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_7232428
_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         'C23 H32 N4 O2'
_chemical_formula_sum            'C23 H32 N4 O2'
_chemical_formula_weight         396.52
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_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                   25.6360(3)
_cell_length_b                   16.5436(2)
_cell_length_c                   5.05085(6)
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.3050
_cell_measurement_theta_min      3.3990
_cell_volume                     2142.12(4)
_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 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega  -74.00   38.20   0.6000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680   77.0000  -30.0000 187

  2 omega  -50.00   35.20   0.6000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680   38.0000 -150.0000 142

  3 omega   55.00  127.00   0.6000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       40.0680 -178.0000 -150.0000 120

  4 omega   28.00   88.60   0.6000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -30.0000    0.0000 101

  5 omega   28.00   88.60   0.6000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -30.0000 -120.0000 101

  6 omega  100.00  178.00   0.6000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  110.0000  170.0000 130

  7 omega   28.00   88.60   0.6000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -30.0000  120.0000 101

  8 omega   28.00   88.60   0.6000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -30.0000   60.0000 101

  9 omega   31.00   97.00   0.6000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -45.0000  -60.0000 110

 10 omega   16.00  178.00   0.6000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400    0.0000  -90.0000 270

 11 omega -114.00  -10.80   0.6000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -57.0000  -30.0000 172

 12 omega -119.00   -6.80   0.6000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -77.0000   90.0000 187

 13 omega -114.00  -10.80   0.6000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -57.0000 -120.0000 172

 14 omega   21.00  108.00   0.6000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -94.0000  120.0000 145

 15 omega   44.00  177.20   0.6000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400   15.0000   90.0000 222

 16 omega   78.00  173.40   0.6000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400   45.0000  -30.0000 159

 17 omega   94.00  178.00   0.6000   21.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  125.0000   30.0000 140
;
_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      0.0310902000
_diffrn_orient_matrix_UB_12      0.0719818000
_diffrn_orient_matrix_UB_13      0.1120155000
_diffrn_orient_matrix_UB_21      -0.0496848000
_diffrn_orient_matrix_UB_22      0.0317995000
_diffrn_orient_matrix_UB_23      0.1363066000
_diffrn_orient_matrix_UB_31      0.0132318000
_diffrn_orient_matrix_UB_32      -0.0497833000
_diffrn_orient_matrix_UB_33      0.2488721000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            19750
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.500
_diffrn_reflns_theta_min         3.448
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75172
_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    1.230
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.3512
_exptl_crystal_size_mid          0.0585
_exptl_crystal_size_min          0.0346
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1601 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4201
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0758P)^2^+0.1340P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1059
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                4027
_reflns_number_total             4201
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce02088d2.cif
_cod_data_source_block           str1750
_cod_depositor_comments
'Adding full bibliography for 7232425--7232430.cif.'
_cod_database_code               7232428
_chemical_oxdiff_formula         'C23 H32 N4 O2'
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N4-H4B = N4-H4A = N3-H3 = N2-H2 = N1-H1A = N1-H1B
 0.97 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C16(H16), C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C1(H1C,H1D), C5(H5A,H5B), C2(H2A,H2B), C8(H8A,H8B), C4(H4C,H4D),
 C17(H17A,H17B)
3.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C10(H10), C12(H12), C14(H14), C11(H11), C23(H23), C22(H22),
 C20(H20), C19(H19), C21(H21)
;
_shelx_res_checksum              56371
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'