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#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/60/1546053.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
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data_1546053
loop_
_publ_author_name
'Ramalhete, Susana'
'Foster, Jamie S.'
'Green, Hayley R.'
'Nartowski, Karol P.'
'Heinrich, Margaux'
'Martin, Peter'
'Khimyak, Yaroslav Z.'
'Lloyd, Gareth O.'
_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 I N O2, H2 O'
_chemical_formula_sum            'C9 H12 I N O3'
_chemical_formula_weight         309.10
_chemical_name_systematic        4-Iodophenylalanine
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-02
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.3139(3)
_cell_length_b                   6.3152(4)
_cell_length_c                   32.741(2)
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.44
_cell_measurement_theta_min      3.29
_cell_volume                     1098.73(11)
_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 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            30824
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         32.535
_diffrn_reflns_theta_min         3.285
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.897
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6036
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0691 before and 0.0491 after correction. The Ratio of minimum to maximum transmission is 0.8087. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.869
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         3.548
_refine_diff_density_min         -5.204
_refine_diff_density_rms         0.201
_refine_ls_abs_structure_details
;
 Flack x determined using 1594 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.321
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         3975
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.321
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0451
_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/[σ²(Fo²)+(0.0278P)²+7.3897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1059
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3947
_reflns_number_total             3975
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7fd00108h2.cif
_cod_data_source_block           5179a
_cod_original_cell_volume        1098.72(12)
_cod_database_code               1546053
_shelxl_version_number           2014/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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. Restrained distances
 O2-H1E
 1.83 with sigma of 0.002
 O1-H1D
 0.95 with sigma of 0.02
 O1-H1E
 0.95 with sigma of 0.02
 H1D-H1E
 1.5 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9)
3.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
I1 I 0.21834(8) 0.36260(7) 0.46518(2) 0.01442(10) Uani 1 1 d .
O1 O 0.4295(11) 1.4222(8) 0.28549(16) 0.0172(10) Uani 1 1 d D
H1D H 0.273(8) 1.355(12) 0.282(3) 0.026 Uiso 1 1 d DR
H1E H 0.538(11) 1.312(8) 0.295(2) 0.026 Uiso 1 1 d DR
N1 N 1.2777(11) 0.8404(8) 0.29179(16) 0.0134(9) Uani 1 1 d .
H1A H 1.2528 0.8785 0.2653 0.016 Uiso 1 1 calc GR
H1B H 1.3368 0.7052 0.2928 0.016 Uiso 1 1 calc GR
H1C H 1.3918 0.9292 0.3034 0.016 Uiso 1 1 calc GR
C1 C 0.8939(13) 1.0583(10) 0.30400(19) 0.0111(11) Uani 1 1 d .
O2 O 0.6820(10) 1.0845(8) 0.32084(15) 0.0146(9) Uani 1 1 d D
C2 C 1.0335(11) 0.8538(11) 0.31458(17) 0.0101(9) Uani 1 1 d .
H2 H 0.9261 0.7317 0.3059 0.012 Uiso 1 1 calc R
O3 O 0.9950(10) 1.1886(8) 0.27970(16) 0.0162(10) Uani 1 1 d .
C3 C 1.0849(13) 0.8323(11) 0.3612(2) 0.0134(12) Uani 1 1 d .
H3A H 1.2398 0.7477 0.3652 0.016 Uiso 1 1 calc R
H3B H 1.1160 0.9751 0.3727 0.016 Uiso 1 1 calc R
C4 C 0.8710(13) 0.7289(10) 0.38502(18) 0.0104(10) Uani 1 1 d .
C5 C 0.7897(16) 0.5251(10) 0.37380(19) 0.0159(11) Uani 1 1 d .
H5 H 0.8613 0.4578 0.3506 0.019 Uiso 1 1 calc R
C6 C 0.6031(13) 0.4198(11) 0.3966(2) 0.0140(11) Uani 1 1 d .
H6 H 0.5497 0.2816 0.3891 0.017 Uiso 1 1 calc R
C7 C 0.4979(14) 0.5206(12) 0.4305(2) 0.0136(12) Uani 1 1 d .
C8 C 0.5743(15) 0.7232(12) 0.4420(2) 0.0158(12) Uani 1 1 d .
H8 H 0.5018 0.7904 0.4651 0.019 Uiso 1 1 calc R
C9 C 0.7603(14) 0.8265(9) 0.41882(18) 0.0155(12) Uani 1 1 d .
H9 H 0.8116 0.9652 0.4263 0.019 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
H1D O1 H1E 104(3)
H1A N1 H1B 109.5
H1A N1 H1C 109.5
H1B N1 H1C 109.5
C2 N1 H1A 109.5
C2 N1 H1B 109.5
C2 N1 H1C 109.5
O2 C1 C2 116.3(6)
O3 C1 O2 124.6(6)
O3 C1 C2 119.1(6)
N1 C2 C1 110.8(5)
N1 C2 H2 108.1
N1 C2 C3 109.4(5)
C1 C2 H2 108.1
C1 C2 C3 112.4(5)
C3 C2 H2 108.1
C2 C3 H3A 108.7
C2 C3 H3B 108.7
H3A C3 H3B 107.6
C4 C3 C2 114.1(5)
C4 C3 H3A 108.7
C4 C3 H3B 108.7
C5 C4 C3 119.2(6)
C9 C4 C3 122.0(6)
C9 C4 C5 118.8(6)
C4 C5 H5 119.7
C4 C5 C6 120.6(6)
C6 C5 H5 119.7
C5 C6 H6 120.4
C7 C6 C5 119.2(6)
C7 C6 H6 120.4
C6 C7 I1 119.5(5)
C6 C7 C8 121.1(7)
C8 C7 I1 119.4(5)
C7 C8 H8 120.5
C7 C8 C9 119.0(7)
C9 C8 H8 120.5
C4 C9 C8 121.2(6)
C4 C9 H9 119.4
C8 C9 H9 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C7 2.120(7)
O1 H1D 0.94(3)
O1 H1E 0.959(16)
N1 H1A 0.9100
N1 H1B 0.9100
N1 H1C 0.9100
N1 C2 1.499(8)
C1 O2 1.265(8)
C1 C2 1.530(9)
C1 O3 1.265(8)
C2 H2 1.0000
C2 C3 1.558(9)
C3 H3A 0.9900
C3 H3B 0.9900
C3 C4 1.525(9)
C4 C5 1.406(9)
C4 C9 1.397(9)
C5 H5 0.9500
C5 C6 1.409(10)
C6 H6 0.9500
C6 C7 1.394(9)
C7 C8 1.394(10)
C8 H8 0.9500
C8 C9 1.406(10)
C9 H9 0.9500
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
I1 C7 C8 C9 179.8(5)
N1 C2 C3 C4 -149.2(5)
C1 C2 C3 C4 87.3(7)
O2 C1 C2 N1 178.5(5)
O2 C1 C2 C3 -58.8(7)
C2 C3 C4 C5 57.4(8)
C2 C3 C4 C9 -125.4(7)
O3 C1 C2 N1 -1.8(8)
O3 C1 C2 C3 120.8(7)
C3 C4 C5 C6 176.1(7)
C3 C4 C9 C8 -175.9(6)
C4 C5 C6 C7 0.5(10)
C5 C4 C9 C8 1.2(10)
C5 C6 C7 I1 -179.7(5)
C5 C6 C7 C8 0.0(10)
C6 C7 C8 C9 0.2(10)
C7 C8 C9 C4 -0.8(11)
C9 C4 C5 C6 -1.1(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139050089
