#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/13/4021362.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_4021362
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-2-methylphenylanthranilic acid'
_chemical_name_systematic        'N-2-methylphenylanthranilic acid'
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.168(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.7804(16)
_cell_length_b                   7.4503(10)
_cell_length_c                   26.627(3)
_cell_measurement_reflns_used    5653
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      3.11
_cell_volume                     2300.3(5)
_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 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'SMART platform CCD, Siemens/Bruker'
_diffrn_measurement_method       'omega scans'
_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  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            9959
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9826
_exptl_absorpt_correction_T_min  0.9572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, G. Scheldrick (1999)'
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2714
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0483
_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)+(0.0784P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1409
_reflns_number_gt                1638
_reflns_number_total             2714
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0518809si20050908_104902.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4021362
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.43144(10) 0.48857(16) 0.54713(5) 0.0396(4) Uani 1 1 d .
O2 O 0.45930(11) 0.26062(16) 0.49675(5) 0.0416(4) Uani 1 1 d .
H2' H 0.4987 0.3388 0.4849 0.050 Uiso 1 1 calc R
N1 N 0.29297(14) 0.4397(2) 0.61364(6) 0.0434(4) Uani 1 1 d .
H1 H 0.3392 0.5078 0.5993 0.052 Uiso 1 1 calc R
C1 C 0.34277(14) 0.2067(2) 0.55819(6) 0.0298(4) Uani 1 1 d .
C2 C 0.33247(16) 0.0279(2) 0.54215(7) 0.0359(4) Uani 1 1 d .
H2 H 0.3727 -0.0114 0.5162 0.043 Uiso 1 1 calc R
C3 C 0.26544(17) -0.0924(2) 0.56298(7) 0.0410(5) Uani 1 1 d .
H3 H 0.2574 -0.2125 0.5509 0.049 Uiso 1 1 calc R
C4 C 0.20961(16) -0.0355(2) 0.60201(7) 0.0376(4) Uani 1 1 d .
H4 H 0.1643 -0.1186 0.6170 0.045 Uiso 1 1 calc R
C5 C 0.21866(15) 0.1375(2) 0.61918(7) 0.0346(4) Uani 1 1 d .
H5 H 0.1806 0.1723 0.6463 0.041 Uiso 1 1 calc R
C6 C 0.28356(14) 0.2653(2) 0.59732(6) 0.0306(4) Uani 1 1 d .
C7 C 0.41399(14) 0.3306(2) 0.53426(6) 0.0308(4) Uani 1 1 d .
C8 C 0.23869(15) 0.5254(2) 0.65033(7) 0.0324(4) Uani 1 1 d .
C9 C 0.12143(16) 0.5140(2) 0.64929(8) 0.0390(5) Uani 1 1 d .
H9 H 0.0749 0.4423 0.6242 0.047 Uiso 1 1 calc R
C10 C 0.07154(17) 0.6072(3) 0.68489(8) 0.0447(5) Uani 1 1 d .
H10 H -0.0090 0.5979 0.6845 0.054 Uiso 1 1 calc R
C11 C 0.13876(19) 0.7133(3) 0.72081(8) 0.0473(5) Uani 1 1 d .
H11 H 0.1050 0.7757 0.7456 0.057 Uiso 1 1 calc R
C12 C 0.25467(18) 0.7281(3) 0.72054(7) 0.0436(5) Uani 1 1 d .
H12 H 0.3003 0.8035 0.7449 0.052 Uiso 1 1 calc R
C13 C 0.30672(16) 0.6361(2) 0.68562(7) 0.0367(4) Uani 1 1 d .
C14 C 0.43283(17) 0.6609(3) 0.68328(8) 0.0521(6) Uani 1 1 d .
H14A H 0.4684 0.7393 0.7112 0.078 Uiso 1 1 calc R
H14B H 0.4405 0.7154 0.6506 0.078 Uiso 1 1 calc R
H14C H 0.4715 0.5439 0.6865 0.078 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 0.0472(8) 0.0323(8) 0.0455(8) -0.0070(6) 0.0250(6) -0.0109(6)
O2 0.0509(8) 0.0348(7) 0.0465(8) -0.0040(6) 0.0292(6) -0.0056(6)
N1 0.0550(10) 0.0281(9) 0.0562(10) -0.0084(7) 0.0353(8) -0.0138(7)
C1 0.0312(9) 0.0281(9) 0.0310(9) 0.0025(7) 0.0084(7) -0.0004(7)
C2 0.0440(11) 0.0298(10) 0.0360(10) -0.0007(8) 0.0133(8) 0.0027(8)
C3 0.0550(12) 0.0239(9) 0.0458(11) 0.0017(8) 0.0139(9) -0.0013(8)
C4 0.0433(11) 0.0270(9) 0.0447(11) 0.0098(8) 0.0141(9) -0.0029(8)
C5 0.0399(11) 0.0298(10) 0.0373(10) 0.0031(8) 0.0158(8) -0.0016(8)
C6 0.0323(9) 0.0275(9) 0.0332(9) 0.0004(7) 0.0092(7) -0.0002(7)
C7 0.0295(9) 0.0321(10) 0.0323(9) 0.0003(8) 0.0093(7) 0.0008(7)
C8 0.0427(11) 0.0220(8) 0.0375(10) 0.0025(7) 0.0206(8) -0.0006(7)
C9 0.0417(11) 0.0303(10) 0.0489(12) 0.0002(8) 0.0184(9) -0.0044(8)
C10 0.0425(12) 0.0344(11) 0.0634(14) 0.0062(9) 0.0268(10) 0.0039(8)
C11 0.0637(14) 0.0348(11) 0.0515(13) 0.0008(9) 0.0320(11) 0.0054(9)
C12 0.0598(13) 0.0364(11) 0.0379(11) -0.0035(8) 0.0172(9) -0.0081(9)
C13 0.0417(11) 0.0316(10) 0.0394(10) 0.0040(8) 0.0144(8) -0.0041(8)
C14 0.0466(13) 0.0565(13) 0.0536(13) -0.0007(11) 0.0099(10) -0.0111(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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 N1 C8 128.93(15)
C2 C1 C6 119.31(15)
C2 C1 C7 119.52(15)
C6 C1 C7 121.17(15)
C3 C2 C1 121.54(17)
C2 C3 C4 118.97(17)
C5 C4 C3 121.23(17)
C4 C5 C6 121.02(16)
N1 C6 C5 121.98(15)
N1 C6 C1 120.13(15)
C5 C6 C1 117.87(15)
O1 C7 O2 121.15(15)
O1 C7 C1 124.09(15)
O2 C7 C1 114.76(15)
C9 C8 C13 120.34(16)
C9 C8 N1 122.18(17)
C13 C8 N1 117.26(16)
C8 C9 C10 119.95(19)
C11 C10 C9 120.04(18)
C12 C11 C10 119.55(18)
C11 C12 C13 121.60(19)
C12 C13 C8 118.46(17)
C12 C13 C14 121.59(18)
C8 C13 C14 119.87(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.233(2)
O2 C7 1.3201(19)
N1 C6 1.368(2)
N1 C8 1.412(2)
C1 C2 1.397(2)
C1 C6 1.421(2)
C1 C7 1.467(2)
C2 C3 1.374(2)
C3 C4 1.390(3)
C4 C5 1.365(2)
C5 C6 1.410(2)
C8 C9 1.379(2)
C8 C13 1.393(3)
C9 C10 1.387(3)
C10 C11 1.378(3)
C11 C12 1.371(3)
C12 C13 1.383(2)
C13 C14 1.509(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 77120
2 PubChem 85510
