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_4517168
_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         'C17 H15 N'
_chemical_formula_sum            'C17 H15 N'
_chemical_formula_weight         233.30
_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
_audit_creation_date             2018-06-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.3043(4)
_cell_length_b                   8.1054(2)
_cell_length_c                   18.5358(5)
_cell_measurement_reflns_used    4309
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.9320
_cell_measurement_theta_min      4.7200
_cell_volume                     2449.56(11)
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.930
_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      2.00  69.00   1.00    0.10    --   48.20 -96.00  90.00   67
  2  \w   -159.00-108.00   1.00    0.10    --  -86.25 -63.00-173.00   51
  3  \w     40.00 100.00   1.00    0.10    --  107.75 -96.00  90.00   60
  4  \w     93.00 151.00   1.00    0.10    --  107.75  66.00 103.00   58
  5  \w   -120.00 -70.00   1.00    0.10    --  -48.20-125.00 120.00   50
  6  \w   -116.00 -82.00   1.00    0.10    --  -48.20-125.00   0.00   34
  7  \w     38.00  91.00   1.00    0.10    --  107.75 -99.00-180.00   53
  8  \w     35.00 120.00   1.00    0.10    --  107.75 -37.00-180.00   85
;
_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      -0.0172748000
_diffrn_orient_matrix_UB_12      0.1452613000
_diffrn_orient_matrix_UB_13      -0.0513585000
_diffrn_orient_matrix_UB_21      -0.0673783000
_diffrn_orient_matrix_UB_22      -0.1019472000
_diffrn_orient_matrix_UB_23      -0.0375510000
_diffrn_orient_matrix_UB_31      -0.0639595000
_diffrn_orient_matrix_UB_32      0.0682478000
_diffrn_orient_matrix_UB_33      0.0534227000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7563
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.032
_diffrn_reflns_theta_min         4.771
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.559
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50245
_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    1.265
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2405
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0715P)^2^+0.7367P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1294
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2106
_reflns_number_total             2405
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b03604_si_002.cif
_cod_data_source_block           6l
_cod_database_code               4517168
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         CNH
_diffrn_oxdiff_ac3_digest_frames
;
013585af86dd30025d5f763c8d5f5bc09c00458cf89
;
_diffrn_oxdiff_ac3_digest_hkl
;
01e11fff39b75cd06ac5553e1a599698c7e653
;
_reflns_odcompleteness_completeness 99.17
_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, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N14(H14), C15(H15), C9(H9), C6(H6), C18(H18), C8(H8), C7(H7), C16(H16),
 C17(H17)
;
_shelx_res_checksum              30170
_shelx_hkl_checksum              69357
_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 1.412
_oxdiff_exptl_absorpt_empirical_full_min 0.706