# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  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_2a
_audit_creation_date             2013-05-09
_audit_creation_method           CRYSTALS_ver_14.43

_oxford_structure_analysis_title '015mwj13 At 13:10 on 22/ 4'
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

#############################################################
_cell_length_a                   8.2507(2)
_cell_length_b                   9.1868(2)
_cell_length_c                   10.7811(3)
_cell_angle_alpha                92.8871(10)
_cell_angle_beta                 100.0815(10)
_cell_angle_gamma                91.7403(10)
_cell_volume                     802.90(3)

_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'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 '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 = C16 H17 Cl2 N1 O2 S1 
# Dc =      1.48 Fooo =    368.00 Mu =      5.40 M =    358.29
# Found Formula = C16 H15 Cl2 N1 O2 S1 
# Dc =      1.47 FOOO =    368.00 Mu =      5.40 M =    356.27

_chemical_formula_sum            'C16 H15 Cl2 N O2 S'
_chemical_formula_moiety         'C16 H15 Cl2 N O2 S'
_chemical_compound_source        .
_chemical_formula_weight         356.27


_cell_measurement_reflns_used    3378
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.170
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_max          0.290

_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    0.540

# Sheldrick geometric approximatio 0.88 0.91 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.91
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_ambient_pressure         101
_diffrn_reflns_number            13254
_reflns_number_total             3627
_diffrn_reflns_av_R_equivalents  0.024
# Number of reflections without Friedels Law is 6384 
# Number of reflections with Friedels Law is 3627 
# Theoretical number of reflections is about 3676 


_diffrn_reflns_theta_min         5.195
_diffrn_reflns_theta_max         27.465
_diffrn_measured_fraction_theta_max 0.989

_diffrn_reflns_theta_full        26.915
_diffrn_measured_fraction_theta_full 0.992


_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   1.89
_oxford_diffrn_Wilson_scale      2.85

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

_refine_diff_density_min         -0.52
_refine_diff_density_max         0.48


# 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         3627
_refine_ls_number_restraints     0
_refine_ls_number_parameters     199
_oxford_refine_ls_R_factor_ref   0.0523
_refine_ls_wR_factor_ref         0.0847
_refine_ls_goodness_of_fit_ref   0.9272
_refine_ls_shift/su_max          0.0001421
_refine_ls_shift/su_mean         0.0000135


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3627
_refine_ls_R_factor_all          0.0523
_refine_ls_wR_factor_all         0.0847

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2821
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_gt          0.0784

# 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= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.50P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

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

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

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


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Cl1 Cl 0.20050(6) 0.20660(5) 0.05841(4) 0.0281 1.0000 Uani . . . . . .
C2 C 0.1255(2) 0.11316(18) 0.17610(16) 0.0194 1.0000 Uani . . . . . .
N3 N 0.24142(17) 0.07304(15) 0.27909(13) 0.0179 1.0000 Uani . . . . . .
S4 S 0.28131(5) 0.19124(5) 0.40560(4) 0.0177 1.0000 Uani . . . . . .
C5 C 0.4499(2) 0.30367(18) 0.38507(16) 0.0180 1.0000 Uani . . . . . .
C6 C 0.4215(2) 0.4370(2) 0.33173(17) 0.0229 1.0000 Uani . . . . . .
C7 C 0.5536(2) 0.5230(2) 0.31130(17) 0.0254 1.0000 Uani . . . . . .
C8 C 0.7148(2) 0.4776(2) 0.34262(17) 0.0247 1.0000 Uani . . . . . .
C9 C 0.8587(3) 0.5695(2) 0.3183(2) 0.0364 1.0000 Uani . . . . . .
C10 C 0.7395(2) 0.3437(2) 0.39675(19) 0.0273 1.0000 Uani . . . . . .
C11 C 0.6097(2) 0.2567(2) 0.41886(18) 0.0240 1.0000 Uani . . . . . .
C12 C 0.3859(2) -0.00787(19) 0.25038(17) 0.0217 1.0000 Uani . . . . . .
C13 C 0.3358(2) -0.14183(18) 0.16421(16) 0.0197 1.0000 Uani . . . . . .
C14 C 0.2073(2) -0.2382(2) 0.17933(17) 0.0221 1.0000 Uani . . . . . .
C15 C 0.1730(2) -0.3640(2) 0.10228(18) 0.0258 1.0000 Uani . . . . . .
C16 C 0.2651(2) -0.3961(2) 0.00983(18) 0.0267 1.0000 Uani . . . . . .
C17 C 0.3920(2) -0.3020(2) -0.00656(17) 0.0264 1.0000 Uani . . . . . .
C18 C 0.4278(2) -0.1758(2) 0.07029(17) 0.0229 1.0000 Uani . . . . . .
C19 C -0.0353(2) 0.0868(2) 0.16106(18) 0.0238 1.0000 Uani . . . . . .
Cl20 Cl -0.12619(6) -0.00371(5) 0.26798(5) 0.0300 1.0000 Uani . . . . . .
O1 O 0.13886(15) 0.27674(14) 0.40029(12) 0.0241 1.0000 Uani . . . . . .
O2 O 0.33331(16) 0.10467(14) 0.51111(11) 0.0251 1.0000 Uani . . . . . .
H61 H 0.3135 0.4691 0.3115 0.0288 1.0000 Uiso R . . . . .
H71 H 0.5358 0.6134 0.2768 0.0303 1.0000 Uiso R . . . . .
H92 H 0.9371 0.5103 0.2888 0.0555 1.0000 Uiso R . . . . .
H91 H 0.9098 0.6246 0.3926 0.0566 1.0000 Uiso R . . . . .
H93 H 0.8226 0.6365 0.2539 0.0558 1.0000 Uiso R . . . . .
H101 H 0.8462 0.3107 0.4192 0.0333 1.0000 Uiso R . . . . .
H111 H 0.6277 0.1695 0.4570 0.0297 1.0000 Uiso R . . . . .
H121 H 0.4462 -0.0367 0.3319 0.0268 1.0000 Uiso R . . . . .
H122 H 0.4577 0.0573 0.2118 0.0252 1.0000 Uiso R . . . . .
H141 H 0.1456 -0.2179 0.2443 0.0274 1.0000 Uiso R . . . . .
H151 H 0.0854 -0.4280 0.1149 0.0314 1.0000 Uiso R . . . . .
H161 H 0.2405 -0.4824 -0.0427 0.0324 1.0000 Uiso R . . . . .
H171 H 0.4546 -0.3246 -0.0697 0.0331 1.0000 Uiso R . . . . .
H181 H 0.5142 -0.1128 0.0603 0.0271 1.0000 Uiso R . . . . .
H191 H -0.1065 0.1167 0.0895 0.0300 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
Cl1 0.0275(3) 0.0322(3) 0.0247(2) 0.00862(19) 0.00321(18) -0.00204(19)
C2 0.0189(9) 0.0183(8) 0.0203(9) 0.0006(7) 0.0016(7) 0.0029(7)
N3 0.0148(7) 0.0176(7) 0.0198(7) -0.0019(6) -0.0001(6) 0.0024(6)
S4 0.0154(2) 0.0197(2) 0.0175(2) -0.00031(16) 0.00176(16) 0.00143(16)
C5 0.0161(8) 0.0193(8) 0.0177(8) -0.0031(7) 0.0019(6) 0.0006(7)
C6 0.0218(9) 0.0234(9) 0.0222(9) 0.0001(7) -0.0001(7) 0.0050(7)
C7 0.0312(11) 0.0204(9) 0.0233(9) 0.0012(7) 0.0017(8) -0.0018(8)
C8 0.0260(10) 0.0278(10) 0.0203(9) -0.0089(8) 0.0082(7) -0.0060(8)
C9 0.0353(12) 0.0429(12) 0.0318(11) -0.0072(9) 0.0134(9) -0.0143(10)
C10 0.0169(9) 0.0274(10) 0.0363(11) -0.0060(8) 0.0032(8) 0.0014(8)
C11 0.0200(9) 0.0205(9) 0.0302(10) -0.0003(8) 0.0008(7) 0.0036(7)
C12 0.0172(9) 0.0219(9) 0.0251(9) -0.0021(7) 0.0018(7) 0.0045(7)
C13 0.0202(9) 0.0169(8) 0.0206(9) 0.0018(7) -0.0012(7) 0.0063(7)
C14 0.0200(9) 0.0250(9) 0.0220(9) 0.0021(7) 0.0048(7) 0.0038(7)
C15 0.0219(10) 0.0223(9) 0.0318(10) 0.0036(8) 0.0011(8) -0.0022(7)
C16 0.0302(10) 0.0224(9) 0.0252(10) -0.0034(8) -0.0003(8) 0.0023(8)
C17 0.0287(10) 0.0279(10) 0.0233(9) -0.0025(8) 0.0074(8) 0.0032(8)
C18 0.0196(9) 0.0225(9) 0.027(1) 0.0047(8) 0.0052(7) 0.0000(7)
C19 0.0214(9) 0.0231(9) 0.0259(9) 0.0001(7) 0.0009(7) 0.0023(7)
Cl20 0.0212(2) 0.0308(3) 0.0395(3) 0.0006(2) 0.01054(19) -0.00328(19)
O1 0.0163(6) 0.0281(7) 0.0274(7) -0.0055(5) 0.0040(5) 0.0044(5)
O2 0.0258(7) 0.0296(7) 0.0194(6) 0.0056(5) 0.0016(5) 0.0001(6)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.5897(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 . C2 . 1.7556(18) yes
C2 . N3 . 1.405(2) yes
C2 . C19 . 1.322(3) yes
N3 . S4 . 1.6792(14) yes
N3 . C12 . 1.493(2) yes
S4 . C5 . 1.7590(17) yes
S4 . O1 . 1.4279(13) yes
S4 . O2 . 1.4323(13) yes
C5 . C6 . 1.388(2) yes
C5 . C11 . 1.393(2) yes
C6 . C7 . 1.382(3) yes
C6 . H61 . 0.940 no
C7 . C8 . 1.395(3) yes
C7 . H71 . 0.932 no
C8 . C9 . 1.504(3) yes
C8 . C10 . 1.393(3) yes
C9 . H92 . 0.944 no
C9 . H91 . 0.950 no
C9 . H93 . 0.965 no
C10 . C11 . 1.379(3) yes
C10 . H101 . 0.935 no
C11 . H111 . 0.923 no
C12 . C13 . 1.506(2) yes
C12 . H121 . 0.984 no
C12 . H122 . 0.986 no
C13 . C14 . 1.397(2) yes
C13 . C18 . 1.396(3) yes
C14 . C15 . 1.381(3) yes
C14 . H141 . 0.949 no
C15 . C16 . 1.381(3) yes
C15 . H151 . 0.951 no
C16 . C17 . 1.378(3) yes
C16 . H161 . 0.946 no
C17 . C18 . 1.384(3) yes
C17 . H171 . 0.943 no
C18 . H181 . 0.929 no
C19 . Cl20 . 1.7157(19) yes
C19 . H191 . 0.943 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
Cl1 . C2 . N3 . 117.27(13) yes
Cl1 . C2 . C19 . 117.46(14) yes
N3 . C2 . C19 . 125.27(17) yes
C2 . N3 . S4 . 117.06(11) yes
C2 . N3 . C12 . 117.28(14) yes
S4 . N3 . C12 . 115.21(11) yes
N3 . S4 . C5 . 106.59(8) yes
N3 . S4 . O1 . 105.78(7) yes
C5 . S4 . O1 . 109.23(8) yes
N3 . S4 . O2 . 105.61(7) yes
C5 . S4 . O2 . 108.15(8) yes
O1 . S4 . O2 . 120.62(8) yes
S4 . C5 . C6 . 119.35(13) yes
S4 . C5 . C11 . 119.94(14) yes
C6 . C5 . C11 . 120.69(16) yes
C5 . C6 . C7 . 119.39(17) yes
C5 . C6 . H61 . 120.1 no
C7 . C6 . H61 . 120.5 no
C6 . C7 . C8 . 121.08(18) yes
C6 . C7 . H71 . 119.9 no
C8 . C7 . H71 . 119.0 no
C7 . C8 . C9 . 121.28(19) yes
C7 . C8 . C10 . 118.23(17) yes
C9 . C8 . C10 . 120.49(18) yes
C8 . C9 . H92 . 110.5 no
C8 . C9 . H91 . 111.1 no
H92 . C9 . H91 . 109.4 no
C8 . C9 . H93 . 110.2 no
H92 . C9 . H93 . 107.3 no
H91 . C9 . H93 . 108.3 no
C8 . C10 . C11 . 121.66(18) yes
C8 . C10 . H101 . 120.2 no
C11 . C10 . H101 . 118.2 no
C5 . C11 . C10 . 118.94(18) yes
C5 . C11 . H111 . 120.1 no
C10 . C11 . H111 . 120.9 no
N3 . C12 . C13 . 112.57(14) yes
N3 . C12 . H121 . 106.2 no
C13 . C12 . H121 . 109.5 no
N3 . C12 . H122 . 109.6 no
C13 . C12 . H122 . 109.6 no
H121 . C12 . H122 . 109.3 no
C12 . C13 . C14 . 122.59(16) yes
C12 . C13 . C18 . 118.67(16) yes
C14 . C13 . C18 . 118.63(16) yes
C13 . C14 . C15 . 120.13(17) yes
C13 . C14 . H141 . 119.6 no
C15 . C14 . H141 . 120.3 no
C14 . C15 . C16 . 120.57(18) yes
C14 . C15 . H151 . 118.5 no
C16 . C15 . H151 . 121.0 no
C15 . C16 . C17 . 120.04(17) yes
C15 . C16 . H161 . 120.0 no
C17 . C16 . H161 . 120.0 no
C16 . C17 . C18 . 119.93(17) yes
C16 . C17 . H171 . 119.7 no
C18 . C17 . H171 . 120.4 no
C13 . C18 . C17 . 120.70(17) yes
C13 . C18 . H181 . 119.1 no
C17 . C18 . H181 . 120.1 no
C2 . C19 . Cl20 . 122.67(15) yes
C2 . C19 . H191 . 121.0 no
Cl20 . C19 . H191 . 116.3 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
C9 . H91 . O1 2_666 142.84(6) 0.950 2.470 3.278(3) yes
C10 . H101 . O1 1_655 156.40(6) 0.935 2.486 3.364(3) yes
C11 . H111 . O2 2_656 161.57(5) 0.923 2.581 3.469(3) yes
C12 . H121 . O2 2_656 160.31(5) 0.984 2.379 3.323(3) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 09/05/13 at 14:12:32
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   9,X'S) H   (  92,X'S) H   (  91,X'S) H   (  93,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 09/05/13 at 14:12:32
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 1022574'
#######################################################################
#
#                 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_2t
_audit_creation_date             2014-08-02
_audit_creation_method           CRYSTALS_ver_14.43

_oxford_structure_analysis_title '010mwj14 At 10:15 on 31/ 7'
_chemical_name_systematic        010mwj14
_chemical_melting_point          'not measured'

#############################################################
_refine_special_details          
; 
The data/parameter ratio for this structure is slightly low which is best explained
by the large proportion of the structure that is duplicated by the disorder. 
This is as a result of the two rotameric forms of the structure about
the N-C bond.
;
#############################################################

_cell_length_a                   5.8679(2)
_cell_length_b                   10.4250(3)
_cell_length_c                   11.8622(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     725.64(4)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 c n '
_symmetry_space_group_name_Hall  'P -2n 2a '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,y+1/2,-z+1/2
x+1/2,-y,-z
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 0.0033 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'
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'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C6 H10 Cl2 N2 O4 
# Dc =      2.24 Fooo =    368.00 Mu =      8.82 M =    245.06
# Found Formula = C5 H5 Cl2 N1 O2 
# Dc =      1.67 FOOO =    368.00 Mu =      8.28 M =    182.01

_chemical_formula_sum            'C5 H5 Cl2 N O2'
_chemical_formula_moiety         'C5 H5 Cl2 N O2'
_chemical_compound_source        .
_chemical_formula_weight         182.01


_cell_measurement_reflns_used    1003
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.080
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_max          0.160

_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    0.828

# Sheldrick geometric approximatio 0.88 0.94 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.94
# 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_ambient_pressure         102
_diffrn_reflns_number            9210
_reflns_number_total             909
_diffrn_reflns_av_R_equivalents  0.018
# Number of reflections without Friedels Law is 1584 
# Number of reflections with Friedels Law is 909 
# Theoretical number of reflections is about 831 


_diffrn_reflns_theta_min         5.207
_diffrn_reflns_theta_max         27.465
_diffrn_measured_fraction_theta_max 0.990

_diffrn_reflns_theta_full        27.465
_diffrn_measured_fraction_theta_full 0.990


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              0
_reflns_limit_h_max              7
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   2.51
_oxford_diffrn_Wilson_scale      3.78

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

_refine_diff_density_min         -0.33
_refine_diff_density_max         0.30


# 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         909
_refine_ls_number_restraints     57
_refine_ls_number_parameters     128
_oxford_refine_ls_R_factor_ref   0.0363
_refine_ls_wR_factor_ref         0.0622
_refine_ls_goodness_of_fit_ref   0.9883
_refine_ls_shift/su_max          0.0055448
_refine_ls_shift/su_mean         0.0004432


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        909
_refine_ls_R_factor_all          0.0363
_refine_ls_wR_factor_all         0.0622

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                814
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_gt          0.0563

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


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    noref #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: 
 5.22 6.36 1.86 
;

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

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

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


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Cl1 Cl 0.4411(4) 0.98413(8) 0.40203(8) 0.0330 1.0000 Uani D . . . . .
C2 C 0.2658(6) 0.8466(3) 0.3960(3) 0.0226 0.724(7) Uani D U P . 3 .
C4 C 0.4049(7) 0.6243(3) 0.4088(2) 0.0206 1.0000 Uani D . . . . .
O5 O 0.4984(6) 0.5507(2) 0.4898(2) 0.0243 1.0000 Uani . . . . . .
C6 C 0.4662(9) 0.6126(4) 0.5983(3) 0.0307 1.0000 Uani . U . . . .
O8 O 0.3994(7) 0.5944(2) 0.31087(18) 0.0288 1.0000 Uani . . . . . .
C9 C 0.0782(9) 0.8558(4) 0.3357(4) 0.0233 0.724(7) Uani D U P . 3 .
Cl10 Cl -0.1101(3) 0.72977(8) 0.32849(8) 0.0308 1.0000 Uani D . . . . .
C22 C 0.1901(17) 0.9216(9) 0.3572(11) 0.0250 0.276(7) Uani D U P . 4 .
C21 C 0.1512(12) 0.8017(5) 0.3841(7) 0.0180 0.276(7) Uani D U P . 4 .
C70 C 0.276(2) 0.7176(12) 0.5736(7) 0.0276 0.276(7) Uani D U P . 4 .
C71 C 0.4186(11) 0.7491(4) 0.5751(4) 0.0289 0.724(7) Uani D U P . 3 .
N30 N 0.2906(10) 0.7226(6) 0.4498(5) 0.0149 0.276(7) Uani D U P . 4 .
N31 N 0.3386(7) 0.7394(3) 0.4583(2) 0.0199 0.724(7) Uani D U P . 3 .
H91 H 0.0455 0.9297 0.2965 0.0275 0.724(7) Uiso . . P . 3 .
H221 H 0.0840 0.9636 0.3172 0.0351 0.276(7) Uiso . . P . 4 .
H701 H 0.3259 0.7969 0.6090 0.0362 0.276(7) Uiso . . P . 4 .
H702 H 0.1352 0.6889 0.5980 0.0358 0.276(7) Uiso . . P . 4 .
H711 H 0.5597 0.8013 0.5791 0.0325 0.724(7) Uiso . . P . 3 .
H712 H 0.3059 0.7874 0.6252 0.0325 0.724(7) Uiso . . P . 3 .
H61 H 0.6031 0.6012 0.6435 0.0365 1.0000 Uiso . . . . . .
H62 H 0.3393 0.5725 0.6399 0.0365 1.0000 Uiso . . . . . .
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
Cl1 0.0382(5) 0.0268(4) 0.0340(4) 0.0029(4) -0.0051(4) -0.0086(5)
C2 0.026(3) 0.022(3) 0.020(2) -0.002(2) 0.006(2) -0.003(2)
C4 0.0177(17) 0.0228(14) 0.0214(14) 0.0020(12) 0.0020(16) -0.0011(15)
O5 0.0270(14) 0.0223(11) 0.0238(12) 0.0027(10) 0.0017(11) 0.0059(11)
C6 0.037(2) 0.0361(18) 0.0194(15) 0.0011(15) -0.0043(16) 0.009(2)
O8 0.0313(14) 0.0340(12) 0.0213(11) -0.0063(10) 0.0038(14) -0.0013(15)
C9 0.028(3) 0.020(2) 0.022(2) 0.004(2) 0.004(2) 0.003(2)
Cl10 0.0261(4) 0.0291(4) 0.0371(4) 0.0009(4) -0.0008(4) -0.0035(5)
C22 0.023(6) 0.030(6) 0.022(6) 0.003(5) -0.008(5) 0.010(5)
C21 0.021(6) 0.015(5) 0.018(5) -0.002(4) 0.001(5) 0.002(5)
C70 0.040(6) 0.034(6) 0.008(4) -0.003(5) -0.005(6) 0.007(5)
C71 0.045(4) 0.026(2) 0.0154(19) -0.0027(17) -0.003(3) 0.005(3)
N30 0.017(5) 0.014(5) 0.013(5) 0.003(4) -0.001(4) 0.003(4)
N31 0.024(3) 0.021(2) 0.015(2) 0.0009(18) -0.0022(17) 0.0028(19)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.4992(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
Cl1 . C2 . 1.766(3) yes
C2 . C9 . 1.317(5) yes
C2 . N31 . 1.406(4) yes
C4 . O5 . 1.347(4) yes
C4 . O8 . 1.203(4) yes
C4 . N31 . 1.391(4) yes
O5 . C6 . 1.452(4) yes
C6 . C71 . 1.475(5) yes
C6 . H61 . 0.973 no
C6 . H62 . 0.987 no
C9 . Cl10 . 1.719(4) yes
C9 . H91 . 0.920 no
C22 . C21 . 1.310(8) yes
C22 . H221 . 0.897 no
C21 . N30 . 1.399(7) yes
C70 . N30 . 1.472(8) yes
C70 . H701 . 0.973 no
C70 . H702 . 0.923 no
C71 . N31 . 1.466(5) yes
C71 . H711 . 0.992 no
C71 . H712 . 0.975 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Cl1 . C2 . C9 . 116.72(8) yes
Cl1 . C2 . N31 . 116.58(8) yes
C9 . C2 . N31 . 126.68(8) yes
O5 . C4 . O8 . 123.6(3) yes
O5 . C4 . N31 . 107.7(2) yes
O8 . C4 . N31 . 128.6(2) yes
C4 . O5 . C6 . 109.0(3) yes
O5 . C6 . C71 . 106.7(3) yes
O5 . C6 . H61 . 109.1 no
C71 . C6 . H61 . 112.1 no
O5 . C6 . H62 . 110.7 no
C71 . C6 . H62 . 111.0 no
H61 . C6 . H62 . 107.2 no
C2 . C9 . Cl10 . 120.6(2) yes
C2 . C9 . H91 . 120.7 no
Cl10 . C9 . H91 . 118.8 no
Cl1 . C22 . C21 . 116.2(4) yes
Cl1 . C22 . H221 . 125.5 no
C21 . C22 . H221 . 118.3 no
Cl10 . C21 . C22 . 116.69(8) yes
Cl10 . C21 . N30 . 116.70(8) yes
C22 . C21 . N30 . 126.61(8) yes
C6 . C70 . N30 . 99.5(4) yes
C6 . C70 . H701 . 107.0 no
N30 . C70 . H701 . 112.5 no
C6 . C70 . H702 . 110.3 no
N30 . C70 . H702 . 112.1 no
H701 . C70 . H702 . 114.3 no
C6 . C71 . N31 . 99.8(3) yes
C6 . C71 . H711 . 111.2 no
N31 . C71 . H711 . 110.5 no
C6 . C71 . H712 . 114.2 no
N31 . C71 . H712 . 112.8 no
H711 . C71 . H712 . 108.2 no
C70 . N30 . C21 . 122.82(10) yes
C70 . N30 . C4 . 111.80(10) yes
C21 . N30 . C4 . 123.36(10) yes
C71 . N31 . C2 . 122.60(9) yes
C71 . N31 . C4 . 111.66(9) yes
C2 . N31 . C4 . 123.25(9) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C9 . H91 . O8 2_455 168.9(3) 0.920 2.303 3.211(9) yes
C22 . H91 . O8 2_455 134.1(5) 1.116 2.303 3.183(9) yes
C9 . H221 . O8 2_455 133.7(3) 1.145 2.312 3.211(9) yes
C22 . H221 . O8 2_455 164.0(7) 0.897 2.312 3.183(9) yes
C70 . H712 . O8 4_565 159.6(6) 0.967 2.583 3.505(9) yes
C71 . H712 . O8 4_565 124.9(3) 0.975 2.583 3.240(9) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 02/08/14 at 19:02:48
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
EQUIV PART(0003,OCC) PART(0004,OCC) 
WEIGHT -1 PART(0004,OCC) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 02/08/14 at 19:02:48
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
DISTANCE 1.450000 , 0.050000 = C(70) TO N(30) 
DISTANCE 1.450000 , 0.050000 = C(21) TO N(30) 
DISTANCE 1.450000 , 0.050000 = C(2) TO N(31) 
U(IJ)'S  0.0, 0.010000 = N(30) TO N(31) 
U(IJ)'S  0.0, 0.010000 = C(2) TO C(21) 
U(IJ)'S  0.0, 0.010000 = C(9) TO C(22) 
U(IJ)'S  0.0, 0.010000 = C(70) TO C(71) 
DISTANCE 1.450000 , 0.050000 = C(4) TO N(30) 
VIBRATION 0.0, 0.010000 = N(30) TO N(31) 
VIBRATION 0.0, 0.010000 = C(70) TO C(71) 
VIBRATION 0.0, 0.010000 = C(2) TO C(21) 
VIBRATION 0.0, 0.010000 = C(9) TO C(22) 
SAME 0.01, 0.1 FOR C(71) N(31) C(4) C(2)  C(9)  CL(1) AND 
CONT               C(70) N(30) C(4) C(21) C(22) CL(10) 
VIBRATION 0.0, 0.010000 = C(6) TO C(70) 
VIBRATION 0.0, 0.010000 = C(70) TO N(30) 
END                                                                             
;

############################################################

# start Validation Reply Form
_vrf_PLAT089_2t                  
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       7.17
RESPONSE: See refine special details.
;
_database_code_depnum_ccdc_archive 'CCDC 1022575'
