The role of the side chain in the conformational and self-assembly patterns of C2-symmetric Val and Phe pseudopeptidic derivatives
Gorla, Lingaraju; Martí-Centelles, Vicente; Altava, Belén; Burguete, M. Isabel; Luis, Santiago V.; CrystEngComm 21 (2019) 2398–; doi:10.1039/C8CE02088D

data_7232430
_publ_section_title
;
 The role of the side chain in the conformational and self-assembly
 patterns of C2-symmetric Val and Phe pseudopeptidic derivatives
;
_journal_issue                   14
_journal_name_full               CrystEngComm
_journal_page_first              2398
_journal_paper_doi               10.1039/C8CE02088D
_journal_volume                  21
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C22 H31 N5 O2'
_chemical_formula_sum            'C22 H31 N5 O2'
_chemical_formula_weight         397.52
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2bc 2'
_space_group_name_H-M_alt        'P 2 21 21'
_symmetry_space_group_name_Hall  'P 2bc 2'
_symmetry_space_group_name_H-M   'P 2 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-11-20
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2018-11-21 deposited with the CCDC.    2019-02-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.01883(14)
_cell_length_b                   16.5007(5)
_cell_length_c                   25.5451(7)
_cell_measurement_reflns_used    3060
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3420
_cell_measurement_theta_min      4.3550
_cell_volume                     2115.50(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4051
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details
;
  1 omega  -49.00   34.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680   38.0000 -120.0000 83

  2 omega  -14.00   51.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0680  -57.0000   60.0000 65

  3 omega   91.00  117.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0680  178.0000  -60.0000 26

  4 omega  134.00  175.00   1.0000  175.0000
omega____ theta____ kappa____ phi______ frames
    -      101.3070  125.0000  120.0000 41

  5 omega   27.00   56.00   1.0000  175.0000
omega____ theta____ kappa____ phi______ frames
    -      101.3070  -45.0000  -60.0000 29

  6 omega   24.00   89.00   1.0000  175.0000
omega____ theta____ kappa____ phi______ frames
    -      101.3070  -30.0000   60.0000 65

  7 omega   39.00   89.00   1.0000  175.0000
omega____ theta____ kappa____ phi______ frames
    -      101.3070  -45.0000    0.0000 50

  8 omega   30.00   91.00   1.0000  175.0000
omega____ theta____ kappa____ phi______ frames
    -      101.3070  -94.0000  -90.0000 61

  9 omega   43.00   87.00   1.0000  175.0000
omega____ theta____ kappa____ phi______ frames
    -      101.3070  -30.0000  -60.0000 44

 10 omega   46.00   86.00   1.0000  175.0000
omega____ theta____ kappa____ phi______ frames
    -      101.3070  -30.0000 -150.0000 40

 11 omega  103.00  130.00   1.0000  175.0000
omega____ theta____ kappa____ phi______ frames
    -      101.3070  125.0000  120.0000 27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0139950000
_diffrn_orient_matrix_UB_12      -0.0388392000
_diffrn_orient_matrix_UB_13      0.0547532000
_diffrn_orient_matrix_UB_21      0.0795742000
_diffrn_orient_matrix_UB_22      0.0824050000
_diffrn_orient_matrix_UB_23      0.0236093000
_diffrn_orient_matrix_UB_31      -0.2962679000
_diffrn_orient_matrix_UB_32      0.0203501000
_diffrn_orient_matrix_UB_33      0.0089492000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6701
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.497
_diffrn_reflns_theta_min         3.460
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.6174
_exptl_crystal_size_mid          0.0395
_exptl_crystal_size_min          0.0248
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1314 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.13(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3869
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0547P)^2^+0.3338P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1119
_reflns_Friedel_coverage         0.666
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.926
_reflns_number_gt                3560
_reflns_number_total             3869
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce02088d2.cif
_cod_data_source_block           str1763
_cod_depositor_comments
'Adding full bibliography for 7232425--7232430.cif.'
_cod_original_cell_volume        2115.49(10)
_cod_database_code               7232430
_chemical_oxdiff_formula         'C22 H31 N5 O2'
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N2-H2 = N4-H4 = N1-H1A = N1-H1B = N5-H5B = N5-H5A
 0.97 with sigma of 0.02
 N3-H3
 0.97 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C6(H6), C15(H15)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C1(H1C,H1D), C2(H2A,H2B), C4(H4A,H4B), C7(H7A,H7B), C16(H16A,H16B)
3.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C18(H18), C19(H19), C21(H21), C22(H22), C9(H9), C13(H13), C11(H11),
 C10(H10), C12(H12)
;
_shelx_res_checksum              76696
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'