New 1:1 and 2:1 salts in the 'DL-norvaline–maleic acid' system as an example of assembling various crystal structures from similar supramolecular building blocks
Arkhipov, Sergey G.; Losev, Evgeniy A.; Boldyreva, Elena V.; Acta Crystallographica, Section C: Structural Chemistry 73 (2017) 13–19; doi:10.1107/s2053229616018271

data_2022659
_publ_section_title
;
 New 1:1 and 2:1 salts in the 'DL-norvaline--maleic acid' system as an
 example of assembling various crystal structures from similar
 supramolecular building blocks
;
_journal_coden_ASTM              ACSCGG
_journal_coeditor_code           SK3642
_journal_issue                   1
_journal_name_full
;
 Acta Crystallographica, Section C: Structural Chemistry
;
_journal_page_first              13
_journal_page_last               19
_journal_paper_doi               10.1107/s2053229616018271
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C5 H12 N O2 +, C4 H3 O4 -'
_chemical_formula_moiety         'C5 H12 N O2 +, C4 H3 O4 -'
_chemical_formula_sum            'C9 H15 N O6'
_chemical_formula_weight         233.22
_chemical_name_common            '<i>DL</i>-Norvalinium hydrogen maleate'
_chemical_name_systematic
;
<i>DL</i>-Norvalinium hydrogen maleate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-10-12
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2016-11-15 # Formatted by IUCr publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 108.283(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.6385(15)
_cell_length_b                   5.62705(18)
_cell_length_c                   23.6867(10)
_cell_measurement_reflns_used    3032
_cell_measurement_temperature    293
_cell_measurement_theta_max      25.1230
_cell_measurement_theta_min      1.8070
_cell_volume                     2485.4(2)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2014)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov <i>et al.</i>, 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov <i>et al.</i>, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 10.3457
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega   85.00  128.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8905   77.0000  -60.0000 43

  2 omega  -14.00   44.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8905   77.0000  -60.0000 58

  3 omega   56.00   98.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8905  179.0000 -150.0000 42

  4 omega  -26.00   71.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8905   77.0000 -180.0000 97

  5 omega  -70.00  -34.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8905 -179.0000  -90.0000 36

  6 omega   64.00  115.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       22.8905  179.0000  120.0000 51

  7 omega -125.00   37.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.3592  -37.0000  -60.0000 162

  8 omega -131.00   79.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.3592   19.0000   60.0000 210

  9 omega -119.00  -34.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.3592 -179.0000  120.0000 85
;
_diffrn_measurement_device_type  'Agilent Xcalibur Ruby Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0331220000
_diffrn_orient_matrix_UB_12      0.0612773000
_diffrn_orient_matrix_UB_13      -0.0064587000
_diffrn_orient_matrix_UB_21      -0.0185743000
_diffrn_orient_matrix_UB_22      -0.1099982000
_diffrn_orient_matrix_UB_23      -0.0053748000
_diffrn_orient_matrix_UB_31      0.0020762000
_diffrn_orient_matrix_UB_32      -0.0064060000
_diffrn_orient_matrix_UB_33      0.0304027000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13186
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         1.811
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2014)
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.232
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2198
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.232
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0681
_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^)+(0.0688P)^2^+1.2674P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1559
_refine_ls_wR_factor_ref         0.1657
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1807
_reflns_number_total             2198
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sk3642sup1_I.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2022659
_publcif_datablock.id            {7719b556-9877-4fbb-9f17-ee6a2fcdd584}
_chemical_oxdiff_formula         'C9 H15 N O6'
_exptl_absorpt_special_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C5B \\sim C4B \\sim C3: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04
3. Others
 Sof(H3BC)=Sof(H3BD)=Sof(C4B)=Sof(H4BA)=Sof(H4BB)=Sof(C5B)=Sof(H5BA)=Sof(H5BB)=
 Sof(H5BC)=1-FVAR(1)
 Sof(H3AA)=Sof(H3AB)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=
 Sof(H5AC)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C2(H2)
4.b Secondary CH2 refined with riding coordinates:
 C3(H3AA,H3AB), C3(H3BC,H3BD), C4A(H4AA,H4AB), C4B(H4BA,H4BB)
4.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7)
4.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C5A(H5AA,H5AB,H5AC), C5B(H5BA,H5BB,H5BC)
4.e Idealised tetrahedral OH refined as rotating group:
 O6(H6), O1(H1)
;
_shelx_res_checksum              55522
_shelx_hkl_checksum              23582
_shelx_shelxl_version_number     2014/7
_cod_database_fobs_code 2022659