# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
#TrackingRef '- Publish Cif for compound 11.cif'

#==============================================================================

_publ_contact_author             'Darren J Dixon'
_publ_contact_author_email       darren.dixon@chem.ox.ac.uk

loop_
_publ_author_name
_publ_author_address
A.Kyle
;
Chemistry Research Laboratory,
University of Oxford,
Mansfield Road,
Oxford OX1 3TA. UK.
;
O.Jakubec
;
School of Chemistry,
The University of Manchester
Oxford Road,
Manchester M13 9PL. UK.
;
D.Cockfield
;
Chemistry Research Laboratory,
University of Oxford,
Mansfield Road,
Oxford OX1 3TA. UK.
;
'Ed Cleator'
;
Chemistry Research Laboratory,
University of Oxford,
Mansfield Road,
Oxford OX1 3TA. UK.
darren.dixon@chem.ox.ac.uk
;
'John Skidmore'
;
Merck Sharp Dohme Research Laboratories,
Global Process Research,
Hoddesdon,Hertfordshire,
EN11 9BU. UK.
;
D.Dixon
;
GlaxoSmithKline,
Neurosciences Centre of Excellence for Drug Discovery,
New Frontiers Science Park,
Harlow,
CM19 5AW. UK.
;
_journal_volume                  ?
_journal_page_first              ?
_journal_page_last               ?
_ccdc_journal_depnumber          ?

_publ_section_title              
;
Total Synthesis of (-)-Nakadomarin A
;

_publ_section_abstract           
;
The combination of a highly diastereoselective bifunctional organocatalyst
controlled Michael addition, a nitro-Mannich / lactamization cascade, furan
N-acyl iminium cyclisation and sequential alkyne RCM / syn-reduction and
alkene ring-closing metathesis key steps has allowed an 18 step, highly
stereoselective synthesis of (-)-nakadomarin A.
;
_publ_contact_author_name        'Darren J Dixon'

#==============================================================================
data_11
_database_code_depnum_ccdc_archive 'CCDC 805604'
#TrackingRef '- Publish Cif for compound 11.cif'

#==============================================================================
_audit_creation_date             10-10-15
_audit_creation_method           CRYSTALS_ver_12.87

_oxford_structure_analysis_title 008DJD10
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_refine_special_details          
;
The ADP of O(11) is enlarged due to a small amount of residual disorder, estimated
at approximately 5%.
;

_cell_length_a                   9.5453(3)
_cell_length_b                   6.9928(2)
_cell_length_c                   13.4491(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.6310(13)
_cell_angle_gamma                90
_cell_volume                     845.53(4)

_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            2

# Given Formula = C19 H23 N3 O6
# Dc = 1.53 Fooo = 372.00 Mu = 1.15 M = 389.41
# Found Formula = C16 H20 N2 O7
# Dc = 1.38 FOOO = 372.00 Mu = 1.10 M = 352.34

_chemical_formula_sum            'C16 H20 N2 O7'
_chemical_formula_moiety         'C16 H20 N2 O7'
_chemical_compound_source        .
_chemical_formula_weight         352.34

_cell_measurement_reflns_used    1788
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.060
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_max          0.340

_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    0.110

# Sheldrick geometric approximatio 0.99 0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.92
_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       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       \w

# 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            5923
_reflns_number_total             1988
_diffrn_reflns_av_R_equivalents  0.027
# Number of reflections without Friedels Law is 3255
# Number of reflections with Friedels Law is 1988
# Theoretical number of reflections is about 1864

_diffrn_reflns_theta_min         5.173
_diffrn_reflns_theta_max         27.093
_diffrn_measured_fraction_theta_max 0.987

_diffrn_reflns_theta_full        26.280
_diffrn_measured_fraction_theta_full 0.988

_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -12
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              8
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   2.85
_oxford_diffrn_Wilson_scale      1.64

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

_refine_diff_density_min         -0.29
_refine_diff_density_max         0.29

# 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         1988
_refine_ls_number_restraints     1
_refine_ls_number_parameters     227
_oxford_refine_ls_R_factor_ref   0.0500
_refine_ls_wR_factor_ref         0.0926
_refine_ls_goodness_of_fit_ref   0.9348
_refine_ls_shift/su_max          0.0001134
_refine_ls_shift/su_mean         0.0000556

# The values computed from all data
_oxford_reflns_number_all        1988
_refine_ls_R_factor_all          0.0500
_refine_ls_wR_factor_all         0.0926

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                1676
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_gt          0.0796

# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration unk

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    none # 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/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
10.5 14.7 6.96 1.84
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.

Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R.,
Munksgaard, Copenhagen, 291-294.

Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
O1 O 0.3956(2) 0.7171(3) 0.27189(17) 0.0325 1.0000 Uani . . . . . . .
C2 C 0.3964(3) 0.5446(5) 0.2553(2) 0.0254 1.0000 Uani . . . . . . .
N3 N 0.3695(3) 0.4029(4) 0.31362(18) 0.0255 1.0000 Uani . . . . . . .
C4 C 0.3849(3) 0.2100(5) 0.2779(2) 0.0258 1.0000 Uani . . . . . . .
C5 C 0.3950(3) 0.2378(5) 0.1674(2) 0.0285 1.0000 Uani . . . . . . .
C6 C 0.4342(3) 0.4555(5) 0.1625(2) 0.0266 1.0000 Uani . . . . . . .
C7 C 0.6006(3) 0.4849(5) 0.1756(2) 0.0271 1.0000 Uani . . . . . . .
C8 C 0.7051(3) 0.4036(5) 0.2770(2) 0.0282 1.0000 Uani . . . . . . .
C9 C 0.7422(4) 0.4798(6) 0.3818(2) 0.0369 1.0000 Uani . . . . . . .
C10 C 0.8436(4) 0.3625(6) 0.4459(3) 0.0416 1.0000 Uani . . . . . . .
O11 O 0.8743(2) 0.2154(5) 0.3908(2) 0.0482 1.0000 Uani . . . . . . .
C12 C 0.7885(3) 0.2433(5) 0.2867(3) 0.0370 1.0000 Uani . . . . . . .
C13 C 0.6350(3) 0.6978(5) 0.1679(2) 0.0312 1.0000 Uani . . . . . . .
N14 N 0.7884(3) 0.7198(4) 0.1631(2) 0.0336 1.0000 Uani . . . . . . .
O15 O 0.8768(3) 0.8214(4) 0.2283(2) 0.0465 1.0000 Uani . . . . . . .
O16 O 0.8171(3) 0.6349(4) 0.09216(19) 0.0471 1.0000 Uani . . . . . . .
C17 C 0.3323(3) 0.5373(5) 0.0593(2) 0.0293 1.0000 Uani . . . . . . .
O18 O 0.3660(2) 0.5664(4) -0.01808(16) 0.0351 1.0000 Uani . . . . . . .
O19 O 0.1957(2) 0.5636(4) 0.06347(17) 0.0414 1.0000 Uani . . . . . . .
C20 C 0.0856(4) 0.6376(7) -0.0317(3) 0.0472 1.0000 Uani . . . . . . .
C21 C 0.2495(4) 0.1162(5) 0.2923(3) 0.0341 1.0000 Uani . . . . . . .
O22 O 0.2434(2) 0.2059(3) 0.38686(17) 0.0339 1.0000 Uani . . . . . . .
C23 C 0.2772(3) 0.4055(5) 0.3827(2) 0.0272 1.0000 Uani . . . . . . .
C24 C 0.3642(4) 0.4699(6) 0.4936(2) 0.0378 1.0000 Uani . . . . . . .
C25 C 0.1363(3) 0.5210(5) 0.3335(3) 0.0341 1.0000 Uani . . . . . . .
H41 H 0.4789 0.1535 0.3279 0.0322 1.0000 Uiso R . . . . . .
H51 H 0.2966 0.2130 0.1148 0.0354 1.0000 Uiso R . . . . . .
H52 H 0.4713 0.1566 0.1563 0.0361 1.0000 Uiso R . . . . . .
H71 H 0.6229 0.4203 0.1160 0.0338 1.0000 Uiso R . . . . . .
H91 H 0.7021 0.5917 0.4016 0.0444 1.0000 Uiso R . . . . . .
H101 H 0.8891 0.3786 0.5206 0.0516 1.0000 Uiso R . . . . . .
H121 H 0.7898 0.1601 0.2324 0.0452 1.0000 Uiso R . . . . . .
H131 H 0.5649 0.7537 0.1024 0.0398 1.0000 Uiso R . . . . . .
H132 H 0.6337 0.7655 0.2320 0.0394 1.0000 Uiso R . . . . . .
H201 H -0.0050 0.6627 -0.0146 0.0721 1.0000 Uiso R . . . . . .
H202 H 0.0671 0.5407 -0.0883 0.0723 1.0000 Uiso R . . . . . .
H203 H 0.1252 0.7571 -0.0500 0.0727 1.0000 Uiso R . . . . . .
H211 H 0.1585 0.1467 0.2312 0.0400 1.0000 Uiso R . . . . . .
H212 H 0.2628 -0.0255 0.3022 0.0405 1.0000 Uiso R . . . . . .
H241 H 0.2994 0.4563 0.5360 0.0578 1.0000 Uiso R . . . . . .
H242 H 0.4547 0.3944 0.5230 0.0583 1.0000 Uiso R . . . . . .
H243 H 0.3876 0.6058 0.4890 0.0583 1.0000 Uiso R . . . . . .
H253 H 0.0753 0.5033 0.3794 0.0535 1.0000 Uiso R . . . . . .
H252 H 0.0848 0.4697 0.2633 0.0531 1.0000 Uiso R . . . . . .
H251 H 0.1632 0.6551 0.3315 0.0530 1.0000 Uiso R . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0396(12) 0.0240(11) 0.0392(11) -0.0014(10) 0.0200(9) -0.0009(10)
C2 0.0261(14) 0.0255(15) 0.0246(13) 0.0001(12) 0.0087(11) 0.0011(12)
N3 0.0281(11) 0.0245(12) 0.0257(11) -0.0016(10) 0.0113(9) 0.0001(10)
C4 0.0296(14) 0.0223(13) 0.0255(13) 0.0000(13) 0.0091(11) 0.0030(13)
C5 0.0339(14) 0.0269(16) 0.0268(13) -0.0024(13) 0.0128(11) -0.0003(13)
C6 0.0299(14) 0.0264(16) 0.0250(13) 0.0001(12) 0.0111(11) 0.0016(12)
C7 0.0289(14) 0.0285(16) 0.0261(13) 0.0011(12) 0.0123(11) 0.0019(12)
C8 0.0295(13) 0.0273(15) 0.0289(14) 0.0041(13) 0.0114(11) 0.0004(13)
C9 0.0403(16) 0.043(2) 0.0304(15) -0.0010(15) 0.0154(13) -0.0075(16)
C10 0.0347(16) 0.058(2) 0.0296(15) 0.0099(16) 0.0078(13) -0.0067(17)
O11 0.0353(12) 0.0536(16) 0.0515(14) 0.0246(14) 0.0090(10) 0.0056(13)
C12 0.0335(15) 0.0362(19) 0.0404(16) 0.0072(15) 0.0113(13) 0.0057(15)
C13 0.0285(14) 0.0301(16) 0.0377(15) 0.0036(14) 0.0148(12) 0.0025(14)
N14 0.0319(12) 0.0309(14) 0.0390(13) 0.0069(14) 0.0134(11) 0.0017(13)
O15 0.0355(12) 0.0334(13) 0.0626(16) -0.0025(13) 0.0062(11) -0.0013(11)
O16 0.0448(13) 0.0620(17) 0.0437(13) 0.0009(13) 0.0269(11) 0.0000(13)
C17 0.0321(14) 0.0293(16) 0.0271(14) -0.0002(13) 0.0107(11) 0.0021(13)
O18 0.0389(11) 0.0443(14) 0.0244(10) 0.0031(10) 0.0135(9) 0.0032(11)
O19 0.0318(11) 0.0640(17) 0.0285(10) 0.0095(12) 0.0104(9) 0.0113(12)
C20 0.0336(16) 0.073(3) 0.0349(16) 0.0104(18) 0.0107(13) 0.0161(19)
C21 0.0415(17) 0.0264(16) 0.0392(16) -0.0047(14) 0.0198(14) -0.0062(14)
O22 0.0452(12) 0.0261(11) 0.0385(11) 0.0015(10) 0.0250(10) -0.0022(11)
C23 0.0297(14) 0.0266(15) 0.0284(14) -0.0003(12) 0.0139(11) -0.0014(13)
C24 0.0439(17) 0.0443(19) 0.0274(15) -0.0016(15) 0.0147(13) 0.0029(17)
C25 0.0304(15) 0.0324(18) 0.0414(17) -0.0008(15) 0.0146(13) 0.0030(14)

_refine_ls_extinction_coef       180(20)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.794(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 . 1.227(4) yes
C2 . N3 . 1.340(4) yes
C2 . C6 . 1.543(4) yes
N3 . C4 . 1.456(4) yes
N3 . C23 . 1.480(3) yes
C4 . C5 . 1.534(4) yes
C4 . C21 . 1.519(4) yes
C4 . H41 . 1.004 no
C5 . C6 . 1.574(5) yes
C5 . H51 . 0.983 no
C5 . H52 . 0.974 no
C6 . C7 . 1.551(4) yes
C6 . C17 . 1.515(4) yes
C7 . C8 . 1.505(4) yes
C7 . C13 . 1.536(5) yes
C7 . H71 . 1.004 no
C8 . C9 . 1.436(4) yes
C8 . C12 . 1.356(5) yes
C9 . C10 . 1.338(5) yes
C9 . H91 . 0.947 no
C10 . O11 . 1.356(5) yes
C10 . H101 . 0.959 no
O11 . C12 . 1.378(4) yes
C12 . H121 . 0.937 no
C13 . N14 . 1.495(4) yes
C13 . H131 . 0.991 no
C13 . H132 . 0.987 no
N14 . O15 . 1.220(4) yes
N14 . O16 . 1.231(3) yes
C17 . O18 . 1.205(3) yes
C17 . O19 . 1.336(3) yes
O19 . C20 . 1.451(4) yes
C20 . H201 . 0.982 no
C20 . H202 . 0.991 no
C20 . H203 . 0.982 no
C21 . O22 . 1.437(4) yes
C21 . H211 . 0.997 no
C21 . H212 . 1.003 no
O22 . C23 . 1.438(4) yes
C23 . C24 . 1.511(4) yes
C23 . C25 . 1.517(4) yes
C24 . H241 . 0.978 no
C24 . H242 . 0.975 no
C24 . H243 . 0.983 no
C25 . H253 . 0.989 no
C25 . H252 . 0.975 no
C25 . H251 . 0.975 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 . N3 . 127.4(3) yes
O1 . C2 . C6 . 124.1(3) yes
N3 . C2 . C6 . 108.5(3) yes
C2 . N3 . C4 . 115.6(2) yes
C2 . N3 . C23 . 129.0(3) yes
C4 . N3 . C23 . 111.5(2) yes
N3 . C4 . C5 . 104.4(2) yes
N3 . C4 . C21 . 100.0(2) yes
C5 . C4 . C21 . 120.7(2) yes
N3 . C4 . H41 . 108.1 no
C5 . C4 . H41 . 111.5 no
C21 . C4 . H41 . 110.6 no
C4 . C5 . C6 . 104.8(2) yes
C4 . C5 . H51 . 108.6 no
C6 . C5 . H51 . 108.9 no
C4 . C5 . H52 . 111.6 no
C6 . C5 . H52 . 110.9 no
H51 . C5 . H52 . 111.7 no
C2 . C6 . C5 . 103.5(2) yes
C2 . C6 . C7 . 111.4(2) yes
C5 . C6 . C7 . 111.8(2) yes
C2 . C6 . C17 . 109.6(2) yes
C5 . C6 . C17 . 108.3(3) yes
C7 . C6 . C17 . 111.8(2) yes
C6 . C7 . C8 . 113.2(2) yes
C6 . C7 . C13 . 110.8(2) yes
C8 . C7 . C13 . 109.6(3) yes
C6 . C7 . H71 . 109.5 no
C8 . C7 . H71 . 107.5 no
C13 . C7 . H71 . 106.0 no
C7 . C8 . C9 . 128.3(3) yes
C7 . C8 . C12 . 126.1(3) yes
C9 . C8 . C12 . 105.6(3) yes
C8 . C9 . C10 . 106.9(3) yes
C8 . C9 . H91 . 126.3 no
C10 . C9 . H91 . 126.8 no
C9 . C10 . O11 . 110.9(3) yes
C9 . C10 . H101 . 125.3 no
O11 . C10 . H101 . 123.9 no
C10 . O11 . C12 . 106.5(3) yes
O11 . C12 . C8 . 110.1(3) yes
O11 . C12 . H121 . 123.0 no
C8 . C12 . H121 . 126.8 no
C7 . C13 . N14 . 109.7(3) yes
C7 . C13 . H131 . 110.3 no
N14 . C13 . H131 . 107.4 no
C7 . C13 . H132 . 110.0 no
N14 . C13 . H132 . 106.7 no
H131 . C13 . H132 . 112.6 no
C13 . N14 . O15 . 118.7(3) yes
C13 . N14 . O16 . 117.4(3) yes
O15 . N14 . O16 . 124.0(3) yes
C6 . C17 . O18 . 125.4(3) yes
C6 . C17 . O19 . 110.4(2) yes
O18 . C17 . O19 . 124.0(3) yes
C17 . O19 . C20 . 116.1(2) yes
O19 . C20 . H201 . 106.9 no
O19 . C20 . H202 . 108.9 no
H201 . C20 . H202 . 111.0 no
O19 . C20 . H203 . 107.4 no
H201 . C20 . H203 . 110.5 no
H202 . C20 . H203 . 111.9 no
C4 . C21 . O22 . 102.3(2) yes
C4 . C21 . H211 . 110.2 no
O22 . C21 . H211 . 110.6 no
C4 . C21 . H212 . 111.7 no
O22 . C21 . H212 . 110.7 no
H211 . C21 . H212 . 110.9 no
C21 . O22 . C23 . 108.2(2) yes
N3 . C23 . O22 . 101.6(2) yes
N3 . C23 . C24 . 112.2(2) yes
O22 . C23 . C24 . 107.9(3) yes
N3 . C23 . C25 . 111.1(2) yes
O22 . C23 . C25 . 110.8(2) yes
C24 . C23 . C25 . 112.6(3) yes
C23 . C24 . H241 . 107.6 no
C23 . C24 . H242 . 111.0 no
H241 . C24 . H242 . 110.9 no
C23 . C24 . H243 . 106.7 no
H241 . C24 . H243 . 109.4 no
H242 . C24 . H243 . 111.1 no
C23 . C25 . H253 . 106.4 no
C23 . C25 . H252 . 108.1 no
H253 . C25 . H252 . 110.4 no
C23 . C25 . H251 . 108.7 no
H253 . C25 . H251 . 110.6 no
H252 . C25 . H251 . 112.3 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 . O15 1_545 134 0.94 2.52 3.236(5) yes
C13 . H131 . O18 . 122 0.99 2.42 3.063(5) yes
C20 . H201 . O16 1_455 156 0.98 2.57 3.495(5) yes
C21 . H212 . O1 1_545 143 1.00 2.32 3.173(5) yes
_chemical_name_common            .

#==============================================================================
data_12
_database_code_depnum_ccdc_archive 'CCDC 805605'
#TrackingRef '- Publish Cif for compound 12.cif'

#==============================================================================

_audit_creation_date             10-11-04
_audit_creation_method           CRYSTALS_ver_14.11

_oxford_structure_analysis_title 009DJD10
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_refine_special_details          
;
The unit cell contains two independent molecules (Z'=2) related by a
pseudo 2-fold axis. The molecular geometries are very similar except
for the orientation of one of furan residues.

In one of the molecules, the furan residue is disordered by rotation
about the C36-C37x bond.
;

_cell_length_a                   9.0669(2)
_cell_length_b                   15.7455(4)
_cell_length_c                   12.0613(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.0302(13)
_cell_angle_gamma                90
_cell_volume                     1712.38(7)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21 '
_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 = C16.50 N2.50 O6
# Dc = 1.28 Fooo = 744.00 Mu = 1.01 M = 658.39
# Found Formula = C16 H20 N2 O7
# Dc = 1.37 FOOO = 744.00 Mu = 1.08 M = 704.69

_chemical_formula_sum            'C16 H20 N2 O7'
_chemical_formula_moiety         'C16 H20 N2 O7'
_chemical_compound_source        .
_chemical_formula_weight         352.34

_cell_measurement_reflns_used    3777
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    123

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.060
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_max          0.340

_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.108

# Sheldrick geometric approximatio 0.98 0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.87
_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       \w

# 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      123
_diffrn_reflns_number            15585
_reflns_number_total             4032
_diffrn_reflns_av_R_equivalents  0.044
# Number of reflections without Friedels Law is 7161
# Number of reflections with Friedels Law is 4032
# Theoretical number of reflections is about 3922

_diffrn_reflns_theta_min         5.099
_diffrn_reflns_theta_max         27.470
_diffrn_measured_fraction_theta_max 0.990

_diffrn_reflns_theta_full        26.646
_diffrn_measured_fraction_theta_full 0.991

_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              20
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   2.97
_oxford_diffrn_Wilson_scale      5.65

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

_refine_diff_density_min         -0.44
_refine_diff_density_max         0.46

# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold

# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns         4032
_refine_ls_number_restraints     91
_refine_ls_number_parameters     489
_oxford_refine_ls_R_factor_ref   0.0794
_refine_ls_wR_factor_ref         0.0978
_refine_ls_goodness_of_fit_ref   0.9620
_refine_ls_shift/su_max          0.0226392
_refine_ls_shift/su_mean         0.0005859

# The values computed from all data
_oxford_reflns_number_all        4032
_refine_ls_R_factor_all          0.0794
_refine_ls_wR_factor_all         0.0978

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                2716
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_gt          0.0854

# 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    none # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.19P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.

Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R.,
Munksgaard, Copenhagen, 291-294.

Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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 0.4200(2) 0.78721(15) 0.25368(16) 0.0335 1.0000 Uani . . . . . .
C2 C 0.4287(3) 0.7929(2) 0.3551(2) 0.0265 1.0000 Uani . . . . . .
N3 N 0.4977(3) 0.73968(16) 0.4304(2) 0.0298 1.0000 Uani . . . . . .
C4 C 0.4886(3) 0.7625(2) 0.5468(2) 0.0324 1.0000 Uani . . . . . .
C5 C 0.4313(4) 0.8538(2) 0.5411(2) 0.0332 1.0000 Uani . . . . . .
C6 C 0.3576(3) 0.8646(2) 0.4201(2) 0.0290 1.0000 Uani . . . . . .
C7 C 0.3967(4) 0.9463(2) 0.3611(3) 0.0328 1.0000 Uani . . . . . .
O8 O 0.5393(3) 0.96688(15) 0.38930(19) 0.0406 1.0000 Uani . . . . . .
C9 C 0.5978(4) 1.0378(2) 0.3302(3) 0.0471 1.0000 Uani . . . . . .
O10 O 0.3139(3) 0.98427(16) 0.29416(19) 0.0434 1.0000 Uani . . . . . .
C11 C 0.1868(3) 0.8528(2) 0.4037(2) 0.0303 1.0000 Uani . . . . . .
C12 C 0.1419(3) 0.7643(2) 0.4330(2) 0.0287 1.0000 Uani . . . . . .
C13 C 0.0951(4) 0.7356(2) 0.5295(3) 0.0348 1.0000 Uani . . . . . .
O14 O 0.0694(3) 0.64996(16) 0.52418(19) 0.0421 1.0000 Uani . . . . . .
C15 C 0.1010(4) 0.6254(2) 0.4210(3) 0.0365 1.0000 Uani . . . . . .
C16 C 0.1458(4) 0.6915(2) 0.3637(3) 0.0396 1.0000 Uani . . . . . .
C17 C 0.1107(3) 0.9208(2) 0.4679(3) 0.0334 1.0000 Uani . . . . . .
N18 N -0.0533(3) 0.91959(19) 0.4348(2) 0.0375 1.0000 Uani . . . . . .
O19 O -0.0974(3) 0.9171(2) 0.33607(18) 0.0576 1.0000 Uani . . . . . .
O20 O -0.1349(3) 0.92115(19) 0.50922(19) 0.0472 1.0000 Uani . . . . . .
C21 C 0.6474(4) 0.7423(3) 0.5932(3) 0.0418 1.0000 Uani . . . . . .
O22 O 0.6800(3) 0.66721(18) 0.53183(18) 0.0488 1.0000 Uani . . . . . .
C23 C 0.6171(4) 0.6777(2) 0.4170(3) 0.0390 1.0000 Uani . . . . . .
C24 C 0.5552(5) 0.5932(3) 0.3776(3) 0.0578 1.0000 Uani . . . . . .
C25 C 0.7292(4) 0.7135(3) 0.3468(3) 0.0548 1.0000 Uani . . . . . .
O26 O 0.8686(2) 0.36604(15) 0.25733(16) 0.0391 1.0000 Uani . . . . . .
C27 C 0.8709(3) 0.3575(2) 0.1555(2) 0.0301 1.0000 Uani . . . . . .
N28 N 0.9317(3) 0.41015(17) 0.08660(19) 0.0306 1.0000 Uani . . . . . .
C29 C 0.9181(4) 0.3837(2) -0.0307(2) 0.0342 1.0000 Uani . . . . . .
C30 C 0.8591(4) 0.2922(2) -0.0276(2) 0.0350 1.0000 Uani . . . . . .
C31 C 0.7977(3) 0.2834(2) 0.0873(2) 0.0299 1.0000 Uani . . . . . .
C32 C 0.8484(4) 0.2018(2) 0.1492(3) 0.0349 1.0000 Uani . . . . . .
O33 O 0.7694(3) 0.15573(17) 0.1949(2) 0.0525 1.0000 Uani . . . . . .
O34 O 0.9938(2) 0.19109(16) 0.14880(19) 0.0411 1.0000 Uani . . . . . .
C35 C 1.0585(4) 0.1166(2) 0.2065(3) 0.0442 1.0000 Uani . . . . . .
C36 C 0.6267(4) 0.2924(2) 0.0870(3) 0.0340 1.0000 Uani . . . . . .
C42 C 0.5471(4) 0.2266(2) 0.0107(3) 0.0410 1.0000 Uani . . . . . .
N43 N 0.3861(3) 0.2203(2) 0.0297(3) 0.0458 1.0000 Uani . . . . . .
O44 O 0.2970(3) 0.2097(2) -0.0506(2) 0.0648 1.0000 Uani . . . . . .
O45 O 0.3528(3) 0.2268(3) 0.1229(2) 0.1025 1.0000 Uani . . . . . .
C46 C 1.0748(4) 0.4008(3) -0.0558(3) 0.0462 1.0000 Uani . . . . . .
O47 O 1.1094(3) 0.47872(18) 0.00390(19) 0.0531 1.0000 Uani . . . . . .
C48 C 1.0472(4) 0.4759(2) 0.1084(3) 0.0396 1.0000 Uani . . . . . .
C49 C 0.9789(5) 0.5615(2) 0.1266(3) 0.0581 1.0000 Uani . . . . . .
C50 C 1.1633(4) 0.4494(3) 0.2018(3) 0.0533 1.0000 Uani . . . . . .
H41 H 0.4192 0.7254 0.5797 0.0382 1.0000 Uiso R . . . . .
H51 H 0.5106 0.8945 0.5569 0.0405 1.0000 Uiso R . . . . .
H52 H 0.3632 0.8627 0.5935 0.0400 1.0000 Uiso R . . . . .
H93 H 0.6807 1.0614 0.3762 0.0715 1.0000 Uiso R . . . . .
H92 H 0.5204 1.0787 0.3119 0.0710 1.0000 Uiso R . . . . .
H91 H 0.6331 1.0160 0.2627 0.0716 1.0000 Uiso R . . . . .
H111 H 0.1544 0.8609 0.3236 0.0353 1.0000 Uiso R . . . . .
H131 H 0.0815 0.7681 0.5916 0.0424 1.0000 Uiso R . . . . .
H151 H 0.0925 0.5688 0.3981 0.0442 1.0000 Uiso R . . . . .
H161 H 0.1747 0.6888 0.2908 0.0468 1.0000 Uiso R . . . . .
H171 H 0.1455 0.9765 0.4465 0.0410 1.0000 Uiso R . . . . .
H172 H 0.1277 0.9124 0.5467 0.0408 1.0000 Uiso R . . . . .
H211 H 0.7142 0.7886 0.5790 0.0500 1.0000 Uiso R . . . . .
H212 H 0.6555 0.7283 0.6733 0.0498 1.0000 Uiso R . . . . .
H241 H 0.6348 0.5526 0.3821 0.0850 1.0000 Uiso R . . . . .
H242 H 0.4806 0.5754 0.4256 0.0847 1.0000 Uiso R . . . . .
H243 H 0.5104 0.5974 0.2989 0.0840 1.0000 Uiso R . . . . .
H253 H 0.8074 0.6715 0.3472 0.0809 1.0000 Uiso R . . . . .
H252 H 0.7687 0.7669 0.3774 0.0808 1.0000 Uiso R . . . . .
H251 H 0.6832 0.7222 0.2720 0.0799 1.0000 Uiso R . . . . .
H291 H 0.8468 0.4210 -0.0754 0.0406 1.0000 Uiso R . . . . .
H301 H 0.9393 0.2520 -0.0328 0.0421 1.0000 Uiso R . . . . .
H302 H 0.7837 0.2824 -0.0884 0.0415 1.0000 Uiso R . . . . .
H353 H 1.1583 0.1119 0.1856 0.0667 1.0000 Uiso R . . . . .
H352 H 1.0613 0.1239 0.2856 0.0671 1.0000 Uiso R . . . . .
H351 H 1.0022 0.0673 0.1834 0.0675 1.0000 Uiso R . . . . .
H361 H 0.6034 0.2794 0.1623 0.0402 1.0000 Uiso R . . . . .
H421 H 0.5563 0.2419 -0.0660 0.0493 1.0000 Uiso R . . . . .
H422 H 0.5928 0.1711 0.0269 0.0494 1.0000 Uiso R . . . . .
H461 H 1.0858 0.4089 -0.1345 0.0549 1.0000 Uiso R . . . . .
H462 H 1.1416 0.3554 -0.0285 0.0547 1.0000 Uiso R . . . . .
H491 H 1.0556 0.6043 0.1323 0.0857 1.0000 Uiso R . . . . .
H492 H 0.9057 0.5749 0.0653 0.0851 1.0000 Uiso R . . . . .
H493 H 0.9330 0.5616 0.1965 0.0858 1.0000 Uiso R . . . . .
H503 H 1.2359 0.4942 0.2141 0.0797 1.0000 Uiso R . . . . .
H502 H 1.2097 0.3981 0.1829 0.0798 1.0000 Uiso R . . . . .
H501 H 1.1152 0.4395 0.2686 0.0793 1.0000 Uiso R . . . . .
C380 C 0.5398(11) 0.4420(4) 0.1310(3) 0.0363 0.607(14) Uani D . P 1 2 .
C381 C 0.5780(18) 0.4492(5) 0.1385(6) 0.0416 0.393(14) Uani D . P 1 1 .
O390 O 0.4860(8) 0.5133(3) 0.0756(6) 0.0424 0.607(14) Uani D . P 1 2 .
C391 C 0.535(2) 0.5200(5) 0.0822(12) 0.0427 0.393(14) Uani D . P 1 1 .
C400 C 0.4619(15) 0.4941(5) -0.0346(7) 0.0508 0.607(14) Uani D . P 1 2 .
O401 O 0.5107(13) 0.5003(5) -0.0280(9) 0.0419 0.393(14) Uani D . P 1 1 .
C410 C 0.5121(13) 0.4151(5) -0.0495(4) 0.0459 0.607(14) Uani D . P 1 2 .
C411 C 0.5479(16) 0.4172(6) -0.0400(5) 0.0415 0.393(14) Uani D . P 1 1 .
C370 C 0.5688(4) 0.38152(16) 0.0573(2) 0.0353 0.607(14) Uani D . P 1 2 .
C371 C 0.5738(4) 0.38027(16) 0.0611(2) 0.0352 0.393(14) Uani D . P 1 1 .
H3801 H 0.5482 0.4347 0.2103 0.0414 0.607(14) Uiso R . P 1 2 .
H3811 H 0.6099 0.4467 0.2160 0.0500 0.393(14) Uiso R . P 1 1 .
H3911 H 0.5193 0.5732 0.1128 0.0509 0.393(14) Uiso R . P 1 1 .
H4001 H 0.4125 0.5295 -0.0895 0.0521 0.607(14) Uiso R . P 1 2 .
H4101 H 0.5061 0.3866 -0.1167 0.0484 0.607(14) Uiso R . P 1 2 .
H4111 H 0.5602 0.3914 -0.1077 0.0512 0.393(14) Uiso R . P 1 1 .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0418(12) 0.0373(13) 0.0217(11) -0.0019(10) 0.0054(9) 0.0004(11)
C2 0.0269(15) 0.0255(18) 0.0274(16) 0.0000(13) 0.0039(12) -0.0011(13)
N3 0.0376(14) 0.0257(15) 0.0260(13) -0.0013(11) 0.0030(11) 0.0009(12)
C4 0.0393(17) 0.033(2) 0.0240(16) 0.0027(14) -0.0008(13) -0.0024(15)
C5 0.0421(18) 0.0310(19) 0.0265(16) -0.0024(14) 0.0032(13) 0.0009(15)
C6 0.0351(16) 0.0236(17) 0.0276(15) 0.0003(13) 0.0000(12) -0.0043(14)
C7 0.0394(18) 0.0269(18) 0.0322(17) -0.0018(14) 0.0051(14) -0.0014(15)
O8 0.0373(13) 0.0354(14) 0.0489(14) 0.0069(11) 0.0044(10) -0.0071(11)
C9 0.050(2) 0.035(2) 0.058(2) 0.0022(18) 0.0088(18) -0.0132(18)
O10 0.0465(14) 0.0352(14) 0.0472(13) 0.0123(12) -0.0019(11) -0.0005(11)
C11 0.0345(16) 0.0275(18) 0.0279(15) -0.0001(14) -0.0019(12) -0.0012(14)
C12 0.0315(16) 0.0285(19) 0.0262(16) -0.0029(13) 0.0033(12) 0.0009(14)
C13 0.0453(19) 0.030(2) 0.0292(17) -0.0016(14) 0.0023(14) -0.0061(15)
O14 0.0503(14) 0.0359(15) 0.0402(13) 0.0049(11) 0.0051(11) -0.0033(12)
C15 0.0435(19) 0.0301(19) 0.0360(18) -0.0095(16) 0.0044(15) -0.0041(16)
C16 0.049(2) 0.031(2) 0.0401(18) -0.0062(16) 0.0083(15) -0.0047(17)
C17 0.0372(18) 0.0327(19) 0.0307(16) -0.0020(15) 0.0052(13) 0.0002(15)
N18 0.0417(16) 0.0350(17) 0.0357(15) -0.0022(13) 0.0028(13) 0.0121(14)
O19 0.0520(15) 0.090(2) 0.0296(13) -0.0021(14) -0.0016(11) 0.0218(16)
O20 0.0418(13) 0.0619(18) 0.0396(13) -0.0046(13) 0.0116(11) 0.0028(13)
C21 0.050(2) 0.052(2) 0.0226(16) -0.0034(16) -0.0043(14) 0.0095(17)
O22 0.0535(15) 0.0575(18) 0.0337(13) 0.0030(12) -0.0036(10) 0.0200(13)
C23 0.0439(19) 0.040(2) 0.0326(17) 0.0034(16) 0.0011(14) 0.0130(17)
C24 0.082(3) 0.034(2) 0.055(2) -0.0065(19) 0.001(2) 0.019(2)
C25 0.040(2) 0.079(3) 0.045(2) 0.002(2) 0.0056(16) 0.014(2)
O26 0.0547(14) 0.0365(14) 0.0259(11) -0.0012(11) 0.0040(9) -0.0036(12)
C27 0.0416(18) 0.0287(18) 0.0210(15) 0.0018(14) 0.0073(13) 0.0009(15)
N28 0.0426(14) 0.0276(15) 0.0218(12) -0.0015(11) 0.0047(10) -0.0029(13)
C29 0.0477(19) 0.037(2) 0.0183(14) 0.0000(14) 0.0048(13) 0.0014(16)
C30 0.0473(18) 0.0280(19) 0.0294(16) -0.0018(14) 0.0028(14) -0.0009(16)
C31 0.0431(17) 0.0236(17) 0.0229(14) 0.0024(13) 0.0030(12) -0.0015(15)
C32 0.0414(19) 0.031(2) 0.0323(17) -0.0005(15) 0.0015(15) -0.0007(16)
O33 0.0556(16) 0.0414(16) 0.0622(16) 0.0244(14) 0.0139(13) 0.0012(13)
O34 0.0433(14) 0.0330(14) 0.0465(13) 0.0083(11) 0.0015(11) 0.0040(11)
C35 0.052(2) 0.034(2) 0.045(2) 0.0057(17) -0.0017(16) 0.0098(17)
C36 0.0451(18) 0.0284(19) 0.0288(16) 0.0025(14) 0.0052(14) -0.0017(16)
C42 0.0437(19) 0.028(2) 0.052(2) 0.0006(16) 0.0061(17) -0.0038(16)
N43 0.0469(18) 0.043(2) 0.0480(19) 0.0024(15) 0.0076(15) -0.0092(15)
O44 0.0495(15) 0.085(2) 0.0576(16) -0.0122(16) -0.0043(13) -0.0150(16)
O45 0.070(2) 0.194(5) 0.0461(17) -0.002(2) 0.0198(15) -0.049(2)
C46 0.057(2) 0.053(3) 0.0310(17) -0.0025(17) 0.0158(16) -0.0122(19)
O47 0.0731(18) 0.0547(18) 0.0331(13) 0.0004(12) 0.0125(12) -0.0310(14)
C48 0.052(2) 0.037(2) 0.0304(17) 0.0022(16) 0.0063(15) -0.0105(17)
C49 0.093(3) 0.028(2) 0.051(2) -0.0015(17) -0.002(2) -0.007(2)
C50 0.050(2) 0.066(3) 0.043(2) 0.0004(19) 0.0020(17) -0.009(2)
C380 0.045(5) 0.032(4) 0.032(3) -0.008(3) 0.002(3) 0.007(3)
C381 0.045(6) 0.027(5) 0.053(5) 0.004(4) 0.008(4) 0.004(4)
O390 0.057(5) 0.031(3) 0.038(3) -0.009(2) -0.001(2) 0.009(2)
C391 0.048(7) 0.026(5) 0.054(5) -0.001(4) 0.004(5) 0.008(5)
C400 0.065(6) 0.043(4) 0.043(4) -0.009(3) -0.003(4) 0.017(4)
O401 0.047(6) 0.033(4) 0.043(4) 0.009(3) -0.008(3) 0.014(3)
C410 0.063(5) 0.035(4) 0.037(3) -0.005(3) -0.004(3) 0.014(3)
C411 0.044(6) 0.033(5) 0.045(5) 0.009(4) -0.005(4) 0.009(4)
C370 0.0484(18) 0.0283(17) 0.0284(16) -0.0048(14) 0.0003(14) 0.0067(15)
C371 0.0375(18) 0.0273(17) 0.0401(16) 0.0100(14) 0.0010(14) 0.0018(15)

_refine_ls_extinction_coef       770(60)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.4375(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 . 1.221(3) yes
C2 . N3 . 1.341(4) yes
C2 . C6 . 1.552(4) yes
N3 . C4 . 1.460(4) yes
N3 . C23 . 1.479(4) yes
C4 . C5 . 1.528(5) yes
C4 . C21 . 1.522(4) yes
C4 . H41 . 0.973 no
C5 . C6 . 1.549(4) yes
C5 . H51 . 0.967 no
C5 . H52 . 0.939 no
C6 . C7 . 1.529(4) yes
C6 . C11 . 1.552(4) yes
C7 . O8 . 1.342(4) yes
C7 . O10 . 1.202(4) yes
O8 . C9 . 1.454(4) yes
C9 . H93 . 0.962 no
C9 . H92 . 0.961 no
C9 . H91 . 0.968 no
C11 . C12 . 1.504(4) yes
C11 . C17 . 1.528(5) yes
C11 . H111 . 0.987 no
C12 . C13 . 1.357(4) yes
C12 . C16 . 1.421(5) yes
C13 . O14 . 1.368(4) yes
C13 . H131 . 0.927 no
O14 . C15 . 1.363(4) yes
C15 . C16 . 1.337(5) yes
C15 . H151 . 0.932 no
C16 . H161 . 0.944 no
C17 . N18 . 1.499(4) yes
C17 . H171 . 0.976 no
C17 . H172 . 0.956 no
N18 . O19 . 1.216(3) yes
N18 . O20 . 1.222(3) yes
C21 . O22 . 1.441(4) yes
C21 . H211 . 0.974 no
C21 . H212 . 0.987 no
O22 . C23 . 1.451(4) yes
C23 . C24 . 1.502(5) yes
C23 . C25 . 1.499(5) yes
C24 . H241 . 0.961 no
C24 . H242 . 0.977 no
C24 . H243 . 0.995 no
C25 . H253 . 0.968 no
C25 . H252 . 0.972 no
C25 . H251 . 0.964 no
O26 . C27 . 1.238(3) yes
C27 . N28 . 1.333(4) yes
C27 . C31 . 1.538(4) yes
N28 . C29 . 1.467(4) yes
N28 . C48 . 1.477(4) yes
C29 . C30 . 1.538(5) yes
C29 . C46 . 1.508(5) yes
C29 . H291 . 0.990 no
C30 . C31 . 1.553(4) yes
C30 . H301 . 0.971 no
C30 . H302 . 0.961 no
C31 . C32 . 1.532(5) yes
C31 . C36 . 1.557(4) yes
C32 . O33 . 1.194(4) yes
C32 . O34 . 1.330(4) yes
O34 . C35 . 1.455(4) yes
C35 . H353 . 0.967 no
C35 . H352 . 0.959 no
C35 . H351 . 0.954 no
C36 . C42 . 1.517(5) yes
C36 . H361 . 0.976 no
C36 . C371 . 1.486(4) yes
C36 . C42 . 1.517(5) yes
C36 . H361 . 0.976 no
C36 . C370 . 1.527(4) yes
C42 . N43 . 1.505(5) yes
C42 . H421 . 0.968 no
C42 . H422 . 0.979 no
N43 . O44 . 1.205(4) yes
N43 . O45 . 1.199(4) yes
C46 . O47 . 1.440(4) yes
C46 . H461 . 0.973 no
C46 . H462 . 0.972 no
O47 . C48 . 1.435(4) yes
C48 . C49 . 1.509(5) yes
C48 . C50 . 1.517(5) yes
C49 . H491 . 0.965 no
C49 . H492 . 0.964 no
C49 . H493 . 0.979 no
C50 . H503 . 0.966 no
C50 . H502 . 0.951 no
C50 . H501 . 0.969 no
C380 . O390 . 1.368(5) yes
C380 . C370 . 1.348(5) yes
C380 . H3801 . 0.959 no
C381 . C391 . 1.343(7) yes
C381 . C371 . 1.429(7) yes
C381 . H3811 . 0.950 no
O390 . C400 . 1.358(6) yes
C391 . O401 . 1.360(7) yes
C391 . H3911 . 0.931 no
C400 . C410 . 1.344(5) yes
C400 . H4001 . 0.942 no
O401 . C411 . 1.363(6) yes
C410 . C370 . 1.437(6) yes
C410 . H4101 . 0.923 no
C411 . C371 . 1.349(7) yes
C411 . H4111 . 0.929 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 . N3 . 127.5(3) yes
O1 . C2 . C6 . 124.9(3) yes
N3 . C2 . C6 . 107.6(2) yes
C2 . N3 . C4 . 115.3(2) yes
C2 . N3 . C23 . 129.3(3) yes
C4 . N3 . C23 . 112.5(2) yes
N3 . C4 . C5 . 104.0(2) yes
N3 . C4 . C21 . 98.9(2) yes
C5 . C4 . C21 . 121.1(3) yes
N3 . C4 . H41 . 110.4 no
C5 . C4 . H41 . 110.6 no
C21 . C4 . H41 . 110.6 no
C4 . C5 . C6 . 104.8(2) yes
C4 . C5 . H51 . 111.8 no
C6 . C5 . H51 . 110.5 no
C4 . C5 . H52 . 110.7 no
C6 . C5 . H52 . 111.7 no
H51 . C5 . H52 . 107.3 no
C5 . C6 . C2 . 103.6(2) yes
C5 . C6 . C7 . 115.6(2) yes
C2 . C6 . C7 . 104.4(2) yes
C5 . C6 . C11 . 115.6(2) yes
C2 . C6 . C11 . 108.1(2) yes
C7 . C6 . C11 . 108.6(2) yes
C6 . C7 . O8 . 110.5(3) yes
C6 . C7 . O10 . 124.9(3) yes
O8 . C7 . O10 . 124.5(3) yes
C7 . O8 . C9 . 116.9(2) yes
O8 . C9 . H93 . 108.5 no
O8 . C9 . H92 . 109.4 no
H93 . C9 . H92 . 112.4 no
O8 . C9 . H91 . 108.1 no
H93 . C9 . H91 . 108.4 no
H92 . C9 . H91 . 110.0 no
C6 . C11 . C12 . 111.8(3) yes
C6 . C11 . C17 . 110.4(2) yes
C12 . C11 . C17 . 112.5(3) yes
C6 . C11 . H111 . 107.5 no
C12 . C11 . H111 . 106.8 no
C17 . C11 . H111 . 107.6 no
C11 . C12 . C13 . 128.8(3) yes
C11 . C12 . C16 . 125.8(3) yes
C13 . C12 . C16 . 105.4(3) yes
C12 . C13 . O14 . 110.8(3) yes
C12 . C13 . H131 . 126.1 no
O14 . C13 . H131 . 123.1 no
C13 . O14 . C15 . 105.8(3) yes
O14 . C15 . C16 . 110.8(3) yes
O14 . C15 . H151 . 121.5 no
C16 . C15 . H151 . 127.7 no
C12 . C16 . C15 . 107.3(3) yes
C12 . C16 . H161 . 127.6 no
C15 . C16 . H161 . 125.1 no
C11 . C17 . N18 . 110.1(2) yes
C11 . C17 . H171 . 108.7 no
N18 . C17 . H171 . 106.2 no
C11 . C17 . H172 . 112.0 no
N18 . C17 . H172 . 108.4 no
H171 . C17 . H172 . 111.3 no
C17 . N18 . O19 . 118.4(3) yes
C17 . N18 . O20 . 117.7(2) yes
O19 . N18 . O20 . 123.9(3) yes
C4 . C21 . O22 . 102.7(3) yes
C4 . C21 . H211 . 111.2 no
O22 . C21 . H211 . 111.0 no
C4 . C21 . H212 . 112.2 no
O22 . C21 . H212 . 108.8 no
H211 . C21 . H212 . 110.8 no
C21 . O22 . C23 . 108.4(2) yes
N3 . C23 . O22 . 100.9(2) yes
N3 . C23 . C24 . 111.5(3) yes
O22 . C23 . C24 . 107.3(3) yes
N3 . C23 . C25 . 111.2(3) yes
O22 . C23 . C25 . 111.1(3) yes
C24 . C23 . C25 . 114.0(3) yes
C23 . C24 . H241 . 108.5 no
C23 . C24 . H242 . 109.0 no
H241 . C24 . H242 . 109.7 no
C23 . C24 . H243 . 110.1 no
H241 . C24 . H243 . 109.2 no
H242 . C24 . H243 . 110.2 no
C23 . C25 . H253 . 106.3 no
C23 . C25 . H252 . 110.8 no
H253 . C25 . H252 . 110.4 no
C23 . C25 . H251 . 109.2 no
H253 . C25 . H251 . 110.3 no
H252 . C25 . H251 . 109.7 no
O26 . C27 . N28 . 127.0(3) yes
O26 . C27 . C31 . 124.2(3) yes
N28 . C27 . C31 . 108.8(2) yes
C27 . N28 . C29 . 115.2(3) yes
C27 . N28 . C48 . 131.1(2) yes
C29 . N28 . C48 . 110.9(2) yes
N28 . C29 . C30 . 103.7(2) yes
N28 . C29 . C46 . 99.1(2) yes
C30 . C29 . C46 . 120.6(3) yes
N28 . C29 . H291 . 110.0 no
C30 . C29 . H291 . 111.0 no
C46 . C29 . H291 . 111.1 no
C29 . C30 . C31 . 105.3(2) yes
C29 . C30 . H301 . 110.1 no
C31 . C30 . H301 . 109.9 no
C29 . C30 . H302 . 110.8 no
C31 . C30 . H302 . 111.8 no
H301 . C30 . H302 . 108.9 no
C27 . C31 . C30 . 103.6(2) yes
C27 . C31 . C32 . 106.6(2) yes
C30 . C31 . C32 . 113.1(3) yes
C27 . C31 . C36 . 107.8(3) yes
C30 . C31 . C36 . 116.1(2) yes
C32 . C31 . C36 . 109.0(3) yes
C31 . C32 . O33 . 124.8(3) yes
C31 . C32 . O34 . 110.6(3) yes
O33 . C32 . O34 . 124.5(3) yes
C32 . O34 . C35 . 116.8(3) yes
O34 . C35 . H353 . 106.2 no
O34 . C35 . H352 . 110.3 no
H353 . C35 . H352 . 109.8 no
O34 . C35 . H351 . 109.9 no
H353 . C35 . H351 . 110.3 no
H352 . C35 . H351 . 110.3 no
C31 . C36 . C42 . 110.4(3) yes
C31 . C36 . H361 . 106.9 no
C42 . C36 . H361 . 106.6 no
C31 . C36 . C371 . 112.6(3) yes
C42 . C36 . C371 . 112.7(3) yes
H361 . C36 . C371 . 107.2 no
C31 . C36 . C42 . 110.4(3) yes
C31 . C36 . H361 . 106.9 no
C42 . C36 . H361 . 106.6 no
C31 . C36 . C370 . 113.7(3) yes
C42 . C36 . C370 . 110.8(3) yes
H361 . C36 . C370 . 108.0 no
C36 . C42 . N43 . 111.1(3) yes
C36 . C42 . H421 . 109.0 no
N43 . C42 . H421 . 110.1 no
C36 . C42 . H422 . 108.9 no
N43 . C42 . H422 . 107.9 no
H421 . C42 . H422 . 109.7 no
C42 . N43 . O44 . 117.7(3) yes
C42 . N43 . O45 . 118.7(3) yes
O44 . N43 . O45 . 123.5(3) yes
C29 . C46 . O47 . 102.2(3) yes
C29 . C46 . H461 . 114.5 no
O47 . C46 . H461 . 109.7 no
C29 . C46 . H462 . 111.6 no
O47 . C46 . H462 . 111.2 no
H461 . C46 . H462 . 107.6 no
C46 . O47 . C48 . 109.2(2) yes
N28 . C48 . O47 . 101.6(2) yes
N28 . C48 . C49 . 111.0(3) yes
O47 . C48 . C49 . 107.8(3) yes
N28 . C48 . C50 . 111.3(3) yes
O47 . C48 . C50 . 110.7(3) yes
C49 . C48 . C50 . 113.7(3) yes
C48 . C49 . H491 . 109.3 no
C48 . C49 . H492 . 110.1 no
H491 . C49 . H492 . 109.7 no
C48 . C49 . H493 . 110.1 no
H491 . C49 . H493 . 107.8 no
H492 . C49 . H493 . 109.9 no
C48 . C50 . H503 . 108.8 no
C48 . C50 . H502 . 110.3 no
H503 . C50 . H502 . 110.2 no
C48 . C50 . H501 . 108.9 no
H503 . C50 . H501 . 110.4 no
H502 . C50 . H501 . 108.2 no
O390 . C380 . C370 . 110.00(9) yes
O390 . C380 . H3801 . 124.9 no
C370 . C380 . H3801 . 124.9 no
C391 . C381 . C371 . 108.29(9) yes
C391 . C381 . H3811 . 125.1 no
C371 . C381 . H3811 . 126.6 no
C380 . O390 . C400 . 107.95(9) yes
C381 . C391 . O401 . 108.24(9) yes
C381 . C391 . H3911 . 126.4 no
O401 . C391 . H3911 . 125.3 no
O390 . C400 . C410 . 108.34(9) yes
O390 . C400 . H4001 . 125.0 no
C410 . C400 . H4001 . 126.6 no
C391 . O401 . C411 . 107.87(9) yes
C400 . C410 . C370 . 108.35(9) yes
C400 . C410 . H4101 . 125.4 no
C370 . C410 . H4101 . 126.2 no
O401 . C411 . C371 . 109.85(10) yes
O401 . C411 . H4111 . 124.5 no
C371 . C411 . H4111 . 125.5 no
C36 . C370 . C410 . 129.0(3) yes
C36 . C370 . C380 . 125.5(3) yes
C410 . C370 . C380 . 104.77(9) yes
C36 . C371 . C381 . 125.7(4) yes
C36 . C371 . C411 . 127.8(4) yes
C381 . C371 . C411 . 104.67(10) yes
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 . O26 2_656 160 0.93 2.39 3.281(6) yes
C15 . H151 . O20 2_546 136 0.93 2.59 3.330(6) yes
C17 . H172 . O26 2_656 168 0.96 2.47 3.410(6) yes
C21 . H212 . O45 2_656 166 0.99 2.47 3.433(6) yes
C30 . H302 . O1 2_645 169 0.96 2.57 3.520(6) yes
C42 . H421 . O1 2_645 177 0.97 2.40 3.372(6) yes
C46 . H461 . O19 2_645 174 0.97 2.45 3.417(6) yes
C50 . H501 . O26 . 120 0.97 2.51 3.112(6) yes
C410 . H4101 . O1 2_645 157 0.92 2.42 3.289(6) yes
C411 . H4101 . O1 2_645 141.1(11) 1.076(12) 2.421(6) 3.328(6) yes
C410 . H4111 . O1 2_645 152.1(16) 0.941(14) 2.427(8) 3.289(6) yes
C411 . H4111 . O1 2_645 163 0.93 2.43 3.328(6) yes

_iucr_refine_instruction_details_constraints 
;
#
# Punched on 04/11/10 at 09:23:26
#
#LIST 12
BLOCK SCALE X'S, U'S
CONT EXTPARAM
RIDE C ( 4,X'S) H ( 41,X'S)
RIDE C ( 5,X'S) H ( 51,X'S) H ( 52,X'S)
RIDE C ( 9,X'S) H ( 93,X'S) H ( 92,X'S) H ( 91,X'S)
RIDE C ( 11,X'S) H ( 111,X'S)
RIDE C ( 13,X'S) H ( 131,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 ( 21,X'S) H ( 211,X'S) H ( 212,X'S)
RIDE C ( 24,X'S) H ( 241,X'S) H ( 242,X'S) H ( 243,X'S)
RIDE C ( 25,X'S) H ( 253,X'S) H ( 252,X'S) H ( 251,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 ( 35,X'S) H ( 353,X'S) H ( 352,X'S) H ( 351,X'S)
RIDE C ( 36,X'S) H ( 361,X'S)
RIDE C ( 42,X'S) H ( 421,X'S) H ( 422,X'S)
RIDE C ( 46,X'S) H ( 461,X'S) H ( 462,X'S)
RIDE C ( 49,X'S) H ( 491,X'S) H ( 492,X'S) H ( 493,X'S)
RIDE C ( 50,X'S) H ( 503,X'S) H ( 502,X'S) H ( 501,X'S)
RIDE C ( 380,X'S) H (3801,X'S)
RIDE C ( 381,X'S) H (3811,X'S)
RIDE C ( 391,X'S) H (3911,X'S)
RIDE C ( 400,X'S) H (4001,X'S)
RIDE C ( 410,X'S) H (4101,X'S)
RIDE C ( 411,X'S) H (4111,X'S)
RIDE C(370,X'S,U'S) C(371,X'S,U'S)
EQUIVALENCE PART(1001,OCC) PART(1002,OCC)
WEIGHT -1 PART(1001,OCC)
END
;

_iucr_refine_instruction_details_restraints 
;
#
# Punched on 04/11/10 at 09:23:26
#
#LIST 16
SAME C(370) C(380) O(390) C(400) C(410) AND C(371) C(411) O(401) C(391) C(381)
DELU 0.01 C(370) C(380) O(390) C(400) C(410) AND
CONT C(371) C(411) O(401) C(391) C(381)
SIMU 0.01 C(370) C(380) O(390) C(400) C(410) AND
CONT C(371) C(411) O(401) C(391) C(381)
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;

_chemical_name_common            .