Heterogeneous h-bonding in a foldamer helix.
Fisher, Brian F.; Guo, Li; Dolinar, Brian S.; Guzei, Ilia A.; Gellman, Samuel H.; Journal of the American Chemical Society 137 (2015) 6484–6487; doi:10.1021/jacs.5b03382

data_4123643
_publ_section_title
;
 Heterogeneous h-bonding in a foldamer helix.
;
_journal_issue                   20
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6484
_journal_page_last               6487
_journal_paper_doi               10.1021/jacs.5b03382
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C41 H65 N5 O8, C2 H6 O, C7 H16'
_chemical_formula_sum            'C50 H87 N5 O9'
_chemical_formula_weight         902.24
_chemical_name_systematic
;
 ?
;
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-02-07
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.01.22 svn.r2872 for OlexSys, GUI svn.r4747)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.534(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4361(18)
_cell_length_b                   18.178(3)
_cell_length_c                   22.458(3)
_cell_measurement_reflns_used    9777
_cell_measurement_temperature    100
_cell_measurement_theta_max      74.403
_cell_measurement_theta_min      3.149
_cell_volume                     5392.7(14)
_computing_cell_refinement       'SAINT+ Ver. 8.34A (Bruker-AXS, 2013)'
_computing_data_collection       'APEX2 Ver. 2013.12-0 (Bruker-AXS, 2013)'
_computing_data_reduction        'SAINT+ Ver. 8.34A (Bruker-AXS, 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008-2013)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008-2013)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008-2013)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       '4-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE diffractometer'
_diffrn_measurement_method       '0.2\ \w and 0.2\ \f scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_laue_measured_fraction_full 0.992
_diffrn_reflns_laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            45447
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         74.508
_diffrn_reflns_theta_min         3.149
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms HB'
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1202 before and 0.0715 after correction.
The Ratio of minimum to maximum transmission is 0.8200.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.111
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1976
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1127
_refine_ls_number_reflns         20128
_refine_ls_number_restraints     64
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0894
_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^)+(0.2500P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2495
_refine_ls_wR_factor_ref         0.2606
_reflns_Friedel_coverage         0.939
_reflns_friedel_fraction_full    0.994
_reflns_friedel_fraction_max     0.982
_reflns_number_gt                18498
_reflns_number_total             20128
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            gellman153.cif
_cod_data_source_block           gellman153
_cod_depositor_comments
'Adding full bibliography for 4123639--4123645.cif.'
_cod_original_cell_volume        5392.7(13)
_cod_database_code               4123643
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.849
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Same fragment restrains
{O9A, C42A, C43A}
{O10, C44, C45}
{O10, C44A, C45A}
as
{O9, C42, C43}
{C53, C54, C55, C56, C57, C58, C59}
{C53A, C54A, C55A, C56A, C57A, C58A, C59A}
as
{C46, C47, C48, C49, C50, C51, C52}
3. Others
 Sof(O9A)=Sof(H9AA)=Sof(C42A)=Sof(H42C)=Sof(H42D)=Sof(C43A)=Sof(H43D)=
 Sof(H43E)=Sof(H43F)=1-FVAR(1)
 Sof(O9)=Sof(H9B)=Sof(C42)=Sof(H42A)=Sof(H42B)=Sof(C43)=Sof(H43A)=Sof(H43B)=
 Sof(H43C)=FVAR(1)
 Uiso(C46)=Uiso(C47)=Uiso(C48)=Uiso(C49)=Uiso(C50)=Uiso(C51)=Uiso(C52)=
 Uiso(C46A)=Uiso(C47A)=Uiso(C48A)=Uiso(C49A)=Uiso(C50A)=Uiso(C51A)=Uiso(C52A)=
 Uiso(C53)=Uiso(C54)=Uiso(C55)=Uiso(C56)=Uiso(C57)=Uiso(C58)=Uiso(C59)=
 Uiso(C53A)=Uiso(C54A)=Uiso(C55A)=Uiso(C56A)=Uiso(C57A)=Uiso(C58A)=Uiso(C59A)=
 FVAR(2)
 Sof(H10E)=Sof(C44A)=Sof(H44A)=Sof(H44B)=Sof(C45A)=Sof(H45A)=Sof(H45B)=
 Sof(H45C)=1-FVAR(3)
 Sof(H10)=Sof(C44)=Sof(H44C)=Sof(H44D)=Sof(C45)=Sof(H45D)=Sof(H45E)=Sof(H45F)=
 FVAR(3)
 Uiso(C44A)=Uiso(C45A)=Uiso(C44)=Uiso(C45)=FVAR(4)
 Fixed Sof: C46(0.5) H46A(0.5) H46B(0.5) H46C(0.5) C47(0.5) H47A(0.5)
 H47B(0.5) C48(0.5) H48A(0.5) H48B(0.5) C49(0.5) H49A(0.5) H49B(0.5) C50(0.5)
 H50A(0.5) H50B(0.5) C51(0.5) H51A(0.5) H51B(0.5) C52(0.5) H52A(0.5) H52B(0.5)
 H52C(0.5) C46A(0.5) H46D(0.5) H46E(0.5) H46F(0.5) C47A(0.5) H47C(0.5)
 H47D(0.5) C48A(0.5) H48C(0.5) H48D(0.5) C49A(0.5) H49C(0.5) H49D(0.5)
 C50A(0.5) H50C(0.5) H50D(0.5) C51A(0.5) H51C(0.5) H51D(0.5) C52A(0.5)
 H52D(0.5) H52E(0.5) H52F(0.5) C53(0.5) H53A(0.5) H53B(0.5) H53C(0.5) C54(0.5)
 H54A(0.5) H54B(0.5) C55(0.5) H55A(0.5) H55B(0.5) C56(0.5) H56A(0.5) H56B(0.5)
 C57(0.5) H57A(0.5) H57B(0.5) C58(0.5) H58A(0.5) H58B(0.5) C59(0.5) H59A(0.5)
 H59B(0.5) H59C(0.5) C53A(0.5) H53D(0.5) H53E(0.5) H53F(0.5) C54A(0.5)
 H54C(0.5) H54D(0.5) C55A(0.5) H55C(0.5) H55D(0.5) C56A(0.5) H56C(0.5)
 H56D(0.5) C57A(0.5) H57C(0.5) H57D(0.5) C58A(0.5) H58C(0.5) H58D(0.5)
 C59A(0.5) H59D(0.5) H59E(0.5) H59F(0.5)
4.a Ternary CH refined with riding coordinates:
 C6(H6), C9(H9), C14(H14), C15(H15), C19(H19), C22(H22), C27(H27), C28(H28),
 C32(H32), C6A(H6A), C9A(H9A), C14A(H14A), C15A(H15A), C19A(H19A), C22A(H22A),
 C27A(H27A), C28A(H28A), C32A(H32A)
4.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C16(H16A,
 H16B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B),
 C29(H29A,H29B), C35(H35A,H35B), C10A(H10C,H10D), C11A(H11C,H11D), C12A(H12C,
 H12D), C13A(H13C,H13D), C16A(H16C,H16D), C23A(H23C,H23D), C24A(H24C,H24D),
 C25A(H25C,H25D), C26A(H26C,H26D), C29A(H29C,H29D), C35A(H35C,H35D), C42(H42A,
 H42B), C42A(H42C,H42D), C44A(H44A,H44B), C44(H44C,H44D), C47(H47A,H47B),
 C48(H48A,H48B), C49(H49A,H49B), C50(H50A,H50B), C51(H51A,H51B), C47A(H47C,
 H47D), C48A(H48C,H48D), C49A(H49C,H49D), C50A(H50C,H50D), C51A(H51C,H51D),
 C54(H54A,H54B), C55(H55A,H55B), C56(H56A,H56B), C57(H57A,H57B), C58(H58A,H58B),
  C54A(H54C,H54D), C55A(H55C,H55D), C56A(H56C,H56D), C57A(H57C,H57D), C58A(H58C,
 H58D)
4.c Me refined with riding coordinates:
 C45A(H45A,H45B,H45C), C45(H45D,H45E,H45F), C46(H46A,H46B,H46C), C52(H52A,H52B,
 H52C), C46A(H46D,H46E,H46F), C52A(H52D,H52E,H52F), C53(H53A,H53B,H53C),
 C59(H59A,H59B,H59C), C53A(H53D,H53E,H53F), C59A(H59D,H59E,H59F)
4.d Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), N4(H4), N5(H5), C37(H37), C38(H38), C39(H39),
 C40(H40), C41(H41), N1A(H1AA), N2A(H2AA), N3A(H3AA), N4A(H4A), N5A(H5A),
 C37A(H37A), C38A(H38A), C39A(H39A), C40A(H40A), C41A(H41A)
4.e Tetrahedral OH refined with riding coordinates:
 O10(H10), O10(H10E)
4.f Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C7(H7A,H7B,H7C), C17(H17A,
 H17B,H17C), C20(H20A,H20B,H20C), C30(H30A,H30B,H30C), C33(H33A,H33B,H33C),
 C1A(H1AB,H1AC,H1AD), C2A(H2AB,H2AC,H2AD), C3A(H3AB,H3AC,H3AD), C7A(H7AA,H7AB,
 H7AC), C17A(H17D,H17E,H17F), C20A(H20D,H20E,H20F), C30A(H30D,H30E,H30F),
 C33A(H33D,H33E,H33F), C43(H43A,H43B,H43C), C43A(H43D,H43E,H43F)
4.g Idealised tetrahedral OH refined as rotating group:
 O9(H9B), O9A(H9AA)
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_shelx_res_checksum              80742
_shelx_hkl_checksum              18108