Heteromolecular compounds in binary systems of amino acids with opposite and same chiralities
Isakov, Anton I.; Lorenz, Heike; Zolotarev, Andrey A.; Kotelnikova, Elena N.; CrystEngComm 22 (2020) 986–997; doi:10.1039/C9CE01333D

data_7239752
_publ_section_title
;
 Heteromolecular compounds in binary systems of amino acids with opposite
 and same chiralities
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              986
_journal_page_last               997
_journal_paper_doi               10.1039/C9CE01333D
_journal_volume                  22
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C5 H11 N O2), 2(C5.5 H12 N O2)'
_chemical_formula_sum            'C21 H46 N4 O8'
_chemical_formula_weight         482.62
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-15 deposited with the CCDC.	2019-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.943(11)
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   9.6267(7)
_cell_length_b                   5.2704(2)
_cell_length_c                   13.8290(17)
_cell_measurement_reflns_used    1940
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.6500
_cell_measurement_theta_min      4.8400
_cell_volume                     659.56(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -61.00 -24.00   0.50    1.40    --  -38.95  67.00 157.00   74
  2  \w   -104.00 -42.00   0.50    1.40    --  -38.95 -67.00  23.00  124
  3  \w     19.00  55.00   0.50    1.40    --   38.95  67.00 157.00   72
  4  \w    127.00 154.00   0.50    4.30    --  107.00  67.00 157.00   54
  5  \w     64.00 129.00   0.50    4.30    --  107.00 -67.00  23.00  130
  6  \w     84.00 123.00   0.50    4.30    --  107.00  67.00 157.00   78
  7  \w    -77.00 -40.00   0.50    1.40    --  -38.95 104.00 -60.00   74
  8  \w    -93.00 -62.00   0.50    1.40    --  -38.95 138.00 150.00   62
  9  \w     -5.00  31.00   0.50    1.40    --  -38.95  21.00-180.00   72
 10  \w    -59.00 -10.00   0.50    1.40    --  -38.95  21.00-180.00   98
 11  \w    -59.00 -16.00   0.50    1.40    --  -38.95 138.00 150.00   86
 12  \w    -18.00   8.00   0.50    1.40    --  -38.95 104.00 -60.00   52
 13  \w    -23.00  34.00   0.50    1.40    --   38.95 -43.00  30.00  114
 14  \w     70.00 102.00   0.50    1.40    --   38.95  21.00  90.00   64
 15  \w    -28.00   1.00   0.50    1.40    --   38.95 -32.00-150.00   58
 16  \w     40.00  98.00   0.50    1.40    --   38.95  43.00 -60.00  116
 17  \w     28.00  54.00   0.50    1.40    --   38.95  32.00 -90.00   52
 18  \w     44.00  69.00   0.50    1.40    --   38.95  32.00  90.00   50
 19  \w     63.00  89.00   0.50    1.40    --   38.95  67.00 157.00   52
 20  \w     22.00  47.00   0.50    1.40    --   38.95 -67.00  23.00   50
 21  \w     68.00  93.00   0.50    1.40    --   38.95  32.00 -30.00   50
 22  \w     27.00  52.00   0.50    1.40    --   38.95  21.00  90.00   50
 23  \w     22.00  83.00   0.50    1.40    --   38.95  43.00   0.00  122
 24  \w     34.00  77.00   0.50    1.40    --   38.95  32.00 -60.00   86
 25  \w    -13.00  49.00   0.50    1.40    --   38.95 -77.00 150.00  124
 26  \w     10.00  48.00   0.50    1.40    --   38.95 -32.00-150.00   76
 27  \w     95.00 121.00   0.50    4.30    --  107.00  37.00-120.00   52
 28  \w     39.00  69.00   0.50    4.30    --  107.00 -30.00-120.00   60
 29  \w     80.00 112.00   0.50    4.30    --  107.00-111.00  30.00   64
 30  \w    129.00 157.00   0.50    4.30    --  107.00  69.00-180.00   56
 31  \w     86.00 111.00   0.50    4.30    --  107.00  69.00-180.00   50
 32  \w    117.00 155.00   0.50    4.30    --  107.00  66.00-100.05   76
 33  \w     83.00 109.00   0.50    4.30    --  107.00  69.00 -90.00   52
 34  \w     83.00 109.00   0.50    4.30    --  107.00 -30.00-120.00   52
 35  \w     39.00  65.00   0.50    4.30    --  107.00-111.00 120.00   52
 36  \w     41.00  76.00   0.50    4.30    --  107.00-111.00 150.00   70
 37  \w    119.00 153.00   0.50    4.30    --  107.00  77.00 -90.00   68
 38  \w     81.00 110.00   0.50    4.30    --  107.00  77.00 -90.00   58
 39  \w     84.00 109.00   0.50    4.30    --  107.00  66.00-100.05   50
 40  \w     46.00  72.00   0.50    4.30    --  107.00-111.00  30.00   52
 41  \w     95.00 120.00   0.50    4.30    --  107.00 133.00  60.00   50
 42  \w    132.00 157.00   0.50    4.30    --  107.00  53.00 -60.00   50
 43  \w     88.00 116.00   0.50    4.30    --  107.00  53.00 -60.00   56
 44  \w    128.00 157.00   0.50    4.30    --  107.00  69.00-150.00   58
 45  \w     82.00 108.00   0.50    4.30    --  107.00-111.00 -60.00   52
 46  \w     83.00 109.00   0.50    4.30    --  107.00  69.00-150.00   52
 47  \w     40.00  73.00   0.50    4.30    --  107.00-111.00 -60.00   66
 48  \w     95.00 148.00   0.50    4.30    --  107.00  22.00  60.00  106
 49  \w     38.00 120.00   0.50    4.30    --  107.00 -22.00 150.00  164
 50  \w     88.00 129.00   0.50    4.30    --  107.00  22.00-120.00   82
 51  \w    115.00 141.00   0.50    4.30    --  107.00   7.00-180.00   52
 52  \w     58.00  96.00   0.50    4.30    --  107.00   7.00-180.00   76
 53  \w     83.00 108.00   0.50    4.30    --  107.00  69.00-120.00   50
 54  \w     39.00 112.00   0.50    4.30    --  107.00-111.00  90.00  146
 55  \w     93.00 155.00   0.50    4.30    --  107.00  45.00-120.00  124
 56  \w     69.00  95.00   0.50    4.30    --  107.00 -53.00 120.00   52
 57  \w    102.00 127.00   0.50    4.30    --  107.00 -53.00 120.00   50
 58  \w     85.00 111.00   0.50    4.30    --  107.00  61.00-120.00   52
 59  \w     89.00 114.00   0.50    4.30    --  107.00  61.00 -90.00   50
 60  \w     87.00 129.00   0.50    4.30    --  107.00  61.00 -60.00   84
 61  \w     39.00  75.00   0.50    4.30    --  107.00 -30.00 -30.00   72
 62  \w     82.00 108.00   0.50    4.30    --  107.00  77.00-120.00   52
 63  \w    121.00 146.00   0.50    4.30    --  107.00  77.00-120.00   50
 64  \w     38.00  86.00   0.50    4.30    --  107.00-111.00  60.00   96
 65  \w     97.00 122.00   0.50    4.30    --  107.00 -37.00  30.00   50
 66  \w     41.00  78.00   0.50    4.30    --  107.00 -37.00  30.00   74
 67  \w     83.00 120.00   0.50    4.30    --  107.00  77.00 -60.00   74
 68  \w     87.00 155.00   0.50    4.30    --  107.00  61.00 120.00  136
 69  \w    124.00 150.00   0.50    4.30    --  107.00 133.00  60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1176440000
_diffrn_orient_matrix_UB_12      -0.0031997000
_diffrn_orient_matrix_UB_13      0.0525556000
_diffrn_orient_matrix_UB_21      -0.0800156000
_diffrn_orient_matrix_UB_22      0.2242189000
_diffrn_orient_matrix_UB_23      -0.0677765000
_diffrn_orient_matrix_UB_31      -0.0935085000
_diffrn_orient_matrix_UB_32      -0.1875282000
_diffrn_orient_matrix_UB_33      -0.0817730000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5431
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.981
_diffrn_reflns_theta_min         3.400
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.764
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_description       prism
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 710 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2475
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0687
_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^)+(0.1467P)^2^+0.0027P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1864
_refine_ls_wR_factor_ref         0.2039
_reflns_Friedel_coverage         0.773
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                1848
_reflns_number_total             2475
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce01333d1.cif
_cod_data_source_block           011018_80
_cod_depositor_comments
;Adding full bibliography for 7239752.cif.

 Adding full bibliography for 7239752.cif.
;
_cod_database_code               7239752
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C21 H46 N4 O8'
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H2A(0.5) H2AA(0.5) C6A(0.5) H6AA(0.5) H6AB(0.5) C4A(0.5) H4AA(0.5)
 H4AB(0.5) H4AC(0.5) C5A(0.5) H5AA(0.5) H5AB(0.5) H5AC(0.5) C7A(0.5) H7A(0.5)
 C9A(0.5) H9AA(0.5) H9AB(0.5) H9AC(0.5) C8A(0.5) H8AA(0.5) H8AB(0.5) H8AC(0.5)
 C3A(0.5) H3A(0.5)
3.a Ternary CH refined with riding coordinates:
 C2A(H2A), C2A(H2AA), C2(H2), C3(H3), C7A(H7A), C3A(H3A)
3.b Secondary CH2 refined with riding coordinates:
 C6A(H6AA,H6AB)
3.c Idealised Me refined as rotating group:
 N1A(H1AA,H1AB,H1AC), N1(H1A,H1B,H1C), C4A(H4AA,H4AB,H4AC), C4(H4A,H4B,H4C),
 C5(H5A,H5B,H5C), C5A(H5AA,H5AB,H5AC), C9A(H9AA,H9AB,H9AC), C8A(H8AA,H8AB,H8AC)
;
_shelx_res_checksum              88502
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.129
_oxdiff_exptl_absorpt_empirical_full_min 0.462