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#$Date: 2025-08-22 01:24:23 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/56/7115653.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_7115653
loop_
_publ_author_name
'Mohammad S. Afzal'
'Jean-Philippe Pitteloud'
'Daniela Buccella'
_publ_section_title
;
 Enhanced ratiometric fluorescent indicators for magnesium based on azoles
 of the heavier chalcogens
;
_journal_name_full               Chem.Commun.
_journal_page_first              11358
_journal_paper_doi               10.1039/C4cc04460F
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C23 H24 N2 O10 S'
_chemical_formula_weight         520.50
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                67.376(2)
_cell_angle_beta                 77.489(2)
_cell_angle_gamma                67.165(2)
_cell_formula_units_Z            2
_cell_length_a                   10.0940(14)
_cell_length_b                   11.5565(16)
_cell_length_c                   11.7894(17)
_cell_measurement_reflns_used    5743
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.12
_cell_measurement_theta_min      2.20
_cell_volume                     1166.3(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21799
_diffrn_reflns_theta_full        28.44
_diffrn_reflns_theta_max         28.44
_diffrn_reflns_theta_min         1.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.9762
_exptl_absorpt_correction_T_min  0.8972
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0419
_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)+(0.0560P)²+0.4232P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1154
_reflns_number_gt                4657
_reflns_number_total             5877
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc04460f2.cif
_cod_data_source_block           db_2
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7115653
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S S 0.77322(4) 0.43290(4) 0.43428(4) 0.02117(11) Uani 1 1 d .
N1 N 0.66295(16) 0.51832(14) 0.61913(13) 0.0248(3) Uani 1 1 d .
N2 N 1.17678(14) 0.92060(14) 0.10322(12) 0.0201(3) Uani 1 1 d .
O1 O 0.89984(12) 0.63872(11) 0.35964(10) 0.0199(2) Uani 1 1 d .
O2 O 1.10029(12) 1.04008(11) 0.28987(11) 0.0243(3) Uani 1 1 d .
O3 O 0.69807(14) 0.20032(12) 0.45143(11) 0.0282(3) Uani 1 1 d .
O4 O 0.55824(12) 0.19044(11) 0.63022(10) 0.0228(3) Uani 1 1 d .
O5 O 1.22030(13) 1.22551(12) 0.22099(12) 0.0270(3) Uani 1 1 d .
O6 O 1.00680(14) 1.38981(12) 0.18417(12) 0.0304(3) Uani 1 1 d .
O7 O 1.37566(14) 0.68396(12) 0.06146(11) 0.0301(3) Uani 1 1 d .
O8 O 1.30223(14) 0.75844(13) -0.12826(11) 0.0313(3) Uani 1 1 d .
O9 O 1.11968(12) 1.19319(11) -0.01360(11) 0.0251(3) Uani 1 1 d .
O10 O 1.35434(13) 1.16468(12) -0.02470(11) 0.0257(3) Uani 1 1 d .
C1 C 0.81331(17) 0.63931(16) 0.46842(14) 0.0206(3) Uani 1 1 d .
C2 C 0.81121(18) 0.73595(16) 0.50765(15) 0.0216(3) Uani 1 1 d .
H2A H 0.7593 0.7554 0.5793 0.026 Uiso 1 1 calc R
C3 C 0.90334(17) 0.80336(16) 0.41913(15) 0.0195(3) Uani 1 1 d .
C4 C 0.95175(17) 0.90746(16) 0.40330(15) 0.0211(3) Uani 1 1 d .
H4A H 0.9208 0.9533 0.4613 0.025 Uiso 1 1 calc R
C5 C 1.04499(17) 0.94254(15) 0.30238(15) 0.0197(3) Uani 1 1 d .
C6 C 1.09359(16) 0.87772(15) 0.21171(14) 0.0180(3) Uani 1 1 d .
C7 C 1.04811(17) 0.77176(15) 0.22995(14) 0.0189(3) Uani 1 1 d .
H7A H 1.0807 0.7232 0.1741 0.023 Uiso 1 1 calc R
C8 C 0.95469(16) 0.73955(15) 0.33112(14) 0.0178(3) Uani 1 1 d .
C9 C 0.74589(17) 0.53845(16) 0.51483(14) 0.0199(3) Uani 1 1 d .
C10 C 0.66683(17) 0.35496(15) 0.54826(14) 0.0195(3) Uani 1 1 d .
C11 C 0.61972(18) 0.41414(17) 0.63684(15) 0.0241(4) Uani 1 1 d .
H11A H 0.5597 0.3841 0.7074 0.029 Uiso 1 1 calc R
C12 C 0.64469(17) 0.24155(16) 0.53628(15) 0.0211(3) Uani 1 1 d .
C13 C 1.00220(18) 1.17253(16) 0.26012(16) 0.0235(3) Uani 1 1 d .
H13A H 0.9356 1.1854 0.3328 0.028 Uiso 1 1 calc R
H13B H 0.9446 1.1924 0.1926 0.028 Uiso 1 1 calc R
C14 C 1.09130(19) 1.26252(16) 0.22025(15) 0.0225(3) Uani 1 1 d .
C15 C 1.17490(17) 0.89033(16) -0.00440(15) 0.0196(3) Uani 1 1 d .
H15A H 1.1815 0.9669 -0.0788 0.024 Uiso 1 1 calc R
H15B H 1.0814 0.8797 -0.0013 0.024 Uiso 1 1 calc R
C16 C 1.29639(17) 0.76484(16) -0.01671(15) 0.0214(3) Uani 1 1 d .
C17 C 1.28555(17) 0.97707(16) 0.09249(15) 0.0210(3) Uani 1 1 d .
H17A H 1.3772 0.9271 0.0559 0.025 Uiso 1 1 calc R
H17B H 1.3022 0.9683 0.1756 0.025 Uiso 1 1 calc R
C18 C 1.24080(17) 1.12282(16) 0.01292(14) 0.0196(3) Uani 1 1 d .
C19 C 0.53443(19) 0.07705(17) 0.62184(17) 0.0268(4) Uani 1 1 d .
H19A H 0.6269 0.0027 0.6243 0.032 Uiso 1 1 calc R
H19B H 0.4923 0.1029 0.5436 0.032 Uiso 1 1 calc R
C20 C 0.4321(2) 0.03492(19) 0.73028(17) 0.0309(4) Uani 1 1 d .
H20A H 0.4139 -0.0412 0.7274 0.046 Uiso 1 1 calc R
H20B H 0.3410 0.1092 0.7268 0.046 Uiso 1 1 calc R
H20C H 0.4751 0.0094 0.8071 0.046 Uiso 1 1 calc R
C21 C 1.0818(2) 1.48493(18) 0.1499(2) 0.0354(4) Uani 1 1 d .
H21A H 1.0123 1.5757 0.1244 0.053 Uiso 1 1 calc R
H21B H 1.1544 1.4723 0.0816 0.053 Uiso 1 1 calc R
H21C H 1.1290 1.4709 0.2208 0.053 Uiso 1 1 calc R
C22 C 1.3213(2) 1.30343(18) -0.10222(18) 0.0332(4) Uani 1 1 d .
H22A H 1.4098 1.3259 -0.1255 0.050 Uiso 1 1 calc R
H22B H 1.2515 1.3601 -0.0568 0.050 Uiso 1 1 calc R
H22C H 1.2803 1.3179 -0.1767 0.050 Uiso 1 1 calc R
C23 C 1.4176(2) 0.6475(2) -0.1567(2) 0.0454(6) Uani 1 1 d .
H23A H 1.4115 0.6527 -0.2404 0.068 Uiso 1 1 calc R
H23B H 1.4081 0.5634 -0.0978 0.068 Uiso 1 1 calc R
H23C H 1.5110 0.6517 -0.1509 0.068 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 0.0033 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
C10 S C9 88.81(8)
C9 N1 C11 109.10(14)
C6 N2 C17 125.05(14)
C6 N2 C15 120.32(13)
C17 N2 C15 113.92(13)
C8 O1 C1 105.45(12)
C5 O2 C13 116.34(12)
C12 O4 C19 113.90(13)
C14 O6 C21 114.65(14)
C16 O8 C23 116.45(14)
C18 O10 C22 114.68(13)
C2 C1 O1 111.84(14)
C2 C1 C9 134.14(15)
O1 C1 C9 114.02(14)
C1 C2 C3 106.43(14)
C8 C3 C4 117.26(15)
C8 C3 C2 105.57(14)
C4 C3 C2 137.16(16)
C5 C4 C3 119.14(15)
C4 C5 O2 119.52(15)
C4 C5 C6 122.62(15)
O2 C5 C6 117.79(14)
C7 C6 N2 118.95(14)
C7 C6 C5 117.86(14)
N2 C6 C5 123.08(14)
C8 C7 C6 118.09(15)
C7 C8 O1 124.33(14)
C7 C8 C3 124.97(15)
O1 C8 C3 110.70(14)
N1 C9 C1 124.16(15)
N1 C9 S 115.66(12)
C1 C9 S 120.18(12)
C11 C10 C12 132.30(15)
C11 C10 S 109.61(13)
C12 C10 S 118.09(12)
N1 C11 C10 116.83(15)
O3 C12 O4 124.36(16)
O3 C12 C10 123.30(15)
O4 C12 C10 112.34(14)
O2 C13 C14 106.75(13)
O5 C14 O6 124.39(16)
O5 C14 C13 125.25(15)
O6 C14 C13 110.37(14)
N2 C15 C16 114.15(13)
O7 C16 O8 124.67(16)
O7 C16 C15 125.55(15)
O8 C16 C15 109.78(13)
N2 C17 C18 111.38(13)
O9 C18 O10 123.69(15)
O9 C18 C17 125.33(15)
O10 C18 C17 110.98(13)
O4 C19 C20 107.39(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S C10 1.7218(16)
S C9 1.7270(17)
N1 C9 1.324(2)
N1 C11 1.363(2)
N2 C6 1.399(2)
N2 C17 1.442(2)
N2 C15 1.445(2)
O1 C8 1.3770(19)
O1 C1 1.3873(19)
O2 C5 1.3887(19)
O2 C13 1.4168(19)
O3 C12 1.205(2)
O4 C12 1.3472(19)
O4 C19 1.463(2)
O5 C14 1.203(2)
O6 C14 1.332(2)
O6 C21 1.455(2)
O7 C16 1.200(2)
O8 C16 1.333(2)
O8 C23 1.454(2)
O9 C18 1.2051(19)
O10 C18 1.3376(19)
O10 C22 1.452(2)
C1 C2 1.355(2)
C1 C9 1.444(2)
C2 C3 1.441(2)
C3 C8 1.396(2)
C3 C4 1.402(2)
C4 C5 1.381(2)
C5 C6 1.431(2)
C6 C7 1.396(2)
C7 C8 1.376(2)
C10 C11 1.366(2)
C10 C12 1.473(2)
C13 C14 1.509(2)
C15 C16 1.527(2)
C17 C18 1.516(2)
C19 C20 1.509(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139185443
