Non-equimolar discrete compounds in binary chiral systems of organic substances
Kotelnikova, Elena N.; Isakov, Anton I.; Lorenz, Heike; CrystEngComm 19 (2017) 1851–; doi:10.1039/C6CE02209J

data_7227922
_publ_section_title
;
 Non-equimolar discrete compounds in binary chiral systems of organic
 substances
;
_journal_issue                   14
_journal_name_full               CrystEngComm
_journal_page_first              1851
_journal_paper_doi               10.1039/C6CE02209J
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C4 H6 O5'
_chemical_formula_sum            'C4 H6 O5'
_chemical_formula_weight         134.09
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-08-31
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-09-01 deposited with the CCDC.
2017-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                107.086(8)
_cell_angle_beta                 95.382(9)
_cell_angle_gamma                93.503(9)
_cell_formula_units_Z            4
_cell_length_a                   4.8168(6)
_cell_length_b                   10.4707(10)
_cell_length_c                   11.0951(9)
_cell_measurement_reflns_used    3436
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.2650
_cell_measurement_theta_min      4.1240
_cell_volume                     530.21(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega    0.00   25.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   91.0000 -121.8032 25

  2 omega  -37.00   -8.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8729  -77.0000  120.0000 29

  3 omega -104.00  -62.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8729  -77.0000  120.0000 42

  4 omega -115.00  -35.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8729 -178.0000 -180.0000 80

  5 omega  -64.00   30.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8729   57.0000 -150.0000 94

  6 omega  -44.00  -17.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8729  -57.0000 -120.0000 27

  7 omega -112.00  -67.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8729  -57.0000 -120.0000 45

  8 omega   62.00  130.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8729  178.0000 -180.0000 68

  9 omega   16.00   41.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   82.0000  -87.2864 25

 10 omega   17.00   42.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   82.0000  -29.3101 25

 11 omega   21.00   46.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000  166.3928 25

 12 omega   21.00   46.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   79.0000 -133.5242 25

 13 omega   25.00   51.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000   25.4835 26

 14 omega   28.00   69.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   75.0000   69.9642 41

 15 omega   28.00   55.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   72.0000  127.3433 27

 16 omega   85.00  113.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   70.0000  -75.2267 28

 17 omega   37.00   70.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   70.0000  -75.2267 33

 18 omega   38.00   94.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000  -35.4151 56

 19 omega   34.00   81.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000  172.0626 47

 20 omega  106.00  142.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000 -139.3734 36

 21 omega   87.00  139.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000  172.0626 52

 22 omega   34.00   65.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000 -139.3734 31

 23 omega   38.00   72.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   75.0000   13.8555 34

 24 omega   48.00   75.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   69.0000 -122.7508 27

 25 omega   51.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   72.0000   57.6747 40

 26 omega   58.00   83.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   63.0000  -92.1762 25

 27 omega   58.00  152.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   64.0000  103.2045 94

 28 omega  127.00  162.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -150.0000 35

 29 omega   85.00  112.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -30.0000 27

 30 omega   84.00  114.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -150.0000 30

 31 omega  112.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   90.0000 64

 32 omega   82.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  150.0000 27

 33 omega   79.00  110.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   90.0000 31

 34 omega   79.00  106.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  120.0000 27

 35 omega   85.00  110.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   90.0000 25

 36 omega   79.00  106.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -90.0000 27

 37 omega   84.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000    0.0000 92

 38 omega   84.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  150.0000 25

 39 omega   48.00   76.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  150.0000 28

 40 omega  123.00  171.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  120.0000 48

 41 omega  107.00  145.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -120.0000 38

 42 omega   41.00   75.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -120.0000 34

 43 omega   84.00  120.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000   30.0000 36

 44 omega  140.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -60.0000 38

 45 omega   83.00  166.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -60.0000 83

 46 omega   86.00  113.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  120.0000 27

 47 omega   83.00  177.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -180.0000 94

 48 omega   79.00  106.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -60.0000 27

 49 omega  112.00  174.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   30.0000 62

 50 omega   80.00  107.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   30.0000 27

 51 omega   75.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  120.0000 34

 52 omega   81.00  108.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -150.0000 27

 53 omega  119.00  144.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   60.0000 25

 54 omega  119.00  144.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  120.0000 25

 55 omega   42.00   81.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   60.0000 39

 56 omega   31.00   69.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  120.0000 38

 57 omega   31.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000   30.0000 78

 58 omega   50.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 41

 59 omega   86.00  131.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   30.0000 45

 60 omega   82.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -180.0000 27

 61 omega   83.00  110.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   60.0000 27

 62 omega  132.00  157.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   60.0000 25

 63 omega  121.00  159.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -120.0000 38

 64 omega   73.00  108.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000 -150.0000 35

 65 omega   86.00  113.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -120.0000 27

 66 omega   46.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000   60.0000 63

 67 omega   86.00  156.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  150.0000 70

 68 omega   83.00  172.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -90.0000 89

 69 omega   94.00  145.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -150.0000 51

 70 omega   36.00   61.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000 -150.0000 25
;
_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      -0.0741320000
_diffrn_orient_matrix_UB_12      -0.1488156000
_diffrn_orient_matrix_UB_13      -0.0764245000
_diffrn_orient_matrix_UB_21      -0.2943225000
_diffrn_orient_matrix_UB_22      0.0062935000
_diffrn_orient_matrix_UB_23      0.0438856000
_diffrn_orient_matrix_UB_31      -0.1094667000
_diffrn_orient_matrix_UB_32      0.0414041000
_diffrn_orient_matrix_UB_33      -0.1167376000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8577
_diffrn_reflns_point_group_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.490
_diffrn_reflns_theta_min         4.197
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.421
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_description       prism
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.841
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 1390 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         3585
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0894P)^2^+0.2562P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1375
_refine_ls_wR_factor_ref         0.1425
_reflns_Friedel_coverage         0.880
_reflns_Friedel_fraction_full    0.876
_reflns_Friedel_fraction_max     0.879
_reflns_number_gt                3310
_reflns_number_total             3585
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ce02209j2.cif
_cod_data_source_block           S3R
_cod_depositor_comments
;
Adding full bibliography for 7227922--7227923.cif.

2017-11-19
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        530.21(9)
_cod_original_formula_moiety     '4(C4 H6 O5)'
_cod_original_formula_sum        'C16 H24 O20'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     536.35
_cod_database_code               7227922
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C6 O5'
_reflns_odcompleteness_completeness 99.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     75.12
_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 O(H) groups
2. Restrained distances
 O2-H2
 0.82 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C16(H16A)
3.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C17(H17A,H17B)
3.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4), O6(H6), O9(H9A), O11(H11), O12(H12), O14(H14), O16(H16),
 O17(H17), O18(H18), O1A(H1A)
;
_shelx_res_checksum              62003
_olex2_submission_special_instructions 'No special instructions were received'