# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_f:\zsy\done\olex2_~1\401-310k
_database_code_depnum_ccdc_archive 'CCDC 1400882'
_audit_update_record             
;
2015-05-14 deposited with the CCDC.
2016-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 N, C2 Cl3 O2'
_chemical_formula_sum            'C24 H24 Cl4.49 N1.50 O3'
_chemical_formula_weight         540.49

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           orthorhombic
_symmetry_space_group_name_H-M   'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   28.2608(3)
_cell_length_b                   17.9257(3)
_cell_length_c                   10.23480(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5184.89(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    310(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2230
_exptl_absorpt_coefficient_mu    4.835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.164
_exptl_absorpt_correction_T_max  0.299
_exptl_absorpt_process_details   
; 
_exptl_special_details 
;



_diffrn_ambient_temperature      310(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14382
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.98
_diffrn_reflns_theta_max         66.60
_reflns_number_total             4693
_reflns_number_gt                3648
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.1176P)²+2.9745P] 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         4693
_refine_ls_number_parameters     344
_refine_ls_number_restraints     352
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0743
_refine_ls_wR_factor_ref         0.2332
_refine_ls_wR_factor_gt          0.2093
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.130
_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
Cl5 Cl 0.72049(6) 0.7500 0.19069(15) 0.0899(5) Uani 1 2 d SU . .
Cl3 Cl 0.59999(6) 0.2500 0.85293(17) 0.1002(6) Uani 1 2 d SU . .
Cl4 Cl 0.68599(6) 0.32927(7) 0.89984(14) 0.1021(5) Uani 1 1 d U . .
Cl6 Cl 0.63431(7) 0.67104(11) 0.15236(17) 0.1364(8) Uani 1 1 d U . .
Cl1A Cl 0.50936(10) 0.17142(11) 0.6314(3) 0.1478(13) Uani 0.893(6) 1 d PU A 4
Cl2A Cl 0.54953(7) 0.2500 0.4182(3) 0.127(2) Uani 0.732(9) 2 d SPU A 1
O5 O 0.63457(13) 0.7500 -0.1066(3) 0.0764(11) Uani 1 2 d SU . .
O6 O 0.71230(13) 0.7500 -0.0906(4) 0.0801(12) Uani 1 2 d SU . .
C25 C 0.65312(17) 0.2500 0.9450(5) 0.0549(10) Uani 1 2 d SU . .
O1 O 0.41938(15) 0.2500 0.5366(4) 0.0927(14) Uani 1 2 d SU . .
O2 O 0.45462(13) 0.2500 0.3468(3) 0.0718(10) Uani 1 2 d SU . .
C27 C 0.66628(17) 0.7500 0.1050(5) 0.0561(11) Uani 1 2 d SU . .
N2 N 0.49584(15) 0.7500 0.8868(4) 0.0602(10) Uani 1 2 d SU . .
H2A H 0.4641 0.7500 0.8949 0.072 Uiso 1 2 calc SR . .
H2B H 0.5027 0.7500 0.8009 0.072 Uiso 1 2 calc SR . .
N3 N 0.69079(14) 0.2500 0.4210(4) 0.0585(10) Uani 1 2 d SU . .
H3A H 0.6843 0.2500 0.3349 0.070 Uiso 1 2 calc SR . .
H3B H 0.7225 0.2500 0.4304 0.070 Uiso 1 2 calc SR . .
N1 N 0.34191(15) 0.2500 0.3738(4) 0.0603(10) Uani 1 2 d SU . .
H1A H 0.3485 0.2500 0.2878 0.072 Uiso 1 2 calc SR . .
H1B H 0.3695 0.2500 0.4175 0.072 Uiso 1 2 calc SR . .
O4 O 0.68220(15) 0.2500 1.1572(4) 0.0861(13) Uani 1 2 d SU . .
O3 O 0.60516(16) 0.2500 1.1372(4) 0.0907(13) Uani 1 2 d SU . .
C26 C 0.67235(16) 0.7500 -0.0465(4) 0.0531(10) Uani 1 2 d SU . .
C23 C 0.50284(19) 0.2500 0.5380(6) 0.0693(13) Uani 1 2 d SU . .
C22 C 0.45374(16) 0.2500 0.4636(5) 0.0550(10) Uani 1 2 d SU A .
C24 C 0.64426(18) 0.2500 1.0959(5) 0.0576(11) Uani 1 2 d SU . .
C2 C 0.34117(14) 0.3885(3) 0.3713(4) 0.0694(9) Uani 1 1 d U . .
C16 C 0.68913(13) 0.3893(2) 0.4227(4) 0.0663(9) Uani 1 1 d U . .
C9 C 0.49250(13) 0.6121(2) 0.8922(4) 0.0659(9) Uani 1 1 d U . .
C8 C 0.51519(15) 0.6805(2) 0.9473(4) 0.0718(10) Uani 1 1 d U . .
H8A H 0.5491 0.6782 0.9324 0.086 Uiso 1 1 calc R . .
H8B H 0.5099 0.6820 1.0409 0.086 Uiso 1 1 calc R . .
C15 C 0.67088(15) 0.3189(2) 0.4816(5) 0.0744(11) Uani 1 1 d U . .
H15A H 0.6367 0.3179 0.4730 0.089 Uiso 1 1 calc R . .
H15B H 0.6783 0.3187 0.5742 0.089 Uiso 1 1 calc R . .
C21 C 0.72204(15) 0.4315(3) 0.4905(4) 0.0742(10) Uani 1 1 d U . .
H21 H 0.7339 0.4138 0.5694 0.089 Uiso 1 1 calc R . .
C7 C 0.37219(15) 0.4227(3) 0.4583(4) 0.0791(11) Uani 1 1 d U . .
H7 H 0.3782 0.4008 0.5390 0.095 Uiso 1 1 calc R . .
C14 C 0.50744(16) 0.5830(2) 0.7756(4) 0.0772(11) Uani 1 1 d U . .
H14 H 0.5322 0.6055 0.7307 0.093 Uiso 1 1 calc R . .
C1 C 0.31501(16) 0.3186(3) 0.4071(5) 0.0796(11) Uani 1 1 d U . .
H1C H 0.3086 0.3190 0.5002 0.096 Uiso 1 1 calc R . .
H1D H 0.2849 0.3179 0.3617 0.096 Uiso 1 1 calc R . .
C17 C 0.67203(17) 0.4166(3) 0.3052(5) 0.0816(11) Uani 1 1 d U . .
H17 H 0.6496 0.3897 0.2582 0.098 Uiso 1 1 calc R . .
C3 C 0.33303(18) 0.4218(3) 0.2527(4) 0.0828(11) Uani 1 1 d U . .
H3 H 0.3120 0.4002 0.1939 0.099 Uiso 1 1 calc R . .
C10 C 0.45629(17) 0.5751(3) 0.9586(5) 0.0841(12) Uani 1 1 d U . .
H10 H 0.4461 0.5932 1.0390 0.101 Uiso 1 1 calc R . .
C19 C 0.72087(19) 0.5256(3) 0.3279(5) 0.0879(13) Uani 1 1 d U . .
H19 H 0.7311 0.5714 0.2959 0.105 Uiso 1 1 calc R . .
C20 C 0.73752(17) 0.4992(3) 0.4429(5) 0.0854(12) Uani 1 1 d U . .
H20 H 0.7595 0.5269 0.4902 0.102 Uiso 1 1 calc R . .
C12 C 0.45032(18) 0.4851(3) 0.7905(5) 0.0915(13) Uani 1 1 d U . .
H12 H 0.4362 0.4425 0.7562 0.110 Uiso 1 1 calc R . .
C11 C 0.43575(18) 0.5130(3) 0.9075(6) 0.0951(14) Uani 1 1 d U . .
H11 H 0.4115 0.4894 0.9529 0.114 Uiso 1 1 calc R . .
C6 C 0.39390(17) 0.4886(3) 0.4260(6) 0.0907(13) Uani 1 1 d U . .
H6 H 0.4143 0.5111 0.4854 0.109 Uiso 1 1 calc R . .
C18 C 0.6884(2) 0.4837(3) 0.2585(5) 0.0913(13) Uani 1 1 d U . .
H18 H 0.6775 0.5013 0.1786 0.110 Uiso 1 1 calc R . .
C5 C 0.38596(19) 0.5218(3) 0.3076(6) 0.0955(14) Uani 1 1 d U . .
H5 H 0.4005 0.5667 0.2862 0.115 Uiso 1 1 calc R . .
C4 C 0.3557(2) 0.4869(3) 0.2203(5) 0.0938(14) Uani 1 1 d U . .
H4 H 0.3506 0.5079 0.1384 0.113 Uiso 1 1 calc R . .
C13 C 0.4858(2) 0.5199(3) 0.7238(5) 0.0883(13) Uani 1 1 d U . .
H13 H 0.4956 0.5014 0.6433 0.106 Uiso 1 1 calc R . .
Cl2B Cl 0.5385(4) 0.3194(7) 0.4908(17) 0.139(6) Uani 0.164(6) 1 d PU A 2
Cl1B Cl 0.4882(7) 0.2500 0.7122(16) 0.130(7) Uani 0.126(7) 2 d SPU A 3


_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
Cl5 C27 1.765(5) . ?
Cl3 C25 1.772(5) . ?
Cl4 C25 1.759(3) . ?
Cl6 C27 1.748(3) . ?
Cl1A C23 1.713(4) . ?
Cl2A C23 1.801(7) . ?
O5 C26 1.232(6) . ?
O6 C26 1.216(6) . ?
C25 C24 1.565(7) . ?
C25 Cl4 1.759(3) 8_565 ?
O1 C22 1.225(6) . ?
O2 C22 1.195(6) . ?
C27 C26 1.560(6) . ?
C27 Cl6 1.748(3) 8_575 ?
N2 C8 1.496(5) . ?
N2 C8 1.496(5) 8_575 ?
N3 C15 1.492(5) 8_565 ?
N3 C15 1.492(5) . ?
N1 C1 1.486(5) 8_565 ?
N1 C1 1.486(5) . ?
O4 C24 1.242(6) . ?
O3 C24 1.183(7) . ?
C23 C22 1.583(7) . ?
C23 Cl2B 1.673(10) . ?
C23 Cl2B 1.673(10) 8_565 ?
C23 Cl1A 1.713(4) 8_565 ?
C23 Cl1B 1.830(19) . ?
C2 C3 1.372(6) . ?
C2 C7 1.393(6) . ?
C2 C1 1.499(6) . ?
C16 C21 1.385(6) . ?
C16 C17 1.385(6) . ?
C16 C15 1.492(6) . ?
C9 C14 1.370(6) . ?
C9 C10 1.396(6) . ?
C9 C8 1.493(6) . ?
C21 C20 1.379(7) . ?
C7 C6 1.372(7) . ?
C14 C13 1.390(7) . ?
C17 C18 1.376(7) . ?
C3 C4 1.371(8) . ?
C10 C11 1.360(7) . ?
C19 C20 1.354(7) . ?
C19 C18 1.381(8) . ?
C12 C11 1.362(8) . ?
C12 C13 1.364(7) . ?
C6 C5 1.369(8) . ?
C5 C4 1.387(8) . ?

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
C24 C25 Cl4 110.1(2) . 8_565 ?
C24 C25 Cl4 110.1(2) . . ?
Cl4 C25 Cl4 107.7(3) 8_565 . ?
C24 C25 Cl3 112.9(3) . . ?
Cl4 C25 Cl3 107.9(2) 8_565 . ?
Cl4 C25 Cl3 107.9(2) . . ?
C26 C27 Cl6 109.4(2) . 8_575 ?
C26 C27 Cl6 109.4(2) . . ?
Cl6 C27 Cl6 108.2(3) 8_575 . ?
C26 C27 Cl5 113.5(3) . . ?
Cl6 C27 Cl5 108.11(19) 8_575 . ?
Cl6 C27 Cl5 108.11(19) . . ?
C8 N2 C8 112.9(4) . 8_575 ?
C15 N3 C15 111.7(4) 8_565 . ?
C1 N1 C1 111.8(5) 8_565 . ?
O6 C26 O5 128.3(5) . . ?
O6 C26 C27 118.1(4) . . ?
O5 C26 C27 113.6(4) . . ?
C22 C23 Cl2B 112.9(5) . . ?
C22 C23 Cl2B 112.9(5) . 8_565 ?
Cl2B C23 Cl2B 96.1(13) . 8_565 ?
C22 C23 Cl1A 111.3(2) . . ?
Cl2B C23 Cl1A 135.1(5) . . ?
Cl2B C23 Cl1A 59.0(7) 8_565 . ?
C22 C23 Cl1A 111.3(2) . 8_565 ?
Cl2B C23 Cl1A 59.0(7) . 8_565 ?
Cl2B C23 Cl1A 135.1(5) 8_565 8_565 ?
Cl1A C23 Cl1A 110.7(4) . 8_565 ?
C22 C23 Cl2A 108.4(4) . . ?
Cl2B C23 Cl2A 50.3(7) . . ?
Cl2B C23 Cl2A 50.3(7) 8_565 . ?
Cl1A C23 Cl2A 107.5(3) . . ?
Cl1A C23 Cl2A 107.5(3) 8_565 . ?
C22 C23 Cl1B 105.7(7) . . ?
Cl2B C23 Cl1B 114.7(8) . . ?
Cl2B C23 Cl1B 114.7(8) 8_565 . ?
Cl1A C23 Cl1B 58.7(3) . . ?
Cl1A C23 Cl1B 58.7(3) 8_565 . ?
Cl2A C23 Cl1B 146.0(7) . . ?
O2 C22 O1 128.8(5) . . ?
O2 C22 C23 117.6(4) . . ?
O1 C22 C23 113.7(4) . . ?
O3 C24 O4 128.7(5) . . ?
O3 C24 C25 120.1(5) . . ?
O4 C24 C25 111.1(4) . . ?
C3 C2 C7 118.6(5) . . ?
C3 C2 C1 119.9(4) . . ?
C7 C2 C1 121.5(4) . . ?
C21 C16 C17 118.5(4) . . ?
C21 C16 C15 119.5(4) . . ?
C17 C16 C15 121.9(4) . . ?
C14 C9 C10 118.0(4) . . ?
C14 C9 C8 120.6(4) . . ?
C10 C9 C8 121.4(4) . . ?
C9 C8 N2 111.7(3) . . ?
C16 C15 N3 113.7(3) . . ?
C20 C21 C16 121.1(4) . . ?
C6 C7 C2 120.5(4) . . ?
C9 C14 C13 120.4(4) . . ?
N1 C1 C2 112.5(3) . . ?
C18 C17 C16 119.5(5) . . ?
C4 C3 C2 120.4(5) . . ?
C11 C10 C9 120.9(4) . . ?
C20 C19 C18 119.2(5) . . ?
C19 C20 C21 120.3(5) . . ?
C11 C12 C13 119.6(5) . . ?
C10 C11 C12 120.7(5) . . ?
C5 C6 C7 121.0(5) . . ?
C17 C18 C19 121.4(5) . . ?
C6 C5 C4 118.4(5) . . ?
C3 C4 C5 121.1(5) . . ?
C12 C13 C14 120.3(5) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        66.60
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.753
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.066
####################################################################### 
# 
# 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_f:\zsy\done\315k\315k
_database_code_depnum_ccdc_archive 'CCDC 1400883'
_audit_update_record             
;
2015-05-14 deposited with the CCDC.
2016-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 N, C2 Cl3 O2'
_chemical_formula_sum            'C24 H24 Cl4.49 N1.50 O3'
_chemical_formula_weight         540.71

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'
O O 0.0492 0.0322 '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'
Cl Cl 0.3639 0.7018 '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 n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   28.2714(3)
_cell_length_b                   17.9408(2)
_cell_length_c                   10.24460(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5196.18(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    315(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2231
_exptl_absorpt_coefficient_mu    4.831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.164
_exptl_absorpt_correction_T_max  0.299
_exptl_absorpt_process_details   
; 
_exptl_special_details 
;



_diffrn_ambient_temperature      315(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27392
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.98
_diffrn_reflns_theta_max         66.59
_reflns_number_total             4744
_reflns_number_gt                3881
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.1168P)²+4.5055P] 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         4744
_refine_ls_number_parameters     339
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0775
_refine_ls_wR_factor_ref         0.2301
_refine_ls_wR_factor_gt          0.2158
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
Cl3 Cl 0.27945(5) 0.2500 -0.18996(14) 0.0895(5) Uani 1 2 d S . .
Cl6 Cl 0.31407(5) 0.67068(7) 1.10086(14) 0.1022(5) Uani 1 1 d . . .
Cl5 Cl 0.39994(6) 0.7500 1.14760(16) 0.1012(6) Uani 1 2 d S . .
Cl4 Cl 0.36526(6) 0.32909(9) -0.15112(16) 0.1375(7) Uani 1 1 d . . .
Cl2A Cl 0.50943(11) 0.32878(11) -0.3687(3) 0.1448(16) Uani 0.867(7) 1 d P A 3
N1 N 0.49581(13) 0.7500 0.8863(4) 0.0561(9) Uani 1 2 d S . .
H26A H 0.5025 0.7500 0.8004 0.067 Uiso 1 2 calc SR . .
H26B H 0.4641 0.7500 0.8949 0.067 Uiso 1 2 calc SR . .
Cl1B Cl 0.54933(7) 0.2500 -0.5808(3) 0.135(3) Uani 0.728(10) 2 d SP A 2
O5 O 0.39475(14) 0.7500 0.8634(4) 0.0916(13) Uani 1 2 d S . .
O3 O 0.36524(11) 0.2500 0.1069(3) 0.0760(11) Uani 1 2 d S . .
O4 O 0.28753(12) 0.2500 0.0910(4) 0.0786(11) Uani 1 2 d S . .
N2 N 0.34197(13) 0.2500 0.3741(4) 0.0583(9) Uani 1 2 d S . .
H34A H 0.3696 0.2500 0.4175 0.070 Uiso 1 2 calc SR . .
H34B H 0.3484 0.2500 0.2880 0.070 Uiso 1 2 calc SR . .
O2 O 0.45454(12) 0.2500 -0.6529(3) 0.0718(10) Uani 1 2 d S . .
N3 N 0.19074(13) 0.2500 0.0808(4) 0.0563(9) Uani 1 2 d S . .
H42A H 0.2224 0.2500 0.0712 0.068 Uiso 1 2 calc SR . .
H42B H 0.1843 0.2500 0.1668 0.068 Uiso 1 2 calc SR . .
O1 O 0.41924(13) 0.2500 -0.4635(4) 0.0964(14) Uani 1 2 d S . .
O6 O 0.31775(14) 0.7500 0.8438(4) 0.0883(12) Uani 1 2 d S . .
C9 C 0.34129(13) 0.3884(2) 0.3721(4) 0.0672(9) Uani 1 1 d . . .
C23 C 0.50232(18) 0.2500 -0.4609(6) 0.0677(13) Uani 1 2 d S . .
C2 C 0.49262(12) 0.6122(2) 0.8925(3) 0.0634(9) Uani 1 1 d . . .
C16 C 0.18897(12) 0.1106(2) 0.0782(4) 0.0639(9) Uani 1 1 d . . .
C8 C 0.31504(14) 0.3189(2) 0.4076(4) 0.0777(11) Uani 1 1 d . . .
H33A H 0.3086 0.3192 0.5006 0.093 Uiso 1 1 calc R . .
H33B H 0.2850 0.3182 0.3621 0.093 Uiso 1 1 calc R . .
C26 C 0.35544(17) 0.7500 0.9055(5) 0.0566(11) Uani 1 2 d S . .
C27 C 0.34703(15) 0.7500 1.0556(4) 0.0534(10) Uani 1 2 d S . .
C1 C 0.51514(14) 0.6801(2) 0.9459(4) 0.0705(9) Uani 1 1 d . . .
H25A H 0.5489 0.6778 0.9302 0.085 Uiso 1 1 calc R . .
H25B H 0.5102 0.6817 1.0396 0.085 Uiso 1 1 calc R . .
C22 C 0.45389(15) 0.2500 -0.5367(4) 0.0535(10) Uani 1 2 d S A .
C10 C 0.37220(14) 0.4231(3) 0.4583(4) 0.0786(11) Uani 1 1 d . . .
H28 H 0.3782 0.4015 0.5391 0.094 Uiso 1 1 calc R . .
C24 C 0.32771(14) 0.2500 0.0471(4) 0.0518(10) Uani 1 2 d S . .
C7 C 0.50727(15) 0.5824(2) 0.7749(4) 0.0751(10) Uani 1 1 d . . .
H20 H 0.5319 0.6049 0.7295 0.090 Uiso 1 1 calc R . .
C4 C 0.43596(16) 0.5124(3) 0.9081(5) 0.0930(13) Uani 1 1 d . . .
H23 H 0.4121 0.4883 0.9543 0.112 Uiso 1 1 calc R . .
C25 C 0.33371(16) 0.2500 -0.1044(4) 0.0548(10) Uani 1 2 d S . .
C20 C 0.23732(15) 0.0014(3) 0.0579(5) 0.0838(11) Uani 1 1 d . . .
H37 H 0.2592 -0.0263 0.0106 0.101 Uiso 1 1 calc R . .
C21 C 0.22198(13) 0.0688(2) 0.0107(4) 0.0725(10) Uani 1 1 d . . .
H36 H 0.2340 0.0866 -0.0679 0.087 Uiso 1 1 calc R . .
C14 C 0.33344(17) 0.4219(2) 0.2534(4) 0.0811(11) Uani 1 1 d . . .
H32 H 0.3128 0.3998 0.1943 0.097 Uiso 1 1 calc R . .
C15 C 0.17061(14) 0.1811(2) 0.0198(4) 0.0746(10) Uani 1 1 d . . .
H41A H 0.1365 0.1820 0.0288 0.089 Uiso 1 1 calc R . .
H41B H 0.1779 0.1814 -0.0728 0.089 Uiso 1 1 calc R . .
C3 C 0.45647(15) 0.5757(3) 0.9587(4) 0.0816(11) Uani 1 1 d . . .
H24 H 0.4460 0.5942 1.0384 0.098 Uiso 1 1 calc R . .
C17 C 0.17211(16) 0.0831(2) 0.1957(4) 0.0809(11) Uani 1 1 d . . .
H40 H 0.1498 0.1101 0.2430 0.097 Uiso 1 1 calc R . .
C11 C 0.39402(16) 0.4891(3) 0.4257(5) 0.0894(13) Uani 1 1 d . . .
H29 H 0.4146 0.5117 0.4846 0.107 Uiso 1 1 calc R . .
C19 C 0.22081(17) -0.0250(3) 0.1730(5) 0.0865(12) Uani 1 1 d . . .
H38 H 0.2313 -0.0705 0.2052 0.104 Uiso 1 1 calc R . .
C12 C 0.38578(17) 0.5215(3) 0.3082(5) 0.0923(13) Uani 1 1 d . . .
H30 H 0.4003 0.5664 0.2865 0.111 Uiso 1 1 calc R . .
C13 C 0.35546(19) 0.4869(3) 0.2209(5) 0.0937(14) Uani 1 1 d . . .
H31 H 0.3501 0.5081 0.1395 0.112 Uiso 1 1 calc R . .
C5 C 0.45016(17) 0.4850(3) 0.7913(5) 0.0904(13) Uani 1 1 d . . .
H22 H 0.4357 0.4428 0.7568 0.109 Uiso 1 1 calc R . .
C6 C 0.48603(18) 0.5199(3) 0.7240(5) 0.0875(12) Uani 1 1 d . . .
H21 H 0.4959 0.5011 0.6438 0.105 Uiso 1 1 calc R . .
C18 C 0.18810(15) 0.0168(2) 0.2419(4) 0.0929(14) Uani 1 1 d . . .
H39 H 0.1769 -0.0008 0.3214 0.111 Uiso 1 1 calc R . .
Cl1A Cl 0.53763(15) 0.1767(2) -0.5046(4) 0.162(12) Uani 0.182(9) 1 d PR A 1
Cl2B Cl 0.48705(15) 0.2500(2) -0.2810(4) 0.205(18) Uani 0.161(9) 2 d SPR A 4


_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
Cl3 C25 1.766(4) . ?
Cl6 C27 1.763(3) . ?
Cl5 C27 1.768(5) . ?
Cl4 C25 1.743(3) . ?
Cl2A C23 1.712(3) . ?
N1 C1 1.498(4) 8_575 ?
N1 C1 1.498(4) . ?
N1 H26A 0.9000 . ?
N1 H26B 0.9000 . ?
Cl1B C23 1.810(6) . ?
O5 C26 1.192(6) . ?
O3 C24 1.225(5) . ?
O4 C24 1.222(5) . ?
N2 C8 1.491(4) . ?
N2 C8 1.491(4) 8_565 ?
N2 H34A 0.9000 . ?
N2 H34B 0.9000 . ?
O2 C22 1.190(6) . ?
N3 C15 1.498(4) . ?
N3 C15 1.498(4) 8_565 ?
N3 H42A 0.9000 . ?
N3 H42B 0.9000 . ?
O1 C22 1.234(6) . ?
O6 C26 1.239(6) . ?
C9 C14 1.374(6) . ?
C9 C10 1.391(6) . ?
C9 C8 1.496(6) . ?
C23 C22 1.574(6) . ?
C23 Cl1A 1.711(6) 8_565 ?
C23 Cl1A 1.711(6) . ?
C23 Cl2A 1.712(3) 8_565 ?
C23 Cl2B 1.893(7) . ?
C2 C7 1.382(6) . ?
C2 C3 1.390(6) . ?
C2 C1 1.480(5) . ?
C16 C21 1.382(5) . ?
C16 C17 1.386(6) . ?
C16 C15 1.492(5) . ?
C8 H33A 0.9700 . ?
C8 H33B 0.9700 . ?
C26 C27 1.556(7) . ?
C27 Cl6 1.763(3) 8_575 ?
C1 H25A 0.9700 . ?
C1 H25B 0.9700 . ?
C10 C11 1.376(7) . ?
C10 H28 0.9300 . ?
C24 C25 1.561(6) . ?
C7 C6 1.375(6) . ?
C7 H20 0.9300 . ?
C4 C5 1.354(7) . ?
C4 C3 1.376(7) . ?
C4 H23 0.9300 . ?
C25 Cl4 1.743(3) 8_565 ?
C20 C19 1.353(7) . ?
C20 C21 1.372(6) . ?
C20 H37 0.9300 . ?
C21 H36 0.9300 . ?
C14 C13 1.363(7) . ?
C14 H32 0.9300 . ?
C15 H41A 0.9700 . ?
C15 H41B 0.9700 . ?
C3 H24 0.9300 . ?
C17 C18 1.357(6) . ?
C17 H40 0.9300 . ?
C11 C12 1.357(7) . ?
C11 H29 0.9300 . ?
C19 C18 1.385(6) . ?
C19 H38 0.9300 . ?
C12 C13 1.386(7) . ?
C12 H30 0.9300 . ?
C13 H31 0.9300 . ?
C5 C6 1.377(7) . ?
C5 H22 0.9300 . ?
C6 H21 0.9300 . ?
C18 H39 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 N1 C1 113.6(4) 8_575 . ?
C1 N1 H26A 108.8 8_575 . ?
C1 N1 H26A 108.8 . . ?
C1 N1 H26B 108.8 8_575 . ?
C1 N1 H26B 108.8 . . ?
H26A N1 H26B 107.7 . . ?
C8 N2 C8 111.9(4) . 8_565 ?
C8 N2 H34A 109.2 . . ?
C8 N2 H34A 109.2 8_565 . ?
C8 N2 H34B 109.2 . . ?
C8 N2 H34B 109.2 8_565 . ?
H34A N2 H34B 107.9 . . ?
C15 N3 C15 111.3(4) . 8_565 ?
C15 N3 H42A 109.4 . . ?
C15 N3 H42A 109.4 8_565 . ?
C15 N3 H42B 109.4 . . ?
C15 N3 H42B 109.4 8_565 . ?
H42A N3 H42B 108.0 . . ?
C14 C9 C10 117.9(4) . . ?
C14 C9 C8 120.0(4) . . ?
C10 C9 C8 122.1(4) . . ?
C22 C23 Cl1A 112.2(3) . 8_565 ?
C22 C23 Cl1A 112.2(3) . . ?
Cl1A C23 Cl1A 100.5(4) 8_565 . ?
C22 C23 Cl2A 112.0(2) . . ?
Cl1A C23 Cl2A 56.0(2) 8_565 . ?
Cl1A C23 Cl2A 135.3(3) . . ?
C22 C23 Cl2A 112.0(2) . 8_565 ?
Cl1A C23 Cl2A 135.3(3) 8_565 8_565 ?
Cl1A C23 Cl2A 56.0(2) . 8_565 ?
Cl2A C23 Cl2A 111.3(4) . 8_565 ?
C22 C23 Cl1B 107.7(4) . . ?
Cl1A C23 Cl1B 52.7(2) 8_565 . ?
Cl1A C23 Cl1B 52.7(2) . . ?
Cl2A C23 Cl1B 106.8(2) . . ?
Cl2A C23 Cl1B 106.8(2) 8_565 . ?
C22 C23 Cl2B 106.4(4) . . ?
Cl1A C23 Cl2B 112.8(3) 8_565 . ?
Cl1A C23 Cl2B 112.8(3) . . ?
Cl2A C23 Cl2B 59.3(2) . . ?
Cl2A C23 Cl2B 59.3(2) 8_565 . ?
Cl1B C23 Cl2B 145.9(3) . . ?
C7 C2 C3 117.6(4) . . ?
C7 C2 C1 120.8(3) . . ?
C3 C2 C1 121.6(4) . . ?
C21 C16 C17 118.3(4) . . ?
C21 C16 C15 119.6(4) . . ?
C17 C16 C15 122.0(4) . . ?
N2 C8 C9 112.4(3) . . ?
N2 C8 H33A 109.1 . . ?
C9 C8 H33A 109.1 . . ?
N2 C8 H33B 109.1 . . ?
C9 C8 H33B 109.1 . . ?
H33A C8 H33B 107.9 . . ?
O5 C26 O6 128.1(5) . . ?
O5 C26 C27 120.0(4) . . ?
O6 C26 C27 111.9(4) . . ?
C26 C27 Cl6 109.9(2) . . ?
C26 C27 Cl6 109.9(2) . 8_575 ?
Cl6 C27 Cl6 107.6(3) . 8_575 ?
C26 C27 Cl5 113.4(3) . . ?
Cl6 C27 Cl5 107.89(18) . . ?
Cl6 C27 Cl5 107.89(18) 8_575 . ?
C2 C1 N1 112.4(3) . . ?
C2 C1 H25A 109.1 . . ?
N1 C1 H25A 109.1 . . ?
C2 C1 H25B 109.1 . . ?
N1 C1 H25B 109.1 . . ?
H25A C1 H25B 107.8 . . ?
O2 C22 O1 128.3(4) . . ?
O2 C22 C23 118.7(4) . . ?
O1 C22 C23 113.0(4) . . ?
C11 C10 C9 120.9(4) . . ?
C11 C10 H28 119.6 . . ?
C9 C10 H28 119.6 . . ?
O4 C24 O3 128.4(4) . . ?
O4 C24 C25 117.8(4) . . ?
O3 C24 C25 113.8(4) . . ?
C6 C7 C2 121.0(4) . . ?
C6 C7 H20 119.5 . . ?
C2 C7 H20 119.5 . . ?
C5 C4 C3 120.5(4) . . ?
C5 C4 H23 119.7 . . ?
C3 C4 H23 119.7 . . ?
C24 C25 Cl4 109.2(2) . . ?
C24 C25 Cl4 109.2(2) . 8_565 ?
Cl4 C25 Cl4 109.0(3) . 8_565 ?
C24 C25 Cl3 113.5(3) . . ?
Cl4 C25 Cl3 107.96(18) . . ?
Cl4 C25 Cl3 107.96(18) 8_565 . ?
C19 C20 C21 120.4(4) . . ?
C19 C20 H37 119.8 . . ?
C21 C20 H37 119.8 . . ?
C20 C21 C16 121.0(4) . . ?
C20 C21 H36 119.5 . . ?
C16 C21 H36 119.5 . . ?
C13 C14 C9 121.1(4) . . ?
C13 C14 H32 119.5 . . ?
C9 C14 H32 119.5 . . ?
C16 C15 N3 113.6(3) . . ?
C16 C15 H41A 108.8 . . ?
N3 C15 H41A 108.8 . . ?
C16 C15 H41B 108.8 . . ?
N3 C15 H41B 108.8 . . ?
H41A C15 H41B 107.7 . . ?
C4 C3 C2 120.9(4) . . ?
C4 C3 H24 119.5 . . ?
C2 C3 H24 119.5 . . ?
C18 C17 C16 120.0(4) . . ?
C18 C17 H40 120.0 . . ?
C16 C17 H40 120.0 . . ?
C12 C11 C10 120.5(5) . . ?
C12 C11 H29 119.8 . . ?
C10 C11 H29 119.8 . . ?
C20 C19 C18 119.0(4) . . ?
C20 C19 H38 120.5 . . ?
C18 C19 H38 120.5 . . ?
C11 C12 C13 119.1(5) . . ?
C11 C12 H30 120.4 . . ?
C13 C12 H30 120.4 . . ?
C14 C13 C12 120.6(5) . . ?
C14 C13 H31 119.7 . . ?
C12 C13 H31 119.7 . . ?
C4 C5 C6 119.8(5) . . ?
C4 C5 H22 120.1 . . ?
C6 C5 H22 120.1 . . ?
C7 C6 C5 120.1(4) . . ?
C7 C6 H21 119.9 . . ?
C5 C6 H21 119.9 . . ?
C17 C18 C19 121.3(4) . . ?
C17 C18 H39 119.4 . . ?
C19 C18 H39 119.4 . . ?

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
N1 H26A O2 0.90 1.94 2.773(5) 153.2 5_665
N1 H26B O5 0.90 1.99 2.867(6) 165.0 .
N2 H34A O1 0.90 1.86 2.746(6) 168.7 1_556
N2 H34B O3 0.90 1.92 2.815(5) 177.4 .
N3 H42A O4 0.90 1.85 2.738(5) 167.4 .
N3 H42B O6 0.90 1.81 2.705(6) 170.1 2_564

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        66.59
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.895
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.074
####################################################################### 
# 
# 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_f:\zsy\done\olex2_~2\320k
_database_code_depnum_ccdc_archive 'CCDC 1400884'
_audit_update_record             
;
2015-05-14 deposited with the CCDC.
2016-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 N, C2 Cl3 O2'
_chemical_formula_sum            'C24 H24 Cl4.50 N1.50 O3'
_chemical_formula_weight         540.97

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'
Cl Cl 0.3639 0.7018 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   28.2869(4)
_cell_length_b                   17.9428(3)
_cell_length_c                   10.25130(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5203.01(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    320(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2232
_exptl_absorpt_coefficient_mu    4.832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.164
_exptl_absorpt_correction_T_max  0.299
_exptl_absorpt_process_details   
; 
_exptl_special_details 
;



_diffrn_ambient_temperature      320(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12575
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         66.58
_reflns_number_total             4755
_reflns_number_gt                3706
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.1284P)²+4.7600P] 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         4755
_refine_ls_number_parameters     344
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0850
_refine_ls_wR_factor_ref         0.2619
_refine_ls_wR_factor_gt          0.2402
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
Cl6 Cl 0.27928(6) 0.2500 0.31134(16) 0.0968(6) Uani 1 2 d S . .
Cl3 Cl 0.68596(6) 0.32933(8) 0.39793(16) 0.1097(5) Uani 1 1 d . . .
Cl4 Cl 0.60026(7) 0.2500 0.35153(18) 0.1086(7) Uani 1 2 d S . .
Cl5 Cl 0.36479(7) 0.32915(11) 0.35045(17) 0.1442(8) Uani 1 1 d . . .
Cl1B Cl 0.5092(2) 0.32891(17) 1.1322(5) 0.146(2) Uani 0.814(14) 1 d P A 3
Cl2B Cl 0.54910(9) 0.2500 0.9197(4) 0.147(4) Uani 0.715(12) 2 d SP A 1
O6 O 0.28714(14) 0.2500 0.5924(4) 0.0851(13) Uani 1 2 d S . .
O2 O 0.45459(14) 0.2500 0.8487(4) 0.0770(11) Uani 1 2 d S . .
O4 O 0.60568(17) 0.2500 0.6352(5) 0.0971(14) Uani 1 2 d S . .
O5 O 0.36501(14) 0.2500 0.6078(4) 0.0814(12) Uani 1 2 d S . .
N3 N 0.30975(15) 0.7500 0.0830(4) 0.0614(10) Uani 1 2 d S . .
H26A H 0.3164 0.7500 0.1689 0.074 Uiso 1 2 calc SR . .
H26B H 0.2781 0.7500 0.0739 0.074 Uiso 1 2 calc SR . .
O3 O 0.68230(17) 0.2500 0.6551(4) 0.0950(14) Uani 1 2 d S . .
N1 N 0.34215(16) 0.2500 0.8744(4) 0.0643(11) Uani 1 2 d S . .
H34A H 0.3481 0.2500 0.7882 0.077 Uiso 1 2 calc SR . .
H34B H 0.3700 0.2500 0.9168 0.077 Uiso 1 2 calc SR . .
C16 C 0.31140(14) 0.6104(2) 0.0802(4) 0.0690(10) Uani 1 1 d . . .
O1 O 0.41932(16) 0.2500 1.0367(4) 0.1031(16) Uani 1 2 d S . .
N2 N 0.50463(16) 0.2500 0.6143(4) 0.0608(10) Uani 1 2 d S . .
H42A H 0.5363 0.2500 0.6049 0.073 Uiso 1 2 calc SR . .
H42B H 0.4982 0.2500 0.7003 0.073 Uiso 1 2 calc SR . .
C22 C 0.45397(18) 0.2500 0.9643(5) 0.0596(12) Uani 1 2 d S A .
C9 C 0.50777(14) 0.3880(2) 0.6088(4) 0.0676(10) Uani 1 1 d . . .
C2 C 0.34188(15) 0.3888(3) 0.8734(4) 0.0720(11) Uani 1 1 d . . .
C21 C 0.27845(16) 0.5689(3) 0.0121(5) 0.0790(12) Uani 1 1 d . . .
H20 H 0.2665 0.5867 -0.0665 0.095 Uiso 1 1 calc R . .
C3 C 0.37228(17) 0.4228(3) 0.9593(4) 0.0837(13) Uani 1 1 d . . .
H29 H 0.3782 0.4013 1.0402 0.100 Uiso 1 1 calc R . .
C14 C 0.54343(18) 0.4239(3) 0.5413(5) 0.0871(13) Uani 1 1 d . . .
H36 H 0.5536 0.4051 0.4615 0.105 Uiso 1 1 calc R . .
C13 C 0.56396(19) 0.4876(3) 0.5915(6) 0.0990(16) Uani 1 1 d . . .
H37 H 0.5877 0.5116 0.5449 0.119 Uiso 1 1 calc R . .
C24 C 0.6451(2) 0.2500 0.5930(6) 0.0640(13) Uani 1 2 d S . .
C4 C 0.39404(19) 0.4890(3) 0.9254(6) 0.0958(15) Uani 1 1 d . . .
H30 H 0.4147 0.5116 0.9839 0.115 Uiso 1 1 calc R . .
C19 C 0.27930(19) 0.4752(3) 0.1750(5) 0.0908(14) Uani 1 1 d . . .
H22 H 0.2686 0.4297 0.2069 0.109 Uiso 1 1 calc R . .
C20 C 0.26314(18) 0.5014(3) 0.0597(6) 0.0907(14) Uani 1 1 d . . .
H21 H 0.2414 0.4735 0.0121 0.109 Uiso 1 1 calc R . .
C10 C 0.49313(17) 0.4176(2) 0.7255(5) 0.0803(12) Uani 1 1 d . . .
H40 H 0.4687 0.3949 0.7713 0.096 Uiso 1 1 calc R . .
C7 C 0.33376(19) 0.4214(3) 0.7548(5) 0.0865(13) Uani 1 1 d . . .
H27 H 0.3131 0.3990 0.6960 0.104 Uiso 1 1 calc R . .
C8 C 0.48494(16) 0.3197(2) 0.5546(4) 0.0755(11) Uani 1 1 d . . .
H41A H 0.4898 0.3182 0.4609 0.091 Uiso 1 1 calc R . .
H41B H 0.4512 0.3218 0.5706 0.091 Uiso 1 1 calc R . .
C5 C 0.38574(19) 0.5217(3) 0.8077(6) 0.0965(15) Uani 1 1 d . . .
H31 H 0.4001 0.5666 0.7859 0.116 Uiso 1 1 calc R . .
C12 C 0.54984(19) 0.5153(3) 0.7083(6) 0.0943(14) Uani 1 1 d . . .
H38 H 0.5642 0.5577 0.7424 0.113 Uiso 1 1 calc R . .
C6 C 0.3559(2) 0.4869(3) 0.7221(5) 0.0977(16) Uani 1 1 d . . .
H32 H 0.3505 0.5080 0.6406 0.117 Uiso 1 1 calc R . .
C1 C 0.31504(17) 0.3187(3) 0.9095(5) 0.0844(13) Uani 1 1 d . . .
H33A H 0.3088 0.3188 1.0026 0.101 Uiso 1 1 calc R . .
H33B H 0.2849 0.3183 0.8645 0.101 Uiso 1 1 calc R . .
C23 C 0.5018(2) 0.2500 1.0403(7) 0.0734(15) Uani 1 2 d S . .
C15 C 0.32983(16) 0.6811(2) 0.0214(5) 0.0810(12) Uani 1 1 d . . .
H25A H 0.3224 0.6815 -0.0710 0.097 Uiso 1 1 calc R . .
H25B H 0.3640 0.6821 0.0300 0.097 Uiso 1 1 calc R . .
C26 C 0.32776(18) 0.2500 0.5482(5) 0.0576(12) Uani 1 2 d S . .
C27 C 0.33336(19) 0.2500 0.3977(5) 0.0595(12) Uani 1 2 d S . .
C17 C 0.32804(19) 0.5833(3) 0.1976(5) 0.0863(13) Uani 1 1 d . . .
H24 H 0.3503 0.6101 0.2450 0.104 Uiso 1 1 calc R . .
C11 C 0.5144(2) 0.4805(3) 0.7752(5) 0.0932(14) Uani 1 1 d . . .
H39 H 0.5046 0.4994 0.8552 0.112 Uiso 1 1 calc R . .
C18 C 0.3112(2) 0.5156(3) 0.2440(5) 0.0966(16) Uani 1 1 d . . .
H23 H 0.3220 0.4976 0.3237 0.116 Uiso 1 1 calc R . .
C25 C 0.65339(18) 0.2500 0.4426(5) 0.0580(12) Uani 1 2 d S . .
Cl1A Cl 0.5355(5) 0.3234(7) 1.013(3) 0.20(2) Uani 0.224(16) 1 d P A 2
Cl2A Cl 0.4898(5) 0.2500 1.2093(13) 0.26(2) Uani 0.209(12) 2 d SP A 4


_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
Cl6 C27 1.767(5) . ?
Cl3 C25 1.756(3) . ?
Cl4 C25 1.770(5) . ?
Cl5 C27 1.744(3) . ?
Cl1B C23 1.714(4) . ?
Cl2B C23 1.822(7) . ?
O6 C26 1.235(6) . ?
O2 C22 1.185(6) . ?
O4 C24 1.196(7) . ?
O5 C26 1.218(6) . ?
N3 C15 1.500(5) . ?
N3 C15 1.500(5) 8_575 ?
O3 C24 1.229(7) . ?
N1 C1 1.496(5) 8_565 ?
N1 C1 1.496(5) . ?
C16 C17 1.380(7) . ?
C16 C21 1.383(6) . ?
C16 C15 1.499(6) . ?
O1 C22 1.229(7) . ?
N2 C8 1.499(5) 8_565 ?
N2 C8 1.499(5) . ?
C22 C23 1.561(8) . ?
C9 C10 1.372(6) . ?
C9 C14 1.383(6) . ?
C9 C8 1.494(6) . ?
C2 C7 1.368(6) . ?
C2 C3 1.374(6) . ?
C2 C1 1.514(6) . ?
C21 C20 1.375(7) . ?
C3 C4 1.382(7) . ?
C14 C13 1.380(8) . ?
C13 C12 1.357(8) . ?
C24 C25 1.559(7) . ?
C4 C5 1.362(8) . ?
C19 C20 1.352(7) . ?
C19 C18 1.356(8) . ?
C10 C11 1.378(7) . ?
C7 C6 1.373(8) . ?
C5 C6 1.368(8) . ?
C12 C11 1.366(7) . ?
C23 Cl1A 1.650(9) . ?
C23 Cl1A 1.650(9) 8_565 ?
C23 Cl1B 1.714(4) 8_565 ?
C23 Cl2A 1.766(16) . ?
C26 C27 1.551(7) . ?
C27 Cl5 1.744(3) 8_565 ?
C17 C18 1.389(8) . ?
C25 Cl3 1.756(3) 8_565 ?

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
C15 N3 C15 111.0(4) . 8_575 ?
C1 N1 C1 111.0(5) 8_565 . ?
C17 C16 C21 118.7(4) . . ?
C17 C16 C15 122.0(4) . . ?
C21 C16 C15 119.2(4) . . ?
C8 N2 C8 113.0(4) 8_565 . ?
O2 C22 O1 128.0(5) . . ?
O2 C22 C23 119.1(5) . . ?
O1 C22 C23 112.9(5) . . ?
C10 C9 C14 118.5(4) . . ?
C10 C9 C8 120.7(4) . . ?
C14 C9 C8 120.8(4) . . ?
C7 C2 C3 119.0(5) . . ?
C7 C2 C1 119.2(4) . . ?
C3 C2 C1 121.7(4) . . ?
C20 C21 C16 120.5(5) . . ?
C2 C3 C4 120.0(5) . . ?
C13 C14 C9 120.4(5) . . ?
C12 C13 C14 120.6(5) . . ?
O4 C24 O3 127.7(6) . . ?
O4 C24 C25 119.8(5) . . ?
O3 C24 C25 112.5(5) . . ?
C5 C4 C3 121.0(5) . . ?
C20 C19 C18 119.7(5) . . ?
C19 C20 C21 120.7(5) . . ?
C9 C10 C11 120.5(4) . . ?
C2 C7 C6 120.4(5) . . ?
C9 C8 N2 111.8(3) . . ?
C4 C5 C6 118.6(5) . . ?
C13 C12 C11 119.4(5) . . ?
C5 C6 C7 121.0(5) . . ?
N1 C1 C2 111.6(3) . . ?
C22 C23 Cl1A 114.5(6) . . ?
C22 C23 Cl1A 114.5(6) . 8_565 ?
Cl1A C23 Cl1A 105.8(17) . 8_565 ?
C22 C23 Cl1B 112.4(3) . 8_565 ?
Cl1A C23 Cl1B 133.0(5) . 8_565 ?
Cl1A C23 Cl1B 50.5(11) 8_565 8_565 ?
C22 C23 Cl1B 112.4(3) . . ?
Cl1A C23 Cl1B 50.5(11) . . ?
Cl1A C23 Cl1B 133.0(5) 8_565 . ?
Cl1B C23 Cl1B 111.4(5) 8_565 . ?
C22 C23 Cl2A 108.8(6) . . ?
Cl1A C23 Cl2A 106.3(13) . . ?
Cl1A C23 Cl2A 106.3(13) 8_565 . ?
Cl1B C23 Cl2A 58.9(3) 8_565 . ?
Cl1B C23 Cl2A 58.9(3) . . ?
C22 C23 Cl2B 107.3(4) . . ?
Cl1A C23 Cl2B 57.2(12) . . ?
Cl1A C23 Cl2B 57.2(12) 8_565 . ?
Cl1B C23 Cl2B 106.4(3) 8_565 . ?
Cl1B C23 Cl2B 106.4(3) . . ?
Cl2A C23 Cl2B 143.8(6) . . ?
C16 C15 N3 113.4(3) . . ?
O5 C26 O6 128.4(5) . . ?
O5 C26 C27 114.2(5) . . ?
O6 C26 C27 117.4(5) . . ?
C26 C27 Cl5 109.2(2) . 8_565 ?
C26 C27 Cl5 109.2(2) . . ?
Cl5 C27 Cl5 109.0(3) 8_565 . ?
C26 C27 Cl6 114.2(4) . . ?
Cl5 C27 Cl6 107.6(2) 8_565 . ?
Cl5 C27 Cl6 107.6(2) . . ?
C16 C17 C18 119.3(5) . . ?
C12 C11 C10 120.6(5) . . ?
C19 C18 C17 121.1(5) . . ?
C24 C25 Cl3 109.7(2) . 8_565 ?
C24 C25 Cl3 109.7(2) . . ?
Cl3 C25 Cl3 108.3(3) 8_565 . ?
C24 C25 Cl4 113.2(4) . . ?
Cl3 C25 Cl4 107.9(2) 8_565 . ?
Cl3 C25 Cl4 107.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        66.58
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.191
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.071
####################################################################### 
# 
# 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_f:\zsy\supern~1\rt\olex2_~1\401-rt
_database_code_depnum_ccdc_archive 'CCDC 1400885'
_audit_update_record             
;
2015-05-14 deposited with the CCDC.
2016-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 N, C2 Cl3 O2'
_chemical_formula_sum            'C24 H24 Cl4.50 N1.50 O3'
_chemical_formula_weight         540.97

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 n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   27.9771(10)
_cell_length_b                   17.8261(7)
_cell_length_c                   10.0751(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5024.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2232
_exptl_absorpt_coefficient_mu    0.552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.793
_exptl_absorpt_correction_T_max  0.871
_exptl_absorpt_process_details   
; 
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16412
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         26.37
_reflns_number_total             5280
_reflns_number_gt                4048
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0420P)²+2.6301P] 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         5280
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1030
_refine_ls_wR_factor_gt          0.0932
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_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 0.27901(3) 0.2500 0.30351(7) 0.0445(2) Uani 1 2 d S . .
Cl5 Cl 0.59883(3) 0.2500 0.35453(8) 0.0500(2) Uani 1 2 d S . .
Cl6 Cl 0.68560(2) 0.33041(3) 0.40260(6) 0.04996(16) Uani 1 1 d . . .
Cl4 Cl 0.55011(3) 0.2500 0.90916(9) 0.0696(3) Uani 1 2 d S . .
Cl2 Cl 0.36631(3) 0.33032(4) 0.33974(7) 0.0728(2) Uani 1 1 d . . .
Cl3 Cl 0.50991(3) 0.33045(4) 1.12799(7) 0.0660(2) Uani 1 1 d . . .
O4 O 0.45242(6) 0.2500 0.83846(18) 0.0368(5) Uani 1 2 d S . .
O1 O 0.28816(7) 0.2500 0.5890(2) 0.0449(5) Uani 1 2 d S . .
O2 O 0.36726(7) 0.2500 0.60311(18) 0.0407(5) Uani 1 2 d S . .
O3 O 0.41981(7) 0.2500 1.03883(19) 0.0460(5) Uani 1 2 d S . .
O6 O 0.68217(7) 0.2500 0.66413(18) 0.0410(5) Uani 1 2 d S . .
O5 O 0.60318(7) 0.2500 0.6427(2) 0.0472(6) Uani 1 2 d S . .
N3 N 0.69099(7) 0.2500 0.9316(2) 0.0279(5) Uani 1 2 d S . .
H3A H 0.7230 0.2500 0.9401 0.033 Uiso 1 2 calc SR . .
H3B H 0.6840 0.2500 0.8444 0.033 Uiso 1 2 calc SR . .
N1 N 0.65862(7) 0.7500 0.1269(2) 0.0289(5) Uani 1 2 d S . .
H1A H 0.6505 0.7500 0.2133 0.035 Uiso 1 2 calc SR . .
H1B H 0.6315 0.7500 0.0788 0.035 Uiso 1 2 calc SR . .
N2 N 0.50260(8) 0.2500 0.6048(2) 0.0288(5) Uani 1 2 d S . .
H2A H 0.5347 0.2500 0.6003 0.035 Uiso 1 2 calc SR . .
H2B H 0.4944 0.2500 0.6912 0.035 Uiso 1 2 calc SR . .
C27 C 0.65225(9) 0.2500 0.4476(3) 0.0264(5) Uani 1 2 d S . .
C23 C 0.33429(9) 0.2500 0.3885(3) 0.0283(6) Uani 1 2 d S . .
C26 C 0.64434(9) 0.2500 0.6018(2) 0.0262(5) Uani 1 2 d S . .
C24 C 0.45338(9) 0.2500 0.9602(3) 0.0268(6) Uani 1 2 d S . .
C22 C 0.32902(9) 0.2500 0.5436(3) 0.0279(6) Uani 1 2 d S . .
C25 C 0.50419(10) 0.2500 1.0276(3) 0.0335(6) Uani 1 2 d S . .
C16 C 0.68954(6) 0.39044(11) 0.93318(19) 0.0319(4) Uani 1 1 d . . .
C2 C 0.65971(7) 0.61071(12) 0.1329(2) 0.0350(5) Uani 1 1 d . . .
C9 C 0.50656(7) 0.38868(11) 0.60094(19) 0.0339(4) Uani 1 1 d . . .
C15 C 0.67112(7) 0.31941(11) 0.9941(2) 0.0356(5) Uani 1 1 d . . .
H18A H 0.6790 0.3193 1.0878 0.043 Uiso 1 1 calc R . .
H18B H 0.6366 0.3185 0.9863 0.043 Uiso 1 1 calc R . .
C21 C 0.72277(7) 0.43377(12) 1.0005(2) 0.0364(5) Uani 1 1 d . . .
H24 H 0.7354 0.4165 1.0803 0.044 Uiso 1 1 calc R . .
C10 C 0.54375(8) 0.42551(13) 0.5368(2) 0.0428(5) Uani 1 1 d . . .
H13 H 0.5546 0.4078 0.4555 0.051 Uiso 1 1 calc R . .
C3 C 0.62804(7) 0.57730(13) 0.0447(2) 0.0403(5) Uani 1 1 d . . .
H3 H 0.6218 0.6000 -0.0366 0.048 Uiso 1 1 calc R . .
C8 C 0.48412(7) 0.32022(11) 0.5415(2) 0.0361(5) Uani 1 1 d . . .
H11A H 0.4497 0.3227 0.5529 0.043 Uiso 1 1 calc R . .
H11B H 0.4908 0.3189 0.4471 0.043 Uiso 1 1 calc R . .
C14 C 0.49106(8) 0.41618(12) 0.7217(2) 0.0393(5) Uani 1 1 d . . .
H17 H 0.4659 0.3927 0.7656 0.047 Uiso 1 1 calc R . .
C20 C 0.73746(8) 0.50208(13) 0.9510(2) 0.0434(5) Uani 1 1 d . . .
H23 H 0.7594 0.5309 0.9981 0.052 Uiso 1 1 calc R . .
C1 C 0.68639(7) 0.68063(12) 0.0967(2) 0.0396(5) Uani 1 1 d . . .
H1C H 0.7163 0.6819 0.1451 0.048 Uiso 1 1 calc R . .
H1D H 0.6938 0.6795 0.0026 0.048 Uiso 1 1 calc R . .
C5 C 0.61428(8) 0.47684(13) 0.1967(2) 0.0481(6) Uani 1 1 d . . .
H5 H 0.5994 0.4317 0.2178 0.058 Uiso 1 1 calc R . .
C19 C 0.71987(8) 0.52749(13) 0.8326(2) 0.0465(6) Uani 1 1 d . . .
H22 H 0.7298 0.5735 0.7990 0.056 Uiso 1 1 calc R . .
C7 C 0.66775(8) 0.57655(12) 0.2541(2) 0.0421(5) Uani 1 1 d . . .
H7 H 0.6886 0.5985 0.3148 0.050 Uiso 1 1 calc R . .
C17 C 0.67188(8) 0.41665(13) 0.8133(2) 0.0423(5) Uani 1 1 d . . .
H20 H 0.6496 0.3884 0.7664 0.051 Uiso 1 1 calc R . .
C12 C 0.54966(8) 0.51425(13) 0.7136(2) 0.0475(6) Uani 1 1 d . . .
H15 H 0.5643 0.5558 0.7519 0.057 Uiso 1 1 calc R . .
C4 C 0.60569(8) 0.51072(13) 0.0767(2) 0.0456(5) Uani 1 1 d . . .
H4 H 0.5847 0.4887 0.0167 0.055 Uiso 1 1 calc R . .
C11 C 0.56467(8) 0.48800(14) 0.5923(2) 0.0494(6) Uani 1 1 d . . .
H14 H 0.5891 0.5126 0.5474 0.059 Uiso 1 1 calc R . .
C13 C 0.51265(8) 0.47843(12) 0.7778(2) 0.0452(5) Uani 1 1 d . . .
H16 H 0.5021 0.4962 0.8595 0.054 Uiso 1 1 calc R . .
C6 C 0.64503(9) 0.51006(13) 0.2857(2) 0.0478(6) Uani 1 1 d . . .
H6 H 0.6506 0.4876 0.3676 0.057 Uiso 1 1 calc R . .
C18 C 0.68724(9) 0.48461(13) 0.7632(2) 0.0491(6) Uani 1 1 d . . .
H21 H 0.6755 0.5016 0.6822 0.059 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 1.768(3) . ?
Cl5 C27 1.764(3) . ?
Cl6 C27 1.7692(16) . ?
Cl4 C25 1.753(3) . ?
Cl2 C23 1.7589(16) . ?
Cl3 C25 1.7620(17) . ?
O4 C24 1.226(3) . ?
O1 C22 1.232(3) . ?
O2 C22 1.227(3) . ?
O3 C24 1.229(3) . ?
O6 C26 1.231(3) . ?
O5 C26 1.223(3) . ?
N3 C15 1.495(2) . ?
N3 C15 1.495(2) 8_565 ?
N1 C1 1.492(2) . ?
N1 C1 1.492(2) 8_575 ?
N2 C8 1.497(2) 8_565 ?
N2 C8 1.497(2) . ?
C27 C26 1.570(3) . ?
C27 Cl6 1.7692(16) 8_565 ?
C23 C22 1.569(4) . ?
C23 Cl2 1.7589(16) 8_565 ?
C24 C25 1.576(4) . ?
C25 Cl3 1.7620(17) 8_565 ?
C16 C21 1.386(3) . ?
C16 C17 1.386(3) . ?
C16 C15 1.498(3) . ?
C2 C7 1.383(3) . ?
C2 C3 1.389(3) . ?
C2 C1 1.498(3) . ?
C9 C14 1.382(3) . ?
C9 C10 1.390(3) . ?
C9 C8 1.498(3) . ?
C21 C20 1.379(3) . ?
C10 C11 1.377(3) . ?
C3 C4 1.380(3) . ?
C14 C13 1.384(3) . ?
C20 C19 1.367(3) . ?
C5 C4 1.373(3) . ?
C5 C6 1.376(3) . ?
C19 C18 1.381(3) . ?
C7 C6 1.382(3) . ?
C17 C18 1.381(3) . ?
C12 C11 1.374(3) . ?
C12 C13 1.378(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
C15 N3 C15 111.7(2) . 8_565 ?
C1 N1 C1 112.0(2) . 8_575 ?
C8 N2 C8 113.5(2) 8_565 . ?
C26 C27 Cl5 113.98(18) . . ?
C26 C27 Cl6 109.14(11) . . ?
Cl5 C27 Cl6 108.10(10) . . ?
C26 C27 Cl6 109.14(11) . 8_565 ?
Cl5 C27 Cl6 108.10(10) . 8_565 ?
Cl6 C27 Cl6 108.23(14) . 8_565 ?
C22 C23 Cl2 109.02(11) . . ?
C22 C23 Cl2 109.02(11) . 8_565 ?
Cl2 C23 Cl2 108.98(15) . 8_565 ?
C22 C23 Cl1 113.59(18) . . ?
Cl2 C23 Cl1 108.08(10) . . ?
Cl2 C23 Cl1 108.08(10) 8_565 . ?
O5 C26 O6 129.6(2) . . ?
O5 C26 C27 117.8(2) . . ?
O6 C26 C27 112.6(2) . . ?
O4 C24 O3 128.9(2) . . ?
O4 C24 C25 116.8(2) . . ?
O3 C24 C25 114.3(2) . . ?
O2 C22 O1 128.9(3) . . ?
O2 C22 C23 113.9(2) . . ?
O1 C22 C23 117.2(2) . . ?
C24 C25 Cl4 111.55(18) . . ?
C24 C25 Cl3 109.23(12) . . ?
Cl4 C25 Cl3 108.92(11) . . ?
C24 C25 Cl3 109.23(12) . 8_565 ?
Cl4 C25 Cl3 108.92(11) . 8_565 ?
Cl3 C25 Cl3 108.95(15) . 8_565 ?
C21 C16 C17 118.54(19) . . ?
C21 C16 C15 120.07(18) . . ?
C17 C16 C15 121.27(19) . . ?
C7 C2 C3 118.7(2) . . ?
C7 C2 C1 120.02(19) . . ?
C3 C2 C1 121.28(19) . . ?
C14 C9 C10 118.5(2) . . ?
C14 C9 C8 120.64(18) . . ?
C10 C9 C8 120.87(18) . . ?
N3 C15 C16 113.53(16) . . ?
C20 C21 C16 121.0(2) . . ?
C11 C10 C9 120.8(2) . . ?
C4 C3 C2 120.6(2) . . ?
N2 C8 C9 111.49(15) . . ?
C9 C14 C13 120.5(2) . . ?
C19 C20 C21 120.1(2) . . ?
N1 C1 C2 112.38(16) . . ?
C4 C5 C6 119.6(2) . . ?
C20 C19 C18 119.8(2) . . ?
C6 C7 C2 120.4(2) . . ?
C18 C17 C16 120.2(2) . . ?
C11 C12 C13 119.3(2) . . ?
C5 C4 C3 120.3(2) . . ?
C12 C11 C10 120.4(2) . . ?
C12 C13 C14 120.5(2) . . ?
C5 C6 C7 120.5(2) . . ?
C19 C18 C17 120.4(2) . . ?

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
N1 H1B O4 0.90 2.49 3.126(3) 127.9 5_666

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.048
