#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/17/7151717.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_7151717
loop_
_publ_author_name
'Raffa, Guillaume'
'Belot, Sébastien'
'Balme, Geneviève'
'Monteiro, Nuno'
_publ_section_title
;
 Iodocyclization versus diiodination in the reaction of
 3-alkynyl-4-methoxycoumarins with iodine: Synthesis of
 3-iodofuro[2,3-b]chromones.
;
_journal_issue                   5
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1474
_journal_page_last               1478
_journal_paper_doi               10.1039/C0OB00935K
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C17 H9 I1 O3'
_chemical_formula_sum            'C17 H9 I O3'
_chemical_formula_weight         388.16
_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
_cell_angle_alpha                90
_cell_angle_beta                 103.46(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.173(2)
_cell_length_b                   14.445(2)
_cell_length_c                   8.223(2)
_cell_measurement_reflns_used    2573
_cell_measurement_temperature    293
_cell_measurement_theta_max      29.4921
_cell_measurement_theta_min      3.4346
_cell_volume                     1406.2(5)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 10.4685
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.846
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.079
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6630
_diffrn_reflns_theta_full        26.302
_diffrn_reflns_theta_max         29.553
_diffrn_reflns_theta_min         3.442
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.284
_exptl_absorpt_correction_T_max  0.869
_exptl_absorpt_correction_T_min  0.471
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
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            colorless
_exptl_crystal_density_diffrn    1.833
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.286
_exptl_crystal_size_min          0.081
_refine_diff_density_max         2.39
_refine_diff_density_min         -1.99
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9991
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1292
_refine_ls_R_factor_gt           0.0934
_refine_ls_shift/su_max          0.0001591
_refine_ls_shift/su_mean         0.0000098
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[σ²(F²) + ( 0.20P)² + 0.00P]
,where P=(max(Fo²,0) + 2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.3093
_refine_ls_wR_factor_gt          0.2532
_refine_ls_wR_factor_ref         0.3093
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                1974
_reflns_number_total             3327
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   4.99
_oxford_diffrn_Wilson_scale      0.15
_oxford_refine_ls_r_factor_ref   0.1292
_oxford_refine_ls_scale          3.74(17)
_oxford_reflns_number_all        3323
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            C0OB00935K.TXT
_cod_data_source_block           2a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_original_formula_sum        'C17 H9 I1 O3'
_cod_database_code               7151717
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S
RIDE C ( 13,X'S) H ( 131,X'S)
RIDE C ( 14,X'S) H ( 141,X'S)
RIDE C ( 15,X'S) H ( 151,X'S)
RIDE C ( 16,X'S) H ( 161,X'S)
RIDE C ( 17,X'S) H ( 171,X'S)
RIDE C ( 18,X'S) H ( 181,X'S)
RIDE C ( 19,X'S) H ( 191,X'S)
RIDE C ( 20,X'S) H ( 201,X'S)
RIDE C ( 21,X'S) H ( 211,X'S)
END
;
_iucr_refine_instruction_details_restraints
;
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
I1 I 0.37354(6) 0.70698(4) 0.28840(9) 0.0818 1.0000 Uani . . . . . .
C2 C 0.3513(6) 0.6043(5) 0.4514(11) 0.0563 1.0000 Uani . . . . . .
C3 C 0.2519(6) 0.5458(5) 0.4253(9) 0.0486 1.0000 Uani . . . . . .
C4 C 0.1466(7) 0.5395(6) 0.3020(10) 0.0553 1.0000 Uani . . . . . .
O5 O 0.1178(5) 0.5905(5) 0.1780(8) 0.0780 1.0000 Uani . . . . . .
C6 C 0.0755(6) 0.4615(5) 0.3364(10) 0.0559 1.0000 Uani . . . . . .
C7 C 0.1078(6) 0.4080(5) 0.4813(9) 0.0497 1.0000 Uani . . . . . .
O8 O 0.2083(4) 0.4201(4) 0.5967(7) 0.0592 1.0000 Uani . . . . . .
C9 C 0.2708(6) 0.4875(5) 0.5571(10) 0.0520 1.0000 Uani . . . . . .
O10 O 0.3720(4) 0.4996(4) 0.6633(7) 0.0537 1.0000 Uani . . . . . .
C11 C 0.4236(6) 0.5736(5) 0.5970(10) 0.0543 1.0000 Uani . . . . . .
C12 C 0.5348(7) 0.5975(5) 0.6951(10) 0.0543 1.0000 Uani . . . . . .
C13 C 0.6009(7) 0.6680(6) 0.6491(13) 0.0697 1.0000 Uani . . . . . .
C14 C 0.7048(8) 0.6884(7) 0.7492(15) 0.0739 1.0000 Uani . . . . . .
C15 C 0.7470(8) 0.6401(7) 0.9006(13) 0.0758 1.0000 Uani . . . . . .
C16 C 0.6848(8) 0.5693(9) 0.9423(12) 0.0808 1.0000 Uani . . . . . .
C17 C 0.5791(7) 0.5489(7) 0.8393(11) 0.0686 1.0000 Uani . . . . . .
C18 C 0.0403(7) 0.3339(6) 0.5126(12) 0.0657 1.0000 Uani . . . . . .
C19 C -0.0583(8) 0.3156(6) 0.4004(13) 0.0684 1.0000 Uani . . . . . .
C20 C -0.0912(8) 0.3689(7) 0.2549(14) 0.0739 1.0000 Uani . . . . . .
C21 C -0.0269(7) 0.4408(6) 0.2260(10) 0.0603 1.0000 Uani . . . . . .
H131 H 0.5739 0.7011 0.5508 0.0832 1.0000 Uiso R . . . . .
H141 H 0.7478 0.7349 0.7172 0.0899 1.0000 Uiso R . . . . .
H151 H 0.8158 0.6555 0.9705 0.0909 1.0000 Uiso R . . . . .
H161 H 0.7128 0.5341 1.0378 0.0962 1.0000 Uiso R . . . . .
H171 H 0.5367 0.5010 0.8713 0.0830 1.0000 Uiso R . . . . .
H181 H 0.0626 0.2989 0.6096 0.0779 1.0000 Uiso R . . . . .
H191 H -0.1042 0.2676 0.4195 0.0819 1.0000 Uiso R . . . . .
H201 H -0.1572 0.3548 0.1768 0.0883 1.0000 Uiso R . . . . .
H211 H -0.0520 0.4779 0.1311 0.0730 1.0000 Uiso R . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
I1 . C2 . C3 . 123.7(6) yes
I1 . C2 . C11 . 129.9(6) yes
C3 . C2 . C11 . 106.4(7) yes
C2 . C3 . C4 . 135.7(7) yes
C2 . C3 . C9 . 105.3(7) yes
C4 . C3 . C9 . 118.9(7) yes
C3 . C4 . O5 . 125.2(8) yes
C3 . C4 . C6 . 112.0(6) yes
O5 . C4 . C6 . 122.7(7) yes
C4 . C6 . C7 . 121.4(6) yes
C4 . C6 . C21 . 120.7(7) yes
C7 . C6 . C21 . 117.9(8) yes
C6 . C7 . O8 . 123.2(7) yes
C6 . C7 . C18 . 121.0(7) yes
O8 . C7 . C18 . 115.7(7) yes
C7 . O8 . C9 . 113.2(6) yes
C3 . C9 . O8 . 131.1(7) yes
C3 . C9 . O10 . 113.6(7) yes
O8 . C9 . O10 . 115.4(6) yes
C9 . O10 . C11 . 105.7(6) yes
O10 . C11 . C2 . 109.1(6) yes
O10 . C11 . C12 . 114.1(6) yes
C2 . C11 . C12 . 136.9(7) yes
C11 . C12 . C13 . 122.9(8) yes
C11 . C12 . C17 . 119.1(7) yes
C13 . C12 . C17 . 117.9(7) yes
C12 . C13 . C14 . 120.1(9) yes
C12 . C13 . H131 . 119.9 no
C14 . C13 . H131 . 120.1 no
C13 . C14 . C15 . 121.2(9) yes
C13 . C14 . H141 . 119.2 no
C15 . C14 . H141 . 119.6 no
C14 . C15 . C16 . 118.8(8) yes
C14 . C15 . H151 . 121.2 no
C16 . C15 . H151 . 120.0 no
C15 . C16 . C17 . 119.6(10) yes
C15 . C16 . H161 . 120.4 no
C17 . C16 . H161 . 120.0 no
C16 . C17 . C12 . 122.4(9) yes
C16 . C17 . H171 . 118.4 no
C12 . C17 . H171 . 119.2 no
C7 . C18 . C19 . 119.0(8) yes
C7 . C18 . H181 . 120.3 no
C19 . C18 . H181 . 120.8 no
C18 . C19 . C20 . 120.3(8) yes
C18 . C19 . H191 . 120.2 no
C20 . C19 . H191 . 119.5 no
C19 . C20 . C21 . 120.6(8) yes
C19 . C20 . H201 . 120.0 no
C21 . C20 . H201 . 119.3 no
C6 . C21 . C20 . 121.1(8) yes
C6 . C21 . H211 . 119.2 no
C20 . C21 . H211 . 119.7 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 . C2 . 2.059(8) yes
C2 . C3 . 1.450(10) yes
C2 . C11 . 1.383(11) yes
C3 . C4 . 1.440(10) yes
C3 . C9 . 1.349(10) yes
C4 . O5 . 1.240(10) yes
C4 . C6 . 1.488(12) yes
C6 . C7 . 1.397(11) yes
C6 . C21 . 1.393(10) yes
C7 . O8 . 1.374(9) yes
C7 . C18 . 1.409(11) yes
O8 . C9 . 1.323(10) yes
C9 . O10 . 1.345(9) yes
O10 . C11 . 1.412(9) yes
C11 . C12 . 1.447(11) yes
C12 . C13 . 1.403(12) yes
C12 . C17 . 1.376(12) yes
C13 . C14 . 1.371(13) yes
C13 . H131 . 0.930 no
C14 . C15 . 1.415(15) yes
C14 . H141 . 0.927 no
C15 . C16 . 1.363(14) yes
C15 . H151 . 0.926 no
C16 . C17 . 1.397(12) yes
C16 . H161 . 0.931 no
C17 . H171 . 0.937 no
C18 . C19 . 1.359(12) yes
C18 . H181 . 0.930 no
C19 . C20 . 1.400(14) yes
C19 . H191 . 0.926 no
C20 . C21 . 1.354(13) yes
C20 . H201 . 0.927 no
C21 . H211 . 0.937 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26995510
2 PubChem 101779812
