#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/26/1502660.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_1502660
loop_
_publ_author_name
'Ivachtchenko, Alexandre V.'
'Dmitriev, Dmitri E.'
'Golovina, Elena S.'
'Kadieva, Madina G.'
'Koryakova, Angela G.'
'Kysil, Volodymyr M.'
'Mitkin, Oleg D.'
'Okun, Ilya M.'
'Tkachenko, Sergey E.'
'Vorobiev, Anton A.'
_publ_contact_author
;
Ilya Okun
;
_publ_section_title
;
 (3-Phenylsulfonylcycloalkano[e and
 d]pyrazolo[1,5-a]pyrimidin-2-yl)amines: potent and selective antagonists
 of the serotonin 5-HT6 receptor.
;
_journal_issue                   14
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              5186
_journal_page_last               5196
_journal_paper_doi               10.1021/jm100350r
_journal_volume                  53
_journal_year                    2010
_chemical_formula_sum            'C18 H20 N4 O2 S'
_chemical_formula_weight         356.44
_chemical_name_systematic
; 
N,N,5-Trimethyl-3-(phenylsulfonyl)-7,8-dihydro-6H-cyclopenta[e]pyrazolo[1,5-a]pyrimidin-amine
;
_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                 98.996(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7051(5)
_cell_length_b                   16.7415(10)
_cell_length_c                   11.6695(6)
_cell_measurement_reflns_used    3400
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.96
_cell_measurement_theta_min      11.30
_cell_volume                     1679.75(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6592
_diffrn_reflns_theta_full        55.00
_diffrn_reflns_theta_max         65.12
_diffrn_reflns_theta_min         11.30
_exptl_absorpt_coefficient_mu    1.882
_exptl_absorpt_correction_T_max  0.8955
_exptl_absorpt_correction_T_min  0.6022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2625
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0828P)²+0.1900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1293
_reflns_number_gt                2148
_reflns_number_total             2625
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jm100350r_si_003.cif
_cod_data_source_block           compound_12
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1679.75(16)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1502660
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
S1 S 0.28332(7) 0.88229(3) 0.21888(5) 0.0231(2) Uani 1 1 d .
O1 O 0.1365(2) 0.84629(11) 0.17372(15) 0.0337(5) Uani 1 1 d .
O2 O 0.4213(2) 0.83405(11) 0.22424(15) 0.0322(5) Uani 1 1 d .
N1 N 0.0821(2) 1.02980(12) 0.30105(17) 0.0223(5) Uani 1 1 d .
N2 N 0.2326(2) 1.00787(11) 0.48871(16) 0.0193(4) Uani 1 1 d .
N3 N 0.3381(2) 0.95613(11) 0.54737(17) 0.0209(5) Uani 1 1 d .
N4 N 0.4721(2) 0.84092(12) 0.49552(17) 0.0216(5) Uani 1 1 d .
C1 C 0.3062(3) 0.96679(14) 0.1318(2) 0.0213(5) Uani 1 1 d .
C2 C 0.1966(3) 0.97998(16) 0.0341(2) 0.0264(6) Uani 1 1 d .
H2B H 0.1096 0.9454 0.0164 0.032 Uiso 1 1 calc R
C3 C 0.2152(3) 1.04414(16) -0.0375(2) 0.0294(6) Uani 1 1 d .
H3B H 0.1410 1.0538 -0.1049 0.035 Uiso 1 1 calc R
C4 C 0.3423(3) 1.09402(17) -0.0104(2) 0.0286(6) Uani 1 1 d .
H4A H 0.3555 1.1379 -0.0595 0.034 Uiso 1 1 calc R
C5 C 0.4505(3) 1.08041(16) 0.0880(2) 0.0269(6) Uani 1 1 d .
H5A H 0.5372 1.1152 0.1061 0.032 Uiso 1 1 calc R
C6 C 0.4334(3) 1.01679(15) 0.1599(2) 0.0244(6) Uani 1 1 d .
H6A H 0.5074 1.0074 0.2275 0.029 Uiso 1 1 calc R
C7 C 0.3655(3) 0.90331(15) 0.4658(2) 0.0210(5) Uani 1 1 d .
C8 C 0.2769(3) 0.92049(14) 0.3552(2) 0.0210(5) Uani 1 1 d .
C9 C 0.1875(3) 0.98790(14) 0.3730(2) 0.0202(5) Uani 1 1 d .
C10 C 0.0234(3) 1.09513(15) 0.3437(2) 0.0226(5) Uani 1 1 d .
C11 C 0.0714(3) 1.11938(14) 0.4593(2) 0.0219(5) Uani 1 1 d .
C12 C 0.0267(3) 1.19232(15) 0.5222(2) 0.0291(6) Uani 1 1 d .
H12A H -0.0827 1.1891 0.5356 0.035 Uiso 1 1 calc R
H12B H 0.0406 1.2416 0.4782 0.035 Uiso 1 1 calc R
C13 C 0.1396(4) 1.19023(18) 0.6375(3) 0.0410(7) Uani 1 1 d .
H13A H 0.0828 1.2014 0.7029 0.049 Uiso 1 1 calc R
H13B H 0.2212 1.2314 0.6372 0.049 Uiso 1 1 calc R
C14 C 0.2141(3) 1.10658(15) 0.6515(2) 0.0262(6) Uani 1 1 d .
H14A H 0.3280 1.1098 0.6764 0.031 Uiso 1 1 calc R
H14B H 0.1676 1.0737 0.7077 0.031 Uiso 1 1 calc R
C15 C 0.1751(3) 1.07475(14) 0.5317(2) 0.0212(5) Uani 1 1 d .
C16 C -0.0952(3) 1.14192(16) 0.2651(2) 0.0289(6) Uani 1 1 d .
H16A H -0.1141 1.1165 0.1886 0.043 Uiso 1 1 calc R
H16B H -0.0571 1.1964 0.2575 0.043 Uiso 1 1 calc R
H16D H -0.1923 1.1436 0.2976 0.043 Uiso 1 1 calc R
C17 C 0.4225(4) 0.76068(17) 0.4623(3) 0.0391(7) Uani 1 1 d .
H17A H 0.3704 0.7606 0.3815 0.059 Uiso 1 1 calc R
H17B H 0.3502 0.7417 0.5128 0.059 Uiso 1 1 calc R
H17C H 0.5133 0.7254 0.4701 0.059 Uiso 1 1 calc R
C18 C 0.5510(3) 0.84317(16) 0.6166(2) 0.0258(6) Uani 1 1 d .
H18A H 0.5836 0.8980 0.6372 0.039 Uiso 1 1 calc R
H18B H 0.6426 0.8083 0.6252 0.039 Uiso 1 1 calc R
H18C H 0.4795 0.8246 0.6680 0.039 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O1 S1 O2 117.93(12)
O1 S1 C8 109.80(11)
O2 S1 C8 108.38(11)
O1 S1 C1 107.34(11)
O2 S1 C1 107.74(11)
C8 S1 C1 104.85(11)
C10 N1 C9 117.3(2)
C15 N2 N3 126.65(19)
C15 N2 C9 119.7(2)
N3 N2 C9 113.63(19)
C7 N3 N2 103.96(18)
C7 N4 C17 117.8(2)
C7 N4 C18 114.2(2)
C17 N4 C18 110.9(2)
C2 C1 C6 121.4(2)
C2 C1 S1 118.34(19)
C6 C1 S1 120.25(19)
C1 C2 C3 119.3(2)
C4 C3 C2 119.6(2)
C3 C4 C5 120.4(2)
C6 C5 C4 120.5(2)
C5 C6 C1 118.7(2)
N3 C7 N4 119.8(2)
N3 C7 C8 112.1(2)
N4 C7 C8 128.1(2)
C9 C8 C7 105.2(2)
C9 C8 S1 122.26(19)
C7 C8 S1 132.03(19)
N1 C9 N2 123.1(2)
N1 C9 C8 131.9(2)
N2 C9 C8 105.0(2)
N1 C10 C11 121.3(2)
N1 C10 C16 118.0(2)
C11 C10 C16 120.7(2)
C15 C11 C10 120.4(2)
C15 C11 C12 109.8(2)
C10 C11 C12 129.8(2)
C11 C12 C13 103.3(2)
C12 C13 C14 108.3(2)
C15 C14 C13 101.3(2)
N2 C15 C11 118.1(2)
N2 C15 C14 127.0(2)
C11 C15 C14 114.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.436(2)
S1 O2 1.4405(19)
S1 C8 1.723(2)
S1 C1 1.772(2)
N1 C10 1.336(3)
N1 C9 1.341(3)
N2 C15 1.355(3)
N2 N3 1.366(3)
N2 C9 1.387(3)
N3 C7 1.348(3)
N4 C7 1.404(3)
N4 C17 1.445(3)
N4 C18 1.472(3)
C1 C2 1.385(4)
C1 C6 1.386(4)
C2 C3 1.386(4)
C3 C4 1.383(4)
C4 C5 1.386(4)
C5 C6 1.378(4)
C7 C8 1.426(3)
C8 C9 1.404(3)
C10 C11 1.408(4)
C10 C16 1.491(4)
C11 C15 1.360(4)
C11 C12 1.507(3)
C12 C13 1.537(4)
C13 C14 1.541(4)
C14 C15 1.485(3)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 24673858 ChemSpider
2 46867524 PubChem
