##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, 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 2.0.1.  #
#                                                                            #
# 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                                                              #
#                                                                            #
# 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     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     98-03-13
_journal_date_accepted     98-05-28
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     1998
_journal_volume     C54
_journal_issue     DEC98
_journal_page_first     1925
_journal_page_last     1927
_journal_paper_category     FO
_publ_contact_author_name     'Professor Hoong-Kun Fun'
_publ_contact_author_address
;
X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM
Penang
Malaysia
;
_publ_contact_author_email     hkfun@usm.my
_publ_contact_author_fax     '6 04 6579150'
_publ_contact_author_phone     '6 04 6577888  Ext. 3690'
_publ_section_title
;
1,9a-Epoxy-1,2,3,4,4a,4b,5,8,8a,9a-decahydro-2-methyl-4-nitro-5,8-methano-9H-
fluoren-9-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Fun, Hoong-Kun' ?
;     X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Chinnakali, Kandasamy'
;     On leave from: Department of Physics
      Anna University, Chennai 600 025, India.
;
;     X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Hazra, Nirmal Kumar' ?
;     Department of Chemistry
      Indian Institute of Technology
      Kharagpur 721 302
      West Bengal
      India
;
    'Mal, Dipakranjan' ?
;     Department of Chemistry
      Indian Institute of Technology
      Kharagpur 721 302
      West Bengal
      India
;
    'Nigam, Gur Dayal' ?
;     Department of Physics and Meteorology
      Indian Institute of Technology
      Kharagpur 721 302
      West Bengal
      India
;
    'Razak, Ibrahim Abdul' ?
;     X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
data_ha1220
_audit_creation_method     SHELXL
_chemical_name_systematic
;
1,4,4a,4b,5,6,7,8,8a,9a-Decahydro-8,8a-epoxy-1,4-methano-7-methyl-5-
nitro fluoren-9(9H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     ?
_chemical_formula_sum     'C15 H17 N O4'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_weight     275.30
_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     11.5320(2)
_cell_length_b     11.2967(2)
_cell_length_c     10.3406(2)
_cell_angle_alpha     90.00
_cell_angle_beta     96.3120(10)
_cell_angle_gamma     90.00
_cell_volume     1338.94(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4864
_cell_measurement_theta_min     1.5
_cell_measurement_theta_max     33.0
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.48
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.28
_exptl_crystal_density_diffrn     1.366
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     584
_exptl_absorpt_coefficient_mu     0.099
_exptl_absorpt_correction_type     none
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     293(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     'Siemens SMART CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_reflns_number     8611
_diffrn_reflns_av_R_equivalents     0.024
_diffrn_reflns_av_sigmaI/netI     0.0310
_diffrn_reflns_theta_min     2.68
_diffrn_reflns_theta_max     27.5
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     3057
_reflns_number_observed     2334
_reflns_observed_criterion     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.066
_refine_ls_R_factor_obs     0.048
_refine_ls_wR_factor_all     0.132
_refine_ls_wR_factor_obs     0.119
_refine_ls_goodness_of_fit_all     1.054
_refine_ls_goodness_of_fit_obs     1.107
_refine_ls_restrained_S_all     1.054
_refine_ls_restrained_S_obs     1.107
_refine_ls_number_reflns     3056
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme
     'calc w = 1/[\s^2^(Fo^2^)+(0.0610P)^2^+0.3308P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_shift/esd_max     0.000
_refine_ls_shift/esd_mean     0.000
_refine_diff_density_max     0.249
_refine_diff_density_min     -0.190
_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     'SMART (Siemens, 1996a)'
_computing_cell_refinement     'SAINT (Siemens, 1996b)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXTL (Siemens, 1996c)'
_computing_structure_refinement     'SHELXTL'
_computing_molecular_graphics     'SHELXTL'
_computing_publication_material     'SHELXTL and PARST (Nardelli, 1995)'
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_group
    _atom_site_type_symbol
    O1 0.77961(13) 0.14612(12) 0.54574(13) 0.0593(4) Uani d . 1 . O
    O2 0.94165(11) 0.08571(10) 0.77657(12) 0.0490(3) Uani d . 1 . O
    O3 0.7453(2) -0.1907(2) 1.0300(2) 0.1047(8) Uani d . 1 . O
    O4 0.8018(2) -0.34985(14) 0.9515(2) 0.0985(7) Uani d . 1 . O
    N1 0.79097(14) -0.24379(14) 0.9485(2) 0.0527(4) Uani d . 1 . N
    C1 0.8403(2) -0.17725(13) 0.8392(2) 0.0390(4) Uani d . 1 . C
    C2 0.9711(2) -0.1632(2) 0.8737(2) 0.0435(4) Uani d . 1 . C
    C3 1.0262(2) -0.1174(2) 0.7547(2) 0.0455(4) Uani d . 1 . C
    C4 0.96062(15) -0.01353(15) 0.6922(2) 0.0428(4) Uani d . 1 . C
    C5 0.84256(14) 0.01519(13) 0.72349(15) 0.0363(3) Uani d . 1 . C
    C6 0.7556(2) 0.07191(13) 0.6235(2) 0.0408(4) Uani d . 1 . C
    C7 0.63699(15) 0.02108(15) 0.6365(2) 0.0418(4) Uani d . 1 . C
    C8 0.5431(2) 0.1133(2) 0.6698(2) 0.0531(5) Uani d . 1 . C
    C9 0.5984(2) 0.1836(2) 0.7853(3) 0.0610(6) Uani d . 1 . C
    C10 0.6079(2) 0.1133(2) 0.8880(2) 0.0601(5) Uani d . 1 . C
    C11 0.5604(2) -0.0070(2) 0.8435(2) 0.0520(5) Uani d . 1 . C
    C12 0.65008(14) -0.06125(14) 0.7579(2) 0.0386(4) Uani d . 1 . C
    C13 0.77952(13) -0.05768(13) 0.81716(15) 0.0339(3) Uani d . 1 . C
    C14 1.1546(2) -0.0855(2) 0.7885(3) 0.0677(6) Uani d . 1 . C
    C15 0.4631(2) 0.0311(2) 0.7385(2) 0.0593(5) Uani d . 1 . C
    H1 0.8247(15) -0.2312(15) 0.7651(17) 0.038(4) Uiso d . 1 . H
    H2A 1.0026(17) -0.2339(18) 0.8971(19) 0.050(5) Uiso d . 1 . H
    H2B 0.9856(18) -0.1066(18) 0.9469(19) 0.055(5) Uiso d . 1 . H
    H3 1.0227(17) -0.1807(17) 0.6835(19) 0.052(5) Uiso d . 1 . H
    H4 0.9857(16) 0.0130(16) 0.6105(19) 0.047(5) Uiso d . 1 . H
    H7 0.6121(17) -0.0195(18) 0.556(2)   0.054(5) Uiso d . 1 . H
    H8 0.508(2)   0.157(2)   0.595(2)   0.073(7) Uiso d . 1 . H
    H9 0.632(2)   0.263(2)   0.778(2)   0.071(7) Uiso d . 1 . H
    H10 0.650(2)   0.129(2)   0.971(2)   0.071(7) Uiso d . 1 . H
    H11 0.5407(18) -0.062(2)   0.910(2)   0.062(6) Uiso d . 1 . H
    H12 0.6285(16) -0.1397(17) 0.7305(18) 0.047(5) Uiso d . 1 . H
    H13 0.7891(14) -0.0162(15) 0.8986(17) 0.037(4) Uiso d . 1 . H
    H14A 1.154(3)   -0.017(3)   0.855(3)   0.105(9) Uiso d . 1 . H
    H14B 1.192(2)   -0.059(2)   0.705(3)   0.084(7) Uiso d . 1 . H
    H14C 1.199(3)   -0.150(3)   0.834(3)   0.105(9) Uiso d . 1 . H
    H15A 0.4312(19) -0.0360(19) 0.681(2)   0.058(6) Uiso d . 1 . H
    H15B 0.395(2)   0.074(2)   0.774(2)   0.080(7) Uiso d . 1 . H
_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 . 1.215(2) yes
    O2 C5 . 1.450(2) yes
    O2 C4 . 1.452(2) yes
    O3 N1 . 1.202(2) yes
    O4 N1 . 1.205(2) yes
    N1 C1 . 1.519(2) yes
    C1 C2 . 1.521(3) ?
    C1 C13 . 1.527(2) ?
    C2 C3 . 1.535(2) ?
    C3 C4 . 1.504(2) ?
    C3 C14 . 1.526(3) ?
    C4 C5 . 1.470(2) yes
    C5 C6 . 1.502(2) ?
    C5 C13 . 1.516(2) ?
    C6 C7 . 1.503(2) ?
    C7 C12 . 1.556(2) ?
    C7 C8 . 1.568(3) ?
    C8 C9 . 1.515(3) ?
    C8 C15 . 1.538(3) ?
    C9 C10 . 1.321(3) yes
    C10 C11 . 1.517(3) ?
    C11 C15 . 1.535(3) ?
    C11 C12 . 1.559(2) ?
    C12 C13 . 1.551(2) ?
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
    C5 O2 C4 . . 60.85(10) ?
    O3 N1 O4 . . 122.0(2) ?
    O3 N1 C1 . . 120.2(2) ?
    O4 N1 C1 . . 117.7(2) ?
    N1 C1 C2 . . 108.66(13) ?
    N1 C1 C13 . . 110.24(13) ?
    C2 C1 C13 . . 111.72(13) ?
    C1 C2 C3 . . 109.55(14) ?
    C4 C3 C14 . . 110.1(2) ?
    C4 C3 C2 . . 112.01(14) ?
    C14 C3 C2 . . 111.9(2) ?
    O2 C4 C5 . . 59.52(10) ?
    O2 C4 C3 . . 116.50(15) ?
    C5 C4 C3 . . 120.80(14) ?
    O2 C5 C4 . . 59.62(10) ?
    O2 C5 C6 . . 117.69(12) ?
    C4 C5 C6 . . 120.45(13) ?
    O2 C5 C13 . . 118.01(13) ?
    C4 C5 C13 . . 122.79(13) ?
    C6 C5 C13 . . 109.91(13) ?
    O1 C6 C5 . . 124.5(2) ?
    O1 C6 C7 . . 126.8(2) ?
    C5 C6 C7 . . 108.72(13) ?
    C6 C7 C12 . . 106.96(14) ?
    C6 C7 C8 . . 115.01(14) ?
    C12 C7 C8 . . 103.19(14) ?
    C9 C8 C15 . . 100.0(2) ?
    C9 C8 C7 . . 106.3(2) ?
    C15 C8 C7 . . 99.43(15) ?
    C10 C9 C8 . . 108.0(2) ?
    C9 C10 C11 . . 107.4(2) ?
    C10 C11 C15 . . 100.1(2) ?
    C10 C11 C12 . . 106.53(14) ?
    C15 C11 C12 . . 100.8(2) ?
    C13 C12 C7 . . 107.88(12) ?
    C13 C12 C11 . . 115.78(14) ?
    C7 C12 C11 . . 102.23(13) ?
    C5 C13 C1 . . 109.35(12) ?
    C5 C13 C12 . . 105.66(12) ?
    C1 C13 C12 . . 116.22(13) ?
    C11 C15 C8 . . 93.83(15) ?
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
    O3 N1 C1 C2 . . . . 98.6(2) ?
    O4 N1 C1 C2 . . . . -79.8(2) ?
    O3 N1 C1 C13 . . . . -24.1(2) ?
    O4 N1 C1 C13 . . . . 157.4(2) ?
    N1 C1 C2 C3 . . . . 169.47(13) ?
    C13 C1 C2 C3 . . . . -68.7(2) ?
    C1 C2 C3 C4 . . . . 48.0(2) ?
    C1 C2 C3 C14 . . . . 172.1(2) ?
    C5 O2 C4 C5 . . . . 0.0 ?
    C5 O2 C4 C3 . . . . -111.7(2) ?
    C14 C3 C4 O2 . . . . -71.5(2) ?
    C2 C3 C4 O2 . . . . 53.7(2) ?
    C14 C3 C4 C5 . . . . -140.2(2) ?
    C2 C3 C4 C5 . . . . -15.1(2) ?
    C4 O2 C5 C4 . . . . 0.0 ?
    C4 O2 C5 C6 . . . . -110.8(2) ?
    C4 O2 C5 C13 . . . . 113.5(2) ?
    O2 C4 C5 O2 . . . . 0.0 ?
    C3 C4 C5 O2 . . . . 104.6(2) ?
    O2 C4 C5 C6 . . . . 106.27(15) ?
    C3 C4 C5 C6 . . . . -149.1(2) ?
    O2 C4 C5 C13 . . . . -105.7(2) ?
    C3 C4 C5 C13 . . . . -1.1(2) ?
    O2 C5 C6 O1 . . . . 31.9(2) ?
    C4 C5 C6 O1 . . . . -37.3(2) ?
    C13 C5 C6 O1 . . . . 170.9(2) ?
    O2 C5 C6 C7 . . . . -148.34(13) ?
    C4 C5 C6 C7 . . . . 142.39(15) ?
    C13 C5 C6 C7 . . . . -9.4(2) ?
    O1 C6 C7 C12 . . . . -174.8(2) ?
    C5 C6 C7 C12 . . . . 5.5(2) ?
    O1 C6 C7 C8 . . . . -60.9(2) ?
    C5 C6 C7 C8 . . . . 119.4(2) ?
    C6 C7 C8 C9 . . . . -50.2(2) ?
    C12 C7 C8 C9 . . . . 65.9(2) ?
    C6 C7 C8 C15 . . . . -153.7(2) ?
    C12 C7 C8 C15 . . . . -37.6(2) ?
    C15 C8 C9 C10 . . . . 32.7(2) ?
    C7 C8 C9 C10 . . . . -70.3(2) ?
    C8 C9 C10 C11 . . . . 0.8(2) ?
    C9 C10 C11 C15 . . . . -34.0(2) ?
    C9 C10 C11 C12 . . . . 70.5(2) ?
    C6 C7 C12 C13 . . . . 0.2(2) ?
    C8 C7 C12 C13 . . . . -121.48(14) ?
    C6 C7 C12 C11 . . . . 122.75(14) ?
    C8 C7 C12 C11 . . . . 1.0(2) ?
    C10 C11 C12 C13 . . . . 49.0(2) ?
    C15 C11 C12 C13 . . . . 153.03(14) ?
    C10 C11 C12 C7 . . . . -68.0(2) ?
    C15 C11 C12 C7 . . . . 36.0(2) ?
    O2 C5 C13 C1 . . . . -86.2(2) ?
    C4 C5 C13 C1 . . . . -16.0(2) ?
    C6 C5 C13 C1 . . . . 135.03(14) ?
    O2 C5 C13 C12 . . . . 148.04(13) ?
    C4 C5 C13 C12 . . . . -141.8(2) ?
    C6 C5 C13 C12 . . . . 9.2(2) ?
    N1 C1 C13 C5 . . . . 171.00(13) ?
    C2 C1 C13 C5 . . . . 50.1(2) ?
    N1 C1 C13 C12 . . . . -69.5(2) ?
    C2 C1 C13 C12 . . . . 169.54(13) ?
    C7 C12 C13 C5 . . . . -5.7(2) ?
    C11 C12 C13 C5 . . . . -119.48(14) ?
    C7 C12 C13 C1 . . . . -127.14(14) ?
    C11 C12 C13 C1 . . . . 119.1(2) ?
    C10 C11 C15 C8 . . . . 50.3(2) ?
    C12 C11 C15 C8 . . . . -58.9(2) ?
    C9 C8 C15 C11 . . . . -49.8(2) ?
    C7 C8 C15 C11 . . . . 58.8(2) ?
