Magnesium-halobenzene bonding: mapping the halogen sigma-hole with a Lewis-acidic complex.
Friedrich, Alexander; Pahl, Jürgen; Eyselein, Jonathan; Langer, Jens; van Eikema Hommes, Nico; Görling, Andreas; Harder, Sjoerd; Chemical science 12 (2020) 2410–2418; doi:10.1039/d0sc06321e

data_1559820
_publ_section_title
;
 Magnesium-halobenzene bonding: mapping the halogen sigma-hole with a
 Lewis-acidic complex.
;
_journal_issue                   7
_journal_name_full               'Chemical science'
_journal_page_first              2410
_journal_page_last               2418
_journal_paper_doi               10.1039/d0sc06321e
_journal_volume                  12
_journal_year                    2020
_chemical_formula_moiety         '2(Al C12 F27.5 O3), C47 H63 F2 Mg N2'
_chemical_formula_sum            'C71 H63 Al2 F57 Mg N2 O6'
_chemical_formula_weight         2201.50
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-11-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2020-11-06 deposited with the CCDC.	2020-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                74.924(3)
_cell_angle_beta                 85.545(2)
_cell_angle_gamma                89.290(2)
_cell_formula_units_Z            2
_cell_length_a                   11.3521(3)
_cell_length_b                   15.9191(5)
_cell_length_c                   24.7380(7)
_cell_measurement_reflns_used    15127
_cell_measurement_temperature    100.0(6)
_cell_measurement_theta_max      72.6250
_cell_measurement_theta_min      3.7760
_cell_volume                     4303.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2903
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.967
_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   -109.00 -16.00   1.00    5.00    --  -41.44 -57.00  90.00   93
  2  \w    -86.00 -55.00   1.00    5.00    --  -41.44 125.00 -60.00   31
  3  \w    -66.00  32.00   1.00    5.00    --  -41.44  57.00-120.00   98
  4  \w    -65.00  32.00   1.00    5.00    --  -41.44  38.00  30.00   97
  5  \w     55.00  84.00   1.00   20.00    --  104.37-146.00  51.00   29
  6  \w     32.00 101.00   1.00   20.00    --  104.37 -61.00  60.00   69
  7  \w     29.00  56.00   1.00   20.00    --  104.37 -77.00-150.00   27
  8  \w     87.00 177.00   1.00   20.00    --  104.37  45.00-150.00   90
  9  \w     52.00 130.00   1.00   20.00    --  104.37 -45.00-180.00   78
 10  \w     72.00 137.00   1.00   20.00    --  104.37 -77.00-150.00   65
 11  \w     24.00 106.00   1.00   20.00    --  104.37 -94.00  60.00   82
 12  \w    103.00 128.00   1.00   20.00    --  104.37-146.00  51.00   25
 13  \w     31.00 111.00   1.00   20.00    --  104.37-125.00  60.00   80
 14  \w     23.00 106.00   1.00   20.00    --  104.37 -94.00-180.00   83
 15  \w     36.00 168.00   1.00   20.00    --  104.37   0.00-180.00  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0986869000
_diffrn_orient_matrix_UB_12      -0.0696010000
_diffrn_orient_matrix_UB_13      0.0141589000
_diffrn_orient_matrix_UB_21      0.0177855000
_diffrn_orient_matrix_UB_22      -0.0159869000
_diffrn_orient_matrix_UB_23      0.0629679000
_diffrn_orient_matrix_UB_31      -0.0920541000
_diffrn_orient_matrix_UB_32      0.0703251000
_diffrn_orient_matrix_UB_33      0.0043626000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            29394
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.755
_diffrn_reflns_theta_min         3.712
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.000
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.439
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_description       plate
_exptl_crystal_F_000             2204
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.249
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1633
_refine_ls_number_reflns         16538
_refine_ls_number_restraints     6852
_refine_ls_restrained_S_all      0.943
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0483P)^2^+2.5675P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1046
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14623
_reflns_number_total             16538
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc06321e2.cif
_cod_data_source_block           hasj200116a
_cod_depositor_comments
;Adding full bibliography for 1559817--1559822.cif.

 Adding full bibliography for 1559817--1559822.cif.
;
_cod_database_code               1559820
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C71 H63 Al2 F57 N2 Mg O6'
_shelx_estimated_absorpt_t_max   0.825
_shelx_estimated_absorpt_t_min   0.590
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Restrained distances
 Al2-O5 \\sim Al2-O5A \\sim Al2-O6A \\sim Al2-O6
 with sigma of 0.02
 O5-C64 \\sim O5A-C64A \\sim O6A-C68A \\sim O6-C68
 with sigma of 0.02
 F48A-C67A \\sim F48-C67 \\sim F47A-C67A \\sim F47-C67 \\sim F49-C67 \\sim
F49A-C67A \\sim F46-C66 ~
 F46A-C66A \\sim F44-C66 \\sim F44A-C66A \\sim F45-C66 \\sim F45A-C66A \\sim
F41-C65 \\sim F41A-C65A ~
 F42A-C65A \\sim F42-C65 \\sim F43-C65 \\sim F43A-C65A \\sim F54A-C70A \\sim
F54-C70 \\sim F55-C70 ~
 F55A-C70A \\sim F53A-C70A \\sim F53-C70 \\sim F56-C71 \\sim F56A-C71A \\sim
F57A-C71A \\sim F57-C71 ~
 F58-C71 \\sim F58A-C71A \\sim F50A-C69A \\sim F50-C69 \\sim F51A-C69A \\sim
F51-C69 \\sim F52A-C69A ~
 F52-C69 \\sim F26-C58 \\sim F26-C58A \\sim F25-C58 \\sim F25-C58A \\sim
F27A-C58A \\sim F27-C58 \\sim F30A-
 C59A \\sim F28-C59A \\sim F28-C59 \\sim F29-C59 \\sim F29-C59A \\sim F30-C59
\\sim F24A-C57A \\sim F23-
 C57A \\sim F23-C57 \\sim F24-C57 \\sim F22-C57 \\sim F22-C57A
 with sigma of 0.02
 C64A-C67A \\sim C67-C64 \\sim C66A-C64A \\sim C66-C64 \\sim C65-C64 \\sim
C64A-C65A \\sim C69-C68 ~
 C69A-C68A \\sim C71-C68 \\sim C68A-C71A \\sim C68A-C70A \\sim C70-C68 \\sim
C58A-C56 \\sim C58-C56 ~
 C59A-C56 \\sim C59-C56 \\sim C57A-C56 \\sim C57-C56
 with sigma of 0.02
 F52-F51 \\sim F51-F50 \\sim F52-F50 \\sim F50A-F52A \\sim F52A-F51A \\sim
F50A-F51A
 with sigma of 0.02
 C43-C47 \\sim C43A-C47A \\sim C37-C41
 with sigma of 0.02
 F2-C42A \\sim F2-C42 \\sim F1-C36
 with sigma of 0.02
 C43-C42 \\sim C43A-C42A \\sim C42-C47 \\sim C42A-C47A \\sim C37-C36 \\sim
C41-C36
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F41 \\sim F42 \\sim F43 \\sim F44 \\sim F45 \\sim F46 \\sim F47 \\sim F48 \\sim
F49 \\sim O5 \\sim C64 \\sim C65 \\sim C66 \\sim C67 \\sim F41A \\sim F42A
\\sim F43A \\sim F44A \\sim F45A \\sim F46A \\sim F47A \\sim F48A \\sim F49A
\\sim O5A \\sim C64A \\sim C65A \\sim C66A \\sim C67A: within 4A with sigma of
0.02 and sigma for terminal atoms of 0.04 within 4A
F50 \\sim F51 \\sim F52 \\sim F53 \\sim F54 \\sim F55 \\sim F56 \\sim F57 \\sim
F58 \\sim O6 \\sim C68 \\sim C69 \\sim C70 \\sim C71 \\sim F50A \\sim F51A
\\sim F52A \\sim F53A \\sim F54A \\sim F55A \\sim F56A \\sim F57A \\sim F58A
\\sim O6A \\sim C68A \\sim C69A \\sim C70A \\sim C71A: within 4A with sigma of
0.02 and sigma for terminal atoms of 0.04 within 4A
F50 \\sim F50A: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
F22 \\sim F23 \\sim F25 \\sim F26 \\sim F28 \\sim F29 \\sim C56 \\sim F24 \\sim
F27 \\sim F30 \\sim C57 \\sim C58 \\sim C59 \\sim F24A \\sim F27A \\sim F30A
\\sim C57A \\sim C58A \\sim C59A: within 4A with sigma of 0.02 and sigma for
terminal atoms of 0.04 within 4A
H21 \\sim C42 \\sim C43 \\sim C44 \\sim C45 \\sim C46 \\sim C47 \\sim C42A
\\sim C43A \\sim C44A \\sim C45A \\sim C46A \\sim C47A: within 4A with sigma of
0.02 and sigma for terminal atoms of 0.04 within 4A
4. Others
 Sof(F41A)=Sof(F42A)=Sof(F43A)=Sof(F44A)=Sof(F45A)=Sof(F46A)=Sof(F47A)=
 Sof(F48A)=Sof(F49A)=Sof(O5A)=Sof(C64A)=Sof(C65A)=Sof(C66A)=Sof(C67A)=1-FVAR(1)
 Sof(F41)=Sof(F42)=Sof(F43)=Sof(F44)=Sof(F45)=Sof(F46)=Sof(F47)=Sof(F48)=
 Sof(F49)=Sof(O5)=Sof(C64)=Sof(C65)=Sof(C66)=Sof(C67)=FVAR(1)
 Sof(F50A)=Sof(F51A)=Sof(F52A)=Sof(F53A)=Sof(F54A)=Sof(F55A)=Sof(F56A)=
 Sof(F57A)=Sof(F58A)=Sof(O6A)=Sof(C68A)=Sof(C69A)=Sof(C70A)=Sof(C71A)=1-FVAR(2)
 Sof(F50)=Sof(F51)=Sof(F52)=Sof(F53)=Sof(F54)=Sof(F55)=Sof(F56)=Sof(F57)=
 Sof(F58)=Sof(O6)=Sof(C68)=Sof(C69)=Sof(C70)=Sof(C71)=FVAR(2)
 Sof(F24A)=Sof(F27A)=Sof(F30A)=Sof(C57A)=Sof(C58A)=Sof(C59A)=1-FVAR(3)
 Sof(F24)=Sof(F27)=Sof(F30)=Sof(C57)=Sof(C58)=Sof(C59)=FVAR(3)
 Sof(C42A)=Sof(C43A)=Sof(H43A)=Sof(C44A)=Sof(H44A)=Sof(C45A)=Sof(H45A)=
 Sof(C46A)=Sof(H46A)=Sof(C47A)=Sof(H47A)=1-FVAR(4)
 Sof(C42)=Sof(C43)=Sof(H43)=Sof(C44)=Sof(H44)=Sof(C45)=Sof(H45)=Sof(C46)=
 Sof(H46)=Sof(C47)=Sof(H47)=FVAR(4)
5.a Ternary CH refined with riding coordinates:
 C18(H18), C21(H21), C30(H30), C33(H33)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C14(H14), C15(H15), C16(H16), C26(H26), C27(H27), C28(H28), C37(H37),
 C38(H38), C39(H39), C40(H40), C41(H41), C43(H43), C44(H44), C45(H45), C46(H46),
  C47(H47), C43A(H43A), C44A(H44A), C45A(H45A), C46A(H46A), C47A(H47A)
5.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C10(H10A,
 H10B,H10C), C11(H11A,H11B,H11C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C),
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C31(H31A,H31B,H31C), C32(H32A,H32B,
 H32C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C)
;
_shelx_res_checksum              71238
_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 1.222
_oxdiff_exptl_absorpt_empirical_full_min 0.700