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


data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
loop_
_publ_author_name
_publ_author_address

K.Avasthi
;
Medicinal and Process Chemistry Division
CSIR-Central Drug Research Institute
Chattar Manzil Palace, Post Box No. 173
Lucknow-226001
India
;
A.Kumar
;
Medicinal and
Process Chemistry
Division CSIR-Central
Drug Research
Institute Chattar
Manzil Palace,
Post Box
No. 173
Lucknow-226001 India
;
S.Aswal
;
Medicinal and Process Chemistry Division
CSIR-Central Drug Research Institute
Chattar Manzil Palace, Post Box No. 173
Lucknow-226001
India
;
R.Kant
;
Molecular and Structural Biology Division
CSIR-Central Drug Research Institute
Chattar Manzil Palace, Post Box No. 173
Lucknow-226001
India
;
Resmi.Raghunandan
;
Molecular and Structural Biology Division
CSIR-Central Drug Research Institute
Chattar Manzil Palace, Post Box No. 173
Lucknow-226001
India
;
P.R.Maulik
;
Molecular and
Structural Biology
Division CSIR-Central
Drug Research
Institute Chattar
Manzil Palace,
Post Box
No. 173
Lucknow-226001 India
;
;
R.Khanna
;
;Department of Chemistry
Banaras Hindu University
Varanasi-221005
India
;

#TrackingRef 'Final935UL.CIF'

_publ_contact_author             'Dr. Kamlakar. Avasthi'
_publ_contact_author_email       kavasthi@rediffmail.com
_publ_contact_author_name        'Dr. Kamlakar. Avasthi'

data_13
_database_code_depnum_ccdc_archive 'CCDC 816595'

#_CDRI_Communication_No. '37/2011/AK'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2-(2-(4,6-bis(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)
ethyl)phthalazin-1(2H)-one
;
_chemical_name_common            ?
_chemical_melting_point          137
_chemical_formula_moiety         'C17 H16 N6 O S2'
_chemical_formula_sum            'C17 H16 N6 O S2'
_chemical_formula_weight         384.48

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   C2/c

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

_cell_length_a                   16.708(2)
_cell_length_b                   15.732(2)
_cell_length_c                   14.4360(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.790(10)
_cell_angle_gamma                90.00
_cell_volume                     3613.1(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    26
_cell_measurement_theta_min      5.14
_cell_measurement_theta_max      12.45

_exptl_crystal_description       'rectangular block'
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.125
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1600
_exptl_absorpt_coefficient_mu    0.314
_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      293(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  'Bruker P4 diffractometer'
_diffrn_measurement_method       \q-2\q
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 97
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5048
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3178
_reflns_number_gt                1688
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_cell_refinement       'XSCANS (Siemens, 1996)'
_computing_data_reduction        'XSCANS (Siemens, 1996)'
_computing_structure_solution    'SHELXTL-NT(Bruker, 1997)'
_computing_structure_refinement  'SHELXTL-NT(Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL-NT(Bruker, 1997)'
_computing_publication_material  'SHELXTL-NT(Bruker, 1997)'

_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^)+(0.0561P)^2^+0.9064P] 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     SHELXL
_refine_ls_extinction_coef       0.0014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3178
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1355
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
C3 C -0.0400(2) 0.4644(2) 0.0802(2) 0.0723(10) Uani 1 1 d . . .
H3 H -0.0358 0.5232 0.0870 0.087 Uiso 1 1 calc R . .
C4 C 0.0998(2) 0.4050(2) 0.2065(2) 0.0583(8) Uani 1 1 d . . .
C6 C 0.0971(2) 0.2592(2) 0.2004(2) 0.0594(8) Uani 1 1 d . . .
C8 C -0.14002(19) 0.2764(2) -0.0287(3) 0.0748(10) Uani 1 1 d . . .
H8A H -0.1983 0.2913 -0.0383 0.090 Uiso 1 1 calc R . .
H8B H -0.1297 0.2217 0.0038 0.090 Uiso 1 1 calc R . .
C9 C -0.1255(2) 0.2689(2) -0.1261(2) 0.0757(10) Uani 1 1 d . . .
H9A H -0.1640 0.2272 -0.1651 0.091 Uiso 1 1 calc R . .
H9B H -0.1376 0.3231 -0.1595 0.091 Uiso 1 1 calc R . .
C12 C 0.0882(3) 0.2906(3) -0.1212(3) 0.0854(11) Uani 1 1 d . . .
H12 H 0.1233 0.3347 -0.1272 0.102 Uiso 1 1 calc R . .
C13 C 0.2060(3) 0.1890(3) -0.1061(3) 0.1006(14) Uani 1 1 d . . .
H13 H 0.2413 0.2324 -0.1136 0.121 Uiso 1 1 calc R . .
C14 C 0.2337(3) 0.1069(4) -0.0928(3) 0.1005(14) Uani 1 1 d . . .
H14 H 0.2885 0.0946 -0.0916 0.121 Uiso 1 1 calc R . .
C15 C 0.1824(3) 0.0420(3) -0.0811(3) 0.0978(13) Uani 1 1 d . . .
H15 H 0.2028 -0.0133 -0.0720 0.117 Uiso 1 1 calc R . .
C16 C 0.1017(3) 0.0581(2) -0.0827(3) 0.0870(11) Uani 1 1 d . . .
H16 H 0.0675 0.0140 -0.0743 0.104 Uiso 1 1 calc R . .
C17 C -0.0155(2) 0.1601(2) -0.1006(2) 0.0737(10) Uani 1 1 d . . .
C18 C 0.2402(2) 0.4650(3) 0.3437(3) 0.0919(12) Uani 1 1 d . . .
H18A H 0.2231 0.4316 0.3901 0.138 Uiso 1 1 calc R . .
H18B H 0.2718 0.5133 0.3759 0.138 Uiso 1 1 calc R . .
H18C H 0.2744 0.4310 0.3155 0.138 Uiso 1 1 calc R . .
C19 C 0.0854(2) 0.0855(2) 0.1859(3) 0.0811(10) Uani 1 1 d . . .
H19A H 0.0299 0.0942 0.1907 0.122 Uiso 1 1 calc R . .
H19B H 0.1063 0.0314 0.2134 0.122 Uiso 1 1 calc R . .
H19C H 0.0834 0.0868 0.1187 0.122 Uiso 1 1 calc R . .
C3A C 0.02126(19) 0.4064(2) 0.1342(2) 0.0581(8) Uani 1 1 d . . .
C7A C -0.01142(19) 0.3270(2) 0.1016(2) 0.0575(8) Uani 1 1 d . . .
C12A C 0.1224(2) 0.2067(2) -0.1083(2) 0.0718(9) Uani 1 1 d . . .
C16A C 0.0710(2) 0.1401(2) -0.0969(2) 0.0668(9) Uani 1 1 d . . .
N1 N -0.08653(16) 0.33958(18) 0.03305(19) 0.0649(7) Uani 1 1 d . . .
N2 N -0.10370(18) 0.42466(19) 0.0192(2) 0.0719(8) Uani 1 1 d . . .
N5 N 0.13737(15) 0.33163(17) 0.23977(18) 0.0614(7) Uani 1 1 d . . .
N7 N 0.02441(16) 0.25074(16) 0.13068(19) 0.0611(7) Uani 1 1 d . . .
N10 N -0.03902(17) 0.24383(18) -0.11770(18) 0.0654(7) Uani 1 1 d . . .
N11 N 0.01186(19) 0.30969(18) -0.1253(2) 0.0732(8) Uani 1 1 d . . .
O1 O -0.06578(15) 0.10772(16) -0.0901(2) 0.1040(9) Uani 1 1 d . . .
S1 S 0.14953(6) 0.50050(5) 0.25043(7) 0.0760(3) Uani 1 1 d . . .
S2 S 0.15338(6) 0.16772(6) 0.25060(7) 0.0795(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
C3 0.080(3) 0.067(2) 0.076(2) -0.003(2) 0.033(2) 0.018(2)
C4 0.064(2) 0.059(2) 0.0594(18) -0.0043(16) 0.0298(16) 0.0023(17)
C6 0.0538(19) 0.060(2) 0.065(2) 0.0022(17) 0.0185(17) 0.0025(16)
C8 0.0442(18) 0.078(2) 0.097(3) 0.006(2) 0.0135(18) 0.0026(17)
C9 0.055(2) 0.073(2) 0.082(3) -0.0032(19) -0.0043(18) 0.0098(17)
C12 0.083(3) 0.087(3) 0.092(3) 0.015(2) 0.034(2) -0.006(2)
C13 0.092(3) 0.126(4) 0.098(3) 0.007(3) 0.051(3) 0.011(3)
C14 0.091(3) 0.141(4) 0.078(3) -0.004(3) 0.038(2) 0.035(3)
C15 0.104(4) 0.102(4) 0.078(3) -0.010(2) 0.013(2) 0.042(3)
C16 0.086(3) 0.071(3) 0.088(3) -0.015(2) 0.002(2) 0.015(2)
C17 0.067(2) 0.062(2) 0.078(2) -0.0095(19) 0.0002(18) -0.001(2)
C18 0.076(3) 0.097(3) 0.094(3) -0.013(2) 0.013(2) -0.014(2)
C19 0.080(2) 0.058(2) 0.098(3) 0.0042(19) 0.017(2) -0.0040(18)
C3A 0.058(2) 0.060(2) 0.0603(19) -0.0058(17) 0.0238(17) 0.0031(17)
C7A 0.0522(19) 0.066(2) 0.0571(18) 0.0009(18) 0.0213(15) 0.0064(18)
C12A 0.079(3) 0.079(3) 0.058(2) 0.0018(18) 0.0219(18) 0.016(2)
C16A 0.068(2) 0.067(2) 0.0571(19) -0.0112(17) 0.0070(17) 0.0076(19)
N1 0.0526(16) 0.0694(19) 0.0702(16) -0.0002(15) 0.0150(13) 0.0089(14)
N2 0.0677(19) 0.069(2) 0.0785(18) 0.0024(16) 0.0210(16) 0.0210(16)
N5 0.0565(16) 0.0612(17) 0.0655(16) -0.0020(15) 0.0171(13) -0.0019(15)
N7 0.0518(16) 0.0605(18) 0.0685(17) 0.0031(13) 0.0147(14) 0.0009(13)
N10 0.0649(18) 0.0593(18) 0.0616(16) -0.0034(13) 0.0038(13) 0.0036(15)
N11 0.076(2) 0.069(2) 0.0736(19) 0.0095(14) 0.0213(16) -0.0006(16)
O1 0.0713(17) 0.0629(17) 0.161(3) -0.0014(17) 0.0102(17) -0.0135(14)
S1 0.0854(7) 0.0618(6) 0.0809(6) -0.0131(5) 0.0256(5) -0.0044(5)
S2 0.0659(6) 0.0627(6) 0.0938(7) 0.0080(5) 0.0004(5) 0.0025(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
C3 N2 1.314(4) . ?
C3 C3A 1.414(4) . ?
C4 N5 1.331(4) . ?
C4 C3A 1.406(4) . ?
C4 S1 1.740(3) . ?
C6 N7 1.326(4) . ?
C6 N5 1.356(4) . ?
C6 S2 1.751(3) . ?
C8 N1 1.447(4) . ?
C8 C9 1.503(5) . ?
C9 N10 1.467(4) . ?
C12 N11 1.295(4) . ?
C12 C12A 1.427(5) . ?
C13 C14 1.366(6) . ?
C13 C12A 1.414(5) . ?
C14 C15 1.377(6) . ?
C15 C16 1.365(5) . ?
C16 C16A 1.380(5) . ?
C17 O1 1.219(4) . ?
C17 N10 1.375(4) . ?
C17 C16A 1.465(5) . ?
C18 S1 1.781(4) . ?
C19 S2 1.785(3) . ?
C3A C7A 1.388(4) . ?
C7A N7 1.349(4) . ?
C7A N1 1.354(4) . ?
C12A C16A 1.396(5) . ?
N1 N2 1.371(4) . ?
N10 N11 1.365(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
N2 C3 C3A 111.4(3) . . ?
N5 C4 C3A 120.8(3) . . ?
N5 C4 S1 119.8(2) . . ?
C3A C4 S1 119.3(2) . . ?
N7 C6 N5 128.7(3) . . ?
N7 C6 S2 118.9(2) . . ?
N5 C6 S2 112.5(2) . . ?
N1 C8 C9 112.6(3) . . ?
N10 C9 C8 112.4(3) . . ?
N11 C12 C12A 124.8(4) . . ?
C14 C13 C12A 118.6(4) . . ?
C13 C14 C15 121.4(4) . . ?
C16 C15 C14 120.7(4) . . ?
C15 C16 C16A 119.7(4) . . ?
O1 C17 N10 120.0(3) . . ?
O1 C17 C16A 124.1(3) . . ?
N10 C17 C16A 115.9(3) . . ?
C7A C3A C4 114.7(3) . . ?
C7A C3A C3 104.5(3) . . ?
C4 C3A C3 140.7(3) . . ?
N7 C7A N1 125.6(3) . . ?
N7 C7A C3A 127.2(3) . . ?
N1 C7A C3A 107.2(3) . . ?
C16A C12A C13 119.3(4) . . ?
C16A C12A C12 118.2(3) . . ?
C13 C12A C12 122.5(4) . . ?
C16 C16A C12A 120.3(3) . . ?
C16 C16A C17 121.6(4) . . ?
C12A C16A C17 118.1(3) . . ?
C7A N1 N2 110.8(3) . . ?
C7A N1 C8 127.5(3) . . ?
N2 N1 C8 121.2(3) . . ?
C3 N2 N1 106.0(3) . . ?
C4 N5 C6 117.3(3) . . ?
C6 N7 C7A 111.3(3) . . ?
N11 N10 C17 126.2(3) . . ?
N11 N10 C9 114.3(3) . . ?
C17 N10 C9 119.5(3) . . ?
C12 N11 N10 116.7(3) . . ?
C4 S1 C18 101.87(17) . . ?
C6 S2 C19 101.74(17) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.045

#===END

# Attachment 'FinalLeo72r.CIF'

data_15
_database_code_depnum_ccdc_archive 'CCDC 816596'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2-(2-(4-chloro-6-(methylthio)-1H-pyrazolo
[3,4-d]pyrimidin-1-yl)ethyl)phthalazin-1(2H)-one

;
_chemical_name_common            ?
_chemical_melting_point          211
_chemical_formula_moiety         'C16 H13 Cl N6 O S'
_chemical_formula_sum            'C16 H13 Cl N6 O S'
_chemical_formula_weight         372.83

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'
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)/n

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                   9.1610(10)
_cell_length_b                   14.0630(10)
_cell_length_c                   13.1090(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.120(10)
_cell_angle_gamma                90.00
_cell_volume                     1651.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    37
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      12.32

_exptl_crystal_description       'rectangular block'
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.376
_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      293(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  'Bruker P4 diffractometer'
_diffrn_measurement_method       \q-2\q
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 97
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4075
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2901
_reflns_number_gt                1957
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_cell_refinement       'XSCANS (Siemens, 1996)'
_computing_data_reduction        'XSCANS (Siemens, 1996)'
_computing_structure_solution    'SHELXTL-NT(Bruker, 1997)'
_computing_structure_refinement  'SHELXTL-NT(Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL-NT(Bruker, 1997)'
_computing_publication_material  'SHELXTL-NT(Bruker, 1997)'

_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^)+(0.0567P)^2^+0.3129P] 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         2901
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1225
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
C3 C 0.6232(3) 0.34227(19) 0.2172(2) 0.0613(8) Uani 1 1 d . . .
H3 H 0.6917 0.3074 0.1894 0.074 Uiso 1 1 calc R . .
C4 C 0.4481(3) 0.21477(17) 0.2779(2) 0.0530(7) Uani 1 1 d . . .
C6 C 0.2762(3) 0.28872(19) 0.3524(2) 0.0509(7) Uani 1 1 d . . .
C8 C 0.4641(3) 0.55650(17) 0.2847(2) 0.0547(7) Uani 1 1 d . . .
H8A H 0.3599 0.5592 0.2892 0.066 Uiso 1 1 calc R . .
H8B H 0.4762 0.5946 0.2253 0.066 Uiso 1 1 calc R . .
C9 C 0.5581(3) 0.59799(18) 0.3823(2) 0.0581(7) Uani 1 1 d . . .
H9A H 0.5566 0.5562 0.4409 0.070 Uiso 1 1 calc R . .
H9B H 0.6606 0.6041 0.3745 0.070 Uiso 1 1 calc R . .
C12 C 0.5077(3) 0.8486(2) 0.3681(2) 0.0594(7) Uani 1 1 d . . .
H12 H 0.5495 0.8996 0.3392 0.071 Uiso 1 1 calc R . .
C13 C 0.3346(3) 0.9620(2) 0.4289(2) 0.0632(8) Uani 1 1 d . . .
H13 H 0.3728 1.0130 0.3976 0.076 Uiso 1 1 calc R . .
C14 C 0.2252(3) 0.9766(2) 0.4831(2) 0.0727(9) Uani 1 1 d . . .
H14 H 0.1894 1.0377 0.4899 0.087 Uiso 1 1 calc R . .
C15 C 0.1672(4) 0.8996(3) 0.5285(3) 0.0814(10) Uani 1 1 d . . .
H15 H 0.0923 0.9100 0.5653 0.098 Uiso 1 1 calc R . .
C16 C 0.2177(3) 0.8101(3) 0.5199(2) 0.0725(9) Uani 1 1 d . . .
H16 H 0.1773 0.7595 0.5504 0.087 Uiso 1 1 calc R . .
C17 C 0.3848(3) 0.69723(19) 0.4546(2) 0.0526(7) Uani 1 1 d . . .
C18 C 0.0619(4) 0.3867(2) 0.4313(3) 0.0791(10) Uani 1 1 d . . .
H18A H 0.1442 0.4278 0.4593 0.119 Uiso 1 1 calc R . .
H18B H -0.0065 0.3854 0.4776 0.119 Uiso 1 1 calc R . .
H18C H 0.0115 0.4099 0.3642 0.119 Uiso 1 1 calc R . .
C3A C 0.5076(3) 0.30182(18) 0.25896(19) 0.0480(6) Uani 1 1 d . . .
C7A C 0.4340(3) 0.37988(17) 0.29107(19) 0.0443(6) Uani 1 1 d . . .
C12A C 0.3900(3) 0.86942(19) 0.42018(19) 0.0493(7) Uani 1 1 d . . .
C16A C 0.3297(3) 0.79392(18) 0.4654(2) 0.0513(7) Uani 1 1 d . . .
Cl1 Cl 0.52274(11) 0.11150(5) 0.23833(7) 0.0824(3) Uani 1 1 d . . .
N1 N 0.5038(2) 0.45851(14) 0.26787(16) 0.0504(6) Uani 1 1 d . . .
N2 N 0.6218(3) 0.43585(16) 0.22270(18) 0.0600(6) Uani 1 1 d . . .
N5 N 0.3348(3) 0.20639(15) 0.32423(17) 0.0555(6) Uani 1 1 d . . .
N7 N 0.3167(2) 0.37684(15) 0.33754(16) 0.0492(5) Uani 1 1 d . . .
N10 N 0.4996(2) 0.69122(15) 0.40198(16) 0.0513(6) Uani 1 1 d . . .
N11 N 0.5614(2) 0.76581(15) 0.35729(18) 0.0556(6) Uani 1 1 d . . .
O1 O 0.3370(2) 0.62609(14) 0.48864(17) 0.0730(6) Uani 1 1 d . . .
S1 S 0.13020(9) 0.26844(6) 0.41751(6) 0.0673(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
C3 0.0675(19) 0.0465(17) 0.0789(19) -0.0043(14) 0.0356(16) 0.0019(14)
C4 0.0633(18) 0.0397(15) 0.0572(16) -0.0068(12) 0.0154(14) -0.0030(13)
C6 0.0495(16) 0.0497(17) 0.0536(15) -0.0001(13) 0.0112(13) -0.0055(13)
C8 0.0654(18) 0.0352(13) 0.0646(17) 0.0015(13) 0.0164(14) 0.0016(13)
C9 0.0559(17) 0.0423(15) 0.0766(19) -0.0048(14) 0.0150(15) 0.0053(13)
C12 0.0647(19) 0.0476(17) 0.0698(18) 0.0010(14) 0.0230(15) -0.0042(14)
C13 0.067(2) 0.0492(17) 0.0699(19) -0.0006(15) 0.0062(16) 0.0006(15)
C14 0.063(2) 0.071(2) 0.082(2) -0.0217(18) 0.0093(18) 0.0213(17)
C15 0.067(2) 0.088(3) 0.098(3) -0.014(2) 0.0372(19) 0.0080(19)
C16 0.066(2) 0.073(2) 0.086(2) -0.0056(18) 0.0335(18) -0.0026(17)
C17 0.0545(17) 0.0475(16) 0.0549(16) 0.0010(13) 0.0097(14) -0.0074(13)
C18 0.070(2) 0.086(2) 0.090(2) -0.0048(18) 0.0359(19) 0.0051(18)
C3A 0.0550(16) 0.0372(14) 0.0536(15) -0.0033(12) 0.0154(13) -0.0003(12)
C7A 0.0491(15) 0.0368(13) 0.0467(14) 0.0015(11) 0.0093(12) -0.0020(12)
C12A 0.0456(15) 0.0515(16) 0.0497(15) -0.0065(12) 0.0074(13) -0.0008(13)
C16A 0.0463(15) 0.0521(16) 0.0550(16) -0.0079(13) 0.0094(13) -0.0016(13)
Cl1 0.1079(7) 0.0392(4) 0.1117(7) -0.0120(4) 0.0494(6) 0.0009(4)
N1 0.0567(14) 0.0371(12) 0.0612(14) 0.0003(10) 0.0211(11) -0.0006(10)
N2 0.0656(16) 0.0468(14) 0.0762(16) 0.0016(12) 0.0348(13) -0.0025(12)
N5 0.0592(14) 0.0444(13) 0.0643(14) -0.0017(11) 0.0163(12) -0.0068(11)
N7 0.0477(13) 0.0458(13) 0.0562(13) -0.0021(10) 0.0159(11) -0.0023(10)
N10 0.0480(13) 0.0456(12) 0.0613(13) -0.0080(11) 0.0143(11) 0.0007(10)
N11 0.0575(14) 0.0440(13) 0.0699(15) -0.0012(11) 0.0238(12) -0.0043(11)
O1 0.0845(15) 0.0525(12) 0.0890(15) 0.0076(11) 0.0344(12) -0.0091(11)
S1 0.0612(5) 0.0693(5) 0.0781(5) 0.0050(4) 0.0299(4) -0.0085(4)

_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
C3 N2 1.318(3) . ?
C3 C3A 1.410(4) . ?
C3 H3 0.9300 . ?
C4 N5 1.313(3) . ?
C4 C3A 1.384(4) . ?
C4 Cl1 1.731(3) . ?
C6 N7 1.320(3) . ?
C6 N5 1.359(3) . ?
C6 S1 1.755(3) . ?
C8 N1 1.454(3) . ?
C8 C9 1.503(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N10 1.460(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C12 N11 1.283(3) . ?
C12 C12A 1.423(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.361(4) . ?
C13 C12A 1.410(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.393(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.355(4) . ?
C15 H15 0.9300 . ?
C16 C16A 1.387(4) . ?
C16 H16 0.9300 . ?
C17 O1 1.214(3) . ?
C17 N10 1.377(3) . ?
C17 C16A 1.467(4) . ?
C18 S1 1.799(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C3A C7A 1.399(3) . ?
C7A N7 1.343(3) . ?
C7A N1 1.344(3) . ?
C12A C16A 1.386(4) . ?
N1 N2 1.374(3) . ?
N10 N11 1.379(3) . ?

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 C3 C3A 111.4(2) . . ?
N2 C3 H3 124.3 . . ?
C3A C3 H3 124.3 . . ?
N5 C4 C3A 122.8(2) . . ?
N5 C4 Cl1 117.63(19) . . ?
C3A C4 Cl1 119.6(2) . . ?
N7 C6 N5 128.4(2) . . ?
N7 C6 S1 119.4(2) . . ?
N5 C6 S1 112.24(19) . . ?
N1 C8 C9 112.4(2) . . ?
N1 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
N10 C9 C8 109.5(2) . . ?
N10 C9 H9A 109.8 . . ?
C8 C9 H9A 109.8 . . ?
N10 C9 H9B 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
N11 C12 C12A 125.9(3) . . ?
N11 C12 H12 117.0 . . ?
C12A C12 H12 117.0 . . ?
C14 C13 C12A 119.9(3) . . ?
C14 C13 H13 120.0 . . ?
C12A C13 H13 120.0 . . ?
C13 C14 C15 119.6(3) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 121.3(3) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C16A 119.8(3) . . ?
C15 C16 H16 120.1 . . ?
C16A C16 H16 120.1 . . ?
O1 C17 N10 120.4(3) . . ?
O1 C17 C16A 124.8(3) . . ?
N10 C17 C16A 114.8(2) . . ?
S1 C18 H18A 109.5 . . ?
S1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
S1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C3A C7A 114.0(2) . . ?
C4 C3A C3 141.5(2) . . ?
C7A C3A C3 104.4(2) . . ?
N7 C7A N1 126.4(2) . . ?
N7 C7A C3A 126.4(2) . . ?
N1 C7A C3A 107.2(2) . . ?
C16A C12A C13 119.4(2) . . ?
C16A C12A C12 117.2(2) . . ?
C13 C12A C12 123.4(3) . . ?
C12A C16A C16 119.9(3) . . ?
C12A C16A C17 119.6(2) . . ?
C16 C16A C17 120.5(3) . . ?
C7A N1 N2 111.2(2) . . ?
C7A N1 C8 126.8(2) . . ?
N2 N1 C8 122.0(2) . . ?
C3 N2 N1 105.8(2) . . ?
C4 N5 C6 116.4(2) . . ?
C6 N7 C7A 111.9(2) . . ?
C17 N10 N11 126.2(2) . . ?
C17 N10 C9 119.4(2) . . ?
N11 N10 C9 114.2(2) . . ?
C12 N11 N10 116.2(2) . . ?
C6 S1 C18 102.43(14) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C8 C9 N10 -172.4(2) . . . . ?
C12A C13 C14 C15 -0.9(5) . . . . ?
C13 C14 C15 C16 0.1(5) . . . . ?
C14 C15 C16 C16A 0.3(5) . . . . ?
N5 C4 C3A C7A -1.6(4) . . . . ?
Cl1 C4 C3A C7A 177.70(19) . . . . ?
N5 C4 C3A C3 177.7(3) . . . . ?
Cl1 C4 C3A C3 -3.0(5) . . . . ?
N2 C3 C3A C4 -179.4(3) . . . . ?
N2 C3 C3A C7A 0.0(3) . . . . ?
C4 C3A C7A N7 0.7(4) . . . . ?
C3 C3A C7A N7 -178.8(2) . . . . ?
C4 C3A C7A N1 180.0(2) . . . . ?
C3 C3A C7A N1 0.4(3) . . . . ?
C14 C13 C12A C16A 1.3(4) . . . . ?
C14 C13 C12A C12 -177.7(3) . . . . ?
N11 C12 C12A C16A 1.5(4) . . . . ?
N11 C12 C12A C13 -179.5(3) . . . . ?
C13 C12A C16A C16 -1.0(4) . . . . ?
C12 C12A C16A C16 178.1(3) . . . . ?
C13 C12A C16A C17 178.7(2) . . . . ?
C12 C12A C16A C17 -2.2(4) . . . . ?
C15 C16 C16A C12A 0.2(5) . . . . ?
C15 C16 C16A C17 -179.5(3) . . . . ?
O1 C17 C16A C12A -177.9(3) . . . . ?
N10 C17 C16A C12A 2.5(4) . . . . ?
O1 C17 C16A C16 1.8(4) . . . . ?
N10 C17 C16A C16 -177.8(2) . . . . ?
N7 C7A N1 N2 178.6(2) . . . . ?
C3A C7A N1 N2 -0.6(3) . . . . ?
N7 C7A N1 C8 -2.4(4) . . . . ?
C3A C7A N1 C8 178.4(2) . . . . ?
C9 C8 N1 C7A 98.8(3) . . . . ?
C9 C8 N1 N2 -82.3(3) . . . . ?
C3A C3 N2 N1 -0.4(3) . . . . ?
C7A N1 N2 C3 0.6(3) . . . . ?
C8 N1 N2 C3 -178.4(2) . . . . ?
C3A C4 N5 C6 0.7(4) . . . . ?
Cl1 C4 N5 C6 -178.58(19) . . . . ?
N7 C6 N5 C4 1.3(4) . . . . ?
S1 C6 N5 C4 -177.93(19) . . . . ?
N5 C6 N7 C7A -2.1(4) . . . . ?
S1 C6 N7 C7A 177.12(17) . . . . ?
N1 C7A N7 C6 -178.1(2) . . . . ?
C3A C7A N7 C6 1.0(4) . . . . ?
O1 C17 N10 N11 178.2(2) . . . . ?
C16A C17 N10 N11 -2.1(4) . . . . ?
O1 C17 N10 C9 3.3(4) . . . . ?
C16A C17 N10 C9 -177.0(2) . . . . ?
C8 C9 N10 C17 84.8(3) . . . . ?
C8 C9 N10 N11 -90.6(3) . . . . ?
C12A C12 N11 N10 -1.0(4) . . . . ?
C17 N10 N11 C12 1.4(4) . . . . ?
C9 N10 N11 C12 176.5(2) . . . . ?
N7 C6 S1 C18 7.0(3) . . . . ?
N5 C6 S1 C18 -173.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.051

data_5g
_database_code_depnum_ccdc_archive 'CCDC 833097'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2-(2-(4-methoxy-6-(methylsulfonyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)
phthalazin-1(2H)-one

;
_chemical_name_common            none
_chemical_melting_point          201
_chemical_formula_moiety         'C17 H16 N6 O4 S'
_chemical_formula_sum            'C17 H16 N6 O4 S'
_chemical_formula_weight         400.42

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

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                   9.2490(10)
_cell_length_b                   17.580(2)
_cell_length_c                   11.550(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.110(10)
_cell_angle_gamma                90.00
_cell_volume                     1813.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    30
_cell_measurement_theta_min      5.13
_cell_measurement_theta_max      12.28

_exptl_crystal_description       'rectangular block'
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.217
_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      293(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  'Bruker P4 diffractometer'
_diffrn_measurement_method       \q-2\q
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 97
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4074
_diffrn_reflns_av_R_equivalents  0.0841
_diffrn_reflns_av_sigmaI/netI    0.0675
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3187
_reflns_number_gt                2148
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_cell_refinement       'XSCANS (Siemens, 1996)'
_computing_data_reduction        'XSCANS (Siemens, 1996)'
_computing_structure_solution    'SHELXTL-NT(Bruker, 1997)'
_computing_structure_refinement  'SHELXTL-NT(Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL-NT(Bruker, 1997)'
_computing_publication_material  'SHELXTL-NT(Bruker, 1997)'

_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^)+(0.0551P)^2^+1.0176P] 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         3187
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1354
_refine_ls_wR_factor_gt          0.1113
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
C3 C 0.5508(4) 0.20801(19) 0.4187(3) 0.0525(8) Uani 1 1 d . . .
H3 H 0.4983 0.1961 0.4749 0.063 Uiso 1 1 calc R . .
C4 C 0.6957(3) 0.08160(17) 0.3967(2) 0.0402(7) Uani 1 1 d . . .
C6 C 0.8253(3) 0.10049(16) 0.2570(2) 0.0371(7) Uani 1 1 d . . .
C8 C 0.6456(4) 0.33150(17) 0.2109(3) 0.0473(8) Uani 1 1 d . . .
H8A H 0.7355 0.3268 0.1830 0.057 Uiso 1 1 calc R . .
H8B H 0.6512 0.3792 0.2540 0.057 Uiso 1 1 calc R . .
C9 C 0.5100(4) 0.33251(18) 0.1041(3) 0.0496(8) Uani 1 1 d . . .
H9A H 0.4200 0.3367 0.1319 0.059 Uiso 1 1 calc R . .
H9B H 0.5149 0.3766 0.0548 0.059 Uiso 1 1 calc R . .
C12 C 0.4088(4) 0.1431(2) 0.0037(3) 0.0561(9) Uani 1 1 d . . .
H12 H 0.3472 0.1049 0.0197 0.067 Uiso 1 1 calc R . .
C13 C 0.4927(4) 0.05414(19) -0.1351(3) 0.0548(9) Uani 1 1 d . . .
H13 H 0.4318 0.0154 -0.1199 0.066 Uiso 1 1 calc R . .
C14 C 0.5809(4) 0.0424(2) -0.2104(3) 0.0610(9) Uani 1 1 d . . .
H14 H 0.5805 -0.0050 -0.2463 0.073 Uiso 1 1 calc R . .
C15 C 0.6714(4) 0.0992(2) -0.2351(3) 0.0650(10) Uani 1 1 d . . .
H15 H 0.7314 0.0895 -0.2867 0.078 Uiso 1 1 calc R . .
C16 C 0.6740(4) 0.1695(2) -0.1848(3) 0.0582(9) Uani 1 1 d . . .
H16 H 0.7336 0.2078 -0.2030 0.070 Uiso 1 1 calc R . .
C17 C 0.5922(4) 0.25683(19) -0.0451(3) 0.0491(8) Uani 1 1 d . . .
C18 C 1.0184(5) 0.1243(2) 0.1081(4) 0.0792(12) Uani 1 1 d . . .
H18A H 1.0838 0.1537 0.1703 0.119 Uiso 1 1 calc R . .
H18B H 0.9418 0.1568 0.0609 0.119 Uiso 1 1 calc R . .
H18C H 1.0750 0.1024 0.0576 0.119 Uiso 1 1 calc R . .
C19 C 0.7077(4) -0.03773(18) 0.4960(3) 0.0573(9) Uani 1 1 d . . .
H19A H 0.6737 -0.0664 0.4232 0.086 Uiso 1 1 calc R . .
H19B H 0.6717 -0.0610 0.5583 0.086 Uiso 1 1 calc R . .
H19C H 0.8152 -0.0368 0.5193 0.086 Uiso 1 1 calc R . .
C3A C 0.6444(3) 0.15699(16) 0.3787(2) 0.0403(7) Uani 1 1 d . . .
C7A C 0.6973(3) 0.19830(16) 0.2952(2) 0.0375(7) Uani 1 1 d . . .
C12A C 0.4945(3) 0.12630(19) -0.0798(3) 0.0454(8) Uani 1 1 d . . .
C16A C 0.5863(3) 0.18300(18) -0.1059(3) 0.0440(7) Uani 1 1 d . . .
N1 N 0.6390(3) 0.26914(13) 0.2913(2) 0.0425(6) Uani 1 1 d . . .
N2 N 0.5468(3) 0.27440(15) 0.3670(2) 0.0525(7) Uani 1 1 d . . .
N5 N 0.7867(3) 0.05344(13) 0.3355(2) 0.0400(6) Uani 1 1 d . . .
N7 N 0.7905(3) 0.17194(13) 0.2307(2) 0.0386(6) Uani 1 1 d . . .
N10 N 0.5025(3) 0.26321(15) 0.0320(2) 0.0458(6) Uani 1 1 d . . .
N11 N 0.4101(3) 0.20734(16) 0.0586(2) 0.0523(7) Uani 1 1 d . . .
O1 O 0.6712(3) 0.30999(14) -0.0584(2) 0.0735(8) Uani 1 1 d . . .
O2 O 0.6507(2) 0.03989(12) 0.47640(19) 0.0511(6) Uani 1 1 d . . .
O3 O 0.8329(3) 0.01120(15) 0.0796(2) 0.0701(7) Uani 1 1 d . . .
O4 O 1.0478(3) 0.00951(15) 0.2532(2) 0.0741(8) Uani 1 1 d . . .
S1 S 0.93619(9) 0.05240(4) 0.17187(7) 0.0435(2) 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
C3 0.064(2) 0.0489(19) 0.0532(19) -0.0009(16) 0.0299(17) 0.0103(16)
C4 0.0449(17) 0.0392(16) 0.0366(15) -0.0014(13) 0.0106(14) -0.0007(14)
C6 0.0347(16) 0.0359(16) 0.0392(15) -0.0028(13) 0.0071(13) 0.0003(12)
C8 0.059(2) 0.0307(16) 0.0520(18) -0.0028(14) 0.0142(16) 0.0029(14)
C9 0.054(2) 0.0446(18) 0.0502(18) -0.0024(15) 0.0141(16) 0.0133(15)
C12 0.0461(19) 0.062(2) 0.060(2) -0.0027(19) 0.0145(16) -0.0107(17)
C13 0.055(2) 0.052(2) 0.0523(19) -0.0084(16) 0.0057(17) -0.0128(17)
C14 0.064(2) 0.057(2) 0.058(2) -0.0197(18) 0.0084(18) -0.0033(18)
C15 0.058(2) 0.077(3) 0.062(2) -0.021(2) 0.0192(18) -0.005(2)
C16 0.053(2) 0.064(2) 0.062(2) -0.0077(18) 0.0220(17) -0.0083(18)
C17 0.0470(19) 0.0474(19) 0.0525(18) -0.0027(15) 0.0125(16) -0.0003(16)
C18 0.088(3) 0.062(2) 0.113(3) 0.001(2) 0.071(3) -0.006(2)
C19 0.083(2) 0.0444(19) 0.0490(19) 0.0101(15) 0.0257(18) 0.0107(18)
C3A 0.0440(17) 0.0379(16) 0.0389(16) -0.0049(13) 0.0106(14) 0.0009(13)
C7A 0.0360(16) 0.0352(16) 0.0381(15) -0.0075(13) 0.0041(13) -0.0004(13)
C12A 0.0347(16) 0.058(2) 0.0396(16) -0.0026(15) 0.0035(13) -0.0009(15)
C16A 0.0372(16) 0.0495(18) 0.0430(17) -0.0059(14) 0.0065(14) 0.0003(14)
N1 0.0472(15) 0.0366(14) 0.0439(14) -0.0030(11) 0.0125(12) 0.0057(12)
N2 0.0615(18) 0.0467(16) 0.0534(16) -0.0041(13) 0.0223(14) 0.0115(13)
N5 0.0461(14) 0.0353(13) 0.0401(13) -0.0022(11) 0.0138(12) 0.0041(11)
N7 0.0386(13) 0.0364(13) 0.0406(13) -0.0039(11) 0.0097(11) 0.0023(11)
N10 0.0444(15) 0.0473(15) 0.0449(14) -0.0037(12) 0.0103(12) 0.0044(12)
N11 0.0465(16) 0.0571(17) 0.0526(16) -0.0062(14) 0.0117(13) -0.0015(14)
O1 0.0901(19) 0.0527(15) 0.0912(19) -0.0131(14) 0.0476(16) -0.0190(14)
O2 0.0688(15) 0.0424(12) 0.0496(12) 0.0059(10) 0.0287(11) 0.0085(11)
O3 0.0645(15) 0.0847(18) 0.0667(15) -0.0371(14) 0.0272(13) -0.0179(14)
O4 0.0695(17) 0.0848(18) 0.0687(16) 0.0055(14) 0.0195(13) 0.0389(14)
S1 0.0440(4) 0.0417(4) 0.0477(4) -0.0035(4) 0.0175(4) 0.0037(4)

_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
C3 N2 1.308(4) . ?
C3 C3A 1.406(4) . ?
C4 O2 1.326(3) . ?
C4 N5 1.327(4) . ?
C4 C3A 1.405(4) . ?
C6 N7 1.312(4) . ?
C6 N5 1.343(4) . ?
C6 S1 1.805(3) . ?
C8 N1 1.448(4) . ?
C8 C9 1.512(4) . ?
C9 N10 1.467(4) . ?
C12 N11 1.293(4) . ?
C12 C12A 1.429(5) . ?
C13 C14 1.354(5) . ?
C13 C12A 1.419(5) . ?
C14 C15 1.380(5) . ?
C15 C16 1.362(5) . ?
C16 C16A 1.388(4) . ?
C17 O1 1.220(4) . ?
C17 N10 1.371(4) . ?
C17 C16A 1.470(4) . ?
C18 S1 1.736(4) . ?
C19 O2 1.459(4) . ?
C3A C7A 1.395(4) . ?
C7A N1 1.353(4) . ?
C7A N7 1.359(4) . ?
C12A C16A 1.393(4) . ?
N1 N2 1.374(4) . ?
N10 N11 1.388(4) . ?
O3 S1 1.429(2) . ?
O4 S1 1.418(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
N2 C3 C3A 111.4(3) . . ?
O2 C4 N5 121.4(3) . . ?
O2 C4 C3A 118.0(3) . . ?
N5 C4 C3A 120.6(3) . . ?
N7 C6 N5 130.8(3) . . ?
N7 C6 S1 117.5(2) . . ?
N5 C6 S1 111.6(2) . . ?
N1 C8 C9 111.5(3) . . ?
N10 C9 C8 111.1(2) . . ?
N11 C12 C12A 125.1(3) . . ?
C14 C13 C12A 119.2(3) . . ?
C13 C14 C15 121.4(3) . . ?
C16 C15 C14 120.8(3) . . ?
C15 C16 C16A 119.2(3) . . ?
O1 C17 N10 120.2(3) . . ?
O1 C17 C16A 124.4(3) . . ?
N10 C17 C16A 115.4(3) . . ?
C7A C3A C4 115.3(3) . . ?
C7A C3A C3 104.6(3) . . ?
C4 C3A C3 140.0(3) . . ?
N1 C7A N7 126.9(3) . . ?
N1 C7A C3A 107.1(2) . . ?
N7 C7A C3A 126.1(3) . . ?
C16A C12A C13 118.5(3) . . ?
C16A C12A C12 118.4(3) . . ?
C13 C12A C12 123.1(3) . . ?
C16 C16A C12A 120.9(3) . . ?
C16 C16A C17 120.7(3) . . ?
C12A C16A C17 118.5(3) . . ?
C7A N1 N2 110.4(2) . . ?
C7A N1 C8 129.4(3) . . ?
N2 N1 C8 119.6(2) . . ?
C3 N2 N1 106.4(2) . . ?
C4 N5 C6 116.6(2) . . ?
C6 N7 C7A 110.6(2) . . ?
C17 N10 N11 126.7(3) . . ?
C17 N10 C9 119.3(3) . . ?
N11 N10 C9 113.7(2) . . ?
C12 N11 N10 115.9(3) . . ?
C4 O2 C19 117.3(2) . . ?
O4 S1 O3 117.03(17) . . ?
O4 S1 C18 110.2(2) . . ?
O3 S1 C18 109.54(19) . . ?
O4 S1 C6 107.86(14) . . ?
O3 S1 C6 106.21(14) . . ?
C18 S1 C6 105.30(16) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.102

#===END


data_5i
_database_code_depnum_ccdc_archive 'CCDC 837594'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
3-(2-(4-methoxy-6-(methylsulfonyl)-
1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)
quinazolin-4(3H)-one

;
_chemical_name_common            none
_chemical_melting_point          219
_chemical_formula_moiety         'C17 H16 N6 O4 S'
_chemical_formula_sum            'C17 H16 N6 O4 S'
_chemical_formula_weight         400.42

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   C2/c

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

_cell_length_a                   18.2274(5)
_cell_length_b                   15.2903(4)
_cell_length_c                   13.9319(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.746(3)
_cell_angle_gamma                90.00
_cell_volume                     3676.87(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       'rectangular block'
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1664
_exptl_absorpt_coefficient_mu    0.214
_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      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7468
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         28.96
_reflns_number_total             4147
_reflns_number_gt                2728
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_structure_solution    'SHELXTL-NT(Bruker, 1997)'
_computing_structure_refinement  'SHELXTL-NT(Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL-NT(Bruker, 1997)'
_computing_publication_material  'SHELXTL-NT(Bruker, 1997)'

_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^)+(0.0645P)^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         4147
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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
C3 C -0.06572(11) 0.46705(13) 0.06421(16) 0.0534(5) Uani 1 1 d . . .
H3 H -0.0668 0.5276 0.0693 0.064 Uiso 1 1 calc R . .
C4 C 0.07375(10) 0.42133(12) 0.18595(14) 0.0436(4) Uani 1 1 d . . .
C6 C 0.08338(9) 0.27349(11) 0.18311(13) 0.0365(4) Uani 1 1 d . . .
C8 C -0.14518(10) 0.26350(13) -0.03782(15) 0.0518(5) Uani 1 1 d . . .
H8A H -0.1996 0.2751 -0.0490 0.062 Uiso 1 1 calc R . .
H8B H -0.1318 0.2093 0.0000 0.062 Uiso 1 1 calc R . .
C9 C -0.13218(10) 0.25311(13) -0.13845(15) 0.0544(5) Uani 1 1 d . . .
H9A H -0.1647 0.2061 -0.1759 0.065 Uiso 1 1 calc R . .
H9B H -0.1475 0.3065 -0.1773 0.065 Uiso 1 1 calc R . .
C11 C -0.00275(14) 0.30159(13) -0.13401(15) 0.0570(5) Uani 1 1 d . . .
H11 H -0.0251 0.3568 -0.1477 0.068 Uiso 1 1 calc R . .
C13 C 0.17798(13) 0.20135(16) -0.09778(17) 0.0667(6) Uani 1 1 d . . .
H13 H 0.2068 0.2498 -0.1046 0.080 Uiso 1 1 calc R . .
C14 C 0.21215(13) 0.1207(2) -0.08025(18) 0.0770(7) Uani 1 1 d . . .
H14 H 0.2639 0.1147 -0.0756 0.092 Uiso 1 1 calc R . .
C15 C 0.17005(15) 0.04740(17) -0.06921(19) 0.0780(7) Uani 1 1 d . . .
H15 H 0.1934 -0.0073 -0.0569 0.094 Uiso 1 1 calc R . .
C16 C 0.09334(13) 0.05736(14) -0.07684(18) 0.0651(6) Uani 1 1 d . . .
H16 H 0.0647 0.0091 -0.0692 0.078 Uiso 1 1 calc R . .
C17 C -0.02370(11) 0.14985(12) -0.10476(15) 0.0509(5) Uani 1 1 d . . .
C18 C 0.18156(12) 0.50654(14) 0.28190(19) 0.0755(7) Uani 1 1 d . . .
H18A H 0.1913 0.4639 0.3351 0.113 Uiso 1 1 calc R . .
H18B H 0.1912 0.5640 0.3110 0.113 Uiso 1 1 calc R . .
H18C H 0.2152 0.4959 0.2424 0.113 Uiso 1 1 calc R . .
C19 C 0.09067(11) 0.08959(13) 0.18670(17) 0.0646(6) Uani 1 1 d . . .
H19A H 0.1219 0.0383 0.2092 0.097 Uiso 1 1 calc R . .
H19B H 0.0723 0.0910 0.1140 0.097 Uiso 1 1 calc R . .
H19C H 0.0473 0.0882 0.2116 0.097 Uiso 1 1 calc R . .
C3A C -0.00249(10) 0.41413(11) 0.11791(13) 0.0423(4) Uani 1 1 d . . .
C7A C -0.02669(9) 0.32943(11) 0.08841(13) 0.0390(4) Uani 1 1 d . . .
C12A C 0.10093(11) 0.21151(13) -0.10551(15) 0.0508(5) Uani 1 1 d . . .
C16A C 0.05849(11) 0.13893(12) -0.09589(14) 0.0500(5) Uani 1 1 d . . .
N1 N -0.09897(8) 0.33454(9) 0.02157(11) 0.0458(4) Uani 1 1 d . . .
N2 N -0.12277(9) 0.41963(10) 0.00612(13) 0.0553(4) Uani 1 1 d . . .
N5 N 0.11653(8) 0.35042(9) 0.21834(11) 0.0436(4) Uani 1 1 d . . .
N7 N 0.01478(7) 0.25504(9) 0.11962(11) 0.0399(3) Uani 1 1 d . . .
N10 N -0.05109(9) 0.23380(9) -0.12736(11) 0.0453(4) Uani 1 1 d . . .
N12 N 0.06812(11) 0.29643(11) -0.12345(14) 0.0636(5) Uani 1 1 d . . .
O1 O -0.06585(9) 0.09212(9) -0.09342(14) 0.0760(5) Uani 1 1 d . . .
O2 O 0.10145(8) 0.50028(8) 0.21719(11) 0.0597(4) Uani 1 1 d . . .
O3 O 0.16644(10) 0.18431(10) 0.33955(11) 0.0830(5) Uani 1 1 d . . .
O4 O 0.20686(9) 0.18567(9) 0.18903(16) 0.0823(5) Uani 1 1 d . . .
S1 S 0.14591(2) 0.18213(3) 0.23238(4) 0.04358(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
C3 0.0573(12) 0.0464(11) 0.0556(13) 0.0044(10) 0.0171(10) 0.0083(9)
C4 0.0481(10) 0.0422(10) 0.0416(10) -0.0032(8) 0.0160(8) -0.0093(8)
C6 0.0299(8) 0.0426(10) 0.0357(9) -0.0007(8) 0.0086(7) -0.0030(7)
C8 0.0311(9) 0.0635(12) 0.0505(12) -0.0049(10) -0.0010(8) -0.0011(8)
C9 0.0470(11) 0.0573(12) 0.0445(12) -0.0005(9) -0.0052(9) 0.0032(9)
C11 0.0699(14) 0.0485(12) 0.0469(12) 0.0081(9) 0.0108(10) -0.0067(10)
C13 0.0579(13) 0.0899(17) 0.0524(13) -0.0017(12) 0.0180(10) -0.0165(12)
C14 0.0536(13) 0.115(2) 0.0644(16) -0.0170(15) 0.0212(11) 0.0044(15)
C15 0.0814(18) 0.0731(16) 0.0733(17) -0.0162(13) 0.0160(13) 0.0169(14)
C16 0.0671(14) 0.0540(13) 0.0717(16) -0.0121(11) 0.0188(12) -0.0078(11)
C17 0.0597(12) 0.0414(10) 0.0498(12) -0.0056(9) 0.0151(10) -0.0069(9)
C18 0.0679(15) 0.0631(14) 0.0826(18) -0.0105(12) 0.0062(13) -0.0307(12)
C19 0.0607(13) 0.0476(11) 0.0694(15) 0.0039(10) -0.0016(11) -0.0091(10)
C3A 0.0446(10) 0.0434(10) 0.0389(10) -0.0001(8) 0.0132(8) 0.0003(8)
C7A 0.0332(8) 0.0475(10) 0.0343(9) -0.0020(8) 0.0081(7) 0.0019(7)
C12A 0.0550(12) 0.0613(12) 0.0350(10) 0.0012(9) 0.0128(8) -0.0052(10)
C16A 0.0539(11) 0.0533(11) 0.0414(11) -0.0078(9) 0.0134(9) -0.0048(9)
N1 0.0352(8) 0.0526(9) 0.0433(9) -0.0006(7) 0.0036(6) 0.0067(7)
N2 0.0500(9) 0.0558(10) 0.0551(11) 0.0048(8) 0.0101(8) 0.0131(8)
N5 0.0373(8) 0.0449(8) 0.0447(9) -0.0032(7) 0.0076(6) -0.0082(7)
N7 0.0317(7) 0.0450(8) 0.0378(8) -0.0040(7) 0.0041(6) 0.0005(6)
N10 0.0488(9) 0.0429(8) 0.0396(9) 0.0013(7) 0.0077(7) -0.0055(7)
N12 0.0686(12) 0.0610(11) 0.0564(12) 0.0117(9) 0.0135(9) -0.0176(9)
O1 0.0696(10) 0.0446(8) 0.1131(14) 0.0001(8) 0.0284(9) -0.0147(7)
O2 0.0657(9) 0.0424(7) 0.0620(9) -0.0024(7) 0.0081(7) -0.0154(6)
O3 0.0990(12) 0.0822(11) 0.0439(9) -0.0024(8) -0.0105(8) 0.0228(9)
O4 0.0491(8) 0.0722(10) 0.1399(17) 0.0170(10) 0.0502(10) 0.0105(7)
S1 0.0308(2) 0.0455(3) 0.0465(3) -0.0020(2) 0.00140(18) -0.00059(19)

_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
C3 N2 1.312(2) . ?
C3 C3A 1.410(2) . ?
C4 O2 1.3268(19) . ?
C4 N5 1.327(2) . ?
C4 C3A 1.413(2) . ?
C6 N7 1.309(2) . ?
C6 N5 1.341(2) . ?
C6 S1 1.7941(17) . ?
C8 N1 1.458(2) . ?
C8 C9 1.503(3) . ?
C9 N10 1.466(2) . ?
C11 N12 1.255(3) . ?
C11 N10 1.383(2) . ?
C13 C14 1.367(3) . ?
C13 C12A 1.382(3) . ?
C14 C15 1.395(3) . ?
C15 C16 1.376(3) . ?
C16 C16A 1.386(3) . ?
C17 O1 1.213(2) . ?
C17 N10 1.377(2) . ?
C17 C16A 1.473(3) . ?
C18 O2 1.452(2) . ?
C19 S1 1.7347(19) . ?
C3A C7A 1.387(2) . ?
C7A N1 1.349(2) . ?
C7A N7 1.358(2) . ?
C12A C16A 1.384(3) . ?
C12A N12 1.418(2) . ?
N1 N2 1.3665(19) . ?
O3 S1 1.4183(16) . ?
O4 S1 1.4257(16) . ?

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 C3 C3A 111.14(16) . . ?
O2 C4 N5 120.78(16) . . ?
O2 C4 C3A 118.66(16) . . ?
N5 C4 C3A 120.56(15) . . ?
N7 C6 N5 131.01(16) . . ?
N7 C6 S1 116.23(12) . . ?
N5 C6 S1 112.75(12) . . ?
N1 C8 C9 111.87(16) . . ?
N10 C9 C8 112.26(15) . . ?
N12 C11 N10 126.81(19) . . ?
C14 C13 C12A 120.5(2) . . ?
C13 C14 C15 120.6(2) . . ?
C16 C15 C14 118.9(2) . . ?
C15 C16 C16A 120.4(2) . . ?
O1 C17 N10 120.66(18) . . ?
O1 C17 C16A 125.18(18) . . ?
N10 C17 C16A 114.16(16) . . ?
C7A C3A C3 104.52(15) . . ?
C7A C3A C4 114.98(16) . . ?
C3 C3A C4 140.47(17) . . ?
N1 C7A N7 126.11(15) . . ?
N1 C7A C3A 107.31(15) . . ?
N7 C7A C3A 126.58(15) . . ?
C13 C12A C16A 119.2(2) . . ?
C13 C12A N12 118.50(19) . . ?
C16A C12A N12 122.29(18) . . ?
C12A C16A C16 120.27(19) . . ?
C12A C16A C17 119.10(17) . . ?
C16 C16A C17 120.63(18) . . ?
C7A N1 N2 110.73(14) . . ?
C7A N1 C8 127.33(14) . . ?
N2 N1 C8 121.58(14) . . ?
C3 N2 N1 106.29(14) . . ?
C4 N5 C6 116.47(14) . . ?
C6 N7 C7A 110.39(14) . . ?
C17 N10 C11 121.49(17) . . ?
C17 N10 C9 119.41(15) . . ?
C11 N10 C9 118.98(16) . . ?
C11 N12 C12A 116.01(17) . . ?
C4 O2 C18 117.67(15) . . ?
O3 S1 O4 117.86(11) . . ?
O3 S1 C19 109.33(10) . . ?
O4 S1 C19 108.36(11) . . ?
O3 S1 C6 107.74(8) . . ?
O4 S1 C6 107.10(8) . . ?
C19 S1 C6 105.80(9) . . ?

_diffrn_measured_fraction_theta_max 0.850
_diffrn_reflns_theta_full        28.96
_diffrn_measured_fraction_theta_full 0.850
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.039
#===END

# Attachment 'FinalAF88.CIF'

data_5g
_database_code_depnum_ccdc_archive 'CCDC 837595'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2-(2-(4-chloro-6-(methylsulfonyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)
phthalazin-1(2H)-one

;
_chemical_name_common            none
_chemical_melting_point          227
_chemical_formula_moiety         'C16 H13 Cl N6 O3 S'
_chemical_formula_sum            'C16 H13 Cl N6 O3 S'
_chemical_formula_weight         404.83

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'
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   Cc

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

_cell_length_a                   13.6729(8)
_cell_length_b                   9.0043(6)
_cell_length_c                   13.8349(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.388(5)
_cell_angle_gamma                90.00
_cell_volume                     1703.24(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6794
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      27.97

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.380
_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      273(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  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9542
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         28.14
_reflns_number_total             3913
_reflns_number_gt                3842
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL-NT(Bruker, 1997)'
_computing_structure_refinement  'SHELXTL-NT(Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL-NT(Bruker, 1997)'
_computing_publication_material  'SHELXTL-NT(Bruker, 1997)'

_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^+0.4352P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_number_reflns         3913
_refine_ls_number_parameters     245
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0816
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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
C3 C 0.50008(14) 1.1658(2) 0.32635(14) 0.0432(4) Uani 1 1 d . . .
H3 H 0.5087 1.2238 0.2714 0.052 Uiso 1 1 calc R . .
C4 C 0.36045(12) 1.29852(18) 0.42661(12) 0.0356(3) Uani 1 1 d . . .
C6 C 0.33518(12) 1.17388(17) 0.56532(12) 0.0330(3) Uani 1 1 d . . .
C8 C 0.55280(14) 0.8578(2) 0.47589(16) 0.0447(4) Uani 1 1 d . . .
H8A H 0.5568 0.8700 0.5455 0.054 Uiso 1 1 calc R . .
H8B H 0.6181 0.8381 0.4522 0.054 Uiso 1 1 calc R . .
C9 C 0.48697(16) 0.7289(2) 0.45193(17) 0.0526(5) Uani 1 1 d . . .
H9A H 0.4202 0.7535 0.4692 0.063 Uiso 1 1 calc R . .
H9B H 0.4886 0.7103 0.3829 0.063 Uiso 1 1 calc R . .
C12 C 0.49418(14) 0.4641(2) 0.64007(16) 0.0485(4) Uani 1 1 d . . .
H12 H 0.4627 0.4498 0.6987 0.058 Uiso 1 1 calc R . .
C13 C 0.58724(16) 0.2316(2) 0.66911(15) 0.0492(4) Uani 1 1 d . . .
H13 H 0.5543 0.2149 0.7267 0.059 Uiso 1 1 calc R . .
C14 C 0.65748(18) 0.1338(2) 0.63865(17) 0.0560(5) Uani 1 1 d . . .
H14 H 0.6723 0.0506 0.6758 0.067 Uiso 1 1 calc R . .
C15 C 0.70655(18) 0.1582(2) 0.5527(2) 0.0605(6) Uani 1 1 d . . .
H15 H 0.7542 0.0911 0.5330 0.073 Uiso 1 1 calc R . .
C16 C 0.68607(17) 0.2793(2) 0.49639(17) 0.0541(5) Uani 1 1 d . . .
H16 H 0.7193 0.2946 0.4388 0.065 Uiso 1 1 calc R . .
C17 C 0.59104(17) 0.5101(2) 0.46805(14) 0.0471(4) Uani 1 1 d . . .
C18 C 0.28554(16) 0.9927(2) 0.72111(17) 0.0524(5) Uani 1 1 d . . .
H18A H 0.3527 0.9771 0.7391 0.079 Uiso 1 1 calc R . .
H18B H 0.2674 0.9236 0.6712 0.079 Uiso 1 1 calc R . .
H18C H 0.2447 0.9777 0.7764 0.079 Uiso 1 1 calc R . .
C3A C 0.43240(12) 1.19739(18) 0.40097(12) 0.0341(3) Uani 1 1 d . . .
C7A C 0.44560(12) 1.08201(17) 0.46802(12) 0.0341(3) Uani 1 1 d . . .
C12A C 0.56543(13) 0.3574(2) 0.61245(13) 0.0386(3) Uani 1 1 d . . .
C16A C 0.61523(13) 0.3786(2) 0.52617(13) 0.0408(4) Uani 1 1 d . . .
Cl1 Cl 0.33070(4) 1.44174(5) 0.35063(3) 0.05300(13) Uani 1 1 d . . .
N1 N 0.51555(11) 0.99282(16) 0.43236(12) 0.0399(3) Uani 1 1 d . . .
N2 N 0.54867(13) 1.04379(18) 0.34550(12) 0.0460(4) Uani 1 1 d . . .
N5 N 0.31189(10) 1.28909(16) 0.50796(11) 0.0371(3) Uani 1 1 d . . .
N7 N 0.39812(10) 1.06623(16) 0.55200(11) 0.0357(3) Uani 1 1 d . . .
N10 N 0.51716(12) 0.59600(18) 0.50341(12) 0.0444(3) Uani 1 1 d . . .
N11 N 0.47028(12) 0.57791(19) 0.59044(14) 0.0496(4) Uani 1 1 d . . .
O1 O 0.63102(19) 0.5436(2) 0.39258(14) 0.0828(6) Uani 1 1 d . . .
O2 O 0.32138(14) 1.2724(2) 0.74139(11) 0.0680(5) Uani 1 1 d . . .
O3 O 0.17026(11) 1.20054(19) 0.65848(12) 0.0575(4) Uani 1 1 d . . .
S1 S 0.27067(3) 1.17352(5) 0.67855(3) 0.03810(10) 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
C3 0.0476(9) 0.0448(9) 0.0374(9) 0.0002(7) 0.0086(7) -0.0003(7)
C4 0.0414(8) 0.0299(7) 0.0355(8) 0.0037(6) -0.0019(6) 0.0021(6)
C6 0.0341(7) 0.0324(7) 0.0323(7) -0.0003(5) 0.0045(6) -0.0013(6)
C8 0.0397(8) 0.0346(8) 0.0600(11) 0.0022(8) 0.0014(8) 0.0085(7)
C9 0.0613(12) 0.0376(9) 0.0588(12) 0.0074(8) -0.0112(9) -0.0005(8)
C12 0.0450(9) 0.0492(10) 0.0516(11) 0.0036(8) 0.0153(8) -0.0046(8)
C13 0.0601(11) 0.0429(10) 0.0446(10) 0.0051(8) 0.0022(8) -0.0091(8)
C14 0.0679(13) 0.0366(9) 0.0633(13) 0.0045(9) -0.0125(10) -0.0007(9)
C15 0.0623(13) 0.0420(11) 0.0773(15) -0.0090(10) 0.0002(11) 0.0095(9)
C16 0.0623(12) 0.0441(10) 0.0562(12) -0.0076(9) 0.0174(10) 0.0034(9)
C17 0.0662(12) 0.0381(9) 0.0371(9) -0.0002(7) 0.0081(8) 0.0005(8)
C18 0.0576(12) 0.0511(11) 0.0487(10) 0.0171(9) 0.0084(8) 0.0016(9)
C3A 0.0383(7) 0.0317(7) 0.0325(8) 0.0006(6) 0.0008(6) -0.0011(6)
C7A 0.0353(7) 0.0292(7) 0.0379(8) -0.0003(6) 0.0024(6) 0.0005(6)
C12A 0.0405(8) 0.0335(8) 0.0419(9) -0.0010(6) 0.0013(7) -0.0054(6)
C16A 0.0480(9) 0.0348(8) 0.0396(9) -0.0018(7) 0.0033(7) -0.0036(7)
Cl1 0.0630(3) 0.0471(2) 0.0489(3) 0.0177(2) 0.0051(2) 0.0145(2)
N1 0.0398(7) 0.0330(7) 0.0470(8) 0.0001(6) 0.0079(6) 0.0044(6)
N2 0.0470(8) 0.0459(8) 0.0453(8) -0.0053(7) 0.0122(6) 0.0016(7)
N5 0.0400(7) 0.0326(7) 0.0387(7) 0.0031(6) 0.0031(6) 0.0051(6)
N7 0.0389(7) 0.0318(6) 0.0364(7) 0.0028(5) 0.0036(5) 0.0012(5)
N10 0.0479(8) 0.0365(7) 0.0487(9) 0.0049(6) -0.0022(6) -0.0002(6)
N11 0.0414(8) 0.0432(8) 0.0643(11) 0.0036(7) 0.0122(7) 0.0013(6)
O1 0.1310(18) 0.0634(11) 0.0545(10) 0.0160(8) 0.0425(11) 0.0211(11)
O2 0.0807(11) 0.0739(11) 0.0496(8) -0.0225(8) 0.0166(8) -0.0308(9)
O3 0.0453(7) 0.0679(9) 0.0593(8) 0.0080(7) 0.0117(6) 0.0100(7)
S1 0.03981(19) 0.0392(2) 0.03538(19) -0.00227(16) 0.00767(14) -0.00327(16)

_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
C3 N2 1.310(3) . ?
C3 C3A 1.420(2) . ?
C4 N5 1.313(2) . ?
C4 C3A 1.388(2) . ?
C4 Cl1 1.7110(16) . ?
C6 N7 1.310(2) . ?
C6 N5 1.343(2) . ?
C6 S1 1.8029(17) . ?
C8 N1 1.448(2) . ?
C8 C9 1.504(3) . ?
C9 N10 1.451(2) . ?
C12 N11 1.275(3) . ?
C12 C12A 1.423(3) . ?
C13 C14 1.372(3) . ?
C13 C12A 1.409(3) . ?
C14 C15 1.387(4) . ?
C15 C16 1.368(3) . ?
C16 C16A 1.383(3) . ?
C17 O1 1.220(3) . ?
C17 N10 1.366(3) . ?
C17 C16A 1.468(3) . ?
C18 S1 1.743(2) . ?
C3A C7A 1.404(2) . ?
C7A N7 1.342(2) . ?
C7A N1 1.345(2) . ?
C12A C16A 1.391(3) . ?
N1 N2 1.366(2) . ?
N10 N11 1.378(2) . ?
O2 S1 1.4217(16) . ?
O3 S1 1.4199(15) . ?

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 C3 C3A 110.67(17) . . ?
N5 C4 C3A 122.66(15) . . ?
N5 C4 Cl1 117.11(12) . . ?
C3A C4 Cl1 120.22(13) . . ?
N7 C6 N5 129.92(16) . . ?
N7 C6 S1 116.52(12) . . ?
N5 C6 S1 113.54(11) . . ?
N1 C8 C9 110.35(15) . . ?
N10 C9 C8 111.12(15) . . ?
N11 C12 C12A 124.87(18) . . ?
C14 C13 C12A 119.45(19) . . ?
C13 C14 C15 120.4(2) . . ?
C16 C15 C14 121.1(2) . . ?
C15 C16 C16A 119.1(2) . . ?
O1 C17 N10 120.21(19) . . ?
O1 C17 C16A 124.6(2) . . ?
N10 C17 C16A 115.17(17) . . ?
C4 C3A C7A 113.88(15) . . ?
C4 C3A C3 141.58(16) . . ?
C7A C3A C3 104.52(15) . . ?
N7 C7A N1 127.12(15) . . ?
N7 C7A C3A 126.13(15) . . ?
N1 C7A C3A 106.74(15) . . ?
C16A C12A C13 118.99(17) . . ?
C16A C12A C12 118.56(17) . . ?
C13 C12A C12 122.46(17) . . ?
C16 C16A C12A 120.99(18) . . ?
C16 C16A C17 120.93(18) . . ?
C12A C16A C17 118.08(16) . . ?
C7A N1 N2 111.27(14) . . ?
C7A N1 C8 126.71(16) . . ?
N2 N1 C8 122.01(15) . . ?
C3 N2 N1 106.79(15) . . ?
C4 N5 C6 115.92(13) . . ?
C6 N7 C7A 111.43(14) . . ?
C17 N10 N11 126.56(16) . . ?
C17 N10 C9 120.01(18) . . ?
N11 N10 C9 113.20(17) . . ?
C12 N11 N10 116.54(16) . . ?
O3 S1 O2 118.63(12) . . ?
O3 S1 C18 109.67(10) . . ?
O2 S1 C18 108.86(12) . . ?
O3 S1 C6 107.93(9) . . ?
O2 S1 C6 106.90(9) . . ?
C18 S1 C6 103.80(9) . . ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        28.14
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.062
#===END