#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/96/2229637.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2229637
loop_
_publ_author_name
'Pereira Silva, P. S.'
'Parveen, Mehtab'
'Ali, Akhtar'
'Ramos Silva, M.'
_publ_section_title
;
 8-Iodo-5,7-dimethoxy-4-methyl-2H-chromen-2-one
;
_journal_coeditor_code           FJ2395
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o776
_journal_paper_doi               10.1107/S1600536811007549
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C12 H11 I O4'
_chemical_formula_moiety         'C12 H11 I O4'
_chemical_formula_sum            'C12 H11 I O4'
_chemical_formula_weight         346.11
_chemical_melting_point          523
_chemical_name_common            8-iodo-5,7-dimethoxy-4-methylcoumarin
_chemical_name_systematic
;
8-Iodo-5,7-dimethoxy-4-methyl-2H-chromen-2-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                109.645(5)
_cell_angle_beta                 94.734(5)
_cell_angle_gamma                104.060(5)
_cell_formula_units_Z            2
_cell_length_a                   7.1103(7)
_cell_length_b                   9.5825(10)
_cell_length_c                   9.9866(9)
_cell_measurement_reflns_used    5373
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1931
_cell_measurement_theta_min      2.5647
_cell_volume                     611.50(11)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'APEX2 (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0149
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17329
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.20
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.618
_exptl_absorpt_correction_T_max  0.712
_exptl_absorpt_correction_T_min  0.511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            'light pink'
_exptl_crystal_density_diffrn    1.880
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.752
_refine_diff_density_min         -0.589
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.281
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2970
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.281
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0210
_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)+(0.0503P)²+0.1088P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0653
_refine_ls_wR_factor_ref         0.0904
_reflns_number_gt                2701
_reflns_number_total             2970
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2395.cif
_cod_data_source_block           I
_cod_original_cell_volume        611.50(10)
_cod_database_code               2229637
_cod_database_fobs_code          2229637
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.85918(3) 0.28855(2) 0.398380(19) 0.04982(11) Uani d . 1 . .
O O1 0.7959(3) 0.3031(2) 0.0951(2) 0.0420(4) Uani d . 1 . .
O O2 0.7759(5) 0.4881(3) 0.0176(3) 0.0674(7) Uani d . 1 . .
O O3 0.6758(4) -0.2218(2) -0.2155(2) 0.0476(5) Uani d . 1 . .
O O4 0.7788(4) -0.0678(3) 0.3021(2) 0.0473(5) Uani d . 1 . .
C C2 0.7757(5) 0.3557(4) -0.0158(4) 0.0463(7) Uani d . 1 . .
C C3 0.7564(5) 0.2457(4) -0.1588(3) 0.0448(6) Uani d . 1 . .
H H3 0.7581 0.2808 -0.2350 0.054 Uiso calc R 1 . .
C C4 0.7360(4) 0.0940(3) -0.1890(3) 0.0378(5) Uani d . 1 . .
C C5 0.7146(4) -0.1155(3) -0.0803(3) 0.0345(5) Uani d . 1 . .
C C6 0.7277(4) -0.1539(3) 0.0418(3) 0.0357(5) Uani d . 1 . .
H H6 0.7109 -0.2565 0.0317 0.043 Uiso calc R 1 . .
C C7 0.7659(4) -0.0396(3) 0.1791(3) 0.0359(5) Uani d . 1 . .
C C8 0.7918(4) 0.1150(3) 0.1944(3) 0.0356(5) Uani d . 1 . .
C C9 0.7759(4) 0.1501(3) 0.0716(3) 0.0335(5) Uani d . 1 . .
C C10 0.7408(4) 0.0401(3) -0.0695(3) 0.0328(5) Uani d . 1 . .
C C11 0.7118(5) -0.0087(4) -0.3441(3) 0.0468(7) Uani d . 1 . .
H H11A 0.7269 0.0532 -0.4030 0.070 Uiso calc R 1 . .
H H11B 0.5830 -0.0819 -0.3742 0.070 Uiso calc R 1 . .
H H11C 0.8100 -0.0630 -0.3545 0.070 Uiso calc R 1 . .
C C12 0.6410(6) -0.3812(4) -0.2349(4) 0.0552(8) Uani d . 1 . .
H H12A 0.7577 -0.3960 -0.1932 0.083 Uiso calc R 1 . .
H H12B 0.6080 -0.4433 -0.3362 0.083 Uiso calc R 1 . .
H H12C 0.5340 -0.4114 -0.1882 0.083 Uiso calc R 1 . .
C C13 0.7526(6) -0.2253(4) 0.2918(4) 0.0543(8) Uani d . 1 . .
H H13A 0.6194 -0.2857 0.2470 0.081 Uiso calc R 1 . .
H H13B 0.7790 -0.2272 0.3869 0.081 Uiso calc R 1 . .
H H13C 0.8418 -0.2677 0.2348 0.081 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 C9 . . 122.5(2) ?
C5 O3 C12 . . 118.9(2) ?
C7 O4 C13 . . 118.3(2) ?
O2 C2 O1 . . 116.5(3) ?
O2 C2 C3 . . 127.3(3) ?
O1 C2 C3 . . 116.3(2) ?
C4 C3 C2 . . 123.6(3) ?
C4 C3 H3 . . 118.2 ?
C2 C3 H3 . . 118.2 ?
C3 C4 C10 . . 118.2(3) ?
C3 C4 C11 . . 117.9(3) ?
C10 C4 C11 . . 123.9(3) ?
O3 C5 C6 . . 122.7(2) ?
O3 C5 C10 . . 115.8(2) ?
C6 C5 C10 . . 121.5(2) ?
C5 C6 C7 . . 120.3(2) ?
C5 C6 H6 . . 119.8 ?
C7 C6 H6 . . 119.8 ?
O4 C7 C6 . . 123.8(2) ?
O4 C7 C8 . . 116.3(2) ?
C6 C7 C8 . . 119.9(2) ?
C9 C8 C7 . . 118.7(2) ?
C9 C8 I1 . . 120.70(19) ?
C7 C8 I1 . . 120.6(2) ?
O1 C9 C8 . . 115.4(2) ?
O1 C9 C10 . . 120.7(2) ?
C8 C9 C10 . . 123.9(2) ?
C9 C10 C5 . . 115.6(2) ?
C9 C10 C4 . . 118.2(2) ?
C5 C10 C4 . . 126.3(2) ?
C4 C11 H11A . . 109.5 ?
C4 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C4 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
O3 C12 H12A . . 109.5 ?
O3 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
O3 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
O4 C13 H13A . . 109.5 ?
O4 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
O4 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 C8 . 2.078(3) ?
O1 C2 . 1.374(4) ?
O1 C9 . 1.374(3) ?
O2 C2 . 1.198(4) ?
O3 C5 . 1.346(3) ?
O3 C12 . 1.429(4) ?
O4 C7 . 1.345(3) ?
O4 C13 . 1.441(4) ?
C2 C3 . 1.433(5) ?
C3 C4 . 1.350(4) ?
C3 H3 . 0.9300 ?
C4 C10 . 1.452(4) ?
C4 C11 . 1.498(4) ?
C5 C6 . 1.389(4) ?
C5 C10 . 1.423(4) ?
C6 C7 . 1.392(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.401(4) ?
C8 C9 . 1.380(4) ?
C9 C10 . 1.405(4) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C6 H6 O2 1_545 0.93 2.56 3.460(4) 163 yes
C13 H13C O2 1_545 0.96 2.51 3.211(5) 130 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 O1 C2 O2 . . . . 172.5(3) ?
C9 O1 C2 C3 . . . . -7.4(4) ?
O2 C2 C3 C4 . . . . -172.5(4) ?
O1 C2 C3 C4 . . . . 7.4(5) ?
C2 C3 C4 C10 . . . . -2.2(4) ?
C2 C3 C4 C11 . . . . 178.4(3) ?
C12 O3 C5 C6 . . . . 1.8(4) ?
C12 O3 C5 C10 . . . . -177.9(3) ?
O3 C5 C6 C7 . . . . -179.2(3) ?
C10 C5 C6 C7 . . . . 0.4(4) ?
C13 O4 C7 C6 . . . . 0.3(4) ?
C13 O4 C7 C8 . . . . 179.8(3) ?
C5 C6 C7 O4 . . . . 179.3(3) ?
C5 C6 C7 C8 . . . . -0.2(4) ?
O4 C7 C8 C9 . . . . -178.6(2) ?
C6 C7 C8 C9 . . . . 0.9(4) ?
O4 C7 C8 I1 . . . . 2.8(3) ?
C6 C7 C8 I1 . . . . -177.7(2) ?
C2 O1 C9 C8 . . . . -177.2(3) ?
C2 O1 C9 C10 . . . . 2.5(4) ?
C7 C8 C9 O1 . . . . 177.7(2) ?
I1 C8 C9 O1 . . . . -3.7(3) ?
C7 C8 C9 C10 . . . . -1.9(4) ?
I1 C8 C9 C10 . . . . 176.7(2) ?
O1 C9 C10 C5 . . . . -177.5(2) ?
C8 C9 C10 C5 . . . . 2.1(4) ?
O1 C9 C10 C4 . . . . 3.0(4) ?
C8 C9 C10 C4 . . . . -177.3(2) ?
O3 C5 C10 C9 . . . . 178.3(2) ?
C6 C5 C10 C9 . . . . -1.3(4) ?
O3 C5 C10 C4 . . . . -2.2(4) ?
C6 C5 C10 C4 . . . . 178.1(3) ?
C3 C4 C10 C9 . . . . -3.1(4) ?
C11 C4 C10 C9 . . . . 176.3(3) ?
C3 C4 C10 C5 . . . . 177.5(3) ?
C11 C4 C10 C5 . . . . -3.1(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656575
