Remote conformational responses to enantiomeric excess in carboxylate-binding dynamic foldamers
Eccles, Natasha; Le Bailly, Bryden; della Sala, Flavio; Vitorica-Yrzebal, Inigo; Clayden, Jonathan; Webb, Simon; Chemical Communications  (2019) –; doi:10.1039/C9CC03895G

data_7123793
_publ_section_title
;
 Remote conformational responses to enantiomeric excess in
 carboxylate-binding dynamic foldamers
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC03895G
_journal_year                    2019
_chemical_formula_moiety         'C45 H56 N10 O7 Zn, 2(Cl O4), 5(H2 O)'
_chemical_formula_sum            'C45 H66 Cl2 N10 O20 Zn'
_chemical_formula_weight         1203.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-10-31
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-05-20 deposited with the CCDC.    2019-07-08 downloaded from the CCDC.
;
_cell_angle_alpha                102.353(2)
_cell_angle_beta                 96.569(2)
_cell_angle_gamma                100.991(2)
_cell_formula_units_Z            2
_cell_length_a                   9.3605(3)
_cell_length_b                   15.3297(4)
_cell_length_c                   20.4443(6)
_cell_measurement_reflns_used    12396
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.7170
_cell_measurement_theta_min      2.3540
_cell_volume                     2776.06(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.30c (Rigaku OD, 2017)'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.840
_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    -71.00  93.00   1.00    7.00    --    5.00 -19.00 -30.00  164
  2  \w    -97.00  26.00   1.00    7.00    --   -7.60 -57.00-120.00  123
  3  \w    -64.00  32.00   1.00    7.00    --   -7.60 -76.00   0.00   96
  4  \w     -8.00  25.00   1.00    7.00    --   -7.60 -76.00  30.00   33
  5  \w    -95.00 -64.00   1.00    7.00    --   -7.60 -57.00 -60.00   31
  6  \w    -34.00  -8.00   1.00    7.00    --   -7.60 -57.00 -60.00   26
  7  \w    -74.00 -49.00   1.00    7.00    --   -7.60 -76.00  30.00   25
  8  \w    -96.00 -18.00   1.00    7.00    --   -7.60 -57.00 150.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0661839000
_diffrn_orient_matrix_UB_12      0.0029626000
_diffrn_orient_matrix_UB_13      0.0218781000
_diffrn_orient_matrix_UB_21      0.0148126000
_diffrn_orient_matrix_UB_22      -0.0374374000
_diffrn_orient_matrix_UB_23      -0.0232418000
_diffrn_orient_matrix_UB_31      0.0389747000
_diffrn_orient_matrix_UB_32      0.0308085000
_diffrn_orient_matrix_UB_33      -0.0166289000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.840
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            49493
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.029
_diffrn_reflns_theta_min         2.067
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.621
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.30c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_description       plate
_exptl_crystal_F_000             1260
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.206
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     784
_refine_ls_number_reflns         13632
_refine_ls_number_restraints     98
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0575
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0522P)^2^+3.6157P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1316
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10640
_reflns_number_total             13632
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc03895g2.cif
_cod_data_source_block           s4986r
_cod_original_cell_volume        2776.06(14)
_cod_database_code               7123793
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         Zn1N2O2C40H40
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.886
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 O11-H11A = O11-H11B
 0.85 with sigma of 0.02
 O74-H74A = O74-H74B
 0.85 with sigma of 0.02
 O76-H76A = O76-H76B
 0.85 with sigma of 0.02
 H11A-H11B
 1.34 with sigma of 0.04
 H74A-H74B
 1.34 with sigma of 0.04
 H76A-H76B
 1.34 with sigma of 0.04
 Zn1-H11A \\sim Zn1-H11B
 with sigma of 0.02
 Cl8A-O9A \\sim Cl8-O10 \\sim Cl8A-O10A \\sim Cl8-O0AA \\sim Cl8-O9 \\sim
Cl8A-O0AB \\sim Cl8-O7 ~
 Cl8A-O7A
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 O10A, Cl8A, O7A, O0AB, O9A, O10, Cl8, O7, O9, O0AA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(Cl8A)=Sof(O7A)=Sof(O0AB)=Sof(O9A)=Sof(O10A)=1-FVAR(1)
 Sof(Cl8)=Sof(O7)=Sof(O9)=Sof(O10)=Sof(O0AA)=FVAR(1)
5.a Free rotating group:
 O73(H73A,H73B), O75(H75A,H75B), O77(H77A,H77B)
5.b Secondary CH2 refined with riding coordinates:
 C46(H46A,H46B), C25(H25A,H25B), C22(H22A,H22B), C24(H24A,H24B)
5.c Aromatic/amide H refined with riding coordinates:
 N33(H33), N45(H45), N42(H42), N36(H36), N39(H39), C28(H28), C20(H20),
 C31(H31), C29(H29), C65(H65), C70(H70), C64(H64), C15(H15), C14(H14), C67(H67),
  C19(H19), C18(H18), C17(H17), C68(H68), C69(H69)
5.d X=CH2 refined with riding coordinates:
 N49(H49A,H49B)
5.e Idealised Me refined as rotating group:
 C51(H51A,H51B,H51C), C52(H52A,H52B,H52C), C57(H57A,H57B,H57C), C54(H54A,H54B,
 H54C), C55(H55A,H55B,H55C), C60(H60A,H60B,H60C), C58(H58A,H58B,H58C), C61(H61A,
 H61B,H61C)
;
_shelx_res_checksum              54414
_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 1.507
_oxdiff_exptl_absorpt_empirical_full_min 0.765