#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/61/2236170.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_2236170
loop_
_publ_author_name
'Alieva, Guloy'
'Ashurov, Jamshid'
'Mukhamedov, Nasir'
'Parpiev, Nusrat'
_publ_section_title
;
 A new polymorph of 2-(2H-benzotriazol-2-yl)acetic acid
;
_journal_coeditor_code           DS2205
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2833
_journal_paper_doi               10.1107/S1600536812036768
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C8 H7 N3 O2'
_chemical_formula_moiety         'C8 H7 N3 O2'
_chemical_formula_sum            'C8 H7 N3 O2'
_chemical_formula_weight         177.17
_chemical_name_systematic
;
2-(2H-benzotriazol-2-yl)acetic 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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.703(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.719(9)
_cell_length_b                   8.308(3)
_cell_length_c                   17.246(5)
_cell_measurement_reflns_used    408
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      43.7309
_cell_measurement_theta_min      5.1460
_cell_volume                     1667.6(15)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.2576
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4907
_diffrn_reflns_theta_full        67.12
_diffrn_reflns_theta_max         67.12
_diffrn_reflns_theta_min         5.16
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.888
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.120
_refine_ls_extinction_coef       0.0012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0355
_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)+(0.0576P)²+0.4124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0997
_reflns_number_gt                1235
_reflns_number_total             1488
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ds2205.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2236170
_cod_database_fobs_code          2236170
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
_atom_site_symmetry_multiplicity
C C1 0.55191(14) 0.2934(2) -0.01273(10) 0.0573(4) Uani d . 1 1
H H1 0.5107 0.2146 0.0103 0.069 Uiso calc R 1 1
C C2 0.52406(16) 0.3401(2) -0.08830(10) 0.0713(6) Uani d . 1 1
H H2 0.4617 0.2915 -0.1175 0.086 Uiso calc R 1 1
C C3 0.58612(18) 0.4597(3) -0.12416(10) 0.0763(6) Uani d . 1 1
H H3 0.5632 0.4868 -0.1760 0.092 Uiso calc R 1 1
C C4 0.67792(18) 0.5361(2) -0.08543(9) 0.0682(5) Uani d . 1 1
H H4 0.7186 0.6142 -0.1094 0.082 Uiso calc R 1 1
C C5 0.70856(14) 0.49131(18) -0.00695(8) 0.0511(4) Uani d . 1 1
C C6 0.64717(12) 0.37216(17) 0.02830(8) 0.0454(4) Uani d . 1 1
C C7 0.85382(12) 0.48491(19) 0.18123(8) 0.0517(4) Uani d . 1 1
H H7A 0.9296 0.5179 0.1701 0.062 Uiso calc R 1 1
H H7B 0.8618 0.3840 0.2096 0.062 Uiso calc R 1 1
C C8 0.80584(12) 0.61084(19) 0.23154(8) 0.0480(4) Uani d . 1 1
N N1 0.79426(11) 0.54651(15) 0.04583(7) 0.0542(4) Uani d . 1 1
N N2 0.78104(10) 0.46083(14) 0.10872(7) 0.0468(3) Uani d . 1 1
N N3 0.69527(10) 0.35514(14) 0.10293(6) 0.0457(3) Uani d . 1 1
O O1 0.87531(9) 0.63393(16) 0.29596(6) 0.0666(4) Uani d . 1 1
H H1A 0.8481 0.7025 0.3227 0.100 Uiso calc R 1 1
O O2 0.71669(10) 0.67914(16) 0.21507(6) 0.0672(4) Uani d . 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0544(9) 0.0607(10) 0.0547(9) 0.0124(7) -0.0024(7) -0.0122(7)
C2 0.0694(11) 0.0844(13) 0.0551(10) 0.0264(10) -0.0136(8) -0.0231(9)
C3 0.1008(15) 0.0870(13) 0.0384(9) 0.0391(12) -0.0026(9) -0.0039(9)
C4 0.0975(13) 0.0652(10) 0.0433(9) 0.0255(10) 0.0145(9) 0.0059(8)
C5 0.0650(9) 0.0475(8) 0.0414(8) 0.0153(7) 0.0087(6) -0.0012(6)
C6 0.0507(8) 0.0468(8) 0.0383(7) 0.0133(6) 0.0031(6) -0.0038(6)
C7 0.0471(8) 0.0582(9) 0.0482(9) 0.0004(7) -0.0008(6) -0.0039(7)
C8 0.0475(8) 0.0574(9) 0.0386(7) -0.0016(7) 0.0026(6) 0.0013(6)
N1 0.0677(8) 0.0487(7) 0.0479(7) 0.0021(6) 0.0132(6) 0.0007(5)
N2 0.0512(7) 0.0488(7) 0.0403(6) 0.0007(5) 0.0046(5) -0.0023(5)
N3 0.0477(7) 0.0483(7) 0.0403(6) 0.0032(5) 0.0027(5) -0.0008(5)
O1 0.0524(6) 0.0924(9) 0.0518(7) 0.0143(6) -0.0069(5) -0.0215(6)
O2 0.0643(7) 0.0858(9) 0.0482(6) 0.0216(6) -0.0072(5) -0.0114(6)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2 C1 C6 115.77(18)
C2 C1 H1 122.1
C6 C1 H1 122.1
C1 C2 C3 122.69(18)
C1 C2 H2 118.7
C3 C2 H2 118.7
C4 C3 C2 122.14(17)
C4 C3 H3 118.9
C2 C3 H3 118.9
C3 C4 C5 116.61(18)
C3 C4 H4 121.7
C5 C4 H4 121.7
N1 C5 C6 108.97(13)
N1 C5 C4 129.93(17)
C6 C5 C4 121.10(16)
N3 C6 C5 107.98(13)
N3 C6 C1 130.32(14)
C5 C6 C1 121.70(14)
N2 C7 C8 111.85(12)
N2 C7 H7A 109.2
C8 C7 H7A 109.2
N2 C7 H7B 109.2
C8 C7 H7B 109.2
H7A C7 H7B 107.9
O2 C8 O1 124.82(14)
O2 C8 C7 124.56(13)
O1 C8 C7 110.62(13)
N2 N1 C5 102.73(13)
N1 N2 N3 117.02(11)
N1 N2 C7 121.50(13)
N3 N2 C7 121.45(12)
N2 N3 C6 103.30(11)
C8 O1 H1A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.362(3)
C1 C6 1.411(2)
C1 H1 0.9300
C2 C3 1.415(3)
C2 H2 0.9300
C3 C4 1.356(3)
C3 H3 0.9300
C4 C5 1.409(2)
C4 H4 0.9300
C5 N1 1.354(2)
C5 C6 1.403(2)
C6 N3 1.3510(17)
C7 N2 1.4431(18)
C7 C8 1.509(2)
C7 H7A 0.9700
C7 H7B 0.9700
C8 O2 1.1937(19)
C8 O1 1.3126(17)
N1 N2 1.3214(17)
N2 N3 1.3296(17)
O1 H1A 0.8200
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 H1A N3 4_655 0.82 1.91 2.7273(17) 170.9
C2 H2 O2 5_665 0.93 2.54 3.365(3) 148.00
C7 H7A O1 2_755 0.97 2.49 3.387(3) 154.00
C7 H7B O2 4_645 0.97 2.39 3.268(3) 150.00
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 560491
