# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ASDF
_database_code_depnum_ccdc_archive 'CCDC 1444745'
_audit_update_record             
;
2015-12-30 deposited with the CCDC.
2016-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H19 Cl N2 O'
_chemical_formula_sum            'C23 H19 Cl N2 O'
_chemical_formula_weight         374.85

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.925(6)
_cell_length_b                   23.667(12)
_cell_length_c                   7.039(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.498(6)
_cell_angle_gamma                90
_cell_volume                     1959.4(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1924
_cell_measurement_theta_min      7.58
_cell_measurement_theta_max      29.03

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.209
_shelx_estimated_absorpt_T_min   0.921
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9209
_exptl_absorpt_correction_T_max  0.9653
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12071
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.721
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.941
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.941
_reflns_number_total             3345
_reflns_number_gt                2627
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0607P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3345
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1448
_refine_ls_wR_factor_gt          0.1374
_refine_ls_goodness_of_fit_ref   1.416
_refine_ls_restrained_S_all      1.416
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.41857(6) -0.13697(4) 0.09457(13) 0.0888(3) Uani 1 1 d . . . . .
C1 C 0.5349(2) -0.09128(11) 0.1279(3) 0.0549(6) Uani 1 1 d . . . . .
C2 C 0.52788(19) -0.04086(11) 0.2209(3) 0.0549(6) Uani 1 1 d . . . . .
H2 H 0.4609 -0.0302 0.2625 0.066 Uiso 1 1 calc R U . . .
C3 C 0.62194(19) -0.00633(10) 0.2516(3) 0.0484(5) Uani 1 1 d . . . . .
H3 H 0.6188 0.0276 0.3172 0.058 Uiso 1 1 calc R U . . .
C4 C 0.72054(17) -0.02121(8) 0.1865(3) 0.0404(5) Uani 1 1 d . . . . .
C7 C 0.82101(17) 0.01675(9) 0.2241(3) 0.0426(5) Uani 1 1 d . . . . .
H7 H 0.8317 0.0361 0.3488 0.051 Uiso 1 1 calc R U . . .
C8 C 0.86768(17) 0.04662(8) 0.0696(3) 0.0409(5) Uani 1 1 d . . . . .
C10 C 0.93023(18) 0.10217(9) 0.1004(3) 0.0470(5) Uani 1 1 d . . . . .
H10A H 0.9926 0.1017 0.0277 0.056 Uiso 1 1 calc R U . . .
H10B H 0.8789 0.1323 0.0487 0.056 Uiso 1 1 calc R U . . .
N2 N 0.97470(15) 0.11491(8) 0.2971(3) 0.0495(5) Uani 1 1 d . . . . .
C11 C 1.09136(19) 0.09913(10) 0.3675(4) 0.0587(6) Uani 1 1 d . . . . .
H11A H 1.1082 0.0651 0.3008 0.070 Uiso 1 1 calc R U . . .
H11B H 1.0980 0.0899 0.5031 0.070 Uiso 1 1 calc R U . . .
C12 C 1.18111(17) 0.14316(9) 0.3450(3) 0.0437(5) Uani 1 1 d . . . . .
C17 C 1.15648(19) 0.19368(9) 0.2488(3) 0.0519(6) Uani 1 1 d . . . . .
H17 H 1.0818 0.2021 0.1952 0.062 Uiso 1 1 calc R U . . .
C16 C 1.2415(2) 0.23162(10) 0.2319(3) 0.0583(6) Uani 1 1 d . . . . .
H16 H 1.2242 0.2651 0.1642 0.070 Uiso 1 1 calc R U . . .
C15 C 1.3519(2) 0.22044(11) 0.3141(3) 0.0612(7) Uani 1 1 d . . . . .
H15 H 1.4090 0.2466 0.3053 0.073 Uiso 1 1 calc R U . . .
C6 C 0.6320(2) -0.10740(11) 0.0626(3) 0.0615(7) Uani 1 1 d . . . . .
H6 H 0.6349 -0.1417 -0.0008 0.074 Uiso 1 1 calc R U . . .
C5 C 0.7254(2) -0.07216(10) 0.0920(3) 0.0567(6) Uani 1 1 d . . . . .
H5 H 0.7918 -0.0827 0.0482 0.068 Uiso 1 1 calc R U . . .
O1 O 0.92420(12) -0.00201(6) 0.1617(2) 0.0504(4) Uani 1 1 d . . . . .
C18 C 0.9121(2) 0.14577(9) 0.4112(3) 0.0481(5) Uani 1 1 d . . . . .
C23 C 0.7957(2) 0.15269(10) 0.3568(4) 0.0612(7) Uani 1 1 d . . . . .
H23 H 0.7593 0.1369 0.2420 0.073 Uiso 1 1 calc R U . . .
C22 C 0.7331(3) 0.18286(13) 0.4717(6) 0.0972(12) Uani 1 1 d . . . . .
H22 H 0.6549 0.1866 0.4340 0.117 Uiso 1 1 calc R U . . .
C21 C 0.7840(5) 0.20683(15) 0.6378(8) 0.1247(19) Uani 1 1 d . . . . .
H21 H 0.7411 0.2270 0.7137 0.150 Uiso 1 1 calc R U . . .
C20 C 0.8978(5) 0.20149(14) 0.6935(5) 0.1060(14) Uani 1 1 d . . . . .
H20 H 0.9327 0.2185 0.8071 0.127 Uiso 1 1 calc R U . . .
C19 C 0.9640(3) 0.17065(11) 0.5823(3) 0.0744(8) Uani 1 1 d . . . . .
H19 H 1.0420 0.1669 0.6227 0.089 Uiso 1 1 calc R U . . .
C13 C 1.29242(19) 0.13216(10) 0.4237(3) 0.0521(6) Uani 1 1 d . . . . .
H13 H 1.3105 0.0982 0.4877 0.063 Uiso 1 1 calc R U . . .
C14 C 1.3770(2) 0.17012(12) 0.4098(3) 0.0611(7) Uani 1 1 d . . . . .
H14 H 1.4516 0.1620 0.4649 0.073 Uiso 1 1 calc R U . . .
C9 C 0.81426(18) 0.03699(9) -0.1293(3) 0.0448(5) Uani 1 1 d . . . . .
N1 N 0.77399(19) 0.03099(9) -0.2848(3) 0.0645(6) Uani 1 1 d . . . . .


_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 C1 1.744(2) . ?
C1 C2 1.370(4) . ?
C1 C6 1.368(4) . ?
C2 C3 1.376(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(3) . ?
C4 C7 1.486(3) . ?
C7 O1 1.443(3) . ?
C7 C8 1.481(3) . ?
C7 H7 0.9800 . ?
C8 O1 1.434(3) . ?
C8 C9 1.457(3) . ?
C8 C10 1.509(3) . ?
C10 N2 1.431(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
N2 C18 1.391(3) . ?
N2 C11 1.447(3) . ?
C11 C12 1.521(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.376(3) . ?
C12 C17 1.381(3) . ?
C17 C16 1.374(3) . ?
C17 H17 0.9300 . ?
C16 C15 1.373(4) . ?
C16 H16 0.9300 . ?
C15 C14 1.376(4) . ?
C15 H15 0.9300 . ?
C6 C5 1.380(3) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
C18 C23 1.388(4) . ?
C18 C19 1.390(3) . ?
C23 C22 1.386(4) . ?
C23 H23 0.9300 . ?
C22 C21 1.350(6) . ?
C22 H22 0.9300 . ?
C21 C20 1.355(6) . ?
C21 H21 0.9300 . ?
C20 C19 1.405(5) . ?
C20 H20 0.9300 . ?
C19 H19 0.9300 . ?
C13 C14 1.366(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C9 N1 1.129(3) . ?

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 121.7(2) . . ?
C2 C1 Cl1 119.6(2) . . ?
C6 C1 Cl1 118.7(2) . . ?
C1 C2 C3 118.7(2) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 121.0(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 119.3(2) . . ?
C3 C4 C7 119.61(18) . . ?
C5 C4 C7 121.1(2) . . ?
O1 C7 C8 58.70(12) . . ?
O1 C7 C4 117.56(17) . . ?
C8 C7 C4 123.21(17) . . ?
O1 C7 H7 115.1 . . ?
C8 C7 H7 115.1 . . ?
C4 C7 H7 115.1 . . ?
O1 C8 C9 114.02(16) . . ?
O1 C8 C7 59.34(13) . . ?
C9 C8 C7 118.24(17) . . ?
O1 C8 C10 116.75(17) . . ?
C9 C8 C10 113.68(17) . . ?
C7 C8 C10 123.18(17) . . ?
N2 C10 C8 114.71(17) . . ?
N2 C10 H10A 108.6 . . ?
C8 C10 H10A 108.6 . . ?
N2 C10 H10B 108.6 . . ?
C8 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C18 N2 C10 121.41(18) . . ?
C18 N2 C11 121.01(19) . . ?
C10 N2 C11 117.32(19) . . ?
N2 C11 C12 116.17(19) . . ?
N2 C11 H11A 108.2 . . ?
C12 C11 H11A 108.2 . . ?
N2 C11 H11B 108.2 . . ?
C12 C11 H11B 108.2 . . ?
H11A C11 H11B 107.4 . . ?
C13 C12 C17 118.3(2) . . ?
C13 C12 C11 118.50(19) . . ?
C17 C12 C11 123.21(19) . . ?
C16 C17 C12 120.5(2) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C15 C16 C17 120.5(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C14 C15 C16 119.3(2) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C1 C6 C5 119.2(2) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C8 O1 C7 61.95(13) . . ?
C23 C18 N2 120.7(2) . . ?
C23 C18 C19 118.1(2) . . ?
N2 C18 C19 121.2(2) . . ?
C22 C23 C18 120.7(3) . . ?
C22 C23 H23 119.6 . . ?
C18 C23 H23 119.6 . . ?
C21 C22 C23 120.9(4) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C22 C21 C20 119.8(3) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C20 C19 121.0(3) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C18 C19 C20 119.4(3) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C14 C13 C12 121.4(2) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
N1 C9 C8 178.0(2) . . ?

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 -1.1(3) . . . . ?
Cl1 C1 C2 C3 177.78(17) . . . . ?
C1 C2 C3 C4 1.5(3) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C2 C3 C4 C7 -179.27(18) . . . . ?
C3 C4 C7 O1 176.94(17) . . . . ?
C5 C4 C7 O1 -1.1(3) . . . . ?
C3 C4 C7 C8 -114.1(2) . . . . ?
C5 C4 C7 C8 67.8(3) . . . . ?
C4 C7 C8 O1 -104.4(2) . . . . ?
O1 C7 C8 C9 102.6(2) . . . . ?
C4 C7 C8 C9 -1.8(3) . . . . ?
O1 C7 C8 C10 -103.7(2) . . . . ?
C4 C7 C8 C10 151.8(2) . . . . ?
O1 C8 C10 N2 -49.4(3) . . . . ?
C9 C8 C10 N2 174.65(18) . . . . ?
C7 C8 C10 N2 20.0(3) . . . . ?
C8 C10 N2 C18 -91.7(2) . . . . ?
C8 C10 N2 C11 94.1(2) . . . . ?
C18 N2 C11 C12 -84.6(3) . . . . ?
C10 N2 C11 C12 89.7(3) . . . . ?
N2 C11 C12 C13 174.7(2) . . . . ?
N2 C11 C12 C17 -5.5(3) . . . . ?
C13 C12 C17 C16 0.4(3) . . . . ?
C11 C12 C17 C16 -179.4(2) . . . . ?
C12 C17 C16 C15 -1.5(4) . . . . ?
C17 C16 C15 C14 1.6(4) . . . . ?
C2 C1 C6 C5 0.3(4) . . . . ?
Cl1 C1 C6 C5 -178.55(19) . . . . ?
C1 C6 C5 C4 0.0(4) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C7 C4 C5 C6 178.5(2) . . . . ?
C9 C8 O1 C7 -109.76(19) . . . . ?
C10 C8 O1 C7 114.4(2) . . . . ?
C4 C7 O1 C8 113.9(2) . . . . ?
C10 N2 C18 C23 16.8(3) . . . . ?
C11 N2 C18 C23 -169.1(2) . . . . ?
C10 N2 C18 C19 -163.0(2) . . . . ?
C11 N2 C18 C19 11.0(3) . . . . ?
N2 C18 C23 C22 179.2(2) . . . . ?
C19 C18 C23 C22 -1.0(3) . . . . ?
C18 C23 C22 C21 0.9(4) . . . . ?
C23 C22 C21 C20 0.0(5) . . . . ?
C22 C21 C20 C19 -0.8(6) . . . . ?
C23 C18 C19 C20 0.2(3) . . . . ?
N2 C18 C19 C20 180.0(2) . . . . ?
C21 C20 C19 C18 0.7(4) . . . . ?
C17 C12 C13 C14 0.7(3) . . . . ?
C11 C12 C13 C14 -179.5(2) . . . . ?
C16 C15 C14 C13 -0.6(4) . . . . ?
C12 C13 C14 C15 -0.5(4) . . . . ?

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-3



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tony240715_0m
_database_code_depnum_ccdc_archive 'CCDC 1444746'
_audit_update_record             
;
2015-12-30 deposited with the CCDC.
2016-01-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H19 Cl N2 O'
_chemical_formula_sum            'C23 H19 Cl N2 O'
_chemical_formula_weight         374.85

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.859(2)
_cell_length_b                   9.973(2)
_cell_length_c                   11.943(3)
_cell_angle_alpha                103.759(14)
_cell_angle_beta                 101.793(14)
_cell_angle_gamma                114.317(12)
_cell_volume                     976.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3630
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      27.08

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    0.210
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.947
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9114
_exptl_absorpt_correction_T_max  0.9474
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9717
_diffrn_reflns_av_unetI/netI     0.2030
_diffrn_reflns_av_R_equivalents  0.0910
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.403
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.932
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.932
_reflns_number_total             3288
_reflns_number_gt                1556
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3288
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3420
_refine_ls_R_factor_gt           0.0923
_refine_ls_wR_factor_ref         0.4100
_refine_ls_wR_factor_gt          0.2626
_refine_ls_goodness_of_fit_ref   1.295
_refine_ls_restrained_S_all      1.295
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.5593(3) 0.3236(3) 0.32773(19) 0.1131(10) Uani 1 1 d . . . . .
O1 O 1.1956(4) 0.8028(5) 0.8549(4) 0.0719(13) Uani 1 1 d . . . . .
N1 N 1.2153(7) 1.0716(7) 1.1050(6) 0.096(2) Uani 1 1 d . . . . .
N2 N 0.8961(4) 0.6643(5) 1.0108(4) 0.0526(13) Uani 1 1 d . . . . .
C1 C 0.7059(7) 0.4658(8) 0.4678(6) 0.0713(19) Uani 1 1 d . . . . .
C2 C 0.8184(8) 0.4386(9) 0.5278(6) 0.078(2) Uani 1 1 d . . . . .
H2 H 0.8182 0.3441 0.4946 0.094 Uiso 1 1 calc R U . . .
C3 C 0.9327(7) 0.5492(8) 0.6368(6) 0.0669(18) Uani 1 1 d . . . . .
H3 H 1.0079 0.5283 0.6782 0.080 Uiso 1 1 calc R U . . .
C4 C 0.9369(7) 0.6921(7) 0.6861(6) 0.0580(16) Uani 1 1 d . . . . .
C5 C 0.8197(8) 0.7187(8) 0.6228(6) 0.0709(18) Uani 1 1 d . . . . .
H5 H 0.8199 0.8134 0.6546 0.085 Uiso 1 1 calc R U . . .
C6 C 0.7045(8) 0.6055(9) 0.5142(7) 0.079(2) Uani 1 1 d . . . . .
H6 H 0.6266 0.6231 0.4725 0.095 Uiso 1 1 calc R U . . .
C7 C 1.0622(7) 0.8223(8) 0.8002(6) 0.0646(18) Uani 1 1 d . . . . .
H7 H 1.0888 0.9291 0.8021 0.078 Uiso 1 1 calc R U . . .
C8 C 1.0922(6) 0.8058(7) 0.9235(5) 0.0542(16) Uani 1 1 d . . . . .
C9 C 1.1618(7) 0.9544(7) 1.0271(7) 0.0663(17) Uani 1 1 d . . . . .
C10 C 1.0042(6) 0.6563(6) 0.9473(5) 0.0474(14) Uani 1 1 d . . . . .
H10A H 0.9453 0.5684 0.8696 0.057 Uiso 1 1 calc R U . . .
H10B H 1.0805 0.6363 0.9958 0.057 Uiso 1 1 calc R U . . .
C11 C 0.9442(6) 0.7214(6) 1.1397(5) 0.0534(16) Uani 1 1 d . . . . .
C12 C 0.8406(7) 0.7328(8) 1.2018(6) 0.0687(18) Uani 1 1 d . . . . .
H12 H 0.7356 0.6972 1.1571 0.082 Uiso 1 1 calc R U . . .
C13 C 0.8924(9) 0.7956(9) 1.3272(7) 0.086(2) Uani 1 1 d . . . . .
H13 H 0.8208 0.8003 1.3659 0.103 Uiso 1 1 calc R U . . .
C14 C 1.0473(10) 0.8521(10) 1.3979(7) 0.087(2) Uani 1 1 d . . . . .
H14 H 1.0817 0.8966 1.4830 0.105 Uiso 1 1 calc R U . . .
C15 C 1.1477(7) 0.8401(8) 1.3381(6) 0.077(2) Uani 1 1 d . . . . .
H15 H 1.2521 0.8749 1.3840 0.092 Uiso 1 1 calc R U . . .
C16 C 1.1006(6) 0.7784(7) 1.2127(5) 0.0557(16) Uani 1 1 d . . . . .
H16 H 1.1739 0.7745 1.1756 0.067 Uiso 1 1 calc R U . . .
C17 C 0.7340(6) 0.6051(7) 0.9303(5) 0.0566(16) Uani 1 1 d . . . . .
H17A H 0.7382 0.6427 0.8626 0.068 Uiso 1 1 calc R U . . .
H17B H 0.6811 0.6479 0.9760 0.068 Uiso 1 1 calc R U . . .
C18 C 0.6368(5) 0.4254(7) 0.8790(6) 0.0540(16) Uani 1 1 d . . . . .
C19 C 0.6087(7) 0.3401(9) 0.9555(7) 0.0702(19) Uani 1 1 d . . . . .
H19 H 0.6501 0.3918 1.0401 0.084 Uiso 1 1 calc R U . . .
C20 C 0.5190(8) 0.1783(11) 0.9055(10) 0.090(3) Uani 1 1 d . . . . .
H20 H 0.4980 0.1220 0.9575 0.108 Uiso 1 1 calc R U . . .
C21 C 0.4602(8) 0.0983(10) 0.7821(12) 0.103(3) Uani 1 1 d . . . . .
H21 H 0.4005 -0.0112 0.7501 0.123 Uiso 1 1 calc R U . . .
C22 C 0.4906(8) 0.1827(11) 0.7048(9) 0.097(3) Uani 1 1 d . . . . .
H22 H 0.4520 0.1294 0.6204 0.116 Uiso 1 1 calc R U . . .
C23 C 0.5784(7) 0.3464(8) 0.7527(7) 0.0700(19) Uani 1 1 d . . . . .
H23 H 0.5980 0.4027 0.7007 0.084 Uiso 1 1 calc R U . . .


_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 C1 1.759(7) . ?
O1 C8 1.438(6) . ?
O1 C7 1.453(7) . ?
N1 C9 1.133(7) . ?
N2 C11 1.408(7) . ?
N2 C10 1.445(5) . ?
N2 C17 1.467(7) . ?
C1 C2 1.354(9) . ?
C1 C6 1.378(10) . ?
C2 C3 1.370(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.402(8) . ?
C4 C7 1.489(9) . ?
C5 C6 1.376(9) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.503(9) . ?
C7 H7 0.9800 . ?
C8 C9 1.463(8) . ?
C8 C10 1.514(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.398(8) . ?
C11 C12 1.403(6) . ?
C12 C13 1.370(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.361(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(8) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.526(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.383(9) . ?
C18 C23 1.391(8) . ?
C19 C20 1.376(10) . ?
C19 H19 0.9300 . ?
C20 C21 1.363(11) . ?
C20 H20 0.9300 . ?
C21 C22 1.387(13) . ?
C21 H21 0.9300 . ?
C22 C23 1.390(11) . ?
C22 H22 0.9300 . ?
C23 H23 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
C8 O1 C7 62.7(3) . . ?
C11 N2 C10 121.8(4) . . ?
C11 N2 C17 123.5(4) . . ?
C10 N2 C17 114.7(4) . . ?
C2 C1 C6 120.9(6) . . ?
C2 C1 Cl1 120.4(5) . . ?
C6 C1 Cl1 118.7(5) . . ?
C1 C2 C3 120.5(6) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 120.5(5) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 118.3(6) . . ?
C3 C4 C7 124.0(5) . . ?
C5 C4 C7 117.7(5) . . ?
C6 C5 C4 120.5(6) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 119.3(6) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
O1 C7 C4 117.1(5) . . ?
O1 C7 C8 58.2(3) . . ?
C4 C7 C8 123.3(5) . . ?
O1 C7 H7 115.3 . . ?
C4 C7 H7 115.3 . . ?
C8 C7 H7 115.3 . . ?
O1 C8 C9 112.9(4) . . ?
O1 C8 C7 59.2(3) . . ?
C9 C8 C7 114.0(5) . . ?
O1 C8 C10 115.9(4) . . ?
C9 C8 C10 116.4(5) . . ?
C7 C8 C10 125.0(5) . . ?
N1 C9 C8 178.0(8) . . ?
N2 C10 C8 113.0(4) . . ?
N2 C10 H10A 109.0 . . ?
C8 C10 H10A 109.0 . . ?
N2 C10 H10B 109.0 . . ?
C8 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C16 C11 C12 116.4(5) . . ?
C16 C11 N2 121.5(4) . . ?
C12 C11 N2 122.0(5) . . ?
C13 C12 C11 120.8(6) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 122.1(5) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C15 C14 C13 117.2(6) . . ?
C15 C14 H14 121.4 . . ?
C13 C14 H14 121.4 . . ?
C14 C15 C16 122.4(6) . . ?
C14 C15 H15 118.8 . . ?
C16 C15 H15 118.8 . . ?
C15 C16 C11 121.0(5) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
N2 C17 C18 113.2(4) . . ?
N2 C17 H17A 108.9 . . ?
C18 C17 H17A 108.9 . . ?
N2 C17 H17B 108.9 . . ?
C18 C17 H17B 108.9 . . ?
H17A C17 H17B 107.8 . . ?
C19 C18 C23 119.7(7) . . ?
C19 C18 C17 121.4(6) . . ?
C23 C18 C17 118.9(6) . . ?
C20 C19 C18 119.6(8) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C21 C20 C19 121.8(9) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C20 C21 C22 119.0(8) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C21 C22 C23 120.5(9) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 119.5(8) . . ?
C22 C23 H23 120.3 . . ?
C18 C23 H23 120.3 . . ?

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
C6 C1 C2 C3 0.7(10) . . . . ?
Cl1 C1 C2 C3 -180.0(5) . . . . ?
C1 C2 C3 C4 -1.5(10) . . . . ?
C2 C3 C4 C5 1.3(9) . . . . ?
C2 C3 C4 C7 -176.3(6) . . . . ?
C3 C4 C5 C6 -0.5(9) . . . . ?
C7 C4 C5 C6 177.3(6) . . . . ?
C4 C5 C6 C1 -0.3(10) . . . . ?
C2 C1 C6 C5 0.2(10) . . . . ?
Cl1 C1 C6 C5 -179.2(5) . . . . ?
C8 O1 C7 C4 -114.1(6) . . . . ?
C3 C4 C7 O1 6.6(9) . . . . ?
C5 C4 C7 O1 -171.0(5) . . . . ?
C3 C4 C7 C8 -61.5(7) . . . . ?
C5 C4 C7 C8 120.8(6) . . . . ?
C7 O1 C8 C9 -105.2(6) . . . . ?
C7 O1 C8 C10 117.0(5) . . . . ?
C4 C7 C8 O1 103.6(5) . . . . ?
O1 C7 C8 C9 103.3(5) . . . . ?
C4 C7 C8 C9 -153.2(5) . . . . ?
O1 C7 C8 C10 -101.7(5) . . . . ?
C4 C7 C8 C10 1.9(7) . . . . ?
C11 N2 C10 C8 -89.5(6) . . . . ?
C17 N2 C10 C8 91.9(5) . . . . ?
O1 C8 C10 N2 -176.8(4) . . . . ?
C9 C8 C10 N2 46.9(6) . . . . ?
C7 C8 C10 N2 -107.6(5) . . . . ?
C10 N2 C11 C16 2.3(8) . . . . ?
C17 N2 C11 C16 -179.2(5) . . . . ?
C10 N2 C11 C12 178.5(5) . . . . ?
C17 N2 C11 C12 -3.0(9) . . . . ?
C16 C11 C12 C13 -0.5(9) . . . . ?
N2 C11 C12 C13 -176.9(6) . . . . ?
C11 C12 C13 C14 0.9(11) . . . . ?
C12 C13 C14 C15 -1.4(11) . . . . ?
C13 C14 C15 C16 1.6(11) . . . . ?
C14 C15 C16 C11 -1.3(10) . . . . ?
C12 C11 C16 C15 0.7(9) . . . . ?
N2 C11 C16 C15 177.1(6) . . . . ?
C11 N2 C17 C18 -99.7(6) . . . . ?
C10 N2 C17 C18 78.9(6) . . . . ?
N2 C17 C18 C19 60.0(6) . . . . ?
N2 C17 C18 C23 -118.8(5) . . . . ?
C23 C18 C19 C20 -2.0(7) . . . . ?
C17 C18 C19 C20 179.3(4) . . . . ?
C18 C19 C20 C21 1.9(8) . . . . ?
C19 C20 C21 C22 -0.5(9) . . . . ?
C20 C21 C22 C23 -0.6(9) . . . . ?
C21 C22 C23 C18 0.5(8) . . . . ?
C19 C18 C23 C22 0.8(7) . . . . ?
C17 C18 C23 C22 179.6(4) . . . . ?

_refine_diff_density_max         0.509
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.126

_shelxl_version_number           2013-3



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane-petroleum ether'
