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_7232429
_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         'C15 H31.7 N4 O2'
_chemical_formula_sum            'C15 H31.56 N4 O2'
_chemical_formula_weight         300.00
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_symmetry_space_group_name_Hall  'I 2y'
_symmetry_space_group_name_H-M   'I 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2017-10-03
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2018-11-21 deposited with the CCDC.    2019-02-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.636(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.4259(4)
_cell_length_b                   4.79492(9)
_cell_length_c                   21.6606(5)
_cell_measurement_reflns_used    5626
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.7810
_cell_measurement_theta_min      4.1460
_cell_volume                     2070.07(8)
_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, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_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 1.000
_diffrn_measurement_details
;
  1 omega -122.00   20.40   0.8000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -19.0000 -180.0000 178

  2 omega  -49.00   42.20   0.8000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057   37.0000 -180.0000 114

  3 omega   20.00  109.60   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -94.0000 -150.0000 112

  4 omega   26.00   90.80   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -30.0000 -180.0000 81

  5 omega   28.00   98.40   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -45.0000  -30.0000 88

  6 omega  100.00  178.40   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  111.0000 -150.0000 98

  7 omega   76.00  178.40   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   45.0000  -60.0000 128

  8 omega   69.00  178.60   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   30.0000    0.0000 137

  9 omega  100.00  178.40   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  111.0000 -120.0000 98

 10 omega -116.00   -4.80   0.8000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -57.0000   60.0000 139

 11 omega -122.00   -2.00   0.8000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.6057  -77.0000  150.0000 150

 12 omega   20.00  109.60   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -94.0000  -30.0000 112

 13 omega   69.00  178.60   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   30.0000 -150.0000 137

 14 omega   74.00  178.00   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   61.0000   60.0000 130

 15 omega   74.00  178.00   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   61.0000    0.0000 130

 16 omega   74.00  178.00   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   61.0000 -120.0000 130

 17 omega   76.00  178.40   0.8000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   45.0000  120.0000 128

 18 omega    2.00  122.00   0.8000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.6057   77.0000    0.0000 150
;
_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      0.0477741000
_diffrn_orient_matrix_UB_12      -0.0722223000
_diffrn_orient_matrix_UB_13      0.0634207000
_diffrn_orient_matrix_UB_21      -0.0577376000
_diffrn_orient_matrix_UB_22      -0.1499630000
_diffrn_orient_matrix_UB_23      0.0217596000
_diffrn_orient_matrix_UB_31      0.0189509000
_diffrn_orient_matrix_UB_32      -0.2748719000
_diffrn_orient_matrix_UB_33      -0.0285449000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9488
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        65.989
_diffrn_reflns_theta_max         65.989
_diffrn_reflns_theta_min         3.364
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.516
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35949
_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    0.963
_exptl_crystal_F_000             662
_exptl_crystal_size_max          0.7711
_exptl_crystal_size_mid          0.0913
_exptl_crystal_size_min          0.0542
_refine_diff_density_max         1.266
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.149
_refine_ls_abs_structure_details
;
 Flack x determined using 1202 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3413
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0613
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1118P)^2^+0.6552P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1717
_refine_ls_wR_factor_ref         0.1775
_reflns_Friedel_coverage         0.668
_reflns_Friedel_fraction_full    0.871
_reflns_Friedel_fraction_max     0.871
_reflns_number_gt                3237
_reflns_number_total             3413
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce02088d2.cif
_cod_data_source_block           str1717_sq
_cod_depositor_comments
'Adding full bibliography for 7232425--7232430.cif.'
_cod_original_cell_volume        2070.08(8)
_cod_database_code               7232429
_chemical_oxdiff_formula         'C15 H32 N4 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
2. Restrained distances
 N3-H3
 0.95 with sigma of 0.02
 N2-H2
 0.95 with sigma of 0.02
 H1C-N1 = N1-H1D
 0.95 with sigma of 0.02
 H4AA-N4A = N4A-H4AB
 0.95 with sigma of 0.01
 H1C-H1D
 1.527 with sigma of 0.04
 H4AA-H4AB
 1.527 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(N4A) \\sim Ueq, Uanis(N4B) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(N4A) \\sim Ueq, Uanis(N4B) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
4. Others
 Sof(H12A)=Sof(N4B)=1-FVAR(1)
 Sof(H12)=Sof(N4A)=Sof(H4AA)=Sof(H4AB)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C12(H12), C12(H12A), C13(H13), C8(H8), C7(H7)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C1(H1A,H1B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
5.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C10(H10A,H10B,H10C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              95649
_shelx_fab_checksum              16164
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'