# Electronic Supplementary Material (ESI) for ChemComm.
# 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
#  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_qq

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H17 Cl2 N O3'
_chemical_formula_sum            'C23 H17 Cl2 N O3'
_chemical_formula_weight         426.28

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'
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'
N N 0.0061 0.0033 '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'

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

_cell_length_a                   9.8294(19)
_cell_length_b                   10.0500(19)
_cell_length_c                   12.169(2)
_cell_angle_alpha                114.2730(10)
_cell_angle_beta                 97.114(2)
_cell_angle_gamma                105.6450(10)
_cell_volume                     1016.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      25.0

_exptl_crystal_description       bulk
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_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  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5172
_diffrn_reflns_av_R_equivalents  0.0123
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3530
_reflns_number_gt                2800
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2006)'
_computing_cell_refinement       CrysAlis
_computing_data_reduction        CrysAlis
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0503P)²+0.3259P] 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         3530
_refine_ls_number_parameters     262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1147
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
C1 C 0.1742(2) -0.9637(2) -0.69528(18) 0.0433(5) Uani 1 1 d . . .
C2 C 0.1686(3) -0.9720(3) -0.5849(2) 0.0561(6) Uani 1 1 d . . .
H2 H 0.1257 -1.0685 -0.5881 0.067 Uiso 1 1 calc R . .
C3 C 0.2253(3) -0.8398(3) -0.4706(2) 0.0620(6) Uani 1 1 d . . .
H3 H 0.2200 -0.8463 -0.3971 0.074 Uiso 1 1 calc R . .
C4 C 0.2899(3) -0.6978(3) -0.4675(2) 0.0562(6) Uani 1 1 d . . .
C5 C 0.2968(3) -0.6856(3) -0.5751(2) 0.0574(6) Uani 1 1 d . . .
H5 H 0.3401 -0.5888 -0.5713 0.069 Uiso 1 1 calc R . .
C6 C 0.2386(2) -0.8188(3) -0.6890(2) 0.0514(5) Uani 1 1 d . . .
H6 H 0.2425 -0.8113 -0.7623 0.062 Uiso 1 1 calc R . .
C7 C 0.1167(2) -1.1130(2) -0.81524(19) 0.0432(5) Uani 1 1 d . . .
C8 C 0.0649(2) -1.1967(2) -1.04645(19) 0.0426(5) Uani 1 1 d . . .
C9 C 0.0964(2) -1.3461(2) -1.08010(18) 0.0420(5) Uani 1 1 d . . .
H9 H 0.0459 -1.3994 -1.0370 0.050 Uiso 1 1 calc R . .
C10 C 0.0404(2) -1.4554(2) -1.22067(19) 0.0464(5) Uani 1 1 d . . .
H10A H 0.0836 -1.3998 -1.2641 0.056 Uiso 1 1 calc R . .
H10B H 0.0740 -1.5427 -1.2394 0.056 Uiso 1 1 calc R . .
C11 C -0.1235(2) -1.5179(2) -1.27092(19) 0.0441(5) Uani 1 1 d . . .
C12 C -0.1894(2) -1.6454(2) -1.40333(19) 0.0455(5) Uani 1 1 d . . .
C13 C -0.3382(3) -1.7310(3) -1.4405(2) 0.0607(6) Uani 1 1 d . . .
H13 H -0.3946 -1.7067 -1.3843 0.073 Uiso 1 1 calc R . .
C14 C -0.4034(3) -1.8523(3) -1.5605(3) 0.0741(8) Uani 1 1 d . . .
H14 H -0.5031 -1.9099 -1.5846 0.089 Uiso 1 1 calc R . .
C15 C -0.3205(3) -1.8875(3) -1.6442(2) 0.0727(8) Uani 1 1 d . . .
H15 H -0.3646 -1.9684 -1.7251 0.087 Uiso 1 1 calc R . .
C16 C -0.1729(3) -1.8040(3) -1.6089(2) 0.0672(7) Uani 1 1 d . . .
H16 H -0.1173 -1.8286 -1.6658 0.081 Uiso 1 1 calc R . .
C17 C -0.1069(3) -1.6829(3) -1.4883(2) 0.0544(6) Uani 1 1 d . . .
H17 H -0.0068 -1.6268 -1.4643 0.065 Uiso 1 1 calc R . .
C18 C 0.2605(2) -1.3076(2) -1.03510(18) 0.0424(5) Uani 1 1 d . . .
C19 C 0.3604(3) -1.2196(3) -1.0718(2) 0.0576(6) Uani 1 1 d . . .
H19 H 0.3275 -1.1790 -1.1216 0.069 Uiso 1 1 calc R . .
C20 C 0.5092(3) -1.1910(3) -1.0352(3) 0.0714(8) Uani 1 1 d . . .
H20 H 0.5755 -1.1325 -1.0610 0.086 Uiso 1 1 calc R . .
C21 C 0.5573(3) -1.2496(3) -0.9609(3) 0.0685(7) Uani 1 1 d . . .
C22 C 0.4613(3) -1.3357(3) -0.9228(2) 0.0679(7) Uani 1 1 d . . .
H22 H 0.4953 -1.3746 -0.8720 0.081 Uiso 1 1 calc R . .
C23 C 0.3133(3) -1.3649(3) -0.9600(2) 0.0552(6) Uani 1 1 d . . .
H23 H 0.2480 -1.4242 -0.9341 0.066 Uiso 1 1 calc R . .
O1 O 0.09737(18) -1.23831(18) -0.81804(14) 0.0585(4) Uani 1 1 d . . .
O2 O -0.20147(17) -1.46978(18) -1.20639(14) 0.0586(4) Uani 1 1 d . . .
O3 O 0.02838(18) -1.15749(17) -1.12432(13) 0.0560(4) Uani 1 1 d . . .
Cl1 Cl 0.74407(8) -1.21203(11) -0.91425(10) 0.1167(4) Uani 1 1 d . . .
Cl2 Cl 0.36597(8) -0.53003(8) -0.32400(6) 0.0830(3) Uani 1 1 d . . .
N1 N 0.08865(19) -1.09425(19) -0.92161(15) 0.0462(4) Uani 1 1 d D . .
H1A H 0.0741 -1.0140 -0.9132 0.069 Uiso 1 1 d RD . .


_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
C1 C2 1.386(3) . ?
C1 C6 1.388(3) . ?
C1 C7 1.496(3) . ?
C2 C3 1.378(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(3) . ?
C4 Cl2 1.740(2) . ?
C5 C6 1.380(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.207(2) . ?
C7 N1 1.388(2) . ?
C8 O3 1.217(2) . ?
C8 N1 1.385(3) . ?
C8 C9 1.515(3) . ?
C9 C18 1.523(3) . ?
C9 C10 1.527(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.504(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O2 1.214(2) . ?
C11 C12 1.501(3) . ?
C12 C13 1.386(3) . ?
C12 C17 1.386(3) . ?
C13 C14 1.383(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.373(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.388(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.382(3) . ?
C18 C23 1.383(3) . ?
C19 C20 1.387(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.368(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.360(4) . ?
C21 Cl1 1.740(3) . ?
C22 C23 1.380(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
N1 H1A 0.8238 . ?

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
C2 C1 C6 118.7(2) . . ?
C2 C1 C7 118.10(19) . . ?
C6 C1 C7 123.16(19) . . ?
C3 C2 C1 121.3(2) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 118.6(2) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 121.5(2) . . ?
C5 C4 Cl2 119.02(19) . . ?
C3 C4 Cl2 119.45(19) . . ?
C4 C5 C6 119.2(2) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 120.7(2) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
O1 C7 N1 123.45(19) . . ?
O1 C7 C1 122.26(18) . . ?
N1 C7 C1 114.29(17) . . ?
O3 C8 N1 118.06(18) . . ?
O3 C8 C9 122.61(18) . . ?
N1 C8 C9 119.16(17) . . ?
C8 C9 C18 109.72(16) . . ?
C8 C9 C10 111.43(16) . . ?
C18 C9 C10 110.53(16) . . ?
C8 C9 H9 108.4 . . ?
C18 C9 H9 108.4 . . ?
C10 C9 H9 108.4 . . ?
C11 C10 C9 114.48(18) . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
O2 C11 C12 120.5(2) . . ?
O2 C11 C10 121.52(19) . . ?
C12 C11 C10 117.95(18) . . ?
C13 C12 C17 119.0(2) . . ?
C13 C12 C11 118.3(2) . . ?
C17 C12 C11 122.7(2) . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.9(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 120.3(2) . . ?
C12 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C23 118.0(2) . . ?
C19 C18 C9 121.2(2) . . ?
C23 C18 C9 120.77(19) . . ?
C18 C19 C20 120.9(2) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C21 C20 C19 119.4(2) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C22 C21 C20 120.9(2) . . ?
C22 C21 Cl1 119.9(2) . . ?
C20 C21 Cl1 119.2(2) . . ?
C21 C22 C23 119.7(3) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C22 C23 C18 121.1(2) . . ?
C22 C23 H23 119.4 . . ?
C18 C23 H23 119.4 . . ?
C8 N1 C7 130.66(17) . . ?
C8 N1 H1A 111.5 . . ?
C7 N1 H1A 117.4 . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 938346'
