# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
#  of the CCDC or of third parties, and may not be copied or further 
#  disseminated in any form, whether machine-readable or not,  
#  except for the purpose of generating routine backup copies 
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# 
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#  data retrieval see:
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#
#  Bona fide researchers may freely download Mercury and enCIFer
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data_1
_database_code_depnum_ccdc_archive 'CCDC 894817'
#TrackingRef '2b_CH_ordered.cif'


_exptl_special_details           
;
The crystal was
placed in the cold stream of an Oxford
Cryosystems open-flow nitrogen cryostat (Cosier &
Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107.
;
_refine_special_details          
;
?
;
#---------------------------------------------------------------
# _oxford_ data items, April 2010:
# There is some uncertainty about the correct way of forming local data
# names, e.g.

# _atom_site_special_shape_oxford
# or
# _oxford_atom_site_special_shape

# see:
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace

# A reserved prefix, e.g. foo, must be used in the following way
# " If the data file contains items defined in a DDL1 dictionary, the
# local data names assigned under the reserved prefix must contain it as
# their first component, e.g. _foo_atom_site_my_item. "

# However, this seems to say the opposite:
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html

# According to advice from the IUCr, CRYSTALS is correct
#---------------------------------------------------------------
# End of 'script/refcif.dat'
#end of refcif
_cell_length_a                   9.32650(10)
_cell_length_b                   5.97390(10)
_cell_length_c                   34.571(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.198(6)
_cell_angle_gamma                90
_cell_volume                     1925.72(17)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C21 H32 N2 O2
# Dc = 1.19 Fooo = 752.00 Mu = 5.95 M = 344.50
# Found Formula = C21 H32 N2 O2
# Dc = 1.19 FOOO = 752.00 Mu = 5.95 M = 344.50

_chemical_formula_sum            'C21 H32 N2 O2'
_chemical_formula_moiety         'C21 H32 N2 O2'
_chemical_compound_source        ?
_chemical_formula_weight         344.50


_cell_measurement_reflns_used    3567
_cell_measurement_theta_min      2
_cell_measurement_theta_max      70
_cell_measurement_temperature    123

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.110
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_max          0.430

_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.595

# Sheldrick geometric approximatio 0.93 0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.94
_diffrn_measurement_device_type  'Image Plate'
_diffrn_measurement_device       'Rigaku RAPID II'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_method       \w

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'CrystalClear 2.0'
_computing_cell_refinement       'CrystalClear 2.0'
_computing_data_reduction        'CrystalStructure 4.0'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_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  1
_diffrn_standards_interval_count .
_diffrn_standards_number         3567
_diffrn_standards_decay_%        0.00

_diffrn_ambient_temperature      123
_diffrn_reflns_number            22422
_reflns_number_total             3567
_diffrn_reflns_av_R_equivalents  0.025
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 3567
# Theoretical number of reflections is about 6968


_diffrn_reflns_theta_min         2.557
_diffrn_reflns_theta_max         72.202
_diffrn_measured_fraction_theta_max 0.936

_diffrn_reflns_theta_full        72.0
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       37
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              7
_reflns_limit_l_min              0
_reflns_limit_l_max              38

_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   geom

_refine_diff_density_min         -0.21
_refine_diff_density_max         0.26


# 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         3309
_refine_ls_number_restraints     110
_refine_ls_number_parameters     322
_oxford_refine_ls_R_factor_ref   0.0509
_refine_ls_wR_factor_ref         0.0727
_refine_ls_goodness_of_fit_ref   0.9681
_refine_ls_shift/su_max          0.0003927
_refine_ls_shift/su_mean         0.0000318


# The values computed from all data
_oxford_reflns_number_all        3309
_refine_ls_R_factor_all          0.0509
_refine_ls_wR_factor_all         0.0727

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                2697
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_gt          0.0632

# 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    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:
11.5 14.8 3.74
;
# Insert your own references if required - in alphabetical order
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.71543(11) 0.47286(19) 0.37591(3) 0.0293 1.0000 Uani . . . . . .
O2 O 0.37301(12) 0.7425(2) 0.29024(3) 0.0334 1.0000 Uani . . . . . .
N1 N 0.47851(14) 0.4966(2) 0.36384(4) 0.0302 1.0000 Uani D . . . . .
N2 N 0.55807(15) 0.2901(2) 0.41889(4) 0.0333 1.0000 Uani D . . . . .
C1 C 0.57897(16) 0.4081(3) 0.38963(5) 0.0292 1.0000 Uani . . . . . .
C2 C 0.55156(16) 0.5966(3) 0.33338(5) 0.0264 1.0000 Uani . . . . . .
C3 C 0.49978(17) 0.7036(3) 0.29806(5) 0.0286 1.0000 Uani D . . . . .
C4 C 0.61838(18) 0.7546(3) 0.27018(5) 0.0297 1.0000 Uani D . . . . .
C5 C 0.75856(17) 0.8419(3) 0.28904(5) 0.0295 1.0000 Uani D . . . . .
C6 C 0.81428(17) 0.6709(3) 0.31941(5) 0.0298 1.0000 Uani D . . . . .
C7 C 0.69320(17) 0.5838(3) 0.34168(5) 0.0273 1.0000 Uani D . . . . .
C8 C 0.73090(19) 1.0675(3) 0.30833(5) 0.0345 1.0000 Uani D . . . . .
C9 C 0.87119(19) 0.8712(3) 0.25793(5) 0.0376 1.0000 Uani D . . . . .
C10 C 0.32623(16) 0.4276(3) 0.36248(5) 0.0305 1.0000 Uani D . . . . .
C11 C 0.31079(18) 0.1798(3) 0.35245(5) 0.0354 1.0000 Uani D . . . . .
C12 C 0.1526(2) 0.1136(4) 0.35051(6) 0.0424 1.0000 Uani D . . . . .
C13 C 0.0781(2) 0.1700(4) 0.38786(6) 0.0466 1.0000 Uani D . . . . .
C14 C 0.09404(19) 0.4172(4) 0.39762(6) 0.0454 1.0000 Uani D . . . . .
C15 C 0.25166(19) 0.4869(3) 0.39990(5) 0.0370 1.0000 Uani D . . . . .
C16 C 0.68014(17) 0.2011(3) 0.44134(5) 0.0295 1.0000 Uani D . . . . .
C17 C 0.6558(2) 0.2389(3) 0.48422(5) 0.0363 1.0000 Uani D . . . . .
C18 C 0.7748(2) 0.1348(4) 0.50910(6) 0.0435 1.0000 Uani D . . . . .
C19 C 0.7919(2) -0.1137(3) 0.50054(5) 0.0396 1.0000 Uani D . . . . .
C20 C 0.81552(19) -0.1549(3) 0.45783(5) 0.0364 1.0000 Uani D . . . . .
C21 C 0.6956(2) -0.0496(3) 0.43301(5) 0.0354 1.0000 Uani D . . . . .
H42 H 0.5828(15) 0.865(2) 0.2515(4) 0.0296 1.0000 Uiso D . . . . .
H41 H 0.6377(16) 0.620(3) 0.2557(4) 0.0420 1.0000 Uiso D . . . . .
H62 H 0.8867(15) 0.742(2) 0.3364(4) 0.0316 1.0000 Uiso D . . . . .
H61 H 0.8592(15) 0.546(2) 0.3067(4) 0.0249 1.0000 Uiso D . . . . .
H83 H 0.8221(16) 1.123(3) 0.3191(5) 0.0489 1.0000 Uiso D . . . . .
H81 H 0.6593(17) 1.051(3) 0.3294(4) 0.0475 1.0000 Uiso D . . . . .
H82 H 0.6946(18) 1.174(3) 0.2886(5) 0.0491 1.0000 Uiso D . . . . .
H91 H 0.8819(18) 0.732(3) 0.2437(5) 0.0542 1.0000 Uiso D . . . . .
H93 H 0.9648(16) 0.910(3) 0.2703(5) 0.0511 1.0000 Uiso D . . . . .
H92 H 0.8397(18) 0.988(3) 0.2397(5) 0.0554 1.0000 Uiso D . . . . .
H101 H 0.2794(15) 0.519(2) 0.3417(4) 0.0265 1.0000 Uiso D . . . . .
H111 H 0.3612(16) 0.089(3) 0.3728(4) 0.0367 1.0000 Uiso D . . . . .
H112 H 0.3544(16) 0.145(3) 0.3276(4) 0.0380 1.0000 Uiso D . . . . .
H121 H 0.1458(17) -0.044(3) 0.3436(5) 0.0498 1.0000 Uiso D . . . . .
H122 H 0.1042(17) 0.198(3) 0.3296(4) 0.0477 1.0000 Uiso D . . . . .
H131 H 0.1218(18) 0.082(3) 0.4086(4) 0.0508 1.0000 Uiso D . . . . .
H132 H -0.0220(16) 0.132(3) 0.3852(5) 0.0529 1.0000 Uiso D . . . . .
H141 H 0.0473(17) 0.448(3) 0.4222(4) 0.0495 1.0000 Uiso D . . . . .
H142 H 0.0455(17) 0.503(3) 0.3772(5) 0.0483 1.0000 Uiso D . . . . .
H151 H 0.3003(16) 0.408(3) 0.4220(4) 0.0426 1.0000 Uiso D . . . . .
H152 H 0.2606(16) 0.645(2) 0.4046(4) 0.0365 1.0000 Uiso D . . . . .
H161 H 0.7694(14) 0.280(2) 0.4349(4) 0.0253 1.0000 Uiso D . . . . .
H172 H 0.6511(16) 0.394(2) 0.4896(4) 0.0380 1.0000 Uiso D . . . . .
H171 H 0.5654(15) 0.173(3) 0.4916(4) 0.0408 1.0000 Uiso D . . . . .
H182 H 0.7532(17) 0.155(3) 0.5358(4) 0.0474 1.0000 Uiso D . . . . .
H181 H 0.8620(16) 0.213(3) 0.5044(5) 0.0482 1.0000 Uiso D . . . . .
H192 H 0.8718(16) -0.178(3) 0.5158(4) 0.0390 1.0000 Uiso D . . . . .
H191 H 0.7072(16) -0.195(3) 0.5083(5) 0.0410 1.0000 Uiso D . . . . .
H202 H 0.9084(15) -0.091(3) 0.4513(4) 0.0414 1.0000 Uiso D . . . . .
H201 H 0.8214(16) -0.315(2) 0.4521(4) 0.0337 1.0000 Uiso D . . . . .
H212 H 0.6024(15) -0.124(3) 0.4384(4) 0.0355 1.0000 Uiso D . . . . .
H211 H 0.7149(16) -0.067(3) 0.4052(4) 0.0395 1.0000 Uiso D . . . . .
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 0.0295(5) 0.0287(6) 0.0296(7) 0.0038(5) -0.0028(4) -0.0015(5)
O2 0.0314(6) 0.0346(6) 0.0338(7) 0.0022(5) -0.0063(5) 0.0009(5)
N1 0.0277(6) 0.0324(7) 0.0303(8) 0.0051(6) -0.0041(5) -0.0027(6)
N2 0.0310(7) 0.0362(8) 0.0327(8) 0.0088(6) -0.0034(6) -0.0021(6)
C1 0.0257(8) 0.0273(8) 0.0346(10) 0.0016(7) -0.0009(6) -0.0015(6)
C2 0.0308(8) 0.0227(8) 0.0258(9) -0.0015(6) 0.0000(6) 0.0005(6)
C3 0.0339(8) 0.0224(8) 0.0293(9) -0.0040(6) -0.0041(7) -0.0001(6)
C4 0.0354(8) 0.0274(8) 0.0264(10) -0.0004(7) -0.0021(7) 0.0009(7)
C5 0.0334(8) 0.0243(8) 0.0307(10) 0.0004(6) -0.0004(7) -0.0006(7)
C6 0.0303(8) 0.0269(8) 0.0321(10) 0.0022(7) -0.0016(7) -0.0002(7)
C7 0.0323(8) 0.0218(8) 0.0277(9) 0.0009(6) -0.0037(6) 0.0004(6)
C8 0.0395(9) 0.0264(9) 0.0374(11) 0.0002(7) -0.0018(8) -0.0023(7)
C9 0.0385(9) 0.0378(10) 0.0365(11) 0.0068(8) 0.0044(8) 0.0005(8)
C10 0.0246(8) 0.0342(9) 0.0326(10) 0.0021(7) -0.0016(7) 0.0016(7)
C11 0.0327(9) 0.0386(10) 0.0348(11) -0.0063(8) 0.0017(7) -0.0036(7)
C12 0.0376(10) 0.0504(12) 0.0392(12) 0.0029(9) -0.0017(8) -0.0131(9)
C13 0.0292(9) 0.0695(14) 0.0411(12) 0.0151(10) -0.0002(8) -0.0088(9)
C14 0.0320(9) 0.0676(14) 0.0369(12) 0.0093(9) 0.0048(8) 0.0116(9)
C15 0.0380(9) 0.0411(10) 0.0320(10) -0.0035(8) 0.0012(7) 0.0065(8)
C16 0.0279(8) 0.0324(9) 0.0281(9) 0.0043(7) -0.0014(6) -0.0023(7)
C17 0.0414(9) 0.0319(9) 0.0357(11) -0.0017(7) 0.0003(8) 0.0025(8)
C18 0.0512(11) 0.0490(11) 0.0299(11) -0.0029(8) -0.0066(8) 0.0076(9)
C19 0.0379(10) 0.0463(11) 0.0346(11) 0.0110(8) -0.0015(8) 0.0074(8)
C20 0.0384(9) 0.0333(9) 0.0374(11) 0.0011(8) -0.0004(7) 0.0052(8)
C21 0.0405(9) 0.0353(9) 0.0303(10) -0.0008(7) -0.0024(7) -0.0004(8)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.6274(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 . C1 . 1.4213(18) yes
O1 . C7 . 1.3682(19) yes
O2 . C3 . 1.2295(19) yes
N1 . C1 . 1.385(2) yes
N1 . C2 . 1.400(2) yes
N1 . C10 . 1.4787(19) yes
N2 . C1 . 1.252(2) yes
N2 . C16 . 1.464(2) yes
C2 . C3 . 1.452(2) yes
C2 . C7 . 1.348(2) yes
C3 . C4 . 1.513(2) yes
C4 . C5 . 1.540(2) yes
C4 . H42 . 0.977(13) no
C4 . H41 . 0.967(14) no
C5 . C6 . 1.547(2) yes
C5 . C8 . 1.528(2) yes
C5 . C9 . 1.529(2) yes
C6 . C7 . 1.475(2) yes
C6 . H62 . 0.984(13) no
C6 . H61 . 0.965(13) no
C8 . H83 . 0.979(14) no
C8 . H81 . 1.003(14) no
C8 . H82 . 0.987(15) no
C9 . H91 . 0.971(15) no
C9 . H93 . 0.992(14) no
C9 . H92 . 0.982(15) no
C10 . C11 . 1.527(2) yes
C10 . C15 . 1.523(2) yes
C10 . H101 . 0.996(13) no
C11 . C12 . 1.528(2) yes
C11 . H111 . 0.996(14) no
C11 . H112 . 0.982(14) no
C12 . C13 . 1.517(3) yes
C12 . H121 . 0.976(15) no
C12 . H122 . 0.983(14) no
C13 . C14 . 1.522(3) yes
C13 . H131 . 0.970(14) no
C13 . H132 . 0.963(14) no
C14 . C15 . 1.528(3) yes
C14 . H141 . 0.980(14) no
C14 . H142 . 0.976(14) no
C15 . H151 . 1.000(14) no
C15 . H152 . 0.959(14) no
C16 . C17 . 1.522(2) yes
C16 . C21 . 1.532(2) yes
C16 . H161 . 0.985(13) no
C17 . C18 . 1.523(3) yes
C17 . H172 . 0.946(14) no
C17 . H171 . 0.970(14) no
C18 . C19 . 1.523(3) yes
C18 . H182 . 0.955(14) no
C18 . H181 . 0.956(14) no
C19 . C20 . 1.517(3) yes
C19 . H192 . 0.982(14) no
C19 . H191 . 0.970(14) no
C20 . C21 . 1.531(2) yes
C20 . H202 . 0.978(14) no
C20 . H201 . 0.980(14) no
C21 . H212 . 0.998(13) no
C21 . H211 . 0.989(14) 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
C1 . O1 . C7 . 107.46(12) yes
C1 . N1 . C2 . 108.30(13) yes
C1 . N1 . C10 . 123.39(14) yes
C2 . N1 . C10 . 125.27(13) yes
C1 . N2 . C16 . 120.02(14) yes
O1 . C1 . N1 . 106.23(13) yes
O1 . C1 . N2 . 125.37(14) yes
N1 . C1 . N2 . 128.38(15) yes
N1 . C2 . C3 . 131.44(14) yes
N1 . C2 . C7 . 107.80(14) yes
C3 . C2 . C7 . 120.76(15) yes
C2 . C3 . O2 . 124.73(15) yes
C2 . C3 . C4 . 112.93(13) yes
O2 . C3 . C4 . 122.29(15) yes
C3 . C4 . C5 . 115.09(13) yes
C3 . C4 . H42 . 108.3(8) no
C5 . C4 . H42 . 109.0(9) no
C3 . C4 . H41 . 108.0(9) no
C5 . C4 . H41 . 109.6(9) no
H42 . C4 . H41 . 106.4(12) no
C4 . C5 . C6 . 109.52(13) yes
C4 . C5 . C8 . 109.50(13) yes
C6 . C5 . C8 . 110.09(14) yes
C4 . C5 . C9 . 109.31(14) yes
C6 . C5 . C9 . 109.08(14) yes
C8 . C5 . C9 . 109.31(14) yes
C5 . C6 . C7 . 109.72(13) yes
C5 . C6 . H62 . 109.6(9) no
C7 . C6 . H62 . 111.4(9) no
C5 . C6 . H61 . 110.2(9) no
C7 . C6 . H61 . 108.0(8) no
H62 . C6 . H61 . 107.9(11) no
C6 . C7 . O1 . 121.24(13) yes
C6 . C7 . C2 . 128.77(15) yes
O1 . C7 . C2 . 109.99(14) yes
C5 . C8 . H83 . 108.1(10) no
C5 . C8 . H81 . 110.6(10) no
H83 . C8 . H81 . 110.1(12) no
C5 . C8 . H82 . 108.8(10) no
H83 . C8 . H82 . 109.2(12) no
H81 . C8 . H82 . 110.0(12) no
C5 . C9 . H91 . 109.7(10) no
C5 . C9 . H93 . 109.5(10) no
H91 . C9 . H93 . 108.6(12) no
C5 . C9 . H92 . 109.5(10) no
H91 . C9 . H92 . 108.4(12) no
H93 . C9 . H92 . 111.1(12) no
N1 . C10 . C11 . 111.32(14) yes
N1 . C10 . C15 . 111.32(14) yes
C11 . C10 . C15 . 112.08(15) yes
N1 . C10 . H101 . 106.1(8) no
C11 . C10 . H101 . 109.1(8) no
C15 . C10 . H101 . 106.6(8) no
C10 . C11 . C12 . 110.33(15) yes
C10 . C11 . H111 . 109.0(9) no
C12 . C11 . H111 . 109.4(9) no
C10 . C11 . H112 . 111.5(9) no
C12 . C11 . H112 . 108.9(9) no
H111 . C11 . H112 . 107.8(12) no
C11 . C12 . C13 . 111.34(16) yes
C11 . C12 . H121 . 108.6(10) no
C13 . C12 . H121 . 113.4(10) no
C11 . C12 . H122 . 109.1(10) no
C13 . C12 . H122 . 107.6(10) no
H121 . C12 . H122 . 106.7(12) no
C12 . C13 . C14 . 111.11(16) yes
C12 . C13 . H131 . 108.4(10) no
C14 . C13 . H131 . 108.8(10) no
C12 . C13 . H132 . 109.1(10) no
C14 . C13 . H132 . 109.8(10) no
H131 . C13 . H132 . 109.5(12) no
C13 . C14 . C15 . 111.42(16) yes
C13 . C14 . H141 . 109.4(10) no
C15 . C14 . H141 . 110.4(10) no
C13 . C14 . H142 . 108.0(10) no
C15 . C14 . H142 . 108.9(10) no
H141 . C14 . H142 . 108.6(12) no
C14 . C15 . C10 . 110.40(15) yes
C14 . C15 . H151 . 109.3(9) no
C10 . C15 . H151 . 109.4(9) no
C14 . C15 . H152 . 110.9(9) no
C10 . C15 . H152 . 109.4(9) no
H151 . C15 . H152 . 107.4(12) no
N2 . C16 . C17 . 109.40(14) yes
N2 . C16 . C21 . 109.28(14) yes
C17 . C16 . C21 . 110.18(14) yes
N2 . C16 . H161 . 111.0(8) no
C17 . C16 . H161 . 107.1(8) no
C21 . C16 . H161 . 109.9(8) no
C16 . C17 . C18 . 111.57(15) yes
C16 . C17 . H172 . 110.2(9) no
C18 . C17 . H172 . 109.0(9) no
C16 . C17 . H171 . 110.0(9) no
C18 . C17 . H171 . 108.2(9) no
H172 . C17 . H171 . 107.8(12) no
C17 . C18 . C19 . 111.53(16) yes
C17 . C18 . H182 . 109.1(10) no
C19 . C18 . H182 . 109.6(10) no
C17 . C18 . H181 . 108.4(10) no
C19 . C18 . H181 . 110.5(10) no
H182 . C18 . H181 . 107.6(12) no
C18 . C19 . C20 . 111.42(15) yes
C18 . C19 . H192 . 111.0(9) no
C20 . C19 . H192 . 109.6(9) no
C18 . C19 . H191 . 110.2(10) no
C20 . C19 . H191 . 108.8(10) no
H192 . C19 . H191 . 105.7(12) no
C19 . C20 . C21 . 111.09(15) yes
C19 . C20 . H202 . 108.0(9) no
C21 . C20 . H202 . 110.4(9) no
C19 . C20 . H201 . 111.5(9) no
C21 . C20 . H201 . 109.3(9) no
H202 . C20 . H201 . 106.4(12) no
C16 . C21 . C20 . 111.51(15) yes
C16 . C21 . H212 . 108.5(9) no
C20 . C21 . H212 . 109.9(9) no
C16 . C21 . H211 . 107.8(9) no
C20 . C21 . H211 . 110.9(9) no
H212 . C21 . H211 . 108.1(11) 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
C10 . H101 . O2 . 132.7(11) 0.996(13) 2.403(14) 3.164(3) yes
C15 . H151 . N2 . 121.3(11) 1.000(14) 2.509(15) 3.147(3) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 03/08/12 at 20:15:37
#
#LIST 12
BLOCK
CONT SCALE
CONT O ( 1 ,X'S,U'S) UNTIL C ( 21 )
CONT H ( 42 ,X'S) UNTIL H ( 211 )
END
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 03/08/12 at 20:15:37
#
#LIST 16
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM NO H NO #H U MULT DIST
REM C-H
REM >4 1.5 .96 DISORDER
REM 1 1 1.2 .93 C C-H (ACETYLENE)
REM 1 2 1.2 .93 C-C(H)-C
REM 1 3 1.2 .98 (C)3-C-H
REM 2 1 1.2 .93 C=C-H(2)
REM 2 2 1.2 .97 (C)2-C-(H)2
REM 3 1 1.5 .96 C-C-(H)3
REM N-H
REM >4 1.5 .89 DISORDER
REM 1 1 1.2 .86 N-N/H
REM 1 2 1.2 .86 (C)2-N-H
REM 1 3 1.2 .89 (C)3-N-H
REM 2 1 1.2 .86 C-N-(H)2
REM 2 2 1.2 .89 (C)2-N-(H)2
REM 3 1 1.2 .89 C-H-(H)3
REM O-H
REM 1 1 1.5 .82 O-H
REM
REM DIST ESD = 0.02
REM VIB ESD = 0.002
REM ANGLE ESD = 2.0
REM 2 H ON SP 3
DIST 0.97, 0.02 =
CONT C ( 4) TO H(42)
CONT C ( 4) TO H(41)
REST 0.036, 0.002 = H(42,U[ISO])
REST 0.036, 0.002 = H(41,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(42) TO C ( 4) TO C(3)
CONT H(42) TO C ( 4) TO C(5)
CONT H(41) TO C ( 4) TO C(3)
CONT H(41) TO C ( 4) TO C(5)
ANGLE 109.54, 2.0 =
CONT H(42) TO C ( 4) TO H(41)
REM 2 H ON SP 3
DIST 0.97, 0.02 =
CONT C ( 6) TO H(62)
CONT C ( 6) TO H(61)
REST 0.036, 0.002 = H(62,U[ISO])
REST 0.036, 0.002 = H(61,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(62) TO C ( 6) TO C(5)
CONT H(62) TO C ( 6) TO C(7)
CONT H(61) TO C ( 6) TO C(5)
CONT H(61) TO C ( 6) TO C(7)
ANGLE 109.54, 2.0 =
CONT H(62) TO C ( 6) TO H(61)
REM 3 H ON SP 3
DIST 0.96, 0.02 =
CONT C ( 8) TO H(83)
CONT C ( 8) TO H(81)
CONT C ( 8) TO H(82)
REST 0.053, 0.002 = H(83,U[ISO])
REST 0.053, 0.002 = H(81,U[ISO])
REST 0.053, 0.002 = H(82,U[ISO])
ANGLE 109.54, 2.0 =
CONT C(5) TO C ( 8) TO H(83)
CONT C(5) TO C ( 8) TO H(81)
CONT C(5) TO C ( 8) TO H(82)
ANGLE 0.0, 2.0 = MEAN H(83) TO C ( 8) TO H(81)
CONT H(83) TO C ( 8) TO H(82)
CONT H(81) TO C ( 8) TO H(82)
REM 3 H ON SP 3
DIST 0.96, 0.02 =
CONT C ( 9) TO H(91)
CONT C ( 9) TO H(93)
CONT C ( 9) TO H(92)
REST 0.057, 0.002 = H(91,U[ISO])
REST 0.057, 0.002 = H(93,U[ISO])
REST 0.057, 0.002 = H(92,U[ISO])
ANGLE 109.54, 2.0 =
CONT C(5) TO C ( 9) TO H(91)
CONT C(5) TO C ( 9) TO H(93)
CONT C(5) TO C ( 9) TO H(92)
ANGLE 0.0, 2.0 = MEAN H(91) TO C ( 9) TO H(93)
CONT H(91) TO C ( 9) TO H(92)
CONT H(93) TO C ( 9) TO H(92)
REM 1 H ON SP 3
DIST 0.98, 0.02 =
CONT C ( 10) TO H(101)
REST 0.037, 0.002 = H(101,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(101) TO C ( 10) TO N(1)
CONT H(101) TO C ( 10) TO C(11)
CONT H(101) TO C ( 10) TO C(15)
REM 2 H ON SP 3
DIST 0.97, 0.02 =
CONT C ( 11) TO H(111)
CONT C ( 11) TO H(112)
REST 0.043, 0.002 = H(111,U[ISO])
REST 0.043, 0.002 = H(112,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(111) TO C ( 11) TO C(10)
CONT H(111) TO C ( 11) TO C(12)
CONT H(112) TO C ( 11) TO C(10)
CONT H(112) TO C ( 11) TO C(12)
ANGLE 109.54, 2.0 =
CONT H(111) TO C ( 11) TO H(112)
REM 2 H ON SP 3
DIST 0.97, 0.02 =
CONT C ( 12) TO H(121)
CONT C ( 12) TO H(122)
REST 0.051, 0.002 = H(121,U[ISO])
REST 0.051, 0.002 = H(122,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(121) TO C ( 12) TO C(11)
CONT H(121) TO C ( 12) TO C(13)
CONT H(122) TO C ( 12) TO C(11)
CONT H(122) TO C ( 12) TO C(13)
ANGLE 109.54, 2.0 =
CONT H(121) TO C ( 12) TO H(122)
REM 2 H ON SP 3
DIST 0.97, 0.02 =
CONT C ( 13) TO H(131)
CONT C ( 13) TO H(132)
REST 0.056, 0.002 = H(131,U[ISO])
REST 0.056, 0.002 = H(132,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(131) TO C ( 13) TO C(12)
CONT H(131) TO C ( 13) TO C(14)
CONT H(132) TO C ( 13) TO C(12)
CONT H(132) TO C ( 13) TO C(14)
ANGLE 109.54, 2.0 =
CONT H(131) TO C ( 13) TO H(132)
REM 2 H ON SP 3
DIST 0.97, 0.02 =
CONT C ( 14) TO H(141)
CONT C ( 14) TO H(142)
REST 0.055, 0.002 = H(141,U[ISO])
REST 0.055, 0.002 = H(142,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(141) TO C ( 14) TO C(13)
CONT H(141) TO C ( 14) TO C(15)
CONT H(142) TO C ( 14) TO C(13)
CONT H(142) TO C ( 14) TO C(15)
ANGLE 109.54, 2.0 =
CONT H(141) TO C ( 14) TO H(142)
REM 2 H ON SP 3
DIST 0.97, 0.02 =
CONT C ( 15) TO H(151)
CONT C ( 15) TO H(152)
REST 0.044, 0.002 = H(151,U[ISO])
REST 0.044, 0.002 = H(152,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(151) TO C ( 15) TO C(14)
CONT H(151) TO C ( 15) TO C(10)
CONT H(152) TO C ( 15) TO C(14)
CONT H(152) TO C ( 15) TO C(10)
ANGLE 109.54, 2.0 =
CONT H(151) TO C ( 15) TO H(152)
REM 1 H ON SP 3
DIST 0.98, 0.02 =
CONT C ( 16) TO H(161)
REST 0.036, 0.002 = H(161,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(161) TO C ( 16) TO N(2)
CONT H(161) TO C ( 16) TO C(17)
CONT H(161) TO C ( 16) TO C(21)
REM 2 H ON SP 3
DIST 0.97, 0.02 =
CONT C ( 17) TO H(172)
CONT C ( 17) TO H(171)
REST 0.044, 0.002 = H(172,U[ISO])
REST 0.044, 0.002 = H(171,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(172) TO C ( 17) TO C(16)
CONT H(172) TO C ( 17) TO C(18)
CONT H(171) TO C ( 17) TO C(16)
CONT H(171) TO C ( 17) TO C(18)
ANGLE 109.54, 2.0 =
CONT H(172) TO C ( 17) TO H(171)
REM 2 H ON SP 3
DIST 0.97, 0.02 =
CONT C ( 18) TO H(182)
CONT C ( 18) TO H(181)
REST 0.053, 0.002 = H(182,U[ISO])
REST 0.053, 0.002 = H(181,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(182) TO C ( 18) TO C(17)
CONT H(182) TO C ( 18) TO C(19)
CONT H(181) TO C ( 18) TO C(17)
CONT H(181) TO C ( 18) TO C(19)
ANGLE 109.54, 2.0 =
CONT H(182) TO C ( 18) TO H(181)
REM 2 H ON SP 3
DIST 0.97, 0.02 =
CONT C ( 19) TO H(192)
CONT C ( 19) TO H(191)
REST 0.048, 0.002 = H(192,U[ISO])
REST 0.048, 0.002 = H(191,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(192) TO C ( 19) TO C(18)
CONT H(192) TO C ( 19) TO C(20)
CONT H(191) TO C ( 19) TO C(18)
CONT H(191) TO C ( 19) TO C(20)
ANGLE 109.54, 2.0 =
CONT H(192) TO C ( 19) TO H(191)
REM 2 H ON SP 3
DIST 0.97, 0.02 =
CONT C ( 20) TO H(202)
CONT C ( 20) TO H(201)
REST 0.045, 0.002 = H(202,U[ISO])
REST 0.045, 0.002 = H(201,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(202) TO C ( 20) TO C(19)
CONT H(202) TO C ( 20) TO C(21)
CONT H(201) TO C ( 20) TO C(19)
CONT H(201) TO C ( 20) TO C(21)
ANGLE 109.54, 2.0 =
CONT H(202) TO C ( 20) TO H(201)
REM 2 H ON SP 3
DIST 0.97, 0.02 =
CONT C ( 21) TO H(212)
CONT C ( 21) TO H(211)
REST 0.043, 0.002 = H(212,U[ISO])
REST 0.043, 0.002 = H(211,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(212) TO C ( 21) TO C(16)
CONT H(212) TO C ( 21) TO C(20)
CONT H(211) TO C ( 21) TO C(16)
CONT H(211) TO C ( 21) TO C(20)
ANGLE 109.54, 2.0 =
CONT H(212) TO C ( 21) TO H(211)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;


data_5a
_database_code_depnum_ccdc_archive 'CCDC 894818'
#TrackingRef '5a.cif'


_exptl_special_details           
;
The crystal was
placed in the cold stream of an Oxford
Cryosystems open-flow nitrogen cryostat (Cosier &
Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107.
;
_refine_special_details          
;
?
;
#---------------------------------------------------------------
# _oxford_ data items, April 2010:
# There is some uncertainty about the correct way of forming local data
# names, e.g.

# _atom_site_special_shape_oxford
# or
# _oxford_atom_site_special_shape

# see:
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace

# A reserved prefix, e.g. foo, must be used in the following way
# " If the data file contains items defined in a DDL1 dictionary, the
# local data names assigned under the reserved prefix must contain it as
# their first component, e.g. _foo_atom_site_my_item. "

# However, this seems to say the opposite:
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html

# According to advice from the IUCr, CRYSTALS is correct
#---------------------------------------------------------------
# End of 'script/refcif.dat'
#end of refcif
_cell_length_a                   7.9997(3)
_cell_length_b                   9.0944(3)
_cell_length_c                   10.6971(7)
_cell_angle_alpha                73.485(5)
_cell_angle_beta                 86.480(6)
_cell_angle_gamma                69.563(5)
_cell_volume                     698.55(7)

_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'
I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 '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 = C15 H17 I1 O3
# Dc = 1.77 Fooo = 368.00 Mu = 22.93 M = 372.20
# Found Formula = C15 H17 I1 O3
# Dc = 1.77 FOOO = 368.00 Mu = 22.93 M = 372.20

_chemical_formula_sum            'C15 H17 I1 O3'
_chemical_formula_moiety         'C15 H17 I1 O3'
_chemical_compound_source        ?
_chemical_formula_weight         372.20


_cell_measurement_reflns_used    3200
_cell_measurement_theta_min      2
_cell_measurement_theta_max      27
_cell_measurement_temperature    123

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.320
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_max          0.580

_exptl_crystal_density_diffrn    1.769
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    2.293

# Sheldrick geometric approximatio 0.37 0.48
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.30
_exptl_absorpt_correction_T_max  0.48
_diffrn_measurement_device_type  'Image Plate'
_diffrn_measurement_device       'Rigaku RAPID II'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_method       \w

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'CrystalClear 2.0'
_computing_cell_refinement       'CrystalClear 2.0'
_computing_data_reduction        'CrystalStructure 4.0'
_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  2
_diffrn_standards_interval_count .
_diffrn_standards_number         3200
_diffrn_standards_decay_%        0.00

_diffrn_ambient_temperature      123
_diffrn_reflns_number            22505
_reflns_number_total             3200
_diffrn_reflns_av_R_equivalents  0.027
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 3200
# Theoretical number of reflections is about 6399


_diffrn_reflns_theta_min         3.245
_diffrn_reflns_theta_max         27.470
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        27.470
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              -11
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   1.45
_oxford_diffrn_Wilson_scale      0.33

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

_refine_diff_density_min         -0.27
_refine_diff_density_max         0.47


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


# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns         3190
_refine_ls_number_restraints     0
_refine_ls_number_parameters     172
_oxford_refine_ls_R_factor_ref   0.0159
_refine_ls_wR_factor_ref         0.0401
_refine_ls_goodness_of_fit_ref   0.9987
_refine_ls_shift/su_max          0.0017521
_refine_ls_shift/su_mean         0.0000341


# The values computed from all data
_oxford_reflns_number_all        3190
_refine_ls_R_factor_all          0.0159
_refine_ls_wR_factor_all         0.0401

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                3072
_refine_ls_R_factor_gt           0.0151
_refine_ls_wR_factor_gt          0.0397

# 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    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^) + ( 0.02P)^2^ + 0.63P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
# Insert your own references if required - in alphabetical order
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
I1 I 0.219809(14) 0.108996(13) 0.916770(10) 0.0178 1.0000 Uani . . . . . .
C1 C 0.4017(2) 0.1633(2) 0.78282(17) 0.0181 1.0000 Uani . . . . . .
C2 C 0.3874(2) 0.1440(2) 0.65597(17) 0.0190 1.0000 Uani . . . . . .
O1 O 0.27577(19) 0.09520(19) 0.62294(14) 0.0290 1.0000 Uani . . . . . .
C3 C 0.5173(2) 0.1950(2) 0.55754(17) 0.0204 1.0000 Uani . . . . . .
C4 C 0.6864(2) 0.1991(2) 0.61455(17) 0.0178 1.0000 Uani . . . . . .
C5 C 0.6357(2) 0.2891(2) 0.72016(17) 0.0197 1.0000 Uani . . . . . .
C6 C 0.5221(2) 0.2239(2) 0.82565(17) 0.0166 1.0000 Uani . . . . . .
O2 O 0.53660(17) 0.22926(17) 0.93921(12) 0.0224 1.0000 Uani . . . . . .
C7 C 0.7797(3) 0.2891(3) 0.50668(19) 0.0264 1.0000 Uani . . . . . .
C8 C 0.8168(3) 0.0258(2) 0.6731(2) 0.0266 1.0000 Uani . . . . . .
C9 C 0.0166(2) 0.3412(2) 0.85774(17) 0.0181 1.0000 Uani . . . . . .
C10 C 0.0109(2) 0.4481(2) 0.73525(19) 0.0222 1.0000 Uani . . . . . .
C11 C -0.1287(3) 0.5975(2) 0.7017(2) 0.0256 1.0000 Uani . . . . . .
C12 C -0.2567(3) 0.6362(2) 0.7923(2) 0.0260 1.0000 Uani . . . . . .
C13 C -0.2500(2) 0.5282(2) 0.91537(19) 0.0227 1.0000 Uani . . . . . .
C14 C -0.1136(2) 0.3767(2) 0.94842(17) 0.0192 1.0000 Uani . . . . . .
O3 O -0.09433(17) 0.25648(17) 1.06226(12) 0.0229 1.0000 Uani . . . . . .
C15 C -0.2313(3) 0.2869(3) 1.15477(18) 0.0253 1.0000 Uani . . . . . .
H31 H 0.4534 0.3036 0.5079 0.0237 1.0000 Uiso R . . . . .
H32 H 0.5539 0.1229 0.5028 0.0249 1.0000 Uiso R . . . . .
H51 H 0.7443 0.2849 0.7591 0.0219 1.0000 Uiso R . . . . .
H52 H 0.5662 0.4029 0.6794 0.0217 1.0000 Uiso R . . . . .
H71 H 0.8861 0.2893 0.5433 0.0373 1.0000 Uiso R . . . . .
H72 H 0.7053 0.4030 0.4693 0.0392 1.0000 Uiso R . . . . .
H73 H 0.8183 0.2329 0.4385 0.0386 1.0000 Uiso R . . . . .
H81 H 0.9260 0.0285 0.7036 0.0395 1.0000 Uiso R . . . . .
H82 H 0.7689 -0.0311 0.7430 0.0390 1.0000 Uiso R . . . . .
H83 H 0.8469 -0.0352 0.6110 0.0384 1.0000 Uiso R . . . . .
H101 H 0.0966 0.4191 0.6772 0.0255 1.0000 Uiso R . . . . .
H111 H -0.1344 0.6699 0.6193 0.0306 1.0000 Uiso R . . . . .
H121 H -0.3519 0.7370 0.7680 0.0299 1.0000 Uiso R . . . . .
H131 H -0.3337 0.5522 0.9770 0.0279 1.0000 Uiso R . . . . .
H151 H -0.2045 0.1899 1.2228 0.0358 1.0000 Uiso R . . . . .
H152 H -0.2289 0.3780 1.1819 0.0361 1.0000 Uiso R . . . . .
H153 H -0.3442 0.3121 1.1115 0.0339 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
I1 0.01514(6) 0.01939(6) 0.01839(6) -0.00552(4) 0.00304(4) -0.00570(4)
C1 0.0151(8) 0.0237(9) 0.0172(8) -0.0078(7) 0.0049(6) -0.0076(7)
C2 0.0166(8) 0.0216(8) 0.0204(8) -0.0091(7) 0.0012(6) -0.0062(7)
O1 0.0276(7) 0.0446(9) 0.0263(7) -0.0177(6) 0.0033(6) -0.0207(7)
C3 0.0207(8) 0.0268(9) 0.0162(8) -0.0091(7) 0.0023(6) -0.0092(7)
C4 0.0165(8) 0.0208(8) 0.0167(8) -0.0061(7) 0.0032(6) -0.0070(7)
C5 0.0192(8) 0.0240(9) 0.0211(8) -0.0108(7) 0.0036(7) -0.0107(7)
C6 0.0144(7) 0.0157(8) 0.0193(8) -0.0077(6) 0.0012(6) -0.0025(6)
O2 0.0229(6) 0.0282(7) 0.0201(6) -0.0133(5) 0.0015(5) -0.0087(5)
C7 0.0282(10) 0.0330(10) 0.0212(9) -0.0070(8) 0.0071(7) -0.0161(8)
C8 0.0223(9) 0.0243(9) 0.0285(10) -0.0085(8) 0.0033(7) -0.0020(8)
C9 0.0144(8) 0.0189(8) 0.0229(8) -0.0083(7) 0.0008(6) -0.0063(6)
C10 0.0186(8) 0.0246(9) 0.0263(9) -0.0066(7) 0.0042(7) -0.0120(7)
C11 0.0229(9) 0.0214(9) 0.0312(10) -0.0021(8) 0.0020(7) -0.0103(8)
C12 0.0198(9) 0.0180(8) 0.0394(11) -0.0073(8) 0.0000(8) -0.0062(7)
C13 0.0166(8) 0.0246(9) 0.0306(10) -0.0143(8) 0.0037(7) -0.0070(7)
C14 0.0167(8) 0.0240(9) 0.0213(8) -0.0098(7) 0.0008(6) -0.0094(7)
O3 0.0175(6) 0.0299(7) 0.0180(6) -0.0070(5) 0.0039(5) -0.0045(5)
C15 0.0206(9) 0.0371(11) 0.0191(9) -0.0128(8) 0.0049(7) -0.0079(8)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.758(5)
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
I1 . C1 . 2.0638(17) yes
I1 . C9 . 2.1146(17) yes
C1 . C2 . 1.433(2) yes
C1 . C6 . 1.417(2) yes
C2 . O1 . 1.235(2) yes
C2 . C3 . 1.525(2) yes
C3 . C4 . 1.534(2) yes
C3 . H31 . 0.950 no
C3 . H32 . 0.960 no
C4 . C5 . 1.532(2) yes
C4 . C7 . 1.530(2) yes
C4 . C8 . 1.528(3) yes
C5 . C6 . 1.523(2) yes
C5 . H51 . 0.971 no
C5 . H52 . 0.971 no
C6 . O2 . 1.244(2) yes
C7 . H71 . 0.960 no
C7 . H72 . 0.975 no
C7 . H73 . 0.981 no
C8 . H81 . 0.961 no
C8 . H82 . 0.926 no
C8 . H83 . 0.950 no
C9 . C10 . 1.384(3) yes
C9 . C14 . 1.396(2) yes
C10 . C11 . 1.391(3) yes
C10 . H101 . 0.916 no
C11 . C12 . 1.390(3) yes
C11 . H111 . 0.931 no
C12 . C13 . 1.392(3) yes
C12 . H121 . 0.943 no
C13 . C14 . 1.391(3) yes
C13 . H131 . 0.926 no
C14 . O3 . 1.360(2) yes
O3 . C15 . 1.438(2) yes
C15 . H151 . 0.936 no
C15 . H152 . 0.959 no
C15 . H153 . 0.964 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
C1 . I1 . C9 . 96.42(7) yes
I1 . C1 . C2 . 117.20(12) yes
I1 . C1 . C6 . 115.49(12) yes
C2 . C1 . C6 . 127.22(16) yes
C1 . C2 . O1 . 124.33(16) yes
C1 . C2 . C3 . 115.50(15) yes
O1 . C2 . C3 . 120.13(16) yes
C2 . C3 . C4 . 116.21(14) yes
C2 . C3 . H31 . 105.8 no
C4 . C3 . H31 . 106.6 no
C2 . C3 . H32 . 109.5 no
C4 . C3 . H32 . 107.7 no
H31 . C3 . H32 . 110.9 no
C3 . C4 . C5 . 109.48(14) yes
C3 . C4 . C7 . 109.77(15) yes
C5 . C4 . C7 . 109.02(15) yes
C3 . C4 . C8 . 110.71(15) yes
C5 . C4 . C8 . 109.66(15) yes
C7 . C4 . C8 . 108.16(15) yes
C4 . C5 . C6 . 114.40(14) yes
C4 . C5 . H51 . 108.6 no
C6 . C5 . H51 . 110.2 no
C4 . C5 . H52 . 108.7 no
C6 . C5 . H52 . 106.6 no
H51 . C5 . H52 . 108.1 no
C5 . C6 . C1 . 115.15(15) yes
C5 . C6 . O2 . 120.03(15) yes
C1 . C6 . O2 . 124.80(16) yes
C4 . C7 . H71 . 109.0 no
C4 . C7 . H72 . 111.9 no
H71 . C7 . H72 . 107.0 no
C4 . C7 . H73 . 111.6 no
H71 . C7 . H73 . 106.2 no
H72 . C7 . H73 . 110.9 no
C4 . C8 . H81 . 110.6 no
C4 . C8 . H82 . 111.2 no
H81 . C8 . H82 . 108.0 no
C4 . C8 . H83 . 111.8 no
H81 . C8 . H83 . 107.4 no
H82 . C8 . H83 . 107.6 no
I1 . C9 . C10 . 121.75(13) yes
I1 . C9 . C14 . 115.68(13) yes
C10 . C9 . C14 . 122.54(17) yes
C9 . C10 . C11 . 118.79(17) yes
C9 . C10 . H101 . 120.1 no
C11 . C10 . H101 . 121.1 no
C10 . C11 . C12 . 119.28(18) yes
C10 . C11 . H111 . 119.5 no
C12 . C11 . H111 . 121.3 no
C11 . C12 . C13 . 121.62(18) yes
C11 . C12 . H121 . 118.6 no
C13 . C12 . H121 . 119.8 no
C12 . C13 . C14 . 119.47(17) yes
C12 . C13 . H131 . 122.8 no
C14 . C13 . H131 . 117.7 no
C9 . C14 . C13 . 118.25(17) yes
C9 . C14 . O3 . 115.72(16) yes
C13 . C14 . O3 . 126.02(16) yes
C14 . O3 . C15 . 116.82(14) yes
O3 . C15 . H151 . 106.0 no
O3 . C15 . H152 . 107.6 no
H151 . C15 . H152 . 113.4 no
O3 . C15 . H153 . 107.8 no
H151 . C15 . H153 . 110.7 no
H152 . C15 . H153 . 110.9 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
C13 . H131 . O2 2_567 144.82(6) 0.92551 2.443 3.244(3) yes
C15 . H153 . O2 1_455 138.10(5) 0.96449 2.526 3.307(3) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 03/08/12 at 21:58:55
#
#LIST 12
BLOCK SCALE X'S, U'S
RIDE C ( 3,X'S) H ( 31,X'S) H ( 32,X'S)
RIDE C ( 5,X'S) H ( 51,X'S) H ( 52,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 ( 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) H ( 152,X'S) H ( 153,X'S)
END
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 03/08/12 at 21:58:55
#
#LIST 16
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;


data_5b
_database_code_depnum_ccdc_archive 'CCDC 894819'
#TrackingRef '5b.cif'


_exptl_special_details           
;
The crystal was
placed in the cold stream of an Oxford
Cryosystems open-flow nitrogen cryostat (Cosier &
Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107.
;
_refine_special_details          
;
?
;
#---------------------------------------------------------------
# _oxford_ data items, April 2010:
# There is some uncertainty about the correct way of forming local data
# names, e.g.

# _atom_site_special_shape_oxford
# or
# _oxford_atom_site_special_shape

# see:
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace

# A reserved prefix, e.g. foo, must be used in the following way
# " If the data file contains items defined in a DDL1 dictionary, the
# local data names assigned under the reserved prefix must contain it as
# their first component, e.g. _foo_atom_site_my_item. "

# However, this seems to say the opposite:
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html

# According to advice from the IUCr, CRYSTALS is correct
#---------------------------------------------------------------
# End of 'script/refcif.dat'
#end of refcif
_cell_length_a                   28.076(2)
_cell_length_b                   16.5298(13)
_cell_length_c                   7.1600(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3322.9(4)

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P b c a '
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,z
x+1/2,-y+1/2,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2
-x+1/2,-y,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 0.0033 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'
I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 '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            8

# Given Formula = C17 H21 I1 O3
# Dc = 1.60 Fooo = 1600.00 Mu = 19.35 M = 400.26
# Found Formula = C17 H21 I1 O3
# Dc = 1.60 FOOO = 1600.00 Mu = 19.35 M = 400.26

_chemical_formula_sum            'C17 H21 I1 O3'
_chemical_formula_moiety         'C17 H21 I1 O3'
_chemical_compound_source        ?
_chemical_formula_weight         400.26


_cell_measurement_reflns_used    3441
_cell_measurement_theta_min      2
_cell_measurement_theta_max      27
_cell_measurement_temperature    123

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.280
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_max          0.490

_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             1600
_exptl_absorpt_coefficient_mu    1.935

# Sheldrick geometric approximatio 0.54 0.58
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.47
_exptl_absorpt_correction_T_max  0.58
_diffrn_measurement_device_type  'Image Plate'
_diffrn_measurement_device       'Rigaku RAPID II'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_method       \w

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'CrystalClear 2.0'
_computing_cell_refinement       'CrystalClear 2.0'
_computing_data_reduction        'CrystalStructure 4.0'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_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  1
_diffrn_standards_interval_count .
_diffrn_standards_number         3441
_diffrn_standards_decay_%        0.00

_diffrn_ambient_temperature      123
_diffrn_reflns_number            9590
_reflns_number_total             3441
_diffrn_reflns_av_R_equivalents  0.021
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 3441
# Theoretical number of reflections is about 7618


_diffrn_reflns_theta_min         3.153
_diffrn_reflns_theta_max         27.481
_diffrn_measured_fraction_theta_max 0.902

_diffrn_reflns_theta_full        25.007
_diffrn_measured_fraction_theta_full 0.923


_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_reflns_limit_h_min              0
_reflns_limit_h_max              36
_reflns_limit_k_min              0
_reflns_limit_k_max              21
_reflns_limit_l_min              0
_reflns_limit_l_max              9

_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   geom

_refine_diff_density_min         -1.60
_refine_diff_density_max         1.41


# 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         3399
_refine_ls_number_restraints     0
_refine_ls_number_parameters     190
_oxford_refine_ls_R_factor_ref   0.0462
_refine_ls_wR_factor_ref         0.0764
_refine_ls_goodness_of_fit_ref   1.2017
_refine_ls_shift/su_max          0.0009672
_refine_ls_shift/su_mean         0.0000234


# The values computed from all data
_oxford_reflns_number_all        3399
_refine_ls_R_factor_all          0.0462
_refine_ls_wR_factor_all         0.0764

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                2962
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_gt          0.0762

# 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    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:
16.5 17.5 6.18
;
# Insert your own references if required - in alphabetical order
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
I1 I 0.428402(11) 0.64261(2) 0.15685(5) 0.0193 1.0000 Uani . . . . . .
C9 C 0.45063(19) 0.5228(3) 0.2143(8) 0.0206 1.0000 Uani . . . . . .
C14 C 0.4995(2) 0.5116(3) 0.2342(8) 0.0197 1.0000 Uani . . . . . .
O3 O 0.52674(13) 0.5785(2) 0.2063(6) 0.0250 1.0000 Uani . . . . . .
C15 C 0.57678(19) 0.5757(3) 0.2481(8) 0.0241 1.0000 Uani . . . . . .
C16 C 0.59418(19) 0.6623(4) 0.2332(10) 0.0315 1.0000 Uani . . . . . .
C17 C 0.6476(2) 0.6691(4) 0.2718(13) 0.0525 1.0000 Uani . . . . . .
C13 C 0.5162(2) 0.4353(3) 0.2796(8) 0.0246 1.0000 Uani . . . . . .
C12 C 0.4845(2) 0.3716(4) 0.2988(8) 0.0295 1.0000 Uani . . . . . .
C11 C 0.4357(2) 0.3843(3) 0.2747(8) 0.0300 1.0000 Uani . . . . . .
C10 C 0.4188(2) 0.4607(3) 0.2318(9) 0.0264 1.0000 Uani . . . . . .
C1 C 0.36728(15) 0.6415(3) 0.3169(8) 0.0177 1.0000 Uani . . . . . .
C2 C 0.37150(18) 0.6732(3) 0.5001(8) 0.0169 1.0000 Uani . . . . . .
O1 O 0.40967(12) 0.6983(2) 0.5700(6) 0.0232 1.0000 Uani . . . . . .
C3 C 0.32637(18) 0.6756(3) 0.6157(8) 0.0218 1.0000 Uani . . . . . .
C4 C 0.28878(19) 0.6125(3) 0.5609(8) 0.0224 1.0000 Uani . . . . . .
C7 C 0.3067(2) 0.5270(3) 0.6093(8) 0.0275 1.0000 Uani . . . . . .
C5 C 0.28038(17) 0.6185(3) 0.3486(9) 0.0248 1.0000 Uani . . . . . .
C6 C 0.3256(2) 0.6118(3) 0.2304(9) 0.0191 1.0000 Uani . . . . . .
O2 O 0.32316(15) 0.5822(3) 0.0732(6) 0.0338 1.0000 Uani . . . . . .
C8 C 0.24259(18) 0.6287(4) 0.6665(10) 0.0336 1.0000 Uani . . . . . .
H51 H 0.5812 0.5568 0.3732 0.0293 1.0000 Uiso R . . . . .
H52 H 0.5929 0.5407 0.1594 0.0290 1.0000 Uiso R . . . . .
H61 H 0.5872 0.6838 0.1090 0.0371 1.0000 Uiso R . . . . .
H62 H 0.5773 0.6939 0.3250 0.0374 1.0000 Uiso R . . . . .
H71 H 0.6572 0.7241 0.2509 0.0842 1.0000 Uiso R . . . . .
H72 H 0.6653 0.6341 0.1909 0.0839 1.0000 Uiso R . . . . .
H73 H 0.6541 0.6546 0.3991 0.0840 1.0000 Uiso R . . . . .
H81 H 0.5491 0.4269 0.2981 0.0294 1.0000 Uiso R . . . . .
H91 H 0.4958 0.3197 0.3277 0.0344 1.0000 Uiso R . . . . .
H101 H 0.4146 0.3411 0.2887 0.0370 1.0000 Uiso R . . . . .
H111 H 0.3864 0.4694 0.2157 0.0284 1.0000 Uiso R . . . . .
H152 H 0.3127 0.7292 0.6014 0.0285 1.0000 Uiso R . . . . .
H151 H 0.3349 0.6674 0.7458 0.0283 1.0000 Uiso R . . . . .
H172 H 0.2843 0.4884 0.5651 0.0400 1.0000 Uiso R . . . . .
H171 H 0.3102 0.5220 0.7431 0.0403 1.0000 Uiso R . . . . .
H173 H 0.3365 0.5177 0.5498 0.0400 1.0000 Uiso R . . . . .
H182 H 0.2655 0.6701 0.3201 0.0299 1.0000 Uiso R . . . . .
H181 H 0.2590 0.5754 0.3122 0.0302 1.0000 Uiso R . . . . .
H212 H 0.2189 0.5899 0.6318 0.0469 1.0000 Uiso R . . . . .
H211 H 0.2317 0.6822 0.6378 0.0469 1.0000 Uiso R . . . . .
H213 H 0.2485 0.6247 0.7987 0.0468 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
I1 0.01867(13) 0.01659(15) 0.02266(16) 0.00344(18) 0.00318(16) 0.00200(15)
C9 0.030(3) 0.016(3) 0.016(3) 0.001(2) 0.002(2) 0.009(2)
C14 0.025(2) 0.018(3) 0.016(3) 0.001(2) 0.003(2) 0.002(2)
O3 0.0222(19) 0.022(2) 0.031(3) 0.005(2) 0.0007(16) 0.0040(16)
C15 0.023(3) 0.024(3) 0.025(3) -0.002(3) -0.004(2) 0.007(2)
C16 0.027(3) 0.030(4) 0.038(4) -0.002(3) -0.003(3) 0.000(2)
C17 0.029(3) 0.043(4) 0.086(6) -0.003(4) -0.009(4) -0.007(3)
C13 0.030(3) 0.023(3) 0.021(3) -0.003(3) -0.001(2) 0.011(2)
C12 0.041(3) 0.022(3) 0.025(3) 0.003(3) 0.002(2) 0.011(2)
C11 0.042(4) 0.019(3) 0.029(3) -0.002(3) 0.007(3) -0.001(2)
C10 0.026(3) 0.024(3) 0.028(3) -0.003(3) 0.006(2) 0.001(2)
C1 0.016(2) 0.014(2) 0.023(3) 0.001(3) 0.003(2) 0.001(2)
C2 0.022(2) 0.004(2) 0.025(3) -0.001(2) -0.002(2) -0.0005(18)
O1 0.0180(17) 0.021(2) 0.030(2) -0.0090(19) -0.0067(16) -0.0066(15)
C3 0.023(3) 0.019(3) 0.023(3) -0.004(3) 0.002(2) -0.001(2)
C4 0.018(3) 0.026(3) 0.023(3) 0.000(3) 0.000(2) -0.005(2)
C7 0.035(3) 0.024(3) 0.023(3) 0.004(3) 0.003(2) -0.007(2)
C5 0.018(2) 0.029(3) 0.028(3) 0.002(3) -0.003(3) -0.005(2)
C6 0.024(3) 0.015(3) 0.018(3) 0.004(3) -0.002(2) -0.005(2)
O2 0.034(2) 0.047(3) 0.020(2) -0.005(2) -0.0028(18) -0.012(2)
C8 0.024(3) 0.040(4) 0.036(3) -0.007(4) 0.009(3) -0.005(2)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.22635(12)
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
I1 . C9 . 2.117(5) yes
I1 . C1 . 2.063(5) yes
C9 . C14 . 1.391(7) yes
C9 . C10 . 1.366(8) yes
C14 . O3 . 1.360(6) yes
C14 . C13 . 1.386(7) yes
O3 . C15 . 1.437(6) yes
C15 . C16 . 1.516(8) yes
C15 . H51 . 0.957 no
C15 . H52 . 0.971 no
C16 . C17 . 1.529(8) yes
C16 . H61 . 0.977 no
C16 . H62 . 0.963 no
C17 . H71 . 0.960 no
C17 . H72 . 0.958 no
C17 . H73 . 0.959 no
C13 . C12 . 1.386(8) yes
C13 . H81 . 0.942 no
C12 . C11 . 1.396(8) yes
C12 . H91 . 0.938 no
C11 . C10 . 1.384(8) yes
C11 . H101 . 0.932 no
C10 . H111 . 0.931 no
C1 . C2 . 1.418(8) yes
C1 . C6 . 1.413(7) yes
C2 . O1 . 1.253(6) yes
C2 . C3 . 1.514(7) yes
C3 . C4 . 1.534(7) yes
C3 . H152 . 0.972 no
C3 . H151 . 0.971 no
C4 . C7 . 1.539(8) yes
C4 . C5 . 1.542(8) yes
C4 . C8 . 1.525(7) yes
C7 . H172 . 0.951 no
C7 . H171 . 0.966 no
C7 . H173 . 0.951 no
C5 . C6 . 1.529(8) yes
C5 . H182 . 0.971 no
C5 . H181 . 0.969 no
C6 . O2 . 1.229(7) yes
C8 . H212 . 0.957 no
C8 . H211 . 0.959 no
C8 . H213 . 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
C9 . I1 . C1 . 97.4(2) yes
I1 . C9 . C14 . 115.8(4) yes
I1 . C9 . C10 . 121.9(4) yes
C14 . C9 . C10 . 122.3(5) yes
C9 . C14 . O3 . 115.6(5) yes
C9 . C14 . C13 . 118.7(5) yes
O3 . C14 . C13 . 125.7(5) yes
C14 . O3 . C15 . 119.6(4) yes
O3 . C15 . C16 . 105.6(4) yes
O3 . C15 . H51 . 109.4 no
C16 . C15 . H51 . 109.4 no
O3 . C15 . H52 . 109.8 no
C16 . C15 . H52 . 111.5 no
H51 . C15 . H52 . 110.9 no
C15 . C16 . C17 . 111.9(5) yes
C15 . C16 . H61 . 110.1 no
C17 . C16 . H61 . 109.5 no
C15 . C16 . H62 . 107.8 no
C17 . C16 . H62 . 108.6 no
H61 . C16 . H62 . 109.0 no
C16 . C17 . H71 . 108.4 no
C16 . C17 . H72 . 110.8 no
H71 . C17 . H72 . 109.4 no
C16 . C17 . H73 . 109.8 no
H71 . C17 . H73 . 109.3 no
H72 . C17 . H73 . 109.0 no
C14 . C13 . C12 . 119.8(5) yes
C14 . C13 . H81 . 119.9 no
C12 . C13 . H81 . 120.3 no
C13 . C12 . C11 . 120.3(5) yes
C13 . C12 . H91 . 119.9 no
C11 . C12 . H91 . 119.7 no
C12 . C11 . C10 . 120.0(6) yes
C12 . C11 . H101 . 119.6 no
C10 . C11 . H101 . 120.4 no
C11 . C10 . C9 . 118.9(5) yes
C11 . C10 . H111 . 120.2 no
C9 . C10 . H111 . 120.9 no
I1 . C1 . C2 . 116.2(3) yes
I1 . C1 . C6 . 116.7(4) yes
C2 . C1 . C6 . 127.1(5) yes
C1 . C2 . O1 . 124.3(5) yes
C1 . C2 . C3 . 116.4(4) yes
O1 . C2 . C3 . 119.3(5) yes
C2 . C3 . C4 . 114.8(4) yes
C2 . C3 . H152 . 107.2 no
C4 . C3 . H152 . 108.8 no
C2 . C3 . H151 . 108.3 no
C4 . C3 . H151 . 108.7 no
H152 . C3 . H151 . 109.0 no
C3 . C4 . C7 . 109.9(4) yes
C3 . C4 . C5 . 108.3(5) yes
C7 . C4 . C5 . 109.3(5) yes
C3 . C4 . C8 . 109.8(5) yes
C7 . C4 . C8 . 109.1(5) yes
C5 . C4 . C8 . 110.3(5) yes
C4 . C7 . H172 . 108.9 no
C4 . C7 . H171 . 109.6 no
H172 . C7 . H171 . 109.8 no
C4 . C7 . H173 . 109.6 no
H172 . C7 . H173 . 108.9 no
H171 . C7 . H173 . 110.0 no
C4 . C5 . C6 . 114.5(5) yes
C4 . C5 . H182 . 109.3 no
C6 . C5 . H182 . 107.7 no
C4 . C5 . H181 . 108.3 no
C6 . C5 . H181 . 108.2 no
H182 . C5 . H181 . 108.8 no
C5 . C6 . C1 . 114.9(5) yes
C5 . C6 . O2 . 119.3(5) yes
C1 . C6 . O2 . 125.8(5) yes
C4 . C8 . H212 . 110.2 no
C4 . C8 . H211 . 109.1 no
H212 . C8 . H211 . 109.9 no
C4 . C8 . H213 . 109.1 no
H212 . C8 . H213 . 109.3 no
H211 . C8 . H213 . 109.2 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
C13 . H81 . O1 2_666 127.92(16) 0.94212 2.553 3.219(8) yes
C7 . H171 . O2 1_556 152.33(16) 0.96638 2.590 3.475(8) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 04/08/12 at 00:02:51
#
#LIST 12
BLOCK SCALE X'S, U'S
RIDE C ( 15,X'S) H ( 51,X'S) H ( 52,X'S)
RIDE C ( 16,X'S) H ( 61,X'S) H ( 62,X'S)
RIDE C ( 17,X'S) H ( 71,X'S) H ( 72,X'S) H ( 73,X'S)
RIDE C ( 13,X'S) H ( 81,X'S)
RIDE C ( 12,X'S) H ( 91,X'S)
RIDE C ( 11,X'S) H ( 101,X'S)
RIDE C ( 10,X'S) H ( 111,X'S)
RIDE C ( 3,X'S) H ( 152,X'S) H ( 151,X'S)
RIDE C ( 7,X'S) H ( 172,X'S) H ( 171,X'S) H ( 173,X'S)
RIDE C ( 5,X'S) H ( 182,X'S) H ( 181,X'S)
RIDE C ( 8,X'S) H ( 212,X'S) H ( 211,X'S) H ( 213,X'S)
END
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 04/08/12 at 00:02:51
#
#LIST 16
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;