# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_121212b_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H32 Cl4 Cu2 N4 O4'
_chemical_formula_weight         661.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   11.6403(9)
_cell_length_b                   14.5767(11)
_cell_length_c                   16.4463(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2790.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      27.70

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1352
_exptl_absorpt_coefficient_mu    1.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7340
_exptl_absorpt_correction_T_max  0.8006
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22830
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         27.69
_reflns_number_total             3261
_reflns_number_gt                2676
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0348P)²+1.1856P] 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         3261
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0722
_refine_ls_wR_factor_gt          0.0676
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
C1 C 0.23725(18) 0.47212(16) 0.27851(11) 0.0427(5) Uani 1 1 d . . .
Cl1 Cl 0.29414(4) 0.49414(4) 0.49771(3) 0.04699(13) Uani 1 1 d . . .
Cu1 Cu 0.12258(2) 0.439212(16) 0.462084(13) 0.03598(9) Uani 1 1 d . . .
N1 N 0.16813(14) 0.42418(11) 0.34287(9) 0.0355(3) Uani 1 1 d . . .
O1 O 0.13826(15) 0.33970(12) 0.23084(8) 0.0597(4) Uani 1 1 d . . .
C2 C 0.1907(2) 0.42510(19) 0.20153(13) 0.0603(6) Uani 1 1 d . . .
H2A H 0.1341 0.4635 0.1748 0.072 Uiso 1 1 calc R . .
H2B H 0.2525 0.4122 0.1636 0.072 Uiso 1 1 calc R . .
Cl2 Cl 0.04473(5) 0.45400(4) 0.58769(3) 0.04468(13) Uani 1 1 d . . .
N2 N 0.04236(14) 0.31277(11) 0.43474(9) 0.0361(3) Uani 1 1 d . . .
O2 O 0.01502(16) 0.21353(11) 0.33192(9) 0.0636(5) Uani 1 1 d . . .
C3 C 0.12400(18) 0.35434(15) 0.30976(11) 0.0407(4) Uani 1 1 d . . .
C4 C 0.3635(2) 0.4493(2) 0.29183(16) 0.0623(7) Uani 1 1 d . . .
H4A H 0.3870 0.4706 0.3445 0.093 Uiso 1 1 calc R . .
H4B H 0.4090 0.4788 0.2508 0.093 Uiso 1 1 calc R . .
H4C H 0.3742 0.3841 0.2886 0.093 Uiso 1 1 calc R . .
C5 C 0.2156(2) 0.57399(17) 0.27943(16) 0.0633(7) Uani 1 1 d . . .
H5A H 0.1347 0.5853 0.2739 0.095 Uiso 1 1 calc R . .
H5B H 0.2558 0.6022 0.2351 0.095 Uiso 1 1 calc R . .
H5C H 0.2423 0.5993 0.3299 0.095 Uiso 1 1 calc R . .
C6 C -0.03006(16) 0.23920(13) 0.47209(12) 0.0377(4) Uani 1 1 d . . .
C7 C -0.0340(3) 0.16759(18) 0.40352(15) 0.0719(8) Uani 1 1 d . . .
H7A H 0.0110 0.1140 0.4179 0.086 Uiso 1 1 calc R . .
H7B H -0.1125 0.1486 0.3930 0.086 Uiso 1 1 calc R . .
C8 C 0.05756(18) 0.29098(13) 0.36118(12) 0.0420(5) Uani 1 1 d . . .
C9 C -0.1458(2) 0.27807(19) 0.4928(2) 0.0747(8) Uani 1 1 d . . .
H9A H -0.1369 0.3272 0.5311 0.112 Uiso 1 1 calc R . .
H9B H -0.1929 0.2309 0.5162 0.112 Uiso 1 1 calc R . .
H9C H -0.1817 0.3009 0.4443 0.112 Uiso 1 1 calc R . .
C10 C 0.0281(2) 0.20112(17) 0.54653(16) 0.0593(6) Uani 1 1 d . . .
H10A H 0.1023 0.1774 0.5319 0.089 Uiso 1 1 calc R . .
H10B H -0.0179 0.1527 0.5690 0.089 Uiso 1 1 calc R . .
H10C H 0.0371 0.2490 0.5862 0.089 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0394(11) 0.0602(12) 0.0285(9) 0.0102(9) 0.0056(8) -0.0031(9)
Cl1 0.0403(3) 0.0548(3) 0.0459(3) -0.0096(2) -0.0061(2) -0.0056(2)
Cu1 0.03615(14) 0.04632(15) 0.02547(12) -0.00395(9) 0.00187(9) -0.00502(10)
N1 0.0349(8) 0.0463(9) 0.0253(7) 0.0021(6) 0.0037(6) -0.0029(7)
O1 0.0818(12) 0.0717(11) 0.0254(7) -0.0082(7) 0.0059(7) -0.0135(9)
C2 0.0675(16) 0.0846(18) 0.0288(10) 0.0069(10) 0.0072(10) -0.0104(13)
Cl2 0.0502(3) 0.0584(3) 0.0254(2) -0.00152(19) 0.00229(19) 0.0052(2)
N2 0.0432(9) 0.0348(8) 0.0304(7) 0.0003(6) 0.0022(7) -0.0061(7)
O2 0.0910(13) 0.0562(10) 0.0435(8) -0.0162(7) 0.0059(8) -0.0281(9)
C3 0.0449(11) 0.0515(12) 0.0257(8) -0.0018(8) 0.0018(8) -0.0005(9)
C4 0.0419(13) 0.096(2) 0.0488(13) 0.0175(13) 0.0091(10) 0.0012(12)
C5 0.0682(17) 0.0632(15) 0.0586(14) 0.0205(12) 0.0116(13) -0.0032(13)
C6 0.0371(10) 0.0322(9) 0.0438(10) 0.0025(8) 0.0031(8) -0.0034(8)
C7 0.105(2) 0.0537(15) 0.0575(15) -0.0083(12) 0.0118(15) -0.0301(15)
C8 0.0494(12) 0.0413(11) 0.0352(9) -0.0043(8) -0.0012(9) -0.0061(9)
C9 0.0393(13) 0.0568(15) 0.128(3) 0.0170(16) 0.0120(15) 0.0032(11)
C10 0.0613(15) 0.0532(14) 0.0635(14) 0.0220(11) -0.0050(12) -0.0020(11)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.502(2) . ?
C1 C5 1.506(3) . ?
C1 C4 1.523(3) . ?
C1 C2 1.538(3) . ?
Cl1 Cu1 2.2299(6) . ?
Cu1 N1 2.0429(15) . ?
Cu1 N2 2.1144(16) . ?
Cu1 Cl2 2.2660(5) . ?
Cu1 Cl2 2.6241(6) 5_566 ?
N1 C3 1.264(3) . ?
O1 C3 1.326(2) . ?
O1 C2 1.468(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
Cl2 Cu1 2.6240(6) 5_566 ?
N2 C8 1.263(2) . ?
N2 C6 1.496(2) . ?
O2 C8 1.323(2) . ?
O2 C7 1.470(3) . ?
C3 C8 1.472(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C9 1.501(3) . ?
C6 C10 1.505(3) . ?
C6 C7 1.537(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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
N1 C1 C5 111.21(18) . . ?
N1 C1 C4 108.30(17) . . ?
C5 C1 C4 112.1(2) . . ?
N1 C1 C2 100.61(17) . . ?
C5 C1 C2 112.9(2) . . ?
C4 C1 C2 111.2(2) . . ?
N1 Cu1 N2 79.46(6) . . ?
N1 Cu1 Cl1 93.34(5) . . ?
N2 Cu1 Cl1 139.85(5) . . ?
N1 Cu1 Cl2 171.46(5) . . ?
N2 Cu1 Cl2 95.75(4) . . ?
Cl1 Cu1 Cl2 94.84(2) . . ?
N1 Cu1 Cl2 87.53(5) . 5_566 ?
N2 Cu1 Cl2 97.06(5) . 5_566 ?
Cl1 Cu1 Cl2 122.25(2) . 5_566 ?
Cl2 Cu1 Cl2 86.052(18) . 5_566 ?
C3 N1 C1 106.79(16) . . ?
C3 N1 Cu1 113.24(13) . . ?
C1 N1 Cu1 139.95(13) . . ?
C3 O1 C2 103.71(17) . . ?
O1 C2 C1 104.72(16) . . ?
O1 C2 H2A 110.8 . . ?
C1 C2 H2A 110.8 . . ?
O1 C2 H2B 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
Cu1 Cl2 Cu1 93.950(18) . 5_566 ?
C8 N2 C6 106.97(16) . . ?
C8 N2 Cu1 111.16(13) . . ?
C6 N2 Cu1 141.85(12) . . ?
C8 O2 C7 104.04(16) . . ?
N1 C3 O1 120.05(19) . . ?
N1 C3 C8 118.13(17) . . ?
O1 C3 C8 121.82(18) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 C9 109.17(17) . . ?
N2 C6 C10 110.16(16) . . ?
C9 C6 C10 111.0(2) . . ?
N2 C6 C7 101.68(15) . . ?
C9 C6 C7 113.3(2) . . ?
C10 C6 C7 111.1(2) . . ?
O2 C7 C6 105.47(17) . . ?
O2 C7 H7A 110.6 . . ?
C6 C7 H7A 110.6 . . ?
O2 C7 H7B 110.6 . . ?
C6 C7 H7B 110.6 . . ?
H7A C7 H7B 108.8 . . ?
N2 C8 O2 120.69(19) . . ?
N2 C8 C3 117.78(17) . . ?
O2 C8 C3 121.53(17) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.69
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 973034'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_e:\single~1\131205~1\131205~1\jwg

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H16 Br2 Cu N2 O2'
_chemical_formula_weight         419.61

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'
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   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                   10.506(5)
_cell_length_b                   12.627(6)
_cell_length_c                   12.057(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.714(5)
_cell_angle_gamma                90.00
_cell_volume                     1441.1(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.934
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             820
_exptl_absorpt_coefficient_mu    7.053
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.3190
_exptl_absorpt_correction_T_max  0.3476
_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            11871
_diffrn_reflns_av_R_equivalents  0.1099
_diffrn_reflns_av_sigmaI/netI    0.1222
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         27.57
_reflns_number_total             3309
_reflns_number_gt                1500
_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)+(0.0797P)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         3309
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1637
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1699
_refine_ls_wR_factor_gt          0.1252
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_restrained_S_all      0.933
_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
Br1 Br 0.66083(9) 0.04753(8) 0.21552(9) 0.0616(3) Uani 1 1 d . . .
Cu1 Cu 0.89615(10) 0.09694(8) 0.34918(10) 0.0485(3) Uani 1 1 d . . .
O1 O 0.9356(7) 0.4013(5) 0.4602(6) 0.0690(19) Uani 1 1 d . . .
N1 N 0.8427(6) 0.2425(5) 0.3870(6) 0.0419(16) Uani 1 1 d . . .
C1 C 0.6690(10) 0.2324(8) 0.4747(10) 0.076(3) Uani 1 1 d . . .
H1A H 0.6233 0.1705 0.4282 0.114 Uiso 1 1 calc R . .
H1B H 0.6023 0.2729 0.4920 0.114 Uiso 1 1 calc R . .
H1C H 0.7460 0.2113 0.5507 0.114 Uiso 1 1 calc R . .
Br2 Br 0.99169(10) -0.07496(8) 0.35994(9) 0.0637(3) Uani 1 1 d . . .
O2 O 1.1852(6) 0.3395(5) 0.4507(5) 0.0597(17) Uani 1 1 d . . .
N2 N 1.0819(6) 0.1819(6) 0.3793(6) 0.0420(16) Uani 1 1 d . . .
C2 C 0.6140(11) 0.3272(9) 0.2741(9) 0.087(4) Uani 1 1 d . . .
H2A H 0.5695 0.2635 0.2314 0.130 Uiso 1 1 calc R . .
H2B H 0.6572 0.3632 0.2291 0.130 Uiso 1 1 calc R . .
H2C H 0.5444 0.3724 0.2811 0.130 Uiso 1 1 calc R . .
C3 C 0.7250(9) 0.2998(7) 0.4005(8) 0.050(2) Uani 1 1 d . . .
C4 C 0.8014(10) 0.4004(8) 0.4719(10) 0.073(3) Uani 1 1 d . . .
H4A H 0.7462 0.4634 0.4355 0.088 Uiso 1 1 calc R . .
H4B H 0.8185 0.3961 0.5575 0.088 Uiso 1 1 calc R . .
C5 C 0.9444(9) 0.3063(7) 0.4208(7) 0.045(2) Uani 1 1 d . . .
C6 C 1.0775(8) 0.2736(7) 0.4158(7) 0.044(2) Uani 1 1 d . . .
C7 C 1.2902(8) 0.2810(8) 0.4244(8) 0.059(3) Uani 1 1 d . . .
H7A H 1.3800 0.2776 0.4970 0.071 Uiso 1 1 calc R . .
H7B H 1.3046 0.3148 0.3585 0.071 Uiso 1 1 calc R . .
C8 C 1.2271(8) 0.1693(7) 0.3857(8) 0.048(2) Uani 1 1 d . . .
C9 C 1.2139(10) 0.1415(9) 0.2579(9) 0.076(3) Uani 1 1 d . . .
H9A H 1.1618 0.1961 0.2008 0.114 Uiso 1 1 calc R . .
H9B H 1.1651 0.0752 0.2318 0.114 Uiso 1 1 calc R . .
H9C H 1.3064 0.1357 0.2608 0.114 Uiso 1 1 calc R . .
C10 C 1.3105(9) 0.0867(8) 0.4832(10) 0.081(3) Uani 1 1 d . . .
H10A H 1.3174 0.1087 0.5618 0.121 Uiso 1 1 calc R . .
H10B H 1.4036 0.0798 0.4876 0.121 Uiso 1 1 calc R . .
H10C H 1.2629 0.0196 0.4614 0.121 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0520(6) 0.0605(7) 0.0723(7) -0.0066(5) 0.0269(5) -0.0104(5)
Cu1 0.0440(6) 0.0411(7) 0.0653(7) -0.0024(5) 0.0284(5) -0.0022(5)
O1 0.077(5) 0.054(5) 0.088(5) -0.021(4) 0.047(4) -0.013(3)
N1 0.043(4) 0.042(4) 0.049(4) 0.000(3) 0.028(3) 0.001(3)
C1 0.075(7) 0.082(8) 0.109(8) 0.008(7) 0.074(7) 0.010(6)
Br2 0.0660(6) 0.0447(6) 0.0785(7) -0.0040(5) 0.0295(5) 0.0039(4)
O2 0.053(4) 0.061(4) 0.075(4) -0.015(3) 0.037(3) -0.019(3)
N2 0.037(4) 0.047(5) 0.046(4) 0.002(3) 0.022(3) -0.004(3)
C2 0.087(8) 0.088(9) 0.076(7) 0.009(6) 0.027(6) 0.049(7)
C3 0.055(5) 0.045(6) 0.061(6) 0.000(4) 0.036(5) 0.011(4)
C4 0.091(8) 0.064(7) 0.092(8) -0.012(6) 0.065(7) 0.010(6)
C5 0.056(5) 0.037(5) 0.048(5) -0.004(4) 0.029(4) 0.000(4)
C6 0.046(5) 0.043(6) 0.044(5) 0.002(4) 0.021(4) -0.004(4)
C7 0.044(5) 0.066(7) 0.077(7) -0.001(5) 0.034(5) -0.010(5)
C8 0.034(4) 0.060(6) 0.061(6) 0.006(5) 0.032(4) 0.001(4)
C9 0.065(6) 0.112(9) 0.074(7) -0.020(6) 0.051(6) -0.009(6)
C10 0.047(6) 0.071(8) 0.114(9) 0.026(7) 0.026(6) 0.003(5)

_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 Cu1 2.3751(16) . ?
Cu1 N1 2.031(7) . ?
Cu1 N2 2.116(6) . ?
Cu1 Br2 2.3712(17) . ?
O1 C5 1.307(9) . ?
O1 C4 1.477(11) . ?
N1 C5 1.256(10) . ?
N1 C3 1.501(10) . ?
C1 C3 1.526(12) . ?
O2 C6 1.319(9) . ?
O2 C7 1.471(10) . ?
N2 C6 1.246(10) . ?
N2 C8 1.502(9) . ?
C2 C3 1.504(12) . ?
C3 C4 1.549(12) . ?
C5 C6 1.484(11) . ?
C7 C8 1.542(12) . ?
C8 C9 1.527(12) . ?
C8 C10 1.532(12) . ?

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
N1 Cu1 N2 80.0(3) . . ?
N1 Cu1 Br2 165.45(18) . . ?
N2 Cu1 Br2 96.8(2) . . ?
N1 Cu1 Br1 94.73(18) . . ?
N2 Cu1 Br1 149.39(18) . . ?
Br2 Cu1 Br1 95.05(6) . . ?
C5 O1 C4 104.4(7) . . ?
C5 N1 C3 106.3(7) . . ?
C5 N1 Cu1 112.0(5) . . ?
C3 N1 Cu1 141.4(5) . . ?
C6 O2 C7 103.6(7) . . ?
C6 N2 C8 105.8(7) . . ?
C6 N2 Cu1 111.0(5) . . ?
C8 N2 Cu1 142.7(6) . . ?
N1 C3 C2 108.3(7) . . ?
N1 C3 C1 109.9(7) . . ?
C2 C3 C1 113.3(9) . . ?
N1 C3 C4 101.7(7) . . ?
C2 C3 C4 111.2(8) . . ?
C1 C3 C4 111.7(8) . . ?
O1 C4 C3 103.8(7) . . ?
N1 C5 O1 121.5(8) . . ?
N1 C5 C6 119.4(8) . . ?
O1 C5 C6 119.1(8) . . ?
N2 C6 O2 122.7(8) . . ?
N2 C6 C5 117.0(7) . . ?
O2 C6 C5 120.3(8) . . ?
O2 C7 C8 105.1(6) . . ?
N2 C8 C9 109.0(7) . . ?
N2 C8 C10 110.0(7) . . ?
C9 C8 C10 112.9(8) . . ?
N2 C8 C7 102.3(6) . . ?
C9 C8 C7 110.8(8) . . ?
C10 C8 C7 111.3(7) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.077
_refine_diff_density_min         -1.037
_refine_diff_density_rms         0.156
_database_code_depnum_ccdc_archive 'CCDC 981179'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_130523b_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H19 Br2 Cu N3 O2'
_chemical_formula_weight         496.69

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'
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   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                   10.5479(7)
_cell_length_b                   15.7383(11)
_cell_length_c                   11.3501(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.8020(10)
_cell_angle_gamma                90.00
_cell_volume                     1856.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6363
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      27.32

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             980
_exptl_absorpt_coefficient_mu    5.491
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4930
_exptl_absorpt_correction_T_max  0.5587
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15784
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         27.41
_reflns_number_total             4219
_reflns_number_gt                3266
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0319P)²+0.5217P] 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         4219
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0282
_refine_ls_wR_factor_ref         0.0702
_refine_ls_wR_factor_gt          0.0639
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.99330(3) 0.09909(2) 0.76732(3) 0.05251(10) Uani 1 1 d . . .
C1 C 0.6851(3) -0.02631(16) 1.0095(2) 0.0349(6) Uani 1 1 d . . .
Cu1 Cu 0.79829(3) 0.047901(18) 0.81786(3) 0.03003(9) Uani 1 1 d . . .
N1 N 0.6980(2) -0.03693(12) 0.89596(19) 0.0317(5) Uani 1 1 d . . .
O1 O 0.6215(2) -0.15690(13) 0.6312(2) 0.0570(6) Uani 1 1 d . . .
Br2 Br 0.60721(3) 0.145031(17) 0.73348(3) 0.04216(9) Uani 1 1 d . . .
C2 C 0.6129(3) -0.08135(18) 1.0656(3) 0.0470(8) Uani 1 1 d . . .
H2 H 0.6046 -0.0736 1.1452 0.056 Uiso 1 1 calc R . .
N2 N 0.7473(2) -0.04330(13) 0.68285(19) 0.0341(5) Uani 1 1 d . . .
O2 O 0.7457(2) 0.07890(13) 1.16507(16) 0.0463(5) Uani 1 1 d . . .
C3 C 0.5537(3) -0.14803(18) 0.9998(3) 0.0536(8) Uani 1 1 d . . .
H3 H 0.5045 -0.1861 1.0355 0.064 Uiso 1 1 calc R . .
N3 N 0.8196(2) 0.09213(12) 0.99199(18) 0.0318(5) Uani 1 1 d . . .
C4 C 0.5660(3) -0.15941(18) 0.8816(3) 0.0472(8) Uani 1 1 d . . .
H4 H 0.5257 -0.2044 0.8369 0.057 Uiso 1 1 calc R . .
C5 C 0.6403(3) -0.10166(16) 0.8323(3) 0.0367(6) Uani 1 1 d . . .
C6 C 0.6719(3) -0.09930(16) 0.7117(2) 0.0365(6) Uani 1 1 d . . .
C7 C 0.6658(4) -0.1318(2) 0.5215(3) 0.0693(11) Uani 1 1 d . . .
H7A H 0.5944 -0.1115 0.4629 0.083 Uiso 1 1 calc R . .
H7B H 0.7055 -0.1795 0.4877 0.083 Uiso 1 1 calc R . .
C8 C 0.7640(3) -0.06070(18) 0.5568(2) 0.0438(7) Uani 1 1 d . . .
C9 C 0.8996(4) -0.0929(3) 0.5589(3) 0.0677(10) Uani 1 1 d . . .
H9A H 0.9600 -0.0516 0.5972 0.102 Uiso 1 1 calc R . .
H9B H 0.9137 -0.1020 0.4784 0.102 Uiso 1 1 calc R . .
H9C H 0.9112 -0.1454 0.6023 0.102 Uiso 1 1 calc R . .
C10 C 0.7370(4) 0.0181(2) 0.4815(3) 0.0753(12) Uani 1 1 d . . .
H10A H 0.6516 0.0378 0.4848 0.113 Uiso 1 1 calc R . .
H10B H 0.7442 0.0053 0.4003 0.113 Uiso 1 1 calc R . .
H10C H 0.7980 0.0615 0.5116 0.113 Uiso 1 1 calc R . .
C11 C 0.7548(3) 0.05075(16) 1.0562(2) 0.0341(6) Uani 1 1 d . . .
C12 C 0.8167(3) 0.1588(2) 1.1772(3) 0.0527(8) Uani 1 1 d . . .
H12A H 0.8834 0.1576 1.2475 0.063 Uiso 1 1 calc R . .
H12B H 0.7593 0.2060 1.1844 0.063 Uiso 1 1 calc R . .
C13 C 0.8766(3) 0.16773(16) 1.0627(2) 0.0382(6) Uani 1 1 d . . .
C14 C 1.0208(3) 0.1592(2) 1.0894(3) 0.0558(8) Uani 1 1 d . . .
H14A H 1.0434 0.1069 1.1314 0.084 Uiso 1 1 calc R . .
H14B H 1.0567 0.2061 1.1380 0.084 Uiso 1 1 calc R . .
H14C H 1.0542 0.1591 1.0159 0.084 Uiso 1 1 calc R . .
C15 C 0.8345(4) 0.24814(18) 0.9956(3) 0.0570(9) Uani 1 1 d . . .
H15A H 0.8696 0.2498 0.9230 0.086 Uiso 1 1 calc R . .
H15B H 0.8648 0.2963 1.0442 0.086 Uiso 1 1 calc R . .
H15C H 0.7423 0.2497 0.9769 0.086 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0472(2) 0.0681(2) 0.04497(19) -0.00267(15) 0.01573(15) -0.01597(15)
C1 0.0384(16) 0.0343(13) 0.0347(15) 0.0058(11) 0.0134(13) 0.0055(11)
Cu1 0.03449(19) 0.02953(15) 0.02646(17) -0.00002(12) 0.00632(14) -0.00293(12)
N1 0.0322(12) 0.0276(10) 0.0364(12) 0.0017(9) 0.0089(10) 0.0007(9)
O1 0.0690(16) 0.0489(12) 0.0514(14) -0.0157(10) 0.0050(12) -0.0238(11)
Br2 0.04092(17) 0.04249(16) 0.04162(17) 0.00695(12) 0.00290(13) 0.00803(12)
C2 0.054(2) 0.0448(16) 0.0479(18) 0.0127(14) 0.0244(16) 0.0056(14)
N2 0.0379(13) 0.0351(11) 0.0289(12) -0.0042(9) 0.0049(10) -0.0015(10)
O2 0.0602(14) 0.0520(12) 0.0289(10) -0.0033(9) 0.0140(10) 0.0050(10)
C3 0.054(2) 0.0406(16) 0.072(2) 0.0153(16) 0.0277(18) -0.0032(14)
N3 0.0390(13) 0.0295(10) 0.0265(11) -0.0014(9) 0.0039(10) 0.0006(9)
C4 0.0442(18) 0.0352(14) 0.063(2) 0.0025(14) 0.0124(16) -0.0063(13)
C5 0.0369(16) 0.0299(13) 0.0430(16) 0.0027(11) 0.0057(13) -0.0005(11)
C6 0.0388(16) 0.0317(13) 0.0374(15) -0.0066(11) 0.0019(13) -0.0009(11)
C7 0.087(3) 0.075(2) 0.044(2) -0.0204(18) 0.003(2) -0.024(2)
C8 0.056(2) 0.0468(16) 0.0273(14) -0.0073(12) 0.0028(14) -0.0040(14)
C9 0.067(3) 0.089(3) 0.050(2) -0.0186(19) 0.0209(19) 0.009(2)
C10 0.127(4) 0.061(2) 0.0364(19) 0.0052(16) 0.008(2) 0.009(2)
C11 0.0400(16) 0.0374(13) 0.0251(13) 0.0028(11) 0.0066(12) 0.0090(12)
C12 0.062(2) 0.0566(18) 0.0390(17) -0.0153(14) 0.0077(16) 0.0008(16)
C13 0.0451(17) 0.0363(14) 0.0298(14) -0.0067(11) -0.0034(13) 0.0022(12)
C14 0.047(2) 0.065(2) 0.052(2) -0.0111(16) -0.0021(16) -0.0038(16)
C15 0.074(2) 0.0363(15) 0.053(2) -0.0025(14) -0.0092(18) 0.0018(15)

_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 Cu1 2.3686(5) . ?
C1 N1 1.330(3) . ?
C1 C2 1.378(4) . ?
C1 C11 1.470(4) . ?
Cu1 N1 2.001(2) . ?
Cu1 N3 2.071(2) . ?
Cu1 N2 2.102(2) . ?
Cu1 Br2 2.5805(4) . ?
N1 C5 1.335(3) . ?
O1 C6 1.332(3) . ?
O1 C7 1.458(4) . ?
C2 C3 1.375(4) . ?
C2 H2 0.9300 . ?
N2 C6 1.267(3) . ?
N2 C8 1.497(3) . ?
O2 C11 1.331(3) . ?
O2 C12 1.458(4) . ?
C3 C4 1.381(5) . ?
C3 H3 0.9300 . ?
N3 C11 1.262(3) . ?
N3 C13 1.502(3) . ?
C4 C5 1.379(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.463(4) . ?
C7 C8 1.531(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C10 1.505(4) . ?
C8 C9 1.513(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 C13 1.545(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.505(4) . ?
C13 C15 1.504(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
N1 C1 C2 121.6(3) . . ?
N1 C1 C11 109.0(2) . . ?
C2 C1 C11 129.3(3) . . ?
N1 Cu1 N3 77.37(8) . . ?
N1 Cu1 N2 77.20(9) . . ?
N3 Cu1 N2 153.90(8) . . ?
N1 Cu1 Br1 151.67(6) . . ?
N3 Cu1 Br1 99.15(6) . . ?
N2 Cu1 Br1 100.41(6) . . ?
N1 Cu1 Br2 96.97(6) . . ?
N3 Cu1 Br2 96.09(6) . . ?
N2 Cu1 Br2 92.71(6) . . ?
Br1 Cu1 Br2 111.361(16) . . ?
C1 N1 C5 120.5(2) . . ?
C1 N1 Cu1 119.65(17) . . ?
C5 N1 Cu1 119.76(18) . . ?
C6 O1 C7 104.6(2) . . ?
C3 C2 C1 117.7(3) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C6 N2 C8 107.5(2) . . ?
C6 N2 Cu1 112.36(18) . . ?
C8 N2 Cu1 139.90(17) . . ?
C11 O2 C12 104.9(2) . . ?
C2 C3 C4 121.2(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C11 N3 C13 107.9(2) . . ?
C11 N3 Cu1 113.35(18) . . ?
C13 N3 Cu1 138.12(17) . . ?
C5 C4 C3 117.5(3) . . ?
C5 C4 H4 121.2 . . ?
C3 C4 H4 121.2 . . ?
N1 C5 C4 121.5(3) . . ?
N1 C5 C6 109.3(2) . . ?
C4 C5 C6 129.2(3) . . ?
N2 C6 O1 119.4(3) . . ?
N2 C6 C5 120.8(2) . . ?
O1 C6 C5 119.8(2) . . ?
O1 C7 C8 106.0(2) . . ?
O1 C7 H7A 110.5 . . ?
C8 C7 H7A 110.5 . . ?
O1 C7 H7B 110.5 . . ?
C8 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
N2 C8 C10 110.5(2) . . ?
N2 C8 C9 108.1(2) . . ?
C10 C8 C9 111.8(3) . . ?
N2 C8 C7 101.5(2) . . ?
C10 C8 C7 113.5(3) . . ?
C9 C8 C7 110.8(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 O2 119.8(2) . . ?
N3 C11 C1 120.3(2) . . ?
O2 C11 C1 119.9(2) . . ?
O2 C12 C13 106.0(2) . . ?
O2 C12 H12A 110.5 . . ?
C13 C12 H12A 110.5 . . ?
O2 C12 H12B 110.5 . . ?
C13 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
C14 C13 N3 109.6(2) . . ?
C14 C13 C15 112.2(3) . . ?
N3 C13 C15 109.8(2) . . ?
C14 C13 C12 111.5(3) . . ?
N3 C13 C12 101.2(2) . . ?
C15 C13 C12 112.0(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 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 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.41
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.071
_database_code_depnum_ccdc_archive 'CCDC 973033'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_e:\single~1\131223~1\ygz

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H19 N O2'
_chemical_formula_weight         233.30

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   14.4443(15)
_cell_length_b                   6.1524(6)
_cell_length_c                   14.5492(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.2260(10)
_cell_angle_gamma                90.00
_cell_volume                     1279.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9888
_exptl_absorpt_correction_T_max  0.9912
_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            10565
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_sigmaI/netI    0.0494
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         27.43
_reflns_number_total             2904
_reflns_number_gt                1552
_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)+(0.0570P)²+0.0716P] 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         2904
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1341
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_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
N1 N 0.66948(10) 0.2107(2) 0.61108(9) 0.0395(4) Uani 1 1 d . . .
O1 O 0.65306(10) 0.2873(2) 0.41748(9) 0.0571(4) Uani 1 1 d . . .
O2 O 0.69289(11) -0.1873(2) 0.76157(10) 0.0700(5) Uani 1 1 d . . .
C5 C 0.63876(12) 0.1565(3) 0.70064(12) 0.0425(5) Uani 1 1 d . . .
H5A H 0.6408 0.2912 0.7368 0.051 Uiso 1 1 calc R . .
C1 C 0.66104(14) 0.0326(3) 0.54439(12) 0.0488(5) Uani 1 1 d . . .
H1A H 0.5958 -0.0077 0.5284 0.059 Uiso 1 1 calc R . .
H1B H 0.6950 -0.0931 0.5717 0.059 Uiso 1 1 calc R . .
C7 C 0.80628(13) 0.0881(3) 0.78926(12) 0.0431(5) Uani 1 1 d . . .
C8 C 0.86801(15) -0.0508(3) 0.84179(14) 0.0554(5) Uani 1 1 d . . .
H8A H 0.8496 -0.1921 0.8529 0.066 Uiso 1 1 calc R . .
C3 C 0.66258(15) 0.4612(3) 0.48193(13) 0.0555(5) Uani 1 1 d . . .
H3A H 0.6304 0.5881 0.4536 0.067 Uiso 1 1 calc R . .
H3B H 0.7283 0.4975 0.4978 0.067 Uiso 1 1 calc R . .
C4 C 0.62299(14) 0.4036(3) 0.56883(13) 0.0523(5) Uani 1 1 d . . .
H4A H 0.6319 0.5239 0.6123 0.063 Uiso 1 1 calc R . .
H4B H 0.5564 0.3764 0.5539 0.063 Uiso 1 1 calc R . .
C12 C 0.83570(14) 0.2979(3) 0.77485(14) 0.0516(5) Uani 1 1 d . . .
H12A H 0.7953 0.3946 0.7402 0.062 Uiso 1 1 calc R . .
C2 C 0.70005(16) 0.1016(3) 0.45820(14) 0.0584(6) Uani 1 1 d . . .
H2A H 0.7662 0.1337 0.4740 0.070 Uiso 1 1 calc R . .
H2B H 0.6936 -0.0168 0.4137 0.070 Uiso 1 1 calc R . .
C10 C 0.98634(14) 0.2266(4) 0.86355(15) 0.0601(6) Uani 1 1 d . . .
C6 C 0.71152(14) 0.0038(3) 0.75200(12) 0.0460(5) Uani 1 1 d . . .
C14 C 0.54055(13) 0.0649(3) 0.69614(15) 0.0579(6) Uani 1 1 d . . .
H14A H 0.4964 0.1658 0.6645 0.087 Uiso 1 1 calc R . .
H14B H 0.5267 0.0416 0.7580 0.087 Uiso 1 1 calc R . .
H14C H 0.5365 -0.0707 0.6631 0.087 Uiso 1 1 calc R . .
C11 C 0.92462(15) 0.3646(3) 0.81155(14) 0.0584(6) Uani 1 1 d . . .
H11A H 0.9432 0.5060 0.8009 0.070 Uiso 1 1 calc R . .
C9 C 0.95615(16) 0.0178(4) 0.87757(15) 0.0648(6) Uani 1 1 d . . .
H9A H 0.9967 -0.0788 0.9122 0.078 Uiso 1 1 calc R . .
C13 C 1.08370(16) 0.3000(5) 0.90259(19) 0.0939(9) Uani 1 1 d . . .
H13A H 1.0920 0.4488 0.8857 0.141 Uiso 1 1 calc R . .
H13B H 1.1288 0.2107 0.8779 0.141 Uiso 1 1 calc R . .
H13C H 1.0922 0.2872 0.9690 0.141 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0511(9) 0.0372(8) 0.0293(8) 0.0006(7) 0.0032(7) 0.0029(7)
O1 0.0773(10) 0.0591(9) 0.0338(8) 0.0015(7) 0.0041(7) 0.0000(7)
O2 0.0854(11) 0.0441(9) 0.0745(11) 0.0122(8) -0.0095(8) -0.0057(8)
C5 0.0518(12) 0.0447(11) 0.0311(10) -0.0007(8) 0.0059(9) 0.0001(9)
C1 0.0643(13) 0.0433(11) 0.0388(11) -0.0030(9) 0.0075(10) 0.0030(9)
C7 0.0531(12) 0.0441(11) 0.0326(10) 0.0006(8) 0.0074(9) 0.0051(9)
C8 0.0627(14) 0.0540(13) 0.0485(13) 0.0088(10) 0.0048(11) 0.0064(11)
C3 0.0750(14) 0.0494(12) 0.0420(12) 0.0053(10) 0.0076(10) 0.0001(11)
C4 0.0695(14) 0.0430(11) 0.0445(12) 0.0035(9) 0.0083(10) 0.0099(10)
C12 0.0561(13) 0.0502(12) 0.0473(12) 0.0069(10) 0.0035(10) 0.0058(10)
C2 0.0825(16) 0.0535(12) 0.0413(12) -0.0017(10) 0.0158(11) 0.0069(12)
C10 0.0520(13) 0.0808(16) 0.0470(13) 0.0051(11) 0.0052(10) -0.0017(12)
C6 0.0615(13) 0.0442(11) 0.0325(10) 0.0029(9) 0.0075(9) 0.0022(10)
C14 0.0554(13) 0.0650(14) 0.0547(13) 0.0033(11) 0.0130(10) -0.0013(11)
C11 0.0618(14) 0.0571(13) 0.0564(14) 0.0023(11) 0.0086(11) -0.0078(11)
C9 0.0588(14) 0.0758(16) 0.0578(14) 0.0159(12) 0.0016(11) 0.0144(12)
C13 0.0632(16) 0.130(2) 0.0846(19) 0.0181(17) -0.0038(14) -0.0174(16)

_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
N1 C4 1.456(2) . ?
N1 C1 1.457(2) . ?
N1 C5 1.474(2) . ?
O1 C2 1.415(2) . ?
O1 C3 1.416(2) . ?
O2 C6 1.219(2) . ?
C5 C14 1.519(2) . ?
C5 C6 1.523(2) . ?
C1 C2 1.508(3) . ?
C7 C8 1.384(3) . ?
C7 C12 1.384(2) . ?
C7 C6 1.491(3) . ?
C8 C9 1.371(3) . ?
C3 C4 1.503(3) . ?
C12 C11 1.381(3) . ?
C10 C11 1.377(3) . ?
C10 C9 1.381(3) . ?
C10 C13 1.508(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
C4 N1 C1 110.02(14) . . ?
C4 N1 C5 112.27(14) . . ?
C1 N1 C5 114.28(13) . . ?
C2 O1 C3 109.72(14) . . ?
N1 C5 C14 116.32(15) . . ?
N1 C5 C6 107.43(14) . . ?
C14 C5 C6 111.53(15) . . ?
N1 C1 C2 109.65(15) . . ?
C8 C7 C12 118.17(19) . . ?
C8 C7 C6 118.14(17) . . ?
C12 C7 C6 123.69(18) . . ?
C9 C8 C7 120.6(2) . . ?
O1 C3 C4 111.50(16) . . ?
N1 C4 C3 109.85(15) . . ?
C11 C12 C7 120.48(19) . . ?
O1 C2 C1 111.21(16) . . ?
C11 C10 C9 117.5(2) . . ?
C11 C10 C13 121.2(2) . . ?
C9 C10 C13 121.3(2) . . ?
O2 C6 C7 120.00(18) . . ?
O2 C6 C5 120.18(18) . . ?
C7 C6 C5 119.81(16) . . ?
C10 C11 C12 121.5(2) . . ?
C8 C9 C10 121.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.43
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.035
_database_code_depnum_ccdc_archive 'CCDC 978999'
