#------------------------------------------------------------------------------
#$Date: 2021-12-21 23:58:16 +0100 (mar 21 de dic de 2021) $
#$Revision: 271563 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/94/7129448.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_7129448
loop_
_publ_author_name
'Yu, Bao'
'selkti, mohamed'
'Ardisson, Janick'
'Lannou, Marie-Isabelle'
'Sorin, Geoffroy'
_publ_section_title
;
 Silver oxide(I) promoted Conia-ene/radical cyclization for a
 straightforward access to furan derivatives
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06379K
_journal_year                    2022
_chemical_formula_sum            'C14 H15 N O'
_chemical_formula_weight         213.27
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           Triclinic'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2021-09-30 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                96.339(4)
_cell_angle_beta                 93.280(4)
_cell_angle_gamma                102.199(4)
_cell_formula_units_Z            2
_cell_length_a                   6.4404(4)
_cell_length_b                   9.0870(6)
_cell_length_c                   9.8469(7)
_cell_measurement_reflns_used    1782
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      63.49
_cell_measurement_theta_min      4.53
_cell_volume                     557.90(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11546
_diffrn_reflns_theta_full        63.59
_diffrn_reflns_theta_max         63.59
_diffrn_reflns_theta_min         4.53
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.6606
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1839
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0455P)²+0.3007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.0977
_reflns_number_gt                1685
_reflns_number_total             1839
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            d1cc06379k2.cif
_cod_data_source_block           by660_bis
_cod_original_cell_volume        557.90(6)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7129448
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3813(2) 0.78438(16) 0.75970(14) 0.0159(3) Uani 1 1 d . . .
H1 H 0.5119 0.7617 0.7413 0.019 Uiso 1 1 calc R . .
C2 C 0.3752(2) 0.92791(16) 0.82219(14) 0.0176(3) Uani 1 1 d . . .
H2 H 0.5012 1.0002 0.8463 0.021 Uiso 1 1 calc R . .
C3 C 0.1814(2) 0.96359(16) 0.84875(15) 0.0207(3) Uani 1 1 d . . .
H3 H 0.1767 1.0599 0.8899 0.025 Uiso 1 1 calc R . .
C4 C -0.0049(2) 0.85494(17) 0.81366(15) 0.0212(3) Uani 1 1 d . . .
H4 H -0.1352 0.8787 0.8310 0.025 Uiso 1 1 calc R . .
C5 C 0.0005(2) 0.71057(16) 0.75267(14) 0.0178(3) Uani 1 1 d . . .
H5 H -0.1258 0.6380 0.7307 0.021 Uiso 1 1 calc R . .
C6 C 0.1945(2) 0.67402(15) 0.72422(13) 0.0144(3) Uani 1 1 d . . .
C7 C 0.1995(2) 0.51814(16) 0.65398(15) 0.0167(3) Uani 1 1 d . . .
H7A H 0.0840 0.4441 0.6829 0.020 Uiso 1 1 calc R . .
H7B H 0.1755 0.5170 0.5557 0.020 Uiso 1 1 calc R . .
C8 C 0.4164(2) 0.33242(15) 0.59833(14) 0.0161(3) Uani 1 1 d . . .
H8A H 0.4598 0.3523 0.5082 0.019 Uiso 1 1 calc R . .
H8B H 0.2828 0.2576 0.5885 0.019 Uiso 1 1 calc R . .
C9 C 0.5854(2) 0.28258(15) 0.68076(14) 0.0147(3) Uani 1 1 d . . .
C10 C 0.6010(2) 0.35411(15) 0.81813(14) 0.0155(3) Uani 1 1 d . . .
C11 C 0.4431(2) 0.45374(16) 0.82934(14) 0.0168(3) Uani 1 1 d . . .
H11A H 0.3149 0.4044 0.8676 0.020 Uiso 1 1 calc R . .
H11B H 0.5037 0.5500 0.8847 0.020 Uiso 1 1 calc R . .
C12 C 0.7530(2) 0.30553(16) 0.88894(15) 0.0180(3) Uani 1 1 d . . .
H12 H 0.7964 0.3345 0.9815 0.022 Uiso 1 1 calc R . .
C13 C 0.7276(2) 0.19253(15) 0.67374(14) 0.0157(3) Uani 1 1 d . . .
C14 C 0.7879(2) 0.08553(16) 0.56609(15) 0.0206(3) Uani 1 1 d . . .
H14A H 0.9392 0.1116 0.5600 0.031 Uiso 1 1 calc R . .
H14B H 0.7159 0.0917 0.4795 0.031 Uiso 1 1 calc R . .
H14C H 0.7477 -0.0160 0.5891 0.031 Uiso 1 1 calc R . .
N1 N 0.40006(18) 0.47372(13) 0.68390(11) 0.0146(3) Uani 1 1 d . . .
O1 O 0.83421(15) 0.20570(11) 0.80215(10) 0.0180(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 0.0192 0.0096 '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 0.0330 0.0189 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0517 0.0336 '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
C2 C1 C6 120.84(13) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 120.09(13) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 119.48(13) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.68(14) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.28(13) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.61(13) . . ?
C1 C6 C7 121.18(12) . . ?
C5 C6 C7 120.19(12) . . ?
N1 C7 C6 113.09(11) . . ?
N1 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
N1 C8 C9 101.40(11) . . ?
N1 C8 H8A 111.5 . . ?
C9 C8 H8A 111.5 . . ?
N1 C8 H8B 111.5 . . ?
C9 C8 H8B 111.5 . . ?
H8A C8 H8B 109.3 . . ?
C13 C9 C10 107.72(13) . . ?
C13 C9 C8 143.25(13) . . ?
C10 C9 C8 109.02(12) . . ?
C12 C10 C9 107.17(13) . . ?
C12 C10 C11 143.92(13) . . ?
C9 C10 C11 108.91(12) . . ?
N1 C11 C10 101.42(10) . . ?
N1 C11 H11A 111.5 . . ?
C10 C11 H11A 111.5 . . ?
N1 C11 H11B 111.5 . . ?
C10 C11 H11B 111.5 . . ?
H11A C11 H11B 109.3 . . ?
C10 C12 O1 109.09(12) . . ?
C10 C12 H12 125.5 . . ?
O1 C12 H12 125.5 . . ?
C9 C13 O1 108.41(12) . . ?
C9 C13 C14 135.71(14) . . ?
O1 C13 C14 115.85(12) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 N1 C11 114.24(11) . . ?
C7 N1 C8 112.61(10) . . ?
C11 N1 C8 107.88(10) . . ?
C12 O1 C13 107.59(11) . . ?
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 C2 1.389(2) . ?
C1 C6 1.393(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.386(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.5138(19) . ?
C7 N1 1.4567(18) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.4827(17) . ?
C8 C9 1.4957(19) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C13 1.350(2) . ?
C9 C10 1.423(2) . ?
C10 C12 1.346(2) . ?
C10 C11 1.499(2) . ?
C11 N1 1.4813(17) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O1 1.3810(17) . ?
C12 H12 0.9300 . ?
C13 O1 1.3846(17) . ?
C13 C14 1.483(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
