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_2022658
_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 -, C5 H11 N O2'
_chemical_formula_moiety         'C5 H12 N O2 +, C4 H3 O4 -, C5 H11 N O2'
_chemical_formula_sum            'C14 H26 N2 O8'
_chemical_formula_weight         350.37
_chemical_name_systematic
;
<i>DL</i>-Norvalinium hydrogen maleate--<i>DL</i>-norvaline (1/1)
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2016-11-26
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8572(4)
_cell_length_b                   27.3614(11)
_cell_length_c                   7.8306(4)
_cell_measurement_reflns_used    6447
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7240
_cell_measurement_theta_min      2.2920
_cell_volume                     1897.71(15)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>,  2008)
;
_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(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3457
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_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     57.00 113.00   1.00   45.00    --   22.89 178.00 -90.00   56
  2  \w     60.00 109.00   1.00   45.00    --   22.89 178.00  30.00   49
  3  \w    -84.00 -41.00   1.00   45.00    --   22.89-178.00-180.00   43
  4  \w   -126.00 -79.00   1.00   45.00    --  -23.36 -99.00  90.00   47
  5  \w    -67.00  45.00   1.00   45.00    --  -23.36  77.00  90.00  112
  6  \w   -115.00   6.00   1.00   45.00    --  -23.36 -57.00-120.00  121
  7  \w   -121.00  16.00   1.00   45.00    --  -23.36 -57.00 120.00  137
  8  \w   -123.00  15.00   1.00   45.00    --  -23.36 -57.00   0.00  138
  9  \w    -73.00  -7.00   1.00   45.00    --  -23.36  37.00  60.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Agilent Xcalibur Ruby Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0140069000
_diffrn_orient_matrix_UB_12      0.0090905000
_diffrn_orient_matrix_UB_13      0.0832628000
_diffrn_orient_matrix_UB_21      0.0709487000
_diffrn_orient_matrix_UB_22      0.0091036000
_diffrn_orient_matrix_UB_23      -0.0278064000
_diffrn_orient_matrix_UB_31      -0.0343846000
_diffrn_orient_matrix_UB_32      0.0225032000
_diffrn_orient_matrix_UB_33      -0.0223991000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            21923
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.361
_diffrn_reflns_theta_min         2.978
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94812
_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    1.226
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         1975
_refine_ls_number_restraints     298
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0792
_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^)+2.5627P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1455
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1731
_reflns_number_total             1975
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sk3642sup1_2dl_nv_mal.cif
_cod_data_source_block           2dl_nv_mal
_cod_database_code               2022658
_publcif_datablock.id            {307aa8eb-dc39-4a3e-a302-f5266e28ea2d}
_exptl_absorpt_special_details
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_reflns_odcompleteness_completeness 99.60
_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 N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H) groups
2. Restrained distances
 C1B-C2B
 1.48 with sigma of 0.02
 O1B-C1B
 1.4 with sigma of 0.02
 O1-H1
 1.289 with sigma of 0.02
 O4-H4
 1.202 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08
5. Others
 Sof(N1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=Sof(O1B)=Sof(O2B)=Sof(C2B)=Sof(H2B)=
 Sof(C1B)=Sof(C3B)=Sof(H3BA)=Sof(H3BB)=Sof(C4B)=Sof(H4BA)=Sof(H4BB)=Sof(C5B)=
 Sof(H5BA)=Sof(H5BB)=Sof(H5BC)=1-FVAR(1)
 Sof(O1)=Sof(O2)=Sof(N1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C1)=Sof(C3)=Sof(H3A)=
 Sof(H3B)=Sof(C2)=Sof(H2)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C5)=Sof(H5A)=Sof(H5B)=
 Sof(H5C)=FVAR(1)
 Sof(O4B)=Sof(C7B)=Sof(H7B)=Sof(O3B)=1-FVAR(2)
 Sof(O4)=Sof(C7)=Sof(H7)=Sof(O3)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C2(H2), C2B(H2B)
6.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C3B(H3BA,H3BB), C4B(H4BA,H4BB)
6.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C7B(H7B)
6.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), N1B(H1BA,H1BB,H1BC), C5(H5A,H5B,H5C), C5B(H5BA,H5BB,H5BC)
;
_shelx_res_checksum              7458
_shelx_hkl_checksum              50616
_shelx_shelxl_version_number     2016/6
_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 1.065
_oxdiff_exptl_absorpt_empirical_full_min 0.921
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
_cod_database_fobs_code 2022658