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_7124407
_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         'C45 H42 N4 O6'
_chemical_formula_sum            'C45 H42 N4 O6'
_chemical_formula_weight         734.82
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-09-04 deposited with the CCDC.    2019-10-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.4730(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.02810(10)
_cell_length_b                   18.2669(2)
_cell_length_c                   20.2604(2)
_cell_measurement_reflns_used    14998
_cell_measurement_temperature    253.00(10)
_cell_measurement_theta_max      70.9760
_cell_measurement_theta_min      4.3890
_cell_volume                     3670.84(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (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 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      253.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_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   -100.00 -34.00   1.00    2.00    --  -41.07 -57.00  90.00   66
  2  \w   -109.00 -11.00   1.00    2.00    --  -41.07 -77.00 -30.00   98
  3  \w    -64.00 -18.00   1.00    2.00    --  -41.07 -57.00 150.00   46
  4  \w    -62.00  32.00   1.00    2.00    --  -41.07  38.00 -90.00   94
  5  \w    -60.00  -8.00   1.00    2.00    --  -41.07 -77.00 150.00   52
  6  \w     43.00  79.00   1.00    2.00    --   41.07 -99.00 -90.00   36
  7  \w     45.00  79.00   1.00    2.00    --   41.07 -99.00 -30.00   34
  8  \w     25.00  52.00   1.00    2.00    --   41.07  38.00  90.00   27
  9  \w      9.00  34.00   1.00    2.00    --   41.07  77.00-180.00   25
 10  \w    142.00 168.00   1.00   10.00    --  101.41  77.00  90.00   26
 11  \w     72.00  99.00   1.00   10.00    --  101.41  61.00  90.00   27
 12  \w     72.00  98.00   1.00   10.00    --  101.41  61.00  60.00   26
 13  \w     69.00  95.00   1.00   10.00    --  101.41  77.00 120.00   26
 14  \w    153.00 178.00   1.00   10.00    --  101.41  77.00 120.00   25
 15  \w     69.00  95.00   1.00   10.00    --  101.41  77.00  90.00   26
 16  \w     76.00 102.00   1.00   10.00    --  101.41  45.00 150.00   26
 17  \w     70.00 177.00   1.00   10.00    --  101.41  77.00  30.00  107
 18  \w     24.00  58.00   1.00   10.00    --  101.41 -94.00  90.00   34
 19  \w     72.00  99.00   1.00   10.00    --  101.41  61.00 150.00   27
 20  \w     72.00  98.00   1.00   10.00    --  101.41  61.00 120.00   26
 21  \w     84.00 109.00   1.00   10.00    --  101.41 -94.00  90.00   25
 22  \w     69.00  95.00   1.00   10.00    --  101.41  77.00  60.00   26
 23  \w     21.00 101.00   1.00   10.00    --  101.41 -94.00-180.00   80
 24  \w     69.00  95.00   1.00   10.00    --  101.41  77.00-180.00   26
 25  \w    119.00 174.00   1.00   10.00    --  101.41  77.00-180.00   55
 26  \w    104.00 174.00   1.00   10.00    --  101.41  77.00 150.00   70
 27  \w     95.00 120.00   1.00   10.00    --  101.41 125.00 -90.00   25
 28  \w     77.00 168.00   1.00   10.00    --  101.41  45.00 120.00   91
 29  \w     77.00 104.00   1.00   10.00    --  101.41  45.00-180.00   27
 30  \w     69.00  95.00   1.00   10.00    --  101.41  77.00 150.00   26
 31  \w     72.00  98.00   1.00   10.00    --  101.41  61.00-180.00   26
 32  \w     95.00 168.00   1.00   10.00    --  101.41 125.00-120.00   73
 33  \w     77.00 102.00   1.00   10.00    --  101.41  45.00-150.00   25
 34  \w     72.00  99.00   1.00   10.00    --  101.41  61.00-150.00   27
 35  \w    125.00 173.00   1.00   10.00    --  101.41  64.00  61.12   48
 36  \w     73.00 100.00   1.00   10.00    --  101.41  64.00  61.12   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      -0.0210565000
_diffrn_orient_matrix_UB_12      0.0143764000
_diffrn_orient_matrix_UB_13      -0.0757318000
_diffrn_orient_matrix_UB_21      0.1485544000
_diffrn_orient_matrix_UB_22      -0.0197180000
_diffrn_orient_matrix_UB_23      -0.0023924000
_diffrn_orient_matrix_UB_31      -0.0400184000
_diffrn_orient_matrix_UB_32      -0.0807649000
_diffrn_orient_matrix_UB_33      -0.0128998000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            34483
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.046
_diffrn_reflns_theta_min         3.274
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.44a (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    1.330
_exptl_crystal_description       plate
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     499
_refine_ls_number_reflns         7044
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0468
_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^)+(0.0681P)^2^+1.3774P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1302
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6122
_reflns_number_total             7044
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07244f2.cif
_cod_data_source_block           cc1exp17
_cod_database_code               7124407
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'c43 h42 n6 o10 Zn1'
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.906
_reflns_odcompleteness_completeness 99.97
_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 C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O7) = Uanis(O1)
Uanis(O8) = Uanis(O2)
Uanis(C49) = Uanis(C8)
Uanis(C50) = Uanis(C9)
Uanis(C51) = Uanis(C10)
Uanis(C11) = Uanis(C46)
Uanis(C12) = Uanis(C47)
Uanis(C48) = Uanis(C13)
3. Others
 Fixed Sof: O1(0.9) O2(0.9) O7(0.1) O8(0.1) H7AA(0.9) H7AB(0.9) H7BC(0.1)
 H7BD(0.1) C11(0.9) C10(0.9) C9(0.9) H9(0.9) C8(0.9) C13(0.9) C12(0.9) H12(0.9)
 H14A(0.9) H14B(0.9) H14C(0.9) H14D(0.1) H14E(0.1) H14F(0.1) H15A(0.9)
 H15B(0.9) H15C(0.1) H15D(0.1) H44A(0.9) H44B(0.9) H44C(0.1) H44D(0.1) C46(0.1)
 C51(0.1) C50(0.1) H50(0.1) C49(0.1) C48(0.1) C47(0.1) H47(0.1)
4.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C7(H7AA,H7AB), C7(H7BC,H7BD), C15(H15A,H15B), C15(H15C,H15D),
 C23(H23A,H23B), C29(H29A,H29B), C30(H30A,H30B), C36(H36A,H36B), C44(H44A,H44B),
  C44(H44C,H44D), C45(H45A,H45B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C9(H9), C12(H12), C18(H18), C21(H21), C25(H25),
 C26(H26), C27(H27), C32(H32), C33(H33), C34(H34), C38(H38), C40(H40), C50(H50),
  C47(H47)
4.c Fitted hexagon refined as free rotating group:
 C11(C10,C9,C8,C13,C12), C46(C51,C50,C49,C48,C47)
4.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C14(H14D,H14E,H14F), C22(H22A,H22B,H22C), C43(H43A,H43B,
 H43C)
;
_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 0.916