Discovery and exploration of new solid forms of dipeptide: l-alanyl-l-glutamine
Fu, Jinqiu; Cai, Mengyang; Shi, Yuzhong; Hou, Yihang; Guo, Rongxi; Wang, Chiyi; Zhao, Jingjing; Zhuang, Wei; Ying, Hanjie; Yang, Pengpeng; Zhang, Keke; CrystEngComm 26 (2024) 943–950; doi:10.1039/D3CE00957B

data_7247952
_publ_section_title
;
 Discovery and exploration of new solid forms of dipeptide:
 l-alanyl-l-glutamine
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              943
_journal_page_last               950
_journal_paper_doi               10.1039/D3CE00957B
_journal_volume                  26
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C8 H15 N3 O4'
_chemical_formula_sum            'C8 H15 N3 O4'
_chemical_formula_weight         217.23
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-06-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-11-10 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.890(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0351(2)
_cell_length_b                   25.7114(10)
_cell_length_c                   8.6670(3)
_cell_measurement_reflns_used    3246
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9230
_cell_measurement_theta_min      5.5760
_cell_volume                     1073.63(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_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   -104.00 -12.00   0.80    4.50    --  -33.50 -37.00  60.00  115
  2  \w   -108.00 -36.00   0.80    4.50    --  -33.50 178.00-150.00   90
  3  \w    -56.00  36.00   0.80    4.50    --  -33.50  37.00-120.00  115
  4  \w   -108.00 -36.00   0.80    4.50    --  -33.50 178.00 -90.00   90
  5  \w    -71.00  38.60   0.80    4.50    --  -33.50  19.00   0.00  137
  6  \w     31.00  99.00   0.80    4.50    --   36.47-138.00 171.00   85
  7  \w     61.00 109.00   0.80    4.50    --   36.47 178.00 -30.00   60
  8  \w    -34.00  58.00   0.80    4.50    --   36.47 -37.00  60.00  115
  9  \w     40.00 128.00   0.80   15.00    --  108.00 -61.00 -90.00  110
 10  \w     88.00 176.00   0.80   15.00    --  108.00  61.00 -90.00  110
 11  \w     39.00 136.60   0.80   15.00    --  108.00 -77.00 150.00  122
 12  \w     38.00 106.00   0.80   15.00    --  108.00 -94.00 -60.00   85
 13  \w    104.00 176.00   0.80   15.00    --  108.00 111.00-180.00   90
 14  \w     88.00 177.60   0.80   15.00    --  108.00  45.00 -60.00  112
 15  \w     40.00 108.00   0.80   15.00    --  108.00-111.00 150.00   85
 16  \w     96.80 176.00   0.80   15.00    --  108.00  61.00-120.00   99
 17  \w     41.00 109.00   0.80   15.00    --  108.00 -30.00 120.00   85
 18  \w     77.00 103.40   0.80   15.00    --  108.00 -94.00 -30.00   33
 19  \w     38.00  98.00   0.80   15.00    --  108.00 -94.00-180.00   75
 20  \w     84.00 123.20   0.80   15.00    --  108.00 178.00-180.00   49
 21  \w     36.00 136.00   0.80   15.00    --  108.00 -15.00-120.00  125
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0339065000
_diffrn_orient_matrix_UB_12      0.0553547000
_diffrn_orient_matrix_UB_13      0.0711632000
_diffrn_orient_matrix_UB_21      -0.1078020000
_diffrn_orient_matrix_UB_22      0.0228683000
_diffrn_orient_matrix_UB_23      -0.1711122000
_diffrn_orient_matrix_UB_31      -0.2991414000
_diffrn_orient_matrix_UB_32      -0.0019659000
_diffrn_orient_matrix_UB_33      0.0120984000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            3910
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.489
_diffrn_reflns_theta_min         3.438
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.918
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       needle
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1456 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3910
_refine_ls_number_restraints     74
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0765P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1334
_reflns_Friedel_coverage         0.933
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                3576
_reflns_number_total             3910
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00957b2.cif
_cod_data_source_block           202305141_tw
_cod_depositor_comments
'Adding full bibliography for 7247952--7247957.cif.'
_cod_database_code               7247952
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C13H9O1N1
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.803
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.569(4)
 0.431(4)
2. 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) groups,
  All N(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C8'A-N3'A
 1.4 with sigma of 0.02
 C8'-N3'
 1.4 with sigma of 0.02
 C8A-N3A
 1.4 with sigma of 0.02
 N3-C8
 1.35 with sigma of 0.02
 C8-O4
 1.2 with sigma of 0.02
 O4A-C8A
 1.2 with sigma of 0.02
 C8'A-O4'A
 1.2 with sigma of 0.02
 C8-C7
 1.72 with sigma of 0.02
 C8A-C7
 1.64 with sigma of 0.02
 C7'-C8'
 1.7 with sigma of 0.02
 C6-C7
 1.65 with sigma of 0.02
 C8'A-C7'
 1.62 with sigma of 0.02
 C2'-C1'
 1.58 with sigma of 0.02
 C7'-C8' \\sim C4'-C5' \\sim C7'-C8'A \\sim C1'-C2' \\sim C4'-C6' \\sim C7'-C6'
 with sigma of 0.01
 C7-C8 \\sim C4-C5 \\sim C7-C8A \\sim C6-C7 \\sim C1-C2 \\sim C2-C3
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(N3A) \\sim Ueq, Uanis(N3) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C8A) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C7) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C8) = Uanis(C8A)
Uanis(N3) = Uanis(N3A)
Uanis(O4) = Uanis(O4A)
Uanis(O4') = Uanis(O4'A)
Uanis(C8') = Uanis(C8'A)
Uanis(N3') = Uanis(N3'A)
5. Others
 Sof(O4A)=Sof(N3A)=Sof(H3AA)=Sof(H3AB)=Sof(H7BC)=Sof(H7BD)=Sof(C8A)=1-FVAR(1)
 Sof(O4)=Sof(N3)=Sof(H3A)=Sof(H3B)=Sof(H7AA)=Sof(H7AB)=Sof(C8)=FVAR(1)
 Sof(O4'A)=Sof(N3'A)=Sof(H3'C)=Sof(H3'D)=Sof(H7'C)=Sof(H7'D)=Sof(C8'A)=1-FVAR(2)
 Sof(O4')=Sof(N3')=Sof(H3'A)=Sof(H3'B)=Sof(H7'A)=Sof(H7'B)=Sof(C8')=FVAR(2)
6.a Rotating group:
 N3'A(H3'C,H3'D)
6.b Ternary CH refined with riding coordinates:
 C2(H2A), C4(H4), C2'(H2'A), C4'(H4')
6.c Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7AA,H7AB), C7(H7BC,H7BD), C6'(H6'A,H6'B), C7'(H7'A,H7'B),
 C7'(H7'C,H7'D)
6.d Aromatic/amide H refined with riding coordinates:
 N2(H2)
6.e X=CH2 refined with riding coordinates:
 N3(H3A,H3B), N3A(H3AA,H3AB), N3'(H3'A,H3'B)
6.f Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C1(H1D,H1E,H1F), N1'(H1'A,H1'B,H1'C), C1'(H1'D,H1'E,H1'F)
;
_shelx_res_checksum              80366
_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 1.143
_oxdiff_exptl_absorpt_empirical_full_min 0.858