##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# 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_I
_audit_creation_method     SHELXL-97
_database_code_depnum_ccdc_archive     'CCDC 967691'
_chemical_name_systematic
;\
({5-[4-({3-Chloro-4-[(3-fluorophenyl)methoxy]phenyl}amino)quinazolin-6-\
yl]furan-2-yl}methyl)[2-(methylsulfonyl)ethyl]azanium 4-methylbenzenesulfonate
;
_chemical_name_common     'Lapatinb monotosylate'
_chemical_formula_moiety     'C29 H27 Cl F N4 O4 S +, C7 H7 O3 S -'
_chemical_formula_sum     'C36 H34 Cl F N4 O7 S2'
_chemical_formula_iupac     'C29 H27 Cl F N4 O4 S +, C7 H7 O3 S -'
_chemical_formula_weight     753.24
_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, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     5.7828(4)
_cell_length_b     20.7395(14)
_cell_length_c     29.4867(19)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     3536.4(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     7472
_cell_measurement_theta_min     2.29
_cell_measurement_theta_max     20.66
_cell_measurement_temperature     294(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.18
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.07
_exptl_crystal_density_diffrn     1.415
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1568
_exptl_absorpt_coefficient_mu     0.287
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SABABS; Bruker, 2001)'
_exptl_absorpt_correction_T_min     0.93
_exptl_absorpt_correction_T_max     0.97
_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     'CCD Area Detector'
_diffrn_measurement_method     'ω scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     34209
_diffrn_reflns_av_R_equivalents     0.0427
_diffrn_reflns_av_sigmaI/netI     0.0318
_diffrn_reflns_theta_min     1.69
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -24
_diffrn_reflns_limit_k_max     24
_diffrn_reflns_limit_l_min     -35
_diffrn_reflns_limit_l_max     35
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     6217
_reflns_number_gt     5614
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0634
_refine_ls_R_factor_gt     0.0568
_refine_ls_wR_factor_gt     0.1332
_refine_ls_wR_factor_ref     0.1373
_refine_ls_goodness_of_fit_ref     1.115
_refine_ls_restrained_S_all     1.115
_refine_ls_number_reflns     6217
_refine_ls_number_parameters     472
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0832P)²+0.1540P] 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     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.393
_refine_diff_density_min     -0.215
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details
                              'Flack & Bernardinelli (2000), 2627 Friedel pairs'
_refine_ls_abs_structure_Flack     -0.04(8)
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'
    'F' 'F' 0.0171 0.0103
                         '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'
    'Cl' 'Cl' 0.1484 0.1585
                         '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, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
   'DIAMOND (Brandenburg & Putz, 2005) and MERCURY (Macrae et al., 2008)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 -1.0966(11) -0.2518(3) 0.90832(19) 0.0939(16) Uani d . 1 1 . .
    C C2 -0.9231(9) -0.2075(3) 0.89817(18) 0.0876(14) Uani d . 1 1 . .
    H H2 -0.8064 -0.1987 0.9190 0.105 Uiso calc R 1 1 . .
    C C3 -0.9284(7) -0.17695(19) 0.85619(14) 0.0598(10) Uani d . 1 1 . .
    C C4 -1.0988(7) -0.1930(2) 0.82603(15) 0.0633(10) Uani d . 1 1 . .
    H H4 -1.1001 -0.1737 0.7975 0.076 Uiso calc R 1 1 . .
    C C5 -1.2687(8) -0.2370(2) 0.83693(18) 0.0808(13) Uani d . 1 1 . .
    H H5 -1.3850 -0.2464 0.8162 0.097 Uiso calc R 1 1 . .
    C C6 -1.2663(10) -0.2671(3) 0.87843(19) 0.0864(15) Uani d . 1 1 . .
    H H6 -1.3788 -0.2973 0.8859 0.104 Uiso calc R 1 1 . .
    C C7 -0.7533(8) -0.1254(2) 0.84659(14) 0.0688(11) Uani d . 1 1 . .
    H H7A -0.8199 -0.0833 0.8525 0.083 Uiso calc R 1 1 . .
    H H7B -0.6202 -0.1309 0.8662 0.083 Uiso calc R 1 1 . .
    C C8 -0.5077(6) -0.08963(17) 0.78753(12) 0.0504(8) Uani d . 1 1 . .
    C C9 -0.4205(7) -0.03953(17) 0.81345(12) 0.0531(9) Uani d . 1 1 . .
    H H9 -0.4882 -0.0298 0.8412 0.064 Uiso calc R 1 1 . .
    C C10 -0.2333(7) -0.00386(17) 0.79834(11) 0.0507(8) Uani d . 1 1 . .
    H H10 -0.1781 0.0297 0.8162 0.061 Uiso calc R 1 1 . .
    C C11 -0.1262(6) -0.01680(16) 0.75751(11) 0.0451(8) Uani d . 1 1 . .
    C C12 -0.2171(7) -0.06552(17) 0.73047(12) 0.0528(9) Uani d . 1 1 . .
    H H12 -0.1505 -0.0750 0.7026 0.063 Uiso calc R 1 1 . .
    C C13 -0.4069(7) -0.09954(17) 0.74545(12) 0.0536(9) Uani d . 1 1 . .
    C C14 0.1867(6) 0.02662(16) 0.70771(12) 0.0474(8) Uani d . 1 1 . .
    C C15 0.3854(6) 0.06920(16) 0.70498(11) 0.0453(8) Uani d . 1 1 . .
    C C16 0.4752(6) 0.10539(15) 0.74121(11) 0.0430(8) Uani d . 1 1 . .
    H H16 0.4025 0.1038 0.7693 0.052 Uiso calc R 1 1 . .
    C C17 0.6687(6) 0.14297(16) 0.73578(11) 0.0455(8) Uani d . 1 1 . .
    C C18 0.7789(7) 0.14502(17) 0.69300(11) 0.0514(8) Uani d . 1 1 . .
    H H18 0.9093 0.1707 0.6891 0.062 Uiso calc R 1 1 . .
    C C19 0.6963(7) 0.10983(19) 0.65744(12) 0.0579(10) Uani d . 1 1 . .
    H H19 0.7726 0.1111 0.6297 0.069 Uiso calc R 1 1 . .
    C C20 0.4972(7) 0.07170(18) 0.66228(11) 0.0525(9) Uani d . 1 1 . .
    C C21 0.2386(9) 0.0027(2) 0.63321(13) 0.0740(13) Uani d . 1 1 . .
    H H21 0.1849 -0.0202 0.6082 0.089 Uiso calc R 1 1 . .
    C C22 0.7739(6) 0.17932(16) 0.77281(10) 0.0436(8) Uani d . 1 1 . .
    C C23 0.9778(6) 0.21085(18) 0.77690(12) 0.0535(9) Uani d . 1 1 . .
    H H25 1.0920 0.2147 0.7549 0.064 Uiso calc R 1 1 . .
    C C24 0.9832(7) 0.23701(19) 0.82147(12) 0.0540(9) Uani d . 1 1 . .
    H H24 1.1022 0.2609 0.8344 0.065 Uiso calc R 1 1 . .
    C C25 0.7839(6) 0.22055(15) 0.84114(11) 0.0435(8) Uani d . 1 1 . .
    C C26 0.6890(6) 0.23139(17) 0.88745(11) 0.0470(8) Uani d . 1 1 . .
    H H26A 0.7457 0.2722 0.8991 0.056 Uiso calc R 1 1 . .
    H H26B 0.5217 0.2337 0.8860 0.056 Uiso calc R 1 1 . .
    C C27 0.6896(6) 0.19041(17) 0.96624(10) 0.0442(8) Uani d . 1 1 . .
    H H27A 0.5223 0.1919 0.9684 0.053 Uiso calc R 1 1 . .
    H H27B 0.7504 0.2317 0.9762 0.053 Uiso calc R 1 1 . .
    C C28 0.7824(7) 0.13714(18) 0.99647(11) 0.0509(8) Uani d . 1 1 . .
    H H28A 0.9493 0.1405 0.9987 0.061 Uiso calc R 1 1 . .
    H H28B 0.7448 0.0954 0.9836 0.061 Uiso calc R 1 1 . .
    C C29 0.8112(10) 0.0891(3) 1.08416(16) 0.0919(16) Uani d . 1 1 . .
    H H29A 0.7593 0.0910 1.1150 0.138 Uiso calc R 1 1 . .
    H H29B 0.9729 0.0994 1.0829 0.138 Uiso calc R 1 1 . .
    H H29C 0.7870 0.0464 1.0725 0.138 Uiso calc R 1 1 . .
    Cl Cl1 -0.5193(3) -0.16048(6) 0.71101(4) 0.0914(4) Uani d . 1 1 . .
    F F1 -1.0903(9) -0.2811(2) 0.94872(14) 0.1661(19) Uani d . 1 1 . .
    N N1 0.0706(5) 0.02027(15) 0.74711(10) 0.0499(7) Uani d D 1 1 . .
    H H1N 0.122(6) 0.0420(13) 0.7699(8) 0.035(8) Uiso d D 1 1 . .
    N N2 0.1165(6) -0.00595(16) 0.67114(10) 0.0620(9) Uani d . 1 1 . .
    N N3 0.4207(7) 0.03795(19) 0.62545(11) 0.0701(10) Uani d . 1 1 . .
    N N4 0.7584(5) 0.17841(14) 0.91859(9) 0.0407(6) Uani d D 1 1 . .
    H H2N 0.906(3) 0.1690(17) 0.9171(12) 0.052(11) Uiso d D 1 1 . .
    H H3N 0.687(5) 0.1424(10) 0.9098(9) 0.027(8) Uiso d D 1 1 . .
    O O1 -0.6837(5) -0.12955(13) 0.80053(9) 0.0622(7) Uani d . 1 1 . .
    O O2 0.6519(4) 0.18415(11) 0.81247(7) 0.0447(5) Uani d . 1 1 . .
    O O3 0.4188(5) 0.12592(16) 1.04900(9) 0.0724(8) Uani d . 1 1 . .
    O O4 0.6994(6) 0.20850(14) 1.06728(9) 0.0729(8) Uani d . 1 1 . .
    S S1 0.65535(16) 0.14452(5) 1.05150(3) 0.0498(2) Uani d . 1 1 . .
    C C30 0.1508(7) 0.01584(18) 0.93247(12) 0.0517(9) Uani d . 1 1 . .
    C C31 0.2522(12) 0.0006(3) 0.97364(16) 0.0996(19) Uani d . 1 1 . .
    H H31 0.3876 0.0212 0.9826 0.120 Uiso calc R 1 1 . .
    C C32 0.1531(13) -0.0448(3) 1.00105(18) 0.113(2) Uani d . 1 1 . .
    H H32 0.2217 -0.0541 1.0288 0.135 Uiso calc R 1 1 . .
    C C33 -0.0432(11) -0.0770(3) 0.98899(16) 0.0861(15) Uani d . 1 1 . .
    C C34 -0.1433(9) -0.0604(2) 0.94913(16) 0.0793(13) Uani d . 1 1 . .
    H H34 -0.2801 -0.0806 0.9406 0.095 Uiso calc R 1 1 . .
    C C35 -0.0499(7) -0.0147(2) 0.92077(14) 0.0622(10) Uani d . 1 1 . .
    H H35 -0.1232 -0.0045 0.8936 0.075 Uiso calc R 1 1 . .
    C C36 -0.1492(17) -0.1276(4) 1.0192(2) 0.144(3) Uani d . 1 1 . .
    H H36A -0.3093 -0.1330 1.0115 0.216 Uiso calc R 1 1 . .
    H H36B -0.1365 -0.1143 1.0503 0.216 Uiso calc R 1 1 . .
    H H36C -0.0692 -0.1677 1.0151 0.216 Uiso calc R 1 1 . .
    O O5 0.1652(5) 0.07126(14) 0.85390(9) 0.0684(8) Uani d . 1 1 . .
    O O6 0.2122(4) 0.13866(12) 0.92030(9) 0.0602(7) Uani d . 1 1 . .
    O O7 0.5173(4) 0.06791(12) 0.89815(9) 0.0594(7) Uani d . 1 1 . .
    S S2 0.26889(15) 0.07797(4) 0.89787(3) 0.0484(2) Uani d . 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 F1 . 1.338(6) ?
    C1 C6 . 1.357(7) ?
    C1 C2 . 1.392(7) ?
    C2 C3 . 1.391(6) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.369(6) ?
    C3 C7 . 1.499(6) ?
    C4 C5 . 1.380(6) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.373(7) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 O1 . 1.419(5) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 O1 . 1.367(4) ?
    C8 C13 . 1.386(5) ?
    C8 C9 . 1.385(5) ?
    C9 C10 . 1.385(5) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.380(5) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.390(5) ?
    C11 N1 . 1.407(4) ?
    C12 C13 . 1.377(5) ?
    C12 H12 . 0.9300 ?
    C13 Cl1 . 1.747(3) ?
    C14 N2 . 1.336(5) ?
    C14 N1 . 1.348(5) ?
    C14 C15 . 1.451(5) ?
    C15 C16 . 1.405(5) ?
    C15 C20 . 1.416(5) ?
    C16 C17 . 1.373(5) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.414(5) ?
    C17 C22 . 1.460(5) ?
    C18 C19 . 1.364(5) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.404(6) ?
    C19 H19 . 0.9300 ?
    C20 N3 . 1.366(5) ?
    C21 N3 . 1.302(6) ?
    C21 N2 . 1.335(5) ?
    C21 H21 . 0.9300 ?
    C22 C23 . 1.354(5) ?
    C22 O2 . 1.369(4) ?
    C23 C24 . 1.422(5) ?
    C23 H25 . 0.9300 ?
    C24 C25 . 1.335(5) ?
    C24 H24 . 0.9300 ?
    C25 O2 . 1.366(4) ?
    C25 C26 . 1.489(5) ?
    C26 N4 . 1.487(4) ?
    C26 H26A . 0.9700 ?
    C26 H26B . 0.9700 ?
    C27 N4 . 1.481(4) ?
    C27 C28 . 1.518(5) ?
    C27 H27A . 0.9700 ?
    C27 H27B . 0.9700 ?
    C28 S1 . 1.788(3) ?
    C28 H28A . 0.9700 ?
    C28 H28B . 0.9700 ?
    C29 S1 . 1.750(5) ?
    C29 H29A . 0.9600 ?
    C29 H29B . 0.9600 ?
    C29 H29C . 0.9600 ?
    N1 H1N . 0.862(18) ?
    N4 H2N . 0.878(19) ?
    N4 H3N . 0.892(17) ?
    O3 S1 . 1.423(3) ?
    O4 S1 . 1.429(3) ?
    C30 C35 . 1.366(5) ?
    C30 C31 . 1.385(6) ?
    C30 S2 . 1.780(4) ?
    C31 C32 . 1.367(8) ?
    C31 H31 . 0.9300 ?
    C32 C33 . 1.364(8) ?
    C32 H32 . 0.9300 ?
    C33 C34 . 1.355(7) ?
    C33 C36 . 1.507(7) ?
    C34 C35 . 1.374(6) ?
    C34 H34 . 0.9300 ?
    C35 H35 . 0.9300 ?
    C36 H36A . 0.9600 ?
    C36 H36B . 0.9600 ?
    C36 H36C . 0.9600 ?
    O5 S2 . 1.435(3) ?
    O6 S2 . 1.459(3) ?
    O7 S2 . 1.452(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
    F1 C1 C6 . . 119.5(5) ?
    F1 C1 C2 . . 118.1(6) ?
    C6 C1 C2 . . 122.4(5) ?
    C3 C2 C1 . . 118.4(5) ?
    C3 C2 H2 . . 120.8 ?
    C1 C2 H2 . . 120.8 ?
    C4 C3 C2 . . 118.9(4) ?
    C4 C3 C7 . . 122.5(4) ?
    C2 C3 C7 . . 118.6(4) ?
    C3 C4 C5 . . 121.5(4) ?
    C3 C4 H4 . . 119.3 ?
    C5 C4 H4 . . 119.3 ?
    C6 C5 C4 . . 120.1(5) ?
    C6 C5 H5 . . 120.0 ?
    C4 C5 H5 . . 120.0 ?
    C1 C6 C5 . . 118.7(5) ?
    C1 C6 H6 . . 120.6 ?
    C5 C6 H6 . . 120.6 ?
    O1 C7 C3 . . 109.2(3) ?
    O1 C7 H7A . . 109.8 ?
    C3 C7 H7A . . 109.8 ?
    O1 C7 H7B . . 109.8 ?
    C3 C7 H7B . . 109.8 ?
    H7A C7 H7B . . 108.3 ?
    O1 C8 C13 . . 118.3(3) ?
    O1 C8 C9 . . 124.8(3) ?
    C13 C8 C9 . . 116.9(4) ?
    C10 C9 C8 . . 120.5(3) ?
    C10 C9 H9 . . 119.7 ?
    C8 C9 H9 . . 119.7 ?
    C11 C10 C9 . . 121.8(3) ?
    C11 C10 H10 . . 119.1 ?
    C9 C10 H10 . . 119.1 ?
    C10 C11 C12 . . 118.1(3) ?
    C10 C11 N1 . . 116.5(3) ?
    C12 C11 N1 . . 125.3(3) ?
    C13 C12 C11 . . 119.3(3) ?
    C13 C12 H12 . . 120.3 ?
    C11 C12 H12 . . 120.3 ?
    C12 C13 C8 . . 123.1(3) ?
    C12 C13 Cl1 . . 118.7(3) ?
    C8 C13 Cl1 . . 118.1(3) ?
    N2 C14 N1 . . 119.7(3) ?
    N2 C14 C15 . . 120.2(3) ?
    N1 C14 C15 . . 120.1(3) ?
    C16 C15 C20 . . 119.2(3) ?
    C16 C15 C14 . . 125.1(3) ?
    C20 C15 C14 . . 115.7(3) ?
    C17 C16 C15 . . 121.1(3) ?
    C17 C16 H16 . . 119.5 ?
    C15 C16 H16 . . 119.5 ?
    C16 C17 C18 . . 119.2(3) ?
    C16 C17 C22 . . 123.1(3) ?
    C18 C17 C22 . . 117.6(3) ?
    C19 C18 C17 . . 120.8(3) ?
    C19 C18 H18 . . 119.6 ?
    C17 C18 H18 . . 119.6 ?
    C18 C19 C20 . . 120.7(3) ?
    C18 C19 H19 . . 119.7 ?
    C20 C19 H19 . . 119.7 ?
    N3 C20 C19 . . 118.3(3) ?
    N3 C20 C15 . . 122.7(4) ?
    C19 C20 C15 . . 119.1(3) ?
    N3 C21 N2 . . 130.6(4) ?
    N3 C21 H21 . . 114.7 ?
    N2 C21 H21 . . 114.7 ?
    C23 C22 O2 . . 109.7(3) ?
    C23 C22 C17 . . 132.8(3) ?
    O2 C22 C17 . . 117.5(3) ?
    C22 C23 C24 . . 106.6(3) ?
    C22 C23 H25 . . 126.7 ?
    C24 C23 H25 . . 126.7 ?
    C25 C24 C23 . . 106.6(3) ?
    C25 C24 H24 . . 126.7 ?
    C23 C24 H24 . . 126.7 ?
    C24 C25 O2 . . 110.8(3) ?
    C24 C25 C26 . . 132.7(3) ?
    O2 C25 C26 . . 116.5(3) ?
    N4 C26 C25 . . 110.8(3) ?
    N4 C26 H26A . . 109.5 ?
    C25 C26 H26A . . 109.5 ?
    N4 C26 H26B . . 109.5 ?
    C25 C26 H26B . . 109.5 ?
    H26A C26 H26B . . 108.1 ?
    N4 C27 C28 . . 109.9(3) ?
    N4 C27 H27A . . 109.7 ?
    C28 C27 H27A . . 109.7 ?
    N4 C27 H27B . . 109.7 ?
    C28 C27 H27B . . 109.7 ?
    H27A C27 H27B . . 108.2 ?
    C27 C28 S1 . . 109.0(2) ?
    C27 C28 H28A . . 109.9 ?
    S1 C28 H28A . . 109.9 ?
    C27 C28 H28B . . 109.9 ?
    S1 C28 H28B . . 109.9 ?
    H28A C28 H28B . . 108.3 ?
    S1 C29 H29A . . 109.5 ?
    S1 C29 H29B . . 109.5 ?
    H29A C29 H29B . . 109.5 ?
    S1 C29 H29C . . 109.5 ?
    H29A C29 H29C . . 109.5 ?
    H29B C29 H29C . . 109.5 ?
    C14 N1 C11 . . 130.1(3) ?
    C14 N1 H1N . . 117(2) ?
    C11 N1 H1N . . 113(2) ?
    C14 N2 C21 . . 116.6(4) ?
    C21 N3 C20 . . 114.2(3) ?
    C27 N4 C26 . . 112.9(3) ?
    C27 N4 H2N . . 110(2) ?
    C26 N4 H2N . . 113(2) ?
    C27 N4 H3N . . 107.0(19) ?
    C26 N4 H3N . . 108.4(19) ?
    H2N N4 H3N . . 104(3) ?
    C8 O1 C7 . . 116.3(3) ?
    C25 O2 C22 . . 106.3(3) ?
    O3 S1 O4 . . 116.1(2) ?
    O3 S1 C29 . . 110.2(2) ?
    O4 S1 C29 . . 109.8(2) ?
    O3 S1 C28 . . 108.96(18) ?
    O4 S1 C28 . . 107.56(18) ?
    C29 S1 C28 . . 103.4(2) ?
    C35 C30 C31 . . 118.4(4) ?
    C35 C30 S2 . . 121.1(3) ?
    C31 C30 S2 . . 120.4(3) ?
    C32 C31 C30 . . 119.9(5) ?
    C32 C31 H31 . . 120.1 ?
    C30 C31 H31 . . 120.1 ?
    C33 C32 C31 . . 122.1(5) ?
    C33 C32 H32 . . 118.9 ?
    C31 C32 H32 . . 118.9 ?
    C34 C33 C32 . . 117.2(5) ?
    C34 C33 C36 . . 121.1(6) ?
    C32 C33 C36 . . 121.6(5) ?
    C33 C34 C35 . . 122.4(5) ?
    C33 C34 H34 . . 118.8 ?
    C35 C34 H34 . . 118.8 ?
    C30 C35 C34 . . 120.0(4) ?
    C30 C35 H35 . . 120.0 ?
    C34 C35 H35 . . 120.0 ?
    C33 C36 H36A . . 109.5 ?
    C33 C36 H36B . . 109.5 ?
    H36A C36 H36B . . 109.5 ?
    C33 C36 H36C . . 109.5 ?
    H36A C36 H36C . . 109.5 ?
    H36B C36 H36C . . 109.5 ?
    O5 S2 O7 . . 113.86(17) ?
    O5 S2 O6 . . 113.54(17) ?
    O7 S2 O6 . . 110.10(15) ?
    O5 S2 C30 . . 106.70(17) ?
    O7 S2 C30 . . 105.82(18) ?
    O6 S2 C30 . . 106.17(17) ?
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
    F1 C1 C2 C3 . . . . 179.9(5) ?
    C6 C1 C2 C3 . . . . 1.6(8) ?
    C1 C2 C3 C4 . . . . -2.1(7) ?
    C1 C2 C3 C7 . . . . 175.1(4) ?
    C2 C3 C4 C5 . . . . 2.1(6) ?
    C7 C3 C4 C5 . . . . -175.0(4) ?
    C3 C4 C5 C6 . . . . -1.5(7) ?
    F1 C1 C6 C5 . . . . -179.3(5) ?
    C2 C1 C6 C5 . . . . -1.0(8) ?
    C4 C5 C6 C1 . . . . 1.0(7) ?
    C4 C3 C7 O1 . . . . -40.2(5) ?
    C2 C3 C7 O1 . . . . 142.8(4) ?
    O1 C8 C9 C10 . . . . 176.5(4) ?
    C13 C8 C9 C10 . . . . -3.3(5) ?
    C8 C9 C10 C11 . . . . -0.4(6) ?
    C9 C10 C11 C12 . . . . 2.6(5) ?
    C9 C10 C11 N1 . . . . -176.4(3) ?
    C10 C11 C12 C13 . . . . -1.0(5) ?
    N1 C11 C12 C13 . . . . 177.9(3) ?
    C11 C12 C13 C8 . . . . -2.9(6) ?
    C11 C12 C13 Cl1 . . . . 179.9(3) ?
    O1 C8 C13 C12 . . . . -174.8(3) ?
    C9 C8 C13 C12 . . . . 5.0(6) ?
    O1 C8 C13 Cl1 . . . . 2.4(5) ?
    C9 C8 C13 Cl1 . . . . -177.8(3) ?
    N2 C14 C15 C16 . . . . -179.6(3) ?
    N1 C14 C15 C16 . . . . 1.1(5) ?
    N2 C14 C15 C20 . . . . -1.6(5) ?
    N1 C14 C15 C20 . . . . 179.1(3) ?
    C20 C15 C16 C17 . . . . 0.1(5) ?
    C14 C15 C16 C17 . . . . 178.0(3) ?
    C15 C16 C17 C18 . . . . -0.1(5) ?
    C15 C16 C17 C22 . . . . -177.4(3) ?
    C16 C17 C18 C19 . . . . -0.5(5) ?
    C22 C17 C18 C19 . . . . 176.9(3) ?
    C17 C18 C19 C20 . . . . 1.2(6) ?
    C18 C19 C20 N3 . . . . 179.3(4) ?
    C18 C19 C20 C15 . . . . -1.3(6) ?
    C16 C15 C20 N3 . . . . 180.0(3) ?
    C14 C15 C20 N3 . . . . 1.9(5) ?
    C16 C15 C20 C19 . . . . 0.6(5) ?
    C14 C15 C20 C19 . . . . -177.5(3) ?
    C16 C17 C22 C23 . . . . 168.7(4) ?
    C18 C17 C22 C23 . . . . -8.7(6) ?
    C16 C17 C22 O2 . . . . -10.9(5) ?
    C18 C17 C22 O2 . . . . 171.8(3) ?
    O2 C22 C23 C24 . . . . -0.2(4) ?
    C17 C22 C23 C24 . . . . -179.8(4) ?
    C22 C23 C24 C25 . . . . -0.7(4) ?
    C23 C24 C25 O2 . . . . 1.3(4) ?
    C23 C24 C25 C26 . . . . 177.8(4) ?
    C24 C25 C26 N4 . . . . -88.6(5) ?
    O2 C25 C26 N4 . . . . 87.7(3) ?
    N4 C27 C28 S1 . . . . -169.7(2) ?
    N2 C14 N1 C11 . . . . -0.4(6) ?
    C15 C14 N1 C11 . . . . 178.9(3) ?
    C10 C11 N1 C14 . . . . -167.5(4) ?
    C12 C11 N1 C14 . . . . 13.6(6) ?
    N1 C14 N2 C21 . . . . 179.8(4) ?
    C15 C14 N2 C21 . . . . 0.5(5) ?
    N3 C21 N2 C14 . . . . 0.6(8) ?
    N2 C21 N3 C20 . . . . -0.4(8) ?
    C19 C20 N3 C21 . . . . 178.4(4) ?
    C15 C20 N3 C21 . . . . -1.0(6) ?
    C28 C27 N4 C26 . . . . -175.5(3) ?
    C25 C26 N4 C27 . . . . 173.8(3) ?
    C13 C8 O1 C7 . . . . 169.0(4) ?
    C9 C8 O1 C7 . . . . -10.8(5) ?
    C3 C7 O1 C8 . . . . -173.9(3) ?
    C24 C25 O2 C22 . . . . -1.5(4) ?
    C26 C25 O2 C22 . . . . -178.6(3) ?
    C23 C22 O2 C25 . . . . 1.0(4) ?
    C17 C22 O2 C25 . . . . -179.3(3) ?
    C27 C28 S1 O3 . . . . 71.8(3) ?
    C27 C28 S1 O4 . . . . -54.8(3) ?
    C27 C28 S1 C29 . . . . -170.9(3) ?
    C35 C30 C31 C32 . . . . 1.0(8) ?
    S2 C30 C31 C32 . . . . 176.5(5) ?
    C30 C31 C32 C33 . . . . 1.0(11) ?
    C31 C32 C33 C34 . . . . -2.6(10) ?
    C31 C32 C33 C36 . . . . 179.2(7) ?
    C32 C33 C34 C35 . . . . 2.1(8) ?
    C36 C33 C34 C35 . . . . -179.6(5) ?
    C31 C30 C35 C34 . . . . -1.5(6) ?
    S2 C30 C35 C34 . . . . -176.9(3) ?
    C33 C34 C35 C30 . . . . -0.1(8) ?
    C35 C30 S2 O5 . . . . -18.8(4) ?
    C31 C30 S2 O5 . . . . 165.8(4) ?
    C35 C30 S2 O7 . . . . -140.4(3) ?
    C31 C30 S2 O7 . . . . 44.2(4) ?
    C35 C30 S2 O6 . . . . 102.6(3) ?
    C31 C30 S2 O6 . . . . -72.8(4) ?
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 O5 . 0.862(18) 2.56(2) 3.367(4) 156(3)
    N4 H3N O7 . 0.892(17) 1.862(18) 2.749(4) 173(3)
    N4 H2N O6 1_655 0.878(19) 1.88(2) 2.751(4) 171(4)
    C10 H10 O5 . 0.93 2.43 3.228(5) 144
    C12 H12 N2 . 0.93 2.30 2.883(5) 120
    C26 H26B O4 4_457 0.97 2.61 3.369(5) 135
    C27 H27A O6 . 0.97 2.54 3.257(4) 131
data_II
_audit_creation_method     SHELXL-97
_database_code_depnum_ccdc_archive     'CCDC 967692'
_chemical_name_systematic
;\
4-({3-Chloro-4-[(3-fluorophenyl)methoxy]phenyl}amino)-6-]5-({[2-\
(methylsulfonyl)ethyl]azaniumyl}methyl)furan-2-yl[quinazolin-1-ium
bis(4-methylbenzenesulfonate)
;
_chemical_name_common     'Lapatinib ditosylate'
_chemical_formula_moiety     'C29 H28 Cl F N4 O4 S 2+, 2(C7 H7 O3 S -)'
_chemical_formula_sum     'C43 H42 Cl F N4 O10 S3'
_chemical_formula_iupac     'C29 H28 Cl F N4 O4 S 2+, 2C7 H7 O3 S -'
_chemical_formula_weight     925.44
_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     9.2122(6)
_cell_length_b     13.2387(9)
_cell_length_c     18.3758(12)
_cell_angle_alpha     95.3870(10)
_cell_angle_beta     92.4630(10)
_cell_angle_gamma     100.3590(10)
_cell_volume     2190.7(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     5462
_cell_measurement_theta_min     2.26
_cell_measurement_theta_max     24.04
_cell_measurement_temperature     294(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.15
_exptl_crystal_size_mid     0.07
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.403
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     964
_exptl_absorpt_coefficient_mu     0.297
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SABABS; Bruker, 2001)'
_exptl_absorpt_correction_T_min     0.95
_exptl_absorpt_correction_T_max     0.99
_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     'CCD Area Detector'
_diffrn_measurement_method     'ω scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     21274
_diffrn_reflns_av_R_equivalents     0.0284
_diffrn_reflns_av_sigmaI/netI     0.0363
_diffrn_reflns_theta_min     1.57
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     7684
_reflns_number_gt     5892
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0802
_refine_ls_R_factor_gt     0.0622
_refine_ls_wR_factor_gt     0.1599
_refine_ls_wR_factor_ref     0.1735
_refine_ls_goodness_of_fit_ref     1.028
_refine_ls_restrained_S_all     1.036
_refine_ls_number_reflns     7684
_refine_ls_number_parameters     633
_refine_ls_number_restraints     244
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0898P)²+1.6704P] 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     0.606
_refine_diff_density_min     -0.576
_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'
    'F' 'F' 0.0171 0.0103
                         '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'
    'Cl' 'Cl' 0.1484 0.1585
                         '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, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
   'DIAMOND (Brandenburg & Putz, 2005) and Mercury (Macrae et al., 2008)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C3 1.4382(5) 0.1251(4) 0.5449(3) 0.0932(11) Uani d DU 1 1 . .
    C C1 1.6136(10) 0.1935(8) 0.6432(4) 0.0994(11) Uani d PDU 0.579(10) 1 A 1
    C C2 1.5598(9) 0.1953(7) 0.5730(4) 0.0973(11) Uani d PDU 0.579(10) 1 A 1
    H H2 1.6059 0.2444 0.5443 0.117 Uiso calc PR 0.579(10) 1 A 1
    C C4 1.3848(10) 0.0436(7) 0.5847(4) 0.0954(12) Uani d PDU 0.579(10) 1 A 1
    H H4 1.3079 -0.0082 0.5647 0.115 Uiso calc PR 0.579(10) 1 A 1
    C C5 1.4465(11) 0.0397(7) 0.6547(4) 0.0966(12) Uani d PDU 0.579(10) 1 A 1
    H H5 1.4121 -0.0156 0.6810 0.116 Uiso calc PR 0.579(10) 1 A 1
    C C6 1.5587(13) 0.1177(10) 0.6850(5) 0.0977(11) Uani d PDU 0.579(10) 1 A 1
    H H6 1.5959 0.1185 0.7329 0.117 Uiso calc PR 0.579(10) 1 A 1
    F F1 1.7237(8) 0.2691(6) 0.6723(3) 0.1044(12) Uani d PDU 0.579(10) 1 A 1
    C C1' 1.6268(11) 0.1817(13) 0.6397(5) 0.0993(11) Uani d PDU 0.421(10) 1 A 2
    C C2' 1.5748(11) 0.1804(12) 0.5687(5) 0.0973(12) Uani d PDU 0.421(10) 1 A 2
    H H2' 1.6327 0.2173 0.5364 0.117 Uiso calc PR 0.421(10) 1 A 2
    C C4' 1.3526(10) 0.0722(11) 0.5949(5) 0.0956(12) Uani d PDU 0.421(10) 1 A 2
    H H4' 1.2594 0.0343 0.5799 0.115 Uiso calc PR 0.421(10) 1 A 2
    C C5' 1.4063(11) 0.0760(12) 0.6672(5) 0.0968(12) Uani d PDU 0.421(10) 1 A 2
    H H5' 1.3473 0.0429 0.7010 0.116 Uiso calc PR 0.421(10) 1 A 2
    C C6' 1.5468(14) 0.1286(16) 0.6890(6) 0.0979(12) Uani d PDU 0.421(10) 1 A 2
    H H6' 1.5861 0.1277 0.7363 0.117 Uiso calc PR 0.421(10) 1 A 2
    F F1' 1.7688(8) 0.2235(9) 0.6585(5) 0.1031(12) Uani d PDU 0.421(10) 1 A 2
    C C7 1.3831(6) 0.1320(5) 0.4684(3) 0.0974(17) Uani d . 1 1 A .
    H H7A 1.3524 0.1978 0.4650 0.117 Uiso calc R 1 1 . .
    H H7B 1.4615 0.1272 0.4354 0.117 Uiso calc R 1 1 . .
    C C8 1.1938(5) 0.0461(3) 0.3811(2) 0.0641(10) Uani d . 1 1 A .
    C C9 1.2369(5) 0.1107(4) 0.3282(2) 0.0742(12) Uani d . 1 1 . .
    H H9 1.3193 0.1631 0.3377 0.089 Uiso calc R 1 1 . .
    C C10 1.1584(5) 0.0981(3) 0.2613(2) 0.0690(11) Uani d . 1 1 . .
    H H10 1.1885 0.1419 0.2260 0.083 Uiso calc R 1 1 . .
    C C11 1.0371(4) 0.0219(3) 0.24671(18) 0.0519(9) Uani d . 1 1 . .
    C C12 0.9934(5) -0.0435(3) 0.2986(2) 0.0622(10) Uani d . 1 1 . .
    H H12 0.9112 -0.0961 0.2887 0.075 Uiso calc R 1 1 . .
    C C13 1.0712(5) -0.0313(3) 0.3650(2) 0.0656(11) Uani d . 1 1 . .
    C C14 0.9585(3) -0.0609(2) 0.12440(16) 0.0383(7) Uani d . 1 1 . .
    C C15 0.8712(3) -0.0654(2) 0.05690(16) 0.0347(6) Uani d . 1 1 . .
    C C16 0.7902(3) 0.0095(2) 0.03956(16) 0.0360(7) Uani d . 1 1 . .
    H H16 0.7911 0.0671 0.0728 0.043 Uiso calc R 1 1 . .
    C C17 0.7090(3) -0.0009(2) -0.02607(16) 0.0356(7) Uani d . 1 1 . .
    C C18 0.7050(3) -0.0896(2) -0.07516(17) 0.0425(7) Uani d . 1 1 . .
    H H18 0.6466 -0.0987 -0.1187 0.051 Uiso calc R 1 1 . .
    C C19 0.7859(4) -0.1627(2) -0.05968(18) 0.0444(8) Uani d . 1 1 . .
    H H19 0.7839 -0.2206 -0.0929 0.053 Uiso calc R 1 1 . .
    C C20 0.8710(3) -0.1504(2) 0.00575(16) 0.0372(7) Uani d . 1 1 . .
    C C21 1.0440(4) -0.2043(2) 0.08338(19) 0.0460(8) Uani d . 1 1 . .
    H H21 1.1052 -0.2516 0.0907 0.055 Uiso calc R 1 1 . .
    C C22 0.6292(3) 0.0791(2) -0.04530(16) 0.0366(7) Uani d . 1 1 . .
    C C23 0.5463(4) 0.0934(3) -0.10440(17) 0.0455(8) Uani d . 1 1 . .
    H H23 0.5205 0.0477 -0.1464 0.055 Uiso calc R 1 1 . .
    C C24 0.5061(4) 0.1910(3) -0.09031(19) 0.0488(8) Uani d . 1 1 . .
    H H24 0.4496 0.2221 -0.1215 0.059 Uiso calc R 1 1 . .
    C C25 0.5647(3) 0.2304(2) -0.02366(18) 0.0426(7) Uani d . 1 1 . .
    C C26 0.5518(4) 0.3228(3) 0.0249(2) 0.0499(8) Uani d . 1 1 . .
    H H26A 0.4847 0.3027 0.0625 0.060 Uiso calc R 1 1 . .
    H H26B 0.5092 0.3698 -0.0033 0.060 Uiso calc R 1 1 . .
    C C27 0.6770(4) 0.4676(3) 0.1117(2) 0.0506(8) Uani d . 1 1 . .
    H H27A 0.6082 0.4448 0.1479 0.061 Uiso calc R 1 1 . .
    H H27B 0.6366 0.5169 0.0848 0.061 Uiso calc R 1 1 . .
    C C28 0.8237(4) 0.5180(3) 0.1492(2) 0.0553(9) Uani d . 1 1 . .
    H H28A 0.8904 0.5436 0.1128 0.066 Uiso calc R 1 1 . .
    H H28B 0.8662 0.4672 0.1734 0.066 Uiso calc R 1 1 . .
    C C29 0.9865(5) 0.6616(3) 0.2530(3) 0.0745(12) Uani d . 1 1 . .
    H H29A 1.0187 0.6051 0.2741 0.112 Uiso calc R 1 1 . .
    H H29B 0.9890 0.7177 0.2905 0.112 Uiso calc R 1 1 . .
    H H29C 1.0510 0.6840 0.2157 0.112 Uiso calc R 1 1 . .
    Cl Cl1 1.0162(2) -0.11460(11) 0.42947(7) 0.1196(6) Uani d . 1 1 . .
    N N1 0.9534(4) 0.0115(2) 0.17828(16) 0.0534(8) Uani d . 1 1 . .
    H H1N 0.883(5) 0.039(3) 0.179(2) 0.065(13) Uiso d . 1 1 . .
    N N2 1.0496(3) -0.1280(2) 0.13479(15) 0.0449(6) Uani d . 1 1 . .
    N N3 0.9598(3) -0.2201(2) 0.02225(17) 0.0450(7) Uani d . 1 1 . .
    H H3N 0.960(4) -0.269(3) -0.0050(19) 0.042(10) Uiso d . 1 1 . .
    N N4 0.6962(3) 0.3779(2) 0.06073(18) 0.0423(6) Uani d . 1 1 . .
    H H4N 0.740(4) 0.342(3) 0.084(2) 0.053(11) Uiso d . 1 1 . .
    H H5N 0.751(4) 0.393(3) 0.025(2) 0.045(10) Uiso d . 1 1 . .
    O O1 1.2627(4) 0.0509(2) 0.44838(15) 0.0827(9) Uani d . 1 1 . .
    O O2 0.6410(2) 0.16301(16) 0.00589(11) 0.0400(5) Uani d . 1 1 . .
    O O3 0.7153(4) 0.5828(3) 0.26913(19) 0.0945(11) Uani d . 1 1 . .
    O O4 0.7649(4) 0.7023(2) 0.1764(2) 0.0884(10) Uani d . 1 1 . .
    S S1 0.80573(10) 0.62160(7) 0.21453(6) 0.0576(3) Uani d . 1 1 . .
    C C30 0.7483(4) 0.2540(3) 0.30262(18) 0.0486(8) Uani d . 1 1 . .
    C C31 0.7192(6) 0.3459(3) 0.3335(2) 0.0774(13) Uani d . 1 1 . .
    H H31 0.6628 0.3833 0.3073 0.093 Uiso calc R 1 1 . .
    C C32 0.7749(6) 0.3825(4) 0.4043(3) 0.0902(16) Uani d . 1 1 . .
    H H32 0.7556 0.4455 0.4246 0.108 Uiso calc R 1 1 . .
    C C33 0.8564(5) 0.3302(3) 0.4452(2) 0.0688(11) Uani d . 1 1 . .
    C C34 0.8843(6) 0.2390(4) 0.4134(2) 0.0795(13) Uani d . 1 1 . .
    H H34 0.9409 0.2017 0.4397 0.095 Uiso calc R 1 1 . .
    C C35 0.8307(5) 0.2009(3) 0.3433(2) 0.0714(12) Uani d . 1 1 . .
    H H35 0.8508 0.1381 0.3232 0.086 Uiso calc R 1 1 . .
    C C36 0.9165(7) 0.3705(4) 0.5223(2) 0.1003(18) Uani d . 1 1 . .
    H H36A 1.0221 0.3772 0.5251 0.151 Uiso calc R 1 1 . .
    H H36B 0.8750 0.3232 0.5557 0.151 Uiso calc R 1 1 . .
    H H36C 0.8906 0.4367 0.5350 0.151 Uiso calc R 1 1 . .
    O O5 0.6890(4) 0.0996(2) 0.20398(15) 0.0761(8) Uani d . 1 1 . .
    O O6 0.5451(4) 0.2338(3) 0.19762(18) 0.0947(11) Uani d . 1 1 . .
    O O7 0.7944(3) 0.2610(2) 0.16591(15) 0.0820(9) Uani d . 1 1 . .
    S S2 0.68687(10) 0.20802(6) 0.21086(5) 0.0480(2) Uani d . 1 1 . .
    C C37 0.7794(4) 0.5348(3) -0.1792(2) 0.0502(8) Uani d . 1 1 . .
    C C38 0.8595(5) 0.6084(3) -0.2176(2) 0.0654(10) Uani d . 1 1 . .
    H H38 0.9395 0.6550 -0.1945 0.078 Uiso calc R 1 1 . .
    C C39 0.8207(6) 0.6125(4) -0.2899(3) 0.0898(15) Uani d . 1 1 . .
    H H39 0.8778 0.6608 -0.3155 0.108 Uiso calc R 1 1 . .
    C C40 0.7027(6) 0.5492(6) -0.3254(3) 0.0962(17) Uani d . 1 1 . .
    C C41 0.6245(5) 0.4751(5) -0.2878(3) 0.1011(19) Uani d . 1 1 . .
    H H41 0.5450 0.4289 -0.3118 0.121 Uiso calc R 1 1 . .
    C C42 0.6612(4) 0.4673(4) -0.2143(2) 0.0773(13) Uani d . 1 1 . .
    H H42 0.6062 0.4169 -0.1895 0.093 Uiso calc R 1 1 . .
    C C43 0.6548(8) 0.5570(7) -0.4050(3) 0.153(3) Uani d . 1 1 . .
    H H43A 0.5880 0.6048 -0.4065 0.229 Uiso calc R 1 1 . .
    H H43B 0.6061 0.4903 -0.4272 0.229 Uiso calc R 1 1 . .
    H H43C 0.7401 0.5808 -0.4312 0.229 Uiso calc R 1 1 . .
    O O8 0.7021(3) 0.5569(2) -0.04567(15) 0.0664(7) Uani d . 1 1 . .
    O O9 0.9604(3) 0.60424(17) -0.06784(13) 0.0503(6) Uani d . 1 1 . .
    O O10 0.8426(3) 0.42505(17) -0.07730(14) 0.0563(6) Uani d . 1 1 . .
    S S3 0.82358(9) 0.52955(6) -0.08538(5) 0.0431(2) Uani d . 1 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
    C3 C2 . 1.368(6) ?
    C3 C2' . 1.368(7) ?
    C3 C4 . 1.389(7) ?
    C3 C4' . 1.393(8) ?
    C3 C7 . 1.491(6) ?
    C1 F1 . 1.343(5) ?
    C1 C6 . 1.359(6) ?
    C1 C2 . 1.366(5) ?
    C2 H2 . 0.9300 ?
    C4 C5 . 1.392(5) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.380(6) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C1' F1' . 1.342(5) ?
    C1' C6' . 1.360(6) ?
    C1' C2' . 1.367(5) ?
    C2' H2' . 0.9300 ?
    C4' C5' . 1.391(6) ?
    C4' H4' . 0.9300 ?
    C5' C6' . 1.378(6) ?
    C5' H5' . 0.9300 ?
    C6' H6' . 0.9300 ?
    C7 O1 . 1.407(6) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 O1 . 1.356(4) ?
    C8 C9 . 1.379(6) ?
    C8 C13 . 1.382(6) ?
    C9 C10 . 1.379(5) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.362(6) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.373(5) ?
    C11 N1 . 1.428(4) ?
    C12 C13 . 1.369(5) ?
    C12 H12 . 0.9300 ?
    C13 Cl1 . 1.725(4) ?
    C14 N1 . 1.320(4) ?
    C14 N2 . 1.347(4) ?
    C14 C15 . 1.440(4) ?
    C15 C16 . 1.396(4) ?
    C15 C20 . 1.396(4) ?
    C16 C17 . 1.374(4) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.407(4) ?
    C17 C22 . 1.454(4) ?
    C18 C19 . 1.366(4) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.387(4) ?
    C19 H19 . 0.9300 ?
    C20 N3 . 1.384(4) ?
    C21 N2 . 1.309(4) ?
    C21 N3 . 1.315(4) ?
    C21 H21 . 0.9300 ?
    C22 C23 . 1.349(4) ?
    C22 O2 . 1.372(3) ?
    C23 C24 . 1.411(5) ?
    C23 H23 . 0.9300 ?
    C24 C25 . 1.336(5) ?
    C24 H24 . 0.9300 ?
    C25 O2 . 1.366(4) ?
    C25 C26 . 1.472(5) ?
    C26 N4 . 1.490(4) ?
    C26 H26A . 0.9700 ?
    C26 H26B . 0.9700 ?
    C27 N4 . 1.484(4) ?
    C27 C28 . 1.502(5) ?
    C27 H27A . 0.9700 ?
    C27 H27B . 0.9700 ?
    C28 S1 . 1.772(4) ?
    C28 H28A . 0.9700 ?
    C28 H28B . 0.9700 ?
    C29 S1 . 1.751(4) ?
    C29 H29A . 0.9600 ?
    C29 H29B . 0.9600 ?
    C29 H29C . 0.9600 ?
    N1 H1N . 0.79(4) ?
    N3 H3N . 0.78(3) ?
    N4 H4N . 0.82(4) ?
    N4 H5N . 0.86(4) ?
    O3 S1 . 1.407(3) ?
    O4 S1 . 1.427(3) ?
    C30 C35 . 1.368(5) ?
    C30 C31 . 1.368(5) ?
    C30 S2 . 1.771(3) ?
    C31 C32 . 1.388(6) ?
    C31 H31 . 0.9300 ?
    C32 C33 . 1.359(6) ?
    C32 H32 . 0.9300 ?
    C33 C34 . 1.362(6) ?
    C33 C36 . 1.510(6) ?
    C34 C35 . 1.376(6) ?
    C34 H34 . 0.9300 ?
    C35 H35 . 0.9300 ?
    C36 H36A . 0.9600 ?
    C36 H36B . 0.9600 ?
    C36 H36C . 0.9600 ?
    O5 S2 . 1.432(3) ?
    O6 S2 . 1.425(3) ?
    O7 S2 . 1.444(3) ?
    C37 C42 . 1.372(5) ?
    C37 C38 . 1.381(5) ?
    C37 S3 . 1.765(4) ?
    C38 C39 . 1.369(6) ?
    C38 H38 . 0.9300 ?
    C39 C40 . 1.348(7) ?
    C39 H39 . 0.9300 ?
    C40 C41 . 1.369(8) ?
    C40 C43 . 1.527(7) ?
    C41 C42 . 1.396(7) ?
    C41 H41 . 0.9300 ?
    C42 H42 . 0.9300 ?
    C43 H43A . 0.9600 ?
    C43 H43B . 0.9600 ?
    C43 H43C . 0.9600 ?
    O8 S3 . 1.443(2) ?
    O9 S3 . 1.458(2) ?
    O10 S3 . 1.446(2) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 C3 C4 . . 118.7(5) ?
    C2' C3 C4 . . 115.4(6) ?
    C2 C3 C4' . . 116.9(6) ?
    C2' C3 C4' . . 118.5(6) ?
    C2 C3 C7 . . 117.6(5) ?
    C2' C3 C7 . . 118.1(5) ?
    C4 C3 C7 . . 123.1(5) ?
    C4' C3 C7 . . 123.2(5) ?
    F1 C1 C6 . . 118.7(5) ?
    F1 C1 C2 . . 119.2(5) ?
    C6 C1 C2 . . 122.1(5) ?
    C1 C2 C3 . . 120.0(5) ?
    C1 C2 H2 . . 120.0 ?
    C3 C2 H2 . . 120.0 ?
    C3 C4 C5 . . 120.0(5) ?
    C3 C4 H4 . . 120.0 ?
    C5 C4 H4 . . 120.0 ?
    C6 C5 C4 . . 120.0(6) ?
    C6 C5 H5 . . 120.0 ?
    C4 C5 H5 . . 120.0 ?
    C1 C6 C5 . . 118.5(5) ?
    C1 C6 H6 . . 120.7 ?
    C5 C6 H6 . . 120.7 ?
    F1' C1' C6' . . 118.3(5) ?
    F1' C1' C2' . . 118.9(5) ?
    C6' C1' C2' . . 122.0(5) ?
    C1' C2' C3 . . 120.5(6) ?
    C1' C2' H2' . . 119.8 ?
    C3 C2' H2' . . 119.8 ?
    C5' C4' C3 . . 120.2(6) ?
    C5' C4' H4' . . 119.9 ?
    C3 C4' H4' . . 119.9 ?
    C6' C5' C4' . . 120.1(6) ?
    C6' C5' H5' . . 120.0 ?
    C4' C5' H5' . . 120.0 ?
    C1' C6' C5' . . 118.6(5) ?
    C1' C6' H6' . . 120.7 ?
    C5' C6' H6' . . 120.7 ?
    O1 C7 C3 . . 109.1(4) ?
    O1 C7 H7A . . 109.9 ?
    C3 C7 H7A . . 109.9 ?
    O1 C7 H7B . . 109.9 ?
    C3 C7 H7B . . 109.9 ?
    H7A C7 H7B . . 108.3 ?
    O1 C8 C9 . . 125.5(4) ?
    O1 C8 C13 . . 116.3(4) ?
    C9 C8 C13 . . 118.2(3) ?
    C8 C9 C10 . . 120.4(4) ?
    C8 C9 H9 . . 119.8 ?
    C10 C9 H9 . . 119.8 ?
    C11 C10 C9 . . 120.5(4) ?
    C11 C10 H10 . . 119.7 ?
    C9 C10 H10 . . 119.7 ?
    C10 C11 C12 . . 119.8(3) ?
    C10 C11 N1 . . 120.2(3) ?
    C12 C11 N1 . . 120.0(4) ?
    C13 C12 C11 . . 119.8(4) ?
    C13 C12 H12 . . 120.1 ?
    C11 C12 H12 . . 120.1 ?
    C12 C13 C8 . . 121.3(4) ?
    C12 C13 Cl1 . . 119.4(3) ?
    C8 C13 Cl1 . . 119.3(3) ?
    N1 C14 N2 . . 117.6(3) ?
    N1 C14 C15 . . 120.4(3) ?
    N2 C14 C15 . . 122.0(3) ?
    C16 C15 C20 . . 118.9(3) ?
    C16 C15 C14 . . 124.4(3) ?
    C20 C15 C14 . . 116.7(3) ?
    C17 C16 C15 . . 120.8(3) ?
    C17 C16 H16 . . 119.6 ?
    C15 C16 H16 . . 119.6 ?
    C16 C17 C18 . . 119.2(3) ?
    C16 C17 C22 . . 120.7(3) ?
    C18 C17 C22 . . 120.1(3) ?
    C19 C18 C17 . . 120.8(3) ?
    C19 C18 H18 . . 119.6 ?
    C17 C18 H18 . . 119.6 ?
    C18 C19 C20 . . 119.7(3) ?
    C18 C19 H19 . . 120.1 ?
    C20 C19 H19 . . 120.1 ?
    N3 C20 C19 . . 121.7(3) ?
    N3 C20 C15 . . 117.8(3) ?
    C19 C20 C15 . . 120.5(3) ?
    N2 C21 N3 . . 126.0(3) ?
    N2 C21 H21 . . 117.0 ?
    N3 C21 H21 . . 117.0 ?
    C23 C22 O2 . . 109.3(3) ?
    C23 C22 C17 . . 134.9(3) ?
    O2 C22 C17 . . 115.7(2) ?
    C22 C23 C24 . . 107.0(3) ?
    C22 C23 H23 . . 126.5 ?
    C24 C23 H23 . . 126.5 ?
    C25 C24 C23 . . 107.0(3) ?
    C25 C24 H24 . . 126.5 ?
    C23 C24 H24 . . 126.5 ?
    C24 C25 O2 . . 110.1(3) ?
    C24 C25 C26 . . 133.8(3) ?
    O2 C25 C26 . . 115.8(3) ?
    C25 C26 N4 . . 113.0(3) ?
    C25 C26 H26A . . 109.0 ?
    N4 C26 H26A . . 109.0 ?
    C25 C26 H26B . . 109.0 ?
    N4 C26 H26B . . 109.0 ?
    H26A C26 H26B . . 107.8 ?
    N4 C27 C28 . . 109.5(3) ?
    N4 C27 H27A . . 109.8 ?
    C28 C27 H27A . . 109.8 ?
    N4 C27 H27B . . 109.8 ?
    C28 C27 H27B . . 109.8 ?
    H27A C27 H27B . . 108.2 ?
    C27 C28 S1 . . 111.5(2) ?
    C27 C28 H28A . . 109.3 ?
    S1 C28 H28A . . 109.3 ?
    C27 C28 H28B . . 109.3 ?
    S1 C28 H28B . . 109.3 ?
    H28A C28 H28B . . 108.0 ?
    S1 C29 H29A . . 109.5 ?
    S1 C29 H29B . . 109.5 ?
    H29A C29 H29B . . 109.5 ?
    S1 C29 H29C . . 109.5 ?
    H29A C29 H29C . . 109.5 ?
    H29B C29 H29C . . 109.5 ?
    C14 N1 C11 . . 124.0(3) ?
    C14 N1 H1N . . 118(3) ?
    C11 N1 H1N . . 115(3) ?
    C21 N2 C14 . . 116.7(3) ?
    C21 N3 C20 . . 120.4(3) ?
    C21 N3 H3N . . 120(3) ?
    C20 N3 H3N . . 119(3) ?
    C27 N4 C26 . . 111.2(3) ?
    C27 N4 H4N . . 107(3) ?
    C26 N4 H4N . . 114(3) ?
    C27 N4 H5N . . 115(2) ?
    C26 N4 H5N . . 105(2) ?
    H4N N4 H5N . . 105(3) ?
    C8 O1 C7 . . 118.0(3) ?
    C25 O2 C22 . . 106.6(2) ?
    O3 S1 O4 . . 118.4(2) ?
    O3 S1 C29 . . 108.4(2) ?
    O4 S1 C29 . . 109.0(2) ?
    O3 S1 C28 . . 108.91(19) ?
    O4 S1 C28 . . 108.3(2) ?
    C29 S1 C28 . . 102.56(19) ?
    C35 C30 C31 . . 118.5(3) ?
    C35 C30 S2 . . 120.9(3) ?
    C31 C30 S2 . . 120.5(3) ?
    C30 C31 C32 . . 119.3(4) ?
    C30 C31 H31 . . 120.3 ?
    C32 C31 H31 . . 120.3 ?
    C33 C32 C31 . . 122.6(4) ?
    C33 C32 H32 . . 118.7 ?
    C31 C32 H32 . . 118.7 ?
    C32 C33 C34 . . 117.1(4) ?
    C32 C33 C36 . . 122.4(4) ?
    C34 C33 C36 . . 120.6(4) ?
    C33 C34 C35 . . 121.5(4) ?
    C33 C34 H34 . . 119.2 ?
    C35 C34 H34 . . 119.2 ?
    C30 C35 C34 . . 120.9(4) ?
    C30 C35 H35 . . 119.5 ?
    C34 C35 H35 . . 119.5 ?
    C33 C36 H36A . . 109.5 ?
    C33 C36 H36B . . 109.5 ?
    H36A C36 H36B . . 109.5 ?
    C33 C36 H36C . . 109.5 ?
    H36A C36 H36C . . 109.5 ?
    H36B C36 H36C . . 109.5 ?
    O6 S2 O5 . . 114.9(2) ?
    O6 S2 O7 . . 111.2(2) ?
    O5 S2 O7 . . 110.6(2) ?
    O6 S2 C30 . . 107.84(18) ?
    O5 S2 C30 . . 105.92(16) ?
    O7 S2 C30 . . 105.89(16) ?
    C42 C37 C38 . . 119.1(4) ?
    C42 C37 S3 . . 120.0(3) ?
    C38 C37 S3 . . 120.9(3) ?
    C39 C38 C37 . . 119.8(4) ?
    C39 C38 H38 . . 120.1 ?
    C37 C38 H38 . . 120.1 ?
    C40 C39 C38 . . 122.5(5) ?
    C40 C39 H39 . . 118.7 ?
    C38 C39 H39 . . 118.7 ?
    C39 C40 C41 . . 117.8(5) ?
    C39 C40 C43 . . 122.7(6) ?
    C41 C40 C43 . . 119.5(6) ?
    C40 C41 C42 . . 121.5(5) ?
    C40 C41 H41 . . 119.2 ?
    C42 C41 H41 . . 119.2 ?
    C37 C42 C41 . . 119.2(5) ?
    C37 C42 H42 . . 120.4 ?
    C41 C42 H42 . . 120.4 ?
    C40 C43 H43A . . 109.5 ?
    C40 C43 H43B . . 109.5 ?
    H43A C43 H43B . . 109.5 ?
    C40 C43 H43C . . 109.5 ?
    H43A C43 H43C . . 109.5 ?
    H43B C43 H43C . . 109.5 ?
    O8 S3 O10 . . 112.16(16) ?
    O8 S3 O9 . . 112.42(16) ?
    O10 S3 O9 . . 112.28(14) ?
    O8 S3 C37 . . 107.22(16) ?
    O10 S3 C37 . . 106.76(16) ?
    O9 S3 C37 . . 105.46(16) ?
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
    F1 C1 C2 C3 . . . . -173.4(11) ?
    C6 C1 C2 C3 . . . . 6.2(15) ?
    C2' C3 C2 C1 . . . . -85(2) ?
    C4 C3 C2 C1 . . . . -9.4(10) ?
    C4' C3 C2 C1 . . . . 16.1(11) ?
    C7 C3 C2 C1 . . . . 179.1(7) ?
    C2 C3 C4 C5 . . . . 5.8(13) ?
    C2' C3 C4 C5 . . . . 17.9(15) ?
    C4' C3 C4 C5 . . . . -85.6(14) ?
    C7 C3 C4 C5 . . . . 176.8(8) ?
    C3 C4 C5 C6 . . . . 1.2(17) ?
    F1 C1 C6 C5 . . . . -179.5(11) ?
    C2 C1 C6 C5 . . . . 1(2) ?
    C4 C5 C6 C1 . . . . -5(2) ?
    F1' C1' C2' C3 . . . . 170.1(16) ?
    C6' C1' C2' C3 . . . . 0(3) ?
    C2 C3 C2' C1' . . . . 86(3) ?
    C4 C3 C2' C1' . . . . -23.9(19) ?
    C4' C3 C2' C1' . . . . 1(2) ?
    C7 C3 C2' C1' . . . . 176.1(12) ?
    C2 C3 C4' C5' . . . . -12.7(17) ?
    C2' C3 C4' C5' . . . . -0.1(19) ?
    C4 C3 C4' C5' . . . . 88.0(16) ?
    C7 C3 C4' C5' . . . . -174.6(10) ?
    C3 C4' C5' C6' . . . . -3(2) ?
    F1' C1' C6' C5' . . . . -173.0(16) ?
    C2' C1' C6' C5' . . . . -3(3) ?
    C4' C5' C6' C1' . . . . 4(3) ?
    C2 C3 C7 O1 . . . . 177.2(7) ?
    C2' C3 C7 O1 . . . . 164.5(10) ?
    C4 C3 C7 O1 . . . . 6.1(10) ?
    C4' C3 C7 O1 . . . . -21.0(11) ?
    O1 C8 C9 C10 . . . . 179.6(4) ?
    C13 C8 C9 C10 . . . . 0.4(7) ?
    C8 C9 C10 C11 . . . . 0.2(7) ?
    C9 C10 C11 C12 . . . . -0.7(6) ?
    C9 C10 C11 N1 . . . . 177.9(4) ?
    C10 C11 C12 C13 . . . . 0.6(6) ?
    N1 C11 C12 C13 . . . . -178.0(4) ?
    C11 C12 C13 C8 . . . . 0.0(6) ?
    C11 C12 C13 Cl1 . . . . -179.5(3) ?
    O1 C8 C13 C12 . . . . -179.8(4) ?
    C9 C8 C13 C12 . . . . -0.5(7) ?
    O1 C8 C13 Cl1 . . . . -0.3(6) ?
    C9 C8 C13 Cl1 . . . . 179.0(4) ?
    N1 C14 C15 C16 . . . . 7.5(5) ?
    N2 C14 C15 C16 . . . . -171.3(3) ?
    N1 C14 C15 C20 . . . . -173.5(3) ?
    N2 C14 C15 C20 . . . . 7.7(4) ?
    C20 C15 C16 C17 . . . . 1.3(4) ?
    C14 C15 C16 C17 . . . . -179.7(3) ?
    C15 C16 C17 C18 . . . . 1.7(4) ?
    C15 C16 C17 C22 . . . . -177.6(3) ?
    C16 C17 C18 C19 . . . . -3.0(4) ?
    C22 C17 C18 C19 . . . . 176.3(3) ?
    C17 C18 C19 C20 . . . . 1.1(5) ?
    C18 C19 C20 N3 . . . . -177.1(3) ?
    C18 C19 C20 C15 . . . . 1.9(5) ?
    C16 C15 C20 N3 . . . . 175.9(3) ?
    C14 C15 C20 N3 . . . . -3.2(4) ?
    C16 C15 C20 C19 . . . . -3.1(4) ?
    C14 C15 C20 C19 . . . . 177.8(3) ?
    C16 C17 C22 C23 . . . . 177.5(3) ?
    C18 C17 C22 C23 . . . . -1.8(5) ?
    C16 C17 C22 O2 . . . . -0.2(4) ?
    C18 C17 C22 O2 . . . . -179.5(2) ?
    O2 C22 C23 C24 . . . . 0.9(3) ?
    C17 C22 C23 C24 . . . . -176.8(3) ?
    C22 C23 C24 C25 . . . . -0.7(4) ?
    C23 C24 C25 O2 . . . . 0.1(4) ?
    C23 C24 C25 C26 . . . . -172.9(4) ?
    C24 C25 C26 N4 . . . . -137.0(4) ?
    O2 C25 C26 N4 . . . . 50.3(4) ?
    N4 C27 C28 S1 . . . . -176.8(3) ?
    N2 C14 N1 C11 . . . . -0.7(5) ?
    C15 C14 N1 C11 . . . . -179.6(3) ?
    C10 C11 N1 C14 . . . . 104.6(4) ?
    C12 C11 N1 C14 . . . . -76.8(5) ?
    N3 C21 N2 C14 . . . . 1.3(5) ?
    N1 C14 N2 C21 . . . . 174.4(3) ?
    C15 C14 N2 C21 . . . . -6.7(4) ?
    N2 C21 N3 C20 . . . . 3.1(5) ?
    C19 C20 N3 C21 . . . . 177.2(3) ?
    C15 C20 N3 C21 . . . . -1.8(4) ?
    C28 C27 N4 C26 . . . . 177.4(3) ?
    C25 C26 N4 C27 . . . . -177.4(3) ?
    C9 C8 O1 C7 . . . . 4.1(7) ?
    C13 C8 O1 C7 . . . . -176.7(4) ?
    C3 C7 O1 C8 . . . . 177.8(4) ?
    C24 C25 O2 C22 . . . . 0.5(3) ?
    C26 C25 O2 C22 . . . . 174.9(3) ?
    C23 C22 O2 C25 . . . . -0.9(3) ?
    C17 C22 O2 C25 . . . . 177.3(2) ?
    C27 C28 S1 O3 . . . . 62.2(3) ?
    C27 C28 S1 O4 . . . . -67.9(3) ?
    C27 C28 S1 C29 . . . . 176.9(3) ?
    C35 C30 C31 C32 . . . . 0.6(7) ?
    S2 C30 C31 C32 . . . . -176.9(4) ?
    C30 C31 C32 C33 . . . . -0.8(8) ?
    C31 C32 C33 C34 . . . . 1.0(8) ?
    C31 C32 C33 C36 . . . . -180.0(5) ?
    C32 C33 C34 C35 . . . . -0.9(7) ?
    C36 C33 C34 C35 . . . . -180.0(5) ?
    C31 C30 C35 C34 . . . . -0.5(7) ?
    S2 C30 C35 C34 . . . . 176.9(4) ?
    C33 C34 C35 C30 . . . . 0.7(8) ?
    C35 C30 S2 O6 . . . . 145.3(4) ?
    C31 C30 S2 O6 . . . . -37.3(4) ?
    C35 C30 S2 O5 . . . . 21.9(4) ?
    C31 C30 S2 O5 . . . . -160.8(4) ?
    C35 C30 S2 O7 . . . . -95.6(4) ?
    C31 C30 S2 O7 . . . . 81.8(4) ?
    C42 C37 C38 C39 . . . . -0.4(6) ?
    S3 C37 C38 C39 . . . . -178.3(3) ?
    C37 C38 C39 C40 . . . . 2.3(7) ?
    C38 C39 C40 C41 . . . . -3.3(8) ?
    C38 C39 C40 C43 . . . . 177.0(5) ?
    C39 C40 C41 C42 . . . . 2.4(8) ?
    C43 C40 C41 C42 . . . . -177.8(5) ?
    C38 C37 C42 C41 . . . . -0.4(6) ?
    S3 C37 C42 C41 . . . . 177.6(4) ?
    C40 C41 C42 C37 . . . . -0.6(8) ?
    C42 C37 S3 O8 . . . . -64.9(4) ?
    C38 C37 S3 O8 . . . . 113.0(3) ?
    C42 C37 S3 O10 . . . . 55.4(3) ?
    C38 C37 S3 O10 . . . . -126.7(3) ?
    C42 C37 S3 O9 . . . . 175.0(3) ?
    C38 C37 S3 O9 . . . . -7.0(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 O5 . 0.79(4) 2.14(4) 2.922(5) 168(4)
    N3 H3N O9 1_545 0.78(3) 1.95(4) 2.726(4) 176(4)
    N4 H4N O7 . 0.82(4) 2.02(4) 2.804(4) 161(4)
    N4 H5N O10 . 0.86(4) 2.14(4) 2.988(4) 167(3)
    C5 H5 O5 2_756 0.93 2.61 3.472(8) 154.4
    C18 H18 O6 2_655 0.93 2.57 3.344(4) 141.5
    C21 H21 O10 2_755 0.93 2.42 3.270(4) 151.6
    C23 H23 O5 2_655 0.93 2.59 3.371(4) 141.5
    C24 H24 O4 2_665 0.93 2.58 3.475(4) 161.9
    C27 H27B O8 . 0.97 2.58 3.228(5) 124.6
    C28 H28A O10 2_765 0.97 2.54 3.387(4) 145.2
    C34 H34 Cl1 2_756 0.93 2.81 3.619(4) 146.8
    C38 H38 O7 2_765 0.93 2.51 3.392(5) 157.6
data_global
_journal_date_recd_electronic     2013-08-21
_journal_date_accepted     2013-10-21
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2013
_journal_volume     69
_journal_issue     12
_journal_page_first     1516
_journal_page_last     1523
_journal_paper_category     FO
_journal_paper_doi     10.1107/S0108270113028965
_journal_coeditor_code     OV3039
_publ_contact_author_name     'K. Ravikumar'
_publ_contact_author_address
;
Laboratory of X-ray Crystallography
CSIR-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
;
Tosylate salts of the anticancer drug lapatinib
;
loop_
    _publ_author_name
    _publ_author_address
    'K. Ravikumar'
;
Centre for X-ray Crystallography
CSIR-Indian Institute of Chemical Technology
Hyderabad 500 007
India
;
    'B. Sridhar'
;
Centre for X-ray Crystallography
CSIR-Indian Institute of Chemical Technology
Hyderabad 500 007
India
;
    'Jagadeesh Babu Nanubolu'
;
Centre for X-ray Crystallography
CSIR-Indian Institute of Chemical Technology
Hyderabad 500 007
India
;
    'A. K. S. Bhujanga Rao'
;
Natco Research Centre
Sanath Nagar
Hyderabad 500 018
India
;
    'R. Jyothiprasad'
;
Natco Research Centre
Sanath Nagar
Hyderabad 500 018
India
;
_publ_section_synopsis
;
Two tosylate salts of lapatinib, an anticancer drug crystallize in the
centrosymmetric and noncentrosymmetric space groups. The crystal packing in
both structures are influenced by a combination of N---H...O hydrogen bonds
and C---H...O interactions
;
