#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/85/7218506.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_7218506
loop_
_publ_author_name
'Dey, Swapan'
'Sain, Dibyendu'
'Kumar, Ashish'
'Kumari, Chanda'
_publ_section_title
;
 A series of ditopic receptors for succinic acid binding
;
_journal_issue                   93
_journal_name_full               'RSC Adv.'
_journal_page_first              51486
_journal_paper_doi               10.1039/C4RA07537D
_journal_volume                  4
_journal_year                    2014
_chemical_formula_sum            'C15 H16 N3 O4 S'
_chemical_formula_weight         334.37
_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   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                78.516(9)
_cell_angle_beta                 83.189(9)
_cell_angle_gamma                68.866(9)
_cell_formula_units_Z            2
_cell_length_a                   8.085(3)
_cell_length_b                   9.738(3)
_cell_length_c                   10.671(4)
_cell_measurement_reflns_used    10043
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.997
_cell_measurement_theta_min      1.950
_cell_volume                     766.9(5)
_computing_data_collection       'APEX 2'
_computing_molecular_graphics    'Mercury 3.1'
_computing_publication_material  'Microsoft word 2007'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker AXS SMART APEX II'
_diffrn_measurement_method       'area detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10043
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_min         1.950
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_description       block
_exptl_crystal_F_000             350
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3232
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0910P)²+0.2955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1550
_refine_ls_wR_factor_ref         0.1646
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2609
_reflns_number_total             3232
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ra07537d2.cif
_cod_data_source_block           shelxl
_cod_original_cell_volume        766.9(4)
_cod_database_code               7218506
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.2878(4) 0.9782(3) 0.0932(3) 0.0612(7) Uani 1 1 d . .
H1A H 0.2986 1.0738 0.0589 0.092 Uiso 1 1 calc R U
H1B H 0.1678 0.9920 0.1251 0.092 Uiso 1 1 calc R U
H1C H 0.3180 0.9182 0.0269 0.092 Uiso 1 1 calc R U
C2 C 0.4107(3) 0.9018(3) 0.1996(2) 0.0508(6) Uani 1 1 d . .
H2A H 0.5313 0.8907 0.1673 0.061 Uiso 1 1 calc R U
H2B H 0.3806 0.9635 0.2657 0.061 Uiso 1 1 calc R U
C3 C 0.4952(3) 0.6431(3) 0.1927(2) 0.0442(5) Uani 1 1 d . .
C4 C 0.4847(3) 0.4956(2) 0.2579(2) 0.0415(5) Uani 1 1 d . .
C5 C 0.5800(4) 0.3738(3) 0.1981(3) 0.0624(7) Uani 1 1 d . .
H5 H 0.6441 0.3875 0.1213 0.075 Uiso 1 1 calc R U
C6 C 0.5800(5) 0.2331(3) 0.2517(3) 0.0720(9) Uani 1 1 d . .
H6 H 0.6447 0.1520 0.2114 0.086 Uiso 1 1 calc R U
C7 C 0.4838(4) 0.2121(3) 0.3657(3) 0.0549(6) Uani 1 1 d . .
H7 H 0.4845 0.1168 0.4019 0.066 Uiso 1 1 calc R U
C8 C 0.3857(3) 0.3331(2) 0.4264(2) 0.0385(5) Uani 1 1 d . .
C9 C 0.3871(3) 0.4750(2) 0.3722(2) 0.0371(5) Uani 1 1 d . .
H9 H 0.3228 0.5562 0.4123 0.045 Uiso 1 1 calc R U
C10 C 0.0821(3) 0.3860(2) 0.7223(2) 0.0372(5) Uani 1 1 d . .
C11 C -0.0959(3) 0.4463(3) 0.8921(2) 0.0472(5) Uani 1 1 d . .
H11 H -0.1682 0.5100 0.9464 0.057 Uiso 1 1 calc R U
C12 C -0.0661(3) 0.2984(3) 0.9150(3) 0.0533(6) Uani 1 1 d . .
H12 H -0.1130 0.2487 0.9855 0.064 Uiso 1 1 calc R U
C13 C 0.0107(4) 0.8144(3) 0.6074(3) 0.0546(6) Uani 1 1 d . .
C14 C -0.0329(5) 0.9792(3) 0.5634(3) 0.0783(10) Uani 1 1 d . .
H14A H -0.1610 1.0272 0.5678 0.094 Uiso 1 1 calc R U
H14B H 0.0148 1.0175 0.6224 0.094 Uiso 1 1 calc R U
C19 C 0.2834(3) 0.2962(2) 0.5476(2) 0.0396(5) Uani 1 1 d . .
N1 N 0.4019(2) 0.75527(17) 0.25536(15) 0.0338(4) Uani 1 1 d . .
H1 H 0.3399 0.7416 0.3249 0.041 Uiso 1 1 calc R U
N2 N 0.1789(2) 0.4099(2) 0.60964(18) 0.0398(4) Uani 1 1 d . .
N3 N -0.0118(3) 0.4960(2) 0.78276(19) 0.0437(4) Uani 1 1 d . .
O1 O 0.5812(3) 0.6591(2) 0.09519(18) 0.0667(6) Uani 1 1 d . .
O2 O 0.2932(2) 0.16761(17) 0.59036(17) 0.0537(5) Uani 1 1 d . .
O3 O 0.0991(3) 0.72168(17) 0.54209(17) 0.0612(5) Uani 1 1 d . .
O4 O -0.0583(3) 0.7817(2) 0.7205(2) 0.0814(8) Uani 1 1 d . .
S1 S 0.07116(9) 0.21465(6) 0.79506(6) 0.0509(2) Uani 1 1 d . .
H4C H -0.025(6) 0.678(5) 0.746(4) 0.125(15) Uiso 1 1 d . .
H2C H 0.171(4) 0.503(3) 0.575(3) 0.055(7) Uiso 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
C2 C1 H1A 109.5 .
C2 C1 H1B 109.5 .
H1A C1 H1B 109.5 .
C2 C1 H1C 109.5 .
H1A C1 H1C 109.5 .
H1B C1 H1C 109.5 .
N1 C2 C1 112.3(2) .
N1 C2 H2A 109.1 .
C1 C2 H2A 109.1 .
N1 C2 H2B 109.1 .
C1 C2 H2B 109.1 .
H2A C2 H2B 107.9 .
O1 C3 N1 123.2(2) .
O1 C3 C4 123.4(2) .
N1 C3 C4 113.35(19) .
C5 C4 C9 119.6(2) .
C5 C4 C3 116.3(2) .
C9 C4 C3 124.05(19) .
C6 C5 C4 120.5(2) .
C6 C5 H5 119.7 .
C4 C5 H5 119.7 .
C5 C6 C7 119.9(2) .
C5 C6 H6 120.0 .
C7 C6 H6 120.0 .
C6 C7 C8 120.4(2) .
C6 C7 H7 119.8 .
C8 C7 H7 119.8 .
C9 C8 C7 119.3(2) .
C9 C8 C19 125.43(18) .
C7 C8 C19 115.2(2) .
C8 C9 C4 120.10(19) .
C8 C9 H9 119.9 .
C4 C9 H9 119.9 .
N3 C10 N2 121.34(19) .
N3 C10 S1 114.15(17) .
N2 C10 S1 124.51(16) .
C12 C11 N3 115.1(2) .
C12 C11 H11 122.4 .
N3 C11 H11 122.4 .
C11 C12 S1 110.34(19) .
C11 C12 H12 124.8 .
S1 C12 H12 124.8 .
O3 C13 O4 123.8(2) .
O3 C13 C14 123.0(2) .
O4 C13 C14 113.2(2) .
C14 C14 C13 115.2(3) 2_576
C14 C14 H14A 108.5 2_576
C13 C14 H14A 108.5 .
C14 C14 H14B 108.5 2_576
C13 C14 H14B 108.5 .
H14A C14 H14B 107.5 .
O2 C19 N2 120.3(2) .
O2 C19 C8 121.15(19) .
N2 C19 C8 118.51(19) .
C3 N1 C2 116.43(18) .
C3 N1 H1 121.8 .
C2 N1 H1 121.8 .
C19 N2 C10 122.42(19) .
C19 N2 H2C 118.8(18) .
C10 N2 H2C 118.8(17) .
C10 N3 C11 111.21(19) .
C13 O4 H4C 110(3) .
C12 S1 C10 89.17(11) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.493(4) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 N1 1.456(3) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 O1 1.197(3) .
C3 N1 1.336(3) .
C3 C4 1.494(3) .
C4 C5 1.390(3) .
C4 C9 1.392(3) .
C5 C6 1.375(4) .
C5 H5 0.9300 .
C6 C7 1.385(4) .
C6 H6 0.9300 .
C7 C8 1.395(3) .
C7 H7 0.9300 .
C8 C9 1.391(3) .
C8 C19 1.504(3) .
C9 H9 0.9300 .
C10 N3 1.309(3) .
C10 N2 1.382(3) .
C10 S1 1.723(2) .
C11 C12 1.347(4) .
C11 N3 1.372(3) .
C11 H11 0.9300 .
C12 S1 1.721(3) .
C12 H12 0.9300 .
C13 O3 1.216(3) .
C13 O4 1.298(3) .
C13 C14 1.501(3) .
C14 C14 1.429(6) 2_576
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C19 O2 1.221(3) .
C19 N2 1.364(3) .
N1 H1 0.8600 .
N2 H2C 0.89(3) .
O4 H4C 0.94(5) .
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
N2 H2C O3 0.89(3) 1.96(3) 2.825(3) 163(3)
O4 H4C N3 0.94(5) 1.70(5) 2.625(3) 167(4)
C9 H9 O3 0.93 2.45 3.344(3) 162.5
N1 H1 O3 0.86 2.87 3.724(3) 173.4
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139199379
