FDHALO17: Halogen effects on the solid-state packing of phenylalanine derivatives and the resultant gelation properties
Ramalhete, Susana; Foster, Jamie S.; Green, Hayley R.; Nartowski, Karol P.; Heinrich, Margaux; Martin, Peter; Khimyak, Yaroslav Z.; Lloyd, Gareth O.; Faraday Discuss.  (2017) –; doi:10.1039/C7FD00108H

data_1546050
_publ_section_title
;
 FDHALO17: Halogen effects on the solid-state packing of phenylalanine
 derivatives and the resultant gelation properties
;
_journal_name_full               'Faraday Discuss.'
_journal_paper_doi               10.1039/C7FD00108H
_journal_year                    2017
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C9 H9 F2 N O2, H2 O'
_chemical_formula_sum            'C9 H11 F2 N O3'
_chemical_formula_weight         219.19
_chemical_name_systematic        '2,4-difluoro-phenylalanine '
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-15
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2017-02-14 deposited with the CCDC.
2017-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.712(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.100(3)
_cell_length_b                   5.4019(12)
_cell_length_c                   14.423(4)
_cell_measurement_reflns_used    2351
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.04
_cell_measurement_theta_min      2.87
_cell_volume                     1002.9(4)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_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  0.0624
_diffrn_reflns_av_unetI/netI     0.0730
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15137
_diffrn_reflns_point_group_measured_fraction_full 0.864
_diffrn_reflns_point_group_measured_fraction_max 0.800
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.040
_diffrn_reflns_theta_min         2.327
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6922
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0564 before and 0.0457 after correction.
The Ratio of minimum to maximum transmission is 0.9279.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 906 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4707
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0369P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0894
_reflns_Friedel_coverage         0.479
_reflns_Friedel_fraction_full    0.697
_reflns_Friedel_fraction_max     0.574
_reflns_number_gt                3394
_reflns_number_total             4707
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7fd00108h2.cif
_cod_data_source_block           final
_cod_original_cell_volume        1002.8(4)
_cod_database_code               1546050
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.879
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O29(H29A,H29B), O28(H28A,H28B)
2.b Ternary CH refined with riding coordinates:
 C15(H15), C2(H2)
2.c Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C19(H19A,H19B)
2.d Aromatic/amide H refined with riding coordinates:
 C22(H22), C11(H11), C25(H25), C21(H21), C7(H7), C8(H8)
2.e Idealised Me refined as rotating group:
 N14(H14A,H14B,H14C), N1(H1A,H1B,H1C)
;
_shelx_res_checksum              52831
_olex2_submission_special_instructions 'No special instructions were received'