#------------------------------------------------------------------------------
#$Date: 2017-04-05 12:18:38 +0300 (Wed, 05 Apr 2017) $
#$Revision: 194978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/97/7119735.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_7119735
loop_
_publ_author_name
'Rao Khandavilli, U. B.'
'Bhogala, Balakrishna R.'
'Maguire, Anita R.'
'Lawrence, Simon E.'
_publ_section_title
;
 Symmetry assisted tuning of bending and brittle multi-component forms of
 probenecid.
;
_journal_issue                   23
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3381
_journal_page_last               3384
_journal_paper_doi               10.1039/c7cc01091e
_journal_volume                  53
_journal_year                    2017
_chemical_formula_iupac          'C18 H23 N2 O4 S'
_chemical_formula_sum            'C18 H23 N2 O4 S'
_chemical_formula_weight         363.44
_chemical_name_common            Probenecid_4,4'-dipyridyl
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2017-02-10 deposited with the CCDC.
2017-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                85.158(9)
_cell_angle_beta                 83.687(7)
_cell_angle_gamma                70.746(6)
_cell_formula_units_Z            2
_cell_length_a                   5.3240(11)
_cell_length_b                   7.8906(14)
_cell_length_c                   23.599(5)
_cell_measurement_reflns_used    2806
_cell_measurement_temperature    300.(2)
_cell_measurement_theta_max      23.2131
_cell_measurement_theta_min      2.6048
_cell_volume                     929.0(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      300.(2)
_diffrn_detector_area_resol_mean 8.3330
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10179
_diffrn_reflns_theta_full        26.43
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_min         3.17
_diffrn_source                   'micro-focus sealed tube'
_diffrn_source_type              'Bruker X2S'
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             386
_exptl_crystal_size_max          0.396
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.477
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3717
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0611P)²+0.6973P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1615
_reflns_number_gt                2644
_reflns_number_total             3717
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7cc01091e7.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 7119734--7119737.cif.'
_cod_database_code               7119735
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 1.5797(5) 0.3121(4) 0.33747(14) 0.0990(10) Uani d . . . 1.0 . .
C C2 1.4402(8) 0.4579(7) 0.35326(18) 0.0858(13) Uani d . . . 1.0 . .
O O3 1.4805(5) 0.5347(4) 0.39633(12) 0.1037(10) Uani d . . . 1.0 . .
H H3 1.6132 0.4687 0.4111 0.156 Uiso calc U . R 1.0 . .
C C4 1.1982(5) 0.5715(4) 0.32347(12) 0.0525(7) Uani d . . . 1.0 . .
C C5 1.1030(6) 0.4904(4) 0.28535(13) 0.0550(7) Uani d . . . 1.0 . .
H H5 1.1826 0.3683 0.2799 0.066 Uiso calc U . R 1.0 . .
C C6 0.8902(5) 0.5890(4) 0.25521(12) 0.0486(7) Uani d . . . 1.0 . .
H H6 0.8245 0.5332 0.2299 0.058 Uiso calc U . R 1.0 . .
C C7 0.7741(5) 0.7719(3) 0.26271(10) 0.0402(6) Uani d . . . 1.0 . .
C C8 0.8645(5) 0.8549(4) 0.30166(11) 0.0487(7) Uani d . . . 1.0 . .
H H8 0.7847 0.9769 0.3073 0.058 Uiso calc U . R 1.0 . .
C C9 1.0757(6) 0.7530(4) 0.33197(12) 0.0560(8) Uani d . . . 1.0 . .
H H9 1.137 0.8071 0.3586 0.067 Uiso calc U . R 1.0 . .
S S10 0.52116(13) 0.90208(10) 0.21944(3) 0.0488(2) Uani d . . . 1.0 . .
O O11 0.3443(4) 1.0448(3) 0.25226(9) 0.0624(6) Uani d . . . 1.0 . .
O O12 0.4185(4) 0.7816(3) 0.19502(9) 0.0651(6) Uani d . . . 1.0 . .
N N13 0.6670(5) 0.9935(3) 0.16748(10) 0.0554(6) Uani d . . . 1.0 . .
C C14 0.8389(7) 0.8712(5) 0.12475(13) 0.0696(9) Uani d . . . 1.0 . .
H H14A 0.8888 0.7491 0.1412 0.084 Uiso calc U . R 1.0 . .
H H14B 1.0011 0.9017 0.1151 0.084 Uiso calc U . R 1.0 . .
C C15 0.7044(9) 0.8797(6) 0.07081(16) 0.0977(14) Uani d . . . 1.0 . .
H H15A 0.5416 0.8499 0.0804 0.117 Uiso calc U . R 1.0 . .
H H15B 0.6559 1.0015 0.0541 0.117 Uiso calc U . R 1.0 . .
C C16 0.8795(12) 0.7545(8) 0.02818(19) 0.139(2) Uani d . . . 1.0 . .
H H16A 1.0445 0.7797 0.0199 0.208 Uiso calc U . R 1.0 . .
H H16B 0.7916 0.77 -0.0062 0.208 Uiso calc U . R 1.0 . .
H H16C 0.9152 0.6329 0.0433 0.208 Uiso calc U . R 1.0 . .
C C17 0.7509(7) 1.1477(4) 0.17966(15) 0.0682(9) Uani d . . . 1.0 . .
H H17A 0.9384 1.1037 0.1866 0.082 Uiso calc U . R 1.0 . .
H H17B 0.6503 1.2007 0.2142 0.082 Uiso calc U . R 1.0 . .
C C18 0.7102(9) 1.2908(5) 0.13197(17) 0.0865(11) Uani d . . . 1.0 . .
H H18A 0.7856 1.3805 0.1411 0.104 Uiso calc U . R 1.0 . .
H H18B 0.8079 1.2367 0.0973 0.104 Uiso calc U . R 1.0 . .
C C19 0.4296(10) 1.3808(6) 0.1210(2) 0.1180(17) Uani d . . . 1.0 . .
H H19A 0.356 1.2945 0.1095 0.177 Uiso calc U . R 1.0 . .
H H19B 0.4191 1.4728 0.0912 0.177 Uiso calc U . R 1.0 . .
H H19C 0.3303 1.4339 0.1551 0.177 Uiso calc U . R 1.0 . .
C C20 0.3815(5) 0.0568(3) 0.48578(11) 0.0437(6) Uani d . . . 1.0 . .
C C21A 0.392(4) 0.026(2) 0.4252(9) 0.047(3) Uani d . P . 0.41(2) A 1
H H21A 0.5435 -0.054 0.4072 0.056 Uiso calc U P R 0.41(2) A 1
C C22A 0.178(4) 0.114(2) 0.3955(6) 0.056(4) Uani d . P . 0.41(2) A 1
H H22A 0.1884 0.0939 0.357 0.068 Uiso calc U P R 0.41(2) A 1
N N23A -0.044(2) 0.228(3) 0.4188(9) 0.061(5) Uani d . P . 0.41(2) A 1
C C24A -0.056(2) 0.252(2) 0.4735(10) 0.071(5) Uani d . P . 0.41(2) A 1
H H24A -0.2126 0.3313 0.49 0.086 Uiso calc U P R 0.41(2) A 1
C C25A 0.147(3) 0.169(2) 0.5081(8) 0.058(4) Uani d . P . 0.41(2) A 1
H H25A 0.123 0.1908 0.5468 0.07 Uiso calc U P R 0.41(2) A 1
C C21B 0.311(3) 0.0448(19) 0.4345(7) 0.071(4) Uani d . P . 0.59(2) A 2
H H21B 0.4168 -0.0486 0.4122 0.086 Uiso calc U P R 0.59(2) A 2
C C22B 0.085(2) 0.1664(15) 0.4132(6) 0.066(3) Uani d . P . 0.59(2) A 2
H H22B 0.0489 0.153 0.3765 0.079 Uiso calc U P R 0.59(2) A 2
N N23B -0.0818(17) 0.2997(13) 0.4418(4) 0.0517(18) Uani d . P . 0.59(2) A 2
C C24B -0.020(2) 0.3168(15) 0.4924(4) 0.076(3) Uani d . P . 0.59(2) A 2
H H24B -0.1344 0.4093 0.5139 0.091 Uiso calc U P R 0.59(2) A 2
C C25B 0.210(3) 0.2041(18) 0.5160(5) 0.068(3) Uani d U P . 0.59(2) A 2
H H25B 0.2493 0.226 0.5515 0.082 Uiso calc U P R 0.59(2) A 2
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_site_symmetry_3
_geom_angle
O1 C2 O3 . 124.7(3)
O1 C2 C4 . 122.5(4)
O3 C2 C4 . 112.8(4)
C2 O3 H3 . 109.5
C5 C4 C9 . 119.4(3)
C5 C4 C2 . 117.9(3)
C9 C4 C2 . 122.7(3)
C4 C5 C6 . 120.4(3)
C4 C5 H5 . 119.8
C6 C5 H5 . 119.8
C5 C6 C7 . 119.8(3)
C5 C6 H6 . 120.1
C7 C6 H6 . 120.1
C8 C7 C6 . 120.5(2)
C8 C7 S10 . 119.6(2)
C6 C7 S10 . 119.8(2)
C9 C8 C7 . 118.7(3)
C9 C8 H8 . 120.7
C7 C8 H8 . 120.7
C8 C9 C4 . 121.2(3)
C8 C9 H9 . 119.4
C4 C9 H9 . 119.4
O12 S10 O11 . 119.80(13)
O12 S10 N13 . 107.29(14)
O11 S10 N13 . 107.05(13)
O12 S10 C7 . 107.60(13)
O11 S10 C7 . 107.88(12)
N13 S10 C7 . 106.52(12)
C14 N13 C17 . 116.6(3)
C14 N13 S10 . 116.1(2)
C17 N13 S10 . 118.3(2)
N13 C14 C15 . 112.8(3)
N13 C14 H14A . 109.0
C15 C14 H14A . 109.0
N13 C14 H14B . 109.0
C15 C14 H14B . 109.0
H14A C14 H14B . 107.8
C16 C15 C14 . 112.2(4)
C16 C15 H15A . 109.2
C14 C15 H15A . 109.2
C16 C15 H15B . 109.2
C14 C15 H15B . 109.2
H15A C15 H15B . 107.9
C15 C16 H16A . 109.5
C15 C16 H16B . 109.5
H16A C16 H16B . 109.5
C15 C16 H16C . 109.5
H16A C16 H16C . 109.5
H16B C16 H16C . 109.5
N13 C17 C18 . 113.2(3)
N13 C17 H17A . 108.9
C18 C17 H17A . 108.9
N13 C17 H17B . 108.9
C18 C17 H17B . 108.9
H17A C17 H17B . 107.7
C19 C18 C17 . 114.3(4)
C19 C18 H18A . 108.7
C17 C18 H18A . 108.7
C19 C18 H18B . 108.7
C17 C18 H18B . 108.7
H18A C18 H18B . 107.6
C18 C19 H19A . 109.5
C18 C19 H19B . 109.5
H19A C19 H19B . 109.5
C18 C19 H19C . 109.5
H19A C19 H19C . 109.5
H19B C19 H19C . 109.5
C21B C20 C25B . 114.5(7)
C25A C20 C21A . 115.2(9)
C21B C20 C20 2_656 129.2(7)
C25A C20 C20 2_656 130.1(8)
C25B C20 C20 2_656 116.2(5)
C21A C20 C20 2_656 114.3(8)
C22A C21A C20 . 119.5(12)
C22A C21A H21A . 120.2
C20 C21A H21A . 120.2
N23A C22A C21A . 123.1(13)
N23A C22A H22A . 118.5
C21A C22A H22A . 118.5
C24A N23A C22A . 117.5(11)
N23A C24A C25A . 124.7(12)
N23A C24A H24A . 117.7
C25A C24A H24A . 117.7
C20 C25A C24A . 119.9(13)
C20 C25A H25A . 120.0
C24A C25A H25A . 120.0
C20 C21B C22B . 122.1(11)
C20 C21B H21B . 118.9
C22B C21B H21B . 118.9
N23B C22B C21B . 123.8(10)
N23B C22B H22B . 118.1
C21B C22B H22B . 118.1
C24B N23B C22B . 116.1(7)
N23B C24B C25B . 123.6(8)
N23B C24B H24B . 118.2
C25B C24B H24B . 118.2
C24B C25B C20 . 119.8(8)
C24B C25B H25B . 120.1
C20 C25B H25B . 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C2 . 1.209(5)
C2 O3 . 1.298(5)
C2 C4 . 1.513(4)
O3 H3 . 0.82
C4 C5 . 1.373(4)
C4 C9 . 1.386(4)
C5 C6 . 1.377(4)
C5 H5 . 0.93
C6 C7 . 1.388(4)
C6 H6 . 0.93
C7 C8 . 1.383(4)
C7 S10 . 1.767(3)
C8 C9 . 1.381(4)
C8 H8 . 0.93
C9 H9 . 0.93
S10 O12 . 1.428(2)
S10 O11 . 1.429(2)
S10 N13 . 1.624(3)
N13 C14 . 1.471(4)
N13 C17 . 1.486(4)
C14 C15 . 1.514(5)
C14 H14A . 0.97
C14 H14B . 0.97
C15 C16 . 1.487(6)
C15 H15A . 0.97
C15 H15B . 0.97
C16 H16A . 0.96
C16 H16B . 0.96
C16 H16C . 0.96
C17 C18 . 1.505(5)
C17 H17A . 0.97
C17 H17B . 0.97
C18 C19 . 1.469(6)
C18 H18A . 0.97
C18 H18B . 0.97
C19 H19A . 0.96
C19 H19B . 0.96
C19 H19C . 0.96
C20 C21B . 1.325(19)
C20 C25A . 1.351(18)
C20 C25B . 1.411(14)
C20 C21A . 1.46(2)
C20 C20 2_656 1.478(5)
C21A C22A . 1.36(3)
C21A H21A . 0.93
C22A N23A . 1.319(15)
C22A H22A . 0.93
N23A C24A . 1.312(19)
C24A C25A . 1.38(2)
C24A H24A . 0.93
C25A H25A . 0.93
C21B C22B . 1.383(18)
C21B H21B . 0.93
C22B N23B . 1.312(12)
C22B H22B . 0.93
N23B C24B . 1.301(10)
C24B C25B . 1.393(14)
C24B H24B . 0.93
C25B H25B . 0.93
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_site_symmetry_1
_geom_torsion
O1 C2 C4 C5 . 14.0(5)
O3 C2 C4 C5 . -166.6(3)
O1 C2 C4 C9 . -164.1(3)
O3 C2 C4 C9 . 15.3(4)
C9 C4 C5 C6 . 0.9(4)
C2 C4 C5 C6 . -177.2(3)
C4 C5 C6 C7 . 1.0(4)
C5 C6 C7 C8 . -2.2(4)
C5 C6 C7 S10 . 174.3(2)
C6 C7 C8 C9 . 1.3(4)
S10 C7 C8 C9 . -175.2(2)
C7 C8 C9 C4 . 0.7(4)
C5 C4 C9 C8 . -1.8(4)
C2 C4 C9 C8 . 176.3(3)
C8 C7 S10 O12 . -165.0(2)
C6 C7 S10 O12 . 18.4(3)
C8 C7 S10 O11 . -34.5(3)
C6 C7 S10 O11 . 149.0(2)
C8 C7 S10 N13 . 80.2(2)
C6 C7 S10 N13 . -96.4(2)
O12 S10 N13 C14 . -44.2(2)
O11 S10 N13 C14 . -174.0(2)
C7 S10 N13 C14 . 70.8(2)
O12 S10 N13 C17 . 169.7(2)
O11 S10 N13 C17 . 39.9(2)
C7 S10 N13 C17 . -75.3(2)
C17 N13 C14 C15 . -112.4(4)
S10 N13 C14 C15 . 100.9(3)
N13 C14 C15 C16 . -179.6(4)
C14 N13 C17 C18 . 72.3(4)
S10 N13 C17 C18 . -141.8(3)
N13 C17 C18 C19 . 64.2(5)
C25A C20 C21A C22A . 2.8(14)
C20 C20 C21A C22A 2_656 175.9(8)
C20 C21A C22A N23A . -0.7(16)
C21A C22A N23A C24A . -1.0(17)
C22A N23A C24A C25A . 0.6(17)
C21A C20 C25A C24A . -3.2(14)
C20 C20 C25A C24A 2_656 -175.0(8)
N23A C24A C25A C20 . 1.7(17)
C25B C20 C21B C22B . -0.7(13)
C20 C20 C21B C22B 2_656 -177.9(7)
C20 C21B C22B N23B . -2.0(15)
C21B C22B N23B C24B . 2.0(14)
C22B N23B C24B C25B . 0.6(13)
N23B C24B C25B C20 . -3.2(14)
C21B C20 C25B C24B . 3.1(12)
C20 C20 C25B C24B 2_656 -179.4(7)
