# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_niapf6
_database_code_depnum_ccdc_archive 'CCDC 1486608'
_audit_update_record             
;
2016-06-20 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H27 F6 N2 O3 P'
_chemical_formula_weight         452.38

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'
P P 0.1023 0.0942 '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                   6.241(4)
_cell_length_b                   9.506(7)
_cell_length_c                   18.651(13)
_cell_angle_alpha                99.873(15)
_cell_angle_beta                 93.890(15)
_cell_angle_gamma                105.674(14)
_cell_volume                     1042.0(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4224
_cell_measurement_theta_min      2.7207
_cell_measurement_theta_max      26.6185

_exptl_crystal_description       Columnar
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5427
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13906
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_sigmaI/netI    0.0613
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.12
_diffrn_reflns_theta_max         26.82
_reflns_number_total             4303
_reflns_number_gt                2786
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1366P)²+0.3654P] 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         4303
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0748
_refine_ls_wR_factor_ref         0.2456
_refine_ls_wR_factor_gt          0.2235
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_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
P1 P 0.31441(15) 0.17201(11) 0.41246(5) 0.0441(3) Uani 1 1 d . . .
F1 F 0.5641(4) 0.1604(4) 0.41842(15) 0.0815(9) Uani 1 1 d . . .
F2 F 0.0675(4) 0.1830(4) 0.40564(16) 0.0832(9) Uani 1 1 d . . .
F3 F 0.2278(6) 0.0071(3) 0.36537(18) 0.0908(10) Uani 1 1 d . . .
F4 F 0.4011(7) 0.3333(4) 0.4596(3) 0.1337(16) Uani 1 1 d . . .
F5 F 0.2784(5) 0.1075(5) 0.48483(16) 0.1099(13) Uani 1 1 d . . .
F6 F 0.3535(5) 0.2339(4) 0.33830(17) 0.0852(10) Uani 1 1 d . . .
O1 O 0.3804(5) 0.3634(3) 0.72101(17) 0.0585(8) Uani 1 1 d . . .
O2 O -0.0939(5) 0.9432(3) 1.22058(16) 0.0567(8) Uani 1 1 d . . .
O3 O -0.0078(5) 0.7315(3) 1.22234(17) 0.0584(8) Uani 1 1 d . . .
H3A H -0.1340 0.7060 1.2373 0.088 Uiso 1 1 calc R . .
N1 N 1.0015(4) 0.5684(3) 0.67702(14) 0.0337(6) Uani 1 1 d . . .
N2 N 0.3641(6) 0.1413(4) 0.6530(2) 0.0655(11) Uani 1 1 d . . .
H2B H 0.2370 0.0970 0.6680 0.079 Uiso 1 1 calc R . .
H2A H 0.4274 0.0896 0.6218 0.079 Uiso 1 1 calc R . .
C1 C 0.7979(5) 0.4968(3) 0.69148(18) 0.0329(7) Uani 1 1 d . . .
H1 H 0.7333 0.5431 0.7301 0.039 Uiso 1 1 calc R . .
C2 C 0.6787(5) 0.3571(4) 0.65163(18) 0.0353(7) Uani 1 1 d . . .
C3 C 0.7708(6) 0.2946(4) 0.59317(19) 0.0403(8) Uani 1 1 d . . .
H3 H 0.6922 0.1998 0.5642 0.048 Uiso 1 1 calc R . .
C4 C 0.9774(6) 0.3713(4) 0.5775(2) 0.0494(10) Uani 1 1 d . . .
H4 H 1.0409 0.3302 0.5370 0.059 Uiso 1 1 calc R . .
C5 C 1.0913(6) 0.5064(4) 0.6202(2) 0.0445(9) Uani 1 1 d . . .
H5 H 1.2355 0.5574 0.6098 0.053 Uiso 1 1 calc R . .
C6 C 1.1294(6) 0.7146(4) 0.7243(2) 0.0410(8) Uani 1 1 d . . .
H6B H 1.0242 0.7730 0.7387 0.049 Uiso 1 1 calc R . .
H6A H 1.2377 0.7716 0.6959 0.049 Uiso 1 1 calc R . .
C7 C 1.2554(6) 0.6945(4) 0.7931(2) 0.0453(9) Uani 1 1 d . . .
H7B H 1.3608 0.7922 0.8168 0.054 Uiso 1 1 calc R . .
H7A H 1.3460 0.6261 0.7779 0.054 Uiso 1 1 calc R . .
C8 C 1.1109(6) 0.6337(4) 0.8505(2) 0.0444(9) Uani 1 1 d . . .
H8B H 0.9995 0.5385 0.8266 0.053 Uiso 1 1 calc R . .
H8A H 1.2083 0.6119 0.8887 0.053 Uiso 1 1 calc R . .
C9 C 0.9883(7) 0.7383(4) 0.8870(2) 0.0496(10) Uani 1 1 d . . .
H9B H 0.8981 0.7650 0.8486 0.060 Uiso 1 1 calc R . .
H9A H 1.1001 0.8311 0.9135 0.060 Uiso 1 1 calc R . .
C10 C 0.8348(7) 0.6744(4) 0.9405(2) 0.0492(9) Uani 1 1 d . . .
H10B H 0.7127 0.5880 0.9132 0.059 Uiso 1 1 calc R . .
H10A H 0.9211 0.6380 0.9761 0.059 Uiso 1 1 calc R . .
C11 C 0.7329(7) 0.7866(4) 0.9821(2) 0.0529(10) Uani 1 1 d . . .
H11B H 0.6503 0.8245 0.9462 0.063 Uiso 1 1 calc R . .
H11A H 0.8557 0.8721 1.0098 0.063 Uiso 1 1 calc R . .
C12 C 0.5745(6) 0.7266(4) 1.0352(2) 0.0476(9) Uani 1 1 d . . .
H12B H 0.6554 0.6880 1.0712 0.057 Uiso 1 1 calc R . .
H12A H 0.4490 0.6426 1.0078 0.057 Uiso 1 1 calc R . .
C13 C 0.4808(7) 0.8455(4) 1.0758(2) 0.0498(9) Uani 1 1 d . . .
H13B H 0.6064 0.9262 1.1054 0.060 Uiso 1 1 calc R . .
H13A H 0.4102 0.8889 1.0393 0.060 Uiso 1 1 calc R . .
C14 C 0.3098(6) 0.7886(4) 1.1257(2) 0.0460(9) Uani 1 1 d . . .
H14B H 0.1792 0.7121 1.0960 0.055 Uiso 1 1 calc R . .
H14A H 0.3770 0.7407 1.1608 0.055 Uiso 1 1 calc R . .
C15 C 0.2310(7) 0.9120(4) 1.1678(2) 0.0574(11) Uani 1 1 d . . .
H15B H 0.3553 0.9751 1.2052 0.069 Uiso 1 1 calc R . .
H15A H 0.2014 0.9750 1.1333 0.069 Uiso 1 1 calc R . .
C16 C 0.0259(6) 0.8657(4) 1.2055(2) 0.0424(8) Uani 1 1 d . . .
C17 C 0.4608(6) 0.2863(4) 0.6776(2) 0.0399(8) 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
P1 F4 1.563(3) . ?
P1 F2 1.571(3) . ?
P1 F5 1.581(3) . ?
P1 F1 1.590(3) . ?
P1 F3 1.590(3) . ?
P1 F6 1.602(3) . ?
O1 C17 1.223(4) . ?
O2 C16 1.199(4) . ?
O3 C16 1.330(4) . ?
O3 H3A 0.8400 . ?
N1 C1 1.339(4) . ?
N1 C5 1.354(4) . ?
N1 C6 1.494(4) . ?
N2 C17 1.331(5) . ?
N2 H2B 0.8800 . ?
N2 H2A 0.8800 . ?
C1 C2 1.387(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.386(4) . ?
C2 C17 1.498(5) . ?
C3 C4 1.377(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.366(5) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.526(6) . ?
C6 H6B 0.9900 . ?
C6 H6A 0.9900 . ?
C7 C8 1.536(5) . ?
C7 H7B 0.9900 . ?
C7 H7A 0.9900 . ?
C8 C9 1.513(5) . ?
C8 H8B 0.9900 . ?
C8 H8A 0.9900 . ?
C9 C10 1.519(5) . ?
C9 H9B 0.9900 . ?
C9 H9A 0.9900 . ?
C10 C11 1.514(5) . ?
C10 H10B 0.9900 . ?
C10 H10A 0.9900 . ?
C11 C12 1.519(5) . ?
C11 H11B 0.9900 . ?
C11 H11A 0.9900 . ?
C12 C13 1.522(5) . ?
C12 H12B 0.9900 . ?
C12 H12A 0.9900 . ?
C13 C14 1.515(5) . ?
C13 H13B 0.9900 . ?
C13 H13A 0.9900 . ?
C14 C15 1.510(5) . ?
C14 H14B 0.9900 . ?
C14 H14A 0.9900 . ?
C15 C16 1.501(5) . ?
C15 H15B 0.9900 . ?
C15 H15A 0.9900 . ?

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
F4 P1 F2 91.13(19) . . ?
F4 P1 F5 89.8(3) . . ?
F2 P1 F5 90.83(17) . . ?
F4 P1 F1 89.24(19) . . ?
F2 P1 F1 179.38(16) . . ?
F5 P1 F1 89.67(17) . . ?
F4 P1 F3 179.2(2) . . ?
F2 P1 F3 89.34(18) . . ?
F5 P1 F3 89.6(2) . . ?
F1 P1 F3 90.30(17) . . ?
F4 P1 F6 91.3(2) . . ?
F2 P1 F6 90.12(15) . . ?
F5 P1 F6 178.53(19) . . ?
F1 P1 F6 89.37(15) . . ?
F3 P1 F6 89.32(19) . . ?
C16 O3 H3A 109.5 . . ?
C1 N1 C5 119.6(3) . . ?
C1 N1 C6 120.0(2) . . ?
C5 N1 C6 120.5(3) . . ?
C17 N2 H2B 120.0 . . ?
C17 N2 H2A 120.0 . . ?
H2B N2 H2A 120.0 . . ?
N1 C1 C2 121.9(3) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 C17 126.0(3) . . ?
C1 C2 C17 115.8(3) . . ?
C4 C3 C2 119.3(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
N1 C5 C4 120.9(3) . . ?
N1 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
N1 C6 C7 111.8(3) . . ?
N1 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
N1 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
H6B C6 H6A 107.9 . . ?
C6 C7 C8 116.2(3) . . ?
C6 C7 H7B 108.2 . . ?
C8 C7 H7B 108.2 . . ?
C6 C7 H7A 108.2 . . ?
C8 C7 H7A 108.2 . . ?
H7B C7 H7A 107.4 . . ?
C9 C8 C7 114.1(3) . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
H8B C8 H8A 107.6 . . ?
C8 C9 C10 114.1(3) . . ?
C8 C9 H9B 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9A 108.7 . . ?
H9B C9 H9A 107.6 . . ?
C11 C10 C9 113.0(3) . . ?
C11 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
H10B C10 H10A 107.8 . . ?
C10 C11 C12 114.8(3) . . ?
C10 C11 H11B 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
H11B C11 H11A 107.5 . . ?
C11 C12 C13 112.0(3) . . ?
C11 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
H12B C12 H12A 107.9 . . ?
C14 C13 C12 114.1(3) . . ?
C14 C13 H13B 108.7 . . ?
C12 C13 H13B 108.7 . . ?
C14 C13 H13A 108.7 . . ?
C12 C13 H13A 108.7 . . ?
H13B C13 H13A 107.6 . . ?
C15 C14 C13 112.1(3) . . ?
C15 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
C15 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
H14B C14 H14A 107.9 . . ?
C16 C15 C14 116.7(3) . . ?
C16 C15 H15B 108.1 . . ?
C14 C15 H15B 108.1 . . ?
C16 C15 H15A 108.1 . . ?
C14 C15 H15A 108.1 . . ?
H15B C15 H15A 107.3 . . ?
O2 C16 O3 123.0(3) . . ?
O2 C16 C15 123.3(3) . . ?
O3 C16 C15 113.7(3) . . ?
O1 C17 N2 122.8(3) . . ?
O1 C17 C2 118.8(3) . . ?
N2 C17 C2 118.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        26.82
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.115
####################################################################### 
# 
# 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_niano3
_database_code_depnum_ccdc_archive 'CCDC 1486609'
_audit_update_record             
;
2016-06-20 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H27 N3 O6'
_chemical_formula_weight         369.42

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'

_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                   5.3095(18)
_cell_length_b                   7.917(3)
_cell_length_c                   23.201(8)
_cell_angle_alpha                84.701(7)
_cell_angle_beta                 83.488(7)
_cell_angle_gamma                80.058(8)
_cell_volume                     951.8(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2203
_cell_measurement_theta_min      2.6581
_cell_measurement_theta_max      22.7728

_exptl_crystal_description       Lamellar
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8128
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13205
_diffrn_reflns_av_R_equivalents  0.0978
_diffrn_reflns_av_sigmaI/netI    0.1149
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         0.89
_diffrn_reflns_theta_max         26.84
_reflns_number_total             3941
_reflns_number_gt                1742
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0938P)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_number_reflns         3941
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1806
_refine_ls_R_factor_gt           0.0685
_refine_ls_wR_factor_ref         0.2048
_refine_ls_wR_factor_gt          0.1474
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_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
O1 O 1.2819(5) 0.1950(4) 0.00811(11) 0.0570(8) Uani 1 1 d . . .
O2 O -0.0468(5) 0.1356(4) 0.77100(13) 0.0613(8) Uani 1 1 d . . .
O3 O -0.3248(5) 0.3649(4) 0.74569(12) 0.0606(9) Uani 1 1 d . . .
H3A H -0.4117 0.3323 0.7759 0.091 Uiso 1 1 calc R . .
O4 O 0.6273(5) 0.7357(4) 0.16078(11) 0.0533(8) Uani 1 1 d . . .
O5 O 0.8741(5) 0.5004(4) 0.18656(11) 0.0506(7) Uani 1 1 d . . .
O6 O 1.0032(5) 0.6687(4) 0.11470(11) 0.0573(8) Uani 1 1 d . . .
N1 N 0.5722(5) 0.2086(4) 0.14873(11) 0.0335(7) Uani 1 1 d . . .
N2 N 1.2558(6) -0.0507(5) 0.06216(14) 0.0620(11) Uani 1 1 d . . .
H2A H 1.4056 -0.1011 0.0466 0.074 Uiso 1 1 calc R . .
H2B H 1.1658 -0.1074 0.0891 0.074 Uiso 1 1 calc R . .
N3 N 0.8362(6) 0.6347(5) 0.15444(13) 0.0413(8) Uani 1 1 d . . .
C1 C 0.7937(6) 0.1237(5) 0.12405(14) 0.0359(9) Uani 1 1 d . . .
H1 H 0.8682 0.0162 0.1416 0.043 Uiso 1 1 calc R . .
C2 C 0.9135(6) 0.1914(5) 0.07360(13) 0.0293(8) Uani 1 1 d . . .
C3 C 0.7990(7) 0.3476(5) 0.04921(15) 0.0389(9) Uani 1 1 d . . .
H3 H 0.8771 0.3965 0.0142 0.047 Uiso 1 1 calc R . .
C4 C 0.5739(7) 0.4326(5) 0.07508(15) 0.0437(10) Uani 1 1 d . . .
H4 H 0.4954 0.5399 0.0582 0.052 Uiso 1 1 calc R . .
C5 C 0.4639(7) 0.3613(5) 0.12541(15) 0.0419(10) Uani 1 1 d . . .
H5 H 0.3094 0.4203 0.1440 0.050 Uiso 1 1 calc R . .
C6 C 0.4503(7) 0.1362(5) 0.20427(14) 0.0473(11) Uani 1 1 d . . .
H6B H 0.4932 0.0092 0.2063 0.057 Uiso 1 1 calc R . .
H6A H 0.2612 0.1680 0.2053 0.057 Uiso 1 1 calc R . .
C7 C 0.5398(7) 0.2018(5) 0.25626(14) 0.0436(10) Uani 1 1 d . . .
H7B H 0.5256 0.3285 0.2508 0.052 Uiso 1 1 calc R . .
H7A H 0.7227 0.1526 0.2593 0.052 Uiso 1 1 calc R . .
C8 C 0.3812(8) 0.1536(6) 0.31182(15) 0.0552(12) Uani 1 1 d . . .
H8B H 0.4040 0.0267 0.3181 0.066 Uiso 1 1 calc R . .
H8A H 0.1973 0.1961 0.3074 0.066 Uiso 1 1 calc R . .
C9 C 0.4526(8) 0.2259(6) 0.36494(15) 0.0570(12) Uani 1 1 d . . .
H9B H 0.6322 0.1756 0.3714 0.068 Uiso 1 1 calc R . .
H9A H 0.4442 0.3518 0.3573 0.068 Uiso 1 1 calc R . .
C10 C 0.2793(9) 0.1903(6) 0.41968(15) 0.0639(13) Uani 1 1 d . . .
H10B H 0.0994 0.2369 0.4124 0.077 Uiso 1 1 calc R . .
H10A H 0.2921 0.0642 0.4276 0.077 Uiso 1 1 calc R . .
C11 C 0.3379(9) 0.2648(6) 0.47336(16) 0.0631(13) Uani 1 1 d . . .
H11B H 0.3288 0.3906 0.4655 0.076 Uiso 1 1 calc R . .
H11A H 0.5158 0.2157 0.4816 0.076 Uiso 1 1 calc R . .
C12 C 0.1557(9) 0.2299(7) 0.52669(16) 0.0676(14) Uani 1 1 d . . .
H12B H -0.0216 0.2795 0.5181 0.081 Uiso 1 1 calc R . .
H12A H 0.1637 0.1040 0.5338 0.081 Uiso 1 1 calc R . .
C13 C 0.2068(8) 0.3001(6) 0.58169(15) 0.0605(13) Uani 1 1 d . . .
H13B H 0.1921 0.4267 0.5754 0.073 Uiso 1 1 calc R . .
H13A H 0.3851 0.2533 0.5902 0.073 Uiso 1 1 calc R . .
C14 C 0.0243(8) 0.2565(6) 0.63368(15) 0.0593(13) Uani 1 1 d . . .
H14B H -0.1535 0.3045 0.6251 0.071 Uiso 1 1 calc R . .
H14A H 0.0372 0.1299 0.6392 0.071 Uiso 1 1 calc R . .
C15 C 0.0720(8) 0.3222(6) 0.68951(15) 0.0554(12) Uani 1 1 d . . .
H15B H 0.2531 0.2815 0.6971 0.067 Uiso 1 1 calc R . .
H15A H 0.0438 0.4495 0.6856 0.067 Uiso 1 1 calc R . .
C16 C -0.1016(7) 0.2623(6) 0.73978(16) 0.0432(10) Uani 1 1 d . . .
C17 C 1.1666(7) 0.1089(5) 0.04529(15) 0.0364(9) 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 C17 1.225(4) . ?
O2 C16 1.195(5) . ?
O3 C16 1.317(5) . ?
O3 H3A 0.8400 . ?
O4 N3 1.253(4) . ?
O5 N3 1.241(4) . ?
O6 N3 1.249(3) . ?
N1 C5 1.340(4) . ?
N1 C1 1.345(4) . ?
N1 C6 1.487(4) . ?
N2 C17 1.310(5) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C1 C2 1.376(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.382(5) . ?
C2 C17 1.497(5) . ?
C3 C4 1.369(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.364(5) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.511(5) . ?
C6 H6B 0.9900 . ?
C6 H6A 0.9900 . ?
C7 C8 1.513(4) . ?
C7 H7B 0.9900 . ?
C7 H7A 0.9900 . ?
C8 C9 1.517(5) . ?
C8 H8B 0.9900 . ?
C8 H8A 0.9900 . ?
C9 C10 1.516(5) . ?
C9 H9B 0.9900 . ?
C9 H9A 0.9900 . ?
C10 C11 1.511(5) . ?
C10 H10B 0.9900 . ?
C10 H10A 0.9900 . ?
C11 C12 1.517(5) . ?
C11 H11B 0.9900 . ?
C11 H11A 0.9900 . ?
C12 C13 1.507(5) . ?
C12 H12B 0.9900 . ?
C12 H12A 0.9900 . ?
C13 C14 1.512(5) . ?
C13 H13B 0.9900 . ?
C13 H13A 0.9900 . ?
C14 C15 1.502(5) . ?
C14 H14B 0.9900 . ?
C14 H14A 0.9900 . ?
C15 C16 1.497(5) . ?
C15 H15B 0.9900 . ?
C15 H15A 0.9900 . ?

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
C16 O3 H3A 109.5 . . ?
C5 N1 C1 121.1(3) . . ?
C5 N1 C6 119.1(3) . . ?
C1 N1 C6 119.7(3) . . ?
C17 N2 H2A 120.0 . . ?
C17 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
O5 N3 O6 120.4(3) . . ?
O5 N3 O4 120.2(3) . . ?
O6 N3 O4 119.3(4) . . ?
N1 C1 C2 120.5(4) . . ?
N1 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C1 C2 C3 118.1(3) . . ?
C1 C2 C17 123.6(3) . . ?
C3 C2 C17 118.3(3) . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 119.2(4) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N1 C5 C4 120.4(3) . . ?
N1 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
N1 C6 C7 111.5(3) . . ?
N1 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
N1 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
H6B C6 H6A 108.0 . . ?
C6 C7 C8 111.1(3) . . ?
C6 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
H7B C7 H7A 108.0 . . ?
C7 C8 C9 113.2(3) . . ?
C7 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
H8B C8 H8A 107.8 . . ?
C10 C9 C8 113.2(3) . . ?
C10 C9 H9B 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9A 108.9 . . ?
H9B C9 H9A 107.8 . . ?
C11 C10 C9 115.1(3) . . ?
C11 C10 H10B 108.5 . . ?
C9 C10 H10B 108.5 . . ?
C11 C10 H10A 108.5 . . ?
C9 C10 H10A 108.5 . . ?
H10B C10 H10A 107.5 . . ?
C10 C11 C12 113.3(4) . . ?
C10 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
H11B C11 H11A 107.7 . . ?
C13 C12 C11 115.5(4) . . ?
C13 C12 H12B 108.4 . . ?
C11 C12 H12B 108.4 . . ?
C13 C12 H12A 108.4 . . ?
C11 C12 H12A 108.4 . . ?
H12B C12 H12A 107.5 . . ?
C12 C13 C14 113.1(3) . . ?
C12 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
H13B C13 H13A 107.8 . . ?
C15 C14 C13 114.6(3) . . ?
C15 C14 H14B 108.6 . . ?
C13 C14 H14B 108.6 . . ?
C15 C14 H14A 108.6 . . ?
C13 C14 H14A 108.6 . . ?
H14B C14 H14A 107.6 . . ?
C16 C15 C14 111.5(3) . . ?
C16 C15 H15B 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C16 C15 H15A 109.3 . . ?
C14 C15 H15A 109.3 . . ?
H15B C15 H15A 108.0 . . ?
O2 C16 O3 123.4(4) . . ?
O2 C16 C15 124.4(4) . . ?
O3 C16 C15 112.2(4) . . ?
O1 C17 N2 123.3(3) . . ?
O1 C17 C2 118.2(4) . . ?
N2 C17 C2 118.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        26.84
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.096
####################################################################### 
# 
# 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_niabr
_database_code_depnum_ccdc_archive 'CCDC 1486610'
_audit_update_record             
;
2016-06-20 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H27 Br N2 O3'
_chemical_formula_weight         387.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Br Br -0.2901 2.4595 '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                   4.6813(3)
_cell_length_b                   8.4396(5)
_cell_length_c                   23.3456(15)
_cell_angle_alpha                80.193(2)
_cell_angle_beta                 88.216(2)
_cell_angle_gamma                80.574(2)
_cell_volume                     896.59(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8543
_cell_measurement_theta_min      2.4814
_cell_measurement_theta_max      26.4041

_exptl_crystal_description       Acicular
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    2.309
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8676
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7795
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         0.89
_diffrn_reflns_theta_max         26.43
_reflns_number_total             3617
_reflns_number_gt                3319
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0417P)²+0.2039P] 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         3617
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0248
_refine_ls_wR_factor_ref         0.0844
_refine_ls_wR_factor_gt          0.0678
_refine_ls_goodness_of_fit_ref   1.230
_refine_ls_restrained_S_all      1.230
_refine_ls_shift/su_max          0.002
_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
Br1 Br 0.96037(5) 0.00558(3) 0.861574(9) 0.01450(9) Uani 1 1 d . . .
O1 O -0.0715(3) 0.7335(2) 0.01593(7) 0.0148(3) Uani 1 1 d . . .
O2 O 0.9860(4) 0.7643(2) 0.73074(8) 0.0275(4) Uani 1 1 d . . .
O3 O 0.6593(4) 0.9798(2) 0.74268(8) 0.0298(5) Uani 1 1 d . . .
H3A H 0.7550 0.9744 0.7730 0.045 Uiso 1 1 calc R . .
N1 N 0.6659(4) 0.5459(2) 0.15081(8) 0.0090(4) Uani 1 1 d . . .
N2 N 0.3286(4) 0.8501(2) -0.00762(8) 0.0123(4) Uani 1 1 d . . .
H2A H 0.2413 0.9217 -0.0361 0.015 Uiso 1 1 calc R . .
H2B H 0.5114 0.8501 0.0001 0.015 Uiso 1 1 calc R . .
C1 C 0.5319(5) 0.6607(3) 0.10876(9) 0.0104(4) Uani 1 1 d . . .
H1 H 0.5639 0.7702 0.1053 0.012 Uiso 1 1 calc R . .
C2 C 0.3478(5) 0.6193(3) 0.07067(9) 0.0105(4) Uani 1 1 d . . .
C3 C 0.3017(5) 0.4582(3) 0.07708(9) 0.0125(5) Uani 1 1 d . . .
H3 H 0.1698 0.4285 0.0523 0.015 Uiso 1 1 calc R . .
C4 C 0.4481(5) 0.3416(3) 0.11959(10) 0.0135(5) Uani 1 1 d . . .
H4 H 0.4228 0.2309 0.1234 0.016 Uiso 1 1 calc R . .
C5 C 0.6305(5) 0.3881(3) 0.15629(10) 0.0123(5) Uani 1 1 d . . .
H5 H 0.7323 0.3090 0.1857 0.015 Uiso 1 1 calc R . .
C6 C 0.8447(5) 0.5938(3) 0.19470(9) 0.0116(4) Uani 1 1 d . . .
H6A H 0.9125 0.6974 0.1784 0.014 Uiso 1 1 calc R . .
H6B H 1.0167 0.5090 0.2045 0.014 Uiso 1 1 calc R . .
C7 C 0.6656(5) 0.6144(3) 0.24932(9) 0.0128(5) Uani 1 1 d . . .
H7A H 0.4980 0.7022 0.2395 0.015 Uiso 1 1 calc R . .
H7B H 0.5901 0.5122 0.2643 0.015 Uiso 1 1 calc R . .
C8 C 0.8446(5) 0.6561(3) 0.29634(9) 0.0145(5) Uani 1 1 d . . .
H8A H 0.9065 0.7628 0.2825 0.017 Uiso 1 1 calc R . .
H8B H 1.0208 0.5730 0.3037 0.017 Uiso 1 1 calc R . .
C9 C 0.6758(5) 0.6634(3) 0.35302(9) 0.0145(5) Uani 1 1 d . . .
H9A H 0.4999 0.7466 0.3454 0.017 Uiso 1 1 calc R . .
H9B H 0.6123 0.5568 0.3663 0.017 Uiso 1 1 calc R . .
C10 C 0.8466(5) 0.7038(3) 0.40160(9) 0.0147(5) Uani 1 1 d . . .
H10A H 0.9219 0.8066 0.3876 0.018 Uiso 1 1 calc R . .
H10B H 1.0146 0.6163 0.4116 0.018 Uiso 1 1 calc R . .
C11 C 0.6645(5) 0.7219(3) 0.45617(10) 0.0148(5) Uani 1 1 d . . .
H11A H 0.5002 0.8118 0.4462 0.018 Uiso 1 1 calc R . .
H11B H 0.5832 0.6205 0.4690 0.018 Uiso 1 1 calc R . .
C12 C 0.8305(5) 0.7565(3) 0.50639(9) 0.0157(5) Uani 1 1 d . . .
H12A H 0.9249 0.8530 0.4928 0.019 Uiso 1 1 calc R . .
H12B H 0.9849 0.6626 0.5186 0.019 Uiso 1 1 calc R . .
C13 C 0.6400(5) 0.7874(3) 0.55860(9) 0.0154(5) Uani 1 1 d . . .
H13A H 0.5361 0.6939 0.5706 0.018 Uiso 1 1 calc R . .
H13B H 0.4931 0.8854 0.5468 0.018 Uiso 1 1 calc R . .
C14 C 0.8062(5) 0.8121(3) 0.61055(10) 0.0161(5) Uani 1 1 d . . .
H14A H 0.9237 0.8994 0.5979 0.019 Uiso 1 1 calc R . .
H14B H 0.9405 0.7105 0.6248 0.019 Uiso 1 1 calc R . .
C15 C 0.6073(5) 0.8577(3) 0.66032(10) 0.0170(5) Uani 1 1 d . . .
H15A H 0.4905 0.9663 0.6477 0.020 Uiso 1 1 calc R . .
H15B H 0.4724 0.7779 0.6696 0.020 Uiso 1 1 calc R . .
C16 C 0.7740(5) 0.8612(3) 0.71447(10) 0.0157(5) Uani 1 1 d . . .
C17 C 0.1843(5) 0.7421(3) 0.02378(9) 0.0105(4) 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 C17 1.233(3) . ?
O2 C16 1.204(3) . ?
O3 C16 1.323(3) . ?
O3 H3A 0.8400 . ?
N1 C1 1.346(3) . ?
N1 C5 1.353(3) . ?
N1 C6 1.490(3) . ?
N2 C17 1.330(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C1 C2 1.381(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.394(3) . ?
C2 C17 1.504(3) . ?
C3 C4 1.382(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.374(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.523(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.522(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.525(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.523(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.526(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.520(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.521(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.522(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.527(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.513(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

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
C16 O3 H3A 109.5 . . ?
C1 N1 C5 121.64(19) . . ?
C1 N1 C6 119.66(19) . . ?
C5 N1 C6 118.61(18) . . ?
C17 N2 H2A 120.0 . . ?
C17 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C1 C2 120.0(2) . . ?
N1 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C1 C2 C3 118.9(2) . . ?
C1 C2 C17 122.9(2) . . ?
C3 C2 C17 118.2(2) . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 119.1(2) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N1 C5 C4 120.3(2) . . ?
N1 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
N1 C6 C7 109.79(17) . . ?
N1 C6 H6A 109.7 . . ?
C7 C6 H6A 109.7 . . ?
N1 C6 H6B 109.7 . . ?
C7 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C8 C7 C6 111.44(18) . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C9 112.11(19) . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 114.08(19) . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 C11 112.59(19) . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C10 114.12(19) . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C10 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 C13 113.22(19) . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 C14 113.8(2) . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 C15 112.66(19) . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C16 C15 C14 112.4(2) . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
O2 C16 O3 123.5(2) . . ?
O2 C16 C15 123.5(2) . . ?
O3 C16 C15 113.0(2) . . ?
O1 C17 N2 124.3(2) . . ?
O1 C17 C2 118.16(19) . . ?
N2 C17 C2 117.53(19) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        26.43
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.113
####################################################################### 
# 
# 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_niabf4
_database_code_depnum_ccdc_archive 'CCDC 1486611'
_audit_update_record             
;
2016-06-20 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H27 B F4 N2 O3'
_chemical_formula_weight         394.22

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'
B B 0.0013 0.0007 '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                   6.9325(4)
_cell_length_b                   9.5052(6)
_cell_length_c                   15.5569(10)
_cell_angle_alpha                100.851(3)
_cell_angle_beta                 90.364(2)
_cell_angle_gamma                104.223(2)
_cell_volume                     974.44(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3235
_cell_measurement_theta_min      3.0340
_cell_measurement_theta_max      26.4554

_exptl_crystal_description       lamollar
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8937
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16473
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.33
_diffrn_reflns_theta_max         26.44
_reflns_number_total             3987
_reflns_number_gt                3504
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0637P)²+0.4366P] 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         3987
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1233
_refine_ls_wR_factor_gt          0.1109
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.8823(3) 0.92309(19) 0.82527(12) 0.0204(4) Uani 1 1 d . . .
F1 F 0.89610(13) 0.77841(10) 0.81743(6) 0.0249(2) Uani 1 1 d . . .
F2 F 1.02265(18) 1.01328(12) 0.88859(8) 0.0446(3) Uani 1 1 d . . .
F3 F 0.92469(14) 0.96616(12) 0.74396(7) 0.0326(3) Uani 1 1 d . . .
F4 F 0.69125(14) 0.93261(11) 0.84512(6) 0.0282(2) Uani 1 1 d . . .
O1 O 0.80606(15) 0.49208(12) 0.92322(7) 0.0208(2) Uani 1 1 d . . .
O2 O 1.65911(17) 0.74984(12) 0.21885(8) 0.0270(3) Uani 1 1 d . . .
O3 O 1.70262(17) 0.96782(13) 0.30899(8) 0.0299(3) Uani 1 1 d . . .
H3A H 1.8205 0.9780 0.2937 0.045 Uiso 1 1 calc R . .
N1 N 0.32386(16) 0.63640(13) 0.86584(8) 0.0141(3) Uani 1 1 d . . .
N2 N 0.89500(18) 0.66083(14) 1.04839(8) 0.0194(3) Uani 1 1 d . . .
H2B H 0.9966 0.6262 1.0604 0.023 Uiso 1 1 calc R . .
H2A H 0.8701 0.7368 1.0843 0.023 Uiso 1 1 calc R . .
C1 C 0.4842(2) 0.59012(15) 0.88551(9) 0.0147(3) Uani 1 1 d . . .
H1 H 0.5150 0.5086 0.8478 0.018 Uiso 1 1 calc R . .
C2 C 0.60457(19) 0.66026(15) 0.96024(9) 0.0138(3) Uani 1 1 d . . .
C3 C 0.5546(2) 0.77688(15) 1.01563(9) 0.0164(3) Uani 1 1 d . . .
H3 H 0.6346 0.8261 1.0675 0.020 Uiso 1 1 calc R . .
C4 C 0.3864(2) 0.82106(16) 0.99450(10) 0.0174(3) Uani 1 1 d . . .
H4 H 0.3492 0.8997 1.0323 0.021 Uiso 1 1 calc R . .
C5 C 0.2745(2) 0.75035(16) 0.91864(9) 0.0161(3) Uani 1 1 d . . .
H5 H 0.1613 0.7819 0.9032 0.019 Uiso 1 1 calc R . .
C6 C 0.1984(2) 0.56144(16) 0.78398(9) 0.0173(3) Uani 1 1 d . . .
H6B H 0.0583 0.5644 0.7936 0.021 Uiso 1 1 calc R . .
H6A H 0.2029 0.4563 0.7697 0.021 Uiso 1 1 calc R . .
C7 C 0.2703(2) 0.63559(17) 0.70721(10) 0.0189(3) Uani 1 1 d . . .
H7B H 0.2747 0.7422 0.7237 0.023 Uiso 1 1 calc R . .
H7A H 0.1727 0.5921 0.6567 0.023 Uiso 1 1 calc R . .
C8 C 0.4757(2) 0.61945(17) 0.67909(10) 0.0196(3) Uani 1 1 d . . .
H8B H 0.5740 0.6658 0.7291 0.024 Uiso 1 1 calc R . .
H8A H 0.4724 0.5129 0.6645 0.024 Uiso 1 1 calc R . .
C9 C 0.5445(2) 0.68924(18) 0.60074(10) 0.0224(3) Uani 1 1 d . . .
H9B H 0.5416 0.7947 0.6140 0.027 Uiso 1 1 calc R . .
H9A H 0.4507 0.6393 0.5496 0.027 Uiso 1 1 calc R . .
C10 C 0.7543(2) 0.67837(19) 0.57728(10) 0.0231(3) Uani 1 1 d . . .
H10B H 0.8476 0.7298 0.6283 0.028 Uiso 1 1 calc R . .
H10A H 0.7570 0.5728 0.5657 0.028 Uiso 1 1 calc R . .
C11 C 0.8276(2) 0.74402(19) 0.49805(10) 0.0240(3) Uani 1 1 d . . .
H11B H 0.8143 0.8471 0.5073 0.029 Uiso 1 1 calc R . .
H11A H 0.7418 0.6868 0.4457 0.029 Uiso 1 1 calc R . .
C12 C 1.0438(2) 0.74401(19) 0.48044(10) 0.0242(3) Uani 1 1 d . . .
H12B H 1.1313 0.8129 0.5290 0.029 Uiso 1 1 calc R . .
H12A H 1.0615 0.6436 0.4798 0.029 Uiso 1 1 calc R . .
C13 C 1.1083(2) 0.78913(19) 0.39441(10) 0.0235(3) Uani 1 1 d . . .
H13B H 1.0844 0.8875 0.3941 0.028 Uiso 1 1 calc R . .
H13A H 1.0240 0.7177 0.3458 0.028 Uiso 1 1 calc R . .
C14 C 1.3265(2) 0.79621(19) 0.37736(10) 0.0233(3) Uani 1 1 d . . .
H14B H 1.3570 0.7036 0.3867 0.028 Uiso 1 1 calc R . .
H14A H 1.4121 0.8795 0.4197 0.028 Uiso 1 1 calc R . .
C15 C 1.3736(2) 0.8171(2) 0.28423(10) 0.0266(4) Uani 1 1 d . . .
H15B H 1.2958 0.7294 0.2424 0.032 Uiso 1 1 calc R . .
H15A H 1.3302 0.9044 0.2735 0.032 Uiso 1 1 calc R . .
C16 C 1.5905(2) 0.83840(17) 0.26661(10) 0.0201(3) Uani 1 1 d . . .
C17 C 0.77957(19) 0.59861(15) 0.97626(9) 0.0140(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
B1 F4 1.3822(19) . ?
B1 F2 1.383(2) . ?
B1 F1 1.3846(19) . ?
B1 F3 1.412(2) . ?
O1 C17 1.2323(17) . ?
O2 C16 1.2051(19) . ?
O3 C16 1.3305(19) . ?
O3 H3A 0.8400 . ?
N1 C1 1.3451(17) . ?
N1 C5 1.3476(19) . ?
N1 C6 1.4920(17) . ?
N2 C17 1.3248(18) . ?
N2 H2B 0.8800 . ?
N2 H2A 0.8800 . ?
C1 C2 1.384(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.387(2) . ?
C2 C17 1.5092(18) . ?
C3 C4 1.3903(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.371(2) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.524(2) . ?
C6 H6B 0.9900 . ?
C6 H6A 0.9900 . ?
C7 C8 1.5273(19) . ?
C7 H7B 0.9900 . ?
C7 H7A 0.9900 . ?
C8 C9 1.520(2) . ?
C8 H8B 0.9900 . ?
C8 H8A 0.9900 . ?
C9 C10 1.525(2) . ?
C9 H9B 0.9900 . ?
C9 H9A 0.9900 . ?
C10 C11 1.519(2) . ?
C10 H10B 0.9900 . ?
C10 H10A 0.9900 . ?
C11 C12 1.525(2) . ?
C11 H11B 0.9900 . ?
C11 H11A 0.9900 . ?
C12 C13 1.518(2) . ?
C12 H12B 0.9900 . ?
C12 H12A 0.9900 . ?
C13 C14 1.525(2) . ?
C13 H13B 0.9900 . ?
C13 H13A 0.9900 . ?
C14 C15 1.526(2) . ?
C14 H14B 0.9900 . ?
C14 H14A 0.9900 . ?
C15 C16 1.501(2) . ?
C15 H15B 0.9900 . ?
C15 H15A 0.9900 . ?

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
F4 B1 F2 111.80(14) . . ?
F4 B1 F1 110.11(13) . . ?
F2 B1 F1 108.97(13) . . ?
F4 B1 F3 108.82(12) . . ?
F2 B1 F3 108.96(13) . . ?
F1 B1 F3 108.11(13) . . ?
C16 O3 H3A 109.5 . . ?
C1 N1 C5 121.17(12) . . ?
C1 N1 C6 119.76(12) . . ?
C5 N1 C6 119.07(11) . . ?
C17 N2 H2B 120.0 . . ?
C17 N2 H2A 120.0 . . ?
H2B N2 H2A 120.0 . . ?
N1 C1 C2 120.55(13) . . ?
N1 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C1 C2 C3 118.93(12) . . ?
C1 C2 C17 116.12(12) . . ?
C3 C2 C17 124.92(12) . . ?
C2 C3 C4 119.37(13) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 119.53(13) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N1 C5 C4 120.43(12) . . ?
N1 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
N1 C6 C7 111.39(11) . . ?
N1 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
N1 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
H6B C6 H6A 108.0 . . ?
C6 C7 C8 113.59(12) . . ?
C6 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
H7B C7 H7A 107.7 . . ?
C9 C8 C7 113.57(12) . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
H8B C8 H8A 107.7 . . ?
C8 C9 C10 112.29(13) . . ?
C8 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
H9B C9 H9A 107.9 . . ?
C11 C10 C9 114.08(13) . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
H10B C10 H10A 107.6 . . ?
C10 C11 C12 113.23(13) . . ?
C10 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
H11B C11 H11A 107.7 . . ?
C13 C12 C11 113.27(13) . . ?
C13 C12 H12B 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12A 108.9 . . ?
H12B C12 H12A 107.7 . . ?
C12 C13 C14 114.12(13) . . ?
C12 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C12 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
H13B C13 H13A 107.6 . . ?
C13 C14 C15 111.58(12) . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
H14B C14 H14A 108.0 . . ?
C16 C15 C14 113.65(13) . . ?
C16 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
H15B C15 H15A 107.7 . . ?
O2 C16 O3 122.47(14) . . ?
O2 C16 C15 124.65(15) . . ?
O3 C16 C15 112.88(13) . . ?
O1 C17 N2 123.32(12) . . ?
O1 C17 C2 118.98(12) . . ?
N2 C17 C2 117.68(12) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.44
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.618
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.088
