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_7232427
_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         'C14 H31 N5 O2, 2(H2 O)'
_chemical_formula_sum            'C14 H35 N5 O4'
_chemical_formula_weight         337.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_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                 105.807(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.1681(6)
_cell_length_b                   4.81178(18)
_cell_length_c                   16.5261(5)
_cell_measurement_reflns_used    6406
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.5460
_cell_measurement_theta_min      3.4500
_cell_volume                     2002.20(11)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega -116.00   -5.60   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -57.0000   60.0000 138

  2 omega  -95.00   46.60   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057   19.0000  150.0000 177

  3 omega -116.00   -5.60   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -57.0000  150.0000 138

  4 omega   57.00  129.00   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       37.6057  178.0000  120.0000 90

  5 omega   66.00  178.00   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   77.0000   30.0000 140

  6 omega  100.00  177.60   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686  111.0000 -180.0000 97

  7 omega   68.00  177.60   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   62.0000  129.3950 137

  8 omega   66.00  178.00   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   77.0000  120.0000 140

  9 omega   66.00  178.00   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   77.0000   60.0000 140

 10 omega   24.00   96.80   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686  -45.0000   90.0000 91

 11 omega   69.00  177.00   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   61.0000   90.0000 135

 12 omega   66.00  178.00   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   77.0000  150.0000 140

 13 omega   69.00  177.00   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   61.0000  150.0000 135

 14 omega   69.00  177.00   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   61.0000   30.0000 135

 15 omega   66.00  178.00   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   77.0000   90.0000 140

 16 omega   15.00  108.60   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686  -94.0000  120.0000 117

 17 omega   69.00  177.00   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   61.0000   60.0000 135

 18 omega   69.00  177.00   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   61.0000  120.0000 135

 19 omega   71.00  177.40   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   45.0000 -180.0000 133

 20 omega   69.00  177.00   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   61.0000 -180.0000 135

 21 omega   67.00  177.40   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   63.0000   95.7746 138

 22 omega   66.00  178.00   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   77.0000 -180.0000 140

 23 omega   67.00  177.40   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   72.0000   59.2020 138

 24 omega -116.00   -5.60   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -57.0000 -120.0000 138

 25 omega  -49.00   41.40   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057   37.0000  -60.0000 113

 26 omega -122.00   -2.00   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -77.0000    0.0000 150

 27 omega    5.00  115.40   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       37.6057   57.0000    0.0000 138

 28 omega   57.00  129.00   0.8000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       37.6057  178.0000  -30.0000 90

 29 omega   64.00  150.40   0.8000   13.0000
omega____ theta____ kappa____ phi______ frames
    -      101.8686   30.0000  -30.0000 108
;
_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      -0.0119660000
_diffrn_orient_matrix_UB_12      0.0150585000
_diffrn_orient_matrix_UB_13      -0.0964118000
_diffrn_orient_matrix_UB_21      0.0588718000
_diffrn_orient_matrix_UB_22      -0.0576936000
_diffrn_orient_matrix_UB_23      0.0066355000
_diffrn_orient_matrix_UB_31      -0.0113228000
_diffrn_orient_matrix_UB_32      -0.3150351000
_diffrn_orient_matrix_UB_33      -0.0057811000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16100
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        64.971
_diffrn_reflns_theta_max         64.971
_diffrn_reflns_theta_min         3.511
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_correction_T_min  0.282
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.9442
_exptl_crystal_size_mid          0.0931
_exptl_crystal_size_min          0.0382
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1164 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3249
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0548
_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^)+(0.0976P)^2^+0.8793P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1514
_refine_ls_wR_factor_ref         0.1564
_reflns_Friedel_coverage         0.676
_reflns_Friedel_fraction_full    0.880
_reflns_Friedel_fraction_max     0.880
_reflns_number_gt                3030
_reflns_number_total             3249
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce02088d2.cif
_cod_data_source_block           str1715
_cod_depositor_comments
'Adding full bibliography for 7232425--7232430.cif.'
_cod_database_code               7232427
_chemical_oxdiff_formula         'C14 H31 N5 O2'
_reflns_odcompleteness_completeness 99.95
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 N4-H4 = N5-H5A = N5-H5B = N2-H2
 0.97 with sigma of 0.02
 H1B-N1 = N1-H1A
 0.95 with sigma of 0.02
 N3-H3
 0.95 with sigma of 0.02
 H1B-H1A
 1.527 with sigma of 0.04
3.a Free rotating group:
 O4(H4C,H4D), O3(H3C,H3D)
3.b Ternary CH refined with riding coordinates:
 C11(H11), C6(H6), C12(H12), C7(H7)
3.c Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C3(H3A,H3B), C1(H1C,H1D), C2(H2A,H2B)
3.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C14(H14A,H14B,H14C), C9(H9A,H9B,H9C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              14117
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'