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_7245754
_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_absolute_configuration rm
_chemical_formula_moiety         'C21 H21 N O4'
_chemical_formula_sum            'C21 H21 N O4'
_chemical_formula_weight         351.39
_chemical_name_systematic
'diethyl 2-acetamido-2-(cyclopropylmethyl)malonate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-16
_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                 109.5159(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.5330(2)
_cell_length_b                   5.04577(4)
_cell_length_c                   30.1674(3)
_cell_measurement_reflns_used    26025
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.7190
_cell_measurement_theta_min      3.1250
_cell_volume                     3519.82(6)
_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 0.999
_diffrn_measured_fraction_theta_max 0.971
_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   -114.00 -27.00   0.50    2.99    --  -49.96 -77.00  30.00  174
  2  \w    -26.00  25.00   0.50    2.99    --  -49.96  19.00  60.00  102
  3  \w    -26.00  25.00   0.50    2.99    --  -49.96  19.00  90.00  102
  4  \w    -43.00 -11.00   0.50   11.97    --  -86.25  38.00   0.00   64
  5  \w    -43.00 -11.00   0.50   11.97    --  -86.25  38.00  60.00   64
  6  \w    -43.00 -11.00   0.50   11.97    --  -86.25  38.00  90.00   64
  7  \w    -43.00 -11.00   0.50   11.97    --  -86.25  38.00  30.00   64
  8  \w    -87.00 -15.00   0.50   11.97    --  -86.25 125.00 -60.00  144
  9  \w    -65.00  21.00   0.50    2.99    --  -49.96  57.00-180.00  172
 10  \w    -43.00 -11.00   0.50   11.97    --  -86.25  38.00-180.00   64
 11  \w    -43.00 -11.00   0.50   11.97    --  -86.25  38.00-150.00   64
 12  \w   -114.00 -27.00   0.50    2.99    --  -49.96 -77.00 -90.00  174
 13  \w   -114.00 -27.00   0.50    2.99    --  -49.96 -77.00  90.00  174
 14  \w   -114.00 -33.00   0.50    2.99    --  -49.96 -77.00 -60.00  162
 15  \w   -114.00 -27.00   0.50    2.99    --  -49.96 -77.00-180.00  174
 16  \w   -114.00 -27.00   0.50    2.99    --  -49.96 -77.00-150.00  174
 17  \w    -25.00  26.00   0.50    2.99    --   49.96 -19.00-120.00  102
 18  \w     37.00  66.00   0.50   11.97    --  107.75 -57.00-150.00   58
 19  \w     37.00  66.00   0.50   11.97    --  107.75 -57.00-180.00   58
 20  \w     37.00  66.00   0.50   11.97    --  107.75 -57.00-120.00   58
 21  \w     43.00 105.00   0.50   11.97    --  107.75 -77.00-180.00  124
 22  \w     97.00 178.00   0.50   11.97    --  107.75  19.00 -60.00  162
 23  \w     97.00 178.00   0.50   11.97    --  107.75  38.00-180.00  162
 24  \w     97.00 178.00   0.50   11.97    --  107.75  19.00 -30.00  162
 25  \w     97.00 178.00   0.50   11.97    --  107.75  38.00 -90.00  162
 26  \w     93.00 178.00   0.50   11.97    --  107.75  57.00   0.00  170
 27  \w     36.00 112.00   0.50   11.97    --  107.75-125.00 150.00  152
 28  \w     43.00 105.00   0.50   11.97    --  107.75 -77.00  30.00  124
 29  \w     37.00  66.00   0.50   11.97    --  107.75 -57.00 150.00   58
 30  \w     43.00 105.00   0.50   11.97    --  107.75 -77.00 120.00  124
 31  \w     37.00  66.00   0.50   11.97    --  107.75 -57.00  30.00   58
 32  \w     37.00  66.00   0.50   11.97    --  107.75 -57.00   0.00   58
 33  \w     37.00  66.00   0.50   11.97    --  107.75 -57.00  60.00   58
 34  \w     37.00  66.00   0.50   11.97    --  107.75 -57.00 120.00   58
 35  \w    -25.00  43.00   0.50    2.99    --   49.96 -38.00  90.00  136
 36  \w   -151.00 -64.00   0.50   11.97    --  -86.25 -77.00  30.00  174
 37  \w   -157.00 -71.00   0.50   11.97    --  -86.25 -57.00  30.00  172
 38  \w   -157.00 -71.00   0.50   11.97    --  -86.25 -57.00 -30.00  172
 39  \w   -161.00 -75.00   0.50   11.97    --  -86.25 -19.00   0.00  172
 40  \w   -157.00 -71.00   0.50   11.97    --  -86.25 -57.00 103.00  172
;
_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  0.0276
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            33288
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.880
_diffrn_reflns_theta_min         3.108
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.722
_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    1.326
_exptl_crystal_description       prism
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 2826 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(4)
_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   1.037
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     518
_refine_ls_number_reflns         7143
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0254
_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^)+(0.0369P)^2^+1.1311P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0648
_refine_ls_wR_factor_ref         0.0655
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.890
_reflns_number_gt                6882
_reflns_number_total             7143
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01231f2.cif
_cod_data_source_block           kk_white
_cod_original_cell_volume        3519.81(6)
_cod_database_code               7245754
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.654
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C3A(H3A), C3(H3), C5(H5), C11(H11), C5A(H5A), C11A(H11A)
1.b Secondary CH2 refined with riding coordinates:
 C10(H10C,H10D), C10A(H10A,H10B), C4A(H4AA,H4AB), C4(H4A,H4B), C6A(H6AA,H6AB),
 C7(H7A,H7B), C6(H6A,H6B), C7A(H7AA,H7AB)
1.c Aromatic/amide H refined with riding coordinates:
 NA(HA), N(H), C13A(H13A), C15A(H15A), C19A(H19A), C16A(H16A), C22A(H22A),
 C20A(H20A), C13(H13), C14A(H14A), C22(H22), C21A(H21A), C14(H14), C16(H16),
 C21(H21), C19(H19), C15(H15), C20(H20)
;
_shelx_res_checksum              72585
_shelx_hkl_checksum              32538
_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
- Detector area scaling
- B-factor correction
;