Analysis of short contacts in crystals of halogenated amino acids: atom–atom interactions vs. energy frameworks
De Beer, Francois J.; Jacobs, Frederick J. F.; Ntsila, Akho; Kama, Dumisani V.; Azov, Vladimir A.; CrystEngComm 26 (2024) 604–619; doi:10.1039/D3CE01029E

data_7247871
_publ_section_title
;
 Analysis of short contacts in crystals of halogenated amino acids:
 atom--atom interactions vs. energy frameworks
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              604
_journal_page_last               619
_journal_paper_doi               10.1039/D3CE01029E
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C15 H20 Cl N O4'
_chemical_formula_sum            'C15 H20 Cl N O4'
_chemical_formula_weight         313.77
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-01-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-01-26 deposited with the CCDC.	2023-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.1069(15)
_cell_length_b                   11.791(3)
_cell_length_c                   26.327(8)
_cell_measurement_reflns_used    2519
_cell_measurement_temperature    105(2)
_cell_measurement_theta_max      58.008
_cell_measurement_theta_min      3.357
_cell_volume                     1585.3(8)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      105.00
_diffrn_measured_fraction_theta_full 0.813
_diffrn_measured_fraction_theta_max 0.813
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0872
_diffrn_reflns_Laue_measured_fraction_full 0.813
_diffrn_reflns_Laue_measured_fraction_max 0.813
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            4985
_diffrn_reflns_point_group_measured_fraction_full 0.759
_diffrn_reflns_point_group_measured_fraction_max 0.759
_diffrn_reflns_theta_full        67.339
_diffrn_reflns_theta_max         67.339
_diffrn_reflns_theta_min         3.357
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.268
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1530 before and 0.0906 after correction.
The Ratio of minimum to maximum transmission is 0.6862.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.021
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details
;
 Flack x determined using 439 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(2)
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         2156
_refine_ls_number_restraints     97
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1294
_refine_ls_R_factor_gt           0.0802
_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^)+(0.1255P)^2^+2.7844P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1981
_refine_ls_wR_factor_ref         0.2465
_reflns_Friedel_coverage         0.566
_reflns_Friedel_fraction_full    0.679
_reflns_Friedel_fraction_max     0.679
_reflns_number_gt                1497
_reflns_number_total             2156
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce01029e2.cif
_cod_data_source_block           cu_v3_22dfd1_b_0m
_cod_depositor_comments
'Adding full bibliography for 7247865--7247871.cif.'
_cod_database_code               7247871
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.639
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H1-N1
 1 with sigma of 0.02
3. Rigid bond restraints
 C11, C6, C7, C8, C9, C10
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C10A, C11A, C6A, C7A, C8A, C9A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C11 \\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 1.7A
C10A \\sim C11A \\sim C6A \\sim C7A \\sim C8A \\sim C9A: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
5. Others
 Sof(O2A)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(H11A)=
 Sof(C6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=1-FVAR(1)
 Sof(O2)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(C11)=Sof(H11)=Sof(C6)=Sof(C7)=Sof(H7)=
 Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C2(H2)
6.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C5A(H5AA,H5AB)
6.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C7(H7), C8(H8), C9(H9), C10(H10), C10A(H10A), C11A(H11A), C7A(H7A),
 C8A(H8A), C9A(H9A)
6.d Fitted hexagon refined as free rotating group:
 C11(C6,C7,C8,C9,C10), C10A(C11A,C6A,C7A,C8A,C9A)
6.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              76465
_olex2_submission_special_instructions 'No special instructions were received'