#------------------------------------------------------------------------------
#$Date: 2025-07-05 13:10:14 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/16/1571674.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_1571674
loop_
_publ_author_name
'Kimble, Marten J.'
'Myers, Shea D.'
'Benedict, Jason B.'
_publ_section_title
;
 Methyl 2-hydroxy-4-iodobenzoate
;
_journal_coeditor_code           HB4468
_journal_issue                   5
_journal_name_full               IUCrData
_journal_page_first              x240394
_journal_paper_doi               10.1107/S2414314624003948
_journal_volume                  9
_journal_year                    2024
_chemical_formula_iupac          'C8 H7 I O3'
_chemical_formula_moiety         'C8 H7 I O3'
_chemical_formula_sum            'C8 H7 I O3'
_chemical_formula_weight         278.04
_chemical_name_systematic
;
Methyl 2-hydroxy-4-iodobenzoate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.744(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.3286(8)
_cell_length_b                   21.334(4)
_cell_length_c                   9.2941(16)
_cell_measurement_reflns_used    6811
_cell_measurement_temperature    90.00
_cell_measurement_theta_max      34.14
_cell_measurement_theta_min      2.91
_cell_volume                     856.4(3)
_computing_cell_refinement
;
SAINT V8.40B (Bruker, 2016)
;
_computing_data_collection
;
APEX2 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT V8.40B (Bruker, 2016)
;
_computing_molecular_graphics
;
Olex2 1.5 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
Olex2 1.5 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018/2 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      90.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23320
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.100
_diffrn_reflns_theta_min         2.395
_exptl_absorpt_coefficient_mu    3.701
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_correction_T_min  0.5639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    2.156
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.269
_refine_diff_density_min         -1.916
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         3651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0299
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+1.6600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0559
_refine_ls_wR_factor_ref         0.0574
_reflns_number_gt                3315
_reflns_number_total             3651
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4468.cif
_cod_data_source_block           I
_cod_database_code               1571674
#BEGIN Tags that were not found in dictionaries:
_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   0.156
_shelx_estimated_absorpt_t_max   0.930
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.05964(3) 0.25795(2) 0.54095(2) 0.01430(4) Uani d 1 . .
O O3 0.7859(4) 0.39459(9) 0.91310(18) 0.0170(3) Uani d 1 . .
O O1 0.4603(4) 0.56516(8) 0.72915(18) 0.0180(3) Uani d 1 . .
O O2 0.7790(4) 0.51960(9) 0.89865(19) 0.0212(4) Uani d 1 . .
C C6 0.2313(5) 0.34266(10) 0.6295(2) 0.0127(4) Uani d 1 . .
C C7 0.4516(5) 0.34172(10) 0.7453(2) 0.0128(4) Uani d 1 . .
H H7 0.522507 0.302965 0.785568 0.015 Uiso calc 1 . .
C C8 0.5675(5) 0.39821(10) 0.8018(2) 0.0121(3) Uani d 1 . .
C C1 0.5827(6) 0.62513(11) 0.7783(3) 0.0203(5) Uani d 1 . .
H H1A 0.499780 0.658300 0.713823 0.030 Uiso calc 1 . .
H H1B 0.809060 0.624553 0.777897 0.030 Uiso calc 1 . .
H H1C 0.522278 0.633151 0.876394 0.030 Uiso calc 1 . .
C C5 0.1189(5) 0.39860(11) 0.5688(2) 0.0161(4) Uani d 1 . .
H H5 -0.033554 0.398522 0.490504 0.019 Uiso calc 1 . .
C C3 0.4577(5) 0.45534(10) 0.7425(2) 0.0123(4) Uani d 1 . .
C C2 0.5823(5) 0.51534(11) 0.7990(2) 0.0144(4) Uani d 1 . .
C C4 0.2359(5) 0.45406(10) 0.6259(2) 0.0156(4) Uani d 1 . .
H H4 0.163744 0.492573 0.584857 0.019 Uiso calc 1 . .
H H3 0.836(8) 0.4252(17) 0.929(4) 0.025(9) Uiso d 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
C8 O3 H3 . . 107(3) ?
C2 O1 C1 . . 115.15(18) ?
C7 C6 I1 . . 119.85(16) ?
C7 C6 C5 . . 121.9(2) ?
C5 C6 I1 . . 118.20(15) ?
C6 C7 H7 . . 120.3 ?
C6 C7 C8 . . 119.4(2) ?
C8 C7 H7 . . 120.3 ?
O3 C8 C7 . . 116.94(19) ?
O3 C8 C3 . . 123.3(2) ?
C7 C8 C3 . . 119.80(19) ?
O1 C1 H1A . . 109.5 ?
O1 C1 H1B . . 109.5 ?
O1 C1 H1C . . 109.5 ?
H1A C1 H1B . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C6 C5 H5 . . 121.0 ?
C4 C5 C6 . . 118.0(2) ?
C4 C5 H5 . . 121.0 ?
C8 C3 C2 . . 120.44(19) ?
C4 C3 C8 . . 118.89(19) ?
C4 C3 C2 . . 120.63(19) ?
O1 C2 C3 . . 113.23(18) ?
O2 C2 O1 . . 122.9(2) ?
O2 C2 C3 . . 123.8(2) ?
C5 C4 C3 . . 122.0(2) ?
C5 C4 H4 . . 119.0 ?
C3 C4 H4 . . 119.0 ?
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 C6 . 2.101(2) ?
O3 C8 . 1.357(3) ?
O3 H3 . 0.70(4) ?
O1 C1 . 1.447(3) ?
O1 C2 . 1.336(3) ?
O2 C2 . 1.220(3) ?
C6 C7 . 1.391(3) ?
C6 C5 . 1.394(3) ?
C7 H7 . 0.9500 ?
C7 C8 . 1.395(3) ?
C8 C3 . 1.407(3) ?
C1 H1A . 0.9800 ?
C1 H1B . 0.9800 ?
C1 H1C . 0.9800 ?
C5 H5 . 0.9500 ?
C5 C4 . 1.379(3) ?
C3 C2 . 1.472(3) ?
C3 C4 . 1.400(3) ?
C4 H4 . 0.9500 ?
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
O3 H3 O2 . 0.70(4) 2.05(4) 2.670(3) 149(4) yes
O3 H3 O2 3_767 0.70(4) 2.53(4) 3.087(2) 139(4) 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
I1 C6 C7 C8 . . . . 178.99(15) ?
I1 C6 C5 C4 . . . . -179.01(17) ?
O3 C8 C3 C2 . . . . 1.0(3) ?
O3 C8 C3 C4 . . . . 178.8(2) ?
C6 C7 C8 O3 . . . . -178.90(19) ?
C6 C7 C8 C3 . . . . 0.9(3) ?
C6 C5 C4 C3 . . . . -0.9(4) ?
C7 C6 C5 C4 . . . . 0.8(3) ?
C7 C8 C3 C2 . . . . -178.8(2) ?
C7 C8 C3 C4 . . . . -0.9(3) ?
C8 C3 C2 O1 . . . . 178.4(2) ?
C8 C3 C2 O2 . . . . -1.0(3) ?
C8 C3 C4 C5 . . . . 0.9(3) ?
C1 O1 C2 O2 . . . . 1.2(3) ?
C1 O1 C2 C3 . . . . -178.26(19) ?
C5 C6 C7 C8 . . . . -0.8(3) ?
C2 C3 C4 C5 . . . . 178.8(2) ?
C4 C3 C2 O1 . . . . 0.6(3) ?
C4 C3 C2 O2 . . . . -178.8(2) ?
