##############################################################################
###                                                                        ###
###        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_global
_audit_creation_method     'SHELXL-97'
_journal_date_recd_electronic     2001-01-22
_journal_date_accepted     2001-01-30
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2001
_journal_volume     57
_journal_issue      3
_journal_page_first     o225
_journal_page_last     o227
_journal_paper_category     EO
_publ_contact_author_name     'Dr Kanji Kubo'
_publ_contact_author_address
;
Institute of Advanced Material Study
Kyushu University
Kasuga-koen, Kasuga
Fukuoka 816-8580
Japan
;
_publ_contact_author_email     kubo-k@cm.kyushu-u.ac.jp
_publ_contact_author_fax     '81(092)5837810'
_publ_contact_author_phone     '81(092)5837807'
_publ_section_title
;
3-Phenylpyrrolo[2,3-b]tropone
;
loop_
    _publ_author_name
    _publ_author_address
    'Kubo, Kanji '
; Institute of Advanced Material Study, 86
Kyushu University
Kasuga-koen, Kasuga
Fukuoka 816-8580
Japan
;
    ' Tsujimoto, Teppei '
; Graduate School of Engineering Sciences, 39
Kyushu University
Kasuga-koen, Kasuga
Fukuoka 816-8580
Japan
;
    'Mori, Akira'
; Institute of Advanced Material Study, 86
Kyushu University
Kasuga-koen, Kasuga
Fukuoka 816-8580
Japan
;
data_I
_chemical_name_systematic
;
3-Phenylpyrrolo[2,3-b]tropone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H11 N O'
_chemical_formula_sum     'C15 H11 N O'
_chemical_formula_iupac     'C15 H11 N O'
_chemical_formula_weight     221.25
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
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     14.2145(10)
_cell_length_b     7.7681(5)
_cell_length_c     10.3928(6)
_cell_angle_alpha     90.00
_cell_angle_beta     101.980(5)
_cell_angle_gamma     90.00
_cell_volume     1122.58(13)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     11.0
_cell_measurement_theta_max     18.2
_cell_measurement_temperature     296(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     'pale yellow'
_exptl_crystal_size_max      .47
_exptl_crystal_size_mid      .47
_exptl_crystal_size_min      .43
_exptl_crystal_density_diffrn     1.309
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     464
_exptl_absorpt_coefficient_mu      .082
_exptl_absorpt_correction_type
; psi-scan
;
_exptl_absorpt_process_details
; (North et al., 1968)
;
_exptl_absorpt_correction_T_min      .978
_exptl_absorpt_correction_T_max      .999
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_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     2851
_diffrn_reflns_av_R_equivalents      .022
_diffrn_reflns_av_sigmaI/netI      .030
_diffrn_reflns_theta_min     2.9
_diffrn_reflns_theta_max     28.0
_diffrn_reflns_theta_full     28.0
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     .000
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     0
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     120
_diffrn_standards_decay_%     3.9
_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     2700
_reflns_number_gt     1921
_reflns_threshold_expression     'I>2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .074
_refine_ls_R_factor_gt      .042
_refine_ls_wR_factor_ref      .116
_refine_ls_goodness_of_fit_ref     1.03
_refine_ls_restrained_S_all     1.03
_refine_ls_number_reflns     2700
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0526P)²+0.2047P] where P = (Fo²+2Fc²)/3'
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/su_mean     <0.001
_refine_diff_density_max     .18
_refine_diff_density_min     -.22
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
; CAD-4 Software (Enraf-Nonius, 1989)
;
_computing_cell_refinement
; CAD-4 Software
;
_computing_data_reduction
; MolEN (Fair, 1990)
;
_computing_structure_solution
; SIR97 (Altomare et al., 1997)
;
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'Xtal_GX (Hall & du Boulay, 1995)'
_computing_publication_material     'SHELXL97'
loop_
    _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
    _atom_site_type_symbol
    N1  .11507(8)  .24901(15)  -.12642(11)  .0408(3) Uani d . 1 . . N
    H1  .0638(12)  .229(2)  -.2009(17)  .059(5) Uiso d . 1 . . H
    O1  .01425(8)  .53883(15)  -.20816(11)  .0581(3) Uani d . 1 . . O
    C1  .07444(10)  .54791(19)  -.10252(15)  .0429(3) Uani d . 1 . . C
    C2  .13198(9)  .39801(17)  -.05691(13)  .0367(3) Uani d . 1 . . C
    C3  .20964(9)  .36788(16)  .05017(13)  .0345(3) Uani d . 1 . . C
    C4  .25393(10)  .48854(18)  .14654(14)  .0423(3) Uani d . 1 . . C
    H4  .3087  .4508  .2051  .051 Uiso calc R 1 . . H
    C5  .22584(12)  .6521(2)  .16325(15)  .0489(4) Uani d . 1 . . C
    H5  .2629  .7120  .2333  .059 Uiso calc R 1 . . H
    C6  .14712(12)  .74387(19)  .08764(16)  .0512(4) Uani d . 1 . . C
    H6  .1370  .8516  .1213  .061 Uiso calc R 1 . . H
    C7  .08409(11)  .70298(19)  -.02457(16)  .0502(4) Uani d . 1 . . C
    H7  .0398  .7888  -.0567  .060 Uiso calc R 1 . . H
    C8  .17702(10)  .12603(18)  -.06909(14)  .0398(3) Uani d . 1 . . C
    H8  .1783  .0133  -.0988  .048 Uiso calc R 1 . . H
    C9  .23780(9)  .19225(17)  .03951(13)  .0361(3) Uani d . 1 . . C
    C10  .31509(9)  .09397(17)  .12569(13)  .0375(3) Uani d . 1 . . C
    C11  .32669(10)  .09459(19)  .26228(14)  .0431(3) Uani d . 1 . . C
    H11  .2870  .1634  .3015  .052 Uiso calc R 1 . . H
    C12  .39655(11)  -.0060(2)  .34035(17)  .0539(4) Uani d . 1 . . C
    H12  .4032  -.0047  .4313  .065 Uiso calc R 1 . . H
    C13  .45612(11)  -.1079(2)  .28404(19)  .0608(5) Uani d . 1 . . C
    H13  .5032  -.1748  .3366  .073 Uiso calc R 1 . . H
    C14  .44574(12)  -.1101(2)  .1495(2)  .0619(5) Uani d . 1 . . C
    H14  .4858  -.1791  .1112  .074 Uiso calc R 1 . . H
    C15  .37617(11)  -.0105(2)  .07085(17)  .0503(4) Uani d . 1 . . C
    H15  .3700  -.0132  -.0200  .060 Uiso calc R 1 . . H
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  .0399(6)  .0405(6)  .0377(6)  -.0053(5)  -.0020(5)  .0007(5)
    O1  .0530(6)  .0540(7)  .0580(7)  .0037(5)  -.0102(5)  .0132(5)
    C1  .0378(7)  .0419(8)  .0474(8)  -.0013(6)  .0053(6)  .0121(6)
    C2  .0349(6)  .0367(7)  .0369(7)  -.0044(5)  .0041(5)  .0034(5)
    C3  .0344(6)  .0338(6)  .0348(7)  -.0025(5)  .0058(5)  .0031(5)
    C4  .0433(7)  .0391(7)  .0404(7)  -.0053(6)  -.0009(6)  .0015(6)
    C5  .0606(9)  .0383(7)  .0452(8)  -.0101(7)  .0048(7)  -.0041(6)
    C6  .0646(10)  .0333(7)  .0581(9)  -.0009(7)  .0182(8)  .0014(6)
    C7  .0506(8)  .0363(7)  .0629(10)  .0047(6)  .0102(7)  .0106(7)
    C8  .0436(7)  .0341(7)  .0407(7)  -.0027(6)  .0063(6)  -.0003(6)
    C9  .0369(6)  .0348(6)  .0356(7)  -.0019(5)  .0056(5)  .0013(5)
    C10  .0350(6)  .0341(6)  .0415(7)  -.0014(5)  .0040(5)  .0007(6)
    C11  .0430(7)  .0419(7)  .0422(7)  .0037(6)  .0038(6)  -.0006(6)
    C12  .0509(9)  .0536(9)  .0494(9)  .0022(7)  -.0075(7)  .0055(7)
    C13  .0440(8)  .0537(10)  .0767(12)  .0105(7)  -.0056(8)  .0123(9)
    C14  .0486(9)  .0572(10)  .0811(13)  .0166(8)  .0161(9)  .0008(9)
    C15  .0499(8)  .0506(9)  .0514(9)  .0066(7)  .0129(7)  -.0004(7)
_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
    N1 C2 . 1.3591(17) yes
    N1 C8 . 1.3510(18) yes
    N1 H1 .  .959(17) yes
    O1 C1 . 1.2460(17) yes
    C1 C2 . 1.4452(19) yes
    C1 C7 . 1.442(2) yes
    C2 C3 . 1.4149(18) yes
    C3 C4 . 1.4199(19) yes
    C3 C9 . 1.4326(19) yes
    C4 C5 . 1.354(2) yes
    C4 H4 .  .9300 ?
    C5 C6 . 1.419(2) yes
    C5 H5 .  .9300 ?
    C6 C7 . 1.353(2) yes
    C6 H6 .  .9300 ?
    C7 H7 .  .9300 ?
    C8 C9 . 1.3712(18) yes
    C8 H8 .  .9300 ?
    C9 C10 . 1.4777(18) yes
    C10 C11 . 1.3948(19) yes
    C10 C15 . 1.394(2) yes
    C11 C12 . 1.386(2) yes
    C11 H11 .  .9300 ?
    C12 C13 . 1.375(3) yes
    C12 H12 .  .9300 ?
    C13 C14 . 1.375(3) yes
    C13 H13 .  .9300 ?
    C14 C15 . 1.382(2) yes
    C14 H14 .  .9300 ?
    C15 H15 .  .9300 ?
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
    C8 N1 C2 . . 109.92(11) ?
    C8 N1 H1 . . 123.7(10) ?
    C2 N1 H1 . . 126.2(10) ?
    O1 C1 C7 . . 120.67(13) ?
    O1 C1 C2 . . 118.80(14) ?
    C7 C1 C2 . . 120.49(13) ?
    N1 C2 C3 . . 107.47(11) ?
    N1 C2 C1 . . 119.09(12) ?
    C3 C2 C1 . . 133.42(12) ?
    C2 C3 C4 . . 127.22(12) ?
    C2 C3 C9 . . 106.36(11) ?
    C4 C3 C9 . . 126.38(12) ?
    C5 C4 C3 . . 127.63(14) ?
    C5 C4 H4 . . 116.2 ?
    C3 C4 H4 . . 116.2 ?
    C4 C5 C6 . . 128.33(14) ?
    C4 C5 H5 . . 115.8 ?
    C6 C5 H5 . . 115.8 ?
    C7 C6 C5 . . 131.65(15) ?
    C7 C6 H6 . . 114.2 ?
    C5 C6 H6 . . 114.2 ?
    C6 C7 C1 . . 130.47(14) ?
    C6 C7 H7 . . 114.8 ?
    C1 C7 H7 . . 114.8 ?
    N1 C8 C9 . . 109.84(12) ?
    N1 C8 H8 . . 125.1 ?
    C9 C8 H8 . . 125.1 ?
    C8 C9 C3 . . 106.41(11) ?
    C8 C9 C10 . . 124.56(12) ?
    C3 C9 C10 . . 129.03(12) ?
    C15 C10 C11 . . 117.78(13) ?
    C15 C10 C9 . . 120.06(13) ?
    C11 C10 C9 . . 122.08(12) ?
    C12 C11 C10 . . 120.86(14) ?
    C12 C11 H11 . . 119.6 ?
    C10 C11 H11 . . 119.6 ?
    C13 C12 C11 . . 120.33(16) ?
    C13 C12 H12 . . 119.8 ?
    C11 C12 H12 . . 119.8 ?
    C12 C13 C14 . . 119.62(15) ?
    C12 C13 H13 . . 120.2 ?
    C14 C13 H13 . . 120.2 ?
    C13 C14 C15 . . 120.47(16) ?
    C13 C14 H14 . . 119.8 ?
    C15 C14 H14 . . 119.8 ?
    C14 C15 C10 . . 120.94(15) ?
    C14 C15 H15 . . 119.5 ?
    C10 C15 H15 . . 119.5 ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C8 N1 C2 C3 . . . .  .43(16) ?
    C8 N1 C2 C1 . . . . 179.03(12) ?
    O1 C1 C2 N1 . . . . -3.7(2) ?
    C7 C1 C2 N1 . . . . 173.98(13) ?
    O1 C1 C2 C3 . . . . 174.47(15) ?
    C7 C1 C2 C3 . . . . -7.9(2) ?
    N1 C2 C3 C4 . . . . 177.89(13) ?
    C1 C2 C3 C4 . . . .  -.4(3) ?
    N1 C2 C3 C9 . . . .  .18(15) ?
    C1 C2 C3 C9 . . . . -178.14(14) ?
    C2 C3 C4 C5 . . . . 6.6(2) ?
    C9 C3 C4 C5 . . . . -176.15(15) ?
    C3 C4 C5 C6 . . . . -1.5(3) ?
    C4 C5 C6 C7 . . . . -5.9(3) ?
    C5 C6 C7 C1 . . . . 2.4(3) ?
    O1 C1 C7 C6 . . . . -175.93(16) ?
    C2 C1 C7 C6 . . . . 6.4(3) ?
    C2 N1 C8 C9 . . . .  -.91(16) ?
    N1 C8 C9 C3 . . . .  .99(15) ?
    N1 C8 C9 C10 . . . . -179.72(12) ?
    C2 C3 C9 C8 . . . .  -.71(15) ?
    C4 C3 C9 C8 . . . . -178.44(14) ?
    C2 C3 C9 C10 . . . . -179.96(13) ?
    C4 C3 C9 C10 . . . . 2.3(2) ?
    C8 C9 C10 C15 . . . . 45.5(2) ?
    C3 C9 C10 C11 . . . . 48.0(2) yes
    C3 C9 C10 C15 . . . . -135.37(15) yes
    C8 C9 C10 C11 . . . . -131.13(15) ?
    C15 C10 C11 C12 . . . .  -.2(2) ?
    C9 C10 C11 C12 . . . . 176.50(13) ?
    C10 C11 C12 C13 . . . .  .3(2) ?
    C11 C12 C13 C14 . . . .  -.3(3) ?
    C12 C13 C14 C15 . . . .  .2(3) ?
    C13 C14 C15 C10 . . . .  -.1(3) ?
    C11 C10 C15 C14 . . . .  .1(2) ?
    C9 C10 C15 C14 . . . . -176.71(14) ?
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
    N1 H1 O1 2_544  .959(17) 1.968(16) 2.773(2) 140.38(10) yes
