#------------------------------------------------------------------------------
#$Date: 2023-11-06 10:04:51 +0200 (Mon, 06 Nov 2023) $
#$Revision: 287399 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/27/7062711.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_7062711
loop_
_publ_author_name
'Guo, Yimei'
'Sun, Zhenhua'
'He, Xiaodan'
'Cao, Penghui'
'Fan, Guangping'
'Gao, Qinghe'
_publ_section_title
;
 KI-mediated three-component annelation for the regioselective synthesis
 of angular azolo[1,5-a]pyrimidine derivatives
;
_journal_issue                   40
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              18618
_journal_page_last               18622
_journal_paper_doi               10.1039/D3NJ03930G
_journal_volume                  47
_journal_year                    2023
_chemical_formula_sum            'C23 H27 N3 O2'
_chemical_formula_weight         377.47
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2023-03-30 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                108.552(5)
_cell_angle_beta                 110.723(4)
_cell_angle_gamma                103.618(5)
_cell_formula_units_Z            2
_cell_length_a                   10.097(4)
_cell_length_b                   10.892(4)
_cell_length_c                   11.599(4)
_cell_measurement_reflns_used    2045
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.22
_cell_measurement_theta_min      2.24
_cell_volume                     1040.3(7)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6262
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.469
_diffrn_reflns_theta_min         2.092
_exptl_absorpt_coefficient_mu    0.078
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4579
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.1018
_refine_ls_R_factor_gt           0.0746
_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)+(0.1900P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2475
_refine_ls_wR_factor_ref         0.2829
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3112
_reflns_number_total             4579
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj03930g2.cif
_cod_data_source_block           H042_0m
_cod_depositor_comments          'Adding full bibliography for 7062711.cif.'
_cod_original_cell_volume        1040.2(7)
_cod_database_code               7062711
_shelx_shelxl_version_number     2016/6
_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   0.986
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7698(3) 0.1231(3) 0.4336(2) 0.0836(8) Uani 1 1 d . . . . .
O2 O 0.7830(2) 0.1080(2) 0.62578(19) 0.0624(6) Uani 1 1 d . . . . .
N1 N 0.4334(2) 0.2858(2) 0.48777(18) 0.0428(5) Uani 1 1 d . . . . .
N2 N 0.4662(3) 0.2879(2) 0.61311(19) 0.0551(6) Uani 1 1 d . . . . .
N3 N 0.4997(2) 0.2187(2) 0.30626(17) 0.0403(5) Uani 1 1 d . . . . .
C1 C 0.3778(3) 0.3454(3) 0.0574(2) 0.0474(6) Uani 1 1 d . . . . .
H1 H 0.381334 0.430436 0.113334 0.057 Uiso 1 1 calc R U . . .
C2 C 0.3682(3) 0.3218(3) -0.0712(3) 0.0568(7) Uani 1 1 d . . . . .
H2 H 0.365699 0.391720 -0.100578 0.068 Uiso 1 1 calc R U . . .
C3 C 0.3624(3) 0.1968(3) -0.1551(3) 0.0598(7) Uani 1 1 d . . . . .
H3 H 0.354115 0.181636 -0.241345 0.072 Uiso 1 1 calc R U . . .
C4 C 0.3689(3) 0.0936(3) -0.1112(3) 0.0569(7) Uani 1 1 d . . . . .
H4 H 0.365985 0.009063 -0.167293 0.068 Uiso 1 1 calc R U . . .
C5 C 0.3797(3) 0.1164(3) 0.0170(2) 0.0459(6) Uani 1 1 d . . . . .
H5 H 0.385466 0.047074 0.046715 0.055 Uiso 1 1 calc R U . . .
C6 C 0.3820(2) 0.2410(2) 0.1018(2) 0.0381(5) Uani 1 1 d . . . . .
C7 C 0.3984(2) 0.2617(2) 0.2408(2) 0.0368(5) Uani 1 1 d . . . . .
C8 C 0.5185(3) 0.2303(2) 0.4308(2) 0.0404(5) Uani 1 1 d . . . . .
C9 C 0.3261(3) 0.3288(2) 0.4207(2) 0.0403(5) Uani 1 1 d . . . . .
C10 C 0.3045(2) 0.3163(2) 0.2937(2) 0.0377(5) Uani 1 1 d . . . . .
C11 C 0.1779(3) 0.3507(3) 0.2106(2) 0.0462(6) Uani 1 1 d . . . . .
H11A H 0.130601 0.284012 0.114633 0.055 Uiso 1 1 calc R U . . .
H11B H 0.222663 0.443910 0.218219 0.055 Uiso 1 1 calc R U . . .
C12 C 0.0540(3) 0.3465(3) 0.2569(2) 0.0491(6) Uani 1 1 d . . . . .
H12 H 0.006430 0.248704 0.239722 0.059 Uiso 1 1 calc R U . . .
C13 C 0.1294(3) 0.4325(4) 0.4104(3) 0.0633(8) Uani 1 1 d . . . . .
H13A H 0.049950 0.432770 0.438964 0.076 Uiso 1 1 calc R U . . .
H13B H 0.187821 0.528984 0.433601 0.076 Uiso 1 1 calc R U . . .
C14 C 0.2353(3) 0.3780(3) 0.4890(2) 0.0532(7) Uani 1 1 d . . . . .
H14A H 0.305559 0.452183 0.581033 0.064 Uiso 1 1 calc R U . . .
H14B H 0.174724 0.300542 0.496984 0.064 Uiso 1 1 calc R U . . .
C15 C -0.0786(3) 0.3803(3) 0.1733(2) 0.0492(6) Uani 1 1 d . . . . .
C16 C -0.1451(4) 0.2877(5) 0.0207(3) 0.0908(12) Uani 1 1 d . . . . .
H16A H -0.235780 0.299856 -0.029097 0.136 Uiso 1 1 calc R U . . .
H16B H -0.171382 0.190871 0.004138 0.136 Uiso 1 1 calc R U . . .
H16C H -0.070242 0.313619 -0.009337 0.136 Uiso 1 1 calc R U . . .
C17 C -0.0257(4) 0.5318(4) 0.2008(4) 0.0985(13) Uani 1 1 d . . . . .
H17A H 0.063110 0.556698 0.186751 0.148 Uiso 1 1 calc R U . . .
H17B H 0.000389 0.589669 0.293994 0.148 Uiso 1 1 calc R U . . .
H17C H -0.106754 0.546248 0.139341 0.148 Uiso 1 1 calc R U . . .
C18 C -0.2105(4) 0.3442(4) 0.2096(4) 0.0863(11) Uani 1 1 d . . . . .
H18A H -0.295377 0.358906 0.153312 0.129 Uiso 1 1 calc R U . . .
H18B H -0.175437 0.403627 0.304604 0.129 Uiso 1 1 calc R U . . .
H18C H -0.243079 0.247410 0.193426 0.129 Uiso 1 1 calc R U . . .
C19 C 0.5701(3) 0.2320(3) 0.6327(2) 0.0545(7) Uani 1 1 d . . . . .
H19 H 0.613117 0.218392 0.710628 0.065 Uiso 1 1 calc R U . . .
C20 C 0.6103(3) 0.1949(3) 0.5265(2) 0.0445(6) Uani 1 1 d . . . . .
C21 C 0.7257(3) 0.1379(3) 0.5190(2) 0.0525(7) Uani 1 1 d . . . . .
C22 C 0.9020(4) 0.0548(4) 0.6354(3) 0.0753(9) Uani 1 1 d . . . . .
H22A H 0.985611 0.118385 0.633501 0.090 Uiso 1 1 calc R U . . .
H22B H 0.861375 -0.036576 0.558218 0.090 Uiso 1 1 calc R U . . .
C23 C 0.9581(4) 0.0424(4) 0.7637(4) 0.0873(11) Uani 1 1 d . . . . .
H23A H 0.872872 -0.012210 0.769285 0.131 Uiso 1 1 calc R U . . .
H23B H 1.009458 0.134528 0.839684 0.131 Uiso 1 1 calc R U . . .
H23C H 1.028937 -0.003295 0.766625 0.131 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 O2 C22 117.2(2) . . ?
N2 N1 C9 125.09(18) . . ?
N2 N1 C8 112.58(19) . . ?
C9 N1 C8 122.30(18) . . ?
C19 N2 N1 103.46(18) . . ?
C7 N3 C8 117.96(18) . . ?
C6 C1 C2 119.6(2) . . ?
C6 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C3 C2 C1 120.9(2) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 119.9(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 121.2(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 118.7(2) . . ?
C5 C6 C7 118.86(19) . . ?
C1 C6 C7 122.3(2) . . ?
N3 C7 C10 123.48(18) . . ?
N3 C7 C6 114.20(18) . . ?
C10 C7 C6 122.22(18) . . ?
N3 C8 N1 120.67(19) . . ?
N3 C8 C20 133.9(2) . . ?
N1 C8 C20 105.43(19) . . ?
C10 C9 N1 117.69(19) . . ?
C10 C9 C14 125.1(2) . . ?
N1 C9 C14 117.09(19) . . ?
C9 C10 C7 117.86(19) . . ?
C9 C10 C11 119.51(19) . . ?
C7 C10 C11 122.51(18) . . ?
C10 C11 C12 112.99(18) . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 109.2(2) . . ?
C13 C12 C15 114.9(2) . . ?
C11 C12 C15 114.43(19) . . ?
C13 C12 H12 105.8 . . ?
C11 C12 H12 105.8 . . ?
C15 C12 H12 105.8 . . ?
C12 C13 C14 113.2(2) . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.8 . . ?
C9 C14 C13 112.1(2) . . ?
C9 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
C9 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C17 C15 C16 109.5(3) . . ?
C17 C15 C18 109.5(3) . . ?
C16 C15 C18 106.2(2) . . ?
C17 C15 C12 111.8(2) . . ?
C16 C15 C12 110.1(2) . . ?
C18 C15 C12 109.4(2) . . ?
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 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 C20 114.5(2) . . ?
N2 C19 H19 122.8 . . ?
C20 C19 H19 122.8 . . ?
C8 C20 C19 104.1(2) . . ?
C8 C20 C21 127.6(2) . . ?
C19 C20 C21 128.3(2) . . ?
O1 C21 O2 123.4(2) . . ?
O1 C21 C20 126.2(2) . . ?
O2 C21 C20 110.4(2) . . ?
O2 C22 C23 108.5(3) . . ?
O2 C22 H22A 110.0 . . ?
C23 C22 H22A 110.0 . . ?
O2 C22 H22B 110.0 . . ?
C23 C22 H22B 110.0 . . ?
H22A C22 H22B 108.4 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C21 1.204(3) . ?
O2 C21 1.346(3) . ?
O2 C22 1.438(3) . ?
N1 N2 1.363(3) . ?
N1 C9 1.368(3) . ?
N1 C8 1.391(3) . ?
N2 C19 1.321(3) . ?
N3 C7 1.321(3) . ?
N3 C8 1.348(3) . ?
C1 C6 1.392(3) . ?
C1 C2 1.394(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.372(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.497(3) . ?
C7 C10 1.440(3) . ?
C8 C20 1.397(3) . ?
C9 C10 1.367(3) . ?
C9 C14 1.493(3) . ?
C10 C11 1.513(3) . ?
C11 C12 1.523(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.507(4) . ?
C12 C15 1.552(3) . ?
C12 H12 0.9800 . ?
C13 C14 1.511(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C17 1.496(4) . ?
C15 C16 1.518(4) . ?
C15 C18 1.537(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.399(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.458(3) . ?
C22 C23 1.456(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 N2 C19 177.4(2) . . . . ?
C8 N1 N2 C19 -0.8(3) . . . . ?
C6 C1 C2 C3 0.2(4) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C4 C5 C6 C1 -1.9(3) . . . . ?
C4 C5 C6 C7 -178.3(2) . . . . ?
C2 C1 C6 C5 1.3(3) . . . . ?
C2 C1 C6 C7 177.6(2) . . . . ?
C8 N3 C7 C10 -1.8(3) . . . . ?
C8 N3 C7 C6 -178.34(19) . . . . ?
C5 C6 C7 N3 41.6(3) . . . . ?
C1 C6 C7 N3 -134.6(2) . . . . ?
C5 C6 C7 C10 -135.0(2) . . . . ?
C1 C6 C7 C10 48.8(3) . . . . ?
C7 N3 C8 N1 0.0(3) . . . . ?
C7 N3 C8 C20 178.8(2) . . . . ?
N2 N1 C8 N3 179.2(2) . . . . ?
C9 N1 C8 N3 1.1(3) . . . . ?
N2 N1 C8 C20 0.2(3) . . . . ?
C9 N1 C8 C20 -178.0(2) . . . . ?
N2 N1 C9 C10 -178.3(2) . . . . ?
C8 N1 C9 C10 -0.4(3) . . . . ?
N2 N1 C9 C14 -1.7(4) . . . . ?
C8 N1 C9 C14 176.2(2) . . . . ?
N1 C9 C10 C7 -1.2(3) . . . . ?
C14 C9 C10 C7 -177.5(2) . . . . ?
N1 C9 C10 C11 174.8(2) . . . . ?
C14 C9 C10 C11 -1.5(4) . . . . ?
N3 C7 C10 C9 2.4(3) . . . . ?
C6 C7 C10 C9 178.7(2) . . . . ?
N3 C7 C10 C11 -173.5(2) . . . . ?
C6 C7 C10 C11 2.8(3) . . . . ?
C9 C10 C11 C12 -20.2(3) . . . . ?
C7 C10 C11 C12 155.6(2) . . . . ?
C10 C11 C12 C13 50.0(3) . . . . ?
C10 C11 C12 C15 -179.6(2) . . . . ?
C11 C12 C13 C14 -61.0(3) . . . . ?
C15 C12 C13 C14 168.8(2) . . . . ?
C10 C9 C14 C13 -7.9(4) . . . . ?
N1 C9 C14 C13 175.8(2) . . . . ?
C12 C13 C14 C9 39.4(3) . . . . ?
C13 C12 C15 C17 57.9(3) . . . . ?
C11 C12 C15 C17 -69.7(3) . . . . ?
C13 C12 C15 C16 179.9(3) . . . . ?
C11 C12 C15 C16 52.4(3) . . . . ?
C13 C12 C15 C18 -63.7(3) . . . . ?
C11 C12 C15 C18 168.8(2) . . . . ?
N1 N2 C19 C20 1.1(3) . . . . ?
N3 C8 C20 C19 -178.4(3) . . . . ?
N1 C8 C20 C19 0.5(3) . . . . ?
N3 C8 C20 C21 3.8(5) . . . . ?
N1 C8 C20 C21 -177.3(2) . . . . ?
N2 C19 C20 C8 -1.0(3) . . . . ?
N2 C19 C20 C21 176.7(3) . . . . ?
C22 O2 C21 O1 -0.5(4) . . . . ?
C22 O2 C21 C20 -178.1(2) . . . . ?
C8 C20 C21 O1 6.7(5) . . . . ?
C19 C20 C21 O1 -170.5(3) . . . . ?
C8 C20 C21 O2 -175.7(2) . . . . ?
C19 C20 C21 O2 7.1(4) . . . . ?
C21 O2 C22 C23 174.5(3) . . . . ?
