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#$Date: 2024-07-05 19:35:34 +0200 (Fri 05 de Jul de 2024) $
#$Revision: 293188 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/31/7063185.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_7063185
loop_
_publ_author_name
'Altia, Minakshi'
'Anbarasan, Pazhamalai'
_publ_section_title
;
 α-Hydroxydimethylacetal/ketal as an α-hydroxycarbonyl equivalent in
 interrupted Heyns/Amadori rearrangement: regioselective synthesis of
 substituted C2- and C3-acylindoles
;
_journal_issue                   22
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              9981
_journal_page_last               9989
_journal_paper_doi               10.1039/D4NJ00771A
_journal_volume                  48
_journal_year                    2024
_chemical_formula_sum            'C16 H13 N O'
_chemical_formula_weight         235.27
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc2gq3q1
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-07-29 deposited with the CCDC.	2024-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                101.137(2)
_cell_angle_beta                 93.235(2)
_cell_angle_gamma                96.394(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4062(4)
_cell_length_b                   7.8098(5)
_cell_length_c                   10.9025(6)
_cell_measurement_reflns_used    9884
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      33.05
_cell_measurement_theta_min      2.78
_cell_volume                     612.92(6)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3(Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker axs kappa apex3 PHOTON II Diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            39332
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.143
_diffrn_reflns_theta_min         3.242
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker 2016'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.006
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         4672
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0575
_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)+(0.1235P)²+0.0886P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1773
_refine_ls_wR_factor_ref         0.2091
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3264
_reflns_number_total             4672
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj00771a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7063185--7063187.cif.'
_cod_database_code               7063185
_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_min   0.970
_shelx_estimated_absorpt_t_max   1.000
loop_
_space_group_symop_operation_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_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
C1 C 0.28208(14) 0.28667(16) 0.58555(11) 0.0358(2) Uani 1 1 d . . . . .
C2 C 0.43381(13) 0.24894(16) 0.51922(12) 0.0360(2) Uani 1 1 d . . . . .
C3 C 0.36456(14) 0.15941(16) 0.39420(12) 0.0363(2) Uani 1 1 d . . . . .
C4 C 0.44327(18) 0.0943(2) 0.28329(14) 0.0467(3) Uani 1 1 d . . . . .
H4 H 0.569301 0.103111 0.281373 0.056 Uiso 1 1 calc R U . . .
C5 C 0.3312(2) 0.0171(2) 0.17716(15) 0.0569(4) Uani 1 1 d . . . . .
H5 H 0.383036 -0.025591 0.103400 0.068 Uiso 1 1 calc R U . . .
C6 C 0.1410(2) 0.0015(2) 0.17800(15) 0.0576(4) Uani 1 1 d . . . . .
H6 H 0.068851 -0.053186 0.105436 0.069 Uiso 1 1 calc R U . . .
C7 C 0.05945(18) 0.0662(2) 0.28510(14) 0.0503(3) Uani 1 1 d . . . . .
H7 H -0.066705 0.056540 0.286294 0.060 Uiso 1 1 calc R U . . .
C8 C 0.17315(15) 0.14635(17) 0.39107(12) 0.0384(3) Uani 1 1 d . . . . .
C9 C 0.26199(14) 0.37489(17) 0.71587(12) 0.0381(3) Uani 1 1 d . . . . .
C10 C 0.1930(2) 0.5346(2) 0.73876(14) 0.0508(3) Uani 1 1 d . . . . .
H10 H 0.160455 0.586491 0.672153 0.061 Uiso 1 1 calc R U . . .
C11 C 0.1722(3) 0.6177(3) 0.86086(16) 0.0652(5) Uani 1 1 d . . . . .
H11 H 0.127831 0.726053 0.875750 0.078 Uiso 1 1 calc R U . . .
C12 C 0.2168(2) 0.5407(3) 0.95993(15) 0.0618(4) Uani 1 1 d . . . . .
H12 H 0.202456 0.596915 1.041483 0.074 Uiso 1 1 calc R U . . .
C13 C 0.2824(3) 0.3811(3) 0.93848(16) 0.0618(4) Uani 1 1 d . . . . .
H13 H 0.311516 0.328506 1.005401 0.074 Uiso 1 1 calc R U . . .
C14 C 0.3053(2) 0.2979(2) 0.81668(15) 0.0533(4) Uani 1 1 d . . . . .
H14 H 0.349965 0.189680 0.802506 0.064 Uiso 1 1 calc R U . . .
C15 C 0.62635(14) 0.29137(18) 0.56180(13) 0.0402(3) Uani 1 1 d . . . . .
C16 C 0.68814(19) 0.4093(3) 0.68595(16) 0.0568(4) Uani 1 1 d . . . . .
H16A H 0.583821 0.444645 0.727951 0.085 Uiso 1 1 calc R U . . .
H16B H 0.756686 0.347198 0.736411 0.085 Uiso 1 1 calc R U . . .
H16C H 0.763506 0.511467 0.673044 0.085 Uiso 1 1 calc R U . . .
N1 N 0.12831(13) 0.22485(16) 0.50772(10) 0.0421(3) Uani 1 1 d . . . . .
H1N H 0.019(3) 0.235(2) 0.5288(17) 0.050 Uiso 1 1 d . U . . .
O1 O 0.74186(12) 0.23210(18) 0.49373(11) 0.0572(3) Uani 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_
_citation_id
_citation_doi
_citation_year
1 10.1039/D3CC04144A 2023
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
N1 C1 C2 108.63(11) . . ?
N1 C1 C9 118.43(9) . . ?
C2 C1 C9 132.94(10) . . ?
C1 C2 C3 106.59(9) . . ?
C1 C2 C15 128.81(12) . . ?
C3 C2 C15 124.59(10) . . ?
C4 C3 C8 118.07(12) . . ?
C4 C3 C2 135.08(11) . . ?
C8 C3 C2 106.80(10) . . ?
C5 C4 C3 119.10(12) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.46(14) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 120.84(14) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 117.38(13) . . ?
C6 C7 H7 121.3 . . ?
C8 C7 H7 121.3 . . ?
N1 C8 C7 129.25(11) . . ?
N1 C8 C3 107.66(10) . . ?
C7 C8 C3 123.09(12) . . ?
C10 C9 C14 118.83(13) . . ?
C10 C9 C1 119.83(12) . . ?
C14 C9 C1 121.31(12) . . ?
C9 C10 C11 120.21(14) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.38(16) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 120.03(15) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 119.95(16) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 120.59(15) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
O1 C15 C2 119.69(13) . . ?
O1 C15 C16 119.00(11) . . ?
C2 C15 C16 121.30(11) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 N1 C8 110.32(9) . . ?
C1 N1 H1N 124.5(12) . . ?
C8 N1 H1N 125.2(12) . . ?
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
C1 N1 1.3639(15) . ?
C1 C2 1.3985(14) . ?
C1 C9 1.4779(17) . ?
C2 C3 1.4432(17) . ?
C2 C15 1.4558(15) . ?
C3 C4 1.4030(17) . ?
C3 C8 1.4080(15) . ?
C4 C5 1.379(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.401(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.380(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.3889(18) . ?
C7 H7 0.9300 . ?
C8 N1 1.3767(16) . ?
C9 C10 1.384(2) . ?
C9 C14 1.390(2) . ?
C10 C11 1.389(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.390(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 O1 1.2346(15) . ?
C15 C16 1.498(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1 H1N 0.860(19) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O1 0.860(19) 2.065(19) 2.8650(13) 154.4(17) 1_455 yes
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
N1 C1 C2 C3 0.11(15) . . . . ?
C9 C1 C2 C3 179.87(13) . . . . ?
N1 C1 C2 C15 178.92(13) . . . . ?
C9 C1 C2 C15 -1.3(2) . . . . ?
C1 C2 C3 C4 176.95(15) . . . . ?
C15 C2 C3 C4 -1.9(2) . . . . ?
C1 C2 C3 C8 -0.31(14) . . . . ?
C15 C2 C3 C8 -179.18(12) . . . . ?
C8 C3 C4 C5 -1.5(2) . . . . ?
C2 C3 C4 C5 -178.49(15) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C6 C7 C8 N1 178.24(15) . . . . ?
C6 C7 C8 C3 -1.8(2) . . . . ?
C4 C3 C8 N1 -177.42(12) . . . . ?
C2 C3 C8 N1 0.40(14) . . . . ?
C4 C3 C8 C7 2.6(2) . . . . ?
C2 C3 C8 C7 -179.59(13) . . . . ?
N1 C1 C9 C10 -66.90(17) . . . . ?
C2 C1 C9 C10 113.36(16) . . . . ?
N1 C1 C9 C14 110.88(15) . . . . ?
C2 C1 C9 C14 -68.9(2) . . . . ?
C14 C9 C10 C11 1.6(2) . . . . ?
C1 C9 C10 C11 179.45(14) . . . . ?
C9 C10 C11 C12 -1.2(3) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C13 C14 C9 -0.1(3) . . . . ?
C10 C9 C14 C13 -1.0(2) . . . . ?
C1 C9 C14 C13 -178.79(13) . . . . ?
C1 C2 C15 O1 172.82(13) . . . . ?
C3 C2 C15 O1 -8.6(2) . . . . ?
C1 C2 C15 C16 -8.5(2) . . . . ?
C3 C2 C15 C16 170.08(13) . . . . ?
C2 C1 N1 C8 0.14(16) . . . . ?
C9 C1 N1 C8 -179.66(11) . . . . ?
C7 C8 N1 C1 179.65(15) . . . . ?
C3 C8 N1 C1 -0.34(15) . . . . ?
