Chirality Transfer in a Cage Controls the Clockwise / Anticlockwise Propeller Arrangement of the tris(2-pyridylmethyl)amine Ligand
Martinez, Alexandre; Qiu, Gege; Colomban, Cédric; Giorgi, Michel; Vanthuyne, Nicolas; Chemical Communications  (2019) –; doi:10.1039/C9CC07244F

data_7124409
_publ_section_title
;
 Chirality Transfer in a Cage Controls the Clockwise / Anticlockwise
 Propeller Arrangement of the tris(2-pyridylmethyl)amine Ligand
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC07244F
_journal_year                    2019
_chemical_formula_moiety         'Cl, C45 H43 N4 O6, C H4 O'
_chemical_formula_sum            'C46 H47 Cl N4 O7'
_chemical_formula_weight         803.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-05-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-04 deposited with the CCDC.    2019-10-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.3700(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.7019(2)
_cell_length_b                   10.84040(10)
_cell_length_c                   17.9416(2)
_cell_measurement_reflns_used    14907
_cell_measurement_temperature    295
_cell_measurement_theta_max      70.8790
_cell_measurement_theta_min      4.5960
_cell_volume                     3947.38(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_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    -70.00  42.00   1.00    1.00    --  -41.07   0.00-120.00  112
  2  \w    -63.00 -12.00   1.00    1.00    --  -41.07  57.00  30.00   51
  3  \w   -112.00 -15.00   1.00    1.00    --  -41.07 -57.00 150.00   97
  4  \w    -65.00  12.00   1.00    1.00    --  -41.07  38.00 -30.00   77
  5  \w     29.00  93.00   1.00    1.00    --   41.07-125.00-180.00   64
  6  \w     52.00 175.00   1.00   10.00    --  101.41  15.00-180.00  123
  7  \w    144.00 171.00   1.00   10.00    --  101.41 125.00-180.00   27
  8  \w     30.00 117.00   1.00   10.00    --  101.41-125.00 -90.00   87
  9  \w     81.00 114.00   1.00   10.00    --  101.41-125.00 150.00   33
 10  \w     28.00  54.00   1.00   10.00    --  101.41-125.00 150.00   26
 11  \w     29.00 108.00   1.00   10.00    --  101.41 -61.00  60.00   79
 12  \w     95.00 170.00   1.00   10.00    --  101.41 125.00  30.00   75
 13  \w    120.00 174.00   1.00   10.00    --  101.41  45.00-150.00   54
 14  \w     76.00 103.00   1.00   10.00    --  101.41  45.00-150.00   27
 15  \w    126.00 172.00   1.00   10.00    --  101.41 125.00 -60.00   46
 16  \w     21.00 106.00   1.00   10.00    --  101.41 -94.00 -30.00   85
 17  \w     29.00 113.00   1.00   10.00    --  101.41 -45.00 -60.00   84
 18  \w    100.00 127.00   1.00   10.00    --  101.41 125.00  60.00   27
 19  \w    103.00 130.00   1.00   10.00    --  101.41  77.00  60.00   27
;
_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      -0.0695937000
_diffrn_orient_matrix_UB_12      -0.0565888000
_diffrn_orient_matrix_UB_13      -0.0135780000
_diffrn_orient_matrix_UB_21      -0.0274740000
_diffrn_orient_matrix_UB_22      0.1217831000
_diffrn_orient_matrix_UB_23      0.0252743000
_diffrn_orient_matrix_UB_31      -0.0128125000
_diffrn_orient_matrix_UB_32      0.0465037000
_diffrn_orient_matrix_UB_33      -0.0827477000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28096
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.964
_diffrn_reflns_theta_min         4.357
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.340
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       prism
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         7529
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0470
_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^)+(0.0784P)^2^+1.0898P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1332
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6675
_reflns_number_total             7529
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07244f2.cif
_cod_data_source_block           cc1exp113
_cod_database_code               7124409
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'c45 h43 Cl1 n4 o6'
_shelx_estimated_absorpt_t_max   0.856
_shelx_estimated_absorpt_t_min   0.757
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C39(H39A,H39B), C29(H29A,H29B), C1(H1A,H1B), C38(H38A,H38B), C45(H45A,H45B),
 C15(H15A,H15B), C30(H30A,H30B), C7(H7A,H7B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C33(H33), C10(H10), C13(H13), C36(H36), C27(H27), C41(H41), C3(H3), C18(H18),
 C43(H43), C25(H25), C5(H5), C26(H26), C21(H21), C42(H42), C4(H4)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C37(H37A,H37B,H37C), C22(H22A,H22B,H22C), C57(H57A,H57B,
 H57C)
2.e Idealised tetrahedral OH refined with riding coordinates:
 O58(H58)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.287
_oxdiff_exptl_absorpt_empirical_full_min 0.784