Regioselective magnesiation of N-heterocyclic molecules: securing insecure cyclic anions by a β-diketiminate-magnesium clamp.
Davin, Laia; McLellan, Ross; Hernán-Gómez, Alberto; Clegg, William; Kennedy, Alan R.; Mertens, Maria; Stepek, Iain A.; Hevia, Eva; Chemical communications (Cambridge, England) 53 (2017) 3653–3656; doi:10.1039/c6cc09675a

data_7119393
_publ_section_title
;
 Regioselective magnesiation of N-heterocyclic molecules: securing
 insecure cyclic anions by a \b-diketiminate-magnesium clamp.
;
_journal_issue                   26
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3653
_journal_page_last               3656
_journal_paper_doi               10.1039/c6cc09675a
_journal_volume                  53
_journal_year                    2017
_chemical_formula_moiety         'C86 H102 Mg2 N10, C7 H8'
_chemical_formula_sum            'C93 H110 Mg2 N10'
_chemical_formula_weight         1416.52
_chemical_properties_physical
', Air-sensitive,Moisture-sensitive,Oxygen-sensitive'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-05-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-11-28 deposited with the CCDC.
2017-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.615(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.3537(5)
_cell_length_b                   14.2772(5)
_cell_length_c                   19.1707(8)
_cell_measurement_reflns_used    10900
_cell_measurement_temperature    123.1
_cell_measurement_theta_max      29.2899
_cell_measurement_theta_min      3.1966
_cell_volume                     4066.4(3)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      123.1
_diffrn_detector_area_resol_mean 16.0727
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_details
;
  1 omega  -13.00   24.00   1.0000   13.7900
omega____ theta____ kappa____ phi______ frames
    -       30.1499   77.0000   60.0000 37

  2 omega   64.00  101.00   1.0000   13.7900
omega____ theta____ kappa____ phi______ frames
    -       30.1499   77.0000   60.0000 37

  3 omega -123.00  -47.00   1.0000   13.7900
omega____ theta____ kappa____ phi______ frames
    -      -30.9312  179.0000   60.0000 76

  4 omega  -66.00   52.00   1.0000   13.7900
omega____ theta____ kappa____ phi______ frames
    -      -30.9312   77.0000   90.0000 118

  5 omega  -43.00   13.00   1.0000   13.7900
omega____ theta____ kappa____ phi______ frames
    -      -30.9312  -81.0000  -93.0000 56

  6 omega  -13.00   55.00   1.0000   13.7900
omega____ theta____ kappa____ phi______ frames
    -       30.1499   77.0000  150.0000 68
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0313915000
_diffrn_orient_matrix_UB_12      0.0362979000
_diffrn_orient_matrix_UB_13      0.0003765000
_diffrn_orient_matrix_UB_21      0.0321802000
_diffrn_orient_matrix_UB_22      0.0232014000
_diffrn_orient_matrix_UB_23      0.0276595000
_diffrn_orient_matrix_UB_31      0.0159191000
_diffrn_orient_matrix_UB_32      0.0247985000
_diffrn_orient_matrix_UB_33      -0.0264084000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            25760
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.355
_diffrn_reflns_theta_min         3.203
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_description       prism
_exptl_crystal_F_000             1524
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         10388
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0449P)^2^+1.5275P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1183
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7675
_reflns_number_total             10388
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc09675a2.cif
_cod_data_source_block           ld361c
_cod_depositor_comments
'Adding full bibliography for 7119393--7119397.cif.'
_cod_database_code               7119393
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: C44(0.5) C45(0.5) H1S(0.5) C46(0.5) H6S(0.5) C47(0.5) H5S(0.5)
 C48(0.5) H4S(0.5) C49(0.5) H3S(0.5) C50(0.5) H7S1(0.5) H7S2(0.5) H7S3(0.5)
3.a Ternary CH refined with riding coordinates:
 C7(H30), C10(H27), C24(H42), C27(H39)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H22), C4(H23), C5(H24), C15(H16), C20(H35), C21(H36), C22(H37), C33(H8),
 C34(H7), C35(H6), C36(H5), C37(H4), C39(H14), C40(H13), C41(H12), C42(H11),
 C43(H10), C45(H1S), C46(H6S), C47(H5S), C48(H4S), C49(H3S)
3.c Idealised Me refined as rotating group:
 C8(H32A,H32B,H32C), C9(H31A,H31B,H31C), C11(H28A,H28B,H28C), C12(H29A,H29B,
 H29C), C13(H19A,H19B,H19C), C17(H18A,H18B,H18C), C25(H43A,H43B,H43C), C26(H44A,
 H44B,H44C), C28(H41A,H41B,H41C), C29(H40A,H40B,H40C), C50(H7S1,H7S2,H7S3)
;
_olex2_submission_original_sample_id LD361
_olex2_submission_special_instructions 'No special instructions were received'