#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/13/4021366.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_4021366
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         'C14 H13 N O2'
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25
_chemical_name_common            'N-(3-methylphenyl)anthranilic acid'
_chemical_name_systematic        'N-(3-methylphenyl)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                98.466(4)
_cell_angle_beta                 92.198(4)
_cell_angle_gamma                101.337(4)
_cell_formula_units_Z            2
_cell_length_a                   4.6299(14)
_cell_length_b                   8.332(2)
_cell_length_c                   15.336(4)
_cell_measurement_reflns_used    2686
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.19
_cell_measurement_theta_min      2.52
_cell_volume                     572.3(3)
_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 0.977
_diffrn_measured_fraction_theta_max 0.977
_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  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4002
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_correction_T_min  0.9570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, G. Scheldrick (1999)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1973
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0380
_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)+(0.0627P)²+0.0514P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1107
_reflns_number_gt                1557
_reflns_number_total             1973
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0518809si20050908_105117.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               4021366
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 0.2646(2) 0.53858(12) 0.57656(6) 0.0385(3) Uani 1 1 d .
O2 O 0.0696(2) 0.28953(12) 0.49974(6) 0.0399(3) Uani 1 1 d .
H2 H -0.0246 0.3469 0.4735 0.048 Uiso 1 1 calc R
C1 C 0.4300(3) 0.30237(17) 0.61420(9) 0.0320(3) Uani 1 1 d .
N1 N 0.6684(3) 0.55898(15) 0.70818(8) 0.0405(3) Uani 1 1 d .
H1 H 0.5805 0.6119 0.6730 0.049 Uiso 1 1 calc R
C7 C 0.2509(3) 0.38696(17) 0.56310(9) 0.0328(3) Uani 1 1 d .
C2 C 0.6298(3) 0.39063(17) 0.68565(9) 0.0331(3) Uani 1 1 d .
C6 C 0.4023(3) 0.13006(18) 0.59273(9) 0.0367(4) Uani 1 1 d .
H6 H 0.2675 0.0709 0.5452 0.044 Uiso 1 1 calc R
C8 C 0.8391(3) 0.65500(17) 0.78383(9) 0.0350(4) Uani 1 1 d .
C4 C 0.7619(4) 0.13211(19) 0.70818(10) 0.0423(4) Uani 1 1 d .
H4 H 0.8757 0.0741 0.7402 0.051 Uiso 1 1 calc R
C3 C 0.7944(3) 0.30046(19) 0.73124(9) 0.0393(4) Uani 1 1 d .
H3 H 0.9309 0.3571 0.7789 0.047 Uiso 1 1 calc R
C10 C 0.9247(4) 0.72533(18) 0.94273(10) 0.0421(4) Uani 1 1 d .
C5 C 0.5647(4) 0.04497(18) 0.63863(10) 0.0413(4) Uani 1 1 d .
H5 H 0.5429 -0.0717 0.6232 0.050 Uiso 1 1 calc R
C11 C 1.1552(3) 0.85003(19) 0.93083(10) 0.0457(4) Uani 1 1 d .
H11 H 1.2667 0.9179 0.9809 0.055 Uiso 1 1 calc R
C13 C 1.0698(4) 0.77975(18) 0.77337(10) 0.0445(4) Uani 1 1 d .
H13 H 1.1214 0.7986 0.7158 0.053 Uiso 1 1 calc R
C9 C 0.7670(4) 0.62880(19) 0.86788(10) 0.0457(4) Uani 1 1 d .
H9 H 0.6055 0.5426 0.8747 0.055 Uiso 1 1 calc R
C12 C 1.2269(4) 0.8781(2) 0.84701(11) 0.0554(5) Uani 1 1 d .
H12 H 1.3856 0.9657 0.8400 0.066 Uiso 1 1 calc R
C14 C 0.8396(5) 0.6972(2) 1.03373(11) 0.0660(6) Uani 1 1 d .
H14A H 0.9704 0.7788 1.0780 0.099 Uiso 1 1 calc R
H14B H 0.8581 0.5852 1.0422 0.099 Uiso 1 1 calc R
H14C H 0.6349 0.7091 1.0404 0.099 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0405(6) 0.0387(6) 0.0339(6) 0.0011(4) -0.0057(4) 0.0075(4)
O2 0.0387(6) 0.0416(6) 0.0362(6) -0.0013(4) -0.0095(5) 0.0083(5)
C1 0.0294(7) 0.0397(8) 0.0265(7) 0.0042(6) 0.0052(6) 0.0062(6)
N1 0.0469(8) 0.0387(7) 0.0342(7) 0.0041(5) -0.0106(6) 0.0082(6)
C7 0.0300(7) 0.0402(8) 0.0262(7) 0.0007(6) 0.0039(6) 0.0053(6)
C2 0.0319(8) 0.0406(8) 0.0269(7) 0.0049(6) 0.0050(6) 0.0071(6)
C6 0.0366(8) 0.0396(8) 0.0318(8) 0.0014(6) 0.0068(6) 0.0051(6)
C8 0.0367(8) 0.0349(8) 0.0331(8) 0.0034(6) -0.0055(6) 0.0101(6)
C4 0.0470(9) 0.0493(9) 0.0362(9) 0.0123(7) 0.0064(7) 0.0189(7)
C3 0.0407(9) 0.0478(9) 0.0300(8) 0.0059(6) 0.0002(6) 0.0115(7)
C10 0.0505(10) 0.0379(8) 0.0364(9) 0.0052(6) -0.0070(7) 0.0081(7)
C5 0.0495(9) 0.0380(8) 0.0384(9) 0.0066(6) 0.0103(7) 0.0122(7)
C11 0.0396(9) 0.0439(9) 0.0459(10) -0.0074(7) -0.0073(7) 0.0031(7)
C13 0.0499(10) 0.0404(8) 0.0412(9) 0.0027(7) 0.0100(7) 0.0059(7)
C9 0.0480(10) 0.0435(9) 0.0384(9) 0.0080(7) -0.0048(7) -0.0076(7)
C12 0.0488(10) 0.0490(10) 0.0562(11) -0.0062(8) 0.0097(8) -0.0093(8)
C14 0.0971(16) 0.0559(11) 0.0348(10) 0.0057(8) -0.0054(9) -0.0055(10)
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
C6 C1 C2 119.16(13)
C6 C1 C7 119.44(13)
C2 C1 C7 121.40(13)
C2 N1 C8 125.14(12)
O1 C7 O2 121.17(13)
O1 C7 C1 123.72(13)
O2 C7 C1 115.11(12)
N1 C2 C3 120.69(13)
N1 C2 C1 121.35(12)
C3 C2 C1 117.93(13)
C5 C6 C1 121.69(14)
C13 C8 C9 119.59(14)
C13 C8 N1 119.55(13)
C9 C8 N1 120.80(13)
C3 C4 C5 121.02(14)
C4 C3 C2 121.22(14)
C11 C10 C9 117.85(14)
C11 C10 C14 121.18(15)
C9 C10 C14 120.95(15)
C6 C5 C4 118.96(14)
C10 C11 C12 120.85(15)
C8 C13 C12 119.54(15)
C8 C9 C10 121.66(14)
C13 C12 C11 120.50(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.2382(16)
O2 C7 1.3210(16)
C1 C6 1.404(2)
C1 C2 1.420(2)
C1 C7 1.463(2)
N1 C2 1.3685(18)
N1 C8 1.4208(18)
C2 C3 1.405(2)
C6 C5 1.371(2)
C8 C13 1.368(2)
C8 C9 1.381(2)
C4 C3 1.372(2)
C4 C5 1.391(2)
C10 C11 1.373(2)
C10 C9 1.390(2)
C10 C14 1.503(2)
C11 C12 1.381(2)
C13 C12 1.381(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 77086
2 PubChem 85472
