#------------------------------------------------------------------------------
#$Date: 2024-06-28 12:32:51 +0300 (Fri, 28 Jun 2024) $
#$Revision: 292638 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/22/7132282.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_7132282
loop_
_publ_author_name
'Bhowmik, arup'
'Naskar, Koushik'
'Roy, Shantonu'
'Karmakar, Sudip'
'Sarkar, Writhabrata'
'Mondal, Imtiaj'
'Sana, Arindam'
'Deb, Indubhusan'
_publ_section_title
;
 A Condition-Tuned Unorthodox Approach to Indole-3-Carboxylic Acids and
 Anthranilic Acids via Carbon Atom Translocation
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04443B
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C10 H9 N O2'
_chemical_formula_sum            'C10 H9 N O2'
_chemical_formula_weight         175.188
_chemical_name_systematic        'AB 03 435'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_Int_Tables_number      4
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2022-10-19 deposited with the CCDC.	2023-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.468(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0202(4)
_cell_length_b                   29.187(2)
_cell_length_c                   5.9119(5)
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      66.537
_cell_measurement_theta_min      7.620
_cell_volume                     851.82(12)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_publication_material  'Bruker ShelXLe(Huebschle et all. 2011)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick 2018)'
_computing_structure_solution    'SHELXT 2018/2(Sheldrick 2014)'
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'CPAD area detector'
_diffrn_detector_area_resol_mean 7.407
_diffrn_detector_type            'Bruker Photon III'
_diffrn_measured_fraction_theta_full 0.9809
_diffrn_measured_fraction_theta_max 0.9803
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX3_IMuS Diamond_Photon III (1)'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.9809
_diffrn_reflns_Laue_measured_fraction_max 0.9803
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            25396
_diffrn_reflns_point_group_measured_fraction_full 0.9755
_diffrn_reflns_point_group_measured_fraction_max 0.9745
_diffrn_reflns_theta_full        66.6018
_diffrn_reflns_theta_max         66.60
_diffrn_reflns_theta_min         7.62
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_type              'Incoatec I\ms Diamond'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_T_max  0.5842
_exptl_absorpt_correction_T_min  0.4300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1300 before and 0.0893 after correction.
The Ratio of minimum to maximum transmission is 0.7360.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       block
_exptl_crystal_F_000             369.258
_exptl_crystal_preparation       'SLOW EVAPORATION'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.3535
_refine_diff_density_min         -0.2399
_refine_diff_density_rms         0.0603
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_d_res_high            0.8400
_refine_ls_d_res_low             5.8135
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0434
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     240
_refine_ls_number_reflns         2910
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0434
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0587
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0949P)²+0.7349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1568
_refine_ls_wR_factor_ref         0.1568
_reflns_Friedel_coverage         0.969
_reflns_limit_h_max              5
_reflns_limit_h_min              -5
_reflns_limit_k_max              34
_reflns_limit_k_min              -34
_reflns_limit_l_max              7
_reflns_limit_l_min              -7
_reflns_number_gt                2905
_reflns_number_total             2910
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3cc04443b2.cif
_cod_data_source_block           AB_03_435_0m_a
_cod_depositor_comments
;

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C20 H18 N2 O4'
_cod_original_formula_weight         350.377
_cod_original_formula_moiety         '2(C10 H9 N O2)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        851.83(12)
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_database_code               7132282
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4), C13(H13), C2(H2), C6(H6), C16(H16), C17(H17), C19(H19),
 C5(H5), C18(H18)
2.b Idealised Me refined as rotating group:
 C20(H20a,H20b,H20c), C9(H9a,H9b,H9c)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3)
;
_olex2_submission_original_sample_id 'AB 03 435'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-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_refinement_flags_posn
O1 O 0.0583(5) 0.49622(8) 0.4916(4) 0.0315(6) Uani 1.000000 .
H1 H 0.055(8) 0.5098(6) 0.366(3) 0.0473(9) Uiso 1.000000 GR
O3 O 0.4833(5) 0.50226(8) 0.0412(4) 0.0318(6) Uani 1.000000 .
H3 H 0.407(5) 0.4830(3) 0.114(6) 0.0477(9) Uiso 1.000000 GR
O2 O 0.3319(5) 0.44693(8) 0.3531(4) 0.0325(6) Uani 1.000000 .
O4 O 0.2097(5) 0.55126(9) 0.1806(4) 0.0314(6) Uani 1.000000 .
N1 N -0.0761(5) 0.38902(8) 0.9229(4) 0.0237(6) Uani 1.000000 .
N2 N 0.6216(5) 0.60974(8) -0.3876(4) 0.0243(6) Uani 1.000000 .
C3 C 0.0849(6) 0.35581(11) 0.8470(5) 0.0228(7) Uani 1.000000 .
C7 C 0.3780(6) 0.34870(11) 0.5672(5) 0.0251(7) Uani 1.000000 .
H7 H 0.4600(6) 0.36103(11) 0.4478(5) 0.0301(8) Uiso 1.000000 R
C1 C 0.1107(6) 0.42233(10) 0.6493(5) 0.0235(7) Uani 1.000000 .
C8 C 0.2053(6) 0.37568(11) 0.6743(5) 0.0212(7) Uani 1.000000 .
C20 C 0.7813(7) 0.61694(12) -0.5664(6) 0.0295(7) Uani 1.000000 .
H20a H 0.6600(7) 0.6218(9) -0.7142(10) 0.0442(11) Uiso 1.000000 GR
H20b H 0.897(4) 0.6439(5) -0.529(2) 0.0442(11) Uiso 1.000000 GR
H20c H 0.895(4) 0.5900(4) -0.577(3) 0.0442(11) Uiso 1.000000 GR
C11 C 0.3643(6) 0.54242(10) 0.0465(5) 0.0240(7) Uani 1.000000 .
C12 C 0.4325(6) 0.57614(11) -0.1139(5) 0.0241(7) Uani 1.000000 .
C15 C 0.3371(6) 0.62298(11) -0.1367(5) 0.0231(7) Uani 1.000000 .
C4 C 0.1299(7) 0.31069(11) 0.9191(6) 0.0266(7) Uani 1.000000 .
H4 H 0.0470(7) 0.29804(11) 1.0372(6) 0.0319(9) Uiso 1.000000 R
C14 C 0.4602(6) 0.64280(11) -0.3097(5) 0.0229(7) Uani 1.000000 .
C13 C 0.6040(7) 0.56981(11) -0.2690(5) 0.0246(7) Uani 1.000000 .
H13 H 0.6956(7) 0.54210(11) -0.2904(5) 0.0296(8) Uiso 1.000000 R
C10 C 0.1785(6) 0.45524(11) 0.4855(5) 0.0249(7) Uani 1.000000 .
C2 C -0.0589(6) 0.42771(11) 0.8038(5) 0.0251(7) Uani 1.000000 .
H2 H -0.1525(6) 0.45526(11) 0.8242(5) 0.0301(8) Uiso 1.000000 R
C6 C 0.4262(7) 0.30414(12) 0.6380(6) 0.0319(8) Uani 1.000000 .
H6 H 0.5463(7) 0.28591(12) 0.5689(6) 0.0383(9) Uiso 1.000000 R
C16 C 0.1642(7) 0.64971(12) -0.0287(6) 0.0291(7) Uani 1.000000 .
H16 H 0.0815(7) 0.63740(12) 0.0903(6) 0.0349(9) Uiso 1.000000 R
C17 C 0.1179(7) 0.69467(11) -0.1013(6) 0.0313(8) Uani 1.000000 .
H17 H -0.0000(7) 0.71320(11) -0.0314(6) 0.0376(9) Uiso 1.000000 R
C19 C 0.4124(7) 0.68817(11) -0.3825(6) 0.0279(7) Uani 1.000000 .
H19 H 0.4949(7) 0.70091(11) -0.5007(6) 0.0335(9) Uiso 1.000000 R
C9 C -0.2358(6) 0.38143(12) 1.1017(5) 0.0274(7) Uani 1.000000 .
H9a H -0.368(3) 0.3569(6) 1.054(2) 0.0411(11) Uiso 1.000000 GR
H9b H -0.1157(9) 0.3725(9) 1.2448(13) 0.0411(11) Uiso 1.000000 GR
H9c H -0.332(4) 0.4097(3) 1.127(3) 0.0411(11) Uiso 1.000000 GR
C5 C 0.3021(7) 0.28503(12) 0.8100(6) 0.0308(8) Uani 1.000000 .
H5 H 0.3364(7) 0.25391(12) 0.8528(6) 0.0369(9) Uiso 1.000000 R
C18 C 0.2402(7) 0.71349(12) -0.2749(6) 0.0343(9) Uani 1.000000 .
H18 H 0.2037(7) 0.74446(12) -0.3195(6) 0.0412(10) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03376 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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 N1 C3 108.7(3) . . ?
C9 N1 C3 123.9(3) . . ?
C9 N1 C2 127.3(3) . . ?
C14 N2 C20 124.9(3) . . ?
C13 N2 C20 126.2(3) . . ?
C13 N2 C14 108.9(2) . . ?
C8 C3 N1 107.4(3) . . ?
C4 C3 N1 129.4(3) . . ?
C4 C3 C8 123.2(3) . . ?
C6 C7 C8 118.8(3) . . ?
C10 C1 C8 125.6(3) . . ?
C2 C1 C8 105.9(3) . . ?
C2 C1 C10 128.4(3) . . ?
C7 C8 C3 118.6(3) . . ?
C1 C8 C3 106.7(3) . . ?
C1 C8 C7 134.6(3) . . ?
O4 C11 O3 122.8(3) . . ?
C12 C11 O3 115.2(3) . . ?
C12 C11 O4 122.0(3) . . ?
C15 C12 C11 126.1(3) . . ?
C13 C12 C11 126.4(3) . . ?
C13 C12 C15 107.5(3) . . ?
C14 C15 C12 105.9(3) . . ?
C16 C15 C12 134.8(3) . . ?
C16 C15 C14 119.3(3) . . ?
C5 C4 C3 116.7(3) . . ?
C15 C14 N2 108.3(3) . . ?
C19 C14 N2 129.2(3) . . ?
C19 C14 C15 122.5(3) . . ?
C12 C13 N2 109.4(3) . . ?
O2 C10 O1 122.3(3) . . ?
C1 C10 O1 114.3(3) . . ?
C1 C10 O2 123.4(3) . . ?
C1 C2 N1 111.2(3) . . ?
C5 C6 C7 121.4(3) . . ?
C17 C16 C15 117.9(3) . . ?
C18 C17 C16 121.8(3) . . ?
C18 C19 C14 116.9(3) . . ?
C6 C5 C4 121.3(3) . . ?
C19 C18 C17 121.6(3) . . ?
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
O1 C10 1.343(4) . ?
O3 C11 1.319(4) . ?
O2 C10 1.218(4) . ?
O4 C11 1.233(4) . ?
N1 C3 1.388(4) . ?
N1 C2 1.342(4) . ?
N1 C9 1.455(4) . ?
N2 C20 1.454(4) . ?
N2 C14 1.391(4) . ?
N2 C13 1.371(4) . ?
C3 C8 1.403(4) . ?
C3 C4 1.390(5) . ?
C7 C8 1.405(4) . ?
C7 C6 1.374(5) . ?
C1 C8 1.441(4) . ?
C1 C10 1.448(4) . ?
C1 C2 1.366(5) . ?
C11 C12 1.450(4) . ?
C12 C15 1.447(5) . ?
C12 C13 1.379(5) . ?
C15 C14 1.411(4) . ?
C15 C16 1.404(5) . ?
C4 C5 1.388(5) . ?
C14 C19 1.400(4) . ?
C6 C5 1.402(5) . ?
C16 C17 1.387(5) . ?
C17 C18 1.400(5) . ?
C19 C18 1.378(5) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C10 C1 C8 178.2(2) . . . . ?
O1 C10 C1 C2 0.7(4) . . . . ?
O3 C11 C12 C15 -177.8(3) . . . . ?
O3 C11 C12 C13 0.8(4) . . . . ?
O2 C10 C1 C8 -2.0(4) . . . . ?
O2 C10 C1 C2 -179.5(3) . . . . ?
O4 C11 C12 C15 1.0(4) . . . . ?
O4 C11 C12 C13 179.5(3) . . . . ?
N1 C3 C8 C7 -179.5(2) . . . . ?
N1 C3 C8 C1 0.1(3) . . . . ?
N1 C3 C4 C5 179.7(3) . . . . ?
N1 C2 C1 C8 0.6(3) . . . . ?
N1 C2 C1 C10 178.4(2) . . . . ?
N2 C14 C15 C12 0.0(3) . . . . ?
N2 C14 C15 C16 179.6(2) . . . . ?
N2 C14 C19 C18 179.6(3) . . . . ?
N2 C13 C12 C11 -178.8(2) . . . . ?
N2 C13 C12 C15 -0.1(3) . . . . ?
C3 C8 C7 C6 -1.1(3) . . . . ?
C3 C8 C1 C10 -178.3(2) . . . . ?
C3 C8 C1 C2 -0.4(3) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C7 C8 C1 C10 1.2(4) . . . . ?
C7 C8 C1 C2 179.1(4) . . . . ?
C7 C6 C5 C4 -1.4(4) . . . . ?
C11 C12 C15 C14 178.8(3) . . . . ?
C11 C12 C15 C16 -0.7(4) . . . . ?
C12 C15 C14 C19 179.0(2) . . . . ?
C12 C15 C16 C17 -179.3(4) . . . . ?
C15 C14 C19 C18 0.9(4) . . . . ?
C15 C16 C17 C18 -0.7(4) . . . . ?
C14 C19 C18 C17 -0.2(4) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?
