#------------------------------------------------------------------------------
#$Date: 2024-09-06 04:54:44 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294624 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/00/7160078.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_7160078
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         'C16 H14 N2 O3'
_chemical_formula_sum            'C10 H22 N2 O7'
_chemical_formula_weight         282.29
_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
_audit_creation_date             2021-06-20
_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                 102.069(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9666(11)
_cell_length_b                   13.3233(10)
_cell_length_c                   8.2903(6)
_cell_measurement_reflns_used    4767
_cell_measurement_temperature    292(3)
_cell_measurement_theta_max      30.4250
_cell_measurement_theta_min      3.9400
_cell_volume                     1400.56(19)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      292(3)
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -37.00  66.00   0.50   85.00    --   -3.82   3.00  90.00  206
  2  ω    -60.00 -26.00   0.50   85.00    --   -3.82  -3.00 -87.00   68
  3  ω     14.00  39.00   0.50   85.00    --    3.51 -99.00-150.00   50
  4  ω    -19.00  32.00   0.50   85.00    --   -3.82 -99.00 -90.00  102
  5  ω    -63.00   0.00   0.50   85.00    --   -3.82 -38.00-120.00  126
  6  ω    -20.00   5.00   0.50   85.00    --   -3.82 -99.00  60.00   50
;
_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  0.0297
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12306
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         3.455
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.021
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.791
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2846
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.791
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0417
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1687
_refine_ls_wR_factor_ref         0.1942
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2181
_reflns_number_total             2846
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00800f2.cif
_cod_data_source_block           nks_ckj_214
_cod_depositor_comments
'Adding full bibliography for 7160076--7160081.cif.'
_cod_database_code               7160078
_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.
;
_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)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C6(H6), C12(H12), C16(H16), C14(H14), C13(H13), C5(H5),
 C15(H15), C2(H2A), C4(H4), C3(H3)
;
_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+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
N1 N 0.89458(11) 0.13720(9) 0.02302(16) 0.0504(4) Uani 1 1 d . . . . .
H1 H 0.836735 0.138493 -0.050030 0.060 Uiso 1 1 calc R . . . .
O2 O 0.95373(10) 0.14633(9) 0.30146(14) 0.0634(4) Uani 1 1 d . . . . .
N2 N 0.75386(11) 0.13680(9) 0.34721(19) 0.0548(4) Uani 1 1 d . . . . .
H2 H 0.808720 0.140390 0.425879 0.066 Uiso 1 1 calc R . . . .
O3 O 0.69681(10) 0.14112(10) 0.07056(18) 0.0737(4) Uani 1 1 d . . . . .
C8 C 0.88284(12) 0.14192(10) 0.17977(19) 0.0470(4) Uani 1 1 d . . . . .
C9 C 0.76658(12) 0.14025(10) 0.1933(2) 0.0509(4) Uani 1 1 d . . . . .
O1 O 0.86436(12) 0.12071(10) -0.28792(16) 0.0724(4) Uani 1 1 d . . . . .
C7 C 0.98589(13) 0.13054(9) -0.03980(19) 0.0467(4) Uani 1 1 d . . . . .
C11 C 0.61526(11) 0.01920(11) 0.3891(2) 0.0536(4) Uani 1 1 d . . . . .
C1 C 0.95934(15) 0.12051(10) -0.2187(2) 0.0550(4) Uani 1 1 d . . . . .
C10 C 0.65041(14) 0.12713(12) 0.3891(3) 0.0641(5) Uani 1 1 d . . . . .
H10A H 0.599104 0.164798 0.310124 0.077 Uiso 1 1 calc R . . . .
H10B H 0.653083 0.155871 0.497387 0.077 Uiso 1 1 calc R . . . .
C6 C 1.08322(15) 0.13247(12) 0.0606(2) 0.0618(5) Uani 1 1 d . . . . .
H6 H 1.083281 0.139495 0.172193 0.074 Uiso 1 1 calc R . . . .
C12 C 0.65736(13) -0.04293(12) 0.5190(2) 0.0622(5) Uani 1 1 d . . . . .
H12 H 0.706394 -0.017473 0.607775 0.075 Uiso 1 1 calc R . . . .
C16 C 0.54215(13) -0.02082(14) 0.2604(2) 0.0669(5) Uani 1 1 d . . . . .
H16 H 0.512218 0.019631 0.171430 0.080 Uiso 1 1 calc R . . . .
C14 C 0.55562(16) -0.18042(14) 0.3915(3) 0.0756(6) Uani 1 1 d . . . . .
H14 H 0.535614 -0.247397 0.392840 0.091 Uiso 1 1 calc R . . . .
C13 C 0.62792(17) -0.14197(13) 0.5194(3) 0.0732(6) Uani 1 1 d . . . . .
H13 H 0.657649 -0.183005 0.607630 0.088 Uiso 1 1 calc R . . . .
C5 C 1.18441(17) 0.12554(16) 0.0229(3) 0.0807(6) Uani 1 1 d . . . . .
H5 H 1.240461 0.126774 0.113573 0.097 Uiso 1 1 calc R . . . .
C15 C 0.51274(16) -0.12095(16) 0.2621(3) 0.0770(6) Uani 1 1 d . . . . .
H15 H 0.463543 -0.147272 0.174427 0.092 Uiso 1 1 calc R . . . .
C2 C 1.0382(2) 0.11206(15) -0.3161(2) 0.0762(6) Uani 1 1 d . . . . .
H2A H 1.010552 0.105715 -0.428584 0.091 Uiso 1 1 calc R . . . .
C4 C 1.21189(18) 0.11741(15) -0.1250(3) 0.0808(7) Uani 1 1 d . . . . .
H4 H 1.283693 0.115615 -0.124192 0.097 Uiso 1 1 calc R . . . .
C3 C 1.1442(2) 0.11148(14) -0.2771(3) 0.0812(7) Uani 1 1 d . . . . .
H3 H 1.176938 0.106291 -0.366414 0.097 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 C7 130.02(14) . . ?
C9 N2 C10 122.63(16) . . ?
N1 C8 C9 112.46(13) . . ?
O2 C8 N1 125.95(15) . . ?
O2 C8 C9 121.59(15) . . ?
N2 C9 C8 113.19(14) . . ?
O3 C9 N2 126.09(16) . . ?
O3 C9 C8 120.72(16) . . ?
N1 C7 C1 110.37(14) . . ?
C6 C7 N1 121.56(16) . . ?
C6 C7 C1 128.07(17) . . ?
C12 C11 C10 120.16(16) . . ?
C12 C11 C16 117.98(16) . . ?
C16 C11 C10 121.85(16) . . ?
O1 C1 C7 118.01(16) . . ?
O1 C1 C2 119.56(17) . . ?
C2 C1 C7 122.43(17) . . ?
N2 C10 C11 112.13(12) . . ?
C7 C6 C5 130.5(2) . . ?
C13 C12 C11 120.92(17) . . ?
C11 C16 C15 120.63(18) . . ?
C15 C14 C13 119.89(18) . . ?
C14 C13 C12 120.45(19) . . ?
C4 C5 C6 129.7(2) . . ?
C14 C15 C16 120.13(18) . . ?
C3 C2 C1 132.7(2) . . ?
C5 C4 C3 126.6(2) . . ?
C2 C3 C4 130.0(2) . . ?
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
N1 C8 1.341(2) . ?
N1 C7 1.392(2) . ?
O2 C8 1.2159(18) . ?
N2 C9 1.321(2) . ?
N2 C10 1.460(2) . ?
O3 C9 1.212(2) . ?
C8 C9 1.535(2) . ?
O1 C1 1.245(2) . ?
C7 C1 1.457(2) . ?
C7 C6 1.359(2) . ?
C11 C10 1.509(2) . ?
C11 C12 1.378(3) . ?
C11 C16 1.378(3) . ?
C1 C2 1.434(3) . ?
C6 C5 1.414(3) . ?
C12 C13 1.374(2) . ?
C16 C15 1.388(3) . ?
C14 C13 1.360(3) . ?
C14 C15 1.356(3) . ?
C5 C4 1.351(4) . ?
C2 C3 1.344(3) . ?
C4 C3 1.380(4) . ?
