#------------------------------------------------------------------------------
#$Date: 2022-09-01 04:28:09 +0300 (Thu, 01 Sep 2022) $
#$Revision: 277530 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/54/7245402.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_7245402
loop_
_publ_author_name
'Mao, Zhenjun'
'Zeng, Hao'
_publ_section_title
;
 Gold-catalyzed synthesis of oxazoles from alkynyl triazenes and
 dioxazoles
;
_journal_issue                   38
_journal_name_full               'RSC Advances'
_journal_page_first              24857
_journal_page_last               24860
_journal_paper_doi               10.1039/D2RA04559A
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C21 H24 N4 O'
_chemical_formula_sum            'C21 H24 N4 O'
_chemical_formula_weight         348.44
_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     dual
_audit_creation_date             2022-06-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-06-25 deposited with the CCDC.	2022-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.6880(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.6474(5)
_cell_length_b                   8.3478(2)
_cell_length_c                   11.4696(3)
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    169(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.64
_cell_volume                     1928.63(8)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      169.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            26386
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.119
_diffrn_reflns_theta_min         2.641
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1095 before and 0.0540 after correction.
The Ratio of minimum to maximum transmission is 0.9518.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0400
_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)+(0.0445P)²+0.5488P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1014
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3708
_reflns_number_total             4258
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra04559a2.cif
_cod_data_source_block           mo_220531_mzj_3_1
_cod_database_code               7245402
_shelx_shelxl_version_number     2018/3
_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_max   0.983
_shelx_estimated_absorpt_t_min   0.967
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16), C19(H19)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C8(H8), C5(H5), C12(H12), C7(H7), C6(H6), C15(H15),
 C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c), C18(H18a,H18b,H18c), C20(H20a,H20b,H20c), C21(H21a,H21b,
 H21c)
;
_olex2_submission_special_instructions 'No special instructions were received'
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_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 0.73133(4) 0.23231(9) 0.54811(7) 0.02809(18) Uani 1 1 d . . . . .
N2 N 0.77826(5) 0.53613(11) 0.76806(8) 0.0291(2) Uani 1 1 d . . . . .
N3 N 0.73837(5) 0.64607(11) 0.78578(8) 0.0281(2) Uani 1 1 d . . . . .
N1 N 0.67861(5) 0.40983(11) 0.64022(8) 0.0284(2) Uani 1 1 d . . . . .
N4 N 0.76450(5) 0.76132(11) 0.85963(8) 0.0310(2) Uani 1 1 d . . . . .
C3 C 0.74672(5) 0.42379(12) 0.68435(9) 0.0262(2) Uani 1 1 d . . . . .
C1 C 0.67232(5) 0.29625(13) 0.56121(9) 0.0273(2) Uani 1 1 d . . . . .
C4 C 0.61184(5) 0.23186(13) 0.48584(10) 0.0297(2) Uani 1 1 d . . . . .
C2 C 0.77937(5) 0.31464(13) 0.62886(9) 0.0271(2) Uani 1 1 d . . . . .
C10 C 0.84810(5) 0.27280(13) 0.63348(10) 0.0291(2) Uani 1 1 d . . . . .
C9 C 0.61468(6) 0.12083(14) 0.39670(11) 0.0354(3) Uani 1 1 d . . . . .
H9 H 0.656468 0.085721 0.384573 0.042 Uiso 1 1 calc R . . . .
C16 C 0.71709(6) 0.88682(13) 0.87625(10) 0.0325(2) Uani 1 1 d . . . . .
H16 H 0.740852 0.961062 0.939861 0.039 Uiso 1 1 calc R . . . .
C11 C 0.86516(6) 0.17034(16) 0.54911(11) 0.0390(3) Uani 1 1 d . . . . .
H11 H 0.831406 0.127174 0.487196 0.047 Uiso 1 1 calc R . . . .
C8 C 0.55680(7) 0.06154(16) 0.32580(12) 0.0438(3) Uani 1 1 d . . . . .
H8 H 0.558888 -0.014117 0.264857 0.053 Uiso 1 1 calc R . . . .
C5 C 0.55012(6) 0.28460(17) 0.50202(12) 0.0435(3) Uani 1 1 d . . . . .
H5 H 0.547686 0.361501 0.561964 0.052 Uiso 1 1 calc R . . . .
C12 C 0.93082(7) 0.13101(18) 0.55479(13) 0.0482(3) Uani 1 1 d . . . . .
H12 H 0.941677 0.060303 0.497045 0.058 Uiso 1 1 calc R . . . .
C17 C 0.65892(6) 0.81494(16) 0.91975(12) 0.0414(3) Uani 1 1 d . . . . .
H17A H 0.634248 0.742348 0.858691 0.062 Uiso 1 1 calc GR . . . .
H17B H 0.629478 0.900946 0.934739 0.062 Uiso 1 1 calc GR . . . .
H17C H 0.675556 0.755227 0.993841 0.062 Uiso 1 1 calc GR . . . .
C19 C 0.83540(6) 0.77267(17) 0.91815(12) 0.0431(3) Uani 1 1 d . . . . .
H19 H 0.858718 0.679857 0.890474 0.052 Uiso 1 1 calc R . . . .
C7 C 0.49587(7) 0.11186(18) 0.34317(13) 0.0493(3) Uani 1 1 d . . . . .
H7 H 0.456163 0.069299 0.295255 0.059 Uiso 1 1 calc R . . . .
C6 C 0.49272(7) 0.2241(2) 0.43025(14) 0.0528(4) Uani 1 1 d . . . . .
H6 H 0.450737 0.259977 0.440868 0.063 Uiso 1 1 calc R . . . .
C15 C 0.89879(7) 0.33572(19) 0.72127(14) 0.0523(4) Uani 1 1 d . . . . .
H15 H 0.888479 0.406907 0.779226 0.063 Uiso 1 1 calc R . . . .
C13 C 0.98053(7) 0.19290(18) 0.64288(15) 0.0516(4) Uani 1 1 d . . . . .
H13 H 1.025552 0.164911 0.646792 0.062 Uiso 1 1 calc R . . . .
C18 C 0.69439(7) 0.98444(17) 0.76301(12) 0.0473(3) Uani 1 1 d . . . . .
H18A H 0.733133 1.030657 0.739102 0.071 Uiso 1 1 calc GR . . . .
H18B H 0.665007 1.070703 0.777768 0.071 Uiso 1 1 calc GR . . . .
H18C H 0.670374 0.914985 0.699053 0.071 Uiso 1 1 calc GR . . . .
C14 C 0.96416(7) 0.2958(2) 0.72516(17) 0.0651(5) Uani 1 1 d . . . . .
H14 H 0.998310 0.340225 0.785752 0.078 Uiso 1 1 calc R . . . .
C20 C 0.84400(9) 0.7585(2) 1.05262(14) 0.0647(5) Uani 1 1 d . . . . .
H20A H 0.823740 0.851422 1.082798 0.097 Uiso 1 1 calc GR . . . .
H20B H 0.891417 0.754555 1.090300 0.097 Uiso 1 1 calc GR . . . .
H20C H 0.822406 0.660305 1.071583 0.097 Uiso 1 1 calc GR . . . .
C21 C 0.86577(8) 0.9253(2) 0.88153(17) 0.0648(5) Uani 1 1 d . . . . .
H21A H 0.860438 0.927027 0.794503 0.097 Uiso 1 1 calc GR . . . .
H21B H 0.913113 0.928817 0.919775 0.097 Uiso 1 1 calc GR . . . .
H21C H 0.843355 1.018382 0.906690 0.097 Uiso 1 1 calc GR . . . .
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
C1 O1 C2 104.93(8) . . ?
N3 N2 C3 111.82(9) . . ?
N2 N3 N4 116.07(9) . . ?
C1 N1 C3 104.67(9) . . ?
N3 N4 C16 114.36(9) . . ?
N3 N4 C19 124.46(9) . . ?
C19 N4 C16 121.12(9) . . ?
N1 C3 N2 126.01(9) . . ?
C2 C3 N2 124.26(10) . . ?
C2 C3 N1 109.66(9) . . ?
O1 C1 C4 117.32(9) . . ?
N1 C1 O1 114.00(9) . . ?
N1 C1 C4 128.68(10) . . ?
C9 C4 C1 120.88(10) . . ?
C9 C4 C5 119.61(11) . . ?
C5 C4 C1 119.50(11) . . ?
O1 C2 C10 117.19(9) . . ?
C3 C2 O1 106.74(9) . . ?
C3 C2 C10 136.05(10) . . ?
C11 C10 C2 121.11(10) . . ?
C15 C10 C2 120.77(10) . . ?
C15 C10 C11 118.11(11) . . ?
C4 C9 H9 120.0 . . ?
C8 C9 C4 120.07(11) . . ?
C8 C9 H9 120.0 . . ?
N4 C16 H16 107.5 . . ?
N4 C16 C17 110.89(10) . . ?
N4 C16 C18 111.09(10) . . ?
C17 C16 H16 107.5 . . ?
C18 C16 H16 107.5 . . ?
C18 C16 C17 112.01(11) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.53(12) . . ?
C12 C11 H11 119.7 . . ?
C9 C8 H8 119.9 . . ?
C9 C8 C7 120.24(12) . . ?
C7 C8 H8 119.9 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.55(13) . . ?
C6 C5 H5 120.2 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.80(13) . . ?
C13 C12 H12 119.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N4 C19 H19 107.8 . . ?
N4 C19 C20 109.92(12) . . ?
N4 C19 C21 110.92(12) . . ?
C20 C19 H19 107.8 . . ?
C20 C19 C21 112.52(13) . . ?
C21 C19 H19 107.8 . . ?
C8 C7 H7 120.0 . . ?
C6 C7 C8 119.96(12) . . ?
C6 C7 H7 120.0 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.56(13) . . ?
C7 C6 H6 119.7 . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.56(13) . . ?
C14 C15 H15 119.7 . . ?
C12 C13 H13 120.5 . . ?
C14 C13 C12 118.97(12) . . ?
C14 C13 H13 120.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C14 H14 119.5 . . ?
C13 C14 C15 121.02(13) . . ?
C13 C14 H14 119.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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 C1 1.3683(13) . ?
O1 C2 1.3821(13) . ?
N2 N3 1.2789(13) . ?
N2 C3 1.3967(14) . ?
N3 N4 1.3165(12) . ?
N1 C3 1.3910(14) . ?
N1 C1 1.2982(14) . ?
N4 C16 1.4745(14) . ?
N4 C19 1.4734(15) . ?
C3 C2 1.3705(15) . ?
C1 C4 1.4566(15) . ?
C4 C9 1.3907(16) . ?
C4 C5 1.3986(16) . ?
C2 C10 1.4511(15) . ?
C10 C11 1.3936(16) . ?
C10 C15 1.3863(17) . ?
C9 H9 0.9500 . ?
C9 C8 1.3811(17) . ?
C16 H16 1.0000 . ?
C16 C17 1.5214(17) . ?
C16 C18 1.5176(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.3823(18) . ?
C8 H8 0.9500 . ?
C8 C7 1.382(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3816(19) . ?
C12 H12 0.9500 . ?
C12 C13 1.373(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19 H19 1.0000 . ?
C19 C20 1.518(2) . ?
C19 C21 1.519(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.381(2) . ?
C6 H6 0.9500 . ?
C15 H15 0.9500 . ?
C15 C14 1.3816(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.372(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C14 H14 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
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
O1 C1 C4 C9 -5.91(15) . . . . ?
O1 C1 C4 C5 175.22(10) . . . . ?
O1 C2 C10 C11 8.61(16) . . . . ?
O1 C2 C10 C15 -172.31(12) . . . . ?
N2 N3 N4 C16 179.16(9) . . . . ?
N2 N3 N4 C19 1.95(16) . . . . ?
N2 C3 C2 O1 -176.54(9) . . . . ?
N2 C3 C2 C10 1.4(2) . . . . ?
N3 N2 C3 N1 -11.63(14) . . . . ?
N3 N2 C3 C2 165.06(10) . . . . ?
N3 N4 C16 C17 56.83(13) . . . . ?
N3 N4 C16 C18 -68.42(13) . . . . ?
N3 N4 C19 C20 -116.34(13) . . . . ?
N3 N4 C19 C21 118.58(12) . . . . ?
N1 C3 C2 O1 0.62(11) . . . . ?
N1 C3 C2 C10 178.60(12) . . . . ?
N1 C1 C4 C9 173.21(11) . . . . ?
N1 C1 C4 C5 -5.66(18) . . . . ?
C3 N2 N3 N4 -177.14(9) . . . . ?
C3 N1 C1 O1 -0.22(12) . . . . ?
C3 N1 C1 C4 -179.36(11) . . . . ?
C3 C2 C10 C11 -169.22(12) . . . . ?
C3 C2 C10 C15 9.9(2) . . . . ?
C1 O1 C2 C3 -0.71(11) . . . . ?
C1 O1 C2 C10 -179.14(9) . . . . ?
C1 N1 C3 N2 176.84(10) . . . . ?
C1 N1 C3 C2 -0.26(12) . . . . ?
C1 C4 C9 C8 -179.75(11) . . . . ?
C1 C4 C5 C6 179.73(12) . . . . ?
C4 C9 C8 C7 -0.1(2) . . . . ?
C4 C5 C6 C7 0.2(2) . . . . ?
C2 O1 C1 N1 0.60(12) . . . . ?
C2 O1 C1 C4 179.85(9) . . . . ?
C2 C10 C11 C12 -179.77(12) . . . . ?
C2 C10 C15 C14 -179.88(15) . . . . ?
C10 C11 C12 C13 -0.5(2) . . . . ?
C10 C15 C14 C13 -0.2(3) . . . . ?
C9 C4 C5 C6 0.8(2) . . . . ?
C9 C8 C7 C6 1.2(2) . . . . ?
C16 N4 C19 C20 66.64(15) . . . . ?
C16 N4 C19 C21 -58.44(15) . . . . ?
C11 C10 C15 C14 -0.8(2) . . . . ?
C11 C12 C13 C14 -0.5(3) . . . . ?
C8 C7 C6 C5 -1.2(2) . . . . ?
C5 C4 C9 C8 -0.88(18) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C19 N4 C16 C17 -125.87(12) . . . . ?
C19 N4 C16 C18 108.88(13) . . . . ?
C15 C10 C11 C12 1.1(2) . . . . ?
