#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/56/2215620.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_2215620
loop_
_publ_author_name
'Betz, Richard'
'Klüfers, Peter'
'Mangstl, Martin M.'
_publ_section_title
;
 tert-Butylglycolic acid
;
_journal_coeditor_code           NG2330
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4144
_journal_page_last               o4144
_journal_paper_doi               10.1107/S1600536807046156
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C6 H12 O3'
_chemical_formula_moiety         'C6 H12 O3'
_chemical_formula_sum            'C6 H12 O3'
_chemical_formula_weight         132.16
_chemical_name_common            'tert-butylglycolic acid'
_chemical_name_systematic
;
tert-Butylglycolic acid
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_cell_angle_alpha                90.00
_cell_angle_beta                 111.537(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   21.236(2)
_cell_length_b                   13.4486(13)
_cell_length_c                   11.4351(13)
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.9999
_cell_measurement_theta_min      3.9121
_cell_volume                     3037.8(6)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2005)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2005)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2005)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Oxford Diffraction XCalibur'
_diffrn_measurement_method       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  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7814
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         4.45
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9878
_exptl_absorpt_correction_T_min  0.9721
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(de Meulenaer & Tompa, 1965)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.206
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3003
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0759P)²+0.3594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1420
_reflns_number_gt                2266
_reflns_number_total             3003
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2330.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2215620
_cod_database_fobs_code          2215620
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_refinement_flags
_atom_site_occupancy
O O12 0.19291(6) 0.25485(9) 0.62987(11) 0.0395(3) Uani d . 1
H H12 0.2237(12) 0.2390(17) 0.608(2) 0.073(7) Uiso d . 1
O O22 0.05822(6) 0.37302(10) 0.12597(12) 0.0476(3) Uani d . 1
H H22 0.0265(11) 0.4000(15) 0.074(2) 0.051(6) Uiso d . 1
O O111 0.17753(5) 0.27864(10) 0.38322(12) 0.0534(4) Uani d . 1
O O112 0.06607(5) 0.27901(10) 0.33272(12) 0.0508(4) Uani d . 1
H H112 0.0644(11) 0.3065(18) 0.267(2) 0.072(7) Uiso d . 1
O O211 0.07378(6) 0.56407(9) 0.05469(13) 0.0541(4) Uani d . 1
O O212 0.18526(5) 0.54759(10) 0.15797(12) 0.0487(4) Uani d . 1
H H212 0.1857(13) 0.612(2) 0.156(2) 0.090(8) Uiso d . 1
C C11 0.12818(7) 0.26207(11) 0.40870(15) 0.0358(4) Uani d . 1
C C12 0.13211(7) 0.21920(11) 0.53441(14) 0.0347(4) Uani d . 1
H H121 0.0932 0.2472 0.5531 0.035(4) Uiso calc R 1
C C13 0.12590(8) 0.10491(12) 0.53469(16) 0.0400(4) Uani d . 1
C C14 0.18576(10) 0.05486(14) 0.5147(2) 0.0636(6) Uani d . 1
H H141 0.2279 0.0739 0.5828 0.0897(19) Uiso calc R 1
H H142 0.1875 0.0761 0.4340 0.0897(19) Uiso calc R 1
H H143 0.1803 -0.0175 0.5146 0.0897(19) Uiso calc R 1
C C15 0.06016(9) 0.07141(15) 0.4313(2) 0.0570(5) Uani d . 1
H H151 0.0548 -0.0005 0.4374 0.0897(19) Uiso calc R 1
H H152 0.0618 0.0875 0.3489 0.0897(19) Uiso calc R 1
H H153 0.0218 0.1058 0.4413 0.0897(19) Uiso calc R 1
C C16 0.12455(12) 0.07342(17) 0.6625(2) 0.0714(7) Uani d . 1
H H161 0.0866 0.1060 0.6762 0.0897(19) Uiso calc R 1
H H162 0.1671 0.0930 0.7292 0.0897(19) Uiso calc R 1
H H163 0.1192 0.0011 0.6640 0.0897(19) Uiso calc R 1
C C21 0.12311(8) 0.51224(12) 0.10414(15) 0.0387(4) Uani d . 1
C C22 0.11975(7) 0.40017(12) 0.11120(15) 0.0380(4) Uani d . 1
H H221 0.1578 0.3786 0.1889 0.031(4) Uiso calc R 1
C C23 0.12843(9) 0.34628(13) -0.00079(17) 0.0464(4) Uani d . 1
C C24 0.07322(13) 0.3743(2) -0.1234(2) 0.0892(8) Uani d . 1
H H241 0.0290 0.3595 -0.1188 0.0897(19) Uiso calc R 1
H H242 0.0787 0.3360 -0.1920 0.0897(19) Uiso calc R 1
H H243 0.0761 0.4455 -0.1390 0.0897(19) Uiso calc R 1
C C25 0.19713(11) 0.37017(18) -0.0065(2) 0.0713(6) Uani d . 1
H H251 0.1996 0.4414 -0.0226 0.0897(19) Uiso calc R 1
H H252 0.2033 0.3319 -0.0744 0.0897(19) Uiso calc R 1
H H253 0.2328 0.3527 0.0737 0.0897(19) Uiso calc R 1
C C26 0.12598(15) 0.23381(17) 0.0209(3) 0.0888(8) Uani d . 1
H H261 0.1634 0.2152 0.0983 0.0897(19) Uiso calc R 1
H H262 0.1302 0.1978 -0.0504 0.0897(19) Uiso calc R 1
H H263 0.0828 0.2167 0.0286 0.0897(19) 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'
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
_geom_angle_publ_flag
C12 O12 H12 106.5(17) ?
C22 O22 H22 110.7(14) ?
C11 O112 H112 112.3(16) ?
C21 O212 H212 111.4(17) ?
O111 C11 O112 124.16(14) ?
O111 C11 C12 123.12(14) ?
O112 C11 C12 112.72(13) ?
O12 C12 C11 108.32(12) ?
O12 C12 C13 112.68(12) ?
C11 C12 C13 113.84(13) ?
O12 C12 H121 107.2 n
C11 C12 H121 107.2 n
C13 C12 H121 107.2 n
C14 C13 C15 109.16(16) ?
C14 C13 C16 109.19(17) ?
C15 C13 C16 108.95(15) ?
C14 C13 C12 111.24(13) ?
C15 C13 C12 110.27(14) ?
C16 C13 C12 107.99(15) ?
C13 C14 H141 109.5 n
C13 C14 H142 109.5 n
H141 C14 H142 109.5 n
C13 C14 H143 109.5 n
H141 C14 H143 109.5 n
H142 C14 H143 109.5 n
C13 C15 H151 109.5 n
C13 C15 H152 109.5 n
H151 C15 H152 109.5 n
C13 C15 H153 109.5 n
H151 C15 H153 109.5 n
H152 C15 H153 109.5 n
C13 C16 H161 109.5 n
C13 C16 H162 109.5 n
H161 C16 H162 109.5 n
C13 C16 H163 109.5 n
H161 C16 H163 109.5 n
H162 C16 H163 109.5 n
O211 C21 O212 123.66(16) ?
O211 C21 C22 123.27(14) ?
O212 C21 C22 113.06(13) ?
O22 C22 C21 108.95(12) ?
O22 C22 C23 111.89(14) ?
C21 C22 C23 113.71(13) ?
O22 C22 H221 107.3 n
C21 C22 H221 107.3 n
C23 C22 H221 107.3 n
C24 C23 C25 109.8(2) ?
C24 C23 C26 109.5(2) ?
C25 C23 C26 107.77(18) ?
C24 C23 C22 111.46(15) ?
C25 C23 C22 110.27(15) ?
C26 C23 C22 107.92(17) ?
C23 C24 H241 109.5 n
C23 C24 H242 109.5 n
H241 C24 H242 109.5 n
C23 C24 H243 109.5 n
H241 C24 H243 109.5 n
H242 C24 H243 109.5 n
C23 C25 H251 109.5 n
C23 C25 H252 109.5 n
H251 C25 H252 109.5 n
C23 C25 H253 109.5 n
H251 C25 H253 109.5 n
H252 C25 H253 109.5 n
C23 C26 H261 109.5 n
C23 C26 H262 109.5 n
H261 C26 H262 109.5 n
C23 C26 H263 109.5 n
H261 C26 H263 109.5 n
H262 C26 H263 109.5 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O12 C12 1.4331(18) ?
O12 H12 0.81(2) ?
O22 C22 1.4253(18) ?
O22 H22 0.80(2) ?
O111 C11 1.2071(18) ?
O112 C11 1.3058(18) ?
O112 H112 0.82(2) ?
O211 C21 1.2116(19) ?
O212 C21 1.3230(19) ?
O212 H212 0.87(3) ?
C11 C12 1.522(2) ?
C12 C13 1.543(2) ?
C12 H121 1.0000 n
C13 C14 1.528(2) ?
C13 C15 1.529(2) ?
C13 C16 1.532(3) ?
C14 H141 0.9800 n
C14 H142 0.9800 n
C14 H143 0.9800 n
C15 H151 0.9800 n
C15 H152 0.9800 n
C15 H153 0.9800 n
C16 H161 0.9800 n
C16 H162 0.9800 n
C16 H163 0.9800 n
C21 C22 1.512(2) ?
C22 C23 1.540(2) ?
C22 H221 1.0000 n
C23 C24 1.508(3) ?
C23 C25 1.519(3) ?
C23 C26 1.537(3) ?
C24 H241 0.9800 n
C24 H242 0.9800 n
C24 H243 0.9800 n
C25 H251 0.9800 n
C25 H252 0.9800 n
C25 H253 0.9800 n
C26 H261 0.9800 n
C26 H262 0.9800 n
C26 H263 0.9800 n
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
O12 H12 O111 7_556 0.81(2) 2.08(2) 2.8456(17) 159(2)
O22 H22 O211 5_565 0.80(2) 2.15(2) 2.9308(18) 163.4(19)
O112 H112 O22 . 0.82(2) 1.81(3) 2.6317(18) 177(2)
O212 H212 O12 6_565 0.87(3) 1.82(3) 2.6883(18) 170(2)
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
O111 C11 C12 O12 32.7(2)
O112 C11 C12 O12 -147.03(13)
O111 C11 C12 C13 -93.44(19)
O112 C11 C12 C13 86.80(16)
O12 C12 C13 C14 -58.85(19)
C11 C12 C13 C14 64.99(18)
O12 C12 C13 C15 179.89(14)
C11 C12 C13 C15 -56.26(18)
O12 C12 C13 C16 60.95(18)
C11 C12 C13 C16 -175.21(15)
O211 C21 C22 O22 -34.9(2)
O212 C21 C22 O22 144.80(14)
O211 C21 C22 C23 90.67(19)
O212 C21 C22 C23 -89.66(17)
O22 C22 C23 C24 62.7(2)
C21 C22 C23 C24 -61.3(2)
O22 C22 C23 C25 -175.10(15)
C21 C22 C23 C25 60.93(19)
O22 C22 C23 C26 -57.62(19)
C21 C22 C23 C26 178.40(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 96480
2 PubChem 121490101
