#------------------------------------------------------------------------------
#$Date: 2022-08-15 23:51:12 +0200 (Mon 15 de Aug de 2022) $
#$Revision: 277244 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/05/7130532.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_7130532
loop_
_publ_author_name
'Mandal, Mou'
'Balamurugan, Rengarajan'
_publ_section_title
;
 TfOH-promoted synthesis of indoles and benzofurans involving cyclative
 transposition of vinyl ketone
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03730K
_journal_year                    2022
_chemical_formula_moiety         'C24 H19 N O'
_chemical_formula_sum            'C24 H19 N O'
_chemical_formula_weight         337.40
_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   geom
_audit_creation_date             2021-11-03
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2022-04-14 deposited with the CCDC.	2022-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.934(4)
_cell_angle_beta                 95.031(4)
_cell_angle_gamma                105.858(3)
_cell_formula_units_Z            2
_cell_length_a                   5.9743(5)
_cell_length_b                   10.7749(9)
_cell_length_c                   14.3140(13)
_cell_measurement_reflns_used    9879
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.38
_cell_volume                     882.17(13)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300.0
_diffrn_measured_fraction_theta_full 0.999
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0757
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            49611
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.639
_diffrn_reflns_theta_min         1.429
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1173 before and 0.0883 after correction. The Ratio of minimum to maximum transmission is 0.8763. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4086
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0679
_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)+(0.0914P)²+0.2398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1700
_refine_ls_wR_factor_ref         0.1896
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2765
_reflns_number_total             4086
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc03730k4.cif
_cod_data_source_block           rb007_0m_a
_cod_original_cell_volume        882.16(13)
_cod_database_code               7130532
_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   0.992
_shelx_estimated_absorpt_t_min   0.985
_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
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C23(H23), C22(H22), C8(H8), C21(H21), C19(H19), C5(H5), C12(H12),
 C3(H3), C20(H20), C4(H4), C1(H1), C2(H2), C15(H15), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
N1 N 1.1726(3) 0.54578(15) 0.65213(11) 0.0475(4) Uani 1 1 d . . . . .
O1 O 0.5672(3) 0.78274(17) 0.90766(11) 0.0755(5) Uani 1 1 d . . . . .
C18 C 1.0187(3) 0.47471(17) 0.80421(13) 0.0408(4) Uani 1 1 d . . . . .
C17 C 1.0373(3) 0.55781(17) 0.72255(13) 0.0411(4) Uani 1 1 d . . . . .
C10 C 0.9344(3) 0.65743(17) 0.70384(13) 0.0418(4) Uani 1 1 d . . . . .
C9 C 0.7989(3) 0.70230(17) 0.76775(14) 0.0444(4) Uani 1 1 d . . . . .
H9 H 0.791186 0.664366 0.825710 0.053 Uiso 1 1 calc R . . . .
C6 C 0.4320(3) 0.92995(17) 0.81414(14) 0.0458(5) Uani 1 1 d . . . . .
C23 C 1.2141(3) 0.47552(19) 0.86405(14) 0.0496(5) Uani 1 1 d . . . . .
H23 H 1.359621 0.528212 0.852314 0.060 Uiso 1 1 calc R . . . .
C11 C 1.0145(3) 0.70940(17) 0.61620(13) 0.0455(5) Uani 1 1 d . . . . .
C22 C 1.1955(4) 0.3990(2) 0.94095(15) 0.0553(5) Uani 1 1 d . . . . .
H22 H 1.328297 0.399753 0.980306 0.066 Uiso 1 1 calc R . . . .
C7 C 0.5627(3) 0.83068(18) 0.83085(14) 0.0482(5) Uani 1 1 d . . . . .
C8 C 0.6824(4) 0.79121(19) 0.75531(14) 0.0500(5) Uani 1 1 d . . . . .
H8 H 0.677095 0.828911 0.697470 0.060 Uiso 1 1 calc R . . . .
C21 C 0.9816(4) 0.3218(2) 0.95945(15) 0.0568(5) Uani 1 1 d . . . . .
H21 H 0.969392 0.270601 1.011471 0.068 Uiso 1 1 calc R . . . .
C16 C 1.1622(3) 0.63753(19) 0.58724(14) 0.0488(5) Uani 1 1 d . . . . .
C19 C 0.8045(3) 0.3952(2) 0.82381(16) 0.0549(5) Uani 1 1 d . . . . .
H19 H 0.671199 0.392432 0.784109 0.066 Uiso 1 1 calc R . . . .
C24 C 1.2980(4) 0.4498(2) 0.64125(16) 0.0583(6) Uani 1 1 d . . . . .
H24A H 1.256229 0.409003 0.579665 0.088 Uiso 1 1 calc GR . . . .
H24B H 1.257922 0.386068 0.687563 0.088 Uiso 1 1 calc GR . . . .
H24C H 1.463150 0.490744 0.649297 0.088 Uiso 1 1 calc GR . . . .
C5 C 0.4189(4) 0.9910(2) 0.73031(16) 0.0588(6) Uani 1 1 d . . . . .
H5 H 0.495879 0.971719 0.680646 0.071 Uiso 1 1 calc R . . . .
C12 C 0.9844(4) 0.8104(2) 0.56121(15) 0.0582(6) Uani 1 1 d . . . . .
H12 H 0.886786 0.859309 0.578049 0.070 Uiso 1 1 calc R . . . .
C3 C 0.1762(4) 1.1100(2) 0.7921(2) 0.0680(7) Uani 1 1 d . . . . .
H3 H 0.089452 1.169386 0.784374 0.082 Uiso 1 1 calc R . . . .
C20 C 0.7864(4) 0.3201(2) 0.90152(17) 0.0620(6) Uani 1 1 d . . . . .
H20 H 0.641252 0.268268 0.914416 0.074 Uiso 1 1 calc R . . . .
C4 C 0.2917(4) 1.0807(2) 0.71997(18) 0.0686(7) Uani 1 1 d . . . . .
H4 H 0.284745 1.121515 0.663460 0.082 Uiso 1 1 calc R . . . .
C1 C 0.3160(4) 0.9619(2) 0.88700(17) 0.0582(6) Uani 1 1 d . . . . .
H1 H 0.323991 0.922552 0.944070 0.070 Uiso 1 1 calc R . . . .
C2 C 0.1892(4) 1.0511(2) 0.8759(2) 0.0686(7) Uani 1 1 d . . . . .
H2 H 0.112399 1.071352 0.925368 0.082 Uiso 1 1 calc R . . . .
C15 C 1.2761(4) 0.6635(3) 0.50617(17) 0.0686(6) Uani 1 1 d . . . . .
H15 H 1.371871 0.614443 0.487636 0.082 Uiso 1 1 calc R . . . .
C13 C 1.1002(5) 0.8369(2) 0.48194(18) 0.0713(7) Uani 1 1 d . . . . .
H13 H 1.082751 0.905376 0.446009 0.086 Uiso 1 1 calc R . . . .
C14 C 1.2423(5) 0.7636(3) 0.45467(19) 0.0785(8) Uani 1 1 d . . . . .
H14 H 1.316452 0.782851 0.400110 0.094 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 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 N1 C16 108.91(15) . . ?
C17 N1 C24 127.62(17) . . ?
C16 N1 C24 123.38(17) . . ?
C23 C18 C17 120.93(17) . . ?
C23 C18 C19 118.17(18) . . ?
C19 C18 C17 120.90(16) . . ?
N1 C17 C18 121.62(15) . . ?
N1 C17 C10 109.66(16) . . ?
C10 C17 C18 128.70(16) . . ?
C17 C10 C9 123.63(17) . . ?
C17 C10 C11 106.23(16) . . ?
C9 C10 C11 129.82(17) . . ?
C8 C9 C10 128.74(19) . . ?
C5 C6 C7 123.86(18) . . ?
C5 C6 C1 118.19(18) . . ?
C1 C6 C7 117.95(18) . . ?
C22 C23 C18 120.72(18) . . ?
C16 C11 C10 106.48(16) . . ?
C12 C11 C10 135.39(19) . . ?
C12 C11 C16 118.09(19) . . ?
C21 C22 C23 120.16(19) . . ?
O1 C7 C6 119.42(18) . . ?
O1 C7 C8 120.61(17) . . ?
C8 C7 C6 119.96(17) . . ?
C9 C8 C7 121.42(18) . . ?
C20 C21 C22 120.02(19) . . ?
N1 C16 C11 108.72(17) . . ?
N1 C16 C15 129.02(19) . . ?
C15 C16 C11 122.24(19) . . ?
C20 C19 C18 120.85(18) . . ?
C6 C5 C4 120.4(2) . . ?
C13 C12 C11 119.4(2) . . ?
C4 C3 C2 119.7(2) . . ?
C21 C20 C19 120.1(2) . . ?
C3 C4 C5 120.7(2) . . ?
C2 C1 C6 121.0(2) . . ?
C3 C2 C1 120.1(2) . . ?
C14 C15 C16 117.7(2) . . ?
C12 C13 C14 121.2(2) . . ?
C15 C14 C13 121.4(2) . . ?
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
N1 C17 1.372(2) . ?
N1 C16 1.377(2) . ?
N1 C24 1.447(2) . ?
O1 C7 1.224(2) . ?
C18 C17 1.478(3) . ?
C18 C23 1.384(3) . ?
C18 C19 1.387(3) . ?
C17 C10 1.394(2) . ?
C10 C9 1.433(3) . ?
C10 C11 1.449(3) . ?
C9 C8 1.335(3) . ?
C6 C7 1.497(3) . ?
C6 C5 1.384(3) . ?
C6 C1 1.390(3) . ?
C23 C22 1.380(3) . ?
C11 C16 1.406(3) . ?
C11 C12 1.395(3) . ?
C22 C21 1.371(3) . ?
C7 C8 1.466(3) . ?
C21 C20 1.366(3) . ?
C16 C15 1.390(3) . ?
C19 C20 1.381(3) . ?
C5 C4 1.386(3) . ?
C12 C13 1.374(3) . ?
C3 C4 1.369(4) . ?
C3 C2 1.372(3) . ?
C1 C2 1.380(3) . ?
C15 C14 1.366(3) . ?
C13 C14 1.382(4) . ?
