Aluminium-mediated carbon-carbon coupling of an isonitrile.
Urwin, Stephanie J.; Nichol, Gary S.; Cowley, Michael J.; Chemical communications (Cambridge, England) 54 (2018) 378–380; doi:10.1039/c7cc08415c

data_7120958
_publ_section_title
;
 Aluminium-mediated carbon-carbon coupling of an isonitrile.
;
_journal_issue                   4
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              378
_journal_page_last               380
_journal_paper_doi               10.1039/c7cc08415c
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C84 H86 Al2 N4, C6 D6'
_chemical_formula_sum            'C90 H86 Al2 D6 N4'
_chemical_formula_weight         1289.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 1'
_symmetry_space_group_name_Hall  'I -2ya'
_symmetry_space_group_name_H-M   'I 1 a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-08-26
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_audit_update_record
;
2017-11-01 deposited with the CCDC.
2017-12-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.336(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4666(6)
_cell_length_b                   15.1699(5)
_cell_length_c                   30.7695(10)
_cell_measurement_reflns_used    7490
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      75.8930
_cell_measurement_theta_min      4.0980
_cell_volume                     7078.5(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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      120.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_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    -70.00  27.00   1.00    5.00    --  -43.17  57.00 120.00   97
  2  \w    -66.00  29.00   1.00    5.00    --  -43.17  38.00  30.00   95
  3  \w    -96.00  -2.00   1.00    5.00    --  -43.17 125.00-180.00   94
  4  \w     82.00 178.00   1.00   17.00    --  111.00  66.00  93.13   96
  5  \w     40.00 135.00   1.00   17.00    --  111.00 -45.00 -60.00   95
  6  \w     39.00 121.00   1.00   17.00    --  111.00-125.00-150.00   82
  7  \w     40.00 135.00   1.00   17.00    --  111.00 -45.00 150.00   95
  8  \w     94.00 178.00   1.00   17.00    --  111.00 125.00-150.00   84
  9  \w     80.00 178.00   1.00   17.00    --  111.00  77.00 -60.00   98
 10  \w     87.00 178.00   1.00   17.00    --  111.00  30.00  30.00   91
 11  \w   -113.00 -17.00   1.00    5.00    --  -43.17 -57.00  90.00   96
 12  \w   -117.00 -12.00   1.00    5.00    --  -43.17 -77.00   0.00  105
 13  \w   -113.00 -17.00   1.00    5.00    --  -43.17 -57.00-150.00   96
 14  \w     30.00 109.00   1.00   17.00    --  111.00 -94.00 -60.00   79
 15  \w     83.00 178.00   1.00   17.00    --  111.00  61.00 -90.00   95
 16  \w     83.00 163.00   1.00   17.00    --  111.00  61.00  60.00   80
 17  \w     66.00 178.00   1.00   17.00    --  111.00  15.00-150.00  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0731029000
_diffrn_orient_matrix_UB_12      0.0678694000
_diffrn_orient_matrix_UB_13      0.0166876000
_diffrn_orient_matrix_UB_21      -0.0241907000
_diffrn_orient_matrix_UB_22      -0.0019216000
_diffrn_orient_matrix_UB_23      0.0462254000
_diffrn_orient_matrix_UB_31      0.0662379000
_diffrn_orient_matrix_UB_32      -0.0755688000
_diffrn_orient_matrix_UB_33      0.0138315000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1336
_diffrn_reflns_av_unetI/netI     0.1270
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            34446
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.497
_diffrn_reflns_theta_min         4.122
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.751
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       prism
_exptl_crystal_F_000             2744
_exptl_crystal_recrystallization_method
'The material was recrystallised from d6-benzene by slow evaporation'
_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.28(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.916
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     884
_refine_ls_number_reflns         13900
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.916
_refine_ls_R_factor_all          0.1037
_refine_ls_R_factor_gt           0.0728
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0947P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1719
_refine_ls_wR_factor_ref         0.1875
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                8661
_reflns_number_total             13900
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc08415c2.cif
_cod_data_source_block           mc16071
_cod_depositor_comments
'Adding full bibliography for 7120958--7120959.cif.'
_cod_database_code               7120958
_chemical_oxdiff_formula         'C90 H92 Al2 N4'
_chemical_oxdiff_usercomment     '@ 120 K SU403'
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.72(8) 0.28(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C19(H19), C20(H20), C21(H21), C27(H27), C28(H28), C29(H29),
  C46(H46), C47(H47), C48(H48), C49(H49), C50(H50), C52(H52), C53(H53),
 C54(H54), C55(H55), C56(H56), C59(H59), C60(H60), C61(H61), C67(H67), C68(H68),
  C69(H69), C91(D91), C92(D92), C93(D93), C94(D94), C95(D95), C96(D96)
3.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C31(H31A,H31B,H31C), C32(H32A,H32B,
 H32C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C41(H41A,
 H41B,H41C), C42(H42A,H42B,H42C), C63(H63A,H63B,H63C), C64(H64A,H64B,H64C),
 C71(H71A,H71B,H71C), C72(H72A,H72B,H72C), C80(H80A,H80B,H80C), C81(H81A,H81B,
 H81C), C82(H82A,H82B,H82C), C83(H83A,H83B,H83C), C84(H84A,H84B,H84C)
;
_shelx_res_checksum              90386
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-08-25
_olex2_date_sample_submission    2016-08-16
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700+'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id SU403
_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 2.147
_oxdiff_exptl_absorpt_empirical_full_min 0.522
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
_twin_special_details
;
Component 2 rotated by -177.1328\% 
 around [-0.02 1.00 0.00] (reciprocal) or [-0.02 1.00 -0.00] (direct)
;