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#$Date: 2020-06-05 14:29:09 +0300 (Fri, 05 Jun 2020) $
#$Revision: 252913 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157480.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_7157480
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            'C40 H32 N0 O12'
_chemical_formula_weight         704.65
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   mixed
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.987(4)
_cell_length_b                   25.021(6)
_cell_length_c                   7.0870(18)
_cell_measurement_reflns_used    400
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      28.455
_cell_measurement_theta_min      3.174
_cell_volume                     3366.8(14)
_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      300(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0355
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8727
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.455
_diffrn_reflns_theta_min         3.174
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       cube
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 545 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.2(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2030
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0466
_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)+(0.0648P)²+1.1827P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1232
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    0.918
_reflns_Friedel_fraction_max     0.904
_reflns_number_gt                1526
_reflns_number_total             2030
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00557f2.cif
_cod_data_source_block           9a
_cod_depositor_comments
'Adding full bibliography for 7157480--7157483.cif.'
_cod_original_cell_volume        3366.9(14)
_cod_database_code               7157480
_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'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
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 0.11975(10) 0.35438(6) 0.1628(4) 0.0598(5) Uani 1 1 d . . . . .
O3 O 0.13960(10) 0.21404(6) 0.1893(4) 0.0623(6) Uani 1 1 d . . . . .
C9 C 0.04578(13) 0.27923(9) 0.1729(5) 0.0436(5) Uani 1 1 d . . . . .
C8 C 0.11306(13) 0.26351(8) 0.1797(5) 0.0468(6) Uani 1 1 d . . . . .
O2 O 0.22261(10) 0.31225(8) 0.1778(6) 0.0769(7) Uani 1 1 d . . . . .
C2 C -0.01905(11) 0.24824(10) 0.1735(5) 0.0464(6) Uani 1 1 d . . . . .
C3 C -0.01913(14) 0.19274(11) 0.1571(5) 0.0539(7) Uani 1 1 d . . . . .
H3 H 0.0234 0.1744 0.1485 0.065 Uiso 1 1 calc R U . . .
C16 C 0.04672(14) 0.33884(10) 0.1620(6) 0.0521(6) Uani 1 1 d . . . . .
H16A H 0.0239 0.3509 0.0473 0.063 Uiso 1 1 calc R U . . .
H16B H 0.0223 0.3542 0.2693 0.063 Uiso 1 1 calc R U . . .
C6 C -0.08355(14) 0.27442(13) 0.1882(6) 0.0645(8) Uani 1 1 d . . . . .
H6 H -0.0849 0.3114 0.2000 0.077 Uiso 1 1 calc R U . . .
C4 C -0.08175(18) 0.16474(13) 0.1533(6) 0.0669(8) Uani 1 1 d . . . . .
H4 H -0.0812 0.1277 0.1407 0.080 Uiso 1 1 calc R U . . .
C13 C 0.15903(14) 0.31019(10) 0.1732(7) 0.0534(6) Uani 1 1 d . . . . .
C5 C -0.14490(17) 0.19128(17) 0.1682(8) 0.0799(10) Uani 1 1 d . . . . .
H5 H -0.1870 0.1724 0.1665 0.096 Uiso 1 1 calc R U . . .
C1 C -0.14529(17) 0.24560(17) 0.1854(8) 0.0824(10) Uani 1 1 d . . . . .
H1 H -0.1881 0.2635 0.1954 0.099 Uiso 1 1 calc R U . . .
H3A H 0.1877(18) 0.2144(13) 0.190(7) 0.075(10) Uiso 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
C13 O1 C16 108.33(19) . . ?
C8 O3 H3A 112(2) . . ?
C8 C9 C2 130.6(2) . . ?
C8 C9 C16 106.5(2) . . ?
C2 C9 C16 122.9(2) . . ?
C9 C8 O3 129.3(2) . . ?
C9 C8 C13 109.6(2) . . ?
O3 C8 C13 121.1(2) . . ?
C6 C2 C3 118.3(2) . . ?
C6 C2 C9 119.6(2) . . ?
C3 C2 C9 122.1(2) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
O1 C16 C9 106.31(19) . . ?
O1 C16 H16A 110.5 . . ?
C9 C16 H16A 110.5 . . ?
O1 C16 H16B 110.5 . . ?
C9 C16 H16B 110.5 . . ?
H16A C16 H16B 108.7 . . ?
C1 C6 C2 120.1(3) . . ?
C1 C6 H6 119.9 . . ?
C2 C6 H6 119.9 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
O2 C13 O1 121.6(2) . . ?
O2 C13 C8 129.1(2) . . ?
O1 C13 C8 109.3(2) . . ?
C1 C5 C4 119.5(3) . . ?
C1 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C1 C6 121.2(3) . . ?
C5 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
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 C13 1.336(3) . ?
O1 C16 1.440(3) . ?
O3 C8 1.338(3) . ?
O3 H3A 0.91(3) . ?
C9 C8 1.337(3) . ?
C9 C2 1.455(3) . ?
C9 C16 1.494(3) . ?
C8 C13 1.459(3) . ?
O2 C13 1.209(3) . ?
C2 C6 1.393(4) . ?
C2 C3 1.393(3) . ?
C3 C4 1.380(4) . ?
C3 H3 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C6 C1 1.376(4) . ?
C6 H6 0.9300 . ?
C4 C5 1.375(5) . ?
C4 H4 0.9300 . ?
C5 C1 1.365(5) . ?
C5 H5 0.9300 . ?
C1 H1 0.9300 . ?
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
C2 C9 C8 O3 -0.1(7) . . . . ?
C16 C9 C8 O3 -179.6(3) . . . . ?
C2 C9 C8 C13 179.4(4) . . . . ?
C16 C9 C8 C13 -0.2(4) . . . . ?
C8 C9 C2 C6 172.3(4) . . . . ?
C16 C9 C2 C6 -8.2(5) . . . . ?
C8 C9 C2 C3 -8.7(6) . . . . ?
C16 C9 C2 C3 170.8(3) . . . . ?
C6 C2 C3 C4 0.7(6) . . . . ?
C9 C2 C3 C4 -178.3(4) . . . . ?
C13 O1 C16 C9 -0.1(4) . . . . ?
C8 C9 C16 O1 0.2(4) . . . . ?
C2 C9 C16 O1 -179.4(3) . . . . ?
C3 C2 C6 C1 -0.3(6) . . . . ?
C9 C2 C6 C1 178.8(4) . . . . ?
C2 C3 C4 C5 -0.8(7) . . . . ?
C16 O1 C13 O2 -179.3(5) . . . . ?
C16 O1 C13 C8 0.0(4) . . . . ?
C9 C8 C13 O2 179.4(5) . . . . ?
O3 C8 C13 O2 -1.1(7) . . . . ?
C9 C8 C13 O1 0.1(5) . . . . ?
O3 C8 C13 O1 179.6(3) . . . . ?
C3 C4 C5 C1 0.4(8) . . . . ?
C4 C5 C1 C6 0.0(8) . . . . ?
C2 C6 C1 C5 0.0(7) . . . . ?
