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_7126500
_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_absolute_configuration unk
_chemical_formula_moiety         'C12 H9 F N2 O3'
_chemical_formula_sum            'C12 H9 F N2 O3'
_chemical_formula_weight         248.21
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7895(17)
_cell_length_b                   20.620(2)
_cell_length_c                   3.8818(7)
_cell_measurement_reflns_used    1495
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.1340
_cell_measurement_theta_min      2.4520
_cell_volume                     1103.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -63.00  70.00   1.00    8.00    --  -20.00   0.00-180.00  133
  2  \w    -96.00  19.00   1.00    8.00    --  -20.00 -72.00  36.00  115
  3  \w    -72.00 -42.00   1.00    8.00    --  -20.00 -72.00-180.00   30
  4  \w   -110.00 -80.00   1.00    8.00    --  -20.00   0.00 108.00   30
;
_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      0.0047214000
_diffrn_orient_matrix_UB_12      -0.0073641000
_diffrn_orient_matrix_UB_13      0.1777968000
_diffrn_orient_matrix_UB_21      0.0471998000
_diffrn_orient_matrix_UB_22      0.0136476000
_diffrn_orient_matrix_UB_23      0.0002543000
_diffrn_orient_matrix_UB_31      -0.0198518000
_diffrn_orient_matrix_UB_32      0.0306910000
_diffrn_orient_matrix_UB_33      0.0426587000
_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  0.1011
_diffrn_reflns_av_unetI/netI     0.1333
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            6191
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         2.467
_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    0.120
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.494
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details
;
 Flack x determined using 250 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.7(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1909
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.1315
_refine_ls_R_factor_gt           0.0710
_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^)+(0.0424P)^2^+0.3265P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1654
_reflns_Friedel_coverage         0.686
_reflns_Friedel_fraction_full    0.949
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                1140
_reflns_number_total             1909
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc02851g2.cif
_cod_data_source_block           dm-aj-l4-50_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_cell_volume        1103.8(3)
_cod_original_formula_moiety     '0.8(C12 H9 F N2 O3)'
_cod_original_formula_sum        'C9.60 H7.20 F0.80 N1.60 O2.40'
_cod_original_formula_units_Z    5
_cod_original_formula_weight     198.57
_cod_database_code               7126500
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.986
_reflns_odcompleteness_completeness 93.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.08
_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:
 C007(H007), C008(H008), C009(H009), C00A(H00A), C00E(H00E), C00I(H00I)
2.b Idealised Me refined as rotating group:
 C00C(H00B,H00C,H00D)
;
_shelx_res_checksum              17819
_shelx_hkl_checksum              14796
_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 1.656
_oxdiff_exptl_absorpt_empirical_full_min 0.659