A directing group-assisted ruthenium-catalyzed approach to access meta-nitrated phenols.
Sasmal, Sheuli; Sinha, Soumya Kumar; Lahiri, Goutam Kumar; Maiti, Debabrata; Chemical communications (Cambridge, England) 56 (2020) 7100–7103; doi:10.1039/d0cc02851g

data_7126501
_publ_section_title
;
 A directing group-assisted ruthenium-catalyzed approach to access
 meta-nitrated phenols.
;
_journal_issue                   52
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7100
_journal_page_last               7103
_journal_paper_doi               10.1039/d0cc02851g
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C12 H10 N2 O4'
_chemical_formula_sum            'C12 H10 N2 O4'
_chemical_formula_weight         246.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-13
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2020-04-13 deposited with the CCDC.	2020-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.333(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5310(4)
_cell_length_b                   11.1285(5)
_cell_length_c                   12.0481(6)
_cell_measurement_reflns_used    4162
_cell_measurement_temperature    150
_cell_measurement_theta_max      31.0820
_cell_measurement_theta_min      3.5960
_cell_volume                     1072.54(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.950
_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    -72.00  53.50   0.50    8.00    --  -20.00   0.00-108.00  251
  2  \w    -13.50  18.00   0.50    8.00    --  -20.00 -72.00 108.00   63
  3  \w    -73.00 -43.00   0.50    8.00    --  -20.00 -72.00  36.00   60
  4  \w   -107.00  -3.50   0.50    8.00    --  -20.00   0.00 -36.00  207
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0700860000
_diffrn_orient_matrix_UB_12      -0.0317796000
_diffrn_orient_matrix_UB_13      0.0381990000
_diffrn_orient_matrix_UB_21      0.0321351000
_diffrn_orient_matrix_UB_22      0.0541235000
_diffrn_orient_matrix_UB_23      0.0305490000
_diffrn_orient_matrix_UB_31      -0.0437565000
_diffrn_orient_matrix_UB_32      -0.0111068000
_diffrn_orient_matrix_UB_33      0.0393876000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5567
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.146
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1797
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0704P)^2^+0.3562P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1143
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1633
_reflns_number_total             1797
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc02851g2.cif
_cod_data_source_block           dm-ta-53_mo
_cod_depositor_comments
;
Adding full bibliography for 7126500--7126501.cif.

2025-01-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C5.33 H4.44 N0.89 O1.78'
_cod_original_formula_weight         109.43
_cod_original_formula_moiety         '0.444(C12 H10 N2 O4)'
_cod_original_formula_units_Z            9
_cod_original_cell_volume        1072.55(9)
_cod_database_code               7126501
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.987
_reflns_odcompleteness_completeness 79.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.06
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00A(H00D), C00B(H00E), C00C(H00F), C00H(H00H),
 C00I(H00I)
2.b Idealised Me refined as rotating group:
 C007(H00A,H00B,H00C)
;
_shelx_res_checksum              36379
_shelx_hkl_checksum              39290
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.811
_oxdiff_exptl_absorpt_empirical_full_min 0.735