# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# 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 
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data_FmocF_100K_P21
_database_code_depnum_ccdc_archive 'CCDC 1060776'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2015-06-11 downloaded from the CCDC.
;
_audit_creation_date             2015-05-19
_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        ?
_chemical_formula_moiety         'C24 H21 N O4'
_chemical_formula_sum            'C24 H21 N O4'
_chemical_formula_weight         387.42
_chemical_absolute_configuration L
_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'
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                   13.1570(13)
_cell_length_b                   4.9083(4)
_cell_length_c                   16.1242(16)
_cell_angle_alpha                90
_cell_angle_beta                 113.135(3)
_cell_angle_gamma                90
_cell_volume                     957.54(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1360
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.564
_cell_measurement_theta_min      2.557
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1111 before and 0.0623 after correction.
The Ratio of minimum to maximum transmission is 0.7462.
The λ/2 correction factor is 0.0000.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0696
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13345
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.420
_diffrn_reflns_theta_min         1.373
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  Rigaku_AFC12K_724P_007HF_Mo
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    0.910
_reflns_Friedel_fraction_max     0.883
_reflns_number_gt                2762
_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.

 Diffraction anisotropy and poor single crystal quality 
 account for the higher than estimated 
 _exptl_absorpt_correction_T_max/_exptl_absorpt_correction
 _T_min ratio of 0.7454/0.5562. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_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         0.157
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 947 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.4(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         3717
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0455
_refine_ls_restrained_S_all      0.996
_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)+(0.0517P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.1027
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H) groups
2.a Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 0.25631(17) 0.3871(5) 0.26226(15) 0.0251(6) Uani 1 1 d . . . . .
O2 O 0.14355(19) 0.7418(5) 0.25786(16) 0.0301(6) Uani 1 1 d . . . . .
O3 O 0.0362(2) 0.0382(5) 0.40860(17) 0.0361(7) Uani 1 1 d . . . . .
H3 H 0.0365 -0.0003 0.4594 0.054 Uiso 1 1 calc GR . . . .
O4 O -0.0241(2) 0.4436(5) 0.43479(17) 0.0410(7) Uani 1 1 d . . . . .
N1 N 0.1058(2) 0.3091(7) 0.2884(2) 0.0238(7) Uani 1 1 d . . . . .
C1 C 0.4837(3) 0.6372(7) 0.1978(2) 0.0238(8) Uani 1 1 d . . . . .
C2 C 0.4467(3) 0.7602(8) 0.1136(3) 0.0282(8) Uani 1 1 d . . . . .
C3 C 0.5124(3) 0.9525(8) 0.0957(3) 0.0281(9) Uani 1 1 d . . . . .
C4 C 0.6152(3) 1.0224(8) 0.1616(3) 0.0318(9) Uani 1 1 d . . . . .
C5 C 0.6542(3) 0.8997(8) 0.2465(3) 0.0311(8) Uani 1 1 d . . . . .
C6 C 0.5877(3) 0.7056(7) 0.2639(2) 0.0262(8) Uani 1 1 d . . . . .
C7 C 0.6056(3) 0.5476(8) 0.3462(2) 0.0275(8) Uani 1 1 d . . . . .
C8 C 0.6958(3) 0.5340(8) 0.4278(2) 0.0349(10) Uani 1 1 d . . . . .
C9 C 0.6921(3) 0.3588(9) 0.4938(3) 0.0393(10) Uani 1 1 d . . . . .
C10 C 0.5988(3) 0.2011(9) 0.4788(3) 0.0352(10) Uani 1 1 d . . . . .
C11 C 0.5078(3) 0.2133(8) 0.3973(2) 0.0293(9) Uani 1 1 d . . . . .
C12 C 0.5114(3) 0.3865(7) 0.3304(2) 0.0258(8) Uani 1 1 d . . . . .
C13 C 0.4250(3) 0.4393(8) 0.2361(2) 0.0255(8) Uani 1 1 d . . . . .
C14 C 0.3207(3) 0.5792(8) 0.2334(3) 0.0257(8) Uani 1 1 d . . . . .
C15 C 0.1658(3) 0.5003(7) 0.2688(2) 0.0234(8) Uani 1 1 d . . . . .
C16 C 0.0035(3) 0.3807(8) 0.2977(2) 0.0248(8) Uani 1 1 d . . . . .
C17 C -0.0997(3) 0.2515(9) 0.2259(2) 0.0283(8) Uani 1 1 d . . . . .
C18 C -0.1247(3) 0.3570(8) 0.1320(2) 0.0268(8) Uani 1 1 d . . . . .
C19 C -0.0761(3) 0.2403(8) 0.0780(2) 0.0284(8) Uani 1 1 d . . . . .
C20 C -0.1004(3) 0.3347(8) -0.0087(2) 0.0318(9) Uani 1 1 d . . . . .
C21 C -0.1725(3) 0.5508(8) -0.0422(3) 0.0323(9) Uani 1 1 d . . . . .
C22 C -0.2221(3) 0.6678(8) 0.0109(3) 0.0330(9) Uani 1 1 d . . . . .
C23 C -0.1986(3) 0.5712(8) 0.0972(3) 0.0303(9) Uani 1 1 d . . . . .
C24 C 0.0059(3) 0.2929(8) 0.3890(2) 0.0263(8) Uani 1 1 d . . . . .
H11 H 0.444(3) 0.110(8) 0.389(2) 0.031(10) Uiso 1 1 d . . . . .
H14A H 0.340(3) 0.735(9) 0.276(2) 0.032(10) Uiso 1 1 d . . . . .
H10 H 0.598(3) 0.070(9) 0.523(3) 0.041(11) Uiso 1 1 d . . . . .
H16 H -0.003(3) 0.578(8) 0.295(2) 0.020(9) Uiso 1 1 d . . . . .
H20 H -0.067(3) 0.248(10) -0.045(3) 0.055(12) Uiso 1 1 d . . . . .
H2 H 0.376(3) 0.722(8) 0.069(2) 0.023(9) Uiso 1 1 d . . . . .
H1 H 0.119(3) 0.142(8) 0.288(2) 0.016(10) Uiso 1 1 d . . . . .
H22 H -0.273(3) 0.814(10) -0.011(3) 0.044(12) Uiso 1 1 d . . . . .
H17A H -0.164(3) 0.309(8) 0.243(2) 0.035(10) Uiso 1 1 d . . . . .
H3A H 0.482(3) 1.035(8) 0.041(3) 0.028(10) Uiso 1 1 d . . . . .
H19 H -0.026(3) 0.072(8) 0.101(2) 0.029(9) Uiso 1 1 d . . . . .
H17B H -0.087(3) 0.054(10) 0.228(3) 0.045(11) Uiso 1 1 d . . . . .
H9 H 0.752(3) 0.359(9) 0.548(3) 0.041(12) Uiso 1 1 d . . . . .
H13 H 0.410(3) 0.261(9) 0.202(2) 0.042(11) Uiso 1 1 d . . . . .
H21 H -0.187(3) 0.632(9) -0.101(3) 0.051(12) Uiso 1 1 d . . . . .
H14B H 0.270(3) 0.634(8) 0.170(3) 0.035(11) Uiso 1 1 d . . . . .
H5 H 0.730(4) 0.950(10) 0.298(3) 0.061(14) Uiso 1 1 d . . . . .
H8 H 0.763(3) 0.636(9) 0.437(3) 0.050(12) Uiso 1 1 d . . . . .
H4 H 0.658(3) 1.159(9) 0.149(2) 0.045(12) Uiso 1 1 d . . . . .
H23 H -0.238(3) 0.649(9) 0.130(3) 0.050(12) Uiso 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
O1 C14 1.460(4) . ?
O1 C15 1.356(4) . ?
O2 C15 1.217(4) . ?
O3 H3 0.8400 . ?
O3 C24 1.312(4) . ?
O4 C24 1.215(4) . ?
N1 C15 1.341(4) . ?
N1 C16 1.454(4) . ?
N1 H1 0.84(4) . ?
C1 C2 1.388(5) . ?
C1 C6 1.406(5) . ?
C1 C13 1.515(5) . ?
C2 C3 1.385(5) . ?
C2 H2 0.94(3) . ?
C3 C4 1.395(5) . ?
C3 H3A 0.90(4) . ?
C4 C5 1.395(5) . ?
C4 H4 0.95(4) . ?
C5 C6 1.395(5) . ?
C5 H5 1.04(4) . ?
C6 C7 1.473(5) . ?
C7 C8 1.385(5) . ?
C7 C12 1.406(5) . ?
C8 C9 1.384(6) . ?
C8 H8 0.98(4) . ?
C9 C10 1.389(6) . ?
C9 H9 0.92(4) . ?
C10 C11 1.388(5) . ?
C10 H10 0.96(4) . ?
C11 C12 1.389(5) . ?
C11 H11 0.94(4) . ?
C12 C13 1.521(5) . ?
C13 C14 1.520(5) . ?
C13 H13 1.01(4) . ?
C14 H14A 0.99(4) . ?
C14 H14B 1.02(4) . ?
C16 C17 1.532(5) . ?
C16 C24 1.523(5) . ?
C16 H16 0.97(4) . ?
C17 C18 1.509(5) . ?
C17 H17A 1.02(4) . ?
C17 H17B 0.98(5) . ?
C18 C19 1.390(5) . ?
C18 C23 1.392(5) . ?
C19 C20 1.386(5) . ?
C19 H19 1.03(4) . ?
C20 C21 1.383(5) . ?
C20 H20 0.96(4) . ?
C21 C22 1.389(5) . ?
C21 H21 0.98(4) . ?
C22 C23 1.384(5) . ?
C22 H22 0.95(4) . ?
C23 H23 0.95(4) . ?

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
C15 O1 C14 113.4(3) . . ?
C24 O3 H3 109.5 . . ?
C15 N1 C16 120.6(3) . . ?
C15 N1 H1 123(2) . . ?
C16 N1 H1 116(2) . . ?
C2 C1 C6 120.1(3) . . ?
C2 C1 C13 129.6(3) . . ?
C6 C1 C13 110.2(3) . . ?
C1 C2 H2 121(2) . . ?
C3 C2 C1 119.5(4) . . ?
C3 C2 H2 119(2) . . ?
C2 C3 C4 120.5(4) . . ?
C2 C3 H3A 116(2) . . ?
C4 C3 H3A 124(2) . . ?
C3 C4 C5 120.9(4) . . ?
C3 C4 H4 119(2) . . ?
C5 C4 H4 120(2) . . ?
C4 C5 H5 123(3) . . ?
C6 C5 C4 118.3(3) . . ?
C6 C5 H5 119(3) . . ?
C1 C6 C7 108.7(3) . . ?
C5 C6 C1 120.8(3) . . ?
C5 C6 C7 130.6(3) . . ?
C8 C7 C6 130.9(3) . . ?
C8 C7 C12 120.6(3) . . ?
C12 C7 C6 108.4(3) . . ?
C7 C8 H8 120(2) . . ?
C9 C8 C7 119.0(4) . . ?
C9 C8 H8 121(2) . . ?
C8 C9 C10 120.5(4) . . ?
C8 C9 H9 117(3) . . ?
C10 C9 H9 123(3) . . ?
C9 C10 H10 121(2) . . ?
C11 C10 C9 121.0(4) . . ?
C11 C10 H10 118(2) . . ?
C10 C11 C12 118.8(4) . . ?
C10 C11 H11 120(2) . . ?
C12 C11 H11 121(2) . . ?
C7 C12 C13 110.1(3) . . ?
C11 C12 C7 120.1(3) . . ?
C11 C12 C13 129.8(3) . . ?
C1 C13 C12 102.4(3) . . ?
C1 C13 C14 107.3(3) . . ?
C1 C13 H13 110(2) . . ?
C12 C13 H13 108(2) . . ?
C14 C13 C12 114.7(3) . . ?
C14 C13 H13 114(2) . . ?
O1 C14 C13 109.2(3) . . ?
O1 C14 H14A 107(2) . . ?
O1 C14 H14B 105(2) . . ?
C13 C14 H14A 110(2) . . ?
C13 C14 H14B 111.8(19) . . ?
H14A C14 H14B 112(3) . . ?
O2 C15 O1 123.8(3) . . ?
O2 C15 N1 125.8(3) . . ?
N1 C15 O1 110.3(3) . . ?
N1 C16 C17 113.8(3) . . ?
N1 C16 C24 111.3(3) . . ?
N1 C16 H16 107.6(19) . . ?
C17 C16 H16 110.3(19) . . ?
C24 C16 C17 106.8(3) . . ?
C24 C16 H16 106.9(19) . . ?
C16 C17 H17A 105(2) . . ?
C16 C17 H17B 107(2) . . ?
C18 C17 C16 113.2(3) . . ?
C18 C17 H17A 107(2) . . ?
C18 C17 H17B 110(2) . . ?
H17A C17 H17B 114(3) . . ?
C19 C18 C17 121.0(3) . . ?
C19 C18 C23 118.6(3) . . ?
C23 C18 C17 120.4(3) . . ?
C18 C19 H19 119.0(19) . . ?
C20 C19 C18 120.9(4) . . ?
C20 C19 H19 119.9(19) . . ?
C19 C20 H20 119(3) . . ?
C21 C20 C19 120.1(4) . . ?
C21 C20 H20 121(3) . . ?
C20 C21 C22 119.4(4) . . ?
C20 C21 H21 122(2) . . ?
C22 C21 H21 118(2) . . ?
C21 C22 H22 122(2) . . ?
C23 C22 C21 120.3(4) . . ?
C23 C22 H22 118(2) . . ?
C18 C23 H23 122(2) . . ?
C22 C23 C18 120.6(4) . . ?
C22 C23 H23 117(2) . . ?
O3 C24 C16 113.0(3) . . ?
O4 C24 O3 125.1(3) . . ?
O4 C24 C16 121.8(3) . . ?

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
O3 H3 O4 0.84 1.80 2.634(4) 173.5 2_546
N1 H1 O2 0.84(4) 2.08(4) 2.904(4) 167(3) 1_545

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
N1 C16 C17 C18 -66.6(4) . . . . ?
N1 C16 C24 O3 -49.8(4) . . . . ?
N1 C16 C24 O4 134.2(3) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C1 C6 C7 C8 177.1(4) . . . . ?
C1 C6 C7 C12 -1.0(4) . . . . ?
C1 C13 C14 O1 175.0(3) . . . . ?
C2 C1 C6 C5 0.9(5) . . . . ?
C2 C1 C6 C7 179.7(3) . . . . ?
C2 C1 C13 C12 -180.0(3) . . . . ?
C2 C1 C13 C14 -58.8(5) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C3 C4 C5 C6 -0.1(6) . . . . ?
C4 C5 C6 C1 -0.5(5) . . . . ?
C4 C5 C6 C7 -178.9(4) . . . . ?
C5 C6 C7 C8 -4.3(6) . . . . ?
C5 C6 C7 C12 177.6(4) . . . . ?
C6 C1 C2 C3 -0.7(5) . . . . ?
C6 C1 C13 C12 -3.9(3) . . . . ?
C6 C1 C13 C14 117.3(3) . . . . ?
C6 C7 C8 C9 -177.8(4) . . . . ?
C6 C7 C12 C11 178.9(3) . . . . ?
C6 C7 C12 C13 -1.5(4) . . . . ?
C7 C8 C9 C10 -0.7(6) . . . . ?
C7 C12 C13 C1 3.2(4) . . . . ?
C7 C12 C13 C14 -112.7(3) . . . . ?
C8 C7 C12 C11 0.6(5) . . . . ?
C8 C7 C12 C13 -179.9(3) . . . . ?
C8 C9 C10 C11 0.6(6) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
C10 C11 C12 C7 -0.6(5) . . . . ?
C10 C11 C12 C13 179.9(4) . . . . ?
C11 C12 C13 C1 -177.3(3) . . . . ?
C11 C12 C13 C14 66.8(5) . . . . ?
C12 C7 C8 C9 0.1(6) . . . . ?
C12 C13 C14 O1 -71.9(4) . . . . ?
C13 C1 C2 C3 175.0(3) . . . . ?
C13 C1 C6 C5 -175.6(3) . . . . ?
C13 C1 C6 C7 3.2(4) . . . . ?
C14 O1 C15 O2 -4.8(5) . . . . ?
C14 O1 C15 N1 175.0(3) . . . . ?
C15 O1 C14 C13 175.1(3) . . . . ?
C15 N1 C16 C17 115.2(4) . . . . ?
C15 N1 C16 C24 -124.2(3) . . . . ?
C16 N1 C15 O1 -179.2(3) . . . . ?
C16 N1 C15 O2 0.6(5) . . . . ?
C16 C17 C18 C19 86.5(4) . . . . ?
C16 C17 C18 C23 -94.6(4) . . . . ?
C17 C16 C24 O3 74.9(4) . . . . ?
C17 C16 C24 O4 -101.0(4) . . . . ?
C17 C18 C19 C20 179.0(3) . . . . ?
C17 C18 C23 C22 -179.7(3) . . . . ?
C18 C19 C20 C21 1.1(5) . . . . ?
C19 C18 C23 C22 -0.7(5) . . . . ?
C19 C20 C21 C22 -1.5(5) . . . . ?
C20 C21 C22 C23 0.8(5) . . . . ?
C21 C22 C23 C18 0.3(5) . . . . ?
C23 C18 C19 C20 0.1(5) . . . . ?
C24 C16 C17 C18 170.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_DA_FmocF_MeOH_100K
_database_code_depnum_ccdc_archive 'CCDC 1060777'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2015-06-11 downloaded from the CCDC.
;
_audit_creation_date             2015-04-20
_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        ?
_chemical_formula_moiety         'C24 H21 N O4, 2(C H4 O)'
_chemical_formula_sum            'C26 H29 N O6'
_chemical_formula_weight         451.50
_chemical_absolute_configuration L
_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'
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                   13.076(6)
_cell_length_b                   4.887(2)
_cell_length_c                   18.998(9)
_cell_angle_alpha                90
_cell_angle_beta                 106.417(11)
_cell_angle_gamma                90
_cell_volume                     1164.4(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1653
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      19.47
_cell_measurement_theta_min      2.22
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7447
_exptl_absorpt_correction_T_min  0.4759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1408 before and 0.0950 after correction.
The Ratio of minimum to maximum transmission is 0.6390.
The λ/2 correction factor is 0.0000.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1336
_diffrn_reflns_av_unetI/netI     0.0956
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16474
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        21.935
_diffrn_reflns_theta_max         21.935
_diffrn_reflns_theta_min         1.691
_diffrn_ambient_temperature      100.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                2138
_reflns_number_total             2788
_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.

  Diffraction anisotropy and poor single crystal quality 
 account for the higher than estimated 
 _exptl_absorpt_correction_T_max/_exptl_absorpt_correction
 _T_min ratio of 0.7447/0.4759.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_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    ?
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.125
_refine_ls_abs_structure_details 
;
 Flack x determined using 744 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         2788
_refine_ls_number_restraints     253
_refine_ls_R_factor_all          0.1548
_refine_ls_R_factor_gt           0.1269
_refine_ls_restrained_S_all      1.098
_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)+(0.1533P)²+8.4284P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3191
_refine_ls_wR_factor_ref         0.3389
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C24) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(N1)
\\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4.a Ternary CH refined with riding coordinates:
 C13(H13), C16(H16)
4.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C18(H18A,H18B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3A), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
4.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
4.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O5(H5A), O6(H6)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.7105(8) 0.4536(19) 0.2081(6) 0.027(2) Uani 1 1 d . U . . .
O2 O 0.5968(8) 0.794(2) 0.2088(6) 0.037(3) Uani 1 1 d . U . . .
O3 O 0.3708(10) 0.388(3) 0.3388(7) 0.052(3) Uani 1 1 d . U . . .
H3 H 0.3665 0.3089 0.3770 0.077 Uiso 1 1 calc GR . . . .
O4 O 0.5103(10) 0.114(3) 0.3526(7) 0.051(3) Uani 1 1 d . U . . .
N1 N 0.5629(9) 0.356(3) 0.2371(6) 0.026(2) Uani 1 1 d . U . . .
H1 H 0.5883 0.1880 0.2434 0.031 Uiso 1 1 calc R . . . .
C1 C 0.9495(12) 0.498(3) 0.2724(9) 0.031(3) Uani 1 1 d . U . . .
C2 C 0.9335(13) 0.337(4) 0.3283(9) 0.035(3) Uani 1 1 d . U . . .
H2 H 0.8742 0.2166 0.3192 0.042 Uiso 1 1 calc R . . . .
C3 C 1.0046(14) 0.354(4) 0.3974(10) 0.045(4) Uani 1 1 d . U . . .
H3A H 0.9939 0.2407 0.4353 0.054 Uiso 1 1 calc R . . . .
C4 C 1.0883(15) 0.525(4) 0.4129(11) 0.047(4) Uani 1 1 d . U . . .
H4 H 1.1362 0.5304 0.4609 0.056 Uiso 1 1 calc R . . . .
C5 C 1.1048(14) 0.700(4) 0.3558(9) 0.042(4) Uani 1 1 d . U . . .
H5 H 1.1617 0.8282 0.3665 0.050 Uiso 1 1 calc R . . . .
C6 C 1.0396(13) 0.680(4) 0.2881(9) 0.036(3) Uani 1 1 d . U . . .
C7 C 1.0378(12) 0.822(3) 0.2198(9) 0.034(3) Uani 1 1 d . U . . .
C8 C 1.1033(13) 1.029(3) 0.2068(10) 0.035(3) Uani 1 1 d . U . . .
H8 H 1.1599 1.1022 0.2452 0.042 Uiso 1 1 calc R . . . .
C9 C 1.0825(13) 1.121(4) 0.1360(9) 0.035(4) Uani 1 1 d . U . . .
H9 H 1.1293 1.2546 0.1258 0.043 Uiso 1 1 calc R . . . .
C10 C 1.0000(12) 1.036(3) 0.0796(10) 0.033(3) Uani 1 1 d . U . . .
H10 H 0.9880 1.1136 0.0320 0.039 Uiso 1 1 calc R . . . .
C11 C 0.9314(12) 0.828(3) 0.0930(9) 0.029(3) Uani 1 1 d . U . . .
H11 H 0.8740 0.7594 0.0543 0.034 Uiso 1 1 calc R . . . .
C12 C 0.9501(12) 0.728(3) 0.1629(9) 0.027(3) Uani 1 1 d . U . . .
C13 C 0.8869(11) 0.521(3) 0.1937(9) 0.027(3) Uani 1 1 d . U . . .
H13 H 0.8822 0.3405 0.1681 0.033 Uiso 1 1 calc R . . . .
C14 C 0.7769(12) 0.648(3) 0.1821(9) 0.030(3) Uani 1 1 d . U . . .
H14A H 0.7828 0.8215 0.2097 0.036 Uiso 1 1 calc R . . . .
H14B H 0.7444 0.6872 0.1294 0.036 Uiso 1 1 calc R . . . .
C15 C 0.6193(12) 0.556(3) 0.2165(9) 0.028(3) Uani 1 1 d . U . . .
C16 C 0.4591(12) 0.418(4) 0.2490(9) 0.032(3) Uani 1 1 d . U . . .
H16 H 0.4502 0.6204 0.2514 0.039 Uiso 1 1 calc R . . . .
C17 C 0.4532(13) 0.290(4) 0.3194(9) 0.039(3) Uani 1 1 d . U . . .
C18 C 0.3685(12) 0.299(4) 0.1871(8) 0.030(3) Uani 1 1 d . U . . .
H18A H 0.3797 0.0995 0.1854 0.036 Uiso 1 1 calc R . . . .
H18B H 0.3010 0.3279 0.1999 0.036 Uiso 1 1 calc R . . . .
C19 C 0.3549(13) 0.410(4) 0.1130(8) 0.034(3) Uani 1 1 d . U . . .
C20 C 0.4132(13) 0.313(4) 0.0668(8) 0.033(3) Uani 1 1 d . U . . .
H20 H 0.4634 0.1702 0.0838 0.040 Uiso 1 1 calc R . . . .
C21 C 0.4006(12) 0.417(3) -0.0017(9) 0.031(3) Uani 1 1 d . U . . .
H21 H 0.4398 0.3408 -0.0321 0.037 Uiso 1 1 calc R . . . .
C22 C 0.3311(12) 0.631(4) -0.0272(9) 0.033(3) Uani 1 1 d . U . . .
H22 H 0.3222 0.7041 -0.0749 0.040 Uiso 1 1 calc R . . . .
C23 C 0.2750(13) 0.737(3) 0.0179(9) 0.035(4) Uani 1 1 d . U . . .
H23 H 0.2275 0.8846 0.0004 0.042 Uiso 1 1 calc R . . . .
C24 C 0.2849(13) 0.639(4) 0.0861(8) 0.034(3) Uani 1 1 d . U . . .
H24 H 0.2460 0.7196 0.1161 0.041 Uiso 1 1 calc R . . . .
O5 O 0.6661(11) 0.648(3) 0.5524(7) 0.058(4) Uiso 1 1 d . U . . .
H5A H 0.6986 0.7032 0.5228 0.087 Uiso 1 1 calc GR . . . .
C25 C 0.6106(16) 0.391(5) 0.5254(11) 0.059(6) Uiso 1 1 d . U . . .
H25A H 0.6007 0.2855 0.5669 0.088 Uiso 1 1 calc GR . . . .
H25B H 0.6532 0.2841 0.5003 0.088 Uiso 1 1 calc GR . . . .
H25C H 0.5409 0.4317 0.4910 0.088 Uiso 1 1 calc GR . . . .
O6 O 0.7025(10) 0.878(3) 0.4318(7) 0.053(3) Uiso 1 1 d . U . . .
H6 H 0.6491 0.9386 0.3998 0.080 Uiso 1 1 calc GR . . . .
C26 C 0.7625(15) 0.721(4) 0.3987(10) 0.046(5) Uiso 1 1 d . U . . .
H26A H 0.8338 0.6946 0.4326 0.068 Uiso 1 1 calc GR . . . .
H26B H 0.7684 0.8129 0.3543 0.068 Uiso 1 1 calc GR . . . .
H26C H 0.7282 0.5422 0.3857 0.068 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
O1 C14 1.462(18) . ?
O1 C15 1.342(18) . ?
O2 C15 1.201(18) . ?
O3 H3 0.8400 . ?
O3 C17 1.32(2) . ?
O4 C17 1.20(2) . ?
N1 H1 0.8800 . ?
N1 C15 1.35(2) . ?
N1 C16 1.469(19) . ?
C1 C2 1.38(2) . ?
C1 C6 1.44(2) . ?
C1 C13 1.49(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.38(2) . ?
C3 H3A 0.9500 . ?
C3 C4 1.34(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.45(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.33(2) . ?
C6 C7 1.47(2) . ?
C7 C8 1.39(2) . ?
C7 C12 1.41(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.37(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.35(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.43(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.37(2) . ?
C12 C13 1.52(2) . ?
C13 H13 1.0000 . ?
C13 C14 1.52(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C16 H16 1.0000 . ?
C16 C17 1.50(2) . ?
C16 C18 1.53(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.47(2) . ?
C19 C20 1.40(2) . ?
C19 C24 1.44(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.36(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.38(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.38(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.35(2) . ?
C24 H24 0.9500 . ?
O5 H5A 0.8400 . ?
O5 C25 1.47(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
O6 H6 0.8400 . ?
O6 C26 1.37(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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
C15 O1 C14 115.5(11) . . ?
C17 O3 H3 109.5 . . ?
C15 N1 H1 120.0 . . ?
C15 N1 C16 120.1(13) . . ?
C16 N1 H1 120.0 . . ?
C2 C1 C6 119.0(15) . . ?
C2 C1 C13 130.8(15) . . ?
C6 C1 C13 110.2(13) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.3(16) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3A 118.9 . . ?
C4 C3 C2 122.3(17) . . ?
C4 C3 H3A 118.9 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.3(18) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.5(17) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C7 107.6(14) . . ?
C5 C6 C1 120.5(16) . . ?
C5 C6 C7 131.8(17) . . ?
C8 C7 C6 130.1(16) . . ?
C8 C7 C12 120.7(15) . . ?
C12 C7 C6 109.1(14) . . ?
C7 C8 H8 121.6 . . ?
C9 C8 C7 116.9(16) . . ?
C9 C8 H8 121.6 . . ?
C8 C9 H9 117.7 . . ?
C10 C9 C8 124.6(16) . . ?
C10 C9 H9 117.7 . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.5(16) . . ?
C11 C10 H10 120.7 . . ?
C10 C11 H11 120.7 . . ?
C12 C11 C10 118.6(15) . . ?
C12 C11 H11 120.7 . . ?
C7 C12 C13 109.6(13) . . ?
C11 C12 C7 120.5(14) . . ?
C11 C12 C13 129.9(14) . . ?
C1 C13 C12 103.4(12) . . ?
C1 C13 H13 111.3 . . ?
C1 C13 C14 113.8(12) . . ?
C12 C13 H13 111.3 . . ?
C12 C13 C14 105.5(12) . . ?
C14 C13 H13 111.3 . . ?
O1 C14 C13 108.2(12) . . ?
O1 C14 H14A 110.1 . . ?
O1 C14 H14B 110.1 . . ?
C13 C14 H14A 110.1 . . ?
C13 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
O1 C15 N1 110.0(13) . . ?
O2 C15 O1 122.8(14) . . ?
O2 C15 N1 127.1(14) . . ?
N1 C16 H16 109.6 . . ?
N1 C16 C17 109.6(13) . . ?
N1 C16 C18 110.7(12) . . ?
C17 C16 H16 109.6 . . ?
C17 C16 C18 107.8(13) . . ?
C18 C16 H16 109.6 . . ?
O3 C17 C16 110.5(15) . . ?
O4 C17 O3 123.4(16) . . ?
O4 C17 C16 126.0(16) . . ?
C16 C18 H18A 108.0 . . ?
C16 C18 H18B 108.0 . . ?
H18A C18 H18B 107.2 . . ?
C19 C18 C16 117.2(14) . . ?
C19 C18 H18A 108.0 . . ?
C19 C18 H18B 108.0 . . ?
C20 C19 C18 122.5(15) . . ?
C20 C19 C24 116.3(14) . . ?
C24 C19 C18 121.0(14) . . ?
C19 C20 H20 118.8 . . ?
C21 C20 C19 122.3(16) . . ?
C21 C20 H20 118.8 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.5(16) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 120.7 . . ?
C23 C22 C21 118.6(15) . . ?
C23 C22 H22 120.7 . . ?
C22 C23 H23 118.6 . . ?
C24 C23 C22 122.7(16) . . ?
C24 C23 H23 118.6 . . ?
C19 C24 H24 120.3 . . ?
C23 C24 C19 119.5(15) . . ?
C23 C24 H24 120.3 . . ?
C25 O5 H5A 109.5 . . ?
O5 C25 H25A 109.5 . . ?
O5 C25 H25B 109.5 . . ?
O5 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C26 O6 H6 109.5 . . ?
O6 C26 H26A 109.5 . . ?
O6 C26 H26B 109.5 . . ?
O6 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

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
O3 H3 O5 0.84 1.71 2.539(18) 169.9 2_646
N1 H1 O2 0.88 2.05 2.855(17) 152.2 1_545
O5 H5A O6 0.84 1.94 2.711(19) 152.1 .
O6 H6 O4 0.84 1.98 2.789(19) 161.9 1_565

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
N1 C16 C17 O3 167.2(14) . . . . ?
N1 C16 C17 O4 -17(2) . . . . ?
N1 C16 C18 C19 -63.9(19) . . . . ?
C1 C2 C3 C4 1(3) . . . . ?
C1 C6 C7 C8 175.9(16) . . . . ?
C1 C6 C7 C12 -1.0(19) . . . . ?
C1 C13 C14 O1 -69.5(16) . . . . ?
C2 C1 C6 C5 -2(2) . . . . ?
C2 C1 C6 C7 179.6(15) . . . . ?
C2 C1 C13 C12 -178.4(16) . . . . ?
C2 C1 C13 C14 68(2) . . . . ?
C2 C3 C4 C5 1(3) . . . . ?
C3 C4 C5 C6 -3(3) . . . . ?
C4 C5 C6 C1 4(3) . . . . ?
C4 C5 C6 C7 -178.3(18) . . . . ?
C5 C6 C7 C8 -2(3) . . . . ?
C5 C6 C7 C12 -179(2) . . . . ?
C6 C1 C2 C3 -1(2) . . . . ?
C6 C1 C13 C12 1.8(16) . . . . ?
C6 C1 C13 C14 -112.0(15) . . . . ?
C6 C7 C8 C9 179.5(17) . . . . ?
C6 C7 C12 C11 -179.4(15) . . . . ?
C6 C7 C12 C13 2.2(18) . . . . ?
C7 C8 C9 C10 4(3) . . . . ?
C7 C12 C13 C1 -2.4(16) . . . . ?
C7 C12 C13 C14 117.3(14) . . . . ?
C8 C7 C12 C11 3(2) . . . . ?
C8 C7 C12 C13 -175.0(14) . . . . ?
C8 C9 C10 C11 -3(3) . . . . ?
C9 C10 C11 C12 2(2) . . . . ?
C10 C11 C12 C7 -2(2) . . . . ?
C10 C11 C12 C13 175.9(14) . . . . ?
C11 C12 C13 C1 179.3(15) . . . . ?
C11 C12 C13 C14 -61(2) . . . . ?
C12 C7 C8 C9 -4(2) . . . . ?
C12 C13 C14 O1 177.9(12) . . . . ?
C13 C1 C2 C3 179.7(16) . . . . ?
C13 C1 C6 C5 177.9(17) . . . . ?
C13 C1 C6 C7 -0.7(18) . . . . ?
C14 O1 C15 O2 -6(2) . . . . ?
C14 O1 C15 N1 177.1(12) . . . . ?
C15 O1 C14 C13 166.2(13) . . . . ?
C15 N1 C16 C17 -133.8(15) . . . . ?
C15 N1 C16 C18 107.4(16) . . . . ?
C16 N1 C15 O1 -179.4(12) . . . . ?
C16 N1 C15 O2 3(3) . . . . ?
C16 C18 C19 C20 84(2) . . . . ?
C16 C18 C19 C24 -91.5(19) . . . . ?
C17 C16 C18 C19 176.2(15) . . . . ?
C18 C16 C17 O3 -72.3(18) . . . . ?
C18 C16 C17 O4 104(2) . . . . ?
C18 C19 C20 C21 -179.7(16) . . . . ?
C18 C19 C24 C23 179.3(16) . . . . ?
C19 C20 C21 C22 2(2) . . . . ?
C20 C19 C24 C23 3(2) . . . . ?
C20 C21 C22 C23 0(2) . . . . ?
C21 C22 C23 C24 0(2) . . . . ?
C22 C23 C24 C19 -1(2) . . . . ?
C24 C19 C20 C21 -4(2) . . . . ?

#==============================================================================
# start Validation Reply Form
#==============================================================================

_THETM01_ALERT_3_A               
;
Problem: The value of sine(theta_max)/wavelength is less than 0.550
Calculated sin(theta_max)/wavelength = 0.5256
Response: Single crystals of FmocF_MeOH were weakly diffracting, diffuse 
scatter beyond 0.95 angstroms was omitted during refinement.    
;

_PLAT340_ALERT_3_B               
;
Problem: Low Bond Precision on C-C Bonds ............... 0.0212 Ang.
Response: Low bond precision is related to quality of the diffraction data. 
;

#==============================================================================
# end Validation Reply Form
#==============================================================================

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_fmoc-l-tyrosine
_database_code_depnum_ccdc_archive 'CCDC 1060778'
_audit_update_record             
;
2015-05-28 deposited with the CCDC.
2015-06-11 downloaded from the CCDC.
;
_audit_creation_date             2015-04-14
_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        ?
_chemical_formula_moiety         'C24 H21 N O5, H2 O'
_chemical_formula_sum            'C24 H23 N O6'
_chemical_formula_weight         421.43
_chemical_absolute_configuration L
_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 0.0030 0.0010 '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'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   18.640(16)
_cell_length_b                   5.992(5)
_cell_length_c                   18.841(15)
_cell_angle_alpha                90
_cell_angle_beta                 98.834(16)
_cell_angle_gamma                90
_cell_volume                     2079(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4804
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.500
_cell_measurement_theta_min      2.230
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1039 before and 0.0602 after correction.
The Ratio of minimum to maximum transmission is 0.7505.
The λ/2 correction factor is 0.0000.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_Laue_measured_fraction_full 0.926
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7927
_diffrn_reflns_point_group_measured_fraction_full 0.818
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.625
_diffrn_reflns_theta_min         1.060
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 0.0350
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.926
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device       'CrystalLogic Kappa (4 circle)'
_diffrn_measurement_device_type  'Kappa Rigaku Saturn724+'
_diffrn_measurement_method       'omega rotation'
_diffrn_radiation_collimation    '0.3 x 1.5 Double Pinhole'
_diffrn_radiation_monochromator  'Synchrotron '
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.6889
_diffrn_source                   Synchrotron
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_reflns_Friedel_coverage         0.611
_reflns_Friedel_fraction_full    0.687
_reflns_Friedel_fraction_max     0.720
_reflns_number_gt                3578
_reflns_number_total             3700
_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.

 Radiation damage was clearly evident during the data 
 collection. Scaling was important for data treatment and
 the Rint was lowered from 0.1039 to 0.0602 after treatment
 by SADABS.

;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_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         0.277
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 1336 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         3700
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.106
_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)+(0.0417P)²+0.7481P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0907
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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 0.29678(7) 0.8883(3) 0.24541(8) 0.0166(4) Uani 1 1 d . . . . .
O2 O 0.24561(8) 0.5449(3) 0.24793(8) 0.0174(4) Uani 1 1 d . . . . .
O3 O 0.48866(8) 0.4611(3) 0.18979(8) 0.0182(4) Uani 1 1 d . . . . .
O4 O 0.46490(8) 0.1011(3) 0.20956(8) 0.0202(4) Uani 1 1 d . . . . .
H4 H 0.5161(18) 0.075(7) 0.2056(17) 0.040(9) Uiso 1 1 d . . . . .
O5 O 0.40377(8) 0.6157(3) -0.12143(8) 0.0220(4) Uani 1 1 d . . . . .
H5 H 0.4380(16) 0.528(6) -0.1367(15) 0.025(7) Uiso 1 1 d . . . . .
O6 O 0.09668(8) 0.5199(4) 0.19161(9) 0.0221(4) Uani 1 1 d . . . . .
H6A H 0.100(2) 0.385(8) 0.170(2) 0.049(11) Uiso 1 1 d . . . . .
H6B H 0.144(2) 0.531(8) 0.218(2) 0.050(10) Uiso 1 1 d . . . . .
N1 N 0.35812(9) 0.5911(4) 0.21756(9) 0.0150(4) Uani 1 1 d . . . . .
H1 H 0.3931(17) 0.688(6) 0.2077(15) 0.025(7) Uiso 1 1 d . . . . .
C1 C 0.29215(11) 1.1531(4) 0.38211(10) 0.0161(5) Uani 1 1 d . . . . .
C2 C 0.36726(11) 1.1334(5) 0.38792(11) 0.0181(5) Uani 1 1 d . . . . .
H2 H 0.3907(14) 1.004(6) 0.3671(14) 0.019(6) Uiso 1 1 d . . . . .
C3 C 0.41049(11) 1.3017(4) 0.42365(11) 0.0189(5) Uani 1 1 d . . . . .
H3 H 0.4607(15) 1.284(6) 0.4276(14) 0.021(7) Uiso 1 1 d . . . . .
C4 C 0.38010(11) 1.4837(4) 0.45357(11) 0.0190(5) Uani 1 1 d . . . . .
H4A H 0.4096(15) 1.606(6) 0.4782(15) 0.022(7) Uiso 1 1 d . . . . .
C5 C 0.30490(11) 1.5033(5) 0.44807(11) 0.0175(5) Uani 1 1 d . . . . .
H5A H 0.2829(13) 1.623(5) 0.4687(13) 0.012(6) Uiso 1 1 d . . . . .
C6 C 0.26201(10) 1.3379(4) 0.41186(10) 0.0150(5) Uani 1 1 d . . . . .
C7 C 0.18217(10) 1.3176(4) 0.39741(10) 0.0161(5) Uani 1 1 d . . . . .
C8 C 0.12809(12) 1.4548(5) 0.41652(12) 0.0196(5) Uani 1 1 d . . . . .
H8 H 0.1419(14) 1.592(6) 0.4440(14) 0.018(6) Uiso 1 1 d . . . . .
C9 C 0.05633(12) 1.3909(5) 0.39603(12) 0.0228(6) Uani 1 1 d . . . . .
H9 H 0.0195(16) 1.475(6) 0.4091(15) 0.025(7) Uiso 1 1 d . . . . .
C10 C 0.03889(12) 1.1933(5) 0.35815(12) 0.0221(5) Uani 1 1 d . . . . .
H10 H -0.0107(18) 1.158(6) 0.3457(17) 0.033(8) Uiso 1 1 d . . . . .
C11 C 0.09298(11) 1.0542(5) 0.33968(11) 0.0194(5) Uani 1 1 d . . . . .
H11 H 0.0812(15) 0.907(6) 0.3131(16) 0.025(7) Uiso 1 1 d . . . . .
C12 C 0.16477(11) 1.1176(4) 0.35980(10) 0.0160(5) Uani 1 1 d . . . . .
C13 C 0.23303(10) 1.0005(4) 0.34475(11) 0.0153(5) Uani 1 1 d . . . . .
H13 H 0.2381(14) 0.839(5) 0.3667(14) 0.016(6) Uiso 1 1 d . . . . .
C14 C 0.23141(11) 0.9894(5) 0.26359(11) 0.0164(5) Uani 1 1 d . . . . .
H14A H 0.1864(14) 0.905(5) 0.2427(14) 0.015(6) Uiso 1 1 d . . . . .
H14B H 0.2298(14) 1.150(6) 0.2428(14) 0.017(6) Uiso 1 1 d . . . . .
C15 C 0.29611(10) 0.6648(4) 0.23791(10) 0.0142(5) Uani 1 1 d . . . . .
C16 C 0.36784(10) 0.3554(4) 0.20504(11) 0.0144(5) Uani 1 1 d . . . . .
H16 H 0.3554(13) 0.258(5) 0.2459(13) 0.011(6) Uiso 1 1 d . . . . .
C17 C 0.44744(11) 0.3128(4) 0.20116(10) 0.0153(5) Uani 1 1 d . . . . .
C18 C 0.32116(10) 0.2699(5) 0.13489(10) 0.0156(5) Uani 1 1 d . . . . .
H18A H 0.2720(14) 0.308(5) 0.1420(13) 0.014(6) Uiso 1 1 d . . . . .
H18B H 0.3242(13) 0.104(6) 0.1340(14) 0.016(6) Uiso 1 1 d . . . . .
C19 C 0.34293(10) 0.3626(4) 0.06696(11) 0.0149(4) Uani 1 1 d . . . . .
C20 C 0.31996(10) 0.5717(4) 0.04036(11) 0.0163(5) Uani 1 1 d . . . . .
H20 H 0.2866(14) 0.667(5) 0.0657(14) 0.016(6) Uiso 1 1 d . . . . .
C21 C 0.34131(11) 0.6559(5) -0.02209(11) 0.0172(5) Uani 1 1 d . . . . .
H21 H 0.3286(15) 0.802(6) -0.0400(15) 0.024(7) Uiso 1 1 d . . . . .
C22 C 0.38527(10) 0.5273(4) -0.05894(10) 0.0170(5) Uani 1 1 d . . . . .
C23 C 0.40825(11) 0.3178(4) -0.03434(11) 0.0179(5) Uani 1 1 d . . . . .
H23 H 0.4414(17) 0.227(6) -0.0604(17) 0.032(8) Uiso 1 1 d . . . . .
C24 C 0.38745(11) 0.2379(5) 0.02883(11) 0.0172(5) Uani 1 1 d . . . . .
H24 H 0.4021(14) 0.089(6) 0.0461(14) 0.019(6) Uiso 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
O1 C14 1.448(3) . ?
O1 C15 1.347(3) . ?
O2 C15 1.222(3) . ?
O3 C17 1.215(3) . ?
O4 H4 0.98(3) . ?
O4 C17 1.313(3) . ?
O5 H5 0.91(3) . ?
O5 C22 1.382(3) . ?
O6 H6A 0.91(5) . ?
O6 H6B 0.95(4) . ?
N1 H1 0.91(3) . ?
N1 C15 1.347(3) . ?
N1 C16 1.448(4) . ?
C1 C2 1.393(3) . ?
C1 C6 1.397(3) . ?
C1 C13 1.519(3) . ?
C2 H2 1.00(3) . ?
C2 C3 1.398(3) . ?
C3 H3 0.93(3) . ?
C3 C4 1.388(4) . ?
C4 H4A 0.99(3) . ?
C4 C5 1.394(3) . ?
C5 H5A 0.94(3) . ?
C5 C6 1.385(3) . ?
C6 C7 1.476(3) . ?
C7 C8 1.390(3) . ?
C7 C12 1.405(4) . ?
C8 H8 0.99(3) . ?
C8 C9 1.388(3) . ?
C9 H9 0.91(3) . ?
C9 C10 1.395(4) . ?
C10 H10 0.94(3) . ?
C10 C11 1.393(4) . ?
C11 H11 1.02(4) . ?
C11 C12 1.387(3) . ?
C12 C13 1.517(3) . ?
C13 H13 1.05(3) . ?
C13 C14 1.526(3) . ?
C14 H14A 1.01(3) . ?
C14 H14B 1.04(3) . ?
C16 H16 1.02(3) . ?
C16 C17 1.518(3) . ?
C16 C18 1.554(3) . ?
C18 H18A 0.97(3) . ?
C18 H18B 1.00(3) . ?
C18 C19 1.507(3) . ?
C19 C20 1.393(4) . ?
C19 C24 1.395(3) . ?
C20 H20 1.02(3) . ?
C20 C21 1.393(3) . ?
C21 H21 0.95(4) . ?
C21 C22 1.387(3) . ?
C22 C23 1.383(4) . ?
C23 H23 1.01(3) . ?
C23 C24 1.392(3) . ?
C24 H24 0.97(3) . ?

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
C15 O1 C14 116.50(18) . . ?
C17 O4 H4 112(2) . . ?
C22 O5 H5 109(2) . . ?
H6A O6 H6B 100(4) . . ?
C15 N1 H1 121(2) . . ?
C15 N1 C16 120.04(19) . . ?
C16 N1 H1 118(2) . . ?
C2 C1 C6 119.8(2) . . ?
C2 C1 C13 129.4(2) . . ?
C6 C1 C13 110.80(19) . . ?
C1 C2 H2 122.0(16) . . ?
C1 C2 C3 118.3(2) . . ?
C3 C2 H2 119.7(16) . . ?
C2 C3 H3 117(2) . . ?
C4 C3 C2 121.5(2) . . ?
C4 C3 H3 122(2) . . ?
C3 C4 H4A 122.9(17) . . ?
C3 C4 C5 120.3(2) . . ?
C5 C4 H4A 116.9(17) . . ?
C4 C5 H5A 122.1(16) . . ?
C6 C5 C4 118.3(2) . . ?
C6 C5 H5A 119.6(16) . . ?
C1 C6 C7 108.5(2) . . ?
C5 C6 C1 121.81(19) . . ?
C5 C6 C7 129.7(2) . . ?
C8 C7 C6 130.8(2) . . ?
C8 C7 C12 121.0(2) . . ?
C12 C7 C6 108.15(19) . . ?
C7 C8 H8 119.3(15) . . ?
C9 C8 C7 118.1(2) . . ?
C9 C8 H8 122.6(15) . . ?
C8 C9 H9 120(2) . . ?
C8 C9 C10 121.0(2) . . ?
C10 C9 H9 119(2) . . ?
C9 C10 H10 117(2) . . ?
C11 C10 C9 121.0(2) . . ?
C11 C10 H10 122(2) . . ?
C10 C11 H11 122.0(16) . . ?
C12 C11 C10 118.2(2) . . ?
C12 C11 H11 119.8(16) . . ?
C7 C12 C13 110.70(18) . . ?
C11 C12 C7 120.7(2) . . ?
C11 C12 C13 128.6(2) . . ?
C1 C13 H13 110.9(14) . . ?
C1 C13 C14 113.06(18) . . ?
C12 C13 C1 101.8(2) . . ?
C12 C13 H13 112.3(14) . . ?
C12 C13 C14 108.62(16) . . ?
C14 C13 H13 109.9(15) . . ?
O1 C14 C13 111.55(17) . . ?
O1 C14 H14A 112.2(16) . . ?
O1 C14 H14B 105.9(15) . . ?
C13 C14 H14A 107.5(15) . . ?
C13 C14 H14B 109.5(15) . . ?
H14A C14 H14B 110(2) . . ?
O1 C15 N1 111.19(19) . . ?
O2 C15 O1 124.30(19) . . ?
O2 C15 N1 124.5(2) . . ?
N1 C16 H16 112.7(16) . . ?
N1 C16 C17 108.64(18) . . ?
N1 C16 C18 113.13(19) . . ?
C17 C16 H16 106.1(14) . . ?
C17 C16 C18 109.11(17) . . ?
C18 C16 H16 106.9(15) . . ?
O3 C17 O4 125.19(19) . . ?
O3 C17 C16 122.3(2) . . ?
O4 C17 C16 112.49(19) . . ?
C16 C18 H18A 102.8(16) . . ?
C16 C18 H18B 108.5(15) . . ?
H18A C18 H18B 107(2) . . ?
C19 C18 C16 114.34(19) . . ?
C19 C18 H18A 114.4(16) . . ?
C19 C18 H18B 109.2(15) . . ?
C20 C19 C18 122.0(2) . . ?
C20 C19 C24 118.1(2) . . ?
C24 C19 C18 119.9(2) . . ?
C19 C20 H20 120.9(16) . . ?
C19 C20 C21 121.2(2) . . ?
C21 C20 H20 117.9(16) . . ?
C20 C21 H21 122.8(17) . . ?
C22 C21 C20 119.3(2) . . ?
C22 C21 H21 117.8(17) . . ?
O5 C22 C21 117.2(2) . . ?
O5 C22 C23 121.9(2) . . ?
C23 C22 C21 120.9(2) . . ?
C22 C23 H23 121(2) . . ?
C22 C23 C24 119.1(2) . . ?
C24 C23 H23 120(2) . . ?
C19 C24 H24 118.5(16) . . ?
C23 C24 C19 121.5(2) . . ?
C23 C24 H24 120.0(16) . . ?

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
O4 H4 O6 0.98(3) 1.60(3) 2.577(3) 174(3) 3_545
O5 H5 O3 0.91(3) 1.86(3) 2.708(3) 155(3) 2_655
O6 H6A O5 0.91(5) 1.85(5) 2.759(3) 173(4) 4_545
O6 H6B O2 0.95(4) 1.89(4) 2.820(3) 166(3) .
N1 H1 O4 0.91(3) 2.81(3) 3.663(4) 156(3) 1_565

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
O5 C22 C23 C24 -179.70(19) . . . . ?
N1 C16 C17 O3 -19.0(3) . . . . ?
N1 C16 C17 O4 162.58(17) . . . . ?
N1 C16 C18 C19 67.1(2) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C1 C6 C7 C8 178.9(2) . . . . ?
C1 C6 C7 C12 0.9(2) . . . . ?
C1 C13 C14 O1 65.2(3) . . . . ?
C2 C1 C6 C5 -0.7(3) . . . . ?
C2 C1 C6 C7 179.48(19) . . . . ?
C2 C1 C13 C12 179.4(2) . . . . ?
C2 C1 C13 C14 -64.3(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C1 0.9(3) . . . . ?
C4 C5 C6 C7 -179.3(2) . . . . ?
C5 C6 C7 C8 -1.0(4) . . . . ?
C5 C6 C7 C12 -178.9(2) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
C6 C1 C13 C12 -2.3(2) . . . . ?
C6 C1 C13 C14 114.0(2) . . . . ?
C6 C7 C8 C9 -179.1(2) . . . . ?
C6 C7 C12 C11 179.3(2) . . . . ?
C6 C7 C12 C13 -2.5(2) . . . . ?
C7 C8 C9 C10 0.8(4) . . . . ?
C7 C12 C13 C1 2.9(2) . . . . ?
C7 C12 C13 C14 -116.6(2) . . . . ?
C8 C7 C12 C11 1.2(3) . . . . ?
C8 C7 C12 C13 179.3(2) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C10 C11 C12 C7 -0.4(3) . . . . ?
C10 C11 C12 C13 -178.2(2) . . . . ?
C11 C12 C13 C1 -179.1(2) . . . . ?
C11 C12 C13 C14 61.4(3) . . . . ?
C12 C7 C8 C9 -1.3(3) . . . . ?
C12 C13 C14 O1 177.39(19) . . . . ?
C13 C1 C2 C3 178.0(2) . . . . ?
C13 C1 C6 C5 -179.18(19) . . . . ?
C13 C1 C6 C7 1.0(2) . . . . ?
C14 O1 C15 O2 -2.7(3) . . . . ?
C14 O1 C15 N1 176.92(16) . . . . ?
C15 O1 C14 C13 88.8(2) . . . . ?
C15 N1 C16 C17 -166.17(17) . . . . ?
C15 N1 C16 C18 72.5(2) . . . . ?
C16 N1 C15 O1 -178.73(16) . . . . ?
C16 N1 C15 O2 0.9(3) . . . . ?
C16 C18 C19 C20 -82.0(2) . . . . ?
C16 C18 C19 C24 98.0(3) . . . . ?
C17 C16 C18 C19 -54.0(3) . . . . ?
C18 C16 C17 O3 104.7(2) . . . . ?
C18 C16 C17 O4 -73.7(2) . . . . ?
C18 C19 C20 C21 179.25(19) . . . . ?
C18 C19 C24 C23 179.60(19) . . . . ?
C19 C20 C21 C22 1.1(3) . . . . ?
C20 C19 C24 C23 -0.5(3) . . . . ?
C20 C21 C22 O5 178.64(18) . . . . ?
C20 C21 C22 C23 -0.3(3) . . . . ?
C21 C22 C23 C24 -0.9(3) . . . . ?
C22 C23 C24 C19 1.2(3) . . . . ?
C24 C19 C20 C21 -0.7(3) . . . . ?

#==============================================================================
# start Validation Reply Form
#==============================================================================

_PLAT018_ALERT_1_B               
;
Problem: _diffrn_measured_fraction_theta_max .NE. _full ! Check     
Response: Due to severe radiation damage two scans, including a fast scan 
were left our during intergration. 
Overall completeness to 0.8 angstroms is 97 %.   
;
#==============================================================================
# end Validation Reply Form
#==============================================================================

_olex2_submission_special_instructions 'No special instructions were received'
