#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/10/2011051.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2011051
loop_
_publ_author_name
'Akkurt, Mehmet'
'Öztürk, Sema'
'Fun, Hoong-Kun'
'Altural, Behzat'
_publ_section_title
3-Acetyl-4-benzoyl-2-methyl-5-phenyl-3,3a-dihydropyrazolo[2,3-c]pyrimidine-7(6H)-thione
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              e276
_journal_page_last               e277
_journal_paper_doi               10.1107/S0108270100007241
_journal_volume                  56
_journal_year                    2000
_chemical_formula_sum            'C22 H19 N3 O2 S'
_chemical_formula_weight         389.46
_chemical_name_systematic
;
3-Acetyl-4-benzoyl-2-methyl-5-phenyl-3,3a-dihydropyrazolo[2,3-c]pyrimidine-
7(6H)-thione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 100.2390(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9505(3)
_cell_length_b                   21.8820(8)
_cell_length_c                   12.9619(5)
_cell_measurement_reflns_used    4312
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.4
_cell_measurement_theta_min      1.9
_cell_volume                     1939.99(13)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_publication_material  'PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens SMART CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .082
_diffrn_reflns_av_sigmaI/netI    .1080
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            13631
_diffrn_reflns_theta_max         28.43
_diffrn_reflns_theta_min         1.85
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .190
_exptl_absorpt_correction_T_max  .985
_exptl_absorpt_correction_T_min  .931
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          .38
_exptl_crystal_size_mid          .12
_exptl_crystal_size_min          .08
_refine_diff_density_max         .228
_refine_diff_density_min         -.284
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   .953
_refine_ls_goodness_of_fit_obs   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4769
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .953
_refine_ls_restrained_S_obs      1.107
_refine_ls_R_factor_all          .143
_refine_ls_R_factor_obs          .061
_refine_ls_shift/esd_max         <0.001
_refine_ls_shift/esd_mean        .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0609P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         .152
_refine_ls_wR_factor_obs         .123
_reflns_number_observed          2422
_reflns_number_total             4769
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            qa0307.cif
_cod_data_source_block           III
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0609P)^2^] where P = (Fo^2^+2Fc^2^)/3' was changed
to 'calc'. New tag '_refine_ls_weighting_details' was created. The
value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0609P)^2^]
where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2011051
_cod_database_fobs_code          2011051
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
S1 .25488(11) .56433(3) .03406(6) .0491(2) Uani d . 1 . S
N1 .2420(3) .44883(8) .0935(2) .0407(6) Uani d . 1 . N
H1A .1193 .45014 .0675 .049 Uiso calc R 1 . H
N2 .5123(3) .49947(8) .1689(2) .0389(5) Uani d . 1 . N
N3 .6484(3) .54688(9) .1832(2) .0435(6) Uani d . 1 . N
O1 .7263(3) .33795(8) .3089(2) .0652(7) Uani d . 1 . O
O2 .7993(3) .45741(10) .4482(2) .0639(6) Uani d . 1 . O
C1 .1992(3) .34024(11) .0794(2) .0359(6) Uani d . 1 . C
C2 .1503(4) .33388(12) -.0286(2) .0508(8) Uani d . 1 . C
H2A .1874 .36356 -.0725 .061 Uiso calc R 1 . H
C3 .0469(5) .28345(15) -.0701(3) .0630(9) Uani d . 1 . C
H3A .0148 .27874 -.1424 .076 Uiso calc R 1 . H
C4 -.0091(4) .24016(14) -.0053(3) .0605(9) Uani d . 1 . C
H4A -.0770 .20573 -.0339 .073 Uiso calc R 1 . H
C5 .0337(4) .24707(13) .1007(3) .0547(8) Uani d . 1 . C
H5A -.0072 .21771 .1440 .066 Uiso calc R 1 . H
C6 .1372(4) .29726(11) .1443(2) .0422(7) Uani d . 1 . C
H6A .1650 .30213 .2167 .051 Uiso calc R 1 . H
C7 .5754(3) .27283(10) .1762(2) .0366(6) Uani d . 1 . C
C8 .5511(4) .26470(12) .0693(2) .0429(7) Uani d . 1 . C
H8A .5482 .29839 .0254 .052 Uiso calc R 1 . H
C9 .5310(4) .20657(14) .0274(3) .0589(9) Uani d . 1 . C
H9A .5132 .20116 -.0448 .071 Uiso calc R 1 . H
C10 .5372(5) .15670(14) .0924(3) .0701(10) Uani d . 1 . C
H10A .5208 .11768 .0637 .084 Uiso calc R 1 . H
C11 .5672(5) .16405(13) .1985(3) .0684(10) Uani d . 1 . C
H11A .5746 .13002 .2420 .082 Uiso calc R 1 . H
C12 .5865(4) .22183(12) .2413(2) .0513(8) Uani d . 1 . C
H12A .6070 .22678 .3137 .062 Uiso calc R 1 . H
C13 .6048(4) .33366(11) .2279(2) .0386(6) Uani d . 1 . C
C14 .4964(4) .38898(10) .1891(2) .0335(6) Uani d . 1 . C
C15 .3226(4) .39217(10) .1238(2) .0336(6) Uani d . 1 . C
C16 .3435(4) .50283(11) .1018(2) .0365(6) Uani d . 1 . C
C17 .8048(4) .52567(11) .2390(2) .0400(6) Uani d . 1 . C
C18 .9806(4) .56480(12) .2706(2) .0567(8) Uani d . 1 . C
H18A .9522 .60568 .2456 .085 Uiso calc R 1 . H
H18B 1.0872 .54873 .2410 .085 Uiso calc R 1 . H
H18C 1.0158 .56523 .3457 .085 Uiso calc R 1 . H
C19 .7957(4) .45852(10) .2648(2) .0360(6) Uani d . 1 . C
H19A .8610 .43433 .2176 .043 Uiso calc R 1 . H
C20 .5758(4) .44763(10) .2404(2) .0351(6) Uani d . 1 . C
H20A .5224 .45331 .3048 .042 Uiso calc R 1 . H
C21 .8872(4) .44533(11) .3794(2) .0440(7) Uani d . 1 . C
C22 1.0900(4) .41983(14) .3985(3) .0681(10) Uani d . 1 . C
H22A 1.1325 .41337 .4723 .102 Uiso calc R 1 . H
H22B 1.1767 .44809 .3733 .102 Uiso calc R 1 . H
H22C 1.0912 .38164 .3621 .102 Uiso calc R 1 . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .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_publ_flag
C16 N1 C15 124.9(2) yes
C16 N2 N3 122.9(2) yes
C16 N2 C20 125.5(2) yes
N3 N2 C20 111.6(2) yes
C17 N3 N2 107.0(2) yes
C6 C1 C2 120.0(2) ?
C6 C1 C15 120.6(2) ?
C2 C1 C15 119.4(2) ?
C3 C2 C1 119.5(3) ?
C4 C3 C2 120.1(3) ?
C5 C4 C3 120.5(3) ?
C4 C5 C6 120.4(3) ?
C5 C6 C1 119.3(3) ?
C8 C7 C12 119.3(2) ?
C8 C7 C13 123.4(2) ?
C12 C7 C13 117.1(2) ?
C7 C8 C9 120.1(3) ?
C10 C9 C8 120.0(3) ?
C11 C10 C9 120.5(3) ?
C10 C11 C12 120.0(3) ?
C11 C12 C7 120.1(3) ?
O1 C13 C14 117.6(2) ?
O1 C13 C7 118.2(2) ?
C14 C13 C7 124.2(2) ?
C15 C14 C13 127.3(2) ?
C15 C14 C20 116.8(2) ?
C13 C14 C20 115.2(2) ?
C14 C15 N1 119.7(2) yes
C14 C15 C1 126.7(2) ?
N1 C15 C1 113.5(2) ?
N2 C16 N1 112.6(2) yes
N2 C16 S1 126.1(2) yes
N1 C16 S1 121.2(2) yes
N3 C17 C18 121.3(2) ?
N3 C17 C19 114.4(2) yes
C18 C17 C19 124.2(2) ?
C17 C19 C20 100.7(2) ?
C17 C19 C21 111.8(2) ?
C20 C19 C21 113.5(2) ?
N2 C20 C14 109.4(2) ?
N2 C20 C19 100.7(2) ?
C14 C20 C19 120.1(2) ?
O2 C21 C22 123.4(3) ?
O2 C21 C19 120.1(3) ?
C22 C21 C19 116.5(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C16 . 1.664(2) yes
N1 C16 . 1.371(3) yes
N1 C15 . 1.388(3) yes
N2 C16 . 1.333(3) yes
N2 N3 . 1.394(3) yes
N2 C20 . 1.481(3) yes
N3 C17 . 1.281(3) yes
O1 C13 . 1.228(3) yes
O2 C21 . 1.197(3) yes
C1 C6 . 1.380(4) ?
C1 C2 . 1.387(4) ?
C1 C15 . 1.477(3) ?
C2 C3 . 1.374(4) ?
C3 C4 . 1.367(5) ?
C4 C5 . 1.362(5) ?
C5 C6 . 1.378(3) ?
C7 C8 . 1.377(4) ?
C7 C12 . 1.393(3) ?
C7 C13 . 1.488(3) ?
C8 C9 . 1.380(4) ?
C9 C10 . 1.374(4) ?
C10 C11 . 1.364(5) ?
C11 C12 . 1.377(4) ?
C13 C14 . 1.467(3) ?
C14 C15 . 1.348(3) ?
C14 C20 . 1.504(3) ?
C17 C18 . 1.489(3) ?
C17 C19 . 1.511(3) ?
C19 C20 . 1.524(3) ?
C19 C21 . 1.535(4) ?
C21 C22 . 1.496(4) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A S1 3_565 .86 2.72 3.565(2) 170 yes
C4 H4A O1 4_465 .93 2.44 3.245(4) 145 yes
C20 H20A O2 . .98 2.43 2.869(3) 107 yes
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
C16 N2 N3 C17 -169.7(2)
C20 N2 N3 C17 12.9(3)
C6 C1 C2 C3 -2.5(4)
C15 C1 C2 C3 175.6(3)
C1 C2 C3 C4 .6(4)
C2 C3 C4 C5 1.2(5)
C3 C4 C5 C6 -1.2(5)
C4 C5 C6 C1 -.7(4)
C2 C1 C6 C5 2.6(4)
C15 C1 C6 C5 -175.5(2)
C12 C7 C8 C9 2.3(4)
C13 C7 C8 C9 177.9(2)
C7 C8 C9 C10 -.6(4)
C8 C9 C10 C11 -1.4(5)
C9 C10 C11 C12 1.7(5)
C10 C11 C12 C7 .0(5)
C8 C7 C12 C11 -2.0(4)
C13 C7 C12 C11 -177.8(3)
C8 C7 C13 O1 -138.7(3)
C12 C7 C13 O1 36.9(4)
C8 C7 C13 C14 42.0(4)
C12 C7 C13 C14 -142.3(3)
O1 C13 C14 C15 -158.3(3)
C7 C13 C14 C15 20.9(4)
O1 C13 C14 C20 12.3(4)
C7 C13 C14 C20 -168.4(2)
C13 C14 C15 N1 -178.9(2)
C20 C14 C15 N1 10.6(4)
C13 C14 C15 C1 2.1(5)
C20 C14 C15 C1 -168.4(2)
C16 N1 C15 C14 17.6(4)
C16 N1 C15 C1 -163.3(2)
C6 C1 C15 C14 56.5(4)
C2 C1 C15 C14 -121.6(3)
C6 C1 C15 N1 -122.5(3)
C2 C1 C15 N1 59.4(3)
N3 N2 C16 N1 174.0(2)
C20 N2 C16 N1 -9.0(4)
N3 N2 C16 S1 -6.7(4)
C20 N2 C16 S1 170.2(2)
C15 N1 C16 N2 -18.4(4)
C15 N1 C16 S1 162.3(2)
N2 N3 C17 C18 -179.1(2)
N2 N3 C17 C19 3.2(3)
N3 C17 C19 C20 -16.8(3)
C18 C17 C19 C20 165.6(3)
N3 C17 C19 C21 -137.7(3)
C18 C17 C19 C21 44.7(4)
C16 N2 C20 C14 32.9(3)
N3 N2 C20 C14 -149.8(2)
C16 N2 C20 C19 160.3(2)
N3 N2 C20 C19 -22.5(3)
C15 C14 C20 N2 -31.8(3)
C13 C14 C20 N2 156.5(2)
C15 C14 C20 C19 -147.4(2)
C13 C14 C20 C19 40.9(3)
C17 C19 C20 N2 21.4(2)
C21 C19 C20 N2 141.1(2)
C17 C19 C20 C14 141.4(2)
C21 C19 C20 C14 -98.9(3)
C17 C19 C21 O2 76.4(3)
C20 C19 C21 O2 -36.7(3)
C17 C19 C21 C22 -101.0(3)
C20 C19 C21 C22 145.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21107232
