Synthesis of mono-nitroxides and of bis-nitroxides with varying electronic through-bond communication.
Giannoulis, Angeliki; Ackermann, Katrin; Bogdanov, Alexey; Cordes, David B.; Higgins, Catherine; Ward, Joshua; Slawin, Alexandra M. Z.; Taylor, James E.; Bode, Bela E.; Organic & biomolecular chemistry 21 (2023) 375–385; doi:10.1039/d2ob01863b

data_7159037
_publ_section_title
;
 Synthesis of mono-nitroxides and of bis-nitroxides with varying
 electronic through-bond communication.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; 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 \c 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       \w
_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+0.001xFc^2^\l^3^/sin(2\q)]^-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/[\s^2^(Fo^2^)+(0.0532P)^2^+0.3761P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_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)
;
_shelx_res_checksum              87992