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#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/71/1517195.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_1517195
loop_
_publ_author_name
'Zhao, Depeng'
'Fañanás-Mastral, Martín'
'Chang, Mu-Chieh'
'Otten, Edwin'
'Feringa, Ben L.'
_publ_section_title
;
 Asymmetric synthesis of N,O-heterocycles via enantioselective
 iridium-catalysed intramolecular allylic amidation
;
_journal_issue                   11
_journal_name_full               'Chem. Sci.'
_journal_page_first              4216
_journal_paper_doi               10.1039/C4SC01940G
_journal_volume                  5
_journal_year                    2014
_chemical_formula_sum            'C16 H12 Br N O'
_chemical_formula_weight         314.18
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_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
_cell_angle_alpha                85.222(3)
_cell_angle_beta                 78.520(3)
_cell_angle_gamma                70.043(3)
_cell_formula_units_Z            2
_cell_length_a                   6.3154(5)
_cell_length_b                   8.1371(7)
_cell_length_c                   14.3362(12)
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      53.933
_cell_measurement_theta_min      5.801
_cell_volume                     678.53(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31603
_diffrn_reflns_theta_full        27.13
_diffrn_reflns_theta_max         27.13
_diffrn_reflns_theta_min         2.90
_exptl_absorpt_coefficient_mu    3.019
_exptl_absorpt_correction_T_max  0.7728
_exptl_absorpt_correction_T_min  0.5697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.972
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.116
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.007(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5756
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0552
_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)+(0.1061P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1339
_refine_ls_wR_factor_ref         0.1434
_reflns_number_gt                4785
_reflns_number_total             5756
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4sc01940g2.cif
_cod_data_source_block           mo_molan093c_0m
_cod_depositor_comments
'Adding full bibliography for 1517194--1517195.cif.'
_cod_original_sg_symbol_H-M      P1
_cod_database_code               1517195
loop_
_symmetry_equiv_pos_as_xyz
'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
Br1_1 Br -0.16293(7) 0.24554(6) 0.88805(4) 0.06805(19) Uani 1 1 d .
O1_1 O 0.3571(5) 0.5421(4) 0.4821(3) 0.0509(8) Uani 1 1 d .
N1_1 N 0.0014(6) 0.5137(5) 0.5490(3) 0.0456(8) Uani 1 1 d .
C1_1 C 0.0401(9) 0.2932(6) 0.7818(3) 0.0481(10) Uani 1 1 d .
C2_1 C 0.2734(10) 0.2332(7) 0.7806(4) 0.0564(12) Uani 1 1 d .
H2_1 H 0.3318 0.1703 0.8324 0.068 Uiso 1 1 calc R
C3_1 C 0.4175(9) 0.2671(7) 0.7026(4) 0.0538(12) Uani 1 1 d .
H3_1 H 0.5746 0.2271 0.7014 0.065 Uiso 1 1 calc R
C4_1 C 0.3306(8) 0.3617(6) 0.6244(3) 0.0444(9) Uani 1 1 d .
C5_1 C 0.0968(7) 0.4196(5) 0.6251(3) 0.0398(8) Uani 1 1 d .
C6_1 C -0.0500(8) 0.3851(6) 0.7052(3) 0.0448(9) Uani 1 1 d .
H6_1 H -0.2073 0.4237 0.7069 0.054 Uiso 1 1 calc R
C7_1 C 0.4851(8) 0.4002(6) 0.5369(4) 0.0468(10) Uani 1 1 d .
H7_1 H 0.6002 0.4369 0.5581 0.056 Uiso 1 1 calc R
C8_1 C 0.6084(9) 0.2468(6) 0.4742(4) 0.0497(10) Uani 1 1 d .
H8_1 H 0.5227 0.1865 0.4556 0.060 Uiso 1 1 calc R
C9_1 C 0.8254(9) 0.1928(8) 0.4445(4) 0.0574(13) Uani 1 1 d .
H9A_1 H 0.9155 0.2505 0.4620 0.069 Uiso 1 1 calc R
H9B_1 H 0.8929 0.0961 0.4055 0.069 Uiso 1 1 calc R
C10_1 C 0.1299(8) 0.5705(6) 0.4843(3) 0.0398(9) Uani 1 1 d .
C11_1 C 0.0478(5) 0.6757(4) 0.40363(19) 0.0430(9) Uani 1 1 d GU
C12_1 C 0.1977(4) 0.7214(4) 0.3297(2) 0.0558(11) Uani 1 1 d G
H12_1 H 0.3539 0.6821 0.3306 0.067 Uiso 1 1 calc R
C13_1 C 0.1141(6) 0.8258(5) 0.2545(2) 0.0680(17) Uani 1 1 d G
H13_1 H 0.2144 0.8564 0.2050 0.082 Uiso 1 1 calc R
C14_1 C -0.1194(6) 0.8845(5) 0.2531(2) 0.0663(14) Uani 1 1 d G
H14_1 H -0.1754 0.9544 0.2028 0.080 Uiso 1 1 calc R
C15_1 C -0.2693(4) 0.8389(5) 0.3270(3) 0.0618(13) Uani 1 1 d G
H15_1 H -0.4256 0.8782 0.3262 0.074 Uiso 1 1 calc R
C16_1 C -0.1857(4) 0.7345(4) 0.4023(2) 0.0554(12) Uani 1 1 d GU
H16_1 H -0.2860 0.7039 0.4517 0.066 Uiso 1 1 calc R
Br2_2 Br 1.32708(8) 0.25947(6) 1.24756(4) 0.0698(2) Uani 1 1 d .
O2_2 O 0.8144(5) 0.7059(5) 0.8894(2) 0.0543(8) Uani 1 1 d .
N2_2 N 1.1647(7) 0.6336(5) 0.9398(3) 0.0479(8) Uani 1 1 d .
C1_2 C 1.1232(9) 0.3967(6) 1.1684(3) 0.0488(10) Uani 1 1 d .
C2_2 C 0.8971(10) 0.4290(8) 1.1944(4) 0.0572(12) Uani 1 1 d .
H2_2 H 0.8402 0.3824 1.2514 0.069 Uiso 1 1 calc R
C3_2 C 0.7455(10) 0.5324(8) 1.1365(4) 0.0559(13) Uani 1 1 d .
H3_2 H 0.5883 0.5572 1.1552 0.067 Uiso 1 1 calc R
C4_2 C 0.8349(8) 0.5975(6) 1.0500(3) 0.0473(10) Uani 1 1 d .
C5_2 C 1.0693(8) 0.5670(6) 1.0245(3) 0.0417(9) Uani 1 1 d .
C6_2 C 1.2185(9) 0.4617(6) 1.0827(3) 0.0484(10) Uani 1 1 d .
H6_2 H 1.3762 0.4357 1.0651 0.058 Uiso 1 1 calc R
C7_2 C 0.6826(8) 0.7096(7) 0.9844(3) 0.0472(10) Uani 1 1 d .
H7_2 H 0.5629 0.6594 0.9825 0.057 Uiso 1 1 calc R
C8_2 C 0.5686(11) 0.8950(7) 1.0150(4) 0.0579(12) Uani 1 1 d .
H8_2 H 0.6594 0.9549 1.0295 0.069 Uiso 1 1 calc R
C9_2 C 0.3490(11) 0.9781(8) 1.0225(4) 0.0602(14) Uani 1 1 d .
H9A_2 H 0.2538 0.9217 1.0084 0.072 Uiso 1 1 calc R
H9B_2 H 0.2877 1.0938 1.0419 0.072 Uiso 1 1 calc R
C10_2 C 1.0359(7) 0.6982(6) 0.8784(3) 0.0418(10) Uani 1 1 d .
C11_2 C 1.1166(5) 0.7645(4) 0.78587(19) 0.0462(9) Uani 1 1 d GU
C12_2 C 0.9651(4) 0.8546(5) 0.7260(2) 0.0560(11) Uani 1 1 d G
H12_2 H 0.8090 0.8739 0.7452 0.067 Uiso 1 1 calc R
C13_2 C 1.0468(6) 0.9157(5) 0.6376(2) 0.0675(17) Uani 1 1 d G
H13_2 H 0.9454 0.9760 0.5975 0.081 Uiso 1 1 calc R
C14_2 C 1.2800(6) 0.8868(5) 0.6089(2) 0.0625(13) Uani 1 1 d G
H14_2 H 1.3347 0.9277 0.5497 0.075 Uiso 1 1 calc R
C15_2 C 1.4315(4) 0.7968(5) 0.6688(2) 0.0670(15) Uani 1 1 d G
H15_2 H 1.5876 0.7774 0.6496 0.080 Uiso 1 1 calc R
C16_2 C 1.3498(5) 0.7356(4) 0.7573(2) 0.0594(13) Uani 1 1 d GU
H16_2 H 1.4512 0.6754 0.7973 0.071 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'
Br Br -0.2901 2.4595 '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
C10_1 O1_1 C7_1 119.9(4)
C10_1 N1_1 C5_1 117.8(4)
C6_1 C1_1 C2_1 121.3(4)
C6_1 C1_1 Br1_1 118.5(4)
C2_1 C1_1 Br1_1 120.2(4)
C3_1 C2_1 C1_1 119.3(4)
C2_1 C3_1 C4_1 120.6(4)
C5_1 C4_1 C3_1 120.0(4)
C5_1 C4_1 C7_1 118.1(4)
C3_1 C4_1 C7_1 121.9(4)
C4_1 C5_1 N1_1 122.3(4)
C4_1 C5_1 C6_1 119.2(4)
N1_1 C5_1 C6_1 118.5(4)
C1_1 C6_1 C5_1 119.6(4)
O1_1 C7_1 C8_1 109.0(4)
O1_1 C7_1 C4_1 110.6(4)
C8_1 C7_1 C4_1 113.6(4)
C9_1 C8_1 C7_1 123.9(5)
N1_1 C10_1 O1_1 125.0(4)
N1_1 C10_1 C11_1 122.8(4)
O1_1 C10_1 C11_1 112.2(4)
C12_1 C11_1 C16_1 120.0
C12_1 C11_1 C10_1 121.1(3)
C16_1 C11_1 C10_1 118.8(3)
C11_1 C12_1 C13_1 120.0
C14_1 C13_1 C12_1 120.0
C13_1 C14_1 C15_1 120.0
C16_1 C15_1 C14_1 120.0
C15_1 C16_1 C11_1 120.0
C10_2 O2_2 C7_2 118.9(3)
C10_2 N2_2 C5_2 117.3(4)
C2_2 C1_2 C6_2 122.1(5)
C2_2 C1_2 Br2_2 120.5(4)
C6_2 C1_2 Br2_2 117.4(4)
C1_2 C2_2 C3_2 120.6(5)
C4_2 C3_2 C2_2 118.8(5)
C5_2 C4_2 C3_2 120.3(4)
C5_2 C4_2 C7_2 117.9(4)
C3_2 C4_2 C7_2 121.7(5)
C4_2 C5_2 N2_2 122.0(4)
C4_2 C5_2 C6_2 120.0(4)
N2_2 C5_2 C6_2 117.9(4)
C5_2 C6_2 C1_2 118.1(4)
O2_2 C7_2 C8_2 109.2(4)
O2_2 C7_2 C4_2 109.5(4)
C8_2 C7_2 C4_2 113.8(4)
C9_2 C8_2 C7_2 123.9(5)
N2_2 C10_2 O2_2 124.8(4)
N2_2 C10_2 C11_2 122.9(4)
O2_2 C10_2 C11_2 112.3(3)
C12_2 C11_2 C16_2 120.0
C12_2 C11_2 C10_2 121.1(3)
C16_2 C11_2 C10_2 118.9(3)
C13_2 C12_2 C11_2 120.0
C12_2 C13_2 C14_2 120.0
C15_2 C14_2 C13_2 120.0
C14_2 C15_2 C16_2 120.0
C15_2 C16_2 C11_2 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1_1 C1_1 1.892(5)
O1_1 C10_1 1.367(6)
O1_1 C7_1 1.438(6)
N1_1 C10_1 1.272(6)
N1_1 C5_1 1.395(5)
C1_1 C6_1 1.382(7)
C1_1 C2_1 1.382(8)
C2_1 C3_1 1.368(8)
C3_1 C4_1 1.401(7)
C4_1 C5_1 1.386(6)
C4_1 C7_1 1.510(7)
C5_1 C6_1 1.399(6)
C7_1 C8_1 1.489(7)
C8_1 C9_1 1.281(8)
C10_1 C11_1 1.453(5)
C11_1 C12_1 1.3900
C11_1 C16_1 1.3900
C12_1 C13_1 1.3900
C13_1 C14_1 1.3900
C14_1 C15_1 1.3900
C15_1 C16_1 1.3900
Br2_2 C1_2 1.892(5)
O2_2 C10_2 1.357(5)
O2_2 C7_2 1.445(6)
N2_2 C10_2 1.275(6)
N2_2 C5_2 1.398(6)
C1_2 C2_2 1.339(8)
C1_2 C6_2 1.403(7)
C2_2 C3_2 1.401(8)
C3_2 C4_2 1.397(7)
C4_2 C5_2 1.391(7)
C4_2 C7_2 1.503(7)
C5_2 C6_2 1.401(6)
C7_2 C8_2 1.493(8)
C8_2 C9_2 1.306(9)
C10_2 C11_2 1.453(5)
C11_2 C12_2 1.3900
C11_2 C16_2 1.3900
C12_2 C13_2 1.3900
C13_2 C14_2 1.3900
C14_2 C15_2 1.3900
C15_2 C16_2 1.3900
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139043931
