# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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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# 
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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.
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data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H13 Cl2 N O'
_chemical_formula_sum            'C23 H13 Cl2 N O'
_chemical_formula_weight         390.24

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           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'

_cell_length_a                   7.8740(13)
_cell_length_b                   8.3670(14)
_cell_length_c                   13.195(2)
_cell_angle_alpha                91.615(14)
_cell_angle_beta                 103.438(13)
_cell_angle_gamma                90.080(14)
_cell_volume                     845.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9572
_cell_measurement_theta_min      3.4
_cell_measurement_theta_max      26.035

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8444
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'

_exptl_special_details           
;
 ;
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Genix 3D I\mS microfocus X-ray source'
_diffrn_radiation_monochromator  'Genix 3D multilayer optics'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8702
_diffrn_reflns_av_R_equivalents  0.0948
_diffrn_reflns_av_sigmaI/netI    0.0682
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.40
_diffrn_reflns_theta_max         25.64
_reflns_number_total             3157
_reflns_number_gt                2582
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008) '
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008) '
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material  SHELXL97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0731P)²+0.0000P] where P=(Fo²+2Fc²)/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         3157
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1249
_refine_ls_wR_factor_gt          0.1187
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 -0.32777(6) 0.50936(8) 0.12730(5) 0.03000(19) Uani 1 1 d . . .
Cl2 Cl 0.11844(7) 0.83877(7) -0.04104(4) 0.02875(18) Uani 1 1 d . . .
O1 O -0.0135(2) 0.4187(2) 0.28159(13) 0.0260(4) Uani 1 1 d . . .
H1O H 0.088(4) 0.399(4) 0.316(3) 0.038(8) Uiso 1 1 d . . .
N1 N 0.3193(2) 0.4041(2) 0.35386(14) 0.0194(4) Uani 1 1 d . . .
C1 C 0.3409(3) 0.5013(3) 0.28431(17) 0.0202(5) Uani 1 1 d . . .
H1 H 0.4556 0.5345 0.2825 0.024 Uiso 1 1 calc R . .
C2 C 0.4618(3) 0.3295(3) 0.42038(16) 0.0183(4) Uani 1 1 d . . .
C3 C 0.4337(3) 0.2665(3) 0.51330(16) 0.0180(4) Uani 1 1 d . . .
C4 C 0.2779(3) 0.2973(3) 0.54912(17) 0.0203(5) Uani 1 1 d . . .
H4 H 0.1898 0.3629 0.5097 0.024 Uiso 1 1 calc R . .
C5 C 0.2546(3) 0.2343(3) 0.63832(17) 0.0223(5) Uani 1 1 d . . .
H5 H 0.1517 0.2597 0.6612 0.027 Uiso 1 1 calc R . .
C6 C 0.3802(3) 0.1305(3) 0.69935(17) 0.0217(5) Uani 1 1 d . . .
C7 C 0.3544(3) 0.0572(3) 0.78874(19) 0.0277(5) Uani 1 1 d . . .
H7 H 0.2495 0.0759 0.8109 0.033 Uiso 1 1 calc R . .
C8 C 0.4800(3) -0.0427(3) 0.84544(19) 0.0315(6) Uani 1 1 d . . .
H8 H 0.4596 -0.0928 0.9052 0.038 Uiso 1 1 calc R . .
C9 C 0.6345(3) -0.0694(3) 0.81541(18) 0.0284(5) Uani 1 1 d . . .
H9 H 0.7197 -0.1373 0.8552 0.034 Uiso 1 1 calc R . .
C10 C 0.6674(3) 0.0021(3) 0.72693(17) 0.0208(5) Uani 1 1 d . . .
C11 C 0.8290(3) -0.0214(3) 0.69554(18) 0.0238(5) Uani 1 1 d . . .
H11 H 0.9171 -0.0865 0.7353 0.029 Uiso 1 1 calc R . .
C12 C 0.8557(3) 0.0492(3) 0.60936(18) 0.0221(5) Uani 1 1 d . . .
H12 H 0.9636 0.0327 0.5902 0.027 Uiso 1 1 calc R . .
C13 C 0.7279(3) 0.1472(3) 0.54656(17) 0.0193(4) Uani 1 1 d . . .
C14 C 0.7519(3) 0.2184(3) 0.45607(18) 0.0213(5) Uani 1 1 d . . .
H14 H 0.8607 0.2065 0.4373 0.026 Uiso 1 1 calc R . .
C15 C 0.6224(3) 0.3051(3) 0.39362(17) 0.0207(5) Uani 1 1 d . . .
H15 H 0.6418 0.3490 0.3316 0.025 Uiso 1 1 calc R . .
C16 C 0.5381(3) 0.1010(3) 0.66729(17) 0.0195(5) Uani 1 1 d . . .
C17 C 0.5655(2) 0.1728(3) 0.57547(16) 0.0171(4) Uani 1 1 d . . .
C21 C 0.1924(3) 0.5616(3) 0.20824(17) 0.0200(5) Uani 1 1 d . . .
C22 C 0.0198(3) 0.5150(3) 0.20934(17) 0.0198(4) Uani 1 1 d . . .
C23 C -0.1164(3) 0.5708(3) 0.13153(17) 0.0215(5) Uani 1 1 d . . .
C24 C -0.0879(3) 0.6712(3) 0.05569(17) 0.0233(5) Uani 1 1 d . . .
H24 H -0.1830 0.7083 0.0037 0.028 Uiso 1 1 calc R . .
C25 C 0.0825(3) 0.7169(3) 0.05672(17) 0.0205(5) Uani 1 1 d . . .
C26 C 0.2207(3) 0.6636(3) 0.13106(17) 0.0205(5) Uani 1 1 d . . .
H26 H 0.3362 0.6958 0.1304 0.025 Uiso 1 1 calc R . .


_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 C23 1.729(2) . ?
Cl2 C25 1.740(2) . ?
O1 C22 1.337(3) . ?
O1 H1O 0.84(4) . ?
N1 C1 1.284(3) . ?
N1 C2 1.412(3) . ?
C1 C21 1.454(3) . ?
C1 H1 0.9500 . ?
C2 C15 1.403(3) . ?
C2 C3 1.412(3) . ?
C3 C17 1.417(3) . ?
C3 C4 1.434(3) . ?
C4 C5 1.353(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.433(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.400(3) . ?
C6 C16 1.423(3) . ?
C7 C8 1.389(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.381(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.403(3) . ?
C9 H9 0.9500 . ?
C10 C16 1.416(3) . ?
C10 C11 1.439(3) . ?
C11 C12 1.355(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.423(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.400(3) . ?
C13 C17 1.432(3) . ?
C14 C15 1.375(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.427(3) . ?
C21 C26 1.403(3) . ?
C21 C22 1.417(3) . ?
C22 C23 1.393(3) . ?
C23 C24 1.381(3) . ?
C24 C25 1.392(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.369(3) . ?
C26 H26 0.9500 . ?

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
C22 O1 H1O 101(2) . . ?
C1 N1 C2 121.82(18) . . ?
N1 C1 C21 120.99(19) . . ?
N1 C1 H1 119.5 . . ?
C21 C1 H1 119.5 . . ?
C15 C2 C3 119.7(2) . . ?
C15 C2 N1 122.71(19) . . ?
C3 C2 N1 117.38(17) . . ?
C2 C3 C17 119.17(18) . . ?
C2 C3 C4 122.5(2) . . ?
C17 C3 C4 118.3(2) . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 122.05(19) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C7 C6 C16 118.8(2) . . ?
C7 C6 C5 123.0(2) . . ?
C16 C6 C5 118.3(2) . . ?
C8 C7 C6 120.9(2) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C9 C8 C7 120.4(2) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.9(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C16 119.0(2) . . ?
C9 C10 C11 121.9(2) . . ?
C16 C10 C11 119.2(2) . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 122.30(19) . . ?
C11 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C14 C13 C12 123.06(18) . . ?
C14 C13 C17 118.0(2) . . ?
C12 C13 C17 119.0(2) . . ?
C15 C14 C13 121.81(18) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C2 120.8(2) . . ?
C14 C15 H15 119.6 . . ?
C2 C15 H15 119.6 . . ?
C10 C16 C6 120.0(2) . . ?
C10 C16 C17 120.51(18) . . ?
C6 C16 C17 119.5(2) . . ?
C3 C17 C16 120.65(18) . . ?
C3 C17 C13 120.5(2) . . ?
C16 C17 C13 118.9(2) . . ?
C26 C21 C22 119.6(2) . . ?
C26 C21 C1 119.59(19) . . ?
C22 C21 C1 120.8(2) . . ?
O1 C22 C23 120.18(19) . . ?
O1 C22 C21 121.7(2) . . ?
C23 C22 C21 118.1(2) . . ?
C24 C23 C22 122.09(19) . . ?
C24 C23 Cl1 118.63(17) . . ?
C22 C23 Cl1 119.26(17) . . ?
C23 C24 C25 118.9(2) . . ?
C23 C24 H24 120.6 . . ?
C25 C24 H24 120.6 . . ?
C26 C25 C24 121.1(2) . . ?
C26 C25 Cl2 120.15(17) . . ?
C24 C25 Cl2 118.75(18) . . ?
C25 C26 C21 120.25(19) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?

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
C2 N1 C1 C21 172.35(18) . . . . ?
C1 N1 C2 C15 -24.6(3) . . . . ?
C1 N1 C2 C3 160.59(19) . . . . ?
C15 C2 C3 C17 -3.1(3) . . . . ?
N1 C2 C3 C17 171.87(18) . . . . ?
C15 C2 C3 C4 175.2(2) . . . . ?
N1 C2 C3 C4 -9.9(3) . . . . ?
C2 C3 C4 C5 179.6(2) . . . . ?
C17 C3 C4 C5 -2.1(3) . . . . ?
C3 C4 C5 C6 -2.0(3) . . . . ?
C4 C5 C6 C7 -176.4(2) . . . . ?
C4 C5 C6 C16 3.6(3) . . . . ?
C16 C6 C7 C8 0.0(3) . . . . ?
C5 C6 C7 C8 180.0(2) . . . . ?
C6 C7 C8 C9 1.0(4) . . . . ?
C7 C8 C9 C10 -0.5(4) . . . . ?
C8 C9 C10 C16 -1.0(3) . . . . ?
C8 C9 C10 C11 178.6(2) . . . . ?
C9 C10 C11 C12 179.7(2) . . . . ?
C16 C10 C11 C12 -0.7(3) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C12 C13 C14 -178.6(2) . . . . ?
C11 C12 C13 C17 0.2(3) . . . . ?
C12 C13 C14 C15 176.2(2) . . . . ?
C17 C13 C14 C15 -2.7(3) . . . . ?
C13 C14 C15 C2 2.0(3) . . . . ?
C3 C2 C15 C14 1.0(3) . . . . ?
N1 C2 C15 C14 -173.67(19) . . . . ?
C9 C10 C16 C6 2.0(3) . . . . ?
C11 C10 C16 C6 -177.62(19) . . . . ?
C9 C10 C16 C17 -178.57(19) . . . . ?
C11 C10 C16 C17 1.8(3) . . . . ?
C7 C6 C16 C10 -1.5(3) . . . . ?
C5 C6 C16 C10 178.5(2) . . . . ?
C7 C6 C16 C17 179.0(2) . . . . ?
C5 C6 C16 C17 -0.9(3) . . . . ?
C2 C3 C17 C16 -177.03(18) . . . . ?
C4 C3 C17 C16 4.7(3) . . . . ?
C2 C3 C17 C13 2.3(3) . . . . ?
C4 C3 C17 C13 -175.99(18) . . . . ?
C10 C16 C17 C3 177.41(18) . . . . ?
C6 C16 C17 C3 -3.1(3) . . . . ?
C10 C16 C17 C13 -1.9(3) . . . . ?
C6 C16 C17 C13 177.51(19) . . . . ?
C14 C13 C17 C3 0.5(3) . . . . ?
C12 C13 C17 C3 -178.44(19) . . . . ?
C14 C13 C17 C16 179.84(19) . . . . ?
C12 C13 C17 C16 0.9(3) . . . . ?
N1 C1 C21 C26 -177.88(19) . . . . ?
N1 C1 C21 C22 0.3(3) . . . . ?
C26 C21 C22 O1 -179.69(19) . . . . ?
C1 C21 C22 O1 2.1(3) . . . . ?
C26 C21 C22 C23 1.1(3) . . . . ?
C1 C21 C22 C23 -177.07(19) . . . . ?
O1 C22 C23 C24 179.7(2) . . . . ?
C21 C22 C23 C24 -1.1(3) . . . . ?
O1 C22 C23 Cl1 -1.9(3) . . . . ?
C21 C22 C23 Cl1 177.26(16) . . . . ?
C22 C23 C24 C25 0.5(3) . . . . ?
Cl1 C23 C24 C25 -177.95(16) . . . . ?
C23 C24 C25 C26 0.2(3) . . . . ?
C23 C24 C25 Cl2 178.24(16) . . . . ?
C24 C25 C26 C21 -0.2(3) . . . . ?
Cl2 C25 C26 C21 -178.19(16) . . . . ?
C22 C21 C26 C25 -0.5(3) . . . . ?
C1 C21 C26 C25 177.74(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O N1 0.84(4) 1.77(3) 2.577(2) 159(3) .

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.075
_database_code_depnum_ccdc_archive 'CCDC 978838'
