#------------------------------------------------------------------------------
#$Date: 2023-10-31 23:57:10 +0100 (Tue 31 de Oct de 2023) $
#$Revision: 287174 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/22/7132283.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_7132283
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_formula_moiety         '0.24(C10 H8 D N O2)'
_chemical_formula_sum            'C2.35 H1.88 D0.24 N0.24 O0.47'
_chemical_formula_weight         41.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-07-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-05-31 deposited with the CCDC.	2023-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.326(5)
_cell_angle_gamma                90
_cell_formula_units_Z            17
_cell_length_a                   5.0244(4)
_cell_length_b                   29.261(2)
_cell_length_c                   5.9187(5)
_cell_measurement_reflns_used    3598
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      65.96
_cell_measurement_theta_min      3.02
_cell_volume                     856.07(12)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0777
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_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            12421
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.700
_diffrn_reflns_theta_max         66.700
_diffrn_reflns_theta_min         3.020
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.788
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1218 before and 0.0794 after correction. The Ratio of minimum to maximum transmission is 0.8300. 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    1.367
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_preparation       'GROWING IN CHCL3'
_exptl_crystal_recrystallization_method 'SLOW EVAPORATION'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.229
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.229
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0918
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+1.7853P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1643
_refine_ls_wR_factor_ref         0.1665
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1413
_reflns_number_total             1498
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc04443b2.cif
_cod_data_source_block           ibd_ab_15_7_0m_a
_cod_original_cell_volume        856.08(12)
_cod_database_code               7132283
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.891
_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(D7), C2(H2A), C5(H5), C3(H3), C4(H4)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.2866(6) 0.49680(9) 0.2241(5) 0.0445(8) Uani 1 1 d . . . . .
H2 H 0.336760 0.514241 0.127041 0.067 Uiso 1 1 calc GR . . . .
O1 O 0.5596(6) 0.44776(9) 0.0848(5) 0.0469(8) Uani 1 1 d . . . . .
N1 N 0.1472(6) 0.38962(10) 0.6510(5) 0.0353(8) Uani 1 1 d . . . . .
C6 C 0.3070(7) 0.35667(13) 0.5747(6) 0.0331(9) Uani 1 1 d . . . . .
C1 C 0.4284(7) 0.37664(12) 0.4002(6) 0.0324(8) Uani 1 1 d . . . . .
C8 C 0.3370(8) 0.42290(12) 0.3780(6) 0.0340(9) Uani 1 1 d . . . . .
C7 C 0.1655(8) 0.42909(13) 0.5351(6) 0.0358(9) Uani 1 1 d . . . . .
D7 D 0.074918 0.456751 0.557808 0.043 Uiso 1 1 calc R . . . .
C9 C 0.4047(8) 0.45636(13) 0.2182(6) 0.0373(9) Uani 1 1 d . . . . .
C2 C 0.5989(8) 0.34966(13) 0.2933(7) 0.0403(10) Uani 1 1 d . . . . .
H2A H 0.682181 0.361938 0.174673 0.048 Uiso 1 1 calc R . . . .
C10 C -0.0141(8) 0.38238(14) 0.8315(7) 0.0429(10) Uani 1 1 d . . . . .
H10A H -0.145203 0.357826 0.785228 0.064 Uiso 1 1 calc GR . . . .
H10B H -0.110540 0.410613 0.855029 0.064 Uiso 1 1 calc GR . . . .
H10C H 0.105575 0.373883 0.974853 0.064 Uiso 1 1 calc GR . . . .
C5 C 0.3500(8) 0.31147(13) 0.6438(7) 0.0424(10) Uani 1 1 d . . . . .
H5 H 0.264162 0.298597 0.759494 0.051 Uiso 1 1 calc R . . . .
C3 C 0.6444(9) 0.30507(14) 0.3626(8) 0.0493(11) Uani 1 1 d . . . . .
H3 H 0.760694 0.286600 0.290889 0.059 Uiso 1 1 calc R . . . .
C4 C 0.5227(9) 0.28622(14) 0.5371(8) 0.0496(11) Uani 1 1 d . . . . .
H4 H 0.560340 0.255407 0.582450 0.060 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O2 H2 109.5 . . ?
C6 N1 C10 124.5(3) . . ?
C7 N1 C6 109.4(3) . . ?
C7 N1 C10 126.0(3) . . ?
N1 C6 C1 107.6(3) . . ?
N1 C6 C5 129.5(3) . . ?
C5 C6 C1 122.9(3) . . ?
C6 C1 C8 106.6(3) . . ?
C2 C1 C6 118.4(3) . . ?
C2 C1 C8 135.0(3) . . ?
C1 C8 C9 126.4(3) . . ?
C7 C8 C1 106.9(3) . . ?
C7 C8 C9 126.7(3) . . ?
N1 C7 C8 109.5(3) . . ?
N1 C7 D7 125.2 . . ?
C8 C7 D7 125.2 . . ?
O2 C9 C8 115.4(3) . . ?
O1 C9 O2 122.5(3) . . ?
O1 C9 C8 122.1(3) . . ?
C1 C2 H2A 120.5 . . ?
C3 C2 C1 118.9(4) . . ?
C3 C2 H2A 120.5 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C5 H5 121.5 . . ?
C4 C5 C6 117.0(4) . . ?
C4 C5 H5 121.5 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.4(4) . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 121.3(4) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
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
O2 H2 0.8400 . ?
O2 C9 1.327(4) . ?
O1 C9 1.230(5) . ?
N1 C6 1.381(5) . ?
N1 C7 1.355(5) . ?
N1 C10 1.467(4) . ?
C6 C1 1.416(5) . ?
C6 C5 1.390(5) . ?
C1 C8 1.428(5) . ?
C1 C2 1.397(5) . ?
C8 C7 1.388(5) . ?
C8 C9 1.444(5) . ?
C7 D7 0.9500 . ?
C2 H2A 0.9500 . ?
C2 C3 1.375(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C5 H5 0.9500 . ?
C5 C4 1.376(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.404(6) . ?
C4 H4 0.9500 . ?
