#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/86/7218654.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_7218654
loop_
_publ_author_name
'Anamimoghadam, Ommid'
'Long, De-Liang'
'Bucher, Götz'
_publ_section_title
;
 9-Iodophenalenone and 9-trifluoromethanesulfonyloxyphenalenone:
 convenient entry points to new phenalenones functionalised at the
 9-position. Iodine-carbonyl interaction studies by X-ray crystallography
;
_journal_issue                   100
_journal_name_full               'RSC Adv.'
_journal_page_first              56654
_journal_paper_doi               10.1039/C4RA00178H
_journal_volume                  4
_journal_year                    2014
_chemical_formula_sum            'C13 H7 I O'
_chemical_formula_weight         306.09
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.649(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.8997(18)
_cell_length_b                   12.184(2)
_cell_length_c                   13.1411(13)
_cell_measurement_reflns_used    2370
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.4
_cell_measurement_theta_min      2.98
_cell_volume                     2022.8(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4383
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Oxford Gemini Ultra A'
_diffrn_measurement_method       'ω & π scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8018
_diffrn_reflns_theta_full        25.47
_diffrn_reflns_theta_max         25.47
_diffrn_reflns_theta_min         2.99
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    3.131
_exptl_absorpt_correction_T_max  0.7878
_exptl_absorpt_correction_T_min  0.6026
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.010
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.53
_refine_diff_density_min         -0.56
_refine_diff_density_rms         0.10
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0163P)²+7.6282P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0712
_reflns_number_gt                1480
_reflns_number_total             1872
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c4ra00178h2.cif
_cod_data_source_block           oa196
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2022.9(5)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7218654
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.3503(3) 0.2145(4) 0.2366(3) 0.0238(10) Uani 1 1 d .
C2 C 0.3500(4) 0.1022(4) 0.2157(3) 0.0279(11) Uani 1 1 d .
H2 H 0.3365 0.0516 0.2665 0.033 Uiso 1 1 calc R
C3 C 0.3688(4) 0.0639(4) 0.1235(4) 0.0308(12) Uani 1 1 d .
H3 H 0.3706 -0.0129 0.1118 0.037 Uiso 1 1 calc R
C4 C 0.3855(3) 0.1374(4) 0.0455(3) 0.0245(10) Uani 1 1 d .
C5 C 0.4038(4) 0.1008(4) -0.0519(4) 0.0297(11) Uani 1 1 d .
H5 H 0.4078 0.0243 -0.0646 0.036 Uiso 1 1 calc R
C6 C 0.4159(4) 0.1739(5) -0.1281(3) 0.0307(12) Uani 1 1 d .
H6 H 0.4290 0.1481 -0.1925 0.037 Uiso 1 1 calc R
C7 C 0.4088(4) 0.2860(4) -0.1107(3) 0.0298(12) Uani 1 1 d .
H7 H 0.4145 0.3362 -0.1647 0.036 Uiso 1 1 calc R
C8 C 0.3935(3) 0.3256(4) -0.0164(3) 0.0239(10) Uani 1 1 d .
C9 C 0.3869(4) 0.4432(4) 0.0010(4) 0.0290(11) Uani 1 1 d .
H9 H 0.3906 0.4928 -0.0540 0.035 Uiso 1 1 calc R
C10 C 0.3756(4) 0.4825(4) 0.0934(3) 0.0292(11) Uani 1 1 d .
H10 H 0.3718 0.5598 0.1017 0.035 Uiso 1 1 calc R
C11 C 0.3688(3) 0.4130(4) 0.1817(4) 0.0262(11) Uani 1 1 d .
C12 C 0.3666(3) 0.2920(4) 0.1641(3) 0.0209(10) Uani 1 1 d .
C13 C 0.3832(3) 0.2512(4) 0.0646(3) 0.0199(9) Uani 1 1 d .
O1 O 0.3658(3) 0.4529(3) 0.2663(3) 0.0404(9) Uani 1 1 d .
I1 I 0.31540(3) 0.25443(3) 0.38237(2) 0.03475(14) Uani 1 1 d .
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
C1 0.023(2) 0.031(3) 0.017(2) -0.002(2) 0.0036(18) -0.002(2)
C2 0.031(3) 0.027(3) 0.025(3) 0.009(2) 0.003(2) -0.001(2)
C3 0.028(3) 0.026(3) 0.036(3) 0.003(2) 0.001(2) 0.004(2)
C4 0.021(2) 0.024(3) 0.027(3) -0.002(2) 0.0013(18) 0.006(2)
C5 0.031(3) 0.026(3) 0.031(3) -0.007(2) 0.002(2) 0.009(2)
C6 0.032(3) 0.043(3) 0.017(2) -0.008(2) 0.004(2) 0.008(2)
C7 0.025(3) 0.046(3) 0.019(2) 0.005(2) 0.0061(19) -0.003(2)
C8 0.017(2) 0.026(3) 0.027(3) 0.003(2) 0.0007(18) 0.001(2)
C9 0.025(3) 0.030(3) 0.030(3) 0.009(2) 0.001(2) -0.001(2)
C10 0.032(3) 0.024(3) 0.032(3) -0.005(2) 0.006(2) -0.002(2)
C11 0.022(3) 0.024(3) 0.032(3) -0.006(2) 0.005(2) -0.001(2)
C12 0.019(2) 0.026(3) 0.017(2) 0.0012(19) 0.0031(17) 0.003(2)
C13 0.014(2) 0.026(3) 0.018(2) -0.002(2) -0.0010(16) 0.003(2)
O1 0.062(3) 0.033(2) 0.029(2) -0.0086(16) 0.0153(17) -0.0036(19)
I1 0.0388(2) 0.0460(2) 0.02207(19) 0.00029(16) 0.01236(13) -0.00526(18)
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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C12 C1 C2 121.8(4)
C12 C1 I1 123.8(3)
C2 C1 I1 114.3(3)
C3 C2 C1 121.1(4)
C2 C3 C4 120.6(5)
C3 C4 C13 118.9(4)
C3 C4 C5 122.2(5)
C13 C4 C5 118.9(4)
C6 C5 C4 121.2(5)
C5 C6 C7 119.8(4)
C8 C7 C6 121.1(4)
C7 C8 C13 120.1(4)
C7 C8 C9 120.5(4)
C13 C8 C9 119.4(4)
C10 C9 C8 120.9(4)
C9 C10 C11 123.4(5)
O1 C11 C10 120.9(4)
O1 C11 C12 122.0(4)
C10 C11 C12 117.1(4)
C1 C12 C13 117.1(4)
C1 C12 C11 124.6(4)
C13 C12 C11 118.4(4)
C4 C13 C8 118.9(4)
C4 C13 C12 120.5(4)
C8 C13 C12 120.5(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C12 1.388(6)
C1 C2 1.395(7)
C1 I1 2.110(4)
C2 C3 1.365(7)
C3 C4 1.410(6)
C4 C13 1.411(6)
C4 C5 1.421(6)
C5 C6 1.373(7)
C6 C7 1.391(8)
C7 C8 1.380(6)
C8 C13 1.425(6)
C8 C9 1.457(7)
C9 C10 1.341(6)
C10 C11 1.452(7)
C11 O1 1.221(5)
C11 C12 1.492(6)
C12 C13 1.454(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139199439
