# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


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#                                CCDC 
# 
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# 
#  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. 
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data_120705_sp162_3
_database_code_depnum_ccdc_archive 'CCDC 890740'
#TrackingRef '120705_sp162_3.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H12 Cl N O'
_chemical_formula_sum            'C20 H12 Cl N O'
_chemical_formula_weight         317.76

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   20.8600(15)
_cell_length_b                   6.7273(4)
_cell_length_c                   21.7338(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3049.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3067
_cell_measurement_theta_min      3.0219
_cell_measurement_theta_max      29.5203

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9164
_exptl_absorpt_correction_T_max  0.9323
_exptl_absorpt_process_details   
;
CrysAlis PRO (Agilent Technologies, 2011)
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 10.3592
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11373
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.32
_diffrn_reflns_theta_max         25.35
_reflns_number_total             2784
_reflns_number_gt                2233
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_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^)+(0.0398P)^2^+1.0794P] 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       ?
_refine_ls_number_reflns         2784
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0960
_refine_ls_wR_factor_gt          0.0880
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.18132(3) 0.70237(10) 0.48482(2) 0.0625(2) Uani 1 1 d . . .
O1 O 0.14396(6) 0.39770(18) 0.39470(5) 0.0393(3) Uani 1 1 d . . .
N1 N 0.12860(7) 0.4502(2) 0.26857(6) 0.0342(3) Uani 1 1 d . . .
C1 C 0.15433(8) 0.5832(3) 0.36937(8) 0.0342(4) Uani 1 1 d . . .
C2 C 0.17355(8) 0.7402(3) 0.40622(8) 0.0398(4) Uani 1 1 d . . .
C3 C 0.18754(9) 0.9239(3) 0.38151(9) 0.0466(5) Uani 1 1 d . . .
H3 H 0.2009 1.0278 0.4067 0.056 Uiso 1 1 calc R . .
C4 C 0.18144(9) 0.9509(3) 0.31898(10) 0.0470(5) Uani 1 1 d . . .
H4 H 0.1911 1.0740 0.3018 0.056 Uiso 1 1 calc R . .
C5 C 0.16117(9) 0.7979(3) 0.28136(9) 0.0407(4) Uani 1 1 d . . .
H5 H 0.1562 0.8195 0.2394 0.049 Uiso 1 1 calc R . .
C6 C 0.14824(8) 0.6122(3) 0.30614(7) 0.0330(4) Uani 1 1 d . . .
C7 C 0.14869(8) 0.4173(3) 0.20801(7) 0.0344(4) Uani 1 1 d . . .
C8 C 0.19956(9) 0.4981(3) 0.17482(8) 0.0413(4) Uani 1 1 d . . .
H8 H 0.2267 0.5926 0.1921 0.050 Uiso 1 1 calc R . .
C9 C 0.20808(10) 0.4322(3) 0.11535(8) 0.0462(5) Uani 1 1 d . . .
H9 H 0.2414 0.4845 0.0920 0.055 Uiso 1 1 calc R . .
C10 C 0.16806(10) 0.2893(3) 0.08918(9) 0.0480(5) Uani 1 1 d . . .
H10 H 0.1750 0.2490 0.0488 0.058 Uiso 1 1 calc R . .
C11 C 0.11872(10) 0.2075(3) 0.12210(9) 0.0465(5) Uani 1 1 d . . .
H11 H 0.0924 0.1118 0.1044 0.056 Uiso 1 1 calc R . .
C12 C 0.10848(9) 0.2702(3) 0.18289(8) 0.0377(4) Uani 1 1 d . . .
C13 C 0.06375(9) 0.2157(3) 0.22927(8) 0.0409(4) Uani 1 1 d . . .
H13 H 0.0311 0.1225 0.2250 0.049 Uiso 1 1 calc R . .
C14 C 0.07671(8) 0.3227(3) 0.28081(8) 0.0344(4) Uani 1 1 d . . .
C15 C 0.04638(9) 0.3043(3) 0.34123(8) 0.0357(4) Uani 1 1 d . . .
C16 C -0.01645(9) 0.2340(3) 0.34612(9) 0.0434(5) Uani 1 1 d . . .
H16 H -0.0399 0.2103 0.3105 0.052 Uiso 1 1 calc R . .
C17 C -0.04455(11) 0.1989(3) 0.40239(9) 0.0520(5) Uani 1 1 d . . .
H17 H -0.0864 0.1515 0.4044 0.062 Uiso 1 1 calc R . .
C18 C -0.01056(11) 0.2343(3) 0.45578(10) 0.0553(6) Uani 1 1 d . . .
H18 H -0.0294 0.2098 0.4938 0.066 Uiso 1 1 calc R . .
C19 C 0.05159(10) 0.3062(3) 0.45264(9) 0.0500(5) Uani 1 1 d . . .
H19 H 0.0744 0.3319 0.4885 0.060 Uiso 1 1 calc R . .
C20 C 0.07932(9) 0.3393(3) 0.39596(8) 0.0372(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 0.0636(4) 0.0828(4) 0.0412(3) -0.0167(3) -0.0089(2) -0.0058(3)
O1 0.0374(7) 0.0386(7) 0.0418(7) 0.0040(6) -0.0078(5) 0.0001(6)
N1 0.0384(8) 0.0305(8) 0.0336(7) -0.0017(6) -0.0036(6) -0.0040(7)
C1 0.0277(9) 0.0333(9) 0.0416(9) -0.0034(8) -0.0040(7) 0.0020(8)
C2 0.0294(9) 0.0470(11) 0.0430(10) -0.0124(9) -0.0045(7) 0.0025(9)
C3 0.0371(11) 0.0400(11) 0.0627(13) -0.0164(10) -0.0042(9) -0.0024(9)
C4 0.0401(11) 0.0312(10) 0.0699(13) -0.0027(10) -0.0034(9) -0.0024(9)
C5 0.0393(11) 0.0356(10) 0.0473(10) 0.0015(9) -0.0053(8) 0.0000(8)
C6 0.0279(9) 0.0308(9) 0.0405(9) -0.0037(8) -0.0047(7) 0.0002(8)
C7 0.0377(10) 0.0317(9) 0.0338(9) -0.0002(8) -0.0037(7) 0.0017(8)
C8 0.0401(11) 0.0399(10) 0.0439(10) 0.0009(9) -0.0039(8) -0.0031(9)
C9 0.0441(11) 0.0515(12) 0.0429(10) 0.0013(10) 0.0054(8) 0.0012(10)
C10 0.0546(12) 0.0524(12) 0.0372(10) -0.0046(9) 0.0016(9) 0.0051(11)
C11 0.0564(13) 0.0440(11) 0.0391(10) -0.0073(9) -0.0072(9) -0.0038(10)
C12 0.0411(10) 0.0342(10) 0.0378(9) -0.0011(8) -0.0057(8) -0.0007(8)
C13 0.0422(11) 0.0391(10) 0.0413(10) -0.0034(9) -0.0065(8) -0.0091(9)
C14 0.0351(10) 0.0300(9) 0.0382(9) 0.0011(8) -0.0044(7) -0.0028(8)
C15 0.0373(10) 0.0284(9) 0.0414(9) 0.0014(8) -0.0010(7) -0.0008(8)
C16 0.0422(11) 0.0399(10) 0.0480(11) -0.0009(9) -0.0019(8) -0.0076(9)
C17 0.0463(12) 0.0483(12) 0.0613(13) 0.0021(11) 0.0092(9) -0.0111(10)
C18 0.0600(14) 0.0564(13) 0.0496(12) 0.0055(10) 0.0147(10) -0.0048(11)
C19 0.0573(13) 0.0547(12) 0.0380(10) 0.0022(9) -0.0026(9) -0.0019(11)
C20 0.0372(10) 0.0320(9) 0.0426(10) 0.0007(8) -0.0025(7) 0.0016(8)

_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
Cl1 C2 1.7346(19) . ?
O1 C1 1.381(2) . ?
O1 C20 1.405(2) . ?
N1 C7 1.399(2) . ?
N1 C14 1.407(2) . ?
N1 C6 1.422(2) . ?
C1 C2 1.385(2) . ?
C1 C6 1.394(2) . ?
C2 C3 1.379(3) . ?
C3 C4 1.377(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(2) . ?
C5 H5 0.9300 . ?
C7 C8 1.393(3) . ?
C7 C12 1.407(2) . ?
C8 C9 1.378(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.395(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.369(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.403(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.422(3) . ?
C13 C14 1.359(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.463(2) . ?
C15 C20 1.394(2) . ?
C15 C16 1.397(3) . ?
C16 C17 1.376(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.386(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.379(3) . ?
C19 H19 0.9300 . ?

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
C1 O1 C20 114.25(13) . . ?
C7 N1 C14 108.18(13) . . ?
C7 N1 C6 125.12(14) . . ?
C14 N1 C6 125.48(14) . . ?
O1 C1 C2 120.27(16) . . ?
O1 C1 C6 120.33(15) . . ?
C2 C1 C6 119.34(17) . . ?
C3 C2 C1 121.30(17) . . ?
C3 C2 Cl1 119.70(14) . . ?
C1 C2 Cl1 118.99(15) . . ?
C4 C3 C2 118.91(18) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 120.95(19) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 120.07(18) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 119.40(16) . . ?
C5 C6 N1 121.56(15) . . ?
C1 C6 N1 119.04(15) . . ?
C8 C7 N1 130.81(16) . . ?
C8 C7 C12 121.82(16) . . ?
N1 C7 C12 107.32(15) . . ?
C9 C8 C7 117.29(17) . . ?
C9 C8 H8 121.4 . . ?
C7 C8 H8 121.4 . . ?
C8 C9 C10 121.80(18) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C11 C10 C9 120.94(18) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 119.06(18) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C7 119.07(17) . . ?
C11 C12 C13 133.63(17) . . ?
C7 C12 C13 107.30(15) . . ?
C14 C13 C12 108.51(16) . . ?
C14 C13 H13 125.7 . . ?
C12 C13 H13 125.7 . . ?
C13 C14 N1 108.68(15) . . ?
C13 C14 C15 127.53(17) . . ?
N1 C14 C15 123.67(15) . . ?
C20 C15 C16 117.04(17) . . ?
C20 C15 C14 122.59(16) . . ?
C16 C15 C14 120.17(16) . . ?
C17 C16 C15 121.67(18) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C18 119.9(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C19 119.95(19) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C20 C19 C18 119.53(18) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C15 121.88(18) . . ?
C19 C20 O1 117.73(16) . . ?
C15 C20 O1 120.26(15) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.045