Cobalt(II)-catalyzed <i>peri</i>-C(sp<sup>2</sup>)-H selective hydroxylation of naphthalene monoimides.
Chand, Tapasi; Gupta, Princi; Oza, Nehali; Kapur, Manmohan; Chemical communications (Cambridge, England) 60 (2024) 1770–1773; doi:10.1039/d3cc06050k

data_7132626
_publ_section_title
;
 Cobalt(II)-catalyzed <i>peri</i>-C(sp<sup>2</sup>)-H selective
 hydroxylation of naphthalene monoimides.
;
_journal_issue                   13
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1770
_journal_page_last               1773
_journal_paper_doi               10.1039/d3cc06050k
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C13 H9 N O3'
_chemical_formula_sum            'C13 H9 N O3'
_chemical_formula_weight         227.22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-28
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-05-29 deposited with the CCDC.	2024-01-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8378(2)
_cell_length_b                   8.6367(5)
_cell_length_c                   29.4303(19)
_cell_measurement_reflns_used    9536
_cell_measurement_temperature    185.00
_cell_measurement_theta_max      74.58
_cell_measurement_theta_min      3.96
_cell_volume                     975.49(10)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      185.00
_diffrn_measured_fraction_theta_full 0.9731
_diffrn_measured_fraction_theta_max 0.9731
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.9731
_diffrn_reflns_Laue_measured_fraction_max 0.9731
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            4526
_diffrn_reflns_point_group_measured_fraction_full 0.9596
_diffrn_reflns_point_group_measured_fraction_max 0.9596
_diffrn_reflns_theta_full        66.5754
_diffrn_reflns_theta_max         66.58
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.927
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_description       irregular
_exptl_crystal_F_000             473.758
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.3834
_refine_diff_density_min         -0.2474
_refine_diff_density_rms         0.0676
_refine_ls_abs_structure_details
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_d_res_high            0.8401
_refine_ls_d_res_low             14.7151
_refine_ls_extinction_coef       0.055(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0463
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1661
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0463
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0949P)^2^+0.1125P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1361
_refine_ls_wR_factor_ref         0.1390
_reflns_Friedel_coverage         0.937
_reflns_limit_h_max              4
_reflns_limit_h_min              -4
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              34
_reflns_limit_l_min              -34
_reflns_number_gt                1509
_reflns_number_total             1661
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3cc06050k2.cif
_cod_data_source_block           NO_01_71_P
_cod_depositor_comments
;
         Adding full bibliography for 7132626.cif.

2025-01-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C2.6 H1.8 N0.2 O0.6'
_cod_original_formula_weight         45.444
_cod_original_formula_moiety         '0.2(C13 H9 N O3)'
_cod_original_formula_units_Z            20
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               7132626
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C009(H009), C00B(H00B), C00E(H00E), C00F(H00F)
2.b Idealised Me refined as rotating group:
 C00H(H00a,H00c,H00d)
2.c Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_olex2_submission_original_sample_id NO-01-71-P
_olex2_submission_special_instructions 'No special instructions were received'