# 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).
# 
# 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_publication_text
_database_code_depnum_ccdc_archive 'CCDC 1003333'
_audit_update_record             
;
2014-08-28 deposited with the CCDC.
2015-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 Tetrabutyl ammonium salt of Naphthyl oxime
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H36 N, C11 H9 N O2, F'
_chemical_formula_sum            'C27 H45 F N2 O2'
_chemical_formula_weight         448.65

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           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_space_group_name_Hall           'P -2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.1130(6)
_cell_length_b                   17.5762(10)
_cell_length_c                   15.6751(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.831(6)
_cell_angle_gamma                90.00
_cell_volume                     2716.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.097
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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            12047
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         25.25
_reflns_number_total             4901
_reflns_number_gt                2959
_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.Alert level A for disorder
C26-C27 bond.
;

_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)+(0.0711P)²+1.2098P] 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         4901
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1120
_refine_ls_R_factor_gt           0.0686
_refine_ls_wR_factor_ref         0.2015
_refine_ls_wR_factor_gt          0.1729
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
F1 F 0.17387(17) 0.28183(9) 0.27413(11) 0.0699(5) Uani 1 1 d . . .
O1 O -0.10749(19) 0.64178(11) 0.24837(15) 0.0659(6) Uani 1 1 d . . .
H1A H -0.1330 0.6857 0.2374 0.099 Uiso 1 1 calc R . .
O2 O 0.1256(2) 0.41683(11) 0.27029(16) 0.0729(6) Uani 1 1 d . . .
H2 H 0.1514 0.3725 0.2739 0.109 Uiso 1 1 calc R . .
N1 N 0.0286(2) 0.63523(13) 0.24381(15) 0.0553(6) Uani 1 1 d . . .
N2 N 0.0756(3) 0.25232(16) 0.50775(16) 0.0771(8) Uani 1 1 d . . .
C11 C 0.3118(3) 0.58757(16) 0.23004(16) 0.0509(7) Uani 1 1 d . . .
C3 C 0.2263(3) 0.46216(16) 0.25696(17) 0.0552(7) Uani 1 1 d . . .
C2 C 0.2038(3) 0.54003(15) 0.24605(16) 0.0498(7) Uani 1 1 d . . .
C1 C 0.0681(3) 0.56690(17) 0.24920(19) 0.0568(7) Uani 1 1 d . . .
C6 C 0.4384(3) 0.55440(18) 0.22653(18) 0.0577(7) Uani 1 1 d . . .
C10 C 0.3008(3) 0.66703(18) 0.2171(2) 0.0616(8) Uani 1 1 d . . .
C4 C 0.3540(3) 0.4304(2) 0.2548(2) 0.0635(8) Uani 1 1 d . . .
C5 C 0.4545(3) 0.4750(2) 0.2391(2) 0.0685(9) Uani 1 1 d . . .
C16 C 0.2019(4) 0.2951(2) 0.5538(2) 0.0852(11) Uani 1 1 d . . .
H16A H 0.1735 0.3418 0.5775 0.102 Uiso 1 1 calc R . .
H16B H 0.2485 0.2645 0.6028 0.102 Uiso 1 1 calc R . .
C8 C 0.5297(3) 0.6765(2) 0.1988(2) 0.0792(10) Uani 1 1 d . . .
H8 H 0.6011 0.7062 0.1891 0.095 Uiso 1 1 calc R . .
C9 C 0.4053(4) 0.7093(2) 0.2016(2) 0.0762(10) Uani 1 1 d . . .
C7 C 0.5445(3) 0.6005(2) 0.2105(2) 0.0722(9) Uani 1 1 d . . .
C12 C -0.0030(4) 0.2959(2) 0.43011(19) 0.0767(9) Uani 1 1 d . . .
H12A H 0.0530 0.3006 0.3875 0.092 Uiso 1 1 calc R . .
H12B H -0.0823 0.2663 0.4032 0.092 Uiso 1 1 calc R . .
C13 C -0.0489(4) 0.3741(2) 0.4495(2) 0.0935(11) Uani 1 1 d . . .
H13A H 0.0291 0.4076 0.4637 0.112 Uiso 1 1 calc R . .
H13B H -0.0891 0.3716 0.5002 0.112 Uiso 1 1 calc R . .
C20 C -0.0097(4) 0.2400(2) 0.5754(2) 0.0885(11) Uani 1 1 d . . .
H20A H 0.0427 0.2096 0.6228 0.106 Uiso 1 1 calc R . .
H20B H -0.0255 0.2890 0.5996 0.106 Uiso 1 1 calc R . .
C17 C 0.3026(4) 0.3155(3) 0.4987(2) 0.1055(14) Uani 1 1 d . . .
H17A H 0.3303 0.2695 0.4731 0.127 Uiso 1 1 calc R . .
H17B H 0.2592 0.3487 0.4513 0.127 Uiso 1 1 calc R . .
C24 C 0.1122(5) 0.1771(2) 0.4717(2) 0.0988(13) Uani 1 1 d . . .
H24A H 0.0294 0.1523 0.4412 0.119 Uiso 1 1 calc R . .
H24B H 0.1666 0.1871 0.4292 0.119 Uiso 1 1 calc R . .
C18 C 0.4252(4) 0.3543(3) 0.5522(3) 0.1153(15) Uani 1 1 d . . .
H18A H 0.4682 0.3204 0.5990 0.138 Uiso 1 1 calc R . .
H18B H 0.3962 0.3993 0.5788 0.138 Uiso 1 1 calc R . .
C25 C 0.1892(7) 0.1231(3) 0.5399(3) 0.175(3) Uani 1 1 d . . .
H25A H 0.1430 0.1191 0.5878 0.210 Uiso 1 1 calc R . .
H25B H 0.2794 0.1431 0.5632 0.210 Uiso 1 1 calc R . .
C14 C -0.1506(4) 0.4065(2) 0.3734(3) 0.1008(12) Uani 1 1 d . . .
H14A H -0.1114 0.4073 0.3222 0.121 Uiso 1 1 calc R . .
H14B H -0.2299 0.3738 0.3606 0.121 Uiso 1 1 calc R . .
C21 C -0.1458(5) 0.2014(3) 0.5426(3) 0.1110(14) Uani 1 1 d . . .
H21A H -0.2000 0.2310 0.4953 0.133 Uiso 1 1 calc R . .
H21B H -0.1320 0.1513 0.5200 0.133 Uiso 1 1 calc R . .
C22 C -0.2201(7) 0.1940(4) 0.6157(4) 0.154(2) Uani 1 1 d . . .
H22A H -0.1656 0.1633 0.6618 0.185 Uiso 1 1 calc R . .
H22B H -0.2282 0.2442 0.6398 0.185 Uiso 1 1 calc R . .
C19 C 0.5286(5) 0.3774(4) 0.5009(3) 0.150(2) Uani 1 1 d . . .
H19A H 0.5548 0.3337 0.4718 0.225 Uiso 1 1 calc R . .
H19B H 0.6069 0.3983 0.5400 0.225 Uiso 1 1 calc R . .
H19C H 0.4899 0.4150 0.4581 0.225 Uiso 1 1 calc R . .
C23 C -0.3534(9) 0.1608(4) 0.5912(6) 0.225(4) Uani 1 1 d . . .
H23A H -0.4158 0.1977 0.5598 0.338 Uiso 1 1 calc R . .
H23B H -0.3825 0.1455 0.6429 0.338 Uiso 1 1 calc R . .
H23C H -0.3508 0.1173 0.5546 0.338 Uiso 1 1 calc R . .
C15 C -0.1926(5) 0.4849(3) 0.3914(4) 0.1402(19) Uani 1 1 d . . .
H15A H -0.2236 0.4852 0.4450 0.210 Uiso 1 1 calc R . .
H15B H -0.2646 0.5013 0.3442 0.210 Uiso 1 1 calc R . .
H15C H -0.1167 0.5187 0.3965 0.210 Uiso 1 1 calc R . .
C26 C 0.2007(11) 0.0415(5) 0.4998(5) 0.238(6) Uani 1 1 d . . .
H26A H 0.2088 0.0021 0.5441 0.285 Uiso 1 1 calc R . .
H26B H 0.1231 0.0305 0.4526 0.285 Uiso 1 1 calc R . .
H10 H 0.220(3) 0.6898(17) 0.2191(18) 0.066(9) Uiso 1 1 d . . .
H9 H 0.392(3) 0.7609(19) 0.1907(19) 0.073(10) Uiso 1 1 d . . .
H7 H 0.629(3) 0.5766(19) 0.212(2) 0.086(10) Uiso 1 1 d . . .
H5 H 0.539(3) 0.4541(17) 0.2379(18) 0.067(8) Uiso 1 1 d . . .
H4 H 0.366(3) 0.3755(19) 0.2618(19) 0.078(10) Uiso 1 1 d . . .
H1 H 0.005(3) 0.531(2) 0.257(2) 0.092(11) Uiso 1 1 d . . .
C27 C 0.2982(15) 0.0469(7) 0.4744(9) 0.339(8) Uani 1 1 d . . .
H27A H 0.3302 0.0985 0.4814 0.509 Uiso 1 1 calc R . .
H27B H 0.2800 0.0333 0.4136 0.509 Uiso 1 1 calc R . .
H27C H 0.3662 0.0135 0.5071 0.509 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.399(3) . ?
O2 C3 1.345(3) . ?
N1 C1 1.262(3) . ?
N2 C12 1.506(4) . ?
N2 C24 1.516(4) . ?
N2 C16 1.520(4) . ?
N2 C20 1.524(4) . ?
C11 C10 1.412(4) . ?
C11 C6 1.419(4) . ?
C11 C2 1.440(4) . ?
C3 C2 1.392(4) . ?
C3 C4 1.415(4) . ?
C2 C1 1.463(4) . ?
C6 C7 1.410(4) . ?
C6 C5 1.414(4) . ?
C10 C9 1.358(4) . ?
C4 C5 1.348(4) . ?
C16 C17 1.518(5) . ?
C8 C7 1.353(5) . ?
C8 C9 1.394(5) . ?
C12 C13 1.503(5) . ?
C13 C14 1.504(5) . ?
C20 C21 1.518(6) . ?
C17 C18 1.498(6) . ?
C24 C25 1.510(6) . ?
C18 C19 1.510(6) . ?
C25 C26 1.580(9) . ?
C14 C15 1.487(6) . ?
C21 C22 1.509(6) . ?
C22 C23 1.441(9) . ?
C26 C27 1.147(13) . ?

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
C1 N1 O1 112.0(2) . . ?
C12 N2 C24 105.7(2) . . ?
C12 N2 C16 111.7(3) . . ?
C24 N2 C16 111.1(3) . . ?
C12 N2 C20 110.9(3) . . ?
C24 N2 C20 111.0(3) . . ?
C16 N2 C20 106.6(2) . . ?
C10 C11 C6 116.3(3) . . ?
C10 C11 C2 124.1(3) . . ?
C6 C11 C2 119.6(3) . . ?
O2 C3 C2 119.5(2) . . ?
O2 C3 C4 119.8(3) . . ?
C2 C3 C4 120.7(3) . . ?
C3 C2 C11 118.8(2) . . ?
C3 C2 C1 116.2(2) . . ?
C11 C2 C1 124.9(3) . . ?
N1 C1 C2 126.1(3) . . ?
C7 C6 C5 121.6(3) . . ?
C7 C6 C11 120.0(3) . . ?
C5 C6 C11 118.5(3) . . ?
C9 C10 C11 121.9(3) . . ?
C5 C4 C3 120.2(3) . . ?
C4 C5 C6 122.1(3) . . ?
C17 C16 N2 116.5(3) . . ?
C7 C8 C9 118.5(3) . . ?
C10 C9 C8 121.5(3) . . ?
C8 C7 C6 121.8(3) . . ?
C13 C12 N2 115.6(3) . . ?
C12 C13 C14 111.9(3) . . ?
C21 C20 N2 116.0(3) . . ?
C18 C17 C16 111.4(3) . . ?
C25 C24 N2 114.5(3) . . ?
C17 C18 C19 114.2(4) . . ?
C24 C25 C26 111.1(4) . . ?
C15 C14 C13 112.0(4) . . ?
C22 C21 C20 110.4(4) . . ?
C23 C22 C21 115.2(6) . . ?
C27 C26 C25 102.0(12) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.036
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_publication_text
_database_code_depnum_ccdc_archive 'CCDC 1012762'
_audit_update_record             
;
2014-08-28 deposited with the CCDC.
2015-02-04 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2 4 dihydroxy aromatic aldoxime
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H13 N2 O6, C16 H36 N'
_chemical_formula_sum            'C30 H49  N3 O6'
_chemical_formula_weight         547.72

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           Monoclinic
_symmetry_space_group_name_H-M   'C2/c  '
_space_group_name_Hall           '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.2317(7)
_cell_length_b                   9.6547(4)
_cell_length_c                   20.2299(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.931(3)
_cell_angle_gamma                90.00
_cell_volume                     3122.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1192
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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            17739
_diffrn_reflns_av_R_equivalents  0.1010
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2711
_reflns_number_gt                1431
_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. 

DFIX .85 0.02 H1A O1  O2 H2A  O3 H3A
DFIX .85 0.02 O1 H1B
DFIX .70 0.02 O1 H1B
DFIX .85 0.02 H1B O1
DFIX 1.54 0.02 O1 H1
DFIX 0.86 0.02 O1 H1
DFIX 0.86 0.02 O1 H1
DFIX 0.86 0.02 O1 H1
DFIX 0.86 0.02 O1 H1
DFIX 1.414 0.02 C9 C16
;

_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)+(0.0000P)²+7.9000P] 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         2711
_refine_ls_number_parameters     189
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0736
_refine_ls_wR_factor_ref         0.1636
_refine_ls_wR_factor_gt          0.1531
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      5.457
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0002(7) 0.3462(14) 0.3111(7) 0.068(4) Uani 1 1 d D . .
O2 O 0.7512(9) 0.6093(17) 0.2631(7) 0.073(4) Uani 1 1 d D . .
O3 O 0.6350(10) 0.7765(19) 0.4022(9) 0.092(5) Uani 1 1 d D . .
N2 N 0.0000 0.887(2) 0.2500 0.059(6) Uani 1 2 d S . .
N1 N 0.6894(10) 0.7083(17) 0.3659(8) 0.065(4) Uani 1 1 d . . .
C5 C 0.9408(11) 0.4205(19) 0.3320(10) 0.054(5) Uani 1 1 d . . .
C4 C 0.8740(11) 0.4759(18) 0.2869(9) 0.054(5) Uani 1 1 d . . .
H4 H 0.8701 0.4595 0.2412 0.064 Uiso 1 1 calc R . .
C3 C 0.8138(10) 0.5551(19) 0.3099(9) 0.053(5) Uani 1 1 d . . .
C1 C 0.7534(12) 0.656(2) 0.4039(10) 0.063(5) Uani 1 1 d . . .
H1A H 0.7588 0.6675 0.4501 0.076 Uiso 1 1 calc RD . .
C2 C 0.8165(11) 0.5796(19) 0.3785(9) 0.053(5) Uani 1 1 d . . .
C6 C 0.9442(11) 0.445(2) 0.4002(10) 0.064(5) Uani 1 1 d . . .
H6 H 0.9879 0.4083 0.4311 0.077 Uiso 1 1 calc R . .
C7 C 0.8834(11) 0.523(2) 0.4221(10) 0.063(5) Uani 1 1 d . . .
H7 H 0.8872 0.5385 0.4679 0.075 Uiso 1 1 calc R . .
C14 C 0.0629(13) 0.792(2) 0.2923(11) 0.075(6) Uani 1 1 d . . .
H14A H 0.0323 0.7268 0.3154 0.089 Uiso 1 1 calc R . .
H14B H 0.0913 0.7388 0.2622 0.089 Uiso 1 1 calc R . .
C8 C -0.0414(14) 0.983(2) 0.2938(12) 0.082(7) Uani 1 1 d . . .
H8A H 0.0015 1.0427 0.3181 0.098 Uiso 1 1 calc R . .
H8B H -0.0803 1.0417 0.2646 0.098 Uiso 1 1 calc R . .
C11 C 0.1276(16) 0.860(3) 0.3431(13) 0.103(8) Uani 1 1 d . . .
H11A H 0.1002 0.9146 0.3731 0.124 Uiso 1 1 calc R . .
H11B H 0.1605 0.9221 0.3205 0.124 Uiso 1 1 calc R . .
C9 C -0.104(2) 1.029(4) 0.3948(17) 0.152(15) Uani 1 1 d . . .
H9A H -0.0527 1.0812 0.4087 0.183 Uiso 1 1 calc R . .
H9B H -0.1457 1.0930 0.3725 0.183 Uiso 1 1 calc R . .
C10 C -0.0873(18) 0.917(3) 0.3434(14) 0.109(9) Uani 1 1 d . . .
H10A H -0.0543 0.8422 0.3664 0.131 Uiso 1 1 calc R . .
H10B H -0.1399 0.8792 0.3205 0.131 Uiso 1 1 calc R . .
C12 C 0.1860(17) 0.755(3) 0.3843(14) 0.117(10) Uani 1 1 d . . .
H12A H 0.2116 0.6986 0.3536 0.140 Uiso 1 1 calc R . .
H12B H 0.2305 0.8053 0.4123 0.140 Uiso 1 1 calc R . .
C15 C 0.149(2) 0.665(3) 0.4259(18) 0.150(13) Uani 1 1 d . . .
H15A H 0.1214 0.7187 0.4556 0.226 Uiso 1 1 calc R . .
H15B H 0.1912 0.6083 0.4517 0.226 Uiso 1 1 calc R . .
H15C H 0.1086 0.6069 0.3985 0.226 Uiso 1 1 calc R . .
C16 C -0.130(3) 0.979(5) 0.450(2) 0.24(3) Uani 1 1 d . . .
H16A H -0.1855 0.9433 0.4379 0.360 Uiso 1 1 calc R . .
H16B H -0.1295 1.0523 0.4822 0.360 Uiso 1 1 calc R . .
H16C H -0.0929 0.9065 0.4692 0.360 Uiso 1 1 calc R . .
H3A H 0.599(11) 0.80(2) 0.372(9) 0.10(10) Uiso 1 1 d D . .
H2A H 0.725(13) 0.67(2) 0.284(11) 0.10(9) Uiso 1 1 d D . .
H1 H 1.0000 0.356(17) 0.2500 0.13(11) Uiso 1 2 d SD . .


_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 C5 1.33(2) . ?
O2 C3 1.37(2) . ?
O3 N1 1.41(2) . ?
N2 C8 1.52(2) . ?
N2 C8 1.52(2) 2 ?
N2 C14 1.52(2) 2 ?
N2 C14 1.52(2) . ?
N1 C1 1.29(2) . ?
C5 C6 1.39(3) . ?
C5 C4 1.40(2) . ?
C4 C3 1.38(2) . ?
C3 C2 1.40(2) . ?
C1 C2 1.43(2) . ?
C2 C7 1.39(2) . ?
C6 C7 1.38(2) . ?
C14 C11 1.49(3) . ?
C8 C10 1.49(3) . ?
C11 C12 1.53(3) . ?
C9 C16 1.35(5) . ?
C9 C10 1.56(4) . ?
C12 C15 1.41(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
C8 N2 C8 104(2) . 2 ?
C8 N2 C14 112.0(12) . 2 ?
C8 N2 C14 111.2(12) 2 2 ?
C8 N2 C14 111.2(12) . . ?
C8 N2 C14 112.0(12) 2 . ?
C14 N2 C14 106(2) 2 . ?
C1 N1 O3 112.9(16) . . ?
O1 C5 C6 119.9(17) . . ?
O1 C5 C4 121.6(17) . . ?
C6 C5 C4 118.4(17) . . ?
C3 C4 C5 120.4(17) . . ?
O2 C3 C4 117.5(16) . . ?
O2 C3 C2 121.0(16) . . ?
C4 C3 C2 121.5(17) . . ?
N1 C1 C2 123.0(18) . . ?
C7 C2 C3 116.8(16) . . ?
C7 C2 C1 120.3(17) . . ?
C3 C2 C1 122.9(17) . . ?
C7 C6 C5 120.2(18) . . ?
C6 C7 C2 122.5(18) . . ?
C11 C14 N2 116.6(18) . . ?
C10 C8 N2 117.0(19) . . ?
C14 C11 C12 112(2) . . ?
C16 C9 C10 115(3) . . ?
C8 C10 C9 108(2) . . ?
C15 C12 C11 116(3) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_publication_text
_database_code_depnum_ccdc_archive 'CCDC 1012763'
_audit_update_record             
;
2014-08-28 deposited with the CCDC.
2015-02-04 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H36 N, 2(C7 H7 N O3), F'
_chemical_formula_sum            'C30 H50 F N3 O6'
_chemical_formula_weight         567.73

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           Monoclinic
_symmetry_space_group_name_H-M   Pc
_space_group_name_Hall           'P -2yc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   9.5189(7)
_cell_length_b                   9.4321(7)
_cell_length_c                   18.7965(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.203(4)
_cell_angle_gamma                90.00
_cell_volume                     1655.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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            18857
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         25.24
_reflns_number_total             2989
_reflns_number_gt                1766
_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.

DFIX 0.84 0.02 H4A O4 
;

_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)+(0.0600P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_number_reflns         5031
_refine_ls_number_parameters     374
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1024
_refine_ls_wR_factor_gt          0.0919
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
C6 C 0.2818(2) 0.1093(2) 0.06309(12) 0.0578(6) Uani 1 1 d . . .
C1 C 0.3113(3) 0.2556(3) 0.06586(12) 0.0617(6) Uani 1 1 d . . .
C5 C 0.2209(2) 0.0472(2) 0.11765(12) 0.0629(6) Uani 1 1 d . . .
C4 C 0.1931(3) 0.1324(3) 0.17428(12) 0.0729(7) Uani 1 1 d . . .
H4 H 0.1534 0.0916 0.2109 0.087 Uiso 1 1 calc R . .
C2 C 0.2823(3) 0.3356(3) 0.12245(14) 0.0696(7) Uani 1 1 d . . .
H2 H 0.3025 0.4321 0.1243 0.084 Uiso 1 1 calc R . .
C7 C 0.1880(3) -0.1037(3) 0.11648(14) 0.0722(7) Uani 1 1 d . . .
H7 H 0.1433 -0.1418 0.1520 0.087 Uiso 1 1 calc R . .
C3 C 0.2230(3) 0.2737(3) 0.17697(13) 0.0765(8) Uani 1 1 d . . .
H3 H 0.2038 0.3285 0.2151 0.092 Uiso 1 1 calc R . .
C11 C 0.5450(4) 0.8480(3) 0.81980(18) 0.0955(10) Uani 1 1 d . . .
H11 H 0.4765 0.8920 0.7847 0.115 Uiso 1 1 calc R . .
O2 O 0.3150(2) 0.03588(16) 0.00678(8) 0.0755(5) Uani 1 1 d . . .
H2A H 0.3080 -0.0493 0.0140 0.113 Uiso 1 1 calc R . .
O1 O 0.3706(2) 0.30859(16) 0.01126(10) 0.0790(5) Uani 1 1 d . . .
H1 H 0.3491 0.3925 0.0050 0.118 Uiso 1 1 calc R . .
O3 O 0.1823(3) -0.32520(17) 0.07523(11) 0.0921(6) Uani 1 1 d . . .
H3A H 0.2154 -0.3741 0.0464 0.138 Uiso 1 1 calc R . .
N1 N 0.2195(2) -0.18381(19) 0.06766(12) 0.0717(6) Uani 1 1 d . . .
C14 C 0.7484(3) 0.7204(2) 0.92518(13) 0.0636(6) Uani 1 1 d . . .
C13 C 0.7890(3) 0.7715(3) 0.86241(13) 0.0698(7) Uani 1 1 d . . .
C9 C 0.6072(3) 0.7290(2) 0.93403(13) 0.0681(7) Uani 1 1 d . . .
C12 C 0.6842(4) 0.8363(3) 0.80963(15) 0.0937(9) Uani 1 1 d . . .
H12 H 0.7088 0.8717 0.7675 0.112 Uiso 1 1 calc R . .
C15 C 0.9325(3) 0.7548(3) 0.84917(15) 0.0811(8) Uani 1 1 d . . .
H15 H 0.9538 0.7905 0.8064 0.097 Uiso 1 1 calc R . .
C10 C 0.5070(3) 0.7950(3) 0.88147(17) 0.0805(8) Uani 1 1 d . . .
H10 H 0.4130 0.8036 0.8879 0.097 Uiso 1 1 calc R . .
O5 O 0.84367(19) 0.6581(2) 0.97989(10) 0.0868(5) Uani 1 1 d . . .
H5 H 0.9186 0.6418 0.9660 0.130 Uiso 1 1 calc R . .
O6 O 1.1591(3) 0.6824(3) 0.87036(13) 0.1094(7) Uani 1 1 d . . .
H6 H 1.2217 0.6549 0.9039 0.164 Uiso 1 1 calc R . .
O4 O 0.5760(2) 0.6714(2) 0.99560(11) 0.0948(6) Uani 1 1 d D . .
N2 N 1.0307(3) 0.6931(2) 0.89383(13) 0.0783(6) Uani 1 1 d . . .
C24 C 0.6397(3) 0.1983(2) -0.06202(12) 0.0634(6) Uani 1 1 d . . .
H24A H 0.6559 0.1141 -0.0889 0.076 Uiso 1 1 calc R . .
H24B H 0.5582 0.1794 -0.0394 0.076 Uiso 1 1 calc R . .
C28 C 0.9015(3) 0.2622(3) -0.03347(13) 0.0669(6) Uani 1 1 d . . .
H28A H 0.8846 0.3544 -0.0564 0.080 Uiso 1 1 calc R . .
H28B H 0.9826 0.2717 0.0064 0.080 Uiso 1 1 calc R . .
C20 C 0.7371(3) 0.3435(2) 0.04575(12) 0.0660(6) Uani 1 1 d . . .
H20A H 0.7198 0.4285 0.0163 0.079 Uiso 1 1 calc R . .
H20B H 0.6489 0.3208 0.0618 0.079 Uiso 1 1 calc R . .
C19 C 0.8032(3) 0.0860(3) 0.04116(13) 0.0681(6) Uani 1 1 d . . .
H19A H 0.8210 0.0114 0.0085 0.082 Uiso 1 1 calc R . .
H19B H 0.8907 0.0997 0.0767 0.082 Uiso 1 1 calc R . .
C25 C 0.6011(3) 0.3195(3) -0.11530(13) 0.0763(7) Uani 1 1 d . . .
H25A H 0.5895 0.4060 -0.0891 0.092 Uiso 1 1 calc R . .
H25B H 0.6779 0.3342 -0.1417 0.092 Uiso 1 1 calc R . .
C30 C 1.0595(3) 0.2178(3) -0.12279(14) 0.0861(8) Uani 1 1 d . . .
H30A H 1.1434 0.2354 -0.0854 0.103 Uiso 1 1 calc R . .
H30B H 1.0288 0.3077 -0.1457 0.103 Uiso 1 1 calc R . .
C26 C 0.4641(3) 0.2870(3) -0.16798(14) 0.0848(8) Uani 1 1 d . . .
H26A H 0.3892 0.2677 -0.1409 0.102 Uiso 1 1 calc R . .
H26B H 0.4778 0.2020 -0.1949 0.102 Uiso 1 1 calc R . .
C29 C 0.9420(3) 0.1596(3) -0.08821(15) 0.0803(8) Uani 1 1 d . . .
H29A H 0.9733 0.0708 -0.0642 0.096 Uiso 1 1 calc R . .
H29B H 0.8585 0.1401 -0.1255 0.096 Uiso 1 1 calc R . .
C21 C 0.8499(3) 0.3765(3) 0.11158(14) 0.0837(8) Uani 1 1 d . . .
H21A H 0.9377 0.4050 0.0967 0.100 Uiso 1 1 calc R . .
H21B H 0.8698 0.2925 0.1416 0.100 Uiso 1 1 calc R . .
C18 C 0.6880(3) 0.0361(3) 0.08035(14) 0.0761(7) Uani 1 1 d . . .
H18A H 0.6601 0.1138 0.1084 0.091 Uiso 1 1 calc R . .
H18B H 0.6044 0.0074 0.0451 0.091 Uiso 1 1 calc R . .
C17 C 0.7378(3) -0.0859(3) 0.12988(15) 0.0862(8) Uani 1 1 d . . .
H17A H 0.8182 -0.0553 0.1667 0.103 Uiso 1 1 calc R . .
H17B H 0.7713 -0.1611 0.1022 0.103 Uiso 1 1 calc R . .
C31 C 1.0993(4) 0.1187(5) -0.17872(17) 0.1161(11) Uani 1 1 d . . .
H31A H 1.0144 0.0904 -0.2121 0.174 Uiso 1 1 calc R . .
H31B H 1.1460 0.0364 -0.1550 0.174 Uiso 1 1 calc R . .
H31C H 1.1630 0.1663 -0.2047 0.174 Uiso 1 1 calc R . .
C16 C 0.6213(4) -0.1442(3) 0.16690(17) 0.1060(10) Uani 1 1 d . . .
H16A H 0.5495 -0.1906 0.1316 0.159 Uiso 1 1 calc R . .
H16B H 0.5784 -0.0678 0.1888 0.159 Uiso 1 1 calc R . .
H16C H 0.6625 -0.2111 0.2036 0.159 Uiso 1 1 calc R . .
C27 C 0.4158(4) 0.4060(4) -0.22095(17) 0.1202(11) Uani 1 1 d . . .
H27A H 0.4909 0.4284 -0.2466 0.180 Uiso 1 1 calc R . .
H27B H 0.3939 0.4882 -0.1950 0.180 Uiso 1 1 calc R . .
H27C H 0.3319 0.3770 -0.2549 0.180 Uiso 1 1 calc R . .
C22 C 0.7983(4) 0.4945(3) 0.15457(15) 0.1072(11) Uani 1 1 d . . .
H22A H 0.7638 0.5716 0.1216 0.129 Uiso 1 1 calc R . .
H22B H 0.7174 0.4597 0.1739 0.129 Uiso 1 1 calc R . .
C23 C 0.9053(6) 0.5520(4) 0.2151(2) 0.166(2) Uani 1 1 d . . .
H23A H 0.9870 0.5855 0.1971 0.249 Uiso 1 1 calc R . .
H23B H 0.9347 0.4789 0.2504 0.249 Uiso 1 1 calc R . .
H23C H 0.8640 0.6291 0.2373 0.249 Uiso 1 1 calc R . .
N3 N 0.7707(2) 0.22235(18) -0.00241(9) 0.0595(5) Uani 1 1 d . . .
F1 F 0.32049(15) 0.57057(14) 0.98217(8) 0.0839(4) Uani 1 1 d . . .
H4A H 0.491(3) 0.642(5) 0.980(2) 0.151(17) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C6 O2 1.353(3) . ?
C6 C5 1.401(3) . ?
C6 C1 1.407(3) . ?
C1 O1 1.359(3) . ?
C1 C2 1.375(3) . ?
C5 C4 1.399(3) . ?
C5 C7 1.457(3) . ?
C4 C3 1.362(4) . ?
C2 C3 1.391(4) . ?
C7 N1 1.269(3) . ?
C11 C10 1.374(5) . ?
C11 C12 1.380(5) . ?
O3 N1 1.394(2) . ?
C14 O5 1.365(3) . ?
C14 C9 1.388(3) . ?
C14 C13 1.397(3) . ?
C13 C12 1.403(4) . ?
C13 C15 1.444(4) . ?
C9 O4 1.363(3) . ?
C9 C10 1.381(4) . ?
C15 N2 1.270(3) . ?
O6 N2 1.381(3) . ?
C24 C25 1.518(3) . ?
C24 N3 1.523(3) . ?
C28 C29 1.516(4) . ?
C28 N3 1.521(3) . ?
C20 C21 1.505(3) . ?
C20 N3 1.530(3) . ?
C19 C18 1.510(3) . ?
C19 N3 1.524(3) . ?
C25 C26 1.508(4) . ?
C30 C29 1.502(4) . ?
C30 C31 1.509(4) . ?
C26 C27 1.512(4) . ?
C21 C22 1.513(4) . ?
C18 C17 1.498(3) . ?
C17 C16 1.522(4) . ?
C22 C23 1.476(5) . ?

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 C6 C5 123.47(19) . . ?
O2 C6 C1 117.1(2) . . ?
C5 C6 C1 119.4(2) . . ?
O1 C1 C2 123.9(2) . . ?
O1 C1 C6 116.2(2) . . ?
C2 C1 C6 119.8(2) . . ?
C4 C5 C6 118.9(2) . . ?
C4 C5 C7 120.0(2) . . ?
C6 C5 C7 121.1(2) . . ?
C3 C4 C5 121.4(2) . . ?
C1 C2 C3 120.7(2) . . ?
N1 C7 C5 120.8(2) . . ?
C4 C3 C2 119.7(2) . . ?
C10 C11 C12 120.3(3) . . ?
C7 N1 O3 113.3(2) . . ?
O5 C14 C9 116.9(2) . . ?
O5 C14 C13 122.2(2) . . ?
C9 C14 C13 120.9(2) . . ?
C14 C13 C12 118.2(3) . . ?
C14 C13 C15 122.3(2) . . ?
C12 C13 C15 119.5(3) . . ?
O4 C9 C10 123.6(3) . . ?
O4 C9 C14 117.1(2) . . ?
C10 C9 C14 119.4(2) . . ?
C11 C12 C13 120.4(3) . . ?
N2 C15 C13 122.4(3) . . ?
C11 C10 C9 120.6(3) . . ?
C15 N2 O6 113.9(2) . . ?
C25 C24 N3 115.57(19) . . ?
C29 C28 N3 115.9(2) . . ?
C21 C20 N3 116.33(19) . . ?
C18 C19 N3 115.80(19) . . ?
C26 C25 C24 110.3(2) . . ?
C29 C30 C31 112.6(3) . . ?
C25 C26 C27 113.3(3) . . ?
C30 C29 C28 111.6(2) . . ?
C20 C21 C22 109.7(2) . . ?
C17 C18 C19 111.7(2) . . ?
C18 C17 C16 113.0(3) . . ?
C23 C22 C21 115.8(3) . . ?
C28 N3 C24 111.64(17) . . ?
C28 N3 C19 108.63(17) . . ?
C24 N3 C19 108.72(16) . . ?
C28 N3 C20 108.86(17) . . ?
C24 N3 C20 108.13(17) . . ?
C19 N3 C20 110.86(16) . . ?

_diffrn_measured_fraction_theta_max 0.99
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.99
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.111
_refine_diff_density_rms         0.028
