Use of (Cyclopentadienone)iron Tricarbonyl Complexes for C-N Bond Formation Reactions between Amines and Alcohols.
Brown, Thomas J.; Cumbes, Madeleine; Diorazio, Louis J.; Clarkson, Guy J.; Wills, Martin; The Journal of organic chemistry 82 (2017) 10489–10503; doi:10.1021/acs.joc.7b01990

data_4032911
_publ_section_title
;
 Use of (Cyclopentadienone)iron Tricarbonyl Complexes for C-N Bond
 Formation Reactions between Amines and Alcohols.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10489
_journal_page_last               10503
_journal_paper_doi               10.1021/acs.joc.7b01990
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C26 H22 Fe O6'
_chemical_formula_sum            'C26 H22 Fe O6'
_chemical_formula_weight         486.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-10-23
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                105.526(2)
_cell_angle_beta                 92.8266(19)
_cell_angle_gamma                109.973(2)
_cell_formula_units_Z            4
_cell_length_a                   11.3053(2)
_cell_length_b                   13.6069(3)
_cell_length_c                   16.3832(4)
_cell_measurement_reflns_used    13061
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.7120
_cell_measurement_theta_min      4.1990
_cell_volume                     2254.48(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_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   -114.00 -13.00   1.00    7.00    --  -41.46 -57.00 150.00  101
  2  \w    -66.00  33.00   1.00    7.00    --  -41.46  38.00  60.00   99
  3  \w   -116.00 -17.00   1.00    7.00    --  -41.46 -38.00-120.00   99
  4  \w     18.00  97.00   1.00    7.00    --   41.46-125.00 -60.00   79
  5  \w     18.00  97.00   1.00    7.00    --   41.46-125.00 120.00   79
  6  \w     -4.00  82.00   1.00    7.00    --   41.46 -99.00 120.00   86
  7  \w     88.00 178.00   1.00   28.00    --  114.00  45.00   0.00   90
  8  \w    100.00 178.00   1.00   28.00    --  114.00 111.00  60.00   78
  9  \w     86.00 178.00   1.00   28.00    --  114.00  30.00 -30.00   92
 10  \w     38.00 142.00   1.00   28.00    --  114.00 -30.00  60.00  104
 11  \w     38.00 116.00   1.00   28.00    --  114.00-111.00 -60.00   78
 12  \w     46.00 116.00   1.00   28.00    --  114.00-111.00-150.00   70
 13  \w     63.00 103.00   1.00   28.00    --  114.00 -95.00  30.00   40
 14  \w     90.00 116.00   1.00   28.00    --  114.00-111.00  60.00   26
 15  \w    114.00 166.00   1.00   28.00    --  114.00  45.00  60.00   52
 16  \w     38.00  65.00   1.00   28.00    --  114.00-111.00  60.00   27
 17  \w     65.00 119.00   1.00   28.00    --  114.00 -77.00  60.00   54
 18  \w    113.00 165.00   1.00   28.00    --  114.00 111.00 120.00   52
 19  \w     50.00 139.00   1.00   28.00    --  114.00 -61.00  90.00   89
 20  \w     63.00  89.00   1.00   28.00    --  114.00  15.00-150.00   26
 21  \w    152.00 178.00   1.00   28.00    --  114.00  15.00-150.00   26
 22  \w     36.00 104.00   1.00   28.00    --  114.00 -95.00 -30.00   68
 23  \w     78.00 145.00   1.00   28.00    --  114.00 178.00 -30.00   67
 24  \w     41.00 140.00   1.00   28.00    --  114.00 -45.00 -30.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1445506000
_diffrn_orient_matrix_UB_12      -0.0330461000
_diffrn_orient_matrix_UB_13      0.0003826000
_diffrn_orient_matrix_UB_21      -0.0075119000
_diffrn_orient_matrix_UB_22      0.0631700000
_diffrn_orient_matrix_UB_23      -0.0641033000
_diffrn_orient_matrix_UB_31      -0.0243105000
_diffrn_orient_matrix_UB_32      -0.1043906000
_diffrn_orient_matrix_UB_33      -0.0751736000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23003
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.129
_diffrn_reflns_theta_min         3.627
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.709
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     599
_refine_ls_number_reflns         9502
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0359
_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^)+(0.0649P)^2^+0.2883P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8935
_reflns_number_total             9502
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01990_si_002.cif
_cod_data_source_block           mc1
_cod_depositor_comments          'Adding full bibliography for 4032911.cif.'
_cod_original_cell_volume        2254.47(10)
_cod_database_code               4032911
_chemical_oxdiff_formula         'C20 H20 Fe1 O5'
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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:
 C105(H10A,H10B), C106(H10C,H10D), C107(H10E,H10F), C108(H10G,H10H), C205(H20A,
 H20B), C206(H20C,H20D), C207(H20E,H20F), C208(H20G,H20H)
2.b Aromatic/amide H refined with riding coordinates:
 C112(H112), C113(H113), C115(H115), C116(H116), C118(H118), C119(H119),
 C121(H121), C122(H122), C212(H212), C213(H213), C215(H215), C216(H216),
 C218(H218), C219(H219), C221(H221), C222(H222)
2.c Idealised Me refined as rotating group:
 C123(H12A,H12B,H12C), C124(H12D,H12E,H12F), C223(H22A,H22B,H22C), C224(H22D,
 H22E,H22F)
;
_shelx_shelxl_version_number     2014/7
_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 2.192
_oxdiff_exptl_absorpt_empirical_full_min 0.642