# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  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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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_global
#TrackingRef 'TOK495.cif'

_audit_creation_date             12-02-06
_audit_creation_method           CRYSTALS_ver_14.11

_oxford_structure_analysis_title 'Hoc_TOK495 in P2(1)'
_chemical_name_systematic        ?
_chemical_melting_point          ?

data_1
#TrackingRef 'TOK495.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          
;
?
;

_cell_length_a                   5.3111(3)
_cell_length_b                   11.1077(6)
_cell_length_c                   19.5383(13)
_cell_angle_alpha                90
_cell_angle_beta                 96.676(6)
_cell_angle_gamma                90
_cell_volume                     1144.84(12)

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.3639 0.7018 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            4


_chemical_formula_sum            'C11 H14 Cl1 N1 O3'
_chemical_formula_moiety         'C11 H14 Cl1 N1 O3'
_chemical_compound_source        ?
_chemical_formula_weight         243.69


_cell_measurement_reflns_used    5945
_cell_measurement_theta_min      5
_cell_measurement_theta_max      77
_cell_measurement_temperature    190

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.260
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_max          0.490

_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    2.908

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.24
_exptl_absorpt_correction_T_max  0.47
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       '\f & \w scans'

_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      190
_diffrn_ambient_pressure         101
_diffrn_reflns_number            10498
_reflns_number_total             4688
_diffrn_reflns_av_R_equivalents  0.026


_diffrn_reflns_theta_min         4.557
_diffrn_reflns_theta_max         77.404
_diffrn_measured_fraction_theta_max 0.982

_diffrn_reflns_theta_full        73.534
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_reflns_limit_h_min              -6
_reflns_limit_h_max              6
_reflns_limit_k_min              -13
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              24

_oxford_diffrn_Wilson_B_factor   2.24
_oxford_diffrn_Wilson_scale      0.02

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.45
_refine_diff_density_max         0.53


_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns         4688
_refine_ls_number_restraints     1
_refine_ls_number_parameters     291
_oxford_refine_ls_R_factor_ref   0.0383
_refine_ls_wR_factor_ref         0.0950
_refine_ls_goodness_of_fit_ref   1.0397
_refine_ls_shift/su_max          0.0004146
_refine_ls_shift/su_mean         0.0000500


_oxford_reflns_number_all        4688
_refine_ls_R_factor_all          0.0383
_refine_ls_wR_factor_all         0.0950

_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                4585
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_gt          0.0923

_refine_ls_abs_structure_Flack   -0.008(12)
_refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs'
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
0.132E+04 0.215E+04 0.120E+04 416.
;


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
C1a' C 0.5395(4) -0.03195(19) 0.11355(10) 0.0242 1.0000 Uani . . . . . .
C2a' C 0.4374(4) -0.1527(2) 0.08680(12) 0.0315 1.0000 Uani . . . . . .
C3a' C 0.5720(4) -0.1715(2) 0.02161(12) 0.0322 1.0000 Uani . . . . . .
C4a' C 0.6857(5) -0.0453(2) 0.00925(11) 0.0354 1.0000 Uani . . . . . .
C5a' C 0.6512(5) 0.0047(3) -0.06312(12) 0.0441 1.0000 Uani . . . . . .
O6a' O 0.5736(4) 0.03566(15) 0.05323(8) 0.0354 1.0000 Uani . . . . . .
O7a' O 0.7831(3) -0.25223(16) 0.03355(8) 0.0340 1.0000 Uani . . . . . .
O8a' O 0.3911(4) 0.0219(2) -0.08552(9) 0.0503 1.0000 Uani . . . . . .
N1a N 0.2102(3) 0.07434(17) 0.26518(9) 0.0256 1.0000 Uani . . . . . .
C2a C 0.3613(4) 0.01962(19) 0.22564(10) 0.0248 1.0000 Uani . . . . . .
C3a C 0.3651(4) 0.03691(17) 0.15534(10) 0.0230 1.0000 Uani . . . . . .
C4a C 0.1907(4) 0.12080(19) 0.12501(11) 0.0276 1.0000 Uani . . . . . .
C5a C 0.0268(4) 0.1798(2) 0.16523(12) 0.0289 1.0000 Uani . . . . . .
C6a C 0.0411(4) 0.15422(18) 0.23491(12) 0.0271 1.0000 Uani . . . . . .
C7a C -0.1261(4) 0.2149(2) 0.28134(13) 0.0351 1.0000 Uani . . . . . .
Cl8a Cl 0.57097(9) -0.08341(7) 0.26941(2) 0.0320 1.0000 Uani . . . . . .
C1b' C 0.4555(4) 0.46704(17) 0.39748(10) 0.0236 1.0000 Uani . . . . . .
C2b' C 0.5491(4) 0.33959(18) 0.41312(11) 0.0241 1.0000 Uani . . . . . .
C3b' C 0.4523(4) 0.31595(18) 0.48270(11) 0.0257 1.0000 Uani . . . . . .
C4b' C 0.4834(4) 0.43910(17) 0.51731(9) 0.0256 1.0000 Uani . . . . . .
C5b' C 0.7366(5) 0.4479(2) 0.56228(11) 0.0357 1.0000 Uani . . . . . .
O6b' O 0.4751(4) 0.52684(14) 0.46308(8) 0.0321 1.0000 Uani . . . . . .
O7b' O 0.1908(3) 0.28477(15) 0.47454(9) 0.0321 1.0000 Uani . . . . . .
O8b' O 0.7814(4) 0.56517(16) 0.58975(8) 0.0438 1.0000 Uani . . . . . .
N1b N 0.6986(3) 0.57398(16) 0.23281(9) 0.0241 1.0000 Uani . . . . . .
C2b C 0.5680(3) 0.52073(18) 0.27812(10) 0.0227 1.0000 Uani . . . . . .
C3b C 0.6047(4) 0.53622(17) 0.34926(10) 0.0231 1.0000 Uani . . . . . .
C4b C 0.7985(4) 0.6154(2) 0.37333(11) 0.0311 1.0000 Uani . . . . . .
C5b C 0.9386(5) 0.6715(2) 0.32738(12) 0.0332 1.0000 Uani . . . . . .
C6b C 0.8862(4) 0.64966(19) 0.25694(11) 0.0256 1.0000 Uani . . . . . .
C7b C 1.0330(4) 0.7078(2) 0.20499(13) 0.0341 1.0000 Uani . . . . . .
Cl8b Cl 0.33232(9) 0.42292(7) 0.24235(2) 0.0296 1.0000 Uani . . . . . .
H5a1 H -0.0978 0.2349 0.1460 0.0349 1.0000 Uiso R . . . . .
H4a1 H 0.1836 0.1349 0.0786 0.0337 1.0000 Uiso R . . . . .
H1a'1 H 0.7058 -0.0425 0.1416 0.0291 1.0000 Uiso R . . . . .
H4a'1 H 0.8772 -0.0487 0.0257 0.0407 1.0000 Uiso R . . . . .
H3a'1 H 0.4547 -0.1959 -0.0189 0.0380 1.0000 Uiso R . . . . .
H2a'2 H 0.2562 -0.1481 0.0748 0.0384 1.0000 Uiso R . . . . .
H2a'1 H 0.4733 -0.2171 0.1198 0.0382 1.0000 Uiso R . . . . .
H5a'2 H 0.7182 -0.0540 -0.0948 0.0510 1.0000 Uiso R . . . . .
H5a'1 H 0.7392 0.0807 -0.0653 0.0511 1.0000 Uiso R . . . . .
H7a1 H -0.2562 0.2579 0.2541 0.0530 1.0000 Uiso R . . . . .
H7a2 H -0.1961 0.1572 0.3089 0.0533 1.0000 Uiso R . . . . .
H7a3 H -0.0270 0.2689 0.3121 0.0531 1.0000 Uiso R . . . . .
H5b1 H 1.0725 0.7246 0.3438 0.0375 1.0000 Uiso R . . . . .
H4b1 H 0.8264 0.6338 0.4211 0.0371 1.0000 Uiso R . . . . .
H1b'1 H 0.2757 0.4641 0.3792 0.0268 1.0000 Uiso R . . . . .
H4b'1 H 0.3417 0.4529 0.5461 0.0303 1.0000 Uiso R . . . . .
H3b'1 H 0.5544 0.2545 0.5093 0.0308 1.0000 Uiso R . . . . .
H2b'1 H 0.4881 0.2822 0.3798 0.0301 1.0000 Uiso R . . . . .
H2b'2 H 0.7302 0.3410 0.4185 0.0301 1.0000 Uiso R . . . . .
H5b'1 H 0.8736 0.4288 0.5347 0.0416 1.0000 Uiso R . . . . .
H5b'2 H 0.7423 0.3911 0.6006 0.0433 1.0000 Uiso R . . . . .
H7b3 H 1.1816 0.7472 0.2256 0.0522 1.0000 Uiso R . . . . .
H7b2 H 1.0864 0.6470 0.1744 0.0531 1.0000 Uiso R . . . . .
H7b1 H 0.9262 0.7649 0.1773 0.0524 1.0000 Uiso R . . . . .
H8b'1 H 0.7580 0.5675 0.6306 0.0622 1.0000 Uiso R . . . . .
H8a'1 H 0.3948 0.0461 -0.1251 0.0734 1.0000 Uiso R . . . . .
H7b'1 H 0.1847 0.2130 0.4614 0.0474 1.0000 Uiso R . . . . .
H7a'1 H 0.7255 -0.3169 0.0476 0.0525 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
C1a' 0.0300(9) 0.0272(9) 0.0160(9) 0.0042(7) 0.0045(7) 0.0007(8)
C2a' 0.0314(10) 0.0288(10) 0.0353(12) -0.0069(9) 0.0082(9) -0.0027(8)
C3a' 0.0333(10) 0.0397(12) 0.0222(10) -0.0085(8) -0.0028(8) 0.0057(9)
C4a' 0.0447(12) 0.0403(12) 0.0220(10) 0.0047(9) 0.0069(9) 0.0102(10)
C5a' 0.0463(13) 0.0603(15) 0.0266(11) 0.0041(11) 0.0080(10) 0.0080(13)
O6a' 0.0523(9) 0.0333(8) 0.0231(8) 0.0061(7) 0.0152(7) 0.0066(7)
O7a' 0.0366(8) 0.0359(8) 0.0306(8) -0.0003(6) 0.0080(6) 0.0076(7)
O8a' 0.0520(10) 0.0770(14) 0.0209(7) 0.0004(9) 0.0002(7) 0.0224(10)
N1a 0.0288(7) 0.0269(8) 0.0216(8) -0.0010(7) 0.0047(6) 0.0003(7)
C2a 0.0268(9) 0.0261(9) 0.0211(9) 0.0016(8) 0.0013(7) -0.0029(8)
C3a 0.0282(9) 0.0206(8) 0.0204(9) -0.0017(7) 0.0034(7) -0.0037(7)
C4a 0.0294(10) 0.0315(10) 0.0210(10) -0.0004(8) -0.0005(8) -0.0013(8)
C5a 0.0291(9) 0.0274(9) 0.0289(11) 0.0001(8) -0.0024(8) 0.0020(8)
C6a 0.0284(9) 0.0262(10) 0.0265(10) -0.0036(8) 0.0028(8) -0.0021(8)
C7a 0.0317(11) 0.0354(12) 0.0396(13) -0.0066(10) 0.0105(9) 0.0051(9)
Cl8a 0.0375(3) 0.0360(2) 0.0226(2) 0.00441(19) 0.00327(19) 0.0090(2)
C1b' 0.0316(10) 0.0207(8) 0.0187(9) -0.0018(7) 0.0038(7) 0.0023(7)
C2b' 0.0300(9) 0.0209(8) 0.0223(10) -0.0002(7) 0.0072(8) 0.0056(7)
C3b' 0.0313(9) 0.0231(9) 0.0231(10) 0.0018(7) 0.0054(7) 0.0013(8)
C4b' 0.0355(9) 0.0254(9) 0.0174(8) 0.0001(8) 0.0089(7) 0.0022(8)
C5b' 0.0507(13) 0.0296(11) 0.0250(10) -0.0006(9) -0.0037(9) 0.0077(9)
O6b' 0.0589(10) 0.0208(6) 0.0169(7) 0.0013(6) 0.0053(7) 0.0093(7)
O7b' 0.0335(7) 0.0310(7) 0.0331(7) -0.0013(7) 0.0089(6) -0.0003(6)
O8b' 0.0764(13) 0.0315(8) 0.0215(7) 0.0014(7) -0.0023(8) -0.0103(8)
N1b 0.0263(7) 0.0268(8) 0.0192(8) 0.0011(7) 0.0036(6) 0.0010(7)
C2b 0.0250(9) 0.0224(8) 0.0196(9) -0.0018(7) -0.0019(7) 0.0019(7)
C3b 0.0314(9) 0.0202(8) 0.0171(9) 0.0009(7) 0.0002(7) 0.0040(7)
C4b 0.0421(12) 0.0311(10) 0.0188(9) -0.0035(8) -0.0014(8) -0.0027(9)
C5b 0.0395(11) 0.0326(11) 0.0253(10) -0.0009(9) -0.0045(9) -0.0053(9)
C6b 0.0283(8) 0.0237(9) 0.0247(10) 0.0003(8) 0.0032(8) -0.0002(8)
C7b 0.0283(10) 0.0377(11) 0.0370(12) 0.0059(10) 0.0067(9) -0.0055(9)
Cl8b 0.0330(2) 0.0331(2) 0.0214(2) 0.00065(18) -0.00187(17) -0.0088(2)

_refine_ls_extinction_coef       72.2(20)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          7.21(18)
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
C1a' . C2a' . 1.517(3) yes
C1a' . O6a' . 1.427(2) yes
C1a' . C3a . 1.512(3) yes
C1a' . H1a'1 . 0.991 no
C2a' . C3a' . 1.546(3) yes
C2a' . H2a'2 . 0.965 no
C2a' . H2a'1 . 0.967 no
C3a' . C4a' . 1.557(4) yes
C3a' . O7a' . 1.433(3) yes
C3a' . H3a'1 . 0.986 no
C4a' . C5a' . 1.510(3) yes
C4a' . O6a' . 1.421(3) yes
C4a' . H4a'1 . 1.032 no
C5a' . O8a' . 1.413(3) yes
C5a' . H5a'2 . 0.993 no
C5a' . H5a'1 . 0.968 no
O7a' . H7a'1 . 0.839 no
O8a' . H8a'1 . 0.821 no
N1a . C2a . 1.325(3) yes
N1a . C6a . 1.349(3) yes
C2a . C3a . 1.389(3) yes
C2a . Cl8a . 1.749(2) yes
C3a . C4a . 1.396(3) yes
C4a . C5a . 1.401(3) yes
C4a . H4a1 . 0.916 no
C5a . C6a . 1.384(3) yes
C5a . H5a1 . 0.947 no
C6a . C7a . 1.501(3) yes
C7a . H7a1 . 0.951 no
C7a . H7a2 . 0.941 no
C7a . H7a3 . 0.962 no
C1b' . C2b' . 1.520(3) yes
C1b' . O6b' . 1.437(2) yes
C1b' . C3b . 1.510(3) yes
C1b' . H1b'1 . 0.980 no
C2b' . C3b' . 1.531(3) yes
C2b' . H2b'1 . 0.941 no
C2b' . H2b'2 . 0.956 no
C3b' . C4b' . 1.526(3) yes
C3b' . O7b' . 1.422(2) yes
C3b' . H3b'1 . 0.982 no
C4b' . C5b' . 1.522(3) yes
C4b' . O6b' . 1.436(2) yes
C4b' . H4b'1 . 1.003 no
C5b' . O8b' . 1.418(3) yes
C5b' . H5b'1 . 0.977 no
C5b' . H5b'2 . 0.977 no
O7b' . H7b'1 . 0.837 no
O8b' . H8b'1 . 0.823 no
N1b . C2b . 1.326(3) yes
N1b . C6b . 1.346(3) yes
C2b . C3b . 1.392(3) yes
C2b . Cl8b . 1.741(2) yes
C3b . C4b . 1.393(3) yes
C4b . C5b . 1.380(3) yes
C4b . H4b1 . 0.950 no
C5b . C6b . 1.393(3) yes
C5b . H5b1 . 0.951 no
C6b . C7b . 1.496(3) yes
C7b . H7b3 . 0.950 no
C7b . H7b2 . 0.966 no
C7b . H7b1 . 0.972 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
C2a' . C1a' . O6a' . 104.80(16) yes
C2a' . C1a' . C3a . 114.62(17) yes
O6a' . C1a' . C3a . 108.94(16) yes
C2a' . C1a' . H1a'1 . 110.2 no
O6a' . C1a' . H1a'1 . 109.1 no
C3a . C1a' . H1a'1 . 108.9 no
C1a' . C2a' . C3a' . 102.87(17) yes
C1a' . C2a' . H2a'2 . 110.0 no
C3a' . C2a' . H2a'2 . 110.6 no
C1a' . C2a' . H2a'1 . 112.9 no
C3a' . C2a' . H2a'1 . 112.0 no
H2a'2 . C2a' . H2a'1 . 108.4 no
C2a' . C3a' . C4a' . 103.35(18) yes
C2a' . C3a' . O7a' . 112.24(18) yes
C4a' . C3a' . O7a' . 106.16(18) yes
C2a' . C3a' . H3a'1 . 112.9 no
C4a' . C3a' . H3a'1 . 110.1 no
O7a' . C3a' . H3a'1 . 111.6 no
C3a' . C4a' . C5a' . 118.0(2) yes
C3a' . C4a' . O6a' . 106.19(18) yes
C5a' . C4a' . O6a' . 108.66(19) yes
C3a' . C4a' . H4a'1 . 107.8 no
C5a' . C4a' . H4a'1 . 108.3 no
O6a' . C4a' . H4a'1 . 107.5 no
C4a' . C5a' . O8a' . 110.3(2) yes
C4a' . C5a' . H5a'2 . 109.2 no
O8a' . C5a' . H5a'2 . 107.7 no
C4a' . C5a' . H5a'1 . 110.8 no
O8a' . C5a' . H5a'1 . 109.1 no
H5a'2 . C5a' . H5a'1 . 109.6 no
C1a' . O6a' . C4a' . 105.60(16) yes
C3a' . O7a' . H7a'1 . 106.3 no
C5a' . O8a' . H8a'1 . 101.9 no
C2a . N1a . C6a . 117.63(18) yes
N1a . C2a . C3a . 126.3(2) yes
N1a . C2a . Cl8a . 114.18(15) yes
C3a . C2a . Cl8a . 119.49(17) yes
C1a' . C3a . C2a . 122.96(18) yes
C1a' . C3a . C4a . 121.76(17) yes
C2a . C3a . C4a . 115.26(18) yes
C3a . C4a . C5a . 119.92(18) yes
C3a . C4a . H4a1 . 118.9 no
C5a . C4a . H4a1 . 121.2 no
C4a . C5a . C6a . 119.27(19) yes
C4a . C5a . H5a1 . 122.1 no
C6a . C5a . H5a1 . 118.6 no
C5a . C6a . N1a . 121.6(2) yes
C5a . C6a . C7a . 122.3(2) yes
N1a . C6a . C7a . 116.15(19) yes
C6a . C7a . H7a1 . 109.3 no
C6a . C7a . H7a2 . 110.0 no
H7a1 . C7a . H7a2 . 110.7 no
C6a . C7a . H7a3 . 109.8 no
H7a1 . C7a . H7a3 . 110.2 no
H7a2 . C7a . H7a3 . 106.9 no
C2b' . C1b' . O6b' . 105.26(16) yes
C2b' . C1b' . C3b . 114.60(17) yes
O6b' . C1b' . C3b . 109.41(16) yes
C2b' . C1b' . H1b'1 . 108.9 no
O6b' . C1b' . H1b'1 . 107.8 no
C3b . C1b' . H1b'1 . 110.5 no
C1b' . C2b' . C3b' . 101.68(16) yes
C1b' . C2b' . H2b'1 . 114.4 no
C3b' . C2b' . H2b'1 . 111.9 no
C1b' . C2b' . H2b'2 . 108.0 no
C3b' . C2b' . H2b'2 . 110.0 no
H2b'1 . C2b' . H2b'2 . 110.4 no
C2b' . C3b' . C4b' . 102.08(15) yes
C2b' . C3b' . O7b' . 111.52(17) yes
C4b' . C3b' . O7b' . 108.79(17) yes
C2b' . C3b' . H3b'1 . 111.5 no
C4b' . C3b' . H3b'1 . 111.3 no
O7b' . C3b' . H3b'1 . 111.2 no
C3b' . C4b' . C5b' . 110.88(17) yes
C3b' . C4b' . O6b' . 106.78(14) yes
C5b' . C4b' . O6b' . 109.37(17) yes
C3b' . C4b' . H4b'1 . 109.6 no
C5b' . C4b' . H4b'1 . 109.7 no
O6b' . C4b' . H4b'1 . 110.4 no
C4b' . C5b' . O8b' . 112.06(18) yes
C4b' . C5b' . H5b'1 . 109.4 no
O8b' . C5b' . H5b'1 . 107.7 no
C4b' . C5b' . H5b'2 . 110.3 no
O8b' . C5b' . H5b'2 . 108.3 no
H5b'1 . C5b' . H5b'2 . 108.9 no
C1b' . O6b' . C4b' . 109.70(14) yes
C3b' . O7b' . H7b'1 . 105.6 no
C5b' . O8b' . H8b'1 . 111.0 no
C2b . N1b . C6b . 117.92(17) yes
N1b . C2b . C3b . 126.03(18) yes
N1b . C2b . Cl8b . 114.70(14) yes
C3b . C2b . Cl8b . 119.27(15) yes
C1b' . C3b . C2b . 122.50(18) yes
C1b' . C3b . C4b . 122.10(17) yes
C2b . C3b . C4b . 115.31(18) yes
C3b . C4b . C5b . 119.91(18) yes
C3b . C4b . H4b1 . 119.5 no
C5b . C4b . H4b1 . 120.5 no
C4b . C5b . C6b . 120.2(2) yes
C4b . C5b . H5b1 . 119.9 no
C6b . C5b . H5b1 . 119.8 no
C5b . C6b . N1b . 120.61(19) yes
C5b . C6b . C7b . 122.3(2) yes
N1b . C6b . C7b . 117.05(18) yes
C6b . C7b . H7b3 . 112.6 no
C6b . C7b . H7b2 . 109.3 no
H7b3 . C7b . H7b2 . 107.2 no
C6b . C7b . H7b1 . 110.0 no
H7b3 . C7b . H7b1 . 109.7 no
H7b2 . C7b . H7b1 . 107.9 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
C4a . H4a1 . O7a' 2_655 159 0.92 2.55 3.421(3) yes
C3b' . H3b'1 . O6b' 2_646 138 0.98 2.59 3.390(3) yes
O8b' . H8b'1 . N1a 2_656 166 0.82 2.03 2.832(3) yes
O8a' . H8a'1 . N1b 2_645 162 0.82 2.13 2.920(3) yes
O7b' . H7b'1 . O8b' 2_646 164 0.84 1.94 2.755(3) yes
O7a' . H7a'1 . O8a' 2_645 176 0.84 2.06 2.898(3) yes


_iucr_refine_instruction_details_constraints 
;
BLOCK SCALE X'S, U'S
CONT EXTPARAM
CONT ENANTIO
RIDE C ( 1a',X'S) H (1a'1,X'S)
RIDE C ( 2a',X'S) H (2a'2,X'S) H (2a'1,X'S)
RIDE C ( 3a',X'S) H (3a'1,X'S)
RIDE C ( 4a',X'S) H (4a'1,X'S)
RIDE C ( 5a',X'S) H (5a'2,X'S) H (5a'1,X'S)
RIDE O ( 7a',X'S) H (7a'1,X'S)
RIDE O ( 8a',X'S) H (8a'1,X'S)
RIDE C ( 4a,X'S) H (4a1,X'S)
RIDE C ( 5a,X'S) H (5a1,X'S)
RIDE C ( 7a,X'S) H (7a1,X'S) H (7a2,X'S) H (7a3,X'S)
RIDE C ( 1b',X'S) H (1b'1,X'S)
RIDE C ( 2b',X'S) H (2b'1,X'S) H (2b'2,X'S)
RIDE C ( 3b',X'S) H (3b'1,X'S)
RIDE C ( 4b',X'S) H (4b'1,X'S)
RIDE C ( 5b',X'S) H (5b'1,X'S) H (5b'2,X'S)
RIDE O ( 7b',X'S) H (7b'1,X'S)
RIDE O ( 8b',X'S) H (8b'1,X'S)
RIDE C ( 4b,X'S) H (4b1,X'S)
RIDE C ( 5b,X'S) H (5b1,X'S)
RIDE C ( 7b,X'S) H (7b3,X'S) H (7b2,X'S) H (7b1,X'S)
END
;


_iucr_refine_instruction_details_restraints 
;
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;
_database_code_depnum_ccdc_archive 'CCDC 927314'
#######################################################################
#
#                 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_global2
#TrackingRef 'TOK_421_FIN.cif'

_audit_creation_date             13-02-27
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'tok_421 in P2(1)'
_chemical_name_systematic        ?
_chemical_melting_point          ?


data_2
#TrackingRef 'TOK_421_FIN.cif'


_exptl_special_details           
;
;
_refine_special_details          
;
?
;
_cell_length_a                   8.9755(9)
_cell_length_b                   6.9472(5)
_cell_length_c                   9.1777(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.968(9)
_cell_angle_gamma                90
_cell_volume                     572.19(9)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1 '
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.3639 0.7018 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'
Br -0.6763 1.2805 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

_chemical_formula_sum            'C10 H11 Br1 Cl1 N1 O3'
_chemical_formula_moiety         'C10 H11 Br1 Cl1 N1 O3'
_chemical_compound_source        ?
_chemical_formula_weight         308.56


_cell_measurement_reflns_used    3239
_cell_measurement_theta_min      4.8152
_cell_measurement_theta_max      77.1283
_cell_measurement_temperature    170

_exptl_crystal_description       block
_exptl_crystal_colour            'light brown'
_exptl_crystal_size_min          0.210
_exptl_crystal_size_mid          0.560
_exptl_crystal_size_max          0.580

_exptl_crystal_density_diffrn    1.791
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             308
_exptl_absorpt_coefficient_mu    7.002

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.02
_exptl_absorpt_correction_T_max  0.23
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       '\f & \w scans'

_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      170
_diffrn_reflns_number            4296
_reflns_number_total             2333
_diffrn_reflns_av_R_equivalents  0.030

_diffrn_reflns_theta_min         4.819
_diffrn_reflns_theta_max         77.338
_diffrn_measured_fraction_theta_max 0.980

_diffrn_reflns_theta_full        71.924
_diffrn_measured_fraction_theta_full 0.996


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

_oxford_diffrn_Wilson_B_factor   3.44
_oxford_diffrn_Wilson_scale      0.01

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.50
_refine_diff_density_max         0.53

_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_refine_ls_number_reflns         2220
_refine_ls_number_restraints     1
_refine_ls_number_parameters     147
_oxford_refine_ls_R_factor_ref   0.0358
_refine_ls_wR_factor_ref         0.0423
_refine_ls_goodness_of_fit_ref   1.0181
_refine_ls_shift/su_max          0.0005443
_refine_ls_shift/su_mean         0.0000442

_oxford_reflns_number_all        2333
_refine_ls_R_factor_all          0.0375
_refine_ls_wR_factor_all         0.0436

_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                2220
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_gt          0.0423

_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_abs_structure_details 'Flack (1983), 1039 Friedel-pairs'
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_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 -3.95 8.34
;


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 0.6647(4) 0.5417(4) 0.5825(3) 0.0329 1.0000 Uani . . . . . .
C2' C 0.7595(4) 0.5594(5) 0.7203(3) 0.0383 1.0000 Uani . . . . . .
C3' C 0.6456(4) 0.6222(4) 0.8317(3) 0.0364 1.0000 Uani . . . . . .
C4' C 0.5491(4) 0.7610(5) 0.7429(4) 0.0356 1.0000 Uani . . . . . .
C5' C 0.6062(4) 0.9662(5) 0.7414(4) 0.0398 1.0000 Uani . . . . . .
O6' O 0.5519(2) 0.6875(4) 0.5954(2) 0.0408 1.0000 Uani . . . . . .
O8' O 0.5685(4) 1.0572(4) 0.8736(3) 0.0594 1.0000 Uani . . . . . .
O7' O 0.5630(4) 0.4571(4) 0.8749(3) 0.0551 1.0000 Uani . . . . . .
C3 C 0.7495(3) 0.5738(4) 0.4439(4) 0.0318 1.0000 Uani . . . . . .
C2 C 0.8442(4) 0.4366(5) 0.3864(3) 0.0338 1.0000 Uani . . . . . .
N1 N 0.9294(3) 0.4568(4) 0.2721(3) 0.0362 1.0000 Uani . . . . . .
C6 C 0.9186(4) 0.6255(5) 0.2037(3) 0.0376 1.0000 Uani . . . . . .
C5 C 0.8248(5) 0.7725(5) 0.2428(4) 0.0441 1.0000 Uani . . . . . .
C4 C 0.7400(4) 0.7429(6) 0.3656(4) 0.0410 1.0000 Uani . . . . . .
Cl8 Cl 0.86029(11) 0.21252(14) 0.47246(11) 0.0496 1.0000 Uani . . . . . .
Br7 Br 1.04641(5) 0.65960(12) 0.04304(4) 0.0537 1.0000 Uani . . . . . .
H41 H 0.6774 0.8398 0.3956 0.0490 1.0000 Uiso R . . . . .
H51 H 0.8195 0.8853 0.1910 0.0534 1.0000 Uiso R . . . . .
H1'1 H 0.6183 0.4132 0.5819 0.0400 1.0000 Uiso R . . . . .
H4'1 H 0.4469 0.7624 0.7800 0.0429 1.0000 Uiso R . . . . .
H3'1 H 0.6919 0.6856 0.9170 0.0436 1.0000 Uiso R . . . . .
H2'1 H 0.8356 0.6569 0.7093 0.0460 1.0000 Uiso R . . . . .
H2'2 H 0.8065 0.4366 0.7436 0.0461 1.0000 Uiso R . . . . .
H5'2 H 0.7140 0.9680 0.7296 0.0483 1.0000 Uiso R . . . . .
H5'1 H 0.5598 1.0364 0.6616 0.0481 1.0000 Uiso R . . . . .
H8'1 H 0.5706 1.1739 0.8889 0.0889 1.0000 Uiso R . . . . .
H7'1 H 0.5230 0.4716 0.9543 0.0830 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
C1' 0.0399(15) 0.0276(15) 0.0314(14) -0.0024(12) 0.0072(12) 0.0031(11)
C2' 0.0469(17) 0.0377(17) 0.0305(15) 0.0058(13) 0.0044(13) 0.0094(14)
C3' 0.0566(17) 0.0214(16) 0.0316(14) 0.0013(11) 0.0109(13) -0.0006(12)
C4' 0.0399(16) 0.0323(17) 0.0350(15) -0.0029(13) 0.0127(13) -0.0001(13)
C5' 0.0559(19) 0.0265(15) 0.0376(17) 0.0034(13) 0.0156(15) 0.0024(14)
O6' 0.0406(10) 0.0481(15) 0.0339(10) -0.0078(11) 0.0023(8) 0.0137(11)
O8' 0.101(2) 0.0267(12) 0.0523(17) -0.0056(12) 0.0414(16) -0.0074(13)
O7' 0.092(2) 0.0259(12) 0.0491(15) 0.0041(11) 0.0347(15) -0.0025(13)
C3 0.0382(14) 0.0268(14) 0.0305(15) -0.0009(12) 0.0011(12) 0.0016(12)
C2 0.0408(16) 0.0287(15) 0.0320(15) -0.0019(12) 0.0022(12) 0.0004(12)
N1 0.0453(15) 0.0333(14) 0.0303(13) -0.0048(11) 0.0071(11) 0.0013(11)
C6 0.0489(16) 0.0372(17) 0.0270(13) -0.0064(13) 0.0076(12) -0.0030(14)
C5 0.063(2) 0.0324(17) 0.0368(17) 0.0090(14) 0.0089(16) 0.0072(15)
C4 0.0468(18) 0.0329(16) 0.0437(18) -0.0016(14) 0.0103(15) 0.0034(13)
Cl8 0.0640(5) 0.0304(4) 0.0550(5) 0.0079(3) 0.0186(4) 0.0095(3)
Br7 0.0760(3) 0.0457(2) 0.0401(2) -0.00444(17) 0.02460(16) -0.0076(2)

_refine_ls_extinction_coef       21.0(18)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          9.06(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1' . C2' . 1.517(4) yes
C1' . O6' . 1.438(4) yes
C1' . C3 . 1.510(4) yes
C1' . H1'1 . 0.985 no
C2' . C3' . 1.522(4) yes
C2' . H2'1 . 0.969 no
C2' . H2'2 . 0.974 no
C3' . C4' . 1.523(4) yes
C3' . O7' . 1.425(4) yes
C3' . H3'1 . 0.985 no
C4' . C5' . 1.515(5) yes
C4' . O6' . 1.448(4) yes
C4' . H4'1 . 0.984 no
C5' . O8' . 1.414(4) yes
C5' . H5'2 . 0.975 no
C5' . H5'1 . 0.968 no
O8' . H8'1 . 0.823 no
O7' . H7'1 . 0.825 no
C3 . C2 . 1.387(4) yes
C3 . C4 . 1.379(5) yes
C2 . N1 . 1.316(4) yes
C2 . Cl8 . 1.751(3) yes
N1 . C6 . 1.332(5) yes
C6 . C5 . 1.375(5) yes
C6 . Br7 . 1.898(3) yes
C5 . C4 . 1.386(5) yes
C5 . H51 . 0.917 no
C4 . H41 . 0.922 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' . O6' . 105.0(2) yes
C2' . C1' . C3 . 114.0(3) yes
O6' . C1' . C3 . 109.3(3) yes
C2' . C1' . H1'1 . 108.0 no
O6' . C1' . H1'1 . 109.9 no
C3 . C1' . H1'1 . 110.4 no
C1' . C2' . C3' . 102.1(3) yes
C1' . C2' . H2'1 . 110.9 no
C3' . C2' . H2'1 . 110.6 no
C1' . C2' . H2'2 . 110.3 no
C3' . C2' . H2'2 . 113.4 no
H2'1 . C2' . H2'2 . 109.3 no
C2' . C3' . C4' . 101.8(2) yes
C2' . C3' . O7' . 108.3(3) yes
C4' . C3' . O7' . 111.4(3) yes
C2' . C3' . H3'1 . 112.5 no
C4' . C3' . H3'1 . 111.8 no
O7' . C3' . H3'1 . 110.7 no
C3' . C4' . C5' . 114.3(3) yes
C3' . C4' . O6' . 105.0(2) yes
C5' . C4' . O6' . 108.2(3) yes
C3' . C4' . H4'1 . 110.2 no
C5' . C4' . H4'1 . 108.2 no
O6' . C4' . H4'1 . 111.0 no
C4' . C5' . O8' . 109.1(3) yes
C4' . C5' . H5'2 . 110.5 no
O8' . C5' . H5'2 . 110.0 no
C4' . C5' . H5'1 . 109.8 no
O8' . C5' . H5'1 . 108.5 no
H5'2 . C5' . H5'1 . 109.0 no
C4' . O6' . C1' . 110.4(2) yes
C5' . O8' . H8'1 . 125.6 no
C3' . O7' . H7'1 . 112.6 no
C1' . C3 . C2 . 122.7(3) yes
C1' . C3 . C4 . 122.5(3) yes
C2 . C3 . C4 . 114.8(3) yes
C3 . C2 . N1 . 126.7(3) yes
C3 . C2 . Cl8 . 119.1(2) yes
N1 . C2 . Cl8 . 114.2(2) yes
C2 . N1 . C6 . 115.5(3) yes
N1 . C6 . C5 . 124.7(3) yes
N1 . C6 . Br7 . 115.9(2) yes
C5 . C6 . Br7 . 119.4(3) yes
C6 . C5 . C4 . 116.7(3) yes
C6 . C5 . H51 . 121.7 no
C4 . C5 . H51 . 121.6 no
C5 . C4 . C3 . 121.3(4) yes
C5 . C4 . H41 . 118.7 no
C3 . C4 . H41 . 119.9 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
O8' . H8'1 . O7' 1_565 166.10(14) 0.823 1.973 2.779(5) yes
O7' . H7'1 . O8' 2_647 168.57(11) 0.825 1.889 2.702(5) yes


_iucr_refine_instruction_details_constraints 
;
BLOCK SCALE X'S, U'S
CONT EXTPARAM
CONT ENANTIO
RIDE C ( 1,X'S) H ( 11,X'S)
RIDE C ( 2,X'S) H ( 21,X'S) H ( 22,X'S)
RIDE C ( 3,X'S) H ( 31,X'S)
RIDE C ( 4,X'S) H ( 41,X'S)
RIDE C ( 5,X'S) H ( 52,X'S) H ( 51,X'S)
RIDE O ( 7,X'S) H ( 71,X'S)
RIDE O ( 8,X'S) H ( 81,X'S)
RIDE C ( 13,X'S) H ( 131,X'S)
RIDE C ( 14,X'S) H ( 141,X'S)
END
;


_iucr_refine_instruction_details_restraints 
;
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;



_database_code_depnum_ccdc_archive 'CCDC 927315'