##############################################################################
###                                                                        ###
###        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                                                              #
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# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
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data_global
_audit_creation_method     'SHELXL-97'
_journal_date_recd_electronic     2009-12-18
_journal_date_accepted     2009-12-28
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      2
_journal_page_first     o381
_journal_page_last     o381
_journal_paper_category     QO
_journal_coeditor_code     BT5154
_publ_contact_author_name
;
'Dr F. Nawaz Khan'
;
_publ_contact_author_address
;
Chemistry Division
School of Advanced Sciences,
VIT University,
Vellore 632 014, Tamil Nadu
India
;
_publ_contact_author_email     'nawaz_f@yahoo.co.in'
_publ_contact_author_fax     '(91) 416 2243092'
_publ_contact_author_phone     '(91) 416 2202334'
_publ_section_title
;
1,3,6-Trimethylpyrano[4,3-<i>b</i>]pyrrol-4(1<i>H</i>)-one
;
loop_
    _publ_author_name
    _publ_author_address
    'V. Krishnakumar'
;
School of Advanced Sciences,
VIT University, Vellore 632 014,
Tamil Nadu, India
;
    'F. Nawaz Khan'
;
School of Advanced Sciences,
VIT University, Vellore 632 014,
Tamil Nadu, India
;
    'Venkatesha R. Hathwar'
;
Solid State and Structural Chemistry Unit
Indian Institute of Science,
Bangalore 560012, Karnataka
India
;
    'P. Nithya'
;
School of Advanced Sciences,
VIT University, Vellore 632 014,
Tamil Nadu, India
;
    'S. Suresh'
;
Department of Chemistry
Aarupadai Veedu Institute of Technology,
Vinayaka Missions University, Paiyanoor,
Chennai 603 104, Tamil Nadu
India
;
data_I
_chemical_name_systematic
;
1,3,6-Trimethylpyrano[4,3-<i>b</i>]pyrrol-4(1<i>H</i>)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H11 N O2'
_chemical_formula_sum     'C10 H11 N O2'
_chemical_formula_structural     'C10 H11 N O2'
_chemical_formula_iupac     'C10 H11 N O2'
_chemical_formula_weight     177.20
_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_site_id
    _symmetry_equiv_pos_as_xyz
    1 x,y,z
    2 1/2-x,1/2+y,1/2-z
    3 -x,-y,-z
    4 1/2+x,1/2-y,1/2+z
_cell_length_a     7.5556(7)
_cell_length_b     8.4819(8)
_cell_length_c     14.3081(14)
_cell_angle_alpha     90
_cell_angle_beta     93.870(6)
_cell_angle_gamma     90
_cell_volume     914.86(15)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1235
_cell_measurement_theta_min     2.85
_cell_measurement_theta_max     20.36
_cell_measurement_temperature     295(2)
_cell_special_details     ?
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.33
_exptl_crystal_size_mid     0.28
_exptl_crystal_size_min     0.15
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.287
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'Not Measured'
_exptl_crystal_F_000     376
_exptl_absorpt_coefficient_mu     0.090
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(CrysAlisPro RED; Oxford Diffraction, 2009)'
_exptl_absorpt_correction_T_min     0.9156
_exptl_absorpt_correction_T_max     0.9866
_exptl_special_details
;
;
_diffrn_ambient_temperature     295(2)
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Oxford Xcalibur Eos (Nova) CCD detector'
_diffrn_measurement_method     '\w scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7291
_diffrn_reflns_av_R_equivalents     0.0340
_diffrn_reflns_av_sigmaI/netI     0.0308
_diffrn_reflns_theta_min     2.79
_diffrn_reflns_theta_max     25.50
_diffrn_reflns_theta_full     25.50
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_reflns_reduction_process     ?
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_refine_special_details
;
;
_reflns_number_total     1692
_reflns_number_gt     1176
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0733
_refine_ls_R_factor_gt     0.0505
_refine_ls_wR_factor_gt     0.1696
_refine_ls_wR_factor_ref     0.1789
_refine_ls_goodness_of_fit_ref     1.176
_refine_ls_restrained_S_all     1.176
_refine_ls_number_reflns     1692
_refine_ls_number_parameters     122
_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^)+(0.0888P)^2^+0.1440P] 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     0.267
_refine_diff_density_min     -0.177
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0040(10)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    O O 0.0106 0.0060 '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'
    H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement     'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_reduction     'CrysAlisPro RED (Oxford Diffraction, 2009)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
            'ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin <i>et al.</i>,  1993)'
_computing_publication_material     'WinGX (Farrugia, 1997)'
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
    N N1 0.1293(2) 0.4172(2) 0.87406(12) 0.0412(5) Uani d . 1 . .
    O O1 0.3720(3) 0.1280(3) 1.12304(13) 0.0818(7) Uani d . 1 . .
    O O2 0.3792(2) 0.3881(2) 1.13262(10) 0.0586(6) Uani d . 1 . .
    C C1 0.1778(3) 0.1674(3) 0.92158(16) 0.0466(6) Uani d . 1 . .
    C C2 0.1079(3) 0.2591(3) 0.85100(16) 0.0466(6) Uani d . 1 . .
    H H2 0.0534 0.2216 0.7951 0.056 Uiso calc R 1 . .
    C C3 0.2612(3) 0.5620(3) 1.01528(16) 0.0460(6) Uani d . 1 . .
    H H3 0.2372 0.6633 0.9929 0.055 Uiso calc R 1 . .
    C C4 0.3421(3) 0.5382(3) 1.09968(17) 0.0507(7) Uani d . 1 . .
    C C5 0.3331(3) 0.2497(3) 1.08310(16) 0.0526(7) Uani d . 1 . .
    C C6 0.2454(3) 0.2744(3) 0.99253(14) 0.0420(6) Uani d . 1 . .
    C C7 0.2128(3) 0.4269(2) 0.96087(14) 0.0389(6) Uani d . 1 . .
    C C8 0.4000(4) 0.6605(4) 1.1693(2) 0.0749(9) Uani d . 1 . .
    H H8A 0.3742 0.7631 1.1435 0.112 Uiso calc R 1 . .
    H H8B 0.5253 0.6511 1.1842 0.112 Uiso calc R 1 . .
    H H8C 0.3380 0.6465 1.2251 0.112 Uiso calc R 1 . .
    C C9 0.1882(4) -0.0092(3) 0.9237(2) 0.0702(9) Uani d . 1 . .
    H H9A 0.1145 -0.0518 0.8725 0.105 Uiso calc R 1 . .
    H H9B 0.1480 -0.0472 0.9818 0.105 Uiso calc R 1 . .
    H H9C 0.3087 -0.0416 0.9181 0.105 Uiso calc R 1 . .
    C C10 0.0743(4) 0.5500(3) 0.81496(17) 0.0551(7) Uani d . 1 . .
    H H10A 0.0008 0.6192 0.8487 0.083 Uiso calc R 1 . .
    H H10B 0.0085 0.5123 0.7597 0.083 Uiso calc R 1 . .
    H H10C 0.1771 0.6063 0.7974 0.083 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
    N1 0.0466(11) 0.0379(11) 0.0382(10) 0.0025(8) -0.0049(8) 0.0018(8)
    O1 0.1038(17) 0.0781(16) 0.0623(12) 0.0317(12) -0.0034(11) 0.0266(11)
    O2 0.0562(11) 0.0777(14) 0.0403(9) 0.0065(9) -0.0082(7) -0.0015(9)
    C1 0.0506(13) 0.0375(13) 0.0521(14) -0.0005(11) 0.0074(11) -0.0007(11)
    C2 0.0488(13) 0.0463(14) 0.0442(12) -0.0021(11) -0.0008(10) -0.0089(12)
    C3 0.0474(13) 0.0415(14) 0.0489(13) -0.0035(10) 0.0016(10) -0.0050(10)
    C4 0.0443(13) 0.0604(17) 0.0471(13) -0.0021(12) 0.0015(10) -0.0097(11)
    C5 0.0541(15) 0.0589(17) 0.0448(13) 0.0102(13) 0.0022(11) 0.0066(13)
    C6 0.0432(12) 0.0416(13) 0.0409(12) 0.0030(10) 0.0017(9) 0.0050(10)
    C7 0.0392(12) 0.0400(13) 0.0372(11) 0.0023(10) 0.0005(9) 0.0033(9)
    C8 0.0654(18) 0.096(2) 0.0630(17) -0.0162(17) -0.0004(13) -0.0329(16)
    C9 0.085(2) 0.0395(16) 0.087(2) 0.0000(15) 0.0159(16) -0.0025(15)
    C10 0.0634(16) 0.0556(17) 0.0450(13) 0.0061(13) -0.0055(11) 0.0116(11)
_geom_special_details
;
;
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 C7 . 1.357(3) ?
    N1 C2 . 1.388(3) ?
    N1 C10 . 1.452(3) ?
    O1 C5 . 1.206(3) ?
    O2 C4 . 1.380(3) ?
    O2 C5 . 1.403(3) ?
    C1 C2 . 1.353(3) ?
    C1 C6 . 1.430(3) ?
    C1 C9 . 1.500(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.332(3) ?
    C3 C7 . 1.419(3) ?
    C3 H3 . 0.9300 ?
    C4 C8 . 1.483(4) ?
    C5 C6 . 1.431(3) ?
    C6 C7 . 1.387(3) ?
    C8 H8A . 0.9600 ?
    C8 H8B . 0.9600 ?
    C8 H8C . 0.9600 ?
    C9 H9A . 0.9600 ?
    C9 H9B . 0.9600 ?
    C9 H9C . 0.9600 ?
    C10 H10A . 0.9600 ?
    C10 H10B . 0.9600 ?
    C10 H10C . 0.9600 ?
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
    C7 N1 C2 . . 108.41(19) ?
    C7 N1 C10 . . 125.64(19) ?
    C2 N1 C10 . . 125.94(19) ?
    C4 O2 C5 . . 124.21(19) ?
    C2 C1 C6 . . 105.5(2) ?
    C2 C1 C9 . . 127.3(2) ?
    C6 C1 C9 . . 127.2(2) ?
    C1 C2 N1 . . 110.2(2) ?
    C1 C2 H2 . . 124.9 ?
    N1 C2 H2 . . 124.9 ?
    C4 C3 C7 . . 117.4(2) ?
    C4 C3 H3 . . 121.3 ?
    C7 C3 H3 . . 121.3 ?
    C3 C4 O2 . . 121.3(2) ?
    C3 C4 C8 . . 126.8(3) ?
    O2 C4 C8 . . 111.9(2) ?
    O1 C5 O2 . . 115.6(2) ?
    O1 C5 C6 . . 129.6(3) ?
    O2 C5 C6 . . 114.8(2) ?
    C7 C6 C1 . . 108.3(2) ?
    C7 C6 C5 . . 119.6(2) ?
    C1 C6 C5 . . 132.2(2) ?
    N1 C7 C6 . . 107.66(19) ?
    N1 C7 C3 . . 129.6(2) ?
    C6 C7 C3 . . 122.7(2) ?
    C4 C8 H8A . . 109.5 ?
    C4 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C4 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    C1 C9 H9A . . 109.5 ?
    C1 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C1 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    N1 C10 H10A . . 109.5 ?
    N1 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    N1 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
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
    C6 C1 C2 N1 . . . . 0.3(2) ?
    C9 C1 C2 N1 . . . . -177.7(2) ?
    C7 N1 C2 C1 . . . . -0.5(2) ?
    C10 N1 C2 C1 . . . . 178.7(2) ?
    C7 C3 C4 O2 . . . . 0.6(3) ?
    C7 C3 C4 C8 . . . . -178.2(2) ?
    C5 O2 C4 C3 . . . . -1.5(3) ?
    C5 O2 C4 C8 . . . . 177.5(2) ?
    C4 O2 C5 O1 . . . . -178.4(2) ?
    C4 O2 C5 C6 . . . . 1.1(3) ?
    C2 C1 C6 C7 . . . . -0.1(2) ?
    C9 C1 C6 C7 . . . . 177.9(2) ?
    C2 C1 C6 C5 . . . . 179.7(2) ?
    C9 C1 C6 C5 . . . . -2.2(4) ?
    O1 C5 C6 C7 . . . . 179.4(2) ?
    O2 C5 C6 C7 . . . . 0.0(3) ?
    O1 C5 C6 C1 . . . . -0.4(4) ?
    O2 C5 C6 C1 . . . . -179.8(2) ?
    C2 N1 C7 C6 . . . . 0.4(2) ?
    C10 N1 C7 C6 . . . . -178.74(19) ?
    C2 N1 C7 C3 . . . . -178.8(2) ?
    C10 N1 C7 C3 . . . . 2.1(4) ?
    C1 C6 C7 N1 . . . . -0.2(2) ?
    C5 C6 C7 N1 . . . . 179.96(18) ?
    C1 C6 C7 C3 . . . . 179.06(19) ?
    C5 C6 C7 C3 . . . . -0.8(3) ?
    C4 C3 C7 N1 . . . . 179.6(2) ?
    C4 C3 C7 C6 . . . . 0.5(3) ?
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
    C10 H10B O1 4_454 0.96 2.46 3.404(3) 170 yes