# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_k2
_database_code_depnum_ccdc_archive 'CCDC 1028899'
_audit_update_record             
;
2014-10-13 deposited with the CCDC.
2015-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H28 Cl F2 N3 O2'
_chemical_formula_sum            'C31 H28 Cl F2 N3 O2'
_chemical_formula_weight         548.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.97300(13)
_cell_length_b                   16.1952(3)
_cell_length_c                   14.09653(16)
_cell_angle_alpha                90
_cell_angle_beta                 93.4721(10)
_cell_angle_gamma                90
_cell_volume                     2728.37(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             1144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.637
_shelx_estimated_absorpt_T_min   0.639
_shelx_estimated_absorpt_T_max   0.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.721
_exptl_absorpt_correction_T_max  0.922
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova (Cu) X-ray Source'
_diffrn_measurement_method       'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.6501
_diffrn_reflns_number            38016
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.162
_diffrn_reflns_theta_max         67.484
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4913
_reflns_number_gt                4248
_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       CrysAlisPro
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    XP
_computing_publication_material  XP

_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)+(0.0465P)²+1.2590P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4913
_refine_ls_number_parameters     356
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0963
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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_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
O1 O 0.61483(8) -0.06591(7) 0.54476(7) 0.0224(2) Uani 1 1 d . . . . .
F2 F 0.65024(8) -0.13139(7) -0.21029(7) 0.0372(3) Uani 1 1 d . . . . .
O3 O 0.93570(9) -0.19107(8) 0.33413(8) 0.0264(3) Uani 1 1 d . . . . .
F4 F 0.69522(11) -0.45475(7) 0.73310(8) 0.0477(3) Uani 1 1 d . . . . .
N5 N 0.59674(11) 0.00995(9) 0.40702(9) 0.0214(3) Uani 1 1 d . . . . .
H5 H 0.5306(19) 0.0297(13) 0.4172(14) 0.038(6) Uiso 1 1 d . . . . .
N6 N 0.85880(10) -0.04675(9) 0.49339(9) 0.0217(3) Uani 1 1 d . . . . .
N7 N 0.59328(10) -0.17949(8) 0.32983(9) 0.0195(3) Uani 1 1 d . . . . .
C8 C 0.83416(12) -0.18648(10) 0.33195(11) 0.0200(3) Uani 1 1 d . . . . .
C9 C 0.76477(12) -0.19598(10) 0.24086(11) 0.0199(3) Uani 1 1 d . . . . .
C10 C 0.65900(12) -0.21049(10) 0.41318(10) 0.0199(3) Uani 1 1 d . . . . .
H10A H 0.6705 -0.2707 0.4069 0.024 Uiso 1 1 calc R U . . .
H10B H 0.6181 -0.2005 0.4711 0.024 Uiso 1 1 calc R U . . .
C11 C 0.81978(13) -0.18714(10) 0.16111(11) 0.0216(3) Uani 1 1 d . . . . .
H11A H 0.8989 -0.1837 0.1703 0.026 Uiso 1 1 calc R U . . .
C12 C 0.77555(13) -0.18197(10) 0.06213(11) 0.0215(3) Uani 1 1 d . . . . .
C13 C 0.83534(13) -0.13321(10) 0.00072(11) 0.0240(3) Uani 1 1 d . . . . .
H13A H 0.9058 -0.1112 0.0228 0.029 Uiso 1 1 calc R U . . .
C14 C 0.63332(13) 0.07536(11) 0.25089(12) 0.0258(4) Uani 1 1 d . . . . .
H14A H 0.5638 0.1037 0.2444 0.031 Uiso 1 1 calc R U . . .
C15 C 0.71278(14) 0.08329(11) 0.18325(12) 0.0272(4) Uani 1 1 d . . . . .
H15A H 0.6967 0.1160 0.1282 0.033 Uiso 1 1 calc R U . . .
C16 C 0.65968(12) 0.02455(10) 0.32801(11) 0.0206(3) Uani 1 1 d . . . . .
C17 C 0.76060(12) -0.01841(10) 0.33843(11) 0.0198(3) Uani 1 1 d . . . . .
C18 C 0.67668(13) -0.21901(11) 0.02559(11) 0.0263(4) Uani 1 1 d . . . . .
H18A H 0.6371 -0.2554 0.0645 0.032 Uiso 1 1 calc R U . . .
C19 C 0.86684(13) -0.10925(11) 0.56827(11) 0.0241(3) Uani 1 1 d . . . . .
H19A H 0.8088 -0.1007 0.6144 0.029 Uiso 1 1 calc R U . . .
H19B H 0.9415 -0.1083 0.6025 0.029 Uiso 1 1 calc R U . . .
C20 C 0.64887(12) -0.04349(10) 0.46834(11) 0.0196(3) Uani 1 1 d . . . . .
C21 C 0.84780(12) -0.19052(10) 0.51387(11) 0.0221(3) Uani 1 1 d . . . . .
H21A H 0.9221 -0.2080 0.4920 0.026 Uiso 1 1 calc R U . . .
C22 C 0.84154(12) -0.00699(10) 0.27394(11) 0.0213(3) Uani 1 1 d . . . . .
H22A H 0.9127 -0.0328 0.2824 0.026 Uiso 1 1 calc R U . . .
C23 C 0.64037(12) -0.20940(10) 0.24299(11) 0.0216(3) Uani 1 1 d . . . . .
H23A H 0.6025 -0.1810 0.1878 0.026 Uiso 1 1 calc R U . . .
H23B H 0.6245 -0.2692 0.2363 0.026 Uiso 1 1 calc R U . . .
C24 C 0.69375(14) -0.15047(11) -0.12159(11) 0.0269(4) Uani 1 1 d . . . . .
C25 C 0.81499(13) 0.04370(10) 0.19600(11) 0.0242(3) Uani 1 1 d . . . . .
C26 C 0.77282(12) -0.16653(10) 0.42218(10) 0.0194(3) Uani 1 1 d . . . . .
C27 C 0.76269(12) -0.06884(10) 0.42925(10) 0.0194(3) Uani 1 1 d . . . . .
C28 C 0.47584(12) -0.20717(10) 0.32961(11) 0.0223(3) Uani 1 1 d . . . . .
H28A H 0.4746 -0.2670 0.3436 0.027 Uiso 1 1 calc R U . . .
H28B H 0.4399 -0.1990 0.2652 0.027 Uiso 1 1 calc R U . . .
C29 C 0.40804(13) -0.16220(12) 0.40094(12) 0.0287(4) Uani 1 1 d . . . . .
H29A H 0.3313 -0.1835 0.3972 0.043 Uiso 1 1 calc R U . . .
H29B H 0.4070 -0.1030 0.3866 0.043 Uiso 1 1 calc R U . . .
H29C H 0.4420 -0.1711 0.4651 0.043 Uiso 1 1 calc R U . . .
C30 C 0.81980(16) -0.40416(12) 0.62368(12) 0.0332(4) Uani 1 1 d . . . . .
H30A H 0.8549 -0.4567 0.6215 0.040 Uiso 1 1 calc R U . . .
C31 C 0.71618(14) -0.25093(11) 0.63123(11) 0.0271(4) Uani 1 1 d . . . . .
H31A H 0.6804 -0.1987 0.6342 0.033 Uiso 1 1 calc R U . . .
C32 C 0.73154(16) -0.39104(12) 0.67964(12) 0.0335(4) Uani 1 1 d . . . . .
C33 C 0.79482(13) -0.11614(11) -0.09108(11) 0.0256(4) Uani 1 1 d . . . . .
H33A H 0.8353 -0.0819 -0.1317 0.031 Uiso 1 1 calc R U . . .
C34 C 0.63556(14) -0.20327(12) -0.06706(12) 0.0302(4) Uani 1 1 d . . . . .
H34A H 0.5685 -0.2286 -0.0919 0.036 Uiso 1 1 calc R U . . .
C35 C 0.67902(15) -0.31593(12) 0.68515(12) 0.0321(4) Uani 1 1 d . . . . .
H35A H 0.6186 -0.3087 0.7250 0.039 Uiso 1 1 calc R U . . .
C36 C 0.80541(13) -0.26092(11) 0.57256(10) 0.0235(3) Uani 1 1 d . . . . .
C37 C 0.85859(13) 0.03822(11) 0.52909(12) 0.0271(4) Uani 1 1 d . . . . .
H37A H 0.8530 0.0767 0.4754 0.041 Uiso 1 1 calc R U . . .
H37B H 0.9281 0.0487 0.5675 0.041 Uiso 1 1 calc R U . . .
H37C H 0.7945 0.0461 0.5683 0.041 Uiso 1 1 calc R U . . .
C38 C 0.85629(14) -0.33828(11) 0.57034(11) 0.0269(4) Uani 1 1 d . . . . .
H38A H 0.9174 -0.3462 0.5314 0.032 Uiso 1 1 calc R U . . .
Cl1 Cl 0.91452(3) 0.05776(3) 0.11171(3) 0.03092(12) 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
O1 C20 1.2294(19) . ?
F2 C24 1.3606(18) . ?
O3 C8 1.2165(18) . ?
F4 C32 1.364(2) . ?
N5 C20 1.349(2) . ?
N5 C16 1.402(2) . ?
N5 H5 0.87(2) . ?
N6 C19 1.461(2) . ?
N6 C27 1.4642(19) . ?
N6 C37 1.465(2) . ?
N7 C23 1.4611(19) . ?
N7 C10 1.4627(19) . ?
N7 C28 1.4758(19) . ?
C8 C9 1.495(2) . ?
C8 C26 1.541(2) . ?
C9 C11 1.345(2) . ?
C9 C23 1.507(2) . ?
C10 C26 1.536(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.465(2) . ?
C11 H11A 0.9500 . ?
C12 C18 1.397(2) . ?
C12 C13 1.400(2) . ?
C13 C33 1.382(2) . ?
C13 H13A 0.9500 . ?
C14 C16 1.385(2) . ?
C14 C15 1.393(2) . ?
C14 H14A 0.9500 . ?
C15 C25 1.384(2) . ?
C15 H15A 0.9500 . ?
C16 C17 1.394(2) . ?
C17 C22 1.381(2) . ?
C17 C27 1.517(2) . ?
C18 C34 1.391(2) . ?
C18 H18A 0.9500 . ?
C19 C21 1.533(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C27 1.5557(19) . ?
C21 C36 1.514(2) . ?
C21 C26 1.577(2) . ?
C21 H21A 1.0000 . ?
C22 C25 1.393(2) . ?
C22 H22A 0.9500 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C34 1.368(3) . ?
C24 C33 1.377(2) . ?
C25 Cl1 1.7479(16) . ?
C26 C27 1.590(2) . ?
C28 C29 1.516(2) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C32 1.373(3) . ?
C30 C38 1.391(3) . ?
C30 H30A 0.9500 . ?
C31 C35 1.387(2) . ?
C31 C36 1.399(2) . ?
C31 H31A 0.9500 . ?
C32 C35 1.374(3) . ?
C33 H33A 0.9500 . ?
C34 H34A 0.9500 . ?
C35 H35A 0.9500 . ?
C36 C38 1.394(2) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 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
C20 N5 C16 111.53(13) . . ?
C20 N5 H5 121.3(14) . . ?
C16 N5 H5 127.2(14) . . ?
C19 N6 C27 106.97(12) . . ?
C19 N6 C37 113.81(13) . . ?
C27 N6 C37 115.08(12) . . ?
C23 N7 C10 110.06(12) . . ?
C23 N7 C28 108.27(12) . . ?
C10 N7 C28 111.32(12) . . ?
O3 C8 C9 121.20(13) . . ?
O3 C8 C26 121.16(13) . . ?
C9 C8 C26 117.57(12) . . ?
C11 C9 C8 115.62(14) . . ?
C11 C9 C23 124.52(14) . . ?
C8 C9 C23 119.76(13) . . ?
N7 C10 C26 109.80(12) . . ?
N7 C10 H10A 109.7 . . ?
C26 C10 H10A 109.7 . . ?
N7 C10 H10B 109.7 . . ?
C26 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C9 C11 C12 129.46(14) . . ?
C9 C11 H11A 115.3 . . ?
C12 C11 H11A 115.3 . . ?
C18 C12 C13 117.88(15) . . ?
C18 C12 C11 125.17(14) . . ?
C13 C12 C11 116.89(14) . . ?
C33 C13 C12 121.87(15) . . ?
C33 C13 H13A 119.1 . . ?
C12 C13 H13A 119.1 . . ?
C16 C14 C15 117.36(15) . . ?
C16 C14 H14A 121.3 . . ?
C15 C14 H14A 121.3 . . ?
C25 C15 C14 120.24(15) . . ?
C25 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C14 C16 C17 122.29(14) . . ?
C14 C16 N5 128.02(14) . . ?
C17 C16 N5 109.65(13) . . ?
C22 C17 C16 120.14(14) . . ?
C22 C17 C27 130.63(14) . . ?
C16 C17 C27 109.11(13) . . ?
C34 C18 C12 120.74(15) . . ?
C34 C18 H18A 119.6 . . ?
C12 C18 H18A 119.6 . . ?
N6 C19 C21 103.41(12) . . ?
N6 C19 H19A 111.1 . . ?
C21 C19 H19A 111.1 . . ?
N6 C19 H19B 111.1 . . ?
C21 C19 H19B 111.1 . . ?
H19A C19 H19B 109.0 . . ?
O1 C20 N5 125.85(14) . . ?
O1 C20 C27 125.20(14) . . ?
N5 C20 C27 108.87(13) . . ?
C36 C21 C19 114.68(13) . . ?
C36 C21 C26 116.13(13) . . ?
C19 C21 C26 104.98(13) . . ?
C36 C21 H21A 106.8 . . ?
C19 C21 H21A 106.8 . . ?
C26 C21 H21A 106.8 . . ?
C17 C22 C25 117.55(14) . . ?
C17 C22 H22A 121.2 . . ?
C25 C22 H22A 121.2 . . ?
N7 C23 C9 113.63(12) . . ?
N7 C23 H23A 108.8 . . ?
C9 C23 H23A 108.8 . . ?
N7 C23 H23B 108.8 . . ?
C9 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
F2 C24 C34 118.59(15) . . ?
F2 C24 C33 118.40(15) . . ?
C34 C24 C33 123.01(15) . . ?
C15 C25 C22 122.24(14) . . ?
C15 C25 Cl1 119.03(13) . . ?
C22 C25 Cl1 118.72(12) . . ?
C10 C26 C8 107.42(12) . . ?
C10 C26 C21 114.31(12) . . ?
C8 C26 C21 110.41(12) . . ?
C10 C26 C27 113.31(12) . . ?
C8 C26 C27 107.60(12) . . ?
C21 C26 C27 103.63(12) . . ?
N6 C27 C17 111.20(12) . . ?
N6 C27 C20 112.91(12) . . ?
C17 C27 C20 100.76(12) . . ?
N6 C27 C26 102.81(12) . . ?
C17 C27 C26 118.69(12) . . ?
C20 C27 C26 110.88(12) . . ?
N7 C28 C29 113.64(13) . . ?
N7 C28 H28A 108.8 . . ?
C29 C28 H28A 108.8 . . ?
N7 C28 H28B 108.8 . . ?
C29 C28 H28B 108.8 . . ?
H28A C28 H28B 107.7 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C32 C30 C38 118.03(17) . . ?
C32 C30 H30A 121.0 . . ?
C38 C30 H30A 121.0 . . ?
C35 C31 C36 121.17(17) . . ?
C35 C31 H31A 119.4 . . ?
C36 C31 H31A 119.4 . . ?
F4 C32 C30 118.85(17) . . ?
F4 C32 C35 118.44(17) . . ?
C30 C32 C35 122.70(17) . . ?
C24 C33 C13 117.63(15) . . ?
C24 C33 H33A 121.2 . . ?
C13 C33 H33A 121.2 . . ?
C24 C34 C18 118.59(15) . . ?
C24 C34 H34A 120.7 . . ?
C18 C34 H34A 120.7 . . ?
C32 C35 C31 118.55(16) . . ?
C32 C35 H35A 120.7 . . ?
C31 C35 H35A 120.7 . . ?
C38 C36 C31 117.87(15) . . ?
C38 C36 C21 120.19(14) . . ?
C31 C36 C21 121.94(15) . . ?
N6 C37 H37A 109.5 . . ?
N6 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
N6 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C30 C38 C36 121.68(16) . . ?
C30 C38 H38A 119.2 . . ?
C36 C38 H38A 119.2 . . ?

_refine_diff_density_max         0.417
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.044




####################################################################### 
# 
# 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_k3
_database_code_depnum_ccdc_archive 'CCDC 1037561'
_audit_update_record             
;
2014-12-04 deposited with the CCDC.
2015-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H17 Cl4 N O'
_chemical_formula_sum            'C21 H17 Cl4 N O'
_chemical_formula_weight         441.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   21.5694(4)
_cell_length_b                   7.03970(10)
_cell_length_c                   25.8262(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.3250(10)
_cell_angle_gamma                90.00
_cell_volume                     3921.44(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1808
_exptl_absorpt_coefficient_mu    5.577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3734
_exptl_absorpt_correction_T_max  0.5090
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  mirror
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.6501
_diffrn_reflns_number            21368
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.42
_diffrn_reflns_theta_max         67.48
_reflns_number_total             3540
_reflns_number_gt                3137
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrysAlisPro
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    XP
_computing_publication_material  XP

_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)+(0.0400P)²+4.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3540
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0754
_refine_ls_wR_factor_gt          0.0706
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001

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 -0.19241(2) 1.15148(6) 0.445104(16) 0.02587(12) Uani 1 1 d . . .
Cl2 Cl -0.19335(2) 0.69887(7) 0.611898(15) 0.02816(12) Uani 1 1 d . . .
Cl3 Cl -0.07418(2) 0.83938(6) 0.105156(16) 0.03028(12) Uani 1 1 d . . .
Cl4 Cl 0.02410(2) 0.18471(6) 0.039405(15) 0.02751(12) Uani 1 1 d . . .
O1 O -0.08114(6) 0.93036(17) 0.29385(5) 0.0283(3) Uani 1 1 d . . .
N1 N -0.18277(6) 0.4615(2) 0.29696(5) 0.0189(3) Uani 1 1 d . . .
C2 C -0.16005(8) 0.5105(2) 0.34891(6) 0.0182(3) Uani 1 1 d . . .
H2A H -0.1292 0.4152 0.3604 0.022 Uiso 1 1 calc R . .
H2B H -0.1949 0.5089 0.3736 0.022 Uiso 1 1 calc R . .
C3 C -0.13079(7) 0.7046(2) 0.34842(6) 0.0171(3) Uani 1 1 d . . .
C4 C -0.10184(8) 0.7699(2) 0.29878(6) 0.0193(4) Uani 1 1 d . . .
C5 C -0.09637(7) 0.6252(2) 0.25649(6) 0.0177(3) Uani 1 1 d . . .
C6 C -0.12880(8) 0.4375(2) 0.26347(6) 0.0198(4) Uani 1 1 d . . .
H6A H -0.1422 0.3879 0.2293 0.024 Uiso 1 1 calc R . .
H6B H -0.0998 0.3445 0.2792 0.024 Uiso 1 1 calc R . .
C7 C -0.21913(9) 0.2841(3) 0.29763(7) 0.0251(4) Uani 1 1 d . . .
H7A H -0.1948 0.1843 0.3156 0.030 Uiso 1 1 calc R . .
H7B H -0.2264 0.2416 0.2616 0.030 Uiso 1 1 calc R . .
C8 C -0.28098(9) 0.3067(3) 0.32440(7) 0.0299(4) Uani 1 1 d . . .
H8A H -0.3031 0.1851 0.3239 0.045 Uiso 1 1 calc R . .
H8B H -0.3057 0.4029 0.3063 0.045 Uiso 1 1 calc R . .
H8C H -0.2741 0.3466 0.3603 0.045 Uiso 1 1 calc R . .
C9 C -0.12908(8) 0.8253(2) 0.38856(6) 0.0189(3) Uani 1 1 d . . .
H9A H -0.1133 0.9486 0.3816 0.023 Uiso 1 1 calc R . .
C10 C -0.14875(7) 0.7891(2) 0.44201(6) 0.0173(3) Uani 1 1 d . . .
C11 C -0.17475(8) 0.9327(2) 0.47268(6) 0.0185(3) Uani 1 1 d . . .
C12 C -0.18855(8) 0.9074(2) 0.52447(6) 0.0193(3) Uani 1 1 d . . .
H12A H -0.2053 1.0084 0.5444 0.023 Uiso 1 1 calc R . .
C13 C -0.17733(8) 0.7321(3) 0.54654(6) 0.0199(4) Uani 1 1 d . . .
C14 C -0.15357(8) 0.5829(2) 0.51783(6) 0.0203(4) Uani 1 1 d . . .
H14A H -0.1474 0.4617 0.5332 0.024 Uiso 1 1 calc R . .
C15 C -0.13903(7) 0.6135(2) 0.46634(6) 0.0185(3) Uani 1 1 d . . .
H15A H -0.1219 0.5121 0.4468 0.022 Uiso 1 1 calc R . .
C16 C -0.06392(8) 0.6745(2) 0.21450(6) 0.0192(3) Uani 1 1 d . . .
H16A H -0.0506 0.8029 0.2125 0.023 Uiso 1 1 calc R . .
C17 C -0.04690(8) 0.5501(2) 0.17118(6) 0.0191(3) Uani 1 1 d . . .
C18 C -0.04528(8) 0.6158(2) 0.11995(6) 0.0194(3) Uani 1 1 d . . .
C19 C -0.02324(8) 0.5059(2) 0.07955(6) 0.0206(4) Uani 1 1 d . . .
H19A H -0.0221 0.5547 0.0453 0.025 Uiso 1 1 calc R . .
C20 C -0.00299(8) 0.3240(2) 0.09020(6) 0.0201(4) Uani 1 1 d . . .
C21 C -0.00435(8) 0.2499(3) 0.13986(6) 0.0224(4) Uani 1 1 d . . .
H21A H 0.0097 0.1244 0.1467 0.027 Uiso 1 1 calc R . .
C22 C -0.02666(8) 0.3633(3) 0.17927(6) 0.0222(4) Uani 1 1 d . . .
H22A H -0.0283 0.3124 0.2133 0.027 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 C11 1.7382(17) . ?
Cl2 C13 1.7407(16) . ?
Cl3 C18 1.7344(18) . ?
Cl4 C20 1.7414(16) . ?
O1 C4 1.222(2) . ?
N1 C6 1.464(2) . ?
N1 C2 1.467(2) . ?
N1 C7 1.475(2) . ?
C2 C3 1.505(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C9 1.341(2) . ?
C3 C4 1.501(2) . ?
C4 C5 1.498(2) . ?
C5 C16 1.340(2) . ?
C5 C6 1.507(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.514(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.469(2) . ?
C9 H9A 0.9500 . ?
C10 C15 1.402(2) . ?
C10 C11 1.403(2) . ?
C11 C12 1.383(2) . ?
C12 C13 1.380(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.386(2) . ?
C14 C15 1.385(2) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 C17 1.469(2) . ?
C16 H16A 0.9500 . ?
C17 C22 1.400(2) . ?
C17 C18 1.402(2) . ?
C18 C19 1.385(2) . ?
C19 C20 1.380(2) . ?
C19 H19A 0.9500 . ?
C20 C21 1.385(2) . ?
C21 C22 1.382(2) . ?
C21 H21A 0.9500 . ?
C22 H22A 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
C6 N1 C2 107.74(13) . . ?
C6 N1 C7 109.52(13) . . ?
C2 N1 C7 111.31(13) . . ?
N1 C2 C3 110.12(13) . . ?
N1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
N1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.2 . . ?
C9 C3 C4 117.15(15) . . ?
C9 C3 C2 125.37(15) . . ?
C4 C3 C2 117.48(14) . . ?
O1 C4 C3 121.75(15) . . ?
O1 C4 C5 121.47(15) . . ?
C3 C4 C5 116.70(14) . . ?
C16 C5 C4 117.26(15) . . ?
C16 C5 C6 124.68(15) . . ?
C4 C5 C6 118.04(14) . . ?
N1 C6 C5 109.94(13) . . ?
N1 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N1 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N1 C7 C8 112.74(15) . . ?
N1 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C9 C10 127.58(16) . . ?
C3 C9 H9A 116.2 . . ?
C10 C9 H9A 116.2 . . ?
C15 C10 C11 116.19(15) . . ?
C15 C10 C9 122.06(15) . . ?
C11 C10 C9 121.62(15) . . ?
C12 C11 C10 122.83(16) . . ?
C12 C11 Cl1 117.53(13) . . ?
C10 C11 Cl1 119.62(13) . . ?
C13 C12 C11 118.44(15) . . ?
C13 C12 H12A 120.8 . . ?
C11 C12 H12A 120.8 . . ?
C12 C13 C14 121.42(15) . . ?
C12 C13 Cl2 119.04(13) . . ?
C14 C13 Cl2 119.54(13) . . ?
C15 C14 C13 118.84(16) . . ?
C15 C14 H14A 120.6 . . ?
C13 C14 H14A 120.6 . . ?
C14 C15 C10 122.23(15) . . ?
C14 C15 H15A 118.9 . . ?
C10 C15 H15A 118.9 . . ?
C5 C16 C17 126.60(16) . . ?
C5 C16 H16A 116.7 . . ?
C17 C16 H16A 116.7 . . ?
C22 C17 C18 116.19(15) . . ?
C22 C17 C16 121.67(15) . . ?
C18 C17 C16 121.96(16) . . ?
C19 C18 C17 122.46(16) . . ?
C19 C18 Cl3 117.73(13) . . ?
C17 C18 Cl3 119.78(13) . . ?
C20 C19 C18 118.54(15) . . ?
C20 C19 H19A 120.7 . . ?
C18 C19 H19A 120.7 . . ?
C19 C20 C21 121.70(15) . . ?
C19 C20 Cl4 118.66(13) . . ?
C21 C20 Cl4 119.64(14) . . ?
C22 C21 C20 118.29(16) . . ?
C22 C21 H21A 120.9 . . ?
C20 C21 H21A 120.9 . . ?
C21 C22 C17 122.80(16) . . ?
C21 C22 H22A 118.6 . . ?
C17 C22 H22A 118.6 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        67.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.048
