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#$Date: 2025-03-04 20:19:01 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298010 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/40/7134040.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_7134040
loop_
_publ_author_name
'Antonkin, Nikita S.'
'Vlasenko, Yulia A.'
'Puylaert, Pim'
'Nachtsheim, Boris J.'
'Postnikov, Pavel S.'
_publ_section_title
;
 N-Heterocycle-coordinated λ⁵-iodanes as IBX
 alternatives for alcohol oxidations.
;
_journal_issue                   4
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              756
_journal_page_last               759
_journal_paper_doi               10.1039/d4cc05058d
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C13 H9 I N2 O2'
_chemical_formula_sum            'C13 H9 I N2 O2'
_chemical_formula_weight         352.12
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-06-21
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-06-21 deposited with the CCDC.	2024-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.555(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5622(6)
_cell_length_b                   11.6742(8)
_cell_length_c                   15.1234(11)
_cell_measurement_reflns_used    9865
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      36.368
_cell_measurement_theta_min      2.207
_cell_volume                     1157.43(16)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            33426
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.351
_diffrn_reflns_theta_min         3.107
_diffrn_source                   'microfocus Ims X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    2.761
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.6449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0936 before and 0.0507 after correction.
The Ratio of minimum to maximum transmission is 0.8632.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.021
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         5599
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0185
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0116P)²+0.8199P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0411
_refine_ls_wR_factor_ref         0.0424
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5131
_reflns_number_total             5599
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc05058d2.cif
_cod_data_source_block           antonkinn231228
_cod_depositor_comments
'Adding full bibliography for 7134040--7134042.cif.'
_cod_database_code               7134040
_shelx_shelxl_version_number     2019/3
_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.
;
_shelx_estimated_absorpt_t_max   0.770
_shelx_estimated_absorpt_t_min   0.288
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C13(H13), C4(H4), C3(H3), C2(H2), C9(H9), C10(H10), C11(H11), C8(H8)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
I1 I 0.25018(2) 0.53497(2) 0.45328(2) 0.00967(2) Uani 1 1 d . . . . .
O1 O 0.11439(14) 0.59242(8) 0.54527(6) 0.01479(16) Uani 1 1 d . . . . .
O2 O 0.48519(14) 0.61525(8) 0.46545(6) 0.01492(16) Uani 1 1 d . . . . .
N2 N 0.41252(16) 0.49883(10) 0.29846(7) 0.01313(17) Uani 1 1 d . . . . .
N1 N 0.34113(16) 0.58235(9) 0.24168(7) 0.01150(16) Uani 1 1 d . . . . .
C5 C 0.05635(19) 0.71097(11) 0.20521(8) 0.0137(2) Uani 1 1 d . . . . .
H5 H 0.097796 0.716499 0.145973 0.016 Uiso 1 1 calc R U . . .
C6 C 0.16818(17) 0.64371(10) 0.26633(7) 0.01067(18) Uani 1 1 d . . . . .
C1 C 0.10218(18) 0.63704(10) 0.35331(7) 0.01103(18) Uani 1 1 d . . . . .
C13 C 0.5752(2) 0.45348(11) 0.26438(9) 0.0145(2) Uani 1 1 d . . . . .
H13 H 0.655395 0.394155 0.291253 0.017 Uiso 1 1 calc R U . . .
C4 C -0.1151(2) 0.76977(11) 0.23072(8) 0.0155(2) Uani 1 1 d . . . . .
H4 H -0.189360 0.815664 0.188617 0.019 Uiso 1 1 calc R U . . .
C3 C -0.18030(19) 0.76273(12) 0.31695(9) 0.0159(2) Uani 1 1 d . . . . .
H3 H -0.297751 0.803501 0.333742 0.019 Uiso 1 1 calc R U . . .
C12 C 0.61436(19) 0.50548(11) 0.18187(8) 0.0136(2) Uani 1 1 d . . . . .
C7 C 0.46239(18) 0.59035(10) 0.16934(8) 0.01154(18) Uani 1 1 d . . . . .
C2 C -0.07084(19) 0.69511(11) 0.37812(8) 0.0137(2) Uani 1 1 d . . . . .
H2 H -0.114565 0.688651 0.436954 0.016 Uiso 1 1 calc R U . . .
C9 C 0.6076(2) 0.64591(12) 0.03504(9) 0.0173(2) Uani 1 1 d . . . . .
H9 H 0.609470 0.694090 -0.015541 0.021 Uiso 1 1 calc R U . . .
C10 C 0.7550(2) 0.55909(13) 0.04519(9) 0.0203(3) Uani 1 1 d . . . . .
H10 H 0.851298 0.548583 0.000841 0.024 Uiso 1 1 calc R U . . .
C11 C 0.7619(2) 0.48884(12) 0.11865(9) 0.0182(2) Uani 1 1 d . . . . .
H11 H 0.863134 0.431085 0.126202 0.022 Uiso 1 1 calc R U . . .
C8 C 0.45998(19) 0.66382(11) 0.09587(8) 0.0145(2) Uani 1 1 d . . . . .
H8 H 0.361499 0.723072 0.088332 0.017 Uiso 1 1 calc R U . . .
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'
I I -0.4742 1.8119 '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'
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
O1 I1 C1 96.53(4) . . ?
O2 I1 O1 100.16(4) . . ?
O2 I1 C1 98.19(4) . . ?
C13 N2 N1 107.56(10) . . ?
N2 N1 C6 117.03(9) . . ?
N2 N1 C7 110.57(9) . . ?
C7 N1 C6 132.39(10) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.20(11) . . ?
C5 C6 N1 121.17(10) . . ?
C5 C6 C1 118.43(11) . . ?
C1 C6 N1 120.40(10) . . ?
C6 C1 I1 123.14(8) . . ?
C2 C1 I1 115.77(8) . . ?
C2 C1 C6 121.06(11) . . ?
N2 C13 H13 124.7 . . ?
N2 C13 C12 110.68(11) . . ?
C12 C13 H13 124.7 . . ?
C5 C4 H4 119.4 . . ?
C5 C4 C3 121.20(11) . . ?
C3 C4 H4 119.4 . . ?
C4 C3 H3 120.5 . . ?
C2 C3 C4 119.00(11) . . ?
C2 C3 H3 120.5 . . ?
C7 C12 C13 105.26(10) . . ?
C11 C12 C13 134.09(12) . . ?
C11 C12 C7 120.65(12) . . ?
N1 C7 C12 105.90(10) . . ?
N1 C7 C8 132.88(11) . . ?
C8 C7 C12 121.19(11) . . ?
C1 C2 C3 120.10(11) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C10 C9 H9 118.8 . . ?
C8 C9 H9 118.8 . . ?
C8 C9 C10 122.43(12) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 120.97(12) . . ?
C11 C10 H10 119.5 . . ?
C12 C11 H11 121.1 . . ?
C10 C11 C12 117.84(12) . . ?
C10 C11 H11 121.1 . . ?
C7 C8 H8 121.6 . . ?
C9 C8 C7 116.84(11) . . ?
C9 C8 H8 121.6 . . ?
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
I1 O1 1.8138(9) . ?
I1 O2 1.8070(9) . ?
I1 C1 2.1256(11) . ?
N2 N1 1.3680(14) . ?
N2 C13 1.3172(16) . ?
N1 C6 1.4064(15) . ?
N1 C7 1.3843(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.3961(17) . ?
C5 C4 1.3872(17) . ?
C6 C1 1.4052(16) . ?
C1 C2 1.3883(16) . ?
C13 H13 0.9500 . ?
C13 C12 1.4213(18) . ?
C4 H4 0.9500 . ?
C4 C3 1.3929(18) . ?
C3 H3 0.9500 . ?
C3 C2 1.3913(18) . ?
C12 C7 1.4126(17) . ?
C12 C11 1.4039(18) . ?
C7 C8 1.4032(17) . ?
C2 H2 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.4047(19) . ?
C9 C8 1.3811(17) . ?
C10 H10 0.9500 . ?
C10 C11 1.380(2) . ?
C11 H11 0.9500 . ?
C8 H8 0.9500 . ?
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
I1 C1 C2 C3 -178.98(10) . . . . ?
N2 N1 C6 C5 -165.06(11) . . . . ?
N2 N1 C6 C1 13.94(16) . . . . ?
N2 N1 C7 C12 1.09(14) . . . . ?
N2 N1 C7 C8 -176.88(13) . . . . ?
N2 C13 C12 C7 1.66(15) . . . . ?
N2 C13 C12 C11 -178.69(15) . . . . ?
N1 N2 C13 C12 -1.01(15) . . . . ?
N1 C6 C1 I1 -0.77(16) . . . . ?
N1 C6 C1 C2 -178.57(11) . . . . ?
N1 C7 C8 C9 -179.69(13) . . . . ?
C5 C6 C1 I1 178.26(9) . . . . ?
C5 C6 C1 C2 0.46(18) . . . . ?
C5 C4 C3 C2 -0.1(2) . . . . ?
C6 N1 C7 C12 179.77(12) . . . . ?
C6 N1 C7 C8 1.8(2) . . . . ?
C6 C5 C4 C3 -0.4(2) . . . . ?
C6 C1 C2 C3 -1.03(19) . . . . ?
C13 N2 N1 C6 -178.97(11) . . . . ?
C13 N2 N1 C7 -0.06(14) . . . . ?
C13 C12 C7 N1 -1.61(14) . . . . ?
C13 C12 C7 C8 176.65(12) . . . . ?
C13 C12 C11 C10 -178.57(15) . . . . ?
C4 C5 C6 N1 179.28(12) . . . . ?
C4 C5 C6 C1 0.26(18) . . . . ?
C4 C3 C2 C1 0.9(2) . . . . ?
C12 C7 C8 C9 2.60(19) . . . . ?
C7 N1 C6 C5 16.3(2) . . . . ?
C7 N1 C6 C1 -164.67(12) . . . . ?
C7 C12 C11 C10 1.0(2) . . . . ?
C9 C10 C11 C12 1.3(2) . . . . ?
C10 C9 C8 C7 -0.3(2) . . . . ?
C11 C12 C7 N1 178.69(12) . . . . ?
C11 C12 C7 C8 -3.05(19) . . . . ?
C8 C9 C10 C11 -1.7(2) . . . . ?
