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_4517165
_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         'C34 H33 Cl Fe N O P S, C3 H7'
_chemical_formula_sum            'C37 H40 Cl Fe N O P S'
_chemical_formula_weight         669.03
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-21
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                76.299(3)
_cell_angle_beta                 75.440(3)
_cell_angle_gamma                73.252(3)
_cell_formula_units_Z            2
_cell_length_a                   9.5205(3)
_cell_length_b                   13.2892(4)
_cell_length_c                   14.2405(4)
_cell_measurement_reflns_used    10142
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      76.8290
_cell_measurement_theta_min      3.4790
_cell_volume                     1643.39(9)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (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 0.989
_diffrn_measured_fraction_theta_max 0.939
_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   -108.00 -80.00   1.00    0.10    --  -48.45 162.00 -22.00   28
  2  \w    -87.00  -5.00   1.00    0.10    --  -48.45 117.00-172.00   82
  3  \w    -80.00 -47.00   1.00    0.10    --  -48.45-162.00 -50.00   33
  4  \w     62.00  87.00   1.00    0.10    --   48.45-162.00 -50.00   25
  5  \w     70.00  95.00   1.00    0.10    --   48.45 162.00 -22.00   25
  6  \w     50.00  92.00   1.00    0.10    --   48.45-117.00  99.00   42
  7  \w   -144.00 -52.00   1.00    0.80    --  -86.25-162.00 -50.00   92
  8  \w   -101.00 -76.00   1.00    0.80    --  -86.25-117.00  99.00   25
  9  \w    -74.00 -49.00   1.00    0.80    --  -86.25 117.00-172.00   25
 10  \w     70.00 130.00   1.00    0.80    --  107.75 162.00 -22.00   60
 11  \w     63.00 113.00   1.00    0.80    --  107.75-117.00  99.00   50
 12  \w    102.00 155.00   1.00    0.80    --  107.75 117.00-172.00   53
 13  \w    103.00 142.00   1.00    0.80    --  107.75-162.00 -50.00   39
 14  \w   -119.00 -27.00   1.00    0.10    --  -48.45 -77.00  90.00   92
 15  \w     29.00 121.00   1.00    0.10    --   48.45  77.00-180.00   92
 16  \w   -156.00 -75.00   1.00    0.80    --  -86.25 -37.00 -30.00   81
 17  \w    103.00 178.00   1.00    0.80    --  107.75  19.00-180.00   75
 18  \w     95.00 178.00   1.00    0.80    --  107.75 125.00-120.00   83
 19  \w     38.00 123.00   1.00    0.80    --  107.75 -77.00-120.00   85
 20  \w     47.00 117.00   1.00    0.80    --  107.75-125.00-180.00   70
 21  \w    100.00 171.00   1.00    0.80    --  107.75 125.00 120.00   71
 22  \w     95.00 177.00   1.00    0.80    --  107.75  19.00 120.00   82
 23  \w     97.00 169.00   1.00    0.80    --  107.75 125.00 -30.00   72
 24  \w     35.00 121.00   1.00    0.80    --  107.75 -57.00-120.00   86
;
_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      -0.0210049000
_diffrn_orient_matrix_UB_12      0.0897905000
_diffrn_orient_matrix_UB_13      -0.0900016000
_diffrn_orient_matrix_UB_21      -0.0446234000
_diffrn_orient_matrix_UB_22      0.0840318000
_diffrn_orient_matrix_UB_23      0.0672507000
_diffrn_orient_matrix_UB_31      0.1651490000
_diffrn_orient_matrix_UB_32      0.0029128000
_diffrn_orient_matrix_UB_33      -0.0166076000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16969
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.991
_diffrn_reflns_theta_min         3.529
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.710
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.16570
_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_density_diffrn    1.352
_exptl_crystal_description       block
_exptl_crystal_F_000             702
_refine_diff_density_max         1.106
_refine_diff_density_min         -0.927
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         6509
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0645
_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^)+(0.1109P)^2^+4.0701P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1721
_refine_ls_wR_factor_ref         0.2070
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5611
_reflns_number_total             6509
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b03604_si_002.cif
_cod_data_source_block           1(ArNO)
_cod_database_code               4517165
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         FePSCN
_reflns_odcompleteness_completeness 98.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C37(H37A,H37B), C36(H36A,H36B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C24(H24), C11(H11), C6(H6), C20(H20), C21(H21), C9(H9),
 C22(H22), C10(H10), C8(H8), C18(H18), C5(H5), C23(H23), C16(H16), C14(H14),
 C17(H17), C15(H15)
2.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C30(H30A,H30B,H30C), C34(H34A,H34B,
 H34C), C33(H33A,H33B,H33C), C35(H35A,H35B,H35C)
;
_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 2.715
_oxdiff_exptl_absorpt_empirical_full_min 0.436