#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/13/4021361.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_4021361
loop_
_publ_author_name
'Xuefeng Mei'
'Adam T. August'
'Christian Wolf'
_publ_section_title
;
 Regioselective Copper-Catalyzed Amination of Chlorobenzoic Acids:
 Synthesis and Solid-State Structures of
 N-Aryl Anthranilic Acid Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              142
_journal_page_last               149
_journal_paper_doi               10.1021/jo0518809
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C21 H19 N O2'
_chemical_formula_sum            'C21 H19 N O2'
_chemical_formula_weight         317.37
_chemical_name_common            'anthranilic acid 19'
_chemical_name_systematic
;
 N-[3-(3',5'-dimethylbiphenyl)]anthranilic acid
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                80.856(3)
_cell_angle_beta                 82.334(3)
_cell_angle_gamma                84.982(3)
_cell_formula_units_Z            4
_cell_length_a                   10.5769(16)
_cell_length_b                   11.4108(17)
_cell_length_c                   14.162(2)
_cell_measurement_reflns_used    853
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.06
_cell_measurement_theta_min      2.58
_cell_volume                     1668.5(4)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'SMART, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'XSEED, L. Barbour (1999); http:\x-seed.net'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12432
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9761
_exptl_absorpt_correction_T_min  0.9606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, G. Scheldrick (1999)'
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         5841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0532P)²+0.1752P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1031
_reflns_number_gt                4353
_reflns_number_total             5841
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0518809si20050908_015909.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4021361
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.55701(10) -0.24219(9) 0.10340(8) 0.0313(3) Uani 1 1 d .
O2 O 0.67226(12) -0.08489(10) 0.08899(9) 0.0341(3) Uani 1 1 d .
O3 O 0.32776(12) -0.13296(10) 0.12088(9) 0.0388(3) Uani 1 1 d .
O4 O 0.43479(10) 0.02809(9) 0.11422(8) 0.0310(3) Uani 1 1 d .
N1 N 0.67514(12) -0.45772(11) 0.15193(9) 0.0272(3) Uani 1 1 d .
H1 H 0.6034 -0.4126 0.1566 0.033 Uiso 1 1 calc R
N2 N 0.29957(12) 0.22872(11) 0.15583(9) 0.0269(3) Uani 1 1 d .
H2 H 0.3703 0.1967 0.1274 0.032 Uiso 1 1 calc R
C1 C 0.78280(15) -0.27443(13) 0.09679(11) 0.0245(4) Uani 1 1 d .
C2 C 0.78528(15) -0.40020(14) 0.12175(10) 0.0240(4) Uani 1 1 d .
C3 C 0.90505(15) -0.46420(15) 0.12040(11) 0.0286(4) Uani 1 1 d .
H3 H 0.9088 -0.5485 0.1358 0.034 Uiso 1 1 calc R
C4 C 1.01654(16) -0.40749(15) 0.09734(12) 0.0338(4) Uani 1 1 d .
H4 H 1.0962 -0.4529 0.0978 0.041 Uiso 1 1 calc R
C5 C 1.01460(16) -0.28414(16) 0.07323(13) 0.0377(4) Uani 1 1 d .
H5 H 1.0922 -0.2454 0.0569 0.045 Uiso 1 1 calc R
C6 C 0.89923(16) -0.21963(15) 0.07335(12) 0.0330(4) Uani 1 1 d .
H6 H 0.8978 -0.1355 0.0572 0.040 Uiso 1 1 calc R
C7 C 0.66278(15) -0.20127(13) 0.09656(10) 0.0247(4) Uani 1 1 d .
C8 C 0.66461(14) -0.58264(13) 0.17648(11) 0.0245(4) Uani 1 1 d .
C9 C 0.60056(14) -0.62651(14) 0.26520(11) 0.0260(4) Uani 1 1 d .
H9 H 0.5730 -0.5742 0.3109 0.031 Uiso 1 1 calc R
C10 C 0.57595(14) -0.74686(14) 0.28840(11) 0.0252(4) Uani 1 1 d .
C11 C 0.61880(15) -0.82183(14) 0.22048(12) 0.0290(4) Uani 1 1 d .
H11 H 0.6022 -0.9037 0.2346 0.035 Uiso 1 1 calc R
C12 C 0.68525(15) -0.77859(14) 0.13266(12) 0.0306(4) Uani 1 1 d .
H12 H 0.7151 -0.8310 0.0874 0.037 Uiso 1 1 calc R
C13 C 0.70838(15) -0.65902(14) 0.11051(11) 0.0282(4) Uani 1 1 d .
H13 H 0.7541 -0.6295 0.0502 0.034 Uiso 1 1 calc R
C14 C 0.50533(15) -0.79315(14) 0.38255(11) 0.0271(4) Uani 1 1 d .
C15 C 0.40937(15) -0.87100(14) 0.38751(12) 0.0306(4) Uani 1 1 d .
H15 H 0.3894 -0.8935 0.3297 0.037 Uiso 1 1 calc R
C16 C 0.34207(16) -0.91650(15) 0.47497(13) 0.0353(4) Uani 1 1 d .
C17 C 0.37540(17) -0.88435(16) 0.55821(13) 0.0416(5) Uani 1 1 d .
H17 H 0.3309 -0.9154 0.6185 0.050 Uiso 1 1 calc R
C18 C 0.47192(17) -0.80815(16) 0.55657(12) 0.0391(4) Uani 1 1 d .
C19 C 0.53471(16) -0.76184(15) 0.46800(12) 0.0327(4) Uani 1 1 d .
H19 H 0.5989 -0.7078 0.4655 0.039 Uiso 1 1 calc R
C20 C 0.23741(18) -0.99880(16) 0.47776(16) 0.0504(5) Uani 1 1 d .
H20A H 0.2752 -1.0794 0.4728 0.076 Uiso 1 1 calc R
H20B H 0.1880 -0.9712 0.4237 0.076 Uiso 1 1 calc R
H20C H 0.1809 -0.9993 0.5386 0.076 Uiso 1 1 calc R
C21 C 0.5099(2) -0.7797(2) 0.64872(14) 0.0592(6) Uani 1 1 d .
H21A H 0.5883 -0.8274 0.6637 0.089 Uiso 1 1 calc R
H21B H 0.4411 -0.7981 0.7013 0.089 Uiso 1 1 calc R
H21C H 0.5250 -0.6950 0.6411 0.089 Uiso 1 1 calc R
C22 C 0.20979(15) 0.03762(14) 0.16604(11) 0.0282(4) Uani 1 1 d .
C23 C 0.10178(17) -0.02941(16) 0.18867(13) 0.0393(4) Uani 1 1 d .
H23 H 0.1104 -0.1109 0.1807 0.047 Uiso 1 1 calc R
C24 C -0.01557(18) 0.01902(17) 0.22189(15) 0.0483(5) Uani 1 1 d .
H24 H -0.0871 -0.0283 0.2377 0.058 Uiso 1 1 calc R
C25 C -0.02788(17) 0.13914(17) 0.23197(14) 0.0420(5) Uani 1 1 d .
H25 H -0.1090 0.1741 0.2542 0.050 Uiso 1 1 calc R
C26 C 0.07493(15) 0.20731(15) 0.21045(12) 0.0326(4) Uani 1 1 d .
H26 H 0.0637 0.2890 0.2178 0.039 Uiso 1 1 calc R
C27 C 0.19708(15) 0.15954(14) 0.17774(11) 0.0253(4) Uani 1 1 d .
C28 C 0.33268(16) -0.02014(14) 0.13191(11) 0.0274(4) Uani 1 1 d .
C29 C 0.30291(14) 0.34699(13) 0.17452(11) 0.0234(3) Uani 1 1 d .
C30 C 0.25708(14) 0.37846(13) 0.26430(11) 0.0241(3) Uani 1 1 d .
H30 H 0.2209 0.3204 0.3138 0.029 Uiso 1 1 calc R
C31 C 0.26347(14) 0.49407(13) 0.28273(11) 0.0243(4) Uani 1 1 d .
C32 C 0.31864(15) 0.57689(14) 0.20945(11) 0.0267(4) Uani 1 1 d .
H32 H 0.3239 0.6562 0.2206 0.032 Uiso 1 1 calc R
C33 C 0.36588(14) 0.54515(14) 0.12076(11) 0.0270(4) Uani 1 1 d .
H33 H 0.4046 0.6024 0.0718 0.032 Uiso 1 1 calc R
C34 C 0.35739(14) 0.43064(14) 0.10238(11) 0.0252(4) Uani 1 1 d .
H34 H 0.3887 0.4097 0.0408 0.030 Uiso 1 1 calc R
C35 C 0.21272(15) 0.52675(14) 0.37897(12) 0.0278(4) Uani 1 1 d .
C36 C 0.22718(15) 0.44670(15) 0.46243(12) 0.0315(4) Uani 1 1 d .
H36 H 0.2730 0.3720 0.4578 0.038 Uiso 1 1 calc R
C37 C 0.17568(17) 0.47420(17) 0.55256(12) 0.0372(4) Uani 1 1 d .
C38 C 0.10995(17) 0.58370(17) 0.55768(14) 0.0417(5) Uani 1 1 d .
H38 H 0.0746 0.6031 0.6190 0.050 Uiso 1 1 calc R
C39 C 0.09400(16) 0.66603(16) 0.47618(14) 0.0384(4) Uani 1 1 d .
C40 C 0.14699(16) 0.63621(15) 0.38691(13) 0.0343(4) Uani 1 1 d .
H40 H 0.1380 0.6919 0.3303 0.041 Uiso 1 1 calc R
C41 C 0.1897(2) 0.38602(19) 0.64250(13) 0.0541(6) Uani 1 1 d .
H41A H 0.2606 0.4061 0.6737 0.081 Uiso 1 1 calc R
H41B H 0.2072 0.3058 0.6254 0.081 Uiso 1 1 calc R
H41C H 0.1104 0.3889 0.6868 0.081 Uiso 1 1 calc R
C42 C 0.0155(2) 0.78176(17) 0.48337(16) 0.0543(6) Uani 1 1 d .
H42A H -0.0756 0.7679 0.4891 0.082 Uiso 1 1 calc R
H42B H 0.0380 0.8389 0.4254 0.082 Uiso 1 1 calc R
H42C H 0.0330 0.8137 0.5402 0.082 Uiso 1 1 calc R
H1O H 0.584(3) -0.048(2) 0.0891(17) 0.090(8) Uiso 1 1 d .
H2O H 0.415(3) -0.168(2) 0.1092(17) 0.085(8) 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
C2 N1 C8 126.89(13)
C27 N2 C29 126.43(13)
C6 C1 C2 118.96(14)
C6 C1 C7 119.48(14)
C2 C1 C7 121.55(14)
N1 C2 C3 120.39(14)
N1 C2 C1 121.52(14)
C3 C2 C1 117.98(14)
C4 C3 C2 121.33(15)
C3 C4 C5 120.90(16)
C6 C5 C4 119.00(16)
C5 C6 C1 121.82(16)
O1 C7 O2 120.46(14)
O1 C7 C1 123.63(14)
O2 C7 C1 115.91(14)
C13 C8 C9 119.91(14)
C13 C8 N1 121.00(14)
C9 C8 N1 118.89(14)
C8 C9 C10 120.89(15)
C11 C10 C9 118.31(15)
C11 C10 C14 120.87(14)
C9 C10 C14 120.82(14)
C12 C11 C10 120.82(15)
C11 C12 C13 120.21(15)
C8 C13 C12 119.82(15)
C15 C14 C19 118.63(15)
C15 C14 C10 120.38(15)
C19 C14 C10 120.99(15)
C16 C15 C14 121.63(17)
C17 C16 C15 117.87(16)
C17 C16 C20 121.78(16)
C15 C16 C20 120.35(17)
C16 C17 C18 122.32(16)
C19 C18 C17 118.32(17)
C19 C18 C21 120.76(18)
C17 C18 C21 120.90(17)
C18 C19 C14 121.20(16)
C23 C22 C27 119.06(15)
C23 C22 C28 119.21(15)
C27 C22 C28 121.73(14)
C24 C23 C22 122.06(17)
C23 C24 C25 118.64(17)
C26 C25 C24 120.99(16)
C25 C26 C27 121.64(16)
N2 C27 C26 121.25(14)
N2 C27 C22 121.13(14)
C26 C27 C22 117.60(15)
O4 C28 O3 120.59(15)
O4 C28 C22 124.94(14)
O3 C28 C22 114.47(14)
C34 C29 C30 119.93(14)
C34 C29 N2 118.75(13)
C30 C29 N2 121.28(13)
C29 C30 C31 120.91(14)
C32 C31 C30 118.37(14)
C32 C31 C35 121.35(14)
C30 C31 C35 120.28(14)
C33 C32 C31 120.70(15)
C32 C33 C34 120.66(15)
C29 C34 C33 119.41(14)
C40 C35 C36 118.82(15)
C40 C35 C31 120.64(15)
C36 C35 C31 120.51(14)
C35 C36 C37 121.11(16)
C38 C37 C36 118.49(17)
C38 C37 C41 120.73(16)
C36 C37 C41 120.77(17)
C37 C38 C39 122.09(16)
C38 C39 C40 118.15(16)
C38 C39 C42 120.92(16)
C40 C39 C42 120.85(18)
C35 C40 C39 121.33(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.2357(18)
O2 C7 1.3267(18)
O3 C28 1.3275(18)
O4 C28 1.2329(18)
N1 C2 1.3720(19)
N1 C8 1.4231(19)
N2 C27 1.3699(19)
N2 C29 1.4202(18)
C1 C6 1.406(2)
C1 C2 1.421(2)
C1 C7 1.457(2)
C2 C3 1.405(2)
C3 C4 1.371(2)
C4 C5 1.394(2)
C5 C6 1.369(2)
C8 C13 1.385(2)
C8 C9 1.386(2)
C9 C10 1.399(2)
C10 C11 1.393(2)
C10 C14 1.481(2)
C11 C12 1.384(2)
C12 C13 1.386(2)
C14 C15 1.394(2)
C14 C19 1.395(2)
C15 C16 1.391(2)
C16 C17 1.385(3)
C16 C20 1.506(3)
C17 C18 1.393(3)
C18 C19 1.386(2)
C18 C21 1.506(3)
C22 C23 1.404(2)
C22 C27 1.420(2)
C22 C28 1.463(2)
C23 C24 1.369(3)
C24 C25 1.394(2)
C25 C26 1.366(2)
C26 C27 1.407(2)
C29 C34 1.384(2)
C29 C30 1.389(2)
C30 C31 1.394(2)
C31 C32 1.391(2)
C31 C35 1.489(2)
C32 C33 1.380(2)
C33 C34 1.385(2)
C35 C40 1.388(2)
C35 C36 1.391(2)
C36 C37 1.391(2)
C37 C38 1.383(3)
C37 C41 1.508(3)
C38 C39 1.387(3)
C39 C40 1.394(2)
C39 C42 1.507(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21108235
2 PubChem 139089800
