#------------------------------------------------------------------------------
#$Date: 2024-05-02 02:22:13 +0200 (Thu 02 de May de 2024) $
#$Revision: 291451 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/31/7063187.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_7063187
loop_
_publ_author_name
'Altia, Minakshi'
'Anbarasan, Pazhamalai'
_publ_section_title
;
 α-Hydroxydimethylacetal/ketal as α-hydroxycarbonyl equivalent in
 interrupted Heyns/Amadori rearrangement: Regioselective synthesis of
 substituted C2- and C3-acylindoles
;
_journal_name_full               'New Journal of Chemistry'
_journal_paper_doi               10.1039/D4NJ00771A
_journal_year                    2024
_chemical_formula_moiety         'C21 H14 Br N O'
_chemical_formula_sum            'C21 H14 Br N O'
_chemical_formula_weight         376.24
_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.cc2gq3p0
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-07-29 deposited with the CCDC.	2024-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                98.203(2)
_cell_angle_beta                 101.166(2)
_cell_angle_gamma                103.107(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6408(5)
_cell_length_b                   9.9341(5)
_cell_length_c                   10.3685(5)
_cell_measurement_reflns_used    5672
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.21
_cell_measurement_theta_min      2.49
_cell_volume                     834.05(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12302
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.041
_exptl_absorpt_coefficient_mu    2.470
_exptl_absorpt_correction_T_max  0.756
_exptl_absorpt_correction_T_min  0.612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       Block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0127(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0302
_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)+(0.0382P)²+0.3547P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0769
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2472
_reflns_number_total             2924
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj00771a2.cif
_cod_data_source_block           958
_cod_database_code               7063187
_shelx_shelxl_version_number     2014/7
_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   0.612
_shelx_estimated_absorpt_t_max   0.756
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
Br1 Br 0.65114(3) 0.43470(3) 0.25377(3) 0.05911(15) Uani 1 1 d . . . . .
C1 C -0.4175(3) 0.1565(3) -0.3298(2) 0.0444(6) Uani 1 1 d . . . . .
H1 H -0.5292 0.1167 -0.3439 0.053 Uiso 1 1 calc R U . . .
C2 C -0.3500(3) 0.2004(3) -0.4305(3) 0.0519(7) Uani 1 1 d . . . . .
H2 H -0.4176 0.1900 -0.5148 0.062 Uiso 1 1 calc R U . . .
C3 C -0.1813(3) 0.2610(3) -0.4101(3) 0.0484(6) Uani 1 1 d . . . . .
H3 H -0.1398 0.2902 -0.4808 0.058 Uiso 1 1 calc R U . . .
C4 C -0.0768(3) 0.2776(2) -0.2875(2) 0.0397(5) Uani 1 1 d . . . . .
H4 H 0.0348 0.3169 -0.2749 0.048 Uiso 1 1 calc R U . . .
C5 C -0.1417(3) 0.2344(2) -0.1818(2) 0.0321(5) Uani 1 1 d . . . . .
C6 C -0.0707(2) 0.2314(2) -0.0460(2) 0.0298(5) Uani 1 1 d . . . . .
C7 C -0.1989(2) 0.1709(2) 0.0081(2) 0.0299(5) Uani 1 1 d . . . . .
C8 C -0.3116(3) 0.1741(2) -0.2050(2) 0.0328(5) Uani 1 1 d . . . . .
C9 C 0.1062(2) 0.2782(2) 0.0172(2) 0.0301(5) Uani 1 1 d . . . . .
C10 C 0.1933(3) 0.4172(2) 0.0307(2) 0.0368(5) Uani 1 1 d . . . . .
H10 H 0.1414 0.4797 -0.0067 0.044 Uiso 1 1 calc R U . . .
C11 C 0.3556(3) 0.4647(2) 0.0987(2) 0.0411(6) Uani 1 1 d . . . . .
H11 H 0.4122 0.5585 0.1086 0.049 Uiso 1 1 calc R U . . .
C12 C 0.4321(3) 0.3706(2) 0.1516(2) 0.0360(5) Uani 1 1 d . . . . .
C13 C 0.3519(3) 0.2307(2) 0.1348(2) 0.0387(5) Uani 1 1 d . . . . .
H13 H 0.4060 0.1675 0.1681 0.046 Uiso 1 1 calc R U . . .
C14 C 0.1896(3) 0.1859(2) 0.0675(2) 0.0352(5) Uani 1 1 d . . . . .
H14 H 0.1347 0.0914 0.0556 0.042 Uiso 1 1 calc R U . . .
C15 C -0.2061(2) 0.1283(2) 0.1362(2) 0.0320(5) Uani 1 1 d . . . . .
C16 C -0.0597(3) 0.1770(2) 0.2505(2) 0.0320(5) Uani 1 1 d . . . . .
C17 C 0.0277(3) 0.3175(2) 0.2912(2) 0.0345(5) Uani 1 1 d . . . . .
H17 H -0.0062 0.3852 0.2478 0.041 Uiso 1 1 calc R U . . .
C18 C 0.1648(3) 0.3569(3) 0.3957(2) 0.0435(6) Uani 1 1 d . . . . .
H18 H 0.2218 0.4514 0.4239 0.052 Uiso 1 1 calc R U . . .
C19 C 0.2174(3) 0.2569(3) 0.4584(3) 0.0510(7) Uani 1 1 d . . . . .
H19 H 0.3114 0.2835 0.5274 0.061 Uiso 1 1 calc R U . . .
C20 C 0.1306(3) 0.1170(3) 0.4191(3) 0.0532(7) Uani 1 1 d . . . . .
H20 H 0.1661 0.0493 0.4615 0.064 Uiso 1 1 calc R U . . .
C21 C -0.0084(3) 0.0777(3) 0.3169(2) 0.0433(6) Uani 1 1 d . . . . .
H21 H -0.0683 -0.0162 0.2923 0.052 Uiso 1 1 calc R U . . .
N1 N -0.3428(2) 0.1379(2) -0.08928(19) 0.0345(4) Uani 1 1 d . . . . .
O1 O -0.33070(19) 0.04688(18) 0.14752(17) 0.0467(4) Uani 1 1 d . . . . .
H1N H -0.429(3) 0.097(3) -0.080(2) 0.036(7) 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'
Br Br -0.2901 2.4595 '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
C2 C1 C8 117.1(2) . . ?
C2 C1 H1 121.4 . . ?
C8 C1 H1 121.4 . . ?
C1 C2 C3 121.8(2) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 118.7(2) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C8 119.1(2) . . ?
C4 C5 C6 133.6(2) . . ?
C8 C5 C6 107.25(18) . . ?
C7 C6 C5 106.44(18) . . ?
C7 C6 C9 128.72(19) . . ?
C5 C6 C9 124.78(18) . . ?
N1 C7 C6 108.64(18) . . ?
N1 C7 C15 117.83(18) . . ?
C6 C7 C15 133.31(19) . . ?
N1 C8 C1 130.0(2) . . ?
N1 C8 C5 107.76(18) . . ?
C1 C8 C5 122.2(2) . . ?
C14 C9 C10 117.87(19) . . ?
C14 C9 C6 121.29(18) . . ?
C10 C9 C6 120.82(19) . . ?
C11 C10 C9 121.3(2) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C12 C11 C10 118.8(2) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C13 C12 C11 121.5(2) . . ?
C13 C12 Br1 118.72(17) . . ?
C11 C12 Br1 119.79(16) . . ?
C12 C13 C14 118.6(2) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
C13 C14 C9 121.7(2) . . ?
C13 C14 H14 119.1 . . ?
C9 C14 H14 119.1 . . ?
O1 C15 C7 119.73(19) . . ?
O1 C15 C16 120.10(19) . . ?
C7 C15 C16 120.08(17) . . ?
C21 C16 C17 119.2(2) . . ?
C21 C16 C15 118.48(19) . . ?
C17 C16 C15 122.31(19) . . ?
C18 C17 C16 120.1(2) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 120.0(2) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 120.0(2) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C16 120.5(2) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
C8 N1 C7 109.90(18) . . ?
C8 N1 H1N 125.3(17) . . ?
C7 N1 H1N 124.5(17) . . ?
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
Br1 C12 1.896(2) . ?
C1 C2 1.367(4) . ?
C1 C8 1.395(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.407(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.401(3) . ?
C4 H4 0.9300 . ?
C5 C8 1.412(3) . ?
C5 C6 1.431(3) . ?
C6 C7 1.392(3) . ?
C6 C9 1.478(3) . ?
C7 N1 1.381(3) . ?
C7 C15 1.459(3) . ?
C8 N1 1.359(3) . ?
C9 C14 1.386(3) . ?
C9 C10 1.388(3) . ?
C10 C11 1.381(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.377(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(3) . ?
C13 C14 1.378(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 O1 1.228(2) . ?
C15 C16 1.489(3) . ?
C16 C21 1.385(3) . ?
C16 C17 1.388(3) . ?
C17 C18 1.380(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.381(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.376(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
N1 H1N 0.79(3) . ?
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
C8 C1 C2 C3 -0.1(4) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C8 0.6(3) . . . . ?
C3 C4 C5 C6 177.5(2) . . . . ?
C4 C5 C6 C7 -177.6(2) . . . . ?
C8 C5 C6 C7 -0.4(2) . . . . ?
C4 C5 C6 C9 -0.3(4) . . . . ?
C8 C5 C6 C9 176.82(19) . . . . ?
C5 C6 C7 N1 0.0(2) . . . . ?
C9 C6 C7 N1 -177.14(19) . . . . ?
C5 C6 C7 C15 174.2(2) . . . . ?
C9 C6 C7 C15 -2.9(4) . . . . ?
C2 C1 C8 N1 -178.3(2) . . . . ?
C2 C1 C8 C5 0.0(3) . . . . ?
C4 C5 C8 N1 178.38(19) . . . . ?
C6 C5 C8 N1 0.7(2) . . . . ?
C4 C5 C8 C1 -0.3(3) . . . . ?
C6 C5 C8 C1 -177.9(2) . . . . ?
C7 C6 C9 C14 57.5(3) . . . . ?
C5 C6 C9 C14 -119.2(2) . . . . ?
C7 C6 C9 C10 -121.0(3) . . . . ?
C5 C6 C9 C10 62.4(3) . . . . ?
C14 C9 C10 C11 -3.6(3) . . . . ?
C6 C9 C10 C11 174.9(2) . . . . ?
C9 C10 C11 C12 1.2(4) . . . . ?
C10 C11 C12 C13 1.9(4) . . . . ?
C10 C11 C12 Br1 -176.59(18) . . . . ?
C11 C12 C13 C14 -2.4(4) . . . . ?
Br1 C12 C13 C14 176.08(17) . . . . ?
C12 C13 C14 C9 -0.1(3) . . . . ?
C10 C9 C14 C13 3.0(3) . . . . ?
C6 C9 C14 C13 -175.4(2) . . . . ?
N1 C7 C15 O1 11.4(3) . . . . ?
C6 C7 C15 O1 -162.4(2) . . . . ?
N1 C7 C15 C16 -172.06(19) . . . . ?
C6 C7 C15 C16 14.1(4) . . . . ?
O1 C15 C16 C21 47.3(3) . . . . ?
C7 C15 C16 C21 -129.2(2) . . . . ?
O1 C15 C16 C17 -133.7(2) . . . . ?
C7 C15 C16 C17 49.8(3) . . . . ?
C21 C16 C17 C18 0.6(3) . . . . ?
C15 C16 C17 C18 -178.5(2) . . . . ?
C16 C17 C18 C19 1.3(4) . . . . ?
C17 C18 C19 C20 -1.6(4) . . . . ?
C18 C19 C20 C21 0.1(4) . . . . ?
C19 C20 C21 C16 1.8(4) . . . . ?
C17 C16 C21 C20 -2.1(4) . . . . ?
C15 C16 C21 C20 177.0(2) . . . . ?
C1 C8 N1 C7 177.7(2) . . . . ?
C5 C8 N1 C7 -0.8(2) . . . . ?
C6 C7 N1 C8 0.5(2) . . . . ?
C15 C7 N1 C8 -174.75(19) . . . . ?
