Retro-Diels-Alder decomposition of norbornadiene mediated by a cationic magnesium complex.
Thum, Katharina; Pahl, Jürgen; Eyselein, Jonathan; Elsen, Holger; Langer, Jens; Harder, Sjoerd; Chemical communications (Cambridge, England) 57 (2021) 5278–5281; doi:10.1039/d1cc01691a

data_7128234
_publ_section_title
;
 Retro-Diels-Alder decomposition of norbornadiene mediated by a cationic
 magnesium complex.
;
_journal_issue                   43
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              5278
_journal_page_last               5281
_journal_paper_doi               10.1039/d1cc01691a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety
'Al C16 F36 O4, C36 H49 Mg N2, C6 H5 Cl, 1[C6H5Cl]'
_chemical_formula_sum            'C64 H59 Al Cl2 F36 Mg N2 O4'
_chemical_formula_weight         1726.32
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-03-29 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.1584(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.66188(8)
_cell_length_b                   20.93276(9)
_cell_length_c                   19.46075(10)
_cell_measurement_reflns_used    32494
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      72.7480
_cell_measurement_theta_min      3.4440
_cell_volume                     7183.94(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (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(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2903
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_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   -116.00 -17.00   1.00    1.50    --  -41.48 -38.00-180.00   99
  2  \w    -87.00  -6.00   1.00    1.50    --  -41.48 125.00 -30.00   81
  3  \w    103.00 178.00   1.00    6.00    --  104.33  77.00 -60.00   75
  4  \w     31.00 130.00   1.00    6.00    --  104.33 -45.00-120.00   99
  5  \w    103.00 178.00   1.00    6.00    --  104.33  77.00-150.00   75
  6  \w     76.00 178.00   1.00    6.00    --  104.33  30.00 -90.00  102
  7  \w     32.00 133.00   1.00    6.00    --  104.33 -61.00-180.00  101
  8  \w     76.00 178.00   1.00    6.00    --  104.33  30.00  60.00  102
  9  \w   -114.00 -13.00   1.00    1.50    --  -41.48 -57.00  90.00  101
 10  \w     13.00 114.00   1.00    1.50    --   41.48  57.00   0.00  101
 11  \w     31.00 112.00   1.00    6.00    --  104.33-125.00  90.00   81
 12  \w     22.00 106.00   1.00    6.00    --  104.33 -94.00 150.00   84
 13  \w     52.00 178.00   1.00    6.00    --  104.33  15.00-180.00  126
;
_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      -0.0704153000
_diffrn_orient_matrix_UB_12      -0.0131716000
_diffrn_orient_matrix_UB_13      -0.0482113000
_diffrn_orient_matrix_UB_21      0.0350516000
_diffrn_orient_matrix_UB_22      -0.0637110000
_diffrn_orient_matrix_UB_23      -0.0218585000
_diffrn_orient_matrix_UB_31      -0.0379780000
_diffrn_orient_matrix_UB_32      -0.0343903000
_diffrn_orient_matrix_UB_33      0.0590517000
_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  0.0204
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            55377
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.702
_diffrn_reflns_theta_min         3.103
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.316
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.247
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_description       block
_exptl_crystal_F_000             3488
_exptl_crystal_size_max          0.539
_exptl_crystal_size_mid          0.308
_exptl_crystal_size_min          0.244
_refine_diff_density_max         0.698
_refine_diff_density_min         -0.743
_refine_diff_density_rms         0.059
_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     1325
_refine_ls_number_reflns         14090
_refine_ls_number_restraints     3968
_refine_ls_restrained_S_all      1.293
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0549
_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^)+(0.0737P)^2^+7.8606P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1489
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13070
_reflns_number_total             14090
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc01691a2.cif
_cod_data_source_block           hasj200427a
_cod_depositor_comments
'Adding full bibliography for 7128228--7128235.cif.'
_cod_database_code               7128234
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         AlC64Cl2F36H59MgN2O4
_reflns_odcompleteness_completeness 99.88
_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
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C51A-C49 \\sim C51-C49 \\sim C49-C50 \\sim C49-C50A \\sim C49-C52A \\sim
C49-C52
 with sigma of 0.02
 F28-F29 \\sim F29-F30 \\sim F28-F30 \\sim F35-F34 \\sim F34-F36 \\sim F35-F36
\\sim F31-F33 \\sim F33-F32
 \\sim F32-F31 \\sim F30A-F28A \\sim F28A-F29A \\sim F30A-F29A \\sim F35A-F34A
\\sim F34A-F36A \\sim F36A-
 F35A \\sim F33A-F31A \\sim F31A-F32A \\sim F32A-F33A
 with sigma of 0.02
 F32A-C51A \\sim F31A-C51A \\sim F33A-C51A \\sim F32-C51 \\sim F33-C51 \\sim
F31-C51 \\sim F34A-C52A ~
 F35A-C52A \\sim F36A-C52A \\sim F34-C52 \\sim F36-C52 \\sim F35-C52 \\sim
F30A-C50A \\sim F28A-C50A ~
 F29-C50 \\sim F29A-C50A \\sim F30-C50 \\sim F28-C50
 with sigma of 0.02
 C34A-C26A \\sim C34-C26
 with sigma of 0.02
 C32-C31 \\sim C32A-C31A \\sim C33-C31 \\sim C33A-C31A \\sim C34-C35 \\sim
C35-C34A \\sim C36-C34 ~
 C36A-C34A
 with sigma of 0.02
 C26A-C25 \\sim C26-C25 \\sim C30A-C25 \\sim C30-C25
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F28 \\sim F29 \\sim F30 \\sim F31 \\sim F32 \\sim F33 \\sim F34 \\sim F35 \\sim
F36 \\sim C50 \\sim C51 \\sim C52 \\sim F28A \\sim F29A \\sim F30A \\sim F31A
\\sim F32A \\sim F33A \\sim F34A \\sim F35A \\sim F36A \\sim C50A \\sim C51A
\\sim C52A: within 4A with sigma of 0.02 and sigma for terminal atoms of 0.04
within 4A
C25 \\sim C35 \\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim
C32 \\sim C33 \\sim C34 \\sim C36 \\sim C26A \\sim C27A \\sim C28A \\sim C29A
\\sim C30A \\sim C31A \\sim C32A \\sim C33A \\sim C34A \\sim C36A: within 4A
with sigma of 0.02 and sigma for terminal atoms of 0.04 within 4A
F20 \\sim F22 \\sim F25 \\sim C45 \\sim F19 \\sim F21 \\sim F23 \\sim F24 \\sim
F26 \\sim F27 \\sim C46 \\sim C47 \\sim C48 \\sim F19A \\sim F21A \\sim F23A
\\sim F24A \\sim F26A \\sim F27A \\sim C46A \\sim C47A \\sim C48A: within 4A
with sigma of 0.02 and sigma for terminal atoms of 0.04 within 4A
4. Rigid body (RIGU) restrains
 C49, F34A, F35A, F36A, C52A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C49, F28A, F29A, F30A, C50A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C49, F28, F29, F30, F31, F32, F33, F34, F35, F36, C50, C51, C52, F28A, F29A,
 F30A, F31A, F32A, F33A, F34A, F35A, F36A, C50A, C51A, C52A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Others
 Sof(Cl1)=Sof(C53)=Sof(C54)=Sof(H54)=Sof(C55)=Sof(H55)=Sof(C56)=Sof(H56)=
 Sof(C57)=Sof(H57)=Sof(C58)=Sof(H58)=1-FVAR(1)
 Sof(Cl1A)=Sof(C53A)=Sof(C58A)=Sof(H58A)=Sof(C57A)=Sof(H57A)=Sof(C56A)=
 Sof(H56A)=Sof(C55A)=Sof(H55A)=Sof(C54A)=Sof(H54A)=FVAR(1)
 Sof(F28A)=Sof(F29A)=Sof(F30A)=Sof(F31A)=Sof(F32A)=Sof(F33A)=Sof(F34A)=
 Sof(F35A)=Sof(F36A)=Sof(C50A)=Sof(C51A)=Sof(C52A)=1-FVAR(2)
 Sof(F28)=Sof(F29)=Sof(F30)=Sof(F31)=Sof(F32)=Sof(F33)=Sof(F34)=Sof(F35)=
 Sof(F36)=Sof(C50)=Sof(C51)=Sof(C52)=FVAR(2)
 Sof(H35D)=Sof(H35E)=Sof(H35F)=Sof(C26A)=Sof(C27A)=Sof(H27A)=Sof(C28A)=
 Sof(H28A)=Sof(C29A)=Sof(H29A)=Sof(C30A)=Sof(C31A)=Sof(H31A)=Sof(C32A)=
 Sof(H32D)=Sof(H32E)=Sof(H32F)=Sof(C33A)=Sof(H33D)=Sof(H33E)=Sof(H33F)=
 Sof(C34A)=Sof(H34A)=Sof(C36A)=Sof(H36D)=Sof(H36E)=Sof(H36F)=1-FVAR(3)
 Sof(H35A)=Sof(H35B)=Sof(H35C)=Sof(C26)=Sof(C27)=Sof(H27)=Sof(C28)=Sof(H28)=
 Sof(C29)=Sof(H29)=Sof(C30)=Sof(C31)=Sof(H31)=Sof(C32)=Sof(H32A)=Sof(H32B)=
 Sof(H32C)=Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(H33C)=Sof(C34)=Sof(H34)=Sof(C36)=
 Sof(H36A)=Sof(H36B)=Sof(H36C)=FVAR(3)
 Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=Sof(C24)=Sof(H24A)=
 Sof(H24B)=Sof(H24C)=1-FVAR(4)
 Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23D)=Sof(H23E)=Sof(H23F)=Sof(C24A)=
 Sof(H24D)=Sof(H24E)=Sof(H24F)=FVAR(4)
 Sof(H19A)=Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=Sof(C21A)=Sof(H21D)=
 Sof(H21E)=Sof(H21F)=1-FVAR(5)
 Sof(H19)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(C21)=Sof(H21A)=Sof(H21B)=
 Sof(H21C)=FVAR(5)
 Sof(F19A)=Sof(F21A)=Sof(F23A)=Sof(F24A)=Sof(F26A)=Sof(F27A)=Sof(C46A)=
 Sof(C47A)=Sof(C48A)=1-FVAR(6)
 Sof(F19)=Sof(F21)=Sof(F23)=Sof(F24)=Sof(F26)=Sof(F27)=Sof(C46)=Sof(C47)=
 Sof(C48)=FVAR(6)
 Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=1-FVAR(7)
 Sof(C12A)=Sof(H12D)=Sof(H12E)=Sof(H12F)=FVAR(7)
6.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6), C19(H19), C19(H19A), C22(H22), C31(H31), C34(H34), C22A(H22A),
  C31A(H31A), C34A(H34A)
6.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C10(H10), C15(H15), C16(H16), C17(H17),
 C27(H27), C28(H28), C29(H29), C27A(H27A), C28A(H28A), C29A(H29A), C58A(H58A),
 C57A(H57A), C56A(H56A), C55A(H55A), C54A(H54A), C54(H54), C55(H55), C56(H56),
 C57(H57), C58(H58)
6.d Fitted hexagon refined as free rotating group:
 C53A(C58A,C57A,C56A,C55A,C54A), C53(C54,C55,C56,C57,C58)
6.e Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C35(H35D,H35E,H35F), C35(H35A,H35B,H35C), C12(H12A,H12B,
 H12C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,
 H24B,H24C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C36(H36A,H36B,H36C),
 C12A(H12D,H12E,H12F), C20A(H20D,H20E,H20F), C21A(H21D,H21E,H21F), C23A(H23D,
 H23E,H23F), C24A(H24D,H24E,H24F), C32A(H32D,H32E,H32F), C33A(H33D,H33E,H33F),
 C36A(H36D,H36E,H36F)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_date_sample_data_collection 2020-04-27
_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 1.132
_oxdiff_exptl_absorpt_empirical_full_min 0.851