#------------------------------------------------------------------------------
#$Date: 2022-05-07 06:13:32 +0300 (Sat, 07 May 2022) $
#$Revision: 275196 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/26/2022602.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_2022602
loop_
_publ_author_name
'Gordon, Matthew N.'
'Liu, Yanyao'
'Shafei, Ibrahim H.'
'Brown, M. Kevin'
'Skrabalak, Sara E.'
_publ_section_title
;
 Crystal structures of three β-halolactic acids: hydrogen bonding
 resulting in differing Z'
;
_journal_coeditor_code           VP3024
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              257
_journal_page_last               264
_journal_paper_doi               10.1107/S2053229622002856
_journal_volume                  78
_journal_year                    2022
_chemical_formula_moiety         'C3 H5 I O3'
_chemical_formula_sum            'C3 H5 I O3'
_chemical_formula_weight         215.97
_chemical_name_common            '3-Iodolactic acid'
_chemical_name_systematic
;
2-Hydroxy-3-iodopropanoic acid
;
_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
_audit_creation_method
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.848(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4762(8)
_cell_length_b                   5.4370(4)
_cell_length_c                   9.1941(7)
_cell_measurement_reflns_used    6362
_cell_measurement_temperature    153.00
_cell_measurement_theta_max      27.035
_cell_measurement_theta_min      3.555
_cell_volume                     572.97(7)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009),
Mercury (Macrae et al., 2020) and
CrystalExplorer (Spackman et al., 2021)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      153.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16586
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         3.555
_exptl_absorpt_coefficient_mu    5.491
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS2016; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.504
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.665
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     69
_refine_ls_number_reflns         1308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0246
_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)+(0.0197P)²+1.2602P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0540
_refine_ls_wR_factor_ref         0.0573
_reflns_number_gt                1102
_reflns_number_total             1308
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vp3024sup1.cif
_cod_data_source_block           21166
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2022602
_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   0.319
_shelx_estimated_absorpt_t_max   0.734
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 0.10060(2) 0.11577(5) 0.18694(3) 0.03582(11) Uani d 1 . .
O O1 0.3689(2) -0.0419(5) 0.2883(3) 0.0280(6) Uani d 1 . .
H H1 0.435419 -0.096878 0.312553 0.042 Uiso calc 1 . .
O O2 0.3384(3) 0.0992(5) -0.0900(3) 0.0337(7) Uani d 1 . .
H H2 0.349(5) 0.211(12) -0.130(7) 0.07(2) Uiso d 1 . .
O O3 0.4187(2) 0.3096(5) 0.0974(3) 0.0314(6) Uani d 1 . .
C C1 0.2156(3) -0.1709(7) 0.1191(4) 0.0303(8) Uani d 1 . .
H H1A 0.202299 -0.321458 0.176539 0.036 Uiso calc 1 . .
H H1B 0.197462 -0.209631 0.015196 0.036 Uiso calc 1 . .
C C2 0.3422(3) -0.0953(6) 0.1394(4) 0.0246(7) Uani d 1 . .
H H2A 0.392167 -0.235737 0.109911 0.030 Uiso calc 1 . .
C C3 0.3704(3) 0.1277(6) 0.0481(4) 0.0213(7) Uani 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 H1 . . 109.5 ?
C3 O2 H2 . . 110(5) ?
I1 C1 H1A . . 109.3 ?
I1 C1 H1B . . 109.3 ?
H1A C1 H1B . . 108.0 ?
C2 C1 I1 . . 111.5(2) ?
C2 C1 H1A . . 109.3 ?
C2 C1 H1B . . 109.3 ?
O1 C2 C1 . . 109.5(3) ?
O1 C2 H2A . . 108.6 ?
O1 C2 C3 . . 109.2(3) ?
C1 C2 H2A . . 108.6 ?
C1 C2 C3 . . 112.2(3) ?
C3 C2 H2A . . 108.6 ?
O2 C3 C2 . . 112.6(3) ?
O3 C3 O2 . . 124.0(3) ?
O3 C3 C2 . . 123.4(3) ?
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 C1 . 2.154(4) ?
O1 H1 . 0.8400 ?
O1 C2 . 1.418(4) ?
O2 H2 . 0.72(6) ?
O2 C3 . 1.313(4) ?
O3 C3 . 1.211(4) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C1 C2 . 1.513(5) ?
C2 H2A . 1.0000 ?
C2 C3 . 1.519(5) ?
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
O2 H2 O1 4_565 0.72(6) 1.97(6) 2.684(4) 172(7) yes
O2 H2 O3 4_565 0.72(6) 2.68(6) 3.101(4) 120(6) 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 C1 C2 O1 . . . . 59.5(3) ?
I1 C1 C2 C3 . . . . -61.9(3) ?
O1 C2 C3 O2 . . . . -174.4(3) ?
O1 C2 C3 O3 . . . . 6.6(5) ?
C1 C2 C3 O2 . . . . -52.8(4) ?
C1 C2 C3 O3 . . . . 128.3(4) ?

_cod_database_fobs_code 2022602
