# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_compound_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 Cu N2 O4'
_chemical_formula_weight         321.77

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'
Cu Cu 0.3201 1.2651 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   7.019(3)
_cell_length_b                   28.604(3)
_cell_length_c                   5.964(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.808(8)
_cell_angle_gamma                90
_cell_volume                     1196.8(8)
_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       Irregular
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_F_000             652
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    1.840
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.49
_exptl_absorpt_correction_T_max  0.71
_exptl_absorpt_process_details   
;
SADABS: Area-Detector Absorption Correction; 
Siemens Industrial Automation, Inc.: Madison, WI, 1996.
;

_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  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_number            12331
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         6.405
_diffrn_reflns_theta_max         27.517
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             2694
_reflns_number_gt                2240
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    CRYSTALMAKER
_computing_publication_material  'PARST97 (Nardelli, 1997)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0054P)²+8.3740P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2694
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0600
_refine_ls_wR_factor_ref         0.1327
_refine_ls_wR_factor_gt          0.1280
_refine_ls_goodness_of_fit_ref   1.214
_refine_ls_restrained_S_all      1.214
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5540(6) 0.21362(17) -0.0011(7) 0.0098(8) Uani 1 1 d . . . . .
C2 C 0.3701(6) 0.18991(16) -0.0979(7) 0.0089(9) Uani 1 1 d . . . . .
H2 H 0.3663 0.1957 -0.2600 0.011 Uiso 1 1 calc R U . . .
C3 C 0.1966(6) 0.21567(17) -0.0013(7) 0.0104(9) Uani 1 1 d . . . . .
C4 C 0.3597(6) 0.13757(16) -0.0667(8) 0.0114(9) Uani 1 1 d . . . . .
C5 C 0.4033(6) 0.11613(18) 0.1399(8) 0.0157(10) Uani 1 1 d . . . . .
H5 H 0.4455 0.1342 0.2612 0.019 Uiso 1 1 calc R U . . .
C6 C 0.3842(7) 0.06835(18) 0.1650(8) 0.0166(10) Uani 1 1 d . . . . .
H6 H 0.4143 0.0544 0.3026 0.020 Uiso 1 1 calc R U . . .
C7 C 0.3203(7) 0.04103(18) -0.0144(9) 0.0190(11) Uani 1 1 d . . . . .
H7 H 0.3060 0.0089 0.0028 0.023 Uiso 1 1 calc R U . . .
C8 C 0.2780(7) 0.06189(18) -0.2183(9) 0.0171(10) Uani 1 1 d . . . . .
H8 H 0.2361 0.0437 -0.3394 0.021 Uiso 1 1 calc R U . . .
C9 C 0.2977(6) 0.10984(18) -0.2438(8) 0.0146(10) Uani 1 1 d . . . . .
H9 H 0.2687 0.1235 -0.3822 0.018 Uiso 1 1 calc R U . . .
C10 C 0.3026(7) 0.37239(18) 0.1385(8) 0.0163(10) Uani 1 1 d . . . . .
H10 H 0.2714 0.3485 0.2367 0.020 Uiso 1 1 calc R U . . .
C11 C 0.2700(7) 0.41813(19) 0.1993(9) 0.0182(10) Uani 1 1 d . . . . .
H11 H 0.2142 0.4240 0.3358 0.022 Uiso 1 1 calc R U . . .
C12 C 0.3945(7) 0.44301(18) -0.1258(9) 0.0163(10) Uani 1 1 d . . . . .
H12 H 0.4306 0.4669 -0.2212 0.020 Uiso 1 1 calc R U . . .
C13 C 0.4234(6) 0.39755(18) -0.1892(8) 0.0144(10) Uani 1 1 d . . . . .
H13 H 0.4761 0.3917 -0.3275 0.017 Uiso 1 1 calc R U . . .
Cu1 Cu 0.37898(7) 0.28923(2) -0.20659(10) 0.00936(17) Uani 1 1 d . . . . .
N1 N 0.3785(5) 0.36132(14) -0.0592(7) 0.0120(8) Uani 1 1 d . . . . .
N2 N 0.3153(6) 0.45420(15) 0.0701(7) 0.0193(9) Uani 1 1 d . . . . .
O1 O 0.6780(4) 0.18737(12) 0.0887(5) 0.0123(7) Uani 1 1 d . . . . .
O2 O 0.5719(4) 0.25688(12) -0.0210(6) 0.0123(7) Uani 1 1 d . . . . .
O3 O 0.0771(4) 0.19046(12) 0.0925(6) 0.0133(7) Uani 1 1 d . . . . .
O4 O 0.1844(4) 0.25912(11) -0.0226(5) 0.0116(7) 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
C1 0.0083(19) 0.018(2) 0.0035(19) -0.0016(18) 0.0036(15) 0.0005(18)
C2 0.0048(19) 0.018(2) 0.004(2) -0.0021(17) 0.0017(15) 0.0009(17)
C3 0.0057(19) 0.020(2) 0.0049(19) -0.0013(18) -0.0044(15) 0.0004(18)
C4 0.006(2) 0.016(2) 0.012(2) -0.0005(18) 0.0015(16) -0.0005(17)
C5 0.007(2) 0.024(3) 0.016(2) -0.003(2) -0.0001(18) 0.0013(18)
C6 0.009(2) 0.025(3) 0.016(3) 0.005(2) 0.0018(18) 0.0034(19)
C7 0.010(2) 0.017(2) 0.030(3) -0.001(2) 0.003(2) 0.0010(19)
C8 0.010(2) 0.021(3) 0.021(3) -0.005(2) -0.0013(19) 0.0005(19)
C9 0.009(2) 0.022(3) 0.013(2) 0.0016(19) 0.0002(17) 0.0015(19)
C10 0.010(2) 0.023(3) 0.017(3) 0.000(2) 0.0013(18) -0.0040(19)
C11 0.011(2) 0.026(3) 0.018(3) -0.006(2) 0.0015(18) -0.002(2)
C12 0.015(2) 0.017(2) 0.017(2) 0.0023(19) 0.0002(19) -0.0007(19)
C13 0.008(2) 0.023(3) 0.012(2) 0.0011(19) -0.0029(17) -0.0009(18)
Cu1 0.0052(2) 0.0139(3) 0.0089(3) 0.0012(2) 0.00007(18) 0.0000(2)
N1 0.0061(17) 0.018(2) 0.011(2) -0.0002(16) -0.0005(14) -0.0009(15)
N2 0.016(2) 0.022(2) 0.020(2) -0.0053(18) 0.0003(17) -0.0009(18)
O1 0.0079(15) 0.0184(17) 0.0106(16) -0.0010(13) -0.0003(12) 0.0021(13)
O2 0.0078(15) 0.0175(17) 0.0115(16) 0.0022(13) -0.0029(12) 0.0003(13)
O3 0.0074(15) 0.0169(17) 0.0159(17) -0.0016(14) 0.0029(13) -0.0016(13)
O4 0.0096(15) 0.0162(17) 0.0092(16) 0.0015(13) 0.0023(12) 0.0014(13)

_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 O2 1.250(6) . ?
C1 O1 1.256(6) . ?
C1 C2 1.554(6) . ?
C2 C4 1.511(6) . ?
C2 C3 1.549(6) . ?
C3 O3 1.252(6) . ?
C3 O4 1.252(6) . ?
C4 C9 1.380(7) . ?
C4 C5 1.402(7) . ?
C5 C6 1.382(7) . ?
C6 C7 1.388(7) . ?
C7 C8 1.378(7) . ?
C8 C9 1.387(7) . ?
C10 N1 1.347(6) . ?
C10 C11 1.379(7) . ?
C11 N2 1.332(7) . ?
C12 N2 1.348(7) . ?
C12 C13 1.371(7) . ?
C13 N1 1.338(6) . ?
Cu1 O3 1.953(3) 4_665 ?
Cu1 O1 1.954(3) 4_565 ?
Cu1 O2 1.955(3) . ?
Cu1 O4 1.976(3) . ?
Cu1 N1 2.242(4) . ?
O1 Cu1 1.955(3) 4_666 ?
O3 Cu1 1.953(3) 4_566 ?

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
O2 C1 O1 124.2(4) . . ?
O2 C1 C2 118.8(4) . . ?
O1 C1 C2 117.0(4) . . ?
C4 C2 C3 112.6(4) . . ?
C4 C2 C1 115.4(4) . . ?
C3 C2 C1 107.9(3) . . ?
O3 C3 O4 124.9(4) . . ?
O3 C3 C2 116.0(4) . . ?
O4 C3 C2 119.1(4) . . ?
C9 C4 C5 118.4(4) . . ?
C9 C4 C2 119.4(4) . . ?
C5 C4 C2 122.1(4) . . ?
C6 C5 C4 120.6(5) . . ?
C5 C6 C7 120.2(5) . . ?
C8 C7 C6 119.5(5) . . ?
C7 C8 C9 120.3(5) . . ?
C4 C9 C8 121.0(5) . . ?
N1 C10 C11 121.8(5) . . ?
N2 C11 C10 122.5(5) . . ?
N2 C12 C13 122.2(5) . . ?
N1 C13 C12 122.4(5) . . ?
O3 Cu1 O1 91.64(14) 4_665 4_565 ?
O3 Cu1 O2 89.68(14) 4_665 . ?
O1 Cu1 O2 171.64(14) 4_565 . ?
O3 Cu1 O4 171.29(14) 4_665 . ?
O1 Cu1 O4 89.89(14) 4_565 . ?
O2 Cu1 O4 87.59(14) . . ?
O3 Cu1 N1 88.67(14) 4_665 . ?
O1 Cu1 N1 85.41(14) 4_565 . ?
O2 Cu1 N1 102.88(14) . . ?
O4 Cu1 N1 100.00(14) . . ?
C13 N1 C10 115.6(4) . . ?
C13 N1 Cu1 118.8(3) . . ?
C10 N1 Cu1 124.4(3) . . ?
C11 N2 C12 115.5(4) . . ?
C1 O1 Cu1 122.6(3) . 4_666 ?
C1 O2 Cu1 116.9(3) . . ?
C3 O3 Cu1 127.1(3) . 4_566 ?
C3 O4 Cu1 116.3(3) . . ?

_refine_diff_density_max         1.843
_refine_diff_density_min         -0.953
_refine_diff_density_rms         0.131




_database_code_depnum_ccdc_archive 'CCDC 996269'
#######################################################################
#
#                 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_compound3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 Cu N2 O4'
_chemical_formula_weight         345.79

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'
Cu Cu 0.3201 1.2651 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   6.9188(8)
_cell_length_b                   31.180(12)
_cell_length_c                   6.2103(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.463(15)
_cell_angle_gamma                90
_cell_volume                     1337.3(6)
_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       Sheets
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_F_000             700
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    1.653
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.53
_exptl_absorpt_correction_T_max  0.72
_exptl_absorpt_process_details   
;
SADABS: Area-Detector Absorption Correction; 
Siemens Industrial Automation, Inc.: Madison, WI, 1996.
;

_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  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_number            11917
_diffrn_reflns_av_unetI/netI     0.0857
_diffrn_reflns_av_R_equivalents  0.0986
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         6.459
_diffrn_reflns_theta_max         30.121
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             3787
_reflns_number_gt                2718
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    CRYSTALMAKER
_computing_publication_material  'PARST97 (Nardelli, 1997)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0720P)²+1.1077P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3787
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1475
_refine_ls_wR_factor_gt          0.1369
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0036(4) 0.28262(10) 1.1773(5) 0.0180(6) Uani 1 1 d . . . . .
C2 C 0.1678(4) 0.30732(10) 1.0870(5) 0.0166(6) Uani 1 1 d . . . . .
H2 H 0.1608 0.3021 0.9311 0.020 Uiso 1 1 calc R U . . .
C3 C 0.3543(4) 0.28607(10) 1.1776(5) 0.0168(6) Uani 1 1 d . . . . .
C4 C 0.1581(4) 0.35530(11) 1.1158(6) 0.0212(7) Uani 1 1 d . . . . .
C5 C 0.1920(5) 0.37464(13) 1.3162(7) 0.0297(8) Uani 1 1 d . . . . .
H5 H 0.2189 0.3577 1.4377 0.036 Uiso 1 1 calc R U . . .
C6 C 0.1861(6) 0.41885(14) 1.3369(8) 0.0426(11) Uani 1 1 d . . . . .
H6 H 0.2098 0.4314 1.4719 0.051 Uiso 1 1 calc R U . . .
C7 C 0.1454(7) 0.44434(14) 1.1595(10) 0.0503(13) Uani 1 1 d . . . . .
H7 H 0.1434 0.4740 1.1741 0.060 Uiso 1 1 calc R U . . .
C8 C 0.1078(6) 0.42591(14) 0.9612(9) 0.0442(12) Uani 1 1 d . . . . .
H8 H 0.0781 0.4430 0.8410 0.053 Uiso 1 1 calc R U . . .
C9 C 0.1143(5) 0.38137(13) 0.9400(7) 0.0304(8) Uani 1 1 d . . . . .
H9 H 0.0887 0.3690 0.8049 0.037 Uiso 1 1 calc R U . . .
C10 C 0.1335(5) 0.14638(13) 1.3381(6) 0.0283(8) Uani 1 1 d . . . . .
H10 H 0.1209 0.1704 1.4253 0.034 Uiso 1 1 calc R U . . .
C11 C 0.0897(5) 0.10685(13) 1.4205(6) 0.0328(9) Uani 1 1 d . . . . .
H11 H 0.0482 0.1044 1.5596 0.039 Uiso 1 1 calc R U . . .
C12 C 0.1081(6) 0.07104(13) 1.2945(7) 0.0355(9) Uani 1 1 d . . . . .
H12 H 0.0774 0.0440 1.3454 0.043 Uiso 1 1 calc R U . . .
C13 C 0.1733(5) 0.07630(12) 1.0904(7) 0.0301(8) Uani 1 1 d . . . . .
C14 C 0.2155(5) 0.11748(11) 1.0188(6) 0.0241(7) Uani 1 1 d . . . . .
H14 H 0.2607 0.1208 0.8819 0.029 Uiso 1 1 calc R U . . .
C15 C 0.1921(7) 0.04080(13) 0.9452(8) 0.0417(11) Uani 1 1 d . . . . .
Cu1 Cu 0.18206(5) 0.21588(2) 0.96989(7) 0.01692(14) Uani 1 1 d . . . . .
N1 N 0.1932(4) 0.15214(9) 1.1398(5) 0.0228(6) Uani 1 1 d . . . . .
N2 N 0.2078(8) 0.01283(14) 0.8300(9) 0.0718(15) Uani 1 1 d . . . . .
O1 O -0.1218(3) 0.30433(7) 1.2770(4) 0.0224(5) Uani 1 1 d . . . . .
O2 O -0.0145(3) 0.24308(7) 1.1434(4) 0.0228(5) Uani 1 1 d . . . . .
O3 O 0.4749(3) 0.30899(7) 1.2815(4) 0.0208(5) Uani 1 1 d . . . . .
O4 O 0.3791(3) 0.24665(8) 1.1436(4) 0.0244(5) 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
C1 0.0130(14) 0.0232(15) 0.0174(15) 0.0019(14) -0.0016(11) 0.0020(11)
C2 0.0153(14) 0.0191(15) 0.0154(15) 0.0018(13) 0.0013(12) -0.0014(11)
C3 0.0131(14) 0.0220(15) 0.0158(15) 0.0007(13) 0.0046(11) -0.0023(11)
C4 0.0125(14) 0.0221(16) 0.0290(18) 0.0041(14) 0.0027(13) -0.0008(12)
C5 0.0231(18) 0.0311(19) 0.035(2) -0.0039(17) 0.0006(15) 0.0023(14)
C6 0.035(2) 0.034(2) 0.058(3) -0.018(2) 0.003(2) -0.0010(17)
C7 0.042(2) 0.024(2) 0.086(4) 0.001(2) 0.012(3) -0.0013(17)
C8 0.033(2) 0.030(2) 0.069(3) 0.021(2) 0.001(2) 0.0034(17)
C9 0.0199(16) 0.035(2) 0.036(2) 0.0097(18) -0.0037(15) -0.0004(14)
C10 0.0207(17) 0.036(2) 0.0281(19) -0.0029(17) 0.0008(14) 0.0060(14)
C11 0.0272(19) 0.047(2) 0.0250(19) 0.0093(18) 0.0044(15) -0.0012(16)
C12 0.035(2) 0.031(2) 0.041(2) 0.0109(18) 0.0070(18) -0.0033(16)
C13 0.0258(18) 0.0258(18) 0.039(2) 0.0022(17) 0.0034(16) 0.0004(14)
C14 0.0250(18) 0.0242(16) 0.0234(18) 0.0025(15) 0.0028(14) 0.0005(13)
C15 0.050(3) 0.0237(19) 0.052(3) -0.001(2) 0.010(2) -0.0043(17)
Cu1 0.0110(2) 0.0179(2) 0.0218(2) -0.00278(16) 0.00089(14) 0.00025(14)
N1 0.0204(14) 0.0236(14) 0.0242(15) 0.0011(13) -0.0003(12) 0.0007(11)
N2 0.096(4) 0.034(2) 0.088(4) -0.018(2) 0.029(3) -0.010(2)
O1 0.0169(11) 0.0217(12) 0.0295(13) 0.0010(11) 0.0087(10) 0.0035(9)
O2 0.0170(11) 0.0233(11) 0.0288(13) -0.0049(10) 0.0078(10) -0.0030(9)
O3 0.0133(10) 0.0231(11) 0.0251(13) 0.0030(10) -0.0075(9) -0.0010(9)
O4 0.0151(11) 0.0257(12) 0.0317(14) -0.0065(11) -0.0032(10) 0.0027(9)

_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 O1 1.253(4) . ?
C1 O2 1.252(4) . ?
C1 C2 1.547(4) . ?
C2 C4 1.509(5) . ?
C2 C3 1.527(4) . ?
C3 O3 1.249(4) . ?
C3 O4 1.261(4) . ?
C4 C9 1.380(5) . ?
C4 C5 1.390(5) . ?
C5 C6 1.385(6) . ?
C6 C7 1.374(7) . ?
C7 C8 1.370(7) . ?
C8 C9 1.396(6) . ?
C10 N1 1.335(5) . ?
C10 C11 1.375(6) . ?
C11 C12 1.374(6) . ?
C12 C13 1.381(6) . ?
C13 C14 1.395(5) . ?
C13 C15 1.438(6) . ?
C14 N1 1.330(5) . ?
C15 N2 1.137(6) . ?
Cu1 O4 1.940(2) . ?
Cu1 O3 1.955(2) 4_565 ?
Cu1 O1 1.968(2) 4_665 ?
Cu1 O2 1.977(2) . ?
Cu1 N1 2.249(3) . ?
O1 Cu1 1.968(2) 4_566 ?
O3 Cu1 1.955(2) 4_666 ?

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 C1 O2 125.5(3) . . ?
O1 C1 C2 116.6(3) . . ?
O2 C1 C2 118.0(3) . . ?
C4 C2 C3 115.4(3) . . ?
C4 C2 C1 114.2(3) . . ?
C3 C2 C1 107.4(2) . . ?
O3 C3 O4 123.4(3) . . ?
O3 C3 C2 117.8(3) . . ?
O4 C3 C2 118.8(3) . . ?
C9 C4 C5 118.0(3) . . ?
C9 C4 C2 120.0(3) . . ?
C5 C4 C2 122.0(3) . . ?
C6 C5 C4 120.7(4) . . ?
C7 C6 C5 120.5(4) . . ?
C6 C7 C8 119.8(4) . . ?
C7 C8 C9 119.8(4) . . ?
C4 C9 C8 121.2(4) . . ?
N1 C10 C11 123.4(4) . . ?
C10 C11 C12 119.1(4) . . ?
C11 C12 C13 118.2(4) . . ?
C12 C13 C14 119.2(4) . . ?
C12 C13 C15 122.1(4) . . ?
C14 C13 C15 118.7(4) . . ?
N1 C14 C13 122.3(3) . . ?
N2 C15 C13 179.7(5) . . ?
O4 Cu1 O3 173.69(10) . 4_565 ?
O4 Cu1 O1 90.55(10) . 4_665 ?
O3 Cu1 O1 90.94(10) 4_565 4_665 ?
O4 Cu1 O2 88.18(10) . . ?
O3 Cu1 O2 89.57(10) 4_565 . ?
O1 Cu1 O2 172.77(10) 4_665 . ?
O4 Cu1 N1 99.97(11) . . ?
O3 Cu1 N1 86.17(10) 4_565 . ?
O1 Cu1 N1 89.85(10) 4_665 . ?
O2 Cu1 N1 97.38(10) . . ?
C14 N1 C10 117.7(3) . . ?
C14 N1 Cu1 117.1(2) . . ?
C10 N1 Cu1 123.2(2) . . ?
C1 O1 Cu1 128.5(2) . 4_566 ?
C1 O2 Cu1 118.5(2) . . ?
C3 O3 Cu1 121.7(2) . 4_666 ?
C3 O4 Cu1 118.5(2) . . ?

_refine_diff_density_max         1.028
_refine_diff_density_min         -0.815
_refine_diff_density_rms         0.113


_database_code_depnum_ccdc_archive 'CCDC 996270'
#######################################################################
#
#                 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_compound_4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 Cu N2 O4'
_chemical_formula_weight         345.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   6.3297(2)
_cell_length_b                   31.7864(11)
_cell_length_c                   6.9390(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.732(3)
_cell_angle_gamma                90
_cell_volume                     1394.53(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2277
_cell_measurement_theta_min      5.5670
_cell_measurement_theta_max      73.2900

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_F_000             700
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4673
_exptl_crystal_size_mid          0.0573
_exptl_crystal_size_min          0.0345
_exptl_absorpt_coefficient_mu    2.406
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.708
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.5953
_diffrn_reflns_number            5281
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         5.567
_diffrn_reflns_theta_max         73.015
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2727
_reflns_number_gt                2393
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    CRYSTALMAKER
_computing_publication_material  'PARST97 (Nardelli, 1997)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0472P)²+0.6628P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2727
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0867
_refine_ls_wR_factor_gt          0.0827
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3518(3) 0.28564(7) 1.0502(3) 0.0210(4) Uani 1 1 d . . . . .
C2 C 0.2669(3) 0.30759(6) 0.8644(3) 0.0214(4) Uani 1 1 d . . . . .
H2 H 0.1130 0.3039 0.8588 0.026 Uiso 1 1 calc R U . . .
C3 C 0.3508(3) 0.28296(6) 0.6913(3) 0.0210(4) Uani 1 1 d . . . . .
C4 C 0.3071(3) 0.35431(7) 0.8580(3) 0.0261(4) Uani 1 1 d . . . . .
C5 C 0.5099(4) 0.37097(8) 0.8886(4) 0.0372(5) Uani 1 1 d . . . . .
H5 H 0.6246 0.3531 0.9117 0.045 Uiso 1 1 calc R U . . .
C6 C 0.5406(5) 0.41428(10) 0.8844(5) 0.0523(7) Uani 1 1 d . . . . .
H6 H 0.6762 0.4252 0.9048 0.063 Uiso 1 1 calc R U . . .
C7 C 0.3727(6) 0.44120(9) 0.8505(5) 0.0575(8) Uani 1 1 d . . . . .
H7 H 0.3946 0.4701 0.8484 0.069 Uiso 1 1 calc R U . . .
C8 C 0.1730(6) 0.42507(9) 0.8197(5) 0.0526(7) Uani 1 1 d . . . . .
H8 H 0.0590 0.4431 0.7961 0.063 Uiso 1 1 calc R U . . .
C9 C 0.1401(4) 0.38161(8) 0.8238(4) 0.0369(5) Uani 1 1 d . . . . .
H9 H 0.0040 0.3710 0.8032 0.044 Uiso 1 1 calc R U . . .
C10 C 0.5149(3) 0.15421(8) 0.8297(3) 0.0313(5) Uani 1 1 d . . . . .
H10 H 0.5855 0.1792 0.8061 0.038 Uiso 1 1 calc R U . . .
C11 C 0.6196(4) 0.11659(8) 0.8030(4) 0.0359(5) Uani 1 1 d . . . . .
H11 H 0.7568 0.1162 0.7606 0.043 Uiso 1 1 calc R U . . .
C12 C 0.5154(4) 0.07964(8) 0.8406(4) 0.0371(5) Uani 1 1 d . . . . .
C13 C 0.3100(4) 0.08113(8) 0.9028(4) 0.0397(6) Uani 1 1 d . . . . .
H13 H 0.2365 0.0566 0.9288 0.048 Uiso 1 1 calc R U . . .
C14 C 0.2187(4) 0.12011(8) 0.9247(4) 0.0339(5) Uani 1 1 d . . . . .
H14 H 0.0818 0.1214 0.9672 0.041 Uiso 1 1 calc R U . . .
C15 C 0.6202(5) 0.03971(10) 0.8192(5) 0.0540(7) Uani 1 1 d . . . . .
Cu1 Cu 0.13977(4) 0.21725(2) 0.87645(4) 0.02085(11) Uani 1 1 d . . . . .
N1 N 0.3179(3) 0.15623(6) 0.8876(3) 0.0267(4) Uani 1 1 d . . . . .
N2 N 0.7041(6) 0.00823(10) 0.8045(6) 0.0849(12) Uani 1 1 d . . . . .
O1 O 0.4566(2) 0.30716(5) 1.1710(2) 0.0256(3) Uani 1 1 d . . . . .
O2 O 0.3107(2) 0.24727(5) 1.0737(2) 0.0292(3) Uani 1 1 d . . . . .
O3 O 0.4528(2) 0.30344(5) 0.5739(2) 0.0264(3) Uani 1 1 d . . . . .
O4 O 0.3104(2) 0.24429(5) 0.6783(2) 0.0280(3) 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
C1 0.0181(8) 0.0272(10) 0.0181(9) -0.0009(7) 0.0045(7) 0.0017(7)
C2 0.0207(8) 0.0263(10) 0.0174(9) 0.0005(8) 0.0037(7) 0.0010(7)
C3 0.0182(8) 0.0271(10) 0.0178(9) -0.0002(7) 0.0005(7) 0.0029(7)
C4 0.0314(10) 0.0285(11) 0.0187(9) -0.0002(8) 0.0046(8) 0.0007(8)
C5 0.0379(12) 0.0336(13) 0.0406(13) -0.0013(10) 0.0073(10) -0.0053(10)
C6 0.0620(18) 0.0412(15) 0.0545(17) -0.0049(13) 0.0102(14) -0.0205(14)
C7 0.092(2) 0.0254(13) 0.0559(18) -0.0014(12) 0.0113(17) -0.0053(14)
C8 0.075(2) 0.0323(14) 0.0504(16) 0.0053(12) 0.0032(14) 0.0148(14)
C9 0.0436(13) 0.0336(13) 0.0334(12) 0.0013(10) -0.0007(10) 0.0077(10)
C10 0.0294(11) 0.0300(11) 0.0349(11) 0.0046(9) 0.0058(9) 0.0000(9)
C11 0.0303(11) 0.0403(13) 0.0378(12) 0.0044(10) 0.0087(9) 0.0078(10)
C12 0.0446(13) 0.0300(12) 0.0369(12) 0.0007(10) 0.0056(10) 0.0094(10)
C13 0.0425(13) 0.0280(12) 0.0489(15) 0.0026(10) 0.0072(11) -0.0031(10)
C14 0.0273(10) 0.0325(12) 0.0421(13) 0.0031(10) 0.0050(9) -0.0003(9)
C15 0.0632(18) 0.0352(15) 0.0651(19) 0.0059(14) 0.0199(15) 0.0131(13)
Cu1 0.02317(17) 0.02191(17) 0.01766(16) 0.00061(11) 0.00296(11) -0.00205(11)
N1 0.0278(9) 0.0255(9) 0.0269(9) 0.0027(7) 0.0027(7) 0.0031(7)
N2 0.097(3) 0.0424(16) 0.119(3) 0.0071(18) 0.042(2) 0.0262(17)
O1 0.0282(7) 0.0265(8) 0.0217(7) -0.0038(6) -0.0022(5) 0.0022(6)
O2 0.0354(8) 0.0292(8) 0.0226(7) 0.0045(6) -0.0037(6) -0.0073(6)
O3 0.0328(7) 0.0249(7) 0.0226(7) 0.0033(6) 0.0117(6) 0.0012(6)
O4 0.0340(8) 0.0260(8) 0.0247(7) -0.0028(6) 0.0087(6) -0.0044(6)

_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 O1 1.248(3) . ?
C1 O2 1.259(3) . ?
C1 C2 1.540(3) . ?
C2 C4 1.508(3) . ?
C2 C3 1.549(3) . ?
C3 O3 1.247(3) . ?
C3 O4 1.258(3) . ?
C4 C9 1.380(3) . ?
C4 C5 1.395(3) . ?
C5 C6 1.391(4) . ?
C6 C7 1.376(5) . ?
C7 C8 1.372(5) . ?
C8 C9 1.397(4) . ?
C10 N1 1.330(3) . ?
C10 C11 1.384(3) . ?
C11 C12 1.378(4) . ?
C12 C13 1.390(4) . ?
C12 C15 1.443(4) . ?
C13 C14 1.379(4) . ?
C14 N1 1.339(3) . ?
C15 N2 1.140(4) . ?
Cu1 O2 1.9530(15) . ?
Cu1 O1 1.9547(15) 4_565 ?
Cu1 O3 1.9660(15) 4_566 ?
Cu1 O4 1.9844(15) . ?
Cu1 N1 2.2429(18) . ?
O1 Cu1 1.9547(15) 4_666 ?
O3 Cu1 1.9659(14) 4_665 ?

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 C1 O2 123.40(19) . . ?
O1 C1 C2 117.83(18) . . ?
O2 C1 C2 118.77(18) . . ?
C4 C2 C1 114.72(17) . . ?
C4 C2 C3 114.23(17) . . ?
C1 C2 C3 107.54(16) . . ?
O3 C3 O4 124.95(19) . . ?
O3 C3 C2 116.77(18) . . ?
O4 C3 C2 118.27(18) . . ?
C9 C4 C5 118.6(2) . . ?
C9 C4 C2 119.7(2) . . ?
C5 C4 C2 121.7(2) . . ?
C6 C5 C4 120.1(3) . . ?
C7 C6 C5 120.8(3) . . ?
C8 C7 C6 119.5(3) . . ?
C7 C8 C9 120.2(3) . . ?
C4 C9 C8 120.8(3) . . ?
N1 C10 C11 123.0(2) . . ?
C12 C11 C10 118.3(2) . . ?
C11 C12 C13 119.5(2) . . ?
C11 C12 C15 120.2(2) . . ?
C13 C12 C15 120.2(3) . . ?
C14 C13 C12 117.9(2) . . ?
N1 C14 C13 123.1(2) . . ?
N2 C15 C12 179.1(5) . . ?
O2 Cu1 O1 174.09(7) . 4_565 ?
O2 Cu1 O3 90.40(7) . 4_566 ?
O1 Cu1 O3 91.11(6) 4_565 4_566 ?
O2 Cu1 O4 88.42(7) . . ?
O1 Cu1 O4 89.43(6) 4_565 . ?
O3 Cu1 O4 173.42(6) 4_566 . ?
O2 Cu1 N1 97.90(7) . . ?
O1 Cu1 N1 87.80(7) 4_565 . ?
O3 Cu1 N1 90.29(7) 4_566 . ?
O4 Cu1 N1 96.28(7) . . ?
C10 N1 C14 118.1(2) . . ?
C10 N1 Cu1 120.56(16) . . ?
C14 N1 Cu1 120.57(15) . . ?
C1 O1 Cu1 123.36(14) . 4_666 ?
C1 O2 Cu1 119.57(13) . . ?
C3 O3 Cu1 128.94(14) . 4_665 ?
C3 O4 Cu1 119.27(13) . . ?

_refine_diff_density_max         0.307
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.062





_database_code_depnum_ccdc_archive 'CCDC 996271'
#######################################################################
#
#                 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_compound_6

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 Cl Cu N O4'
_chemical_formula_weight         355.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   6.2264(11)
_cell_length_b                   30.6016(17)
_cell_length_c                   6.9804(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.297(13)
_cell_angle_gamma                90
_cell_volume                     1327.8(3)
_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       Sheets
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_F_000             716
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    1.860
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_process_details   
;
SADABS: Area-Detector Absorption Correction; 
Siemens Industrial Automation, Inc.: Madison, WI, 1996.
;
_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  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_number            8791
_diffrn_reflns_av_unetI/netI     0.1301
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         6.434
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             3721
_reflns_number_gt                2168
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    CRYSTALMAKER
_computing_publication_material  'PARST97 (Nardelli, 1997)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0388P)²+9.4418P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3721
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1535
_refine_ls_R_factor_gt           0.0876
_refine_ls_wR_factor_ref         0.1960
_refine_ls_wR_factor_gt          0.1791
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_restrained_S_all      1.148
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0900(9) 0.2866(2) 0.3632(8) 0.0174(12) Uani 1 1 d . . . . .
C2 C 1.0026(10) 0.3087(2) 0.1752(9) 0.0183(13) Uani 1 1 d . . . . .
H2 H 0.8466 0.3041 0.1682 0.022 Uiso 1 1 calc R U . . .
C3 C 1.0898(9) 0.2830(2) 0.0047(8) 0.0184(13) Uani 1 1 d . . . . .
C4 C 1.0356(11) 0.3576(2) 0.1658(9) 0.0215(14) Uani 1 1 d . . . . .
C5 C 1.2381(13) 0.3765(2) 0.2052(10) 0.0306(17) Uani 1 1 d . . . . .
H5 H 1.3572 0.3587 0.2325 0.037 Uiso 1 1 calc R U . . .
C6 C 1.2620(15) 0.4211(3) 0.2037(12) 0.041(2) Uani 1 1 d . . . . .
H6 H 1.3961 0.4336 0.2332 0.049 Uiso 1 1 calc R U . . .
C7 C 1.0840(17) 0.4478(3) 0.1578(12) 0.044(2) Uani 1 1 d . . . . .
H7 H 1.0993 0.4780 0.1583 0.053 Uiso 1 1 calc R U . . .
C8 C 0.8881(16) 0.4296(3) 0.1122(12) 0.044(2) Uani 1 1 d . . . . .
H8 H 0.7710 0.4473 0.0778 0.053 Uiso 1 1 calc R U . . .
C9 C 0.8628(12) 0.3847(3) 0.1168(10) 0.0306(17) Uani 1 1 d . . . . .
H9 H 0.7282 0.3725 0.0867 0.037 Uiso 1 1 calc R U . . .
C10 C 1.2528(12) 0.1472(3) 0.1365(10) 0.0322(17) Uani 1 1 d . . . . .
H10 H 1.3325 0.1724 0.1193 0.039 Uiso 1 1 calc R U . . .
C11 C 1.3422(14) 0.1076(3) 0.0966(11) 0.039(2) Uani 1 1 d . . . . .
H11 H 1.4806 0.1063 0.0534 0.047 Uiso 1 1 calc R U . . .
C12 C 1.2272(14) 0.0698(3) 0.1205(12) 0.038(2) Uani 1 1 d . . . . .
H12 H 1.2843 0.0426 0.0929 0.046 Uiso 1 1 calc R U . . .
C13 C 1.0238(14) 0.0739(2) 0.1871(11) 0.0353(18) Uani 1 1 d . . . . .
C14 C 0.9400(11) 0.1144(2) 0.2253(10) 0.0268(16) Uani 1 1 d . . . . .
H14 H 0.8023 0.1164 0.2696 0.032 Uiso 1 1 calc R U . . .
Cl1 Cl 0.8659(5) 0.02787(7) 0.2203(4) 0.0615(7) Uani 1 1 d . . . . .
Cu1 Cu 0.88139(13) 0.21523(3) 0.18980(11) 0.0190(2) Uani 1 1 d . . . . .
N1 N 1.0529(9) 0.15088(19) 0.1999(8) 0.0251(13) Uani 1 1 d . . . . .
O1 O 1.1927(8) 0.30975(15) 0.4840(6) 0.0229(10) Uani 1 1 d . . . . .
O4 O 1.0550(8) 0.24327(15) -0.0071(7) 0.0242(10) Uani 1 1 d . . . . .
O2 O 1.0546(8) 0.24694(16) 0.3850(6) 0.0243(11) Uani 1 1 d . . . . .
O3 O 1.1913(8) 0.30533(15) -0.1134(6) 0.0237(10) 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
C1 0.008(3) 0.030(4) 0.014(3) -0.003(3) 0.003(2) 0.003(3)
C2 0.013(3) 0.029(4) 0.014(3) -0.003(3) 0.008(2) 0.004(3)
C3 0.011(3) 0.035(4) 0.009(3) 0.005(3) 0.002(2) 0.007(3)
C4 0.026(4) 0.028(4) 0.012(3) -0.001(3) 0.004(3) 0.001(3)
C5 0.032(4) 0.035(4) 0.026(4) 0.004(3) 0.007(3) -0.001(3)
C6 0.044(5) 0.045(5) 0.034(4) 0.000(4) 0.002(4) -0.012(4)
C7 0.066(7) 0.033(5) 0.034(4) 0.002(4) 0.006(4) -0.007(4)
C8 0.063(6) 0.034(5) 0.035(4) 0.001(4) 0.000(4) 0.020(4)
C9 0.027(4) 0.041(4) 0.023(3) -0.002(3) -0.002(3) 0.008(3)
C10 0.022(4) 0.046(5) 0.028(4) 0.004(3) 0.001(3) -0.005(3)
C11 0.030(4) 0.058(6) 0.029(4) 0.004(4) 0.007(3) 0.013(4)
C12 0.041(5) 0.040(5) 0.034(4) 0.002(4) 0.008(4) 0.019(4)
C13 0.045(5) 0.029(4) 0.032(4) 0.003(3) 0.006(4) -0.005(4)
C14 0.020(4) 0.029(4) 0.032(4) 0.001(3) 0.001(3) -0.002(3)
Cl1 0.0812(19) 0.0309(11) 0.0753(18) -0.0035(11) 0.0285(14) -0.0125(12)
Cu1 0.0183(4) 0.0245(4) 0.0145(4) 0.0001(4) 0.0026(3) -0.0029(4)
N1 0.023(3) 0.035(3) 0.017(3) 0.003(2) 0.004(2) 0.001(3)
O1 0.023(3) 0.030(3) 0.015(2) -0.0043(19) -0.0011(19) 0.001(2)
O4 0.027(3) 0.023(3) 0.023(2) -0.0015(19) 0.012(2) -0.003(2)
O2 0.026(3) 0.028(3) 0.019(2) 0.0017(19) -0.004(2) -0.006(2)
O3 0.026(3) 0.028(3) 0.017(2) 0.0032(19) 0.009(2) 0.004(2)

_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 O2 1.245(8) . ?
C1 O1 1.248(7) . ?
C1 C2 1.547(9) . ?
C2 C4 1.510(9) . ?
C2 C3 1.551(9) . ?
C3 O4 1.237(8) . ?
C3 O3 1.267(8) . ?
C4 C9 1.385(10) . ?
C4 C5 1.400(10) . ?
C5 C6 1.375(11) . ?
C6 C7 1.399(13) . ?
C7 C8 1.362(13) . ?
C8 C9 1.383(11) . ?
C10 N1 1.349(9) . ?
C10 C11 1.368(11) . ?
C11 C12 1.375(12) . ?
C12 C13 1.379(12) . ?
C13 C14 1.377(10) . ?
C13 Cl1 1.741(8) . ?
C14 N1 1.337(9) . ?
Cu1 O2 1.948(5) . ?
Cu1 O1 1.958(4) 4_565 ?
Cu1 O3 1.967(5) 4_566 ?
Cu1 O4 1.991(5) . ?
Cu1 N1 2.239(6) . ?
O1 Cu1 1.958(4) 4_666 ?
O3 Cu1 1.967(5) 4_665 ?

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
O2 C1 O1 123.9(6) . . ?
O2 C1 C2 118.3(5) . . ?
O1 C1 C2 117.8(6) . . ?
C4 C2 C1 115.3(5) . . ?
C4 C2 C3 114.5(5) . . ?
C1 C2 C3 107.9(5) . . ?
O4 C3 O3 125.4(6) . . ?
O4 C3 C2 118.8(5) . . ?
O3 C3 C2 115.8(6) . . ?
C9 C4 C5 118.6(7) . . ?
C9 C4 C2 119.8(6) . . ?
C5 C4 C2 121.6(6) . . ?
C6 C5 C4 120.4(7) . . ?
C5 C6 C7 119.8(8) . . ?
C8 C7 C6 120.2(8) . . ?
C7 C8 C9 120.2(8) . . ?
C8 C9 C4 120.8(8) . . ?
N1 C10 C11 122.3(7) . . ?
C10 C11 C12 119.9(8) . . ?
C11 C12 C13 117.4(7) . . ?
C14 C13 C12 120.8(7) . . ?
C14 C13 Cl1 118.6(6) . . ?
C12 C13 Cl1 120.6(6) . . ?
N1 C14 C13 121.2(7) . . ?
O2 Cu1 O1 173.0(2) . 4_565 ?
O2 Cu1 O3 90.1(2) . 4_566 ?
O1 Cu1 O3 91.58(19) 4_565 4_566 ?
O2 Cu1 O4 88.1(2) . . ?
O1 Cu1 O4 89.3(2) 4_565 . ?
O3 Cu1 O4 172.8(2) 4_566 . ?
O2 Cu1 N1 99.9(2) . . ?
O1 Cu1 N1 86.8(2) 4_565 . ?
O3 Cu1 N1 90.1(2) 4_566 . ?
O4 Cu1 N1 97.1(2) . . ?
C14 N1 C10 118.4(6) . . ?
C14 N1 Cu1 119.0(5) . . ?
C10 N1 Cu1 120.7(5) . . ?
C1 O1 Cu1 122.4(4) . 4_666 ?
C3 O4 Cu1 118.6(4) . . ?
C1 O2 Cu1 119.7(4) . . ?
C3 O3 Cu1 128.6(4) . 4_665 ?

_refine_diff_density_max         2.129
_refine_diff_density_min         -1.373
_refine_diff_density_rms         0.144



_database_code_depnum_ccdc_archive 'CCDC 996272'
#######################################################################
#
#                 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_compound_7

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 Br Cu N O4'
_chemical_formula_weight         399.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   6.2413(2)
_cell_length_b                   31.0345(7)
_cell_length_c                   6.9777(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.573(2)
_cell_angle_gamma                90
_cell_volume                     1348.92(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4276
_cell_measurement_theta_min      5.6490
_cell_measurement_theta_max      73.2450

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.968
_exptl_crystal_F_000             788
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2180
_exptl_crystal_size_mid          0.1793
_exptl_crystal_size_min          0.0229
_exptl_absorpt_coefficient_mu    5.908
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.397
_exptl_absorpt_correction_T_max  0.872
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.5953
_diffrn_reflns_number            9106
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         5.702
_diffrn_reflns_theta_max         73.451
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2648
_reflns_number_gt                2448
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1060P)²+1.6240P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2648
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1707
_refine_ls_wR_factor_gt          0.1675
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_restrained_S_all      1.184
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5870(6) 0.78639(12) 0.8632(6) 0.0229(8) Uani 1 1 d . . . . .
C2 C 0.4985(6) 0.80830(12) 0.6764(5) 0.0220(7) Uani 1 1 d . . . . .
H2 H 0.3428 0.8038 0.6688 0.026 Uiso 1 1 calc R U . . .
C3 C 0.5864(6) 0.78307(12) 0.5074(5) 0.0207(7) Uani 1 1 d . . . . .
C4 C 0.5334(7) 0.85623(13) 0.6678(5) 0.0260(8) Uani 1 1 d . . . . .
C5 C 0.7343(8) 0.87492(14) 0.7068(7) 0.0346(9) Uani 1 1 d . . . . .
H5 H 0.8533 0.8575 0.7347 0.042 Uiso 1 1 calc R U . . .
C6 C 0.7579(10) 0.91905(17) 0.7044(8) 0.0463(12) Uani 1 1 d . . . . .
H6 H 0.8924 0.9312 0.7322 0.056 Uiso 1 1 calc R U . . .
C7 C 0.5819(11) 0.94550(16) 0.6606(8) 0.0497(13) Uani 1 1 d . . . . .
H7 H 0.5979 0.9753 0.6609 0.060 Uiso 1 1 calc R U . . .
C8 C 0.3829(10) 0.92724(17) 0.6165(8) 0.0477(13) Uani 1 1 d . . . . .
H8 H 0.2653 0.9448 0.5842 0.057 Uiso 1 1 calc R U . . .
C9 C 0.3586(8) 0.88295(14) 0.6205(7) 0.0347(10) Uani 1 1 d . . . . .
H9 H 0.2241 0.8709 0.5914 0.042 Uiso 1 1 calc R U . . .
C10 C 0.7498(7) 0.64957(15) 0.6409(6) 0.0328(9) Uani 1 1 d . . . . .
H10 H 0.8281 0.6747 0.6245 0.039 Uiso 1 1 calc R U . . .
C11 C 0.8422(8) 0.61055(17) 0.6004(7) 0.0382(10) Uani 1 1 d . . . . .
H11 H 0.9803 0.6095 0.5578 0.046 Uiso 1 1 calc R U . . .
C12 C 0.7285(8) 0.57316(16) 0.6235(7) 0.0389(10) Uani 1 1 d . . . . .
H12 H 0.7865 0.5464 0.5960 0.047 Uiso 1 1 calc R U . . .
C13 C 0.5252(8) 0.57675(14) 0.6887(7) 0.0346(9) Uani 1 1 d . . . . .
C14 C 0.4407(7) 0.61657(13) 0.7278(7) 0.0303(9) Uani 1 1 d . . . . .
H14 H 0.3036 0.6183 0.7723 0.036 Uiso 1 1 calc R U . . .
Br1 Br 0.35649(11) 0.52687(2) 0.72266(10) 0.0573(3) Uani 1 1 d . . . . .
Cu1 Cu 0.37667(9) 0.71584(2) 0.69195(8) 0.0222(2) Uani 1 1 d . . . . .
N1 N 0.5515(6) 0.65273(11) 0.7032(5) 0.0277(7) Uani 1 1 d . . . . .
O1 O 0.6895(4) 0.80908(9) 0.9852(4) 0.0251(6) Uani 1 1 d . . . . .
O2 O 0.5493(5) 0.74701(9) 0.8869(4) 0.0303(6) Uani 1 1 d . . . . .
O3 O 0.6870(5) 0.80433(9) 0.3893(4) 0.0268(6) Uani 1 1 d . . . . .
O4 O 0.5500(5) 0.74345(9) 0.4950(4) 0.0282(6) 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
C1 0.0215(18) 0.0280(19) 0.0196(19) 0.0000(13) 0.0053(15) 0.0033(13)
C2 0.0202(17) 0.0277(18) 0.0183(17) 0.0002(13) 0.0028(13) 0.0007(13)
C3 0.0173(16) 0.0288(19) 0.0158(18) -0.0001(12) -0.0005(13) 0.0037(12)
C4 0.031(2) 0.0273(18) 0.0198(18) -0.0011(13) 0.0044(15) 0.0031(15)
C5 0.035(2) 0.035(2) 0.034(2) 0.0013(17) 0.0053(18) -0.0023(17)
C6 0.054(3) 0.041(3) 0.044(3) 0.000(2) 0.006(2) -0.016(2)
C7 0.081(4) 0.025(2) 0.044(3) 0.0018(19) 0.009(3) 0.000(2)
C8 0.068(4) 0.038(3) 0.037(3) 0.0001(19) 0.000(2) 0.019(2)
C9 0.039(2) 0.035(2) 0.029(2) -0.0017(16) -0.0028(18) 0.0097(17)
C10 0.028(2) 0.039(2) 0.031(2) 0.0046(16) 0.0031(16) 0.0001(16)
C11 0.029(2) 0.053(3) 0.032(2) 0.0032(19) 0.0074(18) 0.0098(19)
C12 0.042(2) 0.040(2) 0.035(2) 0.0009(18) 0.0069(19) 0.0163(19)
C13 0.041(2) 0.028(2) 0.035(2) 0.0016(16) 0.0041(19) -0.0002(17)
C14 0.028(2) 0.032(2) 0.032(2) 0.0025(15) 0.0033(17) 0.0008(15)
Br1 0.0753(5) 0.0302(3) 0.0688(5) -0.0027(2) 0.0241(3) -0.0107(2)
Cu1 0.0242(4) 0.0233(4) 0.0193(4) 0.00012(18) 0.0026(2) -0.00305(18)
N1 0.0251(16) 0.0290(17) 0.0288(17) 0.0013(13) 0.0012(13) 0.0011(13)
O1 0.0267(13) 0.0263(13) 0.0219(13) -0.0025(10) -0.0022(10) 0.0011(10)
O2 0.0376(16) 0.0276(14) 0.0251(14) 0.0042(11) -0.0036(12) -0.0078(11)
O3 0.0322(15) 0.0265(13) 0.0228(13) 0.0023(10) 0.0104(11) 0.0028(10)
O4 0.0335(15) 0.0264(13) 0.0257(14) -0.0019(10) 0.0095(11) -0.0037(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 O1 1.250(5) . ?
C1 O2 1.258(5) . ?
C1 C2 1.542(5) . ?
C2 C4 1.505(5) . ?
C2 C3 1.544(5) . ?
C3 O4 1.252(5) . ?
C3 O3 1.254(5) . ?
C4 C5 1.393(6) . ?
C4 C9 1.394(6) . ?
C5 C6 1.378(7) . ?
C6 C7 1.390(9) . ?
C7 C8 1.382(9) . ?
C8 C9 1.383(7) . ?
C10 N1 1.341(6) . ?
C10 C11 1.378(7) . ?
C11 C12 1.375(7) . ?
C12 C13 1.379(7) . ?
C13 C14 1.378(6) . ?
C13 Br1 1.895(5) . ?
C14 N1 1.335(6) . ?
Cu1 O2 1.940(3) . ?
Cu1 O1 1.958(3) 4_575 ?
Cu1 O3 1.973(3) 4_576 ?
Cu1 O4 1.995(3) . ?
Cu1 N1 2.241(3) . ?
O1 Cu1 1.958(3) 4_676 ?
O3 Cu1 1.973(3) 4_675 ?

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 C1 O2 123.4(4) . . ?
O1 C1 C2 117.9(3) . . ?
O2 C1 C2 118.6(3) . . ?
C4 C2 C1 115.1(3) . . ?
C4 C2 C3 114.3(3) . . ?
C1 C2 C3 107.2(3) . . ?
O4 C3 O3 124.6(3) . . ?
O4 C3 C2 118.6(3) . . ?
O3 C3 C2 116.8(3) . . ?
C5 C4 C9 118.7(4) . . ?
C5 C4 C2 122.3(4) . . ?
C9 C4 C2 119.0(4) . . ?
C6 C5 C4 120.5(5) . . ?
C5 C6 C7 120.4(5) . . ?
C8 C7 C6 119.6(5) . . ?
C7 C8 C9 120.1(5) . . ?
C8 C9 C4 120.7(5) . . ?
N1 C10 C11 122.5(4) . . ?
C12 C11 C10 119.5(4) . . ?
C11 C12 C13 117.5(4) . . ?
C12 C13 C14 120.6(4) . . ?
C12 C13 Br1 120.3(3) . . ?
C14 C13 Br1 119.0(4) . . ?
N1 C14 C13 121.4(4) . . ?
O2 Cu1 O1 173.33(12) . 4_575 ?
O2 Cu1 O3 89.99(12) . 4_576 ?
O1 Cu1 O3 91.88(12) 4_575 4_576 ?
O2 Cu1 O4 88.13(13) . . ?
O1 Cu1 O4 89.23(12) 4_575 . ?
O3 Cu1 O4 172.73(12) 4_576 . ?
O2 Cu1 N1 99.40(13) . . ?
O1 Cu1 N1 86.99(12) 4_575 . ?
O3 Cu1 N1 90.59(12) 4_576 . ?
O4 Cu1 N1 96.65(13) . . ?
C14 N1 C10 118.4(4) . . ?
C14 N1 Cu1 119.0(3) . . ?
C10 N1 Cu1 120.7(3) . . ?
C1 O1 Cu1 122.4(2) . 4_676 ?
C1 O2 Cu1 119.5(3) . . ?
C3 O3 Cu1 129.7(2) . 4_675 ?
C3 O4 Cu1 118.6(2) . . ?

_refine_diff_density_max         1.698
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.190




_database_code_depnum_ccdc_archive 'CCDC 996273'
#######################################################################
#
#                 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_compound_8

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 Cu I N O4'
_chemical_formula_weight         446.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   6.2716(2)
_cell_length_b                   31.9680(7)
_cell_length_c                   6.9916(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.949(2)
_cell_angle_gamma                90
_cell_volume                     1398.42(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4354
_cell_measurement_theta_min      5.5250
_cell_measurement_theta_max      73.4140

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.122
_exptl_crystal_F_000             860
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1982
_exptl_crystal_size_mid          0.1798
_exptl_crystal_size_min          0.0295
_exptl_absorpt_coefficient_mu    19.686
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.444
_exptl_absorpt_correction_T_max  0.841
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.5953
_diffrn_reflns_number            9646
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         5.535
_diffrn_reflns_theta_max         73.330
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2780
_reflns_number_gt                2588
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    CRYSTALMAKER
_computing_publication_material  'PARST97 (Nardelli, 1997)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0716P)²+2.8088P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2780
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1392
_refine_ls_wR_factor_gt          0.1364
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_restrained_S_all      1.181
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4353(7) 0.78523(14) 0.1324(6) 0.0209(9) Uani 1 1 d . . . . .
C2 C 0.5219(8) 0.80637(15) 0.3198(6) 0.0233(9) Uani 1 1 d . . . . .
H2 H 0.6771 0.8023 0.3285 0.028 Uiso 1 1 calc R U . . .
C3 C 0.4350(7) 0.78184(14) 0.4896(6) 0.0219(9) Uani 1 1 d . . . . .
C4 C 0.4850(8) 0.85292(15) 0.3279(6) 0.0252(9) Uani 1 1 d . . . . .
C5 C 0.2844(10) 0.87095(18) 0.2899(8) 0.0354(11) Uani 1 1 d . . . . .
H5 H 0.1660 0.8539 0.2628 0.042 Uiso 1 1 calc R U . . .
C6 C 0.2592(12) 0.9137(2) 0.2919(9) 0.0458(14) Uani 1 1 d . . . . .
H6 H 0.1242 0.9252 0.2654 0.055 Uiso 1 1 calc R U . . .
C7 C 0.4341(14) 0.94010(19) 0.3334(10) 0.0511(17) Uani 1 1 d . . . . .
H7 H 0.4174 0.9690 0.3322 0.061 Uiso 1 1 calc R U . . .
C8 C 0.6329(13) 0.9222(2) 0.3764(9) 0.0487(16) Uani 1 1 d . . . . .
H8 H 0.7502 0.9392 0.4076 0.058 Uiso 1 1 calc R U . . .
C9 C 0.6588(10) 0.87936(17) 0.3735(8) 0.0355(12) Uani 1 1 d . . . . .
H9 H 0.7936 0.8679 0.4021 0.043 Uiso 1 1 calc R U . . .
C10 C 0.2715(9) 0.65340(18) 0.3519(8) 0.0333(11) Uani 1 1 d . . . . .
H10 H 0.1953 0.6781 0.3653 0.040 Uiso 1 1 calc R U . . .
C11 C 0.1760(9) 0.61618(19) 0.3948(8) 0.0369(12) Uani 1 1 d . . . . .
H11 H 0.0390 0.6159 0.4380 0.044 Uiso 1 1 calc R U . . .
C12 C 0.2856(10) 0.57931(19) 0.3732(8) 0.0379(12) Uani 1 1 d . . . . .
H12 H 0.2236 0.5537 0.3999 0.045 Uiso 1 1 calc R U . . .
C13 C 0.4900(9) 0.58124(16) 0.3109(7) 0.0311(10) Uani 1 1 d . . . . .
C14 C 0.5765(9) 0.62023(16) 0.2688(8) 0.0301(10) Uani 1 1 d . . . . .
H14 H 0.7124 0.6214 0.2236 0.036 Uiso 1 1 calc R U . . .
I1 I 0.66949(8) 0.52720(2) 0.27818(7) 0.0533(2) Uani 1 1 d . . . . .
N1 N 0.4693(7) 0.65579(13) 0.2918(6) 0.0290(9) Uani 1 1 d . . . . .
O1 O 0.3327(6) 0.80755(11) 0.0109(5) 0.0267(7) Uani 1 1 d . . . . .
O2 O 0.4720(6) 0.74728(11) 0.1081(5) 0.0299(8) Uani 1 1 d . . . . .
O3 O 0.3354(6) 0.80231(11) 0.6061(5) 0.0288(7) Uani 1 1 d . . . . .
O4 O 0.4733(6) 0.74345(11) 0.5007(5) 0.0279(7) Uani 1 1 d . . . . .
Cu1 Cu 0.64592(11) 0.71688(2) 0.30335(9) 0.0220(2) 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
C1 0.020(2) 0.031(2) 0.0114(19) 0.0013(15) 0.0015(16) -0.0019(16)
C2 0.025(2) 0.033(2) 0.0120(19) -0.0004(16) 0.0027(16) -0.0031(18)
C3 0.020(2) 0.028(2) 0.017(2) -0.0020(16) 0.0044(17) -0.0027(16)
C4 0.028(2) 0.032(2) 0.016(2) 0.0004(17) 0.0019(17) -0.0054(19)
C5 0.036(3) 0.038(3) 0.032(3) -0.001(2) 0.007(2) 0.001(2)
C6 0.056(4) 0.042(3) 0.040(3) 0.001(2) 0.011(3) 0.014(3)
C7 0.083(5) 0.030(3) 0.042(3) 0.000(2) 0.014(3) -0.003(3)
C8 0.067(4) 0.039(3) 0.040(3) 0.001(2) 0.002(3) -0.017(3)
C9 0.042(3) 0.040(3) 0.024(3) 0.002(2) -0.002(2) -0.014(2)
C10 0.029(3) 0.045(3) 0.026(3) -0.004(2) 0.002(2) 0.003(2)
C11 0.027(3) 0.053(3) 0.031(3) -0.002(2) 0.005(2) -0.006(2)
C12 0.042(3) 0.040(3) 0.032(3) 0.001(2) 0.006(2) -0.011(2)
C13 0.038(3) 0.030(2) 0.026(2) -0.0033(19) 0.006(2) 0.000(2)
C14 0.028(2) 0.033(3) 0.030(3) -0.0013(19) 0.004(2) -0.0006(19)
I1 0.0712(4) 0.0324(3) 0.0589(3) 0.00229(15) 0.0233(2) 0.00868(16)
N1 0.029(2) 0.031(2) 0.026(2) -0.0013(16) 0.0006(17) -0.0008(16)
O1 0.0284(17) 0.0315(17) 0.0196(16) 0.0023(13) -0.0025(13) -0.0003(13)
O2 0.037(2) 0.0320(18) 0.0196(16) -0.0053(13) -0.0042(14) 0.0063(14)
O3 0.039(2) 0.0307(17) 0.0186(16) -0.0032(13) 0.0116(14) -0.0033(14)
O4 0.0334(19) 0.0301(17) 0.0210(16) 0.0019(13) 0.0083(14) 0.0024(14)
Cu1 0.0252(4) 0.0258(4) 0.0151(3) 0.0000(2) 0.0029(3) 0.0028(2)

_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 O2 1.249(6) . ?
C1 O1 1.253(6) . ?
C1 C2 1.540(6) . ?
C2 C4 1.508(7) . ?
C2 C3 1.552(6) . ?
C3 O3 1.246(6) . ?
C3 O4 1.252(6) . ?
C4 C5 1.393(8) . ?
C4 C9 1.399(7) . ?
C5 C6 1.377(8) . ?
C6 C7 1.398(11) . ?
C7 C8 1.386(11) . ?
C8 C9 1.378(9) . ?
C10 N1 1.339(7) . ?
C10 C11 1.375(8) . ?
C11 C12 1.378(9) . ?
C12 C13 1.384(8) . ?
C13 C14 1.399(8) . ?
C13 I1 2.083(5) . ?
C14 N1 1.336(7) . ?
N1 Cu1 2.244(4) . ?
O1 Cu1 1.963(3) 4_575 ?
O2 Cu1 1.947(4) . ?
O3 Cu1 1.979(3) 4_576 ?
O4 Cu1 2.001(4) . ?
Cu1 O1 1.963(3) 4_676 ?
Cu1 O3 1.979(3) 4_675 ?

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
O2 C1 O1 123.5(4) . . ?
O2 C1 C2 119.0(4) . . ?
O1 C1 C2 117.5(4) . . ?
C4 C2 C1 114.8(4) . . ?
C4 C2 C3 114.0(4) . . ?
C1 C2 C3 107.9(4) . . ?
O3 C3 O4 125.2(4) . . ?
O3 C3 C2 116.9(4) . . ?
O4 C3 C2 117.8(4) . . ?
C5 C4 C9 118.2(5) . . ?
C5 C4 C2 122.7(5) . . ?
C9 C4 C2 119.1(5) . . ?
C6 C5 C4 120.8(6) . . ?
C5 C6 C7 120.8(6) . . ?
C8 C7 C6 118.5(6) . . ?
C9 C8 C7 120.8(6) . . ?
C8 C9 C4 120.8(6) . . ?
N1 C10 C11 123.0(5) . . ?
C10 C11 C12 119.2(5) . . ?
C11 C12 C13 118.5(5) . . ?
C12 C13 C14 119.1(5) . . ?
C12 C13 I1 121.1(4) . . ?
C14 C13 I1 119.7(4) . . ?
N1 C14 C13 121.8(5) . . ?
C14 N1 C10 118.3(5) . . ?
C14 N1 Cu1 119.6(4) . . ?
C10 N1 Cu1 120.3(4) . . ?
C1 O1 Cu1 121.8(3) . 4_575 ?
C1 O2 Cu1 119.3(3) . . ?
C3 O3 Cu1 130.2(3) . 4_576 ?
C3 O4 Cu1 118.9(3) . . ?
O2 Cu1 O1 173.51(15) . 4_676 ?
O2 Cu1 O3 90.03(15) . 4_675 ?
O1 Cu1 O3 92.03(15) 4_676 4_675 ?
O2 Cu1 O4 88.17(15) . . ?
O1 Cu1 O4 89.01(15) 4_676 . ?
O3 Cu1 O4 172.58(15) 4_675 . ?
O2 Cu1 N1 99.07(16) . . ?
O1 Cu1 N1 87.04(15) 4_676 . ?
O3 Cu1 N1 91.36(16) 4_675 . ?
O4 Cu1 N1 96.03(16) . . ?

_refine_diff_density_max         1.846
_refine_diff_density_min         -0.869
_refine_diff_density_rms         0.170




_database_code_depnum_ccdc_archive 'CCDC 996274'
