# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1
_audit_creation_method           'Created with Diamond (www.crystalimpact.com)'
_audit_creation_date             12-07-02
_audit_update_record             12-07-02
_chemical_formula_sum            'C30 H32 F N4 O6'
_chemical_formula_weight         563.600
_refine_ls_R_factor_all          0.070
_cell_length_a                   10.9347(6)
_cell_length_b                   12.6382(7)
_cell_length_c                   12.7232(7)
_cell_angle_alpha                61.420(1)
_cell_angle_beta                 66.901(1)
_cell_angle_gamma                68.104(1)
_cell_volume                     1382.4(1)
_cell_formula_units_Z            2
_symmetry_int_tables_number      2
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  -P_1

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
C ? 1.200
H ? 1.200
F ? 1.200
N ? 1.200
O ? 1.200


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_u_iso_or_equiv
C1 C 0.2456(2) 0.1352(2) -0.4247(2) 1.000 2 i ? d Uani 0.0457(5)
H1A H 0.1740 0.1357 -0.3545 1.000 2 i ? calc Uiso 0.05500
C2 C 0.2571(3) 0.0683(2) -0.4884(2) 1.000 2 i ? d Uani 0.0502(6)
H2A H 0.1935 0.0222 -0.4617 1.000 2 i ? calc Uiso 0.06000
C3 C 0.3657(3) 0.0704(2) -0.5940(2) 1.000 2 i ? d Uani 0.0492(6)
C4 C 0.4641(3) 0.1351(2) -0.6404(2) 1.000 2 i ? d Uani 0.0498(6)
H4A H 0.5350 0.1350 -0.7112 1.000 2 i ? calc Uiso 0.06000
C5 C 0.4494(2) 0.2007(2) -0.5730(2) 1.000 2 i ? d Uani 0.0452(5)
C6 C 0.3437(2) 0.2026(2) -0.4677(2) 1.000 2 i ? d Uani 0.0410(5)
C7 C 0.3711(2) 0.2806(2) -0.4303(2) 1.000 2 i ? d Uani 0.0433(5)
C8 C 0.2895(2) 0.3125(2) -0.3187(2) 1.000 2 i ? d Uani 0.0437(5)
H8A H 0.1936 0.3427 -0.3210 1.000 2 i ? calc Uiso 0.05200
C9 C 0.3292(3) 0.4119(2) -0.3122(2) 1.000 2 i ? d Uani 0.0461(5)
H9A H 0.4241 0.3848 -0.3104 1.000 2 i ? calc Uiso 0.05500
H9B H 0.3197 0.4871 -0.3857 1.000 2 i ? calc Uiso 0.05500
C10 C 0.2398(3) 0.4382(2) -0.1975(2) 1.000 2 i ? d Uani 0.0480(6)
H10A H 0.2692 0.4996 -0.1938 1.000 2 i ? calc Uiso 0.05800
H10B H 0.1460 0.4722 -0.2032 1.000 2 i ? calc Uiso 0.05800
C11 C 0.2068(3) 0.2280(3) -0.0867(2) 1.000 2 i ? d Uani 0.0532(6)
H11A H 0.1126 0.2563 -0.0909 1.000 2 i ? calc Uiso 0.06400
H11B H 0.2134 0.1542 -0.0115 1.000 2 i ? calc Uiso 0.06400
C12 C 0.2989(3) 0.1969(2) -0.1991(2) 1.000 2 i ? d Uani 0.0524(6)
H12A H 0.2714 0.1330 -0.2004 1.000 2 i ? calc Uiso 0.06300
H12B H 0.3926 0.1654 -0.1933 1.000 2 i ? calc Uiso 0.06300
C13 C 0.1599(2) 0.3542(2) 0.0275(2) 1.000 2 i ? d Uani 0.0459(5)
H13A H 0.0653 0.3609 0.0367 1.000 2 i ? calc Uiso 0.05500
H13B H 0.1678 0.4339 0.0140 1.000 2 i ? calc Uiso 0.05500
C14 C 0.1985(2) 0.2572(2) 0.1474(2) 1.000 2 i ? d Uani 0.0437(5)
H14A H 0.1880 0.1779 0.1625 1.000 2 i ? calc Uiso 0.05200
H14B H 0.2937 0.2488 0.1377 1.000 2 i ? calc Uiso 0.05200
C15 C 0.1116(2) 0.2907(2) 0.2581(2) 1.000 2 i ? d Uani 0.0391(5)
C16 C 0.0078(2) 0.2247(2) 0.3447(2) 1.000 2 i ? d Uani 0.0390(5)
C17 C 0.2379(3) 0.4499(3) 0.2022(3) 1.000 2 i ? d Uani 0.0639(8)
H17A H 0.2910 0.4253 0.1337 1.000 2 i ? calc Uiso 0.09600
H17B H 0.2964 0.4343 0.2504 1.000 2 i ? calc Uiso 0.09600
H17C H 0.1957 0.5367 0.1715 1.000 2 i ? calc Uiso 0.09600
C18 C 0.1301(2) 0.3776(2) 0.2817(2) 1.000 2 i ? d Uani 0.0440(5)
C19 C -0.0438(2) 0.3437(2) 0.4635(2) 1.000 2 i ? d Uani 0.0407(5)
C20 C -0.1277(3) 0.3766(3) 0.5763(2) 1.000 2 i ? d Uani 0.0561(7)
C21A C -0.1719(13) 0.2615(11) 0.6854(9) 0.263(9) 2 i ? d Uani 0.059(4)
H21A H -0.0938 0.2077 0.7182 0.263(9) 2 i ? calc Uiso 0.07000
H21B H -0.2410 0.2874 0.7501 0.263(9) 2 i ? calc Uiso 0.07000
C21 C -0.2582(4) 0.3263(4) 0.6446(3) 0.737(9) 2 i ? d Uani 0.0542(12)
H21C H -0.2987 0.3345 0.7240 0.737(9) 2 i ? calc Uiso 0.06500
H21D H -0.3243 0.3724 0.5958 0.737(9) 2 i ? calc Uiso 0.06500
C22 C -0.2200(4) 0.1963(3) 0.6632(3) 1.000 2 i ? d Uani 0.0768(9)
H22A H -0.3173 0.2320 0.6743 1.000 2 i ? calc Uiso 0.09200
H22B H -0.2101 0.1143 0.7286 1.000 2 i ? calc Uiso 0.09200
C23 C -0.1676(3) 0.1782(3) 0.5429(2) 1.000 2 i ? d Uani 0.0517(6)
H23A H -0.1256 0.0914 0.5588 1.000 2 i ? calc Uiso 0.06200
H23B H -0.2438 0.2013 0.5092 1.000 2 i ? calc Uiso 0.06200
C24 C 0.8686(2) 0.1253(2) 0.1284(2) 1.000 2 i ? d Uani 0.0459(5)
C25 C 0.7889(3) 0.2393(2) 0.1296(2) 1.000 2 i ? d Uani 0.0483(6)
H25A H 0.8068 0.2768 0.1679 1.000 2 i ? calc Uiso 0.05800
C26 C 0.6810(3) 0.2983(2) 0.0729(2) 1.000 2 i ? d Uani 0.0459(5)
H26A H 0.6274 0.3751 0.0733 1.000 2 i ? calc Uiso 0.05500
C27 C 0.6540(2) 0.2421(2) 0.0163(2) 1.000 2 i ? d Uani 0.0425(5)
C28 C 0.5350(2) 0.3033(2) -0.0368(2) 1.000 2 i ? d Uani 0.0444(5)
C29 C 0.7344(3) 0.1272(2) 0.0166(2) 1.000 2 i ? d Uani 0.0479(6)
H29A H 0.7160 0.0887 -0.0203 1.000 2 i ? calc Uiso 0.05800
C30 C 0.8405(3) 0.0703(2) 0.0709(2) 1.000 2 i ? d Uani 0.0502(6)
H30A H 0.8944 -0.0060 0.0693 1.000 2 i ? calc Uiso 0.06000
F1 F 0.3735(2) 0.0036(2) -0.6548(2) 1.000 2 i ? d Uani 0.0695(5)
N1 N 0.4802(2) 0.3206(2) -0.5039(2) 1.000 2 i ? d Uani 0.0562(6)
N2 N 0.2462(2) 0.3249(2) -0.0825(2) 1.000 2 i ? d Uani 0.0386(4)
N3 N 0.0485(2) 0.4061(2) 0.3832(2) 1.000 2 i ? d Uani 0.0494(5)
N4 N -0.0658(2) 0.2535(2) 0.4497(2) 1.000 2 i ? d Uani 0.0373(4)
O1 O 0.5334(2) 0.2707(2) -0.5979(2) 1.000 2 i ? d Uani 0.0600(5)
O2 O -0.0206(2) 0.1435(2) 0.3361(2) 1.000 2 i ? d Uani 0.0568(5)
O3 O -0.1734(4) 0.4878(4) 0.5468(4) 0.500 2 i ? d Uani 0.0694(11)
H3 H -0.1103 0.5232 0.5102 0.500 2 i ? calc Uiso 0.10400
O4 O -0.0460(2) 0.3550(2) 0.6432(2) 0.500 2 i ? d Uani 0.0374(6)
H4B H 0.0143 0.3933 0.5989 0.500 2 i ? calc Uiso 0.05600
O5 O 0.9740(2) 0.0633(2) 0.1806(2) 1.000 2 i ? d Uani 0.0589(5)
H5A H 0.9689 0.0929 0.2276 1.000 2 i ? d Uiso 0.08800
O6 O 0.4718(2) 0.4092(2) -0.0525(2) 1.000 2 i ? d Uani 0.0647(5)
O7 O 0.5006(2) 0.2305(2) -0.0642(2) 1.000 2 i ? d Uani 0.0549(5)
H7 H 0.4142 0.2694 -0.0772 1.000 2 i ? d Uiso 0.06600




_database_code_depnum_ccdc_archive 'CCDC 855981'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H26 F N4 O3, C7 H7 N O2'
_chemical_formula_sum            'C30 H33 F N5 O5'
_chemical_formula_weight         562.61

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.9374(7)
_cell_length_b                   12.6162(8)
_cell_length_c                   12.7201(8)
_cell_angle_alpha                61.3960(10)
_cell_angle_beta                 66.8530(10)
_cell_angle_gamma                68.1370(10)
_cell_volume                     1379.57(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3283
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      28.25

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             594
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_T_max  0.9806
_exptl_absorpt_process_details   '(North et al., 1968)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6986
_diffrn_reflns_av_R_equivalents  0.0120
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4799
_reflns_number_gt                3852
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0858P)²+0.4591P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4799
_refine_ls_number_parameters     483
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1577
_refine_ls_wR_factor_gt          0.1494
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4648(2) 0.1966(2) 1.0371(2) 0.0480(5) Uani 1 1 d . . .
C2 C 0.3463(2) 0.2571(2) 0.98380(19) 0.0470(5) Uani 1 1 d . . .
C3 C 0.3188(2) 0.2018(2) 0.9273(2) 0.0497(6) Uani 1 1 d . . .
C4 C 0.2110(2) 0.2606(2) 0.8707(2) 0.0505(6) Uani 1 1 d . . .
C5 C 0.1312(2) 0.3748(2) 0.8720(2) 0.0494(5) Uani 1 1 d . . .
C6 C 0.1597(3) 0.4297(2) 0.9298(2) 0.0538(6) Uani 1 1 d . . .
C7 C 0.2655(2) 0.3724(2) 0.9837(2) 0.0512(6) Uani 1 1 d . . .
C8 C 0.2577(3) 0.5683(2) -0.4883(2) 0.0514(6) Uani 1 1 d . . .
C9 C 0.2463(2) 0.6352(2) -0.4243(2) 0.0482(5) Uani 1 1 d . . .
C10 C 0.3653(3) 0.5708(2) -0.5938(2) 0.0508(6) Uani 1 1 d . . .
C11 C 0.4638(3) 0.6351(2) -0.6399(2) 0.0518(6) Uani 1 1 d . . .
C12 C 0.4495(2) 0.7010(2) -0.5727(2) 0.0473(5) Uani 1 1 d . . .
C13 C 0.3442(2) 0.7024(2) -0.46735(18) 0.0435(5) Uani 1 1 d . . .
C14 C 0.3713(2) 0.7803(2) -0.42956(19) 0.0452(5) Uani 1 1 d . . .
C15 C 0.2904(2) 0.8121(2) -0.3186(2) 0.0456(5) Uani 1 1 d . . .
C16 C 0.2992(3) 0.6970(2) -0.1988(2) 0.0555(6) Uani 1 1 d . . .
C17 C 0.2074(3) 0.7278(3) -0.0869(2) 0.0576(6) Uani 1 1 d . . .
C18 C 0.2395(3) 0.9385(2) -0.1973(2) 0.0510(6) Uani 1 1 d . . .
C19 C 0.3297(3) 0.9118(2) -0.3122(2) 0.0493(6) Uani 1 1 d . . .
C20 C 0.1603(2) 0.8543(2) 0.0275(2) 0.0481(5) Uani 1 1 d . . .
C21 C 0.1122(2) 0.79051(19) 0.25782(18) 0.0407(5) Uani 1 1 d . . .
C22 C 0.1981(2) 0.7572(2) 0.1473(2) 0.0459(5) Uani 1 1 d . . .
C23 C 0.0080(2) 0.7247(2) 0.34399(19) 0.0415(5) Uani 1 1 d . B .
C24 C -0.0423(2) 0.8423(2) 0.46384(19) 0.0437(5) Uani 1 1 d . B .
C25 C -0.1266(3) 0.8762(3) 0.5764(2) 0.0612(7) Uani 1 1 d U . .
C27 C -0.2246(4) 0.7002(4) 0.6595(3) 0.0952(12) Uani 1 1 d . . .
H27A H -0.3054 0.6666 0.7076 0.114 Uiso 1 1 calc R A 1
H27B H -0.1578 0.6549 0.7076 0.114 Uiso 1 1 calc R A 1
C28 C -0.1679(3) 0.6781(3) 0.5422(2) 0.0543(6) Uani 1 1 d . B .
C29 C 0.2389(3) 0.9494(3) 0.2026(2) 0.0675(8) Uani 1 1 d . . .
H29A H 0.3012 0.9158 0.1421 0.101 Uiso 1 1 calc R . .
H29B H 0.2877 0.9444 0.2538 0.101 Uiso 1 1 calc R . .
H29C H 0.1972 1.0345 0.1611 0.101 Uiso 1 1 calc R . .
C30 C 0.1309(2) 0.8768(2) 0.28184(19) 0.0460(5) Uani 1 1 d . B .
C26A C -0.2601(4) 0.8280(4) 0.6420(4) 0.0456(11) Uani 0.59 1 d P B 1
H26A H -0.3022 0.8359 0.7216 0.055 Uiso 0.59 1 calc PR B 1
H26B H -0.3244 0.8759 0.5914 0.055 Uiso 0.59 1 calc PR B 1
C26B C -0.1884(14) 0.7681(12) 0.6815(8) 0.114(4) Uani 0.41 1 d P B 2
H26C H -0.1225 0.7150 0.7298 0.136 Uiso 0.41 1 calc PR B 2
H26D H -0.2677 0.8023 0.7350 0.136 Uiso 0.41 1 calc PR B 2
F1 F 0.37318(18) 0.50384(15) -0.65455(14) 0.0722(5) Uani 1 1 d . . .
H1 H 0.532(3) 0.636(2) -0.708(2) 0.059(7) Uiso 1 1 d . . .
H2 H 0.202(3) 0.515(2) -0.461(2) 0.053(7) Uiso 1 1 d . . .
H3 H 0.172(3) 0.632(2) -0.352(2) 0.058(7) Uiso 1 1 d . . .
H4 H 0.202(3) 0.838(2) -0.323(2) 0.054(7) Uiso 1 1 d . . .
H5 H 0.432(3) 0.877(2) -0.305(2) 0.069(8) Uiso 1 1 d . . .
H6 H 0.320(2) 0.986(2) -0.383(2) 0.053(6) Uiso 1 1 d . . .
H7 H 0.392(3) 0.667(3) -0.195(3) 0.067(8) Uiso 1 1 d . . .
H8 H 0.275(3) 0.629(3) -0.198(3) 0.075(8) Uiso 1 1 d . . .
H9 H 0.217(3) 0.655(3) -0.006(3) 0.082(9) Uiso 1 1 d . . .
H10 H 0.103(3) 0.763(3) -0.091(3) 0.077(9) Uiso 1 1 d . . .
H11 H 0.269(3) 1.001(2) -0.193(2) 0.056(7) Uiso 1 1 d . . .
H12 H 0.137(3) 0.969(2) -0.201(2) 0.058(7) Uiso 1 1 d . . .
H13 H 0.177(2) 0.939(2) 0.009(2) 0.058(7) Uiso 1 1 d . . .
H14 H 0.062(3) 0.864(2) 0.032(2) 0.060(7) Uiso 1 1 d . . .
H15 H 0.289(3) 0.750(2) 0.139(2) 0.050(6) Uiso 1 1 d . . .
H16 H 0.184(3) 0.673(2) 0.166(2) 0.057(7) Uiso 1 1 d . . .
H20 H -0.231(3) 0.693(3) 0.502(3) 0.087(10) Uiso 1 1 d . . .
H21 H -0.113(3) 0.582(3) 0.560(3) 0.076(8) Uiso 1 1 d . . .
H24 H 0.381(3) 0.118(3) 0.928(2) 0.066(7) Uiso 1 1 d . . .
H25 H 0.179(2) 0.210(2) 0.8405(19) 0.042(6) Uiso 1 1 d . . .
H26 H 0.101(3) 0.516(3) 0.927(2) 0.066(8) Uiso 1 1 d . . .
H27 H 0.588(2) 0.226(4) 1.080(5) 0.155(18) Uiso 1 1 d D . .
H28 H 0.299(2) 0.4114(19) 1.0127(19) 0.035(5) Uiso 1 1 d . . .
N1 N 0.02737(18) 0.43538(17) 0.81990(17) 0.0450(4) Uani 1 1 d . . .
H1A H 0.0077 0.4036 0.7836 0.054 Uiso 1 1 calc R . .
H1B H -0.0200 0.5063 0.8226 0.054 Uiso 1 1 calc R . .
N2 N 0.4805(2) 0.8209(2) -0.50391(18) 0.0590(5) Uani 1 1 d . . .
N3 N 0.24696(17) 0.82514(15) -0.08261(15) 0.0404(4) Uani 1 1 d . . .
N4 N -0.06535(17) 0.75332(16) 0.44926(15) 0.0390(4) Uani 1 1 d . . .
N5 N 0.0502(2) 0.90469(19) 0.38375(17) 0.0527(5) Uani 1 1 d . . .
O1 O 0.49943(18) 0.26908(17) 1.06464(17) 0.0594(5) Uani 1 1 d D . .
O2 O 0.52799(19) 0.09048(17) 1.05240(19) 0.0698(5) Uani 1 1 d . . .
O3 O 0.53329(18) 0.77093(18) -0.59770(15) 0.0623(5) Uani 1 1 d . . .
O4 O -0.02049(18) 0.64343(16) 0.33528(16) 0.0597(5) Uani 1 1 d . . .
O5A O -0.0454(3) 0.8539(3) 0.6428(3) 0.0550(7) Uani 0.57 1 d PU B 1
H5A H -0.0364 0.9197 0.6336 0.082 Uiso 0.57 1 calc PR B 1
O5B O -0.1729(4) 0.9886(4) 0.5453(3) 0.0494(8) Uani 0.43 1 d P B 2
H5B H -0.1340 1.0168 0.5664 0.074 Uiso 0.43 1 calc PR B 2


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.215(3) . ?
C1 O1 1.331(3) . ?
C1 C2 1.477(3) . ?
C2 C3 1.378(3) . ?
C2 C7 1.392(3) . ?
C3 C4 1.402(3) . ?
C4 C5 1.383(3) . ?
C5 N1 1.332(3) . ?
C5 C6 1.394(3) . ?
C6 C7 1.364(4) . ?
C8 C9 1.375(3) . ?
C8 C10 1.389(3) . ?
C9 C13 1.392(3) . ?
C10 F1 1.355(3) . ?
C10 C11 1.364(3) . ?
C11 C12 1.388(3) . ?
C12 O3 1.351(3) . ?
C12 C13 1.385(3) . ?
C13 C14 1.437(3) . ?
C14 N2 1.299(3) . ?
C14 C15 1.495(3) . ?
C15 C19 1.516(3) . ?
C15 C16 1.527(3) . ?
C16 C17 1.518(3) . ?
C17 N3 1.475(3) . ?
C18 N3 1.480(3) . ?
C18 C19 1.521(3) . ?
C20 N3 1.479(3) . ?
C20 C22 1.524(3) . ?
C21 C30 1.362(3) . ?
C21 C23 1.429(3) . ?
C21 C22 1.506(3) . ?
C23 O4 1.238(3) . ?
C23 N4 1.404(3) . ?
C24 N5 1.302(3) . ?
C24 N4 1.344(3) . ?
C24 C25 1.528(3) . ?
C25 O5B 1.229(4) . ?
C25 O5A 1.325(4) . ?
C25 C26B 1.528(9) . ?
C25 C26A 1.555(5) . ?
C27 C26B 1.240(9) . ?
C27 C26A 1.435(6) . ?
C27 C28 1.494(4) . ?
C28 N4 1.494(3) . ?
C29 C30 1.495(3) . ?
C30 N5 1.374(3) . ?
N2 O3 1.436(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
O2 C1 O1 122.2(2) . . ?
O2 C1 C2 123.3(2) . . ?
O1 C1 C2 114.43(19) . . ?
C3 C2 C7 119.0(2) . . ?
C3 C2 C1 119.6(2) . . ?
C7 C2 C1 121.3(2) . . ?
C2 C3 C4 120.5(2) . . ?
C5 C4 C3 119.7(2) . . ?
N1 C5 C4 122.6(2) . . ?
N1 C5 C6 118.1(2) . . ?
C4 C5 C6 119.3(2) . . ?
C7 C6 C5 120.7(2) . . ?
C6 C7 C2 120.7(2) . . ?
C9 C8 C10 119.2(2) . . ?
C8 C9 C13 118.5(2) . . ?
F1 C10 C11 117.7(2) . . ?
F1 C10 C8 117.5(2) . . ?
C11 C10 C8 124.7(2) . . ?
C10 C11 C12 114.5(2) . . ?
O3 C12 C13 110.2(2) . . ?
O3 C12 C11 126.4(2) . . ?
C13 C12 C11 123.3(2) . . ?
C12 C13 C9 119.7(2) . . ?
C12 C13 C14 103.81(19) . . ?
C9 C13 C14 136.4(2) . . ?
N2 C14 C13 111.56(19) . . ?
N2 C14 C15 121.7(2) . . ?
C13 C14 C15 126.75(19) . . ?
C14 C15 C19 115.19(19) . . ?
C14 C15 C16 110.8(2) . . ?
C19 C15 C16 108.34(19) . . ?
C17 C16 C15 110.5(2) . . ?
N3 C17 C16 110.7(2) . . ?
N3 C18 C19 111.41(19) . . ?
C15 C19 C18 110.8(2) . . ?
N3 C20 C22 113.22(18) . . ?
C30 C21 C23 118.44(19) . . ?
C30 C21 C22 123.8(2) . . ?
C23 C21 C22 117.76(19) . . ?
C21 C22 C20 112.54(18) . . ?
O4 C23 N4 117.77(19) . . ?
O4 C23 C21 125.9(2) . . ?
N4 C23 C21 116.29(18) . . ?
N5 C24 N4 122.56(19) . . ?
N5 C24 C25 116.72(19) . . ?
N4 C24 C25 120.72(19) . . ?
O5B C25 O5A 102.0(3) . . ?
O5B C25 C26B 130.3(6) . . ?
O5A C25 C26B 88.8(6) . . ?
O5B C25 C24 111.5(3) . . ?
O5A C25 C24 109.7(2) . . ?
C26B C25 C24 109.7(4) . . ?
O5B C25 C26A 101.0(3) . . ?
O5A C25 C26A 119.7(3) . . ?
C26B C25 C26A 36.7(6) . . ?
C24 C25 C26A 112.0(2) . . ?
C26B C27 C26A 41.8(7) . . ?
C26B C27 C28 125.2(4) . . ?
C26A C27 C28 114.7(3) . . ?
C27 C28 N4 111.8(2) . . ?
C21 C30 N5 122.05(19) . . ?
C21 C30 C29 124.3(2) . . ?
N5 C30 C29 113.61(19) . . ?
C27 C26A C25 107.7(3) . . ?
C27 C26B C25 121.2(7) . . ?
C14 N2 O3 106.87(18) . . ?
C17 N3 C20 111.37(18) . . ?
C17 N3 C18 110.51(18) . . ?
C20 N3 C18 110.22(17) . . ?
C24 N4 C23 121.18(17) . . ?
C24 N4 C28 123.27(18) . . ?
C23 N4 C28 115.55(17) . . ?
C24 N5 C30 119.34(19) . . ?
C12 O3 N2 107.53(16) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 948923'
