#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/07/7150773.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_7150773
loop_
_publ_author_name
'Stoffman, Elia J. L.'
'Clive, Derrick L. J.'
_publ_section_title
;
 The coumarin→ indole transformation---a method for
 preparing 4-halo-5-hydroxyindoles from coumarins
;
_journal_issue                   23
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              4862
_journal_page_last               4870
_journal_paper_doi               10.1039/b914580j
_journal_volume                  7
_journal_year                    2009
_chemical_formula_moiety         'C14 H15 I O7 S'
_chemical_formula_sum            'C14 H15 I O7 S'
_chemical_formula_weight         454.22
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 93.3313(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4694(5)
_cell_length_b                   8.8437(4)
_cell_length_c                   17.8168(8)
_cell_measurement_reflns_used    9955
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      2.29
_cell_volume                     1646.84(13)
_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    'DIRDIF-99 (Beurskens et al., 1999)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '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  0.0172
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14030
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    2.103
_exptl_absorpt_correction_T_max  0.5975
_exptl_absorpt_correction_T_min  0.3131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.27
_refine_diff_density_max         1.206
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.0054(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3877
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0208
_refine_ls_R_factor_gt           0.0195
_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)+(0.0232P)²+1.4840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0494
_refine_ls_wR_factor_ref         0.0504
_reflns_number_gt                3691
_reflns_number_total             3877
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b914580j.txt
_cod_data_source_block           6.1
_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 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7150773
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
_atom_site_disorder_assembly
_atom_site_disorder_group
I I 0.250422(11) 0.670008(13) 0.096155(7) 0.02624(6) Uani 1 1 d . . .
S S 0.57397(5) 0.54382(5) 0.23688(3) 0.02872(11) Uani 1 1 d . . .
O1 O 0.33351(13) 0.11822(16) -0.03407(8) 0.0282(3) Uani 1 1 d . . .
O2 O 0.17443(16) -0.0156(2) -0.08474(10) 0.0471(4) Uani 1 1 d . . .
O3 O 0.13650(15) -0.00108(16) 0.09416(9) 0.0381(3) Uani 1 1 d . . .
O4 O 0.06259(14) 0.22977(15) 0.12096(8) 0.0295(3) Uani 1 1 d . . .
O5 O 0.53043(12) 0.57652(14) 0.14995(7) 0.0237(3) Uani 1 1 d . . .
O6 O 0.63714(16) 0.68062(16) 0.25977(10) 0.0403(4) Uani 1 1 d . . .
O7 O 0.64287(16) 0.40463(17) 0.24190(9) 0.0404(4) Uani 1 1 d . . .
C1 C 0.20580(19) 0.0874(2) -0.04439(11) 0.0300(4) Uani 1 1 d . . .
C2 C 0.11744(17) 0.1890(2) -0.00280(11) 0.0246(4) Uani 1 1 d . . .
H2 H 0.0305 0.1836 -0.0290 0.030 Uiso 1 1 calc R . .
C3 C 0.16241(17) 0.3546(2) -0.00423(10) 0.0220(3) Uani 1 1 d . . .
H3 H 0.1078 0.4156 0.0287 0.026 Uiso 1 1 calc R . .
C4 C 0.29862(16) 0.3574(2) 0.02921(10) 0.0203(3) Uani 1 1 d . . .
C5 C 0.35213(16) 0.47173(19) 0.07572(9) 0.0199(3) Uani 1 1 d . . .
C6 C 0.47787(16) 0.45810(19) 0.10516(9) 0.0207(3) Uani 1 1 d . . .
C7 C 0.55331(17) 0.33634(19) 0.08732(11) 0.0234(4) Uani 1 1 d . . .
H7 H 0.6396 0.3305 0.1067 0.028 Uiso 1 1 calc R . .
C8 C 0.50244(17) 0.2232(2) 0.04108(10) 0.0239(3) Uani 1 1 d . . .
H8 H 0.5530 0.1388 0.0283 0.029 Uiso 1 1 calc R . .
C9 C 0.37685(17) 0.2354(2) 0.01382(10) 0.0219(3) Uani 1 1 d . . .
C10 C 0.10809(17) 0.1263(2) 0.07629(11) 0.0255(4) Uani 1 1 d . . .
C11 C 0.0415(2) 0.1814(2) 0.19776(12) 0.0349(5) Uani 1 1 d . . .
H11A H 0.1186 0.1303 0.2203 0.042 Uiso 1 1 calc R . .
H11B H -0.0315 0.1102 0.1980 0.042 Uiso 1 1 calc R . .
C12 C 0.0138(4) 0.3193(3) 0.24046(16) 0.0620(8) Uani 1 1 d . . .
H12A H -0.0019 0.2921 0.2924 0.074 Uiso 1 1 calc R . .
H12B H -0.0622 0.3692 0.2172 0.074 Uiso 1 1 calc R . .
H12C H 0.0870 0.3882 0.2401 0.074 Uiso 1 1 calc R . .
C13 C 0.15071(19) 0.4208(3) -0.08379(11) 0.0313(4) Uani 1 1 d . . .
H13A H 0.0611 0.4175 -0.1029 0.038 Uiso 1 1 calc R . .
H13B H 0.2030 0.3614 -0.1168 0.038 Uiso 1 1 calc R . .
H13C H 0.1805 0.5258 -0.0826 0.038 Uiso 1 1 calc R . .
C14 C 0.4286(2) 0.5259(3) 0.27941(12) 0.0386(5) Uani 1 1 d . . .
H14A H 0.4450 0.5059 0.3332 0.046 Uiso 1 1 calc R . .
H14B H 0.3796 0.4420 0.2562 0.046 Uiso 1 1 calc R . .
H14C H 0.3796 0.6198 0.2727 0.046 Uiso 1 1 calc R . .
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'
S S 0.1246 0.1234 '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
_geom_angle_publ_flag
O6 S O7 119.29(10) . . ?
O6 S O5 102.86(9) . . ?
O7 S O5 109.15(8) . . ?
O6 S C14 110.73(11) . . ?
O7 S C14 110.17(11) . . ?
O5 S C14 103.17(9) . . ?
C1 O1 C9 120.62(14) . . ?
C10 O4 C11 116.16(15) . . ?
C6 O5 S 119.29(11) . . ?
O2 C1 O1 117.77(18) . . ?
O2 C1 C2 126.34(18) . . ?
O1 C1 C2 115.89(16) . . ?
C1 C2 C10 108.10(16) . . ?
C1 C2 C3 111.13(15) . . ?
C10 C2 C3 113.45(15) . . ?
C4 C3 C13 112.37(15) . . ?
C4 C3 C2 106.95(14) . . ?
C13 C3 C2 111.77(15) . . ?
C9 C4 C5 117.11(16) . . ?
C9 C4 C3 117.47(15) . . ?
C5 C4 C3 125.40(15) . . ?
C6 C5 C4 119.73(15) . . ?
C6 C5 I 119.06(12) . . ?
C4 C5 I 121.08(12) . . ?
C7 C6 C5 121.36(16) . . ?
C7 C6 O5 119.95(15) . . ?
C5 C6 O5 118.56(15) . . ?
C8 C7 C6 119.66(16) . . ?
C9 C8 C7 118.65(16) . . ?
C8 C9 C4 123.45(16) . . ?
C8 C9 O1 115.15(15) . . ?
C4 C9 O1 121.34(16) . . ?
O3 C10 O4 125.58(19) . . ?
O3 C10 C2 123.90(18) . . ?
O4 C10 C2 110.51(15) . . ?
O4 C11 C12 106.61(18) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I C5 2.0943(16) . ?
S O6 1.4269(15) . ?
S O7 1.4270(15) . ?
S O5 1.6150(13) . ?
S C14 1.747(2) . ?
O1 C1 1.366(2) . ?
O1 C9 1.401(2) . ?
O2 C1 1.194(2) . ?
O3 C10 1.203(2) . ?
O4 C10 1.320(2) . ?
O4 C11 1.463(2) . ?
O5 C6 1.409(2) . ?
C1 C2 1.514(3) . ?
C2 C10 1.523(3) . ?
C2 C3 1.539(2) . ?
C3 C4 1.513(2) . ?
C3 C13 1.532(3) . ?
C4 C9 1.392(2) . ?
C4 C5 1.403(2) . ?
C5 C6 1.394(2) . ?
C6 C7 1.383(2) . ?
C7 C8 1.383(3) . ?
C8 C9 1.379(3) . ?
C11 C12 1.475(3) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 S O5 C6 172.21(13) . . . . ?
O7 S O5 C6 44.58(15) . . . . ?
C14 S O5 C6 -72.55(14) . . . . ?
C9 O1 C1 O2 -178.6(2) . . . . ?
C9 O1 C1 C2 1.4(3) . . . . ?
O2 C1 C2 C10 94.9(3) . . . . ?
O1 C1 C2 C10 -85.1(2) . . . . ?
O2 C1 C2 C3 -140.0(2) . . . . ?
O1 C1 C2 C3 40.0(2) . . . . ?
C1 C2 C3 C4 -56.59(19) . . . . ?
C10 C2 C3 C4 65.46(18) . . . . ?
C1 C2 C3 C13 66.8(2) . . . . ?
C10 C2 C3 C13 -171.15(15) . . . . ?
C13 C3 C4 C9 -86.8(2) . . . . ?
C2 C3 C4 C9 36.2(2) . . . . ?
C13 C3 C4 C5 94.4(2) . . . . ?
C2 C3 C4 C5 -142.55(17) . . . . ?
C9 C4 C5 C6 -1.1(2) . . . . ?
C3 C4 C5 C6 177.66(16) . . . . ?
C9 C4 C5 I 174.84(12) . . . . ?
C3 C4 C5 I -6.4(2) . . . . ?
C4 C5 C6 C7 2.4(3) . . . . ?
I C5 C6 C7 -173.60(13) . . . . ?
C4 C5 C6 O5 178.21(15) . . . . ?
I C5 C6 O5 2.2(2) . . . . ?
S O5 C6 C7 -66.90(19) . . . . ?
S O5 C6 C5 117.21(15) . . . . ?
C5 C6 C7 C8 -1.9(3) . . . . ?
O5 C6 C7 C8 -177.64(16) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C7 C8 C9 C4 1.3(3) . . . . ?
C7 C8 C9 O1 178.49(16) . . . . ?
C5 C4 C9 C8 -0.7(3) . . . . ?
C3 C4 C9 C8 -179.57(17) . . . . ?
C5 C4 C9 O1 -177.81(16) . . . . ?
C3 C4 C9 O1 3.4(3) . . . . ?
C1 O1 C9 C8 157.67(18) . . . . ?
C1 O1 C9 C4 -25.0(3) . . . . ?
C11 O4 C10 O3 -2.3(3) . . . . ?
C11 O4 C10 C2 176.47(16) . . . . ?
C1 C2 C10 O3 -18.5(3) . . . . ?
C3 C2 C10 O3 -142.25(19) . . . . ?
C1 C2 C10 O4 162.71(15) . . . . ?
C3 C2 C10 O4 39.0(2) . . . . ?
C10 O4 C11 C12 170.0(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 44552438
