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#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/75/1507576.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_1507576
loop_
_publ_author_name
'Zhang, Yicheng'
'Wang, Min'
'Li, Pinhua'
'Wang, Lei'
_publ_section_title
;
 Iron-Promoted Tandem Reaction of Anilines with Styrene Oxides via C-C
 Cleavage for the Synthesis of Quinolines.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2206
_journal_page_last               2209
_journal_paper_doi               10.1021/ol300391t
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C15 H10 Br N'
_chemical_formula_sum            'C15 H10 Br N'
_chemical_formula_weight         284.15
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.122(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.1173(12)
_cell_length_b                   5.8848(7)
_cell_length_c                   14.7685(14)
_cell_measurement_reflns_used    1580
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4080
_cell_measurement_theta_min      2.9162
_cell_volume                     1159.2(2)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2010)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_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  0.0963
_diffrn_reflns_av_sigmaI/netI    0.1008
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7446
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.47
_exptl_absorpt_coefficient_mu    3.519
_exptl_absorpt_correction_T_max  0.4983
_exptl_absorpt_correction_T_min  0.3004
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Oxford Diffraction, 2010) 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.0097(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.1148
_refine_ls_R_factor_gt           0.0550
_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)+(0.0398P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1271
_reflns_number_gt                1160
_reflns_number_total             2111
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300391t_si_002.cif
_cod_data_source_block           110706_wlbao
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1507576
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.03973(4) 0.91149(14) 0.16643(5) 0.0755(4) Uani 1 1 d .
N1 N 0.6140(3) 1.3384(7) 0.4769(3) 0.0455(12) Uani 1 1 d .
C1 C 0.7873(4) 1.2343(10) 0.5279(4) 0.0475(14) Uani 1 1 d .
H1 H 0.8039 1.3718 0.5604 0.057 Uiso 1 1 calc R
C2 C 0.8605(4) 1.0836(11) 0.5288(4) 0.0533(15) Uani 1 1 d .
H2 H 0.9270 1.1187 0.5625 0.064 Uiso 1 1 calc R
C3 C 0.8377(4) 0.8773(10) 0.4801(4) 0.0541(16) Uani 1 1 d .
H3 H 0.8888 0.7773 0.4804 0.065 Uiso 1 1 calc R
C4 C 0.7406(4) 0.8227(9) 0.4322(4) 0.0448(14) Uani 1 1 d .
H4 H 0.7255 0.6834 0.4010 0.054 Uiso 1 1 calc R
C5 C 0.6622(3) 0.9756(9) 0.4291(3) 0.0345(12) Uani 1 1 d .
C6 C 0.6860(4) 1.1821(9) 0.4778(3) 0.0392(13) Uani 1 1 d .
C7 C 0.5212(4) 1.2862(9) 0.4283(3) 0.0450(14) Uani 1 1 d .
H7 H 0.4725 1.3937 0.4270 0.054 Uiso 1 1 calc R
C8 C 0.4879(3) 1.0820(8) 0.3775(3) 0.0309(11) Uani 1 1 d .
C9 C 0.5614(4) 0.9290(8) 0.3792(3) 0.0375(12) Uani 1 1 d .
H9 H 0.5441 0.7919 0.3467 0.045 Uiso 1 1 calc R
C10 C 0.3798(3) 1.0430(9) 0.3266(3) 0.0370(12) Uani 1 1 d .
C11 C 0.3468(4) 0.8493(10) 0.2733(4) 0.0470(14) Uani 1 1 d .
H11 H 0.3936 0.7427 0.2686 0.056 Uiso 1 1 calc R
C12 C 0.2461(4) 0.8088(10) 0.2266(4) 0.0498(14) Uani 1 1 d .
H12 H 0.2254 0.6756 0.1919 0.060 Uiso 1 1 calc R
C13 C 0.1774(4) 0.9669(10) 0.2321(4) 0.0424(14) Uani 1 1 d .
C14 C 0.2068(4) 1.1611(10) 0.2830(4) 0.0548(16) Uani 1 1 d .
H14 H 0.1595 1.2680 0.2862 0.066 Uiso 1 1 calc R
C15 C 0.3069(4) 1.1989(9) 0.3299(4) 0.0460(14) Uani 1 1 d .
H15 H 0.3265 1.3322 0.3648 0.055 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'
Br Br -0.2901 2.4595 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 N1 C6 117.1(4)
C2 C1 C6 119.9(5)
C2 C1 H1 120.0
C6 C1 H1 120.0
C1 C2 C3 121.2(5)
C1 C2 H2 119.4
C3 C2 H2 119.4
C4 C3 C2 119.8(5)
C4 C3 H3 120.1
C2 C3 H3 120.1
C3 C4 C5 120.7(5)
C3 C4 H4 119.6
C5 C4 H4 119.6
C6 C5 C9 118.3(4)
C6 C5 C4 118.9(4)
C9 C5 C4 122.8(5)
N1 C6 C5 121.9(4)
N1 C6 C1 118.7(5)
C5 C6 C1 119.4(5)
N1 C7 C8 126.2(5)
N1 C7 H7 116.9
C8 C7 H7 116.9
C9 C8 C7 115.6(4)
C9 C8 C10 123.8(4)
C7 C8 C10 120.6(4)
C8 C9 C5 121.0(5)
C8 C9 H9 119.5
C5 C9 H9 119.5
C11 C10 C15 116.7(4)
C11 C10 C8 121.1(4)
C15 C10 C8 122.1(5)
C10 C11 C12 121.9(5)
C10 C11 H11 119.1
C12 C11 H11 119.1
C13 C12 C11 119.2(5)
C13 C12 H12 120.4
C11 C12 H12 120.4
C14 C13 C12 120.8(5)
C14 C13 Br1 120.4(4)
C12 C13 Br1 118.8(4)
C13 C14 C15 119.6(5)
C13 C14 H14 120.2
C15 C14 H14 120.2
C14 C15 C10 121.8(5)
C14 C15 H15 119.1
C10 C15 H15 119.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C13 1.894(5)
N1 C7 1.307(6)
N1 C6 1.368(6)
C1 C2 1.358(7)
C1 C6 1.413(6)
C1 H1 0.9300
C2 C3 1.394(8)
C2 H2 0.9300
C3 C4 1.359(7)
C3 H3 0.9300
C4 C5 1.416(7)
C4 H4 0.9300
C5 C6 1.396(7)
C5 C9 1.399(6)
C7 C8 1.413(7)
C7 H7 0.9300
C8 C9 1.368(6)
C8 C10 1.482(6)
C9 H9 0.9300
C10 C11 1.377(7)
C10 C15 1.391(7)
C11 C12 1.382(7)
C11 H11 0.9300
C12 C13 1.365(7)
C12 H12 0.9300
C13 C14 1.357(7)
C14 C15 1.372(7)
C14 H14 0.9300
C15 H15 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 30651848 ChemSpider
2 53993630 PubChem
