 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C10 H8 Cl2 N4'
_chemical_formula_sum
 'C10 H8 Cl2 N4'
_chemical_formula_weight          255.10
 
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'
 'Cl'  'Cl'   0.1484   0.1585
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            orthorhombic
_symmetry_space_group_name_H-M    Pbca
_symmetry_space_group_name_hall   '-P 2ac 2ab'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, -y, -z'
 'x-1/2, y, -z-1/2'
 'x, -y-1/2, z-1/2'
 '-x-1/2, y-1/2, z'
 
_cell_length_a                    7.2300(10)
_cell_length_b                    15.594(3)
_cell_length_c                    19.618(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      2211.8(7)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        unk
_exptl_crystal_colour             unk
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.20
_exptl_crystal_size_min           0.20
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.532
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1040
_exptl_absorpt_coefficient_mu     0.562
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_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         'rotating anode generator'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Delft instruments FAST area detector'
_diffrn_measurement_method
 'Intensity measurements as described by Darr, Drake, Hursthouse & Malik (1993)'
_diffrn_standards_number         'None'
_diffrn_standards_interval_count 'N/A'
_diffrn_standards_interval_time  'N/A'
_diffrn_standards_decay_%        'N/A'
_diffrn_reflns_number             8212
_diffrn_reflns_av_R_equivalents   0.0964
_diffrn_reflns_av_sigmaI/netI     0.1387
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        5
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        17
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          2.08
_diffrn_reflns_theta_max          24.99
_reflns_number_total              1704
_reflns_number_gt                 1062
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        'MADNES (Pflugrath & Messerschmidt, 1989)'
_computing_cell_refinement        REFINE
_computing_data_reduction         'ABSURD (Karaulov, 1992)'
_computing_structure_solution     'SIR92 (Altomare, Cascarano, Giacovazzo & Guaglitardi, 1993)'
_computing_structure_refinement   'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material   SHELXL97
 
_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 > 2σ(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)+(0.0392P)²+0.0000P] 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          1704
_refine_ls_number_parameters      177
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0815
_refine_ls_R_factor_gt            0.0443
_refine_ls_wR_factor_ref          0.1083
_refine_ls_wR_factor_gt           0.1025
_refine_ls_goodness_of_fit_ref    0.903
_refine_ls_restrained_S_all       0.903
_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
Cl1 Cl 0.07872(15) 0.48712(7) 0.12607(6) 0.0268(3) Uani 1 1 d . . .
Cl2 Cl 0.16063(15) 0.84900(7) 0.01415(6) 0.0252(3) Uani 1 1 d . . .
N2 N 0.0386(4) 0.6512(2) 0.12282(17) 0.0190(8) Uani 1 1 d . . .
N4 N 0.1169(4) 0.9419(2) -0.09246(18) 0.0174(9) Uani 1 1 d . . .
N3 N 0.0358(4) 0.7940(2) -0.10818(17) 0.0170(9) Uani 1 1 d . . .
N1 N 0.0519(4) 0.7305(2) 0.09532(18) 0.0184(9) Uani 1 1 d . . .
C9 C 0.0692(5) 0.9584(3) -0.1566(2) 0.0194(11) Uani 1 1 d . . .
C1 C 0.0972(5) 0.5857(3) 0.0864(2) 0.0170(10) Uani 1 1 d . . .
C2 C 0.1719(5) 0.5910(3) 0.0215(2) 0.0163(10) Uani 1 1 d . . .
C8 C 0.0053(6) 0.8936(3) -0.1993(3) 0.0228(11) Uani 1 1 d . . .
C4 C 0.1271(5) 0.7395(3) 0.0342(2) 0.0146(10) Uani 1 1 d . . .
C5 C 0.0967(5) 0.8606(3) -0.0726(2) 0.0166(10) Uani 1 1 d . . .
C7 C -0.0109(5) 0.8119(3) -0.1733(2) 0.0191(11) Uani 1 1 d . . .
C3 C 0.1871(5) 0.6709(3) -0.0059(2) 0.0176(10) Uani 1 1 d . . .
C10 C -0.0804(8) 0.7378(3) -0.2142(3) 0.0275(12) Uani 1 1 d . . .
C11 C 0.0865(13) 1.0489(4) -0.1811(3) 0.0331(15) Uani 1 1 d . . .
H3 H -0.029(5) 0.906(2) -0.242(2) 0.014(11) Uiso 1 1 d . . .
H7 H 0.206(4) 0.541(2) -0.0008(18) 0.007(10) Uiso 1 1 d . . .
H6 H 0.241(5) 0.680(2) -0.048(2) 0.008(10) Uiso 1 1 d . . .
H5 H -0.193(6) 0.716(3) -0.194(2) 0.045(15) Uiso 1 1 d . . .
H4 H -0.086(6) 0.754(3) -0.256(2) 0.030(15) Uiso 1 1 d . . .
H2 H 0.166(7) 1.064(4) -0.173(3) 0.04(3) Uiso 1 1 d . . .
H1 H 0.003(7) 1.070(4) -0.169(3) 0.06(3) Uiso 1 1 d . . .
H8 H 0.003(7) 0.682(4) -0.211(3) 0.070(18) Uiso 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
Cl1 0.0367(7) 0.0202(7) 0.0234(7) 0.0044(5) 0.0022(5) 0.0019(5)
Cl2 0.0315(7) 0.0225(7) 0.0214(7) -0.0005(5) -0.0047(5) -0.0042(5)
N2 0.022(2) 0.021(2) 0.014(2) 0.0003(19) -0.0004(16) 0.0009(15)
N4 0.018(2) 0.016(2) 0.018(2) 0.0012(17) 0.0027(15) -0.0012(15)
N3 0.016(2) 0.020(2) 0.015(2) -0.0013(17) 0.0005(15) -0.0007(15)
N1 0.019(2) 0.020(2) 0.016(2) -0.0003(17) -0.0031(16) 0.0013(16)
C9 0.017(3) 0.020(3) 0.020(3) 0.002(2) 0.0039(19) 0.0009(19)
C1 0.015(2) 0.019(3) 0.017(3) 0.004(2) -0.0034(18) 0.0005(18)
C2 0.013(2) 0.018(3) 0.018(3) -0.004(2) -0.0044(19) 0.0038(19)
C8 0.026(3) 0.023(3) 0.019(3) 0.004(2) -0.001(2) 0.000(2)
C4 0.014(2) 0.016(2) 0.015(3) 0.002(2) -0.0054(18) -0.0030(17)
C5 0.010(2) 0.026(3) 0.014(3) -0.001(2) 0.0028(17) 0.0008(18)
C7 0.011(2) 0.028(3) 0.019(3) -0.003(2) 0.0025(19) 0.0021(19)
C3 0.008(3) 0.029(3) 0.016(3) -0.001(2) -0.0016(18) 0.0004(18)
C10 0.036(3) 0.027(3) 0.019(3) -0.001(3) 0.000(2) -0.008(2)
C11 0.037(5) 0.022(3) 0.040(4) 0.006(3) 0.000(3) -0.002(3)
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Cl1 C1 1.729(4) . ?
Cl2 C4 1.768(4) . ?
Cl2 C5 1.772(4) . ?
N2 C1 1.317(5) . ?
N2 N1 1.353(5) . ?
N4 C9 1.329(5) . ?
N4 C5 1.335(5) . ?
N3 C5 1.327(5) . ?
N3 C7 1.351(5) . ?
N1 C4 1.324(5) . ?
C9 C8 1.391(6) . ?
C9 C11 1.497(7) . ?
C1 C2 1.385(6) . ?
C2 C3 1.361(6) . ?
C2 H7 0.93(4) . ?
C8 C7 1.377(6) . ?
C8 H3 0.90(4) . ?
C4 C3 1.397(6) . ?
C7 C10 1.494(6) . ?
C3 H6 0.93(4) . ?
C10 H5 0.97(5) . ?
C10 H4 0.85(4) . ?
C10 H8 1.06(6) . ?
C11 H2 0.64(5) . ?
C11 H1 0.73(5) . ?
 
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
C4 Cl2 C5 106.04(19) . . ?
C1 N2 N1 118.0(3) . . ?
C9 N4 C5 115.6(4) . . ?
C5 N3 C7 114.8(4) . . ?
C4 N1 N2 119.2(3) . . ?
N4 C9 C8 121.0(4) . . ?
N4 C9 C11 117.7(4) . . ?
C8 C9 C11 121.3(5) . . ?
N2 C1 C2 125.3(4) . . ?
N2 C1 Cl1 114.9(3) . . ?
C2 C1 Cl1 119.8(3) . . ?
C3 C2 C1 116.7(4) . . ?
C3 C2 H7 124(2) . . ?
C1 C2 H7 119(2) . . ?
C7 C8 C9 118.5(4) . . ?
C7 C8 H3 121(3) . . ?
C9 C8 H3 120(3) . . ?
N1 C4 C3 123.8(4) . . ?
N1 C4 Cl2 111.1(3) . . ?
C3 C4 Cl2 124.9(3) . . ?
N3 C5 N4 128.8(4) . . ?
N3 C5 Cl2 120.8(3) . . ?
N4 C5 Cl2 110.4(3) . . ?
N3 C7 C8 121.3(4) . . ?
N3 C7 C10 115.6(4) . . ?
C8 C7 C10 123.0(4) . . ?
C2 C3 C4 117.0(4) . . ?
C2 C3 H6 122(2) . . ?
C4 C3 H6 121(2) . . ?
C7 C10 H5 110(3) . . ?
C7 C10 H4 107(3) . . ?
H5 C10 H4 117(4) . . ?
C7 C10 H8 114(3) . . ?
H5 C10 H8 99(4) . . ?
H4 C10 H8 109(4) . . ?
C9 C11 H2 110(6) . . ?
C9 C11 H1 105(5) . . ?
H2 C11 H1 120(8) . . ?
 
_diffrn_measured_fraction_theta_max    0.873
_diffrn_reflns_theta_full              24.99
_diffrn_measured_fraction_theta_full   0.873
_refine_diff_density_max    0.377
_refine_diff_density_min   -0.515
_refine_diff_density_rms    0.099
