# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2005

data_global

_journal_coden_Cambridge         440

loop_
_publ_author_name
'Philip Gale'
'Simon J. Brooks'
'Peter R. Edwards'
'Mark E. Light'

_publ_contact_author_name        'Philip Gale'
_publ_contact_author_address     
;
Department of Chemistry
University of Southampton
Southampton
SO17 1BJ
UNITED KINGDOM
;

_publ_contact_author_email       PHILIP.GALE@SOTON.AC.UK

_publ_requested_journal          'New Journal of Chemistry'

_publ_section_title              
;
Carboxylate complexation by a family of easy-to-make
ortho-phenylenediamine based bis-ureas: studies in solution and the
solid state
;

data_2005sot0886
_database_code_depnum_ccdc_archive 'CCDC 283635'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H36 N, C16 H14 N4 O2, F'
_chemical_formula_sum            'C32 H50 F N5 O2'
_chemical_formula_weight         555.77

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.07(3)
_cell_length_b                   16.80(3)
_cell_length_c                   17.13(3)
_cell_angle_alpha                72.25(16)
_cell_angle_beta                 74.7(2)
_cell_angle_gamma                71.82(14)
_cell_volume                     3087(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    12678
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.10

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1208
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9890
_exptl_absorpt_correction_T_max  0.9976
_exptl_absorpt_process_details   
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;

_exptl_special_details           
;
SADABS was used to perform the Absorption correction
Parameter refinement on 23580 reflections reduced R(int) from 0.1009 to 0.0634
Ratio of minimum to maximum apparent transmission: 0.617677
The given Tmin and Tmax were generated using the SHELX SIZE command
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating Anode'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_measurement_device_type  'Bruker-Nonius CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans to fill the asymmetric unit'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            61461
_diffrn_reflns_av_R_equivalents  0.1370
_diffrn_reflns_av_sigmaI/netI    0.1452
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         27.48
_reflns_number_total             13602
_reflns_number_gt                6992
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin, et al., 1993)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_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^)+(0.0500P)^2^+2.1613P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         13602
_refine_ls_number_parameters     721
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2021
_refine_ls_R_factor_gt           0.0960
_refine_ls_wR_factor_ref         0.1877
_refine_ls_wR_factor_gt          0.1573
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
F101 F 0.41426(15) 0.38611(11) 0.18065(11) 0.0344(5) Uani 1 1 d . . .
F201 F -0.07801(15) 0.88576(12) 0.17828(11) 0.0368(5) Uani 1 1 d . . .
N101 N 0.1676(2) 0.53028(16) -0.03956(16) 0.0305(6) Uani 1 1 d . . .
H901 H 0.0934 0.5387 -0.0436 0.037 Uiso 1 1 calc R . .
N102 N 0.2001(2) 0.38029(16) 0.16483(16) 0.0278(6) Uani 1 1 d . . .
H902 H 0.2724 0.3830 0.1631 0.033 Uiso 1 1 calc R . .
N103 N 0.2562(2) 0.35511(16) 0.32071(16) 0.0306(6) Uani 1 1 d . . .
H903 H 0.3146 0.3622 0.2779 0.037 Uiso 1 1 calc R . .
N104 N 0.4179(2) 0.45391(17) 0.30092(18) 0.0357(7) Uani 1 1 d . . .
H904 H 0.4231 0.4393 0.2547 0.043 Uiso 1 1 calc R . .
O101 O 0.04443(19) 0.43339(14) 0.09595(14) 0.0351(6) Uani 1 1 d . . .
O102 O 0.1758(2) 0.37958(15) 0.45185(15) 0.0414(6) Uani 1 1 d . . .
C101 C 0.2480(3) 0.5681(2) -0.0980(2) 0.0337(8) Uani 1 1 d . . .
H101 H 0.2339 0.6077 -0.1496 0.040 Uiso 1 1 calc R . .
C102 C 0.3520(3) 0.5398(2) -0.0700(2) 0.0360(8) Uani 1 1 d . . .
H102 H 0.4237 0.5559 -0.0986 0.043 Uiso 1 1 calc R . .
C103 C 0.3350(3) 0.4819(2) 0.0091(2) 0.0316(8) Uani 1 1 d . . .
H103 H 0.3928 0.4523 0.0434 0.038 Uiso 1 1 calc R . .
C104 C 0.2188(3) 0.4766(2) 0.02734(19) 0.0270(7) Uani 1 1 d . . .
C105 C 0.1475(3) 0.4287(2) 0.09763(19) 0.0279(7) Uani 1 1 d . . .
C106 C 0.1470(3) 0.3258(2) 0.2375(2) 0.0300(8) Uani 1 1 d . . .
C107 C 0.0690(3) 0.2828(2) 0.2324(2) 0.0341(8) Uani 1 1 d . . .
H107 H 0.0497 0.2899 0.1800 0.041 Uiso 1 1 calc R . .
C108 C 0.0191(3) 0.2295(2) 0.3030(2) 0.0350(8) Uani 1 1 d . . .
H108 H -0.0368 0.2024 0.2990 0.042 Uiso 1 1 calc R . .
C109 C 0.0498(3) 0.2152(2) 0.3794(2) 0.0356(8) Uani 1 1 d . . .
H109 H 0.0163 0.1776 0.4273 0.043 Uiso 1 1 calc R . .
C110 C 0.1289(3) 0.2556(2) 0.3856(2) 0.0337(8) Uani 1 1 d . . .
H110 H 0.1514 0.2450 0.4377 0.040 Uiso 1 1 calc R . .
C111 C 0.1765(3) 0.3124(2) 0.3153(2) 0.0285(8) Uani 1 1 d . . .
C112 C 0.2509(3) 0.3869(2) 0.3872(2) 0.0329(8) Uani 1 1 d . . .
C113 C 0.3401(3) 0.4334(2) 0.3752(2) 0.0318(8) Uani 1 1 d . . .
C114 C 0.3587(3) 0.4681(2) 0.4319(2) 0.0401(9) Uani 1 1 d . . .
H114 H 0.3175 0.4648 0.4879 0.048 Uiso 1 1 calc R . .
C115 C 0.4502(3) 0.5095(2) 0.3916(3) 0.0490(10) Uani 1 1 d . . .
H115 H 0.4831 0.5389 0.4156 0.059 Uiso 1 1 calc R . .
C116 C 0.4840(3) 0.5000(2) 0.3113(2) 0.0430(9) Uani 1 1 d . . .
H116 H 0.5441 0.5221 0.2700 0.052 Uiso 1 1 calc R . .
N105 N 0.0398(2) 0.62789(16) 0.24160(17) 0.0335(7) Uani 1 1 d . . .
C117 C -0.0369(3) 0.6866(2) 0.1773(2) 0.0356(8) Uani 1 1 d . . .
H11A H -0.0205 0.7443 0.1600 0.043 Uiso 1 1 calc R . .
H11B H -0.1214 0.6936 0.2047 0.043 Uiso 1 1 calc R . .
C118 C -0.0180(3) 0.6545(2) 0.0989(2) 0.0381(9) Uani 1 1 d . . .
H11C H 0.0587 0.6620 0.0627 0.046 Uiso 1 1 calc R . .
H11D H -0.0155 0.5922 0.1149 0.046 Uiso 1 1 calc R . .
C119 C -0.1192(3) 0.7053(2) 0.0512(2) 0.0449(9) Uani 1 1 d . . .
H11E H -0.1345 0.7675 0.0482 0.054 Uiso 1 1 calc R . .
H11F H -0.0945 0.6979 -0.0066 0.054 Uiso 1 1 calc R . .
C120 C -0.2328(3) 0.6768(3) 0.0913(2) 0.0516(10) Uani 1 1 d . . .
H12A H -0.2947 0.7114 0.0587 0.077 Uiso 1 1 calc R . .
H12B H -0.2584 0.6848 0.1482 0.077 Uiso 1 1 calc R . .
H12C H -0.2188 0.6156 0.0930 0.077 Uiso 1 1 calc R . .
C121 C 0.0034(3) 0.5435(2) 0.2843(2) 0.0368(8) Uani 1 1 d . . .
H12D H 0.0627 0.5053 0.3188 0.044 Uiso 1 1 calc R . .
H12E H 0.0072 0.5149 0.2406 0.044 Uiso 1 1 calc R . .
C122 C -0.1193(3) 0.5509(2) 0.3395(2) 0.0437(9) Uani 1 1 d . . .
H12F H -0.1776 0.5997 0.3112 0.052 Uiso 1 1 calc R . .
H12G H -0.1181 0.5621 0.3927 0.052 Uiso 1 1 calc R . .
C123 C -0.1555(3) 0.4666(2) 0.3568(2) 0.0438(9) Uani 1 1 d . . .
H12H H -0.0884 0.4171 0.3727 0.053 Uiso 1 1 calc R . .
H12I H -0.2231 0.4646 0.4044 0.053 Uiso 1 1 calc R . .
C124 C -0.1907(3) 0.4579(2) 0.2818(2) 0.0469(10) Uani 1 1 d . . .
H12J H -0.2134 0.4034 0.2956 0.070 Uiso 1 1 calc R . .
H12K H -0.1234 0.4584 0.2349 0.070 Uiso 1 1 calc R . .
H12L H -0.2580 0.5062 0.2663 0.070 Uiso 1 1 calc R . .
C125 C 0.1686(3) 0.6033(2) 0.1992(2) 0.0361(8) Uani 1 1 d . . .
H12M H 0.1729 0.5760 0.1544 0.043 Uiso 1 1 calc R . .
H12N H 0.2138 0.5592 0.2406 0.043 Uiso 1 1 calc R . .
C126 C 0.2296(3) 0.6765(2) 0.1616(2) 0.0375(9) Uani 1 1 d . . .
H12O H 0.2413 0.6970 0.2065 0.045 Uiso 1 1 calc R . .
H12P H 0.1797 0.7255 0.1266 0.045 Uiso 1 1 calc R . .
C127 C 0.3501(3) 0.6440(2) 0.1083(2) 0.0375(8) Uani 1 1 d . . .
H12Q H 0.3920 0.5878 0.1403 0.045 Uiso 1 1 calc R . .
H12R H 0.3368 0.6344 0.0576 0.045 Uiso 1 1 calc R . .
C128 C 0.4274(3) 0.7067(2) 0.0828(2) 0.0494(10) Uani 1 1 d . . .
H12S H 0.5031 0.6832 0.0490 0.074 Uiso 1 1 calc R . .
H12T H 0.4422 0.7154 0.1328 0.074 Uiso 1 1 calc R . .
H12U H 0.3870 0.7621 0.0501 0.074 Uiso 1 1 calc R . .
C129 C 0.0228(3) 0.6788(2) 0.3053(2) 0.0351(8) Uani 1 1 d . . .
H12V H -0.0626 0.6935 0.3302 0.042 Uiso 1 1 calc R . .
H12W H 0.0452 0.7337 0.2756 0.042 Uiso 1 1 calc R . .
C130 C 0.0926(3) 0.6340(2) 0.3757(2) 0.0448(9) Uani 1 1 d . . .
H13A H 0.1764 0.6092 0.3524 0.054 Uiso 1 1 calc R . .
H13B H 0.0590 0.5863 0.4141 0.054 Uiso 1 1 calc R . .
C131 C 0.0866(3) 0.6990(3) 0.4233(2) 0.0485(10) Uani 1 1 d . . .
H13C H 0.0028 0.7312 0.4368 0.058 Uiso 1 1 calc R . .
H13D H 0.1139 0.6672 0.4766 0.058 Uiso 1 1 calc R . .
C132 C 0.1602(3) 0.7630(3) 0.3760(2) 0.0538(11) Uani 1 1 d . . .
H13E H 0.1518 0.8029 0.4099 0.081 Uiso 1 1 calc R . .
H13F H 0.1328 0.7957 0.3236 0.081 Uiso 1 1 calc R . .
H13G H 0.2438 0.7320 0.3639 0.081 Uiso 1 1 calc R . .
N201 N -0.3368(2) 1.03184(17) -0.03726(17) 0.0336(7) Uani 1 1 d . . .
H801 H -0.4103 1.0378 -0.0412 0.040 Uiso 1 1 calc R . .
N202 N -0.2998(2) 0.88493(16) 0.16791(16) 0.0303(6) Uani 1 1 d . . .
H802 H -0.2298 0.8919 0.1662 0.036 Uiso 1 1 calc R . .
N203 N -0.2284(2) 0.85382(16) 0.32006(16) 0.0301(6) Uani 1 1 d . . .
H803 H -0.1749 0.8646 0.2748 0.036 Uiso 1 1 calc R . .
N204 N -0.0604(2) 0.94903(17) 0.29834(18) 0.0378(7) Uani 1 1 d . . .
H804 H -0.0569 0.9349 0.2522 0.045 Uiso 1 1 calc R . .
O201 O -0.45395(18) 0.93034(14) 0.09847(14) 0.0348(6) Uani 1 1 d . . .
O202 O -0.2925(2) 0.86798(16) 0.45511(15) 0.0430(6) Uani 1 1 d . . .
C201 C 0.0078(3) 0.9943(2) 0.3076(3) 0.0490(10) Uani 1 1 d . . .
H201 H 0.0672 1.0165 0.2655 0.059 Uiso 1 1 calc R . .
C202 C -0.0233(4) 1.0031(2) 0.3886(3) 0.0497(10) Uani 1 1 d . . .
H202 H 0.0113 1.0317 0.4123 0.060 Uiso 1 1 calc R . .
C203 C -0.1151(3) 0.9622(2) 0.4297(2) 0.0420(9) Uani 1 1 d . . .
H203 H -0.1549 0.9584 0.4860 0.050 Uiso 1 1 calc R . .
C204 C -0.1367(3) 0.9284(2) 0.3729(2) 0.0342(8) Uani 1 1 d . . .
C205 C -0.2251(3) 0.8805(2) 0.3869(2) 0.0321(8) Uani 1 1 d . . .
C206 C -0.3090(3) 0.8108(2) 0.3168(2) 0.0281(8) Uani 1 1 d . . .
C207 C -0.3501(3) 0.7504(2) 0.3873(2) 0.0335(8) Uani 1 1 d . . .
H207 H -0.3229 0.7383 0.4379 0.040 Uiso 1 1 calc R . .
C208 C -0.4287(3) 0.7092(2) 0.3833(2) 0.0359(8) Uani 1 1 d . . .
H208 H -0.4566 0.6689 0.4311 0.043 Uiso 1 1 calc R . .
C209 C -0.4679(3) 0.7263(2) 0.3094(2) 0.0401(9) Uani 1 1 d . . .
H209 H -0.5238 0.6983 0.3071 0.048 Uiso 1 1 calc R . .
C210 C -0.4258(3) 0.7845(2) 0.2383(2) 0.0353(8) Uani 1 1 d . . .
H210 H -0.4518 0.7946 0.1876 0.042 Uiso 1 1 calc R . .
C211 C -0.3465(3) 0.8273(2) 0.2413(2) 0.0288(8) Uani 1 1 d . . .
C212 C -0.3524(3) 0.9301(2) 0.1005(2) 0.0288(8) Uani 1 1 d . . .
C213 C -0.2840(3) 0.9807(2) 0.0296(2) 0.0317(8) Uani 1 1 d . . .
C214 C -0.1702(3) 0.9898(2) 0.0122(2) 0.0360(8) Uani 1 1 d . . .
H214 H -0.1127 0.9625 0.0470 0.043 Uiso 1 1 calc R . .
C215 C -0.1546(3) 1.0473(2) -0.0675(2) 0.0397(9) Uani 1 1 d . . .
H215 H -0.0844 1.0656 -0.0960 0.048 Uiso 1 1 calc R . .
C216 C -0.2583(3) 1.0716(2) -0.0960(2) 0.0359(8) Uani 1 1 d . . .
H216 H -0.2731 1.1098 -0.1480 0.043 Uiso 1 1 calc R . .
N205 N -0.5542(2) 0.85819(16) 0.74609(17) 0.0343(7) Uani 1 1 d . . .
C217 C -0.4549(3) 0.8218(2) 0.7968(2) 0.0357(8) Uani 1 1 d . . .
H21A H -0.4512 0.7600 0.8236 0.043 Uiso 1 1 calc R . .
H21B H -0.3784 0.8251 0.7583 0.043 Uiso 1 1 calc R . .
C218 C -0.4691(3) 0.8680(2) 0.8642(2) 0.0416(9) Uani 1 1 d . . .
H21C H -0.4894 0.9313 0.8406 0.050 Uiso 1 1 calc R . .
H21D H -0.5348 0.8538 0.9102 0.050 Uiso 1 1 calc R . .
C219 C -0.3551(3) 0.8412(2) 0.8982(2) 0.0476(10) Uani 1 1 d . . .
H21E H -0.3735 0.8544 0.9534 0.057 Uiso 1 1 calc R . .
H21F H -0.3225 0.7780 0.9061 0.057 Uiso 1 1 calc R . .
C220 C -0.2620(3) 0.8864(3) 0.8411(3) 0.0557(11) Uani 1 1 d . . .
H22A H -0.1907 0.8672 0.8659 0.083 Uiso 1 1 calc R . .
H22B H -0.2932 0.9490 0.8338 0.083 Uiso 1 1 calc R . .
H22C H -0.2418 0.8724 0.7868 0.083 Uiso 1 1 calc R . .
C221 C -0.6748(3) 0.8697(2) 0.8038(2) 0.0373(9) Uani 1 1 d . . .
H22D H -0.7375 0.8946 0.7695 0.045 Uiso 1 1 calc R . .
H22E H -0.6816 0.9114 0.8360 0.045 Uiso 1 1 calc R . .
C222 C -0.6965(3) 0.7858(2) 0.8646(2) 0.0427(9) Uani 1 1 d . . .
H22F H -0.6982 0.7459 0.8329 0.051 Uiso 1 1 calc R . .
H22G H -0.6303 0.7578 0.8956 0.051 Uiso 1 1 calc R . .
C223 C -0.8130(3) 0.8021(3) 0.9260(2) 0.0535(11) Uani 1 1 d . . .
H22H H -0.8200 0.7473 0.9676 0.064 Uiso 1 1 calc R . .
H22I H -0.8116 0.8434 0.9563 0.064 Uiso 1 1 calc R . .
C224 C -0.9189(4) 0.8371(3) 0.8858(3) 0.0825(17) Uani 1 1 d . . .
H22J H -0.9907 0.8464 0.9285 0.124 Uiso 1 1 calc R . .
H22K H -0.9222 0.7959 0.8571 0.124 Uiso 1 1 calc R . .
H22L H -0.9136 0.8921 0.8454 0.124 Uiso 1 1 calc R . .
C225 C -0.5390(3) 0.7941(2) 0.6952(2) 0.0354(8) Uani 1 1 d . . .
H22M H -0.4637 0.7933 0.6542 0.042 Uiso 1 1 calc R . .
H22N H -0.5317 0.7357 0.7331 0.042 Uiso 1 1 calc R . .
C226 C -0.6389(3) 0.8128(2) 0.6486(2) 0.0391(9) Uani 1 1 d . . .
H22O H -0.6540 0.8734 0.6154 0.047 Uiso 1 1 calc R . .
H22P H -0.7125 0.8046 0.6889 0.047 Uiso 1 1 calc R . .
C227 C -0.6049(3) 0.7520(2) 0.5910(2) 0.0426(9) Uani 1 1 d . . .
H22Q H -0.5375 0.7658 0.5464 0.051 Uiso 1 1 calc R . .
H22R H -0.5784 0.6919 0.6233 0.051 Uiso 1 1 calc R . .
C228 C -0.7071(3) 0.7588(3) 0.5516(2) 0.0493(10) Uani 1 1 d . . .
H22S H -0.6814 0.7187 0.5153 0.074 Uiso 1 1 calc R . .
H22T H -0.7326 0.8179 0.5187 0.074 Uiso 1 1 calc R . .
H22U H -0.7735 0.7440 0.5955 0.074 Uiso 1 1 calc R . .
C229 C -0.5469(3) 0.9467(2) 0.6887(2) 0.0373(9) Uani 1 1 d . . .
H22V H -0.5447 0.9841 0.7228 0.045 Uiso 1 1 calc R . .
H22W H -0.6205 0.9727 0.6652 0.045 Uiso 1 1 calc R . .
C230 C -0.4407(3) 0.9475(2) 0.6163(2) 0.0422(9) Uani 1 1 d . . .
H23A H -0.4574 0.9317 0.5702 0.051 Uiso 1 1 calc R . .
H23B H -0.3699 0.9041 0.6351 0.051 Uiso 1 1 calc R . .
C231 C -0.4152(3) 1.0368(2) 0.5847(2) 0.0465(10) Uani 1 1 d . . .
H23C H -0.3631 1.0406 0.5291 0.056 Uiso 1 1 calc R . .
H23D H -0.4908 1.0813 0.5782 0.056 Uiso 1 1 calc R . .
C232 C -0.3569(4) 1.0557(3) 0.6421(3) 0.0587(11) Uani 1 1 d . . .
H23E H -0.3440 1.1139 0.6194 0.088 Uiso 1 1 calc R . .
H23F H -0.2805 1.0133 0.6470 0.088 Uiso 1 1 calc R . .
H23G H -0.4082 1.0524 0.6973 0.088 Uiso 1 1 calc R . .

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
F101 0.0285(10) 0.0367(11) 0.0355(11) -0.0049(9) -0.0072(8) -0.0078(9)
F201 0.0330(10) 0.0429(12) 0.0382(12) -0.0102(9) -0.0038(9) -0.0167(9)
N101 0.0292(15) 0.0318(15) 0.0302(16) -0.0077(13) -0.0063(13) -0.0067(13)
N102 0.0256(14) 0.0289(15) 0.0283(16) -0.0060(12) -0.0039(12) -0.0079(12)
N103 0.0294(15) 0.0339(16) 0.0301(17) -0.0070(13) -0.0028(12) -0.0131(13)
N104 0.0376(16) 0.0374(17) 0.0370(18) -0.0067(14) -0.0136(14) -0.0131(14)
O101 0.0295(13) 0.0394(14) 0.0367(14) -0.0053(11) -0.0061(10) -0.0128(11)
O102 0.0431(14) 0.0479(15) 0.0366(15) -0.0175(12) 0.0002(12) -0.0152(12)
C101 0.043(2) 0.0332(19) 0.026(2) -0.0048(16) -0.0043(16) -0.0152(17)
C102 0.0324(19) 0.045(2) 0.031(2) -0.0089(17) -0.0009(16) -0.0140(17)
C103 0.0299(18) 0.038(2) 0.030(2) -0.0098(16) -0.0091(15) -0.0095(16)
C104 0.0317(18) 0.0288(18) 0.0209(18) -0.0084(15) -0.0062(14) -0.0050(15)
C105 0.0323(19) 0.0267(18) 0.0272(19) -0.0115(15) -0.0037(15) -0.0076(16)
C106 0.0284(18) 0.0237(17) 0.036(2) -0.0089(15) -0.0048(15) -0.0033(15)
C107 0.040(2) 0.0304(19) 0.038(2) -0.0114(17) -0.0090(16) -0.0119(17)
C108 0.0365(19) 0.0316(19) 0.040(2) -0.0082(17) -0.0079(17) -0.0134(16)
C109 0.036(2) 0.0284(19) 0.037(2) -0.0025(16) 0.0008(16) -0.0120(16)
C110 0.0360(19) 0.0337(19) 0.027(2) -0.0080(16) -0.0035(15) -0.0049(16)
C111 0.0245(17) 0.0262(18) 0.034(2) -0.0112(15) -0.0026(15) -0.0035(15)
C112 0.0327(19) 0.0282(18) 0.033(2) -0.0071(16) -0.0081(17) -0.0007(16)
C113 0.0306(18) 0.0284(18) 0.036(2) -0.0083(16) -0.0074(16) -0.0050(15)
C114 0.044(2) 0.038(2) 0.042(2) -0.0132(18) -0.0158(18) -0.0055(18)
C115 0.060(3) 0.045(2) 0.056(3) -0.010(2) -0.029(2) -0.020(2)
C116 0.043(2) 0.043(2) 0.048(3) -0.0012(19) -0.0164(18) -0.0203(18)
N105 0.0327(16) 0.0256(15) 0.0392(18) -0.0117(13) -0.0052(13) -0.0009(13)
C117 0.037(2) 0.0295(18) 0.038(2) -0.0107(16) -0.0112(16) -0.0007(16)
C118 0.042(2) 0.035(2) 0.037(2) -0.0138(17) -0.0034(17) -0.0083(17)
C119 0.061(3) 0.037(2) 0.035(2) -0.0132(17) -0.0139(19) -0.0026(19)
C120 0.051(2) 0.053(2) 0.053(3) -0.019(2) -0.016(2) -0.005(2)
C121 0.040(2) 0.0262(18) 0.041(2) -0.0106(16) -0.0064(17) -0.0022(16)
C122 0.042(2) 0.043(2) 0.042(2) -0.0153(18) 0.0030(17) -0.0091(18)
C123 0.044(2) 0.039(2) 0.042(2) -0.0114(18) 0.0041(17) -0.0110(18)
C124 0.043(2) 0.052(2) 0.046(2) -0.0115(19) -0.0025(18) -0.0177(19)
C125 0.0320(19) 0.0329(19) 0.039(2) -0.0127(16) -0.0055(16) 0.0003(16)
C126 0.038(2) 0.033(2) 0.040(2) -0.0108(17) -0.0089(16) -0.0035(17)
C127 0.0347(19) 0.034(2) 0.043(2) -0.0112(17) -0.0046(16) -0.0074(16)
C128 0.044(2) 0.050(2) 0.057(3) -0.020(2) 0.0018(19) -0.019(2)
C129 0.0349(19) 0.0316(19) 0.038(2) -0.0140(16) -0.0062(16) -0.0018(16)
C130 0.051(2) 0.044(2) 0.037(2) -0.0052(18) -0.0135(18) -0.0079(19)
C131 0.049(2) 0.058(3) 0.038(2) -0.017(2) -0.0141(18) -0.001(2)
C132 0.057(3) 0.059(3) 0.055(3) -0.018(2) -0.023(2) -0.014(2)
N201 0.0298(15) 0.0334(16) 0.0372(18) -0.0088(14) -0.0084(13) -0.0052(13)
N202 0.0286(15) 0.0318(15) 0.0332(17) -0.0086(13) -0.0058(13) -0.0105(13)
N203 0.0277(14) 0.0330(16) 0.0296(16) -0.0105(13) -0.0034(12) -0.0064(13)
N204 0.0439(17) 0.0340(17) 0.0422(19) -0.0064(14) -0.0171(15) -0.0141(14)
O201 0.0271(13) 0.0388(14) 0.0374(14) -0.0067(11) -0.0070(10) -0.0085(11)
O202 0.0363(14) 0.0547(16) 0.0395(16) -0.0186(13) -0.0051(12) -0.0082(12)
C201 0.055(2) 0.046(2) 0.056(3) -0.003(2) -0.020(2) -0.027(2)
C202 0.067(3) 0.037(2) 0.059(3) -0.008(2) -0.035(2) -0.017(2)
C203 0.048(2) 0.036(2) 0.049(2) -0.0140(18) -0.0216(19) -0.0056(18)
C204 0.0344(19) 0.0291(19) 0.039(2) -0.0079(16) -0.0140(17) -0.0018(16)
C205 0.0306(19) 0.0273(18) 0.036(2) -0.0115(16) -0.0100(17) 0.0025(15)
C206 0.0223(17) 0.0252(17) 0.035(2) -0.0097(15) -0.0024(15) -0.0033(14)
C207 0.0309(18) 0.0318(19) 0.035(2) -0.0085(16) -0.0061(15) -0.0044(16)
C208 0.039(2) 0.034(2) 0.033(2) -0.0073(16) -0.0006(16) -0.0128(17)
C209 0.038(2) 0.041(2) 0.046(2) -0.0129(19) -0.0008(17) -0.0194(18)
C210 0.0347(19) 0.037(2) 0.037(2) -0.0120(17) -0.0067(16) -0.0116(17)
C211 0.0258(17) 0.0248(17) 0.034(2) -0.0111(15) -0.0026(15) -0.0025(15)
C212 0.0242(18) 0.0262(18) 0.036(2) -0.0135(16) -0.0040(15) -0.0016(15)
C213 0.0313(19) 0.0288(18) 0.035(2) -0.0115(16) -0.0083(16) -0.0024(16)
C214 0.0322(19) 0.038(2) 0.039(2) -0.0120(17) -0.0062(16) -0.0085(16)
C215 0.036(2) 0.043(2) 0.040(2) -0.0101(18) -0.0011(17) -0.0158(18)
C216 0.041(2) 0.0317(19) 0.033(2) -0.0082(16) -0.0030(17) -0.0102(17)
N205 0.0358(16) 0.0251(15) 0.0381(17) -0.0092(13) -0.0056(13) -0.0016(13)
C217 0.0349(19) 0.0323(19) 0.039(2) -0.0100(16) -0.0092(16) -0.0039(16)
C218 0.049(2) 0.040(2) 0.037(2) -0.0151(17) -0.0035(17) -0.0116(18)
C219 0.057(2) 0.042(2) 0.048(2) -0.0193(19) -0.013(2) -0.008(2)
C220 0.052(2) 0.058(3) 0.066(3) -0.030(2) -0.010(2) -0.011(2)
C221 0.0347(19) 0.033(2) 0.039(2) -0.0112(17) -0.0016(16) -0.0042(16)
C222 0.041(2) 0.044(2) 0.041(2) -0.0052(18) -0.0056(17) -0.0138(18)
C223 0.062(3) 0.058(3) 0.045(2) -0.015(2) 0.003(2) -0.030(2)
C224 0.038(2) 0.078(3) 0.092(4) 0.017(3) 0.004(2) -0.010(2)
C225 0.0350(19) 0.0285(18) 0.039(2) -0.0138(16) -0.0052(16) 0.0004(16)
C226 0.0334(19) 0.037(2) 0.041(2) -0.0079(17) -0.0088(16) 0.0001(17)
C227 0.0336(19) 0.051(2) 0.045(2) -0.0197(19) -0.0091(17) -0.0042(18)
C228 0.048(2) 0.057(3) 0.048(3) -0.014(2) -0.0132(19) -0.015(2)
C229 0.0356(19) 0.0269(18) 0.041(2) -0.0053(16) -0.0021(16) -0.0027(16)
C230 0.041(2) 0.036(2) 0.038(2) -0.0073(17) 0.0007(17) -0.0012(17)
C231 0.035(2) 0.041(2) 0.047(2) -0.0018(19) -0.0002(18) -0.0032(18)
C232 0.056(3) 0.049(3) 0.068(3) -0.011(2) -0.003(2) -0.019(2)

_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
N101 C101 1.353(5) . ?
N101 C104 1.380(5) . ?
N102 C105 1.372(5) . ?
N102 C106 1.431(5) . ?
N103 C112 1.377(5) . ?
N103 C111 1.402(5) . ?
N104 C116 1.346(5) . ?
N104 C113 1.387(5) . ?
O101 C105 1.230(5) . ?
O102 C112 1.233(5) . ?
C101 C102 1.357(6) . ?
C102 C103 1.414(5) . ?
C103 C104 1.380(6) . ?
C104 C105 1.459(6) . ?
C106 C107 1.387(5) . ?
C106 C111 1.404(5) . ?
C107 C108 1.385(6) . ?
C108 C109 1.385(5) . ?
C109 C110 1.373(5) . ?
C110 C111 1.404(5) . ?
C112 C113 1.458(5) . ?
C113 C114 1.370(5) . ?
C114 C115 1.401(6) . ?
C115 C116 1.371(6) . ?
N105 C125 1.516(6) . ?
N105 C129 1.517(5) . ?
N105 C121 1.524(5) . ?
N105 C117 1.532(5) . ?
C117 C118 1.534(5) . ?
C118 C119 1.529(6) . ?
C119 C120 1.514(6) . ?
C121 C122 1.524(6) . ?
C122 C123 1.532(6) . ?
C123 C124 1.516(5) . ?
C125 C126 1.517(6) . ?
C126 C127 1.533(6) . ?
C127 C128 1.513(6) . ?
C129 C130 1.523(6) . ?
C130 C131 1.525(6) . ?
C131 C132 1.513(6) . ?
N201 C216 1.355(5) . ?
N201 C213 1.379(5) . ?
N202 C212 1.367(5) . ?
N202 C211 1.436(5) . ?
N203 C205 1.365(5) . ?
N203 C206 1.402(5) . ?
N204 C201 1.348(5) . ?
N204 C204 1.380(6) . ?
O201 C212 1.233(5) . ?
O202 C205 1.235(5) . ?
C201 C202 1.379(6) . ?
C202 C203 1.401(6) . ?
C203 C204 1.379(5) . ?
C204 C205 1.458(6) . ?
C206 C211 1.403(5) . ?
C206 C207 1.408(5) . ?
C207 C208 1.362(5) . ?
C208 C209 1.384(5) . ?
C209 C210 1.398(6) . ?
C210 C211 1.383(5) . ?
C212 C213 1.469(6) . ?
C213 C214 1.372(6) . ?
C214 C215 1.417(6) . ?
C215 C216 1.361(6) . ?
N205 C221 1.522(6) . ?
N205 C225 1.523(5) . ?
N205 C229 1.526(5) . ?
N205 C217 1.528(6) . ?
C217 C218 1.525(5) . ?
C218 C219 1.519(6) . ?
C219 C220 1.515(6) . ?
C221 C222 1.526(6) . ?
C222 C223 1.522(7) . ?
C223 C224 1.484(7) . ?
C225 C226 1.520(6) . ?
C226 C227 1.523(6) . ?
C227 C228 1.515(6) . ?
C229 C230 1.530(6) . ?
C230 C231 1.530(6) . ?
C231 C232 1.502(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
C101 N101 C104 110.2(3) . . ?
C105 N102 C106 125.4(3) . . ?
C112 N103 C111 125.6(3) . . ?
C116 N104 C113 108.6(3) . . ?
N101 C101 C102 108.1(3) . . ?
C101 C102 C103 107.9(4) . . ?
C104 C103 C102 107.4(4) . . ?
C103 C104 N101 106.5(3) . . ?
C103 C104 C105 134.2(3) . . ?
N101 C104 C105 119.3(3) . . ?
O101 C105 N102 122.4(3) . . ?
O101 C105 C104 120.5(3) . . ?
N102 C105 C104 117.2(3) . . ?
C107 C106 C111 118.6(3) . . ?
C107 C106 N102 121.0(3) . . ?
C111 C106 N102 120.3(3) . . ?
C108 C107 C106 120.6(4) . . ?
C109 C108 C107 120.8(3) . . ?
C110 C109 C108 119.7(3) . . ?
C109 C110 C111 120.2(3) . . ?
N103 C111 C106 118.8(3) . . ?
N103 C111 C110 121.0(3) . . ?
C106 C111 C110 120.2(3) . . ?
O102 C112 N103 124.1(3) . . ?
O102 C112 C113 121.0(3) . . ?
N103 C112 C113 114.9(3) . . ?
C114 C113 N104 108.1(3) . . ?
C114 C113 C112 127.3(4) . . ?
N104 C113 C112 124.6(3) . . ?
C113 C114 C115 106.8(4) . . ?
C116 C115 C114 107.9(4) . . ?
N104 C116 C115 108.6(4) . . ?
C125 N105 C129 112.0(3) . . ?
C125 N105 C121 106.4(3) . . ?
C129 N105 C121 110.1(3) . . ?
C125 N105 C117 110.2(3) . . ?
C129 N105 C117 106.1(3) . . ?
C121 N105 C117 112.1(3) . . ?
N105 C117 C118 115.3(3) . . ?
C119 C118 C117 109.8(3) . . ?
C120 C119 C118 112.7(4) . . ?
N105 C121 C122 116.3(3) . . ?
C121 C122 C123 109.2(3) . . ?
C124 C123 C122 112.2(3) . . ?
N105 C125 C126 116.0(3) . . ?
C125 C126 C127 109.1(3) . . ?
C128 C127 C126 112.4(3) . . ?
N105 C129 C130 116.0(3) . . ?
C129 C130 C131 109.5(3) . . ?
C132 C131 C130 113.9(4) . . ?
C216 N201 C213 109.7(3) . . ?
C212 N202 C211 126.9(3) . . ?
C205 N203 C206 126.1(3) . . ?
C201 N204 C204 109.1(3) . . ?
N204 C201 C202 108.4(4) . . ?
C201 C202 C203 107.7(4) . . ?
C204 C203 C202 107.0(4) . . ?
C203 C204 N204 107.9(3) . . ?
C203 C204 C205 127.0(4) . . ?
N204 C204 C205 125.1(3) . . ?
O202 C205 N203 124.2(3) . . ?
O202 C205 C204 120.4(3) . . ?
N203 C205 C204 115.4(3) . . ?
N203 C206 C211 118.9(3) . . ?
N203 C206 C207 121.0(3) . . ?
C211 C206 C207 120.1(3) . . ?
C208 C207 C206 120.4(4) . . ?
C207 C208 C209 119.9(4) . . ?
C208 C209 C210 120.5(4) . . ?
C211 C210 C209 120.4(4) . . ?
C210 C211 C206 118.7(3) . . ?
C210 C211 N202 120.8(3) . . ?
C206 C211 N202 120.5(3) . . ?
O201 C212 N202 122.3(3) . . ?
O201 C212 C213 120.4(3) . . ?
N202 C212 C213 117.3(3) . . ?
C214 C213 N201 107.2(4) . . ?
C214 C213 C212 133.6(3) . . ?
N201 C213 C212 119.1(3) . . ?
C213 C214 C215 107.2(4) . . ?
C216 C215 C214 107.6(4) . . ?
N201 C216 C215 108.2(4) . . ?
C221 N205 C225 111.0(3) . . ?
C221 N205 C229 107.4(3) . . ?
C225 N205 C229 110.4(3) . . ?
C221 N205 C217 110.3(3) . . ?
C225 N205 C217 106.9(3) . . ?
C229 N205 C217 110.9(3) . . ?
C218 C217 N205 114.5(3) . . ?
C219 C218 C217 110.6(3) . . ?
C220 C219 C218 112.7(4) . . ?
N205 C221 C222 113.6(3) . . ?
C223 C222 C221 111.4(4) . . ?
C224 C223 C222 113.4(4) . . ?
C226 C225 N205 115.0(3) . . ?
C225 C226 C227 109.7(3) . . ?
C228 C227 C226 112.3(3) . . ?
N205 C229 C230 115.9(3) . . ?
C229 C230 C231 110.9(3) . . ?
C232 C231 C230 113.0(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N101 H901 O101 0.88 1.96 2.798(8) 158.9 2_565
N102 H902 F101 0.88 1.83 2.704(7) 169.2 .
N103 H903 F101 0.88 1.79 2.666(8) 170.3 .
N104 H904 F101 0.88 1.80 2.656(5) 163.7 .
N201 H801 O201 0.88 1.98 2.806(8) 156.2 2_475
N202 H802 F201 0.88 1.87 2.733(7) 168.6 .
N203 H803 F201 0.88 1.76 2.639(8) 174.1 .
N204 H804 F201 0.88 1.81 2.666(5) 162.9 .

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.049

#===END

data_2005sot0607
_database_code_depnum_ccdc_archive 'CCDC 283636'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H50 Cl N5 O2'
_chemical_formula_weight         572.22

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.298(5)
_cell_length_b                   9.0305(14)
_cell_length_c                   20.379(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.76(2)
_cell_angle_gamma                90.00
_cell_volume                     3296.8(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7509
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.10

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1240
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9634
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_process_details   
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;

_exptl_special_details           
;
SADABS was used to perform the Absorption correction
Parameter refinement on 18103 reflections reduced R(int) from 0.1416 to 0.0565
Ratio of minimum to maximum apparent transmission: 0.583527
The given Tmin and Tmax were generated using the SHELX SIZE command
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating Anode'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_measurement_device_type  'Bruker-Nonius CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans to fill the asymmetric unit'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            38786
_diffrn_reflns_av_R_equivalents  0.0903
_diffrn_reflns_av_sigmaI/netI    0.0926
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         27.16
_reflns_number_total             7224
_reflns_number_gt                3765
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin, et al., 1993)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_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.

The refinement is, to all intenets and purposes, not a good one. Several
data collections were tried but all gave the same results. It is likely
that the refinement quality is due either to high thermal motion within
the crystal, or some form of undetected twinning.
;

_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^)+(0.2000P)^2^+0.0000P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7224
_refine_ls_number_parameters     361
_refine_ls_number_restraints     460
_refine_ls_R_factor_all          0.2671
_refine_ls_R_factor_gt           0.1843
_refine_ls_wR_factor_ref         0.5371
_refine_ls_wR_factor_gt          0.4916
_refine_ls_goodness_of_fit_ref   1.895
_refine_ls_restrained_S_all      1.942
_refine_ls_shift/su_max          0.042
_refine_ls_shift/su_mean         0.004

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
N1 N 0.5131(3) 1.0212(6) 0.1084(3) 0.0453(14) Uani 1 1 d U . .
H91 H 0.5268 1.0406 0.0704 0.054 Uiso 1 1 calc R . .
N2 N 0.3401(3) 0.8144(6) 0.0600(2) 0.0415(13) Uani 1 1 d U . .
H92 H 0.3317 0.7994 0.1004 0.050 Uiso 1 1 calc R . .
N3 N 0.1833(3) 0.7965(6) 0.0629(3) 0.0517(16) Uani 1 1 d U . .
H93 H 0.2095 0.7807 0.1035 0.062 Uiso 1 1 calc R . .
N4 N 0.0272(3) 0.9901(7) 0.1095(3) 0.0586(17) Uani 1 1 d U . .
H94 H -0.0034 1.0074 0.0710 0.070 Uiso 1 1 calc R . .
O1 O 0.4133(3) 0.9291(7) -0.0022(2) 0.0628(15) Uani 1 1 d U . .
O2 O 0.0775(3) 0.8963(6) 0.0002(2) 0.0647(16) Uani 1 1 d U . .
C1 C 0.5503(4) 1.0657(7) 0.1696(3) 0.0461(17) Uani 1 1 d U . .
H1 H 0.5957 1.1199 0.1788 0.055 Uiso 1 1 calc R . .
C2 C 0.5103(4) 1.0183(7) 0.2161(4) 0.0492(18) Uani 1 1 d U . .
H2 H 0.5228 1.0365 0.2630 0.059 Uiso 1 1 calc R . .
C3 C 0.4478(4) 0.9384(7) 0.1826(3) 0.0413(16) Uani 1 1 d U . .
H3 H 0.4110 0.8921 0.2023 0.050 Uiso 1 1 calc R . .
C4 C 0.4504(4) 0.9404(7) 0.1146(3) 0.0402(15) Uani 1 1 d U . .
C5 C 0.4007(4) 0.8919(7) 0.0545(3) 0.0440(16) Uani 1 1 d U . .
C6 C 0.2882(4) 0.7545(7) 0.0048(3) 0.0461(16) Uani 1 1 d U . .
C7 C 0.3135(5) 0.7016(8) -0.0499(4) 0.061(2) Uani 1 1 d U . .
H7 H 0.3654 0.7052 -0.0497 0.073 Uiso 1 1 calc R . .
C8 C 0.2652(6) 0.6432(10) -0.1051(5) 0.079(3) Uani 1 1 d U . .
H8 H 0.2840 0.6084 -0.1425 0.095 Uiso 1 1 calc R . .
C9 C 0.1930(6) 0.6361(11) -0.1058(5) 0.088(3) Uani 1 1 d U . .
H9 H 0.1597 0.6016 -0.1448 0.106 Uiso 1 1 calc R . .
C10 C 0.1646(6) 0.6796(10) -0.0488(5) 0.076(2) Uani 1 1 d U . .
H10 H 0.1134 0.6648 -0.0478 0.091 Uiso 1 1 calc R . .
C11 C 0.2129(4) 0.7447(8) 0.0062(4) 0.0514(17) Uani 1 1 d U . .
C12 C 0.1164(4) 0.8690(8) 0.0561(4) 0.0509(18) Uani 1 1 d U . .
C13 C 0.0933(4) 0.9168(8) 0.1156(4) 0.0524(18) Uani 1 1 d U . .
C14 C 0.1241(5) 0.9090(9) 0.1850(4) 0.067(2) Uani 1 1 d U . .
H14 H 0.1699 0.8635 0.2055 0.080 Uiso 1 1 calc R . .
C15 C 0.0745(5) 0.9804(10) 0.2173(5) 0.077(3) Uani 1 1 d U . .
H15 H 0.0807 0.9916 0.2645 0.092 Uiso 1 1 calc R . .
C16 C 0.0140(5) 1.0333(9) 0.1699(4) 0.066(2) Uani 1 1 d U . .
H16 H -0.0275 1.0880 0.1782 0.080 Uiso 1 1 calc R . .
N5 N 0.2520(3) 0.2843(6) 0.0917(3) 0.0654(19) Uani 1 1 d DU . .
C17 C 0.3159(4) 0.3773(9) 0.0763(5) 0.076(2) Uani 1 1 d DU . .
H17A H 0.2970 0.4400 0.0366 0.092 Uiso 1 1 calc R . .
H17B H 0.3346 0.4438 0.1147 0.092 Uiso 1 1 calc R . .
C18 C 0.3786(4) 0.2856(9) 0.0631(6) 0.098(3) Uani 1 1 d DU . .
H18A H 0.3594 0.2145 0.0267 0.117 Uiso 1 1 calc R . .
H18B H 0.3999 0.2280 0.1038 0.117 Uiso 1 1 calc R . .
C19 C 0.4388(5) 0.3773(10) 0.0436(4) 0.086(3) Uani 1 1 d DU . .
H19A H 0.4743 0.3121 0.0266 0.103 Uiso 1 1 calc R . .
H19B H 0.4166 0.4464 0.0073 0.103 Uiso 1 1 calc R . .
C20 C 0.4790(6) 0.4621(11) 0.1018(5) 0.095(3) Uani 1 1 d DU . .
H20A H 0.5186 0.5209 0.0884 0.143 Uiso 1 1 calc R . .
H20B H 0.5012 0.3935 0.1376 0.143 Uiso 1 1 calc R . .
H20C H 0.4440 0.5281 0.1179 0.143 Uiso 1 1 calc R . .
C21 C 0.2245(5) 0.1779(9) 0.0346(3) 0.073(2) Uani 1 1 d DU . .
H21A H 0.2656 0.1090 0.0311 0.087 Uiso 1 1 calc R . .
H21B H 0.1833 0.1184 0.0458 0.087 Uiso 1 1 calc R . .
C22 C 0.1981(6) 0.2475(10) -0.0310(3) 0.086(3) Uani 1 1 d DU . .
H22A H 0.2362 0.3173 -0.0408 0.103 Uiso 1 1 calc R . .
H22B H 0.1517 0.3038 -0.0308 0.103 Uiso 1 1 calc R . .
C23 C 0.1834(7) 0.1283(11) -0.0839(4) 0.104(3) Uani 1 1 d DU . .
H23A H 0.2307 0.0786 -0.0872 0.125 Uiso 1 1 calc R . .
H23B H 0.1490 0.0531 -0.0718 0.125 Uiso 1 1 calc R . .
C24 C 0.1495(8) 0.1977(15) -0.1491(4) 0.134(5) Uani 1 1 d DU . .
H24A H 0.1398 0.1215 -0.1840 0.201 Uiso 1 1 calc R . .
H24B H 0.1839 0.2718 -0.1607 0.201 Uiso 1 1 calc R . .
H24C H 0.1024 0.2457 -0.1455 0.201 Uiso 1 1 calc R . .
C25 C 0.2751(5) 0.1877(8) 0.1535(3) 0.062(2) Uani 1 1 d DU . .
H25A H 0.2305 0.1330 0.1609 0.074 Uiso 1 1 calc R . .
H25B H 0.3115 0.1136 0.1442 0.074 Uiso 1 1 calc R . .
C26 C 0.3082(5) 0.2658(8) 0.2161(3) 0.072(2) Uani 1 1 d DU . .
H26A H 0.2758 0.3495 0.2233 0.086 Uiso 1 1 calc R . .
H26B H 0.3578 0.3059 0.2130 0.086 Uiso 1 1 calc R . .
C27 C 0.3162(5) 0.1586(8) 0.2740(3) 0.066(2) Uani 1 1 d DU . .
H27A H 0.2664 0.1209 0.2775 0.079 Uiso 1 1 calc R . .
H27B H 0.3470 0.0732 0.2656 0.079 Uiso 1 1 calc R . .
C28 C 0.3517(6) 0.2309(11) 0.3379(4) 0.087(3) Uani 1 1 d DU . .
H28A H 0.3555 0.1595 0.3747 0.131 Uiso 1 1 calc R . .
H28B H 0.3212 0.3154 0.3463 0.131 Uiso 1 1 calc R . .
H28C H 0.4017 0.2654 0.3350 0.131 Uiso 1 1 calc R . .
C29 C 0.1916(4) 0.3918(8) 0.0999(4) 0.070(2) Uani 1 1 d DU . .
H29A H 0.2107 0.4573 0.1385 0.084 Uiso 1 1 calc R . .
H29B H 0.1793 0.4547 0.0593 0.084 Uiso 1 1 calc R . .
C30 C 0.1224(5) 0.3182(11) 0.1105(7) 0.112(4) Uani 1 1 d DU . .
H30A H 0.1347 0.2378 0.1440 0.135 Uiso 1 1 calc R . .
H30B H 0.0947 0.2751 0.0680 0.135 Uiso 1 1 calc R . .
C31 C 0.0752(7) 0.4364(17) 0.1358(7) 0.162(6) Uani 1 1 d DU . .
H31A H 0.0432 0.3907 0.1640 0.194 Uiso 1 1 calc R . .
H31B H 0.1077 0.5109 0.1630 0.194 Uiso 1 1 calc R . .
C32 C 0.0289(11) 0.5066(19) 0.0769(10) 0.196(8) Uani 1 1 d DU . .
H32A H -0.0027 0.5824 0.0914 0.295 Uiso 1 1 calc R . .
H32B H -0.0026 0.4316 0.0502 0.295 Uiso 1 1 calc R . .
H32C H 0.0611 0.5526 0.0497 0.295 Uiso 1 1 calc R . .
Cl1 Cl 0.29450(10) 0.6993(2) 0.19594(9) 0.0597(7) 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
N1 0.032(3) 0.064(3) 0.041(3) 0.012(3) 0.009(2) 0.004(3)
N2 0.048(3) 0.050(3) 0.024(3) 0.000(2) 0.003(2) 0.002(3)
N3 0.050(4) 0.045(3) 0.049(3) 0.011(3) -0.017(3) -0.010(3)
N4 0.043(4) 0.080(4) 0.048(4) 0.017(3) -0.001(3) -0.013(3)
O1 0.046(3) 0.111(4) 0.029(3) 0.008(3) 0.004(2) -0.001(3)
O2 0.046(3) 0.092(4) 0.047(3) 0.035(3) -0.011(2) -0.010(3)
C1 0.0455(19) 0.0466(19) 0.0460(19) 0.0002(10) 0.0090(10) 0.0002(10)
C2 0.049(2) 0.0498(19) 0.0485(19) -0.0007(10) 0.0097(10) 0.0004(10)
C3 0.0411(18) 0.0420(18) 0.0411(18) -0.0004(10) 0.0090(10) 0.0007(10)
C4 0.0400(18) 0.0408(17) 0.0397(17) 0.0005(10) 0.0078(10) 0.0011(10)
C5 0.0439(18) 0.0448(18) 0.0433(18) 0.0002(10) 0.0091(10) 0.0011(10)
C6 0.0468(19) 0.0452(18) 0.0458(19) 0.0001(10) 0.0084(10) -0.0001(10)
C7 0.062(2) 0.060(2) 0.060(2) -0.0001(10) 0.0110(11) 0.0000(10)
C8 0.080(3) 0.079(3) 0.078(3) -0.0008(10) 0.0154(11) 0.0007(10)
C9 0.089(3) 0.087(3) 0.088(3) -0.0004(10) 0.0162(12) -0.0001(10)
C10 0.076(3) 0.075(3) 0.076(3) 0.0004(10) 0.0137(11) -0.0007(10)
C11 0.052(2) 0.0503(19) 0.0507(19) 0.0003(10) 0.0078(10) -0.0003(10)
C12 0.050(2) 0.051(2) 0.051(2) 0.0026(10) 0.0090(10) -0.0023(10)
C13 0.052(2) 0.053(2) 0.053(2) 0.0017(10) 0.0093(10) -0.0014(10)
C14 0.066(2) 0.067(2) 0.067(2) 0.0011(10) 0.0119(11) -0.0006(10)
C15 0.077(3) 0.078(3) 0.076(3) 0.0009(10) 0.0147(11) -0.0006(10)
C16 0.066(2) 0.067(2) 0.066(2) 0.0004(10) 0.0127(11) 0.0001(10)
N5 0.049(4) 0.043(3) 0.104(5) 0.029(3) 0.017(4) 0.002(3)
C17 0.076(3) 0.075(3) 0.077(3) 0.0017(10) 0.0151(11) -0.0005(10)
C18 0.097(3) 0.098(3) 0.098(3) 0.0015(10) 0.0202(12) -0.0004(10)
C19 0.086(3) 0.086(3) 0.086(3) 0.0006(10) 0.0175(12) -0.0002(10)
C20 0.096(3) 0.095(3) 0.095(3) 0.0006(10) 0.0195(12) -0.0016(10)
C21 0.073(3) 0.072(2) 0.073(3) 0.0007(10) 0.0150(11) -0.0003(10)
C22 0.086(3) 0.085(3) 0.087(3) 0.0007(10) 0.0169(12) -0.0007(10)
C23 0.104(4) 0.104(4) 0.104(4) 0.0012(10) 0.0216(12) -0.0006(10)
C24 0.134(5) 0.134(5) 0.134(5) 0.0008(10) 0.0272(14) -0.0007(10)
C25 0.062(2) 0.061(2) 0.063(2) 0.0013(10) 0.0130(11) 0.0002(10)
C26 0.072(2) 0.071(2) 0.073(2) 0.0012(10) 0.0143(11) -0.0004(10)
C27 0.066(2) 0.066(2) 0.067(2) 0.0002(10) 0.0143(11) 0.0000(10)
C28 0.087(3) 0.087(3) 0.088(3) 0.0003(10) 0.0180(12) 0.0002(10)
C29 0.069(2) 0.069(2) 0.071(2) 0.0008(10) 0.0136(11) -0.0003(10)
C30 0.112(4) 0.112(4) 0.113(4) 0.0000(10) 0.0233(13) 0.0003(10)
C31 0.162(6) 0.162(6) 0.162(6) 0.0003(10) 0.0331(16) 0.0000(10)
C32 0.196(8) 0.196(8) 0.196(8) 0.0000(10) 0.0402(19) -0.0002(10)
Cl1 0.0492(12) 0.0703(13) 0.0505(12) 0.0319(9) -0.0114(8) -0.0115(9)

_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
N1 C1 1.354(9) . ?
N1 C4 1.388(8) . ?
N2 C5 1.336(8) . ?
N2 C6 1.422(8) . ?
N3 C12 1.369(9) . ?
N3 C11 1.449(10) . ?
N4 C16 1.359(10) . ?
N4 C13 1.362(10) . ?
O1 C5 1.267(8) . ?
O2 C12 1.239(8) . ?
C1 C2 1.379(10) . ?
C2 C3 1.405(10) . ?
C3 C4 1.395(9) . ?
C4 C5 1.437(9) . ?
C6 C7 1.375(10) . ?
C6 C11 1.387(10) . ?
C7 C8 1.387(12) . ?
C8 C9 1.319(13) . ?
C9 C10 1.422(14) . ?
C10 C11 1.407(12) . ?
C12 C13 1.430(10) . ?
C13 C14 1.414(11) . ?
C14 C15 1.384(13) . ?
C15 C16 1.397(13) . ?
N5 C29 1.506(7) . ?
N5 C21 1.513(7) . ?
N5 C25 1.519(7) . ?
N5 C17 1.524(7) . ?
C17 C18 1.483(8) . ?
C18 C19 1.495(8) . ?
C19 C20 1.475(8) . ?
C21 C22 1.468(8) . ?
C22 C23 1.508(8) . ?
C23 C24 1.485(8) . ?
C25 C26 1.476(7) . ?
C26 C27 1.509(7) . ?
C27 C28 1.483(8) . ?
C29 C30 1.485(8) . ?
C30 C31 1.527(9) . ?
C31 C32 1.464(9) . ?

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
C1 N1 C4 110.0(5) . . ?
C5 N2 C6 124.4(5) . . ?
C12 N3 C11 123.1(6) . . ?
C16 N4 C13 112.0(6) . . ?
N1 C1 C2 107.7(6) . . ?
C1 C2 C3 108.5(6) . . ?
C4 C3 C2 106.8(6) . . ?
N1 C4 C3 107.0(6) . . ?
N1 C4 C5 118.3(6) . . ?
C3 C4 C5 134.4(6) . . ?
O1 C5 N2 121.6(6) . . ?
O1 C5 C4 119.7(6) . . ?
N2 C5 C4 118.7(6) . . ?
C7 C6 C11 119.6(7) . . ?
C7 C6 N2 119.5(7) . . ?
C11 C6 N2 120.9(6) . . ?
C6 C7 C8 121.7(8) . . ?
C9 C8 C7 119.8(9) . . ?
C8 C9 C10 120.7(10) . . ?
C11 C10 C9 119.3(9) . . ?
C6 C11 C10 118.4(7) . . ?
C6 C11 N3 122.1(6) . . ?
C10 C11 N3 119.5(7) . . ?
O2 C12 N3 121.5(7) . . ?
O2 C12 C13 120.3(7) . . ?
N3 C12 C13 118.2(7) . . ?
N4 C13 C14 106.3(7) . . ?
N4 C13 C12 118.7(7) . . ?
C14 C13 C12 135.0(7) . . ?
C15 C14 C13 106.7(8) . . ?
C14 C15 C16 109.5(9) . . ?
N4 C16 C15 105.4(8) . . ?
C29 N5 C21 111.0(6) . . ?
C29 N5 C25 111.4(5) . . ?
C21 N5 C25 105.4(5) . . ?
C29 N5 C17 106.2(5) . . ?
C21 N5 C17 109.9(6) . . ?
C25 N5 C17 113.1(6) . . ?
C18 C17 N5 112.6(6) . . ?
C17 C18 C19 112.2(7) . . ?
C20 C19 C18 110.4(7) . . ?
C22 C21 N5 115.1(6) . . ?
C21 C22 C23 108.8(6) . . ?
C24 C23 C22 108.6(7) . . ?
C26 C25 N5 116.0(6) . . ?
C25 C26 C27 109.0(6) . . ?
C28 C27 C26 111.1(6) . . ?
C30 C29 N5 113.3(6) . . ?
C29 C30 C31 107.1(7) . . ?
C32 C31 C30 107.4(8) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H91 O1 0.88 1.96 2.809(7) 162.8 3_675
N2 H92 Cl1 0.88 2.37 3.225(5) 164.5 .
N3 H93 Cl1 0.88 2.31 3.165(6) 165.6 .
N4 H94 O2 0.88 1.98 2.825(7) 161.9 3_575

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.16
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         1.649
_refine_diff_density_min         -1.038
_refine_diff_density_rms         0.182

#===END

data_2005sot1055
_database_code_depnum_ccdc_archive 'CCDC 283637'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 N4 S2'
_chemical_formula_weight         378.50

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

_cell_length_a                   7.9841(3)
_cell_length_b                   26.3041(11)
_cell_length_c                   8.9855(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.535(2)
_cell_angle_gamma                90.00
_cell_volume                     1834.68(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4135
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9184
_exptl_absorpt_correction_T_max  0.9940
_exptl_absorpt_process_details   
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;

_exptl_special_details           
;
SADABS was used to perform the Absorption correction
Parameter refinement on 12870 reflections reduced R(int) from 0.1212 to 0.0687
Ratio of minimum to maximum apparent transmission: 0.700294
The given Tmin and Tmax were generated using the SHELX SIZE command
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating Anode'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_measurement_device_type  'Bruker-Nonius CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans to fill the asymmetric unit'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23129
_diffrn_reflns_av_R_equivalents  0.1003
_diffrn_reflns_av_sigmaI/netI    0.0911
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4200
_reflns_number_gt                2774
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin, et al., 1993)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_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^)+(0.0420P)^2^+1.4605P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4200
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1242
_refine_ls_wR_factor_gt          0.1063
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_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
C1 C 0.1561(4) 0.59977(11) 0.4983(3) 0.0215(6) Uani 1 1 d . . .
H1 H 0.0757 0.6237 0.4437 0.026 Uiso 1 1 calc R . .
C2 C 0.1384(4) 0.54897(12) 0.4605(3) 0.0290(7) Uani 1 1 d . . .
H2 H 0.0461 0.5382 0.3793 0.035 Uiso 1 1 calc R . .
C3 C 0.2541(4) 0.51325(12) 0.5399(3) 0.0328(7) Uani 1 1 d . . .
H3 H 0.2418 0.4782 0.5136 0.039 Uiso 1 1 calc R . .
C4 C 0.3868(4) 0.52962(11) 0.6576(3) 0.0282(7) Uani 1 1 d . . .
H4 H 0.4656 0.5054 0.7129 0.034 Uiso 1 1 calc R . .
C5 C 0.4080(4) 0.58035(11) 0.6969(3) 0.0225(6) Uani 1 1 d . . .
H5 H 0.5007 0.5909 0.7779 0.027 Uiso 1 1 calc R . .
C6 C 0.2917(3) 0.61609(11) 0.6163(3) 0.0186(6) Uani 1 1 d . . .
C7 C 0.4133(3) 0.69511(11) 0.7552(3) 0.0171(6) Uani 1 1 d . . .
C8 C 0.5506(3) 0.77951(10) 0.8161(3) 0.0174(6) Uani 1 1 d . . .
C9 C 0.4690(3) 0.82664(10) 0.8082(3) 0.0189(6) Uani 1 1 d . . .
H9 H 0.3584 0.8311 0.7419 0.023 Uiso 1 1 calc R . .
C10 C 0.5482(4) 0.86699(11) 0.8964(3) 0.0209(6) Uani 1 1 d . . .
H10 H 0.4937 0.8993 0.8887 0.025 Uiso 1 1 calc R . .
C11 C 0.7071(4) 0.85984(11) 0.9956(3) 0.0231(6) Uani 1 1 d . . .
H11 H 0.7600 0.8871 1.0585 0.028 Uiso 1 1 calc R . .
C12 C 0.7894(3) 0.81363(10) 1.0043(3) 0.0198(6) Uani 1 1 d . . .
H12 H 0.8975 0.8091 1.0745 0.024 Uiso 1 1 calc R . .
C13 C 0.7151(3) 0.77334(10) 0.9106(3) 0.0183(6) Uani 1 1 d . . .
C14 C 0.9644(3) 0.71966(11) 0.9013(3) 0.0180(6) Uani 1 1 d . . .
C15 C 0.9489(3) 0.62759(11) 0.9633(3) 0.0192(6) Uani 1 1 d . . .
C16 C 0.8737(3) 0.62549(11) 1.0884(3) 0.0215(6) Uani 1 1 d . . .
H16 H 0.8797 0.6540 1.1545 0.026 Uiso 1 1 calc R . .
C17 C 0.7900(4) 0.58135(12) 1.1154(3) 0.0253(7) Uani 1 1 d . . .
H17 H 0.7377 0.5798 1.2001 0.030 Uiso 1 1 calc R . .
C18 C 0.7821(4) 0.53951(12) 1.0198(3) 0.0267(7) Uani 1 1 d . . .
H18 H 0.7223 0.5097 1.0373 0.032 Uiso 1 1 calc R . .
C19 C 0.8616(4) 0.54144(12) 0.8990(3) 0.0269(7) Uani 1 1 d . . .
H19 H 0.8597 0.5124 0.8356 0.032 Uiso 1 1 calc R . .
C20 C 0.9438(4) 0.58509(11) 0.8696(3) 0.0236(6) Uani 1 1 d . . .
H20 H 0.9969 0.5862 0.7855 0.028 Uiso 1 1 calc R . .
N1 N 0.3135(3) 0.66908(8) 0.6366(2) 0.0187(5) Uani 1 1 d . . .
H1A H 0.2539 0.6879 0.5618 0.022 Uiso 1 1 calc R . .
N2 N 0.4674(3) 0.74030(8) 0.7151(2) 0.0171(5) Uani 1 1 d . . .
H2A H 0.4499 0.7464 0.6163 0.020 Uiso 1 1 calc R . .
N3 N 0.8021(3) 0.72623(9) 0.9167(2) 0.0200(5) Uani 1 1 d . . .
H3A H 0.7451 0.6988 0.9319 0.024 Uiso 1 1 calc R . .
N4 N 1.0325(3) 0.67264(9) 0.9289(3) 0.0214(5) Uani 1 1 d . . .
H4A H 1.1412 0.6694 0.9253 0.026 Uiso 1 1 calc R . .
S1 S 0.45891(8) 0.67319(3) 0.93695(7) 0.01809(18) Uani 1 1 d . . .
S2 S 1.08025(9) 0.76575(3) 0.83969(8) 0.02046(18) 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
C1 0.0202(15) 0.0193(16) 0.0249(16) -0.0005(12) 0.0048(12) 0.0018(12)
C2 0.0261(16) 0.0278(19) 0.0310(17) -0.0051(14) 0.0025(13) -0.0055(14)
C3 0.0374(19) 0.0216(18) 0.0391(19) -0.0073(14) 0.0083(15) -0.0040(15)
C4 0.0317(18) 0.0193(17) 0.0340(18) 0.0003(13) 0.0087(13) 0.0022(13)
C5 0.0222(15) 0.0214(17) 0.0235(15) -0.0009(12) 0.0044(12) 0.0001(12)
C6 0.0208(15) 0.0196(16) 0.0171(14) -0.0020(11) 0.0080(11) -0.0016(12)
C7 0.0143(13) 0.0185(15) 0.0199(14) -0.0023(11) 0.0067(10) 0.0021(11)
C8 0.0201(15) 0.0175(15) 0.0163(14) -0.0011(11) 0.0077(11) -0.0021(11)
C9 0.0179(14) 0.0210(16) 0.0193(14) 0.0039(11) 0.0073(11) -0.0009(12)
C10 0.0235(15) 0.0176(16) 0.0256(16) 0.0003(12) 0.0142(12) 0.0017(12)
C11 0.0255(16) 0.0224(17) 0.0224(16) -0.0034(12) 0.0077(12) -0.0040(13)
C12 0.0181(14) 0.0211(16) 0.0197(15) 0.0014(11) 0.0037(11) -0.0028(12)
C13 0.0179(14) 0.0172(16) 0.0210(15) 0.0037(11) 0.0069(11) 0.0018(11)
C14 0.0171(14) 0.0226(16) 0.0132(14) -0.0012(11) 0.0013(10) -0.0022(12)
C15 0.0156(14) 0.0170(15) 0.0238(15) 0.0025(11) 0.0027(11) 0.0045(11)
C16 0.0197(15) 0.0201(16) 0.0240(15) 0.0019(12) 0.0034(11) 0.0035(12)
C17 0.0236(16) 0.0291(18) 0.0243(16) 0.0065(13) 0.0075(12) 0.0045(13)
C18 0.0248(16) 0.0238(17) 0.0299(17) 0.0042(13) 0.0031(12) -0.0047(13)
C19 0.0305(17) 0.0238(17) 0.0249(16) -0.0025(13) 0.0032(12) 0.0048(13)
C20 0.0234(15) 0.0246(17) 0.0238(15) 0.0020(12) 0.0077(12) 0.0030(13)
N1 0.0214(12) 0.0153(13) 0.0174(12) 0.0014(9) 0.0002(9) 0.0018(10)
N2 0.0207(12) 0.0186(13) 0.0122(11) -0.0004(9) 0.0045(9) 0.0001(10)
N3 0.0164(12) 0.0173(13) 0.0263(13) 0.0021(10) 0.0047(9) -0.0019(10)
N4 0.0136(11) 0.0193(13) 0.0318(14) 0.0042(10) 0.0061(10) 0.0018(10)
S1 0.0171(3) 0.0204(4) 0.0169(4) 0.0012(3) 0.0042(3) -0.0005(3)
S2 0.0181(4) 0.0207(4) 0.0230(4) 0.0009(3) 0.0057(3) -0.0021(3)

_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
C1 C2 1.378(4) . ?
C1 C6 1.394(4) . ?
C2 C3 1.392(4) . ?
C3 C4 1.379(4) . ?
C4 C5 1.381(4) . ?
C5 C6 1.398(4) . ?
C6 N1 1.411(3) . ?
C7 N2 1.342(3) . ?
C7 N1 1.357(3) . ?
C7 S1 1.690(3) . ?
C8 C9 1.395(4) . ?
C8 C13 1.397(4) . ?
C8 N2 1.430(3) . ?
C9 C10 1.385(4) . ?
C10 C11 1.382(4) . ?
C11 C12 1.375(4) . ?
C12 C13 1.396(4) . ?
C13 N3 1.416(3) . ?
C14 N3 1.346(3) . ?
C14 N4 1.351(3) . ?
C14 S2 1.695(3) . ?
C15 C16 1.394(4) . ?
C15 C20 1.394(4) . ?
C15 N4 1.429(3) . ?
C16 C17 1.389(4) . ?
C17 C18 1.389(4) . ?
C18 C19 1.380(4) . ?
C19 C20 1.378(4) . ?

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
C2 C1 C6 120.2(3) . . ?
C1 C2 C3 120.7(3) . . ?
C4 C3 C2 118.8(3) . . ?
C3 C4 C5 121.6(3) . . ?
C4 C5 C6 119.4(3) . . ?
C1 C6 C5 119.3(3) . . ?
C1 C6 N1 116.9(2) . . ?
C5 C6 N1 123.4(2) . . ?
N2 C7 N1 113.8(2) . . ?
N2 C7 S1 123.5(2) . . ?
N1 C7 S1 122.7(2) . . ?
C9 C8 C13 119.7(2) . . ?
C9 C8 N2 117.9(2) . . ?
C13 C8 N2 122.2(2) . . ?
C10 C9 C8 120.5(3) . . ?
C11 C10 C9 119.5(3) . . ?
C12 C11 C10 120.7(3) . . ?
C11 C12 C13 120.5(3) . . ?
C12 C13 C8 119.0(2) . . ?
C12 C13 N3 120.4(2) . . ?
C8 C13 N3 120.6(2) . . ?
N3 C14 N4 117.1(2) . . ?
N3 C14 S2 123.6(2) . . ?
N4 C14 S2 119.2(2) . . ?
C16 C15 C20 119.9(3) . . ?
C16 C15 N4 121.2(2) . . ?
C20 C15 N4 118.9(2) . . ?
C17 C16 C15 119.3(3) . . ?
C18 C17 C16 120.5(3) . . ?
C19 C18 C17 119.7(3) . . ?
C20 C19 C18 120.6(3) . . ?
C19 C20 C15 120.0(3) . . ?
C7 N1 C6 129.2(2) . . ?
C7 N2 C8 126.8(2) . . ?
C14 N3 C13 125.7(2) . . ?
C14 N4 C15 127.6(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A S2 0.88 2.47 3.347(2) 175.3 4_475
N2 H2A S1 0.88 2.67 3.369(2) 137.2 4_575
N3 H3A S1 0.88 2.39 3.118(2) 139.9 .
N4 H4A S1 0.88 2.52 3.388(2) 171.0 1_655

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.081

#===END