#------------------------------------------------------------------------------
#$Date: 2024-02-04 14:29:33 +0200 (Sun, 04 Feb 2024) $
#$Revision: 289628 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/97/7159704.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7159704
loop_
_publ_author_name
'Oh, Hyunjin'
'Kim, Ikyon'
_publ_section_title
;
 Catalyst-free assembly of a polyfunctionalized 1,2,4-triazole-fused
 N-heterocycle, 6-acylated
 pyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine.
;
_journal_issue                   2
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              320
_journal_page_last               336
_journal_paper_doi               10.1039/d3ob01747h
_journal_volume                  22
_journal_year                    2024
_chemical_formula_sum            'C16 H12 N4 O'
_chemical_formula_weight         276.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2023-10-25 deposited with the CCDC.	2023-11-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.3854(19)
_cell_length_b                   7.5604(8)
_cell_length_c                   20.364(2)
_cell_measurement_reflns_used    7035
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      28.1070
_cell_measurement_theta_min      2.3181
_cell_volume                     2676.7(5)
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service v2019.11.0.3'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21937
_diffrn_reflns_theta_full        28.15
_diffrn_reflns_theta_max         28.15
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.760
_refine_diff_density_min         -0.398
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3174
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0738
_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)+(0.1196P)²+2.4613P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2067
_refine_ls_wR_factor_ref         0.2302
_reflns_number_gt                2323
_reflns_number_total             3174
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01747h2.cif
_cod_data_source_block           IK2016
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7159704.cif.
;
_cod_database_code               7159704
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.48247(12) 0.1819(3) 0.53394(9) 0.0463(5) Uani d . . . 1 . .
N N1 0.45402(11) 0.3597(3) 0.41369(9) 0.0304(5) Uani d . . . 1 . .
N N2 0.36855(12) 0.6586(3) 0.42624(10) 0.0324(5) Uani d . . . 1 . .
N N3 0.32982(13) 0.8170(3) 0.42583(11) 0.0386(5) Uani d . . . 1 . .
N N4 0.39275(13) 0.7718(3) 0.32896(11) 0.0386(5) Uani d . . . 1 . .
C C11 0.45150(14) 0.4793(3) 0.36044(11) 0.0316(5) Uani d . . . 1 . .
C C8 0.41318(14) 0.3910(3) 0.47217(11) 0.0313(5) Uani d . . . 1 . .
C C10 0.40630(14) 0.6355(3) 0.36845(12) 0.0318(5) Uani d . . . 1 . .
C C1 0.42335(14) 0.2681(3) 0.52890(12) 0.0324(5) Uani d . . . 1 . .
C C3 0.36143(14) 0.2556(3) 0.57967(11) 0.0316(5) Uani d . . . 1 . .
C C9 0.37142(14) 0.5409(3) 0.47814(12) 0.0342(6) Uani d . . . 1 . .
C C12 0.49656(15) 0.4131(4) 0.31086(13) 0.0392(6) Uani d . . . 1 . .
H H12 0.505494 0.465292 0.270215 0.047 Uiso calc U . R 1 . .
C C7 0.28365(15) 0.2834(4) 0.56569(13) 0.0375(6) Uani d . . . 1 . .
C C15 0.34646(15) 0.8783(3) 0.36671(13) 0.0372(6) Uani d . . . 1 . .
C C2 0.38421(17) 0.2033(4) 0.64289(12) 0.0393(6) Uani d . . . 1 . .
C C13 0.52679(16) 0.2506(4) 0.33330(14) 0.0413(6) Uani d . . . 1 . .
H H13 0.559441 0.176919 0.309615 0.05 Uiso calc U . R 1 . .
C C14 0.50023(16) 0.2188(4) 0.39570(13) 0.0384(6) Uani d . . . 1 . .
H H14 0.511319 0.120126 0.42129 0.046 Uiso calc U . R 1 . .
C C6 0.22920(16) 0.2644(4) 0.61507(14) 0.0432(7) Uani d . . . 1 . .
C C4 0.32846(19) 0.1831(4) 0.69184(13) 0.0457(7) Uani d . . . 1 . .
C C5 0.25179(19) 0.2143(4) 0.67823(14) 0.0468(7) Uani d . . . 1 . .
C C16 0.31651(19) 1.0510(4) 0.34256(16) 0.0512(8) Uani d . . . 1 . .
H H16A 0.275774 1.030615 0.311654 0.077 Uiso calc U . R 1 . .
H H16B 0.357263 1.115314 0.321531 0.077 Uiso calc U . R 1 . .
H H16C 0.297205 1.118478 0.378942 0.077 Uiso calc U . R 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
C14 N1 C8 . . 130.3(2) ?
C14 N1 C11 . . 107.9(2) ?
C8 N1 C11 . . 121.8(2) ?
C10 N2 N3 . . 110.09(19) ?
C10 N2 C9 . . 124.2(2) ?
N3 N2 C9 . . 125.7(2) ?
C15 N3 N2 . . 101.8(2) ?
C10 N4 C15 . . 102.7(2) ?
C12 C11 N1 . . 108.2(2) ?
C12 C11 C10 . . 134.4(2) ?
N1 C11 C10 . . 117.3(2) ?
C9 C8 N1 . . 119.2(2) ?
C9 C8 C1 . . 121.1(2) ?
N1 C8 C1 . . 119.4(2) ?
N4 C10 N2 . . 109.8(2) ?
N4 C10 C11 . . 132.1(2) ?
N2 C10 C11 . . 118.1(2) ?
O1 C1 C8 . . 119.8(2) ?
O1 C1 C3 . . 120.9(2) ?
C8 C1 C3 . . 119.3(2) ?
C7 C3 C2 . . 120.1(2) ?
C7 C3 C1 . . 123.1(2) ?
C2 C3 C1 . . 116.7(2) ?
C8 C9 N2 . . 119.4(2) ?
C11 C12 C13 . . 107.0(2) ?
C11 C12 H12 . . 126.5 ?
C13 C12 H12 . . 126.5 ?
C6 C7 C3 . . 119.8(2) ?
N3 C15 N4 . . 115.6(2) ?
N3 C15 C16 . . 122.1(3) ?
N4 C15 C16 . . 122.3(2) ?
C4 C2 C3 . . 119.3(3) ?
C14 C13 C12 . . 109.1(2) ?
C14 C13 H13 . . 125.5 ?
C12 C13 H13 . . 125.5 ?
C13 C14 N1 . . 107.8(2) ?
C13 C14 H14 . . 126.1 ?
N1 C14 H14 . . 126.1 ?
C7 C6 C5 . . 120.2(3) ?
C5 C4 C2 . . 120.5(3) ?
C4 C5 C6 . . 120.1(3) ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
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
O1 C1 . 1.221(3) ?
N1 C14 . 1.384(3) ?
N1 C8 . 1.407(3) ?
N1 C11 . 1.413(3) ?
N2 C10 . 1.359(3) ?
N2 N3 . 1.374(3) ?
N2 C9 . 1.382(3) ?
N3 C15 . 1.322(3) ?
N4 C10 . 1.328(3) ?
N4 C15 . 1.373(3) ?
C11 C12 . 1.373(3) ?
C11 C10 . 1.428(3) ?
C8 C9 . 1.352(4) ?
C8 C1 . 1.493(3) ?
C1 C3 . 1.496(3) ?
C3 C7 . 1.398(4) ?
C3 C2 . 1.404(3) ?
C12 C13 . 1.412(4) ?
C12 H12 . 0.93 ?
C7 C6 . 1.389(4) ?
C15 C16 . 1.489(4) ?
C2 C4 . 1.399(4) ?
C13 C14 . 1.373(4) ?
C13 H13 . 0.93 ?
C14 H14 . 0.93 ?
C6 C5 . 1.397(4) ?
C4 C5 . 1.382(5) ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
