Hydrogen Bonds Stabilize Chloroselenite Anions: Crystal Structure of a New Salt and Donor-Acceptor Bonding to SeO<sub>2</sub>.
Boeré, René T; Molecules (Basel, Switzerland) 28 (2023) 7489–; doi:10.3390/molecules28227489

data_1570525
_publ_section_title
;
 Hydrogen Bonds Stabilize Chloroselenite Anions: Crystal Structure of a
 New Salt and Donor-Acceptor Bonding to SeO<sub>2</sub>.
;
_journal_issue                   22
_journal_name_full               'Molecules (Basel, Switzerland)'
_journal_page_first              7489
_journal_paper_doi               10.3390/molecules28227489
_journal_volume                  28
_journal_year                    2023
_chemical_formula_moiety         'Cl O2 Se, C8 H11 N2'
_chemical_formula_sum            'C8 H11 Cl N2 O2 Se'
_chemical_formula_weight         281.601
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     direct
_audit_creation_date             2023-10-11
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.242(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9773(3)
_cell_length_b                   28.477(2)
_cell_length_c                   9.5781(9)
_cell_measurement_reflns_used    5555
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.24
_cell_volume                     1084.58(15)
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      193.15
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9977
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.9995
_diffrn_reflns_Laue_measured_fraction_max 0.9977
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8245
_diffrn_reflns_point_group_measured_fraction_full 0.9995
_diffrn_reflns_point_group_measured_fraction_max 0.9977
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         2.24
_diffrn_source_current           40.0
_diffrn_source_power             1.8
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    3.685
_exptl_absorpt_correction_T_max  0.6661
_exptl_absorpt_correction_T_min  0.3505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560.842
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.0604
_refine_diff_density_min         -0.7677
_refine_diff_density_rms         0.1194
_refine_ls_d_res_high            0.7987
_refine_ls_d_res_low             9.0764
_refine_ls_goodness_of_fit_ref   1.1032
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2194
_refine_ls_number_restraints     143
_refine_ls_restrained_S_all      1.0647
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0339
_refine_ls_shift/su_max          0.0010
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0423P)^2^+1.2540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0827
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              4
_reflns_limit_h_min              -4
_reflns_limit_k_max              35
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                1967
_reflns_number_total             2194
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            2_TolAmSeO2C_let0507b.cif
_cod_data_source_block           2_Tolylamidinium_ClSeO2
_cod_original_cell_volume        1084.56(16)
_cod_database_code               1570525
_olex2_refinement_description
;
1. Restrained distances
 C7-H7 = C3-H3 = C4-H4 = C6-H6
 1.085 with sigma of 0.02
 N1-H1b = N2-H2b = N2-H2a = N1-H1a
 1.04 with sigma of 0.02
 C8-H8d \\sim C8-H8e \\sim C8-H8f
 with sigma of 0.01
 H8a-H8b \\sim H8a-H8c \\sim H8b-H8c
 with sigma of 0.04
 H8d-H8e \\sim H8d-H8f \\sim H8e-H8f
 with sigma of 0.04
2. Uiso/Uaniso restraints and constraints
H8b \\sim H8f \\sim H8c \\sim H8d \\sim H8a \\sim H8e: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(H8e) \\sim Ueq, Uanis(H8b) \\sim Ueq, Uanis(H8f) \\sim Ueq, Uanis(H8c)
\\sim Ueq, Uanis(H8a) \\sim Ueq, Uanis(H8d) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(H1b) \\sim Ueq, Uanis(H1a) \\sim Ueq, Uanis(H2b) \\sim Ueq, Uanis(H2a)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(H7) \\sim Ueq, Uanis(H3) \\sim Ueq, Uanis(H4) \\sim Ueq, Uanis(H6) \\sim
Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 C7, H7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C6, H6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C3, H3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C4, H4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N2, H2a
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N2, H2b
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1, H1a
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1, H1b
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: H8a(0.5) H8b(0.5) H8c(0.5) H8d(0.5) H8e(0.5) H8f(0.5)
;
_olex2_refine_details
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA 5.0
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         R2SCAN
   BASIS SET:      def2-TZVP
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2023-10-04_04-28-11
;
_olex2_submission_special_instructions 'No special instructions were received'