##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2',2'-dimethyl-3-pyreno[6'5:7,8]coumarin
;
_chemical_name_common     Seselin
_chemical_formula_moiety     'C14 H12 O3'
_chemical_formula_sum     'C14 H12 O3'
_chemical_formula_iupac     'C14 H12 O3'
_chemical_formula_weight     228.24
_chemical_melting_point     120
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_HALL     '-P 2ybc'
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'
_cell_length_a     8.4280(10)
_cell_length_b     11.112(2)
_cell_length_c     12.324(2)
_cell_angle_alpha     90.00
_cell_angle_beta     103.080(10)
_cell_angle_gamma     90.00
_cell_volume     1124.2(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     5.38
_cell_measurement_theta_max     27.70
_cell_measurement_temperature     299(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     'light yellow'
_exptl_crystal_size_max     0.80
_exptl_crystal_size_mid     0.38
_exptl_crystal_size_min     0.30
_exptl_crystal_density_diffrn     1.348
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     480
_exptl_absorpt_coefficient_mu     0.775
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     299(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Enraf--Nonius CAD-4'
_diffrn_measurement_method     ω/2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3435
_diffrn_reflns_av_R_equivalents     0.0233
_diffrn_reflns_av_sigmaI/netI     0.0180
_diffrn_reflns_theta_min     5.39
_diffrn_reflns_theta_max     66.94
_diffrn_reflns_theta_full     66.94
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     0
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     120
_diffrn_standards_decay_%     0.9
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors
based on F² are statistically about twice as large as those based on F,
and R-factors based on ALL data will be even larger.
;
_reflns_number_total     2004
_reflns_number_gt     1834
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0482
_refine_ls_R_factor_gt     0.0451
_refine_ls_wR_factor_gt     0.1160
_refine_ls_wR_factor_ref     0.1193
_refine_ls_goodness_of_fit_ref     1.116
_refine_ls_restrained_S_all     1.116
_refine_ls_number_reflns     2004
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refxyz
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0668P)²+0.1549P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.160
_refine_diff_density_min     -0.271
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.082(4)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection     'CAD-4/PC Software (Enraf--Nonius, 1993)'
_computing_cell_refinement     'CAD-4/PC Software'
_computing_data_reduction     'REDU4 (Stoe & Cie, 1987)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia,
1997) and
PLATON (Spek, 2003)
;
_computing_publication_material     SHELXL97
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.15728(15) 0.19104(11) 0.08977(10) 0.0412(3) Uani d . 1 . .
    C C2 0.21043(18) 0.08416(12) 0.05208(13) 0.0525(4) Uani d . 1 . .
    H H2 0.178(2) 0.0072(15) 0.0753(14) 0.063 Uiso d . 1 . .
    C C3 0.30557(18) 0.08816(13) -0.02519(13) 0.0540(4) Uani d . 1 . .
    H H3 0.340(2) 0.0163(16) -0.0508(14) 0.065 Uiso d . 1 . .
    C C4 0.34820(15) 0.19772(12) -0.06634(11) 0.0447(4) Uani d . 1 . .
    C C5 0.44068(17) 0.20838(15) -0.15091(12) 0.0541(4) Uani d . 1 . .
    H H5 0.476(2) 0.1372(17) -0.1805(14) 0.065 Uiso d . 1 . .
    C C6 0.47152(17) 0.31624(16) -0.18868(12) 0.0565(4) Uani d . 1 . .
    H H6 0.528(2) 0.3307(15) -0.2445(14) 0.068 Uiso d . 1 . .
    C C7 0.41383(16) 0.42564(14) -0.14792(11) 0.0503(4) Uani d . 1 . .
    C C8 0.29445(15) 0.30311(11) -0.02564(10) 0.0382(3) Uani d . 1 . .
    C C9 0.19953(14) 0.30315(10) 0.05391(10) 0.0373(3) Uani d . 1 . .
    C C10 0.14622(16) 0.41074(11) 0.10257(10) 0.0427(3) Uani d . 1 . .
    H H10 0.1980(18) 0.4848(14) 0.0958(13) 0.051 Uiso d . 1 . .
    C C11 0.03097(16) 0.40070(12) 0.16004(10) 0.0443(3) Uani d . 1 . .
    H H11 -0.0082(19) 0.4672(14) 0.1966(13) 0.053 Uiso d . 1 . .
    C C12 -0.05011(15) 0.28219(11) 0.16920(10) 0.0413(3) Uani d . 1 . .
    C C13 -0.09784(19) 0.26890(16) 0.28025(12) 0.0549(4) Uani d . 1 . .
    H H13A -0.188(2) 0.3245(15) 0.2838(14) 0.066 Uiso d . 1 . .
    H H13B -0.137(2) 0.1902(16) 0.2840(15) 0.066 Uiso d . 1 . .
    H H13C -0.005(2) 0.2882(14) 0.3459(14) 0.066 Uiso d . 1 . .
    C C14 -0.19581(18) 0.26483(15) 0.07215(12) 0.0542(4) Uani d . 1 . .
    H H14A -0.277(2) 0.3268(16) 0.0704(14) 0.065 Uiso d . 1 . .
    H H14B -0.247(2) 0.1874(16) 0.0774(14) 0.065 Uiso d . 1 . .
    H H14C -0.159(2) 0.2711(15) 0.0013(16) 0.065 Uiso d . 1 . .
    O O1 0.06529(11) 0.18385(8) 0.16772(8) 0.0485(3) Uani d . 1 . .
    O O2 0.32864(11) 0.41358(8) -0.06463(7) 0.0453(3) Uani d . 1 . .
    O O3 0.43164(14) 0.52618(11) -0.17852(9) 0.0702(4) Uani d . 1 . .
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 0.0411(7) 0.0469(7) 0.0372(6) 0.0028(5) 0.0125(5) 0.0041(5)
    C2 0.0573(8) 0.0403(7) 0.0622(9) 0.0051(6) 0.0182(7) 0.0057(6)
    C3 0.0551(8) 0.0467(8) 0.0622(9) 0.0121(6) 0.0177(7) -0.0082(6)
    C4 0.0386(7) 0.0557(8) 0.0409(7) 0.0074(5) 0.0113(5) -0.0062(5)
    C5 0.0447(8) 0.0757(10) 0.0450(7) 0.0111(6) 0.0166(6) -0.0115(7)
    C6 0.0434(7) 0.0917(11) 0.0396(7) 0.0066(7) 0.0204(6) -0.0007(7)
    C7 0.0430(7) 0.0745(9) 0.0379(7) -0.0026(6) 0.0185(5) 0.0076(6)
    C8 0.0367(6) 0.0473(7) 0.0319(6) 0.0005(5) 0.0105(5) -0.0002(4)
    C9 0.0385(6) 0.0428(7) 0.0323(6) 0.0004(5) 0.0117(5) -0.0009(4)
    C10 0.0517(7) 0.0415(7) 0.0396(7) -0.0029(5) 0.0202(5) -0.0022(5)
    C11 0.0524(7) 0.0461(7) 0.0395(6) 0.0011(5) 0.0213(5) -0.0045(5)
    C12 0.0429(7) 0.0500(7) 0.0345(6) 0.0019(5) 0.0159(5) 0.0025(5)
    C13 0.0536(8) 0.0756(10) 0.0413(7) -0.0020(7) 0.0232(6) 0.0083(7)
    C14 0.0532(8) 0.0628(9) 0.0462(8) -0.0012(7) 0.0103(6) -0.0063(6)
    O1 0.0538(6) 0.0487(5) 0.0494(6) 0.0046(4) 0.0253(4) 0.0136(4)
    O2 0.0513(5) 0.0509(6) 0.0405(5) -0.0014(4) 0.0246(4) 0.0020(4)
    O3 0.0795(8) 0.0788(8) 0.0644(7) -0.0057(6) 0.0417(6) 0.0166(6)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 O1 . 1.3665(14) ?
    C1 C2 . 1.3860(18) ?
    C1 C9 . 1.3947(17) ?
    C2 C3 . 1.377(2) ?
    C2 H2 . 0.960(17) ?
    C3 C4 . 1.397(2) ?
    C3 H3 . 0.928(18) ?
    C4 C8 . 1.3897(17) ?
    C4 C5 . 1.4407(19) ?
    C5 C6 . 1.333(2) ?
    C5 H5 . 0.947(18) ?
    C6 C7 . 1.441(2) ?
    C6 H6 . 0.937(17) ?
    C7 O3 . 1.1994(18) ?
    C7 O2 . 1.3859(14) ?
    C8 O2 . 1.3724(15) ?
    C8 C9 . 1.3986(17) ?
    C9 C10 . 1.4535(17) ?
    C10 C11 . 1.3301(17) ?
    C10 H10 . 0.944(15) ?
    C11 C12 . 1.4996(18) ?
    C11 H11 . 0.962(16) ?
    C12 O1 . 1.4657(15) ?
    C12 C13 . 1.5185(17) ?
    C12 C14 . 1.5202(18) ?
    C13 H13A . 0.988(17) ?
    C13 H13B . 0.939(17) ?
    C13 H13C . 1.015(18) ?
    C14 H14A . 0.969(18) ?
    C14 H14B . 0.970(17) ?
    C14 H14C . 0.991(19) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 C1 C2 . . 117.60(11) ?
    O1 C1 C9 . . 120.08(11) ?
    C2 C1 C9 . . 122.28(12) ?
    C3 C2 C1 . . 119.14(12) ?
    C3 C2 H2 . . 118.8(10) ?
    C1 C2 H2 . . 121.9(10) ?
    C2 C3 C4 . . 121.12(12) ?
    C2 C3 H3 . . 118.8(11) ?
    C4 C3 H3 . . 120.1(11) ?
    C8 C4 C3 . . 118.16(12) ?
    C8 C4 C5 . . 117.76(12) ?
    C3 C4 C5 . . 124.06(12) ?
    C6 C5 C4 . . 120.46(13) ?
    C6 C5 H5 . . 120.9(10) ?
    C4 C5 H5 . . 118.6(10) ?
    C5 C6 C7 . . 121.95(12) ?
    C5 C6 H6 . . 125.7(11) ?
    C7 C6 H6 . . 112.3(11) ?
    O3 C7 O2 . . 116.46(13) ?
    O3 C7 C6 . . 126.88(12) ?
    O2 C7 C6 . . 116.66(12) ?
    O2 C8 C4 . . 121.06(11) ?
    O2 C8 C9 . . 116.36(10) ?
    C4 C8 C9 . . 122.56(11) ?
    C1 C9 C8 . . 116.71(10) ?
    C1 C9 C10 . . 118.62(11) ?
    C8 C9 C10 . . 124.66(11) ?
    C11 C10 C9 . . 118.81(12) ?
    C11 C10 H10 . . 121.9(9) ?
    C9 C10 H10 . . 119.2(9) ?
    C10 C11 C12 . . 120.93(11) ?
    C10 C11 H11 . . 123.7(9) ?
    C12 C11 H11 . . 115.4(9) ?
    O1 C12 C11 . . 109.80(10) ?
    O1 C12 C13 . . 104.52(10) ?
    C11 C12 C13 . . 111.80(11) ?
    O1 C12 C14 . . 108.41(10) ?
    C11 C12 C14 . . 110.66(11) ?
    C13 C12 C14 . . 111.42(11) ?
    C12 C13 H13A . . 110.0(10) ?
    C12 C13 H13B . . 107.5(11) ?
    H13A C13 H13B . . 107.4(14) ?
    C12 C13 H13C . . 112.5(9) ?
    H13A C13 H13C . . 107.3(13) ?
    H13B C13 H13C . . 112.0(14) ?
    C12 C14 H14A . . 111.7(10) ?
    C12 C14 H14B . . 110.5(10) ?
    H14A C14 H14B . . 108.1(14) ?
    C12 C14 H14C . . 109.1(10) ?
    H14A C14 H14C . . 106.9(14) ?
    H14B C14 H14C . . 110.6(14) ?
    C1 O1 C12 . . 116.67(9) ?
    C8 O2 C7 . . 122.06(10) ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O1 C1 C2 C3 . . . . -178.99(12) ?
    C9 C1 C2 C3 . . . . -1.4(2) ?
    C1 C2 C3 C4 . . . . -0.4(2) ?
    C2 C3 C4 C8 . . . . 1.2(2) ?
    C2 C3 C4 C5 . . . . -176.96(12) ?
    C8 C4 C5 C6 . . . . -0.5(2) ?
    C3 C4 C5 C6 . . . . 177.59(14) ?
    C4 C5 C6 C7 . . . . -0.4(2) ?
    C5 C6 C7 O3 . . . . -177.97(15) ?
    C5 C6 C7 O2 . . . . 2.0(2) ?
    C3 C4 C8 O2 . . . . -178.35(11) ?
    C5 C4 C8 O2 . . . . -0.11(19) ?
    C3 C4 C8 C9 . . . . -0.3(2) ?
    C5 C4 C8 C9 . . . . 177.95(10) ?
    O1 C1 C9 C8 . . . . 179.73(10) ?
    C2 C1 C9 C8 . . . . 2.2(2) ?
    O1 C1 C9 C10 . . . . 1.09(19) ?
    C2 C1 C9 C10 . . . . -176.48(12) ?
    O2 C8 C9 C1 . . . . 176.83(10) ?
    C4 C8 C9 C1 . . . . -1.32(19) ?
    O2 C8 C9 C10 . . . . -4.62(19) ?
    C4 C8 C9 C10 . . . . 177.23(11) ?
    C1 C9 C10 C11 . . . . -14.67(19) ?
    C8 C9 C10 C11 . . . . 166.81(12) ?
    C9 C10 C11 C12 . . . . -3.58(19) ?
    C10 C11 C12 O1 . . . . 31.95(16) ?
    C10 C11 C12 C13 . . . . 147.48(13) ?
    C10 C11 C12 C14 . . . . -87.68(15) ?
    C2 C1 O1 C12 . . . . -152.23(12) ?
    C9 C1 O1 C12 . . . . 30.09(16) ?
    C11 C12 O1 C1 . . . . -44.76(14) ?
    C13 C12 O1 C1 . . . . -164.83(11) ?
    C14 C12 O1 C1 . . . . 76.24(13) ?
    C4 C8 O2 C7 . . . . 1.78(19) ?
    C9 C8 O2 C7 . . . . -176.40(10) ?
    O3 C7 O2 C8 . . . . 177.31(12) ?
    C6 C7 O2 C8 . . . . -2.64(18) ?
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
    C5 H5 O3 2_644 0.947(18) 2.400(18) 3.2710(17) 152.9(14)
data_global
_journal_date_recd_electronic     2005-12-13
_journal_date_accepted     2006-03-06
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      4
_journal_page_first     o1340
_journal_page_last     o1341
_journal_paper_category     EO
_journal_coeditor_code     DN6291
_publ_contact_author
;
S K Nayak
;
_publ_contact_author_email     sknayak@magnum.barc.ernet.in
_publ_contact_author_fax     '91-22-25505151'
_publ_contact_author_phone     '91-22-25592410'
_publ_section_title
;
Reinvestigation of seselin
;
loop_
    _publ_author_name
    _publ_author_address
    'Bauri, A. K.'
;
Bioorganic Division
Bhabha Atomic Research Centre
Trombay
Mumbai 400 085
India
;
    'Foro, Sabine'
;
Clemens Schöpf-Institut für Organische Chemie und Biochemie
Technische Universität Darmstadt
Petersenstraße 22
D-64287 Darmstadt
Germany
;
    'Lindner, Hans-Jörg'
;
Clemens Schöpf-Institut für Organische Chemie und Biochemie
Technische Universität Darmstadt
Petersenstraße 22
D-64287 Darmstadt
Germany
;
    'Nayak, Sandip K.'
;
Bhabha Atomic Research Centre
Trombay
Mumbai 400 085
India
;
