#------------------------------------------------------------------------------
#$Date: 2022-08-16 00:51:12 +0300 (Tue, 16 Aug 2022) $
#$Revision: 277244 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/05/7130534.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_7130534
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         'C19 H19 N O3'
_chemical_formula_sum            'C19 H19 N O3'
_chemical_formula_weight         309.35
_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     dual
_audit_creation_date             2022-03-17
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-04-14 deposited with the CCDC.	2022-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.575(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6702(4)
_cell_length_b                   9.9677(4)
_cell_length_c                   15.8095(8)
_cell_measurement_reflns_used    5259
_cell_measurement_temperature    297.42(10)
_cell_measurement_theta_max      26.6140
_cell_measurement_theta_min      2.0240
_cell_volume                     1584.27(13)
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      297.42(10)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'rigaku oxford'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10397
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.157
_diffrn_reflns_theta_min         2.029
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26625
_exptl_absorpt_correction_type   multi-scan
_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    1.297
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3248
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0495
_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)+(0.0720P)²+0.1102P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1437
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2236
_reflns_number_total             3248
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc03730k4.cif
_cod_data_source_block           rb100
_cod_database_code               7130534
_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   0.996
_shelx_estimated_absorpt_t_min   0.994
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C3(H3), C19(H19), C16(H16), C18(H18), C6(H6), C17(H17), C4(H4),
 C5(H5)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C12(H12A,H12B,H12C)
;
_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
O3 O 0.22021(13) 0.17373(13) 0.53140(10) 0.0612(4) Uani 1 1 d . . . . .
O2 O 0.51057(13) 0.46678(15) 0.82108(9) 0.0608(4) Uani 1 1 d . . . . .
O1 O 0.33516(13) 0.35562(17) 0.73247(11) 0.0772(5) Uani 1 1 d . . . . .
N1 N 0.59137(16) 0.16479(16) 0.61087(11) 0.0562(5) Uani 1 1 d . . . . .
C14 C 0.16613(15) 0.38555(17) 0.46341(11) 0.0392(4) Uani 1 1 d . . . . .
C2 C 0.47369(16) 0.28417(17) 0.48665(12) 0.0395(4) Uani 1 1 d . . . . .
C13 C 0.25994(16) 0.28321(18) 0.51907(12) 0.0410(4) Uani 1 1 d . . . . .
C1 C 0.40808(15) 0.31604(17) 0.55595(11) 0.0390(4) Uani 1 1 d . . . . .
H1 H 0.420158 0.411308 0.571942 0.047 Uiso 1 1 calc R . . . .
C7 C 0.57593(17) 0.19193(18) 0.52340(13) 0.0441(4) Uani 1 1 d . . . . .
C8 C 0.48704(16) 0.22951(18) 0.63786(12) 0.0433(4) Uani 1 1 d . . . . .
H8 H 0.428574 0.161143 0.649180 0.052 Uiso 1 1 calc R . . . .
C11 C 0.45127(18) 0.3780(2) 0.75688(12) 0.0479(5) Uani 1 1 d . . . . .
C15 C 0.20555(17) 0.51221(19) 0.44598(13) 0.0478(5) Uani 1 1 d . . . . .
H15 H 0.294414 0.537154 0.470518 0.057 Uiso 1 1 calc R . . . .
C3 C 0.44681(19) 0.32841(19) 0.39982(13) 0.0496(5) Uani 1 1 d . . . . .
H3 H 0.377863 0.388776 0.374763 0.060 Uiso 1 1 calc R . . . .
C19 C 0.03233(17) 0.3519(2) 0.42692(13) 0.0487(5) Uani 1 1 d . . . . .
H19 H 0.003928 0.267576 0.438018 0.058 Uiso 1 1 calc R . . . .
C10 C 0.55006(17) 0.3120(2) 0.72210(12) 0.0482(5) Uani 1 1 d . . . . .
H10A H 0.606931 0.254184 0.768521 0.058 Uiso 1 1 calc R . . . .
H10B H 0.605780 0.380616 0.709423 0.058 Uiso 1 1 calc R . . . .
C16 C 0.11416(19) 0.6016(2) 0.39257(14) 0.0573(5) Uani 1 1 d . . . . .
H16 H 0.141908 0.685779 0.380649 0.069 Uiso 1 1 calc R . . . .
C18 C -0.05876(18) 0.4421(2) 0.37447(14) 0.0580(6) Uani 1 1 d . . . . .
H18 H -0.148158 0.418697 0.350879 0.070 Uiso 1 1 calc R . . . .
C6 C 0.65031(19) 0.1430(2) 0.47308(14) 0.0571(5) Uani 1 1 d . . . . .
H6 H 0.717058 0.079889 0.496800 0.069 Uiso 1 1 calc R . . . .
C17 C -0.01754(19) 0.5665(2) 0.35703(14) 0.0592(6) Uani 1 1 d . . . . .
H17 H -0.078908 0.626951 0.321128 0.071 Uiso 1 1 calc R . . . .
C4 C 0.5228(2) 0.2827(2) 0.35013(14) 0.0633(6) Uani 1 1 d . . . . .
H4 H 0.506489 0.314088 0.292028 0.076 Uiso 1 1 calc R . . . .
C9 C 0.66025(19) 0.0489(2) 0.65839(15) 0.0636(6) Uani 1 1 d . . . . .
H9A H 0.616858 -0.031007 0.628857 0.095 Uiso 1 1 calc GR . . . .
H9B H 0.659278 0.050411 0.718886 0.095 Uiso 1 1 calc GR . . . .
H9C H 0.750590 0.049877 0.659154 0.095 Uiso 1 1 calc GR . . . .
C5 C 0.6222(2) 0.1911(2) 0.38626(15) 0.0663(6) Uani 1 1 d . . . . .
H5 H 0.671975 0.160405 0.351842 0.080 Uiso 1 1 calc R . . . .
C12 C 0.4276(2) 0.5345(2) 0.86307(16) 0.0738(7) Uani 1 1 d . . . . .
H12A H 0.357123 0.580454 0.818171 0.111 Uiso 1 1 calc GR . . . .
H12B H 0.480037 0.598255 0.905943 0.111 Uiso 1 1 calc GR . . . .
H12C H 0.390461 0.470053 0.893076 0.111 Uiso 1 1 calc GR . . . .
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
C11 O2 C12 116.96(16) . . ?
C7 N1 C8 111.21(14) . . ?
C7 N1 C9 123.77(16) . . ?
C9 N1 C8 120.37(16) . . ?
C15 C14 C13 123.45(15) . . ?
C15 C14 C19 118.34(16) . . ?
C19 C14 C13 118.21(16) . . ?
C7 C2 C1 108.81(15) . . ?
C3 C2 C1 131.28(16) . . ?
C3 C2 C7 119.90(17) . . ?
O3 C13 C14 120.64(16) . . ?
O3 C13 C1 120.39(15) . . ?
C14 C13 C1 118.89(15) . . ?
C2 C1 C13 110.39(14) . . ?
C2 C1 H1 109.6 . . ?
C2 C1 C8 103.51(13) . . ?
C13 C1 H1 109.6 . . ?
C13 C1 C8 113.81(14) . . ?
C8 C1 H1 109.6 . . ?
N1 C7 C2 111.40(16) . . ?
N1 C7 C6 127.88(17) . . ?
C6 C7 C2 120.69(18) . . ?
N1 C8 C1 104.76(14) . . ?
N1 C8 H8 109.8 . . ?
N1 C8 C10 109.70(14) . . ?
C1 C8 H8 109.8 . . ?
C10 C8 C1 112.88(15) . . ?
C10 C8 H8 109.8 . . ?
O2 C11 C10 110.99(16) . . ?
O1 C11 O2 123.22(18) . . ?
O1 C11 C10 125.79(19) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.65(17) . . ?
C16 C15 H15 119.7 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.67(18) . . ?
C4 C3 H3 120.2 . . ?
C14 C19 H19 119.6 . . ?
C18 C19 C14 120.77(18) . . ?
C18 C19 H19 119.6 . . ?
C8 C10 H10A 108.8 . . ?
C8 C10 H10B 108.8 . . ?
C11 C10 C8 113.68(15) . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 C19 120.03(18) . . ?
C17 C18 H18 120.0 . . ?
C7 C6 H6 121.0 . . ?
C7 C6 C5 118.06(19) . . ?
C5 C6 H6 121.0 . . ?
C16 C17 C18 120.02(19) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C5 H5 119.3 . . ?
C4 C5 C6 121.49(19) . . ?
C4 C5 H5 119.3 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
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
O3 C13 1.210(2) . ?
O2 C11 1.336(2) . ?
O2 C12 1.440(2) . ?
O1 C11 1.189(2) . ?
N1 C7 1.364(2) . ?
N1 C8 1.468(2) . ?
N1 C9 1.439(2) . ?
C14 C13 1.492(2) . ?
C14 C15 1.387(2) . ?
C14 C19 1.390(2) . ?
C2 C1 1.518(2) . ?
C2 C7 1.396(2) . ?
C2 C3 1.377(2) . ?
C13 C1 1.526(2) . ?
C1 H1 0.9800 . ?
C1 C8 1.549(2) . ?
C7 C6 1.387(3) . ?
C8 H8 0.9800 . ?
C8 C10 1.517(3) . ?
C11 C10 1.495(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.378(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C16 H16 0.9300 . ?
C16 C17 1.372(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.375(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.388(3) . ?
C17 H17 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.371(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C5 H5 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
