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_7247865
_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         'C22 H24 Cl N O4'
_chemical_formula_sum            'C22 H24 Cl N O4'
_chemical_formula_weight         401.87
_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             2023-03-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-03-09 deposited with the CCDC.	2023-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.547(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.207(2)
_cell_length_b                   5.1052(7)
_cell_length_c                   26.456(4)
_cell_measurement_reflns_used    9748
_cell_measurement_temperature    109.0
_cell_measurement_theta_max      53.45
_cell_measurement_theta_min      3.39
_cell_volume                     2025.5(5)
_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      109.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0677
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            19172
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        53.493
_diffrn_reflns_theta_max         53.493
_diffrn_reflns_theta_min         1.693
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.900
_exptl_absorpt_correction_T_max  0.7505
_exptl_absorpt_correction_T_min  0.5923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1657 before and 0.0986 after correction.
The Ratio of minimum to maximum transmission is 0.7892.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       Needle
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.396
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.15(2)
_refine_ls_extinction_coef       0.0041(4)
_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   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         4721
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0389
_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^)+(0.0540P)^2^+1.1613P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1061
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    0.952
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                4454
_reflns_number_total             4721
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce01029e2.cif
_cod_data_source_block           cu_v4_21dfd1_0m
_cod_depositor_comments
'Adding full bibliography for 7247865--7247871.cif.'
_cod_original_cell_volume        2025.4(5)
_cod_database_code               7247865
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.520
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.85(2)
 0.15(2)
2. 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
3. Restrained distances
 C23A-O6
 1.35 with sigma of 0.01
 C23-O6
 1.35 with sigma of 0.01
 C24-H24
 1 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C23A) = Uanis(O5A)
Uanis(C28) = Uanis(C29A)
Uanis(C23) = Uanis(O5)
Uanis(O6A) = Uanis(C23A)
Uanis(O6) = Uanis(C23)
Uanis(C30) = Uanis(C29)
Uanis(C28A) = Uanis(C27A)
5. Others
 Fixed Sof: O6(0.56) C23(0.56) C27(0.56) C29(0.56) H29A(0.56) H29B(0.56)
 H29C(0.56) C28(0.56) H28A(0.56) H28B(0.56) H28C(0.56) C30(0.56) H30A(0.56)
 H30B(0.56) H30C(0.56) O5(0.56) O5A(0.44) C28A(0.44) H28D(0.44) H28E(0.44)
 H28F(0.44) C27A(0.44) C30A(0.44) H30D(0.44) H30E(0.44) H30F(0.44) C29A(0.44)
 H29D(0.44) H29E(0.44) H29F(0.44) C23A(0.44) O6A(0.44)
6.a Ternary CH refined with riding coordinates:
 C32(H32), C10(H10), C2(H2A)
6.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C31(H31A,H31B), C25(H25A,H25B), C3(H3A,H3B)
6.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C12(H12), C21(H21), C34(H34), C36(H36), C35(H35), C15(H15),
 C43(H43), C18(H18), C20(H20), C40(H40), C14(H14), C19(H19), C13(H13), C42(H42),
  C37(H37), C41(H41)
6.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C29(H29A,H29B,H29C),
 C28(H28A,H28B,H28C), C30(H30A,H30B,H30C), C28A(H28D,H28E,H28F), C30A(H30D,H30E,
 H30F), C29A(H29D,H29E,H29F)
;
_shelx_res_checksum              26958
_olex2_submission_special_instructions 'No special instructions were received'