#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/74/7157483.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_7157483
loop_
_publ_author_name
'Roy, Biswajit'
'Das, Eshani'
'Roy, Avijit'
'Mal, Dipakranjan'
_publ_section_title
;
 Ni(ii)-Catalyzed vinylic C-H functionalization of
 2-acetamido-3-arylacrylates to access isotetronic acids.
;
_journal_issue                   19
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3697
_journal_page_last               3706
_journal_paper_doi               10.1039/d0ob00557f
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C11 H7 N O3'
_chemical_formula_weight         201.17
_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_method           SHELXL-2014/7
_audit_update_record
;
2018-10-08 deposited with the CCDC.	2020-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                94.77
_cell_angle_beta                 105.91
_cell_angle_gamma                108.25
_cell_formula_units_Z            4
_cell_length_a                   8.009
_cell_length_b                   9.607
_cell_length_c                   13.044
_cell_measurement_reflns_used    350
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.609
_cell_measurement_theta_min      2.824
_cell_volume                     900.812
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_molecular_graphics    'Diamond 2.1e'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       /w-scans
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8034
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.609
_diffrn_reflns_theta_min         2.824
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3650
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.1281
_refine_ls_R_factor_gt           0.0748
_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)+(0.1120P)²+0.5161P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1975
_refine_ls_wR_factor_ref         0.2304
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2118
_reflns_number_total             3650
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00557f2.cif
_cod_data_source_block           9t
_cod_depositor_comments
;
Adding full bibliography for 7157480--7157483.cif.

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        900.8
_cod_original_formula_sum        'C22 H14 N2 O6'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     402.35
_cod_database_code               7157483
_shelx_shelxl_version_number     2014/7
_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.
;
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
O3 O 0.2808(3) 0.5808(3) -0.0600(2) 0.0601(8) Uani 1 1 d . . . . .
H3A H 0.1960 0.5034 -0.0646 0.090 Uiso 1 1 calc R U . . .
O6 O 0.9215(3) 0.7340(3) 0.4426(2) 0.0603(8) Uani 1 1 d . . . . .
H6A H 0.9925 0.8148 0.4391 0.090 Uiso 1 1 calc R U . . .
O4 O 1.1741(4) 0.7484(3) 0.7165(2) 0.0628(8) Uani 1 1 d . . . . .
O1 O 0.5213(4) 0.5928(3) 0.2158(2) 0.0644(8) Uani 1 1 d . . . . .
O5 O 1.2526(4) 0.9238(3) 0.6204(2) 0.0700(9) Uani 1 1 d . . . . .
O2 O 0.2548(4) 0.4143(3) 0.1178(2) 0.0689(9) Uani 1 1 d . . . . .
C15 C 0.7388(4) 0.4537(3) 0.5314(3) 0.0391(8) Uani 1 1 d . . . . .
N1 N 0.9530(5) 1.3232(3) -0.1367(3) 0.0630(9) Uani 1 1 d . . . . .
N2 N 0.1207(5) -0.0233(4) 0.3592(3) 0.0666(10) Uani 1 1 d . . . . .
C7 C 0.8833(5) 1.2223(4) -0.1044(3) 0.0441(8) Uani 1 1 d . . . . .
C8 C 0.5603(5) 0.7357(3) 0.0823(3) 0.0421(8) Uani 1 1 d . . . . .
C1 C 0.8028(5) 1.0985(3) -0.0568(3) 0.0422(8) Uani 1 1 d . . . . .
C4 C 0.6438(5) 0.8599(3) 0.0306(3) 0.0391(8) Uani 1 1 d . . . . .
C11 C 0.4035(5) 0.6189(3) 0.0404(3) 0.0431(8) Uani 1 1 d . . . . .
C21 C 0.9792(5) 0.7032(4) 0.5418(3) 0.0433(8) Uani 1 1 d . . . . .
C22 C 1.1498(5) 0.8062(4) 0.6268(3) 0.0471(9) Uani 1 1 d . . . . .
C3 C 0.8051(5) 0.9747(4) 0.0943(3) 0.0470(9) Uani 1 1 d . . . . .
H3 H 0.8599 0.9713 0.1664 0.056 Uiso 1 1 calc R U . . .
C12 C 0.4207(4) 0.2052(4) 0.4417(3) 0.0451(9) Uani 1 1 d . . . . .
C16 C 0.6271(5) 0.4396(4) 0.4259(3) 0.0458(9) Uani 1 1 d . . . . .
H16 H 0.6595 0.5142 0.3864 0.055 Uiso 1 1 calc R U . . .
C19 C 0.9069(5) 0.5858(4) 0.5825(3) 0.0431(8) Uani 1 1 d . . . . .
C10 C 0.3774(5) 0.5272(4) 0.1241(3) 0.0475(9) Uani 1 1 d . . . . .
C18 C 0.2520(5) 0.0787(4) 0.3920(3) 0.0461(9) Uani 1 1 d . . . . .
C5 C 0.5633(5) 0.8642(4) -0.0763(3) 0.0455(9) Uani 1 1 d . . . . .
H5 H 0.4562 0.7866 -0.1183 0.055 Uiso 1 1 calc R U . . .
C17 C 0.4678(5) 0.3152(4) 0.3790(3) 0.0466(9) Uani 1 1 d . . . . .
H17 H 0.3938 0.3047 0.3080 0.056 Uiso 1 1 calc R U . . .
C6 C 0.6410(5) 0.9834(4) -0.1216(3) 0.0486(9) Uani 1 1 d . . . . .
H6 H 0.5869 0.9870 -0.1937 0.058 Uiso 1 1 calc R U . . .
C13 C 0.5294(5) 0.2182(4) 0.5444(3) 0.0500(9) Uani 1 1 d . . . . .
H13 H 0.4961 0.1442 0.5842 0.060 Uiso 1 1 calc R U . . .
C2 C 0.8827(5) 1.0941(4) 0.0489(3) 0.0493(9) Uani 1 1 d . . . . .
H2 H 0.9899 1.1716 0.0908 0.059 Uiso 1 1 calc R U . . .
C14 C 0.6909(5) 0.3420(4) 0.5907(3) 0.0493(9) Uani 1 1 d . . . . .
H14 H 0.7664 0.3500 0.6609 0.059 Uiso 1 1 calc R U . . .
C20 C 1.0273(5) 0.6049(4) 0.6966(3) 0.0560(10) Uani 1 1 d . . . . .
H20A H 0.9575 0.6042 0.7467 0.067 Uiso 1 1 calc R U . . .
H20B H 1.0781 0.5256 0.7045 0.067 Uiso 1 1 calc R U . . .
C9 C 0.6448(6) 0.7267(4) 0.1967(3) 0.0556(10) Uani 1 1 d . . . . .
H9A H 0.7671 0.7208 0.2080 0.067 Uiso 1 1 calc R U . . .
H9B H 0.6558 0.8135 0.2453 0.067 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 O3 H3A 109.5 . . ?
C21 O6 H6A 109.5 . . ?
C22 O4 C20 108.9(3) . . ?
C10 O1 C9 109.0(3) . . ?
C16 C15 C14 119.8(3) . . ?
C16 C15 C19 121.1(3) . . ?
C14 C15 C19 119.0(3) . . ?
N1 C7 C1 176.4(4) . . ?
C11 C8 C9 108.1(3) . . ?
C11 C8 C4 129.0(3) . . ?
C9 C8 C4 122.8(3) . . ?
C2 C1 C6 121.0(3) . . ?
C2 C1 C7 120.5(3) . . ?
C6 C1 C7 118.5(3) . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 C8 121.5(3) . . ?
C3 C4 C8 118.0(3) . . ?
C8 C11 O3 129.3(3) . . ?
C8 C11 C10 109.0(3) . . ?
O3 C11 C10 121.7(3) . . ?
C19 C21 O6 129.8(3) . . ?
C19 C21 C22 108.3(3) . . ?
O6 C21 C22 121.8(3) . . ?
O5 C22 O4 122.9(3) . . ?
O5 C22 C21 127.9(4) . . ?
O4 C22 C21 109.1(3) . . ?
C2 C3 C4 119.1(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C13 C12 C17 121.2(3) . . ?
C13 C12 C18 121.5(3) . . ?
C17 C12 C18 117.3(3) . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C21 C19 C15 129.4(3) . . ?
C21 C19 C20 108.4(3) . . ?
C15 C19 C20 122.2(3) . . ?
O2 C10 O1 122.6(3) . . ?
O2 C10 C11 129.1(4) . . ?
O1 C10 C11 108.2(3) . . ?
N2 C18 C12 175.7(4) . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C16 C17 C12 118.4(4) . . ?
C16 C17 H17 120.8 . . ?
C12 C17 H17 120.8 . . ?
C5 C6 C1 118.7(3) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C1 C2 C3 120.4(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
O4 C20 C19 105.2(3) . . ?
O4 C20 H20A 110.7 . . ?
C19 C20 H20A 110.7 . . ?
O4 C20 H20B 110.7 . . ?
C19 C20 H20B 110.7 . . ?
H20A C20 H20B 108.8 . . ?
O1 C9 C8 105.7(3) . . ?
O1 C9 H9A 110.6 . . ?
C8 C9 H9A 110.6 . . ?
O1 C9 H9B 110.6 . . ?
C8 C9 H9B 110.6 . . ?
H9A C9 H9B 108.7 . . ?
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
O3 C11 1.344(4) . ?
O3 H3A 0.8200 . ?
O6 C21 1.341(4) . ?
O6 H6A 0.8200 . ?
O4 C22 1.329(4) . ?
O4 C20 1.452(4) . ?
O1 C10 1.349(5) . ?
O1 C9 1.444(4) . ?
O5 C22 1.197(4) . ?
O2 C10 1.193(4) . ?
C15 C16 1.389(5) . ?
C15 C14 1.393(5) . ?
C15 C19 1.472(5) . ?
N1 C7 1.134(4) . ?
N2 C18 1.135(4) . ?
C7 C1 1.442(4) . ?
C8 C11 1.332(5) . ?
C8 C9 1.482(5) . ?
C8 C4 1.486(4) . ?
C1 C2 1.361(5) . ?
C1 C6 1.401(5) . ?
C4 C5 1.377(5) . ?
C4 C3 1.394(5) . ?
C11 C10 1.476(5) . ?
C21 C19 1.322(5) . ?
C21 C22 1.488(5) . ?
C3 C2 1.386(5) . ?
C3 H3 0.9300 . ?
C12 C13 1.354(5) . ?
C12 C17 1.412(5) . ?
C12 C18 1.443(5) . ?
C16 C17 1.388(5) . ?
C16 H16 0.9300 . ?
C19 C20 1.495(5) . ?
C5 C6 1.384(5) . ?
C5 H5 0.9300 . ?
C17 H17 0.9300 . ?
C6 H6 0.9300 . ?
C13 C14 1.393(5) . ?
C13 H13 0.9300 . ?
C2 H2 0.9300 . ?
C14 H14 0.9300 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168353392
