# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_y3005
_database_code_depnum_ccdc_archive 'CCDC 1040317'
_audit_update_record             
;
2014-12-24 deposited with the CCDC.	2019-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H24 Br2 Cl2 Cu N2 O2'
_chemical_formula_weight         738.77

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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                   10.515(2)
_cell_length_b                   18.508(4)
_cell_length_c                   15.602(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.547(3)
_cell_angle_gamma                90.00
_cell_volume                     2910.5(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    5651
_cell_measurement_theta_min      2.201
_cell_measurement_theta_max      31.507

_exptl_crystal_description       Chip
_exptl_crystal_colour            Black
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1468
_exptl_absorpt_coefficient_mu    3.711
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.3831
_exptl_absorpt_correction_T_max  0.5391
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            18540
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         31.51
_reflns_number_total             4821
_reflns_number_gt                4132
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_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)+(0.0351P)²+0.1600P] 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         4821
_refine_ls_number_parameters     179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0751
_refine_ls_wR_factor_gt          0.0710
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_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
Cu1 Cu 0.5000 0.098570(17) 0.2500 0.01812(8) Uani 1 2 d S . .
Br1 Br 0.738911(18) 0.042175(10) 0.554321(12) 0.02504(6) Uani 1 1 d . . .
Cl1 Cl 0.33373(5) 0.17074(3) 0.65995(3) 0.03704(14) Uani 1 1 d . . .
O1 O 0.55751(13) 0.07811(7) 0.37335(8) 0.0219(3) Uani 1 1 d . . .
N1 N 0.31973(14) 0.12585(8) 0.25347(9) 0.0195(3) Uani 1 1 d . . .
C1 C 0.37738(17) 0.13244(10) 0.41614(11) 0.0187(3) Uani 1 1 d . . .
C2 C 0.50307(17) 0.09841(9) 0.43410(11) 0.0177(3) Uani 1 1 d . . .
C3 C 0.57005(17) 0.08641(9) 0.52611(12) 0.0194(3) Uani 1 1 d . . .
C4 C 0.51895(18) 0.10731(10) 0.59420(12) 0.0226(4) Uani 1 1 d . . .
H4 H 0.5664 0.0980 0.6547 0.027 Uiso 1 1 calc R . .
C5 C 0.39706(19) 0.14225(10) 0.57333(12) 0.0240(4) Uani 1 1 d . . .
C6 C 0.32618(18) 0.15503(10) 0.48646(12) 0.0223(4) Uani 1 1 d . . .
H6 H 0.2429 0.1790 0.4734 0.027 Uiso 1 1 calc R . .
C7 C 0.29142(17) 0.14150(10) 0.32662(12) 0.0200(3) Uani 1 1 d . . .
H7 H 0.2057 0.1608 0.3209 0.024 Uiso 1 1 calc R . .
C8 C 0.21565(17) 0.13824(10) 0.17144(12) 0.0212(4) Uani 1 1 d . . .
C9 C 0.21478(19) 0.20421(10) 0.12743(12) 0.0236(4) Uani 1 1 d . . .
C10 C 0.1150(2) 0.21575(11) 0.04819(13) 0.0285(4) Uani 1 1 d . . .
H10 H 0.1121 0.2601 0.0171 0.034 Uiso 1 1 calc R . .
C11 C 0.0201(2) 0.16368(12) 0.01416(13) 0.0319(5) Uani 1 1 d . . .
H11 H -0.0476 0.1725 -0.0399 0.038 Uiso 1 1 calc R . .
C12 C 0.02334(19) 0.09861(12) 0.05861(13) 0.0315(5) Uani 1 1 d . . .
H12 H -0.0431 0.0633 0.0352 0.038 Uiso 1 1 calc R . .
C13 C 0.12312(19) 0.08426(11) 0.13747(13) 0.0268(4) Uani 1 1 d . . .
C14 C 0.3193(2) 0.26034(11) 0.16422(13) 0.0301(4) Uani 1 1 d . . .
H14A H 0.3014 0.3032 0.1257 0.036 Uiso 1 1 calc R . .
H14B H 0.4067 0.2407 0.1661 0.036 Uiso 1 1 calc R . .
H14C H 0.3181 0.2737 0.2248 0.036 Uiso 1 1 calc R . .
C15 C 0.1334(3) 0.01134(14) 0.18243(16) 0.0441(6) Uani 1 1 d . . .
H15A H 0.2186 -0.0110 0.1841 0.053 Uiso 1 1 calc R . .
H15B H 0.0608 -0.0197 0.1488 0.053 Uiso 1 1 calc R . .
H15C H 0.1276 0.0174 0.2436 0.053 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
Cu1 O1 1.8841(12) 2_655 ?
Cu1 O1 1.8841(12) . ?
Cu1 N1 1.9772(15) . ?
Cu1 N1 1.9772(15) 2_655 ?
Br1 C3 1.8899(18) . ?
Cl1 C5 1.7495(18) . ?
O1 C2 1.295(2) . ?
N1 C7 1.292(2) . ?
N1 C8 1.446(2) . ?
C1 C6 1.416(2) . ?
C1 C2 1.418(2) . ?
C1 C7 1.441(2) . ?
C2 C3 1.425(2) . ?
C3 C4 1.376(2) . ?
C4 C5 1.389(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.368(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C13 1.390(3) . ?
C8 C9 1.400(3) . ?
C9 C10 1.392(3) . ?
C9 C14 1.503(3) . ?
C10 C11 1.380(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.396(3) . ?
C12 H12 0.9500 . ?
C13 C15 1.511(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
O1 Cu1 O1 156.81(8) 2_655 . ?
O1 Cu1 N1 92.75(6) 2_655 . ?
O1 Cu1 N1 93.13(6) . . ?
O1 Cu1 N1 93.13(6) 2_655 2_655 ?
O1 Cu1 N1 92.75(6) . 2_655 ?
N1 Cu1 N1 150.41(9) . 2_655 ?
C2 O1 Cu1 127.53(12) . . ?
C7 N1 C8 116.08(15) . . ?
C7 N1 Cu1 123.05(12) . . ?
C8 N1 Cu1 120.41(11) . . ?
C6 C1 C2 121.11(16) . . ?
C6 C1 C7 116.40(16) . . ?
C2 C1 C7 122.36(15) . . ?
O1 C2 C1 124.45(15) . . ?
O1 C2 C3 119.84(16) . . ?
C1 C2 C3 115.71(15) . . ?
C4 C3 C2 122.99(16) . . ?
C4 C3 Br1 119.32(13) . . ?
C2 C3 Br1 117.66(13) . . ?
C3 C4 C5 119.16(17) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 121.23(16) . . ?
C6 C5 Cl1 119.55(15) . . ?
C4 C5 Cl1 119.21(14) . . ?
C5 C6 C1 119.76(17) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
N1 C7 C1 126.26(16) . . ?
N1 C7 H7 116.9 . . ?
C1 C7 H7 116.9 . . ?
C13 C8 C9 122.27(17) . . ?
C13 C8 N1 119.65(16) . . ?
C9 C8 N1 118.05(16) . . ?
C10 C9 C8 117.88(18) . . ?
C10 C9 C14 121.20(18) . . ?
C8 C9 C14 120.92(17) . . ?
C11 C10 C9 120.96(19) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 120.17(18) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 120.77(19) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C8 C13 C12 117.90(19) . . ?
C8 C13 C15 121.02(18) . . ?
C12 C13 C15 121.03(19) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
O1 Cu1 O1 C2 -122.09(15) 2_655 . . . ?
N1 Cu1 O1 C2 -17.63(15) . . . . ?
N1 Cu1 O1 C2 133.37(15) 2_655 . . . ?
O1 Cu1 N1 C7 174.75(15) 2_655 . . . ?
O1 Cu1 N1 C7 17.20(15) . . . . ?
N1 Cu1 N1 C7 -83.98(15) 2_655 . . . ?
O1 Cu1 N1 C8 -13.29(14) 2_655 . . . ?
O1 Cu1 N1 C8 -170.85(14) . . . . ?
N1 Cu1 N1 C8 87.98(13) 2_655 . . . ?
Cu1 O1 C2 C1 9.1(3) . . . . ?
Cu1 O1 C2 C3 -171.35(12) . . . . ?
C6 C1 C2 O1 -178.10(17) . . . . ?
C7 C1 C2 O1 6.2(3) . . . . ?
C6 C1 C2 C3 2.3(3) . . . . ?
C7 C1 C2 C3 -173.39(16) . . . . ?
O1 C2 C3 C4 179.19(17) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
O1 C2 C3 Br1 1.1(2) . . . . ?
C1 C2 C3 Br1 -179.33(12) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
Br1 C3 C4 C5 177.60(14) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C3 C4 C5 Cl1 -178.53(14) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
Cl1 C5 C6 C1 179.64(14) . . . . ?
C2 C1 C6 C5 -1.8(3) . . . . ?
C7 C1 C6 C5 174.18(17) . . . . ?
C8 N1 C7 C1 178.61(17) . . . . ?
Cu1 N1 C7 C1 -9.1(3) . . . . ?
C6 C1 C7 N1 178.51(18) . . . . ?
C2 C1 C7 N1 -5.6(3) . . . . ?
C7 N1 C8 C13 -87.7(2) . . . . ?
Cu1 N1 C8 C13 99.84(17) . . . . ?
C7 N1 C8 C9 94.34(19) . . . . ?
Cu1 N1 C8 C9 -78.15(19) . . . . ?
C13 C8 C9 C10 1.6(3) . . . . ?
N1 C8 C9 C10 179.58(16) . . . . ?
C13 C8 C9 C14 -177.67(18) . . . . ?
N1 C8 C9 C14 0.3(2) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C14 C9 C10 C11 179.22(18) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C10 C11 C12 C13 -0.9(3) . . . . ?
C9 C8 C13 C12 -2.8(3) . . . . ?
N1 C8 C13 C12 179.34(17) . . . . ?
C9 C8 C13 C15 174.8(2) . . . . ?
N1 C8 C13 C15 -3.1(3) . . . . ?
C11 C12 C13 C8 2.4(3) . . . . ?
C11 C12 C13 C15 -175.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        31.51
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.652
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.090
####################################################################### 
# 
# 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_y2984
_database_code_depnum_ccdc_archive 'CCDC 1040318'
_audit_update_record             
;
2014-12-24 deposited with the CCDC.	2019-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 Br Cl N O'
_chemical_formula_weight         338.62

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   12.621(5)
_cell_length_b                   9.092(3)
_cell_length_c                   13.389(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.556(4)
_cell_angle_gamma                90.00
_cell_volume                     1374.4(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    4766
_cell_measurement_theta_min      2.813
_cell_measurement_theta_max      30.031

_exptl_crystal_description       Chunk
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    3.176
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.4115
_exptl_absorpt_correction_T_max  0.5911
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10049
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0578
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         30.03
_reflns_number_total             3954
_reflns_number_gt                2799
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_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)+(0.0252P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3954
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0740
_refine_ls_wR_factor_gt          0.0698
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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
Br1 Br 0.57884(2) 0.24596(2) 0.497635(19) 0.02287(7) Uani 1 1 d . . .
Cl1 Cl 0.84738(5) 0.54823(7) 0.88772(5) 0.02985(15) Uani 1 1 d . . .
O1 O 0.38307(14) 0.35102(18) 0.55058(13) 0.0236(4) Uani 1 1 d . . .
N1 N 0.29029(16) 0.4858(2) 0.66274(15) 0.0203(4) Uani 1 1 d . . .
C1 C 0.48890(19) 0.3950(2) 0.62994(17) 0.0179(5) Uani 1 1 d . . .
C2 C 0.5922(2) 0.3586(2) 0.62139(17) 0.0187(5) Uani 1 1 d . . .
C3 C 0.70231(19) 0.4032(2) 0.70028(17) 0.0206(5) Uani 1 1 d . . .
H3 H 0.7716 0.3775 0.6932 0.025 Uiso 1 1 calc R . .
C4 C 0.7102(2) 0.4865(2) 0.79065(18) 0.0214(5) Uani 1 1 d . . .
C5 C 0.6107(2) 0.5226(2) 0.80286(19) 0.0212(5) Uani 1 1 d . . .
H5 H 0.6178 0.5782 0.8656 0.025 Uiso 1 1 calc R . .
C6 C 0.49982(19) 0.4774(2) 0.72315(18) 0.0183(5) Uani 1 1 d . . .
C7 C 0.3947(2) 0.5197(2) 0.73508(19) 0.0208(5) Uani 1 1 d . . .
H7 H 0.4042 0.5745 0.7990 0.025 Uiso 1 1 calc R . .
C8 C 0.19137(18) 0.5334(2) 0.68033(18) 0.0175(5) Uani 1 1 d . . .
C9 C 0.1784(2) 0.4863(2) 0.77439(18) 0.0193(5) Uani 1 1 d . . .
C10 C 0.0814(2) 0.5369(2) 0.78672(19) 0.0224(5) Uani 1 1 d . . .
H10 H 0.0708 0.5061 0.8494 0.027 Uiso 1 1 calc R . .
C11 C -0.0004(2) 0.6314(3) 0.70949(18) 0.0275(5) Uani 1 1 d . . .
H11 H -0.0652 0.6674 0.7204 0.033 Uiso 1 1 calc R . .
C12 C 0.0129(2) 0.6730(3) 0.61662(19) 0.0259(5) Uani 1 1 d . . .
H12 H -0.0441 0.7366 0.5633 0.031 Uiso 1 1 calc R . .
C13 C 0.10765(19) 0.6241(2) 0.59898(18) 0.0204(5) Uani 1 1 d . . .
C14 C 0.2625(2) 0.3800(3) 0.85753(18) 0.0257(5) Uani 1 1 d . . .
H14A H 0.3353 0.4316 0.9072 0.031 Uiso 1 1 calc R . .
H14B H 0.2815 0.3014 0.8181 0.031 Uiso 1 1 calc R . .
H14C H 0.2256 0.3375 0.9017 0.031 Uiso 1 1 calc R . .
C15 C 0.1214(2) 0.6714(3) 0.49790(18) 0.0286(6) Uani 1 1 d . . .
H15A H 0.1786 0.7523 0.5181 0.034 Uiso 1 1 calc R . .
H15B H 0.0447 0.7043 0.4396 0.034 Uiso 1 1 calc R . .
H15C H 0.1500 0.5883 0.4700 0.034 Uiso 1 1 calc R . .
H1O H 0.331(3) 0.382(4) 0.578(3) 0.084(12) Uiso 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
Br1 C2 1.890(2) . ?
Cl1 C4 1.729(2) . ?
O1 C1 1.343(3) . ?
O1 H1O 0.93(3) . ?
N1 C7 1.276(3) . ?
N1 C8 1.437(3) . ?
C1 C2 1.398(3) . ?
C1 C6 1.409(3) . ?
C2 C3 1.378(3) . ?
C3 C4 1.393(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(3) . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.457(3) . ?
C7 H7 0.9500 . ?
C8 C13 1.398(3) . ?
C8 C9 1.407(3) . ?
C9 C10 1.385(3) . ?
C9 C14 1.497(3) . ?
C10 C11 1.386(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 C15 1.502(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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 O1 H1O 103.1(19) . . ?
C7 N1 C8 118.7(2) . . ?
O1 C1 C2 119.9(2) . . ?
O1 C1 C6 121.9(2) . . ?
C2 C1 C6 118.2(2) . . ?
C3 C2 C1 121.7(2) . . ?
C3 C2 Br1 119.69(17) . . ?
C1 C2 Br1 118.62(16) . . ?
C2 C3 C4 118.8(2) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 121.2(2) . . ?
C5 C4 Cl1 119.58(18) . . ?
C3 C4 Cl1 119.20(18) . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 C7 119.4(2) . . ?
C1 C6 C7 120.3(2) . . ?
N1 C7 C6 122.3(2) . . ?
N1 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
C13 C8 C9 121.8(2) . . ?
C13 C8 N1 117.37(19) . . ?
C9 C8 N1 120.78(19) . . ?
C10 C9 C8 117.9(2) . . ?
C10 C9 C14 119.7(2) . . ?
C8 C9 C14 122.3(2) . . ?
C9 C10 C11 121.4(2) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C12 C11 C10 119.4(2) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 121.7(2) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C12 C13 C8 117.6(2) . . ?
C12 C13 C15 121.1(2) . . ?
C8 C13 C15 121.3(2) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
O1 C1 C2 C3 179.20(19) . . . . ?
C6 C1 C2 C3 -1.0(3) . . . . ?
O1 C1 C2 Br1 -0.6(3) . . . . ?
C6 C1 C2 Br1 179.22(15) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
Br1 C2 C3 C4 179.80(16) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C2 C3 C4 Cl1 -177.87(17) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
Cl1 C4 C5 C6 177.86(16) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C5 C6 C7 -178.2(2) . . . . ?
O1 C1 C6 C5 -179.20(19) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
O1 C1 C6 C7 -1.0(3) . . . . ?
C2 C1 C6 C7 179.21(19) . . . . ?
C8 N1 C7 C6 -179.24(19) . . . . ?
C5 C6 C7 N1 177.6(2) . . . . ?
C1 C6 C7 N1 -0.6(3) . . . . ?
C7 N1 C8 C13 120.2(2) . . . . ?
C7 N1 C8 C9 -61.6(3) . . . . ?
C13 C8 C9 C10 -2.3(3) . . . . ?
N1 C8 C9 C10 179.7(2) . . . . ?
C13 C8 C9 C14 175.2(2) . . . . ?
N1 C8 C9 C14 -2.8(3) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C14 C9 C10 C11 -177.8(2) . . . . ?
C9 C10 C11 C12 1.9(4) . . . . ?
C10 C11 C12 C13 -1.0(4) . . . . ?
C11 C12 C13 C8 -1.4(4) . . . . ?
C11 C12 C13 C15 -179.5(2) . . . . ?
C9 C8 C13 C12 3.1(3) . . . . ?
N1 C8 C13 C12 -178.8(2) . . . . ?
C9 C8 C13 C15 -178.9(2) . . . . ?
N1 C8 C13 C15 -0.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        30.03
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         1.143
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.090
