3) ?
C2 C1 N1 121.3(3) ?
C9 C1 N1 117.5(3) yes
C1 C2 C3 119.8(4) ?
C4 C3 C2 121.1(4) ?
C3 C4 C10 119.6(4) ?
C6 C5 C10 120.9(4) ?
C5 C6 C7 120.4(4) ?
C8 C7 C6 120.1(4) ?
C7 C8 C9 120.8(4) ?
C8 C9 C10 119.2(3) ?
C8 C9 C1 123.0(3) ?
C10 C9 C1 117.8(3) ?
C4 C10 C9 120.6(4) ?
C4 C10 C5 120.9(4) ?
C9 C10 C5 118.4(4) ?
O1 C11 N1 120.3(3) yes
O1 C11 C12 120.2(3) yes
N1 C11 C12 119.5(3) yes
C20 C12 C13 125.1(3) yes
C20 C12 C11 116.6(3) yes
C13 C12 C11 118.3(3) ?
O2 C13 C12 121.5(3) yes
O2 C13 C14 118.1(3) yes
C12 C13 C14 120.2(3) yes
C15 C14 C19 119.6(4) ?
C15 C14 C13 122.6(3) ?
C19 C14 C13 117.7(3) ?
C14 C15 C16 119.6(4) ?
C17 C16 C15 120.1(4) ?
C16 C17 C18 120.8(4) ?
C19 C18 C17 119.3(4) ?
C18 C19 C14 120.6(4) ?
O3 C20 C12 120.7(3) yes
O3 C20 C21 113.0(3) yes
C12 C20 C21 126.2(3) yes
C22 C21 C26 118.7(4) ?
C22 C21 C20 118.2(3) ?
C26 C21 C20 122.9(4) ?
C23 C22 C21 121.0(4) ?
C24 C23 C22 119.7(4) ?
C23 C24 C25 120.1(4) ?
C26 C25 C24 120.8(4) ?
C25 C26 C21 119.6(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C11 1.334(4) yes
N1 C1 1.422(4) yes
O1 C11 1.271(4) yes
O2 C13 1.239(4) yes
O3 C20 1.316(4) yes
C1 C2 1.369(5) ?
C1 C9 1.419(5) ?
C2 C3 1.410(5) ?
C3 C4 1.367(5) ?
C4 C10 1.406(5) ?
C5 C6 1.357(5) ?
C5 C10 1.425(5) ?
C6 C7 1.411(6) ?
C7 C8 1.369(5) ?
C8 C9 1.409(5) ?
C9 C10 1.418(5) ?
C11 C12 1.482(5) yes
C12 C20 1.392(5) yes
C12 C13 1.474(5) yes
C13 C14 1.495(5) yes
C14 C15 1.389(5) ?
C14 C19 1.398(5) ?
C15 C16 1.396(5) ?
C16 C17 1.381(5) ?
C17 C18 1.386(6) ?
C18 C19 1.384(5) ?
C20 C21 1.473(5) yes
C21 C22 1.398(5) ?
C21 C26 1.399(5) ?
C22 C23 1.383(5) ?
C23 C24 1.375(6) ?
C24 C25 1.387(6) ?
C25 C26 1.384(5) ?
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
C11 N1 C1 C2 46.4(5)
C11 N1 C1 C9 -135.3(4)
C9 C1 C2 C3 -0.8(5)
N1 C1 C2 C3 177.4(3)
C1 C2 C3 C4 1.6(6)
C2 C3 C4 C10 -0.1(6)
C10 C5 C6 C7 -2.0(6)
C5 C6 C7 C8 2.1(6)
C6 C7 C8 C9 -0.5(6)
C7 C8 C9 C10 -1.2(5)
C7 C8 C9 C1 176.9(4)
C2 C1 C9 C8 -179.4(4)
N1 C1 C9 C8 2.3(5)
C2 C1 C9 C10 -1.3(5)
N1 C1 C9 C10 -179.6(3)
C3 C4 C10 C9 -2.1(6)
C3 C4 C10 C5 177.6(4)
C8 C9 C10 C4 -179.0(3)
C1 C9 C10 C4 2.8(5)
C8 C9 C10 C5 1.3(5)
C1 C9 C10 C5 -176.9(3)
C6 C5 C10 C4 -179.4(4)
C6 C5 C10 C9 0.3(5)
C1 N1 C11 O1 -4.4(5)
C1 N1 C11 C12 175.5(3)
O1 C11 C12 C20 -14.1(5)
N1 C11 C12 C20 165.9(3)
O1 C11 C12 C13 163.4(3)
N1 C11 C12 C13 -16.5(5)
C20 C12 C13 O2 -150.7(4)
C11 C12 C13 O2 32.0(5)
C20 C12 C13 C14 34.8(5)
C11 C12 C13 C14 -142.5(3)
O2 C13 C14 C15 -145.4(4)
C12 C13 C14 C15 29.3(5)
O2 C13 C14 C19 31.8(5)
C12 C13 C14 C19 -153.5(3)
C19 C14 C15 C16 1.1(6)
C13 C14 C15 C16 178.3(3)
C14 C15 C16 C17 0.9(6)
C15 C16 C17 C18 -1.2(6)
C16 C17 C18 C19 -0.7(7)
C17 C18 C19 C14 2.7(7)
C15 C14 C19 C18 -3.0(6)
C13 C14 C19 C18 179.7(4)
C13 C12 C20 O3 -166.8(3)
C11 C12 C20 O3 10.5(5)
C13 C12 C20 C21 17.3(6)
C11 C12 C20 C21 -165.4(3)
O3 C20 C21 C22 29.6(5)
C12 C20 C21 C22 -154.2(4)
O3 C20 C21 C26 -145.8(4)
C12 C20 C21 C26 30.4(6)
C26 C21 C22 C23 -3.2(6)
C20 C21 C22 C23 -178.8(4)
C21 C22 C23 C24 1.9(7)
C22 C23 C24 C25 -0.6(7)
C23 C24 C25 C26 0.8(7)
C24 C25 C26 C21 -2.1(6)
C22 C21 C26 C25 3.2(6)
C20 C21 C26 C25 178.6(4)