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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# 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_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(+)-(R,S,S,S)-bis[2-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)-2-\
hydroxyethyl]ammonium chloride dihydrate
;
_chemical_name_common     'L-Nebiviololinium chloride dihydrate'
_chemical_formula_moiety     'C22 H26 F2 N O4 +, Cl -, 2H2 O'
_chemical_formula_sum     'C22 H30 Cl F2 N O6'
_chemical_formula_iupac     'C22 H26 F2 N O4 +, Cl -, 2H2 O'
_chemical_formula_weight     477.92
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
_symmetry_space_group_name_Hall     'P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y+1/2, -z+1/2'
_cell_length_a     4.8026(4)
_cell_length_b     14.5781(12)
_cell_length_c     33.261(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2328.7(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     120
_cell_measurement_theta_min     1.22
_cell_measurement_theta_max     25.4
_cell_measurement_temperature     291(2)
_exptl_crystal_description     'needle'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.60
_exptl_crystal_size_mid     0.12
_exptl_crystal_size_min     0.09
_exptl_crystal_density_diffrn     1.363
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1008
_exptl_absorpt_coefficient_mu     0.218
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker,  2001)'
_exptl_absorpt_correction_T_min     0.865
_exptl_absorpt_correction_T_max     0.981
_diffrn_ambient_temperature     292(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'APEX CCD area-detector'
_diffrn_measurement_method     'ω-scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     26222
_diffrn_reflns_av_R_equivalents     0.0542
_diffrn_reflns_av_sigmaI/netI     0.0300
_diffrn_reflns_theta_min     1.22
_diffrn_reflns_theta_max     26.40
_diffrn_reflns_theta_full     26.40
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -41
_diffrn_reflns_limit_l_max     41
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3401
_reflns_number_gt     2857
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0539
_refine_ls_R_factor_gt     0.0406
_refine_ls_wR_factor_gt     0.0983
_refine_ls_wR_factor_ref     0.1131
_refine_ls_goodness_of_fit_ref     1.053
_refine_ls_restrained_S_all     1.052
_refine_ls_number_reflns     3401
_refine_ls_number_parameters     301
_refine_ls_number_restraints     6
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0545P)²+0.9780P] 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     0.004
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.327
_refine_diff_density_min     -0.241
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), xx Friedel pairs'
_refine_ls_abs_structure_Flack     -0.04(12)
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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'F' 'F' 0.0171 0.0103
                         '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     'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material     'SHELXTL (Bruker, 2001)'
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
    Cl Cl1 0.7060(2) 0.96561(9) 0.28493(3) 0.0826(4) Uani d . 1 . .
    O O1W 0.2063(8) 1.0846(2) 0.24528(8) 0.0899(10) Uani d D 1 . .
    H H1A 0.348(7) 0.866(3) 0.2722(19) 0.135 Uiso d D 1 . .
    H H1B 0.348(8) 1.075(3) 0.2618(13) 0.135 Uiso d D 1 . .
    O O2W 0.2154(7) 0.8243(2) 0.26894(9) 0.0772(8) Uani d D 1 . .
    H H2A 0.064(6) 0.858(3) 0.2719(18) 0.116 Uiso d D 1 . .
    H H2B 0.191(10) 1.0312(17) 0.2332(13) 0.116 Uiso d D 1 . .
    N N1 0.7326(6) 0.57169(17) 0.33807(7) 0.0461(7) Uani d . 1 . .
    H H1 0.8475 0.5622 0.3171 0.069 Uiso calc R 1 . .
    H H2 0.5829 0.6026 0.3290 0.069 Uiso calc R 1 . .
    C C2' 0.8776(7) 0.6276(2) 0.36873(9) 0.0435(8) Uani d . 1 . .
    H H3 1.0288 0.5918 0.3800 0.052 Uiso calc R 1 . .
    H H4 0.7484 0.6414 0.3903 0.052 Uiso calc R 1 . .
    C C2 0.6415(7) 0.4814(2) 0.35470(9) 0.0397(8) Uani d . 1 . .
    H H5 0.5196 0.4920 0.3775 0.048 Uiso calc R 1 . .
    H H6 0.8035 0.4483 0.3643 0.048 Uiso calc R 1 . .
    C C3 0.4905(7) 0.4230(2) 0.32411(9) 0.0390(8) Uani d . 1 . .
    H H7 0.6169 0.4092 0.3018 0.058 Uiso calc R 1 . .
    C C3' 0.9940(7) 0.7165(2) 0.35241(9) 0.0403(8) Uani d . 1 . .
    H H8 0.8498 0.7478 0.3367 0.048 Uiso calc R 1 . .
    O O4 0.2600(5) 0.47447(14) 0.30934(6) 0.0449(5) Uani d . 1 . .
    H H9 0.1744 0.4437 0.2928 0.067 Uiso calc R 1 . .
    O O4' 1.2211(5) 0.69428(15) 0.32678(6) 0.0508(6) Uani d . 1 . .
    H H10 1.2871 0.7415 0.3174 0.076 Uiso calc R 1 . .
    C C5 0.3984(7) 0.3337(2) 0.34381(9) 0.0403(8) Uani d . 1 . .
    H H11 0.5645 0.3008 0.3530 0.060 Uiso calc R 1 . .
    C C5' 1.0904(7) 0.7793(2) 0.38644(9) 0.0390(8) Uani d . 1 . .
    H H12 1.2551 0.7521 0.3991 0.047 Uiso calc R 1 . .
    O O6 0.2381(5) 0.36036(13) 0.37856(6) 0.0455(6) Uani d . 1 . .
    O O6' 0.8676(5) 0.78023(15) 0.41512(6) 0.0473(6) Uani d . 1 . .
    C C7 0.0810(7) 0.2942(2) 0.39725(9) 0.0421(8) Uani d . 1 . .
    C C7' 0.8967(7) 0.8404(2) 0.44712(9) 0.0411(8) Uani d . 1 . .
    C C8 0.0283(7) 0.2085(2) 0.37968(11) 0.0457(9) Uani d . 1 . .
    C C8' 1.0804(7) 0.9139(2) 0.44601(10) 0.0431(8) Uani d . 1 . .
    C C9 0.1485(8) 0.1844(2) 0.33954(11) 0.0571(10) Uani d . 1 . .
    H H13 0.0117 0.1508 0.3239 0.069 Uiso calc R 1 . .
    H H14 0.3097 0.1452 0.3432 0.069 Uiso calc R 1 . .
    C C9' 1.2565(8) 0.9325(2) 0.40927(9) 0.0461(8) Uani d . 1 . .
    H H15 1.4495 0.9183 0.4152 0.055 Uiso calc R 1 . .
    H H16 1.2451 0.9971 0.4025 0.055 Uiso calc R 1 . .
    C C10 0.2340(9) 0.2710(2) 0.31677(9) 0.0506(9) Uani d . 1 . .
    H H17 0.3460 0.2543 0.2936 0.061 Uiso calc R 1 . .
    H H18 0.0692 0.3026 0.3072 0.061 Uiso calc R 1 . .
    C C10' 1.1607(7) 0.8755(2) 0.37343(9) 0.0455(8) Uani d . 1 . .
    H H19 0.9982 0.9038 0.3614 0.055 Uiso calc R 1 . .
    H H20 1.3072 0.8736 0.3534 0.055 Uiso calc R 1 . .
    C C11 -0.0325(8) 0.3188(3) 0.43371(10) 0.0527(9) Uani d . 1 . .
    H H21 0.0097 0.3756 0.4449 0.063 Uiso calc R 1 . .
    C C11' 0.7255(8) 0.8244(2) 0.47963(9) 0.0499(9) Uani d . 1 . .
    H H22 0.6006 0.7757 0.4791 0.060 Uiso calc R 1 . .
    C C12 -0.2092(9) 0.2592(3) 0.45375(12) 0.0668(11) Uani d . 1 . .
    H H23 -0.2908 0.2753 0.4781 0.080 Uiso calc R 1 . .
    C C12' 0.7387(9) 0.8806(3) 0.51317(10) 0.0578(10) Uani d . 1 . .
    H H24 0.6242 0.8707 0.5353 0.069 Uiso calc R 1 . .
    C C13 -0.2590(9) 0.1757(3) 0.43632(13) 0.0660(11) Uani d . 1 . .
    C C13' 0.9266(9) 0.9516(3) 0.51263(10) 0.0581(10) Uani d . 1 . .
    C C14 -0.1492(8) 0.1495(3) 0.40030(13) 0.0615(11) Uani d . 1 . .
    H H25 -0.1928 0.0924 0.3895 0.092 Uiso calc R 1 . .
    C C14' 1.0930(8) 0.9700(3) 0.48011(10) 0.0551(9) Uani d . 1 . .
    H H26 1.2141 1.0198 0.4807 0.066 Uiso calc R 1 . .
    F F1 -0.4347(6) 0.11636(19) 0.45634(9) 0.1020(9) Uani d . 1 . .
    F F1' 0.9452(7) 1.00610(18) 0.54589(7) 0.0957(9) 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
    O1W H1B . 0.89(4) ?
    O1W H2B . 0.88(3) ?
    O2W H1A . 0.89(4) ?
    O2W H2A . 0.92(5) ?
    N1 C2' . 1.479(4) ?
    N1 C2 . 1.493(4) ?
    N1 H1 . 0.9000 ?
    N1 H2 . 0.9000 ?
    C2' C3' . 1.512(4) ?
    C2' H3 . 0.9700 ?
    C2' H4 . 0.9700 ?
    C2 C3 . 1.512(4) ?
    C2 H5 . 0.9700 ?
    C2 H6 . 0.9700 ?
    C3 O4 . 1.424(4) ?
    C3 C5 . 1.524(4) ?
    C3 H7 . 0.9800 ?
    C3' O4' . 1.422(4) ?
    C3' C5' . 1.528(4) ?
    C3' H8 . 0.9800 ?
    O4 H9 . 0.8200 ?
    O4' H10 . 0.8200 ?
    C5 O6 . 1.442(4) ?
    C5 C10 . 1.506(5) ?
    C5 H11 . 0.9800 ?
    C5' O6' . 1.434(4) ?
    C5' C10' . 1.505(4) ?
    C5' H12 . 0.9800 ?
    O6 C7 . 1.373(4) ?
    O6' C7' . 1.386(4) ?
    C7 C11 . 1.377(5) ?
    C7 C8 . 1.402(5) ?
    C7' C11' . 1.378(5) ?
    C7' C8' . 1.388(5) ?
    C8 C14 . 1.391(5) ?
    C8 C9 . 1.496(5) ?
    C8' C14' . 1.400(5) ?
    C8' C9' . 1.511(5) ?
    C9 C10 . 1.528(5) ?
    C9 H13 . 0.9700 ?
    C9 H14 . 0.9700 ?
    C9' C10' . 1.525(4) ?
    C9' H15 . 0.9700 ?
    C9' H16 . 0.9700 ?
    C10 H17 . 0.9700 ?
    C10 H18 . 0.9700 ?
    C10' H19 . 0.9700 ?
    C10' H20 . 0.9700 ?
    C11 C12 . 1.385(5) ?
    C11 H21 . 0.9300 ?
    C11' C12' . 1.386(5) ?
    C11' H22 . 0.9300 ?
    C12 C13 . 1.370(6) ?
    C12 H23 . 0.9300 ?
    C12' C13' . 1.372(5) ?
    C12' H24 . 0.9300 ?
    C13 C14 . 1.363(6) ?
    C13 F1 . 1.379(4) ?
    C13' C14' . 1.371(5) ?
    C13' F1' . 1.365(4) ?
    C14 H25 . 0.9300 ?
    C14' H26 . 0.9300 ?
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
    H1B O1W H2B . . 102(4) ?
    H1A O2W H2A . . 101(4) ?
    C2' N1 C2 . . 111.6(2) ?
    C2' N1 H1 . . 109.3 ?
    C2 N1 H1 . . 109.3 ?
    C2' N1 H2 . . 109.3 ?
    C2 N1 H2 . . 109.3 ?
    H1 N1 H2 . . 108.0 ?
    N1 C2' C3' . . 113.5(3) ?
    N1 C2' H3 . . 108.9 ?
    C3' C2' H3 . . 108.9 ?
    N1 C2' H4 . . 108.9 ?
    C3' C2' H4 . . 108.9 ?
    H3 C2' H4 . . 107.7 ?
    N1 C2 C3 . . 112.8(2) ?
    N1 C2 H5 . . 109.0 ?
    C3 C2 H5 . . 109.0 ?
    N1 C2 H6 . . 109.0 ?
    C3 C2 H6 . . 109.0 ?
    H5 C2 H6 . . 107.8 ?
    O4 C3 C2 . . 108.0(2) ?
    O4 C3 C5 . . 111.9(3) ?
    C2 C3 C5 . . 109.3(2) ?
    O4 C3 H7 . . 109.2 ?
    C2 C3 H7 . . 109.2 ?
    C5 C3 H7 . . 109.2 ?
    O4' C3' C2' . . 107.7(3) ?
    O4' C3' C5' . . 110.4(3) ?
    C2' C3' C5' . . 111.1(2) ?
    O4' C3' H8 . . 109.2 ?
    C2' C3' H8 . . 109.2 ?
    C5' C3' H8 . . 109.2 ?
    C3 O4 H9 . . 109.5 ?
    C3' O4' H10 . . 109.5 ?
    O6 C5 C10 . . 111.3(3) ?
    O6 C5 C3 . . 105.6(2) ?
    C10 C5 C3 . . 114.5(3) ?
    O6 C5 H11 . . 108.4 ?
    C10 C5 H11 . . 108.4 ?
    C3 C5 H11 . . 108.4 ?
    O6' C5' C10' . . 110.5(3) ?
    O6' C5' C3' . . 105.8(2) ?
    C10' C5' C3' . . 114.4(3) ?
    O6' C5' H12 . . 108.7 ?
    C10' C5' H12 . . 108.7 ?
    C3' C5' H12 . . 108.7 ?
    C7 O6 C5 . . 117.8(2) ?
    C7' O6' C5' . . 116.2(2) ?
    O6 C7 C11 . . 115.7(3) ?
    O6 C7 C8 . . 122.4(3) ?
    C11 C7 C8 . . 121.8(3) ?
    C11' C7' O6' . . 115.8(3) ?
    C11' C7' C8' . . 122.0(3) ?
    O6' C7' C8' . . 122.1(3) ?
    C14 C8 C7 . . 117.1(3) ?
    C14 C8 C9 . . 122.1(3) ?
    C7 C8 C9 . . 120.7(3) ?
    C7' C8' C14' . . 117.2(3) ?
    C7' C8' C9' . . 121.1(3) ?
    C14' C8' C9' . . 121.7(3) ?
    C8 C9 C10 . . 110.6(3) ?
    C8 C9 H13 . . 109.5 ?
    C10 C9 H13 . . 109.5 ?
    C8 C9 H14 . . 109.5 ?
    C10 C9 H14 . . 109.5 ?
    H13 C9 H14 . . 108.1 ?
    C8' C9' C10' . . 111.4(3) ?
    C8' C9' H15 . . 109.3 ?
    C10' C9' H15 . . 109.3 ?
    C8' C9' H16 . . 109.3 ?
    C10' C9' H16 . . 109.3 ?
    H15 C9' H16 . . 108.0 ?
    C5 C10 C9 . . 110.3(3) ?
    C5 C10 H17 . . 109.6 ?
    C9 C10 H17 . . 109.6 ?
    C5 C10 H18 . . 109.6 ?
    C9 C10 H18 . . 109.6 ?
    H17 C10 H18 . . 108.1 ?
    C5' C10' C9' . . 110.5(3) ?
    C5' C10' H19 . . 109.5 ?
    C9' C10' H19 . . 109.5 ?
    C5' C10' H20 . . 109.5 ?
    C9' C10' H20 . . 109.5 ?
    H19 C10' H20 . . 108.1 ?
    C7 C11 C12 . . 120.2(3) ?
    C7 C11 H21 . . 119.9 ?
    C12 C11 H21 . . 119.9 ?
    C7' C11' C12' . . 120.3(4) ?
    C7' C11' H22 . . 119.9 ?
    C12' C11' H22 . . 119.9 ?
    C13 C12 C11 . . 117.5(4) ?
    C13 C12 H23 . . 121.3 ?
    C11 C12 H23 . . 121.3 ?
    C13' C12' C11' . . 117.7(4) ?
    C13' C12' H24 . . 121.1 ?
    C11' C12' H24 . . 121.1 ?
    C14 C13 C12 . . 123.5(4) ?
    C14 C13 F1 . . 119.1(4) ?
    C12 C13 F1 . . 117.4(4) ?
    C14' C13' F1' . . 119.1(4) ?
    C14' C13' C12' . . 122.7(3) ?
    F1' C13' C12' . . 118.1(3) ?
    C13 C14 C8 . . 119.9(4) ?
    C13 C14 H25 . . 120.1 ?
    C8 C14 H25 . . 120.1 ?
    C13' C14' C8' . . 120.0(4) ?
    C13' C14' H26 . . 120.0 ?
    C8' C14' H26 . . 120.0 ?
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
    C2 N1 C2' C3' . . . . 175.4(3) ?
    C2' N1 C2 C3 . . . . 179.6(3) ?
    N1 C2 C3 O4 . . . . -56.6(3) ?
    N1 C2 C3 C5 . . . . -178.5(3) ?
    N1 C2' C3' O4' . . . . -70.0(4) ?
    N1 C2' C3' C5' . . . . 169.0(3) ?
    O4 C3 C5 O6 . . . . -64.8(3) ?
    C2 C3 C5 O6 . . . . 54.8(3) ?
    O4 C3 C5 C10 . . . . 58.0(4) ?
    C2 C3 C5 C10 . . . . 177.5(3) ?
    O4' C3' C5' O6' . . . . -167.0(2) ?
    C2' C3' C5' O6' . . . . -47.6(3) ?
    O4' C3' C5' C10' . . . . 71.1(4) ?
    C2' C3' C5' C10' . . . . -169.5(3) ?
    C10 C5 O6 C7 . . . . 41.9(4) ?
    C3 C5 O6 C7 . . . . 166.7(3) ?
    C10' C5' O6' C7' . . . . -49.5(4) ?
    C3' C5' O6' C7' . . . . -173.9(2) ?
    C5 O6 C7 C11 . . . . 170.0(3) ?
    C5 O6 C7 C8 . . . . -12.7(4) ?
    C5' O6' C7' C11' . . . . -163.3(3) ?
    C5' O6' C7' C8' . . . . 18.7(4) ?
    O6 C7 C8 C14 . . . . -175.8(3) ?
    C11 C7 C8 C14 . . . . 1.3(5) ?
    O6 C7 C8 C9 . . . . 1.4(5) ?
    C11 C7 C8 C9 . . . . 178.5(3) ?
    C11' C7' C8' C14' . . . . 2.2(5) ?
    O6' C7' C8' C14' . . . . -179.8(3) ?
    C11' C7' C8' C9' . . . . -177.2(3) ?
    O6' C7' C8' C9' . . . . 0.8(5) ?
    C14 C8 C9 C10 . . . . 157.4(4) ?
    C7 C8 C9 C10 . . . . -19.6(5) ?
    C7' C8' C9' C10' . . . . 11.8(4) ?
    C14' C8' C9' C10' . . . . -167.6(3) ?
    O6 C5 C10 C9 . . . . -59.5(4) ?
    C3 C5 C10 C9 . . . . -179.1(3) ?
    C8 C9 C10 C5 . . . . 47.3(4) ?
    O6' C5' C10' C9' . . . . 61.2(4) ?
    C3' C5' C10' C9' . . . . -179.6(3) ?
    C8' C9' C10' C5' . . . . -41.4(4) ?
    O6 C7 C11 C12 . . . . 175.8(3) ?
    C8 C7 C11 C12 . . . . -1.5(5) ?
    O6' C7' C11' C12' . . . . 179.9(3) ?
    C8' C7' C11' C12' . . . . -2.0(5) ?
    C7 C11 C12 C13 . . . . 1.5(6) ?
    C7' C11' C12' C13' . . . . -0.1(5) ?
    C11 C12 C13 C14 . . . . -1.4(7) ?
    C11 C12 C13 F1 . . . . 179.9(3) ?
    C11' C12' C13' C14' . . . . 1.9(6) ?
    C11' C12' C13' F1' . . . . -178.6(3) ?
    C12 C13 C14 C8 . . . . 1.3(7) ?
    F1 C13 C14 C8 . . . . 180.0(3) ?
    C7 C8 C14 C13 . . . . -1.2(5) ?
    C9 C8 C14 C13 . . . . -178.3(4) ?
    F1' C13' C14' C8' . . . . 178.8(3) ?
    C12' C13' C14' C8' . . . . -1.7(6) ?
    C7' C8' C14' C13' . . . . -0.4(5) ?
    C9' C8' C14' C13' . . . . 179.0(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
    _geom_hbond_publ_flag
    N1 H1 O1W 4_645 0.90 2.12 2.794(3) 131 yes
    N1 H1 O4 1_655 0.90 2.37 3.056(4) 133 yes
    N1 H2 O4' 1_455 0.90 2.19 3.061(4) 162 yes
    O4 H9 Cl1 4_645 0.82 2.67 3.142(2) 118 yes
    O4' H10 O2W 1_655 0.82 2.04 2.701(4) 137 yes
    O1W H1B Cl1 1_555 0.89(4) 2.47(4) 3.242(2) 146(4) yes
    O1W H2B N1 4_655 0.88(3) 2.47(4) 2.794(3) 102(3) yes
    O2W H1A Cl1 1_555 0.89(4) 2.29(4) 3.175(3) 175(3) yes
    O2W H2A Cl1 1_455 0.88(4) 2.37(4) 3.242(3) 171(3) yes
    C2' H4 O6' 1_555 0.97 2.26 2.708(4) 107 yes
    C2 H5 O6 1_555 0.97 2.35 2.738(4) 103 yes
    C2 H6 O6 1_655 0.97 2.49 3.457(4) 172 yes
    C14' H26 F1 1_765 0.93 2.34 3.213(5) 156 yes
data_global
_journal_date_recd_electronic     2007-11-09
_journal_date_accepted     2007-11-21
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      1
_journal_page_first     o54
_journal_page_last     o54
_journal_paper_category     QO
_journal_coeditor_code     HB2656
_publ_contact_author_name     'Franziska Emmerling'
_publ_contact_author_address
;
Bundesanstalt für Materialforschung -und prüfung, Abteilung
Richard-Willstätter-Str.11
D-12489 Berlin-Adlershof
Germany
;
_publ_contact_author_email     franziska.emmerling@bam.de
_publ_contact_author_fax     '00493081041137'
_publ_contact_author_phone     '00493081041133'
_publ_section_title
;
L-Nebiviololinium chloride dihydrate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Gisbert Tuchalski' .
;
Berlin-Chemie AG, Glienicker Weg 125,
D-12489 Berlin,
Germany
;
    'Andre Hänsicke' .
;
Berlin-Chemie AG, Glienicker Weg 125,
D-12489 Berlin,
Germany
;
    'Günther Reck' .
;
Bundesanstalt für Materialforschung und prüfung,
Abteilung Richard-Willstätter-Strasse 11
D-12489 Berlin-Adlershof
Germany
;
    'Franziska Emmerling' .
;
Bundesanstalt für Materialforschung und prüfung,
Abteilung Richard-Willstätter-Strasse 11
D-12489 Berlin-Adlershof
Germany
;
_publ_section_synopsis     .
