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_1546049
_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 H10 Cl N O2, H2 O'
_chemical_formula_sum            'C9 H12 Cl N O3'
_chemical_formula_weight         217.64
_chemical_name_systematic        '4-chlorophenylalanine '
_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
_audit_creation_date             2017-02-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-02-14 deposited with the CCDC.
2017-04-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.421(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5539(8)
_cell_length_b                   5.4096(3)
_cell_length_c                   15.0157(9)
_cell_measurement_reflns_used    2578
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      71.8962
_cell_measurement_theta_min      3.0994
_cell_volume                     1044.56(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector_area_resol_mean 16.1183
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
  1 omega  -68.00  -27.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000 -150.0000 41

  2 omega  -38.00    5.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   90.0000 43

  3 omega  -15.00   26.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000 -150.0000 41

  4 omega -125.00  -29.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -54.9842  -37.0000 -180.0000 96

  5 omega   47.00  100.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       54.9842 -137.0000   51.0000 53

  6 omega  -71.00    7.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.0000   37.0000 -180.0000 78

  7 omega  -72.00  -38.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.0000   25.0000 -180.0000 34

  8 omega   41.00   80.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      109.9684  -50.0000  -60.0000 39

  9 omega   76.00  103.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      109.9684   25.0000 -120.0000 27

 10 omega   38.00   66.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      109.9684  -25.0000  150.0000 28

 11 omega   76.00  176.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      109.9684   25.0000  -30.0000 100

 12 omega  114.00  174.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      109.9684   25.0000 -120.0000 60

 13 omega   40.00   83.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      109.9684  -50.0000 -150.0000 43

 14 omega   45.00  102.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      109.9684  -91.0000   30.0000 57

 15 omega   42.00   71.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      109.9684  -25.0000 -120.0000 29

 16 omega   48.00  103.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      109.9684  -91.0000  -60.0000 55

 17 omega   38.00   64.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      109.9684  -25.0000 -180.0000 26

 18 omega   40.00   67.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      109.9684  -25.0000   90.0000 27

 19 omega  -73.00   44.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -19.0000  -30.0000 117

 20 omega  -72.00   26.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -37.0000  -90.0000 98

 21 omega   34.00   81.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       54.9842   57.0000   90.0000 47
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1175860000
_diffrn_orient_matrix_UB_12      -0.0074618000
_diffrn_orient_matrix_UB_13      -0.0141075000
_diffrn_orient_matrix_UB_21      -0.0226310000
_diffrn_orient_matrix_UB_22      -0.0065480000
_diffrn_orient_matrix_UB_23      -0.1070972000
_diffrn_orient_matrix_UB_31      0.0035004000
_diffrn_orient_matrix_UB_32      -0.2848477000
_diffrn_orient_matrix_UB_33      0.0027599000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4433
_diffrn_reflns_point_group_measured_fraction_full 0.707
_diffrn_reflns_point_group_measured_fraction_max 0.685
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.042
_diffrn_reflns_theta_min         3.102
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.118
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.945
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
;
 Flack x determined using 532 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_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         2825
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0685
_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^)+(0.0607P)^2^+1.7850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1640
_refine_ls_wR_factor_ref         0.1687
_reflns_Friedel_coverage         0.265
_reflns_Friedel_fraction_full    0.341
_reflns_Friedel_fraction_max     0.323
_reflns_number_gt                2655
_reflns_number_total             2825
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7fd00108h2.cif
_cod_data_source_block           phe
_cod_depositor_comments
;

2019-01-23
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C9 H10 Cl N O2), 2(H2 O)'
_cod_original_formula_sum        'C18 H24 Cl2 N2 O6'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     435.29
_cod_database_code               1546049
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 N(H,H,H) groups
2. Restrained distances
 O5-H5B
 0.95 with sigma of 0.02
 O5-H5A
 0.95 with sigma of 0.02
 O6-H6B
 0.95 with sigma of 0.02
 O6-H6A
 0.95 with sigma of 0.02
 H6A-H6B
 1.54 with sigma of 0.05
 H5B-H5A
 1.54 with sigma of 0.05
3.a Ternary CH refined with riding coordinates:
 C2(H2), C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C12(H12A,H12B)
3.c Me refined with riding coordinates:
 N1(H1A,H1B,H1C), N2(H2A,H2B,H2C)
3.d Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C14(H14), C15(H15), C17(H17), C18(H18)
;
_shelx_res_checksum              39513
_olex2_submission_special_instructions 'No special instructions were received'