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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_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                   9.3185(2)
_cell_length_b                   11.8470(2)
_cell_length_c                   13.2263(3)
_cell_angle_alpha                94.2169(9)
_cell_angle_beta                 90.9044(9)
_cell_angle_gamma                109.4296(11)
_cell_volume                     1372.00(5)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1 '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C29.50 H21.50 Cl1.50 N3 O4 
# Dc =      1.30 Fooo =    612.00 Mu =      2.27 M =    535.19
# Found Formula = C30 H22 Cl3.00 N3 O4 
# Dc =      1.44 FOOO =    612.00 Mu =      3.76 M =    594.88

_chemical_formula_sum            'C30 H22 Cl3 N3 O4'
_chemical_formula_moiety         'C30 H22 Cl3 N3 O4'
_chemical_compound_source        syn
_chemical_formula_weight         594.88


_cell_measurement_reflns_used    6124
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_max          0.420

_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             612.000
_exptl_absorpt_coefficient_mu    0.376

# Sheldrick geometric approximatio 0.94 0.96 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.96
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_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            29697
_reflns_number_total             6242
_diffrn_reflns_av_R_equivalents  0.019
# Number of reflections without Friedels Law is 29697 
# Number of reflections with Friedels Law is 6242 
# Theoretical number of reflections is about 6321 


_diffrn_reflns_theta_min         5.130
_diffrn_reflns_theta_max         27.527
_diffrn_measured_fraction_theta_max 0.989

_diffrn_reflns_theta_full        26.976
_diffrn_measured_fraction_theta_full 0.991


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              -15
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   4.13
_oxford_diffrn_Wilson_scale      0.69

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

_refine_diff_density_min         -0.84
_refine_diff_density_max         0.71


# 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         6242
_refine_ls_number_restraints     162
_refine_ls_number_parameters     389
_oxford_refine_ls_R_factor_ref   0.0840
_refine_ls_wR_factor_ref         0.1303
_refine_ls_goodness_of_fit_ref   1.0492
_refine_ls_shift/su_max          0.0020352
_refine_ls_shift/su_mean         0.0000301


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        6242
_refine_ls_R_factor_all          0.0840
_refine_ls_wR_factor_all         0.1303

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4950
_refine_ls_R_factor_gt           0.0693
_refine_ls_wR_factor_gt          0.1173

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


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 28.8 38.6 12.0 
;

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

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

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


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.0110(3) -0.0817(2) 0.14959(19) 0.0311 1.0000 Uani . . . . . .
C2 C -0.0559(3) -0.1966(2) 0.09851(19) 0.0335 1.0000 Uani . . . . . .
C3 C -0.1833(3) -0.2789(2) 0.1365(2) 0.0424 1.0000 Uani . . . . . .
C4 C -0.2410(3) -0.2463(3) 0.2251(3) 0.0508 1.0000 Uani . . . . . .
C5 C -0.1766(3) -0.1344(3) 0.2781(2) 0.0487 1.0000 Uani . . . . . .
C6 C -0.0490(3) -0.0516(2) 0.2408(2) 0.0365 1.0000 Uani . . . . . .
N7 N 0.0154(3) -0.22106(19) 0.01075(17) 0.0390 1.0000 Uani . . . . . .
C8 C -0.0192(3) -0.3247(2) -0.0516(2) 0.0383 1.0000 Uani . . . . . .
O9 O -0.1266(3) -0.41439(18) -0.03938(18) 0.0558 1.0000 Uani . . . . . .
C10 C 0.0879(3) -0.3207(2) -0.1348(2) 0.0390 1.0000 Uani . . . . . .
C11 C 0.1795(4) -0.2158(3) -0.1731(2) 0.0464 1.0000 Uani . . . . . .
C12 C 0.2797(4) -0.2202(3) -0.2486(3) 0.0583 1.0000 Uani . . . . . .
C13 C 0.2885(4) -0.3296(4) -0.2869(2) 0.0587 1.0000 Uani . . . . . .
C14 C 0.1965(4) -0.4334(3) -0.2502(2) 0.0549 1.0000 Uani . . . . . .
C15 C 0.0967(4) -0.4304(3) -0.1755(2) 0.0464 1.0000 Uani . . . . . .
N16 N 0.0283(3) 0.06203(19) 0.29219(18) 0.0401 1.0000 Uani . . . . . .
C17 C -0.0117(3) 0.1107(3) 0.3783(2) 0.0445 1.0000 Uani . . . . . .
O18 O -0.1322(3) 0.0670(2) 0.4182(2) 0.0785 1.0000 Uani . . . . . .
C19 C 0.1003(3) 0.2277(2) 0.4223(2) 0.0384 1.0000 Uani . . . . . .
C20 C 0.2476(4) 0.2405(3) 0.4497(3) 0.0553 1.0000 Uani . . . . . .
C21 C 0.3413(4) 0.3486(3) 0.4976(3) 0.0613 1.0000 Uani . . . . . .
N22 N 0.2961(3) 0.4431(3) 0.5185(2) 0.0562 1.0000 Uani . . . . . .
C23 C 0.1563(4) 0.4305(3) 0.4891(4) 0.0713 1.0000 Uani . . . . . .
C24 C 0.0534(4) 0.3253(3) 0.4424(3) 0.0635 1.0000 Uani . . . . . .
C25 C 0.1414(3) 0.0026(2) 0.10984(18) 0.0319 1.0000 Uani . . . . . .
C26 C 0.2500(3) 0.0754(2) 0.07762(19) 0.0343 1.0000 Uani . . . . . .
C27 C 0.3792(3) 0.1585(2) 0.03552(19) 0.0345 1.0000 Uani . . . . . .
C28 C 0.4482(3) 0.1161(2) -0.0449(2) 0.0418 1.0000 Uani . . . . . .
C29 C 0.5742(4) 0.1923(3) -0.0888(2) 0.0487 1.0000 Uani . . . . . .
C30 C 0.6326(3) 0.3123(3) -0.0534(2) 0.0470 1.0000 Uani . . . . . .
C31 C 0.5643(3) 0.3562(2) 0.0245(2) 0.0400 1.0000 Uani . . . . . .
C32 C 0.4401(3) 0.2809(2) 0.07116(19) 0.0331 1.0000 Uani . . . . . .
C33 C 0.3717(3) 0.3282(2) 0.1580(2) 0.0382 1.0000 Uani . . . . . .
O34 O 0.2772(3) 0.26820(18) 0.21086(17) 0.0579 1.0000 Uani . . . . . .
O35 O 0.4295(2) 0.44809(16) 0.17342(16) 0.0436 1.0000 Uani . . . . . .
C36 C 0.3665(4) 0.4999(3) 0.2566(3) 0.0562 1.0000 Uani . . . . . .
C37 C 0.2707(2) 0.84612(17) 0.39460(11) 0.0677 1.0000 Uani D . . . . .
Cl38 Cl 0.4152(4) 0.8022(3) 0.4437(2) 0.1363 0.846(5) Uani D . P 1 1 .
Cl39 Cl 0.1483(3) 0.72822(18) 0.31330(16) 0.0775 0.846(5) Uani D . P 1 1 .
Cl40 Cl 0.3497(2) 0.97370(13) 0.32654(12) 0.0700 0.846(5) Uani D . P 1 1 .
Cl138 Cl 0.3489(14) 0.7653(10) 0.4692(7) 0.0954 0.154(5) Uani D . P 1 2 .
Cl139 Cl 0.1582(12) 0.7512(8) 0.2963(6) 0.0678 0.154(5) Uani D . P 1 2 .
Cl140 Cl 0.4145(10) 0.9595(8) 0.3454(7) 0.1005 0.154(5) Uani D . P 1 2 .
H31 H -0.2291 -0.3557 0.1024 0.0531 1.0000 Uiso R . . . . .
H41 H -0.3278 -0.3020 0.2506 0.0641 1.0000 Uiso R . . . . .
H51 H -0.2165 -0.1136 0.3391 0.0619 1.0000 Uiso R . . . . .
H111 H 0.1742 -0.1403 -0.1483 0.0584 1.0000 Uiso R . . . . .
H121 H 0.3411 -0.1484 -0.2723 0.0730 1.0000 Uiso R . . . . .
H131 H 0.3556 -0.3320 -0.3347 0.0722 1.0000 Uiso R . . . . .
H141 H 0.2022 -0.5067 -0.2787 0.0680 1.0000 Uiso R . . . . .
H151 H 0.0337 -0.5013 -0.1492 0.0581 1.0000 Uiso R . . . . .
H201 H 0.2843 0.1764 0.4364 0.0681 1.0000 Uiso R . . . . .
H211 H 0.4433 0.3573 0.5139 0.0750 1.0000 Uiso R . . . . .
H231 H 0.1238 0.4948 0.5022 0.0845 1.0000 Uiso R . . . . .
H241 H -0.0464 0.3206 0.4255 0.0794 1.0000 Uiso R . . . . .
H281 H 0.4098 0.0352 -0.0690 0.0532 1.0000 Uiso R . . . . .
H291 H 0.6211 0.1610 -0.1417 0.0598 1.0000 Uiso R . . . . .
H301 H 0.7166 0.3648 -0.0841 0.0593 1.0000 Uiso R . . . . .
H311 H 0.6027 0.4381 0.0484 0.0506 1.0000 Uiso R . . . . .
H362 H 0.4025 0.5867 0.2551 0.0865 1.0000 Uiso R . . . . .
H363 H 0.4028 0.4803 0.3198 0.0868 1.0000 Uiso R . . . . .
H361 H 0.2569 0.4710 0.2533 0.0869 1.0000 Uiso R . . . . .
H161 H 0.1081 0.1037 0.2647 0.0502 1.0000 Uiso R . . . . .
H71 H 0.0926 -0.1636 -0.0060 0.0492 1.0000 Uiso R . . . . .
H371 H 0.2081 0.8655 0.4524 0.1140 0.846(5) Uiso R . P 1 1 .
H372 H 0.2107 0.8818 0.4396 0.1132 0.154(5) Uiso R . P 1 2 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.170(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
C1 . C2 . 1.409(3) yes
C1 . C6 . 1.409(3) yes
C1 . C25 . 1.428(3) yes
C2 . C3 . 1.390(3) yes
C2 . N7 . 1.405(3) yes
C3 . C4 . 1.380(4) yes
C3 . H31 . 0.943 no
C4 . C5 . 1.389(4) yes
C4 . H41 . 0.943 no
C5 . C6 . 1.391(4) yes
C5 . H51 . 0.944 no
C6 . N16 . 1.414(3) yes
N7 . C8 . 1.368(3) yes
N7 . H71 . 0.855 no
C8 . O9 . 1.216(3) yes
C8 . C10 . 1.490(4) yes
C10 . C11 . 1.389(4) yes
C10 . C15 . 1.398(4) yes
C11 . C12 . 1.388(5) yes
C11 . H111 . 0.947 no
C12 . C13 . 1.385(5) yes
C12 . H121 . 0.932 no
C13 . C14 . 1.372(5) yes
C13 . H131 . 0.902 no
C14 . C15 . 1.374(5) yes
C14 . H141 . 0.940 no
C15 . H151 . 0.945 no
N16 . C17 . 1.352(3) yes
N16 . H161 . 0.848 no
C17 . O18 . 1.217(4) yes
C17 . C19 . 1.500(4) yes
C19 . C20 . 1.370(4) yes
C19 . C24 . 1.376(4) yes
C20 . C21 . 1.387(4) yes
C20 . H201 . 0.938 no
C21 . N22 . 1.334(4) yes
C21 . H211 . 0.941 no
N22 . C23 . 1.310(5) yes
C23 . C24 . 1.388(5) yes
C23 . H231 . 0.916 no
C24 . H241 . 0.935 no
C25 . C26 . 1.199(3) yes
C26 . C27 . 1.429(3) yes
C27 . C28 . 1.398(4) yes
C27 . C32 . 1.411(3) yes
C28 . C29 . 1.387(4) yes
C28 . H281 . 0.934 no
C29 . C30 . 1.385(4) yes
C29 . H291 . 0.948 no
C30 . C31 . 1.378(4) yes
C30 . H301 . 0.942 no
C31 . C32 . 1.391(3) yes
C31 . H311 . 0.943 no
C32 . C33 . 1.485(4) yes
C33 . O34 . 1.203(3) yes
C33 . O35 . 1.339(3) yes
O35 . C36 . 1.446(4) yes
C36 . H362 . 0.971 no
C36 . H363 . 0.969 no
C36 . H361 . 0.963 no
C37 . Cl38 . 1.730(2) yes
C37 . Cl39 . 1.757(3) yes
C37 . Cl40 . 1.766(2) yes
C37 . H371 . 1.027 no
C37 . Cl138 . 1.734(6) yes
C37 . Cl139 . 1.735(6) yes
C37 . Cl140 . 1.727(5) yes
C37 . H372 . 0.988 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . C6 . 119.8(2) yes
C2 . C1 . C25 . 119.8(2) yes
C6 . C1 . C25 . 120.4(2) yes
C1 . C2 . C3 . 120.1(2) yes
C1 . C2 . N7 . 116.1(2) yes
C3 . C2 . N7 . 123.8(2) yes
C2 . C3 . C4 . 118.8(2) yes
C2 . C3 . H31 . 120.5 no
C4 . C3 . H31 . 120.6 no
C3 . C4 . C5 . 122.6(3) yes
C3 . C4 . H41 . 118.7 no
C5 . C4 . H41 . 118.7 no
C4 . C5 . C6 . 119.0(3) yes
C4 . C5 . H51 . 121.7 no
C6 . C5 . H51 . 119.3 no
C1 . C6 . C5 . 119.7(2) yes
C1 . C6 . N16 . 117.4(2) yes
C5 . C6 . N16 . 122.8(2) yes
C2 . N7 . C8 . 129.4(2) yes
C2 . N7 . H71 . 115.9 no
C8 . N7 . H71 . 114.7 no
N7 . C8 . O9 . 123.1(3) yes
N7 . C8 . C10 . 114.7(2) yes
O9 . C8 . C10 . 122.2(2) yes
C8 . C10 . C11 . 124.3(3) yes
C8 . C10 . C15 . 117.1(3) yes
C11 . C10 . C15 . 118.6(3) yes
C10 . C11 . C12 . 120.4(3) yes
C10 . C11 . H111 . 120.6 no
C12 . C11 . H111 . 119.0 no
C11 . C12 . C13 . 120.2(3) yes
C11 . C12 . H121 . 118.8 no
C13 . C12 . H121 . 121.0 no
C12 . C13 . C14 . 119.4(3) yes
C12 . C13 . H131 . 120.0 no
C14 . C13 . H131 . 120.6 no
C13 . C14 . C15 . 121.0(3) yes
C13 . C14 . H141 . 117.9 no
C15 . C14 . H141 . 121.0 no
C10 . C15 . C14 . 120.3(3) yes
C10 . C15 . H151 . 118.0 no
C14 . C15 . H151 . 121.7 no
C6 . N16 . C17 . 127.4(2) yes
C6 . N16 . H161 . 115.1 no
C17 . N16 . H161 . 117.5 no
N16 . C17 . O18 . 123.8(3) yes
N16 . C17 . C19 . 116.0(2) yes
O18 . C17 . C19 . 120.1(3) yes
C17 . C19 . C20 . 122.5(3) yes
C17 . C19 . C24 . 119.8(3) yes
C20 . C19 . C24 . 117.6(3) yes
C19 . C20 . C21 . 119.4(3) yes
C19 . C20 . H201 . 120.1 no
C21 . C20 . H201 . 120.5 no
C20 . C21 . N22 . 123.4(3) yes
C20 . C21 . H211 . 118.7 no
N22 . C21 . H211 . 117.9 no
C21 . N22 . C23 . 116.4(3) yes
N22 . C23 . C24 . 124.4(3) yes
N22 . C23 . H231 . 117.6 no
C24 . C23 . H231 . 118.0 no
C23 . C24 . C19 . 118.9(3) yes
C23 . C24 . H241 . 120.6 no
C19 . C24 . H241 . 120.5 no
C1 . C25 . C26 . 178.5(3) yes
C25 . C26 . C27 . 177.4(3) yes
C26 . C27 . C28 . 118.3(2) yes
C26 . C27 . C32 . 123.1(2) yes
C28 . C27 . C32 . 118.6(2) yes
C27 . C28 . C29 . 121.0(3) yes
C27 . C28 . H281 . 119.7 no
C29 . C28 . H281 . 119.3 no
C28 . C29 . C30 . 119.9(3) yes
C28 . C29 . H291 . 119.5 no
C30 . C29 . H291 . 120.6 no
C29 . C30 . C31 . 119.9(3) yes
C29 . C30 . H301 . 120.2 no
C31 . C30 . H301 . 119.8 no
C30 . C31 . C32 . 121.1(3) yes
C30 . C31 . H311 . 120.4 no
C32 . C31 . H311 . 118.5 no
C27 . C32 . C31 . 119.5(2) yes
C27 . C32 . C33 . 120.0(2) yes
C31 . C32 . C33 . 120.5(2) yes
C32 . C33 . O34 . 125.3(2) yes
C32 . C33 . O35 . 112.2(2) yes
O34 . C33 . O35 . 122.4(3) yes
C33 . O35 . C36 . 114.9(2) yes
O35 . C36 . H362 . 109.0 no
O35 . C36 . H363 . 108.6 no
H362 . C36 . H363 . 108.6 no
O35 . C36 . H361 . 112.4 no
H362 . C36 . H361 . 108.9 no
H363 . C36 . H361 . 109.3 no
Cl38 . C37 . Cl39 . 109.57(6) yes
Cl38 . C37 . Cl40 . 109.57(6) yes
Cl39 . C37 . Cl40 . 109.67(6) yes
Cl38 . C37 . H371 . 109.9 no
Cl39 . C37 . H371 . 108.1 no
Cl40 . C37 . H371 . 110.0 no
Cl138 . C37 . Cl139 . 109.63(6) yes
Cl138 . C37 . Cl140 . 109.65(6) yes
Cl139 . C37 . Cl140 . 109.69(6) yes
Cl138 . C37 . H372 . 106.7 no
Cl139 . C37 . H372 . 111.8 no
Cl140 . C37 . H372 . 109.3 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
C3 . H31 . O9 . 120.89(8) 0.943 2.284 2.884(4) yes
C5 . H51 . O18 . 123.04(10) 0.944 2.194 2.822(4) yes
C30 . H301 . O9 1_665 131.67(8) 0.942 2.555 3.258(4) yes
N16 . H161 . O34 . 157.31(8) 0.848 2.233 3.033(4) yes
C37 . H371 . O18 2_566 166.21(9) 1.027 2.070 3.077(4) yes
C37 . H372 . O18 2_566 156.05(11) 0.988 2.148 3.077(4) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 31/01/14 at 07:40:30
#
#LIST     12                                                                    
BLOCK SCALE X'S U'S 
EQUIV PART(1001,OCC) PART(1002,OCC) 
WEIGHT -1 PART(1002,OCC) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE N   (   7,X'S) H   (  71,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE N   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  36,X'S) H   ( 362,X'S) H   ( 363,X'S) H   ( 361,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) H   ( 372,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 31/01/14 at 07:40:30
#
#LIST     16                                                                    
SAME  C(37)  CL(38)  CL(39)  CL(40)  AND 
CONT  C(37)  CL(39)  CL(40)  CL(38)  AND 
CONT  C(37)  CL(40)  CL(38)  CL(39)  AND 
CONT  C(37)  CL(138)  CL(139)  CL(140)  AND 
CONT  C(37)  CL(139)  CL(140)  CL(138)  AND 
CONT  C(37)  CL(140)  CL(138)  CL(139) 
SIMU  0.01   C(37)  CL(38)  CL(39)  CL(40)  AND 
CONT  C(37)  CL(39)  CL(40)  CL(38)  AND 
CONT  C(37)  CL(40)  CL(38)  CL(39)  AND 
CONT  C(37)  CL(138)  CL(139)  CL(140)  AND 
CONT  C(37)  CL(139)  CL(140)  CL(138)  AND 
CONT  C(37)  CL(140)  CL(138)  CL(139) 
DELU  0.01   C(37)  CL(38)  CL(39)  CL(40)  AND 
CONT  C(37)  CL(39)  CL(40)  CL(38)  AND 
CONT  C(37)  CL(40)  CL(38)  CL(39)  AND 
CONT  C(37)  CL(138)  CL(139)  CL(140)  AND 
CONT  C(37)  CL(139)  CL(140)  CL(138)  AND 
CONT  C(37)  CL(140)  CL(138)  CL(139) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

_database_code_depnum_ccdc_archive 'CCDC 993562'
