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_1549684
_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         'C72 H82 N8 O9, 2.75(H2 O)'
_chemical_formula_sum            'C72 H87.5 N8 O11.75'
_chemical_formula_weight         1252.99
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-05-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2018-05-16 deposited with the CCDC.
2018-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.976(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5782(6)
_cell_length_b                   18.4753(5)
_cell_length_c                   24.4315(7)
_cell_measurement_reflns_used    9794
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      68.2500
_cell_measurement_theta_min      2.9820
_cell_volume                     7027.5(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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.0
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.979
_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     86.70 265.70   1.00   11.00    --  113.00  73.87  24.21  179
  2  \f    -25.79 332.43   1.00   11.00 159.16 110.00  73.87    --   358
  3  \f    -23.83 172.29   1.00   11.00  96.79  95.00  73.87    --   196
  4  \w      0.70 147.66   1.00    5.50    --   20.00  73.87  -5.79  147
  5  \f    104.44 275.65   1.00   11.00 163.53  95.00  73.87    --   171
  6  \f     72.34 258.57   1.00   11.00 139.21 113.00  73.87    --   186
  7  \f    177.25 300.40   1.00    5.50  -6.38 -75.00  73.87    --   123
  8  \w     99.74 247.74   1.00   11.00    --  111.00  73.87 184.21  148
  9  \f     36.62 178.71   1.00   11.00 234.21 110.00  73.87    --   142
 10  \f    187.02 268.07   1.00    5.50 121.93  25.00  73.87    --    81
 11  \w    124.93 214.93   1.00   11.00    --  105.00  73.87 129.21   90
 12  \w     87.44 218.44   1.00   11.00    --  113.00  73.87 229.21  131
 13  \w     61.15 134.15   1.00   11.00    --   90.00  73.87 109.21   73
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0371541000
_diffrn_orient_matrix_UB_12      -0.0313456000
_diffrn_orient_matrix_UB_13      -0.0526035000
_diffrn_orient_matrix_UB_21      0.0835487000
_diffrn_orient_matrix_UB_22      -0.0198108000
_diffrn_orient_matrix_UB_23      0.0320695000
_diffrn_orient_matrix_UB_31      -0.0378700000
_diffrn_orient_matrix_UB_32      -0.0746648000
_diffrn_orient_matrix_UB_33      0.0136006000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0999
_diffrn_reflns_av_unetI/netI     0.0865
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            47191
_diffrn_reflns_point_group_measured_fraction_full 0.784
_diffrn_reflns_point_group_measured_fraction_max 0.780
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.485
_diffrn_reflns_theta_min         1.809
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90239
_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    1.184
_exptl_crystal_description       plate
_exptl_crystal_F_000             2678
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2256
_refine_ls_number_reflns         20163
_refine_ls_number_restraints     5703
_refine_ls_restrained_S_all      0.868
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0636P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1572
_reflns_Friedel_coverage         0.542
_reflns_Friedel_fraction_full    0.574
_reflns_Friedel_fraction_max     0.567
_reflns_number_gt                12076
_reflns_number_total             20163
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc02532k2.cif
_cod_data_source_block           s4270
_cod_depositor_comments
'Adding full bibliography for 1549682--1549686.cif.'
_cod_original_formula_sum        'C72 H87.50 N8 O11.75'
_cod_database_code               1549684
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C6 H6 O6 N6'
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.859
_reflns_odcompleteness_completeness 97.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.37
_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,
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 C109-C1_4 \\sim C1_6-C109
 with sigma of 0.02
3. 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
Uanis(C14_7) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C13_5) \\sim Ueq, Uanis(C13_2) \\sim Ueq, Uanis(C12_2) \\sim Ueq,
Uanis(C12_5) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C115) \\sim Ueq, Uanis(C109) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C9_6) \\sim Ueq, Uanis(C9_4) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C12_7) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. 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
5. Same fragment restrains
{C1_2, C2_2, C3_2, C4_2, C5_2, C6_2, C7_2, C8_2, C9_2, C10_2, C11_2, C12_2,
C13_2, C14_2, C15_2, C16_2}
{C1_3, C2_3, C3_3, C4_3, C5_3, C6_3, C7_3, C8_3, C9_3, C10_3, C11_3, C12_3,
C13_3, C14_3, C15_3, C16_3}
{C1_4, C2_4, C3_4, C4_4, C5_4, C6_4, C7_4, C8_4, C9_4, C10_4, C11_4, C12_4,
C13_4, C14_4, C15_4, C16_4}
{C1_5, C2_5, C3_5, C4_5, C5_5, C6_5, C7_5, C8_5, C9_5, C10_5, C11_5, C12_5,
C13_5, C14_5, C15_5, C16_5}
{C1_6, C2_6, C3_6, C4_6, C5_6, C6_6, C7_6, C8_6, C9_6, C10_6, C11_6, C12_6,
C13_6, C14_6, C15_6, C16_6}
{C1_7, C2_7, C3_7, C4_7, C5_7, C6_7, C7_7, C8_7, C9_7, C10_7, C11_7, C12_7,
C13_7, C14_7, C15_7, C16_7}
as
{C1_1, C2_1, C3_1, C4_1, C5_1, C6_1, C7_1, C8_1, C9_1, C10_1, C11_1, C12_1,
C13_1, C14_1, C15_1, C16_1} sigma for 1-2: 0.02 1-3: 0.04
6. Others
 Sof(H10A)=Sof(N116)=Sof(H116)=Sof(H52A)=Sof(H63C)=Sof(H63D)=Sof(O118)=
 Sof(C119)=Sof(H11D)=Sof(H11E)=Sof(H11F)=Sof(C117)=Sof(C62A)=Sof(C61A)=
 Sof(H61A)=Sof(C60A)=Sof(H60A)=Sof(C59A)=Sof(H59A)=Sof(C58A)=Sof(H58A)=
 Sof(C57A)=Sof(H57A)=Sof(O2C)=Sof(H2CA)=Sof(H2CB)=Sof(O1C)=Sof(H1CA)=Sof(H1CB)=
 Sof(C115)=Sof(H115)=Sof(C114)=Sof(H114)=Sof(C1)=Sof(C2)=Sof(H2)=Sof(C3)=
 Sof(H3)=Sof(C4)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(C8)=Sof(H8)=
 Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=
 Sof(C14)=Sof(C15)=Sof(C16)=Sof(C1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=
 Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=
 Sof(C10)=Sof(H10)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=
 Sof(C15)=Sof(C16)=Sof(C1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(C5)=
 Sof(H5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=
 Sof(H10)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(C15)=
 Sof(C16)=1-FVAR(1)
 Sof(H107)=Sof(H52)=Sof(C108)=Sof(H108)=Sof(H63A)=Sof(H63B)=Sof(C109)=
 Sof(H109)=Sof(O5B)=Sof(H5BA)=Sof(H5BB)=Sof(O6B)=Sof(H6BA)=Sof(H6BB)=Sof(C62)=
 Sof(C59)=Sof(H59)=Sof(C58)=Sof(H58)=Sof(C60)=Sof(H60)=Sof(C57)=Sof(H57)=
 Sof(C111)=Sof(C113)=Sof(H11A)=Sof(H11B)=Sof(H11C)=Sof(O112)=Sof(C61)=Sof(H61)=
 Sof(N110)=Sof(H110)=Sof(C1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(C5)=
 Sof(H5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=
 Sof(H10)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(C15)=
 Sof(C16)=Sof(C1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(C5)=Sof(H5)=
 Sof(C6)=Sof(H6)=Sof(C7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=
 Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(C15)=Sof(C16)=
 Sof(C1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(C5)=Sof(H5)=Sof(C6)=
 Sof(H6)=Sof(C7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=Sof(C11)=
 Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(C15)=Sof(C16)=FVAR(1)
 Fixed Sof: O3B(0.5) H3BA(0.5) H3BB(0.5) O4B(0.5) H4BA(0.5) H4BB(0.5) O7B(0.5)
 H7BA(0.5) H7BB(0.5)
7.a Riding coordinates:
 O1B(H1BA,H1BB), O2B(H2BA,H2BB), O5B(H5BA,H5BB), O6B(H6BA,H6BB), O3B(H3BA,
 H3BB), O4B(H4BA,H4BB), O2C(H2CA,H2CB), O1C(H1CA,H1CB), O7B(H7BA,H7BB)
7.b Ternary CH refined with riding coordinates:
 C52(H52), C52(H52A), C70(H70), C78(H78), C108(H108), C51(H51), C21(H21),
 C109(H109), C13(H13), C115(H115), C114(H114)
7.c Secondary CH2 refined with riding coordinates:
 C63(H63A,H63B), C63(H63C,H63D), C7(H7A,H7B)
7.d Aromatic/amide H refined with riding coordinates:
 N26(H26), N95(H95), N38(H38), N67(H67), N44(H44), N83(H83), N50(H50),
 N18(H18), N75(H75), N53(H53), N11(H11), N32(H32), N89(H89), N107(H107),
 N107(H10A), N116(H116), C4(H4), C5(H5), C3(H3), C1(H1), C2(H2), C59(H59),
 C58(H58), C60(H60), C57(H57), C61(H61), C61A(H61A), C60A(H60A), C59A(H59A),
 C58A(H58A), C57A(H57A), N110(H110), N101(H101), C2(H2), C3(H3), C5(H5), C6(H6),
  C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C2(H2), C3(H3), C5(H5), C6(H6),
 C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C2(H2), C3(H3), C5(H5), C6(H6),
 C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C2(H2), C3(H3), C5(H5), C6(H6),
 C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C2(H2), C3(H3), C5(H5), C6(H6),
 C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C2(H2), C3(H3), C5(H5), C6(H6),
 C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C2(H2), C3(H3), C5(H5), C6(H6),
 C8(H8), C9(H9), C10(H10), C12(H12), C13(H13)
7.e Idealised Me refined as rotating group:
 C69(H69A,H69B,H69C), C80(H80A,H80B,H80C), C85(H85A,H85B,H85C), C20(H20A,H20B,
 H20C), C29(H29A,H29B,H29C), C77(H77A,H77B,H77C), C28(H28A,H28B,H28C), C92(H92A,
 H92B,H92C), C34(H34A,H34B,H34C), C56(H56A,H56B,H56C), C86(H86A,H86B,H86C),
 C72(H72A,H72B,H72C), C79(H79A,H79B,H79C), C23(H23A,H23B,H23C), C35(H35A,H35B,
 H35C), C71(H71A,H71B,H71C), C41(H41A,H41B,H41C), C22(H22A,H22B,H22C), C40(H40A,
 H40B,H40C), C91(H91A,H91B,H91C), C97(H97A,H97B,H97C), C98(H98A,H98B,H98C),
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C113(H11A,H11B,
 H11C), C119(H11D,H11E,H11F), C103(H10B,H10C,H10D), C104(H10E,H10F,H10G),
 C47(H47A,H47B,H47C), C46(H46A,H46B,H46C)
;
_shelx_res_checksum              5892
_shelx_fab_checksum              59803
_olex2_diffrn_ambient_temperature_device 'Cryostream 700'
_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 1.235
_oxdiff_exptl_absorpt_empirical_full_min 0.844