#------------------------------------------------------------------------------
#$Date: 2017-05-18 06:26:16 +0200 (Thu 18 de May de 2017) $
#$Revision: 196748 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/56/7155638.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_7155638
loop_
_publ_author_name
'Mancuso, Raffaella'
'Pomelli, Christian Silvio'
'Malafronte, Francesco'
'Maner, Asif'
'Marino, Nadia'
'Chiappe, Cinzia'
'Gabriele, Bartolo'
_publ_section_title
;
 Divergent syntheses of iodinated isobenzofuranones and isochromenones by
 iodolactonization of 2-alkynylbenzoic acids in ionic liquids
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB00962C
_journal_year                    2017
_chemical_formula_moiety         'C13 H13 I O2'
_chemical_formula_sum            'C13 H13 I O2'
_chemical_formula_weight         328.13
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-02-28 deposited with the CCDC.
2017-05-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9685(19)
_cell_length_b                   7.1901(9)
_cell_length_c                   12.5256(16)
_cell_measurement_reflns_used    9811
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.49
_cell_measurement_theta_min      2.83
_cell_volume                     1258.0(3)
_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-2013 (Sheldrick 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_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  0.0242
_diffrn_reflns_av_unetI/netI     0.0102
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22340
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.345
_diffrn_reflns_theta_min         2.184
_exptl_absorpt_coefficient_mu    2.529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_transmission_factor_max   0.7464
_exptl_transmission_factor_min   0.5844
_refine_diff_density_max         0.938
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.144
_refine_ls_extinction_coef       0.070(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.339
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     95
_refine_ls_number_reflns         1204
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.339
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0317
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0585P)²+0.5116P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.1048
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1158
_reflns_number_total             1204
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ob00962c2.cif
_cod_data_source_block           2a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Direct' changed to 'direct'
according to
/home/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7155638
_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_min   0.632
_shelx_estimated_absorpt_t_max   0.884
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
I1 I 0.18718(2) 0.2500 -0.21877(2) 0.0641(3) Uani 1 2 d S T P
O1 O 0.19099(18) 0.2500 0.1245(3) 0.0480(7) Uani 1 2 d S T P
O2 O 0.1239(3) 0.2500 0.2876(2) 0.0678(11) Uani 1 2 d S T P
C1 C 0.1138(3) 0.2500 0.1924(4) 0.0489(10) Uani 1 2 d S T P
C2 C 0.0276(3) 0.2500 0.1248(3) 0.0434(9) Uani 1 2 d S T P
C3 C -0.0686(3) 0.2500 0.1576(4) 0.0581(11) Uani 1 2 d S T P
H3A H -0.0851 0.2500 0.2295 0.070 Uiso 1 2 calc R U P
C4 C -0.1374(3) 0.2500 0.0788(5) 0.0657(14) Uani 1 2 d S T P
H4A H -0.2019 0.2500 0.0974 0.079 Uiso 1 2 calc R U P
C5 C -0.1114(3) 0.2500 -0.0281(5) 0.0634(13) Uani 1 2 d S T P
H5A H -0.1592 0.2500 -0.0797 0.076 Uiso 1 2 calc R U P
C6 C -0.0164(3) 0.2500 -0.0607(4) 0.0528(10) Uani 1 2 d S T P
H6A H -0.0006 0.2500 -0.1328 0.063 Uiso 1 2 calc R U P
C7 C 0.0552(3) 0.2500 0.0178(3) 0.0398(8) Uani 1 2 d S T P
C8 C 0.1612(3) 0.2500 0.0164(3) 0.0388(8) Uani 1 2 d S T P
C9 C 0.2311(3) 0.2500 -0.0578(3) 0.0388(8) Uani 1 2 d S T P
C10 C 0.3397(3) 0.2500 -0.0332(4) 0.0464(9) Uani 1 2 d S T P
C11 C 0.4035(4) 0.2500 -0.1339(4) 0.0643(13) Uani 1 2 d S T P
H11A H 0.4699 0.2500 -0.1110 0.097 Uiso 1 2 d S U P
H11B H 0.3911 0.3590 -0.1743 0.097 Uiso 1 1 d . U .
C12 C 0.3646(2) 0.0726(5) 0.0307(3) 0.0622(9) Uani 1 1 d . . .
H12A H 0.4319 0.0715 0.0464 0.093 Uiso 1 1 calc R U .
H12B H 0.3486 -0.0352 -0.0109 0.093 Uiso 1 1 calc R U .
H12C H 0.3289 0.0712 0.0961 0.093 Uiso 1 1 calc R U .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 O1 C8 111.2(3) . .
O2 C1 O1 121.5(4) . .
O2 C1 C2 131.9(4) . .
O1 C1 C2 106.6(4) . .
C7 C2 C3 123.1(4) . .
C7 C2 C1 109.1(3) . .
C3 C2 C1 127.9(4) . .
C4 C3 C2 117.3(5) . .
C4 C3 H3A 121.4 . .
C2 C3 H3A 121.4 . .
C3 C4 C5 120.5(4) . .
C3 C4 H4A 119.7 . .
C5 C4 H4A 119.7 . .
C4 C5 C6 122.3(5) . .
C4 C5 H5A 118.8 . .
C6 C5 H5A 118.8 . .
C5 C6 C7 118.4(5) . .
C5 C6 H6A 120.8 . .
C7 C6 H6A 120.8 . .
C2 C7 C6 118.5(4) . .
C2 C7 C8 106.7(3) . .
C6 C7 C8 134.8(4) . .
C9 C8 O1 116.5(3) . .
C9 C8 C7 137.1(4) . .
O1 C8 C7 106.4(3) . .
C8 C9 C10 124.9(4) . .
C8 C9 I1 116.7(3) . .
C10 C9 I1 118.4(3) . .
C11 C10 C12 107.0(3) . .
C11 C10 C12 107.0(3) . 7_565
C12 C10 C12 111.3(4) . 7_565
C11 C10 C9 113.7(4) . .
C12 C10 C9 108.9(2) . .
C12 C10 C9 108.9(2) 7_565 .
C10 C11 H11A 108.0 . .
C10 C11 H11B 109.3 . .
H11A C11 H11B 109.4 . .
C10 C12 H12A 109.5 . .
C10 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C10 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C9 2.108(4) .
O1 C1 1.374(5) .
O1 C8 1.416(5) .
O2 C1 1.201(6) .
C1 C2 1.472(6) .
C2 C7 1.394(6) .
C2 C3 1.405(6) .
C3 C4 1.378(8) .
C3 H3A 0.9300 .
C4 C5 1.387(9) .
C4 H4A 0.9300 .
C5 C6 1.388(7) .
C5 H5A 0.9300 .
C6 C7 1.403(6) .
C6 H6A 0.9300 .
C7 C8 1.481(6) .
C8 C9 1.348(6) .
C9 C10 1.548(6) .
C10 C11 1.544(6) .
C10 C12 1.545(4) .
C10 C12 1.546(4) 7_565
C11 H11A 0.9714 .
C11 H11B 0.9492 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
