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#$Date: 2019-12-25 22:58:18 +0200 (Wed, 25 Dec 2019) $
#$Revision: 245978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/15/2311555.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_2311555
loop_
_publ_author_name
'Lee, Seul Gi'
'Ryu, Ji Yeon'
'Lee, Junseong'
_publ_section_title
;
 Crystal structure of methyl
 2-[5-(2-hy-droxy-phen-yl)-2H-tetra-zol-2-yl]acetate.
;
_journal_issue                   'Pt 12'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              1971
_journal_page_last               1973
_journal_paper_doi               10.1107/S205698901701698X
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C10 H10 N4 O3'
_chemical_formula_moiety         'C10 H10 N4 O3'
_chemical_formula_sum            'C10 H10 N4 O3'
_chemical_formula_weight         234.22
_chemical_name_systematic
;
Methyl 2-[5-(2-hydroxyphenyl)-2H-tetrazol-2-yl]acetate
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 104.479(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.060(2)
_cell_length_b                   8.2538(17)
_cell_length_c                   13.536(3)
_cell_measurement_reflns_used    3134
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.32
_cell_measurement_theta_min      2.91
_cell_volume                     1088.2(4)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_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  0.0438
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14003
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.163
_diffrn_reflns_theta_min         2.091
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       needle
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.171
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2372
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1242
_refine_ls_R_factor_gt           0.0565
_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)+(0.0479P)²+0.3171P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1367
_reflns_number_gt                1252
_reflns_number_total             2372
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su5409sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2311555
_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.
;
_shelxl_version_number           2.014
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
O O1 0.3781(3) 0.2337(4) 0.3644(3) 0.0745(14) Uani d 0.531(5) A 1
H H1 0.4534 0.2755 0.3623 0.112 Uiso calc 0.531(5) A 1
O O2 0.92819(16) 0.46762(19) 0.26859(14) 0.0718(5) Uani d 1 . .
O O3 0.92563(18) 0.2756(2) 0.38419(16) 0.0879(6) Uani d 1 . .
O O1A 0.5939(5) 0.1877(6) 0.7094(3) 0.1031(19) Uani d 0.469(5) A 2
H H1A 0.6557 0.2377 0.6900 0.155 Uiso calc 0.469(5) A 2
N N1 0.61929(19) 0.3786(2) 0.43476(16) 0.0618(5) Uani d 1 . .
N N2 0.7415(2) 0.4500(2) 0.46016(19) 0.0679(6) Uani d 1 . .
N N3 0.8043(2) 0.4384(3) 0.5571(2) 0.0890(7) Uani d 1 . .
N N4 0.7203(2) 0.3567(3) 0.59958(17) 0.0826(7) Uani d 1 . .
C C1 0.6085(2) 0.3209(3) 0.5240(2) 0.0574(6) Uani d 1 . .
C C2 0.4922(2) 0.2276(2) 0.53816(19) 0.0555(6) Uani d 1 . .
C C3 0.4899(3) 0.1677(3) 0.6336(3) 0.0749(7) Uani d 1 . .
H H3 0.5638 0.1911 0.6908 0.090 Uiso calc 0.531(5) A 1
C C4 0.3811(4) 0.0744(3) 0.6462(3) 0.0916(10) Uani d 1 . .
H H4 0.3810 0.0334 0.7117 0.110 Uiso calc 1 . .
C C5 0.2743(3) 0.0412(3) 0.5647(3) 0.0913(10) Uani d 1 . .
H H5 0.2001 -0.0237 0.5734 0.110 Uiso calc 1 . .
C C6 0.2733(3) 0.1010(3) 0.4701(3) 0.0831(8) Uani d 1 . .
H H6 0.1978 0.0790 0.4137 0.100 Uiso calc 1 . .
C C7 0.3818(3) 0.1929(3) 0.4565(2) 0.0652(7) Uani d 1 . .
H H7 0.3808 0.2330 0.3905 0.078 Uiso calc 0.469(5) A 2
C C8 0.8045(3) 0.5246(3) 0.3866(2) 0.0778(8) Uani d 1 . .
H H8A 0.8619 0.6170 0.4189 0.093 Uiso calc 1 . .
H H8B 0.7322 0.5670 0.3288 0.093 Uiso calc 1 . .
C C9 0.8923(2) 0.4048(3) 0.3474(2) 0.0635(7) Uani d 1 . .
C C10 1.0223(3) 0.3749(3) 0.2257(2) 0.0834(8) Uani d 1 . .
H H10A 1.0402 0.4334 0.1674 0.125 Uiso calc 1 . .
H H10B 0.9817 0.2691 0.2031 0.125 Uiso calc 1 . .
H H10C 1.1087 0.3594 0.2776 0.125 Uiso calc 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 117.19(18)
C1 N1 N2 101.8(2)
N3 N2 N1 114.2(2)
N3 N2 C8 122.4(2)
N1 N2 C8 123.2(2)
N2 N3 N4 105.9(2)
N3 N4 C1 106.5(2)
N1 C1 N4 111.6(2)
N1 C1 C2 124.2(2)
N4 C1 C2 124.2(2)
C7 C2 C3 118.1(2)
C7 C2 C1 121.0(2)
C3 C2 C1 120.8(2)
O1A C3 C4 119.1(4)
O1A C3 C2 119.9(3)
C4 C3 C2 120.7(3)
C5 C4 C3 120.0(3)
C4 C5 C6 120.3(3)
C5 C6 C7 120.1(3)
O1 C7 C6 116.2(3)
O1 C7 C2 122.9(3)
C6 C7 C2 120.7(3)
N2 C8 C9 111.09(19)
O3 C9 O2 126.0(2)
O3 C9 C8 124.7(2)
O2 C9 C8 109.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.282(4)
O2 C9 1.315(3)
O2 C10 1.447(3)
O3 C9 1.190(3)
O1A C3 1.280(5)
N1 C1 1.328(3)
N1 N2 1.329(3)
N2 N3 1.310(3)
N2 C8 1.445(3)
N3 N4 1.319(3)
N4 C1 1.351(3)
C1 C2 1.452(3)
C2 C7 1.387(3)
C2 C3 1.388(3)
C3 C4 1.383(4)
C4 C5 1.362(4)
C5 C6 1.370(4)
C6 C7 1.378(3)
C8 C9 1.508(3)
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
O1 H1 N1 . 0.84 1.91 2.659(4) 148
C5 H5 O3 3_656 0.95 2.57 3.472(3) 158
