Hydrogen- and halogen bond synergy in the self-assembly of 3,5-dihalo-tyrosines: structural and theoretical insights
Sori, Lorenzo; Pizzi, Andrea; Demitri, Nicola; Terraneo, Giancarlo; Frontera, Antonio; Metrangolo, Pierangelo; CrystEngComm  (2022) –; doi:10.1039/D2CE00670G

data_7244990
_publ_section_title
;
 Hydrogen- and halogen bond synergy in the self-assembly of
 3,5-dihalo-tyrosines: structural and theoretical insights
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00670G
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_sum            'C9 H11 Cl2 N O4'
_chemical_formula_weight         268.09
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-12-15 deposited with the CCDC.	2022-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3436(2)
_cell_length_b                   7.4422(2)
_cell_length_c                   20.8254(7)
_cell_measurement_reflns_used    7570
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.03
_cell_measurement_theta_min      2.94
_cell_volume                     1138.16(6)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8858
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.032
_diffrn_reflns_theta_min         3.914
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.568
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1493 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.027(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         3618
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0186
_refine_ls_R_factor_gt           0.0181
_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^)+(0.0265P)^2^+0.1587P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0505
_refine_ls_wR_factor_ref         0.0508
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3543
_reflns_number_total             3618
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00670g2.cif
_cod_data_source_block           lg216_DiClTr_100k_0m
_cod_database_code               7244990
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              43171