# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 997024'
_audit_update_record             
;
2014-04-12 deposited with the CCDC.
2016-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 Br2 Cu N2 O'
_chemical_formula_weight         505.74

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   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                   7.3937(5)
_cell_length_b                   12.4939(13)
_cell_length_c                   19.6733(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.432(6)
_cell_angle_gamma                90.00
_cell_volume                     1816.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9915
_cell_measurement_theta_min      3.26
_cell_measurement_theta_max      30.00

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04



_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.849
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1004
_exptl_absorpt_coefficient_mu    5.608
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSPACK, Oxford Diffraction Ltd'
_exptl_absorpt_correction_T_min  0.777
_exptl_absorpt_correction_T_max  1.000
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_standards_number         n/a
_diffrn_measurement_device       'Oxford Diffaction X-Calibur System'
_diffrn_measurement_method       '321 frames, counting time 10 s.'
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_decay_%        n/a

_diffrn_reflns_number            9915
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_sigmaI/netI    0.1050
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         30.00
_reflns_number_total             5211
_reflns_number_gt                3506
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_publication_material  'shelxl-97, platon'

_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)+(0.0785P)²+6.7532P] 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         5211
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1198
_refine_ls_R_factor_gt           0.0739
_refine_ls_wR_factor_ref         0.1960
_refine_ls_wR_factor_gt          0.1779
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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
Cu1 Cu 0.39838(11) 0.99826(7) 0.28305(4) 0.0148(2) Uani 1 1 d . . .
Br1 Br 0.13860(9) 0.92459(7) 0.22250(4) 0.0228(2) Uani 1 1 d . . .
Br19 Br 0.71380(11) 0.78462(8) 0.61707(4) 0.0344(2) Uani 1 1 d . . .
C12 C 0.4225(9) 0.8929(5) 0.4126(3) 0.0152(13) Uani 1 1 d . . .
C13 C 0.3294(9) 0.8230(5) 0.4593(3) 0.0149(13) Uani 1 1 d . . .
C14 C 0.1525(9) 0.7858(6) 0.4425(4) 0.0212(15) Uani 1 1 d . . .
H14 H 0.0977 0.8072 0.4016 0.025 Uiso 1 1 calc R . .
C15 C 0.0602(10) 0.7192(6) 0.4849(4) 0.0216(15) Uani 1 1 d . . .
H15 H -0.0556 0.6956 0.4730 0.026 Uiso 1 1 calc R . .
C16 C 0.1436(10) 0.6871(6) 0.5466(4) 0.0229(16) Uani 1 1 d . . .
H16 H 0.0818 0.6428 0.5761 0.027 Uiso 1 1 calc R . .
C17 C 0.3157(10) 0.7208(6) 0.5638(4) 0.0235(16) Uani 1 1 d . . .
H17 H 0.3688 0.6984 0.6047 0.028 Uiso 1 1 calc R . .
C18 C 0.4137(10) 0.7885(6) 0.5207(3) 0.0174(14) Uani 1 1 d . . .
C19 C 0.5934(9) 0.8249(6) 0.5345(3) 0.0159(14) Uani 1 1 d . . .
C20 C 0.6805(9) 0.8885(6) 0.4914(4) 0.0177(14) Uani 1 1 d . . .
H20 H 0.7971 0.9107 0.5032 0.021 Uiso 1 1 calc R . .
C21 C 0.6028(9) 0.9242(6) 0.4280(3) 0.0156(13) Uani 1 1 d . . .
C22 C 0.7048(9) 0.9938(6) 0.3823(4) 0.0173(14) Uani 1 1 d . . .
C24 C 0.7459(10) 1.1041(6) 0.2840(4) 0.0201(15) Uani 1 1 d . . .
H24A H 0.8336 1.0619 0.2598 0.024 Uiso 1 1 calc R . .
H24B H 0.8104 1.1559 0.3122 0.024 Uiso 1 1 calc R . .
C25 C 0.6201(10) 1.1601(6) 0.2346(4) 0.0224(16) Uani 1 1 d . . .
H25A H 0.5553 1.2160 0.2581 0.027 Uiso 1 1 calc R . .
H25B H 0.6898 1.1936 0.1993 0.027 Uiso 1 1 calc R . .
C221 C 0.8985(9) 1.0203(6) 0.4010(4) 0.0199(15) Uani 1 1 d . . .
H22A H 0.9712 1.0143 0.3614 0.030 Uiso 1 1 calc R . .
H22B H 0.9423 0.9714 0.4352 0.030 Uiso 1 1 calc R . .
H22C H 0.9055 1.0921 0.4182 0.030 Uiso 1 1 calc R . .
N23 N 0.6330(8) 1.0334(5) 0.3269(3) 0.0172(12) Uani 1 1 d . . .
N26 N 0.4894(9) 1.0847(5) 0.2035(3) 0.0245(14) Uani 1 1 d . . .
C27 C 0.3567(12) 1.1412(7) 0.1595(4) 0.034(2) Uani 1 1 d . . .
H27A H 0.2833 1.0889 0.1350 0.041 Uiso 1 1 calc R . .
H27B H 0.4208 1.1831 0.1263 0.041 Uiso 1 1 calc R . .
C28 C 0.2354(13) 1.2136(8) 0.1982(5) 0.041(2) Uani 1 1 d . . .
H28A H 0.1833 1.1747 0.2349 0.061 Uiso 1 1 calc R . .
H28B H 0.1407 1.2399 0.1683 0.061 Uiso 1 1 calc R . .
H28C H 0.3043 1.2728 0.2160 0.061 Uiso 1 1 calc R . .
C29 C 0.5842(13) 0.9981(7) 0.1631(5) 0.034(2) Uani 1 1 d . . .
H29A H 0.6612 0.9578 0.1945 0.041 Uiso 1 1 calc R . .
H29B H 0.4926 0.9492 0.1454 0.041 Uiso 1 1 calc R . .
C30 C 0.6971(15) 1.0328(9) 0.1051(6) 0.052(3) Uani 1 1 d . . .
H30A H 0.6242 1.0738 0.0735 0.078 Uiso 1 1 calc R . .
H30B H 0.7439 0.9709 0.0825 0.078 Uiso 1 1 calc R . .
H30C H 0.7958 1.0760 0.1219 0.078 Uiso 1 1 calc R . .
O11 O 0.3282(6) 0.9190(4) 0.3585(3) 0.0215(11) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O11 1.868(5) . ?
Cu1 N23 1.967(6) . ?
Cu1 N26 2.030(6) . ?
Cu1 Br1 2.4168(11) . ?
Br19 C19 1.901(7) . ?
C12 O11 1.300(8) . ?
C12 C21 1.415(9) . ?
C12 C13 1.452(9) . ?
C13 C18 1.414(9) . ?
C13 C14 1.419(10) . ?
C14 C15 1.373(11) . ?
C15 C16 1.406(11) . ?
C16 C17 1.374(11) . ?
C17 C18 1.410(10) . ?
C18 C19 1.424(10) . ?
C19 C20 1.339(10) . ?
C20 C21 1.431(10) . ?
C21 C22 1.472(10) . ?
C22 N23 1.298(9) . ?
C22 C221 1.506(9) . ?
C24 N23 1.492(9) . ?
C24 C25 1.501(11) . ?
C25 N26 1.473(10) . ?
N26 C27 1.472(10) . ?
N26 C29 1.523(10) . ?
C27 C28 1.496(13) . ?
C29 C30 1.495(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
O11 Cu1 N23 91.7(2) . . ?
O11 Cu1 N26 176.7(2) . . ?
N23 Cu1 N26 85.1(3) . . ?
O11 Cu1 Br1 87.51(16) . . ?
N23 Cu1 Br1 169.17(18) . . ?
N26 Cu1 Br1 95.56(19) . . ?
O11 C12 C21 126.1(6) . . ?
O11 C12 C13 114.6(6) . . ?
C21 C12 C13 119.3(6) . . ?
C18 C13 C14 118.9(6) . . ?
C18 C13 C12 121.2(6) . . ?
C14 C13 C12 119.9(6) . . ?
C15 C14 C13 121.8(7) . . ?
C14 C15 C16 118.9(7) . . ?
C17 C16 C15 120.5(7) . . ?
C16 C17 C18 121.5(7) . . ?
C17 C18 C13 118.4(7) . . ?
C17 C18 C19 124.6(7) . . ?
C13 C18 C19 117.0(6) . . ?
C20 C19 C18 122.0(6) . . ?
C20 C19 Br19 118.5(5) . . ?
C18 C19 Br19 119.5(5) . . ?
C19 C20 C21 123.2(6) . . ?
C12 C21 C20 117.1(6) . . ?
C12 C21 C22 121.9(6) . . ?
C20 C21 C22 121.0(6) . . ?
N23 C22 C21 122.1(6) . . ?
N23 C22 C221 119.2(6) . . ?
C21 C22 C221 118.7(6) . . ?
N23 C24 C25 107.2(6) . . ?
N26 C25 C24 111.1(6) . . ?
C22 N23 C24 118.5(6) . . ?
C22 N23 Cu1 128.4(5) . . ?
C24 N23 Cu1 112.6(5) . . ?
C27 N26 C25 111.0(6) . . ?
C27 N26 C29 110.1(7) . . ?
C25 N26 C29 111.5(6) . . ?
C27 N26 Cu1 118.7(5) . . ?
C25 N26 Cu1 104.2(4) . . ?
C29 N26 Cu1 101.0(5) . . ?
N26 C27 C28 113.0(7) . . ?
C30 C29 N26 117.7(8) . . ?
C12 O11 Cu1 129.1(4) . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         1.473
_refine_diff_density_min         -2.015
_refine_diff_density_rms         0.205
