Visible-light-promoted iron-catalyzed C-H functionalization of 1,4-naphthoquinones <i>via</i> oxidative coupling with sulfoximines.
Sharma, Alpa; Kour, Harpreet; Kour, Jaspreet; Kamal, ?; Sawant, Sanghapal D.; Chemical communications (Cambridge, England) 58 (2022) 11312–11315; doi:10.1039/d2cc03319d

data_7130957
_publ_section_title
;
 Visible-light-promoted iron-catalyzed C-H functionalization of
 1,4-naphthoquinones <i>via</i> oxidative coupling with sulfoximines.
;
_journal_issue                   80
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11312
_journal_page_last               11315
_journal_paper_doi               10.1039/d2cc03319d
_journal_volume                  58
_journal_year                    2022
_chemical_formula_moiety         'C17 H12 N2 O5 S'
_chemical_formula_sum            'C17 H12 N2 O5 S'
_chemical_formula_weight         356.35
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-08-03
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.04.25 svn.r3594 for OlexSys, GUI svn.r5751)
;
_audit_update_record
;
2022-08-03 deposited with the CCDC.	2022-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.565(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.173(3)
_cell_length_b                   5.3337(15)
_cell_length_c                   25.755(7)
_cell_measurement_reflns_used    8464
_cell_measurement_temperature    108(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      3.51
_cell_volume                     1527.6(7)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      108.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            43547
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.31
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.7313
_exptl_absorpt_correction_T_min  0.6265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1584 before and 0.1125 after correction.
The Ratio of minimum to maximum transmission is 0.8567.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic greenish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3797
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0397P)^2^+1.0782P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0966
_reflns_number_gt                3479
_reflns_number_total             3797
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cc03319d2.cif
_cod_data_source_block           5n
_cod_database_code               7130957
_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:
 C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P)
2.b Idealised Me refined as rotating group:
 C00K(H00A,H00B,H00C)
;
_olex2_submission_special_instructions 'No special instructions were received'