#------------------------------------------------------------------------------
#$Date: 2021-05-05 11:08:13 +0300 (Wed, 05 May 2021) $
#$Revision: 264881 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/80/7128056.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_7128056
loop_
_publ_author_name
'Yao, Tuanli'
'Wang, Bo'
'Ren, Beige'
'Qin, Xiangyang'
'Li, Tao'
_publ_section_title
;
 Palladium-catalyzed Ugi-type reaction of 2-iodoanilines with isocyanides
 and carboxylic acids affording N-acyl anthranilamides.
;
_journal_issue                   35
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4247
_journal_page_last               4250
_journal_paper_doi               10.1039/d1cc01226f
_journal_volume                  57
_journal_year                    2021
_chemical_formula_sum            'C20 H22 N2 O2'
_chemical_formula_weight         322.39
_chemical_name_systematic        N-(2,6-dimethylphenyl)-2-pivalamidobenzamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-10-24 deposited with the CCDC.	2021-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.281(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.135(2)
_cell_length_b                   10.7195(17)
_cell_length_c                   13.166(2)
_cell_measurement_reflns_used    2749
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      23.24
_cell_measurement_theta_min      2.48
_cell_volume                     1811.4(5)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      302(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1124
_diffrn_reflns_av_unetI/netI     0.0973
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17156
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.607
_diffrn_reflns_theta_min         2.476
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0091(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         4138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1789
_refine_ls_R_factor_gt           0.0621
_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)+(0.0850P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1478
_refine_ls_wR_factor_ref         0.1964
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1734
_reflns_number_total             4138
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc01226f2.cif
_cod_data_source_block           SUST_1495_0ma
_cod_depositor_comments          'Adding full bibliography for 7128056.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7128056
_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.
;
_shelx_estimated_absorpt_t_min   0.989
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C 0.1569(2) 0.6654(3) 0.3682(2) 0.0526(8) Uani 1 1 d . . . . .
C2 C 0.1254(2) 0.6832(3) 0.2624(3) 0.0717(10) Uani 1 1 d . . . . .
H2 H 0.0954 0.6176 0.2203 0.086 Uiso 1 1 calc R U . . .
C3 C 0.1378(3) 0.7968(4) 0.2184(3) 0.0754(10) Uani 1 1 d . . . . .
H3 H 0.1161 0.8071 0.1470 0.090 Uiso 1 1 calc R U . . .
C4 C 0.2146(2) 0.8805(3) 0.3851(2) 0.0527(8) Uani 1 1 d . . . . .
C5 C 0.2019(2) 0.7653(2) 0.4283(2) 0.0429(7) Uani 1 1 d . . . . .
C6 C 0.1404(3) 0.5422(3) 0.4152(3) 0.0811(10) Uani 1 1 d . . . . .
H6A H 0.2065 0.5022 0.4396 0.122 Uiso 1 1 calc R U . . .
H6B H 0.0974 0.4905 0.3637 0.122 Uiso 1 1 calc R U . . .
H6C H 0.1068 0.5546 0.4723 0.122 Uiso 1 1 calc R U . . .
C7 C 0.2630(3) 0.9871(3) 0.4514(3) 0.0834(11) Uani 1 1 d . . . . .
H7A H 0.2214 1.0069 0.5010 0.125 Uiso 1 1 calc R U . . .
H7B H 0.2667 1.0585 0.4083 0.125 Uiso 1 1 calc R U . . .
H7C H 0.3319 0.9643 0.4873 0.125 Uiso 1 1 calc R U . . .
C8 C 0.3191(2) 0.6909(2) 0.5865(2) 0.0421(7) Uani 1 1 d . . . . .
C9 C 0.34913(19) 0.7059(2) 0.7018(2) 0.0409(6) Uani 1 1 d . . . . .
C10 C 0.3347(2) 0.8192(2) 0.7470(2) 0.0504(7) Uani 1 1 d . . . . .
H10 H 0.3042 0.8846 0.7049 0.061 Uiso 1 1 calc R U . . .
C11 C 0.3640(2) 0.8375(3) 0.8514(2) 0.0616(8) Uani 1 1 d . . . . .
H11 H 0.3533 0.9144 0.8801 0.074 Uiso 1 1 calc R U . . .
C12 C 0.4097(2) 0.7413(3) 0.9144(2) 0.0619(9) Uani 1 1 d . . . . .
H12 H 0.4303 0.7536 0.9857 0.074 Uiso 1 1 calc R U . . .
C13 C 0.4251(2) 0.6277(3) 0.8724(2) 0.0527(7) Uani 1 1 d . . . . .
H13 H 0.4551 0.5631 0.9158 0.063 Uiso 1 1 calc R U . . .
C14 C 0.39625(19) 0.6077(2) 0.7658(2) 0.0419(7) Uani 1 1 d . . . . .
C15 C 0.42630(19) 0.3794(2) 0.7626(2) 0.0442(7) Uani 1 1 d . . . . .
C16 C 0.4542(2) 0.2744(2) 0.6958(2) 0.0495(7) Uani 1 1 d . . . . .
C17 C 0.4057(2) 0.1534(3) 0.7238(3) 0.0700(9) Uani 1 1 d . . . . .
H17A H 0.4282 0.1380 0.7970 0.105 Uiso 1 1 calc R U . . .
H17B H 0.4273 0.0856 0.6856 0.105 Uiso 1 1 calc R U . . .
H17C H 0.3312 0.1603 0.7064 0.105 Uiso 1 1 calc R U . . .
C18 C 0.5731(2) 0.2622(3) 0.7229(3) 0.0828(11) Uani 1 1 d . . . . .
H18A H 0.6039 0.3347 0.6988 0.124 Uiso 1 1 calc R U . . .
H18B H 0.5935 0.1892 0.6900 0.124 Uiso 1 1 calc R U . . .
H18C H 0.5965 0.2551 0.7969 0.124 Uiso 1 1 calc R U . . .
C19 C 0.4166(3) 0.2974(3) 0.5795(2) 0.0807(11) Uani 1 1 d . . . . .
H19A H 0.3425 0.3099 0.5639 0.121 Uiso 1 1 calc R U . . .
H19B H 0.4334 0.2266 0.5416 0.121 Uiso 1 1 calc R U . . .
H19C H 0.4503 0.3703 0.5598 0.121 Uiso 1 1 calc R U . . .
C00G C 0.1811(3) 0.8937(3) 0.2776(3) 0.0672(9) Uani 1 1 d . . . . .
H00G H 0.1888 0.9701 0.2465 0.081 Uiso 1 1 calc R U . . .
N1 N 0.23274(16) 0.75314(18) 0.53950(16) 0.0446(6) Uani 1 1 d . . . . .
N2 N 0.41451(16) 0.49433(18) 0.71793(16) 0.0444(6) Uani 1 1 d . . . . .
O1 O 0.37149(15) 0.62714(18) 0.53836(14) 0.0589(6) Uani 1 1 d . . . . .
O2 O 0.41890(16) 0.36114(17) 0.85297(15) 0.0599(6) Uani 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
C2 C1 C5 118.0(3) . . ?
C2 C1 C6 120.1(3) . . ?
C5 C1 C6 121.9(3) . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C00G C3 C2 120.9(3) . . ?
C00G C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C00G 117.9(3) . . ?
C5 C4 C7 121.0(3) . . ?
C00G C4 C7 121.1(3) . . ?
C4 C5 C1 121.9(3) . . ?
C4 C5 N1 117.8(3) . . ?
C1 C5 N1 120.3(2) . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 N1 123.0(2) . . ?
O1 C8 C9 121.7(2) . . ?
N1 C8 C9 115.3(2) . . ?
C10 C9 C14 118.8(3) . . ?
C10 C9 C8 120.1(2) . . ?
C14 C9 C8 121.1(2) . . ?
C11 C10 C9 121.8(3) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 119.5(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.8(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C9 118.7(2) . . ?
C13 C14 N2 123.2(2) . . ?
C9 C14 N2 118.1(2) . . ?
O2 C15 N2 122.5(3) . . ?
O2 C15 C16 121.4(2) . . ?
N2 C15 C16 116.1(2) . . ?
C15 C16 C17 109.0(2) . . ?
C15 C16 C19 113.3(2) . . ?
C17 C16 C19 108.5(2) . . ?
C15 C16 C18 106.7(2) . . ?
C17 C16 C18 109.2(2) . . ?
C19 C16 C18 110.1(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C3 C00G C4 120.6(3) . . ?
C3 C00G H00G 119.7 . . ?
C4 C00G H00G 119.7 . . ?
C8 N1 C5 122.6(2) . . ?
C15 N2 C14 127.0(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
C1 C2 1.380(4) . ?
C1 C5 1.387(4) . ?
C1 C6 1.494(4) . ?
C2 C3 1.372(4) . ?
C2 H2 0.9300 . ?
C3 C00G 1.350(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(4) . ?
C4 C00G 1.397(4) . ?
C4 C7 1.495(4) . ?
C5 N1 1.440(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 O1 1.236(3) . ?
C8 N1 1.348(3) . ?
C8 C9 1.494(3) . ?
C9 C10 1.383(3) . ?
C9 C14 1.407(3) . ?
C10 C11 1.361(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.370(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.391(3) . ?
C13 H13 0.9300 . ?
C14 N2 1.413(3) . ?
C15 O2 1.230(3) . ?
C15 N2 1.360(3) . ?
C15 C16 1.520(4) . ?
C16 C17 1.525(4) . ?
C16 C19 1.526(4) . ?
C16 C18 1.533(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C00G H00G 0.9300 . ?
