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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_s
_database_code_depnum_ccdc_archive 'CCDC 1036466'
_audit_update_record             
;
2014-12-24 deposited with the CCDC.
2015-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H7 Cu I N O2'
_chemical_formula_weight         363.61

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'
I I -0.4742 1.8119 '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)/n  '

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

_cell_length_a                   4.2490(8)
_cell_length_b                   15.962(3)
_cell_length_c                   15.297(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.03(3)
_cell_angle_gamma                90.00
_cell_volume                     1037.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2368
_cell_measurement_theta_min      3.69
_cell_measurement_theta_max      27.46

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    5.056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6318
_exptl_absorpt_correction_T_max  0.6318
_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  'Bruker Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9840
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.69
_diffrn_reflns_theta_max         27.46
_reflns_number_total             2368
_reflns_number_gt                2209
_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, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  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)+(0.0000P)²+66.6049P] 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         2368
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0814
_refine_ls_wR_factor_ref         0.2192
_refine_ls_wR_factor_gt          0.2183
_refine_ls_goodness_of_fit_ref   1.267
_refine_ls_restrained_S_all      1.267
_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
I1 I -0.8121(2) 0.92025(6) 0.08990(7) 0.0269(3) Uani 1 1 d . . .
Cu1 Cu -0.6886(5) 1.06694(12) 0.01722(14) 0.0327(5) Uani 1 1 d . . .
O1 O -1.010(4) 1.3926(8) -0.0118(10) 0.053(4) Uani 1 1 d . . .
H1 H -1.0691 1.4388 -0.0283 0.080 Uiso 1 1 calc R . .
O2 O -0.754(4) 1.4711(8) 0.0851(11) 0.060(4) Uani 1 1 d . . .
N1 N -0.643(3) 1.1746(8) 0.0893(8) 0.027(3) Uani 1 1 d . . .
C1 C -0.754(4) 1.2451(10) 0.0581(11) 0.031(3) Uani 1 1 d . . .
H1A H -0.8817 1.2421 0.0089 0.037 Uiso 1 1 calc R . .
C2 C -0.694(4) 1.3252(9) 0.0934(10) 0.027(3) Uani 1 1 d . . .
C3 C -0.511(5) 1.3294(11) 0.1685(13) 0.040(4) Uani 1 1 d . . .
H3A H -0.4736 1.3811 0.1946 0.048 Uiso 1 1 calc R . .
C4 C -0.381(4) 1.2559(9) 0.2058(11) 0.029(3) Uani 1 1 d . . .
C5 C -0.454(4) 1.1793(10) 0.1636(12) 0.033(3) Uani 1 1 d . . .
C6 C -0.202(4) 1.2560(11) 0.2810(12) 0.034(4) Uani 1 1 d . . .
H6A H -0.1618 1.3062 0.3099 0.041 Uiso 1 1 calc R . .
C7 C -0.084(5) 1.1845(13) 0.3127(14) 0.045(4) Uani 1 1 d . . .
H7A H 0.0469 1.1861 0.3613 0.053 Uiso 1 1 calc R . .
C8 C -0.160(4) 1.1026(12) 0.2719(10) 0.034(4) Uani 1 1 d . . .
H8A H -0.0930 1.0523 0.2965 0.041 Uiso 1 1 calc R . .
C9 C -0.326(4) 1.1046(10) 0.1985(12) 0.035(4) Uani 1 1 d . . .
H9A H -0.3610 1.0547 0.1687 0.041 Uiso 1 1 calc R . .
C10 C -0.830(4) 1.4010(11) 0.0531(13) 0.037(4) Uani 1 1 d . . .

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
I1 0.0239(5) 0.0244(5) 0.0325(5) 0.0054(4) -0.0039(4) -0.0004(4)
Cu1 0.0383(11) 0.0208(9) 0.0389(11) -0.0036(8) -0.0056(9) 0.0014(8)
O1 0.082(11) 0.022(6) 0.056(9) 0.002(6) -0.021(8) 0.001(7)
O2 0.088(12) 0.020(6) 0.072(10) 0.002(6) -0.030(9) 0.003(7)
N1 0.033(7) 0.021(6) 0.028(7) -0.001(5) -0.004(5) -0.004(5)
C1 0.039(9) 0.023(7) 0.031(8) -0.007(6) 0.008(7) -0.002(6)
C2 0.033(8) 0.020(7) 0.029(8) -0.003(6) -0.004(6) -0.001(6)
C3 0.047(11) 0.022(8) 0.051(11) -0.013(8) 0.003(9) -0.003(7)
C4 0.032(8) 0.016(6) 0.038(8) -0.008(6) 0.005(7) -0.008(6)
C5 0.032(8) 0.028(8) 0.038(9) -0.005(7) 0.000(7) 0.002(7)
C6 0.028(8) 0.035(9) 0.040(9) -0.010(7) 0.011(7) 0.000(7)
C7 0.038(10) 0.046(11) 0.050(11) -0.009(9) -0.004(9) -0.004(8)
C8 0.037(9) 0.043(9) 0.023(7) 0.007(7) 0.001(6) 0.021(8)
C9 0.035(9) 0.026(8) 0.042(9) -0.001(7) -0.005(7) -0.004(7)
C10 0.041(9) 0.026(8) 0.045(10) -0.001(7) 0.000(8) -0.006(7)

_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
I1 Cu1 2.645(2) . ?
I1 Cu1 2.688(2) 3_375 ?
I1 Cu1 2.694(3) 3_475 ?
Cu1 N1 2.051(13) . ?
Cu1 I1 2.688(2) 3_375 ?
Cu1 I1 2.694(3) 3_475 ?
Cu1 Cu1 2.723(4) 3_475 ?
O1 C10 1.26(2) . ?
O1 H1 0.8200 . ?
O2 C10 1.26(2) . ?
N1 C1 1.31(2) . ?
N1 C5 1.39(2) . ?
C1 C2 1.41(2) . ?
C1 H1A 0.9300 . ?
C2 C3 1.39(2) . ?
C2 C10 1.48(2) . ?
C3 C4 1.42(2) . ?
C3 H3A 0.9300 . ?
C4 C6 1.38(2) . ?
C4 C5 1.42(2) . ?
C5 C9 1.41(2) . ?
C6 C7 1.34(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.48(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.33(2) . ?
C8 H8A 0.9300 . ?
C9 H9A 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
Cu1 I1 Cu1 80.40(7) . 3_375 ?
Cu1 I1 Cu1 61.32(8) . 3_475 ?
Cu1 I1 Cu1 104.29(8) 3_375 3_475 ?
N1 Cu1 I1 122.3(4) . . ?
N1 Cu1 I1 109.8(4) . 3_375 ?
I1 Cu1 I1 99.60(7) . 3_375 ?
N1 Cu1 I1 100.9(4) . 3_475 ?
I1 Cu1 I1 118.68(8) . 3_475 ?
I1 Cu1 I1 104.29(8) 3_375 3_475 ?
N1 Cu1 Cu1 134.9(4) . 3_475 ?
I1 Cu1 Cu1 60.23(8) . 3_475 ?
I1 Cu1 Cu1 113.96(11) 3_375 3_475 ?
I1 Cu1 Cu1 58.45(9) 3_475 3_475 ?
C10 O1 H1 109.5 . . ?
C1 N1 C5 117.2(14) . . ?
C1 N1 Cu1 119.4(11) . . ?
C5 N1 Cu1 122.5(11) . . ?
N1 C1 C2 125.1(16) . . ?
N1 C1 H1A 117.5 . . ?
C2 C1 H1A 117.5 . . ?
C3 C2 C1 117.5(15) . . ?
C3 C2 C10 121.6(15) . . ?
C1 C2 C10 120.9(15) . . ?
C2 C3 C4 120.7(15) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C6 C4 C5 120.1(16) . . ?
C6 C4 C3 123.3(15) . . ?
C5 C4 C3 116.5(16) . . ?
N1 C5 C9 118.9(15) . . ?
N1 C5 C4 122.9(15) . . ?
C9 C5 C4 118.2(16) . . ?
C7 C6 C4 120.4(16) . . ?
C7 C6 H6A 119.8 . . ?
C4 C6 H6A 119.8 . . ?
C6 C7 C8 121.4(17) . . ?
C6 C7 H7A 119.3 . . ?
C8 C7 H7A 119.3 . . ?
C9 C8 C7 116.7(16) . . ?
C9 C8 H8A 121.7 . . ?
C7 C8 H8A 121.7 . . ?
C8 C9 C5 122.9(17) . . ?
C8 C9 H9A 118.5 . . ?
C5 C9 H9A 118.5 . . ?
O1 C10 O2 123.7(17) . . ?
O1 C10 C2 118.6(15) . . ?
O2 C10 C2 117.7(16) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         3.286
_refine_diff_density_min         -3.494
_refine_diff_density_rms         0.322
