Connecting the conformational behavior of cyclic octadepsipeptides with their ionophoric property and membrane permeability.
Stadelmann, Thomas; Subramanian, Govindan; Menon, Sanjay; Townsend, Chad E.; Lokey, R. Scott; Ebert, Marc-Olivier; Riniker, Sereina; Organic & biomolecular chemistry 18 (2020) 7110–7126; doi:10.1039/d0ob01447h

data_7157702
_publ_section_title
;
 Connecting the conformational behavior of cyclic octadepsipeptides with
 their ionophoric property and membrane permeability.
;
_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7110
_journal_page_last               7126
_journal_paper_doi               10.1039/d0ob01447h
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C52 H76 N4 O12, C H4 O'
_chemical_formula_sum            'C53 H80 N4 O13'
_chemical_formula_weight         981.21
_chemical_name_systematic        PF1022A
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-29
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2020-05-15 deposited with the CCDC.	2020-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.1570(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.40860(10)
_cell_length_b                   13.78330(10)
_cell_length_c                   14.46940(10)
_cell_measurement_reflns_used    60765
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      79.3860
_cell_measurement_theta_min      3.2140
_cell_volume                     2697.59(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.42a (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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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    -61.00  25.00   0.50    0.10    --  -26.00 100.00 -88.71  172
  2  \w     15.00  42.00   0.50    0.10    --   46.00  92.00  66.66   54
  3  \w     38.00  63.00   0.50    0.10    --   49.37  57.00  30.00   50
  4  \w      0.00  73.00   0.50    0.10    --   49.37 -77.00 150.00  146
  5  \w     85.00 112.00   0.50    0.10    --   49.37  57.00   0.00   54
  6  \w     37.00  68.00   0.50    0.10    --   49.37  38.00 -30.00   62
  7  \w     67.00 122.00   0.50    0.10    --   49.37-178.00-180.00  110
  8  \w     34.00  62.00   0.50    0.10    --   49.37  57.00-150.00   56
  9  \w     34.00  59.00   0.50    0.10    --   49.37  57.00 -60.00   50
 10  \w     41.00  72.00   0.50    0.10    --   49.37  38.00-180.00   62
 11  \w     72.00 125.00   0.50    0.10    --   49.37  38.00 -30.00  106
 12  \w     33.00  59.00   0.50    0.10    --   49.37  61.00 -31.09   52
 13  \w     34.00  79.00   0.50    0.10    --   49.37  57.00  90.00   90
 14  \w     65.00 118.00   0.50    0.10    --   49.37 178.00 -90.00  106
 15  \w     38.00  72.00   0.50    0.10    --   49.37  57.00   0.00   68
 16  \w   -104.00 -78.00   0.50    0.10    --  -49.87 -77.00  60.00   52
 17  \w    -79.00 -37.00   0.50    0.10    --  -49.87 -38.00-180.00   84
 18  \w    -64.00 -38.00   0.50    0.10    --  -49.87 -26.00-109.26   52
 19  \w   -111.00 -85.00   0.50    0.10    --  -49.87 -38.00-180.00   52
 20  \w    -91.00 -38.00   0.50    0.10    --  -49.87 -42.00-109.51  106
 21  \w   -120.00 -94.00   0.50    0.10    --  -49.87 -42.00-109.51   52
 22  \w    -53.00 -26.00   0.50    0.10    --  -49.87 -77.00  60.00   54
 23  \w   -107.00 -73.00   0.50    0.10    --  -49.87 -26.00-109.26   68
 24  \w    -56.00 -26.00   0.50    0.10    --  -49.87 -77.00 -30.00   60
 25  \w     20.00  45.00   0.50    0.10    --   50.00  90.00 153.63   50
 26  \w     33.00  59.00   0.50    0.10    --   58.00  80.00  -2.52   52
 27  \w     33.00  79.00   0.50    0.10    --   58.00  81.00  38.95   92
 28  \w     32.00  59.00   0.50    0.10    --   58.00  82.00-134.30   54
 29  \w     88.00 120.00   0.50    0.10    --   58.00  81.00  38.95   64
 30  \w     33.00  59.00   0.50    0.10    --   58.00  80.00 -79.57   52
 31  \w     37.00  63.00   0.50    0.10    --   62.00  80.00  89.56   52
 32  \w     41.00  69.00   0.50    0.10    --   66.00  81.00 128.69   56
 33  \w    -70.00 -43.00   0.50    0.30    --  -70.00 -83.00-128.85   54
 34  \w    -68.00 -43.00   0.50    0.30    --  -70.00 -83.00 -84.52   50
 35  \w    -75.00 -46.00   0.50    0.30    --  -70.00 -78.00 -37.07   58
 36  \w    -72.00 -46.00   0.50    0.30    --  -70.00 -77.00  30.00   52
 37  \w    -37.00   0.00   0.50    0.30    --  -70.00  38.00  30.00   74
 38  \w    -80.00 -46.00   0.50    0.30    --  -70.00 -77.00  90.00   68
 39  \w    -78.00 -48.00   0.50    0.30    --  -70.00 -76.00 -19.18   60
 40  \w    -70.00 -44.00   0.50    0.30    --  -70.00 -81.00 166.86   52
 41  \w    -72.00 -47.00   0.50    0.30    --  -70.00 -75.00  -9.84   50
 42  \w     52.00  87.00   0.50    0.10    --   74.00  73.00-173.87   70
 43  \w     52.00  88.00   0.50    0.10    --   74.00  73.00 111.36   72
 44  \w     49.00  97.00   0.50    0.10    --   74.00  80.00 -61.73   96
 45  \w    112.00 138.00   0.50    0.10    --   74.00  78.00  36.57   52
 46  \w     50.00  76.00   0.50    0.10    --   74.00  78.00  36.57   52
 47  \w     50.00  79.00   0.50    0.10    --   74.00  79.00 146.34   58
 48  \w     50.00  79.00   0.50    0.10    --   74.00  79.00  63.85   58
 49  \w    117.00 145.00   0.50    0.10    --   78.00  70.00 -44.87   56
 50  \w     57.00  96.00   0.50    0.10    --   78.00  70.00 -44.87   78
 51  \w    115.00 146.00   0.50    0.10    --   78.00  68.00-129.16   62
 52  \w     58.00  93.00   0.50    0.10    --   78.00  68.00-129.16   70
 53  \w    112.00 158.00   0.50    0.30    --   86.00  57.00 152.36   92
 54  \w     70.00  99.00   0.50    0.30    --   86.00  57.00 152.36   58
 55  \w     69.00 104.00   0.50    0.30    --   86.00  61.00-106.36   70
 56  \w     86.00 111.00   0.50    0.30    --  110.00  77.00  60.00   50
 57  \w    142.00 170.00   0.50    0.30    --  110.00  77.00   0.00   56
 58  \w     88.00 139.00   0.50    0.30    --  110.00  77.00   0.00  102
 59  \w    124.00 170.00   0.50    0.30    --  110.00  77.00 -30.00   92
 60  \w     86.00 113.00   0.50    0.30    --  110.00  77.00 -30.00   54
 61  \w     94.00 153.00   0.50    0.30    --  110.00  57.00-120.00  118
 62  \w     86.00 164.00   0.50    0.30    --  110.00  77.00  90.00  156
 63  \w     95.00 129.00   0.50    0.30    --  110.00  57.00-180.00   68
 64  \w     43.00 110.00   0.50    0.30    --  110.00 -99.00  90.00  134
 65  \w     38.00  63.00   0.50    0.30    --  110.00 -57.00-180.00   50
 66  \w     94.00 136.00   0.50    0.30    --  110.00  57.00 -30.00   84
 67  \w    132.00 175.00   0.50    0.30    --  110.00  77.00-120.00   86
 68  \w    120.00 172.00   0.50    0.30    --  110.00  77.00-180.00  104
 69  \w     94.00 137.00   0.50    0.30    --  110.00  57.00  30.00   86
 70  \w     88.00 116.00   0.50    0.30    --  110.00  77.00-180.00   56
 71  \w     45.00 126.00   0.50    0.30    --  110.00 -77.00 -90.00  162
 72  \w     48.00 110.00   0.50    0.30    --  110.00 -99.00  60.00  124
 73  \w    138.00 173.00   0.50    0.30    --  110.00  77.00 150.00   70
 74  \w     86.00 112.00   0.50    0.30    --  110.00  77.00 150.00   52
 75  \w     58.00 118.00   0.50    0.30    --  110.00-125.00 -60.00  120
 76  \w     87.00 174.00   0.50    0.30    --  110.00  77.00  30.00  174
 77  \w     97.00 122.00   0.50    0.30    --  110.00  57.00   0.00   50
 78  \w     38.00  63.00   0.50    0.30    --  110.00 -57.00  60.00   50
 79  \w     77.00 130.00   0.50    0.30    --  110.00 -77.00 120.00  106
 80  \w     90.00 174.00   0.50    0.30    --  110.00  77.00 120.00  168
 81  \w    139.00 175.00   0.50    0.30    --  110.00  77.00 -60.00   72
 82  \w     86.00 127.00   0.50    0.30    --  110.00  77.00-120.00   82
 83  \w     45.00  73.00   0.50    0.30    --  110.00 -77.00 120.00   56
 84  \w     86.00 125.00   0.50    0.30    --  110.00  77.00 -60.00   78
 85  \w     96.00 171.00   0.50    0.30    --  110.00  57.00-150.00  150
 86  \w     85.00 110.00   0.50    0.30    --  110.00 -99.00 -30.00   50
 87  \w     86.00 174.00   0.50    0.30    --  110.00  77.00 -90.00  176
 88  \w    124.00 169.00   0.50    0.30    --  110.00  77.00  60.00   90
 89  \w    100.00 130.00   0.50    0.30    --  110.00  38.00  90.00   60
 90  \w     53.00 101.00   0.50    0.30    --  110.00 -99.00-180.00   96
 91  \w     43.00  69.00   0.50    0.30    --  110.00 -99.00 -30.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1011708000
_diffrn_orient_matrix_UB_12      -0.0381466000
_diffrn_orient_matrix_UB_13      -0.0020091000
_diffrn_orient_matrix_UB_21      0.0349864000
_diffrn_orient_matrix_UB_22      0.0063396000
_diffrn_orient_matrix_UB_23      0.1131427000
_diffrn_orient_matrix_UB_31      -0.0388539000
_diffrn_orient_matrix_UB_32      0.1048961000
_diffrn_orient_matrix_UB_33      -0.0074609000
_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  0.0423
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            74402
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.728
_diffrn_reflns_theta_min         3.254
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.532
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.42a (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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description       block
_exptl_crystal_F_000             1060
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.151
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 4954 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     662
_refine_ls_number_reflns         11334
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0280
_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^)+(0.0333P)^2^+0.4259P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0699
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.929
_reflns_number_gt                11065
_reflns_number_total             11334
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01447h2.cif
_cod_data_source_block           loc271019_1_2
_cod_depositor_comments
'Adding full bibliography for 7157702--7157703.cif.'
_cod_database_code               7157702
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C52H78N4O13
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O1A-C1A \\sim O1B-C1B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C1A) = Uanis(C1B)
4. Rigid body (RIGU) restrains
 O1B, C1B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(O1B)=Sof(H1B)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=1-FVAR(1)
 Sof(O1A)=Sof(H1A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C17(H17), C18(H18), C20(H20),
 C24(H24), C36(H36), C42(H42), C48(H48)
6.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C11(H11A,H11B), C12(H12A,H12B), C27(H27A,H27B), C32(H32A,H32B),
 C34(H34A,H34B)
6.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C19(H19), C23(H23), C29(H29), C35(H35), C39(H39), C45(H45),
 C49(H49), C50(H50), C51(H51)
6.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C16(H16A,H16B,H16C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C33(H33A,
 H33B,H33C), C37(H37A,H37B,H37C), C41(H41A,H41B,H41C), C44(H44A,H44B,H44C),
 C46(H46A,H46B,H46C), C47(H47A,H47B,H47C), C52(H52A,H52B,H52C), C1A(H1AA,H1AB,
 H1AC), C1B(H1BA,H1BB,H1BC)
6.e Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1B(H1B)
;
_shelx_res_checksum              58813
_olex2_date_sample_data_collection 2019-10-28
_olex2_date_sample_submission    2019-10-25
_olex2_submission_original_sample_id loc271019_1_2
_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 1.422
_oxdiff_exptl_absorpt_empirical_full_min 0.797