# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2011


data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
R.Thakuria
A.Nangia
_publ_contact_author_name        'Ashwini Nangia'
_publ_contact_author_email       ashwini.nangia@gmail.com

data_an951_OLN-MA_1:1
_database_code_depnum_ccdc_archive 'CCDC 774459'
#TrackingRef 'Olan-Maleic-1-1.cif.txt'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'Olanzapine-Maleic acid 1:1'
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H21 N4 S, C4 H3 O4'
_chemical_formula_sum            'C21 H24 N4 O4 S'
_chemical_formula_weight         428.50

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n '
_symmetry_space_group_name_Hall  '-P 2yn '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.852(5)
_cell_length_b                   13.748(7)
_cell_length_c                   13.879(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.856(8)
_cell_angle_gamma                90.00
_cell_volume                     2051.3(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5026
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      26.04

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9369
_exptl_absorpt_correction_T_max  0.9659
_exptl_absorpt_process_details   'Bruker AXS SADABS program'

_exptl_special_details           
;
Sheldrick,G.M.,(2003),University of gottingen,Germany
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20986
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         26.09
_reflns_number_total             4054
_reflns_number_gt                3375
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0640P)^2^+0.4927P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4054
_refine_ls_number_parameters     285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.1125
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.38626(15) 0.00612(12) 0.75829(11) 0.0366(4) Uani 1 1 d . . .
C3 C 0.25642(15) 0.01388(12) 0.74246(11) 0.0369(4) Uani 1 1 d . . .
C5 C 0.22355(14) 0.09613(11) 0.88626(12) 0.0351(4) Uani 1 1 d . . .
C6 C 0.33926(14) 0.09976(11) 0.93953(12) 0.0343(3) Uani 1 1 d . . .
C7 C 0.45035(14) 0.11291(12) 0.89058(11) 0.0340(3) Uani 1 1 d . . .
C8 C 0.33337(16) 0.09179(12) 1.04145(12) 0.0388(4) Uani 1 1 d . . .
H8 H 0.4039 0.0910 1.0878 0.047 Uiso 1 1 calc R . .
C9 C 0.21667(16) 0.08546(12) 1.06482(13) 0.0415(4) Uani 1 1 d . . .
C10 C 0.1757(2) 0.07747(16) 1.16329(14) 0.0571(5) Uani 1 1 d . . .
H10A H 0.2471 0.0799 1.2124 0.086 Uiso 1 1 calc R . .
H10B H 0.1328 0.0169 1.1680 0.086 Uiso 1 1 calc R . .
H10C H 0.1209 0.1304 1.1725 0.086 Uiso 1 1 calc R . .
C11 C 0.44122(17) -0.07075(13) 0.71463(13) 0.0445(4) Uani 1 1 d . . .
H11 H 0.5274 -0.0763 0.7238 0.053 Uiso 1 1 calc R . .
C12 C 0.37127(19) -0.13886(14) 0.65818(15) 0.0539(5) Uani 1 1 d . . .
H12 H 0.4099 -0.1905 0.6311 0.065 Uiso 1 1 calc R . .
C13 C 0.2441(2) -0.12971(15) 0.64237(15) 0.0583(5) Uani 1 1 d . . .
H13 H 0.1964 -0.1746 0.6034 0.070 Uiso 1 1 calc R . .
C14 C 0.18687(17) -0.05392(14) 0.68427(14) 0.0499(5) Uani 1 1 d . . .
H14 H 0.1007 -0.0483 0.6733 0.060 Uiso 1 1 calc R . .
C15 C 0.53334(15) 0.24603(12) 1.00630(13) 0.0424(4) Uani 1 1 d . . .
H15A H 0.4552 0.2394 1.0322 0.051 Uiso 1 1 calc R . .
H15B H 0.5329 0.3080 0.9728 0.051 Uiso 1 1 calc R . .
C16 C 0.63998(17) 0.24285(14) 1.08794(13) 0.0481(4) Uani 1 1 d . . .
H16A H 0.6323 0.2963 1.1324 0.058 Uiso 1 1 calc R . .
H16B H 0.6367 0.1825 1.1238 0.058 Uiso 1 1 calc R . .
C17 C 0.77144(16) 0.17433(14) 0.97446(14) 0.0482(4) Uani 1 1 d . . .
H17A H 0.7766 0.1105 1.0046 0.058 Uiso 1 1 calc R . .
H17B H 0.8470 0.1848 0.9458 0.058 Uiso 1 1 calc R . .
C18 C 0.66172(15) 0.17732(16) 0.89614(14) 0.0514(5) Uani 1 1 d . . .
H18A H 0.6610 0.2385 0.8613 0.062 Uiso 1 1 calc R . .
H18B H 0.6680 0.1250 0.8502 0.062 Uiso 1 1 calc R . .
C19 C 0.86848(19) 0.24306(17) 1.12947(16) 0.0613(6) Uani 1 1 d . . .
H19A H 0.8678 0.1806 1.1604 0.092 Uiso 1 1 calc R . .
H19B H 0.8616 0.2933 1.1765 0.092 Uiso 1 1 calc R . .
H19C H 0.9449 0.2509 1.1027 0.092 Uiso 1 1 calc R . .
C20 C 0.64630(18) 0.65371(15) 0.80522(14) 0.0522(5) Uani 1 1 d . . .
C21 C 0.77629(17) 0.63875(15) 0.85398(15) 0.0517(5) Uani 1 1 d . . .
H21 H 0.8308 0.6887 0.8436 0.062 Uiso 1 1 calc R . .
C22 C 0.82825(17) 0.56713(14) 0.90949(14) 0.0502(5) Uani 1 1 d . . .
H22 H 0.9125 0.5749 0.9316 0.060 Uiso 1 1 calc R . .
C23 C 0.77181(19) 0.47664(14) 0.94141(15) 0.0509(5) Uani 1 1 d . . .
H1 H 0.600(3) 0.535(2) 0.875(2) 0.100(9) Uiso 1 1 d . . .
H3 H 0.7675(18) 0.3136(16) 1.0211(15) 0.053(5) Uiso 1 1 d . . .
H4 H 0.119(2) 0.0991(15) 0.7644(16) 0.056(6) Uiso 1 1 d . . .
N1 N 0.46751(12) 0.07525(10) 0.80868(10) 0.0376(3) Uani 1 1 d . . .
N2 N 0.54674(12) 0.16714(11) 0.93867(10) 0.0437(4) Uani 1 1 d . . .
N3 N 0.76174(12) 0.24983(10) 1.05017(10) 0.0394(3) Uani 1 1 d . . .
N4 N 0.19784(14) 0.09307(10) 0.78524(10) 0.0394(3) Uani 1 1 d . . .
O1 O 0.56134(13) 0.59540(12) 0.82606(13) 0.0678(4) Uani 1 1 d . . .
O2 O 0.62581(16) 0.71921(15) 0.74703(14) 0.0913(6) Uani 1 1 d . . .
O3 O 0.65509(14) 0.46310(12) 0.92344(14) 0.0760(5) Uani 1 1 d . . .
O4 O 0.84206(15) 0.41582(11) 0.98463(13) 0.0732(5) Uani 1 1 d . . .
S1 S 0.10818(4) 0.08629(3) 0.96033(3) 0.04285(15) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C2 0.0368(8) 0.0390(9) 0.0325(8) 0.0022(7) 0.0001(6) -0.0038(7)
C3 0.0368(8) 0.0387(9) 0.0334(8) 0.0047(7) -0.0020(6) -0.0007(7)
C5 0.0299(8) 0.0345(8) 0.0405(9) 0.0049(6) 0.0038(6) 0.0005(6)
C6 0.0313(8) 0.0339(8) 0.0368(8) 0.0014(6) 0.0019(6) -0.0012(6)
C7 0.0286(8) 0.0362(8) 0.0363(8) 0.0018(6) 0.0009(6) -0.0007(6)
C8 0.0361(9) 0.0410(9) 0.0384(9) 0.0021(7) 0.0017(7) -0.0004(7)
C9 0.0415(9) 0.0421(9) 0.0413(9) 0.0048(7) 0.0067(7) -0.0001(7)
C10 0.0563(12) 0.0685(13) 0.0496(11) 0.0093(9) 0.0181(9) 0.0000(10)
C11 0.0426(9) 0.0487(10) 0.0412(9) -0.0032(8) 0.0016(7) 0.0018(8)
C12 0.0600(12) 0.0476(11) 0.0522(11) -0.0111(9) 0.0007(9) 0.0014(9)
C13 0.0596(12) 0.0514(12) 0.0592(12) -0.0135(9) -0.0091(10) -0.0106(9)
C14 0.0409(10) 0.0531(11) 0.0512(11) -0.0009(9) -0.0098(8) -0.0057(8)
C15 0.0345(8) 0.0411(9) 0.0516(10) -0.0077(8) 0.0061(7) -0.0011(7)
C16 0.0442(10) 0.0537(11) 0.0459(10) -0.0147(8) 0.0050(8) -0.0054(8)
C17 0.0348(9) 0.0488(11) 0.0612(11) -0.0160(9) 0.0074(8) -0.0030(8)
C18 0.0341(9) 0.0740(13) 0.0472(10) -0.0181(9) 0.0098(7) -0.0154(9)
C19 0.0488(11) 0.0674(14) 0.0608(12) -0.0007(10) -0.0174(9) -0.0010(10)
C20 0.0480(11) 0.0578(12) 0.0508(11) -0.0061(9) 0.0063(9) 0.0095(9)
C21 0.0425(10) 0.0534(11) 0.0584(11) 0.0064(9) 0.0033(8) -0.0094(8)
C22 0.0388(9) 0.0529(11) 0.0566(11) 0.0063(9) -0.0017(8) -0.0082(8)
C23 0.0519(11) 0.0462(11) 0.0536(11) 0.0008(9) 0.0033(9) -0.0070(9)
N1 0.0315(7) 0.0443(8) 0.0363(7) -0.0030(6) 0.0027(5) -0.0046(6)
N2 0.0302(7) 0.0581(9) 0.0435(8) -0.0157(7) 0.0072(6) -0.0096(6)
N3 0.0350(7) 0.0358(8) 0.0448(8) -0.0023(6) -0.0044(6) -0.0030(6)
N4 0.0303(7) 0.0455(8) 0.0399(8) 0.0043(6) -0.0037(6) 0.0031(6)
O1 0.0372(7) 0.0717(10) 0.0912(12) 0.0000(9) -0.0032(7) -0.0011(7)
O2 0.0716(11) 0.1069(14) 0.0931(13) 0.0391(12) 0.0028(10) 0.0270(10)
O3 0.0527(9) 0.0655(10) 0.1078(13) 0.0178(9) 0.0035(9) -0.0203(8)
O4 0.0671(10) 0.0529(9) 0.0951(13) 0.0201(8) -0.0048(9) -0.0062(7)
S1 0.0298(2) 0.0489(3) 0.0503(3) 0.00710(19) 0.00707(18) 0.00026(17)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 C11 1.392(2) . ?
C2 C3 1.400(2) . ?
C2 N1 1.415(2) . ?
C3 C14 1.387(2) . ?
C3 N4 1.430(2) . ?
C5 C6 1.368(2) . ?
C5 N4 1.392(2) . ?
C5 S1 1.7305(17) . ?
C6 C8 1.429(2) . ?
C6 C7 1.474(2) . ?
C7 N1 1.286(2) . ?
C7 N2 1.380(2) . ?
C8 C9 1.352(2) . ?
C9 C10 1.498(3) . ?
C9 S1 1.7386(19) . ?
C11 C12 1.380(3) . ?
C12 C13 1.373(3) . ?
C13 C14 1.381(3) . ?
C15 N2 1.455(2) . ?
C15 C16 1.505(2) . ?
C16 N3 1.490(2) . ?
C17 N3 1.491(2) . ?
C17 C18 1.499(3) . ?
C18 N2 1.458(2) . ?
C19 N3 1.488(2) . ?
C20 O2 1.210(3) . ?
C20 O1 1.284(3) . ?
C20 C21 1.493(3) . ?
C21 C22 1.328(3) . ?
C22 C23 1.481(3) . ?
C23 O4 1.231(2) . ?
C23 O3 1.271(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C2 C3 118.12(15) . . ?
C11 C2 N1 116.74(15) . . ?
C3 C2 N1 124.91(15) . . ?
C14 C3 C2 119.74(16) . . ?
C14 C3 N4 121.06(16) . . ?
C2 C3 N4 119.20(14) . . ?
C6 C5 N4 126.02(15) . . ?
C6 C5 S1 111.53(13) . . ?
N4 C5 S1 122.29(12) . . ?
C5 C6 C8 111.73(15) . . ?
C5 C6 C7 120.24(15) . . ?
C8 C6 C7 128.02(15) . . ?
N1 C7 N2 116.96(14) . . ?
N1 C7 C6 125.78(14) . . ?
N2 C7 C6 117.20(14) . . ?
C9 C8 C6 114.36(15) . . ?
C8 C9 C10 128.91(17) . . ?
C8 C9 S1 110.43(14) . . ?
C10 C9 S1 120.65(14) . . ?
C12 C11 C2 121.80(17) . . ?
C13 C12 C11 119.43(18) . . ?
C12 C13 C14 120.11(18) . . ?
C13 C14 C3 120.79(18) . . ?
N2 C15 C16 109.25(14) . . ?
N3 C16 C15 111.15(15) . . ?
N3 C17 C18 111.49(15) . . ?
N2 C18 C17 110.04(15) . . ?
O2 C20 O1 122.9(2) . . ?
O2 C20 C21 118.8(2) . . ?
O1 C20 C21 118.35(18) . . ?
C22 C21 C20 131.70(18) . . ?
C21 C22 C23 129.53(18) . . ?
O4 C23 O3 122.04(19) . . ?
O4 C23 C22 117.55(18) . . ?
O3 C23 C22 120.41(18) . . ?
C7 N1 C2 123.50(14) . . ?
C7 N2 C15 125.38(14) . . ?
C7 N2 C18 119.34(14) . . ?
C15 N2 C18 110.86(14) . . ?
C19 N3 C16 111.96(15) . . ?
C19 N3 C17 110.79(15) . . ?
C16 N3 C17 110.77(13) . . ?
C5 N4 C3 113.69(13) . . ?
C5 S1 C9 91.92(9) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.09
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.042


# Attachment 'Olan-Maleic-1-2.cif.txt'

data_tri_OLN-MA_1:2
_database_code_depnum_ccdc_archive 'CCDC 774460'
#TrackingRef 'Olan-Maleic-1-2.cif.txt'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'Olanzapine-Maleic acid 1:2'
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H22 N4 S, 2(C4 H3 O4)'
_chemical_formula_sum            'C25 H28 N4 O8 S'
_chemical_formula_weight         544.57

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'

_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                   8.518(3)
_cell_length_b                   9.804(4)
_cell_length_c                   16.210(6)
_cell_angle_alpha                95.956(7)
_cell_angle_beta                 97.945(7)
_cell_angle_gamma                107.789(7)
_cell_volume                     1261.2(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1848
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      21.98

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             572
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9376
_exptl_absorpt_correction_T_max  0.9744
_exptl_absorpt_process_details   'Bruker AXS SADABS program'

_exptl_special_details           
;
Sheldrick,G.M.,(2003),University of gottingen,Germany
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13184
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_sigmaI/netI    0.0741
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.28
_diffrn_reflns_theta_max         26.11
_reflns_number_total             4971
_reflns_number_gt                3737
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0628P)^2^+0.5252P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4971
_refine_ls_number_parameters     365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1167
_refine_ls_R_factor_gt           0.0864
_refine_ls_wR_factor_ref         0.1987
_refine_ls_wR_factor_gt          0.1789
_refine_ls_goodness_of_fit_ref   1.243
_refine_ls_restrained_S_all      1.243
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.7490(5) -0.0109(4) -0.0028(2) 0.0314(9) Uani 1 1 d . . .
C3 C 0.6677(5) 0.0578(4) -0.0570(2) 0.0317(9) Uani 1 1 d . . .
C5 C 0.7331(4) 0.2917(4) 0.0297(2) 0.0284(8) Uani 1 1 d . . .
C6 C 0.8353(5) 0.2837(4) 0.1015(2) 0.0292(8) Uani 1 1 d . . .
C7 C 0.8252(5) 0.1517(4) 0.1353(2) 0.0294(8) Uani 1 1 d . . .
C8 C 0.9409(5) 0.4255(4) 0.1439(2) 0.0341(9) Uani 1 1 d . . .
H8 H 1.0202 0.4398 0.1923 0.041 Uiso 1 1 calc R . .
C9 C 0.9146(5) 0.5343(4) 0.1075(2) 0.0327(9) Uani 1 1 d . . .
C10 C 1.0017(6) 0.6936(4) 0.1322(3) 0.0435(11) Uani 1 1 d . . .
H10A H 1.0890 0.7107 0.1801 0.065 Uiso 1 1 calc R . .
H10B H 0.9226 0.7400 0.1464 0.065 Uiso 1 1 calc R . .
H10C H 1.0494 0.7326 0.0860 0.065 Uiso 1 1 calc R . .
C11 C 0.7866(5) -0.1318(5) -0.0350(3) 0.0447(11) Uani 1 1 d . . .
H11 H 0.8419 -0.1768 0.0012 0.054 Uiso 1 1 calc R . .
C12 C 0.7433(6) -0.1857(5) -0.1197(3) 0.0512(12) Uani 1 1 d . . .
H12 H 0.7689 -0.2668 -0.1406 0.061 Uiso 1 1 calc R . .
C13 C 0.6615(5) -0.1190(5) -0.1735(3) 0.0472(12) Uani 1 1 d . . .
H13 H 0.6301 -0.1558 -0.2307 0.057 Uiso 1 1 calc R . .
C14 C 0.6264(5) 0.0024(5) -0.1422(2) 0.0387(10) Uani 1 1 d . . .
H14 H 0.5738 0.0482 -0.1791 0.046 Uiso 1 1 calc R . .
C15 C 0.8063(5) 0.2482(4) 0.2787(2) 0.0368(10) Uani 1 1 d . . .
H15A H 0.7039 0.1880 0.2936 0.044 Uiso 1 1 calc R . .
H15B H 0.7808 0.3242 0.2513 0.044 Uiso 1 1 calc R . .
C16 C 0.9345(6) 0.3154(4) 0.3575(3) 0.0407(10) Uani 1 1 d . . .
H16A H 1.0322 0.3848 0.3438 0.049 Uiso 1 1 calc R . .
H16B H 0.8881 0.3668 0.3968 0.049 Uiso 1 1 calc R . .
C17 C 1.0471(5) 0.1150(5) 0.3364(2) 0.0380(10) Uani 1 1 d . . .
H17A H 1.0768 0.0401 0.3631 0.046 Uiso 1 1 calc R . .
H17B H 1.1472 0.1776 0.3207 0.046 Uiso 1 1 calc R . .
C18 C 0.9159(5) 0.0460(4) 0.2583(3) 0.0379(10) Uani 1 1 d . . .
H18A H 0.9604 -0.0065 0.2186 0.045 Uiso 1 1 calc R . .
H18B H 0.8187 -0.0223 0.2732 0.045 Uiso 1 1 calc R . .
C19 C 1.1113(6) 0.2666(5) 0.4749(3) 0.0506(12) Uani 1 1 d . . .
H19A H 1.1402 0.1913 0.5004 0.076 Uiso 1 1 calc R . .
H19B H 1.0661 0.3183 0.5137 0.076 Uiso 1 1 calc R . .
H19C H 1.2097 0.3323 0.4610 0.076 Uiso 1 1 calc R . .
C20 C 0.4443(6) 0.3178(4) 0.8039(3) 0.0406(10) Uani 1 1 d . . .
C21 C 0.3319(5) 0.3554(4) 0.7373(3) 0.0389(10) Uani 1 1 d . . .
H21 H 0.2182 0.3074 0.7342 0.047 Uiso 1 1 calc R . .
C22 C 0.3670(6) 0.4458(4) 0.6818(3) 0.0406(10) Uani 1 1 d . . .
H22 H 0.2737 0.4486 0.6455 0.049 Uiso 1 1 calc R . .
C23 C 0.5294(7) 0.5430(5) 0.6676(3) 0.0537(13) Uani 1 1 d . . .
C24 C 0.6072(6) 0.9402(5) 0.4164(3) 0.0445(11) Uani 1 1 d . . .
C25 C 0.5012(6) 0.8188(5) 0.4548(3) 0.0471(11) Uani 1 1 d . . .
H25 H 0.5590 0.7920 0.4998 0.056 Uiso 1 1 calc R . .
C26 C 0.3402(6) 0.7446(5) 0.4350(3) 0.0511(12) Uani 1 1 d . . .
H26 H 0.3050 0.6715 0.4671 0.061 Uiso 1 1 calc R . .
C27 C 0.2054(6) 0.7561(5) 0.3710(3) 0.0516(12) Uani 1 1 d . . .
H1 H 0.750(7) -0.052(6) 0.116(3) 0.082(18) Uiso 1 1 d . . .
H3 H 0.893(6) 0.131(5) 0.415(3) 0.064(15) Uiso 1 1 d . . .
H4 H 0.564(5) 0.204(5) -0.067(3) 0.048(13) Uiso 1 1 d . . .
H7 H 0.381(10) 0.922(8) 0.340(4) 0.13(3) Uiso 1 1 d . . .
H3A H 0.660(5) 0.474(5) 0.740(3) 0.041(14) Uiso 1 1 d . . .
N1 N 0.7765(4) 0.0232(4) 0.0877(2) 0.0328(8) Uani 1 1 d . . .
N2 N 0.8666(4) 0.1591(3) 0.21941(19) 0.0328(8) Uani 1 1 d . . .
N3 N 0.9848(4) 0.2015(4) 0.3974(2) 0.0341(8) Uani 1 1 d . . .
N4 N 0.6246(4) 0.1801(4) -0.0279(2) 0.0347(8) Uani 1 1 d . . .
O1 O 0.3781(4) 0.2351(3) 0.85104(19) 0.0523(9) Uani 1 1 d . . .
O2 O 0.6008(4) 0.3715(4) 0.8098(2) 0.0629(10) Uani 1 1 d . . .
O3 O 0.6687(5) 0.5405(4) 0.7099(3) 0.0636(11) Uani 1 1 d . . .
O4 O 0.5278(6) 0.6253(5) 0.6177(3) 0.1027(16) Uani 1 1 d . . .
O5 O 0.7563(4) 0.9931(4) 0.4494(2) 0.0571(9) Uani 1 1 d . . .
O6 O 0.5411(4) 0.9812(4) 0.3532(2) 0.0657(11) Uani 1 1 d . . .
O7 O 0.2379(5) 0.8571(4) 0.3239(2) 0.0646(10) Uani 1 1 d . . .
O8 O 0.0646(4) 0.6696(4) 0.3634(3) 0.0795(12) Uani 1 1 d . . .
S1 S 0.75926(14) 0.46925(11) 0.01737(7) 0.0380(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C2 0.033(2) 0.028(2) 0.029(2) 0.0048(16) 0.0030(17) 0.0051(17)
C3 0.026(2) 0.030(2) 0.035(2) 0.0081(17) 0.0035(17) 0.0038(16)
C5 0.0251(19) 0.032(2) 0.028(2) 0.0075(16) 0.0055(16) 0.0070(16)
C6 0.031(2) 0.028(2) 0.027(2) 0.0078(16) 0.0048(16) 0.0063(16)
C7 0.026(2) 0.031(2) 0.028(2) 0.0048(16) 0.0011(16) 0.0067(16)
C8 0.033(2) 0.034(2) 0.031(2) 0.0073(17) 0.0003(17) 0.0052(18)
C9 0.035(2) 0.032(2) 0.031(2) 0.0089(17) 0.0080(17) 0.0092(17)
C10 0.049(3) 0.031(2) 0.048(3) 0.0101(19) 0.008(2) 0.008(2)
C11 0.048(3) 0.042(3) 0.044(3) 0.004(2) -0.002(2) 0.019(2)
C12 0.052(3) 0.053(3) 0.048(3) -0.008(2) 0.005(2) 0.023(2)
C13 0.046(3) 0.054(3) 0.032(2) -0.006(2) 0.004(2) 0.008(2)
C14 0.039(2) 0.045(3) 0.026(2) 0.0071(18) 0.0017(18) 0.007(2)
C15 0.044(2) 0.042(2) 0.032(2) 0.0153(18) 0.0092(19) 0.022(2)
C16 0.054(3) 0.034(2) 0.037(2) 0.0080(18) 0.006(2) 0.017(2)
C17 0.042(2) 0.042(2) 0.034(2) 0.0113(19) 0.0026(19) 0.019(2)
C18 0.050(3) 0.029(2) 0.033(2) 0.0066(17) -0.0029(19) 0.0142(19)
C19 0.047(3) 0.062(3) 0.036(3) 0.008(2) -0.002(2) 0.012(2)
C20 0.044(3) 0.033(2) 0.042(3) 0.0094(19) 0.004(2) 0.009(2)
C21 0.033(2) 0.041(2) 0.040(2) 0.0113(19) 0.0025(19) 0.0097(19)
C22 0.046(3) 0.041(2) 0.033(2) 0.0086(19) 0.0009(19) 0.014(2)
C23 0.075(4) 0.041(3) 0.042(3) 0.011(2) 0.021(3) 0.009(3)
C24 0.047(3) 0.041(3) 0.044(3) 0.011(2) 0.011(2) 0.009(2)
C25 0.043(3) 0.052(3) 0.051(3) 0.022(2) 0.014(2) 0.016(2)
C26 0.048(3) 0.050(3) 0.059(3) 0.022(2) 0.021(2) 0.013(2)
C27 0.042(3) 0.051(3) 0.057(3) -0.002(2) 0.010(2) 0.011(2)
N1 0.039(2) 0.0271(18) 0.0280(19) 0.0084(15) 0.0039(15) 0.0044(15)
N2 0.044(2) 0.0283(17) 0.0271(18) 0.0064(14) 0.0017(15) 0.0146(15)
N3 0.0357(19) 0.0359(19) 0.0289(19) 0.0098(15) 0.0023(15) 0.0088(16)
N4 0.0341(19) 0.0349(19) 0.032(2) 0.0080(15) -0.0044(15) 0.0099(15)
O1 0.064(2) 0.0397(17) 0.0479(19) 0.0220(15) 0.0019(16) 0.0087(16)
O2 0.0367(19) 0.079(3) 0.070(2) 0.030(2) -0.0033(16) 0.0135(17)
O3 0.049(2) 0.063(3) 0.068(3) 0.016(2) 0.020(2) -0.0018(19)
O4 0.124(4) 0.084(3) 0.094(3) 0.062(3) 0.025(3) 0.007(3)
O5 0.0395(19) 0.057(2) 0.068(2) 0.0200(18) 0.0079(17) 0.0034(16)
O6 0.053(2) 0.074(3) 0.061(2) 0.037(2) 0.0067(18) 0.0015(19)
O7 0.052(2) 0.075(3) 0.061(2) 0.017(2) 0.0010(18) 0.0140(19)
O8 0.040(2) 0.080(3) 0.104(3) 0.008(2) 0.011(2) -0.0001(19)
S1 0.0452(6) 0.0298(5) 0.0373(6) 0.0113(4) -0.0007(5) 0.0115(5)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 C11 1.390(6) . ?
C2 C3 1.394(5) . ?
C2 N1 1.440(5) . ?
C3 C14 1.386(5) . ?
C3 N4 1.412(5) . ?
C5 N4 1.362(5) . ?
C5 C6 1.379(5) . ?
C5 S1 1.723(4) . ?
C6 C7 1.440(5) . ?
C6 C8 1.443(5) . ?
C7 N1 1.321(5) . ?
C7 N2 1.349(5) . ?
C8 C9 1.333(5) . ?
C9 C10 1.493(5) . ?
C9 S1 1.746(4) . ?
C11 C12 1.375(6) . ?
C12 C13 1.379(6) . ?
C13 C14 1.377(6) . ?
C15 N2 1.478(5) . ?
C15 C16 1.503(6) . ?
C16 N3 1.488(5) . ?
C17 N3 1.491(5) . ?
C17 C18 1.510(5) . ?
C18 N2 1.470(5) . ?
C19 N3 1.479(5) . ?
C20 O1 1.235(5) . ?
C20 O2 1.261(5) . ?
C20 C21 1.494(6) . ?
C21 C22 1.328(5) . ?
C22 C23 1.484(6) . ?
C23 O4 1.203(6) . ?
C23 O3 1.294(6) . ?
C24 O5 1.234(5) . ?
C24 O6 1.261(5) . ?
C24 C25 1.507(6) . ?
C25 C26 1.317(6) . ?
C26 C27 1.477(7) . ?
C27 O8 1.220(5) . ?
C27 O7 1.299(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 C2 C3 119.7(4) . . ?
C11 C2 N1 116.2(4) . . ?
C3 C2 N1 123.5(4) . . ?
C14 C3 C2 118.5(4) . . ?
C14 C3 N4 119.1(4) . . ?
C2 C3 N4 122.4(4) . . ?
N4 C5 C6 127.8(4) . . ?
N4 C5 S1 121.0(3) . . ?
C6 C5 S1 111.2(3) . . ?
C5 C6 C7 124.2(3) . . ?
C5 C6 C8 111.7(3) . . ?
C7 C6 C8 123.8(3) . . ?
N1 C7 N2 118.3(3) . . ?
N1 C7 C6 123.0(3) . . ?
N2 C7 C6 118.7(3) . . ?
C9 C8 C6 114.0(4) . . ?
C8 C9 C10 129.0(4) . . ?
C8 C9 S1 111.0(3) . . ?
C10 C9 S1 119.9(3) . . ?
C12 C11 C2 120.9(4) . . ?
C11 C12 C13 119.6(4) . . ?
C14 C13 C12 119.8(4) . . ?
C13 C14 C3 121.5(4) . . ?
N2 C15 C16 111.6(3) . . ?
N3 C16 C15 110.2(3) . . ?
N3 C17 C18 111.1(3) . . ?
N2 C18 C17 109.5(3) . . ?
O1 C20 O2 123.2(4) . . ?
O1 C20 C21 117.8(4) . . ?
O2 C20 C21 119.0(4) . . ?
C22 C21 C20 130.9(4) . . ?
C21 C22 C23 131.0(4) . . ?
O4 C23 O3 121.3(5) . . ?
O4 C23 C22 118.5(5) . . ?
O3 C23 C22 120.1(4) . . ?
O5 C24 O6 123.9(4) . . ?
O5 C24 C25 116.7(4) . . ?
O6 C24 C25 119.4(4) . . ?
C26 C25 C24 130.6(5) . . ?
C25 C26 C27 131.8(5) . . ?
O8 C27 O7 121.1(5) . . ?
O8 C27 C26 119.0(5) . . ?
O7 C27 C26 119.9(4) . . ?
C7 N1 C2 128.7(3) . . ?
C7 N2 C18 123.0(3) . . ?
C7 N2 C15 121.1(3) . . ?
C18 N2 C15 112.2(3) . . ?
C19 N3 C16 110.7(3) . . ?
C19 N3 C17 111.4(3) . . ?
C16 N3 C17 110.6(3) . . ?
C5 N4 C3 121.8(3) . . ?
C5 S1 C9 92.04(18) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.11
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.067