Beta-Strand mimics based on tetrahydropyridazinedione (tpd) peptide stitching
Chang Won Kang; Matthew P. Sarnowski; Sujeewa Ranatunga; Lukasz Wojtas; Rainer S. Metcalf; Wayne C. Guida; Juan R. Del Valle; Chem.Commun. 51 (2015) 16259–; doi:10.1039/C5cc07189E

data_7118031
_publ_section_title
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 Beta-Strand mimics based on tetrahydropyridazinedione (tpd) peptide
 stitching
;
_journal_name_full               Chem.Commun.
_journal_page_first              16259
_journal_paper_doi               10.1039/C5cc07189E
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H22 N4 O5, C2 H6 O'
_chemical_formula_sum            'C24 H28 N4 O6'
_chemical_formula_weight         468.50
_chemical_name_common            Fmoc-tpd-Ala-NH2
_chemical_name_systematic        10
_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   mixed
_audit_creation_date             2015-01-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.06 svn.r3119 for OlexSys, GUI svn.r4979)
;
_audit_update_record
;
2015-08-26 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1328(2)
_cell_length_b                   16.7206(4)
_cell_length_c                   22.9284(6)
_cell_measurement_reflns_used    9768
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.86
_cell_measurement_theta_min      3.27
_cell_volume                     2351.17(11)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.99
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            19352
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.400
_diffrn_reflns_theta_min         3.271
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.6794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1086 before and 0.0678 after correction.
The Ratio of minimum to maximum transmission is 0.9020.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       plate
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1507 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.15(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         4184
_refine_ls_number_restraints     70
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0438P)^2^+0.6271P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0963
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                3827
_reflns_number_total             4184
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc07189e2.cif
_cod_data_source_block           ms113_0m
_cod_database_code               7118031
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.917
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,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
 C28-C27 = C30-C27
 1.52 with sigma of 0.01
 C31-C30 = C33-C30 = C33-C16 = C16-C17 = C35-C17 = C35-C31
 1.39 with sigma of 0.01
 C34-C2 = C2-C13 = C32-C13 = C32-C28 = C29-C28 = C34-C29
 1.39 with sigma of 0.01
 C33-C32
 1.48 with sigma of 0.01
 O23-C25
 1.36 with sigma of 0.01
 O24-C25
 1.205 with sigma of 0.01
 C32-C30 = C33-C28
 2.34 with sigma of 0.02
 C30-C28
 2.37 with sigma of 0.02
 C27-C32 = C33-C27
 2.41 with sigma of 0.02
 O24-O23
 2.27 with sigma of 0.02
 C27-O23
 2.44 with sigma of 0.02
 C16-C31 = C17-C30 = C33-C35 = C13-C29 = C34-C32 = C2-C28
 2.79 with sigma of 0.02
 C33-C17 = C30-C35 = C2-C32 = C34-C28
 2.4 with sigma of 0.02
 C16-C35 = C33-C31 = C13-C28 = C2-C29
 2.4 with sigma of 0.02
 N2-C25
 1.34 with sigma of 0.01
 O23-N2
 2.21 with sigma of 0.02
 N2-O24
 2.26 with sigma of 0.02
 C27-C26
 1.51 with sigma of 0.01
 H29_$1-H20B
 -2.2 with sigma of 0.02
3. Restrained planarity
 C2, C13, C28, C29, C32, C34
 with sigma of 0.01
 C16, C17, C30, C31, C33, C35
 with sigma of 0.01
 C27, C30, C28, C32, C33
 with sigma of 0.01
 N2, O23, C25, O24
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C3 \\sim C34: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
C14 \\sim C32: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
C8 \\sim C25: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.02
5. Others
 Sof(H2B)=Sof(H2BB)=Sof(H13A)=Sof(H16A)=Sof(H17A)=Sof(C26)=Sof(H26A)=Sof(H26B)=
 Sof(C27)=Sof(H27)=Sof(O23)=Sof(C30)=Sof(C28)=Sof(C29)=Sof(H29)=Sof(C25)=
 Sof(O24)=Sof(C31)=Sof(H31)=Sof(C32)=Sof(C33)=Sof(C34)=Sof(H34)=Sof(C35)=
 Sof(H35)=1-FVAR(1)
 Sof(O1)=Sof(H2A)=Sof(O3)=Sof(H2AA)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4A)=Sof(C5)=
 Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(C8)=Sof(H13)=Sof(C14)=Sof(C15)=
 Sof(H16)=Sof(H17)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=Sof(C1A)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C1(H1), C6(H6), C10(H10), C27(H27)
6.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C20(H20A,H20B), C1B(H1BA,H1BB), C26(H26A,H26B)
6.c Aromatic/amide H refined with riding coordinates:
 N2(H2B), C2(H2AA), C2(H2BB), C3(H3), C4(H4A), C13(H13), C13(H13A), C16(H16),
 C16(H16A), C17(H17), C17(H17A), C18(H18), C19(H19), C29(H29), C31(H31),
 C34(H34), C35(H35)
6.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
6.e Idealised tetrahedral OH refined as rotating group:
 O22(H22)
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_olex2_submission_special_instructions 'No special instructions were received'