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#$Date: 2026-04-10 02:28:51 +0200 (Fri 10 de Apr de 2026) $
#$Revision: 305505 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/11/7161108.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_7161108
loop_
_publ_author_name
'Lysenko, Vladyslav'
'Popov, Ioann O.'
'Slobodyanyuk, Evgeniy Y.'
'Rusanov, Eduard'
'Pashenko, Olexandr Ye.'
'Volochnyuk, Dmitriy M.'
'Ryabukhin, Serhiy V.'
_publ_section_title
;
 Cyclooctadiene-Derived Cage-Divergent Synthesis of Heteroadamantanes and
 Alternative Polycyclic Systems
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D6OB00368K
_journal_year                    2025
_chemical_formula_moiety         'C8 H12 I2 O'
_chemical_formula_sum            'C8 H12 I2 O'
_chemical_formula_weight         377.98
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-02-03
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-05-28 deposited with the CCDC.	2026-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 128.734(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.1580(8)
_cell_length_b                   5.3842(2)
_cell_length_c                   13.0363(6)
_cell_measurement_reflns_used    3809
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.30
_cell_measurement_theta_min      2.73
_cell_volume                     1048.95(10)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7025
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.978
_diffrn_reflns_theta_max         24.978
_diffrn_reflns_theta_min         2.726
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.946
_exptl_absorpt_correction_T_max  0.8277
_exptl_absorpt_correction_T_min  0.3537
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.393
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.598
_refine_diff_density_min         -1.336
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     51
_refine_ls_number_reflns         924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0291
_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)+(0.0088P)²+13.7636P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0570
_refine_ls_wR_factor_ref         0.0605
_reflns_Friedel_coverage         0.000
_reflns_number_gt                828
_reflns_number_total             924
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6ob00368k2.cif
_cod_data_source_block           v586
_cod_original_cell_volume        1048.95(9)
_cod_database_code               7161108
_shelx_shelxl_version_number     2016/6
_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   0.717
_shelx_estimated_absorpt_t_min   0.368
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
;
_shelx_res_file
;
TITL v586_a.res in C2/c
    v586.res
    created by SHELXL-2016/6 at 22:11:41 on 03-Feb-2025
REM Old TITL v586_a.res in C2/c
REM SHELXT solution in C2/c
REM R1 0.201, Rweak 0.016, Alpha 0.027, Orientation as input
REM Formula found by SHELXT: C8 O I2
CELL 0.71073 19.158 5.3842 13.0363 90 128.734 90
ZERR 4 0.0008 0.0002 0.0006 0 0.004 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H I O
UNIT 32 48 8 4

L.S. 10
PLAN  2
SIZE 0.21 0.07 0.06
TEMP -100(2)
CONF
BOND $H
LIST 6
MORE -1
fmap 2
acta
OMIT -2 50
REM <olex2.extras>
REM <HklSrc "%.\\v586.hkl">
REM </olex2.extras>

WGHT    0.008800   13.763600
FVAR       0.25035
I1    3    0.311883    0.940185    0.719727    11.00000    0.04686    0.08021 =
         0.05671   -0.02742    0.03779   -0.02407
O1    4    0.500000    0.427731    0.750000    10.50000    0.10891    0.02340 =
         0.07154    0.00000    0.06680    0.00000
C1    1    0.383076    0.716050    0.672885    11.00000    0.05364    0.04142 =
         0.03499   -0.01479    0.02889   -0.01859
AFIX  13
H1    2    0.339959    0.587570    0.608232    11.00000   -1.20000
AFIX   0
C2    1    0.408542    0.872280    0.604267    11.00000    0.04026    0.03510 =
         0.02902    0.00073    0.02009   -0.00433
AFIX  23
H2A   2    0.441717    1.021375    0.657770    11.00000   -1.20000
H2B   2    0.353784    0.928015    0.517904    11.00000   -1.20000
AFIX   0
C3    1    0.466653    0.721293    0.584650    11.00000    0.05507    0.04557 =
         0.03070   -0.00467    0.02886   -0.00071
AFIX  23
H3A   2    0.428205    0.602707    0.511538    11.00000   -1.20000
H3B   2    0.493962    0.834858    0.558897    11.00000   -1.20000
AFIX   0
C4    1    0.540509    0.577966    0.706452    11.00000    0.08152    0.03609 =
         0.04560    0.00183    0.04619    0.01940
AFIX  13
H4    2    0.567115    0.461237    0.679638    11.00000   -1.20000
AFIX   0
HKLF 4




REM  v586_a.res in C2/c
REM R1 =  0.0291 for     828 Fo > 4sig(Fo)  and  0.0337 for all     924 data
REM     51 parameters refined using      0 restraints

END

WGHT      0.0088     13.7601

REM Highest difference peak  1.598,  deepest hole -1.336,  1-sigma level  0.110
Q1    1   0.3416  0.8188  0.7847  11.00000  0.05    1.60
Q2    1   0.5673  0.4434  0.8489  11.00000  0.05    0.66
;
_shelx_res_checksum              48651
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.31188(3) 0.94018(9) 0.71973(4) 0.05757(18) Uani 1 1 d . . . . .
O1 O 0.500000 0.4277(10) 0.750000 0.0609(17) Uani 1 2 d S T P . .
C1 C 0.3831(4) 0.7161(11) 0.6729(5) 0.0426(13) Uani 1 1 d . . . . .
H1 H 0.339959 0.587570 0.608232 0.051 Uiso 1 1 calc R U . . .
C2 C 0.4085(3) 0.8723(10) 0.6043(5) 0.0359(12) Uani 1 1 d . . . . .
H2A H 0.441717 1.021375 0.657770 0.043 Uiso 1 1 calc R U . . .
H2B H 0.353784 0.928015 0.517904 0.043 Uiso 1 1 calc R U . . .
C3 C 0.4667(4) 0.7213(11) 0.5847(5) 0.0424(13) Uani 1 1 d . . . . .
H3A H 0.428205 0.602707 0.511538 0.051 Uiso 1 1 calc R U . . .
H3B H 0.493962 0.834858 0.558897 0.051 Uiso 1 1 calc R U . . .
C4 C 0.5405(4) 0.5780(11) 0.7065(6) 0.0500(15) Uani 1 1 d . . . . .
H4 H 0.567115 0.461237 0.679638 0.060 Uiso 1 1 calc R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.0469(2) 0.0802(3) 0.0567(3) -0.0274(2) 0.0378(2) -0.0241(2)
O1 0.109(5) 0.023(3) 0.072(4) 0.000 0.067(4) 0.000
C1 0.054(3) 0.041(3) 0.035(3) -0.015(2) 0.029(3) -0.019(3)
C2 0.040(3) 0.035(3) 0.029(3) 0.001(2) 0.020(2) -0.004(2)
C3 0.055(3) 0.046(3) 0.031(3) -0.005(2) 0.029(3) -0.001(3)
C4 0.082(4) 0.036(3) 0.046(3) 0.002(3) 0.046(3) 0.019(3)
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'
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
C4 O1 C4 112.7(6) . 2_656 ?
I1 C1 H1 106.7 . . ?
C2 C1 I1 110.4(4) . . ?
C2 C1 H1 106.7 . . ?
C4 C1 I1 110.5(3) 2_656 . ?
C4 C1 H1 106.7 2_656 . ?
C4 C1 C2 115.3(5) 2_656 . ?
C1 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
C1 C2 C3 110.0(4) . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 H2A 109.7 . . ?
C3 C2 H2B 109.7 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 C2 113.3(4) . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
O1 C4 C1 105.8(4) . 2_656 ?
O1 C4 C3 108.3(5) . . ?
O1 C4 H4 107.4 . . ?
C1 C4 C3 120.0(5) 2_656 . ?
C1 C4 H4 107.4 2_656 . ?
C3 C4 H4 107.4 . . ?
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 C1 2.175(6) . ?
O1 C4 1.460(7) . ?
O1 C4 1.460(7) 2_656 ?
C1 H1 1.0000 . ?
C1 C2 1.514(7) . ?
C1 C4 1.513(8) 2_656 ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.524(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.519(8) . ?
C4 H4 1.0000 . ?
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 174.1(3) . . . . ?
C1 C2 C3 C4 -45.8(6) . . . . ?
C2 C3 C4 O1 53.7(6) . . . . ?
C2 C3 C4 C1 -67.7(7) . . . 2_656 ?
C4 O1 C4 C1 64.8(3) 2_656 . . 2_656 ?
C4 O1 C4 C3 -65.0(3) 2_656 . . . ?
C4 C1 C2 C3 48.1(6) 2_656 . . . ?
