#------------------------------------------------------------------------------
#$Date: 2020-06-06 01:28:40 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252949 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/21/2022146.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_2022146
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          'C15 H8 Cl N3 O2'
_chemical_formula_moiety         'C15 H8 Cl N3 O2'
_chemical_formula_sum            'C15 H8 Cl N3 O2'
_chemical_formula_weight         297.69
_chemical_name_systematic
;
1-(3-Chlorophenyl)isochromeno[3,4-d][1,2,3]triazol-5(1H)-one
;
_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     difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 106.675(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0993(8)
_cell_length_b                   12.8996(9)
_cell_length_c                   9.2234(6)
_cell_measurement_reflns_used    2905
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.502
_cell_measurement_theta_min      2.482
_cell_volume                     1265.04(15)
_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 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0442
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            28194
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_min         2.482
_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    0.310
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.364
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2905
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0324
_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)+(0.0355P)²+0.8531P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0890
_reflns_number_gt                2495
_reflns_number_total             2905
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sk3747sup1.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2022146
_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   0.941
_shelx_estimated_absorpt_t_max   0.985
_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
N N1 0.31229(11) 0.37182(9) 0.35005(13) 0.0154(2) Uani d 1 . .
N N2 0.33212(12) 0.37226(9) 0.21107(13) 0.0178(3) Uani d 1 . .
N N3 0.45443(12) 0.37148(9) 0.23045(13) 0.0178(3) Uani d 1 . .
C C3A 0.50995(13) 0.37008(10) 0.38001(15) 0.0150(3) Uani d 1 . .
O O4 0.63690(9) 0.36761(8) 0.43901(11) 0.0173(2) Uani d 1 . .
C C5 0.68473(13) 0.35314(11) 0.59491(16) 0.0169(3) Uani d 1 . .
O O5 0.79506(10) 0.33562(9) 0.64252(12) 0.0235(2) Uani d 1 . .
C C5A 0.59649(13) 0.36403(10) 0.68762(15) 0.0152(3) Uani d 1 . .
C C6 0.64946(14) 0.36544(11) 0.84469(16) 0.0172(3) Uani d 1 . .
H H6 0.7377 0.3578 0.8868 0.021 Uiso calc 1 . .
C C7 0.57345(14) 0.37794(11) 0.93857(16) 0.0184(3) Uani d 1 . .
H H7 0.6092 0.3784 1.0453 0.022 Uiso calc 1 . .
C C8 0.44389(14) 0.38985(11) 0.87597(16) 0.0178(3) Uani d 1 . .
H H8 0.3922 0.3991 0.9411 0.021 Uiso calc 1 . .
C C9 0.38931(13) 0.38851(11) 0.72091(16) 0.0168(3) Uani d 1 . .
H H9 0.3010 0.3971 0.6802 0.020 Uiso calc 1 . .
C C9A 0.46493(13) 0.37448(10) 0.62463(15) 0.0145(3) Uani d 1 . .
C C9B 0.42430(13) 0.37109(10) 0.46111(15) 0.0146(3) Uani d 1 . .
C C11 0.18482(13) 0.37130(11) 0.35641(15) 0.0165(3) Uani d 1 . .
C C12 0.10125(13) 0.43927(11) 0.26168(16) 0.0183(3) Uani d 1 . .
H H12 0.1280 0.4848 0.1961 0.022 Uiso calc 1 . .
C C13 -0.02249(14) 0.43847(12) 0.26588(17) 0.0217(3) Uani d 1 . .
Cl Cl13 -0.12819(4) 0.52194(3) 0.14523(5) 0.03006(12) Uani d 1 . .
C C14 -0.06264(15) 0.37398(14) 0.36282(18) 0.0266(3) Uani d 1 . .
H H14 -0.1474 0.3758 0.3659 0.032 Uiso calc 1 . .
C C15 0.02333(15) 0.30666(14) 0.45542(19) 0.0278(4) Uani d 1 . .
H H15 -0.0031 0.2623 0.5226 0.033 Uiso calc 1 . .
C C16 0.14708(14) 0.30312(12) 0.45149(17) 0.0217(3) Uani d 1 . .
H H16 0.2048 0.2552 0.5124 0.026 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'
Cl Cl 0.1484 0.1585 '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
N2 N1 C9B . . 110.37(11) ?
N2 N1 C11 . . 117.83(11) ?
C9B N1 C11 . . 131.80(12) ?
N3 N2 N1 . . 108.11(11) ?
N2 N3 C3A . . 106.94(12) ?
N3 C3A O4 . . 122.07(12) ?
N3 C3A C9B . . 112.11(13) ?
O4 C3A C9B . . 125.82(12) ?
C3A O4 C5 . . 117.43(11) ?
O5 C5 O4 . . 116.73(12) ?
O5 C5 C5A . . 125.62(13) ?
O4 C5 C5A . . 117.62(12) ?
C6 C5A C9A . . 120.11(13) ?
C6 C5A C5 . . 116.65(12) ?
C9A C5A C5 . . 123.23(12) ?
C7 C6 C5A . . 120.01(13) ?
C7 C6 H6 . . 120.0 ?
C5A C6 H6 . . 120.0 ?
C6 C7 C8 . . 119.72(13) ?
C6 C7 H7 . . 120.1 ?
C8 C7 H7 . . 120.1 ?
C9 C8 C7 . . 121.31(13) ?
C9 C8 H8 . . 119.3 ?
C7 C8 H8 . . 119.3 ?
C8 C9 C9A . . 119.57(13) ?
C8 C9 H9 . . 120.2 ?
C9A C9 H9 . . 120.2 ?
C9 C9A C5A . . 119.26(13) ?
C9 C9A C9B . . 127.04(13) ?
C5A C9A C9B . . 113.69(12) ?
N1 C9B C3A . . 102.46(12) ?
N1 C9B C9A . . 136.62(13) ?
C3A C9B C9A . . 120.87(13) ?
C12 C11 C16 . . 121.95(14) ?
C12 C11 N1 . . 117.43(12) ?
C16 C11 N1 . . 120.60(13) ?
C13 C12 C11 . . 117.81(14) ?
C13 C12 H12 . . 121.1 ?
C11 C12 H12 . . 121.1 ?
C12 C13 C14 . . 121.86(14) ?
C12 C13 Cl13 . . 118.02(12) ?
C14 C13 Cl13 . . 120.12(12) ?
C13 C14 C15 . . 118.77(15) ?
C13 C14 H14 . . 120.6 ?
C15 C14 H14 . . 120.6 ?
C16 C15 C14 . . 121.09(15) ?
C16 C15 H15 . . 119.5 ?
C14 C15 H15 . . 119.5 ?
C15 C16 C11 . . 118.47(14) ?
C15 C16 H16 . . 120.8 ?
C11 C16 H16 . . 120.8 ?
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
N1 N2 . 1.3614(16) ?
N1 C9B . 1.3654(18) ?
N1 C11 . 1.4328(18) ?
N2 N3 . 1.3175(17) ?
N3 C3A . 1.3399(18) ?
C3A O4 . 1.3574(17) ?
C3A C9B . 1.3680(19) ?
O4 C5 . 1.3950(17) ?
C5 O5 . 1.1979(18) ?
C5 C5A . 1.4801(19) ?
C5A C6 . 1.3986(19) ?
C5A C9A . 1.4146(19) ?
C6 C7 . 1.381(2) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.396(2) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.3841(19) ?
C8 H8 . 0.9500 ?
C9 C9A . 1.3977(19) ?
C9 H9 . 0.9500 ?
C9A C9B . 1.4455(18) ?
C11 C12 . 1.388(2) ?
C11 C16 . 1.389(2) ?
C12 C13 . 1.385(2) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.385(2) ?
C13 Cl13 . 1.7392(15) ?
C14 C15 . 1.388(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.385(2) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
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
C8 H8 N3 1_556 0.95 2.58 3.2465(19) 127 no
C16 H16 N2 4_566 0.95 2.56 3.500(2) 169 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
C9B N1 N2 N3 . . . . 0.20(15) ?
C11 N1 N2 N3 . . . . -179.28(11) ?
N1 N2 N3 C3A . . . . 0.28(14) ?
N2 N3 C3A O4 . . . . 179.12(12) ?
N2 N3 C3A C9B . . . . -0.68(16) ?
N3 C3A O4 C5 . . . . -172.11(12) ?
C9B C3A O4 C5 . . . . 7.7(2) ?
C3A O4 C5 O5 . . . . 169.17(13) ?
C3A O4 C5 C5A . . . . -12.78(17) ?
O5 C5 C5A C6 . . . . 7.6(2) ?
O4 C5 C5A C6 . . . . -170.28(12) ?
O5 C5 C5A C9A . . . . -173.50(14) ?
O4 C5 C5A C9A . . . . 8.6(2) ?
C9A C5A C6 C7 . . . . -0.6(2) ?
C5 C5A C6 C7 . . . . 178.40(13) ?
C5A C6 C7 C8 . . . . -0.4(2) ?
C6 C7 C8 C9 . . . . 0.6(2) ?
C7 C8 C9 C9A . . . . 0.3(2) ?
C8 C9 C9A C5A . . . . -1.3(2) ?
C8 C9 C9A C9B . . . . -179.96(13) ?
C6 C5A C9A C9 . . . . 1.4(2) ?
C5 C5A C9A C9 . . . . -177.46(13) ?
C6 C5A C9A C9B . . . . -179.74(12) ?
C5 C5A C9A C9B . . . . 1.38(19) ?
N2 N1 C9B C3A . . . . -0.58(15) ?
C11 N1 C9B C3A . . . . 178.81(14) ?
N2 N1 C9B C9A . . . . 176.95(15) ?
C11 N1 C9B C9A . . . . -3.7(3) ?
N3 C3A C9B N1 . . . . 0.77(15) ?
O4 C3A C9B N1 . . . . -179.02(13) ?
N3 C3A C9B C9A . . . . -177.25(12) ?
O4 C3A C9B C9A . . . . 3.0(2) ?
C9 C9A C9B N1 . . . . -5.6(3) ?
C5A C9A C9B N1 . . . . 175.67(15) ?
C9 C9A C9B C3A . . . . 171.59(14) ?
C5A C9A C9B C3A . . . . -7.14(19) ?
N2 N1 C11 C12 . . . . -45.43(17) ?
C9B N1 C11 C12 . . . . 135.22(15) ?
N2 N1 C11 C16 . . . . 132.99(14) ?
C9B N1 C11 C16 . . . . -46.4(2) ?
C16 C11 C12 C13 . . . . 0.9(2) ?
N1 C11 C12 C13 . . . . 179.30(13) ?
C11 C12 C13 C14 . . . . 1.3(2) ?
C11 C12 C13 Cl13 . . . . -178.97(11) ?
C12 C13 C14 C15 . . . . -1.6(2) ?
Cl13 C13 C14 C15 . . . . 178.64(13) ?
C13 C14 C15 C16 . . . . -0.2(3) ?
C14 C15 C16 C11 . . . . 2.3(2) ?
C12 C11 C16 C15 . . . . -2.6(2) ?
N1 C11 C16 C15 . . . . 179.00(14) ?

_cod_database_fobs_code 2022146
