# Electronic Supplementary Material (ESI) for CrystEngComm
# 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
#  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_bethan
#TrackingRef 'BETHAN.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H17 Cl N2 O2'
_chemical_formula_weight         196.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.0933(6)
_cell_length_b                   16.2066(11)
_cell_length_c                   8.8042(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.749(3)
_cell_angle_gamma                90.00
_cell_volume                     1009.95(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    1750
_cell_measurement_theta_min      5.46
_cell_measurement_theta_max      72.25

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    3.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7894
_exptl_absorpt_correction_T_max  0.9127
_exptl_absorpt_process_details   'CrystalClear (Rigaku/MSC Inc., 2005)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'micro-focus rotating anode'
_diffrn_radiation_monochromator  'Rigaku VariMax mirror'
_diffrn_measurement_device_type  'Rigaku RAXIS Rapid'
_diffrn_measurement_method       \w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5976
_diffrn_reflns_av_R_equivalents  0.1413
_diffrn_reflns_av_sigmaI/netI    0.1050
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         6.83
_diffrn_reflns_theta_max         70.02
_reflns_number_total             1872
_reflns_number_gt                1714
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0645P)^2^+2.1966P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1872
_refine_ls_number_parameters     122
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0739
_refine_ls_wR_factor_ref         0.1921
_refine_ls_wR_factor_gt          0.1797
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.24127(12) 0.99340(5) 0.71048(9) 0.0303(3) Uani 1 1 d . . .
O1 O 0.3671(4) 0.68499(17) 0.2967(3) 0.0376(7) Uani 1 1 d . . .
C2 C 0.3090(5) 0.6711(2) 0.1661(4) 0.0287(8) Uani 1 1 d . . .
N3 N 0.3879(4) 0.6190(2) 0.0709(4) 0.0319(7) Uani 1 1 d D . .
O4 O 0.1585(3) 0.71068(15) 0.0958(3) 0.0289(6) Uani 1 1 d . . .
C5 C 0.0573(5) 0.7680(2) 0.1880(4) 0.0268(7) Uani 1 1 d . . .
H5 H 0.1077 0.7644 0.2966 0.032 Uiso 1 1 calc R . .
C6 C -0.1505(5) 0.7443(2) 0.1756(4) 0.0318(8) Uani 1 1 d . . .
H6A H -0.2040 0.7558 0.0723 0.048 Uiso 1 1 calc R . .
H6B H -0.2183 0.7765 0.2489 0.048 Uiso 1 1 calc R . .
H6C H -0.1632 0.6854 0.1977 0.048 Uiso 1 1 calc R . .
C7 C 0.0789(5) 0.8558(2) 0.1299(4) 0.0281(8) Uani 1 1 d . . .
H7A H 0.0579 0.8547 0.0176 0.034 Uiso 1 1 calc R . .
H7B H -0.0231 0.8897 0.1696 0.034 Uiso 1 1 calc R . .
N8 N 0.2650(4) 0.89922(18) 0.1690(3) 0.0264(7) Uani 1 1 d . . .
C9 C 0.2394(6) 0.9880(2) 0.1238(4) 0.0323(8) Uani 1 1 d . . .
H9A H 0.1350 1.0118 0.1768 0.048 Uiso 1 1 calc R . .
H9B H 0.2107 0.9916 0.0136 0.048 Uiso 1 1 calc R . .
H9C H 0.3558 1.0186 0.1515 0.048 Uiso 1 1 calc R . .
C10 C 0.3190(6) 0.8962(3) 0.3361(4) 0.0364(9) Uani 1 1 d . . .
H10A H 0.4286 0.9320 0.3592 0.055 Uiso 1 1 calc R . .
H10B H 0.3510 0.8394 0.3658 0.055 Uiso 1 1 calc R . .
H10C H 0.2129 0.9153 0.3927 0.055 Uiso 1 1 calc R . .
C11 C 0.4219(5) 0.8651(2) 0.0816(5) 0.0353(9) Uani 1 1 d . . .
H11A H 0.5360 0.8984 0.1023 0.053 Uiso 1 1 calc R . .
H11B H 0.3848 0.8668 -0.0276 0.053 Uiso 1 1 calc R . .
H11C H 0.4473 0.8080 0.1128 0.053 Uiso 1 1 calc R . .
H3A H 0.478(4) 0.589(2) 0.113(4) 0.037(11) Uiso 1 1 d D . .
H3B H 0.323(5) 0.604(2) -0.012(3) 0.040(12) Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0307(5) 0.0302(5) 0.0299(5) -0.0005(3) 0.0009(4) -0.0038(3)
O1 0.0464(16) 0.0359(15) 0.0290(14) -0.0044(11) -0.0092(12) 0.0104(12)
C2 0.0343(19) 0.0229(18) 0.0282(18) 0.0013(13) -0.0036(14) 0.0012(14)
N3 0.0304(16) 0.0331(17) 0.0320(17) -0.0026(13) 0.0012(13) 0.0085(13)
O4 0.0317(13) 0.0276(14) 0.0270(12) -0.0019(10) -0.0018(10) 0.0049(10)
C5 0.0285(18) 0.0251(17) 0.0269(17) 0.0000(13) 0.0018(13) 0.0005(14)
C6 0.0287(18) 0.032(2) 0.0350(18) -0.0014(15) 0.0037(14) -0.0013(14)
C7 0.0265(17) 0.0259(18) 0.0310(18) -0.0017(14) -0.0036(14) 0.0003(13)
N8 0.0276(15) 0.0279(16) 0.0236(14) 0.0000(11) 0.0009(11) -0.0019(11)
C9 0.036(2) 0.030(2) 0.0314(19) 0.0028(15) 0.0038(16) -0.0008(15)
C10 0.044(2) 0.041(2) 0.0232(18) 0.0015(15) -0.0036(15) -0.0127(17)
C11 0.0285(18) 0.035(2) 0.043(2) -0.0023(17) 0.0093(16) 0.0005(15)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.217(4) . ?
C2 N3 1.338(5) . ?
C2 O4 1.359(4) . ?
O4 C5 1.454(4) . ?
C5 C6 1.521(5) . ?
C5 C7 1.522(5) . ?
C7 N8 1.516(4) . ?
N8 C10 1.496(4) . ?
N8 C11 1.499(5) . ?
N8 C9 1.501(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C2 N3 125.4(3) . . ?
O1 C2 O4 123.4(3) . . ?
N3 C2 O4 111.1(3) . . ?
C2 O4 C5 116.6(3) . . ?
O4 C5 C6 108.1(3) . . ?
O4 C5 C7 110.2(3) . . ?
C6 C5 C7 109.3(3) . . ?
N8 C7 C5 117.6(3) . . ?
C10 N8 C11 110.0(3) . . ?
C10 N8 C9 108.1(3) . . ?
C11 N8 C9 107.3(3) . . ?
C10 N8 C7 111.8(3) . . ?
C11 N8 C7 112.1(3) . . ?
C9 N8 C7 107.3(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 O4 C5 -4.2(5) . . . . ?
N3 C2 O4 C5 178.7(3) . . . . ?
C2 O4 C5 C6 -126.4(3) . . . . ?
C2 O4 C5 C7 114.3(3) . . . . ?
O4 C5 C7 N8 -76.8(4) . . . . ?
C6 C5 C7 N8 164.6(3) . . . . ?
C5 C7 N8 C10 -51.9(4) . . . . ?
C5 C7 N8 C11 72.2(4) . . . . ?
C5 C7 N8 C9 -170.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        70.02
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.099


_database_code_depnum_ccdc_archive 'CCDC 818326'