Supramolecular synthon hierarchy in cyclopropyl-containing peptide-derived compounds
Bojarska, Joanna; Wolf, Wojciech M.; Fruziński, Andrzej; Kaczmarek, Krzysztof; Lesnikowski, Zbigniew J.; Kraj, Agata; Zielenkiewicz, Piotr; Madura, Izabela Dorota; Borowiecki, Paweł; Remko, Milan; Breza, Martin; CrystEngComm  (2022) –; doi:10.1039/D2CE01231F

data_7245756
_publ_section_title
;
 Supramolecular synthon hierarchy in cyclopropyl-containing
 peptide-derived compounds
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE01231F
_journal_year                    2022
_chemical_formula_moiety         'C8 H13 N O3'
_chemical_formula_sum            'C8 H13 N O3'
_chemical_formula_weight         171.19
_chemical_name_systematic        '2-acetamido-3-cyclopropylpropanoic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-04-22
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2022-08-28 deposited with the CCDC.	2022-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.6010(10)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   14.66220(10)
_cell_length_b                   11.42930(10)
_cell_length_c                   21.61680(10)
_cell_measurement_reflns_used    84697
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      78.7620
_cell_measurement_theta_min      3.6860
_cell_volume                     3622.32(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_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   -124.00 -39.00   0.50    0.10    --  -49.71 -38.00 -90.00  170
  2  \w    -26.00  26.00   0.50    0.10    --  -49.71  19.00 -90.00  104
  3  \w   -114.00 -27.00   0.50    0.10    --  -49.71 -77.00  30.00  174
  4  \w    -26.00  26.00   0.50    0.10    --  -49.71  19.00-150.00  104
  5  \w   -121.00 -35.00   0.50    0.10    --  -49.71 -57.00  60.00  172
  6  \w    -43.00  25.00   0.50    0.10    --  -49.71  38.00 120.00  136
  7  \w    -26.00  26.00   0.50    0.10    --  -49.71  19.00  90.00  104
  8  \w     62.00 120.00   0.50    0.10    --   49.71 178.00 -30.00  116
  9  \w    -25.00  26.00   0.50    0.10    --   49.71 -19.00 -60.00  102
 10  \w    -43.00 -11.00   0.50    0.13    --  -86.25  38.00 -90.00   64
 11  \w   -161.00 -75.00   0.50    0.13    --  -86.25 -19.00 -30.00  172
 12  \w    -43.00 -11.00   0.50    0.13    --  -86.25  38.00  90.00   64
 13  \w   -151.00 -64.00   0.50    0.13    --  -86.25 -77.00  30.00  174
 14  \w   -151.00 -64.00   0.50    0.13    --  -86.25 -77.00  60.00  174
 15  \w    -43.00 -11.00   0.50    0.13    --  -86.25  38.00  60.00   64
 16  \w   -105.00 -22.00   0.50    0.13    --  -86.25  77.00 -90.00  166
 17  \w    -43.00 -11.00   0.50    0.13    --  -86.25  38.00  30.00   64
 18  \w    -43.00 -11.00   0.50    0.13    --  -86.25  38.00-180.00   64
 19  \w    -43.00 -11.00   0.50    0.13    --  -86.25  38.00   0.00   64
 20  \w   -157.00 -71.00   0.50    0.13    --  -86.25 -57.00 -30.00  172
 21  \w    -66.00 -15.00   0.50    0.13    --  -86.25  57.00-150.00  102
 22  \w     37.00  66.00   0.50    0.13    --  107.75 -57.00 150.00   58
 23  \w     97.00 178.00   0.50    0.13    --  107.75  19.00-120.00  162
 24  \w     37.00  66.00   0.50    0.13    --  107.75 -57.00-150.00   58
 25  \w     93.00 178.00   0.50    0.13    --  107.75  57.00 -30.00  170
 26  \w     37.00  66.00   0.50    0.13    --  107.75 -57.00 -30.00   58
 27  \w     37.00  66.00   0.50    0.13    --  107.75 -57.00  60.00   58
 28  \w     36.00 112.00   0.50    0.13    --  107.75-125.00-180.00  152
 29  \w     37.00  66.00   0.50    0.13    --  107.75 -57.00   0.00   58
 30  \w     97.00 178.00   0.50    0.13    --  107.75  19.00-180.00  162
 31  \w     97.00 178.00   0.50    0.13    --  107.75  38.00  90.00  162
 32  \w     85.00 172.00   0.50    0.13    --  107.75  77.00   0.00  174
 33  \w     93.00 178.00   0.50    0.13    --  107.75  57.00  60.00  170
 34  \w     43.00 105.00   0.50    0.13    --  107.75 -77.00 150.00  124
 35  \w     37.00  66.00   0.50    0.13    --  107.75 -57.00-180.00   58
 36  \w     97.00 178.00   0.50    0.13    --  107.75  38.00  30.00  162
 37  \w     94.00 178.00   0.50    0.13    --  107.75 125.00  90.00  168
 38  \w     37.00  66.00   0.50    0.13    --  107.75 -57.00-120.00   58
 39  \w     37.00  66.00   0.50    0.13    --  107.75 -57.00  30.00   58
 40  \w   -114.00 -27.00   0.50    0.10    --  -49.71 -77.00-180.00  174
 41  \w   -121.00 -35.00   0.50    0.10    --  -49.71 -57.00-120.00  172
 42  \w   -120.00 -34.00   0.50    0.10    --  -49.71 -59.00 132.00  172
 43  \w     35.00 121.00   0.50    0.10    --   49.71  57.00-120.00  172
 44  \w     27.00 114.00   0.50    0.10    --   49.71  77.00-120.00  174
 45  \w     27.00 114.00   0.50    0.10    --   49.71  77.00 120.00  174
 46  \w     60.00 121.00   0.50    0.10    --   49.71-178.00 150.00  122
 47  \w     27.00 114.00   0.50    0.10    --   49.71  77.00  30.00  174
 48  \w     27.00 114.00   0.50    0.10    --   49.71  77.00 -30.00  174
 49  \w   -151.00 -64.00   0.50    0.13    --  -86.25 -77.00-180.00  174
 50  \w   -151.00 -64.00   0.50    0.13    --  -86.25 -77.00-120.00  174
 51  \w   -151.00 -64.00   0.50    0.13    --  -86.25 -77.00   0.00  174
 52  \w   -151.00 -64.00   0.50    0.13    --  -86.25 -77.00 150.00  174
 53  \w   -157.00 -71.00   0.50    0.13    --  -86.25 -59.00 132.00  172
 54  \w   -151.00 -64.00   0.50    0.13    --  -86.25 -77.00  90.00  174
 55  \w   -151.00 -64.00   0.50    0.13    --  -86.25 -77.00 -60.00  174
 56  \w   -151.00 -64.00   0.50    0.13    --  -86.25 -77.00-150.00  174
 57  \w   -151.00 -64.00   0.50    0.13    --  -86.25 -77.00 -30.00  174
 58  \w   -151.00 -64.00   0.50    0.13    --  -86.25 -77.00 120.00  174
 59  \w   -151.00 -64.00   0.50    0.13    --  -86.25 -77.00 -90.00  174
 60  \w     36.00 112.00   0.50    0.13    --  107.75-125.00 -30.00  152
 61  \w     39.00 107.00   0.50    0.13    --  107.75 -99.00 -30.00  136
 62  \w     39.00 107.00   0.50    0.13    --  107.75 -99.00  30.00  136
 63  \w     36.00 112.00   0.50    0.13    --  107.75-125.00 150.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            119641
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.950
_diffrn_reflns_theta_min         3.014
_exptl_absorpt_coefficient_mu    0.801
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.348
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.53a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       needle
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.00026(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         7734
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0423P)^2^+1.5271P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0931
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7387
_reflns_number_total             7734
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01231f2.cif
_cod_data_source_block           kk_big
_cod_database_code               7245756
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.856
_shelx_estimated_absorpt_t_min   0.608
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3A), C3C(H3CA), C3A(H3AB), C3B(H3BA), C5A(H5A), C5C(H5C), C5(H5), C5B(H5B)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C4C(H4CA,H4CB), C4A(H4AA,H4AB), C4B(H4BA,H4BB), C6B(H6BA,H6BB),
 C7(H7A,H7B), C6C(H6CA,H6CB), C6A(H6AA,H6AB), C6(H6A,H6B), C7B(H7BA,H7BB),
 C7C(H7CA,H7CB), C7A(H7AA,H7AB)
2.c Aromatic/amide H refined with riding coordinates:
 NA(HA), N(H), NB(HB), NC(HC)
2.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C2C(H2CA,H2CB,H2CC), C2B(H2BA,H2BB,H2BC), C2A(H2AA,H2AB,H2AC)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O3C(H3C), O3B(H3B), O3A(H3AA)
;
_shelx_res_checksum              95623
_shelx_hkl_checksum              96761
_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
;