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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_CCDC-953446
_audit_creation_date             2013-07-27
_chemical_name_systematic        
;
N-(1-Oxo-2,2,6,6-tetramethylpiperidin-4-yl)-pivalamide
;
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_chemical_formula_moiety         'C14 H27 N2 O2'
_chemical_formula_sum            'C14 H27 N2 O2'
_chemical_formula_weight         255.38
_chemical_oxdiff_formula         'C20 H32 N3 O3 F3'
_chemical_oxdiff_usercomment     '0.8 mm 2 kW'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y-1/2,z-1/2
8 x-1/2,y,-z-1/2

_cell_length_a                   11.7026(4)
_cell_length_b                   9.9471(3)
_cell_length_c                   28.8577(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3359.2(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4836
_cell_measurement_theta_max      26.0050
_cell_measurement_theta_min      3.4020
_cell_measurement_temperature    293
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_diffrn_ambient_temperature      293
_exptl_crystal_colour            'orange '
_exptl_crystal_density_diffrn    1.0099
_exptl_crystal_description       plate
_exptl_crystal_F_000             1128.4824
_exptl_crystal_size_max          0.951
_exptl_crystal_size_mid          0.593
_exptl_crystal_size_min          0.285
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            15894
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.04
_diffrn_detector_area_resol_mean 8.4353
_diffrn_measured_fraction_theta_full 0.9967
_diffrn_measured_fraction_theta_max 0.9969
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0115686000
_diffrn_orient_matrix_UB_12      -0.0687923000
_diffrn_orient_matrix_UB_13      -0.0044953000
_diffrn_orient_matrix_UB_21      -0.0082108000
_diffrn_orient_matrix_UB_22      -0.0149771000
_diffrn_orient_matrix_UB_23      0.0237888000
_diffrn_orient_matrix_UB_31      -0.0589359000
_diffrn_orient_matrix_UB_32      -0.0113650000
_diffrn_orient_matrix_UB_33      -0.0042081000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              0
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              36
_reflns_limit_l_min              0
_reflns_number_gt                2518
_reflns_number_total             3417
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material  
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  
;
OLEX2.REFINE (Dolomanov et al., 2009)
;
_computing_structure_solution    
;
OLEX2.SOLVE (Dolomanov et al., 2009)
;
_refine_diff_density_max         0.2151
_refine_diff_density_min         -0.1593
_refine_diff_density_rms         0.0340
_refine_ls_d_res_high            0.8002
_refine_ls_d_res_low             6.7098
_refine_ls_goodness_of_fit_ref   1.0712
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    65
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3417
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      1.0668
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0731P)²+0.5117P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1554
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C11-C12A = C11-C12B = C11-C12C
 1.54 with sigma of 0.01
 C11-C13A = C11-C13B = C11-C13C
 1.54 with sigma of 0.01
 C11-C14A = C11-C14B = C11-C14C
 1.54 with sigma of 0.01
 C10-C12A \\sim C10-C12B \\sim C10-C12C
 with sigma of 0.02
 C10-C13A \\sim C10-C13B \\sim C10-C13C
 with sigma of 0.02
 C10-C14A \\sim C10-C14B \\sim C10-C14C
 with sigma of 0.02
 C12A-C13A \\sim C12A-C14A \\sim C13A-C14A
 with sigma of 0.02
 C12B-C13B \\sim C12B-C14B \\sim C13B-C14B
 with sigma of 0.02
 C12C-C13C \\sim C12C-C14C \\sim C13C-C14C
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C14A) = Uanis(C14B) = Uanis(C14C)
Uanis(C12A) = Uanis(C12B) = Uanis(C12C)
Uanis(C13A) = Uanis(C13B) = Uanis(C13C)
4. Others
 Fixed Sof: C12A(0.62) H12a(0.62) H12b(0.62) H12c(0.62) C13A(0.62) H13a(0.62)
 H13b(0.62) H13c(0.62) C14A(0.62) H14a(0.62) H14b(0.62) H14c(0.62) C12B(0.22)
 H12d(0.22) H12e(0.22) H12f(0.22) C13B(0.22) H13d(0.22) H13e(0.22) H13f(0.22)
 C14B(0.22) H14d(0.22) H14e(0.22) H14f(0.22) C12C(0.16) H12g(0.16) H12h(0.16)
 H12i(0.16) C13C(0.16) H13g(0.16) H13h(0.16) H13i(0.16) C14C(0.16) H14g(0.16)
 H14h(0.16) H14i(0.16)
5.a Ternary CH refined with riding coordinates:
 C3(H3)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C4(H4a,H4b)
5.c Me refined with riding coordinates:
 C12A(H12a,H12b,H12c), C13A(H13a,H13b,H13c), C14A(H14a,H14b,H14c), C12B(H12d,
 H12e,H12f), C13B(H13d,H13e,H13f), C14B(H14d,H14e,H14f), C12C(H12g,H12h,H12i),
 C13C(H13g,H13h,H13i), C14C(H14g,H14h,H14i)
5.d Aromatic/amide H refined with riding coordinates:
 N2(H2)
5.e Idealised Me refined as rotating group:
 C6(H6a,H6b,H6c), C7(H7a,H7b,H7c), C8(H8a,H8b,H8c), C9(H9a,H9b,H9c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
_atom_site_disorder_group
O1 O 0.09670(9) 0.22903(14) 0.51631(4) 0.0792(4) Uani 1.000000 . .
O2 O -0.29386(12) 0.43413(10) 0.66288(5) 0.0910(5) Uani 1.000000 . .
C1 C 0.05812(13) 0.24403(16) 0.59585(6) 0.0627(4) Uani 1.000000 . .
C2 C -0.03663(14) 0.20677(18) 0.62985(6) 0.0664(4) Uani 1.000000 . .
H2a H -0.03941(14) 0.10969(18) 0.63281(6) 0.0796(5) Uiso 1.000000 R .
H2b H -0.01802(14) 0.24357(18) 0.66005(6) 0.0796(5) Uiso 1.000000 R .
C3 C -0.15320(13) 0.25692(14) 0.61562(6) 0.0590(4) Uani 1.000000 . .
H3 H -0.14995(13) 0.35478(14) 0.61193(6) 0.0708(5) Uiso 1.000000 R .
C4 C -0.18319(12) 0.19451(15) 0.56964(6) 0.0582(4) Uani 1.000000 . .
H4a H -0.18313(12) 0.09746(15) 0.57292(6) 0.0698(5) Uiso 1.000000 R .
H4b H -0.25990(12) 0.22187(15) 0.56109(6) 0.0698(5) Uiso 1.000000 R .
C5 C -0.10121(11) 0.23346(15) 0.53081(5) 0.0547(4) Uani 1.000000 . .
C6 C 0.16118(15) 0.1527(2) 0.60400(7) 0.0926(7) Uani 1.000000 . .
H6a H 0.1400(4) 0.0610(3) 0.5981(5) 0.1389(10) Uiso 1.000000 GR .
H6b H 0.2220(5) 0.1781(10) 0.5835(4) 0.1389(10) Uiso 1.000000 GR .
H6c H 0.1863(9) 0.1615(12) 0.63552(17) 0.1389(10) Uiso 1.000000 GR .
C7 C 0.09259(17) 0.3915(2) 0.60062(7) 0.0879(6) Uani 1.000000 . .
H7a H 0.1452(10) 0.4146(5) 0.5764(3) 0.1318(9) Uiso 1.000000 GR .
H7b H 0.0259(2) 0.4472(2) 0.5983(5) 0.1318(9) Uiso 1.000000 GR .
H7c H 0.1284(12) 0.4054(4) 0.6302(2) 0.1318(9) Uiso 1.000000 GR .
C8 C -0.11672(15) 0.1379(2) 0.49015(6) 0.0744(5) Uani 1.000000 . .
H8a H -0.0651(8) 0.1624(9) 0.46571(19) 0.1117(7) Uiso 1.000000 GR .
H8b H -0.1009(11) 0.0476(3) 0.49999(13) 0.1117(7) Uiso 1.000000 GR .
H8c H -0.1939(3) 0.1434(10) 0.4791(3) 0.1117(7) Uiso 1.000000 GR .
C9 C -0.12214(15) 0.37724(17) 0.51462(7) 0.0717(5) Uani 1.000000 . .
H9a H -0.1142(11) 0.4376(2) 0.54038(11) 0.1075(7) Uiso 1.000000 GR .
H9b H -0.0675(7) 0.4003(5) 0.4911(3) 0.1075(7) Uiso 1.000000 GR .
H9c H -0.1980(4) 0.3844(3) 0.5022(4) 0.1075(7) Uiso 1.000000 GR .
C10 C -0.30296(14) 0.31457(14) 0.67151(6) 0.0624(4) Uani 1.000000 . .
C11 C -0.39063(19) 0.26291(17) 0.70641(8) 0.0890(7) Uani 1.000000 D .
C12A C -0.3296(4) 0.1801(6) 0.74542(15) 0.1180(16) Uani 0.620000 D 1
H12a H -0.2923(4) 0.2405(6) 0.76651(15) 0.177(2) Uiso 0.620000 R 1
H12b H -0.3851(4) 0.1276(6) 0.76192(15) 0.177(2) Uiso 0.620000 R 1
H12c H -0.2739(4) 0.1214(6) 0.73172(15) 0.177(2) Uiso 0.620000 R 1
C13A C -0.4595(5) 0.3754(4) 0.7273(2) 0.131(2) Uani 0.620000 D 1
H13a H -0.4590(5) 0.4512(4) 0.7068(2) 0.196(4) Uiso 0.620000 R 1
H13b H -0.5367(5) 0.3458(4) 0.7321(2) 0.196(4) Uiso 0.620000 R 1
H13c H -0.4266(5) 0.4008(4) 0.7565(2) 0.196(4) Uiso 0.620000 R 1
C14A C -0.4693(4) 0.1579(5) 0.68303(18) 0.1270(19) Uani 0.620000 D 1
H14a H -0.5187(4) 0.2022(5) 0.66127(18) 0.191(3) Uiso 0.620000 R 1
H14b H -0.4235(4) 0.0926(5) 0.66709(18) 0.191(3) Uiso 0.620000 R 1
H14c H -0.5146(4) 0.1138(5) 0.70622(18) 0.191(3) Uiso 0.620000 R 1
C12B C -0.3660(15) 0.1263(11) 0.7246(5) 0.1180(16) Uani 0.220000 D 2
H12d H -0.3193(15) 0.0783(11) 0.7029(5) 0.177(2) Uiso 0.220000 R 2
H12e H -0.3264(15) 0.1336(11) 0.7537(5) 0.177(2) Uiso 0.220000 R 2
H12f H -0.4365(15) 0.0787(11) 0.7292(5) 0.177(2) Uiso 0.220000 R 2
C13B C -0.3883(13) 0.3754(14) 0.7437(5) 0.131(2) Uani 0.220000 D 2
H13d H -0.4049(13) 0.4604(14) 0.7294(5) 0.196(4) Uiso 0.220000 R 2
H13e H -0.4446(13) 0.3566(14) 0.7670(5) 0.196(4) Uiso 0.220000 R 2
H13f H -0.3140(13) 0.3788(14) 0.7577(5) 0.196(4) Uiso 0.220000 R 2
C14B C -0.5030(7) 0.2697(16) 0.6776(4) 0.1270(19) Uani 0.220000 D 2
H14d H -0.5145(7) 0.3599(16) 0.6668(4) 0.191(3) Uiso 0.220000 R 2
H14e H -0.4974(7) 0.2100(16) 0.6516(4) 0.191(3) Uiso 0.220000 R 2
H14f H -0.5663(7) 0.2435(16) 0.6967(4) 0.191(3) Uiso 0.220000 R 2
C12C C -0.3313(14) 0.294(2) 0.7530(3) 0.1180(16) Uani 0.160000 D 3
H12g H -0.3269(14) 0.390(2) 0.7572(3) 0.177(2) Uiso 0.160000 R 3
H12h H -0.3746(14) 0.256(2) 0.7779(3) 0.177(2) Uiso 0.160000 R 3
H12i H -0.2556(14) 0.257(2) 0.7529(3) 0.177(2) Uiso 0.160000 R 3
C13C C -0.4958(13) 0.354(2) 0.6986(7) 0.131(2) Uani 0.160000 D 3
H13g H -0.4715(13) 0.438(2) 0.6854(7) 0.196(4) Uiso 0.160000 R 3
H13h H -0.5481(13) 0.311(2) 0.6778(7) 0.196(4) Uiso 0.160000 R 3
H13i H -0.5331(13) 0.371(2) 0.7277(7) 0.196(4) Uiso 0.160000 R 3
C14C C -0.4142(18) 0.1152(11) 0.6982(10) 0.1270(19) Uani 0.160000 D 3
H14g H -0.4626(18) 0.1052(11) 0.6715(10) 0.191(3) Uiso 0.160000 R 3
H14h H -0.3434(18) 0.0688(11) 0.6929(10) 0.191(3) Uiso 0.160000 R 3
H14i H -0.4515(18) 0.0777(11) 0.7248(10) 0.191(3) Uiso 0.160000 R 3
N1 N 0.01908(10) 0.21990(13) 0.54756(4) 0.0559(3) Uani 1.000000 . .
N2 N -0.23816(13) 0.22442(12) 0.65076(5) 0.0700(4) Uani 1.000000 . .
H2N H -0.24655(13) 0.14146(12) 0.65842(5) 0.0840(5) Uiso 1.000000 R .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 N1 1.2833(16) .
O2 C10 1.2197(17) .
C1 C2 1.526(2) .
C1 C6 1.528(2) .
C1 C7 1.528(2) .
C1 N1 1.486(2) .
C2 H2a 0.9700 .
C2 H2b 0.9700 .
C2 C3 1.509(2) .
C3 H3 0.9800 .
C3 C4 1.506(2) .
C3 N2 1.4564(18) .
C4 H4a 0.9700 .
C4 H4b 0.9700 .
C4 C5 1.525(2) .
C5 C8 1.521(2) .
C5 C9 1.524(2) .
C5 N1 1.4945(18) .
C6 H6a 0.9600 .
C6 H6b 0.9600 .
C6 H6c 0.9600 .
C7 H7a 0.9600 .
C7 H7b 0.9600 .
C7 H7c 0.9600 .
C8 H8a 0.9600 .
C8 H8b 0.9600 .
C8 H8c 0.9600 .
C9 H9a 0.9600 .
C9 H9b 0.9600 .
C9 H9c 0.9600 .
C10 C11 1.527(2) .
C10 N2 1.3183(19) .
C11 C12A 1.567(4) .
C11 C13A 1.505(4) .
C11 C14A 1.547(4) .
C11 C12B 1.485(8) .
C11 C13B 1.553(8) .
C11 C14B 1.557(8) .
C11 C12C 1.546(8) .
C11 C13C 1.548(9) .
C11 C14C 1.514(8) .
C12A H12a 0.9600 .
C12A H12b 0.9600 .
C12A H12c 0.9600 .
C13A H13a 0.9600 .
C13A H13b 0.9600 .
C13A H13c 0.9600 .
C14A H14a 0.9600 .
C14A H14b 0.9600 .
C14A H14c 0.9600 .
C12B H12d 0.9600 .
C12B H12e 0.9600 .
C12B H12f 0.9600 .
C13B H13d 0.9600 .
C13B H13e 0.9600 .
C13B H13f 0.9600 .
C14B H14d 0.9600 .
C14B H14e 0.9600 .
C14B H14f 0.9600 .
C12C H12g 0.9600 .
C12C H12h 0.9600 .
C12C H12i 0.9600 .
C13C H13g 0.9600 .
C13C H13h 0.9600 .
C13C H13i 0.9600 .
C14C H14g 0.9600 .
C14C H14h 0.9600 .
C14C H14i 0.9600 .
N2 H2 0.8600 .

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
C6 C1 C2 109.27(15) . .
C7 C1 C2 111.54(14) . .
C7 C1 C6 110.41(15) . .
N1 C1 C2 109.89(12) . .
N1 C1 C6 106.92(13) . .
N1 C1 C7 108.71(14) . .
H2a C2 C1 108.83(9) . .
H2b C2 C1 108.83(9) . .
H2b C2 H2a 107.7 . .
C3 C2 C1 113.67(13) . .
C3 C2 H2a 108.83(9) . .
C3 C2 H2b 108.83(9) . .
H3 C3 C2 108.83(9) . .
C4 C3 C2 108.30(12) . .
C4 C3 H3 108.83(8) . .
N2 C3 C2 110.74(13) . .
N2 C3 H3 108.83(7) . .
N2 C3 C4 111.27(12) . .
H4a C4 C3 108.91(8) . .
H4b C4 C3 108.91(8) . .
H4b C4 H4a 107.7 . .
C5 C4 C3 113.33(12) . .
C5 C4 H4a 108.91(8) . .
C5 C4 H4b 108.91(8) . .
C8 C5 C4 109.46(13) . .
C9 C5 C4 111.25(13) . .
C9 C5 C8 109.30(14) . .
N1 C5 C4 109.39(12) . .
N1 C5 C8 107.79(12) . .
N1 C5 C9 109.58(12) . .
H6a C6 C1 109.5 . .
H6b C6 C1 109.5 . .
H6b C6 H6a 109.5 . .
H6c C6 C1 109.5 . .
H6c C6 H6a 109.5 . .
H6c C6 H6b 109.5 . .
H7a C7 C1 109.5 . .
H7b C7 C1 109.5 . .
H7b C7 H7a 109.5 . .
H7c C7 C1 109.5 . .
H7c C7 H7a 109.5 . .
H7c C7 H7b 109.5 . .
H8a C8 C5 109.5 . .
H8b C8 C5 109.5 . .
H8b C8 H8a 109.5 . .
H8c C8 C5 109.5 . .
H8c C8 H8a 109.5 . .
H8c C8 H8b 109.5 . .
H9a C9 C5 109.5 . .
H9b C9 C5 109.5 . .
H9b C9 H9a 109.5 . .
H9c C9 C5 109.5 . .
H9c C9 H9a 109.5 . .
H9c C9 H9b 109.5 . .
C11 C10 O2 121.44(14) . .
N2 C10 O2 121.34(14) . .
N2 C10 C11 117.22(13) . .
C13A C11 C12A 110.3(3) . .
C14A C11 C12A 103.3(3) . .
C14A C11 C13A 111.0(3) . .
C13B C11 C12B 114.2(8) . .
C14B C11 C12B 113.1(8) . .
C14B C11 C13B 110.7(8) . .
C13C C11 C12C 111.4(10) . .
C14C C11 C12C 114.5(11) . .
C14C C11 C13C 113.8(11) . .
H12b C12A H12a 109.5 . .
H12c C12A H12a 109.5 . .
H12c C12A H12b 109.5 . .
H13b C13A H13a 109.5 . .
H13c C13A H13a 109.5 . .
H13c C13A H13b 109.5 . .
H14b C14A H14a 109.5 . .
H14c C14A H14a 109.5 . .
H14c C14A H14b 109.5 . .
H12e C12B H12d 109.5 . .
H12f C12B H12d 109.5 . .
H12f C12B H12e 109.5 . .
H13e C13B H13d 109.5 . .
H13f C13B H13d 109.5 . .
H13f C13B H13e 109.5 . .
H14e C14B H14d 109.5 . .
H14f C14B H14d 109.5 . .
H14f C14B H14e 109.5 . .
H12h C12C H12g 109.5 . .
H12i C12C H12g 109.5 . .
H12i C12C H12h 109.5 . .
H13h C13C H13g 109.5 . .
H13i C13C H13g 109.5 . .
H13i C13C H13h 109.5 . .
H14h C14C H14g 109.5 . .
H14i C14C H14g 109.5 . .
H14i C14C H14h 109.5 . .
C1 N1 O1 115.47(11) . .
C5 N1 O1 115.66(12) . .
C5 N1 C1 125.33(12) . .
C10 N2 C3 123.92(12) . .
H2 N2 C3 118.04(7) . .
H2 N2 C10 118.04(8) . .




_database_code_depnum_ccdc_archive 'CCDC 953446'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_CCDC-953447

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 4-tert-Butoxycarbonylamino-2,2,6,6-tetramethylpiperidin-1-oxid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H27 N2 O3'
_chemical_formula_sum            'C14 H27 N2 O3'
_chemical_formula_weight         271.38

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   11.94158(18)
_cell_length_b                   12.0243(2)
_cell_length_c                   11.31901(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1625.29(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(1)
_cell_measurement_reflns_used    13181
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      26.37

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.93
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.109
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             596
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24a (release 19-12-2012 CrysAlis171 .NET)
(compiled Dec 19 2012,11:08:27)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4340
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            45971
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         26.37
_reflns_number_total             1733
_reflns_number_gt                1499
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis CCD'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1998)'
_computing_publication_material  ' enCIFer (Allen et al., 2008)'

_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)+(0.0875P)²+0.4788P] 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         1733
_refine_ls_number_parameters     113
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1727
_refine_ls_wR_factor_gt          0.1661
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.63576(13) 0.36048(14) 0.64181(16) 0.0566(5) Uani 1 1 d . . .
C2 C 0.50857(14) 0.35191(17) 0.6281(2) 0.0675(6) Uani 1 1 d . . .
H2A H 0.473(2) 0.3486(18) 0.704(2) 0.081 Uiso 1 1 d . . .
H2B H 0.4851(19) 0.4227(19) 0.595(2) 0.081 Uiso 1 1 d . . .
C3 C 0.46938(18) 0.2500 0.5604(2) 0.0757(9) Uani 1 2 d S . .
H3A H 0.499(3) 0.2500 0.477(3) 0.091 Uiso 1 2 d S . .
C4 C 0.69246(18) 0.4001(2) 0.5283(2) 0.0901(8) Uani 1 1 d . . .
H4C H 0.7719 0.4042 0.5405 0.108 Uiso 1 1 calc R . .
H4B H 0.6644 0.4723 0.5075 0.108 Uiso 1 1 calc R . .
H4A H 0.6767 0.3486 0.4656 0.108 Uiso 1 1 calc R . .
C5 C 0.66388(19) 0.43909(17) 0.7442(3) 0.0882(8) Uani 1 1 d . . .
H5C H 0.7437 0.4443 0.7527 0.106 Uiso 1 1 calc R . .
H5B H 0.6319 0.4107 0.8159 0.106 Uiso 1 1 calc R . .
H5A H 0.6336 0.5115 0.7281 0.106 Uiso 1 1 calc R . .
C6 C 0.28909(18) 0.2500 0.4530(2) 0.0559(6) Uani 1 2 d S . .
C7 C 0.09154(18) 0.2500 0.3903(2) 0.0583(6) Uani 1 2 d S . .
C8 C 0.0994(2) 0.1484(2) 0.3152(3) 0.1134(11) Uani 1 1 d . . .
H8C H 0.1678 0.1503 0.2707 0.136 Uiso 1 1 calc R . .
H8B H 0.0369 0.1461 0.2619 0.136 Uiso 1 1 calc R . .
H8A H 0.0985 0.0835 0.3646 0.136 Uiso 1 1 calc R . .
C9 C -0.0141(3) 0.2500 0.4606(4) 0.145(2) Uani 1 2 d SD . .
H9B H -0.017(4) 0.190(2) 0.516(3) 0.174 Uiso 1 1 d D . .
H9A H -0.081(3) 0.2500 0.414(4) 0.174 Uiso 1 2 d SD . .
N1 N 0.68198(13) 0.2500 0.67296(15) 0.0439(4) Uani 1 2 d S . .
N2 N 0.34742(17) 0.2500 0.5528(2) 0.1082(13) Uani 1 2 d S . .
H2N H 0.3105 0.2500 0.6181 0.130 Uiso 1 2 calc SR . .
O1 O 0.78597(12) 0.2500 0.70222(16) 0.0592(5) Uani 1 2 d S . .
O2 O 0.17919(13) 0.2500 0.48000(15) 0.0778(7) Uani 1 2 d S . .
O3 O 0.32844(14) 0.2500 0.35638(16) 0.0742(6) Uani 1 2 d S . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.4811(18) . ?
C1 C4 1.528(3) . ?
C1 C2 1.530(2) . ?
C1 C5 1.533(3) . ?
C2 C3 1.519(3) . ?
C2 H2A 0.96(2) . ?
C2 H2B 0.97(2) . ?
C3 N2 1.459(3) . ?
C3 C2 1.519(3) 8_565 ?
C3 H3A 1.00(4) . ?
C4 H4C 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4A 0.9600 . ?
C5 H5C 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5A 0.9600 . ?
C6 O3 1.191(3) . ?
C6 N2 1.327(3) . ?
C6 O2 1.347(3) . ?
C7 O2 1.458(3) . ?
C7 C8 1.491(3) . ?
C7 C8 1.491(3) 8_565 ?
C7 C9 1.492(4) . ?
C8 H8C 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8A 0.9600 . ?
C9 H9B 0.960(3) . ?
C9 H9A 0.960(3) . ?
N1 O1 1.285(2) . ?
N1 C1 1.4811(18) 8_565 ?
N2 H2N 0.8600 . ?

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
N1 C1 C4 108.34(16) . . ?
N1 C1 C2 109.50(14) . . ?
C4 C1 C2 112.04(16) . . ?
N1 C1 C5 106.95(16) . . ?
C4 C1 C5 110.26(18) . . ?
C2 C1 C5 109.62(16) . . ?
C3 C2 C1 114.29(16) . . ?
C3 C2 H2A 106.3(14) . . ?
C1 C2 H2A 110.7(14) . . ?
C3 C2 H2B 115.0(13) . . ?
C1 C2 H2B 105.5(13) . . ?
H2A C2 H2B 104.7(18) . . ?
N2 C3 C2 109.71(13) . 8_565 ?
N2 C3 C2 109.71(13) . . ?
C2 C3 C2 107.6(2) 8_565 . ?
N2 C3 H3A 107(2) . . ?
C2 C3 H3A 111.3(10) 8_565 . ?
C2 C3 H3A 111.3(10) . . ?
C1 C4 H4C 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4C C4 H4B 109.5 . . ?
C1 C4 H4A 109.5 . . ?
H4C C4 H4A 109.5 . . ?
H4B C4 H4A 109.5 . . ?
C1 C5 H5C 109.5 . . ?
C1 C5 H5B 109.5 . . ?
H5C C5 H5B 109.5 . . ?
C1 C5 H5A 109.5 . . ?
H5C C5 H5A 109.5 . . ?
H5B C5 H5A 109.5 . . ?
O3 C6 N2 125.1(2) . . ?
O3 C6 O2 126.3(2) . . ?
N2 C6 O2 108.6(2) . . ?
O2 C7 C8 110.60(14) . . ?
O2 C7 C8 110.60(14) . 8_565 ?
C8 C7 C8 110.0(3) . 8_565 ?
O2 C7 C9 103.6(2) . . ?
C8 C7 C9 110.93(17) . . ?
C8 C7 C9 110.93(17) 8_565 . ?
C7 C8 H8C 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8C C8 H8B 109.5 . . ?
C7 C8 H8A 109.5 . . ?
H8C C8 H8A 109.5 . . ?
H8B C8 H8A 109.5 . . ?
C7 C9 H9B 112(3) . . ?
C7 C9 H9A 114(4) . . ?
H9B C9 H9A 109(3) . . ?
O1 N1 C1 114.93(9) . 8_565 ?
O1 N1 C1 114.92(9) . . ?
C1 N1 C1 127.51(17) 8_565 . ?
C6 N2 C3 125.0(2) . . ?
C6 N2 H2N 117.5 . . ?
C3 N2 H2N 117.5 . . ?
C6 O2 C7 122.77(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -43.2(2) . . . . ?
C4 C1 C2 C3 77.0(2) . . . . ?
C5 C1 C2 C3 -160.26(18) . . . . ?
C1 C2 C3 N2 179.86(17) . . . . ?
C1 C2 C3 C2 60.6(3) . . . 8_565 ?
C4 C1 N1 O1 66.4(2) . . . . ?
C2 C1 N1 O1 -171.10(17) . . . . ?
C5 C1 N1 O1 -52.4(2) . . . . ?
C4 C1 N1 C1 -94.0(2) . . . 8_565 ?
C2 C1 N1 C1 28.4(3) . . . 8_565 ?
C5 C1 N1 C1 147.13(18) . . . 8_565 ?
O3 C6 N2 C3 0.0 . . . . ?
O2 C6 N2 C3 180.0 . . . . ?
C2 C3 N2 C6 -121.02(15) 8_565 . . . ?
C2 C3 N2 C6 121.02(15) . . . . ?
O3 C6 O2 C7 0.0 . . . . ?
N2 C6 O2 C7 180.0 . . . . ?
C8 C7 O2 C6 61.07(19) . . . . ?
C8 C7 O2 C6 -61.07(19) 8_565 . . . ?
C9 C7 O2 C6 180.0 . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N O1 0.86 2.06 2.868(3) 157.3 6_557

_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_theta_full        26.32
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.036
_database_code_depnum_ccdc_archive 'CCDC 953447'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_CCDC-953448

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
3-(2,2,2-Trifluoroacetylamino)-2,2,5,5-tetramethylpyrrolidin-1-oxid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H18 F3 N2 O2'
_chemical_formula_weight         267.27

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   11.9401(7)
_cell_length_b                   11.3109(7)
_cell_length_c                   10.5933(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1430.66(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2412
_cell_measurement_theta_min      3.6090
_cell_measurement_theta_max      26.4540

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow-orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_F_000             564
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.686
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_detector_area_resol_mean 8.4353
_diffrn_reflns_number            6161
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.209
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             1523
_reflns_number_gt                1086
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SIR-2011 (Burla et al., 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0987P)²+0.4353P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1523
_refine_ls_number_parameters     116
_refine_ls_number_restraints     104
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0664
_refine_ls_wR_factor_ref         0.2075
_refine_ls_wR_factor_gt          0.1805
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.262
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.3654(2) 0.2500 1.2210(2) 0.0753(8) Uani 1 2 d S T P . .
O1 O 0.0614(2) 0.2500 0.6958(2) 0.0829(8) Uani 1 2 d S T P B .
N2 N 0.4232(2) 0.2500 1.0177(2) 0.0671(8) Uani 1 2 d S T P . .
H2N H 0.4816 0.2500 0.9702 0.081 Uiso 1 2 calc R U P . .
N1 N 0.1508(2) 0.2500 0.7637(2) 0.0544(7) Uani 1 2 d DS T P . .
C2 C 0.30054(18) 0.1418(2) 0.8754(2) 0.0639(7) Uani 1 1 d D . . . .
H2A H 0.3136 0.0718 0.9262 0.077 Uiso 1 1 calc R U . A 1
H2B H 0.3572 0.1439 0.8098 0.077 Uiso 1 1 calc R U . A 1
C3 C 0.3129(2) 0.2500 0.9577(3) 0.0579(8) Uani 1 2 d DS T P B .
H3 H 0.2545 0.2500 1.0227 0.069 Uiso 1 2 calc R U P . .
C6 C 0.4375(3) 0.2500 1.1417(3) 0.0528(7) Uani 1 2 d S T P B .
C7 C 0.5586(3) 0.2500 1.1829(3) 0.0713(10) Uani 1 2 d DS TU P . .
C1A C 0.1848(4) 0.1323(4) 0.8137(6) 0.0632(8) Uani 0.726(7) 1 d D U P B 1
C4A C 0.0963(6) 0.0909(10) 0.9081(11) 0.117(3) Uani 0.726(7) 1 d D U P B 1
H4A1 H 0.0933 0.1450 0.9778 0.176 Uiso 0.726(7) 1 calc R U P B 1
H4A2 H 0.1154 0.0135 0.9384 0.176 Uiso 0.726(7) 1 calc R U P B 1
H4A3 H 0.0245 0.0882 0.8674 0.176 Uiso 0.726(7) 1 calc R U P B 1
C5A C 0.1911(9) 0.0472(7) 0.7005(9) 0.102(3) Uani 0.726(7) 1 d D U P B 1
H5A1 H 0.2465 0.0749 0.6418 0.153 Uiso 0.726(7) 1 calc R U P B 1
H5A2 H 0.1194 0.0439 0.6594 0.153 Uiso 0.726(7) 1 calc R U P B 1
H5A3 H 0.2112 -0.0303 0.7295 0.153 Uiso 0.726(7) 1 calc R U P B 1
C1B C 0.1897(11) 0.1332(8) 0.8034(16) 0.0632(8) Uani 0.274(7) 1 d D U P B 2
C4B C 0.1005(14) 0.075(3) 0.887(3) 0.117(3) Uani 0.274(7) 1 d D U P B 2
H4B1 H 0.0308 0.0714 0.8421 0.176 Uiso 0.274(7) 1 calc R U P B 2
H4B2 H 0.0912 0.1201 0.9628 0.176 Uiso 0.274(7) 1 calc R U P B 2
H4B3 H 0.1240 -0.0040 0.9083 0.176 Uiso 0.274(7) 1 calc R U P B 2
C5B C 0.209(3) 0.060(2) 0.682(3) 0.102(3) Uani 0.274(7) 1 d D U P B 2
H5B1 H 0.1398 0.0521 0.6369 0.153 Uiso 0.274(7) 1 calc R U P B 2
H5B2 H 0.2375 -0.0164 0.7035 0.153 Uiso 0.274(7) 1 calc R U P B 2
H5B3 H 0.2627 0.1004 0.6290 0.153 Uiso 0.274(7) 1 calc R U P B 2
F1 F 0.6341(3) 0.2500 1.0937(4) 0.128(2) Uani 0.726(7) 2 d DS TU P B 1
F2 F 0.5822(3) 0.1592(3) 1.2556(4) 0.140(2) Uani 0.726(7) 1 d D U P B 1
F3 F 0.5669(9) 0.2500 1.3036(7) 0.128(2) Uani 0.274(7) 2 d DS TU P B 2
F4 F 0.6112(6) 0.1586(5) 1.1372(10) 0.132(5) Uani 0.274(7) 1 d D U P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C6 1.203(4) . y
O1 N1 1.288(3) . y
N2 C6 1.324(4) . y
N2 C3 1.462(4) . ?
N2 H2N 0.8600 . ?
N1 C1B 1.462(9) . ?
N1 C1B 1.462(9) 8_565 ?
N1 C1A 1.489(4) . ?
N1 C1A 1.489(4) 8_565 ?
C2 C3 1.510(3) . ?
C2 C1B 1.530(8) . ?
C2 C1A 1.532(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C2 1.510(3) 8_565 ?
C3 H3 0.9800 . ?
C6 C7 1.511(5) . ?
C7 F3 1.282(7) . ?
C7 F4 1.303(6) 8_565 ?
C7 F4 1.303(6) . ?
C7 F1 1.306(5) . ?
C7 F2 1.314(3) 8_565 ?
C7 F2 1.314(3) . ?
C1A C4A 1.529(5) . ?
C1A C5A 1.540(5) . ?
C4A H4A1 0.9600 . ?
C4A H4A2 0.9600 . ?
C4A H4A3 0.9600 . ?
C5A H5A1 0.9600 . ?
C5A H5A2 0.9600 . ?
C5A H5A3 0.9600 . ?
C1B C4B 1.535(9) . ?
C1B C5B 1.547(9) . ?
C4B H4B1 0.9600 . ?
C4B H4B2 0.9600 . ?
C4B H4B3 0.9600 . ?
C5B H5B1 0.9600 . ?
C5B H5B2 0.9600 . ?
C5B H5B3 0.9600 . ?

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
C6 N2 C3 123.2(3) . . ?
C6 N2 H2N 118.4 . . ?
C3 N2 H2N 118.4 . . ?
O1 N1 C1B 115.1(3) . . ?
O1 N1 C1B 115.1(3) . 8_565 ?
C1B N1 C1B 129.3(7) . 8_565 ?
O1 N1 C1A 115.15(17) . . ?
O1 N1 C1A 115.15(17) . 8_565 ?
C1A N1 C1A 126.8(4) . 8_565 ?
C3 C2 C1B 115.1(5) . . ?
C3 C2 C1A 113.0(3) . . ?
C3 C2 H2A 109.0 . . ?
C1A C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1A C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
N2 C3 C2 109.83(15) . . ?
N2 C3 C2 109.83(15) . 8_565 ?
C2 C3 C2 108.3(2) . 8_565 ?
N2 C3 H3 109.6 . . ?
C2 C3 H3 109.6 . . ?
C2 C3 H3 109.6 8_565 . ?
O2 C6 N2 126.9(3) . . ?
O2 C6 C7 118.9(3) . . ?
N2 C6 C7 114.2(3) . . ?
F3 C7 F4 109.5(5) . 8_565 ?
F3 C7 F4 109.5(5) . . ?
F4 C7 F4 105.0(9) 8_565 . ?
F1 C7 F2 106.0(3) . 8_565 ?
F1 C7 F2 106.0(3) . . ?
F2 C7 F2 102.9(4) 8_565 . ?
F3 C7 C6 111.2(6) . . ?
F4 C7 C6 110.7(3) 8_565 . ?
F4 C7 C6 110.7(3) . . ?
F1 C7 C6 116.8(3) . . ?
F2 C7 C6 112.0(3) 8_565 . ?
F2 C7 C6 112.0(3) . . ?
N1 C1A C4A 108.5(5) . . ?
N1 C1A C2 109.6(3) . . ?
C4A C1A C2 111.5(4) . . ?
N1 C1A C5A 107.2(4) . . ?
C4A C1A C5A 110.6(4) . . ?
C2 C1A C5A 109.4(4) . . ?
C1A C4A H4A1 109.5 . . ?
C1A C4A H4A2 109.5 . . ?
H4A1 C4A H4A2 109.5 . . ?
C1A C4A H4A3 109.5 . . ?
H4A1 C4A H4A3 109.5 . . ?
H4A2 C4A H4A3 109.5 . . ?
C1A C5A H5A1 109.5 . . ?
C1A C5A H5A2 109.5 . . ?
H5A1 C5A H5A2 109.5 . . ?
C1A C5A H5A3 109.5 . . ?
H5A1 C5A H5A3 109.5 . . ?
H5A2 C5A H5A3 109.5 . . ?
N1 C1B C2 111.2(6) . . ?
N1 C1B C4B 109.5(10) . . ?
C2 C1B C4B 109.8(10) . . ?
N1 C1B C5B 106.8(10) . . ?
C2 C1B C5B 108.6(10) . . ?
C4B C1B C5B 110.9(11) . . ?
C1B C4B H4B1 109.5 . . ?
C1B C4B H4B2 109.5 . . ?
H4B1 C4B H4B2 109.5 . . ?
C1B C4B H4B3 109.5 . . ?
H4B1 C4B H4B3 109.5 . . ?
H4B2 C4B H4B3 109.5 . . ?
C1B C5B H5B1 109.5 . . ?
C1B C5B H5B2 109.5 . . ?
H5B1 C5B H5B2 109.5 . . ?
C1B C5B H5B3 109.5 . . ?
H5B1 C5B H5B3 109.5 . . ?
H5B2 C5B H5B3 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N2 C3 C2 -120.49(16) . . . . ?
C6 N2 C3 C2 120.49(16) . . . 8_565 ?
C1B C2 C3 N2 -178.1(7) . . . . ?
C1A C2 C3 N2 177.4(3) . . . . ?
C1B C2 C3 C2 -58.1(8) . . . 8_565 ?
C1A C2 C3 C2 -62.7(4) . . . 8_565 ?
C3 N2 C6 O2 0.000(1) . . . . ?
C3 N2 C6 C7 180.000(1) . . . . ?
O2 C6 C7 F3 0.000(3) . . . . ?
N2 C6 C7 F3 180.000(3) . . . . ?
O2 C6 C7 F4 -122.0(5) . . . 8_565 ?
N2 C6 C7 F4 58.0(5) . . . 8_565 ?
O2 C6 C7 F4 122.0(5) . . . . ?
N2 C6 C7 F4 -58.0(5) . . . . ?
O2 C6 C7 F1 180.000(1) . . . . ?
N2 C6 C7 F1 0.000(1) . . . . ?
O2 C6 C7 F2 -57.5(3) . . . 8_565 ?
N2 C6 C7 F2 122.5(3) . . . 8_565 ?
O2 C6 C7 F2 57.5(3) . . . . ?
N2 C6 C7 F2 -122.5(3) . . . . ?
O1 N1 C1A C4A -66.5(5) . . . . ?
C1B N1 C1A C4A -157(6) . . . . ?
C1B N1 C1A C4A 98.7(7) 8_565 . . . ?
C1A N1 C1A C4A 93.0(9) 8_565 . . . ?
O1 N1 C1A C2 171.6(3) . . . . ?
C1B N1 C1A C2 81(5) . . . . ?
C1B N1 C1A C2 -23.3(6) 8_565 . . . ?
C1A N1 C1A C2 -28.9(10) 8_565 . . . ?
O1 N1 C1A C5A 53.0(5) . . . . ?
C1B N1 C1A C5A -38(5) . . . . ?
C1B N1 C1A C5A -141.9(8) 8_565 . . . ?
C1A N1 C1A C5A -147.5(7) 8_565 . . . ?
C3 C2 C1A N1 44.0(5) . . . . ?
C1B C2 C1A N1 -73(6) . . . . ?
C3 C2 C1A C4A -76.2(6) . . . . ?
C1B C2 C1A C4A 167(6) . . . . ?
C3 C2 C1A C5A 161.2(5) . . . . ?
C1B C2 C1A C5A 44(6) . . . . ?
O1 N1 C1B C2 176.0(8) . . . . ?
C1B N1 C1B C2 -13(3) 8_565 . . . ?
C1A N1 C1B C2 -92(5) . . . . ?
C1A N1 C1B C2 -18.9(14) 8_565 . . . ?
O1 N1 C1B C4B -62.5(11) . . . . ?
C1B N1 C1B C4B 109(2) 8_565 . . . ?
C1A N1 C1B C4B 29(5) . . . . ?
C1A N1 C1B C4B 102.7(14) 8_565 . . . ?
O1 N1 C1B C5B 57.7(11) . . . . ?
C1B N1 C1B C5B -131(2) 8_565 . . . ?
C1A N1 C1B C5B 149(6) . . . . ?
C1A N1 C1B C5B -137.2(13) 8_565 . . . ?
C3 C2 C1B N1 35.4(14) . . . . ?
C1A C2 C1B N1 100(6) . . . . ?
C3 C2 C1B C4B -86.0(15) . . . . ?
C1A C2 C1B C4B -21(6) . . . . ?
C3 C2 C1B C5B 152.6(14) . . . . ?
C1A C2 C1B C5B -143(7) . . . . ?

_refine_diff_density_max         0.219
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.049

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 953448'
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#                                CCDC 
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#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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data_CCDC-953449

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 N-Acetyl-N, N-bis-(1-oxo-2,2,6,6-tetramethylpiperidin-4-yl)-amine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H37 N3 O3'
_chemical_formula_sum            'C20 H37 N3 O3'
_chemical_formula_weight         367.53

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           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.28928(18)
_cell_length_b                   19.4108(4)
_cell_length_c                   26.6839(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4293.48(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(1)
_cell_measurement_reflns_used    22135
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      29.33

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.89
_exptl_crystal_size_mid          0.69
_exptl_crystal_size_min          0.59
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1616
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4340
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            74541
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0091
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         26.37
_reflns_number_total             4381
_reflns_number_gt                3715
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis CCD'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1998)'
_computing_publication_material  ' enCIFer (Allen et al., 2008)'

_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)+(0.0702P)²+1.5321P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4381
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1435
_refine_ls_wR_factor_gt          0.1366
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.39309(19) 0.63570(8) 0.45635(5) 0.0404(4) Uani 1 1 d . . .
C2 C 0.3290(2) 0.59355(10) 0.41250(6) 0.0489(4) Uani 1 1 d . . .
H2B H 0.2217 0.6099 0.4043 0.059 Uiso 1 1 calc R . .
H2A H 0.3191 0.5459 0.4231 0.059 Uiso 1 1 calc R . .
C3 C 0.43222(18) 0.59591(7) 0.36514(5) 0.0346(3) Uani 1 1 d . . .
H3A H 0.4371 0.6439 0.3538 0.042 Uiso 1 1 calc R . .
C4 C 0.60252(18) 0.57322(8) 0.37808(6) 0.0369(3) Uani 1 1 d . . .
H4B H 0.6675 0.5732 0.3478 0.044 Uiso 1 1 calc R . .
H4A H 0.5995 0.5265 0.3909 0.044 Uiso 1 1 calc R . .
C5 C 0.68197(19) 0.62000(9) 0.41706(6) 0.0417(4) Uani 1 1 d . . .
C6 C 0.3498(3) 0.71131(11) 0.45169(8) 0.0712(6) Uani 1 1 d . . .
H6C H 0.3931 0.7361 0.4798 0.085 Uiso 1 1 calc R . .
H6B H 0.2346 0.7162 0.4512 0.085 Uiso 1 1 calc R . .
H6A H 0.3944 0.7294 0.4212 0.085 Uiso 1 1 calc R . .
C7 C 0.3204(3) 0.60842(14) 0.50514(7) 0.0704(6) Uani 1 1 d . . .
H7C H 0.3603 0.6350 0.5328 0.084 Uiso 1 1 calc R . .
H7B H 0.3503 0.5610 0.5095 0.084 Uiso 1 1 calc R . .
H7A H 0.2050 0.6121 0.5037 0.084 Uiso 1 1 calc R . .
C8 C 0.7241(3) 0.69070(10) 0.39520(8) 0.0637(5) Uani 1 1 d . . .
H8C H 0.7745 0.7184 0.4206 0.076 Uiso 1 1 calc R . .
H8B H 0.6274 0.7130 0.3838 0.076 Uiso 1 1 calc R . .
H8A H 0.7970 0.6850 0.3675 0.076 Uiso 1 1 calc R . .
C9 C 0.8343(2) 0.58567(12) 0.43718(9) 0.0669(6) Uani 1 1 d . . .
H9C H 0.8843 0.6153 0.4614 0.080 Uiso 1 1 calc R . .
H9B H 0.9080 0.5775 0.4100 0.080 Uiso 1 1 calc R . .
H9A H 0.8066 0.5426 0.4527 0.080 Uiso 1 1 calc R . .
C10 C 0.07377(18) 0.40675(8) 0.35907(5) 0.0353(3) Uani 1 1 d . . .
C11 C 0.12742(18) 0.47532(8) 0.33633(6) 0.0364(3) Uani 1 1 d . . .
H11B H 0.0885 0.4782 0.3021 0.044 Uiso 1 1 calc R . .
H11A H 0.0793 0.5128 0.3552 0.044 Uiso 1 1 calc R . .
C12 C 0.30962(17) 0.48363(7) 0.33651(5) 0.0328(3) Uani 1 1 d . . .
H12A H 0.3458 0.4745 0.3708 0.039 Uiso 1 1 calc R . .
C13 C 0.38277(19) 0.42760(8) 0.30356(6) 0.0397(4) Uani 1 1 d . . .
H13B H 0.4988 0.4337 0.3022 0.048 Uiso 1 1 calc R . .
H13A H 0.3410 0.4322 0.2698 0.048 Uiso 1 1 calc R . .
C14 C 0.34457(19) 0.35507(8) 0.32331(6) 0.0400(4) Uani 1 1 d . . .
C15 C -0.1047(2) 0.39489(10) 0.34749(8) 0.0520(4) Uani 1 1 d . . .
H15C H -0.1386 0.3519 0.3618 0.062 Uiso 1 1 calc R . .
H15B H -0.1202 0.3937 0.3118 0.062 Uiso 1 1 calc R . .
H15A H -0.1675 0.4317 0.3616 0.062 Uiso 1 1 calc R . .
C16 C 0.0966(2) 0.40485(9) 0.41605(6) 0.0467(4) Uani 1 1 d . . .
H16C H 0.0619 0.3610 0.4287 0.056 Uiso 1 1 calc R . .
H16B H 0.0337 0.4408 0.4312 0.056 Uiso 1 1 calc R . .
H16A H 0.2085 0.4116 0.4239 0.056 Uiso 1 1 calc R . .
C17 C 0.4441(2) 0.33724(10) 0.36994(8) 0.0591(5) Uani 1 1 d . . .
H17C H 0.4167 0.2917 0.3811 0.071 Uiso 1 1 calc R . .
H17B H 0.4211 0.3698 0.3960 0.071 Uiso 1 1 calc R . .
H17A H 0.5569 0.3390 0.3618 0.071 Uiso 1 1 calc R . .
C18 C 0.3790(3) 0.30259(9) 0.28205(8) 0.0636(6) Uani 1 1 d . . .
H18C H 0.3561 0.2571 0.2942 0.076 Uiso 1 1 calc R . .
H18B H 0.4905 0.3054 0.2725 0.076 Uiso 1 1 calc R . .
H18A H 0.3122 0.3122 0.2535 0.076 Uiso 1 1 calc R . .
C19 C 0.34980(19) 0.57749(8) 0.27609(6) 0.0390(3) Uani 1 1 d . . .
C20 C 0.4270(3) 0.64566(9) 0.26310(7) 0.0539(5) Uani 1 1 d . . .
H20C H 0.4090 0.6557 0.2283 0.065 Uiso 1 1 calc R . .
H20B H 0.5409 0.6432 0.2694 0.065 Uiso 1 1 calc R . .
H20A H 0.3803 0.6814 0.2833 0.065 Uiso 1 1 calc R . .
N1 N 0.57120(17) 0.62843(8) 0.46050(5) 0.0450(3) Uani 1 1 d . . .
N2 N 0.16886(15) 0.35003(6) 0.33532(5) 0.0358(3) Uani 1 1 d . . .
N3 N 0.36223(15) 0.55424(6) 0.32402(4) 0.0356(3) Uani 1 1 d . . .
O1 O 0.63390(19) 0.65226(10) 0.50088(5) 0.0820(5) Uani 1 1 d . . .
O2 O 0.11161(15) 0.28893(6) 0.33945(5) 0.0523(3) Uani 1 1 d . . .
O3 O 0.28070(16) 0.54445(6) 0.24354(4) 0.0519(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
C1 N1 1.487(2) . ?
C1 C6 1.516(3) . ?
C1 C2 1.524(2) . ?
C1 C7 1.529(2) . ?
C2 C3 1.527(2) . ?
C2 H2B 0.9700 . ?
C2 H2A 0.9700 . ?
C3 N3 1.4816(17) . ?
C3 C4 1.519(2) . ?
C3 H3A 0.9800 . ?
C4 C5 1.530(2) . ?
C4 H4B 0.9700 . ?
C4 H4A 0.9700 . ?
C5 N1 1.488(2) . ?
C5 C9 1.526(3) . ?
C5 C8 1.532(3) . ?
C6 H6C 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6A 0.9600 . ?
C7 H7C 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7A 0.9600 . ?
C8 H8C 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8A 0.9600 . ?
C9 H9C 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9A 0.9600 . ?
C10 N2 1.4951(19) . ?
C10 C11 1.529(2) . ?
C10 C15 1.529(2) . ?
C10 C16 1.532(2) . ?
C11 C12 1.519(2) . ?
C11 H11B 0.9700 . ?
C11 H11A 0.9700 . ?
C12 N3 1.4764(18) . ?
C12 C13 1.5241(19) . ?
C12 H12A 0.9800 . ?
C13 C14 1.536(2) . ?
C13 H13B 0.9700 . ?
C13 H13A 0.9700 . ?
C14 N2 1.495(2) . ?
C14 C18 1.527(2) . ?
C14 C17 1.532(3) . ?
C15 H15C 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15A 0.9600 . ?
C16 H16C 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16A 0.9600 . ?
C17 H17C 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17A 0.9600 . ?
C18 H18C 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18A 0.9600 . ?
C19 O3 1.2221(19) . ?
C19 N3 1.3601(19) . ?
C19 C20 1.510(2) . ?
C20 H20C 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20A 0.9600 . ?
N1 O1 1.2824(18) . ?
N2 O2 1.2821(16) . ?

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
N1 C1 C6 109.45(16) . . ?
N1 C1 C2 110.63(13) . . ?
C6 C1 C2 111.99(15) . . ?
N1 C1 C7 107.15(14) . . ?
C6 C1 C7 108.17(16) . . ?
C2 C1 C7 109.29(15) . . ?
C1 C2 C3 115.09(13) . . ?
C1 C2 H2B 108.5 . . ?
C3 C2 H2B 108.5 . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2A 108.5 . . ?
H2B C2 H2A 107.5 . . ?
N3 C3 C4 111.96(12) . . ?
N3 C3 C2 112.15(12) . . ?
C4 C3 C2 108.92(13) . . ?
N3 C3 H3A 107.9 . . ?
C4 C3 H3A 107.9 . . ?
C2 C3 H3A 107.9 . . ?
C3 C4 C5 112.49(12) . . ?
C3 C4 H4B 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
H4B C4 H4A 107.8 . . ?
N1 C5 C9 106.55(14) . . ?
N1 C5 C4 109.23(12) . . ?
C9 C5 C4 109.66(15) . . ?
N1 C5 C8 109.82(14) . . ?
C9 C5 C8 109.66(16) . . ?
C4 C5 C8 111.78(14) . . ?
C1 C6 H6C 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6C C6 H6B 109.5 . . ?
C1 C6 H6A 109.5 . . ?
H6C C6 H6A 109.5 . . ?
H6B C6 H6A 109.5 . . ?
C1 C7 H7C 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7C C7 H7B 109.5 . . ?
C1 C7 H7A 109.5 . . ?
H7C C7 H7A 109.5 . . ?
H7B C7 H7A 109.5 . . ?
C5 C8 H8C 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8C C8 H8B 109.5 . . ?
C5 C8 H8A 109.5 . . ?
H8C C8 H8A 109.5 . . ?
H8B C8 H8A 109.5 . . ?
C5 C9 H9C 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9C C9 H9B 109.5 . . ?
C5 C9 H9A 109.5 . . ?
H9C C9 H9A 109.5 . . ?
H9B C9 H9A 109.5 . . ?
N2 C10 C11 108.63(11) . . ?
N2 C10 C15 108.28(13) . . ?
C11 C10 C15 109.41(13) . . ?
N2 C10 C16 109.74(12) . . ?
C11 C10 C16 112.27(13) . . ?
C15 C10 C16 108.44(14) . . ?
C12 C11 C10 112.36(12) . . ?
C12 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
H11B C11 H11A 107.9 . . ?
N3 C12 C11 113.06(12) . . ?
N3 C12 C13 114.50(12) . . ?
C11 C12 C13 108.54(12) . . ?
N3 C12 H12A 106.8 . . ?
C11 C12 H12A 106.8 . . ?
C13 C12 H12A 106.8 . . ?
C12 C13 C14 111.97(12) . . ?
C12 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C12 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
H13B C13 H13A 107.9 . . ?
N2 C14 C18 107.05(14) . . ?
N2 C14 C17 109.62(13) . . ?
C18 C14 C17 109.51(16) . . ?
N2 C14 C13 109.54(12) . . ?
C18 C14 C13 109.00(14) . . ?
C17 C14 C13 112.00(14) . . ?
C10 C15 H15C 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15C C15 H15B 109.5 . . ?
C10 C15 H15A 109.5 . . ?
H15C C15 H15A 109.5 . . ?
H15B C15 H15A 109.5 . . ?
C10 C16 H16C 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16C C16 H16B 109.5 . . ?
C10 C16 H16A 109.5 . . ?
H16C C16 H16A 109.5 . . ?
H16B C16 H16A 109.5 . . ?
C14 C17 H17C 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17C C17 H17B 109.5 . . ?
C14 C17 H17A 109.5 . . ?
H17C C17 H17A 109.5 . . ?
H17B C17 H17A 109.5 . . ?
C14 C18 H18C 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18C C18 H18B 109.5 . . ?
C14 C18 H18A 109.5 . . ?
H18C C18 H18A 109.5 . . ?
H18B C18 H18A 109.5 . . ?
O3 C19 N3 121.98(14) . . ?
O3 C19 C20 119.68(14) . . ?
N3 C19 C20 118.32(14) . . ?
C19 C20 H20C 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20C C20 H20B 109.5 . . ?
C19 C20 H20A 109.5 . . ?
H20C C20 H20A 109.5 . . ?
H20B C20 H20A 109.5 . . ?
O1 N1 C1 115.51(13) . . ?
O1 N1 C5 116.36(14) . . ?
C1 N1 C5 124.41(12) . . ?
O2 N2 C14 116.09(12) . . ?
O2 N2 C10 116.71(12) . . ?
C14 N2 C10 123.81(11) . . ?
C19 N3 C12 119.85(12) . . ?
C19 N3 C3 123.02(12) . . ?
C12 N3 C3 117.09(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -40.8(2) . . . . ?
C6 C1 C2 C3 81.6(2) . . . . ?
C7 C1 C2 C3 -158.59(16) . . . . ?
C1 C2 C3 N3 -179.61(13) . . . . ?
C1 C2 C3 C4 55.89(19) . . . . ?
N3 C3 C4 C5 174.69(12) . . . . ?
C2 C3 C4 C5 -60.71(16) . . . . ?
C3 C4 C5 N1 50.53(17) . . . . ?
C3 C4 C5 C9 166.95(15) . . . . ?
C3 C4 C5 C8 -71.22(18) . . . . ?
N2 C10 C11 C12 -49.75(16) . . . . ?
C15 C10 C11 C12 -167.76(13) . . . . ?
C16 C10 C11 C12 71.80(16) . . . . ?
C10 C11 C12 N3 -168.77(11) . . . . ?
C10 C11 C12 C13 63.04(16) . . . . ?
N3 C12 C13 C14 171.18(12) . . . . ?
C11 C12 C13 C14 -61.45(17) . . . . ?
C12 C13 C14 N2 47.57(17) . . . . ?
C12 C13 C14 C18 164.39(15) . . . . ?
C12 C13 C14 C17 -74.27(17) . . . . ?
C6 C1 N1 O1 67.3(2) . . . . ?
C2 C1 N1 O1 -168.78(16) . . . . ?
C7 C1 N1 O1 -49.7(2) . . . . ?
C6 C1 N1 C5 -90.03(18) . . . . ?
C2 C1 N1 C5 33.8(2) . . . . ?
C7 C1 N1 C5 152.89(16) . . . . ?
C9 C5 N1 O1 45.7(2) . . . . ?
C4 C5 N1 O1 164.07(16) . . . . ?
C8 C5 N1 O1 -73.0(2) . . . . ?
C9 C5 N1 C1 -157.11(16) . . . . ?
C4 C5 N1 C1 -38.7(2) . . . . ?
C8 C5 N1 C1 84.19(19) . . . . ?
C18 C14 N2 O2 44.27(18) . . . . ?
C17 C14 N2 O2 -74.42(17) . . . . ?
C13 C14 N2 O2 162.32(13) . . . . ?
C18 C14 N2 C10 -157.23(15) . . . . ?
C17 C14 N2 C10 84.07(17) . . . . ?
C13 C14 N2 C10 -39.19(19) . . . . ?
C11 C10 N2 O2 -161.65(13) . . . . ?
C15 C10 N2 O2 -42.93(18) . . . . ?
C16 C10 N2 O2 75.27(16) . . . . ?
C11 C10 N2 C14 39.97(18) . . . . ?
C15 C10 N2 C14 158.70(14) . . . . ?
C16 C10 N2 C14 -83.11(17) . . . . ?
O3 C19 N3 C12 7.8(2) . . . . ?
C20 C19 N3 C12 -171.07(14) . . . . ?
O3 C19 N3 C3 -174.33(15) . . . . ?
C20 C19 N3 C3 6.8(2) . . . . ?
C11 C12 N3 C19 -72.65(17) . . . . ?
C13 C12 N3 C19 52.36(19) . . . . ?
C11 C12 N3 C3 109.34(14) . . . . ?
C13 C12 N3 C3 -125.64(14) . . . . ?
C4 C3 N3 C19 -103.13(16) . . . . ?
C2 C3 N3 C19 134.08(16) . . . . ?
C4 C3 N3 C12 74.81(16) . . . . ?
C2 C3 N3 C12 -47.98(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.947
_diffrn_reflns_theta_full        26.32
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.049
_database_code_depnum_ccdc_archive 'CCDC 953449'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_CCDC-953450

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
N-(2,2,2-Trifluoroacetyl)-N,N-bis-
(1-oxo-2,2,6,6-tetramethylpiperidin-4-yl)-amine
1/2 ethanol hemihydrat
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H34 F3 N3 O3, 0.5(C2 H6 O), 0.5(H2 O)'
_chemical_formula_sum            'C21 H38 F3 N3 O4'
_chemical_formula_weight         453.54

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.2418(4)
_cell_length_b                   9.4098(2)
_cell_length_c                   19.4980(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.412(3)
_cell_angle_gamma                90
_cell_volume                     2541.71(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8000
_cell_measurement_theta_min      3.5860
_cell_measurement_theta_max      23.6460


_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.750
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_detector_area_resol_mean 8.4353
_diffrn_reflns_number            30132
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.941
_diffrn_reflns_theta_max         25.242
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4546
_reflns_number_gt                3649
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'OLEX2.SOLVE (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1161P)²+0.6399P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4546
_refine_ls_number_parameters     310
_refine_ls_number_restraints     154
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1837
_refine_ls_wR_factor_gt          0.1690
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.073
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.21828(15) -0.3267(2) 0.49372(10) 0.0866(6) Uani 1 1 d . . . . .
O2 O 0.12515(14) 0.2527(2) 0.85976(10) 0.0855(6) Uani 1 1 d . . . . .
O3 O 0.44580(12) 0.30743(19) 0.72642(9) 0.0724(5) Uani 1 1 d D . . . .
N1 N 0.24595(13) -0.22122(18) 0.53507(10) 0.0553(5) Uani 1 1 d . . . . .
N2 N 0.17991(13) 0.23048(19) 0.81716(9) 0.0554(5) Uani 1 1 d . . . . .
N3 N 0.34962(11) 0.13083(17) 0.66888(8) 0.0465(4) Uani 1 1 d D . . . .
C1 C 0.32679(16) -0.2509(2) 0.59717(12) 0.0559(6) Uani 1 1 d . . . . .
C2 C 0.33439(15) -0.1300(2) 0.65011(11) 0.0497(5) Uani 1 1 d . . . . .
H2A H 0.2815 -0.1371 0.6736 0.060 Uiso 1 1 calc R U . . .
H2B H 0.3942 -0.1396 0.6857 0.060 Uiso 1 1 calc R U . . .
C3 C 0.33172(13) 0.0153(2) 0.61580(10) 0.0429(5) Uani 1 1 d . . . . .
H3 H 0.3836 0.0184 0.5904 0.052 Uiso 1 1 calc R U . . .
C4 C 0.23684(14) 0.0337(2) 0.56209(10) 0.0482(5) Uani 1 1 d . . . . .
H4A H 0.2348 0.1277 0.5413 0.058 Uiso 1 1 calc R U . . .
H4B H 0.1842 0.0271 0.5858 0.058 Uiso 1 1 calc R U . . .
C5 C 0.22249(15) -0.0774(2) 0.50368(11) 0.0526(5) Uani 1 1 d . . . . .
C6 C 0.42007(19) -0.2714(3) 0.57233(17) 0.0827(8) Uani 1 1 d . . . . .
H6A H 0.4099 -0.3411 0.5354 0.124 Uiso 1 1 calc R U . . .
H6B H 0.4703 -0.3031 0.6111 0.124 Uiso 1 1 calc R U . . .
H6C H 0.4386 -0.1828 0.5549 0.124 Uiso 1 1 calc R U . . .
C7 C 0.3035(3) -0.3877(3) 0.63172(17) 0.0878(9) Uani 1 1 d . . . . .
H7A H 0.2438 -0.3766 0.6459 0.132 Uiso 1 1 calc R U . . .
H7B H 0.3544 -0.4081 0.6723 0.132 Uiso 1 1 calc R U . . .
H7C H 0.2978 -0.4646 0.5987 0.132 Uiso 1 1 calc R U . . .
C8 C 0.11684(18) -0.0778(3) 0.46375(14) 0.0796(8) Uani 1 1 d . . . . .
H8A H 0.1086 -0.1412 0.4243 0.119 Uiso 1 1 calc R U . . .
H8B H 0.0981 0.0165 0.4472 0.119 Uiso 1 1 calc R U . . .
H8C H 0.0773 -0.1088 0.4946 0.119 Uiso 1 1 calc R U . . .
C9 C 0.2857(2) -0.0477(3) 0.45136(12) 0.0739(7) Uani 1 1 d . . . . .
H9A H 0.3518 -0.0379 0.4766 0.111 Uiso 1 1 calc R U . . .
H9B H 0.2647 0.0386 0.4261 0.111 Uiso 1 1 calc R U . . .
H9C H 0.2801 -0.1251 0.4186 0.111 Uiso 1 1 calc R U . . .
C10 C 0.24643(16) 0.1063(2) 0.83483(11) 0.0537(5) Uani 1 1 d . . . . .
C11 C 0.32267(15) 0.1148(2) 0.79113(11) 0.0515(5) Uani 1 1 d . . . . .
H11A H 0.3686 0.1890 0.8102 0.062 Uiso 1 1 calc R U . . .
H11B H 0.3575 0.0255 0.7951 0.062 Uiso 1 1 calc R U . . .
C12 C 0.27919(13) 0.1453(2) 0.71421(10) 0.0439(5) Uani 1 1 d . . . . .
H12 H 0.2283 0.0748 0.6979 0.053 Uiso 1 1 calc R U . . .
C13 C 0.23108(15) 0.2901(2) 0.70808(11) 0.0493(5) Uani 1 1 d . . . . .
H13A H 0.2062 0.3125 0.6586 0.059 Uiso 1 1 calc R U . . .
H13B H 0.2788 0.3614 0.7279 0.059 Uiso 1 1 calc R U . . .
C14 C 0.14856(15) 0.2963(2) 0.74599(11) 0.0525(5) Uani 1 1 d . . . . .
C15 C 0.2971(2) 0.1166(3) 0.91323(12) 0.0755(7) Uani 1 1 d . . . . .
H15A H 0.3309 0.2054 0.9220 0.113 Uiso 1 1 calc R U . . .
H15B H 0.3421 0.0396 0.9255 0.113 Uiso 1 1 calc R U . . .
H15C H 0.2499 0.1111 0.9412 0.113 Uiso 1 1 calc R U . . .
C16 C 0.1882(2) -0.0318(3) 0.82137(15) 0.0738(7) Uani 1 1 d . . . . .
H16A H 0.1375 -0.0293 0.8463 0.111 Uiso 1 1 calc R U . . .
H16B H 0.2299 -0.1111 0.8376 0.111 Uiso 1 1 calc R U . . .
H16C H 0.1606 -0.0417 0.7718 0.111 Uiso 1 1 calc R U . . .
C17 C 0.05837(17) 0.2202(3) 0.70444(15) 0.0729(7) Uani 1 1 d . . . . .
H17A H 0.0739 0.1230 0.6968 0.109 Uiso 1 1 calc R U . . .
H17B H 0.0356 0.2665 0.6598 0.109 Uiso 1 1 calc R U . . .
H17C H 0.0090 0.2232 0.7306 0.109 Uiso 1 1 calc R U . . .
C18 C 0.1242(2) 0.4507(3) 0.75633(15) 0.0748(7) Uani 1 1 d . . . . .
H18A H 0.0721 0.4554 0.7799 0.112 Uiso 1 1 calc R U . . .
H18B H 0.1051 0.4966 0.7113 0.112 Uiso 1 1 calc R U . . .
H18C H 0.1798 0.4978 0.7843 0.112 Uiso 1 1 calc R U . . .
C19 C 0.42779(16) 0.2152(2) 0.68144(12) 0.0573(6) Uani 1 1 d D . . . .
C20A C 0.5076(4) 0.1850(6) 0.6411(3) 0.0766(14) Uani 0.669(8) 1 d D U P A 1
F1A F 0.5428(4) 0.0517(5) 0.6482(3) 0.0906(12) Uani 0.669(8) 1 d D U P A 1
F2A F 0.5830(3) 0.2701(6) 0.6629(3) 0.1130(17) Uani 0.669(8) 1 d D U P A 1
F3A F 0.4752(4) 0.2076(6) 0.5705(2) 0.0942(13) Uani 0.669(8) 1 d D U P A 1
C20B C 0.4881(7) 0.2181(11) 0.6266(5) 0.0766(14) Uani 0.331(8) 1 d D U P A 2
F1B F 0.5394(8) 0.0977(11) 0.6290(6) 0.0906(12) Uani 0.331(8) 1 d D U P A 2
F2B F 0.5475(7) 0.3299(11) 0.6385(6) 0.1130(17) Uani 0.331(8) 1 d D U P A 2
F3B F 0.4353(7) 0.2349(13) 0.5596(4) 0.0942(13) Uani 0.331(8) 1 d D U P A 2
O1W O 0.0759(2) -0.1788(5) 0.6440(2) 0.0873(11) Uani 0.5 1 d D U P B -1
H1WA H 0.0734 -0.2179 0.6060 0.131 Uiso 0.5 1 d DR U P B -1
H1WB H 0.0285 -0.1962 0.6597 0.131 Uiso 0.5 1 d DR U P B -1
O1S O 0.0841(8) 0.5461(14) 0.5636(5) 0.244(5) Uani 0.5 1 d G U P B -1
H1S H 0.0747 0.6042 0.5926 0.366 Uiso 0.5 1 calc R U P B -1
C1S C -0.0059(9) 0.510(3) 0.5168(15) 0.307(11) Uani 0.5 1 d G U P B -1
H1SA H -0.0384 0.5953 0.4956 0.368 Uiso 0.5 1 calc R U P B -1
H1SB H -0.0474 0.4621 0.5425 0.368 Uiso 0.5 1 calc R U P B -1
C2S C 0.015(2) 0.413(3) 0.4602(12) 0.307(11) Uani 0.5 1 d G U P B -1
H2SA H -0.0440 0.3873 0.4281 0.460 Uiso 0.5 1 calc R U P B -1
H2SB H 0.0473 0.3289 0.4817 0.460 Uiso 0.5 1 calc R U P B -1
H2SC H 0.0563 0.4616 0.4351 0.460 Uiso 0.5 1 calc R U P B -1


_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 1.282(2) . ?
O2 N2 1.282(2) . ?
O3 C19 1.218(3) . ?
N1 C5 1.491(3) . ?
N1 C1 1.491(3) . ?
N2 C14 1.490(3) . ?
N2 C10 1.493(3) . ?
N3 C19 1.342(3) . ?
N3 C3 1.482(2) . ?
N3 C12 1.489(2) . ?
C1 C2 1.523(3) . ?
C1 C7 1.524(3) . ?
C1 C6 1.528(3) . ?
C2 C3 1.519(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.515(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.524(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C8 1.525(3) . ?
C5 C9 1.534(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.530(3) . ?
C10 C16 1.532(3) . ?
C10 C15 1.535(3) . ?
C11 C12 1.511(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.518(3) . ?
C12 H12 0.9800 . ?
C13 C14 1.528(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C18 1.518(3) . ?
C14 C17 1.529(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20B 1.519(7) . ?
C19 C20A 1.551(5) . ?
C20A F2A 1.328(5) . ?
C20A F1A 1.346(5) . ?
C20A F3A 1.363(5) . ?
C20B F2B 1.336(8) . ?
C20B F1B 1.343(8) . ?
C20B F3B 1.357(8) . ?
O1W H1WA 0.8201 . ?
O1W H1WB 0.8198 . ?
O1S C1S 1.4301 . ?
O1S H1S 0.8200 . ?
C1S C2S 1.5150 . ?
C1S H1SA 0.9700 . ?
C1S H1SB 0.9700 . ?
C2S H2SA 0.9600 . ?
C2S H2SB 0.9600 . ?
C2S H2SC 0.9600 . ?

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
O1 N1 C5 115.96(18) . . ?
O1 N1 C1 115.62(18) . . ?
C5 N1 C1 124.11(16) . . ?
O2 N2 C14 116.08(17) . . ?
O2 N2 C10 115.29(17) . . ?
C14 N2 C10 125.24(16) . . ?
C19 N3 C3 124.20(16) . . ?
C19 N3 C12 118.81(16) . . ?
C3 N3 C12 116.83(14) . . ?
N1 C1 C2 109.29(16) . . ?
N1 C1 C7 108.1(2) . . ?
C2 C1 C7 108.7(2) . . ?
N1 C1 C6 109.3(2) . . ?
C2 C1 C6 112.24(19) . . ?
C7 C1 C6 109.1(2) . . ?
C3 C2 C1 112.56(17) . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
N3 C3 C4 112.37(15) . . ?
N3 C3 C2 111.72(15) . . ?
C4 C3 C2 109.53(16) . . ?
N3 C3 H3 107.7 . . ?
C4 C3 H3 107.7 . . ?
C2 C3 H3 107.7 . . ?
C3 C4 C5 112.43(16) . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
N1 C5 C4 109.72(16) . . ?
N1 C5 C8 107.94(19) . . ?
C4 C5 C8 109.17(19) . . ?
N1 C5 C9 109.17(19) . . ?
C4 C5 C9 111.96(18) . . ?
C8 C5 C9 108.8(2) . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C11 108.96(16) . . ?
N2 C10 C16 109.57(19) . . ?
C11 C10 C16 112.04(18) . . ?
N2 C10 C15 107.86(18) . . ?
C11 C10 C15 108.74(19) . . ?
C16 C10 C15 109.6(2) . . ?
C12 C11 C10 112.47(16) . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
N3 C12 C11 113.22(15) . . ?
N3 C12 C13 112.92(16) . . ?
C11 C12 C13 108.81(16) . . ?
N3 C12 H12 107.2 . . ?
C11 C12 H12 107.2 . . ?
C13 C12 H12 107.2 . . ?
C12 C13 C14 112.34(16) . . ?
C12 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
N2 C14 C18 107.61(18) . . ?
N2 C14 C13 109.68(16) . . ?
C18 C14 C13 109.04(19) . . ?
N2 C14 C17 109.39(19) . . ?
C18 C14 C17 109.2(2) . . ?
C13 C14 C17 111.82(19) . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 N3 125.4(2) . . ?
O3 C19 C20B 115.7(4) . . ?
N3 C19 C20B 117.6(4) . . ?
O3 C19 C20A 116.0(2) . . ?
N3 C19 C20A 118.3(2) . . ?
F2A C20A F1A 106.0(4) . . ?
F2A C20A F3A 106.8(4) . . ?
F1A C20A F3A 106.3(4) . . ?
F2A C20A C19 111.1(4) . . ?
F1A C20A C19 114.7(4) . . ?
F3A C20A C19 111.5(4) . . ?
F2B C20B F1B 110.0(8) . . ?
F2B C20B F3B 105.3(8) . . ?
F1B C20B F3B 107.9(8) . . ?
F2B C20B C19 109.3(7) . . ?
F1B C20B C19 110.6(7) . . ?
F3B C20B C19 113.7(7) . . ?
H1WA O1W H1WB 112.5 . . ?
C1S O1S H1S 109.5 . . ?
O1S C1S C2S 107.8 . . ?
O1S C1S H1SA 110.1 . . ?
C2S C1S H1SA 110.1 . . ?
O1S C1S H1SB 110.1 . . ?
C2S C1S H1SB 110.1 . . ?
H1SA C1S H1SB 108.5 . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 C2 -165.79(19) . . . . ?
C5 N1 C1 C2 38.5(3) . . . . ?
O1 N1 C1 C7 -47.7(3) . . . . ?
C5 N1 C1 C7 156.6(2) . . . . ?
O1 N1 C1 C6 71.0(2) . . . . ?
C5 N1 C1 C6 -84.7(2) . . . . ?
N1 C1 C2 C3 -47.5(2) . . . . ?
C7 C1 C2 C3 -165.29(19) . . . . ?
C6 C1 C2 C3 73.9(2) . . . . ?
C19 N3 C3 C4 -122.7(2) . . . . ?
C12 N3 C3 C4 62.0(2) . . . . ?
C19 N3 C3 C2 113.7(2) . . . . ?
C12 N3 C3 C2 -61.6(2) . . . . ?
C1 C2 C3 N3 -173.93(16) . . . . ?
C1 C2 C3 C4 60.9(2) . . . . ?
N3 C3 C4 C5 174.84(16) . . . . ?
C2 C3 C4 C5 -60.4(2) . . . . ?
O1 N1 C5 C4 166.11(18) . . . . ?
C1 N1 C5 C4 -38.3(3) . . . . ?
O1 N1 C5 C8 47.3(3) . . . . ?
C1 N1 C5 C8 -157.1(2) . . . . ?
O1 N1 C5 C9 -70.9(2) . . . . ?
C1 N1 C5 C9 84.8(2) . . . . ?
C3 C4 C5 N1 46.9(2) . . . . ?
C3 C4 C5 C8 165.0(2) . . . . ?
C3 C4 C5 C9 -74.5(2) . . . . ?
O2 N2 C10 C11 -166.32(19) . . . . ?
C14 N2 C10 C11 35.4(3) . . . . ?
O2 N2 C10 C16 70.8(2) . . . . ?
C14 N2 C10 C16 -87.5(2) . . . . ?
O2 N2 C10 C15 -48.4(3) . . . . ?
C14 N2 C10 C15 153.3(2) . . . . ?
N2 C10 C11 C12 -47.2(2) . . . . ?
C16 C10 C11 C12 74.2(2) . . . . ?
C15 C10 C11 C12 -164.54(19) . . . . ?
C19 N3 C12 C11 -61.0(2) . . . . ?
C3 N3 C12 C11 114.53(18) . . . . ?
C19 N3 C12 C13 63.2(2) . . . . ?
C3 N3 C12 C13 -121.26(18) . . . . ?
C10 C11 C12 N3 -170.67(16) . . . . ?
C10 C11 C12 C13 62.9(2) . . . . ?
N3 C12 C13 C14 171.43(15) . . . . ?
C11 C12 C13 C14 -62.0(2) . . . . ?
O2 N2 C14 C18 48.5(3) . . . . ?
C10 N2 C14 C18 -153.4(2) . . . . ?
O2 N2 C14 C13 166.94(19) . . . . ?
C10 N2 C14 C13 -34.9(3) . . . . ?
O2 N2 C14 C17 -70.1(2) . . . . ?
C10 N2 C14 C17 88.1(2) . . . . ?
C12 C13 C14 N2 45.8(2) . . . . ?
C12 C13 C14 C18 163.43(18) . . . . ?
C12 C13 C14 C17 -75.7(2) . . . . ?
C3 N3 C19 O3 -177.3(2) . . . . ?
C12 N3 C19 O3 -2.1(3) . . . . ?
C3 N3 C19 C20B 16.1(6) . . . . ?
C12 N3 C19 C20B -168.7(5) . . . . ?
C3 N3 C19 C20A -3.7(4) . . . . ?
C12 N3 C19 C20A 171.5(3) . . . . ?
O3 C19 C20A F2A -1.1(5) . . . . ?
N3 C19 C20A F2A -175.3(4) . . . . ?
C20B C19 C20A F2A 92.2(17) . . . . ?
O3 C19 C20A F1A 119.0(4) . . . . ?
N3 C19 C20A F1A -55.2(5) . . . . ?
C20B C19 C20A F1A -147.7(19) . . . . ?
O3 C19 C20A F3A -120.1(4) . . . . ?
N3 C19 C20A F3A 65.6(5) . . . . ?
C20B C19 C20A F3A -26.8(15) . . . . ?
O3 C19 C20B F2B -2.7(9) . . . . ?
N3 C19 C20B F2B 165.2(6) . . . . ?
C20A C19 C20B F2B -97.9(18) . . . . ?
O3 C19 C20B F1B 118.4(7) . . . . ?
N3 C19 C20B F1B -73.6(8) . . . . ?
C20A C19 C20B F1B 23.3(14) . . . . ?
O3 C19 C20B F3B -120.0(7) . . . . ?
N3 C19 C20B F3B 47.9(9) . . . . ?
C20A C19 C20B F3B 145(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2B O3 0.97 2.56 3.528(3) 174 2_646
C3 H3 F1A 0.98 2.31 2.944(5) 122 .
C3 H3 F3A 0.98 2.29 3.011(5) 129 .
C3 H3 F1B 0.98 2.30 3.010(11) 129 .
C3 H3 F3B 0.98 2.29 2.897(11) 119 .
C7 H7A O1S 0.96 2.57 3.162(11) 120 1_545
C11 H11A O3 0.97 2.44 2.997(3) 116 .
C11 H11B F2A 0.97 2.62 3.545(5) 161 2_646
C11 H11B F2B 0.97 2.47 3.362(7) 154 2_646
C13 H13B O3 0.97 2.44 3.000(3) 117 .
O1W H1WA O1S 0.82 2.39 3.042(13) 138 1_545
O1W H1WB O2 0.82 2.19 2.919(4) 149 2_546
O1S H1S O1W 0.82 2.27 3.042(13) 157 1_565

_refine_diff_density_max         0.567
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 953450'
