#------------------------------------------------------------------------------
#$Date: 2024-05-24 04:09:25 +0300 (Fri, 24 May 2024) $
#$Revision: 292013 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/86/7248673.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_7248673
loop_
_publ_author_name
'Dunkel, Petra'
'Bogdán, Dóra'
'Deme, Ruth'
'Zimber, Ádám'
'Ballayová, Veronika'
'Csizmadia, Eszter'
'Kontra, Bence'
'Kalydi, Eszter'
'Bényei, Attila'
'Mátyus, Péter'
'Mucsi, Zoltán'
_publ_section_title
;
 C(sp3)--H cyclizations of 2-(2-vinyl)phenoxy-tert-anilines
;
_journal_issue                   24
_journal_name_full               'RSC Advances'
_journal_page_first              16784
_journal_page_last               16800
_journal_paper_doi               10.1039/D3RA08974F
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C21 H19 N3 O'
_chemical_formula_sum            'C21 H19 N3 O'
_chemical_formula_weight         329.39
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-02-08T10:57:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2023-03-31 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 127.830(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            8
_cell_length_a                   27.317(5)
_cell_length_b                   8.519(5)
_cell_length_c                   19.641(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      11.5
_cell_measurement_theta_min      4.7
_cell_volume                     3610(2)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1992)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1992)'
_computing_data_reduction        'PROFIT (Streltsov & Zavodnik, 1989)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'profiled omega/2theta scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            3725
_diffrn_reflns_theta_full        25.52
_diffrn_reflns_theta_max         25.52
_diffrn_reflns_theta_min         2.57
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        4
_diffrn_standards_interval_count 102
_diffrn_standards_interval_time  5
_diffrn_standards_number         4
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.35
_refine_diff_density_rms         0.07
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.1174
_refine_ls_R_factor_gt           0.0726
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0586P)²+19.9399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1909
_reflns_number_gt                1955
_reflns_number_total             3725
_reflns_threshold_expression     >2σ(I)
_publcif_datablock.id            {a19d3a49-5aa6-4280-bb8a-c01665e751f9}
_cod_data_source_file            d3ra08974f3.cif
_cod_data_source_block           4c
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7248673
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.4624(4) 0.3095(8) -0.5300(4) 0.077(2) Uani d . 1 . . C
C2 0.4442(4) 0.0593(9) -0.4920(4) 0.072(2) Uani d . 1 . . C
C3 0.4778(3) 0.1998(7) -0.4631(4) 0.0616(17) Uani d . 1 . . C
C4 0.5235(3) 0.2395(7) -0.3806(4) 0.0620(17) Uani d . 1 . . C
H4 0.5403 0.3393 -0.3713 0.074 Uiso calc . 1 . . H
C5 0.5493(3) 0.1421(7) -0.3046(4) 0.0570(16) Uani d . 1 . . C
C6 0.5509(4) -0.0212(8) -0.3071(4) 0.082(2) Uani d . 1 . . C
H6 0.5341 -0.0714 -0.3592 0.099 Uiso calc . 1 . . H
C7 0.5774(4) -0.1102(8) -0.2329(5) 0.100(3) Uani d . 1 . . C
H7 0.5779 -0.2191 -0.2352 0.12 Uiso calc . 1 . . H
C8 0.6030(4) -0.0338(8) -0.1556(4) 0.088(3) Uani d . 1 . . C
H8 0.6215 -0.0926 -0.1055 0.106 Uiso calc . 1 . . H
C9 0.6018(3) 0.1253(8) -0.1513(4) 0.0634(17) Uani d . 1 . . C
H9 0.618 0.1744 -0.0991 0.076 Uiso calc . 1 . . H
C10 0.5765(3) 0.2130(7) -0.2245(4) 0.0544(15) Uani d . 1 . . C
C11 0.6083(3) 0.4527(7) -0.1473(4) 0.0536(15) Uani d . 1 . . C
C12 0.5787(3) 0.5188(7) -0.1161(4) 0.0694(18) Uani d . 1 . . C
H12 0.536 0.5101 -0.1474 0.083 Uiso calc . 1 . . H
C13 0.6137(4) 0.5971(8) -0.0382(5) 0.077(2) Uani d . 1 . . C
H13 0.5948 0.6406 -0.0162 0.093 Uiso calc . 1 . . H
C14 0.6751(4) 0.6099(8) 0.0056(4) 0.079(2) Uani d . 1 . . C
H14 0.6985 0.6608 0.0587 0.094 Uiso calc . 1 . . H
C15 0.7048(3) 0.5498(8) -0.0259(4) 0.076(2) Uani d . 1 . . C
H15 0.7473 0.563 0.0048 0.091 Uiso calc . 1 . . H
C16 0.6698(3) 0.4682(7) -0.1049(4) 0.0596(16) Uani d . 1 . . C
C17 0.6790(3) 0.4867(7) -0.2195(4) 0.072(2) Uani d . 1 . . C
H17A 0.6994 0.5881 -0.2036 0.087 Uiso calc R 1 . . H
H17B 0.6346 0.5038 -0.2579 0.087 Uiso calc R 1 . . H
C18 0.6980(4) 0.3892(10) -0.2650(5) 0.098(3) Uani d . 1 . . C
H18A 0.6741 0.2927 -0.2859 0.117 Uiso calc R 1 . . H
H18B 0.6882 0.4471 -0.3145 0.117 Uiso calc R 1 . . H
C19 0.7646(4) 0.3502(11) -0.2083(6) 0.111(3) Uani d . 1 . . C
H19A 0.7889 0.4452 -0.1931 0.133 Uiso calc R 1 . . H
H19B 0.7738 0.2807 -0.2383 0.133 Uiso calc R 1 . . H
C20 0.7815(4) 0.2707(10) -0.1273(6) 0.109(3) Uani d . 1 . . C
H20A 0.7608 0.1699 -0.142 0.131 Uiso calc R 1 . . H
H20B 0.8259 0.2525 -0.0879 0.131 Uiso calc R 1 . . H
C21 0.7625(3) 0.3721(9) -0.0840(4) 0.083(2) Uani d . 1 . . C
H21A 0.7732 0.3196 -0.0327 0.099 Uiso calc R 1 . . H
H21B 0.7849 0.4707 -0.0666 0.099 Uiso calc R 1 . . H
N1 0.4480(4) 0.3873(8) -0.5854(4) 0.109(2) Uani d . 1 . . N
N2 0.4149(3) -0.0502(8) -0.5195(4) 0.096(2) Uani d . 1 . . N
N3 0.6969(2) 0.4024(6) -0.1416(3) 0.0614(14) Uani d . 1 . . N
O1 0.57169(19) 0.3746(4) -0.2261(2) 0.0585(11) Uani d . 1 . . O
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-6 -4 6
1 -3 -3
0 -2 -1
7 -1 -3
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 C3 175.6(8) . . ?
N2 C2 C3 176.3(9) . . ?
C4 C3 C2 126.6(6) . . ?
C4 C3 C1 117.9(6) . . ?
C2 C3 C1 115.5(6) . . ?
C3 C4 C5 126.8(6) . . ?
C3 C4 H4 116.6 . . ?
C5 C4 H4 116.6 . . ?
C6 C5 C10 117.6(6) . . ?
C6 C5 C4 122.5(6) . . ?
C10 C5 C4 119.7(5) . . ?
C7 C6 C5 121.0(6) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C6 118.8(6) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C9 C8 C7 121.5(6) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 119.5(6) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 O1 123.0(5) . . ?
C9 C10 C5 121.5(5) . . ?
O1 C10 C5 115.3(5) . . ?
C16 C11 O1 120.5(5) . . ?
C16 C11 C12 121.8(6) . . ?
O1 C11 C12 117.7(6) . . ?
C13 C12 C11 119.1(7) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 119.5(7) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 122.0(6) . . ?
C13 C14 H14 119 . . ?
C15 C14 H14 119 . . ?
C14 C15 C16 119.1(7) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C11 C16 C15 118.4(6) . . ?
C11 C16 N3 119.0(6) . . ?
C15 C16 N3 122.6(6) . . ?
N3 C17 C18 109.1(5) . . ?
N3 C17 H17A 109.9 . . ?
C18 C17 H17A 109.9 . . ?
N3 C17 H17B 109.9 . . ?
C18 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
C19 C18 C17 112.7(6) . . ?
C19 C18 H18A 109.1 . . ?
C17 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
C17 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 C20 109.5(7) . . ?
C18 C19 H19A 109.8 . . ?
C20 C19 H19A 109.8 . . ?
C18 C19 H19B 109.8 . . ?
C20 C19 H19B 109.8 . . ?
H19A C19 H19B 108.2 . . ?
C21 C20 C19 110.3(6) . . ?
C21 C20 H20A 109.6 . . ?
C19 C20 H20A 109.6 . . ?
C21 C20 H20B 109.6 . . ?
C19 C20 H20B 109.6 . . ?
H20A C20 H20B 108.1 . . ?
N3 C21 C20 110.7(6) . . ?
N3 C21 H21A 109.5 . . ?
C20 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
C16 N3 C21 117.2(5) . . ?
C16 N3 C17 112.9(5) . . ?
C21 N3 C17 111.2(5) . . ?
C10 O1 C11 117.2(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.119(8) ?
C1 C3 . 1.449(8) ?
C2 N2 . 1.128(8) ?
C2 C3 . 1.400(9) ?
C3 C4 . 1.347(8) ?
C4 C5 . 1.457(8) ?
C4 H4 . 0.93 ?
C5 C6 . 1.394(8) ?
C5 C10 . 1.398(8) ?
C6 C7 . 1.388(9) ?
C6 H6 . 0.93 ?
C7 C8 . 1.384(9) ?
C7 H7 . 0.93 ?
C8 C9 . 1.360(9) ?
C8 H8 . 0.93 ?
C9 C10 . 1.373(8) ?
C9 H9 . 0.93 ?
C10 O1 . 1.382(6) ?
C11 C16 . 1.348(8) ?
C11 O1 . 1.393(7) ?
C11 C12 . 1.400(8) ?
C12 C13 . 1.380(9) ?
C12 H12 . 0.93 ?
C13 C14 . 1.342(10) ?
C13 H13 . 0.93 ?
C14 C15 . 1.385(10) ?
C14 H14 . 0.93 ?
C15 C16 . 1.410(9) ?
C15 H15 . 0.93 ?
C16 N3 . 1.425(7) ?
C17 N3 . 1.477(7) ?
C17 C18 . 1.525(9) ?
C17 H17A . 0.97 ?
C17 H17B . 0.97 ?
C18 C19 . 1.474(10) ?
C18 H18A . 0.97 ?
C18 H18B . 0.97 ?
C19 C20 . 1.517(10) ?
C19 H19A . 0.97 ?
C19 H19B . 0.97 ?
C20 C21 . 1.509(10) ?
C20 H20A . 0.97 ?
C20 H20B . 0.97 ?
C21 N3 . 1.440(8) ?
C21 H21A . 0.97 ?
C21 H21B . 0.97 ?
