Calcium catalyzed enantioselective intramolecular alkene hydroamination with chiral <i>C</i><sub>2</sub>-symmetric bis-amide ligands.
Stegner, Philipp C.; Eyselein, Jonathan; Ballmann, Gerd M.; Langer, Jens; Schmidt, Jochen; Harder, Sjoerd; Dalton transactions (Cambridge, England : 2003) 50 (2021) 3178–3185; doi:10.1039/d1dt00173f

data_7706544
_publ_section_title
;
 Calcium catalyzed enantioselective intramolecular alkene hydroamination
 with chiral <i>C</i><sub>2</sub>-symmetric bis-amide ligands.
;
_journal_issue                   9
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3178
_journal_page_last               3185
_journal_paper_doi               10.1039/d1dt00173f
_journal_volume                  50
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C38 H50 Mg N2 O2'
_chemical_formula_sum            'C38 H50 Mg N2 O2'
_chemical_formula_weight         591.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-01-15 deposited with the CCDC.	2021-02-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.7365(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.05338(11)
_cell_length_b                   18.29549(18)
_cell_length_c                   19.0563(2)
_cell_measurement_reflns_used    24370
_cell_measurement_temperature    100.0(6)
_cell_measurement_theta_max      73.7050
_cell_measurement_theta_min      3.3490
_cell_volume                     3443.70(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(6)
_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 0.983
_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   -116.00 -10.00   1.00    4.00    --  -41.69 -77.00 -30.00  106
  2  \w    -73.00  32.00   1.00    4.00    --  -41.69  77.00-120.00  105
  3  \w   -114.00 -19.00   1.00    4.00    --  -41.69 -38.00 -30.00   95
  4  \w    -68.00  28.00   1.00    4.00    --  -41.69  57.00  90.00   96
  5  \w     67.00 118.00   1.00    4.00    --   41.69 166.00-102.00   51
  6  \w     66.00 160.00   1.00   16.00    --  106.00 166.00-102.00   94
  7  \w     31.00 130.00   1.00   16.00    --  106.00 -30.00-120.00   99
  8  \w     31.00 130.00   1.00   16.00    --  106.00 -30.00 -30.00   99
  9  \w     82.00 178.00   1.00   16.00    --  106.00  30.00  90.00   96
 10  \w     82.00 177.00   1.00   16.00    --  106.00  45.00-150.00   95
 11  \w     25.00 109.00   1.00   16.00    --  106.00 -94.00 -60.00   84
 12  \w     25.00 109.00   1.00   16.00    --  106.00 -94.00   0.00   84
 13  \w     94.00 178.00   1.00   16.00    --  106.00 125.00  30.00   84
 14  \w     25.00 109.00   1.00   16.00    --  106.00 -94.00-150.00   84
 15  \w     36.00 134.00   1.00   16.00    --  106.00 -61.00   0.00   98
 16  \w   -112.00 -15.00   1.00    4.00    --  -41.69 -57.00 120.00   97
 17  \w   -116.00 -10.00   1.00    4.00    --  -41.69 -77.00  60.00  106
 18  \w   -119.00 -44.00   1.00    4.00    --  -41.69-166.00-124.00   75
 19  \w   -112.00 -15.00   1.00    4.00    --  -41.69 -57.00-150.00   97
 20  \w     82.00 177.00   1.00   16.00    --  106.00  45.00   0.00   95
;
_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      -0.0326866000
_diffrn_orient_matrix_UB_12      -0.0334994000
_diffrn_orient_matrix_UB_13      -0.0754139000
_diffrn_orient_matrix_UB_21      -0.0120634000
_diffrn_orient_matrix_UB_22      -0.0761004000
_diffrn_orient_matrix_UB_23      0.0328295000
_diffrn_orient_matrix_UB_31      -0.1520548000
_diffrn_orient_matrix_UB_32      0.0132558000
_diffrn_orient_matrix_UB_33      -0.0021254000
_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  0.0331
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            38522
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.675
_diffrn_reflns_theta_min         3.378
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.787
_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    1.140
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 5897 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1038
_refine_ls_number_reflns         13501
_refine_ls_number_restraints     1712
_refine_ls_restrained_S_all      0.937
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0312
_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^)+(0.0457P)^2^+0.4429P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0816
_reflns_Friedel_coverage         0.910
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                12960
_reflns_number_total             13501
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt00173f2.cif
_cod_data_source_block           hasj160602a
_cod_depositor_comments
'Adding full bibliography for 7706544--7706549.cif.'
_cod_original_cell_volume        3443.69(6)
_cod_database_code               7706544
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C38H50MgN2O2
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.96
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C33-C32 \\sim C33A-C32A
 with sigma of 0.02
 O1-C34A \\sim O1-C34 \\sim O1-C31
 with sigma of 0.02
 C34-C33A \\sim C34A-C33 \\sim C32-C31 \\sim C32A-C31
 with sigma of 0.02
 C71-C70 \\sim C71A-C70A
 with sigma of 0.02
 C71A-C72A \\sim C72-C71 \\sim C70-C69 \\sim C70A-C69A
 with sigma of 0.02
 O3-C72 \\sim O3-C72A \\sim O3-C69 \\sim O3-C69A
 with sigma of 0.02
 C27A-C26 \\sim C27-C26
 with sigma of 0.02
 Mg2-O4A \\sim Mg2-O4
 with sigma of 0.02
 O4-C76A \\sim O4A-C76 \\sim O4A-C73A \\sim O4-C73
 with sigma of 0.02
 N4-C58 \\sim N4A-C58A
 with sigma of 0.02
 N4A-C64 \\sim N4-C64
 with sigma of 0.02
 Mg2-N4A \\sim Mg2-N4
 with sigma of 0.02
 C49A-C48 \\sim C49-C48
 with sigma of 0.02
 C54-C53 \\sim C54A-C53A
 with sigma of 0.02
 C50A-C49A \\sim C50-C49
 with sigma of 0.02
 C58-C49 \\sim C58A-C49A
 with sigma of 0.02
 C56-C55 \\sim C56A-C55A
 with sigma of 0.02
 C57-C56 \\sim C57A-C56A
 with sigma of 0.02
 C55A-C50A \\sim C55-C50
 with sigma of 0.02
 C52A-C51A \\sim C52-C51
 with sigma of 0.02
 C53A-C52A \\sim C53-C52
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O1 \\sim C31 \\sim C32A \\sim C33A \\sim C34 \\sim C32 \\sim C33 \\sim C34A:
within 2A with sigma of 0.03 and sigma for terminal atoms of 0.06 within 2A
O3 \\sim C69 \\sim C70 \\sim C71 \\sim C72 \\sim C69A \\sim C70A \\sim C71A
\\sim C72A: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
within 2A
C26 \\sim C27 \\sim C28 \\sim C30 \\sim C27A \\sim C28A \\sim C29A \\sim C30A:
within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
O4 \\sim C73 \\sim C74 \\sim C75 \\sim C76A \\sim O4A \\sim C73A \\sim C74A
\\sim C75A \\sim C76: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08 within 2A
C64 \\sim N4A \\sim N4 \\sim C58A \\sim C58 \\sim C57A \\sim C57 \\sim C56A
\\sim C56 \\sim C55A \\sim C55 \\sim C54A \\sim C54 \\sim C53A \\sim C53 \\sim
C52A \\sim C52 \\sim C51A \\sim C51 \\sim C50A \\sim C50 \\sim C49A \\sim C49:
within 4A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 4A
4. Rigid body (RIGU) restrains
 C49, C50, C51, C52, C53, C54, C55, C56, C57, C58
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C38, C37, C36
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H31c)=Sof(H31d)=Sof(C32)=Sof(H32c)=Sof(H32d)=Sof(C33)=Sof(H33c)=Sof(H33d)=
 Sof(C34A)=Sof(H34c)=Sof(H34d)=1-FVAR(1)
 Sof(H31a)=Sof(H31b)=Sof(C32A)=Sof(H32a)=Sof(H32b)=Sof(C33A)=Sof(H33a)=
 Sof(H33b)=Sof(C34)=Sof(H34a)=Sof(H34b)=FVAR(1)
 Sof(C69A)=Sof(H69c)=Sof(H69d)=Sof(C70A)=Sof(H70c)=Sof(H70d)=Sof(C71A)=
 Sof(H71c)=Sof(H71d)=Sof(C72A)=Sof(H72c)=Sof(H72d)=1-FVAR(2)
 Sof(C69)=Sof(H69a)=Sof(H69b)=Sof(C70)=Sof(H70a)=Sof(H70b)=Sof(C71)=Sof(H71a)=
 Sof(H71b)=Sof(C72)=Sof(H72a)=Sof(H72b)=FVAR(2)
 Sof(H26c)=Sof(H26d)=Sof(C27A)=Sof(C28A)=Sof(H28d)=Sof(H28e)=Sof(H28f)=
 Sof(C29A)=Sof(H29d)=Sof(H29e)=Sof(H29f)=Sof(C30A)=Sof(H30d)=Sof(H30e)=
 Sof(H30f)=1-FVAR(3)
 Sof(H26a)=Sof(H26b)=Sof(C27)=Sof(C28)=Sof(H28a)=Sof(H28b)=Sof(H28c)=Sof(C29)=
 Sof(H29a)=Sof(H29b)=Sof(H29c)=Sof(C30)=Sof(H30a)=Sof(H30b)=Sof(H30c)=FVAR(3)
 Sof(O4A)=Sof(C73A)=Sof(H73c)=Sof(H73d)=Sof(C74A)=Sof(H74c)=Sof(H74d)=
 Sof(C75A)=Sof(H75c)=Sof(H75d)=Sof(C76)=Sof(H76c)=Sof(H76d)=1-FVAR(4)
 Sof(O4)=Sof(C73)=Sof(H73a)=Sof(H73b)=Sof(C74)=Sof(H74a)=Sof(H74b)=Sof(C75)=
 Sof(H75a)=Sof(H75b)=Sof(C76A)=Sof(H76a)=Sof(H76b)=FVAR(4)
 Sof(H64c)=Sof(H64d)=Sof(C58A)=Sof(C57A)=Sof(H57A)=Sof(C56A)=Sof(H56A)=
 Sof(C55A)=Sof(C54A)=Sof(H54A)=Sof(C53A)=Sof(H53A)=Sof(C52A)=Sof(H52A)=
 Sof(C51A)=Sof(H51A)=Sof(C50A)=Sof(C49A)=Sof(N4A)=1-FVAR(5)
 Sof(N4)=Sof(C49)=Sof(C50)=Sof(C51)=Sof(H51)=Sof(C52)=Sof(H52)=Sof(C53)=
 Sof(H53)=Sof(C54)=Sof(H54)=Sof(C55)=Sof(C56)=Sof(H56)=Sof(C57)=Sof(H57)=
 Sof(C58)=Sof(H64a)=Sof(H64b)=FVAR(5)
6.a Secondary CH2 refined with riding coordinates:
 C21(H21a,H21b), C26(H26a,H26b), C26(H26c,H26d), C31(H31a,H31b), C31(H31c,
 H31d), C35(H35a,H35b), C36(H36a,H36b), C37(H37a,H37b), C38(H38a,H38b),
 C32A(H32a,H32b), C33A(H33a,H33b), C34(H34a,H34b), C32(H32c,H32d), C33(H33c,
 H33d), C34A(H34c,H34d), C59(H59a,H59b), C64(H64c,H64d), C64(H64a,H64b),
 C69(H69a,H69b), C70(H70a,H70b), C71(H71a,H71b), C72(H72a,H72b), C73(H73a,H73b),
  C74(H74a,H74b), C75(H75a,H75b), C76A(H76a,H76b), C69A(H69c,H69d), C70A(H70c,
 H70d), C71A(H71c,H71d), C72A(H72c,H72d), C73A(H73c,H73d), C74A(H74c,H74d),
 C75A(H75c,H75d), C76(H76c,H76d)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C16(H16),
 C17(H17), C18(H18), C19(H19), C40(H40), C41(H41), C43(H43), C44(H44), C45(H45),
  C46(H46), C51(H51), C52(H52), C53(H53), C54(H54), C56(H56), C57(H57),
 C57A(H57A), C56A(H56A), C54A(H54A), C53A(H53A), C52A(H52A), C51A(H51A)
6.c Idealised Me refined as rotating group:
 C23(H23a,H23b,H23c), C24(H24a,H24b,H24c), C25(H25a,H25b,H25c), C28(H28a,H28b,
 H28c), C29(H29a,H29b,H29c), C30(H30a,H30b,H30c), C28A(H28d,H28e,H28f),
 C29A(H29d,H29e,H29f), C30A(H30d,H30e,H30f), C61(H61a,H61b,H61c), C62(H62a,H62b,
 H62c), C63(H63a,H63b,H63c), C66(H66a,H66b,H66c), C67(H67a,H67b,H67c), C68(H68a,
 H68b,H68c)
;
_shelx_res_checksum              52615
_shelx_hkl_checksum              10268
_olex2_date_sample_data_collection 2016-06-02
_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 1.524
_oxdiff_exptl_absorpt_empirical_full_min 0.753