# Electronic Supplementary Material (ESI) for Chemical Science
# This journal is © The Royal Society of Chemistry 2013


#######################################################################
#
#                 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 
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#  data retrieval see:
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data_1
_database_code_depnum_ccdc_archive 'CCDC 924289'
#TrackingRef '17682_web_deposit_cif_file_0_OlivierBaudoin_1360704308.Cpd3i.cif'
_exptl_special_details           
;
The crystal was
placed in the cold stream of an Oxford
Cryosystems open-flow nitrogen cryostat (Cosier &
Glazer, 1986) with a nominal stability of 0.1K.
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107.
;
_refine_special_details          
;
?
;
#---------------------------------------------------------------
# _oxford_ data items, April 2010:
# There is some uncertainty about the correct way of forming local data
# names, e.g.
# _atom_site_special_shape_oxford
# or
# _oxford_atom_site_special_shape
# see:
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace
# A reserved prefix, e.g. foo, must be used in the following way
# " If the data file contains items defined in a DDL1 dictionary, the
# local data names assigned under the reserved prefix must contain it as
# their first component, e.g. _foo_atom_site_my_item. "
# However, this seems to say the opposite:
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html
# According to advice from the IUCr, CRYSTALS is correct
#---------------------------------------------------------------
# End of 'script/refcif.dat'
#end of refcif
_cell_length_a                   8.7960(10)
_cell_length_b                   8.8679(7)
_cell_length_c                   10.3885(9)
_cell_angle_alpha                75.311(7)
_cell_angle_beta                 80.306(9)
_cell_angle_gamma                71.263(10)
_cell_volume                     738.95(13)
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z            2
# Given Formula = C15 H18 N3 O3
# Dc = 1.30 Fooo = 284.00 Mu = 7.55 M = 288.33
# Found Formula = C16 H23 N1 O2
# Dc = 1.17 FOOO = 284.00 Mu = 6.05 M = 261.36
_chemical_formula_sum            'C16 H23 N1 O2'
_chemical_formula_moiety         'C16 H23 N1 O2'
_chemical_compound_source        ?
_chemical_formula_weight         261.36
_cell_measurement_reflns_used    4603
_cell_measurement_theta_min      4.4162
_cell_measurement_theta_max      66.9348
_cell_measurement_temperature    100
_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.234
_exptl_crystal_size_mid          0.347
_exptl_crystal_size_max          0.523
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             284
_exptl_absorpt_coefficient_mu    0.605
# Sheldrick geometric approximatio 0.81 0.87
_exptl_absorpt_correction_T_min  0.810
_exptl_absorpt_correction_T_max  0.899
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
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_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector_area_resol_mean 10.4678
_diffrn_measurement_method       \w
# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?
_diffrn_ambient_temperature      100
_diffrn_reflns_number            8622
_reflns_number_total             2588
_diffrn_reflns_av_R_equivalents  0.064
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 2588
# Theoretical number of reflections is about 5275
_diffrn_reflns_theta_min         4.420
_diffrn_reflns_theta_max         67.044
_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        66.220
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              -9
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              12
_oxford_diffrn_Wilson_B_factor   2.80
_oxford_diffrn_Wilson_scale      0.02
_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   difmap
_refine_diff_density_min         -0.30
_refine_diff_density_max         0.78
# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold
# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns         2587
_refine_ls_number_restraints     259
_refine_ls_number_parameters     172
_oxford_refine_ls_R_factor_ref   0.0742
_refine_ls_wR_factor_ref         0.1963
_refine_ls_goodness_of_fit_ref   0.9627
_refine_ls_shift/su_max          0.0007998
_refine_ls_shift/su_mean         0.0002275
# The values computed with all filters except I/sigma
_oxford_reflns_number_all        2587
_refine_ls_R_factor_all          0.0742
_refine_ls_wR_factor_all         0.1963
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                2319
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_gt          0.1905
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
0.265E+04 0.447E+04 0.269E+04 0.108E+04 229.
;
# Insert your own references if required - in alphabetical order
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.39142(17) 0.55799(17) 0.26114(14) 0.0334 1.0000 Uani . . . . . .
C2 C 0.4843(3) 0.6776(3) 0.2219(2) 0.0348 1.0000 Uani . . . . . .
C3 C 0.5906(3) 0.6550(3) 0.0921(2) 0.0427 1.0000 Uani . . . . . .
H31 H 0.6637 0.7168 0.0818 0.0635 1.0000 Uiso R . . . . .
H32 H 0.6493 0.5425 0.0974 0.0640 1.0000 Uiso R . . . . .
H33 H 0.5272 0.6894 0.0170 0.0632 1.0000 Uiso R . . . . .
C4 C 0.3725(3) 0.8483(3) 0.2134(2) 0.0442 1.0000 Uani . . . . . .
H43 H 0.4367 0.9226 0.2017 0.0666 1.0000 Uiso R . . . . .
H42 H 0.3003 0.8501 0.2958 0.0656 1.0000 Uiso R . . . . .
H41 H 0.3066 0.8837 0.1382 0.0649 1.0000 Uiso R . . . . .
C5 C 0.5863(3) 0.6294(3) 0.3375(2) 0.0459 1.0000 Uani . . . . . .
H53 H 0.6509 0.7044 0.3250 0.0684 1.0000 Uiso R . . . . .
H52 H 0.5186 0.6328 0.4200 0.0682 1.0000 Uiso R . . . . .
H51 H 0.6572 0.5217 0.3415 0.0682 1.0000 Uiso R . . . . .
C6 C 0.2818(2) 0.5625(2) 0.18380(19) 0.0310 1.0000 Uani . . . . . .
O7 O 0.25430(18) 0.65528(17) 0.07647(13) 0.0348 1.0000 Uani . . . . . .
N8 N 0.2056(2) 0.4468(2) 0.23917(16) 0.0353 1.0000 Uani . . . . . .
C9 C 0.2125(3) 0.3638(3) 0.3802(2) 0.0386 1.0000 Uani . . . . . .
C10 C 0.1922(3) 0.1950(3) 0.4016(2) 0.0376 1.0000 Uani . . . . . .
C11 C 0.1948(2) 0.1135(3) 0.5498(2) 0.0350 1.0000 Uani . . . . . .
C12 C 0.3141(3) -0.0312(3) 0.5865(2) 0.0374 1.0000 Uani . . . . . .
C13 C 0.3237(3) -0.1106(3) 0.7200(2) 0.0421 1.0000 Uani . . . . . .
C14 C 0.2142(3) -0.0466(3) 0.8179(2) 0.0423 1.0000 Uani . . . . . .
C15 C 0.0936(3) 0.0975(3) 0.7825(2) 0.0420 1.0000 Uani . . . . . .
C16 C 0.0842(3) 0.1759(3) 0.6484(2) 0.0388 1.0000 Uani . . . . . .
H161 H 0.0004 0.2732 0.6231 0.0458 1.0000 Uiso R . . . . .
H151 H 0.0184 0.1404 0.8471 0.0501 1.0000 Uiso R . . . . .
H141 H 0.2181 -0.0992 0.9081 0.0512 1.0000 Uiso R . . . . .
H131 H 0.4080 -0.2102 0.7437 0.0515 1.0000 Uiso R . . . . .
H121 H 0.3906 -0.0746 0.5199 0.0449 1.0000 Uiso R . . . . .
C17 C 0.0371(3) 0.2061(3) 0.3463(2) 0.0398 1.0000 Uani . . . . . .
C18 C 0.0431(3) 0.2906(3) 0.1975(2) 0.0447 1.0000 Uani . . . . . .
C19 C 0.0630(3) 0.4571(3) 0.1789(2) 0.0438 1.0000 Uani . . . . . .
H191 H -0.0358 0.5267 0.2232 0.0534 1.0000 Uiso R . . . . .
H192 H 0.0790 0.5040 0.0815 0.0530 1.0000 Uiso R . . . . .
H182 H 0.1376 0.2284 0.1449 0.0538 1.0000 Uiso R . . . . .
H181 H -0.0622 0.3044 0.1656 0.0545 1.0000 Uiso R . . . . .
H172 H -0.0545 0.2642 0.3973 0.0469 1.0000 Uiso R . . . . .
H171 H 0.0287 0.0967 0.3578 0.0469 1.0000 Uiso R . . . . .
H101 H 0.2892 0.1322 0.3486 0.0443 1.0000 Uiso R . . . . .
H92 H 0.3209 0.3510 0.4056 0.0447 1.0000 Uiso R . . . . .
H91 H 0.1203 0.4292 0.4371 0.0462 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0402(8) 0.0376(8) 0.0275(7) 0.0031(6) -0.0103(6) -0.0224(6)
C2 0.0422(11) 0.0405(11) 0.0294(10) -0.0029(9) -0.0048(9) -0.0251(9)
C3 0.0473(13) 0.0533(13) 0.0348(11) -0.0090(10) 0.0012(9) -0.0274(11)
C4 0.0534(13) 0.0413(12) 0.0456(13) -0.0135(10) -0.0064(10) -0.0203(10)
C5 0.0538(13) 0.0580(14) 0.0363(12) 0.0008(10) -0.0138(10) -0.0341(12)
C6 0.0354(10) 0.0325(10) 0.0266(10) -0.0029(8) -0.0064(8) -0.0126(8)
O7 0.0447(8) 0.0357(8) 0.0250(7) 0.0030(6) -0.0097(6) -0.0175(6)
N8 0.0417(10) 0.0436(10) 0.0247(9) 0.0059(7) -0.0120(7) -0.0239(8)
C9 0.0481(12) 0.0425(12) 0.0291(11) 0.0033(9) -0.0124(9) -0.0224(10)
C10 0.0434(12) 0.0387(11) 0.0330(11) -0.0003(9) -0.0088(9) -0.0180(9)
C11 0.0388(11) 0.0401(11) 0.0315(11) 0.0035(9) -0.0099(9) -0.0243(9)
C12 0.0382(11) 0.0403(11) 0.0378(12) -0.0049(9) -0.0046(9) -0.0190(9)
C13 0.0433(12) 0.0354(11) 0.0477(13) 0.0054(10) -0.0192(10) -0.0153(9)
C14 0.0586(14) 0.0480(13) 0.0274(11) 0.0077(9) -0.0148(10) -0.0321(11)
C15 0.0467(12) 0.0454(12) 0.0378(12) -0.0080(10) 0.0008(9) -0.0220(10)
C16 0.0386(11) 0.0324(11) 0.0455(13) 0.0028(9) -0.0113(9) -0.0154(9)
C17 0.0471(12) 0.0418(12) 0.0346(12) 0.0068(9) -0.0141(9) -0.0249(10)
C18 0.0524(13) 0.0504(13) 0.0396(12) -0.0002(10) -0.0167(10) -0.0273(11)
C19 0.0521(13) 0.0516(13) 0.0335(11) 0.0068(10) -0.0187(10) -0.0277(11)
_refine_ls_extinction_method     None
_oxford_refine_ls_scale          7.9(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.478(2) yes
O1 . C6 . 1.340(2) yes
C2 . C3 . 1.524(3) yes
C2 . C4 . 1.507(3) yes
C2 . C5 . 1.511(3) yes
C3 . H31 . 0.947 no
C3 . H32 . 0.957 no
C3 . H33 . 0.964 no
C4 . H43 . 0.971 no
C4 . H42 . 0.976 no
C4 . H41 . 0.978 no
C5 . H53 . 0.978 no
C5 . H52 . 0.959 no
C5 . H51 . 0.953 no
C6 . O7 . 1.215(2) yes
C6 . N8 . 1.359(3) yes
N8 . C9 . 1.464(3) yes
N8 . C19 . 1.461(3) yes
C9 . C10 . 1.520(3) yes
C9 . H92 . 0.996 no
C9 . H91 . 1.027 no
C10 . C11 . 1.527(3) yes
C10 . C17 . 1.533(3) yes
C10 . H101 . 1.016 no
C11 . C12 . 1.383(3) yes
C11 . C16 . 1.381(3) yes
C12 . C13 . 1.389(3) yes
C12 . H121 . 0.945 no
C13 . C14 . 1.377(4) yes
C13 . H131 . 0.959 no
C14 . C15 . 1.384(4) yes
C14 . H141 . 0.936 no
C15 . C16 . 1.393(3) yes
C15 . H151 . 0.922 no
C16 . H161 . 0.948 no
C17 . C18 . 1.538(3) yes
C17 . H172 . 0.961 no
C17 . H171 . 0.973 no
C18 . C19 . 1.503(3) yes
C18 . H182 . 0.999 no
C18 . H181 . 0.996 no
C19 . H191 . 1.007 no
C19 . H192 . 0.996 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . O1 . C6 . 120.32(15) yes
O1 . C2 . C3 . 110.12(16) yes
O1 . C2 . C4 . 110.34(17) yes
C3 . C2 . C4 . 112.80(19) yes
O1 . C2 . C5 . 101.70(16) yes
C3 . C2 . C5 . 110.6(2) yes
C4 . C2 . C5 . 110.72(18) yes
C2 . C3 . H31 . 106.7 no
C2 . C3 . H32 . 110.3 no
H31 . C3 . H32 . 109.5 no
C2 . C3 . H33 . 111.4 no
H31 . C3 . H33 . 111.5 no
H32 . C3 . H33 . 107.5 no
C2 . C4 . H43 . 108.7 no
C2 . C4 . H42 . 108.0 no
H43 . C4 . H42 . 111.5 no
C2 . C4 . H41 . 112.5 no
H43 . C4 . H41 . 108.0 no
H42 . C4 . H41 . 108.1 no
C2 . C5 . H53 . 109.6 no
C2 . C5 . H52 . 110.1 no
H53 . C5 . H52 . 109.4 no
C2 . C5 . H51 . 110.1 no
H53 . C5 . H51 . 108.7 no
H52 . C5 . H51 . 109.0 no
O1 . C6 . O7 . 125.25(18) yes
O1 . C6 . N8 . 111.40(17) yes
O7 . C6 . N8 . 123.34(18) yes
C6 . N8 . C9 . 121.73(16) yes
C6 . N8 . C19 . 117.15(17) yes
C9 . N8 . C19 . 115.70(17) yes
N8 . C9 . C10 . 110.79(17) yes
N8 . C9 . H92 . 107.9 no
C10 . C9 . H92 . 108.2 no
N8 . C9 . H91 . 109.6 no
C10 . C9 . H91 . 107.7 no
H92 . C9 . H91 . 112.7 no
C9 . C10 . C11 . 109.67(17) yes
C9 . C10 . C17 . 110.28(18) yes
C11 . C10 . C17 . 112.12(17) yes
C9 . C10 . H101 . 105.3 no
C11 . C10 . H101 . 109.8 no
C17 . C10 . H101 . 109.5 no
C10 . C11 . C12 . 117.9(2) yes
C10 . C11 . C16 . 123.52(19) yes
C12 . C11 . C16 . 118.6(2) yes
C11 . C12 . C13 . 120.7(2) yes
C11 . C12 . H121 . 119.2 no
C13 . C12 . H121 . 120.1 no
C12 . C13 . C14 . 120.4(2) yes
C12 . C13 . H131 . 119.5 no
C14 . C13 . H131 . 120.0 no
C13 . C14 . C15 . 119.5(2) yes
C13 . C14 . H141 . 121.5 no
C15 . C14 . H141 . 118.9 no
C14 . C15 . C16 . 119.7(2) yes
C14 . C15 . H151 . 120.2 no
C16 . C15 . H151 . 120.1 no
C15 . C16 . C11 . 121.1(2) yes
C15 . C16 . H161 . 120.2 no
C11 . C16 . H161 . 118.7 no
C10 . C17 . C18 . 108.95(17) yes
C10 . C17 . H172 . 109.4 no
C18 . C17 . H172 . 111.7 no
C10 . C17 . H171 . 108.9 no
C18 . C17 . H171 . 110.6 no
H172 . C17 . H171 . 107.2 no
C17 . C18 . C19 . 110.74(18) yes
C17 . C18 . H182 . 111.3 no
C19 . C18 . H182 . 106.3 no
C17 . C18 . H181 . 107.5 no
C19 . C18 . H181 . 107.9 no
H182 . C18 . H181 . 113.2 no
C18 . C19 . N8 . 110.51(19) yes
C18 . C19 . H191 . 108.4 no
N8 . C19 . H191 . 109.5 no
C18 . C19 . H192 . 109.2 no
N8 . C19 . H192 . 107.6 no
H191 . C19 . H192 . 111.7 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C14 . H141 . O7 1_546 149.69(7) 0.936 2.390 3.232(3) yes
_iucr_refine_instruction_details_constraints 
;
#
# Punched on 19/11/12 at 14:53:05
#
#LIST 12
BLOCK SCALE X'S, U'S
RIDE C ( 3,X'S) H ( 31,X'S) H ( 32,X'S) H ( 33,X'S)
RIDE C ( 4,X'S) H ( 43,X'S) H ( 42,X'S) H ( 41,X'S)
RIDE C ( 5,X'S) H ( 53,X'S) H ( 52,X'S) H ( 51,X'S)
RIDE C ( 9,X'S) H ( 92,X'S) H ( 91,X'S)
RIDE C ( 10,X'S) H ( 101,X'S)
RIDE C ( 12,X'S) H ( 121,X'S)
RIDE C ( 13,X'S) H ( 131,X'S)
RIDE C ( 14,X'S) H ( 141,X'S)
RIDE C ( 15,X'S) H ( 151,X'S)
RIDE C ( 16,X'S) H ( 161,X'S)
RIDE C ( 17,X'S) H ( 172,X'S) H ( 171,X'S)
RIDE C ( 18,X'S) H ( 182,X'S) H ( 181,X'S)
RIDE C ( 19,X'S) H ( 191,X'S) H ( 192,X'S)
END
;
_iucr_refine_instruction_details_restraints 
;
#
# Punched on 19/11/12 at 14:53:05
#
#LIST 16
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
REM SHIFTLIMIT START (DO NOT REMOVE THIS LINE)
LIMIT 0.01000000 U[ISO]
LIMIT 0.01000000 X
LIMIT 0.01000000 Y
LIMIT 0.01000000 Z
LIMIT 0.01000000 U[11]
LIMIT 0.01000000 U[22]
LIMIT 0.01000000 U[33]
LIMIT 0.01000000 U[12]
LIMIT 0.01000000 U[13]
LIMIT 0.01000000 U[23]
LIMIT 0.01000000 OCC
REM SHIFTLIMIT END (DO NOT REMOVE THIS LINE)
END
;
# Manually omitted reflections
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
2 1 0 x .


data_2
_database_code_depnum_ccdc_archive 'CCDC 924290'
#TrackingRef '17683_web_deposit_cif_file_1_OlivierBaudoin_1360704308.Cpd8a.cif'
_exptl_special_details           
;
The crystal was
placed in the cold stream of an Oxford
Cryosystems open-flow nitrogen cryostat (Cosier &
Glazer, 1986) with a nominal stability of 0.1K.
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107.
;
_refine_special_details          
;
?
;
#---------------------------------------------------------------
# _oxford_ data items, April 2010:
# There is some uncertainty about the correct way of forming local data
# names, e.g.
# _atom_site_special_shape_oxford
# or
# _oxford_atom_site_special_shape
# see:
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace
# A reserved prefix, e.g. foo, must be used in the following way
# " If the data file contains items defined in a DDL1 dictionary, the
# local data names assigned under the reserved prefix must contain it as
# their first component, e.g. _foo_atom_site_my_item. "
# However, this seems to say the opposite:
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html
# According to advice from the IUCr, CRYSTALS is correct
#---------------------------------------------------------------
# End of 'script/refcif.dat'
#end of refcif
_cell_length_a                   9.7796(3)
_cell_length_b                   10.0791(3)
_cell_length_c                   21.9689(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.101(2)
_cell_angle_gamma                90
_cell_volume                     2153.20(10)
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z            4
# Given Formula = C15 H18 F9 N3 O3
# Dc = 1.42 Fooo = 888.00 Mu = 13.51 M = 459.31
# Found Formula = C24 H28 F3 N1 O2
# Dc = 1.29 FOOO = 888.00 Mu = 8.27 M = 419.49
_chemical_formula_sum            'C24 H28 F3 N1 O2'
_chemical_formula_moiety         'C24 H28 F3 N1 O2'
_chemical_compound_source        ?
_chemical_formula_weight         419.49
_cell_measurement_reflns_used    12477
_cell_measurement_theta_min      4.0120
_cell_measurement_theta_max      66.8900
_cell_measurement_temperature    100
_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.145
_exptl_crystal_size_mid          0.327
_exptl_crystal_size_max          0.679
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    0.827
# Sheldrick geometric approximatio 0.76 0.89
_exptl_absorpt_correction_T_min  0.711
_exptl_absorpt_correction_T_max  0.885
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
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_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector_area_resol_mean 10.4678
_diffrn_measurement_method       \w
# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
;
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?
_diffrn_ambient_temperature      100
_diffrn_reflns_number            23974
_reflns_number_total             3806
_diffrn_reflns_av_R_equivalents  0.039
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 3806
# Theoretical number of reflections is about 7647
_diffrn_reflns_theta_min         4.047
_diffrn_reflns_theta_max         66.818
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        66.818
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              26
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   difmap
_refine_diff_density_min         -0.34
_refine_diff_density_max         0.47
# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold
# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns         3806
_refine_ls_number_restraints     0
_refine_ls_number_parameters     272
_oxford_refine_ls_R_factor_ref   0.0424
_refine_ls_wR_factor_ref         0.0813
_refine_ls_goodness_of_fit_ref   1.0227
_refine_ls_shift/su_max          0.0004979
_refine_ls_shift/su_mean         0.0000633
# The values computed with all filters except I/sigma
_oxford_reflns_number_all        3806
_refine_ls_R_factor_all          0.0424
_refine_ls_wR_factor_all         0.0813
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                3589
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_gt          0.0796
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
843. 0.133E+04 671. 175.
;
# Insert your own references if required - in alphabetical order
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
F1 F -0.02084(12) 0.56634(15) 0.69874(6) 0.0582 1.0000 Uani . . . . . .
C2 C 0.05850(16) 0.61035(17) 0.74784(7) 0.0273 1.0000 Uani . . . . . .
F3 F -0.02006(11) 0.69575(12) 0.77467(6) 0.0526 1.0000 Uani . . . . . .
F4 F 0.07742(11) 0.50718(13) 0.78540(7) 0.0597 1.0000 Uani . . . . . .
C5 C 0.18993(15) 0.66921(16) 0.73193(7) 0.0225 1.0000 Uani . . . . . .
C6 C 0.22609(16) 0.79818(16) 0.74852(7) 0.0239 1.0000 Uani . . . . . .
C7 C 0.34798(16) 0.85079(15) 0.73175(7) 0.0226 1.0000 Uani . . . . . .
C8 C 0.43439(15) 0.77690(15) 0.69866(6) 0.0195 1.0000 Uani . . . . . .
C9 C 0.56070(14) 0.84105(15) 0.67765(6) 0.0194 1.0000 Uani . . . . . .
C10 C 0.52644(15) 0.90180(15) 0.61268(7) 0.0201 1.0000 Uani . . . . . .
C11 C 0.66173(15) 0.93229(15) 0.58614(7) 0.0230 1.0000 Uani . . . . . .
C12 C 0.73610(16) 0.80318(15) 0.57147(7) 0.0225 1.0000 Uani . . . . . .
N13 N 0.70589(13) 0.70154(13) 0.61648(5) 0.0207 1.0000 Uani . . . . . .
C14 C 0.68769(15) 0.74985(15) 0.67778(7) 0.0211 1.0000 Uani . . . . . .
C15 C 0.70707(14) 0.56933(15) 0.60539(7) 0.0203 1.0000 Uani . . . . . .
O16 O 0.67720(11) 0.48464(11) 0.64138(5) 0.0249 1.0000 Uani . . . . . .
O17 O 0.74395(11) 0.54398(11) 0.54894(5) 0.0229 1.0000 Uani . . . . . .
C18 C 0.75004(16) 0.40600(15) 0.52715(7) 0.0229 1.0000 Uani . . . . . .
C19 C 0.85477(18) 0.32674(18) 0.56843(8) 0.0335 1.0000 Uani . . . . . .
C20 C 0.60852(17) 0.34277(17) 0.52202(8) 0.0303 1.0000 Uani . . . . . .
C21 C 0.79786(18) 0.42459(17) 0.46438(7) 0.0310 1.0000 Uani . . . . . .
C22 C 0.89014(16) 0.82468(17) 0.57090(8) 0.0298 1.0000 Uani . . . . . .
C23 C 0.43056(15) 1.01919(15) 0.61463(7) 0.0208 1.0000 Uani . . . . . .
C24 C 0.29169(16) 1.00688(16) 0.59285(7) 0.0260 1.0000 Uani . . . . . .
C25 C 0.20081(17) 1.11098(17) 0.59796(8) 0.0303 1.0000 Uani . . . . . .
C26 C 0.24664(16) 1.22978(17) 0.62397(7) 0.0282 1.0000 Uani . . . . . .
C27 C 0.38473(17) 1.24366(16) 0.64542(8) 0.0280 1.0000 Uani . . . . . .
C28 C 0.47546(16) 1.13937(16) 0.64094(7) 0.0251 1.0000 Uani . . . . . .
C29 C 0.39782(15) 0.64575(15) 0.68337(7) 0.0219 1.0000 Uani . . . . . .
C30 C 0.27686(16) 0.59270(16) 0.69984(7) 0.0235 1.0000 Uani . . . . . .
H61 H 0.1702 0.8486 0.7706 0.0280 1.0000 Uiso R . . . . .
H71 H 0.3743 0.9368 0.7427 0.0268 1.0000 Uiso R . . . . .
H91 H 0.5861 0.9145 0.7048 0.0220 1.0000 Uiso R . . . . .
H101 H 0.4777 0.8344 0.5868 0.0217 1.0000 Uiso R . . . . .
H112 H 0.7202 0.9849 0.6151 0.0275 1.0000 Uiso R . . . . .
H111 H 0.6469 0.9840 0.5486 0.0280 1.0000 Uiso R . . . . .
H121 H 0.6958 0.7750 0.5307 0.0246 1.0000 Uiso R . . . . .
H141 H 0.7676 0.8023 0.6929 0.0238 1.0000 Uiso R . . . . .
H142 H 0.6817 0.6744 0.7049 0.0252 1.0000 Uiso R . . . . .
H191 H 0.8718 0.2448 0.5465 0.0498 1.0000 Uiso R . . . . .
H192 H 0.8184 0.3077 0.6066 0.0486 1.0000 Uiso R . . . . .
H193 H 0.9402 0.3777 0.5764 0.0501 1.0000 Uiso R . . . . .
H201 H 0.6161 0.2518 0.5088 0.0450 1.0000 Uiso R . . . . .
H202 H 0.5710 0.3440 0.5612 0.0456 1.0000 Uiso R . . . . .
H203 H 0.5473 0.3897 0.4927 0.0458 1.0000 Uiso R . . . . .
H212 H 0.7992 0.3395 0.4434 0.0458 1.0000 Uiso R . . . . .
H211 H 0.8896 0.4627 0.4687 0.0461 1.0000 Uiso R . . . . .
H213 H 0.7355 0.4843 0.4401 0.0460 1.0000 Uiso R . . . . .
H222 H 0.9330 0.7446 0.5584 0.0448 1.0000 Uiso R . . . . .
H221 H 0.9319 0.8510 0.6114 0.0444 1.0000 Uiso R . . . . .
H223 H 0.9054 0.8937 0.5414 0.0440 1.0000 Uiso R . . . . .
H241 H 0.2589 0.9254 0.5734 0.0301 1.0000 Uiso R . . . . .
H251 H 0.1086 1.0995 0.5838 0.0366 1.0000 Uiso R . . . . .
H261 H 0.1847 1.3016 0.6278 0.0334 1.0000 Uiso R . . . . .
H271 H 0.4190 1.3250 0.6634 0.0348 1.0000 Uiso R . . . . .
H281 H 0.5698 1.1490 0.6571 0.0304 1.0000 Uiso R . . . . .
H291 H 0.4569 0.5922 0.6621 0.0255 1.0000 Uiso R . . . . .
H301 H 0.2510 0.5042 0.6889 0.0281 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0349(6) 0.0913(10) 0.0476(7) -0.0066(7) -0.0005(5) -0.0267(6)
C2 0.0225(8) 0.0295(9) 0.0298(8) 0.0042(7) 0.0014(6) 0.0018(7)
F3 0.0347(6) 0.0467(7) 0.0812(9) -0.0050(6) 0.0282(6) 0.0000(5)
F4 0.0304(6) 0.0612(8) 0.0886(10) 0.0497(7) 0.0104(6) 0.0042(5)
C5 0.0204(7) 0.0261(8) 0.0202(7) 0.0041(6) -0.0011(6) 0.0008(6)
C6 0.0229(7) 0.0258(8) 0.0232(8) 0.0005(6) 0.0034(6) 0.0043(6)
C7 0.0275(8) 0.0186(7) 0.0215(7) -0.0012(6) 0.0021(6) 0.0003(6)
C8 0.0214(7) 0.0205(7) 0.0160(7) 0.0011(5) -0.0017(5) 0.0018(6)
C9 0.0211(7) 0.0182(7) 0.0183(7) -0.0027(6) -0.0002(6) 0.0008(6)
C10 0.0229(7) 0.0174(7) 0.0197(7) -0.0015(6) 0.0011(6) -0.0004(6)
C11 0.0248(8) 0.0200(8) 0.0246(8) 0.0011(6) 0.0047(6) 0.0000(6)
C12 0.0254(8) 0.0210(8) 0.0214(7) 0.0008(6) 0.0044(6) -0.0001(6)
N13 0.0230(6) 0.0193(6) 0.0201(6) 0.0003(5) 0.0038(5) 0.0008(5)
C14 0.0208(7) 0.0227(8) 0.0193(7) -0.0011(6) 0.0000(6) 0.0002(6)
C15 0.0180(7) 0.0224(8) 0.0198(7) -0.0015(6) -0.0007(6) 0.0023(6)
O16 0.0304(6) 0.0207(5) 0.0238(5) 0.0025(4) 0.0045(4) 0.0020(5)
O17 0.0273(6) 0.0203(5) 0.0216(5) -0.0023(4) 0.0044(4) 0.0012(4)
C18 0.0256(8) 0.0185(7) 0.0243(8) -0.0038(6) 0.0015(6) 0.0033(6)
C19 0.0348(9) 0.0312(9) 0.0333(9) -0.0034(7) -0.0019(7) 0.0125(8)
C20 0.0302(9) 0.0261(8) 0.0341(9) -0.0050(7) 0.0006(7) -0.0024(7)
C21 0.0385(9) 0.0283(9) 0.0268(9) -0.0052(7) 0.0062(7) 0.0021(7)
C22 0.0272(8) 0.0269(9) 0.0368(9) -0.0015(7) 0.0109(7) 0.0000(7)
C23 0.0221(7) 0.0209(8) 0.0194(7) 0.0014(6) 0.0024(6) 0.0014(6)
C24 0.0255(8) 0.0235(8) 0.0281(8) -0.0023(6) -0.0015(6) -0.0009(6)
C25 0.0228(8) 0.0316(9) 0.0352(9) -0.0002(7) -0.0025(7) 0.0032(7)
C26 0.0281(8) 0.0256(8) 0.0312(9) 0.0016(7) 0.0040(7) 0.0076(7)
C27 0.0309(8) 0.0197(8) 0.0333(9) -0.0026(6) 0.0028(7) 0.0005(6)
C28 0.0223(8) 0.0228(8) 0.0299(8) -0.0015(6) 0.0009(6) 0.0006(6)
C29 0.0233(7) 0.0221(8) 0.0204(7) -0.0017(6) 0.0022(6) 0.0021(6)
C30 0.0263(8) 0.0198(8) 0.0238(8) -0.0004(6) -0.0003(6) -0.0013(6)
_refine_ls_extinction_coef       33.2(12)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          4.84(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 . C2 . 1.336(2) yes
C2 . F3 . 1.332(2) yes
C2 . F4 . 1.328(2) yes
C2 . C5 . 1.491(2) yes
C5 . C6 . 1.386(2) yes
C5 . C30 . 1.394(2) yes
C6 . C7 . 1.390(2) yes
C6 . H61 . 0.921 no
C7 . C8 . 1.388(2) yes
C7 . H71 . 0.929 no
C8 . C9 . 1.509(2) yes
C8 . C29 . 1.401(2) yes
C9 . C10 . 1.557(2) yes
C9 . C14 . 1.545(2) yes
C9 . H91 . 0.967 no
C10 . C11 . 1.533(2) yes
C10 . C23 . 1.513(2) yes
C10 . H101 . 0.977 no
C11 . C12 . 1.541(2) yes
C11 . H112 . 0.967 no
C11 . H111 . 0.973 no
C12 . N13 . 1.4754(19) yes
C12 . C22 . 1.523(2) yes
C12 . H121 . 0.981 no
N13 . C14 . 1.4608(18) yes
N13 . C15 . 1.355(2) yes
C14 . H141 . 0.972 no
C14 . H142 . 0.972 no
C15 . O16 . 1.2198(19) yes
C15 . O17 . 1.3523(18) yes
O17 . C18 . 1.4741(18) yes
C18 . C19 . 1.521(2) yes
C18 . C20 . 1.517(2) yes
C18 . C21 . 1.514(2) yes
C19 . H191 . 0.979 no
C19 . H192 . 0.964 no
C19 . H193 . 0.981 no
C20 . H201 . 0.967 no
C20 . H202 . 0.971 no
C20 . H203 . 0.957 no
C21 . H212 . 0.974 no
C21 . H211 . 0.971 no
C21 . H213 . 0.974 no
C22 . H222 . 0.963 no
C22 . H221 . 0.975 no
C22 . H223 . 0.973 no
C23 . C24 . 1.397(2) yes
C23 . C28 . 1.393(2) yes
C24 . C25 . 1.387(2) yes
C24 . H241 . 0.965 no
C25 . C26 . 1.381(2) yes
C25 . H251 . 0.929 no
C26 . C27 . 1.389(2) yes
C26 . H261 . 0.953 no
C27 . C28 . 1.386(2) yes
C27 . H271 . 0.955 no
C28 . H281 . 0.958 no
C29 . C30 . 1.381(2) yes
C29 . H291 . 0.950 no
C30 . H301 . 0.951 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F1 . C2 . F3 . 105.01(14) yes
F1 . C2 . F4 . 105.80(15) yes
F3 . C2 . F4 . 106.25(14) yes
F1 . C2 . C5 . 112.59(14) yes
F3 . C2 . C5 . 113.51(14) yes
F4 . C2 . C5 . 113.00(13) yes
C2 . C5 . C6 . 120.93(15) yes
C2 . C5 . C30 . 119.08(14) yes
C6 . C5 . C30 . 119.99(14) yes
C5 . C6 . C7 . 119.36(15) yes
C5 . C6 . H61 . 120.4 no
C7 . C6 . H61 . 120.2 no
C6 . C7 . C8 . 121.40(14) yes
C6 . C7 . H71 . 120.6 no
C8 . C7 . H71 . 118.0 no
C7 . C8 . C9 . 119.58(13) yes
C7 . C8 . C29 . 118.53(14) yes
C9 . C8 . C29 . 121.82(13) yes
C8 . C9 . C10 . 110.21(11) yes
C8 . C9 . C14 . 115.36(12) yes
C10 . C9 . C14 . 109.30(12) yes
C8 . C9 . H91 . 107.7 no
C10 . C9 . H91 . 106.4 no
C14 . C9 . H91 . 107.5 no
C9 . C10 . C11 . 108.50(12) yes
C9 . C10 . C23 . 110.81(12) yes
C11 . C10 . C23 . 114.62(12) yes
C9 . C10 . H101 . 107.8 no
C11 . C10 . H101 . 107.8 no
C23 . C10 . H101 . 107.1 no
C10 . C11 . C12 . 110.85(12) yes
C10 . C11 . H112 . 109.5 no
C12 . C11 . H112 . 109.9 no
C10 . C11 . H111 . 111.9 no
C12 . C11 . H111 . 107.8 no
H112 . C11 . H111 . 106.7 no
C11 . C12 . N13 . 108.27(12) yes
C11 . C12 . C22 . 111.76(13) yes
N13 . C12 . C22 . 111.90(13) yes
C11 . C12 . H121 . 106.4 no
N13 . C12 . H121 . 108.7 no
C22 . C12 . H121 . 109.6 no
C12 . N13 . C14 . 116.05(12) yes
C12 . N13 . C15 . 123.81(13) yes
C14 . N13 . C15 . 119.85(13) yes
C9 . C14 . N13 . 111.92(12) yes
C9 . C14 . H141 . 107.1 no
N13 . C14 . H141 . 108.9 no
C9 . C14 . H142 . 111.5 no
N13 . C14 . H142 . 109.0 no
H141 . C14 . H142 . 108.4 no
N13 . C15 . O16 . 124.38(14) yes
N13 . C15 . O17 . 111.02(13) yes
O16 . C15 . O17 . 124.59(14) yes
C15 . O17 . C18 . 119.99(12) yes
O17 . C18 . C19 . 110.48(12) yes
O17 . C18 . C20 . 110.64(13) yes
C19 . C18 . C20 . 112.02(14) yes
O17 . C18 . C21 . 101.89(12) yes
C19 . C18 . C21 . 110.76(14) yes
C20 . C18 . C21 . 110.61(13) yes
C18 . C19 . H191 . 106.8 no
C18 . C19 . H192 . 109.6 no
H191 . C19 . H192 . 111.0 no
C18 . C19 . H193 . 109.8 no
H191 . C19 . H193 . 110.0 no
H192 . C19 . H193 . 109.6 no
C18 . C20 . H201 . 108.8 no
C18 . C20 . H202 . 110.9 no
H201 . C20 . H202 . 109.0 no
C18 . C20 . H203 . 110.1 no
H201 . C20 . H203 . 109.2 no
H202 . C20 . H203 . 108.8 no
C18 . C21 . H212 . 110.0 no
C18 . C21 . H211 . 109.4 no
H212 . C21 . H211 . 109.6 no
C18 . C21 . H213 . 109.9 no
H212 . C21 . H213 . 108.9 no
H211 . C21 . H213 . 109.0 no
C12 . C22 . H222 . 110.1 no
C12 . C22 . H221 . 110.5 no
H222 . C22 . H221 . 109.6 no
C12 . C22 . H223 . 109.2 no
H222 . C22 . H223 . 107.9 no
H221 . C22 . H223 . 109.5 no
C10 . C23 . C24 . 120.25(14) yes
C10 . C23 . C28 . 121.52(13) yes
C24 . C23 . C28 . 118.14(14) yes
C23 . C24 . C25 . 120.87(15) yes
C23 . C24 . H241 . 119.5 no
C25 . C24 . H241 . 119.6 no
C24 . C25 . C26 . 120.45(15) yes
C24 . C25 . H251 . 119.1 no
C26 . C25 . H251 . 120.5 no
C25 . C26 . C27 . 119.25(15) yes
C25 . C26 . H261 . 120.9 no
C27 . C26 . H261 . 119.9 no
C26 . C27 . C28 . 120.41(15) yes
C26 . C27 . H271 . 120.8 no
C28 . C27 . H271 . 118.7 no
C23 . C28 . C27 . 120.87(14) yes
C23 . C28 . H281 . 119.4 no
C27 . C28 . H281 . 119.7 no
C8 . C29 . C30 . 120.43(14) yes
C8 . C29 . H291 . 120.1 no
C30 . C29 . H291 . 119.5 no
C5 . C30 . C29 . 120.26(14) yes
C5 . C30 . H301 . 119.1 no
C29 . C30 . H301 . 120.6 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C29 . H291 . O16 . 157.00 0.950 2.496 3.390(2) yes
_iucr_refine_instruction_details_constraints 
;
#
# Punched on 14/12/12 at 09:56:40
#
#LIST 12
BLOCK SCALE X'S, U'S
CONT EXTPARAM
RIDE C ( 6,X'S) H ( 61,X'S)
RIDE C ( 7,X'S) H ( 71,X'S)
RIDE C ( 9,X'S) H ( 91,X'S)
RIDE C ( 10,X'S) H ( 101,X'S)
RIDE C ( 11,X'S) H ( 112,X'S) H ( 111,X'S)
RIDE C ( 12,X'S) H ( 121,X'S)
RIDE C ( 14,X'S) H ( 141,X'S) H ( 142,X'S)
RIDE C ( 19,X'S) H ( 191,X'S) H ( 192,X'S) H ( 193,X'S)
RIDE C ( 20,X'S) H ( 201,X'S) H ( 202,X'S) H ( 203,X'S)
RIDE C ( 21,X'S) H ( 212,X'S) H ( 211,X'S) H ( 213,X'S)
RIDE C ( 22,X'S) H ( 222,X'S) H ( 221,X'S) H ( 223,X'S)
RIDE C ( 24,X'S) H ( 241,X'S)
RIDE C ( 25,X'S) H ( 251,X'S)
RIDE C ( 26,X'S) H ( 261,X'S)
RIDE C ( 27,X'S) H ( 271,X'S)
RIDE C ( 28,X'S) H ( 281,X'S)
RIDE C ( 29,X'S) H ( 291,X'S)
RIDE C ( 30,X'S) H ( 301,X'S)
END
;
_iucr_refine_instruction_details_restraints 
;
#
# Punched on 14/12/12 at 09:56:40
#
#LIST 16
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;


data_3
_database_code_depnum_ccdc_archive 'CCDC 924291'
#TrackingRef '17684_web_deposit_cif_file_2_OlivierBaudoin_1360704308.Cpd10a.cif'
_exptl_special_details           
;
The crystal was
placed in the cold stream of an Oxford
Cryosystems open-flow nitrogen cryostat (Cosier &
Glazer, 1986) with a nominal stability of 0.1K.
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107.
;
_refine_special_details          
;
?
;
#---------------------------------------------------------------
# _oxford_ data items, April 2010:
# There is some uncertainty about the correct way of forming local data
# names, e.g.
# _atom_site_special_shape_oxford
# or
# _oxford_atom_site_special_shape
# see:
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace
# A reserved prefix, e.g. foo, must be used in the following way
# " If the data file contains items defined in a DDL1 dictionary, the
# local data names assigned under the reserved prefix must contain it as
# their first component, e.g. _foo_atom_site_my_item. "
# However, this seems to say the opposite:
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html
# According to advice from the IUCr, CRYSTALS is correct
#---------------------------------------------------------------
# End of 'script/refcif.dat'
#end of refcif
_cell_length_a                   10.7367(8)
_cell_length_b                   11.1830(5)
_cell_length_c                   16.1060(7)
_cell_angle_alpha                76.241(4)
_cell_angle_beta                 75.622(5)
_cell_angle_gamma                77.643(5)
_cell_volume                     1794.66(18)
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z            4
# Given Formula = C35 H42 N7 O7
# Dc = 1.24 Fooo = 688.00 Mu = 7.26 M = 672.76
# Found Formula = C40 H58 N2 O4
# Dc = 1.17 FOOO = 688.00 Mu = 5.79 M = 630.91
_chemical_formula_sum            'C20 H29 N1 O2'
_chemical_formula_moiety         'C20 H29 N1 O2'
_chemical_compound_source        ?
_chemical_formula_weight         315.44
_cell_measurement_reflns_used    7389
_cell_measurement_theta_min      2.8855
_cell_measurement_theta_max      66.9145
_cell_measurement_temperature    100
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.285
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_max          0.660
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.579
# Sheldrick geometric approximatio 0.77 0.85
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_T_max  0.869
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
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_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector_area_resol_mean 10.4678
_diffrn_measurement_method       \w
# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?
_diffrn_ambient_temperature      100
_diffrn_reflns_number            19429
_reflns_number_total             6316
_diffrn_reflns_av_R_equivalents  0.048
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 6316
# Theoretical number of reflections is about 12805
_diffrn_reflns_theta_min         2.888
_diffrn_reflns_theta_max         67.023
_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        67.023
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              -12
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              19
_oxford_diffrn_Wilson_B_factor   2.10
_oxford_diffrn_Wilson_scale      0.04
_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   difmap
_refine_diff_density_min         -0.29
_refine_diff_density_max         0.30
# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold
# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns         6285
_refine_ls_number_restraints     0
_refine_ls_number_parameters     415
_oxford_refine_ls_R_factor_ref   0.0528
_refine_ls_wR_factor_ref         0.1159
_refine_ls_goodness_of_fit_ref   1.0246
_refine_ls_shift/su_max          0.0004078
_refine_ls_shift/su_mean         0.0000505
# The values computed with all filters except I/sigma
_oxford_reflns_number_all        6285
_refine_ls_R_factor_all          0.0528
_refine_ls_wR_factor_all         0.1159
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                5316
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_gt          0.1072
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.40P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
# Insert your own references if required - in alphabetical order
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.43619(10) 0.56214(9) 0.28066(7) 0.0258 1.0000 Uani . . . . . .
C2 C 0.36951(14) 0.66227(13) 0.25846(9) 0.0207 1.0000 Uani . . . . . .
O3 O 0.25325(10) 0.67544(9) 0.23633(6) 0.0230 1.0000 Uani . . . . . .
C4 C 0.19867(15) 0.56384(13) 0.23965(9) 0.0234 1.0000 Uani . . . . . .
C5 C 0.28919(16) 0.48233(15) 0.17914(10) 0.0290 1.0000 Uani . . . . . .
H51 H 0.2433 0.4200 0.1731 0.0415 1.0000 Uiso R . . . . .
H53 H 0.3650 0.4383 0.2029 0.0418 1.0000 Uiso R . . . . .
H52 H 0.3166 0.5321 0.1212 0.0425 1.0000 Uiso R . . . . .
C6 C 0.16763(17) 0.49332(15) 0.33360(10) 0.0304 1.0000 Uani . . . . . .
H61 H 0.1239 0.4249 0.3355 0.0440 1.0000 Uiso R . . . . .
H63 H 0.1103 0.5494 0.3707 0.0444 1.0000 Uiso R . . . . .
H62 H 0.2465 0.4594 0.3563 0.0441 1.0000 Uiso R . . . . .
C7 C 0.07492(16) 0.62121(15) 0.20564(10) 0.0280 1.0000 Uani . . . . . .
H71 H 0.0303 0.5548 0.2045 0.0408 1.0000 Uiso R . . . . .
H72 H 0.0173 0.6744 0.2440 0.0416 1.0000 Uiso R . . . . .
H73 H 0.0962 0.6713 0.1465 0.0405 1.0000 Uiso R . . . . .
N8 N 0.40215(12) 0.77506(11) 0.25208(8) 0.0220 1.0000 Uani . . . . . .
C9 C 0.53151(15) 0.78181(14) 0.26282(10) 0.0243 1.0000 Uani . . . . . .
C10 C 0.61117(15) 0.85220(14) 0.17854(10) 0.0259 1.0000 Uani . . . . . .
C11 C 0.68842(15) 0.76820(13) 0.11601(9) 0.0254 1.0000 Uani . . . . . .
C12 C 0.62771(17) 0.69865(15) 0.08140(10) 0.0294 1.0000 Uani . . . . . .
C13 C 0.69929(19) 0.62265(15) 0.02363(10) 0.0337 1.0000 Uani . . . . . .
C14 C 0.83296(18) 0.61533(15) -0.00205(10) 0.0339 1.0000 Uani . . . . . .
C15 C 0.89469(17) 0.68418(16) 0.03090(11) 0.0351 1.0000 Uani . . . . . .
C16 C 0.82265(16) 0.75928(15) 0.08989(11) 0.0304 1.0000 Uani . . . . . .
H161 H 0.8670 0.8055 0.1141 0.0362 1.0000 Uiso R . . . . .
H151 H 0.9853 0.6811 0.0148 0.0414 1.0000 Uiso R . . . . .
H141 H 0.8812 0.5634 -0.0428 0.0407 1.0000 Uiso R . . . . .
H131 H 0.6561 0.5760 0.0007 0.0386 1.0000 Uiso R . . . . .
H121 H 0.5350 0.7049 0.0978 0.0363 1.0000 Uiso R . . . . .
C17 C 0.51982(16) 0.96244(14) 0.13396(11) 0.0300 1.0000 Uani . . . . . .
C18 C 0.39602(15) 1.00073(13) 0.19841(10) 0.0259 1.0000 Uani . . . . . .
C19 C 0.31626(14) 0.89436(13) 0.22800(9) 0.0220 1.0000 Uani . . . . . .
C20 C 0.19964(15) 0.92281(13) 0.30059(10) 0.0257 1.0000 Uani . . . . . .
C21 C 0.11240(16) 1.04322(14) 0.26684(11) 0.0300 1.0000 Uani . . . . . .
C22 C 0.18772(17) 1.15231(14) 0.22996(11) 0.0315 1.0000 Uani . . . . . .
C23 C 0.30997(16) 1.11967(14) 0.16182(10) 0.0292 1.0000 Uani . . . . . .
H232 H 0.3621 1.1890 0.1431 0.0360 1.0000 Uiso R . . . . .
H231 H 0.2839 1.1084 0.1100 0.0349 1.0000 Uiso R . . . . .
H222 H 0.2140 1.1755 0.2784 0.0382 1.0000 Uiso R . . . . .
H221 H 0.1318 1.2253 0.2044 0.0376 1.0000 Uiso R . . . . .
H212 H 0.0387 1.0657 0.3142 0.0360 1.0000 Uiso R . . . . .
H211 H 0.0767 1.0283 0.2197 0.0346 1.0000 Uiso R . . . . .
H202 H 0.2339 0.9330 0.3496 0.0314 1.0000 Uiso R . . . . .
H201 H 0.1503 0.8527 0.3207 0.0305 1.0000 Uiso R . . . . .
H191 H 0.2822 0.8879 0.1772 0.0235 1.0000 Uiso R . . . . .
H181 H 0.4196 1.0145 0.2517 0.0306 1.0000 Uiso R . . . . .
H172 H 0.5667 1.0336 0.1090 0.0371 1.0000 Uiso R . . . . .
H171 H 0.4938 0.9373 0.0865 0.0358 1.0000 Uiso R . . . . .
H101 H 0.6729 0.8886 0.1981 0.0306 1.0000 Uiso R . . . . .
H91 H 0.5215 0.8251 0.3105 0.0278 1.0000 Uiso R . . . . .
H92 H 0.5776 0.6955 0.2780 0.0288 1.0000 Uiso R . . . . .
O24 O 0.24586(10) 0.97916(9) 0.58342(7) 0.0244 1.0000 Uani . . . . . .
C25 C 0.21966(15) 1.11457(13) 0.55051(10) 0.0259 1.0000 Uani . . . . . .
C26 C 0.34247(17) 1.15835(16) 0.49127(12) 0.0358 1.0000 Uani . . . . . .
H261 H 0.3215 1.2459 0.4654 0.0522 1.0000 Uiso R . . . . .
H263 H 0.3761 1.1105 0.4446 0.0518 1.0000 Uiso R . . . . .
H262 H 0.4101 1.1499 0.5250 0.0523 1.0000 Uiso R . . . . .
C27 C 0.16563(17) 1.18336(15) 0.62566(11) 0.0324 1.0000 Uani . . . . . .
H271 H 0.1300 1.2695 0.6018 0.0471 1.0000 Uiso R . . . . .
H273 H 0.0950 1.1432 0.6668 0.0479 1.0000 Uiso R . . . . .
H272 H 0.2322 1.1841 0.6570 0.0476 1.0000 Uiso R . . . . .
C28 C 0.11621(17) 1.12612(15) 0.49848(11) 0.0313 1.0000 Uani . . . . . .
H281 H 0.0925 1.2128 0.4725 0.0455 1.0000 Uiso R . . . . .
H282 H 0.1489 1.0771 0.4511 0.0462 1.0000 Uiso R . . . . .
H283 H 0.0379 1.0947 0.5364 0.0462 1.0000 Uiso R . . . . .
C29 C 0.33403(14) 0.93058(13) 0.63475(9) 0.0228 1.0000 Uani . . . . . .
O30 O 0.39207(11) 0.99189(10) 0.66083(7) 0.0291 1.0000 Uani . . . . . .
N31 N 0.34852(12) 0.80410(11) 0.65325(8) 0.0227 1.0000 Uani . . . . . .
C32 C 0.42720(15) 0.73292(14) 0.71594(9) 0.0239 1.0000 Uani . . . . . .
C33 C 0.34316(15) 0.66100(14) 0.79723(9) 0.0243 1.0000 Uani . . . . . .
C34 C 0.28476(15) 0.74056(14) 0.86573(10) 0.0256 1.0000 Uani . . . . . .
C35 C 0.33333(16) 0.71757(15) 0.94146(10) 0.0280 1.0000 Uani . . . . . .
C36 C 0.28410(18) 0.79272(16) 1.00357(10) 0.0334 1.0000 Uani . . . . . .
C37 C 0.18676(18) 0.89303(17) 0.99024(12) 0.0375 1.0000 Uani . . . . . .
C38 C 0.13708(17) 0.91749(17) 0.91528(13) 0.0387 1.0000 Uani . . . . . .
C39 C 0.18504(16) 0.84175(15) 0.85411(11) 0.0326 1.0000 Uani . . . . . .
H391 H 0.1487 0.8596 0.8016 0.0389 1.0000 Uiso R . . . . .
H381 H 0.0714 0.9882 0.9060 0.0450 1.0000 Uiso R . . . . .
H371 H 0.1545 0.9472 1.0310 0.0457 1.0000 Uiso R . . . . .
H361 H 0.3171 0.7736 1.0560 0.0395 1.0000 Uiso R . . . . .
H351 H 0.4034 0.6507 0.9501 0.0337 1.0000 Uiso R . . . . .
C40 C 0.24087(16) 0.60866(15) 0.76939(10) 0.0272 1.0000 Uani . . . . . .
C41 C 0.28219(15) 0.60072(13) 0.67328(9) 0.0236 1.0000 Uani . . . . . .
C42 C 0.28107(14) 0.73255(13) 0.61737(9) 0.0221 1.0000 Uani . . . . . .
C43 C 0.33923(16) 0.72559(14) 0.52193(10) 0.0268 1.0000 Uani . . . . . .
C44 C 0.25941(18) 0.65513(15) 0.48935(10) 0.0321 1.0000 Uani . . . . . .
C45 C 0.24815(18) 0.52576(15) 0.54679(10) 0.0314 1.0000 Uani . . . . . .
C46 C 0.19766(16) 0.53331(14) 0.64280(10) 0.0268 1.0000 Uani . . . . . .
H462 H 0.1071 0.5805 0.6513 0.0319 1.0000 Uiso R . . . . .
H461 H 0.1968 0.4491 0.6787 0.0310 1.0000 Uiso R . . . . .
H452 H 0.1890 0.4873 0.5281 0.0379 1.0000 Uiso R . . . . .
H451 H 0.3337 0.4736 0.5399 0.0373 1.0000 Uiso R . . . . .
H442 H 0.3005 0.6465 0.4287 0.0374 1.0000 Uiso R . . . . .
H441 H 0.1697 0.7042 0.4902 0.0379 1.0000 Uiso R . . . . .
H432 H 0.3406 0.8101 0.4866 0.0316 1.0000 Uiso R . . . . .
H431 H 0.4312 0.6816 0.5166 0.0316 1.0000 Uiso R . . . . .
H421 H 0.1877 0.7732 0.6215 0.0254 1.0000 Uiso R . . . . .
H411 H 0.3720 0.5543 0.6630 0.0278 1.0000 Uiso R . . . . .
H402 H 0.2298 0.5265 0.8053 0.0319 1.0000 Uiso R . . . . .
H401 H 0.1566 0.6653 0.7779 0.0317 1.0000 Uiso R . . . . .
H331 H 0.4020 0.5909 0.8225 0.0272 1.0000 Uiso R . . . . .
H321 H 0.4958 0.6735 0.6872 0.0265 1.0000 Uiso R . . . . .
H322 H 0.4676 0.7904 0.7332 0.0269 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0270(6) 0.0204(5) 0.0308(5) -0.0041(4) -0.0099(4) -0.0020(4)
C2 0.0217(7) 0.0220(7) 0.0184(6) -0.0044(5) -0.0040(5) -0.0033(6)
O3 0.0241(5) 0.0206(5) 0.0266(5) -0.0042(4) -0.0089(4) -0.0050(4)
C4 0.0268(8) 0.0223(7) 0.0237(7) -0.0042(6) -0.0066(6) -0.0088(6)
C5 0.0329(9) 0.0275(8) 0.0300(8) -0.0095(6) -0.0078(6) -0.0061(7)
C6 0.0339(9) 0.0330(8) 0.0261(8) -0.0001(6) -0.0083(6) -0.0131(7)
C7 0.0281(8) 0.0295(8) 0.0287(8) -0.0046(6) -0.0089(6) -0.0074(6)
N8 0.0230(6) 0.0197(6) 0.0240(6) -0.0030(5) -0.0077(5) -0.0033(5)
C9 0.0248(8) 0.0241(7) 0.0259(7) -0.0051(6) -0.0082(6) -0.0041(6)
C10 0.0242(8) 0.0246(7) 0.0307(8) -0.0065(6) -0.0059(6) -0.0063(6)
C11 0.0294(8) 0.0216(7) 0.0239(7) -0.0009(6) -0.0069(6) -0.0038(6)
C12 0.0341(9) 0.0311(8) 0.0249(7) -0.0038(6) -0.0062(6) -0.0107(7)
C13 0.0510(11) 0.0291(8) 0.0234(7) -0.0036(6) -0.0095(7) -0.0113(7)
C14 0.0465(10) 0.0268(8) 0.0254(8) -0.0066(6) -0.0092(7) 0.0043(7)
C15 0.0286(9) 0.0376(9) 0.0349(9) -0.0080(7) -0.0080(7) 0.0063(7)
C16 0.0293(9) 0.0295(8) 0.0343(8) -0.0092(7) -0.0108(7) -0.0007(7)
C17 0.0295(8) 0.0231(8) 0.0331(8) -0.0001(6) -0.0017(7) -0.0066(6)
C18 0.0301(8) 0.0203(7) 0.0270(7) -0.0032(6) -0.0053(6) -0.0057(6)
C19 0.0246(8) 0.0199(7) 0.0218(7) -0.0028(5) -0.0077(6) -0.0023(6)
C20 0.0291(8) 0.0219(7) 0.0244(7) -0.0032(6) -0.0039(6) -0.0037(6)
C21 0.0284(8) 0.0259(8) 0.0313(8) -0.0050(6) -0.0031(6) 0.0005(6)
C22 0.0364(9) 0.0208(7) 0.0334(8) -0.0031(6) -0.0064(7) 0.0005(6)
C23 0.0336(9) 0.0206(7) 0.0304(8) -0.0012(6) -0.0046(6) -0.0046(6)
O24 0.0285(6) 0.0184(5) 0.0272(5) -0.0021(4) -0.0097(4) -0.0035(4)
C25 0.0294(8) 0.0176(7) 0.0282(7) -0.0015(6) -0.0052(6) -0.0027(6)
C26 0.0326(9) 0.0294(8) 0.0384(9) 0.0025(7) -0.0015(7) -0.0075(7)
C27 0.0341(9) 0.0250(8) 0.0381(9) -0.0094(7) -0.0071(7) -0.0015(7)
C28 0.0356(9) 0.0251(8) 0.0310(8) -0.0017(6) -0.0104(7) -0.0005(7)
C29 0.0230(7) 0.0233(7) 0.0214(7) -0.0043(6) -0.0034(6) -0.0043(6)
O30 0.0341(6) 0.0243(5) 0.0337(6) -0.0069(4) -0.0117(5) -0.0078(5)
N31 0.0263(7) 0.0206(6) 0.0228(6) -0.0029(5) -0.0079(5) -0.0055(5)
C32 0.0243(8) 0.0250(7) 0.0236(7) -0.0040(6) -0.0081(6) -0.0039(6)
C33 0.0268(8) 0.0234(7) 0.0228(7) -0.0024(6) -0.0082(6) -0.0029(6)
C34 0.0272(8) 0.0248(7) 0.0241(7) -0.0024(6) -0.0032(6) -0.0080(6)
C35 0.0339(9) 0.0259(8) 0.0244(7) -0.0022(6) -0.0062(6) -0.0079(6)
C36 0.0412(10) 0.0375(9) 0.0237(8) -0.0070(7) -0.0015(7) -0.0161(8)
C37 0.0376(10) 0.0386(9) 0.0375(9) -0.0182(7) 0.0072(7) -0.0144(8)
C38 0.0289(9) 0.0334(9) 0.0509(10) -0.0130(8) -0.0012(8) -0.0017(7)
C39 0.0287(8) 0.0327(9) 0.0350(9) -0.0060(7) -0.0067(7) -0.0027(7)
C40 0.0305(8) 0.0289(8) 0.0225(7) -0.0012(6) -0.0053(6) -0.0101(6)
C41 0.0255(8) 0.0218(7) 0.0238(7) -0.0026(6) -0.0071(6) -0.0040(6)
C42 0.0239(7) 0.0211(7) 0.0225(7) -0.0029(6) -0.0075(6) -0.0047(6)
C43 0.0343(9) 0.0237(7) 0.0226(7) -0.0020(6) -0.0055(6) -0.0082(6)
C44 0.0454(10) 0.0324(8) 0.0217(7) -0.0044(6) -0.0081(7) -0.0130(7)
C45 0.0419(10) 0.0279(8) 0.0288(8) -0.0076(6) -0.0086(7) -0.0118(7)
C46 0.0317(8) 0.0232(7) 0.0264(7) -0.0014(6) -0.0079(6) -0.0083(6)
_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.30(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.2198(18) yes
C2 . O3 . 1.3506(18) yes
C2 . N8 . 1.3542(19) yes
O3 . C4 . 1.4731(17) yes
C4 . C5 . 1.516(2) yes
C4 . C6 . 1.522(2) yes
C4 . C7 . 1.519(2) yes
C5 . H51 . 0.970 no
C5 . H53 . 0.972 no
C5 . H52 . 0.976 no
C6 . H61 . 0.971 no
C6 . H63 . 0.980 no
C6 . H62 . 0.971 no
C7 . H71 . 0.971 no
C7 . H72 . 0.972 no
C7 . H73 . 0.983 no
N8 . C9 . 1.4612(19) yes
N8 . C19 . 1.4784(18) yes
C9 . C10 . 1.548(2) yes
C9 . H91 . 0.975 no
C9 . H92 . 0.990 no
C10 . C11 . 1.512(2) yes
C10 . C17 . 1.552(2) yes
C10 . H101 . 0.992 no
C11 . C12 . 1.394(2) yes
C11 . C16 . 1.386(2) yes
C12 . C13 . 1.386(2) yes
C12 . H121 . 0.957 no
C13 . C14 . 1.381(3) yes
C13 . H131 . 0.952 no
C14 . C15 . 1.379(3) yes
C14 . H141 . 0.959 no
C15 . C16 . 1.394(2) yes
C15 . H151 . 0.938 no
C16 . H161 . 0.969 no
C17 . C18 . 1.520(2) yes
C17 . H172 . 0.983 no
C17 . H171 . 0.992 no
C18 . C19 . 1.529(2) yes
C18 . C23 . 1.530(2) yes
C18 . H181 . 1.006 no
C19 . C20 . 1.522(2) yes
C19 . H191 . 0.998 no
C20 . C21 . 1.533(2) yes
C20 . H202 . 0.989 no
C20 . H201 . 0.986 no
C21 . C22 . 1.528(2) yes
C21 . H212 . 0.989 no
C21 . H211 . 0.992 no
C22 . C23 . 1.527(2) yes
C22 . H222 . 0.996 no
C22 . H221 . 0.975 no
C23 . H232 . 0.998 no
C23 . H231 . 0.986 no
O24 . C25 . 1.4707(17) yes
O24 . C29 . 1.3527(18) yes
C25 . C26 . 1.523(2) yes
C25 . C27 . 1.515(2) yes
C25 . C28 . 1.517(2) yes
C26 . H261 . 0.970 no
C26 . H263 . 0.977 no
C26 . H262 . 0.986 no
C27 . H271 . 0.980 no
C27 . H273 . 0.985 no
C27 . H272 . 0.975 no
C28 . H281 . 0.966 no
C28 . H282 . 0.994 no
C28 . H283 . 0.986 no
C29 . O30 . 1.2184(18) yes
C29 . N31 . 1.3572(19) yes
N31 . C32 . 1.4561(18) yes
N31 . C42 . 1.4747(18) yes
C32 . C33 . 1.549(2) yes
C32 . H321 . 0.983 no
C32 . H322 . 0.971 no
C33 . C34 . 1.512(2) yes
C33 . C40 . 1.547(2) yes
C33 . H331 . 0.971 no
C34 . C35 . 1.391(2) yes
C34 . C39 . 1.394(2) yes
C35 . C36 . 1.390(2) yes
C35 . H351 . 0.952 no
C36 . C37 . 1.375(3) yes
C36 . H361 . 0.956 no
C37 . C38 . 1.385(3) yes
C37 . H371 . 0.951 no
C38 . C39 . 1.383(3) yes
C38 . H381 . 0.950 no
C39 . H391 . 0.978 no
C40 . C41 . 1.519(2) yes
C40 . H402 . 0.977 no
C40 . H401 . 0.987 no
C41 . C42 . 1.5331(19) yes
C41 . C46 . 1.524(2) yes
C41 . H411 . 0.987 no
C42 . C43 . 1.523(2) yes
C42 . H421 . 1.001 no
C43 . C44 . 1.529(2) yes
C43 . H432 . 0.981 no
C43 . H431 . 0.997 no
C44 . C45 . 1.532(2) yes
C44 . H442 . 0.985 no
C44 . H441 . 1.000 no
C45 . C46 . 1.523(2) yes
C45 . H452 . 0.976 no
C45 . H451 . 0.973 no
C46 . H462 . 0.996 no
C46 . H461 . 0.981 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C2 . O3 . 124.41(12) yes
O1 . C2 . N8 . 124.76(13) yes
O3 . C2 . N8 . 110.83(12) yes
C2 . O3 . C4 . 119.73(11) yes
O3 . C4 . C5 . 111.08(12) yes
O3 . C4 . C6 . 109.94(11) yes
C5 . C4 . C6 . 112.37(13) yes
O3 . C4 . C7 . 101.76(11) yes
C5 . C4 . C7 . 110.08(12) yes
C6 . C4 . C7 . 111.15(13) yes
C4 . C5 . H51 . 109.1 no
C4 . C5 . H53 . 111.2 no
H51 . C5 . H53 . 107.4 no
C4 . C5 . H52 . 110.7 no
H51 . C5 . H52 . 108.2 no
H53 . C5 . H52 . 110.1 no
C4 . C6 . H61 . 108.9 no
C4 . C6 . H63 . 109.9 no
H61 . C6 . H63 . 109.2 no
C4 . C6 . H62 . 111.3 no
H61 . C6 . H62 . 108.7 no
H63 . C6 . H62 . 108.8 no
C4 . C7 . H71 . 109.0 no
C4 . C7 . H72 . 110.1 no
H71 . C7 . H72 . 108.6 no
C4 . C7 . H73 . 110.2 no
H71 . C7 . H73 . 109.8 no
H72 . C7 . H73 . 109.1 no
C2 . N8 . C9 . 119.49(12) yes
C2 . N8 . C19 . 123.04(12) yes
C9 . N8 . C19 . 117.31(11) yes
N8 . C9 . C10 . 111.71(12) yes
N8 . C9 . H91 . 108.7 no
C10 . C9 . H91 . 109.2 no
N8 . C9 . H92 . 108.1 no
C10 . C9 . H92 . 109.8 no
H91 . C9 . H92 . 109.3 no
C9 . C10 . C11 . 113.30(12) yes
C9 . C10 . C17 . 109.76(12) yes
C11 . C10 . C17 . 111.76(12) yes
C9 . C10 . H101 . 105.7 no
C11 . C10 . H101 . 108.7 no
C17 . C10 . H101 . 107.3 no
C10 . C11 . C12 . 121.55(14) yes
C10 . C11 . C16 . 120.90(14) yes
C12 . C11 . C16 . 117.54(15) yes
C11 . C12 . C13 . 121.11(16) yes
C11 . C12 . H121 . 118.7 no
C13 . C12 . H121 . 120.2 no
C12 . C13 . C14 . 120.60(15) yes
C12 . C13 . H131 . 119.9 no
C14 . C13 . H131 . 119.5 no
C13 . C14 . C15 . 119.17(16) yes
C13 . C14 . H141 . 119.8 no
C15 . C14 . H141 . 121.1 no
C14 . C15 . C16 . 120.11(16) yes
C14 . C15 . H151 . 121.2 no
C16 . C15 . H151 . 118.6 no
C15 . C16 . C11 . 121.47(15) yes
C15 . C16 . H161 . 119.7 no
C11 . C16 . H161 . 118.9 no
C10 . C17 . C18 . 111.41(12) yes
C10 . C17 . H172 . 109.0 no
C18 . C17 . H172 . 109.9 no
C10 . C17 . H171 . 109.8 no
C18 . C17 . H171 . 107.6 no
H172 . C17 . H171 . 109.2 no
C17 . C18 . C19 . 109.10(12) yes
C17 . C18 . C23 . 114.04(12) yes
C19 . C18 . C23 . 108.61(12) yes
C17 . C18 . H181 . 109.4 no
C19 . C18 . H181 . 107.5 no
C23 . C18 . H181 . 108.0 no
C18 . C19 . N8 . 109.57(12) yes
C18 . C19 . C20 . 110.64(12) yes
N8 . C19 . C20 . 113.58(11) yes
C18 . C19 . H191 . 107.9 no
N8 . C19 . H191 . 107.2 no
C20 . C19 . H191 . 107.7 no
C19 . C20 . C21 . 109.31(12) yes
C19 . C20 . H202 . 107.3 no
C21 . C20 . H202 . 110.6 no
C19 . C20 . H201 . 110.2 no
C21 . C20 . H201 . 110.6 no
H202 . C20 . H201 . 108.8 no
C20 . C21 . C22 . 112.00(13) yes
C20 . C21 . H212 . 110.4 no
C22 . C21 . H212 . 109.1 no
C20 . C21 . H211 . 108.3 no
C22 . C21 . H211 . 108.6 no
H212 . C21 . H211 . 108.4 no
C21 . C22 . C23 . 111.81(13) yes
C21 . C22 . H222 . 109.3 no
C23 . C22 . H222 . 108.7 no
C21 . C22 . H221 . 110.0 no
C23 . C22 . H221 . 109.9 no
H222 . C22 . H221 . 106.9 no
C18 . C23 . C22 . 111.12(12) yes
C18 . C23 . H232 . 108.4 no
C22 . C23 . H232 . 110.3 no
C18 . C23 . H231 . 109.9 no
C22 . C23 . H231 . 109.0 no
H232 . C23 . H231 . 108.0 no
C25 . O24 . C29 . 120.30(11) yes
O24 . C25 . C26 . 109.89(13) yes
O24 . C25 . C27 . 110.57(12) yes
C26 . C25 . C27 . 112.60(13) yes
O24 . C25 . C28 . 102.19(12) yes
C26 . C25 . C28 . 110.79(13) yes
C27 . C25 . C28 . 110.33(13) yes
C25 . C26 . H261 . 108.9 no
C25 . C26 . H263 . 110.5 no
H261 . C26 . H263 . 108.9 no
C25 . C26 . H262 . 110.8 no
H261 . C26 . H262 . 108.0 no
H263 . C26 . H262 . 109.7 no
C25 . C27 . H271 . 108.1 no
C25 . C27 . H273 . 109.4 no
H271 . C27 . H273 . 109.0 no
C25 . C27 . H272 . 112.1 no
H271 . C27 . H272 . 109.2 no
H273 . C27 . H272 . 108.9 no
C25 . C28 . H281 . 109.3 no
C25 . C28 . H282 . 111.0 no
H281 . C28 . H282 . 108.7 no
C25 . C28 . H283 . 110.8 no
H281 . C28 . H283 . 109.2 no
H282 . C28 . H283 . 107.8 no
O24 . C29 . O30 . 124.70(13) yes
O24 . C29 . N31 . 110.49(12) yes
O30 . C29 . N31 . 124.81(14) yes
C29 . N31 . C32 . 119.77(12) yes
C29 . N31 . C42 . 123.39(12) yes
C32 . N31 . C42 . 116.71(11) yes
N31 . C32 . C33 . 111.21(12) yes
N31 . C32 . H321 . 108.5 no
C33 . C32 . H321 . 109.5 no
N31 . C32 . H322 . 108.4 no
C33 . C32 . H322 . 110.1 no
H321 . C32 . H322 . 109.0 no
C32 . C33 . C34 . 111.17(12) yes
C32 . C33 . C40 . 110.10(12) yes
C34 . C33 . C40 . 113.60(13) yes
C32 . C33 . H331 . 106.5 no
C34 . C33 . H331 . 107.0 no
C40 . C33 . H331 . 108.1 no
C33 . C34 . C35 . 120.49(14) yes
C33 . C34 . C39 . 121.76(14) yes
C35 . C34 . C39 . 117.69(15) yes
C34 . C35 . C36 . 121.24(16) yes
C34 . C35 . H351 . 119.4 no
C36 . C35 . H351 . 119.3 no
C35 . C36 . C37 . 120.07(16) yes
C35 . C36 . H361 . 119.7 no
C37 . C36 . H361 . 120.2 no
C36 . C37 . C38 . 119.57(16) yes
C36 . C37 . H371 . 121.0 no
C38 . C37 . H371 . 119.4 no
C37 . C38 . C39 . 120.27(17) yes
C37 . C38 . H381 . 118.9 no
C39 . C38 . H381 . 120.8 no
C34 . C39 . C38 . 121.14(16) yes
C34 . C39 . H391 . 119.4 no
C38 . C39 . H391 . 119.5 no
C33 . C40 . C41 . 110.46(12) yes
C33 . C40 . H402 . 109.8 no
C41 . C40 . H402 . 110.4 no
C33 . C40 . H401 . 109.2 no
C41 . C40 . H401 . 108.1 no
H402 . C40 . H401 . 108.8 no
C40 . C41 . C42 . 109.55(12) yes
C40 . C41 . C46 . 114.28(12) yes
C42 . C41 . C46 . 108.70(12) yes
C40 . C41 . H411 . 108.2 no
C42 . C41 . H411 . 108.7 no
C46 . C41 . H411 . 107.3 no
C41 . C42 . N31 . 109.23(11) yes
C41 . C42 . C43 . 110.09(12) yes
N31 . C42 . C43 . 113.45(12) yes
C41 . C42 . H421 . 107.2 no
N31 . C42 . H421 . 109.1 no
C43 . C42 . H421 . 107.5 no
C42 . C43 . C44 . 109.70(13) yes
C42 . C43 . H432 . 109.8 no
C44 . C43 . H432 . 110.6 no
C42 . C43 . H431 . 109.1 no
C44 . C43 . H431 . 110.0 no
H432 . C43 . H431 . 107.6 no
C43 . C44 . C45 . 111.80(13) yes
C43 . C44 . H442 . 109.4 no
C45 . C44 . H442 . 109.6 no
C43 . C44 . H441 . 109.0 no
C45 . C44 . H441 . 108.5 no
H442 . C44 . H441 . 108.5 no
C44 . C45 . C46 . 111.51(13) yes
C44 . C45 . H452 . 109.6 no
C46 . C45 . H452 . 109.1 no
C44 . C45 . H451 . 109.0 no
C46 . C45 . H451 . 109.1 no
H452 . C45 . H451 . 108.6 no
C41 . C46 . C45 . 110.93(13) yes
C41 . C46 . H462 . 108.2 no
C45 . C46 . H462 . 109.6 no
C41 . C46 . H461 . 109.4 no
C45 . C46 . H461 . 110.1 no
H462 . C46 . H461 . 108.6 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C9 . H91 . O30 2_676 138.22(4) 0.975 2.596 3.385(2) yes
C41 . H411 . O1 2_666 149.80(4) 0.987 2.445 3.335(2) yes
C32 . H321 . O1 2_666 134.47(4) 0.983 2.541 3.305(2) yes
_iucr_refine_instruction_details_constraints 
;
#
# Punched on 06/12/12 at 15:20:56
#
#LIST 12
BLOCK SCALE X'S, U'S
RIDE C ( 5,X'S) H ( 51,X'S) H ( 53,X'S) H ( 52,X'S)
RIDE C ( 6,X'S) H ( 61,X'S) H ( 63,X'S) H ( 62,X'S)
RIDE C ( 7,X'S) H ( 71,X'S) H ( 72,X'S) H ( 73,X'S)
RIDE C ( 9,X'S) H ( 91,X'S) H ( 92,X'S)
RIDE C ( 10,X'S) H ( 101,X'S)
RIDE C ( 12,X'S) H ( 121,X'S)
RIDE C ( 13,X'S) H ( 131,X'S)
RIDE C ( 14,X'S) H ( 141,X'S)
RIDE C ( 15,X'S) H ( 151,X'S)
RIDE C ( 16,X'S) H ( 161,X'S)
RIDE C ( 17,X'S) H ( 172,X'S) H ( 171,X'S)
RIDE C ( 18,X'S) H ( 181,X'S)
RIDE C ( 19,X'S) H ( 191,X'S)
RIDE C ( 20,X'S) H ( 202,X'S) H ( 201,X'S)
RIDE C ( 21,X'S) H ( 212,X'S) H ( 211,X'S)
RIDE C ( 22,X'S) H ( 222,X'S) H ( 221,X'S)
RIDE C ( 23,X'S) H ( 232,X'S) H ( 231,X'S)
RIDE C ( 26,X'S) H ( 261,X'S) H ( 263,X'S) H ( 262,X'S)
RIDE C ( 27,X'S) H ( 271,X'S) H ( 273,X'S) H ( 272,X'S)
RIDE C ( 28,X'S) H ( 281,X'S) H ( 282,X'S) H ( 283,X'S)
RIDE C ( 32,X'S) H ( 321,X'S) H ( 322,X'S)
RIDE C ( 33,X'S) H ( 331,X'S)
RIDE C ( 35,X'S) H ( 351,X'S)
RIDE C ( 36,X'S) H ( 361,X'S)
RIDE C ( 37,X'S) H ( 371,X'S)
RIDE C ( 38,X'S) H ( 381,X'S)
RIDE C ( 39,X'S) H ( 391,X'S)
RIDE C ( 40,X'S) H ( 402,X'S) H ( 401,X'S)
RIDE C ( 41,X'S) H ( 411,X'S)
RIDE C ( 42,X'S) H ( 421,X'S)
RIDE C ( 43,X'S) H ( 432,X'S) H ( 431,X'S)
RIDE C ( 44,X'S) H ( 442,X'S) H ( 441,X'S)
RIDE C ( 45,X'S) H ( 452,X'S) H ( 451,X'S)
RIDE C ( 46,X'S) H ( 462,X'S) H ( 461,X'S)
END
;
_iucr_refine_instruction_details_restraints 
;
#
# Punched on 06/12/12 at 15:20:56
#
#LIST 16
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;