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_4517167
_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         'C18 H24 N2 O'
_chemical_formula_sum            'C18 H24 N2 O'
_chemical_formula_weight         284.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-09-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.3428(3)
_cell_length_b                   11.7215(3)
_cell_length_c                   24.5548(7)
_cell_measurement_reflns_used    3732
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      76.6610
_cell_measurement_theta_min      5.6610
_cell_volume                     3264.67(15)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.944
_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    -85.00 -32.00   1.00    1.40    --  -48.45 104.00-173.00   53
  2  \w    -68.00 -24.00   1.00   10.00    --  -86.25 152.00-114.00   44
  3  \w     97.00 175.00   1.00   10.00    --  107.75  22.00  16.00   78
  4  \w    128.00 160.00   1.00   10.00    --  107.75 104.00-173.00   32
  5  \w   -119.00 -27.00   1.00    1.40    --  -48.45 -77.00  90.00   92
  6  \w     92.00 177.00   1.00   10.00    --  107.75 125.00 -90.00   85
  7  \w     35.00  93.00   1.00   10.00    --  107.75 -99.00  60.00   58
;
_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      0.0933774000
_diffrn_orient_matrix_UB_12      -0.0156756000
_diffrn_orient_matrix_UB_13      -0.0448802000
_diffrn_orient_matrix_UB_21      -0.0914954000
_diffrn_orient_matrix_UB_22      0.0349926000
_diffrn_orient_matrix_UB_23      -0.0434642000
_diffrn_orient_matrix_UB_31      0.0369996000
_diffrn_orient_matrix_UB_32      0.1255210000
_diffrn_orient_matrix_UB_33      0.0064188000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            9693
_diffrn_reflns_theta_full        76.98
_diffrn_reflns_theta_max         76.98
_diffrn_reflns_theta_min         3.60
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.560
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58356
_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    1.157
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3263
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0586
_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^)+(0.0314P)^2^+4.6033P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1517
_reflns_number_gt                2599
_reflns_number_total             3263
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs9b03604_si_002.cif
_cod_data_source_block           4l
_cod_database_code               4517167
_chemical_oxdiff_formula         CNO
_reflns_odcompleteness_completeness 99.10
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C5(H5), C10(H10), C9(H9), C3(H3), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C17(H17A,H17B,
 H17C), C16(H16A,H16B,H16C)
;
_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 1.435
_oxdiff_exptl_absorpt_empirical_full_min 0.590