# Electronic Supplementary Material (ESI) for Faraday Discussions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_phe
_database_code_depnum_ccdc_archive 'CCDC 1532632'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-04-24 downloaded from the CCDC.
;
_audit_creation_date             2017-02-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        '4-chlorophenylalanine '
_chemical_formula_moiety         '2(C9 H10 Cl N O2), 2(H2 O)'
_chemical_formula_sum            'C18 H24 Cl2 N2 O6'
_chemical_formula_weight         435.29
_chemical_absolute_configuration rm
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   13.5539(8)
_cell_length_b                   5.4096(3)
_cell_length_c                   15.0157(9)
_cell_angle_alpha                90
_cell_angle_beta                 108.421(6)
_cell_angle_gamma                90
_cell_volume                     1044.56(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2578
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      71.8962
_cell_measurement_theta_min      3.0994
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -68.00  -27.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000 -150.0000 41

#__ type_ start__ end____ width___ exp.time_
  2 omega  -38.00    5.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   90.0000 43

#__ type_ start__ end____ width___ exp.time_
  3 omega  -15.00   26.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000 -150.0000 41

#__ type_ start__ end____ width___ exp.time_
  4 omega -125.00  -29.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -54.9842  -37.0000 -180.0000 96

#__ type_ start__ end____ width___ exp.time_
  5 omega   47.00  100.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       54.9842 -137.0000   51.0000 53

#__ type_ start__ end____ width___ exp.time_
  6 omega  -71.00    7.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.0000   37.0000 -180.0000 78

#__ type_ start__ end____ width___ exp.time_
  7 omega  -72.00  -38.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -64.0000   25.0000 -180.0000 34

#__ type_ start__ end____ width___ exp.time_
  8 omega   41.00   80.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      109.9684  -50.0000  -60.0000 39

#__ type_ start__ end____ width___ exp.time_
  9 omega   76.00  103.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      109.9684   25.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00   66.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      109.9684  -25.0000  150.0000 28

#__ type_ start__ end____ width___ exp.time_
 11 omega   76.00  176.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      109.9684   25.0000  -30.0000 100

#__ type_ start__ end____ width___ exp.time_
 12 omega  114.00  174.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      109.9684   25.0000 -120.0000 60

#__ type_ start__ end____ width___ exp.time_
 13 omega   40.00   83.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      109.9684  -50.0000 -150.0000 43

#__ type_ start__ end____ width___ exp.time_
 14 omega   45.00  102.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      109.9684  -91.0000   30.0000 57

#__ type_ start__ end____ width___ exp.time_
 15 omega   42.00   71.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      109.9684  -25.0000 -120.0000 29

#__ type_ start__ end____ width___ exp.time_
 16 omega   48.00  103.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      109.9684  -91.0000  -60.0000 55

#__ type_ start__ end____ width___ exp.time_
 17 omega   38.00   64.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      109.9684  -25.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   40.00   67.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      109.9684  -25.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 19 omega  -73.00   44.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -19.0000  -30.0000 117

#__ type_ start__ end____ width___ exp.time_
 20 omega  -72.00   26.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -37.0000  -90.0000 98

#__ type_ start__ end____ width___ exp.time_
 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       'ω 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_source                   'Enhance Ultra (Cu) X-ray Source'
_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_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_computing_structure_solution    ?
_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_coef       .
_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_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0685
_refine_ls_restrained_S_all      1.075
_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/[σ²(Fo²)+(0.0607P)²+1.7850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1640
_refine_ls_wR_factor_ref         0.1687
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.18732(19) 0.3641(5) -0.00633(14) 0.0893(9) Uani 1 1 d . . . . .
O1 O 0.1371(3) 0.5697(8) 0.3844(3) 0.0436(11) Uani 1 1 d . . . . .
N1 N 0.1340(3) 0.0830(10) 0.4119(4) 0.0443(13) Uani 1 1 d . . . . .
H1A H 0.1239 -0.0834 0.4078 0.066 Uiso 1 1 calc R . . . .
H1B H 0.1735 0.1290 0.3757 0.066 Uiso 1 1 calc R . . . .
H1C H 0.1672 0.1252 0.4727 0.066 Uiso 1 1 calc R . . . .
C1 C 0.0499(5) 0.4900(13) 0.3860(6) 0.054(2) Uani 1 1 d . . . . .
H5A H 0.168(5) 0.130(16) 0.631(6) 0.10(3) Uiso 1 1 d D . . . .
H6A H 0.624(2) 0.159(18) 0.364(7) 0.12(4) Uiso 1 1 d D . . . .
Cl2 Cl 0.6781(3) 0.3014(5) 0.06798(18) 0.1133(12) Uani 1 1 d . . . . .
O2 O -0.0236(3) 0.6246(9) 0.3901(5) 0.0735(18) Uani 1 1 d . . . . .
N2 N 0.3526(3) 0.6248(9) 0.4250(3) 0.0289(9) Uani 1 1 d . . . . .
H2A H 0.3527 0.7914 0.4166 0.043 Uiso 1 1 calc R . . . .
H2B H 0.2862 0.5671 0.4026 0.043 Uiso 1 1 calc R . . . .
H2C H 0.3794 0.5892 0.4872 0.043 Uiso 1 1 calc R . . . .
C2 C 0.0316(4) 0.2113(12) 0.3786(6) 0.0523(19) Uani 1 1 d . . . . .
H2 H -0.0101 0.1635 0.4202 0.063 Uiso 1 1 calc R . . . .
O3 O 0.3329(3) 0.1301(8) 0.3917(3) 0.0379(9) Uani 1 1 d . . . . .
C3 C -0.0289(4) 0.1362(13) 0.2772(6) 0.069(3) Uani 1 1 d . . . . .
H3A H -0.0434 -0.0434 0.2760 0.083 Uiso 1 1 calc R . . . .
H3B H -0.0966 0.2233 0.2580 0.083 Uiso 1 1 calc R . . . .
O4 O 0.4977(3) 0.1053(7) 0.3930(2) 0.0312(8) Uani 1 1 d . . . . .
C4 C 0.0260(5) 0.1911(13) 0.2065(6) 0.062(2) Uani 1 1 d . . . . .
O5 O 0.2179(3) 0.1790(11) 0.6029(4) 0.0558(13) Uani 1 1 d D . . . .
C5 C 0.0043(6) 0.4069(14) 0.1539(7) 0.078(3) Uani 1 1 d . . . . .
H5 H -0.0465 0.5179 0.1621 0.093 Uiso 1 1 calc R . . . .
O6 O 0.6969(3) 0.1651(11) 0.3740(4) 0.0552(13) Uani 1 1 d D . . . .
C6 C 0.0551(7) 0.4639(15) 0.0896(6) 0.081(3) Uani 1 1 d . . . . .
H6 H 0.0409 0.6140 0.0551 0.097 Uiso 1 1 calc R . . . .
C7 C 0.1272(6) 0.2969(15) 0.0768(5) 0.066(2) Uani 1 1 d . . . . .
C8 C 0.1498(5) 0.0777(14) 0.1276(5) 0.0563(19) Uani 1 1 d . . . . .
H8 H 0.1990 -0.0354 0.1179 0.068 Uiso 1 1 calc R . . . .
C9 C 0.0992(5) 0.0272(13) 0.1923(5) 0.0540(18) Uani 1 1 d . . . . .
H9 H 0.1145 -0.1214 0.2278 0.065 Uiso 1 1 calc R . . . .
C10 C 0.4163(4) 0.2255(11) 0.3880(3) 0.0300(12) Uani 1 1 d . . . . .
C11 C 0.4166(4) 0.5058(10) 0.3738(4) 0.0266(11) Uani 1 1 d . . . . .
H11 H 0.4896 0.5676 0.4000 0.032 Uiso 1 1 calc R . . . .
C12 C 0.3747(4) 0.5741(12) 0.2696(4) 0.0355(12) Uani 1 1 d . . . . .
H12A H 0.3073 0.4893 0.2409 0.043 Uiso 1 1 calc R . . . .
H12B H 0.3618 0.7544 0.2638 0.043 Uiso 1 1 calc R . . . .
C13 C 0.4474(5) 0.5054(11) 0.2164(4) 0.0374(13) Uani 1 1 d . . . . .
C14 C 0.4349(6) 0.2932(14) 0.1620(4) 0.0499(16) Uani 1 1 d . . . . .
H14 H 0.3773 0.1877 0.1569 0.060 Uiso 1 1 calc R . . . .
C15 C 0.5046(8) 0.2316(15) 0.1147(4) 0.068(2) Uani 1 1 d . . . . .
H15 H 0.4942 0.0879 0.0765 0.082 Uiso 1 1 calc R . . . .
C16 C 0.5894(8) 0.3840(16) 0.1245(5) 0.067(2) Uani 1 1 d . . . . .
C17 C 0.6032(7) 0.5968(15) 0.1770(5) 0.0595(19) Uani 1 1 d . . . . .
H17 H 0.6606 0.7024 0.1815 0.071 Uiso 1 1 calc R . . . .
C18 C 0.5331(5) 0.6552(13) 0.2230(4) 0.0449(15) Uani 1 1 d . . . . .
H18 H 0.5434 0.8010 0.2601 0.054 Uiso 1 1 calc R . . . .
H6B H 0.714(6) 0.331(7) 0.366(6) 0.10(3) Uiso 1 1 d D . . . .
H5B H 0.235(7) 0.346(7) 0.620(6) 0.09(3) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C7 1.731(9) . ?
O1 C1 1.266(7) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C2 1.490(7) . ?
C1 O2 1.252(8) . ?
C1 C2 1.526(9) . ?
Cl2 C16 1.735(8) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
N2 C11 1.476(6) . ?
C2 H2 1.0000 . ?
C2 C3 1.537(11) . ?
O3 C10 1.260(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.506(12) . ?
O4 C10 1.262(6) . ?
C4 C5 1.388(10) . ?
C4 C9 1.396(11) . ?
O5 H5A 0.95(2) . ?
O5 H5B 0.95(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(13) . ?
O6 H6A 0.95(2) . ?
O6 H6B 0.95(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.388(13) . ?
C7 C8 1.390(10) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(11) . ?
C9 H9 0.9500 . ?
C10 C11 1.531(8) . ?
C11 H11 1.0000 . ?
C11 C12 1.532(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.498(8) . ?
C13 C14 1.388(9) . ?
C13 C18 1.394(9) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(11) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(12) . ?
C16 C17 1.374(11) . ?
C17 H17 0.9500 . ?
C17 C18 1.376(9) . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
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 . . ?
O1 C1 C2 117.8(6) . . ?
O2 C1 O1 124.4(6) . . ?
O2 C1 C2 117.7(6) . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C11 N2 H2A 109.5 . . ?
C11 N2 H2B 109.5 . . ?
C11 N2 H2C 109.5 . . ?
N1 C2 C1 108.8(5) . . ?
N1 C2 H2 108.7 . . ?
N1 C2 C3 111.0(6) . . ?
C1 C2 H2 108.7 . . ?
C1 C2 C3 110.9(7) . . ?
C3 C2 H2 108.7 . . ?
C2 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C4 C3 C2 114.7(5) . . ?
C4 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
C5 C4 C3 120.3(8) . . ?
C5 C4 C9 118.7(9) . . ?
C9 C4 C3 121.0(7) . . ?
H5A O5 H5B 108(5) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.4(9) . . ?
C6 C5 H5 119.3 . . ?
H6A O6 H6B 108(5) . . ?
C5 C6 H6 120.7 . . ?
C5 C6 C7 118.6(7) . . ?
C7 C6 H6 120.7 . . ?
C6 C7 Cl1 118.4(6) . . ?
C6 C7 C8 121.4(9) . . ?
C8 C7 Cl1 120.2(8) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 C7 118.8(8) . . ?
C9 C8 H8 120.6 . . ?
C4 C9 H9 119.5 . . ?
C8 C9 C4 121.0(7) . . ?
C8 C9 H9 119.5 . . ?
O3 C10 O4 124.5(5) . . ?
O3 C10 C11 117.0(5) . . ?
O4 C10 C11 118.6(5) . . ?
N2 C11 C10 109.4(4) . . ?
N2 C11 H11 108.8 . . ?
N2 C11 C12 109.7(4) . . ?
C10 C11 H11 108.8 . . ?
C10 C11 C12 111.4(5) . . ?
C12 C11 H11 108.8 . . ?
C11 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 C11 113.0(4) . . ?
C13 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C14 C13 C12 122.7(6) . . ?
C14 C13 C18 117.8(6) . . ?
C18 C13 C12 119.5(5) . . ?
C13 C14 H14 119.2 . . ?
C13 C14 C15 121.5(7) . . ?
C15 C14 H14 119.2 . . ?
C14 C15 H15 120.7 . . ?
C16 C15 C14 118.6(7) . . ?
C16 C15 H15 120.7 . . ?
C15 C16 Cl2 118.4(6) . . ?
C17 C16 Cl2 120.4(7) . . ?
C17 C16 C15 121.2(7) . . ?
C16 C17 H17 120.3 . . ?
C16 C17 C18 119.3(8) . . ?
C18 C17 H17 120.3 . . ?
C13 C18 H18 119.3 . . ?
C17 C18 C13 121.5(7) . . ?
C17 C18 H18 119.3 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C7 C8 C9 -178.9(5) . . . . ?
O1 C1 C2 N1 24.5(11) . . . . ?
O1 C1 C2 C3 -97.9(8) . . . . ?
N1 C2 C3 C4 -59.0(8) . . . . ?
C1 C2 C3 C4 62.1(8) . . . . ?
Cl2 C16 C17 C18 -178.4(6) . . . . ?
O2 C1 C2 N1 -157.9(7) . . . . ?
O2 C1 C2 C3 79.7(10) . . . . ?
N2 C11 C12 C13 168.0(5) . . . . ?
C2 C3 C4 C5 -95.9(7) . . . . ?
C2 C3 C4 C9 84.1(8) . . . . ?
O3 C10 C11 N2 36.2(6) . . . . ?
O3 C10 C11 C12 -85.2(6) . . . . ?
C3 C4 C5 C6 178.8(7) . . . . ?
C3 C4 C9 C8 -179.9(6) . . . . ?
O4 C10 C11 N2 -145.3(4) . . . . ?
O4 C10 C11 C12 93.2(5) . . . . ?
C4 C5 C6 C7 1.5(10) . . . . ?
C5 C4 C9 C8 0.2(9) . . . . ?
C5 C6 C7 Cl1 177.9(5) . . . . ?
C5 C6 C7 C8 -0.7(10) . . . . ?
C6 C7 C8 C9 -0.3(9) . . . . ?
C7 C8 C9 C4 0.6(9) . . . . ?
C9 C4 C5 C6 -1.3(10) . . . . ?
C10 C11 C12 C13 -70.7(6) . . . . ?
C11 C12 C13 C14 99.6(6) . . . . ?
C11 C12 C13 C18 -78.8(7) . . . . ?
C12 C13 C14 C15 -178.9(6) . . . . ?
C12 C13 C18 C17 178.7(6) . . . . ?
C13 C14 C15 C16 1.5(10) . . . . ?
C14 C13 C18 C17 0.2(9) . . . . ?
C14 C15 C16 Cl2 178.2(6) . . . . ?
C14 C15 C16 C17 -2.2(11) . . . . ?
C15 C16 C17 C18 2.0(12) . . . . ?
C16 C17 C18 C13 -1.0(11) . . . . ?
C18 C13 C14 C15 -0.5(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_final
_database_code_depnum_ccdc_archive 'CCDC 1532628'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-04-24 downloaded from the CCDC.
;
_audit_creation_date             2015-06-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        '2,4-difluoro-phenylalanine '
_chemical_formula_moiety         'C9 H9 F2 N O2, H2 O'
_chemical_formula_sum            'C9 H11 F2 N O3'
_chemical_formula_weight         219.19
_chemical_absolute_configuration rm
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   13.100(3)
_cell_length_b                   5.4019(12)
_cell_length_c                   14.423(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.712(8)
_cell_angle_gamma                90
_cell_volume                     1002.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2351
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.04
_cell_measurement_theta_min      2.87
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.879
_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 λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_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       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_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_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_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)'
_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_coef       .
_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_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.030
_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/[σ²(Fo²)+(0.0369P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0894
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.47526(14) 1.0835(3) 0.10634(13) 0.0169(4) Uani 1 1 d . . . . .
F27 F 0.28783(14) 0.7489(3) 0.60722(12) 0.0259(4) Uani 1 1 d . . . . .
F26 F 0.26444(14) 0.3392(3) 0.49863(12) 0.0294(5) Uani 1 1 d . . . . .
F12 F 0.22422(12) 0.8333(4) 0.40712(12) 0.0278(4) Uani 1 1 d . . . . .
F13 F 0.22121(13) 0.4354(4) 0.29421(12) 0.0315(5) Uani 1 1 d . . . . .
N14 N 0.13773(17) 0.5889(4) 0.88677(16) 0.0137(5) Uani 1 1 d . . . . .
H14A H 0.1584 0.5631 0.9498 0.016 Uiso 1 1 calc GR . . . .
H14B H 0.1278 0.7538 0.8756 0.016 Uiso 1 1 calc GR . . . .
H14C H 0.1875 0.5323 0.8557 0.016 Uiso 1 1 calc GR . . . .
C0AA C 0.5588(2) 0.9607(5) 0.12071(19) 0.0136(6) Uani 1 1 d . . . . .
O3 O 0.64899(14) 1.0515(3) 0.12647(14) 0.0204(5) Uani 1 1 d . . . . .
O17 O 0.15216(14) 0.1048(3) 0.85172(14) 0.0169(4) Uani 1 1 d . . . . .
C6 C 0.4815(2) 0.6705(5) 0.2882(2) 0.0151(6) Uani 1 1 d . . . . .
O29 O 0.73269(16) 0.4891(4) 0.89787(17) 0.0286(5) Uani 1 1 d . . . . .
H29A H 0.7508 0.2996 0.8919 0.043 Uiso 1 1 d G . . . .
H29B H 0.6658 0.4736 0.8799 0.043 Uiso 1 1 d G . . . .
C22 C 0.1128(2) 0.2234(6) 0.5580(2) 0.0221(7) Uani 1 1 d . . . . .
H22 H 0.1027 0.0821 0.5181 0.027 Uiso 1 1 calc R . . . .
C15 C 0.0380(2) 0.4532(5) 0.8526(2) 0.0145(6) Uani 1 1 d . . . . .
H15 H -0.0119 0.4937 0.8951 0.017 Uiso 1 1 calc R . . . .
O18 O -0.01010(16) 0.0308(4) 0.87092(17) 0.0311(6) Uani 1 1 d . . . . .
N1 N 0.63322(16) 0.5557(4) 0.08889(16) 0.0143(5) Uani 1 1 d . . . . .
H1A H 0.6158 0.5745 0.0252 0.017 Uiso 1 1 calc GR . . . .
H1B H 0.6361 0.3916 0.1034 0.017 Uiso 1 1 calc GR . . . .
H1C H 0.6964 0.6261 0.1101 0.017 Uiso 1 1 calc GR . . . .
C2 C 0.5531(2) 0.6789(5) 0.1350(2) 0.0128(6) Uani 1 1 d . . . . .
H2 H 0.4826 0.6186 0.1047 0.015 Uiso 1 1 calc R . . . .
C5 C 0.5734(2) 0.6099(5) 0.24084(19) 0.0158(6) Uani 1 1 d . . . . .
H5A H 0.5885 0.4306 0.2475 0.019 Uiso 1 1 calc R . . . .
H5B H 0.6354 0.7006 0.2735 0.019 Uiso 1 1 calc R . . . .
C20 C 0.0581(2) 0.4789(5) 0.6789(2) 0.0178(6) Uani 1 1 d . . . . .
C11 C 0.3925(2) 0.5214(5) 0.26987(19) 0.0180(6) Uani 1 1 d . . . . .
H11 H 0.3901 0.3813 0.2297 0.022 Uiso 1 1 calc R . . . .
C23 C 0.1940(2) 0.3833(5) 0.5550(2) 0.0205(7) Uani 1 1 d . . . . .
C25 C 0.1396(2) 0.6451(5) 0.6729(2) 0.0194(6) Uani 1 1 d . . . . .
H25 H 0.1484 0.7908 0.7104 0.023 Uiso 1 1 calc R . . . .
C10 C 0.3081(2) 0.5802(6) 0.31079(19) 0.0201(7) Uani 1 1 d . . . . .
C16 C 0.0619(2) 0.1743(5) 0.8599(2) 0.0162(6) Uani 1 1 d . . . . .
C21 C 0.0453(2) 0.2716(5) 0.6203(2) 0.0212(7) Uani 1 1 d . . . . .
H21 H -0.0104 0.1609 0.6228 0.025 Uiso 1 1 calc R . . . .
C9 C 0.3106(2) 0.7820(6) 0.3694(2) 0.0203(7) Uani 1 1 d . . . . .
C24 C 0.2068(2) 0.5934(6) 0.6115(2) 0.0186(6) Uani 1 1 d . . . . .
C7 C 0.4829(2) 0.8759(5) 0.3485(2) 0.0190(7) Uani 1 1 d . . . . .
H7 H 0.5429 0.9781 0.3615 0.023 Uiso 1 1 calc R . . . .
C19 C -0.0118(2) 0.5254(6) 0.7506(2) 0.0201(6) Uani 1 1 d . . . . .
H19A H -0.0769 0.4303 0.7317 0.024 Uiso 1 1 calc R . . . .
H19B H -0.0302 0.7033 0.7493 0.024 Uiso 1 1 calc R . . . .
C8 C 0.3969(2) 0.9309(6) 0.3893(2) 0.0230(7) Uani 1 1 d . . . . .
H8 H 0.3981 1.0691 0.4303 0.028 Uiso 1 1 calc R . . . .
O28 O 0.19293(16) 0.4807(4) 0.07686(16) 0.0225(5) Uani 1 1 d . . . . .
H28A H 0.2079 0.3603 0.0825 0.034 Uiso 1 1 d G . . . .
H28B H 0.1363 0.5199 0.1048 0.034 Uiso 1 1 d G . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C0AA 1.264(3) . ?
F27 C24 1.364(3) . ?
F26 C23 1.359(3) . ?
F12 C9 1.372(3) . ?
F13 C10 1.365(3) . ?
N14 H14A 0.9100 . ?
N14 H14B 0.9100 . ?
N14 H14C 0.9100 . ?
N14 C15 1.499(3) . ?
C0AA O3 1.268(3) . ?
C0AA C2 1.540(4) . ?
O17 C16 1.267(3) . ?
C6 C5 1.525(4) . ?
C6 C11 1.402(4) . ?
C6 C7 1.408(4) . ?
O29 H29A 1.0582 . ?
O29 H29B 0.8700 . ?
C22 H22 0.9500 . ?
C22 C23 1.377(4) . ?
C22 C21 1.397(4) . ?
C15 H15 1.0000 . ?
C15 C16 1.538(4) . ?
C15 C19 1.544(4) . ?
O18 C16 1.253(3) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C2 1.499(3) . ?
C2 H2 1.0000 . ?
C2 C5 1.546(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C20 C25 1.410(4) . ?
C20 C21 1.394(4) . ?
C20 C19 1.525(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.384(4) . ?
C23 C24 1.389(4) . ?
C25 H25 0.9500 . ?
C25 C24 1.387(4) . ?
C10 C9 1.375(4) . ?
C21 H21 0.9500 . ?
C9 C8 1.374(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.397(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C8 H8 0.9500 . ?
O28 H28A 0.6800 . ?
O28 H28B 0.9316 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H14A N14 H14B 109.5 . . ?
H14A N14 H14C 109.5 . . ?
H14B N14 H14C 109.5 . . ?
C15 N14 H14A 109.5 . . ?
C15 N14 H14B 109.5 . . ?
C15 N14 H14C 109.5 . . ?
O4 C0AA O3 125.1(3) . . ?
O4 C0AA C2 118.6(2) . . ?
O3 C0AA C2 116.2(2) . . ?
C11 C6 C5 119.4(3) . . ?
C11 C6 C7 119.0(3) . . ?
C7 C6 C5 121.7(2) . . ?
H29A O29 H29B 96.4 . . ?
C23 C22 H22 120.4 . . ?
C23 C22 C21 119.2(3) . . ?
C21 C22 H22 120.4 . . ?
N14 C15 H15 108.7 . . ?
N14 C15 C16 107.6(2) . . ?
N14 C15 C19 112.2(2) . . ?
C16 C15 H15 108.7 . . ?
C16 C15 C19 111.0(2) . . ?
C19 C15 H15 108.7 . . ?
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 . . ?
C0AA C2 H2 109.1 . . ?
C0AA C2 C5 111.5(2) . . ?
N1 C2 C0AA 108.9(2) . . ?
N1 C2 H2 109.1 . . ?
N1 C2 C5 109.0(2) . . ?
C5 C2 H2 109.1 . . ?
C6 C5 C2 112.7(2) . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
C2 C5 H5A 109.1 . . ?
C2 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C25 C20 C19 119.6(3) . . ?
C21 C20 C25 118.8(3) . . ?
C21 C20 C19 121.6(3) . . ?
C6 C11 H11 120.3 . . ?
C10 C11 C6 119.4(3) . . ?
C10 C11 H11 120.3 . . ?
F26 C23 C22 121.5(3) . . ?
F26 C23 C24 118.2(3) . . ?
C22 C23 C24 120.2(3) . . ?
C20 C25 H25 120.4 . . ?
C24 C25 C20 119.2(3) . . ?
C24 C25 H25 120.4 . . ?
F13 C10 C11 120.0(3) . . ?
F13 C10 C9 119.1(3) . . ?
C9 C10 C11 120.9(3) . . ?
O17 C16 C15 117.7(2) . . ?
O18 C16 O17 124.5(3) . . ?
O18 C16 C15 117.8(2) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 C22 121.4(3) . . ?
C20 C21 H21 119.3 . . ?
F12 C9 C10 118.4(3) . . ?
F12 C9 C8 120.4(3) . . ?
C8 C9 C10 121.2(3) . . ?
F27 C24 C23 119.1(2) . . ?
F27 C24 C25 119.8(3) . . ?
C25 C24 C23 121.1(3) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C15 C19 H19A 108.8 . . ?
C15 C19 H19B 108.8 . . ?
C20 C19 C15 113.8(2) . . ?
C20 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C9 C8 C7 118.9(3) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
H28A O28 H28B 113.7 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C0AA C2 N1 142.8(2) . . . . ?
O4 C0AA C2 C5 -96.9(3) . . . . ?
F26 C23 C24 F27 1.1(4) . . . . ?
F26 C23 C24 C25 -177.9(3) . . . . ?
F12 C9 C8 C7 -178.9(3) . . . . ?
F13 C10 C9 F12 -1.6(4) . . . . ?
F13 C10 C9 C8 179.0(3) . . . . ?
N14 C15 C16 O17 -29.2(3) . . . . ?
N14 C15 C16 O18 152.8(3) . . . . ?
N14 C15 C19 C20 58.3(3) . . . . ?
C0AA C2 C5 C6 74.4(3) . . . . ?
O3 C0AA C2 N1 -38.6(3) . . . . ?
O3 C0AA C2 C5 81.7(3) . . . . ?
C6 C11 C10 F13 -179.4(2) . . . . ?
C6 C11 C10 C9 -0.3(4) . . . . ?
C6 C7 C8 C9 -0.4(4) . . . . ?
C22 C23 C24 F27 -179.9(3) . . . . ?
C22 C23 C24 C25 1.0(4) . . . . ?
N1 C2 C5 C6 -165.4(2) . . . . ?
C5 C6 C11 C10 -178.2(2) . . . . ?
C5 C6 C7 C8 178.5(3) . . . . ?
C20 C25 C24 F27 -178.0(2) . . . . ?
C20 C25 C24 C23 1.0(4) . . . . ?
C11 C6 C5 C2 74.0(3) . . . . ?
C11 C6 C7 C8 -0.1(4) . . . . ?
C11 C10 C9 F12 179.3(3) . . . . ?
C11 C10 C9 C8 -0.2(4) . . . . ?
C23 C22 C21 C20 0.5(4) . . . . ?
C25 C20 C21 C22 1.5(4) . . . . ?
C25 C20 C19 C15 -77.6(3) . . . . ?
C10 C9 C8 C7 0.5(5) . . . . ?
C16 C15 C19 C20 -62.1(3) . . . . ?
C21 C22 C23 F26 177.2(3) . . . . ?
C21 C22 C23 C24 -1.8(4) . . . . ?
C21 C20 C25 C24 -2.3(4) . . . . ?
C21 C20 C19 C15 100.7(3) . . . . ?
C7 C6 C5 C2 -104.6(3) . . . . ?
C7 C6 C11 C10 0.4(4) . . . . ?
C19 C15 C16 O17 93.9(3) . . . . ?
C19 C15 C16 O18 -84.1(3) . . . . ?
C19 C20 C25 C24 176.1(3) . . . . ?
C19 C20 C21 C22 -176.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xs
_database_code_depnum_ccdc_archive 'CCDC 1532629'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-04-24 downloaded from the CCDC.
;
_audit_creation_date             2015-03-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        '4-bromophenylalanine '
_chemical_formula_moiety         'C9 H10 Br N O2, H2 O'
_chemical_formula_sum            'C9 H12 Br N O3'
_chemical_formula_weight         262.11
_chemical_absolute_configuration rm
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.3036(4)
_cell_length_b                   5.3042(3)
_cell_length_c                   15.9161(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.947(3)
_cell_angle_gamma                90
_cell_volume                     527.05(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8473
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.11
_cell_measurement_theta_min      2.58
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.881
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.5991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0872 before and 0.0628 after correction.
The Ratio of minimum to maximum transmission is 0.8027.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             264
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15350
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         32.254
_diffrn_reflns_theta_min         3.263
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_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_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.815
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                3516
_reflns_number_total             3717
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_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)'
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 1487 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         3717
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0206
_refine_ls_R_factor_gt           0.0183
_refine_ls_restrained_S_all      1.000
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0388
_refine_ls_wR_factor_ref         0.0392
_refine_special_details          ?
_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:
 O3(H3C,H3D)
2.b Ternary CH refined with riding coordinates:
 C2(H2)
2.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.d Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C9(H9), C6(H6)
2.e Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.87360(2) -0.19862(5) 0.43823(2) 0.01663(5) Uani 1 1 d . . . . .
C3 C 0.3537(3) 0.6604(3) 0.23336(11) 0.0135(3) Uani 1 1 d . . . . .
H3A H 0.4433 0.8142 0.2407 0.016 Uiso 1 1 calc R . . . .
H3B H 0.2203 0.6948 0.2577 0.016 Uiso 1 1 calc R . . . .
O1 O 0.0709(2) 0.2492(2) 0.15122(9) 0.0154(3) Uani 1 1 d . . . . .
C5 C 0.6715(3) 0.3620(3) 0.26049(12) 0.0143(4) Uani 1 1 d . . . . .
H5 H 0.7246 0.4371 0.2134 0.017 Uiso 1 1 calc R . . . .
C8 C 0.5161(3) 0.1420(4) 0.40027(12) 0.0165(4) Uani 1 1 d . . . . .
H8 H 0.4641 0.0674 0.4477 0.020 Uiso 1 1 calc R . . . .
C2 C 0.2952(3) 0.6060(3) 0.13688(12) 0.0117(3) Uani 1 1 d . . . . .
H2 H 0.4104 0.4982 0.1184 0.014 Uiso 1 1 calc R . . . .
C9 C 0.3988(3) 0.3329(4) 0.35304(11) 0.0156(4) Uani 1 1 d . . . . .
H9 H 0.2664 0.3870 0.3690 0.019 Uiso 1 1 calc R . . . .
C6 C 0.7907(3) 0.1722(4) 0.30611(12) 0.0153(3) Uani 1 1 d . . . . .
H6 H 0.9229 0.1174 0.2901 0.018 Uiso 1 1 calc R . . . .
C7 C 0.7115(3) 0.0643(4) 0.37580(12) 0.0146(3) Uani 1 1 d . . . . .
O2 O -0.0729(2) 0.5679(3) 0.06880(9) 0.0160(3) Uani 1 1 d . . . . .
C4 C 0.4737(3) 0.4447(4) 0.28290(12) 0.0134(3) Uani 1 1 d . . . . .
C1 C 0.0791(3) 0.4639(4) 0.11671(12) 0.0118(3) Uani 1 1 d . . . . .
O3 O 0.2993(2) 0.5081(3) 0.93109(9) 0.0170(3) Uani 1 1 d . . . . .
H3C H 0.2168 0.6075 0.9000 0.026 Uiso 1 1 d G . . . .
H3D H 0.2339 0.3710 0.9377 0.026 Uiso 1 1 d G . . . .
N1 N 0.2876(2) 0.8500(3) 0.08842(10) 0.0126(3) Uani 1 1 d . . . . .
H1A H 0.2135 0.9668 0.1146 0.015 Uiso 1 1 calc GR . . . .
H1B H 0.2212 0.8246 0.0346 0.015 Uiso 1 1 calc GR . . . .
H1C H 0.4233 0.9063 0.0868 0.015 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C7 1.9225(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.556(3) . ?
C3 C4 1.529(3) . ?
O1 C1 1.269(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.398(3) . ?
C5 C4 1.413(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.408(3) . ?
C8 C7 1.404(3) . ?
C2 H2 1.0000 . ?
C2 C1 1.551(2) . ?
C2 N1 1.504(2) . ?
C9 H9 0.9500 . ?
C9 C4 1.403(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.400(3) . ?
O2 C1 1.266(2) . ?
O3 H3C 0.8502 . ?
O3 H3D 0.8497 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H3A C3 H3B 107.7 . . ?
C2 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
C4 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C4 C3 C2 113.76(15) . . ?
C6 C5 H5 119.3 . . ?
C6 C5 C4 121.47(17) . . ?
C4 C5 H5 119.3 . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C7 C8 C9 118.62(17) . . ?
C3 C2 H2 108.3 . . ?
C1 C2 C3 112.08(15) . . ?
C1 C2 H2 108.3 . . ?
N1 C2 C3 109.45(14) . . ?
N1 C2 H2 108.3 . . ?
N1 C2 C1 110.30(14) . . ?
C8 C9 H9 119.4 . . ?
C4 C9 C8 121.28(16) . . ?
C4 C9 H9 119.4 . . ?
C5 C6 H6 120.6 . . ?
C5 C6 C7 118.72(17) . . ?
C7 C6 H6 120.6 . . ?
C8 C7 Br1 119.58(14) . . ?
C6 C7 Br1 118.92(14) . . ?
C6 C7 C8 121.50(18) . . ?
C5 C4 C3 119.54(17) . . ?
C9 C4 C3 121.99(17) . . ?
C9 C4 C5 118.40(17) . . ?
O1 C1 C2 115.71(15) . . ?
O2 C1 O1 125.41(17) . . ?
O2 C1 C2 118.88(16) . . ?
H3C O3 H3D 109.5 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C2 C1 O1 -60.9(2) . . . . ?
C3 C2 C1 O2 118.62(18) . . . . ?
C5 C6 C7 Br1 179.53(13) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C8 C9 C4 C3 -177.15(17) . . . . ?
C8 C9 C4 C5 -0.2(3) . . . . ?
C2 C3 C4 C5 59.1(2) . . . . ?
C2 C3 C4 C9 -123.98(19) . . . . ?
C9 C8 C7 Br1 -179.28(15) . . . . ?
C9 C8 C7 C6 0.0(3) . . . . ?
C6 C5 C4 C3 177.48(16) . . . . ?
C6 C5 C4 C9 0.5(3) . . . . ?
C7 C8 C9 C4 0.0(3) . . . . ?
C4 C3 C2 C1 86.59(19) . . . . ?
C4 C3 C2 N1 -150.70(14) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
N1 C2 C1 O1 176.84(15) . . . . ?
N1 C2 C1 O2 -3.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xs
_database_code_depnum_ccdc_archive 'CCDC 1532630'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-04-24 downloaded from the CCDC.
;
_audit_creation_date             2015-03-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        4-fluorophenylalanine
_chemical_formula_moiety         'C9 H10 F N O2, H2 O'
_chemical_formula_sum            'C9 H12 F N O3'
_chemical_formula_weight         201.20
_chemical_absolute_configuration rm
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   13.3028(14)
_cell_length_b                   5.4628(6)
_cell_length_c                   14.0151(15)
_cell_angle_alpha                90
_cell_angle_beta                 104.048(5)
_cell_angle_gamma                90
_cell_volume                     988.02(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9917
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.75
_cell_measurement_theta_min      2.43
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.7037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0655 before and 0.0405 after correction.
The Ratio of minimum to maximum transmission is 0.9427.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25842
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         32.827
_diffrn_reflns_theta_min         1.578
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_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_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.919
_reflns_number_gt                6498
_reflns_number_total             7041
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_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)'
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 2674 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         7041
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.031
_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/[σ²(Fo²)+(0.0512P)²+0.0668P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0844
_refine_special_details          ?
_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:
 O11(H11A,H11B), O13(H13A,H13B)
2.b Ternary CH refined with riding coordinates:
 C7(H7), C12(H12)
2.c Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C21(H21A,H21B)
2.d Aromatic/amide H refined with riding coordinates:
 C24(H24), C25(H25), C26(H26), C27(H27), C18(H18), C19(H19), C22(H22), C23(H23)
2.e Idealised Me refined as rotating group:
 N6(H6A,H6B,H6C), N3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.01225(7) 0.64518(16) 0.11238(7) 0.01679(17) Uani 1 1 d . . . . .
O4 O 0.15825(7) 0.61590(17) 0.12260(8) 0.02048(19) Uani 1 1 d . . . . .
N6 N 0.13840(7) 0.12114(19) 0.08586(8) 0.01463(18) Uani 1 1 d . . . . .
H6A H 0.1415 -0.0416 0.1002 0.018 Uiso 1 1 calc GR . . . .
H6B H 0.2029 0.1873 0.1050 0.018 Uiso 1 1 calc GR . . . .
H6C H 0.1136 0.1421 0.0199 0.018 Uiso 1 1 calc GR . . . .
C7 C 0.06773(8) 0.2456(2) 0.13925(8) 0.01272(19) Uani 1 1 d . . . . .
H7 H -0.0046 0.1857 0.1123 0.015 Uiso 1 1 calc R . . . .
C10 C 0.07091(8) 0.5250(2) 0.12278(8) 0.0130(2) Uani 1 1 d . . . . .
C14 C 0.01945(10) 0.2497(2) 0.30384(9) 0.0171(2) Uani 1 1 d . . . . .
C16 C 0.10173(9) 0.1817(2) 0.25025(9) 0.0178(2) Uani 1 1 d . . . . .
H16A H 0.1160 0.0039 0.2578 0.021 Uiso 1 1 calc R . . . .
H16B H 0.1667 0.2700 0.2804 0.021 Uiso 1 1 calc R . . . .
F20 F -0.21514(10) 0.4342(2) 0.43871(9) 0.0463(3) Uani 1 1 d . . . . .
C24 C 0.02718(12) 0.4614(3) 0.36229(10) 0.0233(3) Uani 1 1 d . . . . .
H24 H 0.0866 0.5632 0.3706 0.028 Uiso 1 1 calc R . . . .
C25 C -0.14808(12) 0.1608(3) 0.33882(11) 0.0259(3) Uani 1 1 d . . . . .
H25 H -0.2075 0.0595 0.3316 0.031 Uiso 1 1 calc R . . . .
C26 C -0.05148(13) 0.5240(3) 0.40838(11) 0.0286(3) Uani 1 1 d . . . . .
H26 H -0.0461 0.6669 0.4479 0.034 Uiso 1 1 calc R . . . .
C27 C -0.06879(10) 0.1010(3) 0.29318(9) 0.0202(2) Uani 1 1 d . . . . .
H27 H -0.0747 -0.0429 0.2542 0.024 Uiso 1 1 calc R . . . .
C28 C -0.13714(13) 0.3731(3) 0.39502(11) 0.0282(3) Uani 1 1 d . . . . .
O2 O 0.35267(7) 0.16832(16) 0.12856(7) 0.01703(17) Uani 1 1 d . . . . .
N3 N 0.36239(7) 0.65214(18) 0.09813(7) 0.01362(18) Uani 1 1 d . . . . .
H3A H 0.3175 0.5982 0.1332 0.016 Uiso 1 1 calc GR . . . .
H3B H 0.3352 0.6239 0.0330 0.016 Uiso 1 1 calc GR . . . .
H3C H 0.3733 0.8155 0.1083 0.016 Uiso 1 1 calc GR . . . .
O5 O 0.51482(8) 0.10268(19) 0.11735(9) 0.0277(2) Uani 1 1 d . . . . .
F8 F 0.28865(8) 0.42455(19) 0.52070(7) 0.0341(2) Uani 1 1 d . . . . .
C9 C 0.44189(9) 0.2411(2) 0.12426(8) 0.0140(2) Uani 1 1 d . . . . .
C12 C 0.46334(9) 0.5182(2) 0.13092(8) 0.0133(2) Uani 1 1 d . . . . .
H12 H 0.5082 0.5607 0.0855 0.016 Uiso 1 1 calc R . . . .
C15 C 0.45779(9) 0.5462(2) 0.31259(8) 0.0162(2) Uani 1 1 d . . . . .
C17 C 0.34326(11) 0.4638(3) 0.45144(9) 0.0217(3) Uani 1 1 d . . . . .
C18 C 0.32562(11) 0.6779(3) 0.39640(9) 0.0206(2) Uani 1 1 d . . . . .
H18 H 0.2756 0.7938 0.4056 0.025 Uiso 1 1 calc R . . . .
C19 C 0.38381(10) 0.7179(2) 0.32683(9) 0.0180(2) Uani 1 1 d . . . . .
H19 H 0.3732 0.8635 0.2886 0.022 Uiso 1 1 calc R . . . .
C21 C 0.52072(9) 0.5922(2) 0.23717(9) 0.0171(2) Uani 1 1 d . . . . .
H21A H 0.5864 0.4991 0.2564 0.021 Uiso 1 1 calc R . . . .
H21B H 0.5385 0.7683 0.2379 0.021 Uiso 1 1 calc R . . . .
C22 C 0.41513(11) 0.2892(2) 0.43993(9) 0.0222(3) Uani 1 1 d . . . . .
H22 H 0.4253 0.1445 0.4786 0.027 Uiso 1 1 calc R . . . .
C23 C 0.47228(11) 0.3319(2) 0.36975(9) 0.0196(2) Uani 1 1 d . . . . .
H23 H 0.5216 0.2140 0.3607 0.024 Uiso 1 1 calc R . . . .
O11 O 0.29015(7) 0.5506(2) 0.89798(7) 0.0250(2) Uani 1 1 d . . . . .
H11A H 0.3510 0.5650 0.8830 0.038 Uiso 1 1 d G . . . .
H11B H 0.2663 0.4065 0.8860 0.038 Uiso 1 1 d G . . . .
O13 O 0.78535(8) 0.5655(2) 0.12728(10) 0.0362(3) Uani 1 1 d . . . . .
H13A H 0.7657 0.4196 0.1336 0.054 Uiso 1 1 d G . . . .
H13B H 0.8509 0.5685 0.1362 0.054 Uiso 1 1 d G . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.2641(14) . ?
O4 C10 1.2641(14) . ?
N6 H6A 0.9100 . ?
N6 H6B 0.9100 . ?
N6 H6C 0.9100 . ?
N6 C7 1.4992(15) . ?
C7 H7 1.0000 . ?
C7 C10 1.5458(16) . ?
C7 C16 1.5509(16) . ?
C14 C16 1.5165(18) . ?
C14 C24 1.4065(19) . ?
C14 C27 1.4052(18) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
F20 C28 1.3679(18) . ?
C24 H24 0.9500 . ?
C24 C26 1.399(2) . ?
C25 H25 0.9500 . ?
C25 C27 1.3985(19) . ?
C25 C28 1.390(2) . ?
C26 H26 0.9500 . ?
C26 C28 1.382(2) . ?
C27 H27 0.9500 . ?
O2 C9 1.2670(14) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 H3C 0.9100 . ?
N3 C12 1.5001(15) . ?
O5 C9 1.2523(15) . ?
F8 C17 1.3633(16) . ?
C9 C12 1.5391(16) . ?
C12 H12 1.0000 . ?
C12 C21 1.5529(16) . ?
C15 C19 1.4085(18) . ?
C15 C21 1.5201(17) . ?
C15 C23 1.4048(17) . ?
C17 C18 1.3891(19) . ?
C17 C22 1.387(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.4015(19) . ?
C19 H19 0.9500 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22 0.9500 . ?
C22 C23 1.401(2) . ?
C23 H23 0.9500 . ?
O11 H11A 0.8884 . ?
O11 H11B 0.8499 . ?
O13 H13A 0.8501 . ?
O13 H13B 0.8498 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H6A N6 H6B 109.5 . . ?
H6A N6 H6C 109.5 . . ?
H6B N6 H6C 109.5 . . ?
C7 N6 H6A 109.5 . . ?
C7 N6 H6B 109.5 . . ?
C7 N6 H6C 109.5 . . ?
N6 C7 H7 109.0 . . ?
N6 C7 C10 109.28(9) . . ?
N6 C7 C16 109.45(9) . . ?
C10 C7 H7 109.0 . . ?
C10 C7 C16 111.11(9) . . ?
C16 C7 H7 109.0 . . ?
O1 C10 O4 125.10(11) . . ?
O1 C10 C7 118.36(10) . . ?
O4 C10 C7 116.53(10) . . ?
C24 C14 C16 122.04(12) . . ?
C27 C14 C16 119.36(11) . . ?
C27 C14 C24 118.58(12) . . ?
C7 C16 H16A 109.3 . . ?
C7 C16 H16B 109.3 . . ?
C14 C16 C7 111.83(9) . . ?
C14 C16 H16A 109.3 . . ?
C14 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C14 C24 H24 119.6 . . ?
C26 C24 C14 120.84(13) . . ?
C26 C24 H24 119.6 . . ?
C27 C25 H25 121.1 . . ?
C28 C25 H25 121.1 . . ?
C28 C25 C27 117.85(14) . . ?
C24 C26 H26 120.8 . . ?
C28 C26 C24 118.46(13) . . ?
C28 C26 H26 120.8 . . ?
C14 C27 H27 119.3 . . ?
C25 C27 C14 121.31(13) . . ?
C25 C27 H27 119.3 . . ?
F20 C28 C25 118.07(15) . . ?
F20 C28 C26 118.97(14) . . ?
C26 C28 C25 122.96(14) . . ?
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C12 N3 H3A 109.5 . . ?
C12 N3 H3B 109.5 . . ?
C12 N3 H3C 109.5 . . ?
O2 C9 C12 117.90(10) . . ?
O5 C9 O2 124.50(12) . . ?
O5 C9 C12 117.58(11) . . ?
N3 C12 C9 108.78(9) . . ?
N3 C12 H12 108.7 . . ?
N3 C12 C21 111.22(9) . . ?
C9 C12 H12 108.7 . . ?
C9 C12 C21 110.78(10) . . ?
C21 C12 H12 108.7 . . ?
C19 C15 C21 120.65(11) . . ?
C23 C15 C19 118.56(12) . . ?
C23 C15 C21 120.79(11) . . ?
F8 C17 C18 118.72(13) . . ?
F8 C17 C22 118.42(12) . . ?
C22 C17 C18 122.85(12) . . ?
C17 C18 H18 121.0 . . ?
C17 C18 C19 118.05(13) . . ?
C19 C18 H18 121.0 . . ?
C15 C19 H19 119.4 . . ?
C18 C19 C15 121.17(12) . . ?
C18 C19 H19 119.4 . . ?
C12 C21 H21A 108.9 . . ?
C12 C21 H21B 108.9 . . ?
C15 C21 C12 113.47(9) . . ?
C15 C21 H21A 108.9 . . ?
C15 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C17 C22 H22 120.9 . . ?
C17 C22 C23 118.29(12) . . ?
C23 C22 H22 120.9 . . ?
C15 C23 H23 119.5 . . ?
C22 C23 C15 121.08(12) . . ?
C22 C23 H23 119.5 . . ?
H11A O11 H11B 110.7 . . ?
H13A O13 H13B 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N6 C7 C10 O1 142.44(10) . . . . ?
N6 C7 C10 O4 -38.79(14) . . . . ?
N6 C7 C16 C14 -166.20(10) . . . . ?
C10 C7 C16 C14 73.03(13) . . . . ?
C14 C24 C26 C28 -0.1(2) . . . . ?
C16 C7 C10 O1 -96.67(12) . . . . ?
C16 C7 C10 O4 82.09(13) . . . . ?
C16 C14 C24 C26 177.93(12) . . . . ?
C16 C14 C27 C25 -178.04(12) . . . . ?
C24 C14 C16 C7 -102.04(13) . . . . ?
C24 C14 C27 C25 0.36(19) . . . . ?
C24 C26 C28 F20 -179.18(14) . . . . ?
C24 C26 C28 C25 0.8(2) . . . . ?
C27 C14 C16 C7 76.31(14) . . . . ?
C27 C14 C24 C26 -0.42(19) . . . . ?
C27 C25 C28 F20 179.12(13) . . . . ?
C27 C25 C28 C26 -0.8(2) . . . . ?
C28 C25 C27 C14 0.2(2) . . . . ?
O2 C9 C12 N3 -24.33(14) . . . . ?
O2 C9 C12 C21 98.22(12) . . . . ?
N3 C12 C21 C15 57.96(13) . . . . ?
O5 C9 C12 N3 157.36(11) . . . . ?
O5 C9 C12 C21 -80.09(14) . . . . ?
F8 C17 C18 C19 178.77(11) . . . . ?
F8 C17 C22 C23 -179.03(12) . . . . ?
C9 C12 C21 C15 -63.15(13) . . . . ?
C17 C18 C19 C15 0.27(18) . . . . ?
C17 C22 C23 C15 0.26(19) . . . . ?
C18 C17 C22 C23 0.11(19) . . . . ?
C19 C15 C21 C12 -83.34(14) . . . . ?
C19 C15 C23 C22 -0.36(17) . . . . ?
C21 C15 C19 C18 -179.75(11) . . . . ?
C21 C15 C23 C22 179.48(11) . . . . ?
C22 C17 C18 C19 -0.37(19) . . . . ?
C23 C15 C19 C18 0.09(17) . . . . ?
C23 C15 C21 C12 96.82(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5179a
_database_code_depnum_ccdc_archive 'CCDC 1532631'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-04-24 downloaded from the CCDC.
;
_audit_creation_date             2015-03-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        4-Iodophenylalanine
_chemical_formula_moiety         'C9 H10 I N O2, H2 O'
_chemical_formula_sum            'C9 H12 I N O3'
_chemical_formula_weight         309.10
_chemical_absolute_configuration rm
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   5.3139(3)
_cell_length_b                   6.3152(4)
_cell_length_c                   32.741(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1098.72(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.44
_cell_measurement_theta_min      3.29
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.869
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_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_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_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_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_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)'
_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_coef       .
_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_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.321
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
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_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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
