#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/75/1557587.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_1557587
loop_
_publ_author_name
'Ikeda, Hideaki'
'Nishi, Kohei'
'Tsurugi, Hayato'
'Mashima, Kazushi'
_publ_section_title
;
 Chromium-catalyzed cyclopropanation of alkenes with bromoform in the
 presence of
 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-dihydropyrazine
;
_journal_issue                   14
_journal_name_full               'Chemical Science'
_journal_page_first              3604
_journal_page_last               3609
_journal_paper_doi               10.1039/D0SC00964D
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C11 H10 Br N O'
_chemical_formula_sum            'C11 H10 Br N O'
_chemical_formula_weight         252.11
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2019-09-18 deposited with the CCDC.	2020-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                80.831(11)
_cell_angle_beta                 86.517(11)
_cell_angle_gamma                62.902(8)
_cell_formula_units_Z            2
_cell_length_a                   6.7320(7)
_cell_length_b                   7.2280(6)
_cell_length_c                   12.0162(17)
_cell_measurement_reflns_used    2078
_cell_measurement_temperature    113
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.20
_cell_volume                     513.81(11)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_molecular_graphics    'CrystalStructure 4.2.4'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL Version 2016/4 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8391
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         3.201
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.976
_exptl_absorpt_correction_T_max  0.370
_exptl_absorpt_correction_T_min  0.173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             252.00
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.92
_refine_diff_density_min         -0.63
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0350P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0690
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2055
_reflns_number_total             2353
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d0sc00964d2.cif
_cod_data_source_block           IKE13067
_cod_depositor_comments
;Adding full bibliography for 1557587.cif.

 Adding full bibliography for 1557587.cif.
;
_cod_database_code               1557587
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -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_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 1.38194(4) 0.91523(4) 0.40487(2) 0.02652(9) Uani 1 1 d . . . . .
O1 O 1.0474(2) 0.7069(2) 0.17122(13) 0.0191(3) Uani 1 1 d . . . . .
N1 N 0.3469(3) 0.7886(3) -0.23197(17) 0.0252(4) Uani 1 1 d . . . . .
C1 C 1.1413(3) 0.8443(4) 0.39454(19) 0.0208(5) Uani 1 1 d . . . . .
H1 H 0.992804 0.964224 0.370469 0.025 Uiso 1 1 calc R U . . .
C2 C 1.1372(4) 0.6709(4) 0.47826(19) 0.0248(5) Uani 1 1 d . . . . .
H2A H 0.990038 0.685147 0.505928 0.030 Uiso 1 1 calc R U . . .
H2B H 1.260184 0.597627 0.534678 0.030 Uiso 1 1 calc R U . . .
C3 C 1.1921(4) 0.6396(4) 0.3571(2) 0.0235(5) Uani 1 1 d . . . . .
H3 H 1.351515 0.547720 0.340412 0.028 Uiso 1 1 calc R U . . .
C4 C 1.0183(3) 0.6349(4) 0.28666(18) 0.0212(5) Uani 1 1 d . . . . .
H4A H 1.035014 0.490088 0.294390 0.025 Uiso 1 1 calc R U . . .
H4B H 0.867273 0.727159 0.311918 0.025 Uiso 1 1 calc R U . . .
C5 C 0.8962(3) 0.7231(3) 0.09476(18) 0.0153(4) Uani 1 1 d . . . . .
C6 C 0.7159(3) 0.6789(3) 0.12198(18) 0.0164(4) Uani 1 1 d . . . . .
H6 H 0.691322 0.634734 0.198098 0.020 Uiso 1 1 calc R U . . .
C7 C 0.5730(3) 0.7001(3) 0.03704(18) 0.0159(4) Uani 1 1 d . . . . .
H7 H 0.449203 0.671888 0.055334 0.019 Uiso 1 1 calc R U . . .
C8 C 0.6099(3) 0.7623(3) -0.07488(18) 0.0157(4) Uani 1 1 d . . . . .
C9 C 0.7905(3) 0.8071(3) -0.10131(18) 0.0170(4) Uani 1 1 d . . . . .
H9 H 0.815797 0.850671 -0.177417 0.020 Uiso 1 1 calc R U . . .
C10 C 0.9315(3) 0.7880(3) -0.01702(18) 0.0161(4) Uani 1 1 d . . . . .
H10 H 1.053378 0.819264 -0.035182 0.019 Uiso 1 1 calc R U . . .
C11 C 0.4629(3) 0.7786(3) -0.16274(18) 0.0184(4) 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 0.0033 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
C5 O1 C4 116.58(16) . . ?
C2 C1 C3 60.66(15) . . ?
C2 C1 BR1 117.87(15) . . ?
C3 C1 BR1 118.62(15) . . ?
C2 C1 H1 116.1 . . ?
C3 C1 H1 116.1 . . ?
BR1 C1 H1 116.1 . . ?
C1 C2 C3 60.01(16) . . ?
C1 C2 H2A 117.8 . . ?
C3 C2 H2A 117.8 . . ?
C1 C2 H2B 117.8 . . ?
C3 C2 H2B 117.8 . . ?
H2A C2 H2B 114.9 . . ?
C1 C3 C4 117.29(19) . . ?
C1 C3 C2 59.33(15) . . ?
C4 C3 C2 117.54(19) . . ?
C1 C3 H3 116.8 . . ?
C4 C3 H3 116.8 . . ?
C2 C3 H3 116.8 . . ?
O1 C4 C3 108.20(18) . . ?
O1 C4 H4A 110.1 . . ?
C3 C4 H4A 110.1 . . ?
O1 C4 H4B 110.1 . . ?
C3 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
O1 C5 C10 115.45(18) . . ?
O1 C5 C6 124.52(19) . . ?
C10 C5 C6 120.04(18) . . ?
C7 C6 C5 119.54(19) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 120.45(19) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C9 119.61(18) . . ?
C7 C8 C11 119.82(19) . . ?
C9 C8 C11 120.57(19) . . ?
C10 C9 C8 120.06(19) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C5 120.29(19) . . ?
C9 C10 H10 119.9 . . ?
C5 C10 H10 119.9 . . ?
N1 C11 C8 179.0(2) . . ?
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 1.925(2) . ?
O1 C5 1.366(2) . ?
O1 C4 1.436(3) . ?
N1 C11 1.147(3) . ?
C1 C2 1.487(3) . ?
C1 C3 1.497(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.507(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.501(3) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.394(3) . ?
C5 C6 1.398(3) . ?
C6 C7 1.388(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.393(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.401(3) . ?
C8 C11 1.445(3) . ?
C9 C10 1.378(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
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
BR1 C1 C2 C3 -108.92(18) . . . . ?
C2 C1 C3 C4 107.4(2) . . . . ?
BR1 C1 C3 C4 -144.90(17) . . . . ?
BR1 C1 C3 C2 107.71(18) . . . . ?
C1 C2 C3 C4 -107.0(2) . . . . ?
C5 O1 C4 C3 -176.94(17) . . . . ?
C1 C3 C4 O1 84.2(2) . . . . ?
C2 C3 C4 O1 152.00(19) . . . . ?
C4 O1 C5 C10 -178.40(18) . . . . ?
C4 O1 C5 C6 1.4(3) . . . . ?
O1 C5 C6 C7 -179.74(18) . . . . ?
C10 C5 C6 C7 0.0(3) . . . . ?
C5 C6 C7 C8 0.8(3) . . . . ?
C6 C7 C8 C9 -1.1(3) . . . . ?
C6 C7 C8 C11 178.47(19) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C11 C8 C9 C10 -179.04(19) . . . . ?
C8 C9 C10 C5 0.4(3) . . . . ?
O1 C5 C10 C9 179.18(18) . . . . ?
C6 C5 C10 C9 -0.6(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168306213
