Dynamic covalent and noncovalent assembly of <i>o</i>-nitrosocumene in organic solvents and water.
Rogers, Cory H.; Pradeep, Anu; Galiano, Layla A.; Kelley, S. Ariel; Varadharajan, Ramkumar; Belmore, Ken; Whitt, Logan M.; Li, Yanmei; Champagne, Pier Alexandre; Ramamurthy, Vaidhyanathan; Blackstock, Silas C.; Chemical communications (Cambridge, England) 60 (2024) 13899–13902; doi:10.1039/d4cc03955f

data_7133940
_publ_section_title
;
 Dynamic covalent and noncovalent assembly of <i>o</i>-nitrosocumene in
 organic solvents and water.
;
_journal_issue                   94
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13899
_journal_page_last               13902
_journal_paper_doi               10.1039/d4cc03955f
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C18 H22 N2 O2'
_chemical_formula_sum            'C18 H22 N2 O2'
_chemical_formula_weight         298.37
_chemical_name_common
'oNC, 2-nitrosocumene, o-isopropylnitrosobenzene'
_chemical_name_systematic        o-nitrosocumene
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-12
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-12-12 deposited with the CCDC.	2024-10-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.592(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7459(4)
_cell_length_b                   10.4541(3)
_cell_length_c                   13.4750(4)
_cell_measurement_reflns_used    2992
_cell_measurement_temperature    117(20)
_cell_measurement_theta_max      70.7220
_cell_measurement_theta_min      4.0760
_cell_volume                     1669.51(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      117(20)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -31.00  -5.00   0.50    0.81    --    0.00 111.00 -45.00   52
  2  \w     13.00  38.00   0.50    0.81    --    0.00-111.00-139.00   50
  3  \w   -147.00 -96.00   0.50    3.23    --  -56.13-111.00-139.00  102
  4  \w     27.00 103.00   0.50    3.23    --   56.13-111.00-139.00  152
  5  \w     88.00 113.00   0.50    3.23    --   56.13 111.00 -45.00   50
  6  \w   -131.00 -88.00   0.50    3.23    -- -102.00-111.00-139.00   86
  7  \w    -64.00 -39.00   0.50    3.23    -- -102.00 111.00 -45.00   50
  8  \w     48.00  88.00   0.50    3.23    --  112.26-111.00-139.00   80
  9  \w    118.00 143.00   0.50    3.23    --  112.26 111.00 -45.00   50
 10  \w     29.00  78.00   0.50    0.81    --    0.00  19.00 -90.00   98
 11  \w    -26.00  10.00   0.50    0.81    --    0.00  19.00 -90.00   72
 12  \w    -35.00  26.00   0.50    3.23    --  -56.13  30.00 -60.00  122
 13  \w    -25.00  26.00   0.50    3.23    --  -56.13  15.00-120.00  102
 14  \w    -28.00  -3.00   0.50    3.23    --  -56.13  15.00 -90.00   50
 15  \w    -24.00  26.00   0.50    3.23    --  -56.13  15.00  90.00  100
 16  \w     92.00 138.00   0.50    3.23    --   56.13 125.00  60.00   92
 17  \w    111.00 136.00   0.50    3.23    --   56.13 125.00-120.00   50
 18  \w     79.00 118.00   0.50    3.23    --   56.13 125.00-150.00   78
 19  \w    -54.00 -19.00   0.50    3.23    -- -102.00  50.00   0.00   70
 20  \w    -56.00 -31.00   0.50    3.23    -- -102.00  50.00  90.00   50
 21  \w   -163.00 -82.00   0.50    3.23    -- -102.00-111.00   0.00  162
 22  \w    110.00 146.00   0.50    3.23    --  112.26 178.00 150.00   72
 23  \w     26.00  51.00   0.50    3.23    --  112.26 -50.00 -90.00   50
 24  \w     49.00  74.00   0.50    3.23    --  112.26 178.00 150.00   50
 25  \w     76.00 104.00   0.50    3.23    --  112.26-111.00 -60.00   56
 26  \w    142.00 173.00   0.50    3.23    --  112.26  50.00-150.00   62
 27  \w    117.00 170.00   0.50    3.23    --  112.26  77.00 -60.00  106
 28  \w     28.00  56.00   0.50    3.23    --  112.26 -50.00  60.00   56
 29  \w     20.00  97.00   0.50    3.23    --  112.26-111.00 -90.00  154
 30  \w     22.00  59.00   0.50    3.23    --  112.26 -63.00  60.00   74
 31  \w     62.00 117.00   0.50    3.23    --  112.26  50.00-150.00  110
 32  \w     48.00  73.00   0.50    3.23    --  112.26 -63.00-150.00   50
 33  \w     27.00 108.00   0.50    3.23    --  112.26-111.00  30.00  162
 34  \w     25.00  57.00   0.50    3.23    --  112.26 -50.00   0.00   64
 35  \w     31.00  63.00   0.50    3.23    --  112.26 -63.00-120.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0294880000
_diffrn_orient_matrix_UB_12      0.0070116000
_diffrn_orient_matrix_UB_13      -0.1215269000
_diffrn_orient_matrix_UB_21      -0.0242190000
_diffrn_orient_matrix_UB_22      0.1441804000
_diffrn_orient_matrix_UB_23      0.0019752000
_diffrn_orient_matrix_UB_31      0.1242042000
_diffrn_orient_matrix_UB_32      0.0296925000
_diffrn_orient_matrix_UB_33      0.0188879000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7988
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.267
_diffrn_reflns_theta_min         4.084
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  0.70654
_exptl_absorpt_correction_T_min  0.68757
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.60a (Rigaku Oxford Diffraction, 2022)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_recrystallization_method
'The material was recrystallised from DCM by slow cooling'
_exptl_crystal_size_max          0.026
_exptl_crystal_size_mid          0.023
_exptl_crystal_size_min          0.018
_exptl_crystal_size_rad          0.400
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3150
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0465
_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^)+(0.0533P)^2^+0.6272P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1192
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2668
_reflns_number_total             3150
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03955f2.cif
_cod_data_source_block           scb297_cu_3
_cod_depositor_comments          'Adding full bibliography for 7133940.cif.'
_cod_database_code               7133940
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         C18H22N2O2
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C00D(H00D), C00E(H00E)
1.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00A(H00A), C00C(H00C), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I)
1.c Idealised Me refined as rotating group:
 C00J(H00B,H00J,H00K), C00K(H00L,H00M,H00N), C00L(H00O,H00P,H00Q), C00M(H00R,
 H00S,H00T)
;
_shelx_res_checksum              25118
_shelx_hkl_checksum              1158
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.083
_oxdiff_exptl_absorpt_empirical_full_min 0.374