#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/13/4021364.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_4021364
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         'C17 H19 N O2'
_chemical_formula_sum            'C17 H19 N O2'
_chemical_formula_weight         269.33
_chemical_name_common            'N-(2-tert-butylphenyl)anthranilic acid'
_chemical_name_systematic        'N-(2-tert-butylphenyl)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                106.582(3)
_cell_angle_beta                 91.207(3)
_cell_angle_gamma                99.212(3)
_cell_formula_units_Z            2
_cell_length_a                   7.4748(12)
_cell_length_b                   9.3856(15)
_cell_length_c                   11.0319(17)
_cell_measurement_reflns_used    776
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.73
_cell_measurement_theta_min      2.53
_cell_volume                     730.4(2)
_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 0.947
_diffrn_measured_fraction_theta_max 0.947
_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  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6614
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9780
_exptl_absorpt_correction_T_min  0.9611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, G. Sheldrick (1999)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0414
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0470P)²+0.0990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1073
_reflns_number_gt                2460
_reflns_number_total             3338
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0518809si20050908_105012.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               4021364
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 0.24062(13) 0.53202(11) 0.05199(9) 0.0389(3) Uani 1 1 d .
O2 O -0.01076(12) 0.40931(10) 0.10647(8) 0.0349(2) Uani 1 1 d .
N1 N 0.02127(15) 0.27716(13) 0.28940(11) 0.0331(3) Uani 1 1 d .
C12 C 0.27536(16) 0.40667(13) 0.20520(11) 0.0278(3) Uani 1 1 d .
C2 C -0.17519(16) 0.06696(14) 0.34072(11) 0.0291(3) Uani 1 1 d .
C1 C -0.06415(16) 0.20996(14) 0.37877(12) 0.0286(3) Uani 1 1 d .
C17 C 0.15658(17) 0.44765(13) 0.11838(11) 0.0283(3) Uani 1 1 d .
C11 C 0.20418(17) 0.32587(13) 0.28958(12) 0.0288(3) Uani 1 1 d .
C6 C -0.03902(17) 0.29445(15) 0.50600(12) 0.0328(3) Uani 1 1 d .
H6 H 0.0370 0.3908 0.5295 0.039 Uiso 1 1 calc R
C13 C 0.46388(18) 0.45140(15) 0.20713(12) 0.0337(3) Uani 1 1 d .
H13 H 0.5112 0.5037 0.1495 0.040 Uiso 1 1 calc R
C15 C 0.51177(18) 0.34237(16) 0.37253(13) 0.0393(3) Uani 1 1 d .
H15 H 0.5925 0.3211 0.4302 0.047 Uiso 1 1 calc R
C4 C -0.23492(19) 0.10166(16) 0.56295(13) 0.0394(3) Uani 1 1 d .
H4 H -0.2950 0.0638 0.6253 0.047 Uiso 1 1 calc R
C16 C 0.32863(18) 0.29442(15) 0.37213(13) 0.0348(3) Uani 1 1 d .
H16 H 0.2848 0.2390 0.4285 0.042 Uiso 1 1 calc R
C14 C 0.58168(18) 0.42169(16) 0.28992(14) 0.0396(3) Uani 1 1 d .
H14 H 0.7088 0.4546 0.2910 0.048 Uiso 1 1 calc R
C5 C -0.12230(19) 0.24094(16) 0.59815(13) 0.0375(3) Uani 1 1 d .
H5 H -0.1027 0.2988 0.6848 0.045 Uiso 1 1 calc R
C3 C -0.25963(18) 0.01797(16) 0.43705(13) 0.0363(3) Uani 1 1 d .
H3 H -0.3376 -0.0774 0.4147 0.044 Uiso 1 1 calc R
C7 C -0.20527(18) -0.03342(15) 0.20180(12) 0.0354(3) Uani 1 1 d .
C10 C -0.0237(2) -0.06250(17) 0.14654(13) 0.0422(3) Uani 1 1 d .
H10A H 0.0520 0.0338 0.1487 0.063 Uiso 1 1 calc R
H10B H -0.0459 -0.1271 0.0587 0.063 Uiso 1 1 calc R
H10C H 0.0390 -0.1128 0.1969 0.063 Uiso 1 1 calc R
C8 C -0.3183(2) -0.18868(17) 0.19131(15) 0.0534(4) Uani 1 1 d .
H8A H -0.2571 -0.2381 0.2433 0.080 Uiso 1 1 calc R
H8B H -0.3310 -0.2511 0.1026 0.080 Uiso 1 1 calc R
H8C H -0.4388 -0.1761 0.2214 0.080 Uiso 1 1 calc R
C9 C -0.3104(2) 0.03909(18) 0.12084(13) 0.0454(4) Uani 1 1 d .
H9A H -0.4231 0.0618 0.1599 0.068 Uiso 1 1 calc R
H9B H -0.3395 -0.0310 0.0354 0.068 Uiso 1 1 calc R
H9C H -0.2355 0.1327 0.1157 0.068 Uiso 1 1 calc R
H1 H -0.048(2) 0.2909(16) 0.2274(14) 0.041(4) Uiso 1 1 d .
H2 H 0.155(2) 0.551(2) -0.0026(17) 0.067(5) 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
C11 N1 C1 125.41(11)
C13 C12 C11 119.32(11)
C13 C12 C17 119.06(11)
C11 C12 C17 121.60(11)
C3 C2 C1 116.08(12)
C3 C2 C7 120.55(11)
C1 C2 C7 123.37(11)
C6 C1 C2 120.90(11)
C6 C1 N1 117.24(11)
C2 C1 N1 121.82(11)
O2 C17 O1 120.97(11)
O2 C17 C12 124.00(11)
O1 C17 C12 115.03(11)
N1 C11 C16 120.84(11)
N1 C11 C12 121.43(11)
C16 C11 C12 117.72(11)
C5 C6 C1 121.17(12)
C14 C13 C12 121.77(12)
C16 C15 C14 121.17(12)
C3 C4 C5 119.75(12)
C15 C16 C11 121.15(12)
C13 C14 C15 118.86(13)
C6 C5 C4 119.08(12)
C4 C3 C2 123.01(13)
C10 C7 C8 106.52(12)
C10 C7 C9 110.50(11)
C8 C7 C9 106.81(12)
C10 C7 C2 110.78(11)
C8 C7 C2 111.40(11)
C9 C7 C2 110.68(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C17 1.3225(14)
O2 C17 1.2383(15)
N1 C11 1.3702(16)
N1 C1 1.4248(16)
C12 C13 1.4024(17)
C12 C11 1.4210(17)
C12 C17 1.4620(17)
C2 C3 1.3977(17)
C2 C1 1.4048(17)
C2 C7 1.5429(18)
C1 C6 1.3928(18)
C11 C16 1.4098(17)
C6 C5 1.3753(19)
C13 C14 1.3702(19)
C15 C16 1.3704(18)
C15 C14 1.3931(19)
C4 C3 1.3784(19)
C4 C5 1.383(2)
C7 C10 1.532(2)
C7 C8 1.5348(19)
C7 C9 1.5385(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21108219
2 PubChem 12166385
