#------------------------------------------------------------------------------
#$Date: 2023-01-06 10:58:08 +0100 (Fri 06 de Jan de 2023) $
#$Revision: 280217 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/20/7062046.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_7062046
loop_
_publ_author_name
'Aragoni, M. Carla'
'Podda, Enrico'
'Arca, Massimiliano'
'Pintus, Anna'
'Lippolis, Vito'
'Caltagirone, Claudia'
'Bartz, Ricardo H.'
'Lenardão, Eder J.'
'Perin, Gelson'
'Schumacher, Ricardo F.'
'Coles, Simon J.'
'Orton, James B.'
_publ_section_title
;
 An unprecedented non-classical polyinterhalogen anion made of
 [I2Cl]− and I2 at the 2-(p-tolyl)selenopheno[2,3-b]pyridinium
 cation template
;
_journal_issue                   45
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              21921
_journal_page_last               21929
_journal_paper_doi               10.1039/D2NJ04689J
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C14 H12 N Se, Cl, 2(H2 O)'
_chemical_formula_sum            'C14 H16 Cl N O2 Se'
_chemical_formula_weight         344.69
_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             2022-01-27
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-09-02 deposited with the CCDC.	2022-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                70.419(2)
_cell_angle_beta                 80.430(2)
_cell_angle_gamma                88.427(2)
_cell_formula_units_Z            2
_cell_length_a                   7.3040(2)
_cell_length_b                   9.1476(2)
_cell_length_c                   11.7026(2)
_cell_measurement_reflns_used    6819
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      70.3150
_cell_measurement_theta_min      4.0660
_cell_volume                     726.09(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_type            'Hybrid Photon Counting Detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00  89.00   0.50    0.50    --    0.00   0.00-180.00  356
  2  ω    -84.00  94.00   0.50    1.00    --    5.00  49.00 -30.00  356
  3  ω   -179.00  -1.00   0.50    1.00    --  -90.00  10.00   0.00  356
  4  ω   -179.00  -1.00   0.50    1.00    --  -90.00  56.00  97.00  356
  5  ω   -179.00  -1.00   0.50    1.00    --  -90.00  58.00 174.44  356
  6  ω   -179.00 -19.00   0.50    1.00    --  -90.00  56.00 134.61  320
  7  ω   -179.00  -1.00   0.50    1.00    --  -90.00  30.00 -30.00  356
  8  ω   -179.00  -1.00   0.50    1.00    --  -90.00  59.00 -27.03  356
  9  ω   -179.00  -1.00   0.50    1.00    --  -90.00  55.00  22.04  356
 10  ω   -179.00  -1.00   0.50    1.00    --  -90.00  55.00  22.04  356
 11  ω   -179.00  -1.00   0.50    1.00    --  -90.00  30.00-150.00  356
 12  ω   -179.00 -19.00   0.50    1.00    --  -90.00  56.00 134.61  320
 13  ω    -48.00 -10.00   0.50    1.00    --  -90.00  30.00 -30.00   76
 14  ω   -157.00-114.00   0.50    1.00    --  -90.00  58.00  27.20   86
 15  ω   -178.00-103.00   0.50    1.00    --  -90.00  59.00 -97.26  150
;
_diffrn_measurement_device       'three-circle quarter χ goniometer'
_diffrn_measurement_device_type  'Rigaku AFC11'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13289
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.225
_diffrn_reflns_theta_min         4.066
_exptl_absorpt_coefficient_mu    5.176
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.577
_exptl_crystal_description       lath
_exptl_crystal_F_000             348
_exptl_crystal_recrystallization_method
'The material was recrystallised from acetonitrile by slow evaporation'
_exptl_crystal_size_max          0.085
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.003
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2632
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0277
_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/[σ²(Fo²)+(0.0369P)²+0.6573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0710
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2466
_reflns_number_total             2632
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj04689j2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7062046--7062047.cif.'
_cod_database_code               7062046
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 O2-H2C
 0.84 with sigma of 0.02
 O1-H1C
 0.84 with sigma of 0.02
3. Others
 Fixed Sof: H1B(0.5) H2B(0.5) H2C(0.5) H1C(0.5)
4.a Free rotating group:
 O1(H1AA,H1B), O2(H2A,H2B)
4.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13)
4.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_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
- Detector area scaling
;
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.73226(3) 0.70229(3) 0.46028(2) 0.01994(10) Uani 1 1 d . . . . .
N1 N 0.9212(3) 0.7590(3) 0.21447(18) 0.0255(5) Uani 1 1 d . . . . .
H1 H 0.903817 0.858378 0.201636 0.031 Uiso 1 1 calc R U . . .
C1 C 1.0112(3) 0.7138(3) 0.1228(2) 0.0293(6) Uani 1 1 d . . . . .
H1A H 1.056669 0.789243 0.045209 0.035 Uiso 1 1 calc R U . . .
C2 C 1.0379(3) 0.5586(3) 0.1407(2) 0.0283(6) Uani 1 1 d . . . . .
H2 H 1.101571 0.527388 0.075411 0.034 Uiso 1 1 calc R U . . .
C3 C 0.9725(3) 0.4479(3) 0.2532(2) 0.0252(5) Uani 1 1 d . . . . .
H3 H 0.990268 0.340793 0.265375 0.030 Uiso 1 1 calc R U . . .
C4 C 0.8801(3) 0.4953(3) 0.3487(2) 0.0203(5) Uani 1 1 d . . . . .
C5 C 0.8570(3) 0.6546(3) 0.3260(2) 0.0208(5) Uani 1 1 d . . . . .
C6 C 0.8004(3) 0.4024(3) 0.4717(2) 0.0209(5) Uani 1 1 d . . . . .
H6 H 0.804497 0.292374 0.500408 0.025 Uiso 1 1 calc R U . . .
C7 C 0.7185(3) 0.4834(3) 0.5441(2) 0.0190(5) Uani 1 1 d . . . . .
C8 C 0.6261(3) 0.4222(3) 0.6729(2) 0.0194(5) Uani 1 1 d . . . . .
C9 C 0.6186(4) 0.2635(3) 0.7364(2) 0.0249(5) Uani 1 1 d . . . . .
H9 H 0.674050 0.194736 0.696140 0.030 Uiso 1 1 calc R U . . .
C10 C 0.5310(4) 0.2041(3) 0.8580(2) 0.0277(6) Uani 1 1 d . . . . .
H10 H 0.526350 0.095100 0.899246 0.033 Uiso 1 1 calc R U . . .
C11 C 0.4494(3) 0.3014(3) 0.9209(2) 0.0225(5) Uani 1 1 d . . . . .
C12 C 0.4562(3) 0.4593(3) 0.8572(2) 0.0217(5) Uani 1 1 d . . . . .
H12 H 0.400709 0.527805 0.897699 0.026 Uiso 1 1 calc R U . . .
C13 C 0.5430(3) 0.5201(3) 0.7348(2) 0.0206(5) Uani 1 1 d . . . . .
H13 H 0.545603 0.628935 0.693187 0.025 Uiso 1 1 calc R U . . .
C14 C 0.3572(4) 0.2329(3) 1.0541(2) 0.0279(5) Uani 1 1 d . . . . .
H14A H 0.450319 0.182132 1.104620 0.042 Uiso 1 1 calc R U . . .
H14B H 0.260759 0.156361 1.061294 0.042 Uiso 1 1 calc R U . . .
H14C H 0.300807 0.315695 1.082476 0.042 Uiso 1 1 calc R U . . .
Cl1 Cl 0.83337(8) 1.09248(7) 0.18902(5) 0.02941(15) Uani 1 1 d . . . . .
O1 O 0.8940(3) -0.0017(3) 0.6107(2) 0.0435(5) Uani 1 1 d DG . . . .
H1AA H 0.957140 -0.030293 0.668959 0.065 Uiso 1 1 d G U . . .
H1B H 0.801466 -0.063990 0.627461 0.065 Uiso 0.5 1 d G U P A 1
O2 O 0.5335(3) -0.0814(2) 0.61708(18) 0.0331(4) Uani 1 1 d DG . . . .
H2A H 0.431121 -0.080924 0.684518 0.050 Uiso 1 1 d G U . . .
H2B H 0.523127 -0.016961 0.546850 0.050 Uiso 0.5 1 d G U P B 1
H2C H 0.634(5) -0.056(7) 0.629(6) 0.039(19) Uiso 0.5 1 d D . P C 2
H1C H 0.955(7) -0.052(6) 0.572(4) 0.021(15) Uiso 0.5 1 d D . P D 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0166
0 -1 0 0.0036
0 1 -1 0.0020
0 -1 1 0.0010
1 0 0 0.0376
-1 0 0 0.0406
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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 Se1 C7 85.52(10) . . ?
C1 N1 H1 119.4 . . ?
C1 N1 C5 121.2(2) . . ?
C5 N1 H1 119.4 . . ?
N1 C1 H1A 119.9 . . ?
N1 C1 C2 120.2(2) . . ?
C2 C1 H1A 119.9 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(2) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 118.2(2) . . ?
C3 C4 C6 129.0(2) . . ?
C5 C4 C6 112.7(2) . . ?
N1 C5 Se1 125.27(19) . . ?
N1 C5 C4 120.7(2) . . ?
C4 C5 Se1 114.00(17) . . ?
C4 C6 H6 122.4 . . ?
C7 C6 C4 115.2(2) . . ?
C7 C6 H6 122.4 . . ?
C6 C7 Se1 112.55(17) . . ?
C6 C7 C8 128.0(2) . . ?
C8 C7 Se1 119.43(17) . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 C13 118.1(2) . . ?
C13 C8 C7 121.6(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.4(2) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C14 120.0(2) . . ?
C12 C11 C10 117.7(2) . . ?
C12 C11 C14 122.4(2) . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.4(2) . . ?
C13 C12 H12 119.3 . . ?
C8 C13 H13 119.7 . . ?
C12 C13 C8 120.6(2) . . ?
C12 C13 H13 119.7 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H1AA O1 H1B 109.4 . . ?
H1AA O1 H1C 93.3 . . ?
H2A O2 H2B 114.8 . . ?
H2A O2 H2C 111.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C5 1.857(2) . ?
Se1 C7 1.909(2) . ?
N1 H1 0.8800 . ?
N1 C1 1.342(3) . ?
N1 C5 1.350(3) . ?
C1 H1A 0.9500 . ?
C1 C2 1.378(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.397(3) . ?
C4 C5 1.401(3) . ?
C4 C6 1.435(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.362(3) . ?
C7 C8 1.468(3) . ?
C8 C9 1.389(3) . ?
C8 C13 1.398(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.398(3) . ?
C11 C12 1.383(4) . ?
C11 C14 1.515(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.395(3) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O1 H1AA 0.8504 . ?
O1 H1B 0.8500 . ?
O1 H1C 0.82(2) . ?
O2 H2A 0.9939 . ?
O2 H2B 0.8498 . ?
O2 H2C 0.82(2) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se1 C7 C8 C9 -178.45(18) . . . . ?
Se1 C7 C8 C13 1.9(3) . . . . ?
N1 C1 C2 C3 -0.1(4) . . . . ?
C1 N1 C5 Se1 179.53(18) . . . . ?
C1 N1 C5 C4 -1.0(3) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C2 C3 C4 C6 179.7(2) . . . . ?
C3 C4 C5 Se1 -179.95(17) . . . . ?
C3 C4 C5 N1 0.5(3) . . . . ?
C3 C4 C6 C7 -179.9(2) . . . . ?
C4 C6 C7 Se1 0.1(3) . . . . ?
C4 C6 C7 C8 -179.9(2) . . . . ?
C5 N1 C1 C2 0.8(4) . . . . ?
C5 C4 C6 C7 -0.4(3) . . . . ?
C6 C4 C5 Se1 0.5(3) . . . . ?
C6 C4 C5 N1 -179.1(2) . . . . ?
C6 C7 C8 C9 1.6(4) . . . . ?
C6 C7 C8 C13 -178.1(2) . . . . ?
C7 Se1 C5 N1 179.2(2) . . . . ?
C7 Se1 C5 C4 -0.31(17) . . . . ?
C7 C8 C9 C10 -179.7(2) . . . . ?
C7 C8 C13 C12 -179.9(2) . . . . ?
C8 C9 C10 C11 -0.7(4) . . . . ?
C9 C8 C13 C12 0.4(3) . . . . ?
C9 C10 C11 C12 1.0(4) . . . . ?
C9 C10 C11 C14 -179.2(2) . . . . ?
C10 C11 C12 C13 -0.6(4) . . . . ?
C11 C12 C13 C8 -0.1(4) . . . . ?
C13 C8 C9 C10 0.0(4) . . . . ?
C14 C11 C12 C13 179.6(2) . . . . ?
