##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'manual editing of form.cif'
_journal_date_recd_electronic     2008-09-22
_journal_date_accepted     2008-10-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue     11
_journal_page_first     o2156
_journal_page_last     o2156
_journal_paper_category     QO
_journal_coeditor_code     HB2804
_publ_contact_author
;
Matthias Zeller
Department of Chemistry
Youngstown State University
One University Plaza
Youngstown, OH 44555
USA
;
_publ_contact_author_email     mzeller@cc.ysu.edu
_publ_contact_author_fax     USA-330-941-1579
_publ_contact_author_phone     USA-330-941-7105
_publ_section_title
;
2,2,9-Trimethyl-2,3-dihydropyrano[2,3-a]carbazol-4-(11H)-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Makuteswaran Sridharan'
;
Department of Chemistry
Bharathiar University
Coimbatore 641 046
Tamil Nadu
India
;
    'Karnam J. Rajendra Prasad'
;
Department of Chemistry
Bharathiar University
Coimbatore 641 046
Tamil Nadu
India
;
    'Matthias Zeller'
;
Department of Chemistry
Youngstown State University
One University Plaza
Youngstown, OH 44555
USA
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2,2,9-Trimethyl-2,3-dihydropyrano[2,3-a]carbazol-4-(11H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H17 N O2'
_chemical_formula_sum     'C18 H17 N O2'
_chemical_formula_iupac     'C18 H17 N O2'
_chemical_formula_weight     279.33
_chemical_melting_point     ?
_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     8.6702(7)
_cell_length_b     6.1647(5)
_cell_length_c     26.617(2)
_cell_angle_alpha     90.00
_cell_angle_beta     99.1000(10)
_cell_angle_gamma     90.00
_cell_volume     1404.7(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5407
_cell_measurement_theta_min     2.38
_cell_measurement_theta_max     26.95
_cell_measurement_temperature     100(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.57
_exptl_crystal_size_mid     0.48
_exptl_crystal_size_min     0.24
_exptl_crystal_density_diffrn     1.321
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     592
_exptl_absorpt_coefficient_mu     0.086
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Bruker, 2007)'
_exptl_absorpt_correction_T_min     0.883
_exptl_absorpt_correction_T_max     0.980
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12327
_diffrn_reflns_av_R_equivalents     0.0305
_diffrn_reflns_av_sigmaI/netI     0.0270
_diffrn_reflns_theta_min     2.38
_diffrn_reflns_theta_max     26.97
_diffrn_reflns_theta_full     26.97
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -33
_diffrn_reflns_limit_l_max     33
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_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 >
σ(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     3044
_reflns_number_gt     2708
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0427
_refine_ls_R_factor_gt     0.0385
_refine_ls_wR_factor_gt     0.0950
_refine_ls_wR_factor_ref     0.0982
_refine_ls_goodness_of_fit_ref     1.044
_refine_ls_restrained_S_all     1.044
_refine_ls_number_reflns     3044
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0431P)²+0.5637P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.270
_refine_diff_density_min     -0.211
_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' 0.0033 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'
_computing_data_collection     'APEX2 (Bruker, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'Mercury (CCDC, 2007)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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 0.17131(13) 0.84678(19) 0.25979(4) 0.0187(2) Uani d . 1 . .
    C C2 0.09703(13) 0.7573(2) 0.29780(4) 0.0211(3) Uani d . 1 . .
    H H2 0.0487 0.6188 0.2934 0.025 Uiso calc R 1 . .
    C C3 0.09548(13) 0.8752(2) 0.34216(4) 0.0226(3) Uani d . 1 . .
    C C4 0.16617(13) 1.0821(2) 0.34766(4) 0.0234(3) Uani d . 1 . .
    H H4 0.1620 1.1628 0.3778 0.028 Uiso calc R 1 . .
    C C5 0.24143(13) 1.1703(2) 0.31029(4) 0.0214(3) Uani d . 1 . .
    H H5 0.2894 1.3090 0.3148 0.026 Uiso calc R 1 . .
    C C6 0.24560(12) 1.05129(18) 0.26567(4) 0.0182(2) Uani d . 1 . .
    C C7 0.31598(12) 1.08697(18) 0.22066(4) 0.0183(2) Uani d . 1 . .
    C C8 0.41054(13) 1.25324(19) 0.20595(4) 0.0211(3) Uani d . 1 . .
    H H8 0.4326 1.3796 0.2262 0.025 Uiso calc R 1 . .
    C C9 0.47011(13) 1.2281(2) 0.16144(4) 0.0224(3) Uani d . 1 . .
    H H9 0.5374 1.3364 0.1516 0.027 Uiso calc R 1 . .
    C C10 0.43349(13) 1.04460(19) 0.12984(4) 0.0203(2) Uani d . 1 . .
    C C11 0.33180(13) 0.88417(18) 0.14256(4) 0.0185(2) Uani d . 1 . .
    C C12 0.27867(12) 0.90402(18) 0.18939(4) 0.0181(2) Uani d . 1 . .
    C C13 0.01770(15) 0.7822(2) 0.38419(5) 0.0301(3) Uani d . 1 . .
    H H13A -0.0933 0.8209 0.3784 0.045 Uiso calc R 1 . .
    H H13B 0.0674 0.8413 0.4170 0.045 Uiso calc R 1 . .
    H H13C 0.0284 0.6239 0.3846 0.045 Uiso calc R 1 . .
    C C14 0.50985(13) 1.0114(2) 0.08483(4) 0.0237(3) Uani d . 1 . .
    C C15 0.47085(14) 0.7998(2) 0.05735(4) 0.0243(3) Uani d . 1 . .
    H H15A 0.5436 0.6861 0.0731 0.029 Uiso calc R 1 . .
    H H15B 0.4857 0.8159 0.0214 0.029 Uiso calc R 1 . .
    C C16 0.30334(14) 0.72833(19) 0.05911(4) 0.0208(2) Uani d . 1 . .
    C C17 0.27377(17) 0.5034(2) 0.03665(5) 0.0290(3) Uani d . 1 . .
    H H17A 0.3465 0.4003 0.0558 0.043 Uiso calc R 1 . .
    H H17B 0.2895 0.5048 0.0010 0.043 Uiso calc R 1 . .
    H H17C 0.1662 0.4598 0.0386 0.043 Uiso calc R 1 . .
    C C18 0.18336(14) 0.8888(2) 0.03275(4) 0.0229(3) Uani d . 1 . .
    H H18A 0.0779 0.8353 0.0345 0.034 Uiso calc R 1 . .
    H H18B 0.1966 0.9043 -0.0030 0.034 Uiso calc R 1 . .
    H H18C 0.1983 1.0300 0.0497 0.034 Uiso calc R 1 . .
    N N1 0.19001(11) 0.76108(16) 0.21306(4) 0.0199(2) Uani d . 1 . .
    H H1 0.1519 0.6366 0.2005 0.024 Uiso calc R 1 . .
    O O1 0.28283(10) 0.70934(13) 0.11287(3) 0.0218(2) Uani d . 1 . .
    O O2 0.60210(11) 1.14169(18) 0.07137(3) 0.0341(2) Uani d . 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 N1 . 1.3845(14) ?
    C1 C2 . 1.3959(16) ?
    C1 C6 . 1.4132(16) ?
    C2 C3 . 1.3887(17) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.4123(18) ?
    C3 C13 . 1.5079(17) ?
    C4 C5 . 1.3843(17) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.4013(16) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.4447(15) ?
    C7 C8 . 1.4064(16) ?
    C7 C12 . 1.4086(16) ?
    C8 C9 . 1.3739(17) ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.4156(17) ?
    C9 H9 . 0.9500 ?
    C10 C11 . 1.4016(16) ?
    C10 C14 . 1.4718(16) ?
    C11 O1 . 1.3638(14) ?
    C11 C12 . 1.4010(15) ?
    C12 N1 . 1.3847(14) ?
    C13 H13A . 0.9800 ?
    C13 H13B . 0.9800 ?
    C13 H13C . 0.9800 ?
    C14 O2 . 1.2263(15) ?
    C14 C15 . 1.5078(18) ?
    C15 C16 . 1.5255(17) ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C16 O1 . 1.4744(13) ?
    C16 C17 . 1.5155(17) ?
    C16 C18 . 1.5239(16) ?
    C17 H17A . 0.9800 ?
    C17 H17B . 0.9800 ?
    C17 H17C . 0.9800 ?
    C18 H18A . 0.9800 ?
    C18 H18B . 0.9800 ?
    C18 H18C . 0.9800 ?
    N1 H1 . 0.8800 ?
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
    N1 C1 C2 . . 129.29(11) ?
    N1 C1 C6 . . 108.89(10) ?
    C2 C1 C6 . . 121.80(10) ?
    C3 C2 C1 . . 118.47(11) ?
    C3 C2 H2 . . 120.8 ?
    C1 C2 H2 . . 120.8 ?
    C2 C3 C4 . . 119.90(11) ?
    C2 C3 C13 . . 119.81(12) ?
    C4 C3 C13 . . 120.28(11) ?
    C5 C4 C3 . . 121.77(11) ?
    C5 C4 H4 . . 119.1 ?
    C3 C4 H4 . . 119.1 ?
    C4 C5 C6 . . 118.78(11) ?
    C4 C5 H5 . . 120.6 ?
    C6 C5 H5 . . 120.6 ?
    C5 C6 C1 . . 119.24(11) ?
    C5 C6 C7 . . 133.95(11) ?
    C1 C6 C7 . . 106.79(10) ?
    C8 C7 C12 . . 120.57(10) ?
    C8 C7 C6 . . 133.09(11) ?
    C12 C7 C6 . . 106.29(10) ?
    C9 C8 C7 . . 118.24(11) ?
    C9 C8 H8 . . 120.9 ?
    C7 C8 H8 . . 120.9 ?
    C8 C9 C10 . . 121.51(11) ?
    C8 C9 H9 . . 119.2 ?
    C10 C9 H9 . . 119.2 ?
    C11 C10 C9 . . 120.74(11) ?
    C11 C10 C14 . . 118.66(11) ?
    C9 C10 C14 . . 120.47(11) ?
    O1 C11 C12 . . 117.93(10) ?
    O1 C11 C10 . . 124.60(10) ?
    C12 C11 C10 . . 117.46(10) ?
    N1 C12 C11 . . 129.31(10) ?
    N1 C12 C7 . . 109.45(10) ?
    C11 C12 C7 . . 121.24(10) ?
    C3 C13 H13A . . 109.5 ?
    C3 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C3 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    O2 C14 C10 . . 123.03(12) ?
    O2 C14 C15 . . 122.10(11) ?
    C10 C14 C15 . . 114.83(10) ?
    C14 C15 C16 . . 112.12(10) ?
    C14 C15 H15A . . 109.2 ?
    C16 C15 H15A . . 109.2 ?
    C14 C15 H15B . . 109.2 ?
    C16 C15 H15B . . 109.2 ?
    H15A C15 H15B . . 107.9 ?
    O1 C16 C17 . . 105.74(9) ?
    O1 C16 C18 . . 108.67(9) ?
    C17 C16 C18 . . 110.60(10) ?
    O1 C16 C15 . . 108.32(9) ?
    C17 C16 C15 . . 110.77(10) ?
    C18 C16 C15 . . 112.48(10) ?
    C16 C17 H17A . . 109.5 ?
    C16 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C16 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    C16 C18 H18A . . 109.5 ?
    C16 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    C16 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    C1 N1 C12 . . 108.55(9) ?
    C1 N1 H1 . . 125.7 ?
    C12 N1 H1 . . 125.7 ?
    C11 O1 C16 . . 115.16(9) ?
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
    N1 C1 C2 C3 . . . . 179.15(11) ?
    C6 C1 C2 C3 . . . . 0.73(17) ?
    C1 C2 C3 C4 . . . . 0.88(17) ?
    C1 C2 C3 C13 . . . . -179.36(10) ?
    C2 C3 C4 C5 . . . . -1.64(17) ?
    C13 C3 C4 C5 . . . . 178.61(11) ?
    C3 C4 C5 C6 . . . . 0.72(17) ?
    C4 C5 C6 C1 . . . . 0.88(16) ?
    C4 C5 C6 C7 . . . . -177.44(11) ?
    N1 C1 C6 C5 . . . . 179.66(10) ?
    C2 C1 C6 C5 . . . . -1.63(16) ?
    N1 C1 C6 C7 . . . . -1.60(12) ?
    C2 C1 C6 C7 . . . . 177.11(10) ?
    C5 C6 C7 C8 . . . . 2.2(2) ?
    C1 C6 C7 C8 . . . . -176.28(12) ?
    C5 C6 C7 C12 . . . . 179.42(12) ?
    C1 C6 C7 C12 . . . . 0.95(12) ?
    C12 C7 C8 C9 . . . . -2.51(16) ?
    C6 C7 C8 C9 . . . . 174.40(11) ?
    C7 C8 C9 C10 . . . . 2.39(17) ?
    C8 C9 C10 C11 . . . . 1.44(17) ?
    C8 C9 C10 C14 . . . . -174.39(11) ?
    C9 C10 C11 O1 . . . . 175.84(10) ?
    C14 C10 C11 O1 . . . . -8.26(17) ?
    C9 C10 C11 C12 . . . . -5.03(16) ?
    C14 C10 C11 C12 . . . . 170.87(10) ?
    O1 C11 C12 N1 . . . . 5.46(17) ?
    C10 C11 C12 N1 . . . . -173.73(11) ?
    O1 C11 C12 C7 . . . . -175.89(10) ?
    C10 C11 C12 C7 . . . . 4.92(16) ?
    C8 C7 C12 N1 . . . . 177.69(10) ?
    C6 C7 C12 N1 . . . . 0.03(12) ?
    C8 C7 C12 C11 . . . . -1.21(16) ?
    C6 C7 C12 C11 . . . . -178.86(10) ?
    C11 C10 C14 O2 . . . . -178.92(11) ?
    C9 C10 C14 O2 . . . . -3.00(18) ?
    C11 C10 C14 C15 . . . . -1.16(15) ?
    C9 C10 C14 C15 . . . . 174.76(10) ?
    O2 C14 C15 C16 . . . . -148.09(12) ?
    C10 C14 C15 C16 . . . . 34.13(14) ?
    C14 C15 C16 O1 . . . . -57.83(12) ?
    C14 C15 C16 C17 . . . . -173.36(10) ?
    C14 C15 C16 C18 . . . . 62.29(13) ?
    C2 C1 N1 C12 . . . . -176.93(11) ?
    C6 C1 N1 C12 . . . . 1.64(12) ?
    C11 C12 N1 C1 . . . . 177.74(11) ?
    C7 C12 N1 C1 . . . . -1.03(12) ?
    C12 C11 O1 C16 . . . . 162.98(10) ?
    C10 C11 O1 C16 . . . . -17.90(15) ?
    C17 C16 O1 C11 . . . . 168.56(10) ?
    C18 C16 O1 C11 . . . . -72.69(12) ?
    C15 C16 O1 C11 . . . . 49.79(12) ?
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
    C15 H15B O2 3_675 0.99 2.48 3.4034(13) 155
    N1 H1 Cg2 2_545 0.88 2.97 3.5822(11) 128
    C2 H2 Cg1 2_545 0.95 2.74 3.5332(13) 141
    C8 H8 Cg1 2_655 0.95 2.91 3.4124(12) 114
    C9 H9 Cg2 2_655 0.95 2.74 3.4372(13) 130
