##############################################################################
###                                                                        ###
###           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     98-06-02
_journal_date_accepted     98-08-11
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     1999
_journal_volume     C55
_journal_issue     JAN99
_journal_page_first     94
_journal_page_last     97
_journal_paper_category     FO
_publ_contact_author_name     'Prof.Fun Hoong Kun'
_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
;
2-Hydroxy-5-methyl-3-(morpholinomethyl)benzaldehyde, (I), and
 4,4'-dimethyl-6,6'-bis(morpholinomethyl)-2,2'-
ethylenedinitrilodimethylidyne)diphenol, (II)
;
loop_
    _publ_author_name
    _publ_author_address
    'S.Shanmuga Sundara Raj'
;     X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'R.Thirumurugan'
;     Department of Crystallography and Biophysics
      University of Madras
      Guindy Campus
      Chennai  600 025
      India
;
    'G.Shanmugam'
;     Department of Crystallography and Biophysics
      University of Madras
      Guindy Campus
      Chennai  600 025
      India
;
    'Hoong-Kun Fun'
;     X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'J.Manonmani'
;     Department of Inorganic Chemistry
      University of Madras
      Guindy Campus
      Chennai  600 025
      India
;
    'M.Kandaswamy'
;     Department of Inorganic Chemistry
      University of Madras
      Guindy Campus
      Chennai  600 025
      India
;
data_I
_audit_creation_method     SHELXL
_chemical_name_systematic
;
2-Hydroxy-5-methyl-3-(morpholinomethyl)benzaldehyde
;
_chemical_name_common     ?
_chemical_formula_moiety     ?
_chemical_formula_sum     'C13 H17 N O3'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_weight     235.28
_chemical_melting_point     175\%C
_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     5.31720(10)
_cell_length_b     15.3099(3)
_cell_length_c     15.34060(10)
_cell_angle_alpha     90.00
_cell_angle_beta     91.8460(10)
_cell_angle_gamma     90.00
_cell_volume     1248.17(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4735
_cell_measurement_theta_min     1.37
_cell_measurement_theta_max     33.22
_cell_measurement_temperature     293(2)
_exptl_crystal_description     parallelepiped
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.52
_exptl_crystal_size_mid     0.42
_exptl_crystal_size_min     0.30
_exptl_crystal_density_diffrn     1.252
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     504
_exptl_absorpt_coefficient_mu     0.089
_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 diffractometer
;
_diffrn_measurement_method     'ω scans'
_diffrn_reflns_number     7859
_diffrn_reflns_av_R_equivalents     0.0208
_diffrn_reflns_av_sigmaI/netI     0.0267
_diffrn_reflns_theta_min     2.97
_diffrn_reflns_theta_max     27.49
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     19
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     2832
_reflns_number_observed     2094
_reflns_observed_criterion     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0667
_refine_ls_R_factor_obs     0.0490
_refine_ls_wR_factor_all     0.1487
_refine_ls_wR_factor_obs     0.1355
_refine_ls_goodness_of_fit_all     1.070
_refine_ls_goodness_of_fit_obs     1.143
_refine_ls_restrained_S_all     1.070
_refine_ls_restrained_S_obs     1.143
_refine_ls_number_reflns     2832
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme
       'calc w = 1/[\s^2^(Fo^2^)+(0.0663P)^2^+0.2732P] 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     0.264
_refine_diff_density_min     -0.201
_refine_ls_extinction_method     SHELXTL
_refine_ls_extinction_coef     0.039(5)
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 (Sheldrick, 1996)'
_computing_structure_refinement     'SHELXTL'
_computing_molecular_graphics     'SHELXTL'
_computing_publication_material     'SHELXTL & 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
    C1 0.2447(3) 0.55635(10) 0.20868(9) 0.0442(4) Uani d . 1 . C
    C2 0.4111(3) 0.62699(10) 0.22080(10) 0.0465(4) Uani d . 1 . C
    C3 0.5867(3) 0.62316(12) 0.28910(11) 0.0532(4) Uani d . 1 . C
    H3A 0.6999(3) 0.66908(12) 0.29643(11) 0.064 Uiso calc R 1 . H
    C4 0.6014(3) 0.55345(12) 0.34743(10) 0.0551(4) Uani d . 1 . C
    C5 0.4348(3) 0.48554(12) 0.33454(11) 0.0546(4) Uani d . 1 . C
    H5A 0.4414(3) 0.43828(12) 0.37264(11) 0.065 Uiso calc R 1 . H
    C6 0.2559(3) 0.48564(11) 0.26583(10) 0.0487(4) Uani d . 1 . C
    O7 0.0739(2) 0.55552(9) 0.14110(8) 0.0575(3) Uani d . 1 . O
    C8 0.7918(4) 0.5526(2) 0.42251(13) 0.0777(6) Uani d . 1 . C
    H8A 0.8914(4) 0.6049(2) 0.42119(13) 0.117 Uiso calc R 1 . H
    H8B 0.8993(4) 0.5026(2) 0.41757(13) 0.117 Uiso calc R 1 . H
    H8C 0.7060(4) 0.5498(2) 0.47654(13) 0.117 Uiso calc R 1 . H
    C9 0.3906(4) 0.70645(11) 0.16330(12) 0.0576(4) Uani d . 1 . C
    H9A 0.2566(4) 0.74366(11) 0.18331(12) 0.069 Uiso calc R 1 . H
    H9B 0.5466(4) 0.73923(11) 0.16801(12) 0.069 Uiso calc R 1 . H
    N10 0.3389(2) 0.68306(8) 0.07112(8) 0.0476(3) Uani d . 1 . N
    C11 0.5541(3) 0.63968(12) 0.03305(12) 0.0589(5) Uani d . 1 . C
    H11A 0.5971(3) 0.58762(12) 0.06635(12) 0.071 Uiso calc R 1 . H
    H11B 0.6985(3) 0.67846(12) 0.03519(12) 0.071 Uiso calc R 1 . H
    C12 0.4911(5) 0.61535(14) -0.05958(13) 0.0736(6) Uani d . 1 . C
    H12A 0.6339(5) 0.58595(14) -0.08424(13) 0.088 Uiso calc R 1 . H
    H12B 0.3502(5) 0.57508(14) -0.06118(13) 0.088 Uiso calc R 1 . H
    O13 0.4285(3) 0.69024(10) -0.11065(9) 0.0814(5) Uani d . 1 . O
    C14 0.2227(4) 0.73414(15) -0.07489(13) 0.0737(6) Uani d . 1 . C
    H14A 0.0762(4) 0.69641(15) -0.07815(13) 0.088 Uiso calc R 1 . H
    H14B 0.1849(4) 0.78596(15) -0.10924(13) 0.088 Uiso calc R 1 . H
    C15 0.2739(4) 0.76016(11) 0.01821(12) 0.0611(5) Uani d . 1 . C
    H15A 0.4116(4) 0.80171(11) 0.02139(12) 0.073 Uiso calc R 1 . H
    H15B 0.1260(4) 0.78815(11) 0.04095(12) 0.073 Uiso calc R 1 . H
    C16 0.0799(4) 0.41244(14) 0.25634(13) 0.0666(5) Uani d . 1 . C
    H16A -0.0394(4) 0.41415(14) 0.21066(13) 0.080 Uiso calc R 1 . H
    O17 0.0807(3) 0.34995(11) 0.30445(13) 0.0968(6) Uani d . 1 . O
    H7 0.117(5)   0.6036(18) 0.1096(17) 0.100(8) 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
    C1 O7 . 1.356(2) yes
    C1 C6 . 1.393(2) ?
    C1 C2 . 1.406(2) ?
    C2 C3 . 1.382(2) ?
    C2 C9 . 1.504(2) ?
    C3 C4 . 1.393(2) ?
    C3 H3A . 0.93 ?
    C4 C5 . 1.376(3) ?
    C4 C8 . 1.509(2) ?
    C5 C6 . 1.397(2) ?
    C5 H5A . 0.93 ?
    C6 C16 . 1.464(3) ?
    O7 H7 . 0.91(3) ?
    C8 H8A . 0.96 ?
    C8 H8B . 0.96 ?
    C8 H8C . 0.96 ?
    C9 N10 . 1.476(2) ?
    C9 H9A . 0.97 ?
    C9 H9B . 0.97 ?
    N10 C11 . 1.461(2) yes
    N10 C15 . 1.468(2) yes
    C11 C12 . 1.496(3) yes
    C11 H11A . 0.97 ?
    C11 H11B . 0.97 ?
    C12 O13 . 1.422(2) yes
    C12 H12A . 0.97 ?
    C12 H12B . 0.97 ?
    O13 C14 . 1.410(2) yes
    C14 C15 . 1.499(3) yes
    C14 H14A . 0.97 ?
    C14 H14B . 0.97 ?
    C15 H15A . 0.97 ?
    C15 H15B . 0.97 ?
    C16 O17 . 1.208(2) yes
    C16 H16A . 0.93 ?
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
    O7 C1 C6 . . 119.20(14) ?
    O7 C1 C2 . . 120.75(14) ?
    C6 C1 C2 . . 120.05(14) ?
    C3 C2 C1 . . 118.33(15) ?
    C3 C2 C9 . . 120.9(2) ?
    C1 C2 C9 . . 120.75(14) ?
    C2 C3 C4 . . 122.8(2) ?
    C2 C3 H3A . . 118.60(10) ?
    C4 C3 H3A . . 118.60(10) ?
    C5 C4 C3 . . 117.65(15) ?
    C5 C4 C8 . . 121.1(2) ?
    C3 C4 C8 . . 121.3(2) ?
    C4 C5 C6 . . 121.8(2) ?
    C4 C5 H5A . . 119.09(10) ?
    C6 C5 H5A . . 119.09(10) ?
    C1 C6 C5 . . 119.3(2) ?
    C1 C6 C16 . . 121.2(2) ?
    C5 C6 C16 . . 119.5(2) ?
    C1 O7 H7 . . 102.9(16) ?
    C4 C8 H8A . . 109.47(13) ?
    C4 C8 H8B . . 109.47(12) ?
    H8A C8 H8B . . 109.5 ?
    C4 C8 H8C . . 109.47(11) ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    N10 C9 C2 . . 111.91(13) yes
    N10 C9 H9A . . 109.23(9) ?
    C2 C9 H9A . . 109.23(9) ?
    N10 C9 H9B . . 109.23(9) ?
    C2 C9 H9B . . 109.23(9) ?
    H9A C9 H9B . . 107.9 ?
    C11 N10 C15 . . 108.55(13) yes
    C11 N10 C9 . . 111.65(14) yes
    C15 N10 C9 . . 111.60(13) yes
    N10 C11 C12 . . 109.8(2) yes
    N10 C11 H11A . . 109.71(9) ?
    C12 C11 H11A . . 109.71(11) ?
    N10 C11 H11B . . 109.71(9) ?
    C12 C11 H11B . . 109.71(12) ?
    H11A C11 H11B . . 108.2 ?
    O13 C12 C11 . . 111.3(2) yes
    O13 C12 H12A . . 109.36(10) ?
    C11 C12 H12A . . 109.36(11) ?
    O13 C12 H12B . . 109.36(12) ?
    C11 C12 H12B . . 109.36(12) ?
    H12A C12 H12B . . 108.0 ?
    C14 O13 C12 . . 109.91(14) yes
    O13 C14 C15 . . 112.2(2) yes
    O13 C14 H14A . . 109.16(12) ?
    C15 C14 H14A . . 109.16(12) ?
    O13 C14 H14B . . 109.16(10) ?
    C15 C14 H14B . . 109.16(10) ?
    H14A C14 H14B . . 107.9 ?
    N10 C15 C14 . . 110.21(15) yes
    N10 C15 H15A . . 109.62(10) ?
    C14 C15 H15A . . 109.62(12) ?
    N10 C15 H15B . . 109.62(9) ?
    C14 C15 H15B . . 109.62(11) ?
    H15A C15 H15B . . 108.1 ?
    O17 C16 C6 . . 123.7(2) yes
    O17 C16 H16A . . 118.13(13) ?
    C6 C16 H16A . . 118.13(10) ?
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
    O7 C1 C2 C3 . . . . -177.95(14) ?
    C6 C1 C2 C3 . . . . 1.3(2) ?
    O7 C1 C2 C9 . . . . 4.7(2) ?
    C6 C1 C2 C9 . . . . -175.98(14) ?
    C1 C2 C3 C4 . . . . -1.6(2) ?
    C9 C2 C3 C4 . . . . 175.7(2) ?
    C2 C3 C4 C5 . . . . 1.0(2) ?
    C2 C3 C4 C8 . . . . -178.5(2) ?
    C3 C4 C5 C6 . . . . -0.1(2) ?
    C8 C4 C5 C6 . . . . 179.4(2) ?
    O7 C1 C6 C5 . . . . 178.81(14) ?
    C2 C1 C6 C5 . . . . -0.5(2) ?
    O7 C1 C6 C16 . . . . -2.6(2) ?
    C2 C1 C6 C16 . . . . 178.1(2) ?
    C4 C5 C6 C1 . . . . -0.1(2) ?
    C4 C5 C6 C16 . . . . -178.7(2) ?
    C3 C2 C9 N10 . . . . 141.7(2) ?
    C1 C2 C9 N10 . . . . -41.1(2) ?
    C2 C9 N10 C11 . . . . -68.7(2) ?
    C2 C9 N10 C15 . . . . 169.64(15) ?
    C15 N10 C11 C12 . . . . -57.9(2) yes
    C9 N10 C11 C12 . . . . 178.67(15) ?
    N10 C11 C12 O13 . . . . 59.7(2) yes
    C11 C12 O13 C14 . . . . -58.4(2) yes
    C12 O13 C14 C15 . . . . 57.2(2) yes
    C11 N10 C15 C14 . . . . 56.5(2) yes
    C9 N10 C15 C14 . . . . 180.0(2) ?
    O13 C14 C15 N10 . . . . -57.2(2) yes
    C1 C6 C16 O17 . . . . -179.5(2) ?
    C5 C6 C16 O17 . . . . -0.9(3) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _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
    O7 H7 N10 . . 1_555 0.91(3) 1.81(3) 2.655(2) 153(2) yes
    C9 H9A O17 . . 2_555 0.97(2) 2.43(3) 3.381(3) 165(2) yes
data_II
_audit_creation_method     SHELXL
_chemical_name_systematic
;
 4,4'-Dimethyl-6,6'-bis(morpholinomethyl)-2,2'-ethylene
dinitrilodimethylidyne)diphenol
;
_chemical_name_common     ?
_chemical_formula_moiety     ?
_chemical_formula_sum     'C28 H38 N4 O4'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_weight     494.62
_chemical_melting_point     193\%C
_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     11.1356(5)
_cell_length_b     9.5825(5)
_cell_length_c     12.4721(6)
_cell_angle_alpha     90.00
_cell_angle_beta     98.828(2)
_cell_angle_gamma     90.00
_cell_volume     1315.09(11)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2700
_cell_measurement_theta_min     1.37
_cell_measurement_theta_max     33.22
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.26
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.249
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     532
_exptl_absorpt_coefficient_mu     0.084
_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 diffractometer
;
_diffrn_measurement_method     'ω scans'
_diffrn_reflns_number     8310
_diffrn_reflns_av_R_equivalents     0.0432
_diffrn_reflns_av_sigmaI/netI     0.0562
_diffrn_reflns_theta_min     2.69
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     3017
_reflns_number_observed     1671
_reflns_observed_criterion     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1268
_refine_ls_R_factor_obs     0.0646
_refine_ls_wR_factor_all     0.1749
_refine_ls_wR_factor_obs     0.1392
_refine_ls_goodness_of_fit_all     1.037
_refine_ls_goodness_of_fit_obs     1.135
_refine_ls_restrained_S_all     1.042
_refine_ls_restrained_S_obs     1.135
_refine_ls_number_reflns     3012
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme
       'calc w = 1/[\s^2^(Fo^2^)+(0.0648P)^2^+0.4623P] 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     0.219
_refine_diff_density_min     -0.207
_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 (Sheldrick, 1996)'
_computing_structure_refinement     'SHELXTL'
_computing_molecular_graphics     'SHELXTL'
_computing_publication_material     'SHELXTL & 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
    C1 0.3621(2) 0.5479(2) 0.1341(2) 0.0437(6) Uani d . 1 . C
    C2 0.3019(2) 0.5446(2) 0.0264(2) 0.0447(6) Uani d . 1 . C
    C3 0.2366(2) 0.6614(3) -0.0130(2) 0.0489(6) Uani d . 1 . C
    H3A 0.1966(2) 0.6603(3) -0.0842(2) 0.059 Uiso calc R 1 . H
    C4 0.2284(2) 0.7802(3) 0.0492(2) 0.0509(6) Uani d . 1 . C
    C5 0.2878(2) 0.7806(2) 0.1550(2) 0.0493(6) Uani d . 1 . C
    H5A 0.2830(2) 0.8593(2) 0.1978(2) 0.059 Uiso calc R 1 . H
    C6 0.3547(2) 0.6653(2) 0.1989(2) 0.0423(6) Uani d . 1 . C
    O7 0.4271(2) 0.4332(2) 0.1719(2) 0.0580(5) Uani d . 1 . O
    C8 0.1514(3) 0.9018(3) 0.0019(3) 0.0769(9) Uani d . 1 . C
    H8A 0.1180(3) 0.8817(3) -0.0721(3) 0.115 Uiso calc R 1 . H
    H8B 0.2007(3) 0.9842(3) 0.0047(3) 0.115 Uiso calc R 1 . H
    H8C 0.0865(3) 0.9166(3) 0.0432(3) 0.115 Uiso calc R 1 . H
    C9 0.3129(2) 0.4150(3) -0.0396(2) 0.0553(7) Uani d . 1 . C
    H9A 0.3919(2) 0.4151(3) -0.0632(2) 0.066 Uiso calc R 1 . H
    H9B 0.3094(2) 0.3342(3) 0.0066(2) 0.066 Uiso calc R 1 . H
    N10 0.2194(2) 0.4003(2) -0.13500(15) 0.0489(5) Uani d . 1 . N
    C11 0.0992(2) 0.3774(3) -0.1058(2) 0.0644(8) Uani d . 1 . C
    H11A 0.0773(2) 0.4555(3) -0.0633(2) 0.077 Uiso calc R 1 . H
    H11B 0.0998(2) 0.2936(3) -0.0621(2) 0.077 Uiso calc R 1 . H
    C12 0.0073(3) 0.3624(4) -0.2073(3) 0.0812(10) Uani d . 1 . C
    H12A -0.0733(3) 0.3520(4) -0.1878(3) 0.097 Uiso calc R 1 . H
    H12B 0.0077(3) 0.4459(4) -0.2512(3) 0.097 Uiso calc R 1 . H
    O13 0.0349(2) 0.2443(2) -0.2680(2) 0.0892(8) Uani d . 1 . O
    C14 0.1522(4) 0.2605(4) -0.2968(2) 0.0812(10) Uani d . 1 . C
    H14A 0.1519(4) 0.3404(4) -0.3446(2) 0.097 Uiso calc R 1 . H
    H14B 0.1717(4) 0.1785(4) -0.3362(2) 0.097 Uiso calc R 1 . H
    C15 0.2488(3) 0.2811(3) -0.1993(2) 0.0658(8) Uani d . 1 . C
    H15A 0.2553(3) 0.1976(3) -0.1549(2) 0.079 Uiso calc R 1 . H
    H15B 0.3267(3) 0.2967(3) -0.2232(2) 0.079 Uiso calc R 1 . H
    C16 0.4111(2) 0.6652(3) 0.3127(2) 0.0471(6) Uani d . 1 . C
    H16A 0.4055(2) 0.7448(3) 0.3544(2) 0.057 Uiso calc R 1 . H
    N17 0.4676(2) 0.5591(2) 0.3565(2) 0.0540(6) Uani d . 1 . N
    C18 0.5188(3) 0.5646(3) 0.4714(2) 0.0585(7) Uani d . 1 . C
    H18A 0.4900(3) 0.6475(3) 0.5041(2) 0.070 Uiso calc R 1 . H
    H18B 0.6067(3) 0.5694(3) 0.4794(2) 0.070 Uiso calc R 1 . H
    H7 0.451(3)   0.456(4)   0.245(3)   0.098(11) 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
    C1 O7 . 1.361(3) yes
    C1 C6 . 1.396(3) ?
    C1 C2 . 1.405(3) ?
    C2 C3 . 1.384(3) ?
    C2 C9 . 1.506(3) ?
    C3 C4 . 1.388(3) ?
    C3 H3A . 0.93 ?
    C4 C5 . 1.382(3) ?
    C4 C8 . 1.511(3) ?
    C5 C6 . 1.397(3) ?
    C5 H5A . 0.93 ?
    C6 C16 . 1.462(3) ?
    O7 H7 . 0.94(4) ?
    C8 H8A . 0.96 ?
    C8 H8B . 0.96 ?
    C8 H8C . 0.96 ?
    C9 N10 . 1.462(3) ?
    C9 H9A . 0.97 ?
    C9 H9B . 0.97 ?
    N10 C11 . 1.457(3) yes
    N10 C15 . 1.461(3) yes
    C11 C12 . 1.507(4) yes
    C11 H11A . 0.97 ?
    C11 H11B . 0.97 ?
    C12 O13 . 1.422(4) yes
    C12 H12A . 0.97 ?
    C12 H12B . 0.97 ?
    O13 C14 . 1.414(4) yes
    C14 C15 . 1.508(4) yes
    C14 H14A . 0.97 ?
    C14 H14B . 0.97 ?
    C15 H15A . 0.97 ?
    C15 H15B . 0.97 ?
    C16 N17 . 1.274(3) yes
    C16 H16A . 0.93 ?
    N17 C18 . 1.460(3) yes
    C18 C18 3_666 1.519(5) yes
    C18 H18A . 0.97 ?
    C18 H18B . 0.97 ?
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
    O7 C1 C6 . . 121.7(2) ?
    O7 C1 C2 . . 117.6(2) ?
    C6 C1 C2 . . 120.6(2) ?
    C3 C2 C1 . . 118.0(2) ?
    C3 C2 C9 . . 123.7(2) ?
    C1 C2 C9 . . 118.3(2) ?
    C2 C3 C4 . . 122.7(2) ?
    C2 C3 H3A . . 118.64(14) ?
    C4 C3 H3A . . 118.64(14) ?
    C5 C4 C3 . . 118.2(2) ?
    C5 C4 C8 . . 122.0(2) ?
    C3 C4 C8 . . 119.8(2) ?
    C4 C5 C6 . . 121.3(2) ?
    C4 C5 H5A . . 119.33(15) ?
    C6 C5 H5A . . 119.33(13) ?
    C1 C6 C5 . . 119.1(2) ?
    C1 C6 C16 . . 120.5(2) ?
    C5 C6 C16 . . 120.4(2) ?
    C1 O7 H7 . . 102.(2)   ?
    C4 C8 H8A . . 109.47(15) ?
    C4 C8 H8B . . 109.5(2) ?
    H8A C8 H8B . . 109.5 ?
    C4 C8 H8C . . 109.5(2) ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    N10 C9 C2 . . 114.7(2) ?
    N10 C9 H9A . . 108.59(13) ?
    C2 C9 H9A . . 108.59(14) ?
    N10 C9 H9B . . 108.59(14) ?
    C2 C9 H9B . . 108.59(14) ?
    H9A C9 H9B . . 107.6 ?
    C11 N10 C15 . . 108.1(2) yes
    C11 N10 C9 . . 112.2(2) yes
    C15 N10 C9 . . 109.3(2) yes
    N10 C11 C12 . . 109.6(2) yes
    N10 C11 H11A . . 109.74(14) ?
    C12 C11 H11A . . 109.7(2) ?
    N10 C11 H11B . . 109.74(15) ?
    C12 C11 H11B . . 109.7(2) ?
    H11A C11 H11B . . 108.2 ?
    O13 C12 C11 . . 110.4(3) yes
    O13 C12 H12A . . 109.6(2) ?
    C11 C12 H12A . . 109.6(2) ?
    O13 C12 H12B . . 109.6(2) ?
    C11 C12 H12B . . 109.6(2) ?
    H12A C12 H12B . . 108.1 ?
    C14 O13 C12 . . 109.3(2) yes
    O13 C14 C15 . . 112.5(3) yes
    O13 C14 H14A . . 109.1(2) ?
    C15 C14 H14A . . 109.1(2) ?
    O13 C14 H14B . . 109.1(2) ?
    C15 C14 H14B . . 109.1(2) ?
    H14A C14 H14B . . 107.8 ?
    N10 C15 C14 . . 110.6(2) yes
    N10 C15 H15A . . 109.52(14) ?
    C14 C15 H15A . . 109.5(2) ?
    N10 C15 H15B . . 109.5(2) ?
    C14 C15 H15B . . 109.5(2) ?
    H15A C15 H15B . . 108.1 ?
    N17 C16 C6 . . 121.8(2) ?
    N17 C16 H16A . . 119.09(14) ?
    C6 C16 H16A . . 119.09(14) ?
    C16 N17 C18 . . 119.0(2) ?
    N17 C18 C18 . 3_666 109.7(2) yes
    N17 C18 H18A . . 109.72(14) ?
    C18 C18 H18A 3_666 . 109.7(2) ?
    N17 C18 H18B . . 109.72(14) ?
    C18 C18 H18B 3_666 . 109.7(2) ?
    H18A C18 H18B . . 108.2 ?
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
    O7 C1 C2 C3 . . . . -179.3(2) ?
    C6 C1 C2 C3 . . . . 0.6(3) ?
    O7 C1 C2 C9 . . . . 0.2(3) ?
    C6 C1 C2 C9 . . . . -179.9(2) ?
    C1 C2 C3 C4 . . . . -0.1(4) ?
    C9 C2 C3 C4 . . . . -179.6(2) ?
    C2 C3 C4 C5 . . . . -0.3(4) ?
    C2 C3 C4 C8 . . . . -177.7(3) ?
    C3 C4 C5 C6 . . . . 0.1(4) ?
    C8 C4 C5 C6 . . . . 177.5(3) ?
    O7 C1 C6 C5 . . . . 179.2(2) ?
    C2 C1 C6 C5 . . . . -0.7(3) ?
    O7 C1 C6 C16 . . . . -3.9(3) ?
    C2 C1 C6 C16 . . . . 176.2(2) ?
    C4 C5 C6 C1 . . . . 0.3(4) ?
    C4 C5 C6 C16 . . . . -176.6(2) ?
    C3 C2 C9 N10 . . . . -19.5(4) ?
    C1 C2 C9 N10 . . . . 161.0(2) ?
    C2 C9 N10 C11 . . . . -67.3(3) ?
    C2 C9 N10 C15 . . . . 172.8(2) ?
    C15 N10 C11 C12 . . . . -59.1(3) yes
    C9 N10 C11 C12 . . . . -179.7(2) ?
    N10 C11 C12 O13 . . . . 62.1(3) yes
    C11 C12 O13 C14 . . . . -59.6(3) yes
    C12 O13 C14 C15 . . . . 57.0(3) yes
    C11 N10 C15 C14 . . . . 55.9(3) yes
    C9 N10 C15 C14 . . . . 178.4(2) ?
    O13 C14 C15 N10 . . . . -56.2(3) yes
    C1 C6 C16 N17 . . . . -0.3(3) ?
    C5 C6 C16 N17 . . . . 176.5(2) ?
    C6 C16 N17 C18 . . . . -178.2(2) ?
    C16 N17 C18 C18 . . . 3_666 130.4(3) yes
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _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
    O7 H7 N17 . . 1_555 0.94(4) 1.69(4) 2.577(3) 156(3) yes
