# 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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# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  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_16
_ccdc_journal_depnumber          ?
#==============================================================================

_cell_length_a                   10.0503(2)
_cell_length_b                   10.9520(2)
_cell_length_c                   11.2054(3)
_cell_angle_alpha                74.3842(8)
_cell_angle_beta                 68.6115(8)
_cell_angle_gamma                80.1552(12)
_cell_volume                     1102.40(4)

_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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 = C27 H27 N1 O2 
# Dc =      1.20 Fooo =    428.00 Mu =      0.75 M =    397.52
# Found Formula = C27 H29 N1 O2 
# Dc =      1.20 FOOO =    428.00 Mu =      0.75 M =    399.53

_chemical_formula_sum            'C27 H29 N1 O2'
_chemical_formula_moiety         'C27 H29 N1 O2'
_chemical_compound_source        .
_chemical_formula_weight         399.53

_cell_measurement_reflns_used    4651
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.170
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_max          0.270

_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             428
_exptl_absorpt_coefficient_mu    0.075

# Sheldrick geometric approximatio 0.98 0.99 
# No experimental values of Tmin/max available 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.99
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_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      150
_diffrn_reflns_number            8403
_reflns_number_total             5018
_diffrn_reflns_av_R_equivalents  0.027
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 5018 
# Theoretical number of reflections is about 6964 

_diffrn_reflns_theta_min         5.173
_diffrn_reflns_theta_max         27.515
_diffrn_measured_fraction_theta_max 0.990

_diffrn_reflns_theta_full        26.964
_diffrn_measured_fraction_theta_full 0.991

_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -12
_reflns_limit_h_max              13
_reflns_limit_k_min              -13
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   2.03
_oxford_diffrn_Wilson_scale      2.36

_atom_sites_solution_primary     Direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.26
_refine_diff_density_max         0.24

# 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>-3.0\s(I)
_refine_ls_number_reflns         3448
_refine_ls_number_restraints     0
_refine_ls_number_parameters     271
_oxford_refine_ls_R_factor_ref   0.0525
_refine_ls_wR_factor_ref         0.1090
_refine_ls_goodness_of_fit_ref   0.9333
_refine_ls_shift/su_max          0.0001297
_refine_ls_shift/su_mean         0.0000151

# The values computed from all data 
_oxford_reflns_number_all        3448
_refine_ls_R_factor_all          0.0525
_refine_ls_wR_factor_all         0.1090

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2850
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_gt          0.0961

# 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 # none, 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/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 15.9 24.2 12.1 3.35 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint

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 0.39184(13) 0.09974(11) 0.38038(11) 0.0329 1.0000 Uani . . . . . .
C2 C 0.40041(16) 0.22421(15) 0.32429(16) 0.0264 1.0000 Uani . . . . . .
O3 O 0.35112(13) 0.30607(12) 0.38512(12) 0.0373 1.0000 Uani . . . . . .
C4 C 0.47854(16) 0.24689(15) 0.17777(15) 0.0240 1.0000 Uani . . . . . .
C5 C 0.62518(17) 0.17138(16) 0.14340(17) 0.0292 1.0000 Uani . . . . . .
C6 C 0.73170(18) 0.20370(17) 0.19315(18) 0.0331 1.0000 Uani . . . . . .
C7 C 0.7196(2) 0.29686(19) 0.2501(2) 0.0407 1.0000 Uani . . . . . .
C8 C 0.38350(16) 0.21326(14) 0.11077(15) 0.0225 1.0000 Uani . . . . . .
N9 N 0.23312(13) 0.26615(12) 0.16505(13) 0.0231 1.0000 Uani . . . . . .
C10 C 0.13469(17) 0.21249(15) 0.12661(16) 0.0249 1.0000 Uani . . . . . .
C11 C 0.12020(16) 0.07156(15) 0.18364(15) 0.0236 1.0000 Uani . . . . . .
C12 C 0.10336(18) -0.00339(15) 0.10832(17) 0.0288 1.0000 Uani . . . . . .
C13 C 0.07909(19) -0.13124(17) 0.16175(18) 0.0348 1.0000 Uani . . . . . .
C14 C 0.07446(19) -0.18609(16) 0.28900(19) 0.0359 1.0000 Uani . . . . . .
C15 C 0.0943(2) -0.11287(17) 0.36354(18) 0.0366 1.0000 Uani . . . . . .
C16 C 0.11549(18) 0.01530(16) 0.31178(17) 0.0304 1.0000 Uani . . . . . .
C17 C 0.21278(17) 0.40640(14) 0.13203(16) 0.0259 1.0000 Uani . . . . . .
C18 C 0.06757(16) 0.45634(14) 0.21446(15) 0.0235 1.0000 Uani . . . . . .
C19 C -0.01733(18) 0.54762(15) 0.15527(16) 0.0281 1.0000 Uani . . . . . .
C20 C -0.14957(19) 0.59563(16) 0.23058(17) 0.0316 1.0000 Uani . . . . . .
C21 C -0.19793(18) 0.55375(16) 0.36571(17) 0.0302 1.0000 Uani . . . . . .
C22 C -0.11362(18) 0.46311(17) 0.42550(17) 0.0319 1.0000 Uani . . . . . .
C23 C 0.01798(18) 0.41455(16) 0.35096(16) 0.0296 1.0000 Uani . . . . . .
C24 C 0.44740(16) 0.24452(14) -0.03890(15) 0.0230 1.0000 Uani . . . . . .
C25 C 0.50125(17) 0.36103(15) -0.11163(16) 0.0283 1.0000 Uani . . . . . .
C26 C 0.55540(19) 0.38746(16) -0.24838(17) 0.0328 1.0000 Uani . . . . . .
C27 C 0.55723(19) 0.29717(17) -0.31486(17) 0.0339 1.0000 Uani . . . . . .
C28 C 0.50572(19) 0.18037(16) -0.24378(17) 0.0321 1.0000 Uani . . . . . .
C29 C 0.45058(17) 0.15461(15) -0.10736(16) 0.0267 1.0000 Uani . . . . . .
C30 C 0.3165(2) 0.0689(2) 0.52061(19) 0.0467 1.0000 Uani . . . . . .
H41 H 0.4941 0.3399 0.1449 0.0268 1.0000 Uiso R . . . . .
H52 H 0.6688 0.1858 0.0459 0.0361 1.0000 Uiso R . . . . .
H51 H 0.6101 0.0794 0.1803 0.0353 1.0000 Uiso R . . . . .
H61 H 0.8201 0.1488 0.1801 0.0398 1.0000 Uiso R . . . . .
H72 H 0.7961 0.3099 0.2776 0.0501 1.0000 Uiso R . . . . .
H71 H 0.6330 0.3563 0.2662 0.0499 1.0000 Uiso R . . . . .
H81 H 0.3789 0.1165 0.1411 0.0255 1.0000 Uiso R . . . . .
H101 H 0.0390 0.2574 0.1601 0.0299 1.0000 Uiso R . . . . .
H102 H 0.1647 0.2301 0.0262 0.0287 1.0000 Uiso R . . . . .
H121 H 0.1097 0.0341 0.0175 0.0331 1.0000 Uiso R . . . . .
H131 H 0.0662 -0.1813 0.1078 0.0407 1.0000 Uiso R . . . . .
H141 H 0.0570 -0.2752 0.3263 0.0435 1.0000 Uiso R . . . . .
H151 H 0.0921 -0.1515 0.4529 0.0450 1.0000 Uiso R . . . . .
H161 H 0.1275 0.0689 0.3645 0.0367 1.0000 Uiso R . . . . .
H171 H 0.2896 0.4396 0.1493 0.0310 1.0000 Uiso R . . . . .
H172 H 0.2247 0.4361 0.0364 0.0307 1.0000 Uiso R . . . . .
H191 H 0.0178 0.5790 0.0593 0.0336 1.0000 Uiso R . . . . .
H201 H -0.2093 0.6581 0.1882 0.0391 1.0000 Uiso R . . . . .
H211 H -0.2911 0.5875 0.4199 0.0362 1.0000 Uiso R . . . . .
H221 H -0.1473 0.4336 0.5206 0.0380 1.0000 Uiso R . . . . .
H231 H 0.0772 0.3514 0.3938 0.0356 1.0000 Uiso R . . . . .
H251 H 0.5023 0.4244 -0.0661 0.0335 1.0000 Uiso R . . . . .
H261 H 0.5920 0.4698 -0.2972 0.0384 1.0000 Uiso R . . . . .
H271 H 0.5963 0.3157 -0.4116 0.0405 1.0000 Uiso R . . . . .
H281 H 0.5090 0.1168 -0.2895 0.0379 1.0000 Uiso R . . . . .
H291 H 0.4143 0.0729 -0.0578 0.0323 1.0000 Uiso R . . . . .
H302 H 0.3167 -0.0243 0.5500 0.0697 1.0000 Uiso R . . . . .
H301 H 0.3675 0.1005 0.5650 0.0689 1.0000 Uiso R . . . . .
H303 H 0.2177 0.1092 0.5401 0.0688 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.692(2)
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 . 1.342(2) yes
O1 . C30 . 1.446(2) yes
C2 . O3 . 1.2020(19) yes
C2 . C4 . 1.510(2) yes
C4 . C5 . 1.531(2) yes
C4 . C8 . 1.550(2) yes
C4 . H41 . 1.004 no
C5 . C6 . 1.501(2) yes
C5 . H52 . 0.996 no
C5 . H51 . 0.996 no
C6 . C7 . 1.310(3) yes
C6 . H61 . 0.971 no
C7 . H72 . 0.969 no
C7 . H71 . 0.984 no
C8 . N9 . 1.4864(19) yes
C8 . C24 . 1.524(2) yes
C8 . H81 . 1.025 no
N9 . C10 . 1.468(2) yes
N9 . C17 . 1.477(2) yes
C10 . C11 . 1.513(2) yes
C10 . H101 . 0.991 no
C10 . H102 . 1.025 no
C11 . C12 . 1.393(2) yes
C11 . C16 . 1.388(2) yes
C12 . C13 . 1.392(2) yes
C12 . H121 . 0.972 no
C13 . C14 . 1.377(3) yes
C13 . H131 . 0.971 no
C14 . C15 . 1.384(3) yes
C14 . H141 . 0.971 no
C15 . C16 . 1.388(2) yes
C15 . H151 . 0.970 no
C16 . H161 . 0.985 no
C17 . C18 . 1.516(2) yes
C17 . H171 . 1.004 no
C17 . H172 . 1.000 no
C18 . C19 . 1.390(2) yes
C18 . C23 . 1.394(2) yes
C19 . C20 . 1.392(2) yes
C19 . H191 . 0.983 no
C20 . C21 . 1.380(2) yes
C20 . H201 . 0.974 no
C21 . C22 . 1.386(2) yes
C21 . H211 . 0.985 no
C22 . C23 . 1.387(2) yes
C22 . H221 . 0.971 no
C23 . H231 . 0.975 no
C24 . C25 . 1.393(2) yes
C24 . C29 . 1.392(2) yes
C25 . C26 . 1.391(2) yes
C25 . H251 . 0.969 no
C26 . C27 . 1.383(3) yes
C26 . H261 . 0.974 no
C27 . C28 . 1.384(3) yes
C27 . H271 . 0.984 no
C28 . C29 . 1.388(2) yes
C28 . H281 . 0.959 no
C29 . H291 . 0.969 no
C30 . H302 . 0.984 no
C30 . H301 . 0.985 no
C30 . H303 . 0.986 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 . C30 . 115.60(14) yes
O1 . C2 . O3 . 123.16(15) yes
O1 . C2 . C4 . 111.69(13) yes
O3 . C2 . C4 . 125.15(15) yes
C2 . C4 . C5 . 112.44(13) yes
C2 . C4 . C8 . 109.21(12) yes
C5 . C4 . C8 . 110.61(12) yes
C2 . C4 . H41 . 107.2 no
C5 . C4 . H41 . 108.1 no
C8 . C4 . H41 . 109.1 no
C4 . C5 . C6 . 115.70(13) yes
C4 . C5 . H52 . 108.8 no
C6 . C5 . H52 . 107.3 no
C4 . C5 . H51 . 108.1 no
C6 . C5 . H51 . 108.0 no
H52 . C5 . H51 . 108.6 no
C5 . C6 . C7 . 127.80(16) yes
C5 . C6 . H61 . 115.2 no
C7 . C6 . H61 . 117.0 no
C6 . C7 . H72 . 121.0 no
C6 . C7 . H71 . 121.3 no
H72 . C7 . H71 . 117.6 no
C4 . C8 . N9 . 110.28(12) yes
C4 . C8 . C24 . 113.14(12) yes
N9 . C8 . C24 . 114.96(12) yes
C4 . C8 . H81 . 105.7 no
N9 . C8 . H81 . 104.7 no
C24 . C8 . H81 . 107.3 no
C8 . N9 . C10 . 111.54(12) yes
C8 . N9 . C17 . 114.46(12) yes
C10 . N9 . C17 . 109.80(12) yes
N9 . C10 . C11 . 114.51(13) yes
N9 . C10 . H101 . 106.5 no
C11 . C10 . H101 . 107.6 no
N9 . C10 . H102 . 110.4 no
C11 . C10 . H102 . 109.4 no
H101 . C10 . H102 . 108.3 no
C10 . C11 . C12 . 119.33(14) yes
C10 . C11 . C16 . 122.00(14) yes
C12 . C11 . C16 . 118.58(15) yes
C11 . C12 . C13 . 120.51(16) yes
C11 . C12 . H121 . 119.4 no
C13 . C12 . H121 . 120.1 no
C12 . C13 . C14 . 120.44(16) yes
C12 . C13 . H131 . 119.0 no
C14 . C13 . H131 . 120.5 no
C13 . C14 . C15 . 119.38(16) yes
C13 . C14 . H141 . 120.4 no
C15 . C14 . H141 . 120.2 no
C14 . C15 . C16 . 120.45(17) yes
C14 . C15 . H151 . 119.5 no
C16 . C15 . H151 . 120.0 no
C11 . C16 . C15 . 120.61(16) yes
C11 . C16 . H161 . 118.2 no
C15 . C16 . H161 . 121.2 no
N9 . C17 . C18 . 112.31(13) yes
N9 . C17 . H171 . 107.5 no
C18 . C17 . H171 . 108.8 no
N9 . C17 . H172 . 109.0 no
C18 . C17 . H172 . 110.2 no
H171 . C17 . H172 . 109.0 no
C17 . C18 . C19 . 120.42(14) yes
C17 . C18 . C23 . 120.96(14) yes
C19 . C18 . C23 . 118.60(15) yes
C18 . C19 . C20 . 120.73(15) yes
C18 . C19 . H191 . 119.1 no
C20 . C19 . H191 . 120.2 no
C19 . C20 . C21 . 120.32(15) yes
C19 . C20 . H201 . 120.2 no
C21 . C20 . H201 . 119.5 no
C20 . C21 . C22 . 119.29(15) yes
C20 . C21 . H211 . 120.9 no
C22 . C21 . H211 . 119.8 no
C21 . C22 . C23 . 120.65(16) yes
C21 . C22 . H221 . 119.5 no
C23 . C22 . H221 . 119.9 no
C18 . C23 . C22 . 120.40(15) yes
C18 . C23 . H231 . 119.4 no
C22 . C23 . H231 . 120.2 no
C8 . C24 . C25 . 122.80(14) yes
C8 . C24 . C29 . 119.31(14) yes
C25 . C24 . C29 . 117.88(15) yes
C24 . C25 . C26 . 121.22(15) yes
C24 . C25 . H251 . 119.4 no
C26 . C25 . H251 . 119.4 no
C25 . C26 . C27 . 120.13(15) yes
C25 . C26 . H261 . 119.8 no
C27 . C26 . H261 . 120.1 no
C26 . C27 . C28 . 119.27(16) yes
C26 . C27 . H271 . 120.0 no
C28 . C27 . H271 . 120.7 no
C27 . C28 . C29 . 120.50(15) yes
C27 . C28 . H281 . 119.5 no
C29 . C28 . H281 . 120.0 no
C24 . C29 . C28 . 120.99(15) yes
C24 . C29 . H291 . 118.7 no
C28 . C29 . H291 . 120.3 no
O1 . C30 . H302 . 108.1 no
O1 . C30 . H301 . 108.8 no
H302 . C30 . H301 . 109.4 no
O1 . C30 . H303 . 109.8 no
H302 . C30 . H303 . 111.0 no
H301 . C30 . H303 . 109.7 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
C21 . H211 . O3 2_566 129.75(5) 0.985 2.582 3.300(3) yes
C26 . H261 . O3 2_665 168.83(5) 0.974 2.467 3.429(3) yes

_iucr_refine_instruction_details_constraints 
;
#
# Punched on 12/07/12 at 14:47:00
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  52,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  72,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,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   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,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   ( 302,X'S) H   ( 301,X'S) H   ( 303,X'S) 
END                                                                             
;

_iucr_refine_instruction_details_restraints 
;
#
# Punched on 12/07/12 at 14:47:00
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 982697'
#######################################################################
#
#                 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_18
_ccdc_journal_depnumber          ?
#==============================================================================

_cell_length_a                   8.66504(13)
_cell_length_b                   9.9818(2)
_cell_length_c                   18.4067(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1592.04(5)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,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'

_cell_formula_units_Z            4

# Given Formula = C16 H25 N1 O2 
# Dc =      1.10 Fooo =    576.00 Mu =      5.62 M =    263.38
# Found Formula = C16 H25 N1 O2 
# Dc =      1.10 FOOO =    576.00 Mu =      5.62 M =    263.38

_chemical_formula_sum            'C16 H25 N1 O2'
_chemical_formula_moiety         'C16 H25 N1 O2'
_chemical_compound_source        .
_chemical_formula_weight         263.38

_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_max          0.210

_exptl_crystal_density_diffrn    1.099
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.562

# Sheldrick geometric approximatio 0.90 0.97 
_exptl_absorpt_correction_type   none
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_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      150
_diffrn_reflns_number            7321
_reflns_number_total             1913
_diffrn_reflns_av_R_equivalents  0.024
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1913 
# Theoretical number of reflections is about 3095 

_diffrn_reflns_theta_min         4.805
_diffrn_reflns_theta_max         76.386
_diffrn_measured_fraction_theta_max 0.992

_diffrn_reflns_theta_full        74.858
_diffrn_measured_fraction_theta_full 0.996

_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              0
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              23

_oxford_diffrn_Wilson_B_factor   3.09
_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         -0.17
_refine_diff_density_max         0.15

# 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>-3.0\s(I)
_refine_ls_number_reflns         7067
_refine_ls_number_restraints     0
_refine_ls_number_parameters     173
_oxford_refine_ls_R_factor_ref   0.0338
_refine_ls_wR_factor_ref         0.0826
_refine_ls_goodness_of_fit_ref   1.0003
_refine_ls_shift/su_max          0.0003703
_refine_ls_shift/su_mean         0.0000513

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        7068
_refine_ls_R_factor_all          0.0339
_refine_ls_wR_factor_all         0.0839

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6792
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_gt          0.0811

_refine_ls_abs_structure_Flack   -0.02(13)
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
# 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 ad

_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/[σ²(F²) + ( 0.04P)² + 0.18P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint

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 0.39363(6) 0.83056(7) 0.20505(4) 0.0396 1.0000 Uani . . . . . .
C2 C 0.43382(9) 0.71523(9) 0.20167(5) 0.0288 1.0000 Uani . . . . . .
O3 O 0.34289(6) 0.61715(7) 0.17648(4) 0.0344 1.0000 Uani . . . . . .
C4 C 0.19204(10) 0.65868(11) 0.15053(6) 0.0396 1.0000 Uani . . . . . .
C5 C 0.59490(8) 0.66697(9) 0.22108(5) 0.0288 1.0000 Uani . . . . . .
C6 C 0.63340(8) 0.71388(9) 0.29872(5) 0.0274 1.0000 Uani . . . . . .
N7 N 0.52983(7) 0.64364(8) 0.34876(4) 0.0309 1.0000 Uani . . . . . .
C8 C 0.55018(9) 0.67470(12) 0.42633(5) 0.0385 1.0000 Uani . . . . . .
C9 C 0.45431(13) 0.57664(14) 0.47032(7) 0.0539 1.0000 Uani . . . . . .
C10 C 0.50202(14) 0.81758(13) 0.44216(6) 0.0519 1.0000 Uani . . . . . .
C11 C 0.80529(8) 0.69804(9) 0.31530(5) 0.0284 1.0000 Uani . . . . . .
C12 C 0.86934(9) 0.57394(11) 0.32986(6) 0.0355 1.0000 Uani . . . . . .
C13 C 1.02760(10) 0.56166(13) 0.34202(6) 0.0430 1.0000 Uani . . . . . .
C14 C 1.12167(9) 0.67360(14) 0.33965(5) 0.0468 1.0000 Uani . . . . . .
C15 C 1.05836(10) 0.79725(13) 0.32517(6) 0.0467 1.0000 Uani . . . . . .
C16 C 0.90079(10) 0.80983(11) 0.31319(6) 0.0375 1.0000 Uani . . . . . .
C17 C 0.70603(9) 0.72314(11) 0.16375(5) 0.0354 1.0000 Uani . . . . . .
C18 C 0.67961(11) 0.67176(14) 0.08716(6) 0.0475 1.0000 Uani . . . . . .
C19 C 0.80153(13) 0.72530(18) 0.03441(6) 0.0610 1.0000 Uani . . . . . .
H41 H 0.1594 0.5816 0.1141 0.0639 1.0000 Uiso R . . . . .
H43 H 0.1201 0.6627 0.1913 0.0623 1.0000 Uiso R . . . . .
H42 H 0.2035 0.7420 0.1218 0.0645 1.0000 Uiso R . . . . .
H51 H 0.5952 0.5625 0.2193 0.0356 1.0000 Uiso R . . . . .
H61 H 0.6105 0.8158 0.3001 0.0350 1.0000 Uiso R . . . . .
H81 H 0.6658 0.6597 0.4400 0.0458 1.0000 Uiso R . . . . .
H93 H 0.4686 0.5876 0.5237 0.0834 1.0000 Uiso R . . . . .
H92 H 0.3421 0.5824 0.4566 0.0820 1.0000 Uiso R . . . . .
H91 H 0.4936 0.4835 0.4586 0.0844 1.0000 Uiso R . . . . .
H103 H 0.5114 0.8398 0.4966 0.0835 1.0000 Uiso R . . . . .
H102 H 0.5655 0.8852 0.4128 0.0837 1.0000 Uiso R . . . . .
H101 H 0.3908 0.8376 0.4257 0.0855 1.0000 Uiso R . . . . .
H121 H 0.8012 0.4906 0.3296 0.0459 1.0000 Uiso R . . . . .
H131 H 1.0771 0.4714 0.3522 0.0541 1.0000 Uiso R . . . . .
H141 H 1.2368 0.6602 0.3465 0.0555 1.0000 Uiso R . . . . .
H151 H 1.1285 0.8773 0.3242 0.0606 1.0000 Uiso R . . . . .
H161 H 0.8503 0.9009 0.3006 0.0470 1.0000 Uiso R . . . . .
H171 H 0.6966 0.8252 0.1649 0.0466 1.0000 Uiso R . . . . .
H172 H 0.8109 0.6927 0.1792 0.0428 1.0000 Uiso R . . . . .
H182 H 0.5727 0.6937 0.0709 0.0587 1.0000 Uiso R . . . . .
H181 H 0.6833 0.5694 0.0875 0.0646 1.0000 Uiso R . . . . .
H193 H 0.7887 0.6735 -0.0160 0.0933 1.0000 Uiso R . . . . .
H192 H 0.7802 0.8324 0.0299 0.0974 1.0000 Uiso R . . . . .
H191 H 0.9057 0.7043 0.0539 0.0913 1.0000 Uiso R . . . . .
H71 H 0.5329 0.5487 0.3391 0.0463 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          6.41(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 . 1.2044(12) yes
C2 . O3 . 1.3395(11) yes
C2 . C5 . 1.5191(10) yes
O3 . C4 . 1.4521(10) yes
C4 . H41 . 1.059 no
C4 . H43 . 0.977 no
C4 . H42 . 0.991 no
C5 . C6 . 1.5405(12) yes
C5 . C17 . 1.5345(12) yes
C5 . H51 . 1.044 no
C6 . N7 . 1.4646(11) yes
C6 . C11 . 1.5286(10) yes
C6 . H61 . 1.037 no
N7 . C8 . 1.4716(12) yes
N7 . H71 . 0.965 no
C8 . C9 . 1.5179(16) yes
C8 . C10 . 1.5143(17) yes
C8 . H81 . 1.044 no
C9 . H93 . 0.996 no
C9 . H92 . 1.007 no
C9 . H91 . 1.013 no
C10 . H103 . 1.029 no
C10 . H102 . 1.025 no
C10 . H101 . 1.030 no
C11 . C12 . 1.3835(13) yes
C11 . C16 . 1.3898(13) yes
C12 . C13 . 1.3949(12) yes
C12 . H121 . 1.020 no
C13 . C14 . 1.3838(17) yes
C13 . H131 . 1.015 no
C14 . C15 . 1.3767(18) yes
C14 . H141 . 1.015 no
C15 . C16 . 1.3887(13) yes
C15 . H151 . 1.004 no
C16 . H161 . 1.035 no
C17 . C18 . 1.5176(14) yes
C17 . H171 . 1.023 no
C17 . H172 . 0.999 no
C18 . C19 . 1.5312(17) yes
C18 . H182 . 0.998 no
C18 . H181 . 1.023 no
C19 . H193 . 1.068 no
C19 . H192 . 1.088 no
C19 . H191 . 0.994 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 . 123.12(7) yes
O1 . C2 . C5 . 123.82(8) yes
O3 . C2 . C5 . 112.96(7) yes
C2 . O3 . C4 . 115.77(7) yes
O3 . C4 . H41 . 104.0 no
O3 . C4 . H43 . 109.5 no
H41 . C4 . H43 . 110.2 no
O3 . C4 . H42 . 109.0 no
H41 . C4 . H42 . 107.3 no
H43 . C4 . H42 . 116.1 no
C2 . C5 . C6 . 108.70(7) yes
C2 . C5 . C17 . 107.40(7) yes
C6 . C5 . C17 . 113.01(7) yes
C2 . C5 . H51 . 108.2 no
C6 . C5 . H51 . 109.4 no
C17 . C5 . H51 . 110.0 no
C5 . C6 . N7 . 107.77(7) yes
C5 . C6 . C11 . 111.39(7) yes
N7 . C6 . C11 . 114.96(7) yes
C5 . C6 . H61 . 106.2 no
N7 . C6 . H61 . 109.7 no
C11 . C6 . H61 . 106.5 no
C6 . N7 . C8 . 115.84(7) yes
C6 . N7 . H71 . 109.7 no
C8 . N7 . H71 . 112.5 no
N7 . C8 . C9 . 108.43(9) yes
N7 . C8 . C10 . 110.62(8) yes
C9 . C8 . C10 . 110.72(9) yes
N7 . C8 . H81 . 108.6 no
C9 . C8 . H81 . 107.7 no
C10 . C8 . H81 . 110.7 no
C8 . C9 . H93 . 112.8 no
C8 . C9 . H92 . 110.9 no
H93 . C9 . H92 . 111.2 no
C8 . C9 . H91 . 107.1 no
H93 . C9 . H91 . 105.6 no
H92 . C9 . H91 . 108.9 no
C8 . C10 . H103 . 111.7 no
C8 . C10 . H102 . 111.8 no
H103 . C10 . H102 . 109.2 no
C8 . C10 . H101 . 112.6 no
H103 . C10 . H101 . 108.6 no
H102 . C10 . H101 . 102.6 no
C6 . C11 . C12 . 121.48(8) yes
C6 . C11 . C16 . 119.44(8) yes
C12 . C11 . C16 . 119.04(7) yes
C11 . C12 . C13 . 120.28(10) yes
C11 . C12 . H121 . 119.8 no
C13 . C12 . H121 . 119.9 no
C12 . C13 . C14 . 120.21(11) yes
C12 . C13 . H131 . 121.5 no
C14 . C13 . H131 . 118.3 no
C13 . C14 . C15 . 119.69(8) yes
C13 . C14 . H141 . 118.0 no
C15 . C14 . H141 . 122.3 no
C14 . C15 . C16 . 120.24(11) yes
C14 . C15 . H151 . 118.4 no
C16 . C15 . H151 . 121.3 no
C11 . C16 . C15 . 120.55(11) yes
C11 . C16 . H161 . 117.4 no
C15 . C16 . H161 . 122.0 no
C5 . C17 . C18 . 114.88(8) yes
C5 . C17 . H171 . 107.4 no
C18 . C17 . H171 . 110.1 no
C5 . C17 . H172 . 105.3 no
C18 . C17 . H172 . 107.4 no
H171 . C17 . H172 . 111.7 no
C17 . C18 . C19 . 111.53(10) yes
C17 . C18 . H182 . 110.1 no
C19 . C18 . H182 . 112.0 no
C17 . C18 . H181 . 109.1 no
C19 . C18 . H181 . 109.3 no
H182 . C18 . H181 . 104.5 no
C18 . C19 . H193 . 108.1 no
C18 . C19 . H192 . 105.9 no
H193 . C19 . H192 . 113.1 no
C18 . C19 . H191 . 108.9 no
H193 . C19 . H191 . 107.8 no
H192 . C19 . H191 . 112.9 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
C12 . H121 . O1 3_645 161.30(3) 1.020 2.410 3.3922(15) yes
C14 . H141 . N7 1_655 172.65(3) 1.015 2.544 3.5532(15) yes
N7 . H71 . O1 3_645 163.18(2) 0.965 2.410 3.3447(15) yes

_iucr_refine_instruction_details_constraints 
;
#
# Punched on 29/08/12 at 16:03:48
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   4,X'S) H   (  41,X'S) H   (  43,X'S) H   (  42,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE N   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  93,X'S) H   (  92,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 103,X'S) H   ( 102,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   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  18,X'S) H   ( 182,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 193,X'S) H   ( 192,X'S) H   ( 191,X'S) 
END                                                                             
;

_iucr_refine_instruction_details_restraints 
;
#
# Punched on 29/08/12 at 16:03:48
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 982698'
#######################################################################
#
#                 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_19
_ccdc_journal_depnumber          ?
#==============================================================================

_cell_length_a                   11.23757(10)
_cell_length_b                   11.23757(10)
_cell_length_c                   31.9939(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3498.98(6)

_symmetry_cell_setting           Trigonal
_symmetry_space_group_name_H-M   'P 31 2 1'
_symmetry_space_group_name_Hall  'P 31 2" '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-y,x-y,z+1/3
-x+y,-x,z+2/3
y,x,-z
x-y,-y,-z+2/3
-x,-x+y,-z+1/3

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            6

# Given Formula = C27 H29 N1 O3 
# Dc =      1.18 Fooo =   1284.00 Mu =      6.06 M =    415.53
# Found Formula = C27 H29 N1 O2 
# Dc =      1.14 FOOO =   1284.00 Mu =      5.53 M =    399.53

_chemical_formula_sum            'C27 H29 N1 O2'
_chemical_formula_moiety         'C27 H29 N1 O2'
_chemical_compound_source        .
_chemical_formula_weight         399.53

_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.230
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_max          0.270

_exptl_crystal_density_diffrn    1.138
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1284
_exptl_absorpt_coefficient_mu    0.553

# Sheldrick geometric approximatio 0.88 0.88 
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.8756
_exptl_absorpt_correction_T_max  0.8805
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_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      150
_diffrn_reflns_number            25382
_reflns_number_total             4879
_diffrn_reflns_av_R_equivalents  0.093
# Number of reflections without Friedels Law is 4879 
# Number of reflections with Friedels Law is 2823 
# Theoretical number of reflections is about 2453 

_diffrn_reflns_theta_min         4.543
_diffrn_reflns_theta_max         76.543
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        76.543
_diffrn_measured_fraction_theta_full 0.997

_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       40
_reflns_limit_h_min              -14
_reflns_limit_h_max              7
_reflns_limit_k_min              0
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              40

_oxford_diffrn_Wilson_B_factor   3.04
_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         -0.19
_refine_diff_density_max         0.13

# 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>-3.0\s(I)
_refine_ls_number_reflns         4158
_refine_ls_number_restraints     0
_refine_ls_number_parameters     272
_oxford_refine_ls_R_factor_ref   0.0336
_refine_ls_wR_factor_ref         0.0854
_refine_ls_goodness_of_fit_ref   1.0089
_refine_ls_shift/su_max          0.0006895
_refine_ls_shift/su_mean         0.0000529

# The values computed from all data 
_oxford_reflns_number_all        4158
_refine_ls_R_factor_all          0.0336
_refine_ls_wR_factor_all         0.0854

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4067
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_gt          0.0849

_refine_ls_abs_structure_Flack   -0.02(18)
_refine_ls_abs_structure_details 'Flack (1983), 2056 Friedel-pairs'
# 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 ad

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.06P)² + 0.35P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint

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 0.86639(9) 0.52631(9) 0.67415(3) 0.0363 1.0000 Uani . . . . . .
C2 C 0.80740(13) 0.39673(12) 0.67636(3) 0.0291 1.0000 Uani . . . . . .
O3 O 0.87015(9) 0.32949(9) 0.67612(3) 0.0402 1.0000 Uani . . . . . .
C4 C 0.65267(12) 0.31691(11) 0.67954(3) 0.0287 1.0000 Uani . . . . . .
C5 C 0.59200(12) 0.32766(11) 0.63719(3) 0.0271 1.0000 Uani . . . . . .
N6 N 0.66484(10) 0.30593(9) 0.60221(3) 0.0286 1.0000 Uani . . . . . .
C7 C 0.65474(13) 0.36236(13) 0.56104(4) 0.0339 1.0000 Uani . . . . . .
C8 C 0.70653(13) 0.51520(13) 0.56561(3) 0.0331 1.0000 Uani . . . . . .
C9 C 0.83986(14) 0.59984(14) 0.57974(4) 0.0406 1.0000 Uani . . . . . .
C10 C 0.89201(16) 0.73977(14) 0.58536(4) 0.0466 1.0000 Uani . . . . . .
C11 C 0.81236(17) 0.79792(14) 0.57615(4) 0.0477 1.0000 Uani . . . . . .
C12 C 0.68085(17) 0.71580(16) 0.56124(4) 0.0480 1.0000 Uani . . . . . .
C13 C 0.62734(15) 0.57506(15) 0.55615(4) 0.0414 1.0000 Uani . . . . . .
C14 C 0.51753(15) 0.28084(15) 0.53835(4) 0.0439 1.0000 Uani . . . . . .
C15 C 0.64723(14) 0.16780(13) 0.59884(4) 0.0356 1.0000 Uani . . . . . .
C16 C 0.75255(16) 0.16476(15) 0.56993(4) 0.0411 1.0000 Uani . . . . . .
C17 C 0.7108(2) 0.05772(17) 0.54142(4) 0.0551 1.0000 Uani . . . . . .
C18 C 0.8051(3) 0.0513(2) 0.51532(5) 0.0766 1.0000 Uani . . . . . .
C19 C 0.9408(3) 0.1511(3) 0.51657(5) 0.0849 1.0000 Uani . . . . . .
C20 C 0.9846(2) 0.2594(3) 0.54479(6) 0.0773 1.0000 Uani . . . . . .
C21 C 0.89041(18) 0.2651(2) 0.57170(5) 0.0568 1.0000 Uani . . . . . .
C22 C 0.43609(12) 0.24048(12) 0.63729(3) 0.0301 1.0000 Uani . . . . . .
C23 C 0.35767(14) 0.30186(14) 0.62840(4) 0.0395 1.0000 Uani . . . . . .
C24 C 0.21521(15) 0.22388(17) 0.62636(5) 0.0529 1.0000 Uani . . . . . .
C25 C 0.14963(15) 0.08424(17) 0.63315(5) 0.0539 1.0000 Uani . . . . . .
C26 C 0.22509(14) 0.02195(15) 0.64353(5) 0.0475 1.0000 Uani . . . . . .
C27 C 0.36751(13) 0.09988(13) 0.64587(4) 0.0365 1.0000 Uani . . . . . .
C28 C 0.60257(13) 0.37142(13) 0.71552(4) 0.0348 1.0000 Uani . . . . . .
C29 C 0.66207(15) 0.36540(16) 0.75684(4) 0.0448 1.0000 Uani . . . . . .
C30 C 0.7381(2) 0.4718(2) 0.78018(5) 0.0751 1.0000 Uani . . . . . .
H41 H 0.6263 0.2215 0.6849 0.0339 1.0000 Uiso R . . . . .
H51 H 0.6158 0.4249 0.6350 0.0296 1.0000 Uiso R . . . . .
H71 H 0.7197 0.3526 0.5432 0.0390 1.0000 Uiso R . . . . .
H91 H 0.8928 0.5577 0.5863 0.0484 1.0000 Uiso R . . . . .
H101 H 0.9811 0.7949 0.5955 0.0566 1.0000 Uiso R . . . . .
H111 H 0.8489 0.8954 0.5798 0.0578 1.0000 Uiso R . . . . .
H121 H 0.6285 0.7574 0.5556 0.0576 1.0000 Uiso R . . . . .
H131 H 0.5346 0.5196 0.5460 0.0508 1.0000 Uiso R . . . . .
H142 H 0.5265 0.3201 0.5100 0.0641 1.0000 Uiso R . . . . .
H141 H 0.4413 0.2835 0.5537 0.0603 1.0000 Uiso R . . . . .
H143 H 0.4917 0.1811 0.5356 0.0635 1.0000 Uiso R . . . . .
H152 H 0.6617 0.1421 0.6271 0.0409 1.0000 Uiso R . . . . .
H151 H 0.5529 0.0986 0.5895 0.0416 1.0000 Uiso R . . . . .
H171 H 0.6145 -0.0126 0.5391 0.0668 1.0000 Uiso R . . . . .
H181 H 0.7747 -0.0224 0.4961 0.0914 1.0000 Uiso R . . . . .
H191 H 1.0010 0.1457 0.4979 0.1039 1.0000 Uiso R . . . . .
H201 H 1.0785 0.3309 0.5456 0.0934 1.0000 Uiso R . . . . .
H211 H 0.9215 0.3384 0.5923 0.0673 1.0000 Uiso R . . . . .
H231 H 0.4035 0.3978 0.6236 0.0433 1.0000 Uiso R . . . . .
H241 H 0.1641 0.2653 0.6206 0.0636 1.0000 Uiso R . . . . .
H251 H 0.0534 0.0323 0.6305 0.0660 1.0000 Uiso R . . . . .
H261 H 0.1811 -0.0738 0.6498 0.0582 1.0000 Uiso R . . . . .
H271 H 0.4186 0.0559 0.6536 0.0423 1.0000 Uiso R . . . . .
H282 H 0.6284 0.4679 0.7089 0.0420 1.0000 Uiso R . . . . .
H281 H 0.5038 0.3170 0.7169 0.0418 1.0000 Uiso R . . . . .
H291 H 0.6408 0.2742 0.7667 0.0536 1.0000 Uiso R . . . . .
H302 H 0.7742 0.4600 0.8062 0.0910 1.0000 Uiso R . . . . .
H301 H 0.7574 0.5597 0.7706 0.0913 1.0000 Uiso R . . . . .
H11 H 0.9512 0.5773 0.6700 0.0548 0.5000 Uiso R . . . . .
H31 H 0.9545 0.3676 0.6713 0.0593 0.5000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.63(10)
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 . 1.2647(14) yes
O1 . H11 . 0.842 no
C2 . O3 . 1.2653(15) yes
C2 . C4 . 1.5095(16) yes
O3 . H31 . 0.837 no
C4 . C5 . 1.5484(14) yes
C4 . C28 . 1.5370(16) yes
C4 . H41 . 0.974 no
C5 . N6 . 1.4774(14) yes
C5 . C22 . 1.5208(16) yes
C5 . H51 . 0.990 no
N6 . C7 . 1.4905(15) yes
N6 . C15 . 1.4673(15) yes
C7 . C8 . 1.5200(17) yes
C7 . C14 . 1.5268(18) yes
C7 . H71 . 0.975 no
C8 . C9 . 1.3889(19) yes
C8 . C13 . 1.3908(18) yes
C9 . C10 . 1.388(2) yes
C9 . H91 . 0.951 no
C10 . C11 . 1.378(2) yes
C10 . H101 . 0.934 no
C11 . C12 . 1.378(2) yes
C11 . H111 . 0.966 no
C12 . C13 . 1.392(2) yes
C12 . H121 . 0.934 no
C13 . H131 . 0.964 no
C14 . H142 . 0.991 no
C14 . H141 . 1.001 no
C14 . H143 . 1.011 no
C15 . C16 . 1.5159(18) yes
C15 . H152 . 0.988 no
C15 . H151 . 0.997 no
C16 . C17 . 1.391(2) yes
C16 . C21 . 1.389(2) yes
C17 . C18 . 1.379(3) yes
C17 . H171 . 0.972 no
C18 . C19 . 1.369(4) yes
C18 . H181 . 0.949 no
C19 . C20 . 1.393(4) yes
C19 . H191 . 0.926 no
C20 . C21 . 1.390(2) yes
C20 . H201 . 0.955 no
C21 . H211 . 0.972 no
C22 . C23 . 1.3933(18) yes
C22 . C27 . 1.3957(17) yes
C23 . C24 . 1.390(2) yes
C23 . H231 . 0.947 no
C24 . C25 . 1.377(2) yes
C24 . H241 . 0.921 no
C25 . C26 . 1.383(2) yes
C25 . H251 . 0.942 no
C26 . C27 . 1.3901(18) yes
C26 . H261 . 0.954 no
C27 . H271 . 0.960 no
C28 . C29 . 1.4982(18) yes
C28 . H282 . 0.996 no
C28 . H281 . 0.964 no
C29 . C30 . 1.302(2) yes
C29 . H291 . 0.981 no
C30 . H302 . 0.963 no
C30 . H301 . 0.950 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 . H11 . 123.8 no
O1 . C2 . O3 . 124.01(11) yes
O1 . C2 . C4 . 118.22(10) yes
O3 . C2 . C4 . 117.76(10) yes
C2 . O3 . H31 . 121.5 no
C2 . C4 . C5 . 108.42(9) yes
C2 . C4 . C28 . 110.88(9) yes
C5 . C4 . C28 . 111.15(10) yes
C2 . C4 . H41 . 107.0 no
C5 . C4 . H41 . 109.6 no
C28 . C4 . H41 . 109.7 no
C4 . C5 . N6 . 110.37(9) yes
C4 . C5 . C22 . 111.00(9) yes
N6 . C5 . C22 . 116.75(9) yes
C4 . C5 . H51 . 105.2 no
N6 . C5 . H51 . 105.2 no
C22 . C5 . H51 . 107.4 no
C5 . N6 . C7 . 115.65(9) yes
C5 . N6 . C15 . 115.96(9) yes
C7 . N6 . C15 . 112.74(9) yes
N6 . C7 . C8 . 109.16(9) yes
N6 . C7 . C14 . 115.70(10) yes
C8 . C7 . C14 . 115.15(11) yes
N6 . C7 . H71 . 104.4 no
C8 . C7 . H71 . 107.3 no
C14 . C7 . H71 . 104.0 no
C7 . C8 . C9 . 118.53(11) yes
C7 . C8 . C13 . 123.33(12) yes
C9 . C8 . C13 . 118.14(12) yes
C8 . C9 . C10 . 121.18(13) yes
C8 . C9 . H91 . 117.4 no
C10 . C9 . H91 . 121.4 no
C9 . C10 . C11 . 120.19(13) yes
C9 . C10 . H101 . 120.1 no
C11 . C10 . H101 . 119.7 no
C10 . C11 . C12 . 119.32(13) yes
C10 . C11 . H111 . 120.2 no
C12 . C11 . H111 . 120.4 no
C11 . C12 . C13 . 120.70(13) yes
C11 . C12 . H121 . 117.7 no
C13 . C12 . H121 . 121.5 no
C12 . C13 . C8 . 120.44(13) yes
C12 . C13 . H131 . 119.1 no
C8 . C13 . H131 . 120.4 no
C7 . C14 . H142 . 108.7 no
C7 . C14 . H141 . 111.8 no
H142 . C14 . H141 . 109.5 no
C7 . C14 . H143 . 110.5 no
H142 . C14 . H143 . 108.9 no
H141 . C14 . H143 . 107.4 no
N6 . C15 . C16 . 112.01(11) yes
N6 . C15 . H152 . 106.7 no
C16 . C15 . H152 . 107.9 no
N6 . C15 . H151 . 112.1 no
C16 . C15 . H151 . 109.7 no
H152 . C15 . H151 . 108.2 no
C15 . C16 . C17 . 119.34(15) yes
C15 . C16 . C21 . 121.56(13) yes
C17 . C16 . C21 . 119.08(15) yes
C16 . C17 . C18 . 120.4(2) yes
C16 . C17 . H171 . 120.7 no
C18 . C17 . H171 . 118.9 no
C17 . C18 . C19 . 120.68(19) yes
C17 . C18 . H181 . 119.2 no
C19 . C18 . H181 . 120.1 no
C18 . C19 . C20 . 119.78(17) yes
C18 . C19 . H191 . 118.5 no
C20 . C19 . H191 . 121.7 no
C19 . C20 . C21 . 119.8(2) yes
C19 . C20 . H201 . 120.7 no
C21 . C20 . H201 . 119.5 no
C20 . C21 . C16 . 120.23(19) yes
C20 . C21 . H211 . 119.9 no
C16 . C21 . H211 . 119.9 no
C5 . C22 . C23 . 119.39(10) yes
C5 . C22 . C27 . 122.40(10) yes
C23 . C22 . C27 . 118.21(11) yes
C22 . C23 . C24 . 120.78(13) yes
C22 . C23 . H231 . 118.6 no
C24 . C23 . H231 . 120.6 no
C23 . C24 . C25 . 120.16(14) yes
C23 . C24 . H241 . 120.2 no
C25 . C24 . H241 . 119.6 no
C24 . C25 . C26 . 120.03(13) yes
C24 . C25 . H251 . 119.1 no
C26 . C25 . H251 . 120.9 no
C25 . C26 . C27 . 119.88(13) yes
C25 . C26 . H261 . 121.2 no
C27 . C26 . H261 . 118.9 no
C22 . C27 . C26 . 120.85(13) yes
C22 . C27 . H271 . 120.0 no
C26 . C27 . H271 . 119.1 no
C4 . C28 . C29 . 112.46(11) yes
C4 . C28 . H282 . 108.0 no
C29 . C28 . H282 . 110.2 no
C4 . C28 . H281 . 108.4 no
C29 . C28 . H281 . 109.3 no
H282 . C28 . H281 . 108.4 no
C28 . C29 . C30 . 124.55(16) yes
C28 . C29 . H291 . 116.7 no
C30 . C29 . H291 . 118.7 no
C29 . C30 . H302 . 119.8 no
C29 . C30 . H301 . 118.2 no
H302 . C30 . H301 . 122.0 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
O1 . H11 . O1 6_766 170.214(11) 0.842 1.811 2.644(2) yes
O3 . H31 . O3 6_766 173.80(4) 0.837 1.765 2.599(2) yes

_iucr_refine_instruction_details_constraints 
;
#
# Punched on 05/12/13 at 11:14:57
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE O   (   1,X'S) H   (  11,X'S) 
RIDE O   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,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   ( 111,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   ( 142,X'S) H   ( 141,X'S) H   ( 143,X'S) 
RIDE C   (  15,X'S) H   ( 152,X'S) H   ( 151,X'S) 
RIDE C   (  17,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   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  23,X'S) H   ( 231,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   ( 282,X'S) H   ( 281,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 302,X'S) H   ( 301,X'S) 
END                                                                             
;

_iucr_refine_instruction_details_restraints 
;
#
# Punched on 05/12/13 at 11:14:57
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 982699'
#######################################################################
#
#                 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_20
_ccdc_journal_depnumber          ?
#==============================================================================

_cell_length_a                   9.7215(3)
_cell_length_b                   13.5384(2)
_cell_length_c                   10.1187(3)
_cell_angle_alpha                90
_cell_angle_beta                 116.959(3)
_cell_angle_gamma                90
_cell_volume                     1187.05(6)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-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 = C28 H31 N1 O2 
# Dc =      1.16 Fooo =    444.00 Mu =      5.59 M =    413.56
# Found Formula = C28 H31 N1 O2 
# Dc =      1.16 FOOO =    444.00 Mu =      5.59 M =    413.56

_chemical_formula_sum            'C28 H31 N1 O2'
_chemical_formula_moiety         'C28 H31 N1 O2'
_chemical_compound_source        .
_chemical_formula_weight         413.56

_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.250
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_max          0.400

_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             444
_exptl_absorpt_coefficient_mu    0.559

# Sheldrick geometric approximatio 0.84 0.87 
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.8409
_exptl_absorpt_correction_T_max  0.8695
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_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      150
_diffrn_reflns_number            10522
_reflns_number_total             2574
_diffrn_reflns_av_R_equivalents  0.031
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2574 
# Theoretical number of reflections is about 4221 

_diffrn_reflns_theta_min         5.104
_diffrn_reflns_theta_max         76.600
_diffrn_measured_fraction_theta_max 0.988

_diffrn_reflns_theta_full        74.302
_diffrn_measured_fraction_theta_full 0.996

_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_reflns_limit_h_min              -12
_reflns_limit_h_max              10
_reflns_limit_k_min              -16
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              12

_oxford_diffrn_Wilson_B_factor   3.35
_oxford_diffrn_Wilson_scale      0.01

_atom_sites_solution_primary     Direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.15
_refine_diff_density_max         0.25

# 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>-3.0\s(I)
_refine_ls_number_reflns         9573
_refine_ls_number_restraints     1
_refine_ls_number_parameters     281
_oxford_refine_ls_R_factor_ref   0.0383
_refine_ls_wR_factor_ref         0.1007
_refine_ls_goodness_of_fit_ref   0.9976
_refine_ls_shift/su_max          0.0003397
_refine_ls_shift/su_mean         0.0000312

# The values computed from all data 
_oxford_reflns_number_all        9574
_refine_ls_R_factor_all          0.0383
_refine_ls_wR_factor_all         0.1008

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                9180
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_gt          0.0986

_refine_ls_abs_structure_Flack   -0.02(15)
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
# 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 ad

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.06P)² + 0.15P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint

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 0.37621(10) 0.30394(8) 0.83994(9) 0.0413 1.0000 Uani . . . . . .
C2 C 0.45393(13) 0.24053(9) 0.79783(13) 0.0318 1.0000 Uani . . . . . .
O3 O 0.58323(10) 0.21314(8) 0.87745(10) 0.0436 1.0000 Uani . . . . . .
C4 C 0.35526(13) 0.20447(9) 0.64128(12) 0.0300 1.0000 Uani . . . . . .
C5 C 0.31944(12) 0.28887(9) 0.52756(12) 0.0293 1.0000 Uani . . . . . .
N6 N 0.46287(10) 0.33875(8) 0.54923(10) 0.0301 1.0000 Uani . . . . . .
C7 C 0.56927(14) 0.28208(10) 0.51124(14) 0.0382 1.0000 Uani . . . . . .
C8 C 0.73022(13) 0.32528(10) 0.58636(14) 0.0364 1.0000 Uani . . . . . .
C9 C 0.79554(15) 0.36896(10) 0.50302(16) 0.0427 1.0000 Uani . . . . . .
C10 C 0.94085(15) 0.41231(10) 0.57299(17) 0.0444 1.0000 Uani . . . . . .
C11 C 1.02304(15) 0.41121(11) 0.72438(17) 0.0483 1.0000 Uani . . . . . .
C12 C 0.96023(16) 0.36656(12) 0.80875(18) 0.0533 1.0000 Uani . . . . . .
C13 C 0.81419(15) 0.32419(11) 0.73909(15) 0.0458 1.0000 Uani . . . . . .
C14 C 0.44521(14) 0.44207(9) 0.49644(13) 0.0354 1.0000 Uani . . . . . .
C15 C 0.39037(13) 0.50522(9) 0.58774(13) 0.0329 1.0000 Uani . . . . . .
C16 C 0.48226(14) 0.50933(10) 0.74044(14) 0.0383 1.0000 Uani . . . . . .
C17 C 0.44283(16) 0.56716(11) 0.83064(16) 0.0461 1.0000 Uani . . . . . .
C18 C 0.30864(16) 0.62217(11) 0.76963(19) 0.0500 1.0000 Uani . . . . . .
C19 C 0.21668(15) 0.61941(10) 0.6195(2) 0.0522 1.0000 Uani . . . . . .
C20 C 0.25646(14) 0.56165(10) 0.52771(16) 0.0428 1.0000 Uani . . . . . .
C21 C 0.35801(19) 0.45726(12) 0.32863(16) 0.0538 1.0000 Uani . . . . . .
C22 C 0.21067(13) 0.25255(10) 0.37131(12) 0.0320 1.0000 Uani . . . . . .
C23 C 0.06773(13) 0.29711(10) 0.29220(13) 0.0358 1.0000 Uani . . . . . .
C24 C -0.03686(14) 0.26212(11) 0.15271(14) 0.0431 1.0000 Uani . . . . . .
C25 C 0.00022(17) 0.18168(11) 0.09235(14) 0.0473 1.0000 Uani . . . . . .
C26 C 0.14184(18) 0.13653(11) 0.16924(15) 0.0499 1.0000 Uani . . . . . .
C27 C 0.24747(16) 0.17199(11) 0.30768(14) 0.0421 1.0000 Uani . . . . . .
C28 C 0.20568(14) 0.15721(10) 0.62880(13) 0.0366 1.0000 Uani . . . . . .
C29 C 0.23271(15) 0.07771(11) 0.74105(14) 0.0425 1.0000 Uani . . . . . .
C30 C 0.16233(19) 0.07132(14) 0.82477(16) 0.0613 1.0000 Uani . . . . . .
C31 C 0.45207(19) 0.33607(12) 0.99165(15) 0.0560 1.0000 Uani . . . . . .
H41 H 0.4128 0.1545 0.6201 0.0351 1.0000 Uiso R . . . . .
H51 H 0.2592 0.3382 0.5515 0.0346 1.0000 Uiso R . . . . .
H72 H 0.5663 0.2147 0.5413 0.0425 1.0000 Uiso R . . . . .
H71 H 0.5390 0.2797 0.3991 0.0429 1.0000 Uiso R . . . . .
H91 H 0.7373 0.3677 0.3939 0.0528 1.0000 Uiso R . . . . .
H101 H 0.9860 0.4414 0.5168 0.0543 1.0000 Uiso R . . . . .
H111 H 1.1163 0.4387 0.7645 0.0594 1.0000 Uiso R . . . . .
H121 H 1.0162 0.3597 0.9143 0.0627 1.0000 Uiso R . . . . .
H131 H 0.7747 0.2929 0.8022 0.0505 1.0000 Uiso R . . . . .
H141 H 0.5527 0.4621 0.5267 0.0410 1.0000 Uiso R . . . . .
H161 H 0.5738 0.4729 0.7807 0.0437 1.0000 Uiso R . . . . .
H171 H 0.5149 0.5730 0.9398 0.0550 1.0000 Uiso R . . . . .
H181 H 0.2730 0.6580 0.8258 0.0589 1.0000 Uiso R . . . . .
H191 H 0.1291 0.6581 0.5793 0.0619 1.0000 Uiso R . . . . .
H201 H 0.1902 0.5579 0.4273 0.0535 1.0000 Uiso R . . . . .
H211 H 0.3732 0.5196 0.2816 0.0767 1.0000 Uiso R . . . . .
H212 H 0.2395 0.4454 0.2801 0.0764 1.0000 Uiso R . . . . .
H213 H 0.3961 0.4090 0.2734 0.0750 1.0000 Uiso R . . . . .
H231 H 0.0398 0.3511 0.3303 0.0420 1.0000 Uiso R . . . . .
H241 H -0.1333 0.2962 0.0935 0.0534 1.0000 Uiso R . . . . .
H251 H -0.0741 0.1610 -0.0072 0.0564 1.0000 Uiso R . . . . .
H261 H 0.1647 0.0794 0.1253 0.0581 1.0000 Uiso R . . . . .
H271 H 0.3422 0.1383 0.3608 0.0493 1.0000 Uiso R . . . . .
H281 H 0.1456 0.1347 0.5249 0.0423 1.0000 Uiso R . . . . .
H282 H 0.1455 0.2094 0.6465 0.0428 1.0000 Uiso R . . . . .
H291 H 0.3086 0.0263 0.7591 0.0510 1.0000 Uiso R . . . . .
H301 H 0.1801 0.0207 0.8901 0.0686 1.0000 Uiso R . . . . .
H302 H 0.0902 0.1186 0.8229 0.0714 1.0000 Uiso R . . . . .
H311 H 0.3889 0.3824 1.0196 0.0779 1.0000 Uiso R . . . . .
H312 H 0.4711 0.2804 1.0536 0.0771 1.0000 Uiso R . . . . .
H313 H 0.5476 0.3659 1.0153 0.0780 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          13.0(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 . 1.3346(14) yes
O1 . C31 . 1.4363(16) yes
C2 . O3 . 1.2035(15) yes
C2 . C4 . 1.5133(16) yes
C4 . C5 . 1.5452(15) yes
C4 . C28 . 1.5406(15) yes
C4 . H41 . 0.963 no
C5 . N6 . 1.4735(13) yes
C5 . C22 . 1.5309(15) yes
C5 . H51 . 0.988 no
N6 . C7 . 1.4720(13) yes
N6 . C14 . 1.4793(14) yes
C7 . C8 . 1.5132(17) yes
C7 . H72 . 0.966 no
C7 . H71 . 1.036 no
C8 . C9 . 1.3963(16) yes
C8 . C13 . 1.3824(19) yes
C9 . C10 . 1.3909(19) yes
C9 . H91 . 0.986 no
C10 . C11 . 1.369(2) yes
C10 . H101 . 0.947 no
C11 . C12 . 1.393(2) yes
C11 . H111 . 0.890 no
C12 . C13 . 1.391(2) yes
C12 . H121 . 0.958 no
C13 . H131 . 0.978 no
C14 . C15 . 1.5217(16) yes
C14 . C21 . 1.5294(18) yes
C14 . H141 . 0.984 no
C15 . C16 . 1.3917(18) yes
C15 . C20 . 1.3893(17) yes
C16 . C17 . 1.3821(18) yes
C16 . H161 . 0.934 no
C17 . C18 . 1.381(2) yes
C17 . H171 . 1.008 no
C18 . C19 . 1.370(2) yes
C18 . H181 . 0.926 no
C19 . C20 . 1.396(2) yes
C19 . H191 . 0.922 no
C20 . H201 . 0.925 no
C21 . H211 . 1.012 no
C21 . H212 . 1.040 no
C21 . H213 . 1.032 no
C22 . C23 . 1.3883(17) yes
C22 . C27 . 1.3931(17) yes
C23 . C24 . 1.3961(18) yes
C23 . H231 . 0.922 no
C24 . C25 . 1.374(2) yes
C24 . H241 . 0.970 no
C25 . C26 . 1.380(2) yes
C25 . H251 . 0.977 no
C26 . C27 . 1.3939(19) yes
C26 . H261 . 0.967 no
C27 . H271 . 0.947 no
C28 . C29 . 1.4990(18) yes
C28 . H281 . 0.991 no
C28 . H282 . 0.984 no
C29 . C30 . 1.311(2) yes
C29 . H291 . 0.969 no
C30 . H301 . 0.913 no
C30 . H302 . 0.944 no
C31 . H311 . 1.004 no
C31 . H312 . 0.944 no
C31 . H313 . 0.939 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 . C31 . 116.45(10) yes
O1 . C2 . O3 . 123.72(10) yes
O1 . C2 . C4 . 111.09(9) yes
O3 . C2 . C4 . 125.12(10) yes
C2 . C4 . C5 . 111.27(9) yes
C2 . C4 . C28 . 110.28(8) yes
C5 . C4 . C28 . 111.12(9) yes
C2 . C4 . H41 . 107.7 no
C5 . C4 . H41 . 108.2 no
C28 . C4 . H41 . 108.2 no
C4 . C5 . N6 . 110.46(8) yes
C4 . C5 . C22 . 110.39(8) yes
N6 . C5 . C22 . 117.70(8) yes
C4 . C5 . H51 . 106.0 no
N6 . C5 . H51 . 106.3 no
C22 . C5 . H51 . 105.2 no
C5 . N6 . C7 . 116.86(8) yes
C5 . N6 . C14 . 115.63(9) yes
C7 . N6 . C14 . 112.26(9) yes
N6 . C7 . C8 . 110.87(9) yes
N6 . C7 . H72 . 106.5 no
C8 . C7 . H72 . 112.3 no
N6 . C7 . H71 . 114.7 no
C8 . C7 . H71 . 106.1 no
H72 . C7 . H71 . 106.4 no
C7 . C8 . C9 . 120.67(11) yes
C7 . C8 . C13 . 120.63(10) yes
C9 . C8 . C13 . 118.69(11) yes
C8 . C9 . C10 . 120.42(13) yes
C8 . C9 . H91 . 118.8 no
C10 . C9 . H91 . 120.8 no
C9 . C10 . C11 . 120.51(11) yes
C9 . C10 . H101 . 120.7 no
C11 . C10 . H101 . 118.8 no
C10 . C11 . C12 . 119.65(13) yes
C10 . C11 . H111 . 117.6 no
C12 . C11 . H111 . 122.7 no
C11 . C12 . C13 . 119.92(14) yes
C11 . C12 . H121 . 122.7 no
C13 . C12 . H121 . 117.3 no
C12 . C13 . C8 . 120.79(11) yes
C12 . C13 . H131 . 117.4 no
C8 . C13 . H131 . 121.8 no
N6 . C14 . C15 . 109.10(9) yes
N6 . C14 . C21 . 116.31(10) yes
C15 . C14 . C21 . 115.35(11) yes
N6 . C14 . H141 . 102.4 no
C15 . C14 . H141 . 105.8 no
C21 . C14 . H141 . 106.5 no
C14 . C15 . C16 . 118.12(10) yes
C14 . C15 . C20 . 124.07(11) yes
C16 . C15 . C20 . 117.78(11) yes
C15 . C16 . C17 . 121.68(12) yes
C15 . C16 . H161 . 117.9 no
C17 . C16 . H161 . 120.4 no
C16 . C17 . C18 . 119.92(13) yes
C16 . C17 . H171 . 120.3 no
C18 . C17 . H171 . 119.6 no
C17 . C18 . C19 . 119.35(12) yes
C17 . C18 . H181 . 123.3 no
C19 . C18 . H181 . 117.2 no
C18 . C19 . C20 . 120.97(12) yes
C18 . C19 . H191 . 118.7 no
C20 . C19 . H191 . 120.3 no
C19 . C20 . C15 . 120.29(13) yes
C19 . C20 . H201 . 119.8 no
C15 . C20 . H201 . 119.8 no
C14 . C21 . H211 . 120.6 no
C14 . C21 . H212 . 116.2 no
H211 . C21 . H212 . 105.8 no
C14 . C21 . H213 . 111.2 no
H211 . C21 . H213 . 96.2 no
H212 . C21 . H213 . 103.9 no
C5 . C22 . C23 . 119.87(10) yes
C5 . C22 . C27 . 121.80(10) yes
C23 . C22 . C27 . 118.26(11) yes
C22 . C23 . C24 . 121.02(11) yes
C22 . C23 . H231 . 120.7 no
C24 . C23 . H231 . 118.3 no
C23 . C24 . C25 . 120.04(12) yes
C23 . C24 . H241 . 121.3 no
C25 . C24 . H241 . 118.5 no
C24 . C25 . C26 . 119.75(12) yes
C24 . C25 . H251 . 117.7 no
C26 . C25 . H251 . 122.5 no
C25 . C26 . C27 . 120.42(12) yes
C25 . C26 . H261 . 118.3 no
C27 . C26 . H261 . 121.3 no
C26 . C27 . C22 . 120.50(13) yes
C26 . C27 . H271 . 119.2 no
C22 . C27 . H271 . 120.2 no
C4 . C28 . C29 . 113.66(10) yes
C4 . C28 . H281 . 107.2 no
C29 . C28 . H281 . 113.5 no
C4 . C28 . H282 . 107.7 no
C29 . C28 . H282 . 107.0 no
H281 . C28 . H282 . 107.5 no
C28 . C29 . C30 . 124.98(14) yes
C28 . C29 . H291 . 121.0 no
C30 . C29 . H291 . 114.0 no
C29 . C30 . H301 . 122.3 no
C29 . C30 . H302 . 122.9 no
H301 . C30 . H302 . 114.8 no
O1 . C31 . H311 . 114.0 no
O1 . C31 . H312 . 108.6 no
H311 . C31 . H312 . 105.8 no
O1 . C31 . H313 . 111.8 no
H311 . C31 . H313 . 108.7 no
H312 . C31 . H313 . 107.5 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
C13 . H131 . O3 . 159.14(4) 0.978 2.549 3.480(2) yes

_iucr_refine_instruction_details_constraints 
;
#
# Punched on 21/06/12 at 17:50:47
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   7,X'S) H   (  72,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   ( 111,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   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,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   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) H   ( 213,X'S) 
RIDE C   (  23,X'S) H   ( 231,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) H   ( 282,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) H   ( 302,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) H   ( 312,X'S) H   ( 313,X'S) 
END                                                                             
;

_iucr_refine_instruction_details_restraints 
;
#
# Punched on 21/06/12 at 17:50:47
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 982700'
#######################################################################
#
#                 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_25
_ccdc_journal_depnumber          ?
#==============================================================================

_cell_length_a                   10.27494(11)
_cell_length_b                   10.27815(10)
_cell_length_c                   12.21513(16)
_cell_angle_alpha                90
_cell_angle_beta                 107.2702(13)
_cell_angle_gamma                90
_cell_volume                     1231.85(3)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-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 = C29 H33 N1 O2 
# Dc =      1.15 Fooo =    460.00 Mu =      5.54 M =    427.59
# Found Formula = C29 H33 N1 O2 
# Dc =      1.15 FOOO =    460.00 Mu =      5.54 M =    427.59

_chemical_formula_sum            'C29 H33 N1 O2'
_chemical_formula_moiety         'C29 H33 N1 O2'
_chemical_compound_source        .
_chemical_formula_weight         427.59

_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.150
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_max          0.190

_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             460
_exptl_absorpt_coefficient_mu    0.554

# Sheldrick geometric approximatio 0.91 0.92 
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9052
_exptl_absorpt_correction_T_max  0.9203
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_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      150
_diffrn_reflns_number            11386
_reflns_number_total             2711
_diffrn_reflns_av_R_equivalents  0.019
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2711 
# Theoretical number of reflections is about 5196 

_diffrn_reflns_theta_min         3.790
_diffrn_reflns_theta_max         76.799
_diffrn_measured_fraction_theta_max 0.993

_diffrn_reflns_theta_full        75.263
_diffrn_measured_fraction_theta_full 0.996

_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              -12
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   2.56
_oxford_diffrn_Wilson_scale      0.01

_atom_sites_solution_primary     Direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.16
_refine_diff_density_max         0.12

# 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>-3.0\s(I)
_refine_ls_number_reflns         10142
_refine_ls_number_restraints     1
_refine_ls_number_parameters     290
_oxford_refine_ls_R_factor_ref   0.0293
_refine_ls_wR_factor_ref         0.0763
_refine_ls_goodness_of_fit_ref   0.9348
_refine_ls_shift/su_max          0.0005254
_refine_ls_shift/su_mean         0.0000587

# The values computed from all data 
_oxford_reflns_number_all        10142
_refine_ls_R_factor_all          0.0293
_refine_ls_wR_factor_all         0.0763

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                9820
_refine_ls_R_factor_gt           0.0282
_refine_ls_wR_factor_gt          0.0748

_refine_ls_abs_structure_Flack   -0.09(10)
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
# 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 ad

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, 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/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.195E+04 0.333E+04 0.213E+04 993. 263. 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint

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 0.44545(6) 0.37346(7) 0.77686(6) 0.0308 1.0000 Uani . . . . . .
C2 C 0.42873(8) 0.26669(9) 0.73470(8) 0.0231 1.0000 Uani . . . . . .
O3 O 0.31161(6) 0.22412(7) 0.66149(5) 0.0261 1.0000 Uani . . . . . .
C4 C 0.19481(9) 0.31455(10) 0.62504(8) 0.0297 1.0000 Uani . . . . . .
C5 C 0.16060(8) 0.36760(11) 0.72781(8) 0.0317 1.0000 Uani . . . . . .
C6 C 0.10536(12) 0.48140(13) 0.73397(11) 0.0524 1.0000 Uani . . . . . .
C7 C 0.22736(12) 0.41649(12) 0.54815(10) 0.0454 1.0000 Uani . . . . . .
C8 C 0.07955(9) 0.22498(12) 0.55929(10) 0.0450 1.0000 Uani . . . . . .
C9 C 0.53543(8) 0.16066(9) 0.75970(7) 0.0236 1.0000 Uani . . . . . .
C10 C 0.67888(8) 0.22035(9) 0.78421(7) 0.0216 1.0000 Uani . . . . . .
N11 N 0.78544(6) 0.11947(8) 0.82155(6) 0.0206 1.0000 Uani . . . . . .
C12 C 0.77478(8) 0.04535(9) 0.92135(7) 0.0233 1.0000 Uani . . . . . .
C13 C 0.68777(8) -0.07649(9) 0.89304(8) 0.0235 1.0000 Uani . . . . . .
C14 C 0.62500(8) -0.12325(10) 0.97125(8) 0.0274 1.0000 Uani . . . . . .
C15 C 0.55140(9) -0.23913(10) 0.95034(9) 0.0341 1.0000 Uani . . . . . .
C16 C 0.53881(9) -0.30881(10) 0.85056(10) 0.0372 1.0000 Uani . . . . . .
C17 C 0.59957(10) -0.26130(9) 0.77190(9) 0.0366 1.0000 Uani . . . . . .
C18 C 0.67405(9) -0.14624(10) 0.79254(8) 0.0312 1.0000 Uani . . . . . .
C19 C 0.92439(8) 0.17628(9) 0.84328(8) 0.0241 1.0000 Uani . . . . . .
C20 C 1.02625(8) 0.06783(9) 0.84494(7) 0.0239 1.0000 Uani . . . . . .
C21 C 1.15522(8) 0.06175(10) 0.92535(8) 0.0285 1.0000 Uani . . . . . .
C22 C 1.24793(8) -0.03327(11) 0.91781(9) 0.0355 1.0000 Uani . . . . . .
C23 C 1.21415(10) -0.12487(11) 0.83128(10) 0.0408 1.0000 Uani . . . . . .
C24 C 1.08604(10) -0.12093(12) 0.75118(9) 0.0409 1.0000 Uani . . . . . .
C25 C 0.99395(9) -0.02443(11) 0.75794(8) 0.0322 1.0000 Uani . . . . . .
C26 C 0.96822(9) 0.26684(11) 0.94686(10) 0.0363 1.0000 Uani . . . . . .
C27 C 0.68914(8) 0.28832(9) 0.67657(8) 0.0252 1.0000 Uani . . . . . .
C28 C 0.68395(9) 0.21680(10) 0.57810(8) 0.0313 1.0000 Uani . . . . . .
C29 C 0.69052(10) 0.27959(12) 0.47891(9) 0.0410 1.0000 Uani . . . . . .
C30 C 0.70085(11) 0.41380(12) 0.47636(11) 0.0489 1.0000 Uani . . . . . .
C31 C 0.70485(12) 0.48468(11) 0.57324(12) 0.0511 1.0000 Uani . . . . . .
C32 C 0.69984(10) 0.42250(10) 0.67282(10) 0.0368 1.0000 Uani . . . . . .
H51 H 0.1717 0.3084 0.7932 0.0377 1.0000 Uiso R . . . . .
H61 H 0.0873 0.5054 0.8005 0.0596 1.0000 Uiso R . . . . .
H62 H 0.0815 0.5362 0.6679 0.0597 1.0000 Uiso R . . . . .
H71 H 0.1483 0.4645 0.5192 0.0692 1.0000 Uiso R . . . . .
H72 H 0.2953 0.4727 0.5891 0.0692 1.0000 Uiso R . . . . .
H73 H 0.2565 0.3804 0.4875 0.0692 1.0000 Uiso R . . . . .
H81 H -0.0059 0.2676 0.5314 0.0760 1.0000 Uiso R . . . . .
H82 H 0.0687 0.1531 0.6086 0.0763 1.0000 Uiso R . . . . .
H83 H 0.1069 0.1876 0.4948 0.0768 1.0000 Uiso R . . . . .
H91 H 0.5327 0.1161 0.8282 0.0287 1.0000 Uiso R . . . . .
H92 H 0.5188 0.1012 0.7018 0.0240 1.0000 Uiso R . . . . .
H101 H 0.6887 0.2831 0.8440 0.0213 1.0000 Uiso R . . . . .
H121 H 0.8669 0.0142 0.9573 0.0267 1.0000 Uiso R . . . . .
H122 H 0.7499 0.0966 0.9825 0.0307 1.0000 Uiso R . . . . .
H141 H 0.6315 -0.0773 1.0362 0.0361 1.0000 Uiso R . . . . .
H151 H 0.5070 -0.2723 1.0020 0.0432 1.0000 Uiso R . . . . .
H161 H 0.4957 -0.3893 0.8385 0.0474 1.0000 Uiso R . . . . .
H171 H 0.5905 -0.3064 0.6998 0.0472 1.0000 Uiso R . . . . .
H181 H 0.7132 -0.1149 0.7367 0.0359 1.0000 Uiso R . . . . .
H191 H 0.9271 0.2281 0.7793 0.0318 1.0000 Uiso R . . . . .
H211 H 1.1770 0.1281 0.9854 0.0365 1.0000 Uiso R . . . . .
H221 H 1.3359 -0.0343 0.9776 0.0427 1.0000 Uiso R . . . . .
H231 H 1.2800 -0.1843 0.8282 0.0485 1.0000 Uiso R . . . . .
H241 H 1.0600 -0.1850 0.6906 0.0480 1.0000 Uiso R . . . . .
H251 H 0.9092 -0.0222 0.6999 0.0358 1.0000 Uiso R . . . . .
H263 H 1.0524 0.3126 0.9517 0.0529 1.0000 Uiso R . . . . .
H262 H 0.9840 0.2260 1.0210 0.0558 1.0000 Uiso R . . . . .
H261 H 0.8976 0.3308 0.9471 0.0560 1.0000 Uiso R . . . . .
H281 H 0.6796 0.1243 0.5850 0.0398 1.0000 Uiso R . . . . .
H291 H 0.6842 0.2313 0.4121 0.0520 1.0000 Uiso R . . . . .
H301 H 0.7062 0.4536 0.4092 0.0557 1.0000 Uiso R . . . . .
H311 H 0.7113 0.5748 0.5702 0.0613 1.0000 Uiso R . . . . .
H321 H 0.7038 0.4757 0.7387 0.0434 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          9.60(14)
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 . 1.2027(11) yes
C2 . O3 . 1.3418(10) yes
C2 . C9 . 1.5113(11) yes
O3 . C4 . 1.4782(10) yes
C4 . C5 . 1.5029(14) yes
C4 . C7 . 1.5094(14) yes
C4 . C8 . 1.5266(14) yes
C5 . C6 . 1.3119(16) yes
C5 . H51 . 0.983 no
C6 . H61 . 0.919 no
C6 . H62 . 0.955 no
C7 . H71 . 0.927 no
C7 . H72 . 0.929 no
C7 . H73 . 0.953 no
C8 . H81 . 0.949 no
C8 . H82 . 0.980 no
C8 . H83 . 0.989 no
C9 . C10 . 1.5416(11) yes
C9 . H91 . 0.961 no
C9 . H92 . 0.911 no
C10 . N11 . 1.4783(10) yes
C10 . C27 . 1.5200(12) yes
C10 . H101 . 0.957 no
N11 . C12 . 1.4690(11) yes
N11 . C19 . 1.4915(10) yes
C12 . C13 . 1.5178(12) yes
C12 . H121 . 0.972 no
C12 . H122 . 1.007 no
C13 . C14 . 1.3877(13) yes
C13 . C18 . 1.3921(13) yes
C14 . C15 . 1.3932(13) yes
C14 . H141 . 0.908 no
C15 . C16 . 1.3863(16) yes
C15 . H151 . 0.946 no
C16 . C17 . 1.3811(16) yes
C16 . H161 . 0.929 no
C17 . C18 . 1.3904(13) yes
C17 . H171 . 0.976 no
C18 . H181 . 0.946 no
C19 . C20 . 1.5250(11) yes
C19 . C26 . 1.5270(13) yes
C19 . H191 . 0.953 no
C20 . C21 . 1.3971(11) yes
C20 . C25 . 1.3890(13) yes
C21 . C22 . 1.3863(13) yes
C21 . H211 . 0.977 no
C22 . C23 . 1.3806(16) yes
C22 . H221 . 0.979 no
C23 . C24 . 1.3881(14) yes
C23 . H231 . 0.921 no
C24 . C25 . 1.3900(14) yes
C24 . H241 . 0.967 no
C25 . H251 . 0.946 no
C26 . H263 . 0.971 no
C26 . H262 . 0.967 no
C26 . H261 . 0.980 no
C27 . C28 . 1.3971(14) yes
C27 . C32 . 1.3853(13) yes
C28 . C29 . 1.3920(14) yes
C28 . H281 . 0.956 no
C29 . C30 . 1.3845(18) yes
C29 . H291 . 0.940 no
C30 . C31 . 1.3799(19) yes
C30 . H301 . 0.933 no
C31 . C32 . 1.3885(16) yes
C31 . H311 . 0.930 no
C32 . H321 . 0.963 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 . 124.66(7) yes
O1 . C2 . C9 . 124.65(7) yes
O3 . C2 . C9 . 110.66(7) yes
C2 . O3 . C4 . 118.88(7) yes
O3 . C4 . C5 . 110.29(7) yes
O3 . C4 . C7 . 108.29(7) yes
C5 . C4 . C7 . 114.70(9) yes
O3 . C4 . C8 . 102.29(7) yes
C5 . C4 . C8 . 108.72(8) yes
C7 . C4 . C8 . 111.83(9) yes
C4 . C5 . C6 . 125.72(10) yes
C4 . C5 . H51 . 117.1 no
C6 . C5 . H51 . 116.9 no
C5 . C6 . H61 . 119.6 no
C5 . C6 . H62 . 119.0 no
H61 . C6 . H62 . 121.4 no
C4 . C7 . H71 . 106.0 no
C4 . C7 . H72 . 111.4 no
H71 . C7 . H72 . 107.9 no
C4 . C7 . H73 . 113.1 no
H71 . C7 . H73 . 110.7 no
H72 . C7 . H73 . 107.5 no
C4 . C8 . H81 . 113.7 no
C4 . C8 . H82 . 110.1 no
H81 . C8 . H82 . 107.8 no
C4 . C8 . H83 . 107.1 no
H81 . C8 . H83 . 110.2 no
H82 . C8 . H83 . 107.9 no
C2 . C9 . C10 . 110.28(7) yes
C2 . C9 . H91 . 108.2 no
C10 . C9 . H91 . 107.1 no
C2 . C9 . H92 . 111.7 no
C10 . C9 . H92 . 111.4 no
H91 . C9 . H92 . 108.0 no
C9 . C10 . N11 . 111.02(6) yes
C9 . C10 . C27 . 108.83(6) yes
N11 . C10 . C27 . 110.74(6) yes
C9 . C10 . H101 . 107.1 no
N11 . C10 . H101 . 109.7 no
C27 . C10 . H101 . 109.4 no
C10 . N11 . C12 . 112.89(6) yes
C10 . N11 . C19 . 111.25(6) yes
C12 . N11 . C19 . 111.02(6) yes
N11 . C12 . C13 . 115.01(7) yes
N11 . C12 . H121 . 104.1 no
C13 . C12 . H121 . 105.1 no
N11 . C12 . H122 . 116.3 no
C13 . C12 . H122 . 109.8 no
H121 . C12 . H122 . 105.3 no
C12 . C13 . C14 . 119.44(8) yes
C12 . C13 . C18 . 121.63(8) yes
C14 . C13 . C18 . 118.86(8) yes
C13 . C14 . C15 . 120.52(9) yes
C13 . C14 . H141 . 119.5 no
C15 . C14 . H141 . 120.0 no
C14 . C15 . C16 . 120.45(9) yes
C14 . C15 . H151 . 122.0 no
C16 . C15 . H151 . 117.6 no
C15 . C16 . C17 . 119.05(8) yes
C15 . C16 . H161 . 121.0 no
C17 . C16 . H161 . 119.8 no
C16 . C17 . C18 . 120.85(9) yes
C16 . C17 . H171 . 121.3 no
C18 . C17 . H171 . 117.9 no
C13 . C18 . C17 . 120.27(9) yes
C13 . C18 . H181 . 120.5 no
C17 . C18 . H181 . 119.2 no
N11 . C19 . C20 . 109.45(6) yes
N11 . C19 . C26 . 114.67(7) yes
C20 . C19 . C26 . 113.71(7) yes
N11 . C19 . H191 . 109.4 no
C20 . C19 . H191 . 103.4 no
C26 . C19 . H191 . 105.4 no
C19 . C20 . C21 . 123.09(8) yes
C19 . C20 . C25 . 118.80(7) yes
C21 . C20 . C25 . 117.95(8) yes
C20 . C21 . C22 . 120.79(8) yes
C20 . C21 . H211 . 117.1 no
C22 . C21 . H211 . 122.2 no
C21 . C22 . C23 . 120.65(8) yes
C21 . C22 . H221 . 117.3 no
C23 . C22 . H221 . 122.0 no
C22 . C23 . C24 . 119.34(9) yes
C22 . C23 . H231 . 117.6 no
C24 . C23 . H231 . 123.0 no
C23 . C24 . C25 . 119.92(9) yes
C23 . C24 . H241 . 120.6 no
C25 . C24 . H241 . 119.5 no
C24 . C25 . C20 . 121.36(8) yes
C24 . C25 . H251 . 117.6 no
C20 . C25 . H251 . 121.0 no
C19 . C26 . H263 . 112.6 no
C19 . C26 . H262 . 115.9 no
H263 . C26 . H262 . 104.8 no
C19 . C26 . H261 . 112.0 no
H263 . C26 . H261 . 108.8 no
H262 . C26 . H261 . 102.0 no
C10 . C27 . C28 . 120.54(7) yes
C10 . C27 . C32 . 120.85(9) yes
C28 . C27 . C32 . 118.59(9) yes
C27 . C28 . C29 . 120.40(9) yes
C27 . C28 . H281 . 116.0 no
C29 . C28 . H281 . 123.6 no
C28 . C29 . C30 . 120.35(11) yes
C28 . C29 . H291 . 120.1 no
C30 . C29 . H291 . 119.5 no
C29 . C30 . C31 . 119.32(10) yes
C29 . C30 . H301 . 118.8 no
C31 . C30 . H301 . 121.9 no
C30 . C31 . C32 . 120.59(10) yes
C30 . C31 . H311 . 118.4 no
C32 . C31 . H311 . 121.0 no
C31 . C32 . C27 . 120.74(11) yes
C31 . C32 . H321 . 117.8 no
C27 . C32 . H321 . 121.4 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
C16 . H161 . O1 1_545 160.07(3) 0.929 2.559 3.4470(14) yes

_iucr_refine_instruction_details_constraints 
;
#
# Punched on 22/06/12 at 11:18:30
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,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   (   8,X'S) H   (  81,X'S) H   (  82,X'S) H   (  83,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) H   ( 122,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   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,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   ( 263,X'S) H   ( 262,X'S) H   ( 261,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) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
END                                                                             
;

_iucr_refine_instruction_details_restraints 
;
#
# Punched on 22/06/12 at 11:18:30
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 982701'
#######################################################################
#
#                 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_29
_ccdc_journal_depnumber          ?
#==============================================================================

_cell_length_a                   12.4852(2)
_cell_length_b                   9.9345(2)
_cell_length_c                   15.0329(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.0163(9)
_cell_angle_gamma                90
_cell_volume                     1836.17(6)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 = C18 H29 N1 O2 
# Dc =      1.05 Fooo =    640.00 Mu =      0.67 M =    582.87
# Found Formula = C18 H29 N1 O2 
# Dc =      1.05 FOOO =    640.00 Mu =      0.67 M =    582.87

_chemical_formula_sum            'C18 H29 N1 O2'
_chemical_formula_moiety         'C18 H29 N1 O2'
_chemical_compound_source        .
_chemical_formula_weight         291.43

_cell_measurement_reflns_used    4247
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.270
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_max          0.380

_exptl_crystal_density_diffrn    1.054
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.067

# Sheldrick geometric approximatio 0.98 0.98 
# No experimental values of Tmin/max available 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.98
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_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      150
_diffrn_reflns_number            7390
_reflns_number_total             4416
_diffrn_reflns_av_R_equivalents  0.019
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 4416 
# Theoretical number of reflections is about 7612 

_diffrn_reflns_theta_min         5.246
_diffrn_reflns_theta_max         27.489
_diffrn_measured_fraction_theta_max 0.989

_diffrn_reflns_theta_full        26.939
_diffrn_measured_fraction_theta_full 0.990

_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_reflns_limit_h_min              -16
_reflns_limit_h_max              15
_reflns_limit_k_min              0
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              19

_oxford_diffrn_Wilson_B_factor   2.93
_oxford_diffrn_Wilson_scale      1.25

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.19
_refine_diff_density_max         0.42

# 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>-3.0\s(I)
_refine_ls_number_reflns         4002
_refine_ls_number_restraints     1
_refine_ls_number_parameters     379
_oxford_refine_ls_R_factor_ref   0.0491
_refine_ls_wR_factor_ref         0.1086
_refine_ls_goodness_of_fit_ref   0.9156
_refine_ls_shift/su_max          0.0001859
_refine_ls_shift/su_mean         0.0000167

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4002
_refine_ls_R_factor_all          0.0491
_refine_ls_wR_factor_all         0.1086

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3635
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_gt          0.1031

# 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 unk

_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/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 40.1 65.4 39.0 15.9 3.52 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint

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 0.22849(15) 0.87017(18) 0.33366(11) 0.0416 1.0000 Uani . . . . . .
C2 C 0.20350(16) 0.7553(2) 0.31379(14) 0.0300 1.0000 Uani . . . . . .
O3 O 0.21499(13) 0.65482(17) 0.37420(9) 0.0350 1.0000 Uani . . . . . .
C4 C 0.2530(2) 0.6958(3) 0.46694(14) 0.0427 1.0000 Uani . . . . . .
C5 C 0.14951(15) 0.7101(2) 0.22075(13) 0.0282 1.0000 Uani . . . . . .
C6 C 0.21510(15) 0.7660(2) 0.15093(12) 0.0262 1.0000 Uani . . . . . .
N7 N 0.32135(13) 0.6981(2) 0.16841(11) 0.0297 1.0000 Uani . . . . . .
C8 C 0.39745(17) 0.7400(3) 0.10871(15) 0.0364 1.0000 Uani . . . . . .
C9 C 0.4461(2) 0.8766(3) 0.1382(2) 0.0531 1.0000 Uani . . . . . .
C10 C 0.4852(2) 0.6336(3) 0.1126(2) 0.0576 1.0000 Uani . . . . . .
C11 C 0.15264(15) 0.7535(2) 0.05489(13) 0.0277 1.0000 Uani . . . . . .
C12 C 0.10765(17) 0.8681(2) 0.00940(15) 0.0336 1.0000 Uani . . . . . .
C13 C 0.04609(18) 0.8590(3) -0.07705(16) 0.0411 1.0000 Uani . . . . . .
C14 C 0.02906(18) 0.7355(3) -0.11899(15) 0.0422 1.0000 Uani . . . . . .
C15 C 0.07477(19) 0.6219(3) -0.07478(16) 0.0401 1.0000 Uani . . . . . .
C16 C 0.13616(18) 0.6302(2) 0.01160(14) 0.0341 1.0000 Uani . . . . . .
C17 C 0.02995(17) 0.7575(3) 0.20539(14) 0.0360 1.0000 Uani . . . . . .
C18 C -0.03362(18) 0.6988(3) 0.27485(16) 0.0442 1.0000 Uani . . . . . .
C19 C -0.1581(2) 0.7039(3) 0.24741(19) 0.0509 1.0000 Uani . . . . . .
C20 C -0.2111(2) 0.6310(5) 0.3184(2) 0.0731 1.0000 Uani . . . . . .
C21 C -0.2007(3) 0.8422(5) 0.2299(4) 0.0996 1.0000 Uani . . . . . .
O22 O 0.23996(13) 0.38389(17) 0.16610(10) 0.0366 1.0000 Uani . . . . . .
C23 C 0.27039(16) 0.2695(2) 0.18182(14) 0.0287 1.0000 Uani . . . . . .
O24 O 0.26137(12) 0.17414(17) 0.11765(10) 0.0351 1.0000 Uani . . . . . .
C25 C 0.2226(2) 0.2197(3) 0.02662(15) 0.0447 1.0000 Uani . . . . . .
C26 C 0.33111(15) 0.2202(2) 0.27168(13) 0.0277 1.0000 Uani . . . . . .
C27 C 0.26764(15) 0.2586(2) 0.34779(12) 0.0272 1.0000 Uani . . . . . .
N28 N 0.16451(13) 0.18327(19) 0.33117(11) 0.0303 1.0000 Uani . . . . . .
C29 C 0.09398(17) 0.2039(3) 0.39901(16) 0.0398 1.0000 Uani . . . . . .
C30 C 0.0067(2) 0.0949(3) 0.3849(2) 0.0586 1.0000 Uani . . . . . .
C31 C 0.0426(2) 0.3433(3) 0.3879(2) 0.0562 1.0000 Uani . . . . . .
C32 C 0.33734(15) 0.2367(2) 0.44046(13) 0.0275 1.0000 Uani . . . . . .
C33 C 0.36092(18) 0.1075(2) 0.47459(15) 0.0337 1.0000 Uani . . . . . .
C34 C 0.42954(19) 0.0892(3) 0.55739(15) 0.0402 1.0000 Uani . . . . . .
C35 C 0.47559(18) 0.1986(3) 0.60701(15) 0.0430 1.0000 Uani . . . . . .
C36 C 0.4508(2) 0.3271(3) 0.57414(16) 0.0452 1.0000 Uani . . . . . .
C37 C 0.38206(18) 0.3457(3) 0.49172(15) 0.0375 1.0000 Uani . . . . . .
C38 C 0.44509(16) 0.2841(2) 0.28565(13) 0.0325 1.0000 Uani . . . . . .
C39 C 0.50858(17) 0.2575(3) 0.20940(14) 0.0374 1.0000 Uani . . . . . .
C40 C 0.62450(18) 0.3120(3) 0.22912(15) 0.0457 1.0000 Uani . . . . . .
C41 C 0.6745(2) 0.3188(5) 0.14430(19) 0.0714 1.0000 Uani . . . . . .
C42 C 0.6957(2) 0.2320(6) 0.3003(2) 0.0889 1.0000 Uani . . . . . .
H41 H 0.2473 0.6178 0.5056 0.0665 1.0000 Uiso R . . . . .
H43 H 0.2074 0.7696 0.4810 0.0662 1.0000 Uiso R . . . . .
H42 H 0.3272 0.7254 0.4722 0.0658 1.0000 Uiso R . . . . .
H51 H 0.1497 0.6101 0.2180 0.0332 1.0000 Uiso R . . . . .
H61 H 0.2273 0.8624 0.1637 0.0331 1.0000 Uiso R . . . . .
H81 H 0.3581 0.7498 0.0454 0.0483 1.0000 Uiso R . . . . .
H92 H 0.4960 0.8980 0.0981 0.0825 1.0000 Uiso R . . . . .
H91 H 0.3872 0.9430 0.1333 0.0825 1.0000 Uiso R . . . . .
H93 H 0.4852 0.8642 0.2011 0.0827 1.0000 Uiso R . . . . .
H101 H 0.5323 0.6575 0.0706 0.0900 1.0000 Uiso R . . . . .
H102 H 0.4498 0.5455 0.0982 0.0904 1.0000 Uiso R . . . . .
H103 H 0.5269 0.6326 0.1740 0.0901 1.0000 Uiso R . . . . .
H121 H 0.1196 0.9531 0.0393 0.0438 1.0000 Uiso R . . . . .
H131 H 0.0182 0.9407 -0.1066 0.0522 1.0000 Uiso R . . . . .
H141 H -0.0147 0.7288 -0.1784 0.0536 1.0000 Uiso R . . . . .
H151 H 0.0651 0.5360 -0.1031 0.0483 1.0000 Uiso R . . . . .
H161 H 0.1672 0.5516 0.0428 0.0422 1.0000 Uiso R . . . . .
H171 H -0.0058 0.7288 0.1446 0.0442 1.0000 Uiso R . . . . .
H172 H 0.0297 0.8569 0.2104 0.0444 1.0000 Uiso R . . . . .
H181 H -0.0117 0.6026 0.2861 0.0556 1.0000 Uiso R . . . . .
H182 H -0.0152 0.7530 0.3293 0.0556 1.0000 Uiso R . . . . .
H191 H -0.1804 0.6535 0.1876 0.0708 1.0000 Uiso R . . . . .
H202 H -0.2916 0.6258 0.2994 0.1133 1.0000 Uiso R . . . . .
H201 H -0.1805 0.5368 0.3275 0.1139 1.0000 Uiso R . . . . .
H203 H -0.1912 0.6879 0.3749 0.1132 1.0000 Uiso R . . . . .
H212 H -0.2799 0.8381 0.2133 0.1548 1.0000 Uiso R . . . . .
H211 H -0.1648 0.8793 0.1828 0.1555 1.0000 Uiso R . . . . .
H213 H -0.1759 0.8848 0.2876 0.1550 1.0000 Uiso R . . . . .
H251 H 0.2274 0.1429 -0.0135 0.0696 1.0000 Uiso R . . . . .
H252 H 0.1472 0.2503 0.0221 0.0695 1.0000 Uiso R . . . . .
H253 H 0.2693 0.2936 0.0130 0.0688 1.0000 Uiso R . . . . .
H261 H 0.3389 0.1211 0.2717 0.0334 1.0000 Uiso R . . . . .
H271 H 0.2509 0.3554 0.3409 0.0352 1.0000 Uiso R . . . . .
H291 H 0.1378 0.1967 0.4606 0.0522 1.0000 Uiso R . . . . .
H301 H -0.0370 0.1083 0.4317 0.0939 1.0000 Uiso R . . . . .
H302 H -0.0369 0.1085 0.3260 0.0941 1.0000 Uiso R . . . . .
H303 H 0.0434 0.0090 0.3908 0.0940 1.0000 Uiso R . . . . .
H312 H -0.0016 0.3550 0.4342 0.0915 1.0000 Uiso R . . . . .
H311 H -0.0037 0.3425 0.3272 0.0915 1.0000 Uiso R . . . . .
H313 H 0.0986 0.4125 0.3928 0.0914 1.0000 Uiso R . . . . .
H331 H 0.3296 0.0323 0.4395 0.0425 1.0000 Uiso R . . . . .
H341 H 0.4439 0.0024 0.5812 0.0508 1.0000 Uiso R . . . . .
H351 H 0.5231 0.1865 0.6627 0.0536 1.0000 Uiso R . . . . .
H361 H 0.4808 0.4023 0.6078 0.0580 1.0000 Uiso R . . . . .
H371 H 0.3648 0.4343 0.4689 0.0483 1.0000 Uiso R . . . . .
H381 H 0.4373 0.3811 0.2917 0.0404 1.0000 Uiso R . . . . .
H382 H 0.4866 0.2484 0.3409 0.0400 1.0000 Uiso R . . . . .
H392 H 0.5149 0.1593 0.2007 0.0461 1.0000 Uiso R . . . . .
H391 H 0.4690 0.3004 0.1521 0.0461 1.0000 Uiso R . . . . .
H401 H 0.6218 0.4068 0.2531 0.0588 1.0000 Uiso R . . . . .
H413 H 0.7471 0.3591 0.1580 0.1093 1.0000 Uiso R . . . . .
H412 H 0.6796 0.2221 0.1248 0.1092 1.0000 Uiso R . . . . .
H411 H 0.6272 0.3723 0.0975 0.1089 1.0000 Uiso R . . . . .
H423 H 0.7684 0.2721 0.3133 0.1521 1.0000 Uiso R . . . . .
H422 H 0.6966 0.1417 0.2737 0.1524 1.0000 Uiso R . . . . .
H421 H 0.6639 0.2295 0.3541 0.1518 1.0000 Uiso R . . . . .
H71 H 0.3090 0.6096 0.1634 0.0387 1.0000 Uiso R . . . . .
H281 H 0.1838 0.0964 0.3327 0.0408 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.929(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 . 1.207(3) yes
C2 . O3 . 1.341(3) yes
C2 . C5 . 1.511(3) yes
O3 . C4 . 1.451(3) yes
C4 . H41 . 0.978 no
C4 . H43 . 0.974 no
C4 . H42 . 0.962 no
C5 . C6 . 1.542(3) yes
C5 . C17 . 1.544(3) yes
C5 . H51 . 0.995 no
C6 . N7 . 1.471(2) yes
C6 . C11 . 1.522(3) yes
C6 . H61 . 0.983 no
N7 . C8 . 1.476(3) yes
N7 . H71 . 0.893 no
C8 . C9 . 1.521(4) yes
C8 . C10 . 1.516(4) yes
C8 . H81 . 0.997 no
C9 . H92 . 0.963 no
C9 . H91 . 0.981 no
C9 . H93 . 0.994 no
C10 . H101 . 0.964 no
C10 . H102 . 0.987 no
C10 . H103 . 0.979 no
C11 . C12 . 1.395(3) yes
C11 . C16 . 1.386(3) yes
C12 . C13 . 1.393(3) yes
C12 . H121 . 0.956 no
C13 . C14 . 1.379(4) yes
C13 . H131 . 0.962 no
C14 . C15 . 1.381(4) yes
C14 . H141 . 0.965 no
C15 . C16 . 1.391(3) yes
C15 . H151 . 0.952 no
C16 . H161 . 0.958 no
C17 . C18 . 1.533(3) yes
C17 . H171 . 0.986 no
C17 . H172 . 0.990 no
C18 . C19 . 1.537(3) yes
C18 . H181 . 1.000 no
C18 . H182 . 0.974 no
C19 . C20 . 1.532(4) yes
C19 . C21 . 1.480(5) yes
C19 . H191 . 1.025 no
C20 . H202 . 0.997 no
C20 . H201 . 1.011 no
C20 . H203 . 1.014 no
C21 . H212 . 0.978 no
C21 . H211 . 0.974 no
C21 . H213 . 0.966 no
O22 . C23 . 1.209(3) yes
C23 . O24 . 1.343(3) yes
C23 . C26 . 1.511(3) yes
O24 . C25 . 1.443(3) yes
C25 . H251 . 0.980 no
C25 . H252 . 0.980 no
C25 . H253 . 0.981 no
C26 . C27 . 1.549(3) yes
C26 . C38 . 1.539(3) yes
C26 . H261 . 0.989 no
C27 . N28 . 1.472(3) yes
C27 . C32 . 1.524(3) yes
C27 . H271 . 0.986 no
N28 . C29 . 1.473(3) yes
N28 . H281 . 0.895 no
C29 . C30 . 1.525(4) yes
C29 . C31 . 1.523(4) yes
C29 . H291 . 0.993 no
C30 . H301 . 0.971 no
C30 . H302 . 0.965 no
C30 . H303 . 0.966 no
C31 . H312 . 0.969 no
C31 . H311 . 0.991 no
C31 . H313 . 0.974 no
C32 . C33 . 1.394(3) yes
C32 . C37 . 1.389(3) yes
C33 . C34 . 1.395(3) yes
C33 . H331 . 0.958 no
C34 . C35 . 1.386(4) yes
C34 . H341 . 0.939 no
C35 . C36 . 1.384(4) yes
C35 . H351 . 0.946 no
C36 . C37 . 1.391(3) yes
C36 . H361 . 0.942 no
C37 . H371 . 0.956 no
C38 . C39 . 1.526(3) yes
C38 . H381 . 0.974 no
C38 . H382 . 0.966 no
C39 . C40 . 1.525(3) yes
C39 . H392 . 0.989 no
C39 . H391 . 1.010 no
C40 . C41 . 1.516(3) yes
C40 . C42 . 1.495(4) yes
C40 . H401 . 1.011 no
C41 . H413 . 0.979 no
C41 . H412 . 1.011 no
C41 . H411 . 0.990 no
C42 . H423 . 0.979 no
C42 . H422 . 0.983 no
C42 . H421 . 0.962 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 . 122.95(19) yes
O1 . C2 . C5 . 124.4(2) yes
O3 . C2 . C5 . 112.55(18) yes
C2 . O3 . C4 . 114.87(19) yes
O3 . C4 . H41 . 107.7 no
O3 . C4 . H43 . 108.3 no
H41 . C4 . H43 . 111.1 no
O3 . C4 . H42 . 108.3 no
H41 . C4 . H42 . 111.2 no
H43 . C4 . H42 . 110.1 no
C2 . C5 . C6 . 108.58(16) yes
C2 . C5 . C17 . 108.17(16) yes
C6 . C5 . C17 . 113.73(16) yes
C2 . C5 . H51 . 109.4 no
C6 . C5 . H51 . 109.0 no
C17 . C5 . H51 . 107.9 no
C5 . C6 . N7 . 106.40(15) yes
C5 . C6 . C11 . 111.79(15) yes
N7 . C6 . C11 . 115.43(16) yes
C5 . C6 . H61 . 107.5 no
N7 . C6 . H61 . 107.9 no
C11 . C6 . H61 . 107.5 no
C6 . N7 . C8 . 114.69(16) yes
C6 . N7 . H71 . 107.4 no
C8 . N7 . H71 . 110.3 no
N7 . C8 . C9 . 110.0(2) yes
N7 . C8 . C10 . 108.5(2) yes
C9 . C8 . C10 . 111.2(2) yes
N7 . C8 . H81 . 110.2 no
C9 . C8 . H81 . 107.2 no
C10 . C8 . H81 . 109.7 no
C8 . C9 . H92 . 106.5 no
C8 . C9 . H91 . 108.8 no
H92 . C9 . H91 . 111.3 no
C8 . C9 . H93 . 105.7 no
H92 . C9 . H93 . 111.0 no
H91 . C9 . H93 . 113.1 no
C8 . C10 . H101 . 108.8 no
C8 . C10 . H102 . 108.5 no
H101 . C10 . H102 . 112.1 no
C8 . C10 . H103 . 107.8 no
H101 . C10 . H103 . 109.6 no
H102 . C10 . H103 . 109.9 no
C6 . C11 . C12 . 119.65(19) yes
C6 . C11 . C16 . 121.82(19) yes
C12 . C11 . C16 . 118.50(18) yes
C11 . C12 . C13 . 120.9(2) yes
C11 . C12 . H121 . 118.3 no
C13 . C12 . H121 . 120.8 no
C12 . C13 . C14 . 120.0(2) yes
C12 . C13 . H131 . 118.2 no
C14 . C13 . H131 . 121.7 no
C13 . C14 . C15 . 119.25(19) yes
C13 . C14 . H141 . 120.1 no
C15 . C14 . H141 . 120.6 no
C14 . C15 . C16 . 121.0(2) yes
C14 . C15 . H151 . 120.5 no
C16 . C15 . H151 . 118.4 no
C15 . C16 . C11 . 120.2(2) yes
C15 . C16 . H161 . 121.3 no
C11 . C16 . H161 . 118.4 no
C5 . C17 . C18 . 112.57(18) yes
C5 . C17 . H171 . 108.7 no
C18 . C17 . H171 . 108.4 no
C5 . C17 . H172 . 108.0 no
C18 . C17 . H172 . 108.6 no
H171 . C17 . H172 . 110.6 no
C17 . C18 . C19 . 115.1(2) yes
C17 . C18 . H181 . 108.7 no
C19 . C18 . H181 . 108.1 no
C17 . C18 . H182 . 106.7 no
C19 . C18 . H182 . 106.6 no
H181 . C18 . H182 . 111.7 no
C18 . C19 . C20 . 109.7(2) yes
C18 . C19 . C21 . 113.2(3) yes
C20 . C19 . C21 . 112.1(3) yes
C18 . C19 . H191 . 109.1 no
C20 . C19 . H191 . 107.2 no
C21 . C19 . H191 . 105.3 no
C19 . C20 . H202 . 111.2 no
C19 . C20 . H201 . 109.4 no
H202 . C20 . H201 . 109.2 no
C19 . C20 . H203 . 104.3 no
H202 . C20 . H203 . 110.8 no
H201 . C20 . H203 . 111.8 no
C19 . C21 . H212 . 108.9 no
C19 . C21 . H211 . 106.5 no
H212 . C21 . H211 . 113.6 no
C19 . C21 . H213 . 101.5 no
H212 . C21 . H213 . 113.6 no
H211 . C21 . H213 . 111.8 no
O22 . C23 . O24 . 122.59(19) yes
O22 . C23 . C26 . 124.84(19) yes
O24 . C23 . C26 . 112.35(18) yes
C23 . O24 . C25 . 115.65(18) yes
O24 . C25 . H251 . 107.1 no
O24 . C25 . H252 . 108.8 no
H251 . C25 . H252 . 111.0 no
O24 . C25 . H253 . 108.6 no
H251 . C25 . H253 . 110.6 no
H252 . C25 . H253 . 110.6 no
C23 . C26 . C27 . 109.83(16) yes
C23 . C26 . C38 . 107.26(16) yes
C27 . C26 . C38 . 112.18(16) yes
C23 . C26 . H261 . 110.9 no
C27 . C26 . H261 . 107.9 no
C38 . C26 . H261 . 108.8 no
C26 . C27 . N28 . 107.12(16) yes
C26 . C27 . C32 . 110.86(15) yes
N28 . C27 . C32 . 115.22(16) yes
C26 . C27 . H271 . 106.8 no
N28 . C27 . H271 . 108.3 no
C32 . C27 . H271 . 108.2 no
C27 . N28 . C29 . 114.97(17) yes
C27 . N28 . H281 . 105.1 no
C29 . N28 . H281 . 107.9 no
N28 . C29 . C30 . 107.7(2) yes
N28 . C29 . C31 . 110.0(2) yes
C30 . C29 . C31 . 110.7(2) yes
N28 . C29 . H291 . 109.7 no
C30 . C29 . H291 . 110.1 no
C31 . C29 . H291 . 108.7 no
C29 . C30 . H301 . 106.3 no
C29 . C30 . H302 . 107.7 no
H301 . C30 . H302 . 110.3 no
C29 . C30 . H303 . 107.4 no
H301 . C30 . H303 . 111.9 no
H302 . C30 . H303 . 113.0 no
C29 . C31 . H312 . 108.2 no
C29 . C31 . H311 . 105.2 no
H312 . C31 . H311 . 110.4 no
C29 . C31 . H313 . 110.5 no
H312 . C31 . H313 . 110.6 no
H311 . C31 . H313 . 111.8 no
C27 . C32 . C33 . 121.19(18) yes
C27 . C32 . C37 . 120.44(19) yes
C33 . C32 . C37 . 118.34(19) yes
C32 . C33 . C34 . 120.4(2) yes
C32 . C33 . H331 . 118.4 no
C34 . C33 . H331 . 121.2 no
C33 . C34 . C35 . 120.7(2) yes
C33 . C34 . H341 . 120.5 no
C35 . C34 . H341 . 118.8 no
C34 . C35 . C36 . 119.0(2) yes
C34 . C35 . H351 . 121.0 no
C36 . C35 . H351 . 120.0 no
C35 . C36 . C37 . 120.3(2) yes
C35 . C36 . H361 . 119.8 no
C37 . C36 . H361 . 119.9 no
C36 . C37 . C32 . 121.1(2) yes
C36 . C37 . H371 . 120.5 no
C32 . C37 . H371 . 118.4 no
C26 . C38 . C39 . 114.51(17) yes
C26 . C38 . H381 . 108.4 no
C39 . C38 . H381 . 108.3 no
C26 . C38 . H382 . 108.1 no
C39 . C38 . H382 . 108.1 no
H381 . C38 . H382 . 109.3 no
C38 . C39 . C40 . 113.07(18) yes
C38 . C39 . H392 . 109.5 no
C40 . C39 . H392 . 106.3 no
C38 . C39 . H391 . 109.0 no
C40 . C39 . H391 . 108.9 no
H392 . C39 . H391 . 110.1 no
C39 . C40 . C41 . 111.6(2) yes
C39 . C40 . C42 . 112.1(3) yes
C41 . C40 . C42 . 110.2(2) yes
C39 . C40 . H401 . 108.1 no
C41 . C40 . H401 . 107.6 no
C42 . C40 . H401 . 107.0 no
C40 . C41 . H413 . 110.1 no
C40 . C41 . H412 . 104.9 no
H413 . C41 . H412 . 110.3 no
C40 . C41 . H411 . 109.8 no
H413 . C41 . H411 . 110.2 no
H412 . C41 . H411 . 111.3 no
C40 . C42 . H423 . 110.0 no
C40 . C42 . H422 . 104.0 no
H423 . C42 . H422 . 112.2 no
C40 . C42 . H421 . 109.5 no
H423 . C42 . H421 . 110.2 no
H422 . C42 . H421 . 110.7 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
C16 . H161 . O22 . 162.87(6) 0.958 2.540 3.466(4) yes
C33 . H331 . O1 1_545 169.60(6) 0.958 2.454 3.400(4) yes
N7 . H71 . O22 . 166.66(6) 0.893 2.405 3.281(4) yes
N28 . H281 . O1 1_545 178.11(5) 0.895 2.315 3.210(4) yes

_iucr_refine_instruction_details_constraints 
;
#
# Punched on 30/08/12 at 16:32:47
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   4,X'S) H   (  41,X'S) H   (  43,X'S) H   (  42,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE N   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  92,X'S) H   (  91,X'S) H   (  93,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) H   ( 103,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   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 202,X'S) H   ( 201,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   (  25,X'S) H   ( 251,X'S) H   ( 252,X'S) H   ( 253,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE N   (  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) H   ( 302,X'S) H   ( 303,X'S) 
RIDE C   (  31,X'S) H   ( 312,X'S) H   ( 311,X'S) H   ( 313,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) 
RIDE C   (  34,X'S) H   ( 341,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) H   ( 382,X'S) 
RIDE C   (  39,X'S) H   ( 392,X'S) H   ( 391,X'S) 
RIDE C   (  40,X'S) H   ( 401,X'S) 
RIDE C   (  41,X'S) H   ( 413,X'S) H   ( 412,X'S) H   ( 411,X'S) 
RIDE C   (  42,X'S) H   ( 423,X'S) H   ( 422,X'S) H   ( 421,X'S) 
END                                                                             
;

_iucr_refine_instruction_details_restraints 
;
#
# Punched on 30/08/12 at 16:32:47
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 982702'
#######################################################################
#
#                 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_37
_ccdc_journal_depnumber          ?
#==============================================================================

_cell_length_a                   12.31500(10)
_cell_length_b                   15.4817(2)
_cell_length_c                   29.8308(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5687.45(10)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,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'

_cell_formula_units_Z            8

# Given Formula = C33 H37 N1 O2 
# Dc =      1.12 Fooo =   2160.00 Mu =      5.31 M =    959.32
# Found Formula = C34.50 H36 N1 O2.50 
# Dc =      1.18 FOOO =   2160.00 Mu =      5.71 M =   1009.34

_chemical_formula_sum            'C34.50 H36 N1 O2.50'
_chemical_formula_moiety         'C34.50 H36 N1 O2.50'
_chemical_compound_source        .
_chemical_formula_weight         504.67

_cell_measurement_reflns_used    49571
_cell_measurement_theta_min      3
_cell_measurement_theta_max      77
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.150
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_max          0.260

_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             2160
_exptl_absorpt_coefficient_mu    0.571

# Sheldrick geometric approximatio 0.89 0.92 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.62
_exptl_absorpt_correction_T_max  0.92
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_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      150
_diffrn_reflns_number            93762
_reflns_number_total             11951
_diffrn_reflns_av_R_equivalents  0.044
# Number of reflections without Friedels Law is 11951 
# Number of reflections with Friedels Law is 6612 
# Theoretical number of reflections is about 6006 

_diffrn_reflns_theta_min         3.216
_diffrn_reflns_theta_max         76.899
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        76.899
_diffrn_measured_fraction_theta_full 0.997

_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       37
_reflns_limit_h_min              -15
_reflns_limit_h_max              15
_reflns_limit_k_min              0
_reflns_limit_k_max              19
_reflns_limit_l_min              0
_reflns_limit_l_max              37

_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         -0.35
_refine_diff_density_max         0.62

# 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>-3.0\s(I)
_refine_ls_number_reflns         11907
_refine_ls_number_restraints     0
_refine_ls_number_parameters     686
_oxford_refine_ls_R_factor_ref   0.0454
_refine_ls_wR_factor_ref         0.1179
_refine_ls_goodness_of_fit_ref   0.9978
_refine_ls_shift/su_max          0.0003193
_refine_ls_shift/su_mean         0.0000453

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        11907
_refine_ls_R_factor_all          0.0454
_refine_ls_wR_factor_all         0.1179

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                11422
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_gt          0.1164

_refine_ls_abs_structure_Flack   0.02(16)
_refine_ls_abs_structure_details 'Flack (1983), 5339 Friedel-pairs'
# 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 ad

_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/[σ²(F²) + ( 0.07P)² + 1.53P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint

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 0.65945(11) 0.58919(8) 0.11239(4) 0.0404 1.0000 Uani . . . . . .
C2 C 0.67556(12) 0.51792(11) 0.09217(5) 0.0311 1.0000 Uani . . . . . .
O3 O 0.64895(11) 0.44583(9) 0.10814(4) 0.0426 1.0000 Uani . . . . . .
C4 C 0.72934(12) 0.51974(11) 0.04645(5) 0.0303 1.0000 Uani . . . . . .
C5 C 0.85133(12) 0.54354(10) 0.05166(5) 0.0287 1.0000 Uani . . . . . .
N6 N 0.89932(11) 0.49483(9) 0.08938(4) 0.0311 1.0000 Uani . . . . . .
C7 C 1.00438(14) 0.52657(14) 0.10610(6) 0.0402 1.0000 Uani . . . . . .
C8 C 0.99460(15) 0.61840(13) 0.12257(7) 0.0446 1.0000 Uani . . . . . .
C9 C 0.9146(2) 0.63927(14) 0.15368(7) 0.0512 1.0000 Uani . . . . . .
C10 C 0.9091(3) 0.71997(16) 0.17266(10) 0.0729 1.0000 Uani . . . . . .
C11 C 0.9863(3) 0.78256(17) 0.15998(15) 0.0971 1.0000 Uani . . . . . .
C12 C 1.0643(3) 0.7620(2) 0.12866(18) 0.1061 1.0000 Uani . . . . . .
C13 C 1.0685(2) 0.68207(18) 0.11027(12) 0.0760 1.0000 Uani . . . . . .
C14 C 1.10267(17) 0.5046(2) 0.07641(8) 0.0612 1.0000 Uani . . . . . .
C15 C 0.89757(17) 0.40018(12) 0.08440(6) 0.0417 1.0000 Uani . . . . . .
C16 C 0.91290(15) 0.35315(12) 0.12847(6) 0.0379 1.0000 Uani . . . . . .
C17 C 0.87059(19) 0.38389(15) 0.16860(7) 0.0505 1.0000 Uani . . . . . .
C18 C 0.8842(2) 0.33722(18) 0.20808(8) 0.0601 1.0000 Uani . . . . . .
C19 C 0.93601(19) 0.25810(17) 0.20721(8) 0.0607 1.0000 Uani . . . . . .
C20 C 0.9744(2) 0.22554(16) 0.16738(9) 0.0629 1.0000 Uani . . . . . .
C21 C 0.96319(17) 0.27336(13) 0.12817(8) 0.0490 1.0000 Uani . . . . . .
C22 C 0.90750(12) 0.53489(11) 0.00604(5) 0.0310 1.0000 Uani . . . . . .
C23 C 0.89873(13) 0.46047(11) -0.01983(5) 0.0329 1.0000 Uani . . . . . .
C24 C 0.95196(14) 0.45409(13) -0.06104(6) 0.0381 1.0000 Uani . . . . . .
C25 C 1.01439(15) 0.52186(14) -0.07647(6) 0.0438 1.0000 Uani . . . . . .
C26 C 1.02206(16) 0.59656(14) -0.05141(6) 0.0449 1.0000 Uani . . . . . .
C27 C 0.96844(14) 0.60342(12) -0.01046(6) 0.0385 1.0000 Uani . . . . . .
C28 C 0.67056(14) 0.57897(13) 0.01167(6) 0.0398 1.0000 Uani . . . . . .
C29 C 0.55660(15) 0.54471(14) 0.00344(6) 0.0412 1.0000 Uani . . . . . .
C30 C 0.46504(16) 0.58060(16) 0.02273(7) 0.0500 1.0000 Uani . . . . . .
C31 C 0.36251(17) 0.54592(17) 0.01451(8) 0.0574 1.0000 Uani . . . . . .
C32 C 0.34967(18) 0.47604(18) -0.01277(8) 0.0615 1.0000 Uani . . . . . .
C33 C 0.4387(2) 0.4384(2) -0.03193(9) 0.0666 1.0000 Uani . . . . . .
C34 C 0.54206(18) 0.47307(17) -0.02412(7) 0.0563 1.0000 Uani . . . . . .
C35 C 0.67615(17) 0.67392(14) 0.02278(7) 0.0485 1.0000 Uani . . . . . .
C36 C 0.7188(2) 0.73165(18) -0.00383(11) 0.0748 1.0000 Uani . . . . . .
O37 O 0.56991(10) 0.57699(8) 0.19276(4) 0.0356 1.0000 Uani . . . . . .
C38 C 0.56319(11) 0.50468(10) 0.21182(5) 0.0274 1.0000 Uani . . . . . .
O39 O 0.59482(10) 0.43422(8) 0.19429(4) 0.0360 1.0000 Uani . . . . . .
C40 C 0.51645(11) 0.49849(10) 0.25857(5) 0.0277 1.0000 Uani . . . . . .
C41 C 0.39175(12) 0.51464(11) 0.25627(5) 0.0289 1.0000 Uani . . . . . .
N42 N 0.34673(10) 0.48225(9) 0.21353(4) 0.0285 1.0000 Uani . . . . . .
C43 C 0.32678(16) 0.38900(12) 0.21191(6) 0.0379 1.0000 Uani . . . . . .
C44 C 0.32015(14) 0.35403(11) 0.16437(6) 0.0351 1.0000 Uani . . . . . .
C45 C 0.25690(17) 0.28209(13) 0.15556(7) 0.0474 1.0000 Uani . . . . . .
C46 C 0.2591(2) 0.24387(16) 0.11338(9) 0.0642 1.0000 Uani . . . . . .
C47 C 0.3241(2) 0.27749(18) 0.07992(8) 0.0644 1.0000 Uani . . . . . .
C48 C 0.38601(19) 0.34955(16) 0.08817(7) 0.0540 1.0000 Uani . . . . . .
C49 C 0.38426(16) 0.38749(14) 0.13042(6) 0.0421 1.0000 Uani . . . . . .
C50 C 0.25751(13) 0.53480(12) 0.19440(5) 0.0346 1.0000 Uani . . . . . .
C51 C 0.29823(13) 0.62469(12) 0.18194(6) 0.0353 1.0000 Uani . . . . . .
C52 C 0.35501(16) 0.63560(13) 0.14206(6) 0.0418 1.0000 Uani . . . . . .
C53 C 0.39460(19) 0.71589(14) 0.12973(8) 0.0509 1.0000 Uani . . . . . .
C54 C 0.37737(19) 0.78754(14) 0.15702(8) 0.0557 1.0000 Uani . . . . . .
C55 C 0.3216(2) 0.77757(14) 0.19649(8) 0.0568 1.0000 Uani . . . . . .
C56 C 0.28174(17) 0.69682(13) 0.20870(7) 0.0471 1.0000 Uani . . . . . .
C57 C 0.15198(16) 0.53318(17) 0.22034(7) 0.0522 1.0000 Uani . . . . . .
C58 C 0.33604(12) 0.48373(13) 0.29920(5) 0.0352 1.0000 Uani . . . . . .
C59 C 0.26919(14) 0.54056(16) 0.32286(6) 0.0463 1.0000 Uani . . . . . .
C60 C 0.21312(17) 0.5140(2) 0.36101(7) 0.0601 1.0000 Uani . . . . . .
C61 C 0.22347(18) 0.4299(2) 0.37599(7) 0.0647 1.0000 Uani . . . . . .
C62 C 0.29156(18) 0.37305(18) 0.35404(6) 0.0559 1.0000 Uani . . . . . .
C63 C 0.34833(15) 0.40038(13) 0.31599(5) 0.0403 1.0000 Uani . . . . . .
C64 C 0.57004(12) 0.56151(11) 0.29306(5) 0.0324 1.0000 Uani . . . . . .
C65 C 0.69128(13) 0.54454(11) 0.29857(6) 0.0344 1.0000 Uani . . . . . .
C66 C 0.76625(14) 0.56700(15) 0.26560(7) 0.0471 1.0000 Uani . . . . . .
C67 C 0.87632(15) 0.54985(17) 0.27170(8) 0.0546 1.0000 Uani . . . . . .
C68 C 0.91304(15) 0.51182(13) 0.31036(8) 0.0514 1.0000 Uani . . . . . .
C69 C 0.84044(17) 0.49167(13) 0.34373(8) 0.0512 1.0000 Uani . . . . . .
C70 C 0.72968(15) 0.50765(12) 0.33790(7) 0.0407 1.0000 Uani . . . . . .
C71 C 0.54544(14) 0.65537(12) 0.28406(6) 0.0396 1.0000 Uani . . . . . .
C72 C 0.48510(18) 0.70298(15) 0.31050(9) 0.0554 1.0000 Uani . . . . . .
O73 O 0.7619(3) 0.2794(3) 0.02228(8) 0.1792 1.0000 Uani . . . . . .
C74 C 0.6805(3) 0.24735(17) 0.03508(9) 0.0727 1.0000 Uani . . . . . .
C75 C 0.6649(2) 0.22399(19) 0.08330(9) 0.0671 1.0000 Uani . . . . . .
C76 C 0.5911(3) 0.2251(3) 0.00285(10) 0.0881 1.0000 Uani . . . . . .
H41 H 0.7245 0.4579 0.0352 0.0364 1.0000 Uiso R . . . . .
H51 H 0.8558 0.6063 0.0612 0.0346 1.0000 Uiso R . . . . .
H71 H 1.0178 0.4899 0.1336 0.0519 1.0000 Uiso R . . . . .
H91 H 0.8611 0.5955 0.1614 0.0637 1.0000 Uiso R . . . . .
H101 H 0.8520 0.7313 0.1933 0.0932 1.0000 Uiso R . . . . .
H111 H 0.9802 0.8381 0.1733 0.1142 1.0000 Uiso R . . . . .
H121 H 1.1167 0.8062 0.1187 0.1339 1.0000 Uiso R . . . . .
H131 H 1.1266 0.6697 0.0898 0.0978 1.0000 Uiso R . . . . .
H142 H 1.1743 0.5171 0.0934 0.1092 1.0000 Uiso R . . . . .
H141 H 1.0952 0.5395 0.0476 0.1090 1.0000 Uiso R . . . . .
H143 H 1.0911 0.4338 0.0679 0.1090 1.0000 Uiso R . . . . .
H151 H 0.9620 0.3805 0.0650 0.0527 1.0000 Uiso R . . . . .
H152 H 0.8234 0.3845 0.0699 0.0531 1.0000 Uiso R . . . . .
H171 H 0.8333 0.4417 0.1685 0.0656 1.0000 Uiso R . . . . .
H181 H 0.8545 0.3597 0.2363 0.0753 1.0000 Uiso R . . . . .
H191 H 0.9430 0.2264 0.2344 0.0773 1.0000 Uiso R . . . . .
H201 H 1.0075 0.1683 0.1654 0.0772 1.0000 Uiso R . . . . .
H211 H 0.9906 0.2508 0.1005 0.0631 1.0000 Uiso R . . . . .
H231 H 0.8525 0.4126 -0.0092 0.0403 1.0000 Uiso R . . . . .
H241 H 0.9454 0.3997 -0.0792 0.0475 1.0000 Uiso R . . . . .
H251 H 1.0521 0.5184 -0.1049 0.0563 1.0000 Uiso R . . . . .
H261 H 1.0663 0.6457 -0.0630 0.0562 1.0000 Uiso R . . . . .
H271 H 0.9735 0.6542 0.0066 0.0489 1.0000 Uiso R . . . . .
H281 H 0.7106 0.5702 -0.0179 0.0483 1.0000 Uiso R . . . . .
H301 H 0.4768 0.6317 0.0410 0.0643 1.0000 Uiso R . . . . .
H311 H 0.2994 0.5737 0.0267 0.0708 1.0000 Uiso R . . . . .
H321 H 0.2775 0.4530 -0.0189 0.0786 1.0000 Uiso R . . . . .
H331 H 0.4328 0.3859 -0.0512 0.0807 1.0000 Uiso R . . . . .
H341 H 0.6041 0.4478 -0.0391 0.0699 1.0000 Uiso R . . . . .
H351 H 0.6473 0.6925 0.0505 0.0614 1.0000 Uiso R . . . . .
H362 H 0.7506 0.7125 -0.0317 0.0963 1.0000 Uiso R . . . . .
H361 H 0.7219 0.7924 0.0041 0.0974 1.0000 Uiso R . . . . .
H401 H 0.5273 0.4367 0.2690 0.0351 1.0000 Uiso R . . . . .
H411 H 0.3829 0.5814 0.2561 0.0367 1.0000 Uiso R . . . . .
H432 H 0.2474 0.3747 0.2264 0.0474 1.0000 Uiso R . . . . .
H431 H 0.3899 0.3598 0.2280 0.0468 1.0000 Uiso R . . . . .
H451 H 0.2134 0.2594 0.1792 0.0593 1.0000 Uiso R . . . . .
H461 H 0.2158 0.1909 0.1081 0.0787 1.0000 Uiso R . . . . .
H471 H 0.3243 0.2508 0.0513 0.0809 1.0000 Uiso R . . . . .
H481 H 0.4330 0.3731 0.0633 0.0688 1.0000 Uiso R . . . . .
H491 H 0.4286 0.4400 0.1367 0.0530 1.0000 Uiso R . . . . .
H501 H 0.2388 0.5045 0.1647 0.0440 1.0000 Uiso R . . . . .
H521 H 0.3661 0.5853 0.1222 0.0539 1.0000 Uiso R . . . . .
H531 H 0.4347 0.7218 0.1016 0.0631 1.0000 Uiso R . . . . .
H541 H 0.4064 0.8451 0.1490 0.0687 1.0000 Uiso R . . . . .
H551 H 0.3091 0.8285 0.2154 0.0705 1.0000 Uiso R . . . . .
H561 H 0.2361 0.6901 0.2362 0.0581 1.0000 Uiso R . . . . .
H571 H 0.0922 0.5661 0.2008 0.0847 1.0000 Uiso R . . . . .
H572 H 0.1627 0.5629 0.2522 0.0853 1.0000 Uiso R . . . . .
H573 H 0.1289 0.4677 0.2258 0.0849 1.0000 Uiso R . . . . .
H591 H 0.2603 0.6004 0.3121 0.0621 1.0000 Uiso R . . . . .
H601 H 0.1651 0.5526 0.3770 0.0753 1.0000 Uiso R . . . . .
H611 H 0.1855 0.4103 0.4012 0.0799 1.0000 Uiso R . . . . .
H621 H 0.2990 0.3145 0.3652 0.0706 1.0000 Uiso R . . . . .
H631 H 0.3979 0.3618 0.3016 0.0521 1.0000 Uiso R . . . . .
H641 H 0.5330 0.5463 0.3230 0.0404 1.0000 Uiso R . . . . .
H661 H 0.7390 0.5955 0.2380 0.0591 1.0000 Uiso R . . . . .
H671 H 0.9285 0.5650 0.2492 0.0688 1.0000 Uiso R . . . . .
H681 H 0.9903 0.4997 0.3149 0.0611 1.0000 Uiso R . . . . .
H691 H 0.8674 0.4655 0.3709 0.0636 1.0000 Uiso R . . . . .
H701 H 0.6804 0.4908 0.3611 0.0515 1.0000 Uiso R . . . . .
H711 H 0.5751 0.6803 0.2562 0.0504 1.0000 Uiso R . . . . .
H721 H 0.4718 0.7641 0.3037 0.0702 1.0000 Uiso R . . . . .
H722 H 0.4524 0.6746 0.3365 0.0701 1.0000 Uiso R . . . . .
H751 H 0.6449 0.1605 0.0838 0.1073 1.0000 Uiso R . . . . .
H752 H 0.6065 0.2617 0.0950 0.1089 1.0000 Uiso R . . . . .
H753 H 0.7362 0.2328 0.0990 0.1075 1.0000 Uiso R . . . . .
H763 H 0.5211 0.2540 0.0149 0.1331 1.0000 Uiso R . . . . .
H762 H 0.6110 0.2456 -0.0295 0.1331 1.0000 Uiso R . . . . .
H761 H 0.5820 0.1586 0.0035 0.1338 1.0000 Uiso R . . . . .
H11 H 0.6248 0.5910 0.1376 0.0649 1.0000 Uiso R . . . . .
H391 H 0.6122 0.4357 0.1667 0.0603 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.33(3)
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 . 1.273(2) yes
O1 . H11 . 0.864 no
C2 . O3 . 1.257(2) yes
C2 . C4 . 1.516(2) yes
C4 . C5 . 1.555(2) yes
C4 . C28 . 1.562(2) yes
C4 . H41 . 1.016 no
C5 . N6 . 1.4777(19) yes
C5 . C22 . 1.533(2) yes
C5 . H51 . 1.014 no
N6 . C7 . 1.471(2) yes
N6 . C15 . 1.473(2) yes
C7 . C8 . 1.509(3) yes
C7 . C14 . 1.538(3) yes
C7 . H71 . 1.011 no
C8 . C9 . 1.391(3) yes
C8 . C13 . 1.391(3) yes
C9 . C10 . 1.373(3) yes
C9 . H91 . 0.973 no
C10 . C11 . 1.409(5) yes
C10 . H101 . 0.951 no
C11 . C12 . 1.377(6) yes
C11 . H111 . 0.950 no
C12 . C13 . 1.355(5) yes
C12 . H121 . 0.987 no
C13 . H131 . 0.961 no
C14 . H142 . 1.035 no
C14 . H141 . 1.018 no
C14 . H143 . 1.135 no
C15 . C16 . 1.515(2) yes
C15 . H151 . 1.030 no
C15 . H152 . 1.039 no
C16 . C17 . 1.390(3) yes
C16 . C21 . 1.382(3) yes
C17 . C18 . 1.392(3) yes
C17 . H171 . 1.006 no
C18 . C19 . 1.382(4) yes
C18 . H181 . 0.980 no
C19 . C20 . 1.375(4) yes
C19 . H191 . 0.952 no
C20 . C21 . 1.391(3) yes
C20 . H201 . 0.978 no
C21 . H211 . 0.959 no
C22 . C23 . 1.391(2) yes
C22 . C27 . 1.390(2) yes
C23 . C24 . 1.397(2) yes
C23 . H231 . 0.987 no
C24 . C25 . 1.380(3) yes
C24 . H241 . 1.004 no
C25 . C26 . 1.380(3) yes
C25 . H251 . 0.970 no
C26 . C27 . 1.393(3) yes
C26 . H261 . 0.998 no
C27 . H271 . 0.939 no
C28 . C29 . 1.520(3) yes
C28 . C35 . 1.508(3) yes
C28 . H281 . 1.020 no
C29 . C30 . 1.382(3) yes
C29 . C34 . 1.392(3) yes
C30 . C31 . 1.394(3) yes
C30 . H301 . 0.972 no
C31 . C32 . 1.363(4) yes
C31 . H311 . 0.959 no
C32 . C33 . 1.367(4) yes
C32 . H321 . 0.975 no
C33 . C34 . 1.401(3) yes
C33 . H331 . 0.999 no
C34 . H341 . 0.968 no
C35 . C36 . 1.306(3) yes
C35 . H351 . 0.946 no
C36 . H362 . 0.966 no
C36 . H361 . 0.970 no
O37 . C38 . 1.258(2) yes
C38 . O39 . 1.2709(19) yes
C38 . C40 . 1.512(2) yes
O39 . H391 . 0.851 no
C40 . C41 . 1.557(2) yes
C40 . C64 . 1.564(2) yes
C40 . H401 . 1.015 no
C41 . N42 . 1.4781(18) yes
C41 . C58 . 1.529(2) yes
C41 . H411 . 1.040 no
N42 . C43 . 1.465(2) yes
N42 . C50 . 1.481(2) yes
C43 . C44 . 1.520(2) yes
C43 . H432 . 1.091 no
C43 . H431 . 1.019 no
C44 . C45 . 1.384(3) yes
C44 . C49 . 1.385(3) yes
C45 . C46 . 1.391(3) yes
C45 . H451 . 0.953 no
C46 . C47 . 1.381(4) yes
C46 . H461 . 0.991 no
C47 . C48 . 1.374(4) yes
C47 . H471 . 0.948 no
C48 . C49 . 1.391(3) yes
C48 . H481 . 1.009 no
C49 . H491 . 0.997 no
C50 . C51 . 1.525(3) yes
C50 . C57 . 1.513(2) yes
C50 . H501 . 1.030 no
C51 . C52 . 1.390(2) yes
C51 . C56 . 1.388(3) yes
C52 . C53 . 1.385(3) yes
C52 . H521 . 0.987 no
C53 . C54 . 1.392(3) yes
C53 . H531 . 0.978 no
C54 . C55 . 1.372(3) yes
C54 . H541 . 0.989 no
C55 . C56 . 1.392(3) yes
C55 . H551 . 0.981 no
C56 . H561 . 1.000 no
C57 . H571 . 1.069 no
C57 . H572 . 1.063 no
C57 . H573 . 1.065 no
C58 . C59 . 1.396(3) yes
C58 . C63 . 1.393(3) yes
C59 . C60 . 1.393(3) yes
C59 . H591 . 0.987 no
C60 . C61 . 1.382(4) yes
C60 . H601 . 0.966 no
C61 . C62 . 1.380(4) yes
C61 . H611 . 0.936 no
C62 . C63 . 1.399(2) yes
C62 . H621 . 0.970 no
C63 . H631 . 0.956 no
C64 . C65 . 1.525(2) yes
C64 . C71 . 1.508(3) yes
C64 . H641 . 1.029 no
C65 . C66 . 1.393(3) yes
C65 . C70 . 1.388(3) yes
C66 . C67 . 1.393(3) yes
C66 . H661 . 0.992 no
C67 . C68 . 1.372(3) yes
C67 . H671 . 0.959 no
C68 . C69 . 1.374(3) yes
C68 . H681 . 0.979 no
C69 . C70 . 1.397(3) yes
C69 . H691 . 0.965 no
C70 . H701 . 0.955 no
C71 . C72 . 1.310(3) yes
C71 . H711 . 0.987 no
C72 . H721 . 0.981 no
C72 . H722 . 0.978 no
O73 . C74 . 1.182(3) yes
C74 . C75 . 1.495(4) yes
C74 . C76 . 1.502(5) yes
C75 . H751 . 1.014 no
C75 . H752 . 0.990 no
C75 . H753 . 1.006 no
C76 . H763 . 1.036 no
C76 . H762 . 1.046 no
C76 . H761 . 1.035 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 . H11 . 121.1 no
O1 . C2 . O3 . 123.33(14) yes
O1 . C2 . C4 . 118.56(14) yes
O3 . C2 . C4 . 118.11(15) yes
C2 . C4 . C5 . 109.66(12) yes
C2 . C4 . C28 . 113.94(13) yes
C5 . C4 . C28 . 112.03(13) yes
C2 . C4 . H41 . 104.7 no
C5 . C4 . H41 . 108.3 no
C28 . C4 . H41 . 107.8 no
C4 . C5 . N6 . 109.98(12) yes
C4 . C5 . C22 . 109.07(12) yes
N6 . C5 . C22 . 116.80(13) yes
C4 . C5 . H51 . 108.0 no
N6 . C5 . H51 . 104.7 no
C22 . C5 . H51 . 108.0 no
C5 . N6 . C7 . 116.07(13) yes
C5 . N6 . C15 . 115.16(13) yes
C7 . N6 . C15 . 112.30(14) yes
N6 . C7 . C8 . 110.79(15) yes
N6 . C7 . C14 . 115.03(16) yes
C8 . C7 . C14 . 117.29(18) yes
N6 . C7 . H71 . 103.4 no
C8 . C7 . H71 . 106.1 no
C14 . C7 . H71 . 102.4 no
C7 . C8 . C9 . 119.50(17) yes
C7 . C8 . C13 . 122.0(2) yes
C9 . C8 . C13 . 118.3(2) yes
C8 . C9 . C10 . 121.4(2) yes
C8 . C9 . H91 . 118.4 no
C10 . C9 . H91 . 120.1 no
C9 . C10 . C11 . 118.8(3) yes
C9 . C10 . H101 . 118.1 no
C11 . C10 . H101 . 123.1 no
C10 . C11 . C12 . 119.6(3) yes
C10 . C11 . H111 . 117.2 no
C12 . C11 . H111 . 123.2 no
C11 . C12 . C13 . 120.8(3) yes
C11 . C12 . H121 . 120.0 no
C13 . C12 . H121 . 119.2 no
C8 . C13 . C12 . 121.0(3) yes
C8 . C13 . H131 . 121.0 no
C12 . C13 . H131 . 117.9 no
C7 . C14 . H142 . 110.3 no
C7 . C14 . H141 . 107.3 no
H142 . C14 . H141 . 113.0 no
C7 . C14 . H143 . 104.1 no
H142 . C14 . H143 . 113.4 no
H141 . C14 . H143 . 108.2 no
N6 . C15 . C16 . 112.89(15) yes
N6 . C15 . H151 . 109.9 no
C16 . C15 . H151 . 104.5 no
N6 . C15 . H152 . 106.7 no
C16 . C15 . H152 . 111.0 no
H151 . C15 . H152 . 112.0 no
C15 . C16 . C17 . 122.44(17) yes
C15 . C16 . C21 . 118.69(18) yes
C17 . C16 . C21 . 118.66(18) yes
C16 . C17 . C18 . 120.4(2) yes
C16 . C17 . H171 . 118.2 no
C18 . C17 . H171 . 121.3 no
C17 . C18 . C19 . 120.0(2) yes
C17 . C18 . H181 . 119.8 no
C19 . C18 . H181 . 120.2 no
C18 . C19 . C20 . 120.0(2) yes
C18 . C19 . H191 . 118.8 no
C20 . C19 . H191 . 121.1 no
C19 . C20 . C21 . 119.8(2) yes
C19 . C20 . H201 . 122.0 no
C21 . C20 . H201 . 118.2 no
C20 . C21 . C16 . 121.0(2) yes
C20 . C21 . H211 . 119.7 no
C16 . C21 . H211 . 119.3 no
C5 . C22 . C23 . 122.00(14) yes
C5 . C22 . C27 . 119.44(15) yes
C23 . C22 . C27 . 118.55(15) yes
C22 . C23 . C24 . 120.69(16) yes
C22 . C23 . H231 . 119.3 no
C24 . C23 . H231 . 120.0 no
C23 . C24 . C25 . 120.09(17) yes
C23 . C24 . H241 . 119.7 no
C25 . C24 . H241 . 120.2 no
C24 . C25 . C26 . 119.64(16) yes
C24 . C25 . H251 . 121.1 no
C26 . C25 . H251 . 119.2 no
C25 . C26 . C27 . 120.43(17) yes
C25 . C26 . H261 . 119.3 no
C27 . C26 . H261 . 120.3 no
C26 . C27 . C22 . 120.56(17) yes
C26 . C27 . H271 . 120.5 no
C22 . C27 . H271 . 118.9 no
C4 . C28 . C29 . 109.28(14) yes
C4 . C28 . C35 . 113.89(15) yes
C29 . C28 . C35 . 114.68(16) yes
C4 . C28 . H281 . 105.8 no
C29 . C28 . H281 . 105.1 no
C35 . C28 . H281 . 107.3 no
C28 . C29 . C30 . 123.06(18) yes
C28 . C29 . C34 . 119.48(17) yes
C30 . C29 . C34 . 117.46(19) yes
C29 . C30 . C31 . 120.7(2) yes
C29 . C30 . H301 . 116.1 no
C31 . C30 . H301 . 123.1 no
C30 . C31 . C32 . 121.1(2) yes
C30 . C31 . H311 . 119.7 no
C32 . C31 . H311 . 119.2 no
C31 . C32 . C33 . 119.7(2) yes
C31 . C32 . H321 . 120.5 no
C33 . C32 . H321 . 119.8 no
C32 . C33 . C34 . 119.8(2) yes
C32 . C33 . H331 . 121.9 no
C34 . C33 . H331 . 118.3 no
C33 . C34 . C29 . 121.3(2) yes
C33 . C34 . H341 . 119.1 no
C29 . C34 . H341 . 119.5 no
C28 . C35 . C36 . 123.5(2) yes
C28 . C35 . H351 . 118.1 no
C36 . C35 . H351 . 118.4 no
C35 . C36 . H362 . 118.5 no
C35 . C36 . H361 . 122.2 no
H362 . C36 . H361 . 119.3 no
O37 . C38 . O39 . 123.89(13) yes
O37 . C38 . C40 . 119.89(14) yes
O39 . C38 . C40 . 116.22(14) yes
C38 . O39 . H391 . 116.8 no
C38 . C40 . C41 . 108.94(12) yes
C38 . C40 . C64 . 113.99(12) yes
C41 . C40 . C64 . 110.18(12) yes
C38 . C40 . H401 . 107.0 no
C41 . C40 . H401 . 107.2 no
C64 . C40 . H401 . 109.3 no
C40 . C41 . N42 . 110.70(12) yes
C40 . C41 . C58 . 110.80(13) yes
N42 . C41 . C58 . 116.60(12) yes
C40 . C41 . H411 . 105.3 no
N42 . C41 . H411 . 107.1 no
C58 . C41 . H411 . 105.5 no
C41 . N42 . C43 . 115.18(13) yes
C41 . N42 . C50 . 115.10(12) yes
C43 . N42 . C50 . 113.84(13) yes
N42 . C43 . C44 . 112.99(14) yes
N42 . C43 . H432 . 109.7 no
C44 . C43 . H432 . 104.4 no
N42 . C43 . H431 . 107.1 no
C44 . C43 . H431 . 108.7 no
H432 . C43 . H431 . 114.1 no
C43 . C44 . C45 . 119.60(17) yes
C43 . C44 . C49 . 121.23(16) yes
C45 . C44 . C49 . 118.87(17) yes
C44 . C45 . C46 . 120.2(2) yes
C44 . C45 . H451 . 118.2 no
C46 . C45 . H451 . 121.6 no
C45 . C46 . C47 . 120.3(2) yes
C45 . C46 . H461 . 119.0 no
C47 . C46 . H461 . 120.6 no
C46 . C47 . C48 . 119.9(2) yes
C46 . C47 . H471 . 119.2 no
C48 . C47 . H471 . 120.9 no
C47 . C48 . C49 . 119.8(2) yes
C47 . C48 . H481 . 118.7 no
C49 . C48 . H481 . 121.5 no
C48 . C49 . C44 . 120.9(2) yes
C48 . C49 . H491 . 120.5 no
C44 . C49 . H491 . 118.6 no
N42 . C50 . C51 . 110.56(13) yes
N42 . C50 . C57 . 115.53(14) yes
C51 . C50 . C57 . 114.97(16) yes
N42 . C50 . H501 . 104.4 no
C51 . C50 . H501 . 106.2 no
C57 . C50 . H501 . 103.9 no
C50 . C51 . C52 . 119.00(16) yes
C50 . C51 . C56 . 123.11(16) yes
C52 . C51 . C56 . 117.90(18) yes
C51 . C52 . C53 . 120.89(18) yes
C51 . C52 . H521 . 119.1 no
C53 . C52 . H521 . 120.0 no
C52 . C53 . C54 . 120.41(19) yes
C52 . C53 . H531 . 119.4 no
C54 . C53 . H531 . 120.2 no
C53 . C54 . C55 . 119.2(2) yes
C53 . C54 . H541 . 121.4 no
C55 . C54 . H541 . 119.3 no
C54 . C55 . C56 . 120.1(2) yes
C54 . C55 . H551 . 118.8 no
C56 . C55 . H551 . 121.1 no
C55 . C56 . C51 . 121.40(19) yes
C55 . C56 . H561 . 120.4 no
C51 . C56 . H561 . 118.1 no
C50 . C57 . H571 . 107.7 no
C50 . C57 . H572 . 110.0 no
H571 . C57 . H572 . 111.5 no
C50 . C57 . H573 . 108.8 no
H571 . C57 . H573 . 110.7 no
H572 . C57 . H573 . 108.1 no
C41 . C58 . C59 . 119.38(17) yes
C41 . C58 . C63 . 122.85(15) yes
C59 . C58 . C63 . 117.78(16) yes
C58 . C59 . C60 . 121.3(2) yes
C58 . C59 . H591 . 119.5 no
C60 . C59 . H591 . 119.2 no
C59 . C60 . C61 . 119.8(2) yes
C59 . C60 . H601 . 121.5 no
C61 . C60 . H601 . 118.7 no
C60 . C61 . C62 . 120.19(19) yes
C60 . C61 . H611 . 121.3 no
C62 . C61 . H611 . 118.5 no
C61 . C62 . C63 . 119.7(2) yes
C61 . C62 . H621 . 119.3 no
C63 . C62 . H621 . 120.9 no
C62 . C63 . C58 . 121.2(2) yes
C62 . C63 . H631 . 119.6 no
C58 . C63 . H631 . 119.2 no
C40 . C64 . C65 . 112.12(13) yes
C40 . C64 . C71 . 113.52(14) yes
C65 . C64 . C71 . 112.45(14) yes
C40 . C64 . H641 . 103.9 no
C65 . C64 . H641 . 107.5 no
C71 . C64 . H641 . 106.6 no
C64 . C65 . C66 . 122.00(16) yes
C64 . C65 . C70 . 119.70(15) yes
C66 . C65 . C70 . 118.28(16) yes
C65 . C66 . C67 . 120.3(2) yes
C65 . C66 . H661 . 118.2 no
C67 . C66 . H661 . 121.5 no
C66 . C67 . C68 . 120.8(2) yes
C66 . C67 . H671 . 120.9 no
C68 . C67 . H671 . 118.3 no
C67 . C68 . C69 . 119.48(17) yes
C67 . C68 . H681 . 121.3 no
C69 . C68 . H681 . 119.2 no
C68 . C69 . C70 . 120.3(2) yes
C68 . C69 . H691 . 118.7 no
C70 . C69 . H691 . 121.0 no
C69 . C70 . C65 . 120.71(19) yes
C69 . C70 . H701 . 118.8 no
C65 . C70 . H701 . 120.5 no
C64 . C71 . C72 . 123.26(19) yes
C64 . C71 . H711 . 116.9 no
C72 . C71 . H711 . 119.8 no
C71 . C72 . H721 . 120.8 no
C71 . C72 . H722 . 117.3 no
H721 . C72 . H722 . 121.9 no
O73 . C74 . C75 . 121.5(3) yes
O73 . C74 . C76 . 120.7(3) yes
C75 . C74 . C76 . 117.8(2) yes
C74 . C75 . H751 . 106.3 no
C74 . C75 . H752 . 106.9 no
H751 . C75 . H752 . 113.0 no
C74 . C75 . H753 . 107.6 no
H751 . C75 . H753 . 109.7 no
H752 . C75 . H753 . 113.0 no
C74 . C76 . H763 . 106.8 no
C74 . C76 . H762 . 110.5 no
H763 . C76 . H762 . 112.6 no
C74 . C76 . H761 . 107.2 no
H763 . C76 . H761 . 109.4 no
H762 . C76 . H761 . 110.2 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 . C27 . 147.12(6) 1.018 2.533 3.433(3) yes
C15 . H152 . O73 . 135.65(13) 1.039 2.289 3.118(3) yes
C23 . H231 . O73 . 170.88(12) 0.987 2.526 3.504(3) yes
C41 . H411 . C56 . 137.44(6) 1.040 2.597 3.436(3) yes
C47 . H471 . O73 2_455 156.58(8) 0.948 2.373 3.264(3) yes
C57 . H572 . C59 . 139.11(7) 1.063 2.508 3.384(3) yes
C66 . H661 . O37 . 132.72(6) 0.992 2.499 3.254(3) yes
O1 . H11 . O37 . 168.62(6) 0.864 1.793 2.646(3) yes
O39 . H391 . O3 . 176.64(6) 0.851 1.811 2.661(3) yes

_iucr_refine_instruction_details_constraints 
;
#
# Punched on 28/03/13 at 15:06:10
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE O   (   1,X'S) H   (  11,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,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   ( 111,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   ( 142,X'S) H   ( 141,X'S) H   ( 143,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 152,X'S) 
RIDE C   (  17,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   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  23,X'S) H   ( 231,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   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) 
RIDE C   (  36,X'S) H   ( 362,X'S) H   ( 361,X'S) 
RIDE O   (  39,X'S) H   ( 391,X'S) 
RIDE C   (  40,X'S) H   ( 401,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) 
RIDE C   (  43,X'S) H   ( 432,X'S) H   ( 431,X'S) 
RIDE C   (  45,X'S) H   ( 451,X'S) 
RIDE C   (  46,X'S) H   ( 461,X'S) 
RIDE C   (  47,X'S) H   ( 471,X'S) 
RIDE C   (  48,X'S) H   ( 481,X'S) 
RIDE C   (  49,X'S) H   ( 491,X'S) 
RIDE C   (  50,X'S) H   ( 501,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) 
RIDE C   (  54,X'S) H   ( 541,X'S) 
RIDE C   (  55,X'S) H   ( 551,X'S) 
RIDE C   (  56,X'S) H   ( 561,X'S) 
RIDE C   (  57,X'S) H   ( 571,X'S) H   ( 572,X'S) H   ( 573,X'S) 
RIDE C   (  59,X'S) H   ( 591,X'S) 
RIDE C   (  60,X'S) H   ( 601,X'S) 
RIDE C   (  61,X'S) H   ( 611,X'S) 
RIDE C   (  62,X'S) H   ( 621,X'S) 
RIDE C   (  63,X'S) H   ( 631,X'S) 
RIDE C   (  64,X'S) H   ( 641,X'S) 
RIDE C   (  66,X'S) H   ( 661,X'S) 
RIDE C   (  67,X'S) H   ( 671,X'S) 
RIDE C   (  68,X'S) H   ( 681,X'S) 
RIDE C   (  69,X'S) H   ( 691,X'S) 
RIDE C   (  70,X'S) H   ( 701,X'S) 
RIDE C   (  71,X'S) H   ( 711,X'S) 
RIDE C   (  72,X'S) H   ( 721,X'S) H   ( 722,X'S) 
RIDE C   (  75,X'S) H   ( 751,X'S) H   ( 752,X'S) H   ( 753,X'S) 
RIDE C   (  76,X'S) H   ( 763,X'S) H   ( 762,X'S) H   ( 761,X'S) 
END                                                                             
;

_iucr_refine_instruction_details_restraints 
;
#
# Punched on 28/03/13 at 15:06:10
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 982703'
#######################################################################
#
#                 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_86.HBF4
_ccdc_journal_depnumber          ?
#==============================================================================

_cell_length_a                   8.93933(11)
_cell_length_b                   14.19427(18)
_cell_length_c                   10.40085(16)
_cell_angle_alpha                90
_cell_angle_beta                 98.8420(13)
_cell_angle_gamma                90
_cell_volume                     1304.05(3)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-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'
B 0.0090 0.0039 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 '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'
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 = C27 H36 B1 F4 N1 O2 
# Dc =      1.26 Fooo =    524.00 Mu =      8.08 M =    493.39
# Found Formula = C27 H36 B1 F4 N1 O2 
# Dc =      1.26 FOOO =    524.00 Mu =      8.08 M =    493.39

_chemical_formula_sum            'C27 H36 B1 F4 N1 O2'
_chemical_formula_moiety         'C27 H36 B1 F4 N1 O2'
_chemical_compound_source        .
_chemical_formula_weight         493.39

_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.080
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_max          0.190

_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             524
_exptl_absorpt_coefficient_mu    0.808

# Sheldrick geometric approximatio 0.92 0.94 
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9224
_exptl_absorpt_correction_T_max  0.9374
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_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      150
_diffrn_reflns_number            28792
_reflns_number_total             5399
_diffrn_reflns_av_R_equivalents  0.025
# Number of reflections without Friedels Law is 5399 
# Number of reflections with Friedels Law is 2829 
# Theoretical number of reflections is about 2733 

_diffrn_reflns_theta_min         4.302
_diffrn_reflns_theta_max         76.274
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        76.274
_diffrn_measured_fraction_theta_full 0.997

_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              -17
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   2.47
_oxford_diffrn_Wilson_scale      0.01

_atom_sites_solution_primary     Direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.14
_refine_diff_density_max         0.17

# 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>-3.0\s(I)
_refine_ls_number_reflns         5377
_refine_ls_number_restraints     43
_refine_ls_number_parameters     345
_oxford_refine_ls_R_factor_ref   0.0285
_refine_ls_wR_factor_ref         0.0695
_refine_ls_goodness_of_fit_ref   0.9882
_refine_ls_shift/su_max          0.0004040
_refine_ls_shift/su_mean         0.0000347

# The values computed from all data 
_oxford_reflns_number_all        5378
_refine_ls_R_factor_all          0.0285
_refine_ls_wR_factor_all         0.0696

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5232
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_gt          0.0686

_refine_ls_abs_structure_Flack   0.03(9)
_refine_ls_abs_structure_details 'Flack (1983), 2570 Friedel-pairs'
# 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 ad

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.25P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint

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 0.99089(8) 0.59676(7) 0.22796(9) 0.0369 1.0000 Uani . . . . . .
B2 B 1.13548(17) 0.63229(13) 0.28009(18) 0.0329 1.0000 Uani . U . . . .
O6 O 0.81794(11) 0.86815(8) 0.33806(10) 0.0317 1.0000 Uani . . . . . .
C7 C 0.71945(14) 0.85497(10) 0.22843(13) 0.0252 1.0000 Uani . . . . . .
O8 O 0.60290(11) 0.89802(8) 0.20106(10) 0.0336 1.0000 Uani . . . . . .
C9 C 0.77892(13) 0.78185(10) 0.14239(12) 0.0220 1.0000 Uani . . . . . .
C10 C 0.67303(13) 0.69762(9) 0.10197(12) 0.0207 1.0000 Uani . . . . . .
N11 N 0.67617(11) 0.62664(8) 0.21466(10) 0.0193 1.0000 Uani . . . . . .
C12 C 0.59187(14) 0.66285(10) 0.32171(12) 0.0229 1.0000 Uani . . . . . .
C13 C 0.65892(14) 0.62916(10) 0.45561(12) 0.0228 1.0000 Uani . . . . . .
C14 C 0.81059(15) 0.64526(11) 0.50540(13) 0.0278 1.0000 Uani . . . . . .
C15 C 0.87009(16) 0.60983(12) 0.62711(14) 0.0352 1.0000 Uani . . . . . .
C16 C 0.77938(19) 0.56052(12) 0.69960(15) 0.0375 1.0000 Uani . . . . . .
C17 C 0.62648(18) 0.54750(11) 0.65289(14) 0.0338 1.0000 Uani . . . . . .
C18 C 0.56695(15) 0.58181(10) 0.53071(13) 0.0259 1.0000 Uani . . . . . .
C19 C 0.61411(14) 0.52978(10) 0.16516(12) 0.0222 1.0000 Uani . . . . . .
C20 C 0.62715(14) 0.45871(9) 0.27513(12) 0.0213 1.0000 Uani . . . . . .
C21 C 0.76588(14) 0.43575(10) 0.34939(13) 0.0234 1.0000 Uani . . . . . .
C22 C 0.77302(16) 0.36683(10) 0.44498(13) 0.0290 1.0000 Uani . . . . . .
C23 C 0.64344(17) 0.31857(11) 0.46448(14) 0.0334 1.0000 Uani . . . . . .
C24 C 0.50594(16) 0.33934(11) 0.38889(15) 0.0313 1.0000 Uani . . . . . .
C25 C 0.49738(14) 0.41010(10) 0.29554(13) 0.0251 1.0000 Uani . . . . . .
C26 C 0.69120(17) 0.49279(11) 0.05417(13) 0.0292 1.0000 Uani . . . . . .
C27 C 0.51255(13) 0.71886(10) 0.04380(12) 0.0240 1.0000 Uani . . . . . .
C28 C 0.45795(15) 0.69825(11) -0.07850(14) 0.0293 1.0000 Uani . . . . . .
C29 C 0.29845(16) 0.71607(12) -0.14075(16) 0.0380 1.0000 Uani . . . . . .
C30 C 0.81423(14) 0.83659(10) 0.02034(12) 0.0236 1.0000 Uani . . . . . .
C31 C 0.91697(15) 0.91817(10) 0.06548(14) 0.0282 1.0000 Uani . . . . . .
C32 C 0.88368(19) 1.00710(11) 0.04166(17) 0.0379 1.0000 Uani . . . . . .
C33 C 0.88668(18) 0.77410(11) -0.07416(15) 0.0338 1.0000 Uani . . . . . .
C34 C 0.92809(16) 0.82851(11) -0.18951(14) 0.0319 1.0000 Uani . . . . . .
C35 C 0.7820(2) 0.94402(13) 0.42132(17) 0.0449 1.0000 Uani . . . . . .
H91 H 0.8747 0.7556 0.1869 0.0277 1.0000 Uiso R . . . . .
H101 H 0.7214 0.6640 0.0359 0.0262 1.0000 Uiso R . . . . .
H122 H 0.4886 0.6408 0.2999 0.0286 1.0000 Uiso R . . . . .
H121 H 0.5905 0.7311 0.3169 0.0298 1.0000 Uiso R . . . . .
H141 H 0.8747 0.6797 0.4535 0.0350 1.0000 Uiso R . . . . .
H151 H 0.9748 0.6222 0.6578 0.0471 1.0000 Uiso R . . . . .
H161 H 0.8223 0.5366 0.7846 0.0475 1.0000 Uiso R . . . . .
H171 H 0.5634 0.5139 0.7057 0.0447 1.0000 Uiso R . . . . .
H181 H 0.4610 0.5736 0.4995 0.0312 1.0000 Uiso R . . . . .
H191 H 0.5027 0.5392 0.1323 0.0287 1.0000 Uiso R . . . . .
H211 H 0.8545 0.4707 0.3334 0.0305 1.0000 Uiso R . . . . .
H221 H 0.8687 0.3497 0.4987 0.0371 1.0000 Uiso R . . . . .
H231 H 0.6471 0.2688 0.5280 0.0399 1.0000 Uiso R . . . . .
H241 H 0.4161 0.3063 0.4028 0.0398 1.0000 Uiso R . . . . .
H251 H 0.4009 0.4270 0.2461 0.0315 1.0000 Uiso R . . . . .
H262 H 0.6554 0.4286 0.0428 0.0474 1.0000 Uiso R . . . . .
H261 H 0.6608 0.5290 -0.0262 0.0482 1.0000 Uiso R . . . . .
H263 H 0.8024 0.4943 0.0824 0.0479 1.0000 Uiso R . . . . .
H271 H 0.4467 0.7497 0.0982 0.0312 1.0000 Uiso R . . . . .
H281 H 0.5272 0.6692 -0.1298 0.0393 1.0000 Uiso R . . . . .
H292 H 0.2545 0.6570 -0.1767 0.0628 1.0000 Uiso R . . . . .
H291 H 0.2362 0.7404 -0.0754 0.0611 1.0000 Uiso R . . . . .
H293 H 0.2957 0.7619 -0.2107 0.0619 1.0000 Uiso R . . . . .
H301 H 0.7143 0.8620 -0.0236 0.0296 1.0000 Uiso R . . . . .
H311 H 1.0139 0.9041 0.1132 0.0344 1.0000 Uiso R . . . . .
H321 H 0.7858 1.0216 -0.0043 0.0480 1.0000 Uiso R . . . . .
H322 H 0.9550 1.0569 0.0691 0.0475 1.0000 Uiso R . . . . .
H332 H 0.8112 0.7241 -0.1068 0.0413 1.0000 Uiso R . . . . .
H331 H 0.9768 0.7438 -0.0225 0.0416 1.0000 Uiso R . . . . .
H342 H 0.9705 0.7893 -0.2539 0.0487 1.0000 Uiso R . . . . .
H341 H 0.8390 0.8611 -0.2348 0.0493 1.0000 Uiso R . . . . .
H343 H 1.0026 0.8760 -0.1607 0.0497 1.0000 Uiso R . . . . .
H352 H 0.8677 0.9509 0.4913 0.0664 1.0000 Uiso R . . . . .
H353 H 0.7648 1.0032 0.3701 0.0665 1.0000 Uiso R . . . . .
H351 H 0.6885 0.9285 0.4560 0.0661 1.0000 Uiso R . . . . .
H111 H 0.7757 0.6177 0.2476 0.0322 1.0000 Uiso R . . . . .
F50 F 1.1635(4) 0.7155(2) 0.2300(5) 0.0815 0.620(7) Uani . U P 1 2 .
F51 F 1.1884(6) 0.6762(6) 0.1773(5) 0.0855 0.380(7) Uani . U P 1 1 .
F30 F 1.2258(9) 0.5640(5) 0.3180(9) 0.1013 0.380(7) Uani . U P 1 1 .
F31 F 1.2424(4) 0.5681(3) 0.2628(5) 0.0860 0.620(7) Uani . U P 1 2 .
F40 F 1.1093(5) 0.6944(5) 0.3661(7) 0.0798 0.380(7) Uani . U P 1 1 .
F41 F 1.1475(4) 0.6425(3) 0.4169(2) 0.0702 0.620(7) Uani . U P 1 2 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          9.7(2)
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 . B2 . 1.4154(17) yes
B2 . F51 . 1.382(5) yes
B2 . F30 . 1.284(6) yes
B2 . F40 . 1.302(4) yes
B2 . F50 . 1.330(3) yes
B2 . F31 . 1.352(3) yes
B2 . F41 . 1.418(3) yes
O6 . C7 . 1.3423(17) yes
O6 . C35 . 1.4486(18) yes
C7 . O8 . 1.2036(16) yes
C7 . C9 . 1.5189(17) yes
C9 . C10 . 1.5427(17) yes
C9 . C30 . 1.5613(17) yes
C9 . H91 . 0.982 no
C10 . N11 . 1.5426(14) yes
C10 . C27 . 1.4994(16) yes
C10 . H101 . 0.989 no
N11 . C12 . 1.5263(15) yes
N11 . C19 . 1.5411(15) yes
N11 . H111 . 0.912 no
C12 . C13 . 1.5069(18) yes
C12 . H122 . 0.968 no
C12 . H121 . 0.970 no
C13 . C14 . 1.3939(18) yes
C13 . C18 . 1.3910(17) yes
C14 . C15 . 1.390(2) yes
C14 . H141 . 0.977 no
C15 . C16 . 1.380(2) yes
C15 . H151 . 0.958 no
C16 . C17 . 1.391(2) yes
C16 . H161 . 0.970 no
C17 . C18 . 1.388(2) yes
C17 . H171 . 0.971 no
C18 . H181 . 0.960 no
C19 . C20 . 1.5160(17) yes
C19 . C26 . 1.5257(18) yes
C19 . H191 . 1.011 no
C20 . C21 . 1.3951(18) yes
C20 . C25 . 1.3938(17) yes
C21 . C22 . 1.3892(19) yes
C21 . H211 . 0.970 no
C22 . C23 . 1.387(2) yes
C22 . H221 . 0.978 no
C23 . C24 . 1.385(2) yes
C23 . H231 . 0.964 no
C24 . C25 . 1.3909(19) yes
C24 . H241 . 0.960 no
C25 . H251 . 0.964 no
C26 . H262 . 0.967 no
C26 . H261 . 0.983 no
C26 . H263 . 0.993 no
C27 . C28 . 1.3232(19) yes
C27 . H271 . 0.980 no
C28 . C29 . 1.4941(18) yes
C28 . H281 . 0.970 no
C29 . H292 . 0.976 no
C29 . H291 . 1.003 no
C29 . H293 . 0.974 no
C30 . C31 . 1.5074(18) yes
C30 . C33 . 1.5389(18) yes
C30 . H301 . 1.005 no
C31 . C32 . 1.312(2) yes
C31 . H311 . 0.951 no
C32 . H321 . 0.953 no
C32 . H322 . 0.966 no
C33 . C34 . 1.5196(19) yes
C33 . H332 . 1.002 no
C33 . H331 . 0.995 no
C34 . H342 . 0.990 no
C34 . H341 . 0.977 no
C34 . H343 . 0.962 no
C35 . H352 . 0.977 no
C35 . H353 . 0.994 no
C35 . H351 . 0.985 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 . B2 . F51 . 105.4(2) yes
F1 . B2 . F30 . 110.0(4) yes
F51 . B2 . F30 . 107.7(5) yes
F1 . B2 . F40 . 104.74(19) yes
F51 . B2 . F40 . 110.1(4) yes
F30 . B2 . F40 . 118.1(5) yes
F1 . B2 . F50 . 112.48(17) yes
F1 . B2 . F31 . 109.4(2) yes
F50 . B2 . F31 . 111.5(3) yes
F1 . B2 . F41 . 110.17(15) yes
F50 . B2 . F41 . 108.2(2) yes
F31 . B2 . F41 . 104.9(2) yes
C7 . O6 . C35 . 115.76(12) yes
O6 . C7 . O8 . 124.13(12) yes
O6 . C7 . C9 . 110.64(11) yes
O8 . C7 . C9 . 125.18(12) yes
C7 . C9 . C10 . 115.75(10) yes
C7 . C9 . C30 . 105.77(10) yes
C10 . C9 . C30 . 110.88(10) yes
C7 . C9 . H91 . 109.9 no
C10 . C9 . H91 . 106.8 no
C30 . C9 . H91 . 107.6 no
C9 . C10 . N11 . 111.13(9) yes
C9 . C10 . C27 . 117.59(10) yes
N11 . C10 . C27 . 110.03(9) yes
C9 . C10 . H101 . 104.4 no
N11 . C10 . H101 . 104.7 no
C27 . C10 . H101 . 108.0 no
C10 . N11 . C12 . 112.39(9) yes
C10 . N11 . C19 . 111.42(9) yes
C12 . N11 . C19 . 110.57(9) yes
C10 . N11 . H111 . 106.2 no
C12 . N11 . H111 . 109.6 no
C19 . N11 . H111 . 106.3 no
N11 . C12 . C13 . 113.36(9) yes
N11 . C12 . H122 . 106.3 no
C13 . C12 . H122 . 110.1 no
N11 . C12 . H121 . 107.6 no
C13 . C12 . H121 . 111.4 no
H122 . C12 . H121 . 107.9 no
C12 . C13 . C14 . 121.16(11) yes
C12 . C13 . C18 . 119.13(11) yes
C14 . C13 . C18 . 119.71(12) yes
C13 . C14 . C15 . 119.56(13) yes
C13 . C14 . H141 . 119.8 no
C15 . C14 . H141 . 120.6 no
C14 . C15 . C16 . 120.43(13) yes
C14 . C15 . H151 . 117.1 no
C16 . C15 . H151 . 122.5 no
C15 . C16 . C17 . 120.34(14) yes
C15 . C16 . H161 . 119.5 no
C17 . C16 . H161 . 120.1 no
C16 . C17 . C18 . 119.41(13) yes
C16 . C17 . H171 . 119.5 no
C18 . C17 . H171 . 121.0 no
C13 . C18 . C17 . 120.46(13) yes
C13 . C18 . H181 . 120.4 no
C17 . C18 . H181 . 119.1 no
N11 . C19 . C20 . 111.07(10) yes
N11 . C19 . C26 . 112.24(10) yes
C20 . C19 . C26 . 110.52(10) yes
N11 . C19 . H191 . 106.3 no
C20 . C19 . H191 . 107.5 no
C26 . C19 . H191 . 109.0 no
C19 . C20 . C21 . 122.13(11) yes
C19 . C20 . C25 . 118.36(11) yes
C21 . C20 . C25 . 119.33(12) yes
C20 . C21 . C22 . 119.99(12) yes
C20 . C21 . H211 . 117.7 no
C22 . C21 . H211 . 122.3 no
C21 . C22 . C23 . 120.32(12) yes
C21 . C22 . H221 . 121.6 no
C23 . C22 . H221 . 118.0 no
C22 . C23 . C24 . 120.00(13) yes
C22 . C23 . H231 . 121.4 no
C24 . C23 . H231 . 118.6 no
C23 . C24 . C25 . 119.91(13) yes
C23 . C24 . H241 . 120.0 no
C25 . C24 . H241 . 120.0 no
C20 . C25 . C24 . 120.40(12) yes
C20 . C25 . H251 . 119.5 no
C24 . C25 . H251 . 120.0 no
C19 . C26 . H262 . 103.7 no
C19 . C26 . H261 . 111.4 no
H262 . C26 . H261 . 110.2 no
C19 . C26 . H263 . 108.5 no
H262 . C26 . H263 . 110.7 no
H261 . C26 . H263 . 111.9 no
C10 . C27 . C28 . 122.15(12) yes
C10 . C27 . H271 . 118.6 no
C28 . C27 . H271 . 119.2 no
C27 . C28 . C29 . 124.44(14) yes
C27 . C28 . H281 . 116.8 no
C29 . C28 . H281 . 118.8 no
C28 . C29 . H292 . 108.8 no
C28 . C29 . H291 . 110.9 no
H292 . C29 . H291 . 108.8 no
C28 . C29 . H293 . 110.5 no
H292 . C29 . H293 . 109.1 no
H291 . C29 . H293 . 108.9 no
C9 . C30 . C31 . 108.59(11) yes
C9 . C30 . C33 . 112.95(10) yes
C31 . C30 . C33 . 110.22(11) yes
C9 . C30 . H301 . 105.8 no
C31 . C30 . H301 . 108.8 no
C33 . C30 . H301 . 110.4 no
C30 . C31 . C32 . 124.80(13) yes
C30 . C31 . H311 . 117.6 no
C32 . C31 . H311 . 117.6 no
C31 . C32 . H321 . 117.8 no
C31 . C32 . H322 . 121.9 no
H321 . C32 . H322 . 120.2 no
C30 . C33 . C34 . 112.88(11) yes
C30 . C33 . H332 . 107.3 no
C34 . C33 . H332 . 109.0 no
C30 . C33 . H331 . 106.8 no
C34 . C33 . H331 . 111.8 no
H332 . C33 . H331 . 108.9 no
C33 . C34 . H342 . 114.5 no
C33 . C34 . H341 . 110.0 no
H342 . C34 . H341 . 108.0 no
C33 . C34 . H343 . 110.6 no
H342 . C34 . H343 . 106.6 no
H341 . C34 . H343 . 107.0 no
O6 . C35 . H352 . 107.4 no
O6 . C35 . H353 . 109.7 no
H352 . C35 . H353 . 110.7 no
O6 . C35 . H351 . 109.4 no
H352 . C35 . H351 . 111.3 no
H353 . C35 . H351 . 108.4 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
C12 . H121 . C7 . 139.41(4) 0.970 2.365 3.165(2) yes
C17 . H171 . O8 2_646 166.10(4) 0.971 2.510 3.460(2) yes

_iucr_refine_instruction_details_constraints 
;
#
# Punched on 10/10/13 at 10:45:16
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE N   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 122,X'S) H   ( 121,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   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,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   ( 262,X'S) H   ( 261,X'S) H   ( 263,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   ( 292,X'S) H   ( 291,X'S) H   ( 293,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) H   ( 322,X'S) 
RIDE C   (  33,X'S) H   ( 332,X'S) H   ( 331,X'S) 
RIDE C   (  34,X'S) H   ( 342,X'S) H   ( 341,X'S) H   ( 343,X'S) 
RIDE C   (  35,X'S) H   ( 352,X'S) H   ( 353,X'S) H   ( 351,X'S) 
EQUIV PART (1001,OCC) PART (1002, OCC) 
WEIGHT -1 PART (1002,OCC) 
END                                                                             
;

_iucr_refine_instruction_details_restraints 
;
#
# Punched on 10/10/13 at 10:45:16
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
VIB 0, .002 = F(51) TO B(2) 
CONT F(30) TO B(2) 
CONT F(40) TO B(2) 
CONT F(50) TO B(2) 
CONT F(31) TO B(2) 
CONT F(41) TO B(2) 
U(IJ) 0, .01 = F(51) TO B(2) 
CONT F(30) TO B(2) 
CONT F(40) TO B(2) 
CONT F(50) TO B(2) 
CONT F(31) TO B(2) 
CONT F(41) TO B(2) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 982704'
#######################################################################
#
#                 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_87
_ccdc_journal_depnumber          ?
#==============================================================================

_cell_length_a                   10.7026(7)
_cell_length_b                   15.0868(9)
_cell_length_c                   16.8872(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2726.8(3)

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 2 21 21'
_symmetry_space_group_name_Hall  'P 2bc 2'
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'

_cell_formula_units_Z            4

# Given Formula = C31 H35 N1 O2 
# Dc =      1.10 Fooo =    976.00 Mu =      5.27 M =    453.62
# Found Formula = C31 H35 N1 O2 
# Dc =      1.10 FOOO =    976.00 Mu =      5.27 M =    453.62

_chemical_formula_sum            'C31 H35 N1 O2'
_chemical_formula_moiety         'C31 H35 N1 O2'
_chemical_compound_source        .
_chemical_formula_weight         453.62

_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    150

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.080
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_max          0.190

_exptl_crystal_density_diffrn    1.105
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    0.527

# Sheldrick geometric approximatio 0.94 0.96 
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9437
_exptl_absorpt_correction_T_max  0.9587
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_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      150
_diffrn_reflns_number            19630
_reflns_number_total             5681
_diffrn_reflns_av_R_equivalents  0.079
# Number of reflections without Friedels Law is 5681 
# Number of reflections with Friedels Law is 3216 
# Theoretical number of reflections is about 2585 

_diffrn_reflns_theta_min         2.929
_diffrn_reflns_theta_max         76.683
_diffrn_measured_fraction_theta_max 0.990

_diffrn_reflns_theta_full        75.149
_diffrn_measured_fraction_theta_full 0.997

_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_reflns_limit_h_min              -13
_reflns_limit_h_max              13
_reflns_limit_k_min              0
_reflns_limit_k_max              18
_reflns_limit_l_min              0
_reflns_limit_l_max              21

_oxford_diffrn_Wilson_B_factor   3.73
_oxford_diffrn_Wilson_scale      0.06

_atom_sites_solution_primary     Direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.36
_refine_diff_density_max         0.92

# 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>-3.0\s(I)
_refine_ls_number_reflns         5154
_refine_ls_number_restraints     0
_refine_ls_number_parameters     308
_oxford_refine_ls_R_factor_ref   0.0794
_refine_ls_wR_factor_ref         0.2054
_refine_ls_goodness_of_fit_ref   0.9966
_refine_ls_shift/su_max          0.0001625
_refine_ls_shift/su_mean         0.0000133

# The values computed from all data 
_oxford_reflns_number_all        5154
_refine_ls_R_factor_all          0.0794
_refine_ls_wR_factor_all         0.2054

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4652
_refine_ls_R_factor_gt           0.0740
_refine_ls_wR_factor_gt          0.1998

_refine_ls_abs_structure_Flack   -0.7(4)
_refine_ls_abs_structure_details 'Flack (1983), 2465 Friedel-pairs'
# 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 ad

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.12P)² + 1.52P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint

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 0.4245(3) 0.61383(14) 0.46644(11) 0.0481 1.0000 Uani . . . . . .
C2 C 0.4209(3) 0.56235(18) 0.40322(16) 0.0343 1.0000 Uani . . . . . .
O3 O 0.4497(2) 0.48514(14) 0.40450(11) 0.0472 1.0000 Uani . . . . . .
C4 C 0.3715(3) 0.6086(2) 0.33033(15) 0.0331 1.0000 Uani . . . . . .
C5 C 0.4559(3) 0.58678(19) 0.25853(15) 0.0322 1.0000 Uani . . . . . .
N6 N 0.4022(2) 0.62504(16) 0.18569(13) 0.0350 1.0000 Uani . . . . . .
C7 C 0.4472(3) 0.5814(2) 0.11314(16) 0.0427 1.0000 Uani . . . . . .
C8 C 0.4079(3) 0.4850(2) 0.10740(14) 0.0411 1.0000 Uani . . . . . .
C9 C 0.2824(3) 0.4619(2) 0.0995(2) 0.0479 1.0000 Uani . . . . . .
C10 C 0.2467(4) 0.3743(3) 0.0897(2) 0.0622 1.0000 Uani . . . . . .
C11 C 0.3360(5) 0.3078(3) 0.0866(2) 0.0636 1.0000 Uani . . . . . .
C12 C 0.4585(5) 0.3296(3) 0.0943(3) 0.0668 1.0000 Uani . . . . . .
C13 C 0.4948(4) 0.4175(2) 0.1060(2) 0.0542 1.0000 Uani . . . . . .
C15 C 0.4084(4) 0.7215(2) 0.18035(19) 0.0478 1.0000 Uani . . . . . .
C16 C 0.3002(3) 0.7602(2) 0.13278(16) 0.0393 1.0000 Uani . . . . . .
C17 C 0.1948(4) 0.7120(3) 0.1147(2) 0.0590 1.0000 Uani . . . . . .
C18 C 0.0993(4) 0.7470(4) 0.0702(2) 0.0718 1.0000 Uani . . . . . .
C19 C 0.1036(5) 0.8292(4) 0.0448(3) 0.0896 1.0000 Uani . . . . . .
C20 C 0.2063(7) 0.8804(4) 0.0627(4) 0.0998 1.0000 Uani . . . . . .
C21 C 0.3058(5) 0.8452(2) 0.1060(3) 0.0653 1.0000 Uani . . . . . .
C22 C 0.5384(5) 0.7542(3) 0.1406(3) 0.0743 1.0000 Uani . . . . . .
C23 C 0.5887(3) 0.6127(2) 0.27594(16) 0.0439 1.0000 Uani . . . . . .
C24 C 0.6853(4) 0.5596(3) 0.2732(3) 0.0692 1.0000 Uani . . . . . .
C25 C 0.8180(5) 0.5869(5) 0.2911(4) 0.1115 1.0000 Uani . . . . . .
C26 C 0.2318(3) 0.5832(2) 0.31909(18) 0.0417 1.0000 Uani . . . . . .
C27 C 0.1492(3) 0.6224(3) 0.3843(2) 0.0524 1.0000 Uani . . . . . .
C28 C 0.1488(3) 0.7223(3) 0.3877(3) 0.0646 1.0000 Uani . . . . . .
C29 C 0.1943(4) 0.7665(3) 0.4549(3) 0.0753 1.0000 Uani . . . . . .
C30 C 0.1890(6) 0.8589(4) 0.4585(5) 0.1045 1.0000 Uani . . . . . .
C31 C 0.1415(6) 0.9081(4) 0.3959(6) 0.1099 1.0000 Uani . . . . . .
C32 C 0.0976(6) 0.8642(4) 0.3280(6) 0.1156 1.0000 Uani . . . . . .
C33 C 0.1013(5) 0.7725(3) 0.3246(4) 0.0802 1.0000 Uani . . . . . .
C34 C 0.2136(4) 0.4855(3) 0.3075(2) 0.0532 1.0000 Uani . . . . . .
C35 C 0.1407(5) 0.4330(3) 0.3492(3) 0.0751 1.0000 Uani . . . . . .
H41 H 0.3765 0.6762 0.3390 0.0450 1.0000 Uiso R . . . . .
H51 H 0.4521 0.5192 0.2542 0.0447 1.0000 Uiso R . . . . .
H71 H 0.5493 0.5971 0.1019 0.0543 1.0000 Uiso R . . . . .
H72 H 0.4013 0.6125 0.0710 0.0583 1.0000 Uiso R . . . . .
H91 H 0.2214 0.5089 0.1004 0.0624 1.0000 Uiso R . . . . .
H101 H 0.1597 0.3573 0.0841 0.0788 1.0000 Uiso R . . . . .
H111 H 0.3102 0.2471 0.0796 0.0814 1.0000 Uiso R . . . . .
H121 H 0.5232 0.2828 0.0924 0.0860 1.0000 Uiso R . . . . .
H131 H 0.5814 0.4332 0.1126 0.0730 1.0000 Uiso R . . . . .
H151 H 0.4028 0.7466 0.2347 0.0624 1.0000 Uiso R . . . . .
H171 H 0.1895 0.6513 0.1332 0.0757 1.0000 Uiso R . . . . .
H181 H 0.0259 0.7112 0.0571 0.0970 1.0000 Uiso R . . . . .
H191 H 0.0347 0.8527 0.0152 0.1130 1.0000 Uiso R . . . . .
H201 H 0.2097 0.9398 0.0461 0.1354 1.0000 Uiso R . . . . .
H211 H 0.3787 0.8807 0.1171 0.0878 1.0000 Uiso R . . . . .
H221 H 0.5498 0.8228 0.1444 0.1466 1.0000 Uiso R . . . . .
H222 H 0.6119 0.7241 0.1664 0.1464 1.0000 Uiso R . . . . .
H223 H 0.5386 0.7374 0.0822 0.1471 1.0000 Uiso R . . . . .
H231 H 0.6028 0.6734 0.2915 0.0615 1.0000 Uiso R . . . . .
H241 H 0.6711 0.4999 0.2629 0.0959 1.0000 Uiso R . . . . .
H251 H 0.8551 0.5447 0.3277 0.1701 1.0000 Uiso R . . . . .
H252 H 0.8166 0.6464 0.3148 0.1701 1.0000 Uiso R . . . . .
H253 H 0.8651 0.5888 0.2409 0.1704 1.0000 Uiso R . . . . .
H261 H 0.2049 0.6103 0.2673 0.0545 1.0000 Uiso R . . . . .
H271 H 0.1777 0.6006 0.4363 0.0669 1.0000 Uiso R . . . . .
H272 H 0.0584 0.6035 0.3747 0.0670 1.0000 Uiso R . . . . .
H291 H 0.2284 0.7341 0.4978 0.1023 1.0000 Uiso R . . . . .
H301 H 0.2161 0.8885 0.5041 0.1354 1.0000 Uiso R . . . . .
H311 H 0.1354 0.9721 0.3983 0.1334 1.0000 Uiso R . . . . .
H321 H 0.0667 0.8957 0.2841 0.1435 1.0000 Uiso R . . . . .
H331 H 0.0683 0.7421 0.2811 0.1005 1.0000 Uiso R . . . . .
H341 H 0.2641 0.4581 0.2675 0.0665 1.0000 Uiso R . . . . .
H351 H 0.0921 0.4553 0.3912 0.0982 1.0000 Uiso R . . . . .
H352 H 0.1334 0.3719 0.3374 0.0982 1.0000 Uiso R . . . . .
H11 H 0.4273 0.5858 0.5113 0.0791 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.71(14)
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 . 1.321(3) yes
O1 . H11 . 0.868 no
C2 . O3 . 1.205(3) yes
C2 . C4 . 1.511(4) yes
C4 . C5 . 1.547(4) yes
C4 . C26 . 1.556(4) yes
C4 . H41 . 1.031 no
C5 . N6 . 1.475(3) yes
C5 . C23 . 1.504(4) yes
C5 . H51 . 1.023 no
N6 . C7 . 1.472(4) yes
N6 . C15 . 1.460(4) yes
C7 . C8 . 1.516(4) yes
C7 . H71 . 1.134 no
C7 . H72 . 0.984 no
C8 . C9 . 1.394(5) yes
C8 . C13 . 1.381(5) yes
C9 . C10 . 1.385(5) yes
C9 . H91 . 0.964 no
C10 . C11 . 1.388(7) yes
C10 . H101 . 0.970 no
C11 . C12 . 1.357(7) yes
C11 . H111 . 0.964 no
C12 . C13 . 1.395(6) yes
C12 . H121 . 0.991 no
C13 . H131 . 0.962 no
C15 . C16 . 1.526(4) yes
C15 . C22 . 1.621(6) yes
C15 . H151 . 0.994 no
C16 . C17 . 1.377(5) yes
C16 . C21 . 1.360(5) yes
C17 . C18 . 1.374(6) yes
C17 . H171 . 0.970 no
C18 . C19 . 1.313(8) yes
C18 . H181 . 0.978 no
C19 . C20 . 1.377(9) yes
C19 . H191 . 0.959 no
C20 . C21 . 1.397(7) yes
C20 . H201 . 0.940 no
C21 . H211 . 0.965 no
C22 . H221 . 1.044 no
C22 . H222 . 1.008 no
C22 . H223 . 1.018 no
C23 . C24 . 1.308(6) yes
C23 . H231 . 0.964 no
C24 . C25 . 1.509(6) yes
C24 . H241 . 0.931 no
C25 . H251 . 0.972 no
C25 . H252 . 0.983 no
C25 . H253 . 0.986 no
C26 . C27 . 1.531(4) yes
C26 . C34 . 1.499(5) yes
C26 . H261 . 1.007 no
C27 . C28 . 1.509(6) yes
C27 . H271 . 0.986 no
C27 . H272 . 1.026 no
C28 . C29 . 1.405(6) yes
C28 . C33 . 1.402(7) yes
C29 . C30 . 1.395(8) yes
C29 . H291 . 0.947 no
C30 . C31 . 1.390(11) yes
C30 . H301 . 0.936 no
C31 . C32 . 1.406(12) yes
C31 . H311 . 0.968 no
C32 . C33 . 1.385(8) yes
C32 . H321 . 0.941 no
C33 . H331 . 0.936 no
C34 . C35 . 1.317(5) yes
C34 . H341 . 0.959 no
C35 . H351 . 0.941 no
C35 . H352 . 0.946 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 . H11 . 114.9 no
O1 . C2 . O3 . 123.1(3) yes
O1 . C2 . C4 . 113.4(2) yes
O3 . C2 . C4 . 123.4(2) yes
C2 . C4 . C5 . 109.6(2) yes
C2 . C4 . C26 . 108.8(2) yes
C5 . C4 . C26 . 114.4(2) yes
C2 . C4 . H41 . 108.9 no
C5 . C4 . H41 . 107.0 no
C26 . C4 . H41 . 108.1 no
C4 . C5 . N6 . 110.0(2) yes
C4 . C5 . C23 . 110.1(2) yes
N6 . C5 . C23 . 115.5(2) yes
C4 . C5 . H51 . 104.2 no
N6 . C5 . H51 . 108.4 no
C23 . C5 . H51 . 108.1 no
C5 . N6 . C7 . 113.0(2) yes
C5 . N6 . C15 . 115.1(2) yes
C7 . N6 . C15 . 112.3(2) yes
N6 . C7 . C8 . 113.0(2) yes
N6 . C7 . H71 . 111.2 no
C8 . C7 . H71 . 117.2 no
N6 . C7 . H72 . 103.0 no
C8 . C7 . H72 . 105.8 no
H71 . C7 . H72 . 105.1 no
C7 . C8 . C9 . 120.9(3) yes
C7 . C8 . C13 . 121.4(3) yes
C9 . C8 . C13 . 117.6(3) yes
C8 . C9 . C10 . 121.1(4) yes
C8 . C9 . H91 . 117.8 no
C10 . C9 . H91 . 121.0 no
C9 . C10 . C11 . 120.3(4) yes
C9 . C10 . H101 . 122.0 no
C11 . C10 . H101 . 117.8 no
C10 . C11 . C12 . 119.1(4) yes
C10 . C11 . H111 . 119.7 no
C12 . C11 . H111 . 121.2 no
C11 . C12 . C13 . 120.9(4) yes
C11 . C12 . H121 . 120.0 no
C13 . C12 . H121 . 119.1 no
C12 . C13 . C8 . 121.0(4) yes
C12 . C13 . H131 . 121.3 no
C8 . C13 . H131 . 117.7 no
N6 . C15 . C16 . 112.3(3) yes
N6 . C15 . C22 . 111.6(3) yes
C16 . C15 . C22 . 108.4(3) yes
N6 . C15 . H151 . 108.7 no
C16 . C15 . H151 . 107.1 no
C22 . C15 . H151 . 108.6 no
C15 . C16 . C17 . 122.5(3) yes
C15 . C16 . C21 . 120.2(3) yes
C17 . C16 . C21 . 117.4(4) yes
C16 . C17 . C18 . 121.9(4) yes
C16 . C17 . H171 . 118.4 no
C18 . C17 . H171 . 119.7 no
C17 . C18 . C19 . 121.0(5) yes
C17 . C18 . H181 . 120.6 no
C19 . C18 . H181 . 118.4 no
C18 . C19 . C20 . 119.1(4) yes
C18 . C19 . H191 . 119.4 no
C20 . C19 . H191 . 121.4 no
C19 . C20 . C21 . 120.7(5) yes
C19 . C20 . H201 . 120.0 no
C21 . C20 . H201 . 119.3 no
C20 . C21 . C16 . 119.9(5) yes
C20 . C21 . H211 . 120.4 no
C16 . C21 . H211 . 119.6 no
C15 . C22 . H221 . 112.1 no
C15 . C22 . H222 . 110.6 no
H221 . C22 . H222 . 109.2 no
C15 . C22 . H223 . 109.1 no
H221 . C22 . H223 . 107.9 no
H222 . C22 . H223 . 107.8 no
C5 . C23 . C24 . 125.5(4) yes
C5 . C23 . H231 . 116.6 no
C24 . C23 . H231 . 117.9 no
C23 . C24 . C25 . 124.7(5) yes
C23 . C24 . H241 . 118.1 no
C25 . C24 . H241 . 117.1 no
C24 . C25 . H251 . 109.5 no
C24 . C25 . H252 . 108.4 no
H251 . C25 . H252 . 110.1 no
C24 . C25 . H253 . 108.5 no
H251 . C25 . H253 . 110.9 no
H252 . C25 . H253 . 109.4 no
C4 . C26 . C27 . 111.8(3) yes
C4 . C26 . C34 . 112.5(3) yes
C27 . C26 . C34 . 113.5(3) yes
C4 . C26 . H261 . 106.3 no
C27 . C26 . H261 . 107.6 no
C34 . C26 . H261 . 104.4 no
C26 . C27 . C28 . 114.5(3) yes
C26 . C27 . H271 . 109.5 no
C28 . C27 . H271 . 107.5 no
C26 . C27 . H272 . 109.0 no
C28 . C27 . H272 . 106.3 no
H271 . C27 . H272 . 110.0 no
C27 . C28 . C29 . 120.2(4) yes
C27 . C28 . C33 . 120.8(4) yes
C29 . C28 . C33 . 118.9(5) yes
C28 . C29 . C30 . 119.7(6) yes
C28 . C29 . H291 . 120.4 no
C30 . C29 . H291 . 119.9 no
C29 . C30 . C31 . 121.0(6) yes
C29 . C30 . H301 . 120.0 no
C31 . C30 . H301 . 119.0 no
C30 . C31 . C32 . 119.4(6) yes
C30 . C31 . H311 . 121.8 no
C32 . C31 . H311 . 118.8 no
C31 . C32 . C33 . 119.7(7) yes
C31 . C32 . H321 . 121.5 no
C33 . C32 . H321 . 118.9 no
C28 . C33 . C32 . 121.3(6) yes
C28 . C33 . H331 . 117.9 no
C32 . C33 . H331 . 120.7 no
C26 . C34 . C35 . 126.7(4) yes
C26 . C34 . H341 . 116.3 no
C35 . C34 . H341 . 116.9 no
C34 . C35 . H351 . 121.1 no
C34 . C35 . H352 . 121.5 no
H351 . C35 . H352 . 117.4 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
C21 . H211 . O3 3_655 159.30(12) 0.965 2.447 3.367(6) yes
C22 . H221 . O3 3_655 156.84(13) 1.044 2.585 3.568(6) yes
C22 . H222 . C23 . 122.96(14) 1.008 2.511 3.174(6) yes
O1 . H11 . O3 2_566 170.34(11) 0.868 1.796 2.656(6) yes

_iucr_refine_instruction_details_constraints 
;
#
# Punched on 22/11/13 at 09:31:35
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE O   (   1,X'S) H   (  11,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,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   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  17,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   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) H   ( 223,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) H   ( 252,X'S) H   ( 253,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) H   ( 272,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) H   ( 352,X'S) 
END                                                                             
;

_iucr_refine_instruction_details_restraints 
;
#
# Punched on 22/11/13 at 09:31:35
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 982705'
#######################################################################
#
#                 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_96.HCl
_ccdc_journal_depnumber          ?
#==============================================================================

_cell_length_a                   5.42100(10)
_cell_length_b                   8.9375(3)
_cell_length_c                   11.4409(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.8270(12)
_cell_angle_gamma                90
_cell_volume                     542.55(3)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-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 0.0033 0.0016 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'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 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 0.0106 0.0060 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 = C9 H18 Cl1 N1 O2 
# Dc =      1.27 Fooo =    224.00 Mu =      3.23 M =    207.70
# Found Formula = C9 H18 Cl1 N1 O2 
# Dc =      1.27 FOOO =    224.00 Mu =      3.23 M =    207.70

_chemical_formula_sum            'C9 H18 Cl1 N1 O2'
_chemical_formula_moiety         'C9 H18 Cl1 N1 O2'
_chemical_compound_source        .
_chemical_formula_weight         207.70

_cell_measurement_reflns_used    1236
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.210
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_max          0.240

_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             224
_exptl_absorpt_coefficient_mu    0.323

# Sheldrick geometric approximatio 0.93 0.93 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  0.93
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_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      150
_diffrn_reflns_number            2115
_reflns_number_total             2115
_diffrn_reflns_av_R_equivalents  0.000
# Number of reflections without Friedels Law is 2115 
# Number of reflections with Friedels Law is 1301 
# Theoretical number of reflections is about 1245 

_diffrn_reflns_theta_min         5.244
_diffrn_reflns_theta_max         27.490
_diffrn_measured_fraction_theta_max 0.985

_diffrn_reflns_theta_full        27.490
_diffrn_measured_fraction_theta_full 0.985

_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -7
_reflns_limit_h_max              6
_reflns_limit_k_min              -11
_reflns_limit_k_max              8
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   1.81
_oxford_diffrn_Wilson_scale      0.28

_atom_sites_solution_primary     Direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.14
_refine_diff_density_max         0.18

# 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>-3.0\s(I)
_refine_ls_number_reflns         2115
_refine_ls_number_restraints     1
_refine_ls_number_parameters     119
_oxford_refine_ls_R_factor_ref   0.0254
_refine_ls_wR_factor_ref         0.0563
_refine_ls_goodness_of_fit_ref   1.0066
_refine_ls_shift/su_max          0.0004402
_refine_ls_shift/su_mean         0.0000229

# The values computed from all data 
_oxford_reflns_number_all        2115
_refine_ls_R_factor_all          0.0254
_refine_ls_wR_factor_all         0.0563

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2067
_refine_ls_R_factor_gt           0.0242
_refine_ls_wR_factor_gt          0.0553

_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_abs_structure_details 'Flack (1983), 814 Friedel-pairs'
# 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 ad

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.01P)² + 0.14P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint

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
Cl1 Cl 0.28777(5) 0.30053(11) 0.57927(3) 0.0231 1.0000 Uani . . . . . .
O2 O 0.5691(2) 0.21543(16) 0.33405(9) 0.0286 1.0000 Uani . . . . . .
C3 C 0.3816(2) 0.2905(2) 0.30133(10) 0.0203 1.0000 Uani . . . . . .
O4 O 0.14909(19) 0.23353(15) 0.27195(9) 0.0254 1.0000 Uani . . . . . .
C5 C 0.1281(4) 0.0753(2) 0.29348(17) 0.0348 1.0000 Uani . . . . . .
C6 C 0.3865(2) 0.45735(18) 0.28357(12) 0.0186 1.0000 Uani . . . . . .
C7 C 0.3917(2) 0.50103(18) 0.15080(12) 0.0203 1.0000 Uani . . . . . .
C8 C 0.1385(3) 0.5796(2) 0.10623(13) 0.0261 1.0000 Uani . . . . . .
C9 C 0.0927(3) 0.6621(2) 0.21618(13) 0.0241 1.0000 Uani . . . . . .
C10 C 0.1584(3) 0.54309(19) 0.31260(13) 0.0183 1.0000 Uani . . . . . .
N11 N 0.2170(2) 0.60970(17) 0.43491(10) 0.0200 1.0000 Uani . . . . . .
C12 C 0.4500(3) 0.3738(2) 0.07152(13) 0.0278 1.0000 Uani . . . . . .
C13 C 0.4634(3) 0.4295(2) -0.05356(13) 0.0326 1.0000 Uani . . . . . .
H51 H -0.0563 0.0507 0.2804 0.0562 1.0000 Uiso R . . . . .
H52 H 0.2051 0.0543 0.3769 0.0556 1.0000 Uiso R . . . . .
H53 H 0.2055 0.0184 0.2395 0.0566 1.0000 Uiso R . . . . .
H61 H 0.5433 0.4977 0.3358 0.0244 1.0000 Uiso R . . . . .
H71 H 0.5316 0.5754 0.1543 0.0245 1.0000 Uiso R . . . . .
H81 H 0.1413 0.6454 0.0373 0.0326 1.0000 Uiso R . . . . .
H82 H 0.0065 0.5021 0.0812 0.0341 1.0000 Uiso R . . . . .
H91 H 0.2114 0.7444 0.2373 0.0317 1.0000 Uiso R . . . . .
H92 H -0.0776 0.6963 0.2094 0.0328 1.0000 Uiso R . . . . .
H101 H 0.0174 0.4741 0.3094 0.0233 1.0000 Uiso R . . . . .
H121 H 0.6108 0.3272 0.1077 0.0347 1.0000 Uiso R . . . . .
H122 H 0.3183 0.2978 0.0657 0.0354 1.0000 Uiso R . . . . .
H131 H 0.5046 0.3461 -0.1021 0.0519 1.0000 Uiso R . . . . .
H133 H 0.5911 0.5082 -0.0470 0.0510 1.0000 Uiso R . . . . .
H132 H 0.2994 0.4705 -0.0930 0.0517 1.0000 Uiso R . . . . .
H112 H 0.3572 0.6729 0.4424 0.0319 1.0000 Uiso R . . . . .
H111 H 0.2474 0.5343 0.4896 0.0325 1.0000 Uiso R . . . . .
H113 H 0.0792 0.6612 0.4458 0.0319 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.920(10)
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
O2 . C3 . 1.2114(17) yes
C3 . O4 . 1.3369(16) yes
C3 . C6 . 1.506(2) yes
O4 . C5 . 1.444(2) yes
C5 . H51 . 1.004 no
C5 . H52 . 0.979 no
C5 . H53 . 0.961 no
C6 . C7 . 1.5743(18) yes
C6 . C10 . 1.5473(19) yes
C6 . H61 . 1.001 no
C7 . C8 . 1.5328(19) yes
C7 . C12 . 1.527(2) yes
C7 . H71 . 1.003 no
C8 . C9 . 1.522(2) yes
C8 . H81 . 0.986 no
C8 . H82 . 0.995 no
C9 . C10 . 1.521(2) yes
C9 . H91 . 0.975 no
C9 . H92 . 0.960 no
C10 . N11 . 1.4937(18) yes
C10 . H101 . 0.977 no
N11 . H112 . 0.937 no
N11 . H111 . 0.912 no
N11 . H113 . 0.908 no
C12 . C13 . 1.531(2) yes
C12 . H121 . 0.978 no
C12 . H122 . 0.978 no
C13 . H131 . 0.983 no
C13 . H133 . 0.979 no
C13 . H132 . 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
O2 . C3 . O4 . 123.68(16) yes
O2 . C3 . C6 . 123.61(13) yes
O4 . C3 . C6 . 112.65(12) yes
C3 . O4 . C5 . 115.70(13) yes
O4 . C5 . H51 . 107.5 no
O4 . C5 . H52 . 108.8 no
H51 . C5 . H52 . 108.4 no
O4 . C5 . H53 . 110.4 no
H51 . C5 . H53 . 110.0 no
H52 . C5 . H53 . 111.7 no
C3 . C6 . C7 . 112.34(11) yes
C3 . C6 . C10 . 115.12(12) yes
C7 . C6 . C10 . 104.93(11) yes
C3 . C6 . H61 . 108.2 no
C7 . C6 . H61 . 107.8 no
C10 . C6 . H61 . 108.2 no
C6 . C7 . C8 . 104.03(11) yes
C6 . C7 . C12 . 115.80(12) yes
C8 . C7 . C12 . 115.05(12) yes
C6 . C7 . H71 . 106.8 no
C8 . C7 . H71 . 109.2 no
C12 . C7 . H71 . 105.7 no
C7 . C8 . C9 . 103.52(11) yes
C7 . C8 . H81 . 112.3 no
C9 . C8 . H81 . 113.8 no
C7 . C8 . H82 . 108.6 no
C9 . C8 . H82 . 110.2 no
H81 . C8 . H82 . 108.3 no
C8 . C9 . C10 . 101.95(12) yes
C8 . C9 . H91 . 111.0 no
C10 . C9 . H91 . 107.7 no
C8 . C9 . H92 . 113.9 no
C10 . C9 . H92 . 111.1 no
H91 . C9 . H92 . 110.8 no
C6 . C10 . C9 . 105.63(11) yes
C6 . C10 . N11 . 111.87(11) yes
C9 . C10 . N11 . 111.97(12) yes
C6 . C10 . H101 . 109.4 no
C9 . C10 . H101 . 110.4 no
N11 . C10 . H101 . 107.5 no
C10 . N11 . H112 . 109.8 no
C10 . N11 . H111 . 108.8 no
H112 . N11 . H111 . 110.8 no
C10 . N11 . H113 . 107.9 no
H112 . N11 . H113 . 110.9 no
H111 . N11 . H113 . 108.5 no
C7 . C12 . C13 . 111.60(13) yes
C7 . C12 . H121 . 109.9 no
C13 . C12 . H121 . 109.0 no
C7 . C12 . H122 . 108.7 no
C13 . C12 . H122 . 109.6 no
H121 . C12 . H122 . 107.9 no
C12 . C13 . H131 . 110.0 no
C12 . C13 . H133 . 109.3 no
H131 . C13 . H133 . 110.4 no
C12 . C13 . H132 . 109.8 no
H131 . C13 . H132 . 108.2 no
H133 . C13 . H132 . 109.1 no

_iucr_refine_instruction_details_constraints 
;
#
# Punched on 10/10/13 at 10:44:22
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   5,X'S) H   (  51,X'S) H   (  52,X'S) H   (  53,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,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 N   (  11,X'S) H   ( 112,X'S) H   ( 111,X'S) H   ( 113,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 133,X'S) H   ( 132,X'S) 
END                                                                             
;

_iucr_refine_instruction_details_restraints 
;
#
# Punched on 10/10/13 at 10:44:22
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 982706'
