# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_nelson04
_database_code_depnum_ccdc_archive 'CCDC 1437724'
_audit_update_record             
;
2015-11-19 deposited with the CCDC.
2016-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        Nelson04
_chemical_name_common            SSB-10-102
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H39 N O4'
_chemical_formula_weight         561.69

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.4721(7)
_cell_length_b                   20.8688(13)
_cell_length_c                   14.2792(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.592(4)
_cell_angle_gamma                90
_cell_volume                     3085.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4360
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      25.18

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24843
_diffrn_reflns_av_unetI/netI     0.0780
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.952
_diffrn_reflns_theta_max         28.435
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7665
_reflns_number_gt                4826
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0680P)²+0.8700P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7665
_refine_ls_number_parameters     389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1592
_refine_ls_wR_factor_gt          0.1349
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.007
_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
O1 O 0.21646(13) 0.16938(7) 0.30543(9) 0.0226(3) Uani 1 1 d . . . . .
O2 O 0.34702(12) 0.13238(7) 0.47814(9) 0.0211(3) Uani 1 1 d . . . . .
O3 O -0.18676(14) -0.14131(7) 0.30286(10) 0.0288(3) Uani 1 1 d . . . . .
O4 O -0.07964(15) -0.17815(7) 0.44010(11) 0.0328(4) Uani 1 1 d . . . . .
N1 N 0.08719(16) -0.06498(8) 0.44493(11) 0.0222(4) Uani 1 1 d . . . . .
C1 C 0.5453(3) -0.08758(12) 1.07128(14) 0.0378(6) Uani 1 1 d . . . . .
H36 H 0.4512 -0.0916 1.0647 0.057 Uiso 1 1 calc R U . . .
H1 H 0.5688 -0.0422 1.0703 0.057 Uiso 1 1 calc R U . . .
H37 H 0.5846 -0.1067 1.1314 0.057 Uiso 1 1 calc R U . . .
C2 C 0.59470(19) -0.12249(10) 0.98865(13) 0.0220(4) Uani 1 1 d . . . . .
C3 C 0.53583(18) -0.09039(9) 0.89532(13) 0.0192(4) Uani 1 1 d . . . . .
C4 C 0.40172(18) -0.09102(10) 0.86762(13) 0.0225(4) Uani 1 1 d . . . . .
H4 H 0.3486 -0.1121 0.9064 0.027 Uiso 1 1 calc R U . . .
C5 C 0.34464(19) -0.06143(10) 0.78463(14) 0.0243(4) Uani 1 1 d . . . . .
H5 H 0.2535 -0.0627 0.7674 0.029 Uiso 1 1 calc R U . . .
C6 C 0.42042(19) -0.02967(9) 0.72617(13) 0.0207(4) Uani 1 1 d . . . . .
C7 C 0.36059(19) -0.00199(10) 0.63806(13) 0.0229(4) Uani 1 1 d . . . . .
C8 C 0.30532(18) 0.01565(9) 0.56246(13) 0.0207(4) Uani 1 1 d . . . . .
C9 C 0.23589(18) 0.03235(9) 0.47145(12) 0.0188(4) Uani 1 1 d . . . . .
C10 C 0.13933(18) -0.00771(9) 0.42056(13) 0.0185(4) Uani 1 1 d . . . . .
C11 C 0.07571(17) 0.00992(9) 0.32946(13) 0.0188(4) Uani 1 1 d . . . . .
C12 C 0.10284(17) 0.06902(9) 0.28753(12) 0.0173(4) Uani 1 1 d . . . . .
C13 C 0.03787(17) 0.08770(9) 0.19638(13) 0.0198(4) Uani 1 1 d . . . . .
C14 C -0.01479(18) 0.10204(9) 0.11906(13) 0.0198(4) Uani 1 1 d . . . . .
C15 C -0.07752(17) 0.12343(9) 0.02739(13) 0.0191(4) Uani 1 1 d . . . . .
C16 C -0.07914(19) 0.18833(10) 0.00470(13) 0.0219(4) Uani 1 1 d . . . . .
H20 H -0.0358 0.2181 0.0487 0.026 Uiso 1 1 calc R U . . .
C17 C -0.14314(19) 0.20984(10) -0.08125(13) 0.0230(4) Uani 1 1 d . . . . .
H19 H -0.1434 0.2544 -0.0948 0.028 Uiso 1 1 calc R U . . .
C18 C -0.20753(17) 0.16789(9) -0.14891(12) 0.0189(4) Uani 1 1 d . . . . .
C19 C -0.28310(19) 0.19482(10) -0.24104(13) 0.0232(4) Uani 1 1 d . . . . .
C20 C -0.3534(2) 0.14170(12) -0.30303(15) 0.0378(6) Uani 1 1 d . . . . .
H18 H -0.4117 0.1187 -0.2670 0.057 Uiso 1 1 calc R U . . .
H17 H -0.2899 0.1117 -0.3219 0.057 Uiso 1 1 calc R U . . .
H2 H -0.4034 0.1608 -0.3597 0.057 Uiso 1 1 calc R U . . .
C21 C 0.7421(2) -0.12041(14) 1.00378(18) 0.0477(7) Uani 1 1 d . . . . .
H38 H 0.7757 -0.1430 1.0624 0.072 Uiso 1 1 calc R U . . .
H3 H 0.7712 -0.0757 1.0084 0.072 Uiso 1 1 calc R U . . .
H39 H 0.7741 -0.1411 0.9502 0.072 Uiso 1 1 calc R U . . .
C22 C 0.60980(19) -0.05917(9) 0.83596(13) 0.0204(4) Uani 1 1 d . . . . .
H32 H 0.7011 -0.0586 0.8525 0.025 Uiso 1 1 calc R U . . .
C23 C 0.55374(19) -0.02883(9) 0.75312(13) 0.0215(4) Uani 1 1 d . . . . .
H31 H 0.6069 -0.0074 0.7147 0.026 Uiso 1 1 calc R U . . .
C24 C 0.1277(2) -0.10115(12) 0.53191(16) 0.0413(6) Uani 1 1 d . . . . .
H7 H 0.2039 -0.1269 0.5249 0.062 Uiso 1 1 calc R U . . .
H6 H 0.0574 -0.1295 0.5442 0.062 Uiso 1 1 calc R U . . .
H8 H 0.1489 -0.0714 0.5850 0.062 Uiso 1 1 calc R U . . .
C25 C -0.00890(18) -0.08265(10) 0.37134(13) 0.0210(4) Uani 1 1 d . . . . .
C26 C -0.01651(18) -0.03833(9) 0.29975(14) 0.0197(4) Uani 1 1 d . . . . .
H27 H -0.0731 -0.0398 0.2412 0.024 Uiso 1 1 calc R U . . .
C27 C -0.2005(2) 0.10294(10) -0.12711(14) 0.0271(5) Uani 1 1 d . . . . .
H10 H -0.2398 0.0730 -0.1726 0.032 Uiso 1 1 calc R U . . .
C28 C -0.1375(2) 0.08056(10) -0.04061(14) 0.0281(5) Uani 1 1 d . . . . .
H9 H -0.1352 0.0359 -0.0277 0.034 Uiso 1 1 calc R U . . .
C29 C -0.3828(2) 0.24313(11) -0.21592(15) 0.0297(5) Uani 1 1 d . . . . .
H11 H -0.3383 0.2786 -0.1797 0.045 Uiso 1 1 calc R U . . .
H13 H -0.4408 0.2219 -0.1777 0.045 Uiso 1 1 calc R U . . .
H12 H -0.4332 0.2598 -0.2742 0.045 Uiso 1 1 calc R U . . .
C30 C -0.1909(2) 0.22907(12) -0.29884(15) 0.0366(6) Uani 1 1 d . . . . .
H14 H -0.2395 0.2444 -0.3586 0.055 Uiso 1 1 calc R U . . .
H16 H -0.1239 0.1991 -0.3122 0.055 Uiso 1 1 calc R U . . .
H15 H -0.1505 0.2655 -0.2625 0.055 Uiso 1 1 calc R U . . .
C31 C 0.19269(18) 0.10944(9) 0.33998(13) 0.0185(4) Uani 1 1 d . . . . .
C32 C 0.1431(2) 0.21785(10) 0.34601(16) 0.0340(5) Uani 1 1 d . . . . .
H23 H 0.0507 0.2082 0.3307 0.051 Uiso 1 1 calc R U . . .
H22 H 0.1606 0.2598 0.3200 0.051 Uiso 1 1 calc R U . . .
H21 H 0.1681 0.2184 0.4149 0.051 Uiso 1 1 calc R U . . .
C33 C 0.25973(17) 0.09047(9) 0.42897(12) 0.0179(4) Uani 1 1 d . . . . .
C34 C 0.46617(19) 0.13724(10) 0.44023(14) 0.0265(5) Uani 1 1 d . . . . .
H24 H 0.5141 0.0969 0.4510 0.040 Uiso 1 1 calc R U . . .
H26 H 0.5181 0.1723 0.4717 0.040 Uiso 1 1 calc R U . . .
H25 H 0.4477 0.1458 0.3721 0.040 Uiso 1 1 calc R U . . .
C35 C -0.09215(19) -0.13879(10) 0.37702(14) 0.0247(4) Uani 1 1 d . . . . .
C36 C -0.2844(2) -0.18949(12) 0.31174(17) 0.0361(6) Uani 1 1 d . . . . .
H29 H -0.2429 -0.2314 0.3234 0.054 Uiso 1 1 calc R U . . .
H30 H -0.3462 -0.1911 0.2531 0.054 Uiso 1 1 calc R U . . .
H28 H -0.3298 -0.1784 0.3648 0.054 Uiso 1 1 calc R U . . .
C37 C 0.5529(2) -0.19268(10) 0.98881(15) 0.0323(5) Uani 1 1 d . . . . .
H35 H 0.5815 -0.2150 0.9352 0.048 Uiso 1 1 calc R U . . .
H33 H 0.4586 -0.1950 0.9832 0.048 Uiso 1 1 calc R U . . .
H34 H 0.5918 -0.2130 1.0481 0.048 Uiso 1 1 calc R U . . .


_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 C31 1.381(2) . ?
O1 C32 1.443(3) . ?
O2 C33 1.379(2) . ?
O2 C34 1.436(2) . ?
O3 C35 1.339(2) . ?
O3 C36 1.453(3) . ?
O4 C35 1.212(2) . ?
N1 C10 1.380(3) . ?
N1 C25 1.392(2) . ?
N1 C24 1.461(3) . ?
C1 C2 1.540(3) . ?
C2 C21 1.527(3) . ?
C2 C37 1.529(3) . ?
C2 C3 1.536(2) . ?
C3 C22 1.393(3) . ?
C3 C4 1.401(3) . ?
C4 C5 1.390(3) . ?
C5 C6 1.401(3) . ?
C6 C23 1.392(3) . ?
C6 C7 1.440(3) . ?
C7 C8 1.204(3) . ?
C8 C9 1.434(2) . ?
C9 C33 1.395(3) . ?
C9 C10 1.425(3) . ?
C10 C11 1.419(2) . ?
C11 C26 1.416(3) . ?
C11 C12 1.418(3) . ?
C12 C31 1.395(3) . ?
C12 C13 1.430(3) . ?
C13 C14 1.196(3) . ?
C14 C15 1.445(3) . ?
C15 C16 1.392(3) . ?
C15 C28 1.398(3) . ?
C16 C17 1.382(3) . ?
C17 C18 1.400(3) . ?
C18 C27 1.390(3) . ?
C18 C19 1.537(3) . ?
C19 C29 1.532(3) . ?
C19 C20 1.536(3) . ?
C19 C30 1.537(3) . ?
C22 C23 1.392(3) . ?
C25 C26 1.372(3) . ?
C25 C35 1.470(3) . ?
C27 C28 1.391(3) . ?
C31 C33 1.413(2) . ?

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
C31 O1 C32 110.87(15) . . ?
C33 O2 C34 113.58(14) . . ?
C35 O3 C36 113.91(16) . . ?
C10 N1 C25 107.93(15) . . ?
C10 N1 C24 125.89(17) . . ?
C25 N1 C24 126.17(18) . . ?
C21 C2 C37 108.11(19) . . ?
C21 C2 C3 112.11(17) . . ?
C37 C2 C3 109.95(16) . . ?
C21 C2 C1 109.03(19) . . ?
C37 C2 C1 108.85(18) . . ?
C3 C2 C1 108.73(16) . . ?
C22 C3 C4 117.25(17) . . ?
C22 C3 C2 123.00(17) . . ?
C4 C3 C2 119.75(17) . . ?
C5 C4 C3 121.45(18) . . ?
C4 C5 C6 120.56(18) . . ?
C23 C6 C5 118.37(17) . . ?
C23 C6 C7 121.61(18) . . ?
C5 C6 C7 119.93(18) . . ?
C8 C7 C6 173.9(2) . . ?
C7 C8 C9 176.1(2) . . ?
C33 C9 C10 116.60(16) . . ?
C33 C9 C8 120.38(17) . . ?
C10 C9 C8 123.01(18) . . ?
N1 C10 C11 107.84(16) . . ?
N1 C10 C9 131.07(17) . . ?
C11 C10 C9 121.05(18) . . ?
C26 C11 C12 131.52(17) . . ?
C26 C11 C10 107.23(17) . . ?
C12 C11 C10 121.09(17) . . ?
C31 C12 C11 117.43(16) . . ?
C31 C12 C13 120.99(17) . . ?
C11 C12 C13 121.55(17) . . ?
C14 C13 C12 178.2(2) . . ?
C13 C14 C15 176.5(2) . . ?
C16 C15 C28 118.18(17) . . ?
C16 C15 C14 119.97(17) . . ?
C28 C15 C14 121.85(18) . . ?
C17 C16 C15 120.66(18) . . ?
C16 C17 C18 121.95(19) . . ?
C27 C18 C17 116.82(17) . . ?
C27 C18 C19 123.47(17) . . ?
C17 C18 C19 119.70(17) . . ?
C29 C19 C20 108.97(17) . . ?
C29 C19 C18 108.79(15) . . ?
C20 C19 C18 111.75(17) . . ?
C29 C19 C30 108.94(18) . . ?
C20 C19 C30 108.16(18) . . ?
C18 C19 C30 110.19(16) . . ?
C23 C22 C3 121.85(18) . . ?
C6 C23 C22 120.51(18) . . ?
C26 C25 N1 109.81(17) . . ?
C26 C25 C35 127.56(18) . . ?
N1 C25 C35 122.51(17) . . ?
C25 C26 C11 107.17(17) . . ?
C18 C27 C28 121.89(18) . . ?
C27 C28 C15 120.40(19) . . ?
O1 C31 C12 119.93(16) . . ?
O1 C31 C33 118.88(17) . . ?
C12 C31 C33 121.19(17) . . ?
O2 C33 C9 118.55(16) . . ?
O2 C33 C31 118.86(17) . . ?
C9 C33 C31 122.49(17) . . ?
O4 C35 O3 123.13(19) . . ?
O4 C35 C25 125.61(19) . . ?
O3 C35 C25 111.26(17) . . ?

_refine_diff_density_max         0.773
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-3



####################################################################### 
# 
# 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_nelson05
_database_code_depnum_ccdc_archive 'CCDC 1437725'
_audit_update_record             
;
2015-11-19 deposited with the CCDC.
2016-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        Nelson05
_chemical_name_common            SSB-14-17
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H21 N3 O8'
_chemical_formula_weight         539.49

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.0196(3)
_cell_length_b                   13.8603(4)
_cell_length_c                   12.8511(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.7780(10)
_cell_angle_gamma                90
_cell_volume                     2496.94(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7538
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      28.20

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   0.878
_shelx_estimated_absorpt_T_max   0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25296
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.066
_diffrn_reflns_theta_max         28.316
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6198
_reflns_number_gt                4871
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+0.7400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6198
_refine_ls_number_parameters     365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1082
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
O1 O -0.47803(8) -0.32327(8) 0.99943(9) 0.0356(3) Uani 1 1 d . . . . .
O2 O -0.55456(7) -0.19384(9) 1.04135(9) 0.0342(3) Uani 1 1 d . . . . .
O3 O -0.12344(6) 0.22171(7) 1.00191(7) 0.0208(2) Uani 1 1 d . . . . .
O4 O -0.01108(7) 0.37816(6) 0.96731(7) 0.0209(2) Uani 1 1 d . . . . .
O5 O 0.26016(7) -0.09496(7) 0.73426(8) 0.0287(2) Uani 1 1 d . . . . .
O6 O 0.31137(7) 0.03270(7) 0.64241(8) 0.0257(2) Uani 1 1 d . . . . .
O7 O 0.45809(8) 0.81086(8) 0.79396(9) 0.0361(3) Uani 1 1 d . . . . .
O8 O 0.55953(8) 0.70614(9) 0.73746(9) 0.0374(3) Uani 1 1 d . . . . .
N1 N -0.48217(8) -0.23590(9) 1.01375(9) 0.0263(3) Uani 1 1 d . . . . .
N2 N 0.10560(8) 0.03027(7) 0.80361(8) 0.0181(2) Uani 1 1 d . . . . .
N3 N 0.48043(9) 0.72825(9) 0.76983(9) 0.0283(3) Uani 1 1 d . . . . .
C1 C 0.01840(12) 0.39034(11) 1.07379(11) 0.0311(3) Uani 1 1 d . . . . .
H16 H -0.0072 0.3375 1.1157 0.047 Uiso 1 1 calc R U . . .
H17 H -0.0057 0.4520 1.0999 0.047 Uiso 1 1 calc R U . . .
H15 H 0.0882 0.3899 1.0785 0.047 Uiso 1 1 calc R U . . .
C2 C 0.40864(10) 0.65164(10) 0.78224(10) 0.0234(3) Uani 1 1 d . . . . .
C3 C 0.31779(10) 0.67663(10) 0.81230(11) 0.0239(3) Uani 1 1 d . . . . .
H18 H 0.3005 0.7423 0.8214 0.029 Uiso 1 1 calc R U . . .
C4 C 0.25243(10) 0.60331(9) 0.82884(11) 0.0226(3) Uani 1 1 d . . . . .
H19 H 0.1895 0.6187 0.8497 0.027 Uiso 1 1 calc R U . . .
C5 C 0.27865(9) 0.50648(9) 0.81500(10) 0.0199(3) Uani 1 1 d . . . . .
C6 C 0.21286(9) 0.42983(9) 0.83591(10) 0.0206(3) Uani 1 1 d . . . . .
C7 C 0.16047(9) 0.36366(9) 0.85407(10) 0.0194(3) Uani 1 1 d . . . . .
C8 C 0.09996(9) 0.28238(9) 0.87132(10) 0.0181(3) Uani 1 1 d . . . . .
C9 C 0.12437(9) 0.19017(9) 0.83154(10) 0.0178(3) Uani 1 1 d . . . . .
C10 C 0.06342(9) 0.11005(9) 0.84737(10) 0.0170(3) Uani 1 1 d . . . . .
C11 C -0.02310(9) 0.11897(9) 0.90173(10) 0.0176(3) Uani 1 1 d . . . . .
C12 C -0.09092(9) 0.04430(9) 0.91851(10) 0.0186(3) Uani 1 1 d . . . . .
C13 C -0.15579(9) -0.00963(9) 0.93631(10) 0.0199(3) Uani 1 1 d . . . . .
C14 C -0.23683(9) -0.06879(9) 0.95772(10) 0.0191(3) Uani 1 1 d . . . . .
C15 C -0.23789(10) -0.16717(9) 0.93237(10) 0.0210(3) Uani 1 1 d . . . . .
H11 H -0.1835 -0.1958 0.9016 0.025 Uiso 1 1 calc R U . . .
C16 C -0.31769(10) -0.22289(10) 0.95193(10) 0.0225(3) Uani 1 1 d . . . . .
H10 H -0.3187 -0.2898 0.9357 0.027 Uiso 1 1 calc R U . . .
C17 C -0.39580(9) -0.17849(10) 0.99573(10) 0.0218(3) Uani 1 1 d . . . . .
C18 C 0.43616(10) 0.55705(11) 0.76504(11) 0.0256(3) Uani 1 1 d . . . . .
H21 H 0.4988 0.5425 0.7424 0.031 Uiso 1 1 calc R U . . .
C19 C 0.37058(10) 0.48427(10) 0.78147(11) 0.0241(3) Uani 1 1 d . . . . .
H20 H 0.3880 0.4190 0.7700 0.029 Uiso 1 1 calc R U . . .
C20 C 0.19093(9) 0.05972(9) 0.76093(10) 0.0188(3) Uani 1 1 d . . . . .
C21 C 0.20412(9) 0.15699(9) 0.77623(10) 0.0187(3) Uani 1 1 d . . . . .
H1 H 0.2567 0.1945 0.7539 0.022 Uiso 1 1 calc R U . . .
C22 C 0.25624(9) -0.01015(9) 0.71290(10) 0.0205(3) Uani 1 1 d . . . . .
C23 C 0.37596(10) -0.03162(11) 0.58838(12) 0.0277(3) Uani 1 1 d . . . . .
H2 H 0.4119 -0.0702 0.6394 0.042 Uiso 1 1 calc R U . . .
H3 H 0.4204 0.0065 0.5469 0.042 Uiso 1 1 calc R U . . .
H4 H 0.3391 -0.0745 0.5425 0.042 Uiso 1 1 calc R U . . .
C24 C 0.06327(10) -0.06609(9) 0.79585(11) 0.0228(3) Uani 1 1 d . . . . .
H7 H 0.0824 -0.1044 0.8567 0.034 Uiso 1 1 calc R U . . .
H6 H 0.0854 -0.0978 0.7325 0.034 Uiso 1 1 calc R U . . .
H5 H -0.0064 -0.0605 0.7932 0.034 Uiso 1 1 calc R U . . .
C25 C -0.39682(10) -0.08161(10) 1.02253(11) 0.0237(3) Uani 1 1 d . . . . .
H8 H -0.4516 -0.0536 1.0531 0.028 Uiso 1 1 calc R U . . .
C26 C -0.31672(10) -0.02664(10) 1.00388(11) 0.0227(3) Uani 1 1 d . . . . .
H9 H -0.3157 0.0397 1.0223 0.027 Uiso 1 1 calc R U . . .
C27 C -0.04371(9) 0.21031(9) 0.94252(10) 0.0178(3) Uani 1 1 d . . . . .
C28 C -0.20725(11) 0.24516(13) 0.94146(13) 0.0356(4) Uani 1 1 d . . . . .
H12 H -0.1990 0.3084 0.9088 0.053 Uiso 1 1 calc R U . . .
H14 H -0.2628 0.2469 0.9869 0.053 Uiso 1 1 calc R U . . .
H13 H -0.2172 0.1961 0.8874 0.053 Uiso 1 1 calc R U . . .
C29 C 0.01620(9) 0.29049(9) 0.92744(10) 0.0180(3) 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
O1 N1 1.2264(16) . ?
O2 N1 1.2270(16) . ?
O3 C27 1.3711(16) . ?
O3 C28 1.4371(17) . ?
O4 C29 1.3751(15) . ?
O4 C1 1.4340(17) . ?
O5 C22 1.2081(16) . ?
O6 C22 1.3379(16) . ?
O6 C23 1.4539(16) . ?
O7 N3 1.2279(17) . ?
O8 N3 1.2286(17) . ?
N1 C17 1.4698(17) . ?
N2 C10 1.3776(16) . ?
N2 C20 1.3844(17) . ?
N2 C24 1.4644(16) . ?
N3 C2 1.4732(17) . ?
C2 C3 1.380(2) . ?
C2 C18 1.385(2) . ?
C3 C4 1.3866(19) . ?
C4 C5 1.4035(18) . ?
C5 C19 1.3987(19) . ?
C5 C6 1.4348(18) . ?
C6 C7 1.1998(19) . ?
C7 C8 1.4294(18) . ?
C8 C29 1.3909(19) . ?
C8 C9 1.4201(17) . ?
C9 C21 1.4101(18) . ?
C9 C10 1.4175(17) . ?
C10 C11 1.4133(18) . ?
C11 C27 1.4019(17) . ?
C11 C12 1.4237(18) . ?
C12 C13 1.2015(18) . ?
C13 C14 1.4310(18) . ?
C14 C15 1.4020(18) . ?
C14 C26 1.4021(19) . ?
C15 C16 1.3853(19) . ?
C16 C17 1.383(2) . ?
C17 C25 1.3864(19) . ?
C18 C19 1.383(2) . ?
C20 C21 1.3745(18) . ?
C20 C22 1.4739(18) . ?
C25 C26 1.3807(19) . ?
C27 C29 1.4080(18) . ?

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
C27 O3 C28 113.07(11) . . ?
C29 O4 C1 112.43(10) . . ?
C22 O6 C23 114.87(11) . . ?
O1 N1 O2 123.61(12) . . ?
O1 N1 C17 118.05(12) . . ?
O2 N1 C17 118.34(12) . . ?
C10 N2 C20 107.64(10) . . ?
C10 N2 C24 125.74(11) . . ?
C20 N2 C24 126.41(11) . . ?
O7 N3 O8 123.55(12) . . ?
O7 N3 C2 117.89(13) . . ?
O8 N3 C2 118.55(13) . . ?
C3 C2 C18 122.84(13) . . ?
C3 C2 N3 118.94(13) . . ?
C18 C2 N3 118.21(13) . . ?
C2 C3 C4 118.24(13) . . ?
C3 C4 C5 120.45(13) . . ?
C19 C5 C4 119.57(12) . . ?
C19 C5 C6 119.48(12) . . ?
C4 C5 C6 120.95(12) . . ?
C7 C6 C5 177.74(14) . . ?
C6 C7 C8 177.15(14) . . ?
C29 C8 C9 117.95(11) . . ?
C29 C8 C7 121.58(12) . . ?
C9 C8 C7 120.47(12) . . ?
C21 C9 C10 107.49(11) . . ?
C21 C9 C8 132.19(12) . . ?
C10 C9 C8 120.31(12) . . ?
N2 C10 C11 130.39(11) . . ?
N2 C10 C9 107.89(11) . . ?
C11 C10 C9 121.70(11) . . ?
C27 C11 C10 116.51(11) . . ?
C27 C11 C12 117.28(12) . . ?
C10 C11 C12 126.20(11) . . ?
C13 C12 C11 171.78(14) . . ?
C12 C13 C14 176.48(14) . . ?
C15 C14 C26 119.84(12) . . ?
C15 C14 C13 121.24(12) . . ?
C26 C14 C13 118.91(12) . . ?
C16 C15 C14 120.41(13) . . ?
C17 C16 C15 118.15(12) . . ?
C16 C17 C25 122.90(12) . . ?
C16 C17 N1 118.81(12) . . ?
C25 C17 N1 118.29(12) . . ?
C19 C18 C2 118.60(13) . . ?
C18 C19 C5 120.25(13) . . ?
C21 C20 N2 110.36(11) . . ?
C21 C20 C22 128.40(12) . . ?
N2 C20 C22 121.14(11) . . ?
C20 C21 C9 106.61(11) . . ?
O5 C22 O6 124.11(13) . . ?
O5 C22 C20 124.80(13) . . ?
O6 C22 C20 111.08(11) . . ?
C26 C25 C17 118.70(13) . . ?
C25 C26 C14 119.98(13) . . ?
O3 C27 C11 119.07(11) . . ?
O3 C27 C29 118.56(11) . . ?
C11 C27 C29 122.34(12) . . ?
O4 C29 C8 120.38(11) . . ?
O4 C29 C27 118.47(12) . . ?
C8 C29 C27 121.13(12) . . ?

_refine_diff_density_max         0.319
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.047

_shelxl_version_number           2013-3



####################################################################### 
# 
# 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_nelson02
_database_code_depnum_ccdc_archive 'CCDC 1437726'
_audit_update_record             
;
2015-11-19 deposited with the CCDC.
2016-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        Nelson002
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H21 F2 N O4'
_chemical_formula_weight         485.47

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   23.809(4)
_cell_length_b                   13.756(3)
_cell_length_c                   7.2297(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2367.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2133
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      22.17

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4831
_diffrn_reflns_av_unetI/netI     0.1533
_diffrn_reflns_av_R_equivalents  0.0944
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.710
_diffrn_reflns_theta_max         23.286
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.816
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.816
_diffrn_reflns_point_group_measured_fraction_max 0.742
_diffrn_reflns_point_group_measured_fraction_full 0.606
_reflns_number_total             2531
_reflns_number_gt                1670
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.364
_reflns_Friedel_fraction_max     0.438
_reflns_Friedel_fraction_full    0.355

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0010P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0060(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 326 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.2(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2531
_refine_ls_number_parameters     330
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0671
_refine_ls_wR_factor_ref         0.1652
_refine_ls_wR_factor_gt          0.1461
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_restrained_S_all      0.942
_refine_ls_shift/su_max          0.003
_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 0.3157(2) -0.1924(3) 0.6568(8) 0.0606(15) Uani 1 1 d . . . . .
F2 F -0.0467(2) 1.0394(3) 0.3449(8) 0.0650(16) Uani 1 1 d . . . . .
O1 O 0.0907(2) 0.2731(3) 0.4404(9) 0.0448(15) Uani 1 1 d . . . . .
O2 O 0.04076(18) 0.4484(3) 0.3807(8) 0.0386(13) Uani 1 1 d . . . . .
O3 O 0.3392(2) 0.6806(4) 0.3224(9) 0.0579(17) Uani 1 1 d . . . . .
O4 O 0.3841(3) 0.5383(5) 0.3736(10) 0.0684(18) Uani 1 1 d . . . . .
N1 N 0.2737(2) 0.4429(5) 0.3905(9) 0.0450(18) Uani 1 1 d . . . . .
C1 C 0.3938(3) 0.7266(7) 0.3246(17) 0.071(3) Uani 1 1 d . . . . .
H1A H 0.3894 0.7970 0.3089 0.106 Uiso 1 1 calc R U . . .
H1B H 0.4168 0.7007 0.2235 0.106 Uiso 1 1 calc R U . . .
H1C H 0.4124 0.7134 0.4430 0.106 Uiso 1 1 calc R U . . .
C2 C 0.3413(3) 0.5835(7) 0.3522(13) 0.050(2) Uani 1 1 d . . . . .
C3 C 0.2843(3) 0.5419(6) 0.3615(14) 0.051(2) Uani 1 1 d . . . . .
C4 C 0.2340(3) 0.5900(6) 0.3476(12) 0.040(2) Uani 1 1 d . . . . .
H4A H 0.2294 0.6578 0.3281 0.048 Uiso 1 1 calc R U . . .
C5 C 0.1902(3) 0.5212(5) 0.3671(11) 0.0354(18) Uani 1 1 d . . . . .
C6 C 0.2163(3) 0.4287(5) 0.3953(11) 0.040(2) Uani 1 1 d . . . . .
C7 C 0.1827(3) 0.3427(5) 0.4175(12) 0.042(2) Uani 1 1 d . . . . .
C8 C 0.1249(3) 0.3535(5) 0.4123(12) 0.0369(19) Uani 1 1 d . . . . .
C9 C 0.0985(3) 0.4457(5) 0.3898(12) 0.0367(19) Uani 1 1 d . . . . .
C10 C 0.1311(3) 0.5293(4) 0.3634(12) 0.0324(18) Uani 1 1 d . . . . .
C11 C 0.0634(4) 0.2389(6) 0.2745(14) 0.055(3) Uani 1 1 d . . . . .
H11A H 0.0348 0.1908 0.3072 0.082 Uiso 1 1 calc R U . . .
H11B H 0.0914 0.2088 0.1928 0.082 Uiso 1 1 calc R U . . .
H11C H 0.0457 0.2937 0.2107 0.082 Uiso 1 1 calc R U . . .
C12 C 0.0146(3) 0.4806(5) 0.5517(14) 0.041(2) Uani 1 1 d . . . . .
H12A H -0.0261 0.4704 0.5442 0.062 Uiso 1 1 calc R U . . .
H12B H 0.0223 0.5499 0.5704 0.062 Uiso 1 1 calc R U . . .
H12C H 0.0298 0.4434 0.6556 0.062 Uiso 1 1 calc R U . . .
C13 C 0.1031(3) 0.6216(5) 0.3466(12) 0.0350(18) Uani 1 1 d . . . . .
C14 C 0.0775(3) 0.6967(5) 0.3369(11) 0.0333(18) Uani 1 1 d . . . . .
C15 C 0.0450(3) 0.7856(5) 0.3349(11) 0.0373(19) Uani 1 1 d . . . . .
C16 C 0.0709(3) 0.8737(5) 0.3893(12) 0.039(2) Uani 1 1 d . . . . .
H16A H 0.1094 0.8744 0.4248 0.047 Uiso 1 1 calc R U . . .
C17 C 0.0396(4) 0.9591(5) 0.3902(12) 0.047(2) Uani 1 1 d . . . . .
H17A H 0.0563 1.0192 0.4245 0.057 Uiso 1 1 calc R U . . .
C18 C -0.0148(4) 0.9543(5) 0.3414(13) 0.047(2) Uani 1 1 d . . . . .
C19 C -0.0420(4) 0.8701(6) 0.2900(15) 0.058(3) Uani 1 1 d . . . . .
H19A H -0.0807 0.8699 0.2589 0.069 Uiso 1 1 calc R U . . .
C20 C -0.0105(3) 0.7865(6) 0.2855(14) 0.049(2) Uani 1 1 d . . . . .
H20A H -0.0278 0.7275 0.2472 0.058 Uiso 1 1 calc R U . . .
C21 C 0.2057(3) 0.2481(5) 0.4501(12) 0.041(2) Uani 1 1 d . . . . .
C22 C 0.2225(3) 0.1681(6) 0.4890(12) 0.043(2) Uani 1 1 d . . . . .
C23 C 0.2468(3) 0.0735(5) 0.5250(12) 0.038(2) Uani 1 1 d . . . . .
C24 C 0.3036(3) 0.0616(5) 0.5299(12) 0.045(2) Uani 1 1 d . . . . .
H24A H 0.3272 0.1158 0.5062 0.053 Uiso 1 1 calc R U . . .
C25 C 0.3281(4) -0.0287(6) 0.5690(12) 0.045(2) Uani 1 1 d . . . . .
H25A H 0.3676 -0.0380 0.5671 0.054 Uiso 1 1 calc R U . . .
C26 C 0.2914(4) -0.1034(6) 0.6106(13) 0.047(2) Uani 1 1 d . . . . .
C27 C 0.2355(4) -0.0955(5) 0.6112(13) 0.046(2) Uani 1 1 d . . . . .
H27A H 0.2125 -0.1499 0.6395 0.055 Uiso 1 1 calc R U . . .
C28 C 0.2115(3) -0.0055(5) 0.5694(11) 0.039(2) Uani 1 1 d . . . . .
H28A H 0.1719 0.0024 0.5709 0.047 Uiso 1 1 calc R U . . .
C29 C 0.3168(4) 0.3681(6) 0.4101(16) 0.063(3) Uani 1 1 d . . . . .
H29A H 0.3018 0.3140 0.4833 0.094 Uiso 1 1 calc R U . . .
H29B H 0.3496 0.3956 0.4727 0.094 Uiso 1 1 calc R U . . .
H29C H 0.3277 0.3444 0.2874 0.094 Uiso 1 1 calc R U . . .


_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 C26 1.393(9) . ?
F2 C18 1.395(8) . ?
O1 C8 1.388(8) . ?
O1 C11 1.444(10) . ?
O2 C9 1.377(8) . ?
O2 C12 1.454(10) . ?
O3 C2 1.353(11) . ?
O3 C1 1.448(9) . ?
O4 C2 1.204(9) . ?
N1 C6 1.380(9) . ?
N1 C3 1.401(10) . ?
N1 C29 1.460(10) . ?
C2 C3 1.474(11) . ?
C3 C4 1.371(10) . ?
C4 C5 1.416(10) . ?
C5 C10 1.410(10) . ?
C5 C6 1.431(10) . ?
C6 C7 1.438(10) . ?
C7 C8 1.385(10) . ?
C7 C21 1.432(10) . ?
C8 C9 1.424(9) . ?
C9 C10 1.401(10) . ?
C10 C13 1.439(10) . ?
C13 C14 1.202(9) . ?
C14 C15 1.446(9) . ?
C15 C20 1.370(11) . ?
C15 C16 1.416(10) . ?
C16 C17 1.392(10) . ?
C17 C18 1.345(11) . ?
C18 C19 1.378(11) . ?
C19 C20 1.373(11) . ?
C21 C22 1.204(10) . ?
C22 C23 1.447(11) . ?
C23 C24 1.364(11) . ?
C23 C28 1.410(10) . ?
C24 C25 1.400(10) . ?
C25 C26 1.382(11) . ?
C26 C27 1.338(12) . ?
C27 C28 1.395(10) . ?

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
C8 O1 C11 113.7(6) . . ?
C9 O2 C12 113.3(6) . . ?
C2 O3 C1 113.3(7) . . ?
C6 N1 C3 108.7(6) . . ?
C6 N1 C29 126.3(7) . . ?
C3 N1 C29 125.0(7) . . ?
O4 C2 O3 124.2(8) . . ?
O4 C2 C3 125.0(9) . . ?
O3 C2 C3 110.8(8) . . ?
C4 C3 N1 108.8(6) . . ?
C4 C3 C2 127.9(8) . . ?
N1 C3 C2 123.3(8) . . ?
C3 C4 C5 108.3(7) . . ?
C10 C5 C4 132.8(6) . . ?
C10 C5 C6 120.5(7) . . ?
C4 C5 C6 106.7(6) . . ?
N1 C6 C5 107.5(6) . . ?
N1 C6 C7 132.2(7) . . ?
C5 C6 C7 120.3(7) . . ?
C8 C7 C21 118.8(7) . . ?
C8 C7 C6 117.5(6) . . ?
C21 C7 C6 123.6(7) . . ?
C7 C8 O1 119.5(6) . . ?
C7 C8 C9 122.5(6) . . ?
O1 C8 C9 117.9(6) . . ?
O2 C9 C10 121.6(6) . . ?
O2 C9 C8 118.0(6) . . ?
C10 C9 C8 120.2(6) . . ?
C9 C10 C5 119.0(6) . . ?
C9 C10 C13 118.6(6) . . ?
C5 C10 C13 122.3(6) . . ?
C14 C13 C10 176.8(8) . . ?
C13 C14 C15 176.8(9) . . ?
C20 C15 C16 119.0(7) . . ?
C20 C15 C14 121.7(7) . . ?
C16 C15 C14 119.2(6) . . ?
C17 C16 C15 119.4(7) . . ?
C18 C17 C16 118.3(7) . . ?
C17 C18 C19 124.4(7) . . ?
C17 C18 F2 118.6(8) . . ?
C19 C18 F2 117.1(7) . . ?
C20 C19 C18 117.0(7) . . ?
C15 C20 C19 121.9(8) . . ?
C22 C21 C7 175.1(9) . . ?
C21 C22 C23 175.0(9) . . ?
C24 C23 C28 119.4(7) . . ?
C24 C23 C22 120.6(7) . . ?
C28 C23 C22 119.8(7) . . ?
C23 C24 C25 121.7(7) . . ?
C26 C25 C24 116.2(7) . . ?
C27 C26 C25 124.7(8) . . ?
C27 C26 F1 119.0(8) . . ?
C25 C26 F1 116.4(7) . . ?
C26 C27 C28 118.6(8) . . ?
C27 C28 C23 119.4(7) . . ?

_refine_diff_density_max         0.333
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.064

_shelxl_version_number           2013-3



