 
data_04alb001
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C31 H17 Cl3 F4 N4 S6'
_chemical_formula_weight          820.20
 
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'
 'F'  'F'   0.0171   0.0103
 '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            Triclinic
_symmetry_space_group_name_H-M    P-1
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    11.3216(3)
_cell_length_b                    13.2873(6)
_cell_length_c                    13.9320(9)
_cell_angle_alpha                 110.438(4)
_cell_angle_beta                  98.073(4)
_cell_angle_gamma                 115.161(4)
_cell_volume                      1671.26(14)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     43156
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        block
_exptl_crystal_colour             'dark yellow'
_exptl_crystal_size_max           0.16
_exptl_crystal_size_mid           0.12
_exptl_crystal_size_min           0.08
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.630
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              828
_exptl_absorpt_coefficient_mu     0.703
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   0.8958
_exptl_absorpt_correction_T_max   0.9459
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_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   'graphite'
_diffrn_measurement_device_type   
'Bruker-Nonius 95mm CCD camera on κ-goniostat' 
_diffrn_measurement_method        'φ & ω scans'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             33949
_diffrn_reflns_av_R_equivalents   0.0487
_diffrn_reflns_av_sigmaI/netI     0.0368
_diffrn_reflns_limit_h_min        -14
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_k_min        -17
_diffrn_reflns_limit_k_max        17
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          2.98
_diffrn_reflns_theta_max          27.50
_reflns_number_total              7667
_reflns_number_gt                 6356
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_cell_refinement        'DENZO & COLLECT'
_computing_data_reduction         'DENZO & COLLECT'
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0690P)²+6.3898P] where P=(Fo²+2Fc²)/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          7667
_refine_ls_number_parameters      534
_refine_ls_number_restraints      6
_refine_ls_R_factor_all           0.0493
_refine_ls_R_factor_gt            0.0382
_refine_ls_wR_factor_ref          0.1038
_refine_ls_wR_factor_gt           0.0927
_refine_ls_goodness_of_fit_ref    0.669
_refine_ls_restrained_S_all       0.674
_refine_ls_shift/su_max           0.503
_refine_ls_shift/su_mean          0.013
 
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 0.3852(2) 0.6253(2) 0.16486(17) 0.0171(4) Uani 1 1 d . . .
C2 C 0.4137(2) 0.66693(19) 0.34224(17) 0.0149(4) Uani 1 1 d . . .
C3 C 0.3181(2) 0.69491(19) 0.30895(16) 0.0144(4) Uani 1 1 d . . .
C4 C 0.2511(2) 0.74845(18) 0.37371(16) 0.0139(4) Uani 1 1 d . . .
C5 C 0.1703(2) 0.70197(18) 0.42879(16) 0.0141(4) Uani 1 1 d . . .
C6 C 0.2016(2) 0.89457(19) 0.46808(16) 0.0146(4) Uani 1 1 d . . .
C7 C 0.2059(2) 0.6827(2) 0.13313(17) 0.0176(4) Uani 1 1 d . . .
C8 C 0.0686(2) 0.6296(2) 0.12753(19) 0.0217(4) Uani 1 1 d . . .
C9 C -0.0242(3) 0.6396(3) 0.0604(2) 0.0303(5) Uani 1 1 d . . .
C10 C 0.0246(3) 0.7008(3) 0.0005(2) 0.0352(6) Uani 1 1 d . . .
C11 C 0.1606(3) 0.7555(3) 0.0059(2) 0.0330(6) Uani 1 1 d . . .
C12 C 0.2535(3) 0.7468(2) 0.07386(19) 0.0246(5) Uani 1 1 d . . .
C13 C 0.5458(2) 0.5761(2) 0.24911(17) 0.0176(4) Uani 1 1 d . . .
C14 C 0.6829(2) 0.6537(2) 0.2644(2) 0.0255(5) Uani 1 1 d . . .
C15 C 0.7710(3) 0.6061(3) 0.2550(2) 0.0325(6) Uani 1 1 d . . .
C16 C 0.7182(3) 0.4832(3) 0.2311(2) 0.0321(6) Uani 1 1 d . . .
C17 C 0.5839(3) 0.4056(3) 0.2168(2) 0.0347(6) Uani 1 1 d . . .
C18 C 0.4951(3) 0.4527(2) 0.2258(2) 0.0270(5) Uani 1 1 d . . .
C19 C 0.0582(2) 0.78305(19) 0.55647(17) 0.0153(4) Uani 1 1 d . . .
C20 C 0.0909(2) 0.75713(19) 0.64133(17) 0.0165(4) Uani 1 1 d . . .
C21 C 0.0120(2) 0.7507(2) 0.70932(18) 0.0193(4) Uani 1 1 d . . .
C22 C -0.0963(2) 0.7713(2) 0.69025(18) 0.0208(4) Uani 1 1 d . . .
C23 C -0.1305(2) 0.7973(2) 0.60652(19) 0.0212(4) Uani 1 1 d . . .
C24 C -0.0520(2) 0.8031(2) 0.53876(18) 0.0178(4) Uani 1 1 d . . .
C25 C 0.3422(2) 0.94291(19) 0.35071(16) 0.0155(4) Uani 1 1 d . . .
C26 C 0.2780(2) 0.9857(2) 0.29620(18) 0.0188(4) Uani 1 1 d . . .
C27 C 0.3504(3) 1.0568(2) 0.24867(19) 0.0233(5) Uani 1 1 d . . .
C28 C 0.4831(3) 1.0800(2) 0.25670(19) 0.0224(5) Uani 1 1 d . . .
C29 C 0.5474(2) 1.0370(2) 0.30886(18) 0.0202(4) Uani 1 1 d . . .
C30 C 0.4762(2) 0.96883(19) 0.35851(17) 0.0163(4) Uani 1 1 d . . .
N1 N 0.30112(18) 0.67012(16) 0.20068(14) 0.0157(3) Uani 1 1 d . . .
N2 N 0.45335(18) 0.62370(17) 0.25341(14) 0.0165(3) Uani 1 1 d . . .
N3 N 0.13972(18) 0.79215(16) 0.48666(14) 0.0146(3) Uani 1 1 d . . .
N4 N 0.26632(18) 0.86463(16) 0.39569(14) 0.0145(3) Uani 1 1 d . . .
S1 S 0.09363(5) 0.54996(5) 0.41202(4) 0.01562(11) Uani 1 1 d . . .
S2 S 0.22755(5) 0.55880(5) 0.53695(4) 0.01808(12) Uani 1 1 d . . .
S3 S 0.36991(6) 0.53138(5) 0.47535(5) 0.01902(12) Uani 1 1 d . . .
S4 S 0.49565(5) 0.69719(5) 0.47225(4) 0.01694(12) Uani 1 1 d . . .
S5 S 0.40138(6) 0.57953(6) 0.04310(5) 0.02475(13) Uani 1 1 d . . .
S6 S 0.20874(6) 1.03064(5) 0.52690(5) 0.01975(12) Uani 1 1 d . . .
F1 F -0.0670(2) 0.7052(2) -0.06963(15) 0.0575(6) Uani 1 1 d . . .
F2 F 0.8044(2) 0.4367(2) 0.22077(14) 0.0501(5) Uani 1 1 d . . .
F3 F -0.17253(15) 0.76670(14) 0.75700(12) 0.0303(3) Uani 1 1 d . . .
F4 F 0.55372(16) 1.14733(14) 0.20888(13) 0.0325(3) Uani 1 1 d . . .
H8 H 0.040(3) 0.585(2) 0.167(2) 0.016(6) Uiso 1 1 d . . .
H9 H -0.121(3) 0.601(3) 0.053(3) 0.036(8) Uiso 1 1 d . . .
H11 H 0.190(4) 0.797(3) -0.035(3) 0.048(9) Uiso 1 1 d . . .
H12 H 0.346(3) 0.782(3) 0.081(2) 0.029(7) Uiso 1 1 d . . .
H14 H 0.713(3) 0.738(3) 0.278(2) 0.034(8) Uiso 1 1 d . . .
H15 H 0.870(4) 0.660(3) 0.266(3) 0.044(9) Uiso 1 1 d . . .
H17 H 0.551(4) 0.323(3) 0.202(3) 0.052(10) Uiso 1 1 d . . .
H18 H 0.399(3) 0.400(3) 0.217(2) 0.035(8) Uiso 1 1 d . . .
H20 H 0.166(3) 0.746(2) 0.655(2) 0.016(6) Uiso 1 1 d . . .
H21 H 0.030(3) 0.730(3) 0.763(2) 0.024(7) Uiso 1 1 d . . .
H23 H -0.210(3) 0.807(3) 0.592(2) 0.031(7) Uiso 1 1 d . . .
H24 H -0.074(3) 0.821(2) 0.480(2) 0.019(6) Uiso 1 1 d . . .
H26 H 0.187(3) 0.966(2) 0.294(2) 0.017(6) Uiso 1 1 d . . .
H27 H 0.309(3) 1.086(3) 0.211(2) 0.027(7) Uiso 1 1 d . . .
H29 H 0.636(3) 1.050(2) 0.310(2) 0.021(6) Uiso 1 1 d . . .
H30 H 0.516(3) 0.936(2) 0.397(2) 0.018(6) Uiso 1 1 d . . .
C311 C 0.3046(5) 0.1389(5) 0.9354(4) 0.0395(11) Uani 0.759(4) 1 d PD A 1
H311 H 0.3761 0.2294 0.9660 0.047 Uiso 0.759(4) 1 calc PR A 1
Cl31 Cl 0.1941(2) 0.1246(2) 1.01153(17) 0.0713(6) Uani 0.759(4) 1 d PD A 1
Cl32 Cl 0.38949(13) 0.05854(14) 0.95101(10) 0.0479(4) Uani 0.759(4) 1 d PD A 1
Cl33 Cl 0.22038(14) 0.08378(10) 0.79821(8) 0.0464(4) Uani 0.759(4) 1 d PD A 1
C411 C 0.270(2) 0.144(2) 0.9365(17) 0.39(6) Uani 0.241(4) 1 d PD A 2
H411 H 0.3233 0.2365 0.9815 0.466 Uiso 0.241(4) 1 calc PR A 2
Cl41 Cl 0.357(3) 0.0707(19) 0.959(2) 0.48(3) Uani 0.241(4) 1 d PD A 2
Cl42 Cl 0.194(3) 0.0953(19) 0.8050(17) 0.50(3) Uani 0.241(4) 1 d PD A 2
Cl43 Cl 0.1258(15) 0.0677(15) 0.9682(10) 0.181(6) Uani 0.241(4) 1 d PD A 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
C1 N2 1.372(3) . ?
C1 N1 1.385(3) . ?
C1 S5 1.656(2) . ?
C2 C3 1.359(3) . ?
C2 N2 1.394(3) . ?
C2 S4 1.734(2) . ?
C3 N1 1.392(3) . ?
C3 C4 1.449(3) . ?
C4 C5 1.362(3) . ?
C4 N4 1.391(3) . ?
C5 N3 1.401(2) . ?
C5 S1 1.735(2) . ?
C6 N4 1.374(3) . ?
C6 N3 1.377(3) . ?
C6 S6 1.664(2) . ?
C7 C8 1.384(3) . ?
C7 C12 1.387(3) . ?
C7 N1 1.433(3) . ?
C8 C9 1.388(3) . ?
C8 H8 0.93(3) . ?
C9 C10 1.373(4) . ?
C9 H9 0.96(3) . ?
C10 F1 1.357(3) . ?
C10 C11 1.372(4) . ?
C11 C12 1.384(3) . ?
C11 H11 0.92(4) . ?
C12 H12 0.92(3) . ?
C13 C18 1.377(3) . ?
C13 C14 1.382(3) . ?
C13 N2 1.434(3) . ?
C14 C15 1.388(3) . ?
C14 H14 0.96(3) . ?
C15 C16 1.368(4) . ?
C15 H15 0.99(3) . ?
C16 F2 1.358(3) . ?
C16 C17 1.361(4) . ?
C17 C18 1.390(3) . ?
C17 H17 0.93(4) . ?
C18 H18 0.97(3) . ?
C19 C20 1.387(3) . ?
C19 C24 1.389(3) . ?
C19 N3 1.432(3) . ?
C20 C21 1.390(3) . ?
C20 H20 0.92(3) . ?
C21 C22 1.376(3) . ?
C21 H21 0.91(3) . ?
C22 F3 1.354(2) . ?
C22 C23 1.377(3) . ?
C23 C24 1.384(3) . ?
C23 H23 0.96(3) . ?
C24 H24 0.97(3) . ?
C25 C30 1.384(3) . ?
C25 C26 1.388(3) . ?
C25 N4 1.435(3) . ?
C26 C27 1.391(3) . ?
C26 H26 0.94(3) . ?
C27 C28 1.379(3) . ?
C27 H27 0.93(3) . ?
C28 F4 1.356(2) . ?
C28 C29 1.371(3) . ?
C29 C30 1.387(3) . ?
C29 H29 0.93(3) . ?
C30 H30 0.97(3) . ?
S1 S2 2.0752(7) . ?
S2 S3 2.0338(7) . ?
S3 S4 2.0734(8) . ?
C311 Cl33 1.736(5) . ?
C311 Cl31 1.743(5) . ?
C311 Cl32 1.758(4) . ?
C311 H311 1.0000 . ?
C411 Cl42 1.666(18) . ?
C411 Cl41 1.72(2) . ?
C411 Cl43 1.726(18) . ?
C411 H411 1.0000 . ?
 
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
N2 C1 N1 104.54(17) . . ?
N2 C1 S5 126.03(16) . . ?
N1 C1 S5 129.42(16) . . ?
C3 C2 N2 106.95(18) . . ?
C3 C2 S4 129.26(16) . . ?
N2 C2 S4 123.17(15) . . ?
C2 C3 N1 107.36(17) . . ?
C2 C3 C4 127.58(19) . . ?
N1 C3 C4 124.95(18) . . ?
C5 C4 N4 107.13(17) . . ?
C5 C4 C3 128.41(18) . . ?
N4 C4 C3 124.36(18) . . ?
C4 C5 N3 107.19(17) . . ?
C4 C5 S1 126.43(15) . . ?
N3 C5 S1 125.45(15) . . ?
N4 C6 N3 105.24(17) . . ?
N4 C6 S6 126.45(15) . . ?
N3 C6 S6 128.16(16) . . ?
C8 C7 C12 121.6(2) . . ?
C8 C7 N1 119.40(19) . . ?
C12 C7 N1 119.0(2) . . ?
C7 C8 C9 119.4(2) . . ?
C7 C8 H8 119.3(16) . . ?
C9 C8 H8 121.3(16) . . ?
C10 C9 C8 117.9(2) . . ?
C10 C9 H9 120.5(19) . . ?
C8 C9 H9 121.5(19) . . ?
F1 C10 C11 118.1(3) . . ?
F1 C10 C9 118.3(3) . . ?
C11 C10 C9 123.6(2) . . ?
C10 C11 C12 118.4(2) . . ?
C10 C11 H11 121(2) . . ?
C12 C11 H11 120(2) . . ?
C11 C12 C7 119.1(2) . . ?
C11 C12 H12 121.9(18) . . ?
C7 C12 H12 119.0(18) . . ?
C18 C13 C14 121.4(2) . . ?
C18 C13 N2 119.3(2) . . ?
C14 C13 N2 119.2(2) . . ?
C13 C14 C15 119.4(2) . . ?
C13 C14 H14 118.8(18) . . ?
C15 C14 H14 121.8(18) . . ?
C16 C15 C14 118.3(2) . . ?
C16 C15 H15 121(2) . . ?
C14 C15 H15 121(2) . . ?
F2 C16 C17 118.8(3) . . ?
F2 C16 C15 118.0(3) . . ?
C17 C16 C15 123.2(2) . . ?
C16 C17 C18 118.7(3) . . ?
C16 C17 H17 121(2) . . ?
C18 C17 H17 120(2) . . ?
C13 C18 C17 119.1(2) . . ?
C13 C18 H18 120.2(18) . . ?
C17 C18 H18 120.7(18) . . ?
C20 C19 C24 120.92(19) . . ?
C20 C19 N3 120.32(18) . . ?
C24 C19 N3 118.75(18) . . ?
C19 C20 C21 119.5(2) . . ?
C19 C20 H20 121.2(16) . . ?
C21 C20 H20 119.3(16) . . ?
C22 C21 C20 118.5(2) . . ?
C22 C21 H21 121.4(17) . . ?
C20 C21 H21 120.1(18) . . ?
F3 C22 C21 118.8(2) . . ?
F3 C22 C23 118.3(2) . . ?
C21 C22 C23 123.0(2) . . ?
C22 C23 C24 118.4(2) . . ?
C22 C23 H23 121.4(18) . . ?
C24 C23 H23 120.1(18) . . ?
C23 C24 C19 119.8(2) . . ?
C23 C24 H24 119.4(16) . . ?
C19 C24 H24 120.8(16) . . ?
C30 C25 C26 121.63(19) . . ?
C30 C25 N4 118.66(18) . . ?
C26 C25 N4 119.63(19) . . ?
C25 C26 C27 119.1(2) . . ?
C25 C26 H26 118.7(16) . . ?
C27 C26 H26 122.2(16) . . ?
C28 C27 C26 118.0(2) . . ?
C28 C27 H27 121.4(18) . . ?
C26 C27 H27 120.6(18) . . ?
F4 C28 C29 117.9(2) . . ?
F4 C28 C27 118.5(2) . . ?
C29 C28 C27 123.6(2) . . ?
C28 C29 C30 118.2(2) . . ?
C28 C29 H29 122.2(17) . . ?
C30 C29 H29 119.6(17) . . ?
C25 C30 C29 119.4(2) . . ?
C25 C30 H30 118.7(15) . . ?
C29 C30 H30 121.9(15) . . ?
C1 N1 C3 110.27(17) . . ?
C1 N1 C7 124.11(17) . . ?
C3 N1 C7 125.56(17) . . ?
C1 N2 C2 110.88(17) . . ?
C1 N2 C13 122.65(17) . . ?
C2 N2 C13 126.37(17) . . ?
C6 N3 C5 109.88(16) . . ?
C6 N3 C19 123.74(17) . . ?
C5 N3 C19 126.38(17) . . ?
C6 N4 C4 110.48(16) . . ?
C6 N4 C25 125.12(17) . . ?
C4 N4 C25 124.38(17) . . ?
C5 S1 S2 104.22(7) . . ?
S3 S2 S1 105.21(3) . . ?
S2 S3 S4 104.78(3) . . ?
C2 S4 S3 101.68(7) . . ?
Cl33 C311 Cl31 113.6(3) . . ?
Cl33 C311 Cl32 110.2(3) . . ?
Cl31 C311 Cl32 108.1(3) . . ?
Cl33 C311 H311 108.3 . . ?
Cl31 C311 H311 108.3 . . ?
Cl32 C311 H311 108.3 . . ?
Cl42 C411 Cl41 113.5(18) . . ?
Cl42 C411 Cl43 99.8(14) . . ?
Cl41 C411 Cl43 99.1(17) . . ?
Cl42 C411 H411 114.2 . . ?
Cl41 C411 H411 114.3 . . ?
Cl43 C411 H411 114.1 . . ?
 
_diffrn_measured_fraction_theta_max    0.998
_diffrn_reflns_theta_full              27.50
_diffrn_measured_fraction_theta_full   0.998
_refine_diff_density_max    0.810
_refine_diff_density_min   -0.779
_refine_diff_density_rms    0.074
