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_7232425
_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         'C12 H26 N4 O2, 2(H2 O)'
_chemical_formula_sum            'C12 H30 N4 O4'
_chemical_formula_weight         294.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 112.756(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.5640(3)
_cell_length_b                   4.80981(7)
_cell_length_c                   15.8319(3)
_cell_measurement_reflns_used    5235
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.2740
_cell_measurement_theta_min      5.6860
_cell_volume                     882.26(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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega -116.00  -14.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -37.0000  -60.0000 204

  2 omega  -70.00   34.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680   57.0000  150.0000 208

  3 omega    1.00   82.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       40.0680  -99.0000  -90.0000 162

  4 omega   31.00  122.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400 -125.0000  -90.0000 182

  5 omega   28.00   91.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -30.0000   90.0000 126

  6 omega   27.00  139.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -77.0000  -60.0000 224

  7 omega   28.00   91.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -30.0000    0.0000 126

  8 omega   28.00   91.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -30.0000 -180.0000 126

  9 omega   28.00   91.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -30.0000  -60.0000 126

 10 omega   44.00  178.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400   15.0000   90.0000 268

 11 omega -119.00   -6.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -77.0000  -90.0000 226

 12 omega -114.00  -10.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -57.0000   60.0000 208

 13 omega -114.00  -10.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.0680  -57.0000 -180.0000 208

 14 omega   75.00  178.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400   61.0000  -30.0000 206

 15 omega   75.00  178.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400   30.0000 -180.0000 206

 16 omega   21.00  108.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400  -94.0000  120.0000 174

 17 omega   72.00  104.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400   77.0000 -180.0000 64

 18 omega   75.00  178.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400   61.0000  120.0000 206

 19 omega   75.00  178.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      105.5400   30.0000  -90.0000 206
;
_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      -0.0529811000
_diffrn_orient_matrix_UB_12      -0.2936589000
_diffrn_orient_matrix_UB_13      -0.0149187000
_diffrn_orient_matrix_UB_21      0.0085236000
_diffrn_orient_matrix_UB_22      -0.0040824000
_diffrn_orient_matrix_UB_23      0.0997152000
_diffrn_orient_matrix_UB_31      -0.1216726000
_diffrn_orient_matrix_UB_32      0.1277475000
_diffrn_orient_matrix_UB_33      -0.0311505000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8173
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        65.999
_diffrn_reflns_theta_max         65.999
_diffrn_reflns_theta_min         3.815
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.963
_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    1.108
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.3977
_exptl_crystal_size_mid          0.1078
_exptl_crystal_size_min          0.0509
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1132 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3066
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0459
_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^)+(0.0822P)^2^+0.0244P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1244
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                2835
_reflns_number_total             3066
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce02088d2.cif
_cod_data_source_block           str1737
_cod_depositor_comments
'Adding full bibliography for 7232425--7232430.cif.'
_cod_database_code               7232425
_chemical_oxdiff_formula         'C12 H26 N4 O2'
_reflns_odcompleteness_completeness 99.94
_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
 N3-H3 = N2-H2 = N4-H4A = N4-H4B = N1-H1A = N1-H1B
 0.97 with sigma of 0.02
3.a Free rotating group:
 O3(H3A,H3B), O4(H4C,H4D)
3.b Ternary CH refined with riding coordinates:
 C9(H9), C4(H4), C5(H5), C10(H10)
3.c Secondary CH2 refined with riding coordinates:
 C1(H1C,H1D), C2(H2A,H2B)
3.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C6(H6A,H6B,H6C), C12(H12A,H12B,H12C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              73822
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'