##############################################################################
###                                                                        ###
###           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/  #
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data_global
_audit_creation_method     'SHELXL'
_journal_date_recd_electronic     99-07-19
_journal_date_accepted     99-08-24
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     1999
_journal_volume     C55
_journal_issue     DEC99
_journal_page_first     2084
_journal_page_last     2087
_journal_paper_category     FO
_publ_contact_author_name     'Dr Yoshinobu Inouye'
_publ_contact_author_address
;
Department of Chemistry
University of Tsukuba
Tsukuba
Ibaraki 305-8571
Japan
;
_publ_contact_author_email     inouye@staff.chem.tsukuba.ac.jp
_publ_contact_author_fax     '0298(53)6503'
_publ_contact_author_phone     '0298(53)4215'
_publ_section_title
;
An ethyl acetate inclusion complex of
4,5-bis(4-methoxyphenyl)-2-(3-nitrophenyl)-1H-imidazole
;
loop_
    _publ_author_name
    _publ_author_address
    'Inouye, Yoshinobu'
;
Department of Chemistry
University of Tsukuba
Tsukuba
Ibaraki 305-8571
Japan
;
    'Shimokoshi, Shuko'
;
Department of Chemistry
University of Tsukuba
Tsukuba
Ibaraki 305-8571
Japan
;
    'Sakaino, Yoshiko'
;
Department of Chemistry
Faculty of Education
Gunma University
Maebashi
Gunma 371-0044
Japan
;
data_1
_audit_creation_method     SHELXL
_chemical_name_systematic
;
4,5-Bis(4-methoxyphenyl)-2-(3-nitrophenyl)-1H-imidazole/ethyl
acetate(3:1)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H19 N3 O4, 0.33C4 H8 O2'
_chemical_formula_sum     'C24.33 H21.67 N3 O4.67'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C23 H19 N3 O4, 0.33C4 H8 O2'
_chemical_formula_weight     430.78
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P n a 21'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    'x+1/2, -y+1/2, z'
    '-x+1/2, y+1/2, z+1/2'
_cell_length_a     8.9483(14)
_cell_length_b     27.469(5)
_cell_length_c     9.111(2)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2239.4(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     11.57
_cell_measurement_theta_max     13.90
_cell_measurement_temperature     293(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.60
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.278
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     904
_exptl_absorpt_coefficient_mu     0.090
_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_type     'Enraf-Nonius CAD-4'
_diffrn_measurement_method     ω--2θ
_diffrn_reflns_number     3452
_diffrn_reflns_av_R_equivalents     ?
_diffrn_reflns_av_sigmaI/netI     0.0759
_diffrn_reflns_theta_min     1.48
_diffrn_reflns_theta_max     30
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     38
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     0
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     120
_diffrn_standards_decay_%     0.1
_reflns_number_total     3452
_reflns_number_gt     1652
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.189
_refine_ls_R_factor_gt     0.077
_refine_ls_wR_factor_all     0.256
_refine_ls_wR_factor_ref     0.182
_refine_ls_goodness_of_fit_all     1.192
_refine_ls_goodness_of_fit_ref     1.403
_refine_ls_restrained_S_all     1.310
_refine_ls_restrained_S_obs     1.402
_refine_ls_number_reflns     3436
_refine_ls_number_parameters     285
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme
                'calc w = 1/[\s^2^(Fo^2^)+(0.1P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/esd_mean     0.000
_refine_diff_density_max     0.619
_refine_diff_density_min     -0.263
_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     'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_cell_refinement     'CAD-4 Software'
_computing_data_reduction     'MolEN (Fair, 1990)'
_computing_structure_solution     'SHELXS86 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL93 (Sheldrick, 1993)'
_computing_molecular_graphics     'ORTEPII (Johnson, 1976)'
_computing_publication_material     ?
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 1.0781(6) 0.2049(2) 0.9982(7) 0.100(2) Uani d . 1 . O
    O2 1.0794(7) 0.1276(2) 1.0067(9) 0.125(2) Uani d . 1 . O
    N3 1.0252(6) 0.1653(3) 0.9677(7) 0.071(2) Uani d . 1 . N
    C4 0.8946(7) 0.1642(2) 0.8712(7) 0.056(2) Uani d . 1 . C
    C5 0.8433(6) 0.2065(2) 0.8132(6) 0.0469(13) Uani d . 1 . C
    H5 0.8883 0.2359 0.8378 0.070 Uiso calc R 1 . H
    C6 0.7214(6) 0.2055(2) 0.7155(6) 0.0427(12) Uani d . 1 . C
    C7 0.6565(7) 0.1613(2) 0.6844(7) 0.054(2) Uani d . 1 . C
    H7 0.5767 0.1599 0.6192 0.082 Uiso calc R 1 . H
    C8 0.7089(8) 0.1183(2) 0.7496(9) 0.069(2) Uani d . 1 . C
    H8 0.6628 0.0887 0.7297 0.104 Uiso calc R 1 . H
    C9 0.8303(8) 0.1205(3) 0.8439(8) 0.071(2) Uani d . 1 . C
    H9 0.8669 0.0924 0.8879 0.107 Uiso calc R 1 . H
    C10 0.6768(5) 0.2494(2) 0.6378(6) 0.0405(11) Uani d . 1 . C
    N11 0.5482(4) 0.25286(15) 0.5596(5) 0.0415(10) Uani d . 1 . N
    H11 0.4800 0.2309 0.5527 0.062 Uiso calc R 1 . H
    C12 0.5464(5) 0.2986(2) 0.4922(6) 0.0430(12) Uani d . 1 . C
    C13 0.6787(5) 0.3199(2) 0.5351(6) 0.0419(12) Uani d . 1 . C
    N14 0.7590(4) 0.28952(14) 0.6248(5) 0.0442(10) Uani d . 1 . N
    C15 0.4218(5) 0.3139(2) 0.3998(6) 0.0461(13) Uani d . 1 . C
    C16 0.3414(6) 0.2800(2) 0.3188(7) 0.0496(14) Uani d . 1 . C
    H16 0.3678 0.2473 0.3234 0.074 Uiso calc R 1 . H
    C17 0.2216(6) 0.2942(2) 0.2306(7) 0.0541(15) Uani d . 1 . C
    H17 0.1703 0.2712 0.1755 0.081 Uiso calc R 1 . H
    C18 0.1791(7) 0.3424(2) 0.2248(8) 0.059(2) Uani d . 1 . C
    C19 0.2602(7) 0.3762(2) 0.3087(9) 0.064(2) Uani d . 1 . C
    H19 0.2330 0.4089 0.3058 0.097 Uiso calc R 1 . H
    C20 0.3775(6) 0.3624(2) 0.3941(7) 0.0549(15) Uani d . 1 . C
    H20 0.4285 0.3856 0.4492 0.082 Uiso calc R 1 . H
    O21 0.0674(5) 0.3606(2) 0.1407(6) 0.0808(15) Uani d . 1 . O
    C22 -0.0196(7) 0.3264(3) 0.0580(9) 0.080(2) Uani d . 1 . C
    H22A -0.0912 0.3435 -0.0009 0.121 Uiso calc R 1 . H
    H22B -0.0709 0.3049 0.1241 0.121 Uiso calc R 1 . H
    H22C 0.0452 0.3077 -0.0045 0.121 Uiso calc R 1 . H
    C23 0.7418(5) 0.3676(2) 0.4923(6) 0.0462(13) Uani d . 1 . C
    C24 0.8128(7) 0.3966(2) 0.5964(7) 0.056(2) Uani d . 1 . C
    H24 0.8165 0.3865 0.6937 0.084 Uiso calc R 1 . H
    C25 0.8780(8) 0.4402(2) 0.5568(8) 0.066(2) Uani d . 1 . C
    H25 0.9256 0.4591 0.6275 0.099 Uiso calc R 1 . H
    C26 0.8731(7) 0.4560(2) 0.4142(8) 0.062(2) Uani d . 1 . C
    C27 0.8016(7) 0.4282(2) 0.3107(8) 0.068(2) Uani d . 1 . C
    H27 0.7967 0.4389 0.2139 0.102 Uiso calc R 1 . H
    C28 0.7368(7) 0.3844(2) 0.3496(7) 0.059(2) Uani d . 1 . C
    H28 0.6890 0.3658 0.2783 0.089 Uiso calc R 1 . H
    O29 0.9320(6) 0.4990(2) 0.3645(6) 0.093(2) Uani d . 1 . O
    C30A 1.0348(18) 0.5252(6) 0.4523(18) 0.070(4) Uiso d P 0.50 1 C
    H30A 1.0745 0.5520 0.3971 0.104 Uiso calc PR 0.50 1 H
    H30B 1.1148 0.5040 0.4815 0.104 Uiso calc PR 0.50 1 H
    H30C 0.9848 0.5373 0.5381 0.104 Uiso calc PR 0.50 1 H
    C30B 0.979(2) 0.5350(6) 0.483(2) 0.077(5) Uiso d P 0.50 2 C
    H30D 1.0085 0.5651 0.4385 0.116 Uiso calc PR 0.50 2 H
    H30E 1.0607 0.5218 0.5382 0.116 Uiso calc PR 0.50 2 H
    H30F 0.8959 0.5408 0.5481 0.116 Uiso calc PR 0.50 2 H
    C31 0.9445(19) 0.0128(7) 0.1489(11) 0.091(7) Uiso d PG 0.33 2 C
    C32 1.0403(12) -0.0019(4) 0.0229(11) 0.064(5) Uiso d PG 0.33 2 C
    O33 1.1630(14) -0.0223(6) 0.0250(16) 0.147(8) Uiso d PG 0.33 2 O
    O34 0.9791(10) 0.0094(3) -0.1103(11) 0.064(3) Uiso d PG 0.33 2 O
    C35 1.0643(14) -0.0038(5) -0.2381(11) 0.108(9) Uiso d PG 0.33 2 C
    C36 0.974(2)   0.0123(7) -0.3691(11) 0.088(7) Uiso d PG 0.33 2 C
_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 N3 . 1.219(7) ?
    O2 N3 . 1.196(7) ?
    N3 C4 . 1.462(8) ?
    C4 C9 . 1.355(9) ?
    C4 C5 . 1.354(8) ?
    C5 C6 . 1.408(7) ?
    C5 H5 . 0.93 ?
    C6 C7 . 1.376(8) ?
    C6 C10 . 1.453(7) ?
    C7 C8 . 1.402(8) ?
    C7 H7 . 0.93 ?
    C8 C9 . 1.386(9) ?
    C8 H8 . 0.93 ?
    C9 H9 . 0.93 ?
    C10 N14 . 1.330(6) ?
    C10 N11 . 1.357(6) ?
    N11 C12 . 1.400(7) ?
    N11 H11 . 0.86 ?
    C12 C13 . 1.377(7) ?
    C12 C15 . 1.458(7) ?
    C13 N14 . 1.373(7) ?
    C13 C23 . 1.479(7) ?
    C15 C16 . 1.391(8) ?
    C15 C20 . 1.390(8) ?
    C16 C17 . 1.396(8) ?
    C16 H16 . 0.93 ?
    C17 C18 . 1.378(8) ?
    C17 H17 . 0.93 ?
    C18 O21 . 1.355(8) ?
    C18 C19 . 1.405(10) ?
    C19 C20 . 1.361(8) ?
    C19 H19 . 0.93 ?
    C20 H20 . 0.93 ?
    O21 C22 . 1.435(9) ?
    C22 H22A . 0.96 ?
    C22 H22B . 0.96 ?
    C22 H22C . 0.96 ?
    C23 C28 . 1.379(9) ?
    C23 C24 . 1.392(8) ?
    C24 C25 . 1.380(8) ?
    C24 H24 . 0.93 ?
    C25 C26 . 1.370(9) ?
    C25 H25 . 0.93 ?
    C26 O29 . 1.371(7) ?
    C26 C27 . 1.372(9) ?
    C27 C28 . 1.383(8) ?
    C27 H27 . 0.93 ?
    C28 H28 . 0.93 ?
    O29 C30A . 1.41(2) ?
    O29 C30B . 1.52(2) ?
    C30A H30A . 0.96 ?
    C30A H30B . 0.96 ?
    C30A H30C . 0.96 ?
    C30B H30D . 0.96 ?
    C30B H30E . 0.96 ?
    C30B H30F . 0.96 ?
    C31 C35 2_755 1.062(12) ?
    C31 C36 2_755 1.02(3) ?
    C31 C32 . 1.49 ?
    C32 C36 2_755 1.032(9) ?
    C32 O33 . 1.23 ?
    C32 O34 . 1.37 ?
    O33 C36 2_755 1.58(3) ?
    O34 C35 . 1.44 ?
    C35 C31 2_754 1.062(9) ?
    C35 C36 . 1.51 ?
    C36 C31 2_754 1.02(2) ?
    C36 C32 2_754 1.032(14) ?
    C36 O33 2_754 1.58(4) ?
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
    O2 N3 O1 . . 123.1(6) ?
    O2 N3 C4 . . 119.1(7) ?
    O1 N3 C4 . . 117.7(6) ?
    C9 C4 C5 . . 122.9(5) ?
    C9 C4 N3 . . 117.8(6) ?
    C5 C4 N3 . . 119.2(6) ?
    C4 C5 C6 . . 119.6(5) ?
    C4 C5 H5 . . 120.2 ?
    C6 C5 H5 . . 120.2 ?
    C7 C6 C5 . . 118.2(5) ?
    C7 C6 C10 . . 121.1(5) ?
    C5 C6 C10 . . 120.4(5) ?
    C6 C7 C8 . . 121.0(5) ?
    C6 C7 H7 . . 119.5 ?
    C8 C7 H7 . . 119.5 ?
    C7 C8 C9 . . 119.2(6) ?
    C7 C8 H8 . . 120.4 ?
    C9 C8 H8 . . 120.4 ?
    C4 C9 C8 . . 119.0(6) ?
    C4 C9 H9 . . 120.5 ?
    C8 C9 H9 . . 120.5 ?
    N14 C10 N11 . . 111.4(4) ?
    N14 C10 C6 . . 125.3(4) ?
    N11 C10 C6 . . 123.1(4) ?
    C12 N11 C10 . . 107.6(4) ?
    C12 N11 H11 . . 126.2 ?
    C10 N11 H11 . . 126.2 ?
    N11 C12 C13 . . 104.3(4) ?
    N11 C12 C15 . . 121.4(4) ?
    C13 C12 C15 . . 134.3(5) ?
    N14 C13 C12 . . 111.1(4) ?
    N14 C13 C23 . . 119.8(4) ?
    C12 C13 C23 . . 129.0(5) ?
    C10 N14 C13 . . 105.6(4) ?
    C16 C15 C20 . . 118.4(5) ?
    C16 C15 C12 . . 120.6(5) ?
    C20 C15 C12 . . 121.0(5) ?
    C15 C16 C17 . . 121.0(5) ?
    C15 C16 H16 . . 119.5 ?
    C17 C16 H16 . . 119.5 ?
    C18 C17 C16 . . 120.3(6) ?
    C18 C17 H17 . . 119.9 ?
    C16 C17 H17 . . 119.9 ?
    C17 C18 O21 . . 125.4(6) ?
    C17 C18 C19 . . 118.1(6) ?
    O21 C18 C19 . . 116.4(6) ?
    C20 C19 C18 . . 121.7(6) ?
    C20 C19 H19 . . 119.1 ?
    C18 C19 H19 . . 119.1 ?
    C19 C20 C15 . . 120.6(6) ?
    C19 C20 H20 . . 119.7 ?
    C15 C20 H20 . . 119.7 ?
    C18 O21 C22 . . 117.1(5) ?
    O21 C22 H22A . . 109.5 ?
    O21 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    O21 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    C28 C23 C24 . . 117.8(5) ?
    C28 C23 C13 . . 122.1(5) ?
    C24 C23 C13 . . 120.1(5) ?
    C25 C24 C23 . . 120.7(6) ?
    C25 C24 H24 . . 119.7 ?
    C23 C24 H24 . . 119.7 ?
    C24 C25 C26 . . 120.7(6) ?
    C24 C25 H25 . . 119.7 ?
    C26 C25 H25 . . 119.7 ?
    C25 C26 O29 . . 125.0(6) ?
    C25 C26 C27 . . 119.4(6) ?
    O29 C26 C27 . . 115.6(6) ?
    C28 C27 C26 . . 120.2(6) ?
    C28 C27 H27 . . 119.9 ?
    C26 C27 H27 . . 119.9 ?
    C27 C28 C23 . . 121.2(6) ?
    C27 C28 H28 . . 119.4 ?
    C23 C28 H28 . . 119.4 ?
    C26 O29 C30A . . 120.0(8) ?
    C26 O29 C30B . . 115.5(8) ?
    O29 C30A H30A . . 109.5 ?
    O29 C30A H30B . . 109.5 ?
    H30A C30A H30B . . 109.5 ?
    O29 C30A H30C . . 109.5 ?
    H30A C30A H30C . . 109.5 ?
    H30B C30A H30C . . 109.5 ?
    O29 C30B H30D . . 109.5 ?
    O29 C30B H30E . . 109.5 ?
    H30D C30B H30E . . 109.5 ?
    O29 C30B H30F . . 109.5 ?
    H30D C30B H30F . . 109.5 ?
    H30E C30B H30F . . 109.5 ?
    C35 C31 C36 2_755 2_755 93.(3)   ?
    C35 C31 C32 2_755 . 137.(3)   ?
    C36 C31 C32 2_755 . 43.8(5) ?
    C36 C32 O33 2_755 . 88.1(19) ?
    C36 C32 O34 2_755 . 149.4(18) ?
    O33 C32 O34 . . 118.3 ?
    C36 C32 C31 2_755 . 43.1(19) ?
    O33 C32 C31 . . 128.6 ?
    O34 C32 C31 . . 113.1 ?
    C32 O33 C36 . 2_755 40.7(8) ?
    C32 O34 C35 . . 116.6 ?
    C31 C35 O34 2_754 . 143.5(9) ?
    C31 C35 C36 2_754 . 42.4(9) ?
    O34 C35 C36 . . 106.3 ?
    C31 C36 C32 2_754 2_754 93.(2)   ?
    C31 C36 C35 2_754 . 44.6(5) ?
    C32 C36 C35 2_754 . 138.(3)   ?
    C31 C36 O33 2_754 2_754 140.6(18) ?
    C32 C36 O33 2_754 2_754 51.2(17) ?
    C35 C36 O33 . 2_754 161.7(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
    N11 H11 N14 3_455 0.86 2.16 2.899(6) 144 yes
data_2
_audit_creation_method     SHELXL
_chemical_name_systematic
;4,5-Bis(4-methoxyphenyl)-2-(3-nitrophenyl)-1H-imidazole
;
_chemical_name_common     ?
_chemical_formula_moiety     ?
_chemical_formula_sum     'C23 H19 N3 O4'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_weight     401.41
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P n a 21'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    'x+1/2, -y+1/2, z'
    '-x+1/2, y+1/2, z+1/2'
_cell_length_a     8.8960(10)
_cell_length_b     26.771(5)
_cell_length_c     9.209(2)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2193.2(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     9.83
_cell_measurement_theta_max     13.57
_cell_measurement_temperature     293(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.60
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.03
_exptl_crystal_density_diffrn     1.216
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     840
_exptl_absorpt_coefficient_mu     0.085
_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_type     'Enraf-Nonius CAD4'
_diffrn_measurement_method     ω--2θ
_diffrn_reflns_number     3365
_diffrn_reflns_av_R_equivalents     ?
_diffrn_reflns_av_sigmaI/netI     0.1402
_diffrn_reflns_theta_min     1.52
_diffrn_reflns_theta_max     30
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -37
_diffrn_reflns_limit_k_max     0
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     120
_diffrn_standards_decay_%     0.0
_reflns_number_total     3365
_reflns_number_gt     1352
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.225
_refine_ls_R_factor_gt     0.065
_refine_ls_wR_factor_all     0.213
_refine_ls_wR_factor_ref     0.142
_refine_ls_goodness_of_fit_all     0.950
_refine_ls_goodness_of_fit_ref     1.060
_refine_ls_restrained_S_all     0.950
_refine_ls_restrained_S_obs     1.060
_refine_ls_number_reflns     3365
_refine_ls_number_parameters     273
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme
                'calc w = 1/[\s^2^(Fo^2^)+(0.1P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/esd_mean     0.000
_refine_diff_density_max     0.199
_refine_diff_density_min     -0.205
_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     'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_cell_refinement     'CAD-4 Software'
_computing_data_reduction     'MolEN (Fair, 1990)'
_computing_structure_solution     'SHELXS86 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL93 (Sheldrick, 1993)'
_computing_molecular_graphics     'ORTEPII (Johnson, 1976)'
_computing_publication_material     ?
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 1.0658(6) 0.2046(2) 1.0006(7) 0.103(2) Uani d . 1 . O
    O2 1.0738(8) 0.1246(2) 1.0034(9) 0.133(3) Uani d . 1 . O
    N3 1.0145(7) 0.1644(3) 0.9673(7) 0.079(2) Uani d . 1 . N
    C4 0.8837(7) 0.1623(2) 0.8701(7) 0.055(2) Uani d . 1 . C
    C5 0.8279(6) 0.2056(2) 0.8150(6) 0.0477(14) Uani d . 1 . C
    H5 0.8690 0.2361 0.8428 0.057 Uiso calc R 1 . H
    C6 0.7102(6) 0.2041(2) 0.7179(6) 0.0416(13) Uani d . 1 . C
    C7 0.6455(7) 0.1579(2) 0.6850(7) 0.054(2) Uani d . 1 . C
    H7 0.5654 0.1564 0.6203 0.065 Uiso calc R 1 . H
    C8 0.6988(8) 0.1146(3) 0.7472(9) 0.077(2) Uani d . 1 . C
    H8 0.6531 0.0842 0.7269 0.092 Uiso calc R 1 . H
    C9 0.8209(8) 0.1168(3) 0.8404(9) 0.074(2) Uani d . 1 . C
    H9 0.8594 0.0878 0.8820 0.089 Uiso calc R 1 . H
    C10 0.6620(5) 0.2492(2) 0.6429(6) 0.0403(12) Uani d . 1 . C
    N11 0.5336(4) 0.2531(2) 0.5634(5) 0.0434(10) Uani d . 1 . N
    H11 0.4645 0.2307 0.5571 0.052 Uiso calc R 1 . H
    C12 0.5326(6) 0.2990(2) 0.4945(7) 0.0442(13) Uani d . 1 . C
    C13 0.6632(6) 0.3217(2) 0.5380(6) 0.0445(13) Uani d . 1 . C
    N14 0.7435(5) 0.2902(2) 0.6294(5) 0.0468(11) Uani d . 1 . N
    C15 0.4067(6) 0.3147(2) 0.4021(6) 0.0441(13) Uani d . 1 . C
    C16 0.3247(6) 0.2807(2) 0.3237(6) 0.0495(14) Uani d . 1 . C
    H16 0.3494 0.2471 0.3309 0.059 Uiso calc R 1 . H
    C17 0.2059(6) 0.2946(2) 0.2335(7) 0.0531(15) Uani d . 1 . C
    H17 0.1518 0.2706 0.1824 0.064 Uiso calc R 1 . H
    C18 0.1708(7) 0.3440(2) 0.2218(8) 0.059(2) Uani d . 1 . C
    C19 0.2506(8) 0.3789(2) 0.3011(9) 0.068(2) Uani d . 1 . C
    H19 0.2255 0.4126 0.2943 0.082 Uiso calc R 1 . H
    C20 0.3666(7) 0.3644(2) 0.3897(8) 0.063(2) Uani d . 1 . C
    H20 0.4191 0.3884 0.4423 0.075 Uiso calc R 1 . H
    O21 0.0588(5) 0.3632(2) 0.1349(6) 0.082(2) Uani d . 1 . O
    C22 -0.0309(8) 0.3291(3) 0.0572(9) 0.085(2) Uani d . 1 . C
    H22A 0.0304 0.3113 -0.0113 0.128 Uiso calc R 1 . H
    H22B -0.1083 0.3469 0.0062 0.128 Uiso calc R 1 . H
    H22C -0.0760 0.3059 0.1235 0.128 Uiso calc R 1 . H
    C23 0.7293(6) 0.3702(2) 0.4941(6) 0.0439(13) Uani d . 1 . C
    C24 0.7974(7) 0.4006(2) 0.5949(7) 0.057(2) Uani d . 1 . C
    H24 0.7960 0.3912 0.6922 0.068 Uiso calc R 1 . H
    C25 0.8681(7) 0.4447(2) 0.5557(8) 0.064(2) Uani d . 1 . C
    H25 0.9147 0.4646 0.6254 0.077 Uiso calc R 1 . H
    C26 0.8680(8) 0.4587(2) 0.4120(8) 0.063(2) Uani d . 1 . C
    C27 0.7965(8) 0.4296(2) 0.3110(8) 0.069(2) Uani d . 1 . C
    H27 0.7945 0.4397 0.2143 0.083 Uiso calc R 1 . H
    C28 0.7276(7) 0.3858(2) 0.3511(7) 0.059(2) Uani d . 1 . C
    H28 0.6795 0.3665 0.2813 0.070 Uiso calc R 1 . H
    O29 0.9382(6) 0.5013(2) 0.3594(6) 0.091(2) Uani d . 1 . O
    C30 1.0271(11) 0.5287(3) 0.4578(10) 0.106(3) Uani d . 1 . C
    H30A 1.0761 0.5555 0.4073 0.159 Uiso calc R 1 . H
    H30B 1.1014 0.5071 0.5001 0.159 Uiso calc R 1 . H
    H30C 0.9643 0.5422 0.5331 0.159 Uiso calc R 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 N3 . 1.208(7) ?
    O2 N3 . 1.234(7) ?
    N3 C4 . 1.470(8) ?
    C4 C5 . 1.359(8) ?
    C4 C9 . 1.368(9) ?
    C5 C6 . 1.378(7) ?
    C5 H5 . 0.93 ?
    C6 C7 . 1.397(8) ?
    C6 C10 . 1.454(7) ?
    C7 C8 . 1.375(9) ?
    C7 H7 . 0.93 ?
    C8 C9 . 1.385(10) ?
    C8 H8 . 0.93 ?
    C9 H9 . 0.93 ?
    C10 N14 . 1.321(6) ?
    C10 N11 . 1.361(6) ?
    N11 C12 . 1.382(7) ?
    N11 H11 . 0.86 ?
    C12 C13 . 1.371(7) ?
    C12 C15 . 1.468(8) ?
    C13 N14 . 1.388(7) ?
    C13 C23 . 1.482(7) ?
    C15 C16 . 1.372(8) ?
    C15 C20 . 1.382(8) ?
    C16 C17 . 1.394(8) ?
    C16 H16 . 0.93 ?
    C17 C18 . 1.364(8) ?
    C17 H17 . 0.93 ?
    C18 O21 . 1.377(8) ?
    C18 C19 . 1.381(9) ?
    C19 C20 . 1.372(9) ?
    C19 H19 . 0.93 ?
    C20 H20 . 0.93 ?
    O21 C22 . 1.406(8) ?
    C22 H22A . 0.96 ?
    C22 H22B . 0.96 ?
    C22 H22C . 0.96 ?
    C23 C28 . 1.381(8) ?
    C23 C24 . 1.374(8) ?
    C24 C25 . 1.386(8) ?
    C24 H24 . 0.93 ?
    C25 C26 . 1.375(9) ?
    C25 H25 . 0.93 ?
    C26 C27 . 1.368(9) ?
    C26 O29 . 1.386(7) ?
    C27 C28 . 1.373(8) ?
    C27 H27 . 0.93 ?
    C28 H28 . 0.93 ?
    O29 C30 . 1.409(9) ?
    C30 H30A . 0.96 ?
    C30 H30B . 0.96 ?
    C30 H30C . 0.96 ?
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
    O1 N3 O2 . . 122.6(6) ?
    O1 N3 C4 . . 119.2(6) ?
    O2 N3 C4 . . 118.0(7) ?
    C5 C4 C9 . . 122.4(5) ?
    C5 C4 N3 . . 118.9(6) ?
    C9 C4 N3 . . 118.7(6) ?
    C4 C5 C6 . . 119.6(5) ?
    C4 C5 H5 . . 120.2 ?
    C6 C5 H5 . . 120.2 ?
    C7 C6 C5 . . 118.7(5) ?
    C7 C6 C10 . . 120.6(5) ?
    C5 C6 C10 . . 120.5(5) ?
    C8 C7 C6 . . 120.8(6) ?
    C8 C7 H7 . . 119.6 ?
    C6 C7 H7 . . 119.6 ?
    C7 C8 C9 . . 119.6(6) ?
    C7 C8 H8 . . 120.2 ?
    C9 C8 H8 . . 120.2 ?
    C4 C9 C8 . . 118.7(6) ?
    C4 C9 H9 . . 120.6 ?
    C8 C9 H9 . . 120.6 ?
    N14 C10 N11 . . 110.3(5) ?
    N14 C10 C6 . . 124.8(4) ?
    N11 C10 C6 . . 124.5(5) ?
    C10 N11 C12 . . 108.7(4) ?
    C10 N11 H11 . . 125.6 ?
    C12 N11 H11 . . 125.6 ?
    C13 C12 N11 . . 104.7(5) ?
    C13 C12 C15 . . 133.6(5) ?
    N11 C12 C15 . . 121.7(5) ?
    C12 C13 N14 . . 110.2(5) ?
    C12 C13 C23 . . 130.1(5) ?
    N14 C13 C23 . . 119.5(4) ?
    C10 N14 C13 . . 106.1(4) ?
    C16 C15 C20 . . 117.2(5) ?
    C16 C15 C12 . . 121.4(5) ?
    C20 C15 C12 . . 121.4(5) ?
    C15 C16 C17 . . 122.8(5) ?
    C15 C16 H16 . . 118.6 ?
    C17 C16 H16 . . 118.6 ?
    C18 C17 C16 . . 118.6(6) ?
    C18 C17 H17 . . 120.7 ?
    C16 C17 H17 . . 120.7 ?
    O21 C18 C17 . . 125.0(6) ?
    O21 C18 C19 . . 115.3(6) ?
    C17 C18 C19 . . 119.7(6) ?
    C20 C19 C18 . . 120.7(6) ?
    C20 C19 H19 . . 119.7 ?
    C18 C19 H19 . . 119.7 ?
    C15 C20 C19 . . 121.0(6) ?
    C15 C20 H20 . . 119.5 ?
    C19 C20 H20 . . 119.5 ?
    C18 O21 C22 . . 117.7(5) ?
    O21 C22 H22A . . 109.5 ?
    O21 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    O21 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    C28 C23 C24 . . 117.9(5) ?
    C28 C23 C13 . . 121.4(5) ?
    C24 C23 C13 . . 120.6(5) ?
    C23 C24 C25 . . 121.9(6) ?
    C23 C24 H24 . . 119.0 ?
    C25 C24 H24 . . 119.0 ?
    C26 C25 C24 . . 118.8(6) ?
    C26 C25 H25 . . 120.6 ?
    C24 C25 H25 . . 120.6 ?
    C27 C26 O29 . . 116.1(6) ?
    C27 C26 C25 . . 120.0(6) ?
    O29 C26 C25 . . 123.9(6) ?
    C26 C27 C28 . . 120.7(6) ?
    C26 C27 H27 . . 119.7 ?
    C28 C27 H27 . . 119.7 ?
    C23 C28 C27 . . 120.6(6) ?
    C23 C28 H28 . . 119.7 ?
    C27 C28 H28 . . 119.7 ?
    C26 O29 C30 . . 117.2(5) ?
    O29 C30 H30A . . 109.5 ?
    O29 C30 H30B . . 109.5 ?
    H30A C30 H30B . . 109.5 ?
    O29 C30 H30C . . 109.5 ?
    H30A C30 H30C . . 109.5 ?
    H30B C30 H30C . . 109.5 ?
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
    N11 H11 N14 3_455 0.86 2.15 2.894(6) 145 yes
