#------------------------------------------------------------------------------
#$Date: 2020-06-06 01:28:40 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252949 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/21/2022148.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_2022148
loop_
_publ_author_name
'Vicentes, Daniel E.'
'Romero, Andrea L.'
'Rodríguez, Ricuarte'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;
 Conversion of 3-amino-4-arylamino-1H-isochromen-1-ones to
 1-arylisochromeno[3,4-d][1,2,3]triazol-5(1H)-ones:
 synthesis, spectroscopic characterization and the structures of four
 products and one ring-opened derivative
;
_journal_coeditor_code           SK3747
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              446
_journal_page_last               453
_journal_paper_doi               10.1107/S2053229620003757
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C17 H15 N3 O3'
_chemical_formula_moiety         'C17 H15 N3 O3'
_chemical_formula_sum            'C17 H15 N3 O3'
_chemical_formula_weight         309.32
_chemical_name_systematic
;
Methyl 2-[4-hydroxy-1-(2-methylphenyl)-1H-1,2,3-triazol-5-yl]benzoate
;
_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   mixed
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 98.655(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1518(5)
_cell_length_b                   9.3143(4)
_cell_length_c                   14.2417(6)
_cell_measurement_reflns_used    3361
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.518
_cell_measurement_theta_min      2.622
_cell_volume                     1462.46(11)
_computing_cell_refinement
;
APEX3 (Bruker, 2018)
;
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
APEX3 (Bruker, 2018)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33834
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         27.518
_diffrn_reflns_theta_min         2.622
_diffrn_source
'INCOATEC high brilliance microfocus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0333P)²+1.1492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.0976
_reflns_number_gt                3084
_reflns_number_total             3360
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sk3747sup1.cif
_cod_data_source_block           V
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2022148
_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.
;
_shelx_estimated_absorpt_t_min   0.981
_shelx_estimated_absorpt_t_max   0.993
_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
C C1 0.09089(12) 0.58783(14) 0.64445(9) 0.0143(3) Uani d 1 . .
C C2 0.20897(12) 0.64468(14) 0.66637(9) 0.0140(3) Uani d 1 . .
C C3 0.22319(12) 0.79047(15) 0.68731(9) 0.0171(3) Uani d 1 . .
H H3 0.3024 0.8295 0.7027 0.021 Uiso calc 1 . .
C C4 0.12250(13) 0.87957(15) 0.68594(10) 0.0194(3) Uani d 1 . .
H H4 0.1333 0.9789 0.6998 0.023 Uiso calc 1 . .
C C5 0.00649(13) 0.82309(16) 0.66441(10) 0.0194(3) Uani d 1 . .
H H5 -0.0622 0.8837 0.6633 0.023 Uiso calc 1 . .
C C6 -0.00894(12) 0.67859(15) 0.64454(9) 0.0176(3) Uani d 1 . .
H H6 -0.0886 0.6403 0.6307 0.021 Uiso calc 1 . .
C C7 0.07137(12) 0.43259(15) 0.61927(9) 0.0158(3) Uani d 1 . .
O O1 0.15037(9) 0.34535(11) 0.61744(8) 0.0255(2) Uani d 1 . .
O O2 -0.04681(9) 0.40148(11) 0.59904(7) 0.0205(2) Uani d 1 . .
C C8 -0.07555(14) 0.25126(16) 0.58262(11) 0.0227(3) Uani d 1 . .
H H8A -0.0554 0.1980 0.6423 0.034 Uiso calc 1 . .
H H8B -0.0284 0.2131 0.5355 0.034 Uiso calc 1 . .
H H8C -0.1623 0.2410 0.5590 0.034 Uiso calc 1 . .
N N21 0.38126(10) 0.47254(12) 0.72720(8) 0.0142(2) Uani d 1 . .
N N22 0.47490(10) 0.40735(12) 0.69580(8) 0.0160(2) Uani d 1 . .
N N23 0.47309(10) 0.45003(12) 0.60673(8) 0.0157(2) Uani d 1 . .
C C24 0.38003(11) 0.54203(14) 0.58314(9) 0.0152(3) Uani d 1 . .
C C25 0.31891(11) 0.55871(14) 0.65953(9) 0.0140(3) Uani d 1 . .
C C211 0.35990(11) 0.44834(15) 0.82315(9) 0.0155(3) Uani d 1 . .
C C212 0.33495(12) 0.30970(15) 0.85228(9) 0.0171(3) Uani d 1 . .
C C213 0.31541(12) 0.29355(16) 0.94627(10) 0.0210(3) Uani d 1 . .
H H213 0.2981 0.2009 0.9688 0.025 Uiso calc 1 . .
C C214 0.32075(13) 0.40992(18) 1.00731(10) 0.0241(3) Uani d 1 . .
H H214 0.3062 0.3962 1.0707 0.029 Uiso calc 1 . .
C C215 0.34696(14) 0.54549(17) 0.97710(10) 0.0235(3) Uani d 1 . .
H H215 0.3513 0.6246 1.0196 0.028 Uiso calc 1 . .
C C216 0.36705(12) 0.56555(15) 0.88384(10) 0.0191(3) Uani d 1 . .
H H216 0.3854 0.6582 0.8621 0.023 Uiso calc 1 . .
C C217 0.32682(14) 0.18273(15) 0.78655(10) 0.0226(3) Uani d 1 . .
H H27A 0.3030 0.0975 0.8196 0.034 Uiso calc 1 . .
H H27B 0.4060 0.1661 0.7665 0.034 Uiso calc 1 . .
H H27C 0.2662 0.2018 0.7306 0.034 Uiso calc 1 . .
O O24 0.35119(9) 0.60183(12) 0.49726(7) 0.0208(2) Uani d 1 . .
H H24 0.4112(18) 0.587(2) 0.4622(14) 0.031 Uiso d 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 119.34(12) ?
C6 C1 C7 . . 119.80(12) ?
C2 C1 C7 . . 120.85(12) ?
C3 C2 C1 . . 119.05(12) ?
C3 C2 C25 . . 118.19(12) ?
C1 C2 C25 . . 122.52(12) ?
C4 C3 C2 . . 120.76(13) ?
C4 C3 H3 . . 119.6 ?
C2 C3 H3 . . 119.6 ?
C5 C4 C3 . . 119.98(13) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C6 C5 C4 . . 119.88(13) ?
C6 C5 H5 . . 120.1 ?
C4 C5 H5 . . 120.1 ?
C5 C6 C1 . . 120.99(13) ?
C5 C6 H6 . . 119.5 ?
C1 C6 H6 . . 119.5 ?
O1 C7 O2 . . 123.40(13) ?
O1 C7 C1 . . 125.27(12) ?
O2 C7 C1 . . 111.32(11) ?
C7 O2 C8 . . 115.56(11) ?
O2 C8 H8A . . 109.5 ?
O2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N22 N21 C25 . . 111.77(10) ?
N22 N21 C211 . . 119.60(10) ?
C25 N21 C211 . . 128.62(11) ?
N23 N22 N21 . . 106.42(10) ?
N22 N23 C24 . . 109.21(10) ?
O24 C24 N23 . . 124.20(12) ?
O24 C24 C25 . . 126.57(12) ?
N23 C24 C25 . . 109.19(11) ?
N21 C25 C24 . . 103.41(11) ?
N21 C25 C2 . . 127.75(11) ?
C24 C25 C2 . . 128.80(12) ?
C216 C211 C212 . . 122.52(12) ?
C216 C211 N21 . . 117.77(12) ?
C212 C211 N21 . . 119.70(12) ?
C213 C212 C211 . . 116.82(13) ?
C213 C212 C217 . . 120.60(13) ?
C211 C212 C217 . . 122.58(12) ?
C214 C213 C212 . . 121.27(14) ?
C214 C213 H213 . . 119.4 ?
C212 C213 H213 . . 119.4 ?
C215 C214 C213 . . 120.78(13) ?
C215 C214 H214 . . 119.6 ?
C213 C214 H214 . . 119.6 ?
C214 C215 C216 . . 119.50(14) ?
C214 C215 H215 . . 120.3 ?
C216 C215 H215 . . 120.3 ?
C211 C216 C215 . . 119.10(13) ?
C211 C216 H216 . . 120.5 ?
C215 C216 H216 . . 120.5 ?
C212 C217 H27A . . 109.5 ?
C212 C217 H27B . . 109.5 ?
H27A C217 H27B . . 109.5 ?
C212 C217 H27C . . 109.5 ?
H27A C217 H27C . . 109.5 ?
H27B C217 H27C . . 109.5 ?
C24 O24 H24 . . 110.1(12) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.3981(18) ?
C1 C2 . 1.4100(18) ?
C1 C7 . 1.4977(19) ?
C2 C3 . 1.3941(19) ?
C2 C25 . 1.4798(17) ?
C3 C4 . 1.3941(19) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.387(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.381(2) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 O1 . 1.2017(17) ?
C7 O2 . 1.3378(16) ?
O2 C8 . 1.4466(17) ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
N21 N22 . 1.3415(15) ?
N21 C25 . 1.3619(16) ?
N21 C211 . 1.4396(16) ?
N22 N23 . 1.3265(15) ?
N23 C24 . 1.3489(17) ?
C24 O24 . 1.3383(16) ?
C24 C25 . 1.3768(17) ?
C211 C216 . 1.3873(19) ?
C211 C212 . 1.3971(19) ?
C212 C213 . 1.3963(19) ?
C212 C217 . 1.503(2) ?
C213 C214 . 1.385(2) ?
C213 H213 . 0.9500 ?
C214 C215 . 1.379(2) ?
C214 H214 . 0.9500 ?
C215 C216 . 1.3924(19) ?
C215 H215 . 0.9500 ?
C216 H216 . 0.9500 ?
C217 H27A . 0.9800 ?
C217 H27B . 0.9800 ?
C217 H27C . 0.9800 ?
O24 H24 . 0.90(2) ?
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
O24 H24 N23 3_666 0.90(2) 1.77(2) 2.6721(15) 177.5(19) no
C8 H8A Cg2 2_546 0.98 2.90 3.6605(16) 135 no
C8 H8B Cg2 3_566 0.98 2.90 3.5007(16) 120 no
C8 H8C O24 3_566 0.98 2.59 3.4004(19) 140 no
C215 H215 O24 4_576 0.95 2.57 3.2972(19) 134 no
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.23(18) ?
C7 C1 C2 C3 . . . . 178.54(12) ?
C6 C1 C2 C25 . . . . -174.48(12) ?
C7 C1 C2 C25 . . . . 4.29(18) ?
C1 C2 C3 C4 . . . . -0.53(19) ?
C25 C2 C3 C4 . . . . 173.97(12) ?
C2 C3 C4 C5 . . . . 0.6(2) ?
C3 C4 C5 C6 . . . . 0.1(2) ?
C4 C5 C6 C1 . . . . -0.9(2) ?
C2 C1 C6 C5 . . . . 0.94(19) ?
C7 C1 C6 C5 . . . . -177.84(12) ?
C6 C1 C7 O1 . . . . -179.60(13) ?
C2 C1 C7 O1 . . . . 1.6(2) ?
C6 C1 C7 O2 . . . . 0.11(17) ?
C2 C1 C7 O2 . . . . -178.66(11) ?
O1 C7 O2 C8 . . . . 5.37(19) ?
C1 C7 O2 C8 . . . . -174.35(11) ?
C25 N21 N22 N23 . . . . -0.60(14) ?
C211 N21 N22 N23 . . . . -179.36(11) ?
N21 N22 N23 C24 . . . . 0.61(14) ?
N22 N23 C24 O24 . . . . -178.16(12) ?
N22 N23 C24 C25 . . . . -0.41(15) ?
N22 N21 C25 C24 . . . . 0.34(14) ?
C211 N21 C25 C24 . . . . 178.96(12) ?
N22 N21 C25 C2 . . . . 178.22(12) ?
C211 N21 C25 C2 . . . . -3.2(2) ?
O24 C24 C25 N21 . . . . 177.72(13) ?
N23 C24 C25 N21 . . . . 0.04(14) ?
O24 C24 C25 C2 . . . . -0.1(2) ?
N23 C24 C25 C2 . . . . -177.80(13) ?
C3 C2 C25 N21 . . . . 98.58(16) ?
C1 C2 C25 N21 . . . . -87.12(17) ?
C3 C2 C25 C24 . . . . -84.07(18) ?
C1 C2 C25 C24 . . . . 90.23(18) ?
N22 N21 C211 C216 . . . . 117.83(14) ?
C25 N21 C211 C216 . . . . -60.69(18) ?
N22 N21 C211 C212 . . . . -61.17(16) ?
C25 N21 C211 C212 . . . . 120.30(15) ?
C216 C211 C212 C213 . . . . 0.88(19) ?
N21 C211 C212 C213 . . . . 179.84(11) ?
C216 C211 C212 C217 . . . . 179.82(13) ?
N21 C211 C212 C217 . . . . -1.23(19) ?
C211 C212 C213 C214 . . . . 0.0(2) ?
C217 C212 C213 C214 . . . . -179.00(13) ?
C212 C213 C214 C215 . . . . -0.7(2) ?
C213 C214 C215 C216 . . . . 0.7(2) ?
C212 C211 C216 C215 . . . . -1.0(2) ?
N21 C211 C216 C215 . . . . -179.93(12) ?
C214 C215 C216 C211 . . . . 0.2(2) ?

_cod_database_fobs_code 2022148
