#------------------------------------------------------------------------------
#$Date: 2016-03-26 19:27:03 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180435 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/04/7210467.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_7210467
loop_
_publ_author_name
'Avasthi, Kamlakar'
'Ansari, Amantullah'
'Kant, Ruchir'
'Maulik, Prakas R.'
'Ravikumar, Krishnan'
'Chattopadhyay, Partha'
'Adhikary, Nirmal D.'
_publ_section_title
;
 An alternative to ‘propylene/Leonard linker’ for studying
 arene interactions in flexible pyrazolo[3,4-d]pyrimidine core based
 models both at molecular and supramolecular levels
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              2039
_journal_paper_doi               10.1039/c0ce00336k
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C23 H21 N5 S2'
_chemical_formula_sum            'C23 H21 N5 S2'
_chemical_formula_weight         431.57
_chemical_melting_point          118
_chemical_name_common
;
1-(9H-carbazol-9-yl)-3-(4,6-dimethylsulfanyl-1H-pyrazolo (3,4-
d)pyrimidin-1-yl)-2-methylenepropane
;
_chemical_name_systematic
;
1-(9H-carbazol-9-yl)-3-(4,6-dimethylsulfanyl-1H-pyrazolo
[3,4-d]pyrimidin-1-yl)-2-methylenepropane
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.961
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1518(10)
_cell_length_b                   8.7585(9)
_cell_length_c                   24.492(3)
_cell_measurement_reflns_used    7371
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.96
_cell_measurement_theta_min      2.38
_cell_volume                     2130.4(4)
_computing_cell_refinement       'SAINT (Bruker)'
_computing_data_collection       Apex2,(Bruker)
_computing_data_reduction        SAINT(Bruker)
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXTL (Bruker, 1997)'
_computing_structure_solution    'SHELXTL (Bruker, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Kappa Apex 2'
_diffrn_measurement_method       θ-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20703
_diffrn_reflns_theta_full        27.65
_diffrn_reflns_theta_max         27.65
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular block'
_exptl_crystal_F_000             904
_exptl_crystal_size_max          .25
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .20
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4931
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0434
_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)+(0.0609P)²+0.1231P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1224
_reflns_number_gt                3446
_reflns_number_total             4931
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00336k.txt
_cod_data_source_block           13A
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P2(1)/n '
_cod_database_code               7210467
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'
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
C1 C 0.28794(16) -0.06265(19) 0.14276(7) 0.0488(4) Uani 1 1 d .
H1 H 0.2320 -0.0955 0.1661 0.059 Uiso 1 1 calc R
C2 C 0.42230(17) -0.1026(2) 0.15312(8) 0.0569(5) Uani 1 1 d .
H2 H 0.4574 -0.1635 0.1838 0.068 Uiso 1 1 calc R
C3 C 0.50580(17) -0.0532(2) 0.11840(8) 0.0602(5) Uani 1 1 d .
H3 H 0.5964 -0.0799 0.1264 0.072 Uiso 1 1 calc R
C4 C 0.45605(16) 0.0347(2) 0.07243(8) 0.0534(4) Uani 1 1 d .
H4 H 0.5126 0.0665 0.0492 0.064 Uiso 1 1 calc R
C5 C 0.25901(18) 0.2456(2) -0.02919(7) 0.0545(4) Uani 1 1 d .
H5 H 0.3439 0.2462 -0.0380 0.065 Uiso 1 1 calc R
C6 C 0.1535(2) 0.3227(2) -0.06212(8) 0.0635(5) Uani 1 1 d .
H6 H 0.1683 0.3769 -0.0929 0.076 Uiso 1 1 calc R
C7 C 0.0262(2) 0.3213(2) -0.05037(8) 0.0650(5) Uani 1 1 d .
H7 H -0.0434 0.3724 -0.0739 0.078 Uiso 1 1 calc R
C8 C 0.00035(17) 0.2455(2) -0.00444(8) 0.0561(5) Uani 1 1 d .
H8 H -0.0852 0.2456 0.0036 0.067 Uiso 1 1 calc R
C10 C -0.00468(15) 0.0581(2) 0.10327(7) 0.0489(4) Uani 1 1 d .
H10A H 0.0245 -0.0042 0.1363 0.059 Uiso 1 1 calc R
H10B H -0.0711 0.0001 0.0773 0.059 Uiso 1 1 calc R
C11 C -0.07027(15) 0.19989(19) 0.11949(8) 0.0517(4) Uani 1 1 d .
C12 C -0.20172(19) 0.2119(3) 0.10918(11) 0.0903(8) Uani 1 1 d .
H12A H -0.2550 0.1324 0.0917 0.108 Uiso 1 1 calc R
H12B H -0.2418 0.3000 0.1193 0.108 Uiso 1 1 calc R
C13 C 0.01764(17) 0.32836(19) 0.14677(9) 0.0592(5) Uani 1 1 d .
H13A H 0.0405 0.3921 0.1177 0.071 Uiso 1 1 calc R
H13B H -0.0342 0.3904 0.1675 0.071 Uiso 1 1 calc R
C16 C 0.2702(2) 0.1745(2) 0.25464(8) 0.0598(5) Uani 1 1 d .
H16 H 0.2998 0.1188 0.2872 0.072 Uiso 1 1 calc R
C17 C 0.35634(18) 0.24924(19) 0.22480(7) 0.0495(4) Uani 1 1 d .
C18 C 0.49420(18) 0.2664(2) 0.22519(7) 0.0521(4) Uani 1 1 d .
C20 C 0.43529(15) 0.40919(18) 0.14514(7) 0.0446(4) Uani 1 1 d .
C22 C 0.26865(16) 0.31824(17) 0.18004(7) 0.0447(4) Uani 1 1 d .
C23 C 0.35879(18) 0.5900(2) 0.05120(8) 0.0610(5) Uani 1 1 d .
H23A H 0.2942 0.5112 0.0382 0.092 Uiso 1 1 calc R
H23B H 0.3852 0.6380 0.0199 0.092 Uiso 1 1 calc R
H23C H 0.3193 0.6647 0.0716 0.092 Uiso 1 1 calc R
C24 C 0.7672(2) 0.2084(3) 0.25671(12) 0.1018(9) Uani 1 1 d .
H24A H 0.7611 0.1674 0.2199 0.153 Uiso 1 1 calc R
H24B H 0.8383 0.1578 0.2823 0.153 Uiso 1 1 calc R
H24C H 0.7861 0.3158 0.2564 0.153 Uiso 1 1 calc R
C4A C 0.32055(15) 0.07637(18) 0.06048(7) 0.0424(4) Uani 1 1 d .
C8A C 0.10704(15) 0.16882(17) 0.02951(7) 0.0435(4) Uani 1 1 d .
C9A C 0.23860(14) 0.02801(17) 0.09651(7) 0.0406(4) Uani 1 1 d .
C4B C 0.23680(16) 0.16662(18) 0.01760(7) 0.0442(4) Uani 1 1 d .
N9 N 0.10990(12) 0.08686(15) 0.07793(5) 0.0433(3) Uani 1 1 d .
N14 N 0.14189(14) 0.28264(16) 0.18444(6) 0.0512(4) Uani 1 1 d .
N15 N 0.14259(17) 0.19351(17) 0.23054(7) 0.0611(4) Uani 1 1 d .
N19 N 0.53291(14) 0.34546(16) 0.18543(6) 0.0514(4) Uani 1 1 d .
N21 N 0.30270(13) 0.40204(14) 0.13940(5) 0.0448(3) Uani 1 1 d .
S1 S 0.50412(4) 0.50802(5) 0.09602(2) 0.05869(16) Uani 1 1 d .
S2 S 0.61260(6) 0.17951(8) 0.27801(2) 0.0850(2) 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'
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
C2 C1 C9A 118.07(16)
C1 C2 C3 120.93(17)
C4 C3 C2 120.68(16)
C3 C4 C4A 119.92(17)
C6 C5 C4B 119.05(17)
C5 C6 C7 121.42(17)
C8 C7 C6 121.32(18)
C7 C8 C8A 117.59(16)
N9 C10 C11 114.15(13)
C12 C11 C10 120.38(19)
C12 C11 C13 120.83(18)
C10 C11 C13 118.79(13)
N14 C13 C11 115.60(14)
N15 C16 C17 111.49(17)
C22 C17 C18 115.49(15)
C22 C17 C16 104.15(15)
C18 C17 C16 140.24(17)
N19 C18 C17 119.96(16)
N19 C18 S2 120.70(14)
C17 C18 S2 119.33(14)
N21 C20 N19 128.81(15)
N21 C20 S1 119.61(12)
N19 C20 S1 111.57(11)
N21 C22 N14 125.69(15)
N21 C22 C17 126.83(15)
N14 C22 C17 107.46(14)
C4 C4A C9A 118.58(16)
C4 C4A C4B 134.69(16)
C9A C4A C4B 106.71(13)
N9 C8A C8 129.65(15)
N9 C8A C4B 108.47(13)
C8 C8A C4B 121.88(15)
C1 C9A N9 129.36(14)
C1 C9A C4A 121.79(14)
N9 C9A C4A 108.84(14)
C5 C4B C8A 118.72(15)
C5 C4B C4A 134.27(15)
C8A C4B C4A 107.00(14)
C8A N9 C9A 108.94(12)
C8A N9 C10 125.58(13)
C9A N9 C10 125.36(13)
C22 N14 N15 110.78(14)
C22 N14 C13 126.93(15)
N15 N14 C13 122.29(14)
C16 N15 N14 106.12(14)
C18 N19 C20 117.75(14)
C20 N21 C22 111.10(14)
C20 S1 C23 102.98(8)
C18 S2 C24 103.61(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.380(2)
C1 C9A 1.389(2)
C2 C3 1.388(2)
C3 C4 1.371(3)
C4 C4A 1.394(2)
C5 C6 1.376(3)
C5 C4B 1.396(2)
C6 C7 1.381(3)
C7 C8 1.377(2)
C8 C8A 1.394(2)
C10 N9 1.4493(18)
C10 C11 1.501(2)
C11 C12 1.310(2)
C11 C13 1.504(2)
C13 N14 1.456(2)
C16 N15 1.318(2)
C16 C17 1.412(2)
C17 C22 1.398(2)
C17 C18 1.406(2)
C18 N19 1.319(2)
C18 S2 1.7472(18)
C20 N21 1.3255(19)
C20 N19 1.365(2)
C20 S1 1.7417(17)
C22 N21 1.338(2)
C22 N14 1.350(2)
C23 S1 1.7962(18)
C24 S2 1.772(2)
C4A C9A 1.398(2)
C4A C4B 1.442(2)
C8A N9 1.382(2)
C8A C4B 1.407(2)
C9A N9 1.3905(18)
N14 N15 1.371(2)
