#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:41:14 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281574 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/90/7159037.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_7159037
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_formula_moiety         'C9 H15.56 N2 O1.44, H2 O'
_chemical_formula_sum            'C9 H17.56 N2 O2.44'
_chemical_formula_weight         192.85
_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   mixed
_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                102.84(3)
_cell_angle_beta                 94.37(2)
_cell_angle_gamma                117.329(10)
_cell_formula_units_Z            2
_cell_length_a                   7.7049(9)
_cell_length_b                   8.1609(17)
_cell_length_c                   10.0105(16)
_cell_measurement_reflns_used    1152
_cell_measurement_temperature    173
_cell_measurement_theta_max      25.30
_cell_measurement_theta_min      2.10
_cell_volume                     533.5(2)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 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    'SIR2011 (Burla, et al., 2012)'
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_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  0.0452
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10852
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.383
_diffrn_reflns_theta_min         3.021
_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    0.087
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.825
_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    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             210
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Water'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.039(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1942
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0578
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0532P)²+0.3761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1494
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1538
_reflns_number_total             1942
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01863b2.cif
_cod_data_source_block           8-9
_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_cell_volume        533.55(17)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7159037
_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   0.999
_shelx_estimated_absorpt_t_min   0.988
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All N(H,H) groups, All O(H,H) groups
2. Restrained distances
 O11-H11A = O11-H11B = N8-H8A = N8-H8B
 0.98 with sigma of 0.02
 H11A-H11B
 1.6 with sigma of 0.04
 N1-O1
 1.27 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
N1 \\sim O1: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
within 2A
4. Others
 Sof(H1)=1-FVAR(1)
 Sof(O1)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4)
5.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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
O1 O 0.4361(5) 0.9652(5) 0.3758(4) 0.0407(17) Uani 0.437(8) 1 d D U P A 1
O8 O 0.2046(2) 0.2363(2) 0.10092(19) 0.0416(5) Uani 1 1 d . . . . .
O11 O 0.5263(3) 0.1668(4) 0.1979(3) 0.0802(8) Uani 1 1 d D . . . .
H11A H 0.521(7) 0.161(7) 0.296(3) 0.120 Uiso 1 1 d D U . . .
H11B H 0.432(6) 0.209(6) 0.179(4) 0.120 Uiso 1 1 d D U . . .
N1 N 0.3044(3) 0.7992(3) 0.3271(2) 0.0382(5) Uani 1 1 d D U . . .
H1 H 0.412716 0.932818 0.364164 0.046 Uiso 0.563(8) 1 calc R U P A 2
N8 N -0.1200(3) 0.1355(3) 0.1034(2) 0.0411(6) Uani 1 1 d D . . . .
H8A H -0.154(4) 0.009(3) 0.046(3) 0.062 Uiso 1 1 d D U . . .
H8B H -0.221(4) 0.163(4) 0.133(3) 0.062 Uiso 1 1 d D U . . .
C2 C 0.3347(3) 0.6357(3) 0.2579(3) 0.0350(6) Uani 1 1 d . . . . .
C3 C 0.1209(3) 0.4709(3) 0.2154(2) 0.0325(5) Uani 1 1 d . . . . .
C4 C -0.0061(3) 0.5293(3) 0.2569(3) 0.0371(6) Uani 1 1 d . . . . .
H4 H -0.146248 0.446144 0.239258 0.045 Uiso 1 1 calc R U . . .
C5 C 0.0934(3) 0.7388(3) 0.3340(3) 0.0352(6) Uani 1 1 d . . . . .
C6 C 0.4307(4) 0.6777(4) 0.1339(3) 0.0533(8) Uani 1 1 d . . . . .
H6A H 0.559093 0.797279 0.166405 0.064 Uiso 1 1 calc R U . . .
H6B H 0.342721 0.691774 0.066867 0.064 Uiso 1 1 calc R U . . .
H6C H 0.452335 0.571071 0.088467 0.064 Uiso 1 1 calc R U . . .
C7 C 0.4648(4) 0.6083(4) 0.3643(3) 0.0502(7) Uani 1 1 d . . . . .
H7A H 0.395344 0.573732 0.440149 0.060 Uiso 1 1 calc R U . . .
H7B H 0.591647 0.728503 0.403037 0.060 Uiso 1 1 calc R U . . .
H7C H 0.490902 0.505084 0.318067 0.060 Uiso 1 1 calc R U . . .
C8 C 0.0716(3) 0.2712(3) 0.1362(2) 0.0352(6) Uani 1 1 d . . . . .
C9 C 0.0680(4) 0.7730(4) 0.4859(3) 0.0460(7) Uani 1 1 d . . . . .
H9A H 0.142830 0.911440 0.534542 0.055 Uiso 1 1 calc R U . . .
H9B H 0.118718 0.705369 0.532590 0.055 Uiso 1 1 calc R U . . .
H9C H -0.073782 0.724186 0.488043 0.055 Uiso 1 1 calc R U . . .
C10 C 0.0222(4) 0.8487(4) 0.2607(3) 0.0478(7) Uani 1 1 d . . . . .
H10A H 0.098689 0.986679 0.310705 0.057 Uiso 1 1 calc R U . . .
H10B H -0.119931 0.802383 0.260260 0.057 Uiso 1 1 calc R U . . .
H10C H 0.042128 0.827799 0.164181 0.057 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'
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
H11A O11 H11B 102(3) . . ?
O1 N1 C2 124.9(3) . . ?
O1 N1 C5 122.2(3) . . ?
C2 N1 H1 123.6 . . ?
C5 N1 H1 123.6 . . ?
C5 N1 C2 112.85(18) . . ?
H8A N8 H8B 121(3) . . ?
C8 N8 H8A 117.7(18) . . ?
C8 N8 H8B 121.3(19) . . ?
N1 C2 C3 100.88(17) . . ?
N1 C2 C6 109.1(2) . . ?
N1 C2 C7 109.2(2) . . ?
C3 C2 C7 112.6(2) . . ?
C6 C2 C3 113.1(2) . . ?
C6 C2 C7 111.4(2) . . ?
C4 C3 C2 111.6(2) . . ?
C4 C3 C8 127.0(2) . . ?
C8 C3 C2 121.43(19) . . ?
C3 C4 H4 123.4 . . ?
C3 C4 C5 113.2(2) . . ?
C5 C4 H4 123.4 . . ?
N1 C5 C4 101.42(18) . . ?
N1 C5 C9 110.8(2) . . ?
N1 C5 C10 109.7(2) . . ?
C4 C5 C9 112.0(2) . . ?
C4 C5 C10 112.2(2) . . ?
C10 C5 C9 110.4(2) . . ?
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 . . ?
O8 C8 N8 122.0(2) . . ?
O8 C8 C3 120.7(2) . . ?
N8 C8 C3 117.4(2) . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
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 . . ?
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
O1 N1 1.213(4) . ?
O8 C8 1.239(3) . ?
O11 H11A 0.995(19) . ?
O11 H11B 0.956(19) . ?
N1 H1 0.9800 . ?
N1 C2 1.489(3) . ?
N1 C5 1.479(3) . ?
N8 H8A 0.963(18) . ?
N8 H8B 0.957(18) . ?
N8 C8 1.333(3) . ?
C2 C3 1.519(3) . ?
C2 C6 1.517(4) . ?
C2 C7 1.530(4) . ?
C3 C4 1.327(3) . ?
C3 C8 1.496(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.492(3) . ?
C5 C9 1.528(4) . ?
C5 C10 1.526(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O11 H11A O1 0.995(19) 1.82(4) 2.608(5) 134(4) 1_545 yes
O11 H11B O8 0.956(19) 1.99(2) 2.928(3) 166(4) . yes
N8 H8A O8 0.963(18) 2.053(19) 3.006(3) 170(3) 2 yes
N8 H8B O11 0.957(18) 2.107(19) 3.052(3) 169(3) 1_455 yes
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 -178.0(3) . . . . ?
O1 N1 C2 C6 -58.7(4) . . . . ?
O1 N1 C2 C7 63.2(4) . . . . ?
O1 N1 C5 C4 177.9(3) . . . . ?
O1 N1 C5 C9 -63.1(4) . . . . ?
O1 N1 C5 C10 59.0(4) . . . . ?
N1 C2 C3 C4 -1.7(3) . . . . ?
N1 C2 C3 C8 178.2(2) . . . . ?
C2 N1 C5 C4 -3.3(3) . . . . ?
C2 N1 C5 C9 115.8(2) . . . . ?
C2 N1 C5 C10 -122.1(2) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C2 C3 C8 O8 -1.4(4) . . . . ?
C2 C3 C8 N8 179.9(2) . . . . ?
C3 C4 C5 N1 2.1(3) . . . . ?
C3 C4 C5 C9 -116.0(2) . . . . ?
C3 C4 C5 C10 119.1(2) . . . . ?
C4 C3 C8 O8 178.4(2) . . . . ?
C4 C3 C8 N8 -0.2(4) . . . . ?
C5 N1 C2 C3 3.1(2) . . . . ?
C5 N1 C2 C6 122.5(2) . . . . ?
C5 N1 C2 C7 -115.6(2) . . . . ?
C6 C2 C3 C4 -118.1(2) . . . . ?
C6 C2 C3 C8 61.8(3) . . . . ?
C7 C2 C3 C4 114.5(2) . . . . ?
C7 C2 C3 C8 -65.6(3) . . . . ?
C8 C3 C4 C5 179.9(2) . . . . ?
