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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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/  #
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data_global
_audit_creation_method     'SHELXL97 CIF, edited IUCr template'
_journal_date_recd_electronic     2007-11-19
_journal_date_accepted     2007-11-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      1
_journal_page_first     o158
_journal_page_last     o158
_journal_paper_category     QO
_journal_coeditor_code     OM2194
_publ_contact_author_name     'Dr P.A. Crooks'
_publ_contact_author_address
;
Dept. of Pharm. Sciences
College of Pharmacy
University of Kentucky
Lexington KY 40536
USA
;
_publ_contact_author_email     'pcrooks@email.uky.edu'
_publ_contact_author_fax     '859 257 2585'
_publ_contact_author_phone     '859 257 1718'
_publ_section_title
;
3-Ethyl-2-methyl-5-methylene-6,7-dihydroindol-4(5<i>H</i>)-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Sonar, Vijayakumar N.'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington KY 40536
USA
;
    'Parkin, Sean'
;
Department of Chemistry
University of Kentucky
Lexington KY 40536
USA
;
    'Crooks, Peter A.'
;
Department of Pharmaceutical Sciences
College of Pharmacy
University of Kentucky
Lexington KY 40536
USA
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
3-Ethyl-2-methyl-5-methylene-6,7-dihydroindol-4(5<i>H</i>)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H15 N O'
_chemical_formula_sum     'C12 H15 N O'
_chemical_formula_iupac     'C12 H15 N O'
_chemical_formula_weight     189.25
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
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'
_cell_length_a     9.0451(3)
_cell_length_b     8.5840(3)
_cell_length_c     14.3557(5)
_cell_angle_alpha     90.00
_cell_angle_beta     107.3550(10)
_cell_angle_gamma     90.00
_cell_volume     1063.88(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9990
_cell_measurement_theta_min     3.2
_cell_measurement_theta_max     69.4
_cell_measurement_temperature     90.0(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.15
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.182
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     408
_exptl_absorpt_coefficient_mu     0.589
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS in APEX2; Bruker, 2006)'
_exptl_absorpt_correction_T_min     0.837
_exptl_absorpt_correction_T_max     0.944
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     90.0(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source     'fine-focus rotating anode'
_diffrn_radiation_monochromator     'graded multilayer optics'
_diffrn_measurement_device_type     'Bruker X8 Proteum diffractometer'
_diffrn_measurement_method     '\f and \w scans'
_diffrn_detector_area_resol_mean     18
_diffrn_reflns_number     15160
_diffrn_reflns_av_R_equivalents     0.0394
_diffrn_reflns_av_sigmaI/netI     0.0223
_diffrn_reflns_theta_min     5.2
_diffrn_reflns_theta_max     69.4
_diffrn_reflns_theta_full     69.40
_diffrn_measured_fraction_theta_max     0.989
_diffrn_measured_fraction_theta_full     0.989
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ 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     1972
_reflns_number_gt     1893
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0389
_refine_ls_R_factor_gt     0.0377
_refine_ls_wR_factor_gt     0.0952
_refine_ls_wR_factor_ref     0.0967
_refine_ls_goodness_of_fit_ref     1.050
_refine_ls_restrained_S_all     1.050
_refine_ls_number_reflns     1972
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+0.4320P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.243
_refine_diff_density_min     -0.196
_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' 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'
    'N' 'N' 0.0311 0.0180
                         '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     'APEX2 (Bruker, 2006)'
_computing_cell_refinement     'APEX2 (Bruker, 2006)'
_computing_data_reduction     'APEX2 (Bruker, 2006)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'XP in SHELXTL (Sheldrick, 1995)'
_computing_publication_material
;
SHELX97 (Sheldrick, 1997) and local procedures
;
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
    O O1 0.68573(9) 0.20035(10) 0.42456(6) 0.0247(2) Uani d . 1 . .
    N N1 0.35484(10) 0.23361(11) 0.11591(6) 0.0186(2) Uani d . 1 . .
    H H1 0.3128 0.2575 0.0540 0.022 Uiso calc R 1 . .
    C C2 0.49707(13) 0.27649(13) 0.17035(8) 0.0181(2) Uani d . 1 . .
    C C3 0.60968(13) 0.37109(14) 0.13708(8) 0.0232(3) Uani d . 1 . .
    H H3A 0.5914 0.4835 0.1445 0.028 Uiso calc R 1 . .
    H H3B 0.5977 0.3499 0.0674 0.028 Uiso calc R 1 . .
    C C4 0.77279(13) 0.32599(14) 0.20002(8) 0.0239(3) Uani d . 1 . .
    H H4A 0.7983 0.2212 0.1805 0.029 Uiso calc R 1 . .
    H H4B 0.8484 0.4006 0.1879 0.029 Uiso calc R 1 . .
    C C5 0.78799(13) 0.32500(13) 0.30777(8) 0.0212(3) Uani d . 1 . .
    C C6 0.66379(13) 0.24233(12) 0.33901(8) 0.0184(2) Uani d . 1 . .
    C C7 0.52110(12) 0.21662(12) 0.26362(8) 0.0168(2) Uani d . 1 . .
    C C8 0.38323(12) 0.13283(12) 0.26393(8) 0.0179(3) Uani d . 1 . .
    C C9 0.28372(13) 0.14590(12) 0.17184(8) 0.0190(3) Uani d . 1 . .
    C C10 0.12335(13) 0.08583(15) 0.12770(9) 0.0270(3) Uani d . 1 . .
    H H10A 0.1004 0.0069 0.1708 0.041 Uiso calc R 1 . .
    H H10B 0.1149 0.0391 0.0640 0.041 Uiso calc R 1 . .
    H H10C 0.0494 0.1719 0.1193 0.041 Uiso calc R 1 . .
    C C11 0.35382(13) 0.04614(13) 0.34712(8) 0.0224(3) Uani d . 1 . .
    H H11A 0.4509 -0.0057 0.3850 0.027 Uiso calc R 1 . .
    H H11B 0.2761 -0.0362 0.3205 0.027 Uiso calc R 1 . .
    C C12 0.29655(17) 0.14824(17) 0.41558(10) 0.0342(3) Uani d . 1 . .
    H H12A 0.3746 0.2276 0.4444 0.051 Uiso calc R 1 . .
    H H12B 0.2784 0.0839 0.4675 0.051 Uiso calc R 1 . .
    H H12C 0.1996 0.1991 0.3790 0.051 Uiso calc R 1 . .
    C C13 0.90486(14) 0.39164(15) 0.37417(9) 0.0283(3) Uani d . 1 . .
    H H13A 0.9101 0.3872 0.4412 0.034 Uiso calc R 1 . .
    H H13B 0.9835 0.4439 0.3548 0.034 Uiso calc R 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
    O1 0.0246(4) 0.0296(5) 0.0160(4) -0.0050(3) 0.0003(3) 0.0018(3)
    N1 0.0188(5) 0.0208(5) 0.0137(4) 0.0021(4) 0.0010(4) -0.0001(3)
    C2 0.0186(5) 0.0177(5) 0.0177(5) 0.0014(4) 0.0046(4) -0.0012(4)
    C3 0.0249(6) 0.0265(6) 0.0184(5) -0.0025(5) 0.0070(5) 0.0024(4)
    C4 0.0204(6) 0.0266(6) 0.0260(6) -0.0032(5) 0.0091(5) 0.0003(5)
    C5 0.0180(5) 0.0193(5) 0.0245(6) 0.0003(4) 0.0040(4) 0.0025(4)
    C6 0.0198(6) 0.0166(5) 0.0174(5) 0.0004(4) 0.0033(4) -0.0008(4)
    C7 0.0172(5) 0.0165(5) 0.0158(5) 0.0003(4) 0.0037(4) -0.0009(4)
    C8 0.0176(5) 0.0163(5) 0.0194(5) 0.0001(4) 0.0049(4) -0.0012(4)
    C9 0.0178(5) 0.0169(5) 0.0212(6) 0.0005(4) 0.0043(4) -0.0018(4)
    C10 0.0189(6) 0.0272(6) 0.0304(6) -0.0025(5) 0.0002(5) -0.0010(5)
    C11 0.0221(6) 0.0218(6) 0.0233(6) -0.0024(4) 0.0067(4) 0.0028(4)
    C12 0.0415(8) 0.0368(7) 0.0303(7) 0.0054(6) 0.0200(6) 0.0059(5)
    C13 0.0245(6) 0.0282(6) 0.0280(6) -0.0066(5) 0.0011(5) 0.0058(5)
_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
    O1 C6 . 1.2377(14) ?
    N1 C2 . 1.3423(14) ?
    N1 C9 . 1.3905(14) ?
    N1 H1 . 0.8800 ?
    C2 C7 . 1.3894(15) ?
    C2 C3 . 1.4883(15) ?
    C3 C4 . 1.5322(16) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 C5 . 1.5115(16) ?
    C4 H4A . 0.9900 ?
    C4 H4B . 0.9900 ?
    C5 C13 . 1.3237(17) ?
    C5 C6 . 1.5058(15) ?
    C6 C7 . 1.4327(15) ?
    C7 C8 . 1.4407(15) ?
    C8 C9 . 1.3640(15) ?
    C8 C11 . 1.4968(15) ?
    C9 C10 . 1.4911(15) ?
    C10 H10A . 0.9800 ?
    C10 H10B . 0.9800 ?
    C10 H10C . 0.9800 ?
    C11 C12 . 1.5185(17) ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C12 H12A . 0.9800 ?
    C12 H12B . 0.9800 ?
    C12 H12C . 0.9800 ?
    C13 H13A . 0.9500 ?
    C13 H13B . 0.9500 ?
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
    C2 N1 C9 . . 109.90(9) ?
    C2 N1 H1 . . 125.1 ?
    C9 N1 H1 . . 125.1 ?
    N1 C2 C7 . . 107.88(10) ?
    N1 C2 C3 . . 126.27(10) ?
    C7 C2 C3 . . 125.85(10) ?
    C2 C3 C4 . . 107.68(9) ?
    C2 C3 H3A . . 110.2 ?
    C4 C3 H3A . . 110.2 ?
    C2 C3 H3B . . 110.2 ?
    C4 C3 H3B . . 110.2 ?
    H3A C3 H3B . . 108.5 ?
    C5 C4 C3 . . 112.49(9) ?
    C5 C4 H4A . . 109.1 ?
    C3 C4 H4A . . 109.1 ?
    C5 C4 H4B . . 109.1 ?
    C3 C4 H4B . . 109.1 ?
    H4A C4 H4B . . 107.8 ?
    C13 C5 C6 . . 119.71(11) ?
    C13 C5 C4 . . 122.95(11) ?
    C6 C5 C4 . . 117.34(10) ?
    O1 C6 C7 . . 123.12(10) ?
    O1 C6 C5 . . 121.31(10) ?
    C7 C6 C5 . . 115.57(9) ?
    C2 C7 C6 . . 121.18(10) ?
    C2 C7 C8 . . 107.51(9) ?
    C6 C7 C8 . . 131.31(10) ?
    C9 C8 C7 . . 106.11(9) ?
    C9 C8 C11 . . 126.25(10) ?
    C7 C8 C11 . . 127.64(10) ?
    C8 C9 N1 . . 108.61(9) ?
    C8 C9 C10 . . 131.34(11) ?
    N1 C9 C10 . . 120.05(10) ?
    C9 C10 H10A . . 109.5 ?
    C9 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C9 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C8 C11 C12 . . 113.92(10) ?
    C8 C11 H11A . . 108.8 ?
    C12 C11 H11A . . 108.8 ?
    C8 C11 H11B . . 108.8 ?
    C12 C11 H11B . . 108.8 ?
    H11A C11 H11B . . 107.7 ?
    C11 C12 H12A . . 109.5 ?
    C11 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C11 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    C5 C13 H13A . . 120.0 ?
    C5 C13 H13B . . 120.0 ?
    H13A C13 H13B . . 120.0 ?
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
    C9 N1 C2 C7 . . . . 0.04(12) ?
    C9 N1 C2 C3 . . . . 179.92(10) ?
    N1 C2 C3 C4 . . . . -152.52(11) ?
    C7 C2 C3 C4 . . . . 27.34(15) ?
    C2 C3 C4 C5 . . . . -48.30(13) ?
    C3 C4 C5 C13 . . . . -133.03(12) ?
    C3 C4 C5 C6 . . . . 47.57(14) ?
    C13 C5 C6 O1 . . . . -18.54(17) ?
    C4 C5 C6 O1 . . . . 160.88(10) ?
    C13 C5 C6 C7 . . . . 161.42(11) ?
    C4 C5 C6 C7 . . . . -19.16(14) ?
    N1 C2 C7 C6 . . . . 179.76(9) ?
    C3 C2 C7 C6 . . . . -0.13(17) ?
    N1 C2 C7 C8 . . . . -0.05(12) ?
    C3 C2 C7 C8 . . . . -179.93(10) ?
    O1 C6 C7 C2 . . . . 174.83(10) ?
    C5 C6 C7 C2 . . . . -5.13(15) ?
    O1 C6 C7 C8 . . . . -5.42(19) ?
    C5 C6 C7 C8 . . . . 174.62(10) ?
    C2 C7 C8 C9 . . . . 0.04(12) ?
    C6 C7 C8 C9 . . . . -179.74(11) ?
    C2 C7 C8 C11 . . . . 179.14(10) ?
    C6 C7 C8 C11 . . . . -0.63(19) ?
    C7 C8 C9 N1 . . . . -0.02(12) ?
    C11 C8 C9 N1 . . . . -179.14(10) ?
    C7 C8 C9 C10 . . . . -179.29(11) ?
    C11 C8 C9 C10 . . . . 1.6(2) ?
    C2 N1 C9 C8 . . . . -0.01(12) ?
    C2 N1 C9 C10 . . . . 179.35(10) ?
    C9 C8 C11 C12 . . . . -96.71(14) ?
    C7 C8 C11 C12 . . . . 84.36(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
    N1 H1 O1 4_565 0.88 1.91 2.7749(12) 169.1