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_4123642
_publ_section_title
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 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_formula_moiety         'C69 H94 N6 O9, 1.6(C H Cl3), 1.4(C5 H12)'
_chemical_formula_sum            'C77.57 H112.32 Cl4.82 N6 O9'
_chemical_formula_weight         1443.83
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-05-06
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.111(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9161(8)
_cell_length_b                   27.097(4)
_cell_length_c                   25.5162(16)
_cell_measurement_reflns_used    9122
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      73.23
_cell_measurement_theta_min      2.39
_cell_volume                     8175.6(14)
_computing_cell_refinement       'SAINT+ Ver. 8.34A (Bruker-AXS, 2014)'
_computing_data_collection       'APEX2 Ver. 2014.1-1 (Bruker-AXS, 2014)'
_computing_data_reduction        'SAINT+ Ver. 8.34A (Bruker-AXS, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '0.60\ \w and 0.6\ \f scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'equatorially mounted graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_laue_measured_fraction_full 0.981
_diffrn_reflns_laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            137980
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         73.224
_diffrn_reflns_theta_min         3.262
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Siemens, K FFCU 2K 90'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.001
_exptl_absorpt_correction_T_max  0.6156
_exptl_absorpt_correction_T_min  0.3626
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0766 before and 0.0421 after correction.
The Ratio of minimum to maximum transmission is 0.5890.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3095
_exptl_crystal_size_max          0.79
_exptl_crystal_size_mid          0.548
_exptl_crystal_size_min          0.358
_refine_diff_density_max         1.134
_refine_diff_density_min         -0.904
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1076
_refine_ls_number_reflns         15878
_refine_ls_number_restraints     559
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0573
_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^)+(0.0665P)^2^+8.3827P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.1488
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15162
_reflns_number_total             15878
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            Gellman157.cif
_cod_data_source_block           gellman157
_cod_depositor_comments
'Adding full bibliography for 4123639--4123645.cif.'
_cod_original_cell_volume        8175.4(14)
_cod_database_code               4123642
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.534
_shelx_estimated_absorpt_t_min   0.301
_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
2. Restrained distances
 O9A-C62 \\sim O9-C62
 with sigma of 0.01
 O9-C62 \\sim O9A-C62
 with sigma of 0.01
 O9-C63 \\sim O9A-C63A
 with sigma of 0.01
 C64-C63 \\sim C64A-C63A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Cl8B \\sim Cl7A \\sim C77A \\sim Cl9A \\sim Cl8A \\sim C76 \\sim Cl7C \\sim C77
\\sim C78 \\sim C77C \\sim C79 \\sim Cl9C \\sim Cl8C \\sim C80 \\sim Cl7B \\sim
Cl9B \\sim C77B: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.02
O9 \\sim C63 \\sim C64 \\sim C65 \\sim C66 \\sim C67 \\sim C68 \\sim C69 \\sim
O9A \\sim C63A \\sim C64A \\sim C65A \\sim C66A \\sim C67A \\sim C68A \\sim
C69A: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
C72 \\sim C73 \\sim C74 \\sim C75 \\sim C71A \\sim C72A \\sim C73A \\sim C74A
\\sim C75A \\sim Cl4B \\sim Cl6B \\sim Cl5B \\sim C71B \\sim C71: within 1.7A
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uiso(Cl9C) = Uiso(Cl7C) = Uiso(Cl8C)
4. Others
 1*[Sof(C71)+Sof(H71A)+Sof(H71B)+Sof(H71C)+Sof(C72)+Sof(H72A)+Sof(H72B)+
 Sof(C73)+Sof(H73A)+Sof(H73B)+Sof(C74)+Sof(H74A)+Sof(H74B)+Sof(C75)+Sof(H75A)+
 Sof(H75B)+Sof(H75C)]+1*[Sof(C71A)+Sof(H71D)+Sof(H71E)+Sof(H71F)+Sof(C72A)+
 Sof(H72C)+Sof(H72D)+Sof(C73A)+Sof(H73C)+Sof(H73D)+Sof(C74A)+Sof(H74C)+
 Sof(H74D)+Sof(C75A)+Sof(H75D)+Sof(H75E)+Sof(H75F)]+1*[Sof(Cl4B)+Sof(Cl6B)+
 Sof(Cl5B)+Sof(C71B)+Sof(H71G)]=1 with esd of 0
 1*[Sof(C76)+Sof(H76A)+Sof(H76B)+Sof(H76C)+Sof(C77)+Sof(H77A)+Sof(H77B)+
 Sof(C78)+Sof(H78A)+Sof(H78B)+Sof(C79)+Sof(H79A)+Sof(H79B)+Sof(C80)+Sof(H80A)+
 Sof(H80B)+Sof(H80C)]+1*[Sof(Cl7A)+Sof(Cl8A)+Sof(Cl9A)+Sof(C77A)+Sof(H77C)]+1*
 [Sof(Cl7B)+Sof(Cl8B)+Sof(Cl9B)+Sof(C77B)+Sof(H77D)]+1*[Sof(Cl9C)+Sof(Cl7C)+
 Sof(Cl8C)+Sof(C77C)+Sof(H77E)]=1 with esd of 0
 Sof(O9A)=Sof(C63A)=Sof(H63C)=Sof(H63D)=Sof(C64A)=Sof(C69A)=Sof(H69A)=
 Sof(C68A)=Sof(H68A)=Sof(C67A)=Sof(H67A)=Sof(C66A)=Sof(H66A)=Sof(C65A)=
 Sof(H65A)=1-FVAR(1)
 Sof(O9)=Sof(C63)=Sof(H63A)=Sof(H63B)=Sof(C64)=Sof(C65)=Sof(H65)=Sof(C66)=
 Sof(H66)=Sof(C67)=Sof(H67)=Sof(C68)=Sof(H68)=Sof(C69)=Sof(H69)=FVAR(1)
 Sof(C71)=Sof(H71A)=Sof(H71B)=Sof(H71C)=Sof(C72)=Sof(H72A)=Sof(H72B)=Sof(C73)=
 Sof(H73A)=Sof(H73B)=Sof(C74)=Sof(H74A)=Sof(H74B)=Sof(C75)=Sof(H75A)=Sof(H75B)=
 Sof(H75C)=FVAR(2)
 Sof(C71A)=Sof(H71D)=Sof(H71E)=Sof(H71F)=Sof(C72A)=Sof(H72C)=Sof(H72D)=
 Sof(C73A)=Sof(H73C)=Sof(H73D)=Sof(C74A)=Sof(H74C)=Sof(H74D)=Sof(C75A)=
 Sof(H75D)=Sof(H75E)=Sof(H75F)=FVAR(3)
 Sof(Cl4B)=Sof(Cl6B)=Sof(Cl5B)=Sof(C71B)=Sof(H71G)=FVAR(4)
 Sof(C76)=Sof(H76A)=Sof(H76B)=Sof(H76C)=Sof(C77)=Sof(H77A)=Sof(H77B)=Sof(C78)=
 Sof(H78A)=Sof(H78B)=Sof(C79)=Sof(H79A)=Sof(H79B)=Sof(C80)=Sof(H80A)=Sof(H80B)=
 Sof(H80C)=FVAR(5)
 Sof(Cl7A)=Sof(Cl8A)=Sof(Cl9A)=Sof(C77A)=Sof(H77C)=FVAR(6)
 Sof(Cl7B)=Sof(Cl8B)=Sof(Cl9B)=Sof(C77B)=Sof(H77D)=FVAR(7)
 Sof(Cl9C)=Sof(Cl7C)=Sof(Cl8C)=Sof(C77C)=Sof(H77E)=FVAR(8)
5.a Free rotating group:
 C71A(C72A,C73A,C74A,C75A), Cl4B(Cl6B,Cl5B,C71B), C76(C77,C78,C79,C80),
 Cl7A(Cl8A,Cl9A,C77A), Cl7B(Cl8B,Cl9B,C77B), Cl9C(Cl7C,Cl8C,C77C)
5.b Ternary CH refined with riding coordinates:
 C6(H6A), C15(H15), C20(H20), C21(H21), C25(H25), C34(H34), C39(H39), C40(H40),
  C44(H44), C53(H53), C58(H58), C59(H59), C70(H70), C71B(H71G), C77A(H77C),
 C77B(H77D), C77C(H77E)
5.c Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B),
 C22(H22A,H22B), C26(H26A,H26B), C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B),
  C38(H38A,H38B), C41(H41A,H41B), C45(H45A,H45B), C54(H54A,H54B), C55(H55A,
 H55B), C56(H56A,H56B), C57(H57A,H57B), C60(H60A,H60B), C63(H63A,H63B),
 C63A(H63C,H63D), C72(H72A,H72B), C73(H73A,H73B), C74(H74A,H74B), C72A(H72C,
 H72D), C73A(H73C,H73D), C74A(H74C,H74D), C77(H77A,H77B), C78(H78A,H78B),
 C79(H79A,H79B)
5.d Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), N4(H4), N5(H5), N6(H6), C9(H9), C10(H10), C11(H11),
 C12(H12), C13(H13), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C47(H47),
  C48(H48), C49(H49), C50(H50), C51(H51), C65(H65), C66(H66), C67(H67),
 C68(H68), C69(H69), C69A(H69A), C68A(H68A), C67A(H67A), C66A(H66A), C65A(H65A)
5.e Fitted hexagon refined as free rotating group:
 C64(C65,C66,C67,C68,C69), C64A(C69A,C68A,C67A,C66A,C65A)
5.f Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C23(H23A,H23B,H23C),
 C42(H42A,H42B,H42C), C61(H61A,H61B,H61C), C71(H71A,H71B,H71C), C75(H75A,H75B,
 H75C), C71A(H71D,H71E,H71F), C75A(H75D,H75E,H75F), C76(H76A,H76B,H76C),
 C80(H80A,H80B,H80C)
;
_shelx_res_checksum              67533
_shelx_hkl_checksum              89316