The influence of backbone fluorination on the helicity of α/γ-hybrid peptides
Patel, Alpesh Ramanlal; Lawer, Aggie; Bhadbhade, Mohan; Hunter, Luke; Organic & Biomolecular Chemistry 22 (2024) 1608–1612; doi:10.1039/D3OB02016A

data_7159792
_publ_section_title
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 The influence of backbone fluorination on the helicity of \a/\g-hybrid
 peptides
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_journal_issue                   8
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              1608
_journal_page_last               1612
_journal_paper_doi               10.1039/D3OB02016A
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C56 H97 N9 O12'
_chemical_formula_sum            'C56 H97 N9 O12'
_chemical_formula_weight         1088.42
_space_group_crystal_system      tetragonal
_space_group_IT_number           78
_space_group_name_Hall           'P 4cw'
_space_group_name_H-M_alt        'P 43'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-04-03
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
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2023-08-03 deposited with the CCDC.	2024-01-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   17.7179(7)
_cell_length_b                   17.7179(7)
_cell_length_c                   81.727(3)
_cell_measurement_temperature    152.41
_cell_volume                     25656.1(17)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      152.41
_diffrn_measured_fraction_theta_full 0.902
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_device_type  'Bruker ApexII'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_av_unetI/netI     0.1218
_diffrn_reflns_Laue_measured_fraction_full 0.902
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       99
_diffrn_reflns_limit_l_min       -68
_diffrn_reflns_number            47584
_diffrn_reflns_point_group_measured_fraction_full 0.635
_diffrn_reflns_point_group_measured_fraction_max 0.617
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.868
_diffrn_reflns_theta_min         1.789
_exptl_absorpt_coefficient_mu    0.079
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_description       plate
_exptl_crystal_F_000             9472
_refine_diff_density_max         0.947
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 3886 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2813
_refine_ls_number_reflns         30683
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1274
_refine_ls_R_factor_gt           0.0748
_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^)+(0.1206P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1913
_refine_ls_wR_factor_ref         0.2284
_reflns_Friedel_coverage         0.386
_reflns_Friedel_fraction_full    0.364
_reflns_Friedel_fraction_max     0.346
_reflns_number_gt                18677
_reflns_number_total             30683
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob02016a2.cif
_cod_data_source_block           partial_a(1)(2)
_cod_depositor_comments
'Adding full bibliography for 7159791--7159792.cif.'
_cod_original_cell_volume        25656(2)
_cod_database_code               7159792
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
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1. Fixed Uiso
 At 1.2 times of:
  All C(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) groups
2. Restrained distances
 C24W-C24V \\sim C24X-C24W \\sim C24Y-C24X \\sim C24Y-C24Z \\sim C23D-C24Z
\\sim C23D-C24V
 with sigma of 0.02
 C23Q-C23C \\sim C23U-C23C \\sim C23T-C23U \\sim C23T-C23S \\sim C23R-C23S
\\sim C23R-C23Q
 with sigma of 0.02
 C24V-C24W \\sim C24V-C23D
 with sigma of 0.02
 C1G-C25D \\sim C24D-C25D \\sim C23D-C24D \\sim C1G-C1F
 with sigma of 0.02
 N8D-C22D \\sim N8D-C1L
 with sigma of 0.02
 C24D-C25D \\sim C1G-C25D
 with sigma of 0.02
 C24C-C25C \\sim C1P-C25C \\sim C1O-C1P \\sim C23C-C24C
 with sigma of 0.02
 N8C-C22C \\sim N8C-C1S
 with sigma of 0.02
3. Others
 Fixed Sof: C22C(0.65) H22C(0.65) H22D(0.65) C23C(0.65) C23Q(0.65) H23A(0.65)
 H23B(0.65) C23R(0.65) H23C(0.65) H23D(0.65) C23S(0.65) H23E(0.65) H23F(0.65)
 C23T(0.65) H23G(0.65) H23H(0.65) C23U(0.65) H23I(0.65) H23J(0.65) C24C(0.65)
 H24M(0.65) H24N(0.65) C1N(0.35) H1NA(0.35) H1NB(0.35) C1O(0.35) C1P(0.35)
 H1PA(0.35) H1PB(0.35) C1Q(0.35) H1QA(0.35) H1QB(0.35) C1R(0.35) H1RA(0.35)
 H1RB(0.35) C1S(0.35) H1SA(0.35) H1SB(0.35) C20(0.35) H20J(0.35) H20K(0.35)
 C23(0.35) H23K(0.35) H23L(0.35) H8D(0.65) H8DA(0.35) C22D(0.65) H22A(0.65)
 H22B(0.65) C23D(0.65) C24D(0.65) H24A(0.65) H24B(0.65) C24V(0.65) H24C(0.65)
 H24D(0.65) C24W(0.65) H24E(0.65) H24F(0.65) C24X(0.65) H24G(0.65) H24H(0.65)
 C24Y(0.65) H24I(0.65) H24J(0.65) C24Z(0.65) H24K(0.65) H24L(0.65) C1F(0.35)
 C1G(0.35) H1GA(0.35) H1GB(0.35) C1H(0.35) H1HA(0.35) H1HB(0.35) C1I(0.35)
 H1IA(0.35) H1IB(0.35) C1J(0.35) H1JA(0.35) H1JB(0.35) C1K(0.35) H1KA(0.35)
 H1KB(0.35) C1L(0.35) H1LA(0.35) H1LB(0.35) C1M(0.35) H1MA(0.35) H1MB(0.35)
4.a Secondary CH2 refined with riding coordinates:
 C4A(H4AA,H4AB), C5E(H5EA,H5EB), C5F(H5FA,H5FB), C5G(H5GA,H5GB), C5H(H5HA,
 H5HB), C5I(H5IA,H5IB), C6A(H6AA,H6AB), C10A(H10E,H10F), C11A(H11G,H11H),
 C12A(H12F,H12G), C16A(H16E,H16F), C17E(H17U,H17V), C17F(H17W,H17X), C17G(H17Y,
 H), C17H(H17Z,HA), C17I(H17,HB), C18A(H18H,H18I), C22A(H22E,H22F), C23E(H23M,
 H23N), C23F(H23O,H23P), C23G(H23Q,H23R), C23H(H23S,H23T), C23I(H23U,H23V),
 C24A(H24O,H24P), C4B(H4BA,H4BB), C5K(H5KA,H5KB), C5L(H5LA,H5LB), C5M(H5MA,
 H5MB), C5N(H5NA,H5NB), C5O(H5OA,H5OB), C6B(H6BA,H6BB), C10B(H10G,H10H),
 C11B(H11J,H11K), C12B(H12H,H12I), C16B(H16G,H16H), C17K(H2,HE), C17L(H3,HF),
 C17M(H4,HG), C17N(H5,HH), C17O(H6,HI), C18B(H18J,H18K), C22B(H22G,H22H),
 C23K(H23W,H23X), C23L(H23Y,HJ), C23M(H23Z,HK), C23N(H23,HL), C23O(H7,HM),
 C24B(H24Q,H24R), C4C(H4CA,H4CB), C5Q(H5QA,H5QB), C5R(H5RA,H5RB), C5S(H5SA,
 H5SB), C5T(H5TA,H5TB), C5U(H5UA,H5UB), C6C(H6CA,H6CB), C10C(H10C,H10D),
 C11C(H11E,H11F), C12C(H12C,H12D), C16C(H16C,H16D), C17Q(H17K,H17L), C17R(H17M,
 H17N), C17S(H17O,H17P), C17T(H17Q,H17R), C17U(H17S,H17T), C18C(H18C,H18D),
 C22C(H22C,H22D), C23Q(H23A,H23B), C23R(H23C,H23D), C23S(H23E,H23F), C23T(H23G,
 H23H), C23U(H23I,H23J), C24C(H24M,H24N), C1N(H1NA,H1NB), C1P(H1PA,H1PB),
 C1Q(H1QA,H1QB), C1R(H1RA,H1RB), C1S(H1SA,H1SB), C20(H20J,H20K), C23(H23K,H23L),
  C4D(H4DA,H4DB), C5V(H5VA,H5VB), C5W(H5WA,H5WB), C5X(H5XA,H5XB), C5Y(H5YA,
 H5YB), C5Z(H5ZA,H5ZB), C6D(H6DA,H6DB), C10D(H10A,H10B), C11D(H11A,H11B),
 C12D(H12A,H12B), C16D(H16A,H16B), C17V(H17A,H17B), C17W(H17C,H17D), C17X(H17E,
 H17F), C17Y(H17G,H17H), C17Z(H17I,H17J), C18D(H18A,H18B), C22D(H22A,H22B),
 C24D(H24A,H24B), C24V(H24C,H24D), C24W(H24E,H24F), C24X(H24G,H24H), C24Y(H24I,
 H24J), C24Z(H24K,H24L), C1G(H1GA,H1GB), C1H(H1HA,H1HB), C1I(H1IA,H1IB),
 C1J(H1JA,H1JB), C1K(H1KA,H1KB), C1L(H1LA,H1LB), C1M(H1MA,H1MB)
4.b Aromatic/amide H refined with riding coordinates:
 N1A(H1A), N2A(H2A), N3A(H3A), N4A(H4A), N5A(H5A), N6A(H6A), N7A(H7A),
 N8A(H8A), N9A(H9A), N1(H1), N1B(H1B), N2B(H2B), N3B(H3B), N5B(H5B), N6B(H6B),
 N7B(H7B), N8B(H8B), N9B(H9B), N1C(H1C), N2C(H2C), N3C(H3C), N4C(H4C), N5C(H5C),
  N6C(H6C), N7C(H7C), N8C(H8C), N9C(H9C), N1D(H1D), N2D(H2D), N3D(H3D),
 N4D(H4D), N5D(H5D), N6D(H6D), N7D(H7D), N8D(H8D), N8D(H8DA), N9D(H9D)
4.c Idealised Me refined as rotating group:
 C2E(H2EA,H2EB,H2EC), C2F(H2FA,H2FB,H2FC), C8E(H8EA,H8EB,H8EC), C8F(H8FA,H8FB,
 H8FC), C14E(H14G,H14H,H14I), C14F(H14J,H14K,H14L), C20E(H20L,H20M,H20N),
 C20F(H20O,H20P,H20Q), C26E(H26M,H26N,H26O), C26F(H26P,H26Q,H26R), C28E(H28S,
 H28T,H28U), C28F(H28V,H28W,H28X), C28G(H28Y,HC,HD), C2K(H2KA,H2KB,H2KC),
 C2L(H2LA,H2LB,H2LC), C8K(H8KA,H8KB,H8KC), C8L(H8LA,H8LB,H8LC), C14K(H14M,H14N,
 H14O), C14L(H14P,H14Q,H14R), C20K(H20R,H20S,H20T), C20L(H20U,H20V,H20W),
 C26K(H26S,H26T,H26U), C26L(H26V,H26W,H26X), C28K(H28Z,HN,HO), C28L(H28,HP,HQ),
 C28M(H8,HR,HS), C2Q(H2QA,H2QB,H2QC), C2R(H2RA,H2RB,H2RC), C8Q(H8QA,H8QB,H8QC),
 C8R(H8RA,H8RB,H8RC), C14Q(H14A,H14B,H14C), C14R(H14D,H14E,H14F), C18Q(H18E,
 H18F,H18G), C20R(H20G,H20H,H20I), C26Q(H26G,H26H,H26I), C26R(H26J,H26K,H26L),
 C28Q(H28J,H28K,H28L), C28R(H28M,H28N,H28O), C28S(H28P,H28Q,H28R), C2V(H2VA,
 H2VB,H2VC), C2W(H2WA,H2WB,H2WC), C8V(H8VA,H8VB,H8VC), C8W(H8WA,H8WB,H8WC),
 C13V(H13A,H13B,H13C), C13W(H13D,H13E,H13F), C20V(H20A,H20B,H20C), C20W(H20D,
 H20E,H20F), C26V(H26A,H26B,H26C), C26W(H26D,H26E,H26F), C28V(H28A,H28B,H28C),
 C28W(H28D,H28E,H28F), C28X(H28G,H28H,H28I)
4.d Idealised tetrahedral OH refined as rotating group:
 O12A(H12E), O11B(H11I), O11C(H11C), O11D(H11D)
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_shelx_res_checksum              74752
_olex2_submission_special_instructions 'No special instructions were received'