Calcium(ii)-catalyzed enantioselective conjugate additions of amines.
Uno, Brice E.; Dicken, Rachel D.; Redfern, Louis R.; Stern, Charlotte M.; Krzywicki, Greg G.; Scheidt, Karl A.; Chemical science 9 (2018) 1634–1639; doi:10.1039/c7sc05205g

data_1548656
_publ_section_title
;
 Calcium(ii)-catalyzed enantioselective conjugate additions of amines.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              1634
_journal_page_last               1639
_journal_paper_doi               10.1039/c7sc05205g
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C144 H99 Ca2 O22 P3, C48 H28 O4 P, 3(H2 O)'
_chemical_formula_sum            'C192 H133 Ca2 O29 P4'
_chemical_formula_weight         3108.02
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2016-11-21
_audit_creation_method
;
Olex2 1.2
(compiled Nov  7 2016 13:22:42 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2017-02-06 deposited with the CCDC.
2017-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7157(4)
_cell_length_b                   21.3880(7)
_cell_length_c                   65.483(2)
_cell_measurement_reflns_used    6897
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      63.71
_cell_measurement_theta_min      2.47
_cell_volume                     19209.5(10)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.99
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0898
_diffrn_reflns_av_unetI/netI     0.1338
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       73
_diffrn_reflns_limit_l_min       -76
_diffrn_reflns_number            57991
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        63.725
_diffrn_reflns_theta_max         63.725
_diffrn_reflns_theta_min         2.467
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.339
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.6249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0852 before and 0.0613 after correction.
The Ratio of minimum to maximum transmission is 0.8305.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.075
_exptl_crystal_description       needle
_exptl_crystal_F_000             6468
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Toluene'
_exptl_crystal_size_max          0.528
_exptl_crystal_size_mid          0.036
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 6354 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.026(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2078
_refine_ls_number_reflns         31133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0630
_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^)+(0.0478P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1434
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                20787
_reflns_number_total             31133
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc05205g2.cif
_cod_data_source_block           xrd_0818abeu
_cod_depositor_comments
'Adding full bibliography for 1548656--1548657.cif.'
_cod_original_cell_volume        19209.6(11)
_cod_database_code               1548656
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.538
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1(H1AA,H2AA), O2(H3AA,H4AA), O3(H5AA,H6AA)
2.b Rotating group:
 O2L(H2LA,H2LB), O3L(H3LA,H3LB), O5L(H5LA,H5LB), O6L(H6LA,H6LB), O10L(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C3B(H3B), C3C(H3C), C5A(H5A), C5B(H5B), C5C(H5C), C6A(H6A),
 C6B(H6B), C6C(H6C), C7A(H7A), C7B(H7B), C7C(H7C), C8A(H8A), C8B(H8B), C8C(H8C),
  C13A(H13A), C13B(H13B), C13C(H13C), C14A(H14A), C14B(H14B), C14C(H14C),
 C15A(H15A), C15B(H15B), C15C(H15C), C16A(H16A), C16B(H16B), C16C(H16C),
 C19A(H19A), C19B(H19B), C19C(H19C), C20A(H20A), C20B(H20B), C20C(H20C),
 C21A(H21A), C21B(H21B), C21C(H21C), C22A(H22A), C22B(H22B), C22C(H22C),
 C24A(H24A), C24B(H24B), C24C(H24C), C27A(H27A), C27B(H27B), C27C(H27C),
 C29A(H29A), C29B(H29B), C29C(H29C), C30A(H30A), C30B(H30B), C30C(H30C),
 C31A(H31A), C31B(H31B), C31C(H31C), C32A(H32A), C32B(H32B), C32C(H32C),
 C37A(H37A), C37B(H37B), C37C(H37C), C38A(H38A), C38B(H38B), C38C(H38C),
 C39A(H39A), C39B(H39B), C39C(H39C), C40A(H40A), C40B(H40B), C40C(H40C),
 C43A(H43A), C43B(H43B), C43C(H43C), C44A(H44A), C44B(H44B), C44C(H44C),
 C45A(H45A), C45B(H45B), C45C(H45C), C46A(H46A), C46B(H46B), C46C(H46C),
 C48A(H48A), C48B(H48B), C48C(H48C), C3D(H), C5D(HA), C6D(HB), C7D(HC), C8D(HD),
  C13D(HE), C14D(HF), C15D(HG), C16D(HH), C19D(HI), C20D(HJ), C21D(HK),
 C22D(HL), C24D(HM), C27D(HN), C29D(HO), C30D(HP), C31D(HQ), C32D(HR), C37D(HS),
  C38D(HT), C39D(HU), C40D(HV), C43D(HW), C44D(HX), C45D(HY), C46D(HZ),
 C48D(H0AA)
;
_shelx_res_checksum              40668
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'