#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/38/2233816.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_2233816
loop_
_publ_author_name
'N. Al-Mohammed, Nassir'
'Alias, Yatimah'
'Abdullah, Zanariah'
'Khaledi, Hamid'
_publ_section_title
;
 tert-Butyl 2-(1H-benzimidazol-1-yl)acetate
;
_journal_coeditor_code           GK2453
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o571
_journal_paper_doi               10.1107/S1600536812002814
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C13 H16 N2 O2'
_chemical_formula_moiety         'C13 H16 N2 O2'
_chemical_formula_sum            'C13 H16 N2 O2'
_chemical_formula_weight         232.28
_chemical_name_systematic
;
tert-Butyl 2-(1H-benzimidazol-1-yl)acetate
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 96.609(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.4204(2)
_cell_length_b                   11.3319(4)
_cell_length_c                   19.8771(7)
_cell_measurement_reflns_used    1057
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      3.60
_cell_volume                     1212.81(8)
_computing_cell_refinement       'APEX2 (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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            3829
_diffrn_reflns_theta_full        26.46
_diffrn_reflns_theta_max         26.46
_diffrn_reflns_theta_min         3.60
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.195
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1244
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0343
_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)+(0.0394P)²+0.1800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0764
_reflns_number_gt                1091
_reflns_number_total             1244
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2453.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2233816
_cod_database_fobs_code          2233816
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'
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 0.0330(4) 0.41863(16) 0.04890(10) 0.0302(5) Uani d . 1 1
O O2 0.2082(3) 0.59850(13) 0.07085(9) 0.0174(4) Uani d . 1 1
N N1 0.3020(3) 0.38525(17) -0.05825(10) 0.0193(5) Uani d . 1 1
N N2 0.3571(4) 0.19170(18) -0.07541(12) 0.0243(5) Uani d . 1 1
C C1 0.4419(5) 0.2870(2) -0.04255(14) 0.0227(6) Uani d . 1 1
H H1 0.5871 0.2872 -0.0108 0.027 Uiso calc R 1 1
C C2 0.1057(4) 0.3507(2) -0.10483(12) 0.0183(5) Uani d . 1 1
C C3 -0.0961(4) 0.4127(2) -0.13641(13) 0.0222(6) Uani d . 1 1
H H3 -0.1195 0.4943 -0.1282 0.027 Uiso calc R 1 1
C C4 -0.2609(5) 0.3489(2) -0.18058(14) 0.0250(6) Uani d . 1 1
H H4 -0.4014 0.3879 -0.2035 0.030 Uiso calc R 1 1
C C5 -0.2268(5) 0.2281(2) -0.19258(13) 0.0228(6) Uani d . 1 1
H H5 -0.3446 0.1872 -0.2232 0.027 Uiso calc R 1 1
C C6 -0.0250(5) 0.1677(2) -0.16060(14) 0.0225(6) Uani d . 1 1
H H6 -0.0019 0.0862 -0.1690 0.027 Uiso calc R 1 1
C C7 0.1446(4) 0.2301(2) -0.11554(13) 0.0192(5) Uani d . 1 1
C C8 0.3234(4) 0.4973(2) -0.02268(13) 0.0183(5) Uani d . 1 1
H H8A 0.2671 0.5617 -0.0544 0.022 Uiso calc R 1 1
H H8B 0.4997 0.5119 -0.0056 0.022 Uiso calc R 1 1
C C9 0.1684(4) 0.4977(2) 0.03638(13) 0.0187(5) Uani d . 1 1
C C10 0.0928(4) 0.6199(2) 0.13424(13) 0.0200(5) Uani d . 1 1
C C11 0.1856(5) 0.5282(2) 0.18666(14) 0.0264(6) Uani d . 1 1
H H11A 0.1199 0.4505 0.1722 0.040 Uiso calc R 1 1
H H11B 0.1293 0.5487 0.2303 0.040 Uiso calc R 1 1
H H11C 0.3675 0.5260 0.1914 0.040 Uiso calc R 1 1
C C12 0.1849(5) 0.7429(2) 0.15475(15) 0.0256(6) Uani d . 1 1
H H12A 0.3668 0.7432 0.1612 0.038 Uiso calc R 1 1
H H12B 0.1214 0.7655 0.1971 0.038 Uiso calc R 1 1
H H12C 0.1257 0.7992 0.1191 0.038 Uiso calc R 1 1
C C13 -0.1878(5) 0.6198(2) 0.11925(15) 0.0271(6) Uani d . 1 1
H H13A -0.2380 0.6743 0.0819 0.041 Uiso calc R 1 1
H H13B -0.2616 0.6451 0.1596 0.041 Uiso calc R 1 1
H H13C -0.2454 0.5400 0.1065 0.041 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
C9 O2 C10 120.91(18)
C1 N1 C2 106.6(2)
C1 N1 C8 126.3(2)
C2 N1 C8 125.84(19)
C1 N2 C7 104.24(19)
N2 C1 N1 113.8(2)
N2 C1 H1 123.1
N1 C1 H1 123.1
N1 C2 C3 131.6(2)
N1 C2 C7 105.1(2)
C3 C2 C7 123.3(2)
C4 C3 C2 116.1(2)
C4 C3 H3 121.9
C2 C3 H3 121.9
C3 C4 C5 122.0(2)
C3 C4 H4 119.0
C5 C4 H4 119.0
C6 C5 C4 121.1(2)
C6 C5 H5 119.5
C4 C5 H5 119.5
C5 C6 C7 118.2(2)
C5 C6 H6 120.9
C7 C6 H6 120.9
N2 C7 C6 130.4(2)
N2 C7 C2 110.3(2)
C6 C7 C2 119.4(2)
N1 C8 C9 111.03(18)
N1 C8 H8A 109.4
C9 C8 H8A 109.4
N1 C8 H8B 109.4
C9 C8 H8B 109.4
H8A C8 H8B 108.0
O1 C9 O2 126.7(2)
O1 C9 C8 124.2(2)
O2 C9 C8 109.14(18)
O2 C10 C11 109.36(19)
O2 C10 C13 110.1(2)
C11 C10 C13 112.4(2)
O2 C10 C12 102.64(19)
C11 C10 C12 111.8(2)
C13 C10 C12 110.1(2)
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C10 C12 H12A 109.5
C10 C12 H12B 109.5
H12A C12 H12B 109.5
C10 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C10 C13 H13A 109.5
C10 C13 H13B 109.5
H13A C13 H13B 109.5
C10 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.203(3)
O2 C9 1.336(3)
O2 C10 1.490(3)
N1 C1 1.363(3)
N1 C2 1.384(3)
N1 C8 1.451(3)
N2 C1 1.317(3)
N2 C7 1.394(3)
C1 H1 0.9500
C2 C3 1.388(3)
C2 C7 1.402(3)
C3 C4 1.383(4)
C3 H3 0.9500
C4 C5 1.406(4)
C4 H4 0.9500
C5 C6 1.382(4)
C5 H5 0.9500
C6 C7 1.399(4)
C6 H6 0.9500
C8 C9 1.520(3)
C8 H8A 0.9900
C8 H8B 0.9900
C10 C11 1.516(4)
C10 C13 1.516(3)
C10 C12 1.520(4)
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 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
_geom_hbond_publ_flag
C11 H11A O1 . 0.98 2.47 3.033(3) 116.4 n
C13 H13C O1 . 0.98 2.42 2.995(3) 116.6 n
C3 H3 N2 3_455 0.95 2.48 3.406(3) 164.8 y
loop_
_iucr_refine_instructions_details
;
TITL 1 in Cc
CELL 0.71073   5.4204  11.3319  19.8771  90.000  96.609  90.000
ZERR    4.00   0.0002   0.0004   0.0007   0.000   0.003   0.000
LATT -7
SYMM X, -Y, 0.5+Z
SFAC C  H  N  O
UNIT 52  64  8  8
L.S. 24
ACTA
HTAB C11 O1
HTAB C13 O1
HTAB C3 N2_$1
EQIV $1 -1/2+x,1/2+y,z
OMIT 0 0 2
BOND $H
MERG 3
SIZE 0.04 0.13 0.19
TEMP -173
WGHT    0.039400    0.180000
FVAR       0.21684
O1    4    0.033036    0.418627    0.048905    11.00000    0.04021    0.02408 =
         0.02789   -0.00465    0.01090   -0.01246
O2    4    0.208237    0.598500    0.070853    11.00000    0.01964    0.01577 =
         0.01718   -0.00256    0.00349    0.00048
N1    3    0.302039    0.385245   -0.058246    11.00000    0.02210    0.01651 =
         0.01906   -0.00111    0.00133    0.00289
N2    3    0.357138    0.191700   -0.075409    11.00000    0.02876    0.01911 =
         0.02394   -0.00124   -0.00133    0.00408
C1    1    0.441890    0.286968   -0.042550    11.00000    0.02527    0.02250 =
         0.01964   -0.00025    0.00012    0.00589
AFIX  43
H1    2    0.587078    0.287180   -0.010837    11.00000   -1.20000
AFIX   0
C2    1    0.105686    0.350675   -0.104829    11.00000    0.02137    0.01850 =
         0.01529   -0.00177    0.00371    0.00025
C3    1   -0.096059    0.412732   -0.136406    11.00000    0.02491    0.01867 =
         0.02240   -0.00234    0.00006    0.00445
AFIX  43
H3    2   -0.119523    0.494312   -0.128153    11.00000   -1.20000
AFIX   0
C4    1   -0.260912    0.348896   -0.180576    11.00000    0.02735    0.02501 =
         0.02205   -0.00081    0.00082    0.00670
AFIX  43
H4    2   -0.401393    0.387863   -0.203495    11.00000   -1.20000
AFIX   0
C5    1   -0.226845    0.228059   -0.192581    11.00000    0.02661    0.02506 =
         0.01627   -0.00511   -0.00006    0.00011
AFIX  43
H5    2   -0.344593    0.187199   -0.223189    11.00000   -1.20000
AFIX   0
C6    1   -0.024952    0.167747   -0.160601    11.00000    0.03170    0.01643 =
         0.01965   -0.00239    0.00452    0.00104
AFIX  43
H6    2   -0.001888    0.086180   -0.168980    11.00000   -1.20000
AFIX   0
C7    1    0.144563    0.230123   -0.115538    11.00000    0.02420    0.01857 =
         0.01481   -0.00038    0.00224    0.00311
C8    1    0.323431    0.497279   -0.022680    11.00000    0.02048    0.01757 =
         0.01667   -0.00304    0.00194   -0.00132
AFIX  23
H8A   2    0.267109    0.561679   -0.054447    11.00000   -1.20000
H8B   2    0.499665    0.511880   -0.005645    11.00000   -1.20000
AFIX   0
C9    1    0.168402    0.497741    0.036376    11.00000    0.02096    0.01801 =
         0.01628    0.00068   -0.00111    0.00172
C10   1    0.092795    0.619861    0.134245    11.00000    0.01885    0.02641 =
         0.01521   -0.00325    0.00357   -0.00153
C11   1    0.185567    0.528153    0.186657    11.00000    0.02678    0.03408 =
         0.01799    0.00081    0.00163   -0.00066
AFIX 137
H11A  2    0.119909    0.450491    0.172180    11.00000   -1.50000
H11B  2    0.129289    0.548661    0.230296    11.00000   -1.50000
H11C  2    0.367483    0.526016    0.191380    11.00000   -1.50000
AFIX   0
C12   1    0.184856    0.742885    0.154749    11.00000    0.02551    0.02503 =
         0.02725   -0.00922    0.00711   -0.00105
AFIX 137
H12A  2    0.366839    0.743235    0.161241    11.00000   -1.50000
H12B  2    0.121392    0.765498    0.197131    11.00000   -1.50000
H12C  2    0.125672    0.799214    0.119091    11.00000   -1.50000
AFIX   0
C13   1   -0.187823    0.619810    0.119246    11.00000    0.01665    0.03937 =
         0.02552   -0.00288    0.00312   -0.00036
AFIX 137
H13A  2   -0.237970    0.674270    0.081863    11.00000   -1.50000
H13B  2   -0.261555    0.645105    0.159639    11.00000   -1.50000
H13C  2   -0.245351    0.540021    0.106539    11.00000   -1.50000
HKLF 4
REM  sad in Cc
REM R1 =  0.0343 for   1091 Fo > 4sig(Fo)  and  0.0426 for all   1244 data
REM    157 parameters refined using      2 restraints
END
WGHT      0.0392      0.1911
REM Highest difference peak  0.166,  deepest hole -0.195,  1-sigma level  0.040
Q1    1  -0.1327  0.7412  0.2212  11.00000  0.05    0.17
Q2    1   0.2066  0.4944 -0.0011  11.00000  0.05    0.14
Q3    1   0.1766  0.6250 -0.1226  11.00000  0.05    0.14
Q4    1  -0.1557  0.5377 -0.0580  11.00000  0.05    0.14
;
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657490
