# Electronic Supplementary Material (ESI) for Chemical Communications
# 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.
# 
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#  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_bz_057_2

# This structure was measured,
# solved and refined by:
# Elli Maennel

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;

_chemical_formula_moiety         'C19 H20 N2 O2, 0.5 (C2 H4 Cl2)'
_chemical_formula_sum            'C20 H22 Cl N2 O2'
_chemical_formula_weight         357.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_int_tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1957(9)
_cell_length_b                   8.7315(9)
_cell_length_c                   12.9688(14)
_cell_angle_alpha                96.755(2)
_cell_angle_beta                 99.390(2)
_cell_angle_gamma                92.439(2)
_cell_volume                     907.46(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2357
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      30.05

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             378
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9394
_exptl_absorpt_correction_T_max  0.9866
_exptl_absorpt_process_details   SADABS-2004/1

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11358
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_sigmaI/netI    0.0847
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         28.70
_reflns_number_total             4654
_reflns_number_gt                2918
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0513P)^2^+0.0000P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       'not measured'
_refine_ls_number_reflns         4654
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_restrained_S_all      0.907
_refine_ls_shift/su_max          0.002
_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 0.39810(7) 0.18385(6) 0.58961(5) 0.04042(17) Uani 1 1 d . . .
C20 C 0.5010(3) 0.0124(2) 0.55768(16) 0.0344(5) Uani 1 1 d . . .
H20A H 0.6168 0.0232 0.5955 0.041 Uiso 1 1 calc R . .
H20B H 0.4441 -0.0774 0.5798 0.041 Uiso 1 1 calc R . .
O1 O 0.32551(15) 0.50641(13) 1.04028(9) 0.0215(3) Uani 1 1 d . . .
H1 H 0.3720 0.4385 1.0733 0.032 Uiso 1 1 calc R . .
O2 O 0.32644(15) 0.32988(14) 0.89996(10) 0.0250(3) Uani 1 1 d . . .
N1 N 0.48358(16) 0.67003(15) 0.84076(11) 0.0144(3) Uani 1 1 d . . .
N2 N 0.24502(16) 0.82351(15) 0.81183(10) 0.0142(3) Uani 1 1 d . . .
C1 C 0.3137(2) 0.65097(19) 0.66156(13) 0.0167(4) Uani 1 1 d . . .
C2 C 0.22353(19) 0.76989(19) 0.70133(13) 0.0158(4) Uani 1 1 d . . .
C3 C 0.1054(2) 0.8350(2) 0.63217(14) 0.0214(4) Uani 1 1 d . . .
H3 H 0.0450 0.9172 0.6583 0.026 Uiso 1 1 calc R . .
C4 C 0.0757(2) 0.7803(2) 0.52557(15) 0.0261(4) Uani 1 1 d . . .
H4 H -0.0036 0.8269 0.4792 0.031 Uiso 1 1 calc R . .
C5 C 0.1602(2) 0.6584(2) 0.48547(14) 0.0250(4) Uani 1 1 d . . .
C6 C 0.2792(2) 0.5962(2) 0.55451(14) 0.0220(4) Uani 1 1 d . . .
H6 H 0.3390 0.5138 0.5280 0.026 Uiso 1 1 calc R . .
C7 C 0.1235(3) 0.5953(3) 0.36986(15) 0.0369(5) Uani 1 1 d . . .
H7A H 0.2138 0.6291 0.3351 0.055 Uiso 1 1 calc R . .
H7B H 0.0194 0.6337 0.3371 0.055 Uiso 1 1 calc R . .
H7C H 0.1136 0.4821 0.3624 0.055 Uiso 1 1 calc R . .
C8 C 0.4453(2) 0.58063(19) 0.73376(13) 0.0178(4) Uani 1 1 d . . .
H8A H 0.4073 0.4734 0.7399 0.021 Uiso 1 1 calc R . .
H8B H 0.5477 0.5762 0.7024 0.021 Uiso 1 1 calc R . .
C9 C 0.32553(19) 0.71307(18) 0.87603(13) 0.0152(3) Uani 1 1 d . . .
H9 H 0.3536 0.7650 0.9502 0.018 Uiso 1 1 calc R . .
C10 C 0.34094(19) 0.97351(18) 0.84101(13) 0.0158(3) Uani 1 1 d . . .
H10A H 0.3206 1.0207 0.9106 0.019 Uiso 1 1 calc R . .
H10B H 0.3030 1.0439 0.7887 0.019 Uiso 1 1 calc R . .
C11 C 0.52459(19) 0.95541(18) 0.84568(12) 0.0145(3) Uani 1 1 d . . .
C12 C 0.6344(2) 1.08453(19) 0.85367(13) 0.0169(4) Uani 1 1 d . . .
H12 H 0.5921 1.1842 0.8555 0.020 Uiso 1 1 calc R . .
C13 C 0.8044(2) 1.0715(2) 0.85905(13) 0.0182(4) Uani 1 1 d . . .
C14 C 0.8630(2) 0.9234(2) 0.85304(14) 0.0207(4) Uani 1 1 d . . .
H14 H 0.9781 0.9116 0.8549 0.025 Uiso 1 1 calc R . .
C15 C 0.7572(2) 0.7945(2) 0.84449(13) 0.0187(4) Uani 1 1 d . . .
H15 H 0.7995 0.6948 0.8402 0.022 Uiso 1 1 calc R . .
C16 C 0.58758(19) 0.80965(19) 0.84216(12) 0.0145(3) Uani 1 1 d . . .
C17 C 0.9244(2) 1.2104(2) 0.87282(15) 0.0258(4) Uani 1 1 d . . .
H17A H 0.8631 1.3042 0.8711 0.039 Uiso 1 1 calc R . .
H17B H 0.9897 1.2020 0.8157 0.039 Uiso 1 1 calc R . .
H17C H 0.9987 1.2155 0.9407 0.039 Uiso 1 1 calc R . .
C18 C 0.2078(2) 0.57195(19) 0.87550(14) 0.0181(4) Uani 1 1 d . . .
H18A H 0.1096 0.6053 0.9056 0.022 Uiso 1 1 calc R . .
H18B H 0.1692 0.5242 0.8020 0.022 Uiso 1 1 calc R . .
C19 C 0.2914(2) 0.45454(19) 0.93822(14) 0.0179(4) Uani 1 1 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 0.0517(3) 0.0256(3) 0.0468(3) -0.0016(2) 0.0194(3) 0.0088(2)
C20 0.0444(13) 0.0273(11) 0.0326(12) 0.0020(9) 0.0097(10) 0.0080(9)
O1 0.0253(7) 0.0181(6) 0.0210(7) 0.0060(5) 0.0000(5) 0.0061(5)
O2 0.0272(7) 0.0172(6) 0.0298(7) 0.0010(5) 0.0036(6) 0.0008(5)
N1 0.0141(7) 0.0124(7) 0.0163(7) 0.0012(5) 0.0014(5) 0.0018(5)
N2 0.0145(7) 0.0136(7) 0.0141(7) 0.0025(5) 0.0002(5) 0.0019(5)
C1 0.0177(8) 0.0138(8) 0.0180(9) 0.0022(7) 0.0015(7) -0.0013(6)
C2 0.0148(8) 0.0161(8) 0.0158(9) 0.0028(7) 0.0000(7) -0.0009(6)
C3 0.0199(9) 0.0204(9) 0.0236(10) 0.0055(7) 0.0002(7) 0.0032(7)
C4 0.0244(10) 0.0314(11) 0.0210(10) 0.0101(8) -0.0048(8) -0.0003(8)
C5 0.0285(10) 0.0277(10) 0.0171(9) 0.0038(8) -0.0002(8) -0.0037(8)
C6 0.0279(10) 0.0183(9) 0.0192(9) 0.0007(7) 0.0040(7) -0.0004(7)
C7 0.0465(13) 0.0421(13) 0.0181(10) 0.0014(9) -0.0039(9) -0.0006(10)
C8 0.0211(9) 0.0151(8) 0.0160(9) -0.0009(7) 0.0012(7) 0.0046(7)
C9 0.0137(8) 0.0158(8) 0.0160(8) 0.0026(7) 0.0014(6) 0.0030(6)
C10 0.0153(8) 0.0135(8) 0.0183(9) 0.0012(7) 0.0019(7) 0.0022(6)
C11 0.0147(8) 0.0156(8) 0.0127(8) 0.0011(6) 0.0011(6) 0.0021(6)
C12 0.0199(9) 0.0158(8) 0.0153(9) 0.0032(7) 0.0029(7) 0.0030(7)
C13 0.0177(9) 0.0218(9) 0.0154(8) 0.0052(7) 0.0019(7) -0.0012(7)
C14 0.0132(8) 0.0272(10) 0.0231(10) 0.0070(8) 0.0044(7) 0.0024(7)
C15 0.0170(9) 0.0201(9) 0.0204(9) 0.0044(7) 0.0046(7) 0.0052(7)
C16 0.0148(8) 0.0158(8) 0.0133(8) 0.0030(6) 0.0024(6) 0.0016(6)
C17 0.0199(9) 0.0279(10) 0.0297(11) 0.0071(8) 0.0031(8) -0.0049(8)
C18 0.0160(8) 0.0179(9) 0.0197(9) 0.0046(7) -0.0002(7) -0.0014(7)
C19 0.0143(8) 0.0178(9) 0.0215(9) 0.0041(7) 0.0022(7) -0.0016(7)

_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. 

 Least-squares planes (x,y,z in crystal coordinates) and deviations from them
 (* indicates atom used to define plane)

  5.7939 (0.0043) x + 5.7423 (0.0049) y - 4.6709 (0.0086) z = 2.4526 (0.0064) 

 *    0.0129 (0.0012)  C1
 *   -0.0124 (0.0012)  C2
 *   -0.0001 (0.0012)  C3
 *    0.0119 (0.0013)  C4
 *   -0.0113 (0.0013)  C5
 *   -0.0012 (0.0012)  C6

 Rms deviation of fitted atoms =   0.0099


 - 0.3337 (0.0056) x - 0.5504 (0.0061) y + 12.8462 (0.0019) z = 10.1658 (0.0061) 

 Angle to previous plane (with approximate esd) = 76.39 ( 0.06 )

 *   -0.0030 (0.0011)  C11
 *   -0.0082 (0.0012)  C12
 *    0.0115 (0.0012)  C13
 *   -0.0038 (0.0012)  C14
 *   -0.0074 (0.0012)  C15
 *    0.0109 (0.0012)  C16

 Rms deviation of fitted atoms =   0.0081
;

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
Cl1 C20 1.7884(19) . ?
C20 C20 1.484(4) 2_656 ?
O1 C19 1.328(2) . ?
O2 C19 1.208(2) . ?
N1 C16 1.454(2) . ?
N1 C8 1.489(2) . ?
N1 C9 1.491(2) . ?
N2 C2 1.434(2) . ?
N2 C9 1.457(2) . ?
N2 C10 1.475(2) . ?
C1 C6 1.393(2) . ?
C1 C2 1.398(2) . ?
C1 C8 1.510(2) . ?
C2 C3 1.396(2) . ?
C3 C4 1.387(2) . ?
C4 C5 1.390(3) . ?
C5 C6 1.387(3) . ?
C5 C7 1.512(3) . ?
C9 C18 1.531(2) . ?
C10 C11 1.512(2) . ?
C11 C16 1.392(2) . ?
C11 C12 1.396(2) . ?
C12 C13 1.393(2) . ?
C13 C14 1.397(2) . ?
C13 C17 1.503(2) . ?
C14 C15 1.373(2) . ?
C15 C16 1.398(2) . ?
C18 C19 1.502(2) . ?

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
C20 C20 Cl1 109.10(19) 2_656 . ?
C16 N1 C8 111.84(13) . . ?
C16 N1 C9 109.13(12) . . ?
C8 N1 C9 109.11(12) . . ?
C2 N2 C9 112.23(12) . . ?
C2 N2 C10 113.17(13) . . ?
C9 N2 C10 108.07(12) . . ?
C6 C1 C2 119.25(16) . . ?
C6 C1 C8 120.16(15) . . ?
C2 C1 C8 120.58(14) . . ?
C3 C2 C1 119.21(15) . . ?
C3 C2 N2 118.94(14) . . ?
C1 C2 N2 121.81(14) . . ?
C4 C3 C2 120.35(16) . . ?
C3 C4 C5 121.07(17) . . ?
C6 C5 C4 118.12(16) . . ?
C6 C5 C7 120.85(17) . . ?
C4 C5 C7 121.03(17) . . ?
C5 C6 C1 121.94(16) . . ?
N1 C8 C1 112.30(13) . . ?
N2 C9 N1 110.43(13) . . ?
N2 C9 C18 110.81(13) . . ?
N1 C9 C18 112.36(13) . . ?
N2 C10 C11 111.51(13) . . ?
C16 C11 C12 118.63(15) . . ?
C16 C11 C10 120.69(14) . . ?
C12 C11 C10 120.67(14) . . ?
C13 C12 C11 121.95(15) . . ?
C12 C13 C14 117.93(15) . . ?
C12 C13 C17 122.26(16) . . ?
C14 C13 C17 119.80(15) . . ?
C15 C14 C13 121.18(16) . . ?
C14 C15 C16 120.22(16) . . ?
C11 C16 C15 120.04(15) . . ?
C11 C16 N1 122.20(14) . . ?
C15 C16 N1 117.70(14) . . ?
C19 C18 C9 111.33(13) . . ?
O2 C19 O1 124.36(16) . . ?
O2 C19 C18 124.02(16) . . ?
O1 C19 C18 111.60(14) . . ?

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
C6 C1 C2 C3 -2.4(3) . . . . ?
C8 C1 C2 C3 178.51(15) . . . . ?
C6 C1 C2 N2 175.46(15) . . . . ?
C8 C1 C2 N2 -3.6(2) . . . . ?
C9 N2 C2 C3 159.85(15) . . . . ?
C10 N2 C2 C3 -77.50(18) . . . . ?
C9 N2 C2 C1 -18.0(2) . . . . ?
C10 N2 C2 C1 104.63(17) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
N2 C2 C3 C4 -176.73(16) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 -2.1(3) . . . . ?
C3 C4 C5 C7 177.88(18) . . . . ?
C4 C5 C6 C1 0.9(3) . . . . ?
C7 C5 C6 C1 -179.13(17) . . . . ?
C2 C1 C6 C5 1.4(3) . . . . ?
C8 C1 C6 C5 -179.52(17) . . . . ?
C16 N1 C8 C1 -77.06(17) . . . . ?
C9 N1 C8 C1 43.76(18) . . . . ?
C6 C1 C8 N1 170.69(15) . . . . ?
C2 C1 C8 N1 -10.2(2) . . . . ?
C2 N2 C9 N1 53.24(16) . . . . ?
C10 N2 C9 N1 -72.25(15) . . . . ?
C2 N2 C9 C18 -71.92(17) . . . . ?
C10 N2 C9 C18 162.59(13) . . . . ?
C16 N1 C9 N2 55.04(16) . . . . ?
C8 N1 C9 N2 -67.42(16) . . . . ?
C16 N1 C9 C18 179.32(13) . . . . ?
C8 N1 C9 C18 56.86(17) . . . . ?
C2 N2 C10 C11 -77.73(17) . . . . ?
C9 N2 C10 C11 47.20(17) . . . . ?
N2 C10 C11 C16 -11.3(2) . . . . ?
N2 C10 C11 C12 168.76(14) . . . . ?
C16 C11 C12 C13 -0.5(2) . . . . ?
C10 C11 C12 C13 179.42(15) . . . . ?
C11 C12 C13 C14 1.9(2) . . . . ?
C11 C12 C13 C17 -177.04(16) . . . . ?
C12 C13 C14 C15 -1.4(3) . . . . ?
C17 C13 C14 C15 177.50(17) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C12 C11 C16 C15 -1.3(2) . . . . ?
C10 C11 C16 C15 178.76(15) . . . . ?
C12 C11 C16 N1 175.93(15) . . . . ?
C10 C11 C16 N1 -4.0(2) . . . . ?
C14 C15 C16 C11 1.7(3) . . . . ?
C14 C15 C16 N1 -175.61(15) . . . . ?
C8 N1 C16 C11 103.75(17) . . . . ?
C9 N1 C16 C11 -17.1(2) . . . . ?
C8 N1 C16 C15 -78.99(17) . . . . ?
C9 N1 C16 C15 160.20(14) . . . . ?
N2 C9 C18 C19 177.92(13) . . . . ?
N1 C9 C18 C19 53.86(19) . . . . ?
C9 C18 C19 O2 -110.95(19) . . . . ?
C9 C18 C19 O1 67.45(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.70
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.067
_database_code_depnum_ccdc_archive 'CCDC 938744'