##############################################################################
###                                                                        ###
###           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 2.1.    #
#                                                                            #
# 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                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N,N-dimethyl-2-[5-(pyrrolidin-1-ylsulfonylmethyl)-1H-
indol-3-yl]-ethanamine
;
_chemical_name_common     Almotriptan
_chemical_formula_moiety     'C17 H25 N3 O2 S'
_chemical_formula_sum     'C17 H25 N3 O2 S'
_chemical_formula_iupac     'C17 H25 N3 O2 S'
_chemical_formula_weight     335.46
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
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'
    '-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     20.5023(17)
_cell_length_b     7.6894(6)
_cell_length_c     22.8470(19)
_cell_angle_alpha     90.00
_cell_angle_beta     104.904(2)
_cell_angle_gamma     90.00
_cell_volume     3480.7(5)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     1760
_cell_measurement_theta_min     2.39
_cell_measurement_theta_max     19.79
_cell_measurement_temperature     294(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.22
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.09
_exptl_crystal_density_diffrn     1.280
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1440
_exptl_absorpt_coefficient_mu     0.199
_exptl_absorpt_correction_type     none
_diffrn_ambient_temperature     294(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 SMART APEX CCD area-detector'
_diffrn_measurement_device     'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method     'ω scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     16157
_diffrn_reflns_av_R_equivalents     0.0679
_diffrn_reflns_av_sigmaI/netI     0.0502
_diffrn_reflns_theta_min     1.84
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -24
_diffrn_reflns_limit_h_max     24
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -27
_diffrn_reflns_limit_l_max     27
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     3057
_reflns_number_gt     2285
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1068
_refine_ls_R_factor_gt     0.0779
_refine_ls_wR_factor_gt     0.1496
_refine_ls_wR_factor_ref     0.1622
_refine_ls_goodness_of_fit_ref     1.174
_refine_ls_restrained_S_all     1.174
_refine_ls_number_reflns     3057
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0557P)²+4.6989P] 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     0.366
_refine_diff_density_min     -0.242
_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'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SAINT (Bruker, 2001)'
_computing_data_reduction     'SAINT (Bruker, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
SHELXTL/PC (Sheldrick, 1990) and PLATON (Spek, 2003)
;
_computing_publication_material     'SHELXL97 (Sheldrick, 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
    C C1 0.12062(18) 0.5985(4) 0.37559(15) 0.0366(9) Uani d . 1 . .
    H H1 0.1327 0.5861 0.4175 0.044 Uiso calc R 1 . .
    C C2 0.10799(17) 0.4643(4) 0.33577(14) 0.0323(8) Uani d . 1 . .
    C C3 0.09142(16) 0.5423(4) 0.27666(14) 0.0300(8) Uani d . 1 . .
    C C4 0.07313(16) 0.4779(5) 0.21760(14) 0.0342(8) Uani d . 1 . .
    H H4 0.0689 0.3585 0.2112 0.041 Uiso calc R 1 . .
    C C5 0.06124(17) 0.5886(5) 0.16879(14) 0.0354(8) Uani d . 1 . .
    C C6 0.06594(18) 0.7693(5) 0.17914(16) 0.0433(9) Uani d . 1 . .
    H H6 0.0575 0.8442 0.1461 0.052 Uiso calc R 1 . .
    C C7 0.08251(18) 0.8378(5) 0.23618(16) 0.0420(9) Uani d . 1 . .
    H H7 0.0851 0.9575 0.2421 0.050 Uiso calc R 1 . .
    C C8 0.09548(16) 0.7245(4) 0.28526(14) 0.0320(8) Uani d . 1 . .
    C C9 0.1075(2) 0.2737(5) 0.34959(15) 0.0443(10) Uani d . 1 . .
    H H9A 0.1245 0.2101 0.3200 0.053 Uiso calc R 1 . .
    H H9B 0.0613 0.2370 0.3455 0.053 Uiso calc R 1 . .
    C C10 0.1490(2) 0.2273(5) 0.41182(16) 0.0498(10) Uani d . 1 . .
    H H10A 0.1964 0.2432 0.4135 0.060 Uiso calc R 1 . .
    H H10B 0.1379 0.3061 0.4410 0.060 Uiso calc R 1 . .
    C C11 0.0775(2) 0.0334(5) 0.45010(19) 0.0573(11) Uani d . 1 . .
    H H11A 0.0716 -0.0849 0.4612 0.086 Uiso calc R 1 . .
    H H11B 0.0392 0.0687 0.4184 0.086 Uiso calc R 1 . .
    H H11C 0.0813 0.1073 0.4847 0.086 Uiso calc R 1 . .
    C C12 0.1960(2) -0.0103(6) 0.47694(18) 0.0612(12) Uani d . 1 . .
    H H12A 0.2010 0.0638 0.5116 0.092 Uiso calc R 1 . .
    H H12B 0.2362 -0.0046 0.4627 0.092 Uiso calc R 1 . .
    H H12C 0.1889 -0.1279 0.4880 0.092 Uiso calc R 1 . .
    C C13 0.04359(18) 0.5201(5) 0.10521(15) 0.0443(9) Uani d . 1 . .
    H H13A 0.0126 0.6006 0.0794 0.053 Uiso calc R 1 . .
    H H13B 0.0203 0.4100 0.1044 0.053 Uiso calc R 1 . .
    C C14 0.2182(2) 0.4049(6) 0.17041(19) 0.0595(12) Uani d . 1 . .
    H H14A 0.2044 0.5030 0.1911 0.071 Uiso calc R 1 . .
    H H14B 0.2592 0.4352 0.1589 0.071 Uiso calc R 1 . .
    C C15 0.2286(2) 0.2452(7) 0.2097(2) 0.0759(15) Uani d . 1 . .
    H H15A 0.2008 0.2493 0.2382 0.091 Uiso calc R 1 . .
    H H15B 0.2755 0.2338 0.2320 0.091 Uiso calc R 1 . .
    C C16 0.2077(2) 0.0975(7) 0.1657(2) 0.0767(15) Uani d . 1 . .
    H H16A 0.2433 0.0679 0.1466 0.092 Uiso calc R 1 . .
    H H16B 0.1961 -0.0048 0.1858 0.092 Uiso calc R 1 . .
    C C17 0.1470(2) 0.1683(5) 0.12026(19) 0.0596(12) Uani d . 1 . .
    H H17A 0.1408 0.1121 0.0812 0.072 Uiso calc R 1 . .
    H H17B 0.1063 0.1540 0.1341 0.072 Uiso calc R 1 . .
    N N1 0.11326(16) 0.7545(4) 0.34578(13) 0.0399(8) Uani d . 1 . .
    H H1N 0.1201(16) 0.845(4) 0.3638(15) 0.040(10) Uiso d . 1 . .
    N N2 0.13825(16) 0.0472(4) 0.42904(12) 0.0401(8) Uani d . 1 . .
    N N3 0.16437(16) 0.3539(4) 0.11721(13) 0.0487(8) Uani d . 1 . .
    O O1 0.15023(16) 0.6501(4) 0.07875(14) 0.0703(9) Uani d . 1 . .
    O O2 0.08893(16) 0.4082(4) 0.01711(11) 0.0717(10) Uani d . 1 . .
    S S1 0.11450(5) 0.48884(14) 0.07475(4) 0.0467(3) Uani d . 1 . .
_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 C2 . 1.356(4) y
    C1 N1 . 1.369(4) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.436(4) ?
    C2 C9 . 1.499(5) y
    C3 C4 . 1.395(4) ?
    C3 C8 . 1.415(4) ?
    C4 C5 . 1.374(5) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.408(5) ?
    C5 C13 . 1.499(4) y
    C6 C7 . 1.365(5) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.390(5) ?
    C7 H7 . 0.9300 ?
    C8 N1 . 1.356(4) y
    C9 C10 . 1.500(5) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 N2 . 1.472(4) y
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 N2 . 1.451(5) ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    C12 N2 . 1.459(5) ?
    C12 H12A . 0.9600 ?
    C12 H12B . 0.9600 ?
    C12 H12C . 0.9600 ?
    C13 S1 . 1.782(4) y
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    C14 N3 . 1.470(5) ?
    C14 C15 . 1.503(6) ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
    C15 C16 . 1.504(7) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C16 C17 . 1.504(6) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C17 N3 . 1.477(5) ?
    C17 H17A . 0.9700 ?
    C17 H17B . 0.9700 ?
    N1 H1N . 0.80(3) ?
    N3 S1 . 1.598(3) y
    O1 S1 . 1.431(3) ?
    O2 S1 . 1.428(3) ?
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
    C2 C1 N1 . . 110.8(3) ?
    C2 C1 H1 . . 124.6 ?
    N1 C1 H1 . . 124.6 ?
    C1 C2 C3 . . 105.7(3) ?
    C1 C2 C9 . . 127.8(3) ?
    C3 C2 C9 . . 126.4(3) ?
    C4 C3 C8 . . 118.5(3) ?
    C4 C3 C2 . . 134.5(3) ?
    C8 C3 C2 . . 107.0(3) ?
    C5 C4 C3 . . 120.8(3) ?
    C5 C4 H4 . . 119.6 ?
    C3 C4 H4 . . 119.6 ?
    C4 C5 C6 . . 119.0(3) ?
    C4 C5 C13 . . 121.1(3) ?
    C6 C5 C13 . . 119.9(3) ?
    C7 C6 C5 . . 122.0(3) ?
    C7 C6 H6 . . 119.0 ?
    C5 C6 H6 . . 119.0 ?
    C6 C7 C8 . . 118.5(3) ?
    C6 C7 H7 . . 120.8 ?
    C8 C7 H7 . . 120.8 ?
    N1 C8 C7 . . 131.4(3) ?
    N1 C8 C3 . . 107.5(3) ?
    C7 C8 C3 . . 121.1(3) ?
    C2 C9 C10 . . 113.5(3) ?
    C2 C9 H9A . . 108.9 ?
    C10 C9 H9A . . 108.9 ?
    C2 C9 H9B . . 108.9 ?
    C10 C9 H9B . . 108.9 ?
    H9A C9 H9B . . 107.7 ?
    N2 C10 C9 . . 112.9(3) ?
    N2 C10 H10A . . 109.0 ?
    C9 C10 H10A . . 109.0 ?
    N2 C10 H10B . . 109.0 ?
    C9 C10 H10B . . 109.0 ?
    H10A C10 H10B . . 107.8 ?
    N2 C11 H11A . . 109.5 ?
    N2 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    N2 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    N2 C12 H12A . . 109.5 ?
    N2 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    N2 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    C5 C13 S1 . . 114.1(2) ?
    C5 C13 H13A . . 108.7 ?
    S1 C13 H13A . . 108.7 ?
    C5 C13 H13B . . 108.7 ?
    S1 C13 H13B . . 108.7 ?
    H13A C13 H13B . . 107.6 ?
    N3 C14 C15 . . 103.7(4) ?
    N3 C14 H14A . . 111.0 ?
    C15 C14 H14A . . 111.0 ?
    N3 C14 H14B . . 111.0 ?
    C15 C14 H14B . . 111.0 ?
    H14A C14 H14B . . 109.0 ?
    C14 C15 C16 . . 104.2(4) ?
    C14 C15 H15A . . 110.9 ?
    C16 C15 H15A . . 110.9 ?
    C14 C15 H15B . . 110.9 ?
    C16 C15 H15B . . 110.9 ?
    H15A C15 H15B . . 108.9 ?
    C17 C16 C15 . . 103.4(4) ?
    C17 C16 H16A . . 111.1 ?
    C15 C16 H16A . . 111.1 ?
    C17 C16 H16B . . 111.1 ?
    C15 C16 H16B . . 111.1 ?
    H16A C16 H16B . . 109.1 ?
    N3 C17 C16 . . 102.4(4) ?
    N3 C17 H17A . . 111.3 ?
    C16 C17 H17A . . 111.3 ?
    N3 C17 H17B . . 111.3 ?
    C16 C17 H17B . . 111.3 ?
    H17A C17 H17B . . 109.2 ?
    C8 N1 C1 . . 108.9(3) y
    C8 N1 H1N . . 130(2) ?
    C1 N1 H1N . . 122(2) ?
    C11 N2 C12 . . 109.3(3) y
    C11 N2 C10 . . 111.0(3) y
    C12 N2 C10 . . 109.7(3) y
    C14 N3 C17 . . 111.0(3) y
    C14 N3 S1 . . 123.8(3) ?
    C17 N3 S1 . . 122.1(3) ?
    O2 S1 O1 . . 119.74(19) ?
    O2 S1 N3 . . 107.68(18) ?
    O1 S1 N3 . . 106.67(19) ?
    O2 S1 C13 . . 106.01(18) ?
    O1 S1 C13 . . 108.28(19) ?
    N3 S1 C13 . . 108.02(17) y
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 . . . . -0.1(4) ?
    N1 C1 C2 C9 . . . . -177.1(3) ?
    C1 C2 C3 C4 . . . . -179.3(4) ?
    C9 C2 C3 C4 . . . . -2.2(6) ?
    C1 C2 C3 C8 . . . . 0.1(4) ?
    C9 C2 C3 C8 . . . . 177.2(3) ?
    C8 C3 C4 C5 . . . . 1.9(5) ?
    C2 C3 C4 C5 . . . . -178.8(3) ?
    C3 C4 C5 C6 . . . . -1.8(5) ?
    C3 C4 C5 C13 . . . . 178.1(3) ?
    C4 C5 C6 C7 . . . . 0.6(5) ?
    C13 C5 C6 C7 . . . . -179.3(3) ?
    C5 C6 C7 C8 . . . . 0.4(5) ?
    C6 C7 C8 N1 . . . . 179.4(4) ?
    C6 C7 C8 C3 . . . . -0.3(5) ?
    C4 C3 C8 N1 . . . . 179.4(3) ?
    C2 C3 C8 N1 . . . . -0.1(4) ?
    C4 C3 C8 C7 . . . . -0.9(5) ?
    C2 C3 C8 C7 . . . . 179.6(3) ?
    C1 C2 C9 C10 . . . . -23.7(6) ?
    C3 C2 C9 C10 . . . . 159.8(3) ?
    C2 C9 C10 N2 . . . . 169.3(3) y
    C4 C5 C13 S1 . . . . -92.2(4) y
    C6 C5 C13 S1 . . . . 87.7(4) ?
    N3 C14 C15 C16 . . . . 27.4(4) ?
    C14 C15 C16 C17 . . . . -39.3(5) ?
    C15 C16 C17 N3 . . . . 35.0(4) ?
    C7 C8 N1 C1 . . . . -179.6(4) ?
    C3 C8 N1 C1 . . . . 0.1(4) ?
    C2 C1 N1 C8 . . . . 0.0(4) ?
    C9 C10 N2 C11 . . . . -81.0(4) ?
    C9 C10 N2 C12 . . . . 158.1(3) ?
    C15 C14 N3 C17 . . . . -5.4(4) ?
    C15 C14 N3 S1 . . . . 154.9(3) ?
    C16 C17 N3 C14 . . . . -18.6(5) ?
    C16 C17 N3 S1 . . . . -179.3(3) ?
    C14 N3 S1 O2 . . . . 157.1(3) ?
    C17 N3 S1 O2 . . . . -44.7(4) ?
    C14 N3 S1 O1 . . . . 27.4(4) ?
    C17 N3 S1 O1 . . . . -174.4(3) ?
    C14 N3 S1 C13 . . . . -88.8(3) ?
    C17 N3 S1 C13 . . . . 69.4(3) ?
    C5 C13 S1 O2 . . . . 174.5(3) ?
    C5 C13 S1 O1 . . . . -55.9(3) ?
    C5 C13 S1 N3 . . . . 59.3(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
    N1 H1N N2 1_565 0.80(3) 2.12(3) 2.906(4) 167(3)
    C15 H15B Cg2 6_545 0.97 2.96 3.909(5) 166
data_II
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N,N-dimethyl-2-[5-(pyrrolidin-1-ylsulfonylmethyl)-1H-
indol-3-yl]-ethanaminium malate
;
_chemical_name_common     'Almotriptan Malate'
_chemical_formula_moiety     'C17 H26 N3 O2 S +, C4 H5 O5 -'
_chemical_formula_sum     'C21 H31 N3 O7 S'
_chemical_formula_iupac     'C17 H26 N3 O2 S +, C4 H5 O5 -'
_chemical_formula_weight     469.55
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.5542(7)
_cell_length_b     9.3561(9)
_cell_length_c     17.3608(17)
_cell_angle_alpha     104.081(2)
_cell_angle_beta     101.121(2)
_cell_angle_gamma     92.681(2)
_cell_volume     1162.13(19)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     8093
_cell_measurement_theta_min     2.28
_cell_measurement_theta_max     27.87
_cell_measurement_temperature     294(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.19
_exptl_crystal_size_mid     0.14
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.342
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     500
_exptl_absorpt_coefficient_mu     0.186
_exptl_absorpt_correction_type     none
_diffrn_ambient_temperature     294(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 SMART APEX CCD area-detector'
_diffrn_measurement_device     'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method     'ω scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11188
_diffrn_reflns_av_R_equivalents     0.0173
_diffrn_reflns_av_sigmaI/netI     0.0187
_diffrn_reflns_theta_min     2.26
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     4062
_reflns_number_gt     3743
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0511
_refine_ls_R_factor_gt     0.0485
_refine_ls_wR_factor_gt     0.1306
_refine_ls_wR_factor_ref     0.1332
_refine_ls_goodness_of_fit_ref     1.029
_refine_ls_restrained_S_all     1.038
_refine_ls_number_reflns     4062
_refine_ls_number_parameters     307
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0713P)²+0.5979P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.434
_refine_diff_density_min     -0.326
_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'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SAINT (Bruker, 2001)'
_computing_data_reduction     'SAINT (Bruker, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
SHELXTL/PC (Sheldrick, 1990) and PLATON (Spek, 2003)
;
_computing_publication_material     'SHELXL97 (Sheldrick, 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
    C C1 0.3565(3) 0.5689(2) 0.81591(13) 0.0496(5) Uani d . 1 . .
    H H1 0.4444 0.5665 0.8611 0.059 Uiso calc R 1 . .
    C C2 0.3736(3) 0.6561(2) 0.76450(12) 0.0421(4) Uani d . 1 . .
    C C3 0.2072(3) 0.6248(2) 0.70411(11) 0.0387(4) Uani d . 1 . .
    C C4 0.1382(3) 0.6780(2) 0.63659(11) 0.0392(4) Uani d . 1 . .
    H H4 0.2083 0.7475 0.6222 0.047 Uiso calc R 1 . .
    C C5 -0.0348(3) 0.6265(2) 0.59154(12) 0.0425(4) Uani d . 1 . .
    C C6 -0.1393(3) 0.5187(2) 0.61262(14) 0.0514(5) Uani d . 1 . .
    H H6 -0.2548 0.4842 0.5814 0.062 Uiso calc R 1 . .
    C C7 -0.0752(3) 0.4635(2) 0.67779(14) 0.0522(5) Uani d . 1 . .
    H H7 -0.1452 0.3921 0.6909 0.063 Uiso calc R 1 . .
    C C8 0.0977(3) 0.5175(2) 0.72382(12) 0.0434(4) Uani d . 1 . .
    C C9 0.5257(3) 0.7690(2) 0.76954(13) 0.0504(5) Uani d . 1 . .
    H H9A 0.4934 0.8667 0.7933 0.060 Uiso calc R 1 . .
    H H9B 0.5410 0.7664 0.7150 0.060 Uiso calc R 1 . .
    C C10 0.7042(3) 0.7446(2) 0.81952(13) 0.0449(5) Uani d . 1 . .
    H H10A 0.6826 0.7217 0.8687 0.054 Uiso calc R 1 . .
    H H10B 0.7526 0.6600 0.7888 0.054 Uiso calc R 1 . .
    C C11 1.0119(3) 0.8527(3) 0.89491(14) 0.0593(6) Uani d . 1 . .
    H H11A 1.0923 0.9423 0.9127 0.089 Uiso calc R 1 . .
    H H11B 1.0693 0.7750 0.8648 0.089 Uiso calc R 1 . .
    H H11C 0.9839 0.8252 0.9413 0.089 Uiso calc R 1 . .
    C C12 0.8827(3) 0.9256(3) 0.77177(14) 0.0596(6) Uani d . 1 . .
    H H12A 0.9356 0.8486 0.7388 0.089 Uiso calc R 1 . .
    H H12B 0.9662 1.0134 0.7909 0.089 Uiso calc R 1 . .
    H H12C 0.7726 0.9463 0.7401 0.089 Uiso calc R 1 . .
    C C13 -0.1144(3) 0.6828(2) 0.51917(12) 0.0476(5) Uani d . 1 . .
    H H13A -0.1778 0.6000 0.4756 0.057 Uiso calc R 1 . .
    H H13B -0.0168 0.7252 0.5002 0.057 Uiso calc R 1 . .
    C C14 -0.2510(4) 0.9455(3) 0.41993(16) 0.0735(8) Uani d . 1 . .
    H H14A -0.1244 0.9268 0.4288 0.088 Uiso calc R 1 . .
    H H14B -0.2590 1.0501 0.4421 0.088 Uiso calc R 1 . .
    C C15 -0.3352(6) 0.8996(5) 0.33358(19) 0.1132(15) Uani d D 1 . .
    H H15A -0.3753 0.9851 0.3152 0.136 Uiso calc R 1 . .
    H H15B -0.2473 0.8575 0.3028 0.136 Uiso calc R 1 . .
    C C16 -0.4875(5) 0.7917(4) 0.31961(18) 0.1004(12) Uani d D 1 . .
    H H16A -0.4744 0.7036 0.2789 0.120 Uiso calc R 1 . .
    H H16B -0.5987 0.8317 0.3000 0.120 Uiso calc R 1 . .
    C C17 -0.4956(4) 0.7541(3) 0.39624(16) 0.0737(8) Uani d . 1 . .
    H H17A -0.6137 0.7684 0.4094 0.088 Uiso calc R 1 . .
    H H17B -0.4719 0.6520 0.3929 0.088 Uiso calc R 1 . .
    N N1 0.1925(3) 0.4855(2) 0.79181(12) 0.0516(5) Uani d . 1 . .
    H H1N 0.163(3) 0.423(3) 0.8129(15) 0.053(7) Uiso d . 1 . .
    N N2 0.8417(2) 0.8767(2) 0.84211(10) 0.0405(4) Uani d . 1 . .
    H H2N 0.795(3) 0.948(2) 0.8705(13) 0.041(6) Uiso d . 1 . .
    N N3 -0.3541(2) 0.8557(2) 0.45714(12) 0.0555(5) Uani d . 1 . .
    O O1 -0.1631(2) 0.95083(19) 0.59370(10) 0.0642(5) Uani d . 1 . .
    O O2 -0.4126(2) 0.7547(2) 0.56822(11) 0.0696(5) Uani d . 1 . .
    S S1 -0.26839(7) 0.81938(6) 0.54157(3) 0.04687(18) Uani d . 1 . .
    C C18 0.8886(3) 0.3345(2) 0.91463(15) 0.0514(5) Uani d . 1 . .
    C C19 0.7153(3) 0.3468(2) 0.94722(16) 0.0541(6) Uani d . 1 . .
    H H19A 0.7453 0.3690 1.0061 0.065 Uiso calc R 1 . .
    H H19B 0.6528 0.4273 0.9320 0.065 Uiso calc R 1 . .
    C C20 0.5928(3) 0.2046(2) 0.91385(13) 0.0432(5) Uani d . 1 . .
    H H20 0.5662 0.1827 0.8544 0.052 Uiso calc R 1 . .
    C C21 0.4134(2) 0.2173(2) 0.94254(13) 0.0432(5) Uani d . 1 . .
    O O3 0.8941(2) 0.3315(3) 0.84577(13) 0.0913(7) Uani d . 1 . .
    O O4 1.0288(2) 0.3294(2) 0.96938(13) 0.0739(6) Uani d D 1 . .
    H H4O 1.125(3) 0.325(4) 0.952(2) 0.109(12) Uiso d D 1 . .
    O O5 0.6814(2) 0.08617(16) 0.93734(9) 0.0453(4) Uani d . 1 . .
    H H5O 0.615(4) 0.048(3) 0.9593(17) 0.071(9) Uiso d . 1 . .
    O O6 0.3180(2) 0.3113(2) 0.91909(13) 0.0735(6) Uani d . 1 . .
    O O7 0.3758(2) 0.13715(18) 0.98469(10) 0.0578(4) Uani d . 1 . .
_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 N1 . 1.367(3) ?
    C1 C2 . 1.367(3) y
    C1 H1 . 0.9300 ?
    C2 C3 . 1.440(3) ?
    C2 C9 . 1.499(3) y
    C3 C4 . 1.402(3) ?
    C3 C8 . 1.417(3) ?
    C4 C5 . 1.383(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.411(3) ?
    C5 C13 . 1.509(3) y
    C6 C7 . 1.370(3) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.393(3) ?
    C7 H7 . 0.9300 ?
    C8 N1 . 1.364(3) y
    C9 C10 . 1.516(3) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 N2 . 1.499(3) y
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 N2 . 1.489(2) ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    C12 N2 . 1.483(3) ?
    C12 H12A . 0.9600 ?
    C12 H12B . 0.9600 ?
    C12 H12C . 0.9600 ?
    C13 S1 . 1.791(2) y
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    C14 N3 . 1.459(3) ?
    C14 C15 . 1.459(4) ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
    C15 C16 . 1.437(4) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C16 C17 . 1.468(4) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C17 N3 . 1.464(3) ?
    C17 H17A . 0.9700 ?
    C17 H17B . 0.9700 ?
    N1 H1N . 0.81(2) ?
    N2 H2N . 0.86(2) ?
    N3 S1 . 1.6064(18) y
    O1 S1 . 1.4331(17) ?
    O2 S1 . 1.4272(17) ?
    C18 O3 . 1.198(3) ?
    C18 O4 . 1.290(3) ?
    C18 C19 . 1.522(3) ?
    C19 C20 . 1.505(3) y
    C19 H19A . 0.9700 ?
    C19 H19B . 0.9700 ?
    C20 O5 . 1.424(2) ?
    C20 C21 . 1.531(3) ?
    C20 H20 . 0.9800 ?
    C21 O7 . 1.227(2) ?
    C21 O6 . 1.257(2) ?
    O4 H4O . 0.833(10) ?
    O5 H5O . 0.80(3) ?
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 . . 110.68(18) ?
    N1 C1 H1 . . 124.7 ?
    C2 C1 H1 . . 124.7 ?
    C1 C2 C3 . . 105.87(18) ?
    C1 C2 C9 . . 129.03(18) ?
    C3 C2 C9 . . 125.02(17) ?
    C4 C3 C8 . . 118.72(18) ?
    C4 C3 C2 . . 134.48(18) ?
    C8 C3 C2 . . 106.78(17) ?
    C5 C4 C3 . . 119.70(18) ?
    C5 C4 H4 . . 120.2 ?
    C3 C4 H4 . . 120.2 ?
    C4 C5 C6 . . 119.97(18) ?
    C4 C5 C13 . . 121.15(18) ?
    C6 C5 C13 . . 118.88(18) ?
    C7 C6 C5 . . 121.8(2) ?
    C7 C6 H6 . . 119.1 ?
    C5 C6 H6 . . 119.1 ?
    C6 C7 C8 . . 118.0(2) ?
    C6 C7 H7 . . 121.0 ?
    C8 C7 H7 . . 121.0 ?
    N1 C8 C7 . . 130.5(2) ?
    N1 C8 C3 . . 107.71(18) ?
    C7 C8 C3 . . 121.78(18) ?
    C2 C9 C10 . . 113.23(17) ?
    C2 C9 H9A . . 108.9 ?
    C10 C9 H9A . . 108.9 ?
    C2 C9 H9B . . 108.9 ?
    C10 C9 H9B . . 108.9 ?
    H9A C9 H9B . . 107.7 ?
    N2 C10 C9 . . 112.71(16) ?
    N2 C10 H10A . . 109.1 ?
    C9 C10 H10A . . 109.1 ?
    N2 C10 H10B . . 109.1 ?
    C9 C10 H10B . . 109.1 ?
    H10A C10 H10B . . 107.8 ?
    N2 C11 H11A . . 109.5 ?
    N2 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    N2 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    N2 C12 H12A . . 109.5 ?
    N2 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    N2 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    C5 C13 S1 . . 112.92(14) ?
    C5 C13 H13A . . 109.0 ?
    S1 C13 H13A . . 109.0 ?
    C5 C13 H13B . . 109.0 ?
    S1 C13 H13B . . 109.0 ?
    H13A C13 H13B . . 107.8 ?
    N3 C14 C15 . . 104.6(2) ?
    N3 C14 H14A . . 110.8 ?
    C15 C14 H14A . . 110.8 ?
    N3 C14 H14B . . 110.8 ?
    C15 C14 H14B . . 110.8 ?
    H14A C14 H14B . . 108.9 ?
    C16 C15 C14 . . 110.1(3) ?
    C16 C15 H15A . . 109.6 ?
    C14 C15 H15A . . 109.6 ?
    C16 C15 H15B . . 109.6 ?
    C14 C15 H15B . . 109.6 ?
    H15A C15 H15B . . 108.2 ?
    C15 C16 C17 . . 108.8(2) ?
    C15 C16 H16A . . 109.9 ?
    C17 C16 H16A . . 109.9 ?
    C15 C16 H16B . . 109.9 ?
    C17 C16 H16B . . 109.9 ?
    H16A C16 H16B . . 108.3 ?
    N3 C17 C16 . . 104.8(2) ?
    N3 C17 H17A . . 110.8 ?
    C16 C17 H17A . . 110.8 ?
    N3 C17 H17B . . 110.8 ?
    C16 C17 H17B . . 110.8 ?
    H17A C17 H17B . . 108.9 ?
    C8 N1 C1 . . 108.96(18) y
    C8 N1 H1N . . 126.7(18) ?
    C1 N1 H1N . . 124.2(18) ?
    C12 N2 C11 . . 110.40(17) y
    C12 N2 C10 . . 114.21(17) y
    C11 N2 C10 . . 111.52(17) y
    C12 N2 H2N . . 107.3(14) ?
    C11 N2 H2N . . 107.0(15) ?
    C10 N2 H2N . . 105.9(15) ?
    C14 N3 C17 . . 111.4(2) y
    C14 N3 S1 . . 121.76(16) ?
    C17 N3 S1 . . 121.28(16) ?
    O2 S1 O1 . . 119.06(12) ?
    O2 S1 N3 . . 107.34(10) ?
    O1 S1 N3 . . 107.64(10) ?
    O2 S1 C13 . . 108.35(11) ?
    O1 S1 C13 . . 107.29(11) ?
    N3 S1 C13 . . 106.52(10) y
    O3 C18 O4 . . 123.9(2) ?
    O3 C18 C19 . . 123.4(2) ?
    O4 C18 C19 . . 112.7(2) ?
    C20 C19 C18 . . 110.68(19) ?
    C20 C19 H19A . . 109.5 ?
    C18 C19 H19A . . 109.5 ?
    C20 C19 H19B . . 109.5 ?
    C18 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 108.1 ?
    O5 C20 C19 . . 110.07(16) ?
    O5 C20 C21 . . 109.95(16) ?
    C19 C20 C21 . . 111.50(17) ?
    O5 C20 H20 . . 108.4 ?
    C19 C20 H20 . . 108.4 ?
    C21 C20 H20 . . 108.4 ?
    O7 C21 O6 . . 126.49(18) ?
    O7 C21 C20 . . 118.75(17) ?
    O6 C21 C20 . . 114.75(17) ?
    C18 O4 H4O . . 113(3) ?
    C20 O5 H5O . . 107(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
    N1 C1 C2 C3 . . . . 0.2(2) ?
    N1 C1 C2 C9 . . . . 177.0(2) ?
    C1 C2 C3 C4 . . . . 178.6(2) ?
    C9 C2 C3 C4 . . . . 1.6(4) ?
    C1 C2 C3 C8 . . . . 0.0(2) ?
    C9 C2 C3 C8 . . . . -176.91(19) ?
    C8 C3 C4 C5 . . . . 0.8(3) ?
    C2 C3 C4 C5 . . . . -177.6(2) ?
    C3 C4 C5 C6 . . . . -1.3(3) ?
    C3 C4 C5 C13 . . . . 179.18(18) ?
    C4 C5 C6 C7 . . . . 0.8(3) ?
    C13 C5 C6 C7 . . . . -179.7(2) ?
    C5 C6 C7 C8 . . . . 0.4(3) ?
    C6 C7 C8 N1 . . . . 178.3(2) ?
    C6 C7 C8 C3 . . . . -0.9(3) ?
    C4 C3 C8 N1 . . . . -179.05(17) ?
    C2 C3 C8 N1 . . . . -0.2(2) ?
    C4 C3 C8 C7 . . . . 0.3(3) ?
    C2 C3 C8 C7 . . . . 179.17(19) ?
    C1 C2 C9 C10 . . . . 22.9(3) ?
    C3 C2 C9 C10 . . . . -160.94(19) ?
    C2 C9 C10 N2 . . . . -165.28(17) ?
    C4 C5 C13 S1 . . . . -100.7(2) ?
    C6 C5 C13 S1 . . . . 79.8(2) ?
    N3 C14 C15 C16 . . . . 2.5(5) ?
    C14 C15 C16 C17 . . . . -5.4(5) ?
    C15 C16 C17 N3 . . . . 5.9(4) ?
    C7 C8 N1 C1 . . . . -179.0(2) ?
    C3 C8 N1 C1 . . . . 0.4(2) ?
    C2 C1 N1 C8 . . . . -0.4(3) ?
    C9 C10 N2 C12 . . . . -57.1(2) ?
    C9 C10 N2 C11 . . . . 176.86(18) ?
    C15 C14 N3 C17 . . . . 1.4(4) ?
    C15 C14 N3 S1 . . . . 155.3(3) ?
    C16 C17 N3 C14 . . . . -4.5(4) ?
    C16 C17 N3 S1 . . . . -158.6(2) ?
    C14 N3 S1 O2 . . . . 169.3(2) ?
    C17 N3 S1 O2 . . . . -39.3(3) ?
    C14 N3 S1 O1 . . . . 40.0(2) ?
    C17 N3 S1 O1 . . . . -168.5(2) ?
    C14 N3 S1 C13 . . . . -74.8(2) ?
    C17 N3 S1 C13 . . . . 76.6(2) ?
    C5 C13 S1 O2 . . . . -59.60(18) ?
    C5 C13 S1 O1 . . . . 70.15(18) ?
    C5 C13 S1 N3 . . . . -174.81(15) ?
    O3 C18 C19 C20 . . . . 71.6(3) ?
    O4 C18 C19 C20 . . . . -109.1(2) ?
    C18 C19 C20 O5 . . . . 60.5(2) ?
    C18 C19 C20 C21 . . . . -177.14(17) y
    O5 C20 C21 O7 . . . . 5.1(3) ?
    C19 C20 C21 O7 . . . . -117.3(2) ?
    O5 C20 C21 O6 . . . . -174.6(2) ?
    C19 C20 C21 O6 . . . . 63.0(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
    N1 H1N O3 1_455 0.81(2) 2.39(3) 3.034(3) 138(2)
    N1 H1N O6 . 0.81(2) 2.47(2) 3.087(2) 135(2)
    N2 H2N O5 1_565 0.86(2) 1.88(2) 2.731(2) 173(2)
    O4 H4O O6 1_655 0.830(10)
                            1.670(10)
                                    2.503(2) 178(4)
    O5 H5O O7 . 0.80(3) 2.11(3) 2.623(2) 122(3)
    O5 H5O O7 2_657 0.80(3) 2.19(3) 2.811(2) 135(3)
    C11 H11C O4 2_767 0.96 2.38 3.276(3) 156
    C14 H14A O1 2_576 0.97 2.55 3.301(3) 134
    C11 H11B Cg1 1_655 0.96 2.87 3.819(3) 172
    C12 H12A Cg2 1_655 0.96 2.83 3.767(3) 164
    C13 H13A Cg2 2_566 0.97 2.91 3.5770(10)
                                          127
data_global
_journal_date_recd_electronic     2007-11-01
_journal_date_accepted     2007-11-18
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2008
_journal_volume     64
_journal_issue      1
_journal_page_first     o15
_journal_page_last     o17
_journal_paper_category     FO
_journal_coeditor_code     DN3071
_publ_contact_author_name     'K. Ravikumar'
_publ_contact_author_address
;
Laboratory of X-ray Crystallography
Indian Institute of Chemical Technology
Hyderabad- 500 007
India
;
_publ_contact_author_email     sshiya@yahoo.com
_publ_contact_author_fax     '09104027193118'
_publ_contact_author_phone     '09104027193118'
_publ_section_title
;
Almotriptan, an antimigraine agent, and its malate salt
;
loop_
    _publ_author_name
    _publ_author_address
    'K. Ravikumar'
;
Laboratory of X-ray Crystallography
Indian Institute of Chemical Technology
Hyderabad 500 007
India
;
    'B. Sridhar'
;Laboratory of X-ray Crystallography
Indian Institute of Chemical Technology
Hyderabad 500 007
India
;
    'Harihara Krishnan'
;
SMS Pharma Research Centre
Hyderabad 500 038
India
;
    'A. N. Singh'
;
SMS Pharma Research Centre
Hyderabad 500 038
India
;
