#------------------------------------------------------------------------------
#$Date: 2024-09-06 04:54:44 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294624 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/00/7160079.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_7160079
loop_
_publ_author_name
'Jena, Chinmay K.'
'Sharma, Nagendra K.'
_publ_section_title
;
 Non-benzenoid N-aryl oxalamide: synthesis of troponyl-oxalamide
 peptides by Pd(II)-catalyzed C(sp³)-H functionalization of
 glycinamides.
;
_journal_issue                   33
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6822
_journal_page_last               6832
_journal_paper_doi               10.1039/d4ob00800f
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         '0.182(C12 H12 N2 O5)'
_chemical_formula_sum            'C2.18 H2.18 N0.36 O0.91'
_chemical_formula_weight         48.04
_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_date             2023-06-28
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-01-29 deposited with the CCDC.	2024-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                113.570(7)
_cell_angle_beta                 95.895(8)
_cell_angle_gamma                112.019(9)
_cell_formula_units_Z            11
_cell_length_a                   8.1779(9)
_cell_length_b                   9.0116(6)
_cell_length_c                   10.0761(8)
_cell_measurement_reflns_used    3146
_cell_measurement_temperature    205(6)
_cell_measurement_theta_max      27.9960
_cell_measurement_theta_min      4.0910
_cell_volume                     602.44(12)
_computing_cell_refinement       'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.52a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      205.15
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.798
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     11.00  59.00   0.50    0.50    --    3.51-134.00-128.00   96
  2  ω     11.00  60.00   0.50    0.50    --    3.51-135.00  52.00   98
  3  ω      0.00  70.00   0.50    0.50    --    3.51  37.00 120.00  140
  4  ω     -8.00  66.00   0.50    0.50    --    3.51  57.00 -60.00  148
  5  ω    -42.00  19.00   0.50    0.50    --   -4.14 -77.00-120.00  122
  6  ω    -27.00  21.00   0.50    0.50    --   -4.14  77.00   0.00   96
  7  ω    -15.00  29.00   0.50    0.50    --   -4.14 -99.00 150.00   88
  8  ω    -18.00  21.00   0.50    0.50    --   -4.14  77.00 150.00   78
  9  ω    -42.00  19.00   0.50    0.50    --   -4.14 -77.00  30.00  122
 10  ω    -16.00  59.00   0.50    0.50    --   -4.14  57.00-150.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.798
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10853
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.798
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.469
_diffrn_reflns_theta_min         3.406
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.52a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_description       plate
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0499
_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)+(0.0686P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1371
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1937
_reflns_number_total             2925
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00800f2.cif
_cod_data_source_block           nks-ckj-999_auto
_cod_depositor_comments
'Adding full bibliography for 7160076--7160081.cif.'
_cod_original_cell_volume        602.44(10)
_cod_database_code               7160079
_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   1.000
_shelx_estimated_absorpt_t_min   0.999
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C3(H3), C7(H7), C5(H5), C4(H4), C6(H6)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
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
O5 O 0.13561(18) 0.89379(16) 0.00593(13) 0.0527(3) Uani 1 1 d . . . . .
O3 O 0.02685(18) 0.53166(15) 0.26671(14) 0.0557(4) Uani 1 1 d . . . . .
O2 O 0.43558(19) 0.84357(16) 0.56307(14) 0.0585(4) Uani 1 1 d . . . . .
O1 O 0.07505(19) 0.22113(15) 0.44184(14) 0.0580(4) Uani 1 1 d . . . . .
O4 O 0.3363(2) 0.8029(2) 0.06851(16) 0.0649(4) Uani 1 1 d . . . . .
N1 N 0.24103(19) 0.54816(16) 0.49622(14) 0.0406(3) Uani 1 1 d . . . . .
H1 H 0.134024 0.460814 0.433476 0.049 Uiso 1 1 calc R U . . .
N2 N 0.2212(2) 0.82123(18) 0.32536(15) 0.0456(4) Uani 1 1 d . . . . .
H2 H 0.324964 0.915953 0.386449 0.055 Uiso 1 1 calc R U . . .
C11 C 0.2119(2) 0.8387(2) 0.08791(18) 0.0424(4) Uani 1 1 d . . . . .
C9 C 0.1659(2) 0.6743(2) 0.34531(18) 0.0398(4) Uani 1 1 d . . . . .
C2 C 0.3251(2) 0.5072(2) 0.59466(16) 0.0371(4) Uani 1 1 d . . . . .
C1 C 0.2146(2) 0.3145(2) 0.55389(18) 0.0408(4) Uani 1 1 d . . . . .
C8 C 0.2976(2) 0.7006(2) 0.48175(17) 0.0395(4) Uani 1 1 d . . . . .
C3 C 0.4866(3) 0.6333(2) 0.70685(18) 0.0459(4) Uani 1 1 d . . . . .
H3 H 0.533046 0.750228 0.715167 0.055 Uiso 1 1 calc R U . . .
C7 C 0.2615(3) 0.2319(2) 0.63802(19) 0.0473(4) Uani 1 1 d . . . . .
H7 H 0.174947 0.110670 0.604166 0.057 Uiso 1 1 calc R U . . .
C5 C 0.5622(3) 0.4704(2) 0.83557(18) 0.0502(4) Uani 1 1 d . . . . .
H5 H 0.652585 0.486597 0.912789 0.060 Uiso 1 1 calc R U . . .
C10 C 0.1165(3) 0.8297(2) 0.2071(2) 0.0498(4) Uani 1 1 d . . . . .
H10A H 0.095812 0.937218 0.252169 0.060 Uiso 1 1 calc R U . . .
H10B H -0.004482 0.722022 0.158631 0.060 Uiso 1 1 calc R U . . .
C4 C 0.5956(3) 0.6159(2) 0.81292(19) 0.0513(5) Uani 1 1 d . . . . .
H4 H 0.707194 0.720388 0.876718 0.062 Uiso 1 1 calc R U . . .
C6 C 0.4078(3) 0.2977(3) 0.7570(2) 0.0514(4) Uani 1 1 d . . . . .
H6 H 0.406196 0.215597 0.792746 0.062 Uiso 1 1 calc R U . . .
C12 C 0.2096(3) 0.9030(3) -0.1166(2) 0.0607(5) Uani 1 1 d . . . . .
H12A H 0.206702 0.787328 -0.179981 0.091 Uiso 1 1 calc R U . . .
H12B H 0.336108 0.998427 -0.074978 0.091 Uiso 1 1 calc R U . . .
H12C H 0.135627 0.929425 -0.176959 0.091 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
C11 O5 C12 115.67(15) . . ?
C2 N1 H1 114.6 . . ?
C8 N1 H1 114.6 . . ?
C8 N1 C2 130.80(13) . . ?
C9 N2 H2 118.6 . . ?
C9 N2 C10 122.80(14) . . ?
C10 N2 H2 118.6 . . ?
O5 C11 C10 109.57(15) . . ?
O4 C11 O5 124.32(16) . . ?
O4 C11 C10 126.11(15) . . ?
O3 C9 N2 125.62(15) . . ?
O3 C9 C8 121.34(14) . . ?
N2 C9 C8 113.04(14) . . ?
N1 C2 C1 109.46(13) . . ?
C3 C2 N1 121.92(13) . . ?
C3 C2 C1 128.61(14) . . ?
O1 C1 C2 117.74(14) . . ?
O1 C1 C7 119.26(14) . . ?
C7 C1 C2 123.00(15) . . ?
O2 C8 N1 126.27(15) . . ?
O2 C8 C9 122.10(14) . . ?
N1 C8 C9 111.63(13) . . ?
C2 C3 H3 115.0 . . ?
C2 C3 C4 130.09(15) . . ?
C4 C3 H3 115.0 . . ?
C1 C7 H7 114.3 . . ?
C6 C7 C1 131.46(16) . . ?
C6 C7 H7 114.3 . . ?
C4 C5 H5 116.2 . . ?
C4 C5 C6 127.56(17) . . ?
C6 C5 H5 116.2 . . ?
N2 C10 C11 112.67(15) . . ?
N2 C10 H10A 109.1 . . ?
N2 C10 H10B 109.1 . . ?
C11 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C3 C4 H4 115.4 . . ?
C5 C4 C3 129.26(17) . . ?
C5 C4 H4 115.4 . . ?
C7 C6 C5 129.79(16) . . ?
C7 C6 H6 115.1 . . ?
C5 C6 H6 115.1 . . ?
O5 C12 H12A 109.5 . . ?
O5 C12 H12B 109.5 . . ?
O5 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
O5 C11 1.3312(19) . ?
O5 C12 1.448(2) . ?
O3 C9 1.216(2) . ?
O2 C8 1.2164(19) . ?
O1 C1 1.241(2) . ?
O4 C11 1.189(2) . ?
N1 H1 0.8700 . ?
N1 C2 1.3910(19) . ?
N1 C8 1.3492(19) . ?
N2 H2 0.8700 . ?
N2 C9 1.3347(19) . ?
N2 C10 1.439(2) . ?
C11 C10 1.511(2) . ?
C9 C8 1.533(2) . ?
C2 C1 1.476(2) . ?
C2 C3 1.362(2) . ?
C1 C7 1.439(2) . ?
C3 H3 0.9400 . ?
C3 C4 1.416(2) . ?
C7 H7 0.9400 . ?
C7 C6 1.351(2) . ?
C5 H5 0.9400 . ?
C5 C4 1.352(2) . ?
C5 C6 1.407(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C4 H4 0.9400 . ?
C6 H6 0.9400 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
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
O5 C11 C10 N2 -163.73(13) . . . . ?
O3 C9 C8 O2 -178.65(16) . . . . ?
O3 C9 C8 N1 1.9(2) . . . . ?
O1 C1 C7 C6 175.97(18) . . . . ?
O4 C11 C10 N2 16.2(2) . . . . ?
N1 C2 C1 O1 2.2(2) . . . . ?
N1 C2 C1 C7 -177.63(15) . . . . ?
N1 C2 C3 C4 -177.22(16) . . . . ?
N2 C9 C8 O2 1.3(2) . . . . ?
N2 C9 C8 N1 -178.15(13) . . . . ?
C9 N2 C10 C11 -112.34(18) . . . . ?
C2 N1 C8 O2 -5.3(3) . . . . ?
C2 N1 C8 C9 174.11(14) . . . . ?
C2 C1 C7 C6 -4.2(3) . . . . ?
C2 C3 C4 C5 -3.9(3) . . . . ?
C1 C2 C3 C4 1.5(3) . . . . ?
C1 C7 C6 C5 -0.4(3) . . . . ?
C8 N1 C2 C1 -174.18(15) . . . . ?
C8 N1 C2 C3 4.7(3) . . . . ?
C3 C2 C1 O1 -176.59(17) . . . . ?
C3 C2 C1 C7 3.5(3) . . . . ?
C10 N2 C9 O3 1.8(3) . . . . ?
C10 N2 C9 C8 -178.12(14) . . . . ?
C4 C5 C6 C7 3.2(3) . . . . ?
C6 C5 C4 C3 0.2(3) . . . . ?
C12 O5 C11 O4 2.0(2) . . . . ?
C12 O5 C11 C10 -178.02(13) . . . . ?
