#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:41:14 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281574 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/90/7159038.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_7159038
loop_
_publ_author_name
'Giannoulis, Angeliki'
'Ackermann, Katrin'
'Bogdanov, Alexey'
'Cordes, David B.'
'Higgins, Catherine'
'Ward, Joshua'
'Slawin, Alexandra M. Z.'
'Taylor, James E.'
'Bode, Bela E.'
_publ_section_title
;
 Synthesis of mono-nitroxides and of bis-nitroxides with varying
 electronic through-bond communication.
;
_journal_issue                   2
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              375
_journal_page_last               385
_journal_paper_doi               10.1039/d2ob01863b
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H14 Br2 N O'
_chemical_formula_sum            'C10 H14 Br2 N O'
_chemical_formula_weight         324.04
_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
_audit_creation_date             2022-10-08
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-10-10 deposited with the CCDC.	2022-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4876(9)
_cell_length_b                   10.2177(11)
_cell_length_c                   12.7098(14)
_cell_measurement_reflns_used    3959
_cell_measurement_temperature    173
_cell_measurement_theta_max      25.40
_cell_measurement_theta_min      2.60
_cell_volume                     1232.1(2)
_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    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'DIRDIF99-PATTY (Gould, et al., 1999)'
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'AFC10: Fixed χ 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       ω
_diffrn_measurement_specimen_support Loop
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15200
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.362
_diffrn_reflns_theta_min         2.558
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           66.0
_diffrn_source_power             2.97
_diffrn_source_type              'Rigaku FR-X'
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.550
_exptl_absorpt_correction_T_max  0.518
_exptl_absorpt_correction_T_min  0.391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             636
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 778 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         2256
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0188
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0238P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0421
_refine_ls_wR_factor_ref         0.0426
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2005
_reflns_number_total             2256
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01863b2.cif
_cod_data_source_block           15
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7159031--7159038.cif.
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7159038
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.560
_shelx_estimated_absorpt_t_min   0.420
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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_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 0.93366(5) 0.11988(3) 0.68928(3) 0.04772(12) Uani 1 1 d . . . . .
Br2 Br 1.05671(4) 0.36970(4) 0.57782(3) 0.04608(12) Uani 1 1 d . . . . .
O1 O 0.4630(2) 0.7268(2) 0.63970(18) 0.0320(5) Uani 1 1 d . . . . .
N1 N 0.5676(3) 0.6514(2) 0.62237(19) 0.0251(5) Uani 1 1 d . . . . .
C2 C 0.5827(3) 0.5229(3) 0.6742(2) 0.0246(7) Uani 1 1 d . . . . .
C3 C 0.7235(3) 0.4791(3) 0.6283(3) 0.0246(7) Uani 1 1 d . . . . .
C4 C 0.7788(3) 0.5703(3) 0.5657(2) 0.0243(7) Uani 1 1 d . . . . .
H4 H 0.867060 0.560629 0.531251 0.029 Uiso 1 1 calc R U . . .
C5 C 0.6876(3) 0.6903(3) 0.5548(3) 0.0237(7) Uani 1 1 d . . . . .
C6 C 0.5894(4) 0.5425(3) 0.7936(2) 0.0327(8) Uani 1 1 d . . . . .
H6A H 0.502404 0.584619 0.817756 0.039 Uiso 1 1 calc R U . . .
H6B H 0.670229 0.598017 0.811157 0.039 Uiso 1 1 calc R U . . .
H6C H 0.599694 0.457337 0.828220 0.039 Uiso 1 1 calc R U . . .
C7 C 0.4590(4) 0.4361(3) 0.6442(3) 0.0348(8) Uani 1 1 d . . . . .
H7A H 0.459609 0.421191 0.568055 0.042 Uiso 1 1 calc R U . . .
H7B H 0.370675 0.479063 0.664400 0.042 Uiso 1 1 calc R U . . .
H7C H 0.466867 0.352053 0.680907 0.042 Uiso 1 1 calc R U . . .
C8 C 0.7747(4) 0.3482(3) 0.6573(3) 0.0290(7) Uani 1 1 d . . . . .
H8 H 0.707737 0.294830 0.692643 0.035 Uiso 1 1 calc R U . . .
C9 C 0.8986(4) 0.2929(3) 0.6423(3) 0.0304(8) Uani 1 1 d . . . . .
C10 C 0.7549(3) 0.8156(3) 0.5993(3) 0.0346(9) Uani 1 1 d . . . . .
H10A H 0.791396 0.798161 0.670066 0.041 Uiso 1 1 calc R U . . .
H10B H 0.683722 0.884960 0.602802 0.041 Uiso 1 1 calc R U . . .
H10C H 0.832287 0.843359 0.553438 0.041 Uiso 1 1 calc R U . . .
C11 C 0.6383(3) 0.7125(3) 0.4418(3) 0.0300(8) Uani 1 1 d . . . . .
H11A H 0.568094 0.782795 0.440507 0.036 Uiso 1 1 calc R U . . .
H11B H 0.596193 0.631790 0.414486 0.036 Uiso 1 1 calc R U . . .
H11C H 0.719055 0.737124 0.397995 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 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'
O O 0.0106 0.0060 '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
O1 N1 C2 122.4(2) . . ?
O1 N1 C5 122.5(2) . . ?
C2 N1 C5 115.0(2) . . ?
N1 C2 C3 100.1(2) . . ?
N1 C2 C6 109.3(2) . . ?
N1 C2 C7 109.4(3) . . ?
C3 C2 C6 112.4(3) . . ?
C7 C2 C3 114.2(2) . . ?
C7 C2 C6 110.8(3) . . ?
C4 C3 C2 111.6(3) . . ?
C4 C3 C8 131.0(3) . . ?
C8 C3 C2 117.4(3) . . ?
C3 C4 H4 123.3 . . ?
C3 C4 C5 113.4(3) . . ?
C5 C4 H4 123.3 . . ?
N1 C5 C4 99.8(2) . . ?
N1 C5 C10 109.2(3) . . ?
N1 C5 C11 110.5(3) . . ?
C4 C5 C10 113.9(2) . . ?
C4 C5 C11 112.5(3) . . ?
C11 C5 C10 110.4(3) . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8 114.8 . . ?
C9 C8 C3 130.4(3) . . ?
C9 C8 H8 114.8 . . ?
Br2 C9 Br1 112.73(17) . . ?
C8 C9 Br1 120.7(3) . . ?
C8 C9 Br2 126.5(3) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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 C9 1.895(3) . ?
Br2 C9 1.881(3) . ?
O1 N1 1.275(3) . ?
N1 C2 1.475(4) . ?
N1 C5 1.481(4) . ?
C2 C3 1.524(4) . ?
C2 C6 1.532(4) . ?
C2 C7 1.520(4) . ?
C3 C4 1.333(5) . ?
C3 C8 1.471(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.506(4) . ?
C5 C10 1.538(5) . ?
C5 C11 1.527(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8 0.9500 . ?
C8 C9 1.318(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
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
O1 N1 C2 C3 -178.5(3) . . . . ?
O1 N1 C2 C6 -60.3(4) . . . . ?
O1 N1 C2 C7 61.2(4) . . . . ?
O1 N1 C5 C4 177.9(3) . . . . ?
O1 N1 C5 C10 58.2(4) . . . . ?
O1 N1 C5 C11 -63.4(4) . . . . ?
N1 C2 C3 C4 2.3(3) . . . . ?
N1 C2 C3 C8 -177.0(3) . . . . ?
C2 N1 C5 C4 2.1(3) . . . . ?
C2 N1 C5 C10 -117.6(3) . . . . ?
C2 N1 C5 C11 120.7(3) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
C2 C3 C8 C9 -169.2(3) . . . . ?
C3 C4 C5 N1 -0.5(3) . . . . ?
C3 C4 C5 C10 115.7(3) . . . . ?
C3 C4 C5 C11 -117.6(3) . . . . ?
C3 C8 C9 Br1 -180.0(3) . . . . ?
C3 C8 C9 Br2 1.2(5) . . . . ?
C4 C3 C8 C9 11.6(6) . . . . ?
C5 N1 C2 C3 -2.7(3) . . . . ?
C5 N1 C2 C6 115.5(3) . . . . ?
C5 N1 C2 C7 -123.0(3) . . . . ?
C6 C2 C3 C4 -113.6(3) . . . . ?
C6 C2 C3 C8 67.1(4) . . . . ?
C7 C2 C3 C4 119.0(3) . . . . ?
C7 C2 C3 C8 -60.3(4) . . . . ?
C8 C3 C4 C5 178.0(3) . . . . ?
