Iron-Catalyzed Reductive Coupling of Nitroarenes with Olefins: Intermediate of Iron‒Nitroso Complex
Song, Heng; Yang, Zhuoyi; Tung, Chen-Ho; Wang, Wenguang; ACS Catalysis  (2019) 276–; doi:10.1021/acscatal.9b03604

data_4517166
_publ_section_title
;
 Iron-Catalyzed Reductive Coupling of Nitroarenes with Olefins:
 Intermediate of Iron--Nitroso Complex
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              276
_journal_paper_doi               10.1021/acscatal.9b03604
_journal_year                    2019
_chemical_formula_moiety         'C46 H43 Fe O P2 S2, C3 H7'
_chemical_formula_sum            'C49 H50 Fe O P2 S2'
_chemical_formula_weight         836.80
_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
_audit_creation_date             2019-07-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.058(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.0306(7)
_cell_length_b                   14.4302(6)
_cell_length_c                   20.0912(9)
_cell_measurement_reflns_used    9320
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      30.7280
_cell_measurement_theta_min      3.4840
_cell_volume                     4187.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.30d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.30d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.30d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.796
_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    -16.00  19.00   1.00   30.00    --    5.49  80.00 -92.00   35
  2  \w    -55.00  30.00   1.00   30.00    --    5.49 -80.00 143.00   85
  3  \w    -26.00  29.00   1.00   30.00    --   -4.48 -99.00  90.00   55
  4  \w    -26.00  29.00   1.00   30.00    --   -4.48 -99.00 -30.00   55
  5  \w    -21.00  29.00   1.00   30.00    --   -4.48 -99.00-120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0295422000
_diffrn_orient_matrix_UB_12      0.0380157000
_diffrn_orient_matrix_UB_13      0.0009744000
_diffrn_orient_matrix_UB_21      0.0334804000
_diffrn_orient_matrix_UB_22      0.0179460000
_diffrn_orient_matrix_UB_23      0.0292969000
_diffrn_orient_matrix_UB_31      0.0204508000
_diffrn_orient_matrix_UB_32      0.0254865000
_diffrn_orient_matrix_UB_33      -0.0221339000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_unetI/netI     0.0811
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.796
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            39264
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.796
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.899
_diffrn_reflns_theta_min         3.202
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.573
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.30d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_refine_diff_density_max         0.894
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     502
_refine_ls_number_reflns         10520
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0697P)^2^+0.3454P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1292
_refine_ls_wR_factor_ref         0.1430
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7136
_reflns_number_total             10520
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b03604_si_002.cif
_cod_data_source_block           1'
_cod_database_code               4517166
_shelxl_version_number           2013-4
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C46(H46A,H46B), C47(H47A,H47B)
2.b Aromatic/amide H refined with riding coordinates:
 C33(H33), C15(H15), C12(H12), C40(H40), C30(H30), C13(H13), C24(H24),
 C32(H32), C25(H25), C14(H14), C36(H36), C39(H39), C28(H28), C31(H31), C26(H26),
  C22(H22), C44(H44), C18(H18), C38(H38), C49(H49), C37(H37), C27(H27),
 C42(H42), C19(H19), C45(H45), C21(H21), C20(H20), C43(H43)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C8(H8A,H8B,H8C), C6(H6A,H6B,H6C), C9(H9A,H9B,H9C),
 C7(H7A,H7B,H7C), C48(H48A,H48B,H48C)
;
_shelx_res_checksum              74464
_shelx_hkl_checksum              45203
_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 2.519
_oxdiff_exptl_absorpt_empirical_full_min 0.304