#------------------------------------------------------------------------------
#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/29/7222922.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_7222922
loop_
_publ_author_name
'Cai, Qun'
'Yang, Yan'
'Li, Deng-Kui'
'Jia, Feng-Cheng'
'Xu, Cheng'
'Wu, An-Xin'
_publ_section_title
;
 CuO/I2-mediated intramolecular annulation for the synthesis of
 2-aroyl-3-hydroxy-4-iodonaphthalenes
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA17651D
_journal_year                    2015
_chemical_formula_sum            'C17 H11 I O2'
_chemical_formula_weight         374.16
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-08-01 deposited with the CCDC.
2015-10-12 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.540(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.327(4)
_cell_length_b                   11.780(5)
_cell_length_c                   10.747(4)
_cell_measurement_reflns_used    1824
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.22
_cell_measurement_theta_min      2.50
_cell_volume                     1429.5(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6008
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    2.238
_exptl_absorpt_correction_T_max  0.6758
_exptl_absorpt_correction_T_min  0.6271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2592
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0385
_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)+(0.0328P)²+1.3095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0879
_reflns_number_gt                1793
_reflns_number_total             2592
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra17651d2.cif
_cod_data_source_block           p21c
_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 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_cell_volume        1429.5(9)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7222922
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.3705(4) 0.8299(4) 0.5624(4) 0.0441(11) Uani 1 1 d .
C2 C 0.4900(4) 0.8152(4) 0.5563(4) 0.0462(12) Uani 1 1 d .
C3 C 0.5736(4) 0.8891(4) 0.6172(4) 0.0389(10) Uani 1 1 d .
C4 C 0.6969(5) 0.8762(4) 0.6174(4) 0.0550(13) Uani 1 1 d .
H4 H 0.7273 0.8157 0.5744 0.066 Uiso 1 1 calc R
C5 C 0.7721(5) 0.9494(5) 0.6783(5) 0.0622(14) Uani 1 1 d .
H5 H 0.8533 0.9380 0.6776 0.075 Uiso 1 1 calc R
C6 C 0.7300(4) 1.0425(5) 0.7427(5) 0.0597(14) Uani 1 1 d .
H6 H 0.7829 1.0930 0.7837 0.072 Uiso 1 1 calc R
C7 C 0.6122(4) 1.0586(4) 0.7451(4) 0.0493(12) Uani 1 1 d .
H7 H 0.5845 1.1204 0.7880 0.059 Uiso 1 1 calc R
C8 C 0.5309(4) 0.9832(3) 0.6836(4) 0.0374(10) Uani 1 1 d .
C9 C 0.4088(4) 0.9964(3) 0.6892(4) 0.0405(11) Uani 1 1 d .
H9 H 0.3810 1.0580 0.7324 0.049 Uiso 1 1 calc R
C10 C 0.3288(4) 0.9218(3) 0.6335(4) 0.0397(10) Uani 1 1 d .
C11 C 0.1995(4) 0.9382(4) 0.6396(5) 0.0530(13) Uani 1 1 d .
C12 C 0.1543(4) 1.0186(4) 0.7305(5) 0.0504(12) Uani 1 1 d .
C13 C 0.1853(5) 1.0095(5) 0.8574(5) 0.0636(14) Uani 1 1 d .
H13 H 0.2405 0.9555 0.8868 0.076 Uiso 1 1 calc R
C14 C 0.1347(5) 1.0800(6) 0.9396(6) 0.0817(18) Uani 1 1 d .
H14 H 0.1537 1.0722 1.0250 0.098 Uiso 1 1 calc R
C15 C 0.0564(5) 1.1617(6) 0.8961(7) 0.0814(18) Uani 1 1 d .
H15 H 0.0234 1.2103 0.9521 0.098 Uiso 1 1 calc R
C16 C 0.0263(5) 1.1727(5) 0.7723(8) 0.0831(19) Uani 1 1 d .
H16 H -0.0262 1.2293 0.7436 0.100 Uiso 1 1 calc R
C17 C 0.0738(4) 1.0995(5) 0.6879(6) 0.0652(15) Uani 1 1 d .
H17 H 0.0512 1.1054 0.6031 0.078 Uiso 1 1 calc R
I1 I 0.54250(4) 0.68029(3) 0.44782(3) 0.07476(18) Uani 1 1 d .
O1 O 0.2919(3) 0.7563(3) 0.5039(3) 0.0642(10) Uani 1 1 d .
H1 H 0.3026 0.7537 0.4294 0.096 Uiso 1 1 calc R
O2 O 0.1279(3) 0.8852(3) 0.5695(4) 0.0719(11) Uani 1 1 d .
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
O1 C1 C2 120.7(4)
O1 C1 C10 119.9(4)
C2 C1 C10 119.4(4)
C1 C2 C3 122.0(4)
C1 C2 I1 116.7(3)
C3 C2 I1 121.3(3)
C4 C3 C2 124.4(4)
C4 C3 C8 117.4(4)
C2 C3 C8 118.2(4)
C5 C4 C3 121.5(5)
C5 C4 H4 119.3
C3 C4 H4 119.3
C4 C5 C6 121.0(5)
C4 C5 H5 119.5
C6 C5 H5 119.5
C7 C6 C5 119.7(5)
C7 C6 H6 120.2
C5 C6 H6 120.2
C6 C7 C8 121.0(5)
C6 C7 H7 119.5
C8 C7 H7 119.5
C9 C8 C7 121.6(4)
C9 C8 C3 119.0(4)
C7 C8 C3 119.4(4)
C10 C9 C8 122.3(4)
C10 C9 H9 118.9
C8 C9 H9 118.9
C9 C10 C1 119.2(4)
C9 C10 C11 121.3(4)
C1 C10 C11 119.5(4)
O2 C11 C12 118.9(4)
O2 C11 C10 120.7(5)
C12 C11 C10 120.4(4)
C17 C12 C13 119.5(5)
C17 C12 C11 118.7(5)
C13 C12 C11 121.7(5)
C14 C13 C12 120.1(5)
C14 C13 H13 120.0
C12 C13 H13 120.0
C15 C14 C13 120.0(6)
C15 C14 H14 120.0
C13 C14 H14 120.0
C16 C15 C14 120.7(6)
C16 C15 H15 119.7
C14 C15 H15 119.7
C15 C16 C17 120.1(6)
C15 C16 H16 119.9
C17 C16 H16 119.9
C12 C17 C16 119.6(6)
C12 C17 H17 120.2
C16 C17 H17 120.2
C1 O1 H1 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.360(5)
C1 C2 1.371(7)
C1 C10 1.427(6)
C2 C3 1.409(6)
C2 I1 2.085(4)
C3 C4 1.405(6)
C3 C8 1.424(6)
C4 C5 1.345(7)
C4 H4 0.9300
C5 C6 1.401(7)
C5 H5 0.9300
C6 C7 1.349(6)
C6 H6 0.9300
C7 C8 1.406(6)
C7 H7 0.9300
C8 C9 1.398(6)
C9 C10 1.366(6)
C9 H9 0.9300
C10 C11 1.485(6)
C11 O2 1.232(5)
C11 C12 1.480(7)
C12 C17 1.372(7)
C12 C13 1.385(7)
C13 C14 1.371(8)
C13 H13 0.9300
C14 C15 1.366(8)
C14 H14 0.9300
C15 C16 1.353(9)
C15 H15 0.9300
C16 C17 1.389(8)
C16 H16 0.9300
C17 H17 0.9300
O1 H1 0.8200
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
O1 C1 C2 C3 -179.2(4)
C10 C1 C2 C3 -0.7(6)
O1 C1 C2 I1 2.6(5)
C10 C1 C2 I1 -179.0(3)
C1 C2 C3 C4 178.0(4)
I1 C2 C3 C4 -3.8(6)
C1 C2 C3 C8 -1.8(6)
I1 C2 C3 C8 176.3(3)
C2 C3 C4 C5 -179.5(4)
C8 C3 C4 C5 0.4(7)
C3 C4 C5 C6 -0.9(8)
C4 C5 C6 C7 0.7(8)
C5 C6 C7 C8 -0.1(7)
C6 C7 C8 C9 177.5(4)
C6 C7 C8 C3 -0.4(7)
C4 C3 C8 C9 -177.7(4)
C2 C3 C8 C9 2.1(6)
C4 C3 C8 C7 0.3(6)
C2 C3 C8 C7 -179.9(4)
C7 C8 C9 C10 -177.8(4)
C3 C8 C9 C10 0.2(6)
C8 C9 C10 C1 -2.8(6)
C8 C9 C10 C11 -179.4(4)
O1 C1 C10 C9 -178.5(4)
C2 C1 C10 C9 3.0(6)
O1 C1 C10 C11 -1.8(6)
C2 C1 C10 C11 179.7(4)
C9 C10 C11 O2 165.2(4)
C1 C10 C11 O2 -11.4(7)
C9 C10 C11 C12 -14.9(6)
C1 C10 C11 C12 168.5(4)
O2 C11 C12 C17 -52.2(6)
C10 C11 C12 C17 127.8(5)
O2 C11 C12 C13 123.6(5)
C10 C11 C12 C13 -56.3(6)
C17 C12 C13 C14 0.8(8)
C11 C12 C13 C14 -175.0(5)
C12 C13 C14 C15 -2.1(9)
C13 C14 C15 C16 1.2(9)
C14 C15 C16 C17 0.9(9)
C13 C12 C17 C16 1.2(7)
C11 C12 C17 C16 177.2(5)
C15 C16 C17 C12 -2.1(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139201074
