# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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. 
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data_FMOC4BrPhe
_database_code_depnum_ccdc_archive 'CCDC 1521994'
_audit_update_record             
;
2017-01-27 deposited with the CCDC.
2017-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 Br N O4, 0.333(H2 O)'
_chemical_formula_sum            'C24 H20.67 Br N O4.33'
_chemical_formula_weight         472.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0059 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0105 0.0059 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2350 2.4064 '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'

_space_group_crystal_system      hexagonal
_space_group_IT_number           173
_space_group_name_H-M_alt        'P 63'
_space_group_name_Hall           'P 6c'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x-y, z'
'y, -x+y, z+1/2'
'-x+y, -x, z'
'x-y, x, z+1/2'

_cell_length_a                   26.744(4)
_cell_length_b                   26.744(4)
_cell_length_c                   4.9970(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3095.2(11)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    359
_cell_measurement_theta_min      1.500
_cell_measurement_theta_max      22.864

_exptl_crystal_description       'Thin plates'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_F_000             1448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.893
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.700


_diffrn_radiation_type           Synchrotron
_diffrn_source                   'Elettra Synchrotron - XRD1 BL'
_diffrn_measurement_device_type  
;
'Huber 4-circles Kappa Goniometer, Pilatus 2M detector'
;
_diffrn_measurement_method       'Rotating crystal'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4309
_diffrn_reflns_av_unetI/netI     0.1327
_diffrn_reflns_av_R_equivalents  0.0958
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         1.500
_diffrn_reflns_theta_max         22.864
_diffrn_reflns_theta_full        22.864
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_point_group_measured_fraction_full 0.852
_reflns_number_total             2529
_reflns_number_gt                1639
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.534
_reflns_Friedel_fraction_max     0.685
_reflns_Friedel_fraction_full    0.685

_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.
;

_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0

_computing_data_collection       'Elettra XRD1 Data Collection SW'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_molecular_graphics    'Ortep3 for Windows - Coot'
_computing_publication_material  'enCIFer - publCIF'

_refine_special_details          
;
Hydrogen atoms were included at calculated positions with isotropic 
Ufactors=1.2Ueq (Ufactors=1.5Ueq for H bound to oxygens). 
Anisotropic thermal motion modeling as then been applied to atoms 
with full occupancy. Geometric restrains (DFIX, DANG and FLAT) have 
been applied to carboxylate group. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0914P)²+1.9693P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 421 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2529
_refine_ls_number_parameters     226
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1208
_refine_ls_R_factor_gt           0.0691
_refine_ls_wR_factor_ref         0.2006
_refine_ls_wR_factor_gt          0.1693
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.55088(6) 0.92360(6) 0.0698(14) 0.0473(5) Uani 1 1 d . . . . .
C1 C 0.6178(3) 0.9332(4) 0.244(2) 0.037(4) Uani 1 1 d G . . . .
C2 C 0.6724(4) 0.9738(4) 0.153(2) 0.036(5) Uani 1 1 d G . . . .
H2 H 0.676376 0.997611 0.004344 0.043 Uiso 1 1 calc R U . . .
C4 C 0.7212(3) 0.9795(3) 0.280(2) 0.034(4) Uani 1 1 d G . . . .
H4 H 0.758586 1.007261 0.218249 0.041 Uiso 1 1 calc R U . . .
C6 C 0.7155(3) 0.9447(4) 0.498(2) 0.033(4) Uani 1 1 d G . . . .
C5 C 0.6608(3) 0.9041(4) 0.589(2) 0.040(4) Uani 1 1 d G . . . .
H5 H 0.656866 0.880268 0.737428 0.048 Uiso 1 1 calc R U . . .
C3 C 0.6120(3) 0.8984(4) 0.462(2) 0.036(4) Uani 1 1 d G . . . .
H3 H 0.574655 0.870616 0.523524 0.043 Uiso 1 1 calc R U . . .
C13 C 0.5258(3) 0.6367(3) 0.098(2) 0.029(4) Uani 1 1 d G . . . .
C14 C 0.5371(3) 0.5985(4) -0.043(3) 0.037(4) Uani 1 1 d G . . . .
H14 H 0.571146 0.596979 -0.006868 0.044 Uiso 1 1 calc R U . . .
C15 C 0.4984(4) 0.5627(4) -0.237(2) 0.042(5) Uani 1 1 d G . . . .
H15 H 0.506123 0.536669 -0.332938 0.051 Uiso 1 1 calc R U . . .
C16 C 0.4486(4) 0.5650(4) -0.289(2) 0.047(5) Uani 1 1 d G . . . .
H16 H 0.422198 0.540522 -0.421539 0.057 Uiso 1 1 calc R U . . .
C17 C 0.4374(3) 0.6031(4) -0.148(3) 0.045(4) Uani 1 1 d G . . . .
H17 H 0.403296 0.604684 -0.184071 0.054 Uiso 1 1 calc R U . . .
C18 C 0.4760(4) 0.6389(4) 0.046(3) 0.035(4) Uani 1 1 d G . . . .
C19 C 0.4736(2) 0.6804(2) 0.2124(3) 0.034(4) Uani 1 1 d G . . . .
C20 C 0.43234(19) 0.6971(3) 0.2435(9) 0.038(4) Uani 1 1 d G . . . .
H20 H 0.398710 0.680254 0.134675 0.046 Uiso 1 1 calc R U . . .
C21 C 0.44026(19) 0.7383(3) 0.4339(15) 0.043(4) Uani 1 1 d G . . . .
H21 H 0.412044 0.749672 0.455102 0.051 Uiso 1 1 calc R U . . .
C22 C 0.4895(2) 0.7629(3) 0.5931(14) 0.044(4) Uani 1 1 d G . . . .
H22 H 0.494877 0.791092 0.723215 0.053 Uiso 1 1 calc R U . . .
C23 C 0.53075(19) 0.7463(2) 0.5621(7) 0.031(3) Uani 1 1 d G . . . .
H23 H 0.564377 0.763094 0.670905 0.037 Uiso 1 1 calc R U . . .
C24 C 0.52283(19) 0.70504(19) 0.3717(3) 0.029(4) Uani 1 1 d G . . . .
O4 O 0.6561(4) 0.7645(4) 0.387(3) 0.029(2) Uani 1 1 d . . . . .
N1 N 0.7354(5) 0.8453(5) 0.508(3) 0.029(4) Uani 1 1 d . . . . .
HN1 H 0.728758 0.830995 0.671662 0.035 Uiso 1 1 calc R U . . .
O3 O 0.7120(4) 0.8296(4) 0.072(3) 0.038(2) Uani 1 1 d . . . . .
C12 C 0.5624(6) 0.6814(6) 0.303(4) 0.036(4) Uani 1 1 d . . . . .
H12 H 0.569832 0.663428 0.462332 0.044 Uiso 1 1 calc R U . . .
C10 C 0.70291(18) 0.8146(2) 0.3074(15) 0.025(3) Uani 1 1 d G . . . .
C7 C 0.7714(2) 0.9487(2) 0.636(3) 0.041(5) Uani 1 1 d G . . . .
H7A H 0.763655 0.935989 0.824924 0.050 Uiso 1 1 calc R U . . .
H7B H 0.804581 0.988523 0.628118 0.050 Uiso 1 1 calc R U . . .
C9 C 0.83745(19) 0.9114(3) 0.596(3) 0.061(6) Uani 1 1 d DG . . . .
C11 C 0.6195(2) 0.7273(3) 0.1709(11) 0.025(4) Uani 1 1 d G . . . .
H11A H 0.638528 0.708542 0.078644 0.030 Uiso 1 1 calc R U . . .
H11B H 0.611818 0.750181 0.038296 0.030 Uiso 1 1 calc R U . . .
C8 C 0.78335(18) 0.9043(2) 0.454(2) 0.050(6) Uani 1 1 d G . . . .
H8 H 0.789272 0.914404 0.259846 0.060 Uiso 1 1 calc R U . . .
O1 O 0.8860(6) 0.9609(6) 0.535(5) 0.138(9) Uani 1 1 d D . . . .
H1 H 0.877777 0.981213 0.436231 0.206 Uiso 1 1 calc R U . . .
O2 O 0.8400(6) 0.8770(6) 0.753(4) 0.137(10) Uani 1 1 d D . . . .
OW1A O 1.000000 1.000000 0.696(12) 0.13(2) Uiso 0.6 3 d S . P A 1
OW1B O 0.966(3) 0.940(2) 0.57(2) 0.033(16) Uiso 0.1333 1 d . . P B 2


_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 C1 1.888(6) . ?
C1 C2 1.3900 . ?
C1 C3 1.3900 . ?
C2 C4 1.3900 . ?
C2 H2 0.9500 . ?
C4 C6 1.3900 . ?
C4 H4 0.9500 . ?
C6 C5 1.3900 . ?
C6 C7 1.600(9) . ?
C5 C3 1.3900 . ?
C5 H5 0.9500 . ?
C3 H3 0.9500 . ?
C13 C14 1.3900 . ?
C13 C18 1.3900 . ?
C13 C12 1.504(18) . ?
C14 C15 1.3900 . ?
C14 H14 0.9500 . ?
C15 C16 1.3900 . ?
C15 H15 0.9500 . ?
C16 C17 1.3900 . ?
C16 H16 0.9500 . ?
C17 C18 1.3900 . ?
C17 H17 0.9500 . ?
C18 C19 1.415(10) . ?
C19 C20 1.3900 . ?
C19 C24 1.3900 . ?
C20 C21 1.3900 . ?
C20 H20 0.9500 . ?
C21 C22 1.3900 . ?
C21 H21 0.9500 . ?
C22 C23 1.3900 . ?
C22 H22 0.9500 . ?
C23 C24 1.3900 . ?
C23 H23 0.9500 . ?
C24 C12 1.520(16) . ?
O4 C10 1.359(10) . ?
O4 C11 1.463(12) . ?
N1 C10 1.313(14) . ?
N1 C8 1.478(12) . ?
N1 HN1 0.8800 . ?
O3 C10 1.229(17) . ?
C12 C11 1.549(16) . ?
C12 H12 1.0000 . ?
C7 C8 1.6475 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 O2 1.237(10) . ?
C9 O1 1.346(13) . ?
C9 C8 1.5342 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C8 H8 1.0000 . ?
O1 H1 0.8400 . ?

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
C2 C1 C3 120.0 . . ?
C2 C1 Br1 120.7(5) . . ?
C3 C1 Br1 119.3(5) . . ?
C1 C2 C4 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C2 H2 120.0 . . ?
C6 C4 C2 120.0 . . ?
C6 C4 H4 120.0 . . ?
C2 C4 H4 120.0 . . ?
C4 C6 C5 120.0 . . ?
C4 C6 C7 120.3(6) . . ?
C5 C6 C7 119.6(6) . . ?
C6 C5 C3 120.0 . . ?
C6 C5 H5 120.0 . . ?
C3 C5 H5 120.0 . . ?
C5 C3 C1 120.0 . . ?
C5 C3 H3 120.0 . . ?
C1 C3 H3 120.0 . . ?
C14 C13 C18 120.0 . . ?
C14 C13 C12 129.4(8) . . ?
C18 C13 C12 110.5(8) . . ?
C13 C14 C15 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 120.0 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C13 120.0 . . ?
C17 C18 C19 129.9(6) . . ?
C13 C18 C19 110.1(6) . . ?
C20 C19 C24 120.0 . . ?
C20 C19 C18 132.2(5) . . ?
C24 C19 C18 107.8(5) . . ?
C19 C20 C21 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 120.0 . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 120.0 . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 120.0 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C19 120.0 . . ?
C23 C24 C12 128.6(7) . . ?
C19 C24 C12 111.4(7) . . ?
C10 O4 C11 115.3(9) . . ?
C10 N1 C8 118.4(11) . . ?
C10 N1 HN1 120.8 . . ?
C8 N1 HN1 120.8 . . ?
C13 C12 C24 100.0(10) . . ?
C13 C12 C11 109.4(12) . . ?
C24 C12 C11 112.4(10) . . ?
C13 C12 H12 111.5 . . ?
C24 C12 H12 111.5 . . ?
C11 C12 H12 111.5 . . ?
O3 C10 N1 124.7(8) . . ?
O3 C10 O4 122.5(8) . . ?
N1 C10 O4 112.8(9) . . ?
C6 C7 C8 103.1(5) . . ?
C6 C7 H7A 111.1 . . ?
C8 C7 H7A 111.1 . . ?
C6 C7 H7B 111.1 . . ?
C8 C7 H7B 111.1 . . ?
H7A C7 H7B 109.1 . . ?
O2 C9 O1 119.3(9) . . ?
O2 C9 C8 126.9(6) . . ?
O1 C9 C8 113.8(8) . . ?
O4 C11 C12 106.5(9) . . ?
O4 C11 H11A 110.4 . . ?
C12 C11 H11A 110.4 . . ?
O4 C11 H11B 110.4 . . ?
C12 C11 H11B 110.4 . . ?
H11A C11 H11B 108.6 . . ?
N1 C8 C9 108.0(5) . . ?
N1 C8 C7 106.9(5) . . ?
C9 C8 C7 99.7 . . ?
N1 C8 H8 113.7 . . ?
C9 C8 H8 113.7 . . ?
C7 C8 H8 113.7 . . ?
C9 O1 H1 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 C1 C2 C4 0.0 . . . . ?
Br1 C1 C2 C4 -178.7(7) . . . . ?
C1 C2 C4 C6 0.0 . . . . ?
C2 C4 C6 C5 0.0 . . . . ?
C2 C4 C6 C7 176.8(8) . . . . ?
C4 C6 C5 C3 0.0 . . . . ?
C7 C6 C5 C3 -176.8(8) . . . . ?
C6 C5 C3 C1 0.0 . . . . ?
C2 C1 C3 C5 0.0 . . . . ?
Br1 C1 C3 C5 178.7(7) . . . . ?
C18 C13 C14 C15 0.0 . . . . ?
C12 C13 C14 C15 -176.1(13) . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 C13 0.0 . . . . ?
C16 C17 C18 C19 -179.8(11) . . . . ?
C14 C13 C18 C17 0.0 . . . . ?
C12 C13 C18 C17 176.8(11) . . . . ?
C14 C13 C18 C19 179.8(9) . . . . ?
C12 C13 C18 C19 -3.3(10) . . . . ?
C17 C18 C19 C20 2.6(12) . . . . ?
C13 C18 C19 C20 -177.2(5) . . . . ?
C17 C18 C19 C24 -179.8(6) . . . . ?
C13 C18 C19 C24 0.4(7) . . . . ?
C24 C19 C20 C21 0.0 . . . . ?
C18 C19 C20 C21 177.4(9) . . . . ?
C19 C20 C21 C22 0.0 . . . . ?
C20 C21 C22 C23 0.0 . . . . ?
C21 C22 C23 C24 0.0 . . . . ?
C22 C23 C24 C19 0.0 . . . . ?
C22 C23 C24 C12 179.2(9) . . . . ?
C20 C19 C24 C23 0.0 . . . . ?
C18 C19 C24 C23 -178.0(7) . . . . ?
C20 C19 C24 C12 -179.3(7) . . . . ?
C18 C19 C24 C12 2.7(8) . . . . ?
C14 C13 C12 C24 -179.0(7) . . . . ?
C18 C13 C12 C24 4.5(12) . . . . ?
C14 C13 C12 C11 62.8(14) . . . . ?
C18 C13 C12 C11 -113.7(9) . . . . ?
C23 C24 C12 C13 176.4(6) . . . . ?
C19 C24 C12 C13 -4.4(11) . . . . ?
C23 C24 C12 C11 -67.7(16) . . . . ?
C19 C24 C12 C11 111.6(10) . . . . ?
C8 N1 C10 O3 6.0(14) . . . . ?
C8 N1 C10 O4 -171.9(7) . . . . ?
C11 O4 C10 O3 4.4(12) . . . . ?
C11 O4 C10 N1 -177.6(7) . . . . ?
C4 C6 C7 C8 -86.0(6) . . . . ?
C5 C6 C7 C8 90.8(6) . . . . ?
C10 O4 C11 C12 -166.5(8) . . . . ?
C13 C12 C11 O4 -172.2(9) . . . . ?
C24 C12 C11 O4 77.6(13) . . . . ?
C10 N1 C8 C9 -133.1(7) . . . . ?
C10 N1 C8 C7 120.4(8) . . . . ?
O2 C9 C8 N1 -7.7(12) . . . . ?
O1 C9 C8 N1 172.2(12) . . . . ?
O2 C9 C8 C7 103.8(10) . . . . ?
O1 C9 C8 C7 -76.4(10) . . . . ?
C6 C7 C8 N1 -68.5(7) . . . . ?
C6 C7 C8 C9 179.2(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 HN1 O3 0.88 2.04 2.87(2) 155.3 1_556
O1 H1 O2 0.84 1.76 2.58(2) 166.3 4_564

_refine_diff_density_max         0.573
_refine_diff_density_min         -0.709
_refine_diff_density_rms         0.111



# start Validation Reply Form

_vrf_THETM01_FMOC4BrPhe          
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: After several crystallization trials, the compound crystallized
forming very thin plates, prone to radiation damage. Several of them have 
been tried and merged to get a complete dataset. None of them diffracted 
better than 0.9A.
;

_vrf_PLAT023_FMOC4BrPhe          
;
PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6]..      22.86 Degree
RESPONSE: After several crystallization trials, the compound crystallized
forming very thin plates, prone to radiation damage. Several of them have 
been tried and merged to get a complete dataset. None of them diffracted 
better than 0.9A.
;

# end Validation Reply Form
####################################################################### 
# 
# 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_FMOC4FPhe
_database_code_depnum_ccdc_archive 'CCDC 1521995'
_audit_update_record             
;
2017-02-13 deposited with the CCDC.
2017-02-17 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 F N O4, C2 H6 O S'
_chemical_formula_sum            'C26 H26 F N O5 S'
_chemical_formula_weight         483.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0043 0.0021 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0082 0.0043 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0142 0.0079 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0225 0.0133 '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'
S S 0.1502 0.1577 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.920(1)
_cell_length_b                   13.034(3)
_cell_length_c                   36.789(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2359.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    135
_cell_measurement_theta_min      1.633
_cell_measurement_theta_max      21.614

_exptl_crystal_description       'Thin needles'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.246
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.800

_diffrn_measurement_method       'Rotating crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'Elettra Synchrotron - XRD1 BL'
_diffrn_measurement_device_type  
;
'Huber 4-circles Kappa Goniometer, Pilatus 2M detector'
;

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5409
_diffrn_reflns_av_unetI/netI     0.0870
_diffrn_reflns_av_R_equivalents  0.0819
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         1.866
_diffrn_reflns_theta_max         26.073
_diffrn_reflns_theta_full        26.073
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.578
_diffrn_reflns_point_group_measured_fraction_full 0.578
_reflns_number_total             1905
_reflns_number_gt                1363
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.000
_reflns_Friedel_fraction_full    0.000

_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.
;

_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0

_computing_data_collection       'Elettra XRD1 Data Collection SW'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_molecular_graphics    'Ortep3 for Windows - Coot'
_computing_publication_material  'enCIFer - publCIF'

_refine_special_details          
;
Hydrogen atoms were included at calculated positions with isotropic 
Ufactors=1.2Ueq (Ufactors=1.5Ueq for hydroxyl groups). Anisotropic 
thermal motion modeling has been applied to all atoms with full 
occupancy. Geometric and thermal restrains (DFIX, DANG, DELU and 
SIMU) have been used for disordered DMSO solvent molecule.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1522P)²+10.6031P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.024(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.4(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1905
_refine_ls_number_parameters     271
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.1150
_refine_ls_wR_factor_ref         0.3191
_refine_ls_wR_factor_gt          0.2979
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
F1 F 0.5212(19) 0.0949(6) 0.5221(3) 0.075(3) Uani 1 1 d . . . . .
C13 C 0.2247(19) 0.6184(6) 0.3748(2) 0.043(3) Uani 1 1 d G . . . .
C14 C 0.0361(18) 0.5986(6) 0.3475(3) 0.064(4) Uani 1 1 d G . . . .
H14 H -0.073099 0.538548 0.348656 0.076 Uiso 1 1 calc R U . . .
C15 C 0.007(2) 0.6665(8) 0.3187(3) 0.073(5) Uani 1 1 d G . . . .
H15 H -0.121616 0.652949 0.300068 0.087 Uiso 1 1 calc R U . . .
C16 C 0.167(2) 0.7544(7) 0.3171(3) 0.084(6) Uani 1 1 d G . . . .
H16 H 0.147379 0.800804 0.297328 0.101 Uiso 1 1 calc R U . . .
C17 C 0.356(2) 0.7742(6) 0.3443(3) 0.060(4) Uani 1 1 d G . . . .
H17 H 0.464894 0.834259 0.343177 0.071 Uiso 1 1 calc R U . . .
C18 C 0.3845(18) 0.7063(6) 0.3732(2) 0.055(4) Uani 1 1 d G . . . .
C19 C 0.5591(18) 0.7118(6) 0.4048(2) 0.053(4) Uani 1 1 d G . . . .
C20 C 0.7553(18) 0.7823(5) 0.4156(2) 0.057(4) Uani 1 1 d G . . . .
H20 H 0.801418 0.837966 0.400049 0.068 Uiso 1 1 calc R U . . .
C21 C 0.8840(16) 0.7715(5) 0.4490(3) 0.056(4) Uani 1 1 d G . . . .
H21 H 1.018033 0.819668 0.456302 0.067 Uiso 1 1 calc R U . . .
C22 C 0.8165(17) 0.6901(6) 0.4717(2) 0.048(4) Uani 1 1 d G . . . .
H22 H 0.904426 0.682654 0.494492 0.057 Uiso 1 1 calc R U . . .
C23 C 0.6203(17) 0.6196(5) 0.4609(2) 0.050(4) Uani 1 1 d G . . . .
H23 H 0.574204 0.563937 0.476428 0.060 Uiso 1 1 calc R U . . .
C24 C 0.4917(16) 0.6304(5) 0.4275(2) 0.038(3) Uani 1 1 d G . . . .
C12 C 0.284(3) 0.5624(8) 0.4100(3) 0.040(3) Uani 1 1 d . . . . .
H12 H 0.116024 0.558599 0.425307 0.048 Uiso 1 1 calc R U . . .
C11 C 0.407(3) 0.4551(9) 0.4048(4) 0.048(3) Uani 1 1 d . . . . .
H11A H 0.568573 0.459297 0.388929 0.058 Uiso 1 1 calc R U . . .
H11B H 0.463657 0.426979 0.428616 0.058 Uiso 1 1 calc R U . . .
O4 O 0.2035(15) 0.3883(5) 0.3884(2) 0.038(2) Uani 1 1 d . . . . .
C10 C 0.294(3) 0.2943(11) 0.3801(4) 0.053(4) Uani 1 1 d . . . . .
O3 O 0.5285(19) 0.2682(7) 0.3831(3) 0.059(3) Uani 1 1 d . . . . .
N1 N 0.088(2) 0.2384(7) 0.3666(3) 0.047(3) Uani 1 1 d . . . . .
HN1 H -0.071622 0.267006 0.363067 0.056 Uiso 1 1 calc R U . . .
C8 C 0.130(3) 0.1302(9) 0.3577(4) 0.048(4) Uani 1 1 d . . . . .
H8 H 0.329624 0.116342 0.357858 0.058 Uiso 1 1 calc R U . . .
C9 C 0.023(3) 0.1025(11) 0.3209(5) 0.063(5) Uani 1 1 d . . . . .
O1 O 0.097(4) 0.0160(8) 0.3095(4) 0.107(5) Uani 1 1 d . . . . .
H1 H 0.022081 0.003995 0.289395 0.160 Uiso 1 1 calc R U . . .
O2 O -0.153(4) 0.1543(12) 0.3041(5) 0.148(8) Uani 1 1 d . . . . .
C7 C -0.003(3) 0.0609(9) 0.3860(4) 0.061(4) Uani 1 1 d . . . . .
H7A H -0.197483 0.078857 0.388034 0.074 Uiso 1 1 calc R U . . .
H7B H 0.009340 -0.011202 0.377655 0.074 Uiso 1 1 calc R U . . .
C1 C 0.399(2) 0.0874(7) 0.4891(2) 0.069(5) Uani 1 1 d G . . . .
C3 C 0.187(2) 0.1540(6) 0.4807(2) 0.062(4) Uani 1 1 d G . . . .
H3 H 0.134526 0.205490 0.497603 0.074 Uiso 1 1 calc R U . . .
C5 C 0.0517(17) 0.1451(5) 0.4477(3) 0.055(4) Uani 1 1 d G . . . .
H5 H -0.093103 0.190545 0.442007 0.066 Uiso 1 1 calc R U . . .
C6 C 0.1283(18) 0.0697(6) 0.4230(2) 0.047(3) Uani 1 1 d G . . . .
C4 C 0.3401(18) 0.0032(6) 0.4314(2) 0.059(4) Uani 1 1 d G . . . .
H4 H 0.392479 -0.048353 0.414509 0.071 Uiso 1 1 calc R U . . .
C2 C 0.4753(17) 0.0121(7) 0.4644(3) 0.057(4) Uani 1 1 d G . . . .
H2A H 0.620112 -0.033409 0.470105 0.068 Uiso 1 1 calc R U . . .
O1S O -0.079(3) -0.0605(10) 0.2482(4) 0.114(5) Uani 0.75 1 d D U P A 1
S1S S -0.3822(12) -0.0841(5) 0.24884(16) 0.0705(17) Uani 0.75 1 d D U P A 1
C2S C -0.418(5) -0.2108(11) 0.2299(7) 0.215(17) Uiso 0.75 1 d D . P A 1
H2S1 H -0.610403 -0.230178 0.229656 0.322 Uiso 0.75 1 calc R U P A 1
H2S2 H -0.347200 -0.211353 0.204982 0.322 Uiso 0.75 1 calc R U P A 1
H2S3 H -0.315588 -0.259950 0.244706 0.322 Uiso 0.75 1 calc R U P A 1
C1S C -0.528(5) -0.0072(19) 0.2129(7) 0.37(4) Uiso 0.75 1 d D . P A 1
H1S1 H -0.724676 -0.018997 0.211895 0.562 Uiso 0.75 1 calc R U P A 1
H1S2 H -0.492753 0.065494 0.217742 0.562 Uiso 0.75 1 calc R U P A 1
H1S3 H -0.445957 -0.026520 0.189629 0.562 Uiso 0.75 1 calc R U P A 1
O2S O -0.079(3) -0.0605(10) 0.2482(4) 0.114(5) Uani 0.25 1 d D U P B 2
S2S S -0.246(4) -0.0957(15) 0.2155(6) 0.110(8) Uani 0.25 1 d D U P B 2
C3S C -0.528(5) -0.0072(19) 0.2129(7) 0.37(4) Uiso 0.25 1 d D . P B 2
H3S1 H -0.644480 -0.025633 0.192304 0.562 Uiso 0.25 1 calc R U P B 2
H3S2 H -0.633776 -0.010763 0.235460 0.562 Uiso 0.25 1 calc R U P B 2
H3S3 H -0.459028 0.062659 0.209586 0.562 Uiso 0.25 1 calc R U P B 2
C4S C -0.418(5) -0.2108(11) 0.2299(7) 0.215(17) Uiso 0.25 1 d D . P B 2
H4S1 H -0.529128 -0.237230 0.209859 0.322 Uiso 0.25 1 calc R U P B 2
H4S2 H -0.283277 -0.262615 0.236884 0.322 Uiso 0.25 1 calc R U P B 2
H4S3 H -0.534827 -0.195309 0.250738 0.322 Uiso 0.25 1 calc R U P B 2


_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
F1 C1 1.358(11) . ?
C13 C14 1.3900 . ?
C13 C18 1.3900 . ?
C13 C12 1.514(14) . ?
C14 C15 1.3900 . ?
C14 H14 0.9500 . ?
C15 C16 1.3900 . ?
C15 H15 0.9500 . ?
C16 C17 1.3900 . ?
C16 H16 0.9500 . ?
C17 C18 1.3900 . ?
C17 H17 0.9500 . ?
C18 C19 1.449(10) . ?
C19 C20 1.3900 . ?
C19 C24 1.3900 . ?
C20 C21 1.3900 . ?
C20 H20 0.9500 . ?
C21 C22 1.3900 . ?
C21 H21 0.9500 . ?
C22 C23 1.3900 . ?
C22 H22 0.9500 . ?
C23 C24 1.3900 . ?
C23 H23 0.9500 . ?
C24 C12 1.500(14) . ?
C12 C11 1.536(17) . ?
C12 H12 1.0000 . ?
C11 O4 1.457(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
O4 C10 1.339(15) . ?
C10 O3 1.206(16) . ?
C10 N1 1.344(18) . ?
N1 C8 1.463(15) . ?
N1 HN1 0.8800 . ?
C8 C9 1.50(2) . ?
C8 C7 1.524(19) . ?
C8 H8 1.0000 . ?
C9 O2 1.26(2) . ?
C9 O1 1.259(18) . ?
O1 H1 0.8400 . ?
C7 C6 1.512(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C1 C3 1.3900 . ?
C1 C2 1.3900 . ?
C3 C5 1.3900 . ?
C3 H3 0.9500 . ?
C5 C6 1.3900 . ?
C5 H5 0.9500 . ?
C6 C4 1.3900 . ?
C4 C2 1.3900 . ?
C4 H4 0.9500 . ?
C2 H2A 0.9500 . ?
O1S S1S 1.522(14) . ?
S1S C2S 1.802(10) . ?
S1S C1S 1.807(10) . ?
C2S H2S1 0.9800 . ?
C2S H2S2 0.9800 . ?
C2S H2S3 0.9800 . ?
C1S H1S1 0.9800 . ?
C1S H1S2 0.9800 . ?
C1S H1S3 0.9800 . ?
O2S S2S 1.53(2) . ?
S2S C4S 1.803(10) . ?
S2S C3S 1.807(10) . ?
C3S H3S1 0.9800 . ?
C3S H3S2 0.9800 . ?
C3S H3S3 0.9800 . ?
C4S H4S1 0.9800 . ?
C4S H4S2 0.9800 . ?
C4S H4S3 0.9800 . ?

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
C14 C13 C18 120.0 . . ?
C14 C13 C12 130.8(7) . . ?
C18 C13 C12 109.0(7) . . ?
C15 C14 C13 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C13 120.0 . . ?
C17 C18 C19 130.0(6) . . ?
C13 C18 C19 110.0(6) . . ?
C20 C19 C24 120.0 . . ?
C20 C19 C18 132.3(6) . . ?
C24 C19 C18 107.6(6) . . ?
C19 C20 C21 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 120.0 . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.0 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C24 C23 C22 120.0 . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C19 120.0 . . ?
C23 C24 C12 129.1(6) . . ?
C19 C24 C12 110.8(6) . . ?
C24 C12 C13 102.3(8) . . ?
C24 C12 C11 108.8(10) . . ?
C13 C12 C11 114.1(10) . . ?
C24 C12 H12 110.4 . . ?
C13 C12 H12 110.4 . . ?
C11 C12 H12 110.4 . . ?
O4 C11 C12 109.0(11) . . ?
O4 C11 H11A 109.9 . . ?
C12 C11 H11A 109.9 . . ?
O4 C11 H11B 109.9 . . ?
C12 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
C10 O4 C11 114.4(10) . . ?
O3 C10 O4 123.8(14) . . ?
O3 C10 N1 127.0(13) . . ?
O4 C10 N1 109.1(11) . . ?
C10 N1 C8 120.0(11) . . ?
C10 N1 HN1 120.0 . . ?
C8 N1 HN1 120.0 . . ?
N1 C8 C9 112.7(12) . . ?
N1 C8 C7 111.1(11) . . ?
C9 C8 C7 108.9(11) . . ?
N1 C8 H8 108.0 . . ?
C9 C8 H8 108.0 . . ?
C7 C8 H8 108.0 . . ?
O2 C9 O1 121.0(17) . . ?
O2 C9 C8 123.9(14) . . ?
O1 C9 C8 114.6(16) . . ?
C9 O1 H1 109.5 . . ?
C6 C7 C8 112.9(11) . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
F1 C1 C3 119.1(8) . . ?
F1 C1 C2 120.9(7) . . ?
C3 C1 C2 120.0 . . ?
C1 C3 C5 120.0 . . ?
C1 C3 H3 120.0 . . ?
C5 C3 H3 120.0 . . ?
C3 C5 C6 120.0 . . ?
C3 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C6 C5 120.0 . . ?
C4 C6 C7 118.1(8) . . ?
C5 C6 C7 121.8(7) . . ?
C2 C4 C6 120.0 . . ?
C2 C4 H4 120.0 . . ?
C6 C4 H4 120.0 . . ?
C4 C2 C1 120.0 . . ?
C4 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
O1S S1S C2S 105.9(8) . . ?
O1S S1S C1S 105.3(8) . . ?
C2S S1S C1S 100.8(6) . . ?
S1S C2S H2S1 109.5 . . ?
S1S C2S H2S2 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
S1S C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 109.5 . . ?
S1S C1S H1S1 109.5 . . ?
S1S C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
S1S C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?
O2S S2S C4S 105.7(11) . . ?
O2S S2S C3S 105.2(10) . . ?
C4S S2S C3S 100.7(7) . . ?
S2S C3S H3S1 109.5 . . ?
S2S C3S H3S2 109.5 . . ?
H3S1 C3S H3S2 109.5 . . ?
S2S C3S H3S3 109.5 . . ?
H3S1 C3S H3S3 109.5 . . ?
H3S2 C3S H3S3 109.5 . . ?
S2S C4S H4S1 109.5 . . ?
S2S C4S H4S2 109.5 . . ?
H4S1 C4S H4S2 109.5 . . ?
S2S C4S H4S3 109.5 . . ?
H4S1 C4S H4S3 109.5 . . ?
H4S2 C4S H4S3 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
C18 C13 C14 C15 0.0 . . . . ?
C12 C13 C14 C15 175.2(11) . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 C13 0.0 . . . . ?
C16 C17 C18 C19 -178.1(11) . . . . ?
C14 C13 C18 C17 0.0 . . . . ?
C12 C13 C18 C17 -176.2(9) . . . . ?
C14 C13 C18 C19 178.4(9) . . . . ?
C12 C13 C18 C19 2.2(9) . . . . ?
C17 C18 C19 C20 -2.8(13) . . . . ?
C13 C18 C19 C20 178.9(6) . . . . ?
C17 C18 C19 C24 173.8(6) . . . . ?
C13 C18 C19 C24 -4.4(7) . . . . ?
C24 C19 C20 C21 0.0 . . . . ?
C18 C19 C20 C21 176.4(10) . . . . ?
C19 C20 C21 C22 0.0 . . . . ?
C20 C21 C22 C23 0.0 . . . . ?
C21 C22 C23 C24 0.0 . . . . ?
C22 C23 C24 C19 0.0 . . . . ?
C22 C23 C24 C12 177.7(10) . . . . ?
C20 C19 C24 C23 0.0 . . . . ?
C18 C19 C24 C23 -177.2(8) . . . . ?
C20 C19 C24 C12 -178.1(8) . . . . ?
C18 C19 C24 C12 4.8(8) . . . . ?
C23 C24 C12 C13 178.8(7) . . . . ?
C19 C24 C12 C13 -3.3(10) . . . . ?
C23 C24 C12 C11 -60.1(12) . . . . ?
C19 C24 C12 C11 117.8(9) . . . . ?
C14 C13 C12 C24 -175.1(7) . . . . ?
C18 C13 C12 C24 0.6(10) . . . . ?
C14 C13 C12 C11 67.6(13) . . . . ?
C18 C13 C12 C11 -116.8(10) . . . . ?
C24 C12 C11 O4 179.0(9) . . . . ?
C13 C12 C11 O4 -67.5(13) . . . . ?
C12 C11 O4 C10 175.3(11) . . . . ?
C11 O4 C10 O3 -6(2) . . . . ?
C11 O4 C10 N1 177.5(11) . . . . ?
O3 C10 N1 C8 7(2) . . . . ?
O4 C10 N1 C8 -175.8(11) . . . . ?
C10 N1 C8 C9 -132.4(14) . . . . ?
C10 N1 C8 C7 105.1(15) . . . . ?
N1 C8 C9 O2 -20(2) . . . . ?
C7 C8 C9 O2 103.3(19) . . . . ?
N1 C8 C9 O1 167.6(14) . . . . ?
C7 C8 C9 O1 -68.7(17) . . . . ?
N1 C8 C7 C6 -65.6(14) . . . . ?
C9 C8 C7 C6 169.7(11) . . . . ?
F1 C1 C3 C5 -177.5(9) . . . . ?
C2 C1 C3 C5 0.0 . . . . ?
C1 C3 C5 C6 0.0 . . . . ?
C3 C5 C6 C4 0.0 . . . . ?
C3 C5 C6 C7 -176.6(10) . . . . ?
C8 C7 C6 C4 -91.2(10) . . . . ?
C8 C7 C6 C5 85.5(12) . . . . ?
C5 C6 C4 C2 0.0 . . . . ?
C7 C6 C4 C2 176.7(9) . . . . ?
C6 C4 C2 C1 0.0 . . . . ?
F1 C1 C2 C4 177.4(10) . . . . ?
C3 C1 C2 C4 0.0 . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 HN1 O3 0.88 2.10 2.847(15) 142.1 1_455
O1 H1 O1S 0.84 1.80 2.61(2) 161.2 .
O1 H1 S1S 0.84 2.74 3.498(17) 151.2 .
C2S H2S1 O2 0.98 2.27 3.02(2) 132.1 3_445
C1S H1S1 O1S 0.98 2.26 3.09(3) 140.9 1_455
C3S H3S2 O2S 0.98 2.33 3.09(3) 132.9 1_455
C4S H4S1 O2 0.98 2.17 3.02(2) 144.0 3_445

_refine_diff_density_max         0.648
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.095




# start Validation Reply Form

_vrf_PLAT023_FMOC4FPhe           
; 
PROBLEM:  Resolution (too) Low [sin(theta)/Lambda < 0.6].. 26.07 Degree
RESPONSE: Crystals diffracted poorly (best ones show reflections at a
          maximum resolution of 0.9 Ang). Radiation damage have been found 
          and limited the maximum dose allowed per data collection.
;
_vrf_THETM01_FMOC4FPhe           
; 
PROBLEM:  The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Crystals diffracted poorly (best ones show reflections at a
          maximum resolution of 0.9 Ang). Radiation damage have been found 
          and limited the maximum dose allowed per data collection.
;
_vrf_PLAT340_FMOC4FPhe           
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01344 Ang.
RESPONSE: Crystals diffracted poorly (best ones show reflections at a
          maximum resolution of 0.9 Ang) and were prone to radiation damage.
          High model e.s.d., mainly in disordered DMSO fragment, are  
          responsible for this alert.
;



# end Validation Reply Form
####################################################################### 
# 
# 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_FMOC4ClPhe
_database_code_depnum_ccdc_archive 'CCDC 1521996'
_audit_update_record             
;
2017-01-27 deposited with the CCDC.
2017-02-17 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 Cl N O4'
_chemical_formula_sum            'C24 H20 Cl N O4'
_chemical_formula_weight         421.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0059 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0105 0.0059 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1456 0.1550 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   13.168(3)
_cell_length_b                   4.8390(10)
_cell_length_c                   17.400(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.41(3)
_cell_angle_gamma                90
_cell_volume                     1032.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    48
_cell_measurement_theta_min      1.238
_cell_measurement_theta_max      24.311

_exptl_crystal_description       'Thin needles'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.205
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.700

_diffrn_measurement_method       'Rotating crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'Elettra Synchrotron - XRD1 BL'
_diffrn_measurement_device_type  
;
'Huber 4-circles Kappa Goniometer, Pilatus 2M detector'
;

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5367
_diffrn_reflns_av_unetI/netI     0.0902
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.238
_diffrn_reflns_theta_max         24.311
_diffrn_reflns_theta_full        24.311
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_point_group_measured_fraction_full 0.902
_reflns_number_total             3196
_reflns_number_gt                2068
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.640
_reflns_Friedel_fraction_max     0.810
_reflns_Friedel_fraction_full    0.810

_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.
;

_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0

_computing_data_collection       'Elettra XRD1 Data Collection SW'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_molecular_graphics    'Ortep3 for Windows - Coot'
_computing_publication_material  'enCIFer - publCIF'

_refine_special_details          
;
Hydrogen atoms were included at calculated positions with isotropic 
Ufactors=1.2Ueq (Ufactors=1.5Ueq for hydroxyl groups). Anisotropic 
thermal motion modeling has been applied to all atoms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.7311P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 598 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3196
_refine_ls_number_parameters     272
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0665
_refine_ls_wR_factor_ref         0.1977
_refine_ls_wR_factor_gt          0.1645
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.59938(18) 0.3534(5) 0.40485(15) 0.0553(7) Uani 1 1 d . . . . .
O4 O 0.5265(4) 0.6262(12) 0.7831(4) 0.0442(15) Uani 1 1 d . . . . .
O1 O 0.8811(5) 0.9914(15) 0.9160(5) 0.062(2) Uani 1 1 d . . . . .
H1A H 0.925332 1.027979 0.963708 0.093 Uiso 1 1 calc R U . . .
O3 O 0.6370(5) 0.2748(12) 0.7773(5) 0.0578(19) Uani 1 1 d . . . . .
O2 O 0.9659(5) 0.5841(14) 0.9376(5) 0.0617(19) Uani 1 1 d . . . . .
N1 N 0.7002(5) 0.7150(14) 0.8059(4) 0.0385(17) Uani 1 1 d . . . . .
H1 H 0.683278 0.887124 0.812264 0.046 Uiso 1 1 calc R U . . .
C10 C 0.6238(7) 0.5212(19) 0.7887(6) 0.041(2) Uani 1 1 d . . . . .
C6 C 0.7844(6) 0.6840(18) 0.6626(6) 0.042(2) Uani 1 1 d . . . . .
C1 C 0.6693(7) 0.478(2) 0.5024(6) 0.048(2) Uani 1 1 d . . . . .
C5 C 0.6803(7) 0.7874(19) 0.6125(6) 0.045(2) Uani 1 1 d . . . . .
H5 H 0.648083 0.929472 0.633727 0.053 Uiso 1 1 calc R U . . .
C24 C 0.2383(6) 0.379(2) 0.7192(6) 0.045(2) Uani 1 1 d . . . . .
C13 C 0.3330(6) 0.6216(18) 0.8445(6) 0.043(2) Uani 1 1 d . . . . .
C23 C 0.1981(6) 0.2741(18) 0.6404(7) 0.047(2) Uani 1 1 d . . . . .
H23 H 0.228622 0.328578 0.600985 0.057 Uiso 1 1 calc R U . . .
C3 C 0.6246(7) 0.688(2) 0.5343(6) 0.047(2) Uani 1 1 d . . . . .
H3 H 0.555504 0.763062 0.502060 0.056 Uiso 1 1 calc R U . . .
C9 C 0.8943(7) 0.7348(19) 0.8979(7) 0.047(2) Uani 1 1 d . . . . .
C12 C 0.3342(6) 0.5745(18) 0.7574(6) 0.044(2) Uani 1 1 d . . . . .
H12 H 0.321999 0.752223 0.726045 0.052 Uiso 1 1 calc R U . . .
C4 C 0.8275(7) 0.4710(19) 0.6285(6) 0.046(2) Uani 1 1 d . . . . .
H4 H 0.895907 0.392622 0.660796 0.056 Uiso 1 1 calc R U . . .
C11 C 0.4361(6) 0.4321(19) 0.7568(6) 0.046(2) Uani 1 1 d . . . . .
H11A H 0.453006 0.271132 0.794477 0.055 Uiso 1 1 calc R U . . .
H11B H 0.424309 0.364730 0.700430 0.055 Uiso 1 1 calc R U . . .
C8 C 0.8113(6) 0.6485(19) 0.8142(6) 0.042(2) Uani 1 1 d . . . . .
H8 H 0.816596 0.443829 0.808572 0.051 Uiso 1 1 calc R U . . .
C18 C 0.2485(7) 0.4562(19) 0.8541(6) 0.046(2) Uani 1 1 d . . . . .
C2 C 0.7729(7) 0.372(2) 0.5491(6) 0.046(2) Uani 1 1 d . . . . .
H2 H 0.805290 0.233964 0.526648 0.056 Uiso 1 1 calc R U . . .
C22 C 0.1122(7) 0.087(2) 0.6192(7) 0.055(3) Uani 1 1 d . . . . .
H22 H 0.082961 0.014433 0.564785 0.066 Uiso 1 1 calc R U . . .
C21 C 0.0686(7) 0.006(2) 0.6783(7) 0.056(3) Uani 1 1 d . . . . .
H21 H 0.011667 -0.127450 0.663791 0.067 Uiso 1 1 calc R U . . .
C14 C 0.3960(7) 0.7866(19) 0.9058(6) 0.048(2) Uani 1 1 d . . . . .
H14 H 0.451111 0.896641 0.897858 0.058 Uiso 1 1 calc R U . . .
C20 C 0.1071(6) 0.115(2) 0.7571(7) 0.050(2) Uani 1 1 d . . . . .
H20 H 0.076019 0.061662 0.796247 0.061 Uiso 1 1 calc R U . . .
C15 C 0.3806(8) 0.796(2) 0.9810(7) 0.056(3) Uani 1 1 d . . . . .
H15 H 0.424968 0.912266 1.024356 0.067 Uiso 1 1 calc R U . . .
C7 C 0.8449(7) 0.789(2) 0.7479(6) 0.047(2) Uani 1 1 d . . . . .
H7A H 0.832463 0.989977 0.749120 0.056 Uiso 1 1 calc R U . . .
H7B H 0.923973 0.759208 0.761524 0.056 Uiso 1 1 calc R U . . .
C16 C 0.2981(8) 0.632(2) 0.9917(7) 0.059(3) Uani 1 1 d . . . . .
H16 H 0.286284 0.639560 1.042352 0.070 Uiso 1 1 calc R U . . .
C17 C 0.2349(8) 0.461(2) 0.9300(7) 0.059(3) Uani 1 1 d . . . . .
H17 H 0.181922 0.345160 0.938897 0.070 Uiso 1 1 calc R U . . .
C19 C 0.1938(6) 0.3091(19) 0.7785(6) 0.049(2) Uani 1 1 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 C1 1.718(11) . ?
O4 C10 1.348(9) . ?
O4 C11 1.453(10) . ?
O1 C9 1.308(11) . ?
O1 H1A 0.8400 . ?
O3 C10 1.232(10) . ?
O2 C9 1.193(11) . ?
N1 C10 1.328(11) . ?
N1 C8 1.452(9) . ?
N1 H1 0.8800 . ?
C6 C4 1.407(12) . ?
C6 C5 1.420(12) . ?
C6 C7 1.494(13) . ?
C1 C3 1.387(13) . ?
C1 C2 1.406(12) . ?
C5 C3 1.377(13) . ?
C5 H5 0.9500 . ?
C24 C23 1.374(13) . ?
C24 C19 1.401(12) . ?
C24 C12 1.522(12) . ?
C13 C14 1.349(13) . ?
C13 C18 1.430(12) . ?
C13 C12 1.537(13) . ?
C23 C22 1.389(12) . ?
C23 H23 0.9500 . ?
C3 H3 0.9500 . ?
C9 C8 1.525(13) . ?
C12 C11 1.512(11) . ?
C12 H12 1.0000 . ?
C4 C2 1.389(13) . ?
C4 H4 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C8 C7 1.536(13) . ?
C8 H8 1.0000 . ?
C18 C17 1.397(13) . ?
C18 C19 1.437(14) . ?
C2 H2 0.9500 . ?
C22 C21 1.404(14) . ?
C22 H22 0.9500 . ?
C21 C20 1.383(14) . ?
C21 H21 0.9500 . ?
C14 C15 1.395(14) . ?
C14 H14 0.9500 . ?
C20 C19 1.419(13) . ?
C20 H20 0.9500 . ?
C15 C16 1.414(14) . ?
C15 H15 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C16 C17 1.370(14) . ?
C16 H16 0.9500 . ?
C17 H17 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
C10 O4 C11 115.3(7) . . ?
C9 O1 H1A 109.5 . . ?
C10 N1 C8 121.3(7) . . ?
C10 N1 H1 119.4 . . ?
C8 N1 H1 119.4 . . ?
O3 C10 N1 125.4(8) . . ?
O3 C10 O4 122.7(8) . . ?
N1 C10 O4 111.9(8) . . ?
C4 C6 C5 116.6(9) . . ?
C4 C6 C7 121.0(8) . . ?
C5 C6 C7 122.4(8) . . ?
C3 C1 C2 120.0(9) . . ?
C3 C1 Cl1 120.0(7) . . ?
C2 C1 Cl1 120.0(7) . . ?
C3 C5 C6 122.0(8) . . ?
C3 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C23 C24 C19 122.2(8) . . ?
C23 C24 C12 128.5(8) . . ?
C19 C24 C12 109.3(8) . . ?
C14 C13 C18 121.3(9) . . ?
C14 C13 C12 130.1(8) . . ?
C18 C13 C12 108.7(8) . . ?
C24 C23 C22 119.0(9) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C5 C3 C1 120.1(8) . . ?
C5 C3 H3 119.9 . . ?
C1 C3 H3 119.9 . . ?
O2 C9 O1 125.9(10) . . ?
O2 C9 C8 121.7(8) . . ?
O1 C9 C8 112.2(8) . . ?
C11 C12 C24 108.1(7) . . ?
C11 C12 C13 113.8(7) . . ?
C24 C12 C13 102.6(7) . . ?
C11 C12 H12 110.7 . . ?
C24 C12 H12 110.7 . . ?
C13 C12 H12 110.7 . . ?
C2 C4 C6 122.0(8) . . ?
C2 C4 H4 119.0 . . ?
C6 C4 H4 119.0 . . ?
O4 C11 C12 109.3(7) . . ?
O4 C11 H11A 109.8 . . ?
C12 C11 H11A 109.8 . . ?
O4 C11 H11B 109.8 . . ?
C12 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
N1 C8 C9 112.3(7) . . ?
N1 C8 C7 112.5(7) . . ?
C9 C8 C7 107.1(7) . . ?
N1 C8 H8 108.3 . . ?
C9 C8 H8 108.3 . . ?
C7 C8 H8 108.3 . . ?
C17 C18 C13 118.4(9) . . ?
C17 C18 C19 132.8(8) . . ?
C13 C18 C19 108.8(8) . . ?
C4 C2 C1 119.3(9) . . ?
C4 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C23 C22 C21 120.0(10) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C20 C21 C22 121.2(9) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C13 C14 C15 120.3(8) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C21 C20 C19 118.8(9) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C14 C15 C16 119.1(9) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C6 C7 C8 113.7(8) . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C17 C16 C15 120.9(10) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 120.0(9) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C24 C19 C20 118.7(9) . . ?
C24 C19 C18 110.5(8) . . ?
C20 C19 C18 130.9(9) . . ?

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
C8 N1 C10 O3 -1.0(15) . . . . ?
C8 N1 C10 O4 -179.6(7) . . . . ?
C11 O4 C10 O3 -4.2(13) . . . . ?
C11 O4 C10 N1 174.4(7) . . . . ?
C4 C6 C5 C3 -0.9(13) . . . . ?
C7 C6 C5 C3 -179.3(8) . . . . ?
C19 C24 C23 C22 -1.6(13) . . . . ?
C12 C24 C23 C22 177.0(8) . . . . ?
C6 C5 C3 C1 0.8(13) . . . . ?
C2 C1 C3 C5 -1.8(13) . . . . ?
Cl1 C1 C3 C5 179.8(7) . . . . ?
C23 C24 C12 C11 -62.0(12) . . . . ?
C19 C24 C12 C11 116.7(8) . . . . ?
C23 C24 C12 C13 177.5(8) . . . . ?
C19 C24 C12 C13 -3.7(9) . . . . ?
C14 C13 C12 C11 66.9(12) . . . . ?
C18 C13 C12 C11 -113.7(8) . . . . ?
C14 C13 C12 C24 -176.6(9) . . . . ?
C18 C13 C12 C24 2.8(9) . . . . ?
C5 C6 C4 C2 1.9(12) . . . . ?
C7 C6 C4 C2 -179.6(8) . . . . ?
C10 O4 C11 C12 177.2(8) . . . . ?
C24 C12 C11 O4 172.8(7) . . . . ?
C13 C12 C11 O4 -74.0(9) . . . . ?
C10 N1 C8 C9 -123.0(9) . . . . ?
C10 N1 C8 C7 116.1(9) . . . . ?
O2 C9 C8 N1 134.2(9) . . . . ?
O1 C9 C8 N1 -50.3(10) . . . . ?
O2 C9 C8 C7 -101.8(10) . . . . ?
O1 C9 C8 C7 73.7(9) . . . . ?
C14 C13 C18 C17 -2.4(13) . . . . ?
C12 C13 C18 C17 178.1(8) . . . . ?
C14 C13 C18 C19 178.5(8) . . . . ?
C12 C13 C18 C19 -0.9(9) . . . . ?
C6 C4 C2 C1 -2.9(13) . . . . ?
C3 C1 C2 C4 2.8(13) . . . . ?
Cl1 C1 C2 C4 -178.7(7) . . . . ?
C24 C23 C22 C21 -0.8(13) . . . . ?
C23 C22 C21 C20 2.3(14) . . . . ?
C18 C13 C14 C15 0.8(13) . . . . ?
C12 C13 C14 C15 -179.8(9) . . . . ?
C22 C21 C20 C19 -1.4(14) . . . . ?
C13 C14 C15 C16 -0.1(14) . . . . ?
C4 C6 C7 C8 -94.2(9) . . . . ?
C5 C6 C7 C8 84.2(11) . . . . ?
N1 C8 C7 C6 -67.0(10) . . . . ?
C9 C8 C7 C6 169.2(7) . . . . ?
C14 C15 C16 C17 1.1(16) . . . . ?
C15 C16 C17 C18 -2.7(16) . . . . ?
C13 C18 C17 C16 3.4(14) . . . . ?
C19 C18 C17 C16 -177.9(9) . . . . ?
C23 C24 C19 C20 2.5(13) . . . . ?
C12 C24 C19 C20 -176.4(8) . . . . ?
C23 C24 C19 C18 -177.7(8) . . . . ?
C12 C24 C19 C18 3.4(10) . . . . ?
C21 C20 C19 C24 -0.9(13) . . . . ?
C21 C20 C19 C18 179.3(9) . . . . ?
C17 C18 C19 C24 179.6(10) . . . . ?
C13 C18 C19 C24 -1.5(10) . . . . ?
C17 C18 C19 C20 -0.6(17) . . . . ?
C13 C18 C19 C20 178.3(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A O2 0.84 1.81 2.645(11) 172.4 2_757
N1 H1 O3 0.88 2.00 2.824(9) 156.0 1_565
C12 H12 Cl1 1.00 2.87 3.516(9) 123.3 2_656

_refine_diff_density_max         0.418
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.063



# start Validation Reply Form

_vrf_PLAT340_FMOC4ClPhe          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.014 Ang.
RESPONSE: Crystals diffracted poorly (best ones show reflections at a
          maximum resolution of 0.85 Ang) and were prone to radiation damage.
;

# end Validation Reply Form
####################################################################### 
# 
# 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_FMOC4IPhe
_database_code_depnum_ccdc_archive 'CCDC 1521993'
_audit_update_record             
;
2017-02-13 deposited with the CCDC.
2017-02-17 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 I N O4, 0.333(H2 O)'
_chemical_formula_sum            'C24 H20.67 I N O4.33'
_chemical_formula_weight         519.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0059 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0105 0.0059 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4630 1.7726 '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'

_space_group_crystal_system      hexagonal
_space_group_IT_number           173
_space_group_name_H-M_alt        'P 63'
_space_group_name_Hall           'P 6c'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x-y, z'
'y, -x+y, z+1/2'
'-x+y, -x, z'
'x-y, x, z+1/2'

_cell_length_a                   26.878(4)
_cell_length_b                   26.878(4)
_cell_length_c                   4.999(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3127.6(11)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    640
_cell_measurement_theta_min      1.492
_cell_measurement_theta_max      21.606

_exptl_crystal_description       'Thin needles'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_F_000             1556
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.458
_shelx_estimated_absorpt_T_min   0.880
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.700


_diffrn_measurement_method       'Rotating crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'Elettra Synchrotron - XRD1 BL'
_diffrn_measurement_device_type  
;
'Huber 4-circles Kappa Goniometer, Pilatus 2M detector'
;

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4718
_diffrn_reflns_av_unetI/netI     0.1964
_diffrn_reflns_av_R_equivalents  0.1514
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         1.492
_diffrn_reflns_theta_max         21.606
_diffrn_reflns_theta_full        21.606
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_point_group_measured_fraction_full 0.844
_reflns_number_total             2162
_reflns_number_gt                1263
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.515
_reflns_Friedel_fraction_max     0.668
_reflns_Friedel_fraction_full    0.668

_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.
;

_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_decay_%        0

_computing_data_collection       'Elettra XRD1 Data Collection SW'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2015)'
_computing_molecular_graphics    'Ortep3 for Windows - Coot'
_computing_publication_material  'enCIFer - publCIF'

_refine_special_details          
;
Hydrogen atoms were included at calculated positions with isotropic 
Ufactors=1.2Ueq (Ufactors=1.5Ueq for H bound to oxygens). 
Anisotropic thermal motion modeling as then been applied to atoms 
with full occupancy. Geometric restrains (FLAT) have been applied to 
carboxylate group. Thermal restrains (DELU and SIMU) have been applied 
to the molecule scaffold atoms, showing disturbed electron densities 
related to the presence of crystal defects (due to solvent loss and 
radiation damage).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0185P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 288 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(13)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2162
_refine_ls_number_parameters     227
_refine_ls_number_restraints     55
_refine_ls_R_factor_all          0.1424
_refine_ls_R_factor_gt           0.0733
_refine_ls_wR_factor_ref         0.1896
_refine_ls_wR_factor_gt          0.1554
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.54668(6) 0.92323(7) 0.032(3) 0.0464(6) Uani 1 1 d . . . . .
C1 C 0.6215(5) 0.9361(7) 0.213(4) 0.044(9) Uani 1 1 d G . . . .
C2 C 0.6754(7) 0.9764(7) 0.117(4) 0.034(4) Uani 1 1 d G U . . .
H2 H 0.678629 0.999952 -0.031063 0.041 Uiso 1 1 calc R U . . .
C4 C 0.7246(5) 0.9822(6) 0.239(4) 0.034(4) Uani 1 1 d G U . . .
H4 H 0.761410 1.009798 0.173312 0.041 Uiso 1 1 calc R U . . .
C6 C 0.7198(5) 0.9478(7) 0.455(4) 0.034(4) Uani 1 1 d G U . . .
C5 C 0.6659(7) 0.9075(7) 0.551(4) 0.052(7) Uani 1 1 d G . . . .
H5 H 0.662648 0.883893 0.699208 0.062 Uiso 1 1 calc R U . . .
C3 C 0.6167(5) 0.9016(6) 0.430(4) 0.037(9) Uani 1 1 d G . . . .
H3 H 0.579866 0.874046 0.494835 0.044 Uiso 1 1 calc R U . . .
C13 C 0.5275(6) 0.6447(6) 0.058(5) 0.036(6) Uani 1 1 d G U . . .
C14 C 0.5383(6) 0.6069(7) -0.086(5) 0.039(6) Uani 1 1 d G U . . .
H14 H 0.572377 0.605384 -0.052396 0.047 Uiso 1 1 calc R U . . .
C15 C 0.4994(7) 0.5711(7) -0.277(4) 0.043(7) Uani 1 1 d G U . . .
H15 H 0.506837 0.545244 -0.375384 0.052 Uiso 1 1 calc R U . . .
C16 C 0.4496(6) 0.5733(7) -0.326(4) 0.036(6) Uani 1 1 d G U . . .
H16 H 0.422981 0.548857 -0.457208 0.044 Uiso 1 1 calc R U . . .
C17 C 0.4387(5) 0.6111(7) -0.183(5) 0.043(6) Uani 1 1 d G U . . .
H17 H 0.404666 0.612610 -0.216047 0.051 Uiso 1 1 calc R U . . .
C18 C 0.4776(6) 0.6469(6) 0.009(5) 0.030(5) Uani 1 1 d G U . . .
C19 C 0.4745(4) 0.6864(4) 0.18452(2) 0.035(7) Uani 1 1 d G U . . .
C20 C 0.4343(4) 0.7040(5) 0.2215(14) 0.034(7) Uani 1 1 d G . . . .
H20 H 0.400269 0.687596 0.116548 0.041 Uiso 1 1 calc R U . . .
C21 C 0.4439(4) 0.7455(5) 0.412(3) 0.054(10) Uani 1 1 d G . . . .
H21 H 0.416405 0.757489 0.437437 0.065 Uiso 1 1 calc R U . . .
C22 C 0.4936(4) 0.7695(5) 0.566(3) 0.052(8) Uani 1 1 d G U . . .
H22 H 0.500183 0.797849 0.696022 0.062 Uiso 1 1 calc R U . . .
C23 C 0.5338(4) 0.7519(4) 0.5287(14) 0.041(6) Uani 1 1 d G U . . .
H23 H 0.567825 0.768317 0.633723 0.049 Uiso 1 1 calc R U . . .
C24 C 0.5242(4) 0.7104(4) 0.3381(6) 0.043(8) Uani 1 1 d G U . . .
O4 O 0.6584(7) 0.7699(7) 0.348(5) 0.030(4) Uani 1 1 d . U . . .
N1 N 0.7393(8) 0.8486(8) 0.462(5) 0.025(5) Uani 1 1 d . U . . .
HN1 H 0.733727 0.834798 0.625510 0.030 Uiso 1 1 calc R U . . .
O3 O 0.7139(6) 0.8333(6) 0.030(7) 0.036(4) Uani 1 1 d . U . . .
C12 C 0.5633(12) 0.6881(11) 0.263(7) 0.037(6) Uani 1 1 d . U . . .
H12 H 0.570583 0.669388 0.419667 0.044 Uiso 1 1 calc R U . . .
C10 C 0.7045(4) 0.8174(5) 0.255(3) 0.025(5) Uani 1 1 d G U . . .
C7 C 0.7765(4) 0.9517(4) 0.581(5) 0.038(9) Uani 1 1 d G . . . .
H7A H 0.770482 0.939792 0.771108 0.045 Uiso 1 1 calc R U . . .
H7B H 0.809598 0.991214 0.567392 0.045 Uiso 1 1 calc R U . . .
C9 C 0.8410(4) 0.9128(6) 0.531(5) 0.075(5) Uani 1 1 d G U . . .
C11 C 0.6196(4) 0.7308(5) 0.126(2) 0.044(8) Uani 1 1 d G U . . .
H11A H 0.637227 0.710394 0.037711 0.053 Uiso 1 1 calc R U . . .
H11B H 0.612685 0.753378 -0.010598 0.053 Uiso 1 1 calc R U . . .
C8 C 0.7866(3) 0.9065(5) 0.396(4) 0.074(6) Uani 1 1 d G U . . .
H8 H 0.791020 0.915603 0.200482 0.088 Uiso 1 1 calc R U . . .
O1 O 0.8879(8) 0.9599(8) 0.482(7) 0.087(6) Uani 1 1 d . U . . .
H1 H 0.880834 0.980914 0.383579 0.131 Uiso 1 1 calc R U . . .
O2 O 0.8464(9) 0.8795(10) 0.678(6) 0.080(6) Uani 1 1 d . U . . .
OW1A O 1.000000 1.000000 0.66(2) 0.14(8) Uani 0.6 3 d S T P A 1
OW1B O 0.948(5) 0.976(5) 1.05(6) 0.04(3) Uiso 0.1333 1 d . . P B 2


_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 C1 2.069(12) . ?
C1 C2 1.3900 . ?
C1 C3 1.3900 . ?
C2 C4 1.3900 . ?
C2 H2 0.9500 . ?
C4 C6 1.3900 . ?
C4 H4 0.9500 . ?
C6 C5 1.3900 . ?
C6 C7 1.601(18) . ?
C5 C3 1.3900 . ?
C5 H5 0.9500 . ?
C3 H3 0.9500 . ?
C13 C14 1.3900 . ?
C13 C18 1.3900 . ?
C13 C12 1.49(3) . ?
C14 C15 1.3900 . ?
C14 H14 0.9500 . ?
C15 C16 1.3900 . ?
C15 H15 0.9500 . ?
C16 C17 1.3900 . ?
C16 H16 0.9500 . ?
C17 C18 1.3900 . ?
C17 H17 0.9500 . ?
C18 C19 1.414(18) . ?
C19 C20 1.3900 . ?
C19 C24 1.3900 . ?
C20 C21 1.3900 . ?
C20 H20 0.9500 . ?
C21 C22 1.3900 . ?
C21 H21 0.9500 . ?
C22 C23 1.3900 . ?
C22 H22 0.9500 . ?
C23 C24 1.3900 . ?
C23 H23 0.9500 . ?
C24 C12 1.49(3) . ?
O4 C10 1.342(19) . ?
O4 C11 1.53(2) . ?
N1 C10 1.36(2) . ?
N1 C8 1.47(2) . ?
N1 HN1 0.8800 . ?
O3 C10 1.18(3) . ?
C12 C11 1.53(3) . ?
C12 H12 1.0000 . ?
C7 C8 1.6536 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 O2 1.22(3) . ?
C9 O1 1.29(2) . ?
C9 C8 1.5404 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C8 H8 1.0000 . ?
O1 H1 0.8400 . ?

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
C2 C1 C3 120.0 . . ?
C2 C1 I1 121.8(8) . . ?
C3 C1 I1 118.1(9) . . ?
C1 C2 C4 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C2 H2 120.0 . . ?
C6 C4 C2 120.0 . . ?
C6 C4 H4 120.0 . . ?
C2 C4 H4 120.0 . . ?
C4 C6 C5 120.0 . . ?
C4 C6 C7 119.6(12) . . ?
C5 C6 C7 120.2(11) . . ?
C3 C5 C6 120.0 . . ?
C3 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C3 C1 120.0 . . ?
C5 C3 H3 120.0 . . ?
C1 C3 H3 120.0 . . ?
C14 C13 C18 120.0 . . ?
C14 C13 C12 129.6(13) . . ?
C18 C13 C12 110.3(13) . . ?
C15 C14 C13 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 120.0 . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C13 120.0 . . ?
C17 C18 C19 129.8(11) . . ?
C13 C18 C19 110.2(11) . . ?
C20 C19 C24 120.0 . . ?
C20 C19 C18 133.4(8) . . ?
C24 C19 C18 106.6(8) . . ?
C19 C20 C21 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 120.0 . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.0 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C24 C23 C22 120.0 . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C19 120.0 . . ?
C23 C24 C12 127.5(12) . . ?
C19 C24 C12 112.4(12) . . ?
C10 O4 C11 113.1(15) . . ?
C10 N1 C8 116.4(17) . . ?
C10 N1 HN1 121.8 . . ?
C8 N1 HN1 121.8 . . ?
C13 C12 C24 100.2(18) . . ?
C13 C12 C11 107(2) . . ?
C24 C12 C11 116.1(18) . . ?
C13 C12 H12 111.1 . . ?
C24 C12 H12 111.1 . . ?
C11 C12 H12 111.1 . . ?
O3 C10 O4 126.9(13) . . ?
O3 C10 N1 122.8(14) . . ?
O4 C10 N1 110.2(14) . . ?
C6 C7 C8 103.5(8) . . ?
C6 C7 H7A 111.1 . . ?
C8 C7 H7A 111.1 . . ?
C6 C7 H7B 111.1 . . ?
C8 C7 H7B 111.1 . . ?
H7A C7 H7B 109.0 . . ?
O2 C9 O1 114.7(17) . . ?
O2 C9 C8 129.6(11) . . ?
O1 C9 C8 115.7(14) . . ?
O4 C11 C12 105.6(15) . . ?
O4 C11 H11A 110.6 . . ?
C12 C11 H11A 110.6 . . ?
O4 C11 H11B 110.6 . . ?
C12 C11 H11B 110.6 . . ?
H11A C11 H11B 108.8 . . ?
N1 C8 C9 106.8(8) . . ?
N1 C8 C7 106.2(8) . . ?
C9 C8 C7 99.9 . . ?
N1 C8 H8 114.2 . . ?
C9 C8 H8 114.2 . . ?
C7 C8 H8 114.2 . . ?
C9 O1 H1 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 C1 C2 C4 0.0 . . . . ?
I1 C1 C2 C4 -177.7(12) . . . . ?
C1 C2 C4 C6 0.0 . . . . ?
C2 C4 C6 C5 0.0 . . . . ?
C2 C4 C6 C7 175.7(14) . . . . ?
C4 C6 C5 C3 0.0 . . . . ?
C7 C6 C5 C3 -175.7(14) . . . . ?
C6 C5 C3 C1 0.0 . . . . ?
C2 C1 C3 C5 0.0 . . . . ?
I1 C1 C3 C5 177.8(12) . . . . ?
C18 C13 C14 C15 0.0 . . . . ?
C12 C13 C14 C15 -178(2) . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 C13 0.0 . . . . ?
C16 C17 C18 C19 -177.0(19) . . . . ?
C14 C13 C18 C17 0.0 . . . . ?
C12 C13 C18 C17 178.0(19) . . . . ?
C14 C13 C18 C19 177.5(16) . . . . ?
C12 C13 C18 C19 -4.5(18) . . . . ?
C17 C18 C19 C20 -2(2) . . . . ?
C13 C18 C19 C20 -179.1(8) . . . . ?
C17 C18 C19 C24 179.1(11) . . . . ?
C13 C18 C19 C24 1.9(11) . . . . ?
C24 C19 C20 C21 0.0 . . . . ?
C18 C19 C20 C21 -178.9(15) . . . . ?
C19 C20 C21 C22 0.0 . . . . ?
C20 C21 C22 C23 0.0 . . . . ?
C21 C22 C23 C24 0.0 . . . . ?
C22 C23 C24 C19 0.0 . . . . ?
C22 C23 C24 C12 177.4(16) . . . . ?
C20 C19 C24 C23 0.0 . . . . ?
C18 C19 C24 C23 179.1(12) . . . . ?
C20 C19 C24 C12 -177.8(14) . . . . ?
C18 C19 C24 C12 1.4(15) . . . . ?
C14 C13 C12 C24 -177.4(13) . . . . ?
C18 C13 C12 C24 5(2) . . . . ?
C14 C13 C12 C11 61(3) . . . . ?
C18 C13 C12 C11 -116.6(15) . . . . ?
C23 C24 C12 C13 178.7(11) . . . . ?
C19 C24 C12 C13 -4(2) . . . . ?
C23 C24 C12 C11 -67(3) . . . . ?
C19 C24 C12 C11 110.7(18) . . . . ?
C11 O4 C10 O3 8(2) . . . . ?
C11 O4 C10 N1 -176.1(11) . . . . ?
C8 N1 C10 O3 6(2) . . . . ?
C8 N1 C10 O4 -170.3(12) . . . . ?
C4 C6 C7 C8 -86.2(10) . . . . ?
C5 C6 C7 C8 89.5(11) . . . . ?
C10 O4 C11 C12 -166.1(13) . . . . ?
C13 C12 C11 O4 -172.7(15) . . . . ?
C24 C12 C11 O4 77(2) . . . . ?
C10 N1 C8 C9 -133.6(12) . . . . ?
C10 N1 C8 C7 120.5(12) . . . . ?
O2 C9 C8 N1 -3.9(16) . . . . ?
O1 C9 C8 N1 176.0(16) . . . . ?
O2 C9 C8 C7 106.5(12) . . . . ?
O1 C9 C8 C7 -73.6(12) . . . . ?
C6 C7 C8 N1 -68.8(12) . . . . ?
C6 C7 C8 C9 -179.6(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 HN1 O3 0.88 2.09 2.90(4) 153.9 1_556
O1 H1 O2 0.84 1.76 2.59(3) 169.7 4_564

_refine_diff_density_max         0.939
_refine_diff_density_min         -0.761
_refine_diff_density_rms         0.138



# start Validation Reply Form

_vrf_PLAT023_FMOC4IPhe           
; 
PROBLEM:  Resolution (too) Low [sin(theta)/Lambda < 0.6].. 21.61 Degree
RESPONSE: Crystals diffracted poorly (best ones show reflections at a
          maximum resolution of 0.9 Ang). Radiation damage have been found 
          and limited the maximum dose allowed per data collection.
;
_vrf_THETM01_FMOC4IPhe           
; 
PROBLEM:  The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Crystals diffracted poorly (best ones show reflections at a
          maximum resolution of 0.9 Ang). Radiation damage have been found 
          and limited the maximum dose allowed per data collection.
;
_vrf_PLAT342_FMOC4IPhe           
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.0258 Ang.
RESPONSE: Crystals diffracted poorly (best ones show reflections at a
          maximum resolution of 0.9 Ang) and were prone to radiation damage.
;

# end Validation Reply Form
