#------------------------------------------------------------------------------
#$Date: 2024-02-04 12:12:15 +0100 (Sun 04 de Feb de 2024) $
#$Revision: 289354 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/25/7132503.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_7132503
loop_
_publ_author_name
'Ishida, Moeka'
'Adachi, Rina'
'Kobayashi, Kazuki'
'Yamamoto, Yukiko'
'Kawahara, Chinatsu'
'Yamada, Tsuyoshi'
'Aoyama, Hiroshi'
'Kanomata, Kyohei'
'Akai, Shuji'
'Lam, Patrick Y. S.'
'Sajiki, Hironao'
'Ikawa, Takashi'
_publ_section_title
;
 First atroposelective Chan-Lam coupling for the synthesis of C-N linked
 biaryls.
;
_journal_issue                   6
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              678
_journal_page_last               681
_journal_paper_doi               10.1039/d3cc05447k
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C18 H13 Br N2 O'
_chemical_formula_sum            'C18 H13 Br N2 O'
_chemical_formula_weight         353.22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2023-09-21 deposited with the CCDC.	2023-12-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   7.0262(11)
_cell_length_b                   9.2338(14)
_cell_length_c                   24.100(4)
_cell_measurement_reflns_used    4428
_cell_measurement_temperature    273
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.02
_cell_volume                     1563.6(4)
_computing_cell_refinement       DTREK
_computing_data_collection       DTREK
_computing_data_reduction        DTREK
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      273
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            10418
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         3.020
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.639
_exptl_absorpt_correction_T_max  0.453
_exptl_absorpt_correction_T_min  0.184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712.00
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.50
_refine_diff_density_min         -0.59
_refine_ls_abs_structure_details
;
 Flack x determined using 1165 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3443
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0277
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[σ²(Fo²)]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0539
_refine_ls_wR_factor_ref         0.0543
_reflns_Friedel_coverage         0.676
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.926
_reflns_number_gt                3099
_reflns_number_total             3443
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d3cc05447k3.cif
_cod_data_source_block           C18H13BrN2O-1
_cod_depositor_comments          'Adding full bibliography for 7132503.cif.'
_cod_original_cell_volume        1563.5(4)
_cod_database_code               7132503
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-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_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
Br1 Br 1.20762(5) -0.07175(4) 0.60195(2) 0.01913(10) Uani 1 1 d . . . . .
O1 O 0.7320(4) -0.2184(2) 0.65752(8) 0.0228(6) Uani 1 1 d . . . . .
N1 N 1.0885(4) 0.1317(3) 0.68184(10) 0.0158(6) Uani 1 1 d . . . . .
N2 N 0.8492(3) 0.0455(3) 0.62824(10) 0.0139(6) Uani 1 1 d . . . . .
C1 C 1.0398(4) 0.0457(4) 0.64145(12) 0.0142(7) Uani 1 1 d . . . . .
C2 C 0.9154(5) 0.1946(4) 0.69782(12) 0.0151(7) Uani 1 1 d . . . . .
C3 C 0.8791(6) 0.2962(4) 0.73991(13) 0.0211(8) Uani 1 1 d . . . . .
H3 H 0.976751 0.332925 0.761854 0.025 Uiso 1 1 calc R U . . .
C4 C 0.6929(5) 0.3394(4) 0.74739(12) 0.0198(8) Uani 1 1 d . . . . .
H4 H 0.664643 0.405377 0.775346 0.024 Uiso 1 1 calc R U . . .
C5 C 0.5455(5) 0.2865(4) 0.71407(13) 0.0199(8) Uani 1 1 d . . . . .
H5 H 0.422197 0.319719 0.719994 0.024 Uiso 1 1 calc R U . . .
C6 C 0.5783(5) 0.1861(4) 0.67247(13) 0.0178(8) Uani 1 1 d . . . . .
H6 H 0.480601 0.149527 0.650513 0.021 Uiso 1 1 calc R U . . .
C7 C 0.7668(5) 0.1434(3) 0.66566(12) 0.0136(7) Uani 1 1 d . . . . .
C8 C 0.7529(4) -0.0430(3) 0.58858(11) 0.0132(7) Uani 1 1 d . . . . .
C9 C 0.7255(5) 0.0099(4) 0.53385(12) 0.0143(7) Uani 1 1 d . . . . .
C10 C 0.7994(5) 0.1440(4) 0.51525(13) 0.0224(8) Uani 1 1 d . . . . .
H10 H 0.863266 0.204410 0.539868 0.027 Uiso 1 1 calc R U . . .
C11 C 0.7768(6) 0.1849(4) 0.46080(13) 0.0313(9) Uani 1 1 d . . . . .
H11 H 0.827852 0.272408 0.448803 0.038 Uiso 1 1 calc R U . . .
C12 C 0.6777(5) 0.0969(4) 0.42290(14) 0.0325(10) Uani 1 1 d . . . . .
H12 H 0.664531 0.126178 0.386180 0.039 Uiso 1 1 calc R U . . .
C13 C 0.6013(5) -0.0309(4) 0.43986(13) 0.0260(9) Uani 1 1 d . . . . .
H13 H 0.533832 -0.087513 0.414737 0.031 Uiso 1 1 calc R U . . .
C14 C 0.6234(4) -0.0792(4) 0.49577(12) 0.0167(7) Uani 1 1 d . . . . .
C15 C 0.5538(4) -0.2139(4) 0.51404(13) 0.0195(8) Uani 1 1 d . . . . .
H15 H 0.483202 -0.270633 0.489677 0.023 Uiso 1 1 calc R U . . .
C16 C 0.5869(5) -0.2638(4) 0.56667(13) 0.0192(8) Uani 1 1 d . . . . .
H16 H 0.542250 -0.354394 0.577416 0.023 Uiso 1 1 calc R U . . .
C17 C 0.6890(4) -0.1771(3) 0.60442(13) 0.0150(7) Uani 1 1 d . . . . .
C18 C 0.6822(6) -0.3629(4) 0.67442(13) 0.0297(9) Uani 1 1 d . . . . .
H18A H 0.720005 -0.377645 0.712285 0.036 Uiso 1 1 calc R U . . .
H18B H 0.547110 -0.375920 0.671174 0.036 Uiso 1 1 calc R U . . .
H18C H 0.746297 -0.431635 0.651090 0.036 Uiso 1 1 calc R U . . .
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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(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
C17 O1 C18 118.0(3) . . ?
C1 N1 C2 103.3(3) . . ?
C1 N2 C7 104.6(3) . . ?
C1 N2 C8 128.1(3) . . ?
C7 N2 C8 127.1(2) . . ?
N1 C1 N2 115.5(3) . . ?
N1 C1 Br1 124.8(2) . . ?
N2 C1 Br1 119.8(2) . . ?
C7 C2 N1 111.1(3) . . ?
C7 C2 C3 119.7(3) . . ?
N1 C2 C3 129.2(3) . . ?
C4 C3 C2 117.3(3) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C3 C4 C5 121.8(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 121.7(3) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 115.7(3) . . ?
C5 C6 H6 122.2 . . ?
C7 C6 H6 122.2 . . ?
C2 C7 C6 123.8(3) . . ?
C2 C7 N2 105.6(3) . . ?
C6 C7 N2 130.6(3) . . ?
C17 C8 C9 121.7(3) . . ?
C17 C8 N2 119.0(3) . . ?
C9 C8 N2 119.3(3) . . ?
C10 C9 C8 123.1(3) . . ?
C10 C9 C14 119.0(3) . . ?
C8 C9 C14 117.9(3) . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 121.2(4) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.8(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C9 118.9(3) . . ?
C15 C14 C13 122.3(3) . . ?
C9 C14 C13 118.8(3) . . ?
C16 C15 C14 121.9(3) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C17 119.6(3) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
O1 C17 C8 116.1(3) . . ?
O1 C17 C16 123.9(3) . . ?
C8 C17 C16 120.0(3) . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
Br1 C1 1.864(3) . ?
O1 C17 1.369(3) . ?
O1 C18 1.439(4) . ?
N1 C1 1.302(4) . ?
N1 C2 1.402(4) . ?
N2 C1 1.376(4) . ?
N2 C7 1.402(4) . ?
N2 C8 1.428(3) . ?
C2 C7 1.383(4) . ?
C2 C3 1.405(4) . ?
C3 C4 1.380(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.399(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.392(5) . ?
C6 H6 0.9300 . ?
C8 C17 1.371(4) . ?
C8 C9 1.420(4) . ?
C9 C10 1.416(5) . ?
C9 C14 1.426(4) . ?
C10 C11 1.375(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.407(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.359(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.428(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.407(5) . ?
C15 C16 1.369(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.409(4) . ?
C16 H16 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 N2 0.5(4) . . . . ?
C2 N1 C1 Br1 -179.7(2) . . . . ?
C7 N2 C1 N1 -0.6(4) . . . . ?
C8 N2 C1 N1 -175.9(3) . . . . ?
C7 N2 C1 Br1 179.6(2) . . . . ?
C8 N2 C1 Br1 4.3(4) . . . . ?
C1 N1 C2 C7 -0.2(4) . . . . ?
C1 N1 C2 C3 179.6(3) . . . . ?
C7 C2 C3 C4 0.6(5) . . . . ?
N1 C2 C3 C4 -179.3(3) . . . . ?
C2 C3 C4 C5 -1.0(5) . . . . ?
C3 C4 C5 C6 1.2(5) . . . . ?
C4 C5 C6 C7 -0.9(5) . . . . ?
N1 C2 C7 C6 179.5(3) . . . . ?
C3 C2 C7 C6 -0.4(5) . . . . ?
N1 C2 C7 N2 -0.1(4) . . . . ?
C3 C2 C7 N2 -180.0(3) . . . . ?
C5 C6 C7 C2 0.5(5) . . . . ?
C5 C6 C7 N2 180.0(3) . . . . ?
C1 N2 C7 C2 0.4(3) . . . . ?
C8 N2 C7 C2 175.7(3) . . . . ?
C1 N2 C7 C6 -179.2(3) . . . . ?
C8 N2 C7 C6 -3.8(5) . . . . ?
C1 N2 C8 C17 86.4(4) . . . . ?
C7 N2 C8 C17 -87.9(4) . . . . ?
C1 N2 C8 C9 -93.7(4) . . . . ?
C7 N2 C8 C9 92.0(4) . . . . ?
C17 C8 C9 C10 -176.2(3) . . . . ?
N2 C8 C9 C10 3.9(5) . . . . ?
C17 C8 C9 C14 1.9(5) . . . . ?
N2 C8 C9 C14 -178.0(3) . . . . ?
C8 C9 C10 C11 176.3(3) . . . . ?
C14 C9 C10 C11 -1.8(5) . . . . ?
C9 C10 C11 C12 1.2(6) . . . . ?
C10 C11 C12 C13 0.4(6) . . . . ?
C11 C12 C13 C14 -1.3(6) . . . . ?
C10 C9 C14 C15 178.6(3) . . . . ?
C8 C9 C14 C15 0.4(4) . . . . ?
C10 C9 C14 C13 0.8(5) . . . . ?
C8 C9 C14 C13 -177.3(3) . . . . ?
C12 C13 C14 C15 -177.0(3) . . . . ?
C12 C13 C14 C9 0.7(5) . . . . ?
C9 C14 C15 C16 -2.3(5) . . . . ?
C13 C14 C15 C16 175.4(3) . . . . ?
C14 C15 C16 C17 1.8(5) . . . . ?
C18 O1 C17 C8 -174.7(3) . . . . ?
C18 O1 C17 C16 4.7(5) . . . . ?
C9 C8 C17 O1 177.0(3) . . . . ?
N2 C8 C17 O1 -3.1(4) . . . . ?
C9 C8 C17 C16 -2.5(5) . . . . ?
N2 C8 C17 C16 177.4(3) . . . . ?
C15 C16 C17 O1 -178.8(3) . . . . ?
C15 C16 C17 C8 0.6(5) . . . . ?
