Monosulfonated dibenzo-24-crown-8 and its properties
Woźny, Mateusz; Trzybiński, Damian; Dąbrowa, Kajetan; Narodowiec, Jakub; Wozniak, Krzysztof; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB00851C

data_7158731
_publ_section_title
;
 Monosulfonated dibenzo-24-crown-8 and its properties
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00851C
_journal_year                    2022
_chemical_formula_moiety         'C24 H31 O11 S, H3 O'
_chemical_formula_sum            'C24 H34 O12 S'
_chemical_formula_weight         546.57
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-03-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2022-01-19 deposited with the CCDC.	2022-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                68.283(4)
_cell_angle_beta                 88.338(3)
_cell_angle_gamma                66.351(4)
_cell_formula_units_Z            2
_cell_length_a                   9.3346(4)
_cell_length_b                   11.4965(5)
_cell_length_c                   14.0008(5)
_cell_measurement_reflns_used    11484
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.1290
_cell_measurement_theta_min      3.4170
_cell_volume                     1265.98(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1014085000
_diffrn_orient_matrix_UB_12      -0.0460088000
_diffrn_orient_matrix_UB_13      -0.0497382000
_diffrn_orient_matrix_UB_21      0.1026953000
_diffrn_orient_matrix_UB_22      0.0003608000
_diffrn_orient_matrix_UB_23      -0.0881622000
_diffrn_orient_matrix_UB_31      0.1108268000
_diffrn_orient_matrix_UB_32      -0.1521674000
_diffrn_orient_matrix_UB_33      0.0637452000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17259
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.059
_diffrn_reflns_theta_max         67.059
_diffrn_reflns_theta_min         3.432
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.706
_exptl_absorpt_correction_T_max  0.827
_exptl_absorpt_correction_T_min  0.590
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       needle
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         4517
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.219
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0547P)^2^+1.0829P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1098
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4265
_reflns_number_total             4517
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob00851c2.cif
_cod_data_source_block           2018_03_08_dt_sdb24c8-h2o_n
_cod_original_cell_volume        1265.99(10)
_cod_database_code               7158731
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H14A,H14B,H14C,H14D} of C14, {H12A,H12B,H12C,H12D} of C12,
   All C(H,H) groups
 At 1.5 times of:
  {H1WA,H1WB,H1WC,H1W} of C2B
2. Restrained distances
 C13B-C12
 1.5 with sigma of 0.02
 C3A-C2A
 1.54 with sigma of 0.002
 H1WC-O1W
 0.82 with sigma of 0.02
 O1W-H1WA
 0.82 with sigma of 0.02
 O1W-H1WB
 0.82 with sigma of 0.02
 O1W-H1W
 0.82 with sigma of 0.02
 C4A-C5A \\sim C4B-C5B
 with sigma of 0.02
 O3A-C6A \\sim O3B-C6B
 with sigma of 0.02
 C6B-C7B \\sim C6A-C7A
 with sigma of 0.02
 C7B-O4 \\sim O4-C7A
 with sigma of 0.02
 C14-O7B \\sim O7B-O7A
 with sigma of 0.02
 C3A-O2A \\sim C3B-O2B
 with sigma of 0.02
 C13B-O7B \\sim C13A-O7A
 with sigma of 0.02
 C12-C13B \\sim C13B-C13A
 with sigma of 0.02
 C2A-C3A \\sim C3A-C3B
 with sigma of 0.02
 C3B-C2A \\sim C2A-C3A
 with sigma of 0.02
 C3A-C2A \\sim C2A-C3B
 with sigma of 0.02
3. Others
 Sof(C2B)=Sof(H2BA)=Sof(H2BB)=Sof(C3B)=Sof(H3BA)=Sof(H3BB)=Sof(C4B)=Sof(H4BA)=
 Sof(H4BB)=Sof(C5B)=Sof(H5BA)=Sof(H5BB)=Sof(C6B)=Sof(H6BA)=Sof(H6BB)=Sof(C7B)=
 Sof(H7BA)=Sof(H7BB)=Sof(O2B)=Sof(O3B)=1-FVAR(1)
 Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(C4A)=Sof(H4AA)=
 Sof(H4AB)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(C6A)=Sof(H6AA)=Sof(H6AB)=Sof(C7A)=
 Sof(H7AA)=Sof(H7AB)=Sof(O2A)=Sof(O3A)=FVAR(1)
 Sof(H12C)=Sof(H12D)=Sof(C13B)=Sof(H13C)=Sof(H13D)=Sof(H14C)=Sof(H14D)=
 Sof(O7B)=1-FVAR(2)
 Sof(H12A)=Sof(H12B)=Sof(C13A)=Sof(H13A)=Sof(H13B)=Sof(H14A)=Sof(H14B)=
 Sof(O7A)=FVAR(2)
 Sof(H1WC)=1-FVAR(3)
 Sof(H1W)=FVAR(3)
4.a Secondary CH2 refined with riding coordinates:
 C2A(H2AA,H2AB), C2B(H2BA,H2BB), C3A(H3AA,H3AB), C3B(H3BA,H3BB), C4A(H4AA,
 H4AB), C4B(H4BA,H4BB), C5A(H5AA,H5AB), C5B(H5BA,H5BB), C6A(H6AA,H6AB),
 C6B(H6BA,H6BB), C7A(H7AA,H7AB), C7B(H7BA,H7BB), C10(H10A,H10B), C11(H11A,H11B),
  C12(H12A,H12B), C12(H12C,H12D), C13A(H13A,H13B), C13B(H13C,H13D), C14(H14A,
 H14B), C14(H14C,H14D), C15(H15A,H15B)
4.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.275
_oxdiff_exptl_absorpt_empirical_full_min 0.677