#------------------------------------------------------------------------------
#$Date: 2024-09-06 04:54:44 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294624 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/00/7160077.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_7160077
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         'C17 H16 N2 O3'
_chemical_formula_sum            'C17 H16 N2 O3'
_chemical_formula_weight         296.32
_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             2021-12-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-01-29 deposited with the CCDC.	2024-07-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.208(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8803(10)
_cell_length_b                   13.7121(9)
_cell_length_c                   8.2130(5)
_cell_measurement_reflns_used    4711
_cell_measurement_temperature    248(50)
_cell_measurement_theta_max      30.0990
_cell_measurement_theta_min      3.7440
_cell_volume                     1515.35(18)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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_environment      N~2~
_diffrn_ambient_temperature      248(50)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.819
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00   7.00   0.50   31.67    --    3.35 -36.00 -75.00  134
  2  ω      0.00  70.00   0.50   31.67    --    3.35  36.00  80.00  140
  3  ω    -17.00  19.00   0.50   31.67    --   -3.98  77.00 -60.00   72
  4  ω     -6.00  27.00   0.50   31.67    --   -3.98 -99.00 -30.00   66
  5  ω    -25.00   2.00   0.50   31.67    --   -3.98  77.00  90.00   54
  6  ω    -23.00   5.00   0.50   31.67    --   -3.98  77.00-120.00   56
  7  ω    -27.00  18.00   0.50   31.67    --   -3.98  77.00 150.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0367950000
_diffrn_orient_matrix_UB_12      -0.0237283000
_diffrn_orient_matrix_UB_13      0.0322425000
_diffrn_orient_matrix_UB_21      0.0335431000
_diffrn_orient_matrix_UB_22      -0.0023585000
_diffrn_orient_matrix_UB_23      0.0804144000
_diffrn_orient_matrix_UB_31      -0.0173096000
_diffrn_orient_matrix_UB_32      0.0458955000
_diffrn_orient_matrix_UB_33      0.0207847000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.819
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14346
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.132
_diffrn_reflns_theta_min         3.335
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear brownish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0433
_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)+(0.0533P)²+0.1540P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1252
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2428
_reflns_number_total             3667
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00800f2.cif
_cod_data_source_block           nks-ckj-420(a)
_cod_depositor_comments
'Adding full bibliography for 7160076--7160081.cif.'
_cod_database_code               7160077
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C68 H64 N8 O12 '
_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
_diffrn_oxdiff_digest_frames
;
01e3172aa315766ee2e3e380e12caae8fa00025c825
;
_diffrn_oxdiff_digest_hkl
;
01c26d0cd56c4973b969add3ae14b3357bfb6b
;
_reflns_odcompleteness_completeness 99.17
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C3(H3), C17(H17), C13(H13), C5(H5), C4(H4), C14(H14),
 C15(H15), C16(H16), C7(H7), C6(H6)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.513
_oxdiff_exptl_absorpt_empirical_full_min 0.718
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 0.64260(8) 0.63379(8) 0.87355(12) 0.0687(3) Uani 1 1 d . . . . .
O2 O 0.57267(8) 0.63220(9) 0.27162(12) 0.0680(3) Uani 1 1 d . . . . .
N1 N 0.62027(8) 0.63381(8) 0.55835(13) 0.0501(3) Uani 1 1 d . . . . .
H1 H 0.673215 0.638002 0.638551 0.060 Uiso 1 1 calc R . . . .
N2 N 0.76713(8) 0.64212(8) 0.25844(14) 0.0528(3) Uani 1 1 d . . . . .
H2 H 0.719730 0.635541 0.169399 0.063 Uiso 1 1 calc R . . . .
O3 O 0.80830(8) 0.63660(10) 0.54260(14) 0.0810(4) Uani 1 1 d . . . . .
C2 C 0.53246(9) 0.62789(9) 0.60950(15) 0.0444(3) Uani 1 1 d . . . . .
C8 C 0.63577(10) 0.63403(9) 0.40206(16) 0.0486(3) Uani 1 1 d . . . . .
C1 C 0.55412(10) 0.62709(9) 0.79383(16) 0.0499(3) Uani 1 1 d . . . . .
C9 C 0.74713(10) 0.63767(10) 0.40787(17) 0.0524(3) Uani 1 1 d . . . . .
C12 C 0.88675(9) 0.50002(10) 0.09235(16) 0.0514(3) Uani 1 1 d . . . . .
C3 C 0.44242(10) 0.62343(11) 0.49753(18) 0.0575(4) Uani 1 1 d . . . . .
H3 H 0.444611 0.626648 0.385388 0.069 Uiso 1 1 calc R . . . .
C10 C 0.86825(11) 0.65800(11) 0.2426(2) 0.0622(4) Uani 1 1 d . . . . .
H10A H 0.914581 0.632630 0.341823 0.075 Uiso 1 1 calc R . . . .
H10B H 0.879956 0.727536 0.237434 0.075 Uiso 1 1 calc R . . . .
C17 C 0.82751(11) 0.44772(11) -0.0378(2) 0.0639(4) Uani 1 1 d . . . . .
H17 H 0.787798 0.480701 -0.128848 0.077 Uiso 1 1 calc R . . . .
C13 C 0.94568(11) 0.44789(11) 0.22451(19) 0.0643(4) Uani 1 1 d . . . . .
H13 H 0.987368 0.481450 0.312645 0.077 Uiso 1 1 calc R . . . .
C11 C 0.88820(11) 0.60958(10) 0.0881(2) 0.0617(4) Uani 1 1 d . . . . .
H11A H 0.838653 0.631645 -0.009967 0.074 Uiso 1 1 calc R . . . .
H11B H 0.952645 0.630807 0.075494 0.074 Uiso 1 1 calc R . . . .
C5 C 0.31737(12) 0.60877(12) 0.6689(2) 0.0684(4) Uani 1 1 d . . . . .
H5 H 0.249505 0.602929 0.659811 0.082 Uiso 1 1 calc R . . . .
C4 C 0.34582(11) 0.61467(12) 0.5242(2) 0.0674(4) Uani 1 1 d . . . . .
H4 H 0.294455 0.612701 0.427197 0.081 Uiso 1 1 calc R . . . .
C14 C 0.94384(13) 0.34819(12) 0.2281(2) 0.0722(5) Uani 1 1 d . . . . .
H14 H 0.983165 0.314748 0.318936 0.087 Uiso 1 1 calc R . . . .
C15 C 0.88416(13) 0.29763(12) 0.0981(2) 0.0744(5) Uani 1 1 d . . . . .
H15 H 0.882986 0.229831 0.100268 0.089 Uiso 1 1 calc R . . . .
C16 C 0.82636(13) 0.34699(12) -0.0348(2) 0.0751(5) Uani 1 1 d . . . . .
H16 H 0.786098 0.312713 -0.123608 0.090 Uiso 1 1 calc R . . . .
C7 C 0.47807(13) 0.61848(13) 0.88297(19) 0.0723(5) Uani 1 1 d . . . . .
H7 H 0.501767 0.618383 0.999170 0.087 Uiso 1 1 calc R . . . .
C6 C 0.37828(13) 0.61046(13) 0.8301(2) 0.0765(5) Uani 1 1 d . . . . .
H6 H 0.345219 0.605247 0.915485 0.092 Uiso 1 1 calc R . . . .
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
C8 N1 C2 130.12(11) . . ?
C9 N2 C10 120.99(13) . . ?
N1 C2 C1 109.87(11) . . ?
C3 C2 N1 121.92(11) . . ?
C3 C2 C1 128.20(12) . . ?
O2 C8 N1 126.36(13) . . ?
O2 C8 C9 122.29(12) . . ?
N1 C8 C9 111.34(11) . . ?
O1 C1 C2 117.86(12) . . ?
O1 C1 C7 119.59(13) . . ?
C7 C1 C2 122.56(13) . . ?
N2 C9 C8 114.27(12) . . ?
O3 C9 N2 125.76(13) . . ?
O3 C9 C8 119.97(12) . . ?
C17 C12 C13 117.63(14) . . ?
C17 C12 C11 120.69(14) . . ?
C13 C12 C11 121.66(14) . . ?
C2 C3 C4 130.37(14) . . ?
N2 C10 C11 112.75(12) . . ?
C12 C17 C16 120.88(15) . . ?
C14 C13 C12 121.44(15) . . ?
C12 C11 C10 114.30(12) . . ?
C4 C5 C6 126.99(15) . . ?
C5 C4 C3 129.58(15) . . ?
C13 C14 C15 120.03(16) . . ?
C16 C15 C14 119.81(16) . . ?
C15 C16 C17 120.19(16) . . ?
C6 C7 C1 132.09(15) . . ?
C7 C6 C5 130.20(15) . . ?
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 1.2453(17) . ?
O2 C8 1.2061(16) . ?
N1 C2 1.3856(16) . ?
N1 C8 1.3526(16) . ?
N2 C9 1.3244(17) . ?
N2 C10 1.4572(17) . ?
O3 C9 1.2184(17) . ?
C2 C1 1.4694(17) . ?
C2 C3 1.3591(19) . ?
C8 C9 1.5356(19) . ?
C1 C7 1.430(2) . ?
C12 C17 1.379(2) . ?
C12 C13 1.386(2) . ?
C12 C11 1.503(2) . ?
C3 C4 1.416(2) . ?
C10 C11 1.517(2) . ?
C17 C16 1.382(2) . ?
C13 C14 1.368(2) . ?
C5 C4 1.343(2) . ?
C5 C6 1.386(2) . ?
C14 C15 1.369(2) . ?
C15 C16 1.365(2) . ?
C7 C6 1.351(2) . ?
