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_7706549
_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         'C52 H48 Ca N2 O2 P2, C6 H6'
_chemical_formula_sum            'C58 H54 Ca N2 O2 P2'
_chemical_formula_weight         913.05
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.5914(3)
_cell_length_b                   20.9696(3)
_cell_length_c                   22.3214(3)
_cell_measurement_reflns_used    33350
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      73.4820
_cell_measurement_theta_min      3.5560
_cell_volume                     9638.2(2)
_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 1.000
_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   -114.00 -13.00   1.00   15.00    --  -41.15 -57.00-120.00  101
  2  \w    -54.00  33.00   1.00   15.00    --  -41.15  38.00  30.00   87
  3  \w    -79.00  -2.00   1.00   15.00    --  -41.15 125.00   0.00   77
  4  \w     31.00  81.00   1.00   15.00    --   41.15-125.00 150.00   50
  5  \w     32.00 109.00   1.00   15.00    --   41.15  38.00 120.00   77
  6  \w     76.00 170.00   1.00   60.00    --  106.54  68.00   6.00   94
  7  \w     33.00 126.00   1.00   60.00    --  106.54 -68.00-126.00   93
  8  \w     34.00 117.00   1.00   60.00    --  106.54 -45.00  90.00   83
  9  \w     78.00 168.00   1.00   60.00    --  106.54  30.00 150.00   90
 10  \w     94.00 168.00   1.00   60.00    --  106.54  45.00 -90.00   74
 11  \w    136.00 176.00   1.00   60.00    --  106.54  61.00  90.00   40
 12  \w     77.00 113.00   1.00   60.00    --  106.54  61.00  90.00   36
 13  \w     80.00 176.00   1.00   60.00    --  106.54  30.00 -30.00   96
 14  \w     91.00 178.00   1.00   60.00    --  106.54  45.00  60.00   87
;
_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      -0.0293399000
_diffrn_orient_matrix_UB_12      0.0424606000
_diffrn_orient_matrix_UB_13      -0.0493918000
_diffrn_orient_matrix_UB_21      0.0499129000
_diffrn_orient_matrix_UB_22      0.0524241000
_diffrn_orient_matrix_UB_23      0.0145652000
_diffrn_orient_matrix_UB_31      0.0474778000
_diffrn_orient_matrix_UB_32      -0.0288690000
_diffrn_orient_matrix_UB_33      -0.0459937000
_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  0.0250
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            63403
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.684
_diffrn_reflns_theta_min         2.891
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.097
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.582
_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    1.258
_exptl_crystal_description       plate
_exptl_crystal_F_000             3856
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.199
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 8055 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0000(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1171
_refine_ls_number_reflns         19026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0275
_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^)+(0.0384P)^2^+2.3684P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0703
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                18378
_reflns_number_total             19026
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt00173f2.cif
_cod_data_source_block           hasj170516a
_cod_depositor_comments
'Adding full bibliography for 7706544--7706549.cif.'
_cod_database_code               7706549
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C58H54CaN2O2P2
_reflns_odcompleteness_completeness 99.90
_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
2.a Secondary CH2 refined with riding coordinates:
 C45(H45A,H45B), C97(H97A,H97B), C46(H46A,H46B), C49(H49A,H49B), C99(H99A,
 H99B), C103(H10A,H10B), C47(H47A,H47B), C100(H10C,H10D), C98(H98A,H98B),
 C102(H10E,H10F), C101(H10G,H10H), C51(H51A,H51B), C50(H50A,H50B), C48(H48A,
 H48B), C104(H10I,H10J), C52(H52A,H52B)
2.b Aromatic/amide H refined with riding coordinates:
 C88(H88), C32(H32), C60(H60), C31(H31), C19(H19), C14(H14), C87(H87),
 C86(H86), C13(H13), C66(H66), C70(H70), C116(H116), C26(H26), C2(H2), C55(H55),
  C71(H71), C3(H3), C65(H65), C90(H90), C8(H8), C6(H6), C89(H89), C29(H29),
 C7(H7), C34(H34), C5(H5), C115(H115), C28(H28), C114(H114), C35(H35), C59(H59),
  C54(H54), C38(H38), C30(H30), C113(H113), C84(H84), C18(H18), C68(H68),
 C111(H111), C22(H22), C58(H58), C92(H92), C16(H16), C25(H25), C57(H57),
 C69(H69), C17(H17), C112(H112), C105(H105), C36(H36), C24(H24), C23(H23),
 C94(H94), C93(H93), C78(H78), C96(H96), C106(H106), C107(H107), C76(H76),
 C37(H37), C83(H83), C110(H110), C74(H74), C109(H109), C41(H41), C82(H82),
 C95(H95), C108(H108), C40(H40), C75(H75), C77(H77), C80(H80), C81(H81),
 C44(H44), C43(H43), C42(H42)
;
_shelx_res_checksum              76034
_shelx_hkl_checksum              63264
_olex2_date_sample_data_collection 2017-05-16
_olex2_submission_original_sample_id hasj170516a
_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 3.141
_oxdiff_exptl_absorpt_empirical_full_min 0.774