#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/97/1519796.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1519796
loop_
_publ_author_name
'Collins, Ian'
'Horton, Peter N.'
'Hursthouse, Michael B.'
_publ_section_title
;
 3-Amino-6-methyl-2-(toluene-4-sulfonyl)-2,5-dihydro-pyrazolo[4,3-c]pyridin-
 4-one
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              439
_journal_year                    2007
_chemical_formula_sum            'C14 H14 N4 O3 S'
_chemical_formula_weight         318.35
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                112.574(2)
_cell_angle_beta                 90.804(2)
_cell_angle_gamma                96.144(2)
_cell_formula_units_Z            2
_cell_length_a                   6.6318(3)
_cell_length_b                   9.4254(4)
_cell_length_c                   12.0872(4)
_cell_measurement_reflns_used    2950
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     692.39(5)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997b)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_sigmaI/netI    0.0507
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11744
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  0.9899
_exptl_absorpt_correction_T_min  0.9775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            'Light Brown'
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3162
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0572
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0100P)²+1.4129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1203
_reflns_number_gt                2534
_reflns_number_total             3162
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-439.cif
_cod_data_source_block           2007src1290
_cod_depositor_comments
;
Citation :
Collins, Ian and Horton, Peter N. and Hursthouse, Michael B. (2007) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/439)

More at:
http://ecrystals.chem.soton.ac.uk/439/
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1519796
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.5588(4) 0.8454(3) 0.3216(2) 0.0186(5) Uani 1 1 d . . .
C2 C 0.4481(4) 0.7907(3) 0.3951(2) 0.0184(5) Uani 1 1 d . . .
C3 C 0.2684(4) 0.8640(3) 0.4161(2) 0.0187(5) Uani 1 1 d . . .
C4 C 0.1258(4) 0.8315(3) 0.4934(2) 0.0192(5) Uani 1 1 d . . .
H4 H 0.0044 0.8791 0.5099 0.023 Uiso 1 1 calc R . .
C5 C 0.1703(4) 0.7299(3) 0.5423(2) 0.0209(5) Uani 1 1 d . . .
C6 C 0.4893(4) 0.6776(3) 0.4425(2) 0.0207(5) Uani 1 1 d . . .
C7 C 0.0408(4) 0.6919(3) 0.6296(2) 0.0259(6) Uani 1 1 d . . .
H7A H -0.0833 0.7420 0.6376 0.039 Uiso 1 1 calc R . .
H7B H 0.1159 0.7292 0.7078 0.039 Uiso 1 1 calc R . .
H7C H 0.0049 0.5795 0.6005 0.039 Uiso 1 1 calc R . .
C8 C 0.2986(4) 0.8585(3) 0.0753(2) 0.0205(5) Uani 1 1 d . . .
C9 C 0.3740(4) 0.7211(3) 0.0077(3) 0.0286(6) Uani 1 1 d . . .
H9 H 0.5117 0.7084 0.0197 0.034 Uiso 1 1 calc R . .
C10 C 0.2451(5) 0.6031(3) -0.0772(3) 0.0341(7) Uani 1 1 d . . .
H10 H 0.2954 0.5090 -0.1241 0.041 Uiso 1 1 calc R . .
C11 C 0.0434(5) 0.6205(3) -0.0947(2) 0.0294(6) Uani 1 1 d . . .
C12 C -0.0271(4) 0.7595(3) -0.0266(3) 0.0290(6) Uani 1 1 d . . .
H12 H -0.1641 0.7732 -0.0394 0.035 Uiso 1 1 calc R . .
C13 C 0.0989(4) 0.8793(3) 0.0601(2) 0.0238(6) Uani 1 1 d . . .
H13 H 0.0486 0.9731 0.1077 0.029 Uiso 1 1 calc R . .
C14 C -0.0977(5) 0.4904(4) -0.1862(3) 0.0418(8) Uani 1 1 d . . .
H14A H -0.1258 0.4060 -0.1582 0.063 Uiso 1 1 calc R . .
H14B H -0.0336 0.4523 -0.2630 0.063 Uiso 1 1 calc R . .
H14C H -0.2254 0.5288 -0.1967 0.063 Uiso 1 1 calc R . .
N1 N 0.4467(3) 0.9512(2) 0.30370(19) 0.0191(5) Uani 1 1 d . . .
N2 N 0.2591(3) 0.9591(2) 0.35879(19) 0.0205(5) Uani 1 1 d . . .
N3 N 0.7392(3) 0.8082(3) 0.2752(2) 0.0236(5) Uani 1 1 d D . .
H3A H 0.8025 0.7576 0.3109 0.035 Uiso 1 1 d D . .
H3B H 0.8137 0.8715 0.2485 0.035 Uiso 1 1 d D . .
N4 N 0.3437(3) 0.6551(2) 0.5156(2) 0.0226(5) Uani 1 1 d . . .
H4A H 0.3614 0.5880 0.5482 0.027 Uiso 1 1 calc R . .
O1 O 0.6388(3) 0.6040(2) 0.41884(18) 0.0266(4) Uani 1 1 d . . .
O2 O 0.6648(3) 0.9974(2) 0.15408(17) 0.0252(4) Uani 1 1 d . . .
O3 O 0.3721(3) 1.1473(2) 0.22096(17) 0.0262(4) Uani 1 1 d . . .
S1 S 0.45816(10) 1.00628(7) 0.18650(6) 0.02028(17) Uani 1 1 d . . .
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'
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
N3 C1 C2 129.1(2) . .
N3 C1 N1 125.6(2) . .
C2 C1 N1 105.3(2) . .
C1 C2 C3 106.9(2) . .
C1 C2 C6 130.1(2) . .
C3 C2 C6 123.1(2) . .
N2 C3 C2 112.4(2) . .
N2 C3 C4 128.5(2) . .
C2 C3 C4 119.0(2) . .
C5 C4 C3 117.5(2) . .
C5 C4 H4 121.3 . .
C3 C4 H4 121.3 . .
C4 C5 N4 121.9(2) . .
C4 C5 C7 123.2(2) . .
N4 C5 C7 114.9(2) . .
O1 C6 N4 122.4(2) . .
O1 C6 C2 124.3(2) . .
N4 C6 C2 113.2(2) . .
C5 C7 H7A 109.5 . .
C5 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C5 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C13 C8 C9 121.6(3) . .
C13 C8 S1 119.1(2) . .
C9 C8 S1 119.3(2) . .
C10 C9 C8 118.9(3) . .
C10 C9 H9 120.5 . .
C8 C9 H9 120.5 . .
C9 C10 C11 120.9(3) . .
C9 C10 H10 119.6 . .
C11 C10 H10 119.6 . .
C10 C11 C12 118.9(3) . .
C10 C11 C14 120.7(3) . .
C12 C11 C14 120.4(3) . .
C11 C12 C13 121.3(3) . .
C11 C12 H12 119.3 . .
C13 C12 H12 119.3 . .
C8 C13 C12 118.4(3) . .
C8 C13 H13 120.8 . .
C12 C13 H13 120.8 . .
C11 C14 H14A 109.5 . .
C11 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C11 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C1 N1 N2 112.4(2) . .
C1 N1 S1 126.03(18) . .
N2 N1 S1 116.11(16) . .
C3 N2 N1 102.9(2) . .
C1 N3 H3A 112.4 . .
C1 N3 H3B 119.9 . .
H3A N3 H3B 118.5 . .
C6 N4 C5 125.1(2) . .
C6 N4 H4A 117.4 . .
C5 N4 H4A 117.4 . .
O3 S1 O2 121.25(12) . .
O3 S1 N1 107.16(11) . .
O2 S1 N1 104.42(11) . .
O3 S1 C8 109.70(12) . .
O2 S1 C8 109.65(12) . .
N1 S1 C8 102.95(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N3 1.352(3) .
C1 C2 1.372(4) .
C1 N1 1.384(3) .
C2 C3 1.419(4) .
C2 C6 1.437(3) .
C3 N2 1.332(3) .
C3 C4 1.430(4) .
C4 C5 1.357(4) .
C4 H4 0.9500 .
C5 N4 1.390(3) .
C5 C7 1.493(4) .
C6 O1 1.245(3) .
C6 N4 1.372(3) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 C13 1.379(4) .
C8 C9 1.390(4) .
C8 S1 1.754(3) .
C9 C10 1.384(4) .
C9 H9 0.9500 .
C10 C11 1.388(4) .
C10 H10 0.9500 .
C11 C12 1.389(4) .
C11 C14 1.512(4) .
C12 C13 1.391(4) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
N1 N2 1.415(3) .
N1 S1 1.685(2) .
N3 H3A 0.8859 .
N3 H3B 0.8907 .
N4 H4A 0.8800 .
O2 S1 1.4326(19) .
O3 S1 1.4177(19) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A O1 0.89 2.48 3.080(3) 125.8 .
N3 H3B O2 0.89 2.22 2.783(3) 120.3 .
N4 H4A O1 0.88 2.00 2.854(3) 164.5 2_666
