Bis-pyrene probes of foldamer conformation in solution and in phospholipid bilayers.
Lister, Francis G. A.; Eccles, Natasha; Pike, Sarah J.; Brown, Robert A.; Whitehead, George F. S.; Raftery, James; Webb, Simon J.; Clayden, Jonathan; Chemical science 9 (2018) 6860–6870; doi:10.1039/c8sc02532k

data_1549686
_publ_section_title
;
 Bis-pyrene probes of foldamer conformation in solution and in
 phospholipid bilayers.
;
_journal_issue                   33
_journal_name_full               'Chemical science'
_journal_page_first              6860
_journal_page_last               6870
_journal_paper_doi               10.1039/c8sc02532k
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C66 H71 N7 O8, C4 H10 O, 0.57(C H4 O)'
_chemical_formula_sum            'C70.57 H83.27 N7 O9.57'
_chemical_formula_weight         1182.59
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-05-16 deposited with the CCDC.
2018-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5967(4)
_cell_length_b                   21.5835(8)
_cell_length_c                   28.6986(6)
_cell_measurement_reflns_used    12464
_cell_measurement_temperature    150.06(10)
_cell_measurement_theta_max      60.5840
_cell_measurement_theta_min      2.5520
_cell_volume                     6563.8(4)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.06(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -85.00  55.00   1.00    1.00    --    0.00  60.00-180.00  140
  2  \w    -57.00   1.00   1.00    1.00    --    0.00  29.00 150.00   58
  3  \w      0.00  38.00   1.00    6.00    --   55.00  60.00   0.00   38
  4  \w     80.00 143.00   1.00    6.00    --   55.00  43.00 -60.00   63
  5  \w    -33.00 134.00   1.00    6.00    --   55.00  60.00-150.00  167
  6  \w    -34.00 111.00   1.00    6.00    --   55.00  57.00  60.00  145
  7  \w     41.00  78.00   1.00    6.00    --   55.00  60.00 150.00   37
  8  \w     22.00  48.00   1.00    6.00    --   55.00  43.00 -60.00   26
  9  \w     -2.00  92.00   1.00    6.00    --   55.00  29.00 -60.00   94
 10  \w    100.00 138.00   1.00    6.00    --   55.00  29.00 -60.00   38
 11  \w     95.00 140.00   1.00    6.00    --   55.00  60.00   0.00   45
 12  \w    -30.00 142.00   1.00    6.00    --   55.00  57.00-120.00  172
 13  \w     50.00 151.00   1.00   12.00    --  110.00  60.00-180.00  101
 14  \w     77.00 148.00   1.00   12.00    --  110.00  60.00   0.00   71
 15  \w     29.00 198.00   1.00   12.00    --  110.00  19.00 -30.00  169
 16  \w     56.00  93.00   1.00   12.00    --  110.00  60.00 -60.00   37
 17  \w     27.00  53.00   1.00   12.00    --  110.00  60.00  30.00   26
 18  \w     87.00 171.00   1.00   12.00    --  110.00  60.00  90.00   84
 19  \w     92.00 181.00   1.00   12.00    --  110.00  60.00 -30.00   89
 20  \w     51.00  77.00   1.00   12.00    --  110.00  60.00 -30.00   26
 21  \w    100.00 199.00   1.00   12.00    --  110.00  60.00-120.00   99
 22  \w     86.00 197.00   1.00   12.00    --  110.00  60.00-150.00  111
 23  \w     21.00 199.00   1.00   12.00    --  110.00  10.00  30.00  178
 24  \w    174.00 199.00   1.00   12.00    --  110.00  60.00-180.00   25
 25  \w     58.00 162.00   1.00   12.00    --  110.00  60.00 -90.00  104
 26  \w     83.00 169.00   1.00   12.00    --  110.00  60.00  30.00   86
 27  \w    145.00 172.00   1.00   12.00    --  110.00  60.00 -60.00   27
 28  \w     85.00 177.00   1.00   12.00    --  110.00  60.00 120.00   92
 29  \w     79.00 175.00   1.00   12.00    --  110.00  48.00  90.00   96
 30  \w    120.00 145.00   1.00   12.00    --  110.00  60.00  60.00   25
 31  \w     48.00 197.00   1.00   12.00    --  110.00  19.00-150.00  149
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0243012000
_diffrn_orient_matrix_UB_12      0.0687161000
_diffrn_orient_matrix_UB_13      0.0114617000
_diffrn_orient_matrix_UB_21      0.0595891000
_diffrn_orient_matrix_UB_22      0.0091769000
_diffrn_orient_matrix_UB_23      -0.0484535000
_diffrn_orient_matrix_UB_31      -0.1302895000
_diffrn_orient_matrix_UB_32      0.0171129000
_diffrn_orient_matrix_UB_33      -0.0200635000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0731
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            67099
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.236
_diffrn_reflns_theta_min         2.562
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52686
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_description       needle
_exptl_crystal_F_000             2529
_exptl_crystal_size_max          0.442
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 3251 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.19(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1128
_refine_ls_number_reflns         12007
_refine_ls_number_restraints     2988
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0687
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1014P)^2^+1.1888P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1928
_refine_ls_wR_factor_ref         0.2035
_reflns_Friedel_coverage         0.808
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                9692
_reflns_number_total             12007
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc02532k2.cif
_cod_data_source_block           s5080l
_cod_depositor_comments
'Adding full bibliography for 1549682--1549686.cif.'
_cod_database_code               1549686
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.765
_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, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Same fragment restrains
{C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16} sigma
for 1-2: 0.02, 1-3: 0.04
as
{C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, C31, C32}
{C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16} sigma
for 1-2: 0.02, 1-3: 0.04
as
{C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A, C10A, C11A, C12A, C13A, C14A,
C15A, C16A}
{C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16} sigma
for 1-2: 0.02, 1-3: 0.04
as
{C17A, C18A, C19A, C20A, C21A, C22A, C23A, C24A, C25A, C26A, C27A, C28A, C29A,
C30A, C31A, C32A}
5. Others
 Sof(H34A)=Sof(H33A)=Sof(H75C)=Sof(H75D)=Sof(C76A)=Sof(C77A)=Sof(H77A)=
 Sof(C78A)=Sof(H78A)=Sof(C79A)=Sof(H79A)=Sof(C80A)=Sof(H80A)=Sof(C81A)=
 Sof(H81A)=Sof(C1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(C5A)=
 Sof(C6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(C10A)=Sof(C11A)=
 Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=
 Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=
 Sof(H19A)=Sof(C20A)=Sof(C21A)=Sof(C22A)=Sof(C23A)=Sof(H23A)=Sof(C24A)=
 Sof(H24A)=Sof(C25A)=Sof(C26A)=Sof(C27A)=Sof(H27A)=Sof(C28A)=Sof(H28A)=
 Sof(C29A)=Sof(C30A)=Sof(H30A)=Sof(C31A)=Sof(H31A)=Sof(C32A)=Sof(H32A)=1-FVAR(1)
 Sof(H34)=Sof(H33)=Sof(H75A)=Sof(H75B)=Sof(O2B)=Sof(H2B)=Sof(C76)=Sof(C77)=
 Sof(H77)=Sof(C78)=Sof(H78)=Sof(C79)=Sof(H79)=Sof(C80)=Sof(H80)=Sof(C81)=
 Sof(H81)=Sof(C1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(C5)=Sof(C6)=
 Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(C10)=Sof(C11)=Sof(H11)=Sof(C12)=
 Sof(H12)=Sof(C13)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=
 Sof(C17)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(C21)=Sof(C22)=
 Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24)=Sof(C25)=Sof(C26)=Sof(C27)=Sof(H27)=
 Sof(C28)=Sof(H28)=Sof(C29)=Sof(C30)=Sof(H30)=Sof(C31)=Sof(H31)=Sof(C32)=
 Sof(H32)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C34(H34), C34(H34A), C33(H33), C33(H33A), C68(H68)
6.b Secondary CH2 refined with riding coordinates:
 C75(H75A,H75B), C75(H75C,H75D), C2C(H2CA,H2CB), C4C(H4CA,H4CB)
6.c Aromatic/amide H refined with riding coordinates:
 N45(H45), N71(H71), N63(H63), N38(H38), N39(H39), N51(H51), N57(H57),
 C77(H77), C78(H78), C79(H79), C80(H80), C81(H81), C2(H2), C3(H3), C7(H7),
 C8(H8), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19),
 C23(H23), C24(H24), C27(H27), C28(H28), C30(H30), C31(H31), C32(H32),
 C77A(H77A), C78A(H78A), C79A(H79A), C80A(H80A), C81A(H81A), C2A(H2A), C3A(H3A),
  C7A(H7A), C8A(H8A), C11A(H11A), C12A(H12A), C14A(H14A), C15A(H15A),
 C16A(H16A), C18A(H18A), C19A(H19A), C23A(H23A), C24A(H24A), C27A(H27A),
 C28A(H28A), C30A(H30A), C31A(H31A), C32A(H32A)
6.d Fitted hexagon refined as free rotating group:
 C76(C77,C78,C79,C80,C81), C76A(C77A,C78A,C79A,C80A,C81A)
6.e Idealised Me refined as rotating group:
 C67(H67A,H67B,H67C), C49(H49A,H49B,H49C), C50(H50A,H50B,H50C), C55(H55A,H55B,
 H55C), C43(H43A,H43B,H43C), C56(H56A,H56B,H56C), C35(H35A,H35B,H35C), C62(H62A,
 H62B,H62C), C61(H61A,H61B,H61C), C70(H70A,H70B,H70C), C69(H69A,H69B,H69C),
 C44(H44A,H44B,H44C), C5C(H5CA,H5CB,H5CC), C1C(H1CA,H1CB,H1CC), C1B(H1BA,H1BB,
 H1BC)
6.f Idealised tetrahedral OH refined as rotating group:
 O2B(H2B)
;
_shelx_res_checksum              23045
_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 4.743
_oxdiff_exptl_absorpt_empirical_full_min 0.389