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_7244989
_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_moiety         'C9 H9 Br2 N O3, 2 H2 O'
_chemical_formula_sum            'C9 H13 Br2 N O5'
_chemical_formula_weight         375.02
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-07-25 deposited with the CCDC.	2022-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.14(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.692(1)
_cell_length_b                   10.588(2)
_cell_length_c                   10.925(2)
_cell_measurement_reflns_used    1181
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.999
_cell_measurement_theta_min      1.839
_cell_volume                     657.4(2)
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_collection       'Elettra XRD1 Data Collection SW'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_molecular_graphics    'Ortep3 for Windows - Coot'
_computing_publication_material  'enCIFer - publCIF'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type
;
'Huber 4-circles Kappa Goniometer, Pilatus 2M detector'
;
_diffrn_measurement_method       '\p scans'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7037
_diffrn_reflns_point_group_measured_fraction_full 0.925
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         1.839
_diffrn_source                   'Elettra Synchrotron - XRD1 BL'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.951
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.894
_exptl_crystal_description       'Thin needles'
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.927
_refine_diff_density_min         -1.866
_refine_diff_density_rms         0.257
_refine_ls_abs_structure_details
;
 Flack x determined using 1596 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.010(10)
_refine_ls_extinction_coef       0.98(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   1.139
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         3669
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0606P)^2^+0.4072P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1097
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_full    0.873
_reflns_Friedel_fraction_max     0.858
_reflns_number_gt                3643
_reflns_number_total             3669
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00670g2.cif
_cod_data_source_block           DiBrY
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7244989
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.469
_shelx_estimated_absorpt_t_max   0.647
_shelx_res_checksum              91345