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#$Date: 2024-07-05 19:31:38 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293078 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/62/7716249.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_7716249
loop_
_publ_author_name
'Kao, Cheng-Po'
'Lee, Jhen-Yi'
'Tang, Min-Cheng'
'Lee, Hon Man'
_publ_section_title
;
 Design and synthesis of versatile ligand precursors based on phosphonium
 ylides for palladalactam formation and catalytic investigation.
;
_journal_issue                   25
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              10475
_journal_page_last               10485
_journal_paper_doi               10.1039/d4dt00862f
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C4 H6 N3 O, N O3'
_chemical_formula_sum            'C4 H6 N4 O4'
_chemical_formula_weight         174.13
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-03-15 deposited with the CCDC.	2024-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                97.482(5)
_cell_angle_beta                 92.225(5)
_cell_angle_gamma                92.406(5)
_cell_formula_units_Z            4
_cell_length_a                   4.6869(7)
_cell_length_b                   11.2109(18)
_cell_length_c                   13.967(2)
_cell_measurement_reflns_used    4995
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.50
_cell_volume                     726.27(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.42
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11335
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.601
_diffrn_reflns_theta_min         2.195
_diffrn_source.source            'Ius 2.0'
_diffrn_source.type              microfocus
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3329
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0511
_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)+(0.0659P)²+0.2826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.1393
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2368
_reflns_number_total             3329
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt00862f2.cif
_cod_data_source_block           YF_117_a
_cod_depositor_comments
'Adding full bibliography for 7716247--7716254.cif.'
_cod_original_cell_volume        726.28(19)
_cod_database_code               7716249
_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_min   0.969
_shelx_estimated_absorpt_t_max   0.992
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
C1 C 0.7043(4) 0.48369(16) 0.71137(13) 0.0353(4) Uani 1 1 d . . . . .
C2 C 0.4030(5) 0.5779(2) 0.80874(15) 0.0478(5) Uani 1 1 d . . . . .
H2 H 0.270897 0.632255 0.833191 0.057 Uiso 1 1 calc R U . . .
C3 C 0.5108(5) 0.4891(2) 0.85261(15) 0.0534(6) Uani 1 1 d . . . . .
H3A H 0.466847 0.470210 0.913405 0.064 Uiso 1 1 calc R U . . .
C4 C 0.8732(4) 0.45363(17) 0.62843(14) 0.0373(4) Uani 1 1 d . . . . .
H4 H 0.853592 0.493964 0.574593 0.045 Uiso 1 1 calc R U . . .
C5 C 0.5276(4) 0.95424(17) 0.25137(13) 0.0368(4) Uani 1 1 d . . . . .
C6 C 0.5341(5) 1.0595(2) 0.12882(16) 0.0525(6) Uani 1 1 d . . . . .
H6 H 0.581282 1.086003 0.070815 0.063 Uiso 1 1 calc R U . . .
C7 C 0.3422(5) 1.10637(19) 0.19004(14) 0.0456(5) Uani 1 1 d . . . . .
H7 H 0.230849 1.171498 0.182407 0.055 Uiso 1 1 calc R U . . .
C8 C 0.6069(4) 0.86284(19) 0.31020(15) 0.0456(5) Uani 1 1 d . . . . .
H8 H 0.750792 0.813735 0.286919 0.055 Uiso 1 1 calc R U . . .
N1 N 0.5250(3) 0.57299(14) 0.72115(11) 0.0385(4) Uani 1 1 d . . . . .
H1 H 0.491036 0.620382 0.678768 0.046 Uiso 1 1 calc R U . . .
N2 N 0.6964(4) 0.43168(16) 0.79177(12) 0.0455(4) Uani 1 1 d . . . . .
H2A H 0.793268 0.371303 0.803431 0.055 Uiso 1 1 calc R U . . .
N3 N 1.0496(3) 0.37072(14) 0.63037(11) 0.0376(4) Uani 1 1 d . . . . .
N4 N 0.6468(4) 0.96564(16) 0.16765(12) 0.0465(4) Uani 1 1 d . . . . .
H4A H 0.775241 0.920600 0.142125 0.056 Uiso 1 1 calc R U . . .
N5 N 0.3411(3) 1.04037(14) 0.26586(11) 0.0368(4) Uani 1 1 d . . . . .
H5 H 0.236447 1.052619 0.315095 0.044 Uiso 1 1 calc R U . . .
N6 N 0.5057(4) 0.84075(15) 0.38970(13) 0.0462(4) Uani 1 1 d . . . . .
N7 N 0.9351(5) 0.2406(2) 0.94388(14) 0.0644(6) Uani 1 1 d . . . . .
N8 N 0.1699(3) 0.78009(14) 0.62076(11) 0.0378(4) Uani 1 1 d . . . . .
O1 O 1.2015(3) 0.35634(14) 0.54684(10) 0.0466(4) Uani 1 1 d . . . . .
H1A H 1.306(6) 0.293(3) 0.554(2) 0.086(10) Uiso 1 1 d . . . . .
O2 O 0.2927(3) 0.91554(14) 0.41844(11) 0.0500(4) Uani 1 1 d . . . . .
H2B H 0.249(6) 0.898(3) 0.479(2) 0.088(9) Uiso 1 1 d . . . . .
O3 O 0.9700(4) 0.23841(16) 0.85614(11) 0.0662(5) Uani 1 1 d . . . . .
O4 O 0.8083(9) 0.3201(3) 0.98627(16) 0.1759(19) Uani 1 1 d . . . . .
O5 O 1.0260(5) 0.1590(2) 0.98455(16) 0.0967(8) Uani 1 1 d . . . . .
O6 O 0.3753(3) 0.72884(14) 0.58262(11) 0.0522(4) Uani 1 1 d . . . . .
O7 O 0.0796(3) 0.87293(12) 0.59047(10) 0.0474(4) Uani 1 1 d . . . . .
O8 O 0.0550(3) 0.74041(15) 0.68902(11) 0.0584(4) Uani 1 1 d . . . . .
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
N2 C1 N1 106.97(16) . . ?
N2 C1 C4 128.33(17) . . ?
N1 C1 C4 124.69(17) . . ?
C3 C2 N1 106.64(18) . . ?
C3 C2 H2 126.7 . . ?
N1 C2 H2 126.7 . . ?
C2 C3 N2 107.42(18) . . ?
C2 C3 H3A 126.3 . . ?
N2 C3 H3A 126.3 . . ?
N3 C4 C1 118.58(17) . . ?
N3 C4 H4 120.7 . . ?
C1 C4 H4 120.7 . . ?
N5 C5 N4 107.04(16) . . ?
N5 C5 C8 130.60(17) . . ?
N4 C5 C8 122.35(17) . . ?
C7 C6 N4 107.02(19) . . ?
C7 C6 H6 126.5 . . ?
N4 C6 H6 126.5 . . ?
C6 C7 N5 107.11(18) . . ?
C6 C7 H7 126.4 . . ?
N5 C7 H7 126.4 . . ?
N6 C8 C5 128.52(19) . . ?
N6 C8 H8 115.7 . . ?
C5 C8 H8 115.7 . . ?
C1 N1 C2 109.65(16) . . ?
C1 N1 H1 125.2 . . ?
C2 N1 H1 125.2 . . ?
C1 N2 C3 109.32(16) . . ?
C1 N2 H2A 125.3 . . ?
C3 N2 H2A 125.3 . . ?
C4 N3 O1 111.18(15) . . ?
C5 N4 C6 109.58(17) . . ?
C5 N4 H4A 125.2 . . ?
C6 N4 H4A 125.2 . . ?
C5 N5 C7 109.24(16) . . ?
C5 N5 H5 125.4 . . ?
C7 N5 H5 125.4 . . ?
C8 N6 O2 112.25(16) . . ?
O4 N7 O5 121.5(2) . . ?
O4 N7 O3 119.9(2) . . ?
O5 N7 O3 118.6(2) . . ?
O8 N8 O6 120.15(16) . . ?
O8 N8 O7 119.72(16) . . ?
O6 N8 O7 120.13(16) . . ?
N3 O1 H1A 103.6(19) . . ?
N6 O2 H2B 105.3(19) . . ?
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
C1 N2 1.332(2) . ?
C1 N1 1.331(2) . ?
C1 C4 1.440(3) . ?
C2 C3 1.341(3) . ?
C2 N1 1.366(3) . ?
C2 H2 0.9300 . ?
C3 N2 1.362(3) . ?
C3 H3A 0.9300 . ?
C4 N3 1.272(2) . ?
C4 H4 0.9300 . ?
C5 N5 1.331(2) . ?
C5 N4 1.334(2) . ?
C5 C8 1.446(3) . ?
C6 C7 1.341(3) . ?
C6 N4 1.361(3) . ?
C6 H6 0.9300 . ?
C7 N5 1.369(2) . ?
C7 H7 0.9300 . ?
C8 N6 1.274(3) . ?
C8 H8 0.9300 . ?
N1 H1 0.8600 . ?
N2 H2A 0.8600 . ?
N3 O1 1.385(2) . ?
N4 H4A 0.8600 . ?
N5 H5 0.8600 . ?
N6 O2 1.369(2) . ?
N7 O4 1.197(3) . ?
N7 O5 1.221(2) . ?
N7 O3 1.240(2) . ?
N8 O8 1.236(2) . ?
N8 O6 1.244(2) . ?
N8 O7 1.257(2) . ?
O1 H1A 0.89(3) . ?
O2 H2B 0.93(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 O4 0.93 2.55 3.154(3) 122.7 2_667 yes
C3 H3A O4 0.93 2.64 3.156(3) 115.6 . yes
C4 H4 O1 0.93 2.55 3.465(2) 168.0 2_766 yes
C6 H6 O5 0.93 2.60 3.369(3) 140.0 1_564 yes
C7 H7 O8 0.93 2.41 3.004(3) 121.3 2_576 yes
C8 H8 N3 0.93 2.68 3.310(3) 125.6 2_766 yes
C8 H8 O3 0.93 2.45 3.237(3) 142.2 2_766 yes
N1 H1 N8 0.86 2.58 3.334(2) 147.6 . yes
N1 H1 O6 0.86 2.00 2.858(2) 174.9 . yes
N1 H1 O8 0.86 2.49 3.011(2) 119.6 . yes
N2 H2A N7 0.86 2.68 3.399(2) 142.4 . yes
N2 H2A O3 0.86 1.95 2.793(2) 167.5 . yes
N4 H4A N7 0.86 2.51 3.360(3) 168.2 2_766 yes
N4 H4A O3 0.86 2.19 2.960(2) 149.1 2_766 yes
N4 H4A O5 0.86 2.14 2.912(3) 149.2 2_766 yes
N5 H5 O2 0.86 2.26 2.709(2) 112.8 . yes
N5 H5 O7 0.86 2.14 2.970(2) 160.7 2_576 yes
O1 H1A N6 0.89(3) 2.00(3) 2.867(2) 162(3) 2_766 yes
O2 H2B N8 0.93(3) 2.55(3) 3.434(2) 161(3) . yes
O2 H2B O6 0.93(3) 2.60(3) 3.322(2) 135(2) . yes
O2 H2B O7 0.93(3) 1.82(3) 2.728(2) 166(3) . yes
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
N1 C2 C3 N2 0.1(3) . . . . ?
N2 C1 C4 N3 -3.3(3) . . . . ?
N1 C1 C4 N3 175.80(18) . . . . ?
N4 C6 C7 N5 0.2(2) . . . . ?
N5 C5 C8 N6 3.0(4) . . . . ?
N4 C5 C8 N6 -178.2(2) . . . . ?
N2 C1 N1 C2 0.2(2) . . . . ?
C4 C1 N1 C2 -179.06(19) . . . . ?
C3 C2 N1 C1 -0.2(3) . . . . ?
N1 C1 N2 C3 -0.1(2) . . . . ?
C4 C1 N2 C3 179.1(2) . . . . ?
C2 C3 N2 C1 0.0(3) . . . . ?
C1 C4 N3 O1 -177.75(16) . . . . ?
N5 C5 N4 C6 -0.2(2) . . . . ?
C8 C5 N4 C6 -179.3(2) . . . . ?
C7 C6 N4 C5 0.0(3) . . . . ?
N4 C5 N5 C7 0.3(2) . . . . ?
C8 C5 N5 C7 179.3(2) . . . . ?
C6 C7 N5 C5 -0.3(2) . . . . ?
C5 C8 N6 O2 0.9(3) . . . . ?
