#------------------------------------------------------------------------------
#$Date: 2022-10-03 16:40:12 +0200 (Mon 03 de Oct de 2022) $
#$Revision: 278324 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/97/2009729.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_2009729
loop_
_publ_author_name
'Lewanowicz, A.'
'Baert, F.'
_publ_section_title
;
 2-(2-Hydroxy-5-methylphenyl)-5-chlorobenzotriazole, C~13~H~10~ClN~3~O
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              801
_journal_page_last               803
_journal_paper_doi               10.1107/S0108270193010303
_journal_volume                  50
_journal_year                    1994
_chemical_formula_moiety         'C13 H10 Cl1 N3 O1'
_chemical_formula_sum            'C13 H10 Cl N3 O'
_chemical_formula_weight         259.68
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_type_scat_source
; IntTabIV (non-H); Stewart, Davidson & Simpson
(1965) (H)
;
_cell_angle_alpha                90.
_cell_angle_beta                 98.8(4)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   11.222(5)
_cell_length_b                   3.917(3)
_cell_length_c                   26.949(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      2
_cell_volume                     1170.6(17)
_diffrn_measurement_device       'Nonius CAD-4 Rotating Anode'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2248
_diffrn_reflns_theta_max         20
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  120
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.47
_exptl_crystal_description       needle
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   6.25
_refine_ls_hydrogen_treatment    'constrained refinement of H atoms'
_refine_ls_number_parameters     198
_refine_ls_number_reflns         1043
_refine_ls_R_factor_obs          0.059
_refine_ls_shift/esd_max         0.013
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      unit
_refine_ls_wR_factor_obs         0.059
_reflns_number_observed          1043
_reflns_observed_criterion       I>=3\s(I)
_cod_data_source_file            pa1056.cif
_cod_data_source_block           pa1056_structure_1_of_1
_cod_original_cell_volume        1171.0(10)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C13 H10 Cl1 N3 O1'
_cod_database_code               2009729
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x+1/2,-y+1/2,z+1/2
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
C1 C .7564(5) -.1021(17) .5846(2) .041(9)
C2 C .6580(6) -.2739(18) .5976(3) .049(10)
O1 O .5638(4) -.3933(15) .5650(2) .061(7)
C3 C .6574(6) -.340(2) .6481(3) .066(12)
C4 C .7523(7) -.243(2) .6831(3) .070(11)
C5 C .8513(6) -.0772(18) .6710(3) .055(10)
CMe C .9551(8) .030(2) .7107(3) .058(12)
C6 C .8516(6) -.0044(18) .6213(3) .051(10)
N1 N .7628(5) -.0137(14) .5334(2) .045(8)
N2 N .8554(4) .1503(15) .5203(2) .049(8)
N3 N .6743(4) -.1077(15) .4966(2) .039(8)
C7 C .7146(5) .0093(17) .4550(2) .044(9)
C8 C .6612(6) -.011(2) .4039(3) .049(11)
C9 C .7272(6) .131(2) .3711(2) .051(10)
C10 C .8380(7) .296(2) .3856(3) .061(11)
C11 C .8895(6) .318(2) .4340(3) .050(11)
C12 C .8261(5) .1704(18) .4698(2) .045(9)
Cl Cl .6714(2) .1078(7) .30700(10) .084(3)
H3 H .597 -.448 .659 .044
H4 H .751 -.286 .715 .044
H(Me) H 1.028 .088 .701 .104
H'(Me) H .945 .260 .717 .104
H"(Me) H .973 -.140 .735 .104
H6 H .916 .095 .612 .044
H8 H .588 -.101 .395 .044
H10 H .876 .360 .361 .044
H11 H .955 .448 .441 .044
H(01) H .569 -.316 .534 .044
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
C2 C1 C6 120.6(6) yes
C6 C1 N1 118.1(6) yes
C1 C2 C3 117.6(6) yes
C2 C3 C4 120.5(7) yes
C4 C5 CMe 121.8(7) yes
CMe C5 C6 121.1(6) yes
C1 N1 N2 122.2(5) yes
N2 N1 N3 117.5(5) yes
N1 N3 C7 102.5(5) yes
N3 C7 C12 108.3(6) yes
C7 C8 C9 114.8(6) yes
C8 C9 Cl 118.3(6) yes
C9 C10 C11 122.1(7) yes
N2 C12 C7 109.2(6) yes
C7 C12 C11 120.8(6) yes
C2 C1 N1 121.3(6) yes
C1 C2 O1 125.4(6) yes
O1 C2 C3 116.9(6) yes
C3 C4 C5 122.8(7) yes
C4 C5 C6 117.1(6) yes
C1 C6 C5 121.4(6) yes
C1 N1 N3 120.2(5) yes
N1 N2 C12 102.6(5) yes
N3 C7 C8 129.9(6) yes
C8 C7 C12 121.8(6) yes
C8 C9 C10 123.7(7) yes
C10 C9 Cl 118.0(6) yes
C10 C11 C12 116.8(7) yes
N2 C12 C11 130.0(6) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.382(9) yes
C1 C6 1.394(9) yes
C1 N1 1.436(8) yes
C2 O1 1.351(8) yes
C2 C3 1.385(10) yes
C3 C4 1.366(11) yes
C4 C5 1.368(10) yes
C5 CMe 1.516(11) yes
C5 C6 1.369(10) yes
N1 N2 1.315(7) yes
N1 N3 1.343(7) yes
N2 C12 1.352(8) yes
N3 C7 1.351(8) yes
C7 C8 1.417(10) yes
C7 C12 1.404(9) yes
C8 C9 1.356(10) yes
C9 C10 1.403(11) yes
C9 Cl 1.748(7) yes
C10 C11 1.344(10) yes
C11 C12 1.408(9) yes
loop_
_cod_changelog_entry_id
_cod_changelog_entry_author
_cod_changelog_entry_date
_cod_changelog_entry_text
1 'Vaitkus, Antanas' 2022-09-28T21:12:00+03:00
;
 Added the '_atom_site_type_symbol' data item.
;
