#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/35/2233534.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_2233534
loop_
_publ_author_name
'Al-Mohammed, Nassir N.'
'Alias, Yatimah'
'Abdullah, Zanariah'
'Khaledi, Hamid'
_publ_section_title
;
 tert-Butyl 2-(1H-imidazol-1-yl)acetate
;
_journal_coeditor_code           IS5051
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o445
_journal_paper_doi               10.1107/S1600536812001067
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C9 H14 N2 O2'
_chemical_formula_moiety         'C9 H14 N2 O2'
_chemical_formula_sum            'C9 H14 N2 O2'
_chemical_formula_weight         182.22
_chemical_name_systematic
;
tert-Butyl 2-(1H-imidazol-1-yl)acetate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 117.157(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.558(2)
_cell_length_b                   9.287(2)
_cell_length_c                   11.047(2)
_cell_measurement_reflns_used    771
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.96
_cell_measurement_theta_min      3.02
_cell_volume                     963.8(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_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_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6535
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9955
_exptl_absorpt_correction_T_min  0.9710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.272
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         2208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0401
_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)+(0.0352P)²+0.2973P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0965
_reflns_number_gt                1688
_reflns_number_total             2208
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            is5051.cif
_cod_data_source_block           I
_cod_original_cell_volume        963.9(4)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2233534
_cod_database_fobs_code          2233534
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_symmetry_multiplicity
O O1 0.58413(11) 0.82030(11) 0.21337(11) 0.0244(3) Uani d . 1 1
O O2 0.42983(10) 0.63596(10) 0.11631(10) 0.0177(2) Uani d . 1 1
N N1 1.01459(13) 0.74927(14) 0.30780(13) 0.0250(3) Uani d . 1 1
N N2 0.79333(12) 0.67798(12) 0.17766(12) 0.0164(3) Uani d . 1 1
C C1 0.91215(15) 0.66189(16) 0.29694(15) 0.0210(3) Uani d . 1 1
H H1 0.9207 0.5949 0.3653 0.025 Uiso calc R 1 1
C C2 0.95672(16) 0.82623(16) 0.18788(16) 0.0231(3) Uani d . 1 1
H H2 1.0055 0.8989 0.1650 0.028 Uiso calc R 1 1
C C3 0.82115(15) 0.78441(15) 0.10713(15) 0.0197(3) Uani d . 1 1
H H3 0.7584 0.8211 0.0198 0.024 Uiso calc R 1 1
C C4 0.65738(15) 0.60761(15) 0.13621(15) 0.0188(3) Uani d . 1 1
H H4A 0.6720 0.5166 0.1876 0.023 Uiso calc R 1 1
H H4B 0.6155 0.5835 0.0382 0.023 Uiso calc R 1 1
C C5 0.55466(15) 0.70313(15) 0.16122(14) 0.0169(3) Uani d . 1 1
C C6 0.30955(14) 0.69930(15) 0.13399(14) 0.0178(3) Uani d . 1 1
C C7 0.35240(16) 0.71586(17) 0.28396(15) 0.0228(3) Uani d . 1 1
H H7A 0.3916 0.6247 0.3308 0.034 Uiso calc R 1 1
H H7B 0.2688 0.7420 0.2957 0.034 Uiso calc R 1 1
H H7C 0.4245 0.7916 0.3225 0.034 Uiso calc R 1 1
C C8 0.26438(16) 0.84140(16) 0.05766(16) 0.0230(3) Uani d . 1 1
H H8A 0.3393 0.9133 0.1028 0.035 Uiso calc R 1 1
H H8B 0.1761 0.8747 0.0572 0.035 Uiso calc R 1 1
H H8C 0.2487 0.8278 -0.0362 0.035 Uiso calc R 1 1
C C9 0.19439(15) 0.58562(16) 0.06881(15) 0.0230(3) Uani d . 1 1
H H9A 0.1688 0.5775 -0.0281 0.034 Uiso calc R 1 1
H H9B 0.1102 0.6134 0.0790 0.034 Uiso calc R 1 1
H H9C 0.2299 0.4927 0.1135 0.034 Uiso calc R 1 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'
N N 0.0061 0.0033 '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
C5 O2 C6 121.56(10)
C1 N1 C2 104.32(12)
C1 N2 C3 106.85(12)
C1 N2 C4 127.15(12)
C3 N2 C4 125.75(12)
N1 C1 N2 112.36(13)
N1 C1 H1 123.8
N2 C1 H1 123.8
C3 C2 N1 110.88(13)
C3 C2 H2 124.6
N1 C2 H2 124.6
C2 C3 N2 105.60(13)
C2 C3 H3 127.2
N2 C3 H3 127.2
N2 C4 C5 111.43(11)
N2 C4 H4A 109.3
C5 C4 H4A 109.3
N2 C4 H4B 109.3
C5 C4 H4B 109.3
H4A C4 H4B 108.0
O1 C5 O2 126.65(13)
O1 C5 C4 124.35(13)
O2 C5 C4 108.99(11)
O2 C6 C7 109.68(11)
O2 C6 C9 102.05(11)
C7 C6 C9 111.34(12)
O2 C6 C8 109.88(11)
C7 C6 C8 112.35(12)
C9 C6 C8 111.06(12)
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C6 C8 H8A 109.5
C6 C8 H8B 109.5
H8A C8 H8B 109.5
C6 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C6 C9 H9A 109.5
C6 C9 H9B 109.5
H9A C9 H9B 109.5
C6 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.2039(17)
O2 C5 1.3325(16)
O2 C6 1.4910(16)
N1 C1 1.3131(19)
N1 C2 1.379(2)
N2 C1 1.3503(18)
N2 C3 1.3709(18)
N2 C4 1.4482(17)
C1 H1 0.9500
C2 C3 1.353(2)
C2 H2 0.9500
C3 H3 0.9500
C4 C5 1.5208(19)
C4 H4A 0.9900
C4 H4B 0.9900
C6 C7 1.513(2)
C6 C9 1.5207(19)
C6 C8 1.5209(19)
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
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
C4 H4B O2 3_665 0.99 2.56 3.3768(18) 139.8
loop_
_iucr_refine_instructions_details
;
TITL 1 in P2(1)/n
CELL 0.71073  10.5580   9.2875  11.0474  90.000 117.157  90.000
ZERR    4.00   0.0023   0.0020   0.0023   0.000   0.004   0.000
LATT 1
SYMM 0.5-X, 0.5+Y, 0.5-Z
SFAC C  H  N  O
UNIT 36  56  8  8
OMIT -2 55
L.S. 12
ACTA
BOND $H
HTAB C7 O1
HTAB C8 O1
HTAB C4 O2_$1
EQIV $1 -X+1, -Y+1, -Z
SIZE 0.05 0.27 0.33
TEMP -173
WGHT    0.035200    0.297300
FVAR       0.74767
O1    4    0.584131    0.820297    0.213373    11.00000    0.02310    0.02019 =
         0.03199   -0.00864    0.01435   -0.00446
O2    4    0.429829    0.635960    0.116315    11.00000    0.01411    0.01816 =
         0.02223   -0.00351    0.00956   -0.00151
N1    3    1.014589    0.749268    0.307800    11.00000    0.01847    0.03057 =
         0.02381   -0.00523    0.00768   -0.00118
N2    3    0.793335    0.677981    0.177662    11.00000    0.01426    0.01743 =
         0.01767   -0.00271    0.00753   -0.00160
C1    1    0.912151    0.661889    0.296939    11.00000    0.01946    0.02296 =
         0.01925    0.00057    0.00757    0.00364
AFIX  43
H1    2    0.920667    0.594932    0.365258    11.00000   -1.20000
AFIX   0
C2    1    0.956718    0.826228    0.187881    11.00000    0.01993    0.02335 =
         0.02903   -0.00264    0.01384   -0.00390
AFIX  43
H2    2    1.005485    0.898856    0.165027    11.00000   -1.20000
AFIX   0
C3    1    0.821152    0.784415    0.107132    11.00000    0.02129    0.02094 =
         0.01911    0.00099    0.01113    0.00008
AFIX  43
H3    2    0.758356    0.821123    0.019814    11.00000   -1.20000
AFIX   0
C4    1    0.657377    0.607611    0.136209    11.00000    0.01590    0.01772 =
         0.02414   -0.00371    0.01022   -0.00264
AFIX  23
H4A   2    0.672002    0.516634    0.187601    11.00000   -1.20000
H4B   2    0.615534    0.583483    0.038249    11.00000   -1.20000
AFIX   0
C5    1    0.554665    0.703130    0.161216    11.00000    0.01634    0.01877 =
         0.01482    0.00029    0.00643   -0.00153
C6    1    0.309553    0.699301    0.133991    11.00000    0.01466    0.01912 =
         0.02097   -0.00016    0.00941    0.00241
C7    1    0.352399    0.715863    0.283959    11.00000    0.02185    0.02677 =
         0.02165   -0.00147    0.01164    0.00200
AFIX 137
H7A   2    0.391649    0.624710    0.330792    11.00000   -1.50000
H7B   2    0.268761    0.741989    0.295731    11.00000   -1.50000
H7C   2    0.424540    0.791619    0.322495    11.00000   -1.50000
AFIX   0
C8    1    0.264384    0.841402    0.057656    11.00000    0.02165    0.02216 =
         0.02594    0.00277    0.01141    0.00282
AFIX 137
H8A   2    0.339325    0.913306    0.102759    11.00000   -1.50000
H8B   2    0.176067    0.874666    0.057172    11.00000   -1.50000
H8C   2    0.248657    0.827794   -0.036150    11.00000   -1.50000
AFIX   0
C9    1    0.194389    0.585616    0.068807    11.00000    0.01646    0.02407 =
         0.02877   -0.00114    0.01071   -0.00107
AFIX 137
H9A   2    0.168773    0.577454   -0.028086    11.00000   -1.50000
H9B   2    0.110234    0.613448    0.079010    11.00000   -1.50000
H9C   2    0.229944    0.492683    0.113489    11.00000   -1.50000
HKLF 4
REM  sad in P2(1)/n
REM R1 =  0.0401 for   1688 Fo > 4sig(Fo)  and  0.0590 for all   2208 data
REM    121 parameters refined using      0 restraints
END
WGHT      0.0348      0.3009
REM Highest difference peak  0.229,  deepest hole -0.272,  1-sigma level  0.046
Q1    1   0.6197  0.6501  0.1655  11.00000  0.05    0.22
Q2    1   0.8796  0.8557  0.1810  11.00000  0.05    0.21
Q3    1   0.2841  0.7685  0.0956  11.00000  0.05    0.19
Q4    1   0.2581  0.6432  0.0951  11.00000  0.05    0.17
;
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8279337
2 PubChem 10103810
