# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

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

data_Crystal1
_database_code_depnum_ccdc_archive 'CCDC 1442110'
_audit_update_record             
;
2016-01-06 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;

_audit_creation_method           'by CrystalStructure 4.0'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C24 H20 Cu F2 N2 O5'
_chemical_formula_moiety         'C24 H20 Cu F2 N2 O5'
_chemical_formula_weight         517.98
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-Y,1/2+Z
5 1/2+X,1/2+Y,+Z
6 1/2-X,1/2+Y,1/2-Z
7 1/2-X,1/2-Y,-Z
8 1/2+X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   15.9217(3)
_cell_length_b                   6.07159(11)
_cell_length_c                   23.7095(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.1815(9)
_cell_angle_gamma                90.0000
_cell_volume                     2290.34(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11113
_cell_measurement_theta_min      3.73
_cell_measurement_theta_max      68.27
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.046
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1060.00
_exptl_absorpt_coefficient_mu    1.835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_T_max  0.919

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            18057
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_theta_max         68.19
_diffrn_reflns_theta_full        68.20
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2102
_reflns_number_gt                1693
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1486
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2102
_refine_ls_number_parameters     156
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0834P)²+0.9434P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.450
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Cu Cu -1.9646 0.5888
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.22714(10) 0.2500 0.0527(3) Uani 1.0 4 d . . .
F1 F 0.3499(3) 0.2238(6) -0.08214(11) 0.1665(18) Uani 1.0 8 d . . .
O1 O 0.44240(14) 0.2327(4) 0.17635(9) 0.0601(6) Uani 1.0 8 d . . .
O2 O 0.45533(16) -0.1264(5) 0.15980(9) 0.0792(8) Uani 1.0 8 d . . .
O3 O 0.5000 0.6018(5) 0.2500 0.0703(9) Uani 1.0 4 d . . .
N1 N 0.61020(15) 0.1918(5) 0.21108(10) 0.0534(6) Uani 1.0 8 d . . .
C1 C 0.43959(18) 0.0630(6) 0.14469(12) 0.0571(8) Uani 1.0 8 d . . .
C2 C 0.41426(19) 0.1071(6) 0.08375(12) 0.0605(8) Uani 1.0 8 d . . .
C3 C 0.4097(4) 0.3143(8) 0.06334(17) 0.1064(17) Uani 1.0 8 d . . .
C4 C 0.3884(5) 0.3549(10) 0.00688(19) 0.144(3) Uani 1.0 8 d . . .
C5 C 0.3702(4) 0.1836(10) -0.02661(18) 0.1113(18) Uani 1.0 8 d . . .
C6 C 0.3741(4) -0.0215(9) -0.00878(18) 0.132(3) Uani 1.0 8 d . . .
C7 C 0.3965(4) -0.0605(8) 0.04728(16) 0.1113(18) Uani 1.0 8 d . . .
C8 C 0.6370(2) 0.3434(7) 0.17533(13) 0.0653(9) Uani 1.0 8 d . . .
C9 C 0.7131(3) 0.3289(8) 0.15062(15) 0.0786(11) Uani 1.0 8 d . . .
C10 C 0.7638(3) 0.1514(8) 0.16183(15) 0.0775(11) Uani 1.0 8 d . . .
C11 C 0.7358(2) -0.0097(7) 0.19727(14) 0.0720(10) Uani 1.0 8 d . . .
C12 C 0.6593(2) 0.0161(6) 0.22113(13) 0.0630(8) Uani 1.0 8 d . . .
H3 H 0.4210 0.4322 0.0875 0.1277 Uiso 1.0 8 calc R . .
H3A H 0.4832 0.6468 0.2190 0.0844 Uiso 1.0 8 calc R . .
H4 H 0.3870 0.4978 -0.0072 0.1725 Uiso 1.0 8 calc R . .
H6 H 0.3621 -0.1377 -0.0333 0.1587 Uiso 1.0 8 calc R . .
H7 H 0.3995 -0.2049 0.0603 0.1336 Uiso 1.0 8 calc R . .
H8 H 0.6027 0.4638 0.1668 0.0784 Uiso 1.0 8 calc R . .
H9 H 0.7302 0.4391 0.1264 0.0943 Uiso 1.0 8 calc R . .
H10 H 0.8161 0.1398 0.1459 0.0930 Uiso 1.0 8 calc R . .
H11 H 0.7682 -0.1343 0.2049 0.0864 Uiso 1.0 8 calc R . .
H12 H 0.6409 -0.0929 0.2453 0.0756 Uiso 1.0 8 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2002 (Burla, et al., 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Cu1 O1 1.942(3) yes . .
Cu1 O1 1.942(3) yes . 2_655
Cu1 N1 2.025(3) yes . .
Cu1 N1 2.025(3) yes . 2_655
F1 C5 1.366(6) yes . .
O1 C1 1.275(4) yes . .
O2 C1 1.228(5) yes . .
N1 C8 1.332(5) yes . .
N1 C12 1.339(5) yes . .
C1 C2 1.509(4) yes . .
C2 C3 1.349(6) yes . .
C2 C7 1.358(6) yes . .
C3 C4 1.390(7) yes . .
C4 C5 1.334(8) yes . .
C5 C6 1.316(8) yes . .
C6 C7 1.383(6) yes . .
C8 C9 1.368(5) yes . .
C9 C10 1.366(6) yes . .
C10 C11 1.375(6) yes . .
C11 C12 1.370(5) yes . .
O3 H3A 0.820 no . .
O3 H3A 0.820 no . 2_655
C3 H3 0.930 no . .
C4 H4 0.930 no . .
C6 H6 0.930 no . .
C7 H7 0.930 no . .
C8 H8 0.930 no . .
C9 H9 0.930 no . .
C10 H10 0.930 no . .
C11 H11 0.930 no . .
C12 H12 0.930 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
O1 Cu1 O1 178.00(10) yes . . 2_655
O1 Cu1 N1 88.84(10) yes . . .
O1 Cu1 N1 91.37(10) yes . . 2_655
O1 Cu1 N1 91.37(10) yes 2_655 . .
O1 Cu1 N1 88.84(10) yes 2_655 . 2_655
N1 Cu1 N1 167.84(11) yes . . 2_655
Cu1 O1 C1 121.4(2) yes . . .
Cu1 N1 C8 121.4(3) yes . . .
Cu1 N1 C12 120.9(2) yes . . .
C8 N1 C12 117.6(3) yes . . .
O1 C1 O2 125.7(3) yes . . .
O1 C1 C2 115.0(3) yes . . .
O2 C1 C2 119.3(3) yes . . .
C1 C2 C3 121.2(4) yes . . .
C1 C2 C7 121.2(4) yes . . .
C3 C2 C7 117.6(4) yes . . .
C2 C3 C4 121.2(5) yes . . .
C3 C4 C5 118.3(5) yes . . .
F1 C5 C4 118.2(5) yes . . .
F1 C5 C6 119.0(5) yes . . .
C4 C5 C6 122.7(5) yes . . .
C5 C6 C7 118.6(5) yes . . .
C2 C7 C6 121.5(5) yes . . .
N1 C8 C9 122.6(4) yes . . .
C8 C9 C10 119.6(4) yes . . .
C9 C10 C11 118.5(4) yes . . .
C10 C11 C12 119.0(4) yes . . .
N1 C12 C11 122.7(4) yes . . .
H3A O3 H3A 141.046 no . . 2_655
C2 C3 H3 119.377 no . . .
C4 C3 H3 119.395 no . . .
C3 C4 H4 120.838 no . . .
C5 C4 H4 120.818 no . . .
C5 C6 H6 120.722 no . . .
C7 C6 H6 120.716 no . . .
C2 C7 H7 119.234 no . . .
C6 C7 H7 119.234 no . . .
N1 C8 H8 118.713 no . . .
C9 C8 H8 118.711 no . . .
C8 C9 H9 120.207 no . . .
C10 C9 H9 120.224 no . . .
C9 C10 H10 120.766 no . . .
C11 C10 H10 120.756 no . . .
C10 C11 H11 120.481 no . . .
C12 C11 H11 120.491 no . . .
N1 C12 H12 118.670 no . . .
C11 C12 H12 118.675 no . . .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O1 Cu1 N1 C8 60.38(18) no . . . .
O1 Cu1 N1 C12 -120.65(18) no . . . .
N1 Cu1 O1 C1 67.12(18) no . . . .
O1 Cu1 N1 C8 -117.63(18) no . . 2_655 2_655
O1 Cu1 N1 C12 61.35(18) no . . 2_655 2_655
N1 Cu1 O1 C1 -100.71(18) no 2_655 . . .
O1 Cu1 N1 C8 -117.63(18) no 2_655 . . .
O1 Cu1 N1 C12 61.35(18) no 2_655 . . .
N1 Cu1 O1 C1 -100.71(18) no . . 2_655 2_655
O1 Cu1 N1 C8 60.38(18) no 2_655 . 2_655 2_655
O1 Cu1 N1 C12 -120.65(18) no 2_655 . 2_655 2_655
N1 Cu1 O1 C1 67.12(18) no 2_655 . 2_655 2_655
Cu1 O1 C1 O2 16.1(4) no . . . .
Cu1 O1 C1 C2 -164.05(15) no . . . .
Cu1 N1 C8 C9 176.70(19) no . . . .
Cu1 N1 C12 C11 -177.48(18) no . . . .
C8 N1 C12 C11 1.5(5) no . . . .
C12 N1 C8 C9 -2.3(5) no . . . .
O1 C1 C2 C3 11.0(4) no . . . .
O1 C1 C2 C7 -170.1(3) no . . . .
O2 C1 C2 C3 -169.1(3) no . . . .
O2 C1 C2 C7 9.8(5) no . . . .
C1 C2 C3 C4 178.4(4) no . . . .
C1 C2 C7 C6 -179.3(4) no . . . .
C3 C2 C7 C6 -0.4(7) no . . . .
C7 C2 C3 C4 -0.6(7) no . . . .
C2 C3 C4 C5 1.8(9) no . . . .
C3 C4 C5 F1 -179.5(5) no . . . .
C3 C4 C5 C6 -2.2(10) no . . . .
F1 C5 C6 C7 178.6(5) no . . . .
C4 C5 C6 C7 1.3(10) no . . . .
C5 C6 C7 C2 0.0(9) no . . . .
N1 C8 C9 C10 1.1(6) no . . . .
C8 C9 C10 C11 0.9(6) no . . . .
C9 C10 C11 C12 -1.7(5) no . . . .
C10 C11 C12 N1 0.4(5) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Cu1 O2 3.094(3) no . .
Cu1 O2 3.094(3) no . 2_655
Cu1 C1 2.823(3) no . 2_655
Cu1 C8 2.947(4) no . 2_655
Cu1 C12 2.946(4) no . 2_655
F1 C3 3.586(5) no . .
F1 C7 3.574(5) no . .
O1 C3 2.755(5) no . .
O1 C7 3.591(5) no . .
O1 C8 3.172(4) no . .
O1 C12 3.250(4) no . 2_655
O2 N1 3.326(4) no . .
O2 C3 3.576(6) no . .
O2 C7 2.822(5) no . .
O2 C12 3.528(4) no . 2_655
N1 C1 3.185(4) no . .
N1 C10 2.761(5) no . .
C2 C5 2.723(6) no . .
C3 C6 2.707(7) no . .
C4 C7 2.699(7) no . .
C8 C11 2.697(6) no . .
C9 C12 2.691(6) no . .
Cu1 O3 2.275(3) no . .
F1 C8 3.445(5) no . 3_665
F1 C9 3.301(6) no . 3_665
F1 C10 3.432(6) no . 3_655
F1 C11 3.274(5) no . 3_655
O1 O3 2.965(4) no . .
O2 O3 2.773(3) no . 1_545
O2 C10 3.336(5) no . 5_445
O3 Cu1 2.275(3) no . .
O3 O1 2.965(4) no . .
O3 O1 2.965(4) no . 2_655
O3 O2 2.773(3) no . 1_565
O3 O2 2.773(3) no . 2_665
O3 N1 3.201(4) no . .
O3 N1 3.201(4) no . 2_655
O3 C8 3.264(4) no . .
O3 C8 3.264(4) no . 2_655
N1 O3 3.201(4) no . .
C8 F1 3.445(5) no . 3_665
C8 O3 3.264(4) no . .
C9 F1 3.301(6) no . 3_665
C10 F1 3.432(6) no . 3_655
C10 O2 3.336(5) no . 5_555
C11 F1 3.274(5) no . 3_655
Cu1 H8 2.9786 no . .
Cu1 H8 2.9786 no . 2_655
Cu1 H12 2.9726 no . .
Cu1 H12 2.9726 no . 2_655
F1 H4 2.4889 no . .
F1 H6 2.4857 no . .
O1 H3 2.4427 no . .
O1 H8 2.9288 no . .
O1 H12 3.0506 no . 2_655
O2 H7 2.5343 no . .
O2 H12 3.5239 no . .
O2 H12 2.7776 no . 2_655
N1 H9 3.1988 no . .
N1 H11 3.2090 no . .
C1 H3 2.6308 no . .
C1 H7 2.6381 no . .
C1 H8 3.5832 no . .
C1 H12 3.0980 no . 2_655
C2 H4 3.2239 no . .
C2 H6 3.2296 no . .
C3 H7 3.1573 no . .
C4 H6 3.1621 no . .
C5 H3 3.1758 no . .
C5 H7 3.1552 no . .
C6 H4 3.1600 no . .
C7 H3 3.1596 no . .
C8 H10 3.2084 no . .
C8 H12 3.1244 no . .
C9 H11 3.2012 no . .
C10 H8 3.1957 no . .
C10 H12 3.2000 no . .
C11 H9 3.2010 no . .
C12 H8 3.1256 no . .
C12 H10 3.2117 no . .
H3 H4 2.3238 no . .
H3 H8 3.3954 no . .
H6 H7 2.3127 no . .
H8 H9 2.2832 no . .
H9 H10 2.3100 no . .
H10 H11 2.3222 no . .
H11 H12 2.2884 no . .
Cu1 H3A 2.6630 no . .
Cu1 H3A 2.6630 no . 2_655
F1 H8 2.8838 no . 3_665
F1 H9 2.6101 no . 3_665
F1 H11 3.4481 no . 3_655
O1 H3A 2.7775 no . .
O1 H10 3.2505 no . 5_455
O1 H11 2.9910 no . 5_455
O2 H3 3.2168 no . 1_545
O2 H3A 2.0033 no . 1_545
O2 H3A 3.3016 no . 2_645
O2 H8 3.4200 no . 1_545
O2 H10 2.6427 no . 5_445
O3 H8 2.7405 no . .
O3 H8 2.7405 no . 2_655
O3 H12 2.9152 no . 1_565
O3 H12 2.9152 no . 2_665
N1 H3A 3.4334 no . .
N1 H3A 3.5748 no . 2_655
N1 H11 2.9215 no . 6_655
C1 H3A 3.1424 no . 1_545
C1 H9 3.4289 no . 5_445
C1 H10 3.2364 no . 5_445
C2 H9 3.2975 no . 5_445
C2 H10 3.5831 no . 5_445
C3 H7 2.9244 no . 1_565
C3 H10 3.1905 no . 5_455
C4 H6 3.2474 no . 1_565
C4 H7 2.9602 no . 1_565
C6 H4 2.9256 no . 1_545
C7 H3 3.2432 no . 1_545
C7 H4 2.9776 no . 1_545
C7 H9 3.3023 no . 5_445
C7 H10 3.2622 no . 5_445
C8 H3A 3.2653 no . .
C8 H6 3.5914 no . 3_655
C8 H11 3.1667 no . 6_655
C9 H6 3.2033 no . 3_655
C9 H11 3.4337 no . 6_655
C9 H12 3.3595 no . 6_655
C10 H3 3.3884 no . 5_545
C10 H6 3.5837 no . 3_655
C10 H7 3.4089 no . 5_555
C10 H11 3.4722 no . 6_655
C10 H12 3.0515 no . 6_655
C11 H11 3.2538 no . 6_655
C11 H12 3.4516 no . 6_655
C12 H3A 3.5901 no . 1_545
C12 H3A 3.5264 no . 2_645
C12 H11 2.9591 no . 6_655
H3 O2 3.2168 no . 1_565
H3 C7 3.2432 no . 1_565
H3 C10 3.3884 no . 5_455
H3 H3A 3.4872 no . .
H3 H7 2.3174 no . 1_565
H3 H10 2.5443 no . 5_455
H3A Cu1 2.6630 no . .
H3A O1 2.7775 no . .
H3A O2 2.0033 no . 1_565
H3A O2 3.3016 no . 2_665
H3A N1 3.4334 no . .
H3A N1 3.5748 no . 2_655
H3A C1 3.1424 no . 1_565
H3A C8 3.2653 no . .
H3A C12 3.5901 no . 1_565
H3A C12 3.5264 no . 2_665
H3A H3 3.4872 no . .
H3A H8 2.5627 no . .
H3A H8 3.2734 no . 2_655
H3A H10 3.1196 no . 5_455
H3A H12 3.0120 no . 1_565
H3A H12 2.6911 no . 2_665
H4 C6 2.9256 no . 1_565
H4 C7 2.9776 no . 1_565
H4 H6 2.3276 no . 1_565
H4 H7 2.4152 no . 1_565
H4 H9 3.3480 no . 3_665
H6 C4 3.2474 no . 1_545
H6 C8 3.5914 no . 3_655
H6 C9 3.2033 no . 3_655
H6 C10 3.5837 no . 3_655
H6 H4 2.3276 no . 1_545
H6 H9 3.1823 no . 3_655
H7 C3 2.9244 no . 1_545
H7 C4 2.9602 no . 1_545
H7 C10 3.4089 no . 5_445
H7 H3 2.3174 no . 1_545
H7 H4 2.4152 no . 1_545
H7 H9 3.2871 no . 5_445
H7 H10 2.6408 no . 5_445
H8 F1 2.8838 no . 3_665
H8 O2 3.4200 no . 1_565
H8 O3 2.7405 no . .
H8 H3A 2.5627 no . .
H8 H3A 3.2734 no . 2_655
H8 H12 3.3147 no . 1_565
H9 F1 2.6101 no . 3_665
H9 C1 3.4289 no . 5_555
H9 C2 3.2975 no . 5_555
H9 C7 3.3023 no . 5_555
H9 H4 3.3480 no . 3_665
H9 H6 3.1823 no . 3_655
H9 H7 3.2871 no . 5_555
H9 H11 3.2344 no . 1_565
H10 O1 3.2505 no . 5_545
H10 O2 2.6427 no . 5_555
H10 C1 3.2364 no . 5_555
H10 C2 3.5831 no . 5_555
H10 C3 3.1905 no . 5_545
H10 C7 3.2622 no . 5_555
H10 H3 2.5443 no . 5_545
H10 H3A 3.1196 no . 5_545
H10 H7 2.6408 no . 5_555
H10 H12 3.1037 no . 6_655
H11 F1 3.4481 no . 3_655
H11 O1 2.9910 no . 5_545
H11 N1 2.9215 no . 6_645
H11 C8 3.1667 no . 6_645
H11 C9 3.4337 no . 6_645
H11 C10 3.4722 no . 6_645
H11 C11 3.2538 no . 6_645
H11 C12 2.9591 no . 6_645
H11 H9 3.2344 no . 1_545
H11 H12 3.3337 no . 6_645
H12 O3 2.9152 no . 1_545
H12 C9 3.3595 no . 6_645
H12 C10 3.0515 no . 6_645
H12 C11 3.4516 no . 6_645
H12 H3A 3.0120 no . 1_545
H12 H3A 2.6911 no . 2_645
H12 H8 3.3147 no . 1_545
H12 H10 3.1037 no . 6_645
H12 H11 3.3337 no . 6_655

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H3A O2 . . 1_565 2.773(3) 0.820 2.003 156.0 no
O3 H3A O2 . 2_655 2_665 2.773(3) 0.820 2.003 156.0 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_Crystal2
_database_code_depnum_ccdc_archive 'CCDC 1442111'
_audit_update_record             
;
2016-01-06 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;
_audit_creation_method           'by CrystalStructure 4.0'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C24 H20 Cl2 Cu N2 O5'
_chemical_formula_moiety         'C24 H20 Cl2 Cu N2 O5'
_chemical_formula_weight         550.88
_chemical_melting_point          ?
_chemical_absolute_configuration ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_Int_Tables_number      5
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,+Y,-Z
3 1/2+X,1/2+Y,+Z
4 1/2-X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   15.8329(4)
_cell_length_b                   5.82472(13)
_cell_length_c                   14.7176(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 122.0724(9)
_cell_angle_gamma                90.0000
_cell_volume                     1150.14(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3489
_cell_measurement_theta_min      3.54
_cell_measurement_theta_max      68.23
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             562.00
_exptl_absorpt_coefficient_mu    3.824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.721
_exptl_absorpt_correction_T_max  0.962

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            6233
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_full        68.24
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2052
_reflns_number_gt                1822
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1125
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2052
_refine_ls_number_parameters     156
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0522P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.490
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  890 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.01(3)

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cu Cu -1.9646 0.5888
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.53791(12) 0.5000 0.0196(3) Uani 1.0 2 d . . .
Cl1 Cl 0.97420(9) 0.6265(2) 1.15792(8) 0.0355(4) Uani 1.0 4 d . . .
O1 O 0.62222(18) 0.5572(7) 0.64065(19) 0.0211(7) Uani 1.0 4 d . . .
O2 O 0.6355(2) 0.1799(6) 0.6769(3) 0.0250(8) Uani 1.0 4 d . . .
O3 O 0.5000 0.9191(7) 0.5000 0.0237(10) Uani 1.0 2 d . . .
N1 N 0.4232(3) 0.4868(6) 0.5725(3) 0.0203(9) Uani 1.0 4 d . . .
C1 C 0.6584(4) 0.3852(9) 0.7026(4) 0.0210(10) Uani 1.0 4 d . . .
C2 C 0.7367(3) 0.4441(9) 0.8172(4) 0.0202(10) Uani 1.0 4 d . . .
C3 C 0.8076(3) 0.2825(9) 0.8838(4) 0.0242(11) Uani 1.0 4 d . . .
C4 C 0.8815(4) 0.3349(8) 0.9885(4) 0.0245(11) Uani 1.0 4 d . . .
C5 C 0.8817(3) 0.5540(12) 1.0268(3) 0.0258(11) Uani 1.0 4 d . . .
C6 C 0.8104(3) 0.7156(9) 0.9641(4) 0.0250(11) Uani 1.0 4 d . . .
C7 C 0.7384(3) 0.6609(9) 0.8577(4) 0.0230(11) Uani 1.0 4 d . . .
C8 C 0.4281(4) 0.6440(9) 0.6422(3) 0.0248(10) Uani 1.0 4 d . . .
C9 C 0.3719(3) 0.6216(9) 0.6895(3) 0.0222(10) Uani 1.0 4 d . . .
C10 C 0.3129(4) 0.4304(9) 0.6675(4) 0.0254(11) Uani 1.0 4 d . . .
C11 C 0.3095(3) 0.2672(9) 0.5981(3) 0.0235(10) Uani 1.0 4 d . . .
C12 C 0.3655(3) 0.2991(8) 0.5525(4) 0.0241(11) Uani 1.0 4 d . . .
H3 H 0.4501 0.9672 0.4428 0.0285 Uiso 1.0 4 calc R . .
H3A H 0.8053 0.1329 0.8569 0.0290 Uiso 1.0 4 calc R . .
H4 H 0.9306 0.2248 1.0328 0.0294 Uiso 1.0 4 calc R . .
H6 H 0.8102 0.8617 0.9927 0.0301 Uiso 1.0 4 calc R . .
H7 H 0.6904 0.7725 0.8129 0.0276 Uiso 1.0 4 calc R . .
H8 H 0.4707 0.7731 0.6596 0.0298 Uiso 1.0 4 calc R . .
H9 H 0.3744 0.7371 0.7365 0.0267 Uiso 1.0 4 calc R . .
H10 H 0.2750 0.4115 0.6998 0.0305 Uiso 1.0 4 calc R . .
H11 H 0.2691 0.1343 0.5818 0.0282 Uiso 1.0 4 calc R . .
H12 H 0.3634 0.1849 0.5053 0.0289 Uiso 1.0 4 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Cu1 O1 1.946(2) yes . .
Cu1 O1 1.946(2) yes . 2_656
Cu1 O3 2.220(5) yes . .
Cu1 N1 2.021(5) yes . .
Cu1 N1 2.021(5) yes . 2_656
Cl1 C5 1.745(4) yes . .
O1 C1 1.269(6) yes . .
O2 C1 1.249(6) yes . .
N1 C8 1.347(7) yes . .
N1 C12 1.354(6) yes . .
C1 C2 1.509(6) yes . .
C2 C3 1.392(6) yes . .
C2 C7 1.391(8) yes . .
C3 C4 1.386(6) yes . .
C4 C5 1.395(9) yes . .
C5 C6 1.381(7) yes . .
C6 C7 1.399(6) yes . .
C8 C9 1.396(9) yes . .
C9 C10 1.377(7) yes . .
C10 C11 1.375(8) yes . .
C11 C12 1.379(9) yes . .
O3 H3 0.840 no . .
O3 H3 0.840 no . 2_656
C3 H3A 0.950 no . .
C4 H4 0.950 no . .
C6 H6 0.950 no . .
C7 H7 0.950 no . .
C8 H8 0.950 no . .
C9 H9 0.950 no . .
C10 H10 0.950 no . .
C11 H11 0.950 no . .
C12 H12 0.950 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
O1 Cu1 O1 173.37(16) yes . . 2_656
O1 Cu1 O3 86.69(11) yes . . .
O1 Cu1 N1 89.08(13) yes . . .
O1 Cu1 N1 91.90(13) yes . . 2_656
O1 Cu1 O3 86.69(11) yes 2_656 . .
O1 Cu1 N1 91.90(13) yes 2_656 . .
O1 Cu1 N1 89.08(13) yes 2_656 . 2_656
O3 Cu1 N1 98.47(11) yes . . .
O3 Cu1 N1 98.47(11) yes . . 2_656
N1 Cu1 N1 163.06(15) yes . . 2_656
Cu1 O1 C1 122.2(3) yes . . .
Cu1 N1 C8 119.7(4) yes . . .
Cu1 N1 C12 122.0(4) yes . . .
C8 N1 C12 118.2(5) yes . . .
O1 C1 O2 126.2(4) yes . . .
O1 C1 C2 114.4(4) yes . . .
O2 C1 C2 119.4(4) yes . . .
C1 C2 C3 120.7(5) yes . . .
C1 C2 C7 120.2(4) yes . . .
C3 C2 C7 119.2(4) yes . . .
C2 C3 C4 121.5(5) yes . . .
C3 C4 C5 118.1(4) yes . . .
Cl1 C5 C4 119.3(4) yes . . .
Cl1 C5 C6 118.8(5) yes . . .
C4 C5 C6 121.9(4) yes . . .
C5 C6 C7 118.9(5) yes . . .
C2 C7 C6 120.4(4) yes . . .
N1 C8 C9 121.5(5) yes . . .
C8 C9 C10 119.4(5) yes . . .
C9 C10 C11 119.2(6) yes . . .
C10 C11 C12 119.1(5) yes . . .
N1 C12 C11 122.5(5) yes . . .
Cu1 O3 H3 109.471 no . . .
Cu1 O3 H3 109.471 no . . 2_656
H3 O3 H3 141.057 no . . 2_656
C2 C3 H3A 119.233 no . . .
C4 C3 H3A 119.242 no . . .
C3 C4 H4 120.962 no . . .
C5 C4 H4 120.972 no . . .
C5 C6 H6 120.535 no . . .
C7 C6 H6 120.528 no . . .
C2 C7 H7 119.815 no . . .
C6 C7 H7 119.817 no . . .
N1 C8 H8 119.247 no . . .
C9 C8 H8 119.238 no . . .
C8 C9 H9 120.327 no . . .
C10 C9 H9 120.314 no . . .
C9 C10 H10 120.399 no . . .
C11 C10 H10 120.396 no . . .
C10 C11 H11 120.451 no . . .
C12 C11 H11 120.454 no . . .
N1 C12 H12 118.734 no . . .
C11 C12 H12 118.736 no . . .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O3 Cu1 O1 C1 166.4(3) no . . . .
O1 Cu1 N1 C8 57.7(3) no . . . .
O1 Cu1 N1 C12 -123.0(3) no . . . .
N1 Cu1 O1 C1 67.9(3) no . . . .
O1 Cu1 N1 C8 -115.7(3) no . . 2_656 2_656
O1 Cu1 N1 C12 63.6(3) no . . 2_656 2_656
N1 Cu1 O1 C1 -95.2(3) no 2_656 . . .
O3 Cu1 O1 C1 166.4(3) no . . 2_656 2_656
O1 Cu1 N1 C8 -115.7(3) no 2_656 . . .
O1 Cu1 N1 C12 63.6(3) no 2_656 . . .
N1 Cu1 O1 C1 -95.2(3) no . . 2_656 2_656
O1 Cu1 N1 C8 57.7(3) no 2_656 . 2_656 2_656
O1 Cu1 N1 C12 -123.0(3) no 2_656 . 2_656 2_656
N1 Cu1 O1 C1 67.9(3) no 2_656 . 2_656 2_656
O3 Cu1 N1 C8 -28.8(2) no . . . .
O3 Cu1 N1 C12 150.48(19) no . . . .
O3 Cu1 N1 C8 -28.8(2) no . . 2_656 2_656
O3 Cu1 N1 C12 150.48(19) no . . 2_656 2_656
Cu1 O1 C1 O2 15.4(9) no . . . .
Cu1 O1 C1 C2 -165.0(3) no . . . .
Cu1 N1 C8 C9 176.4(2) no . . . .
Cu1 N1 C12 C11 -177.2(2) no . . . .
C8 N1 C12 C11 2.1(5) no . . . .
C12 N1 C8 C9 -2.9(5) no . . . .
O1 C1 C2 C3 -156.2(5) no . . . .
O1 C1 C2 C7 24.1(8) no . . . .
O2 C1 C2 C3 23.4(9) no . . . .
O2 C1 C2 C7 -156.2(5) no . . . .
C1 C2 C3 C4 178.5(5) no . . . .
C1 C2 C7 C6 179.5(5) no . . . .
C3 C2 C7 C6 -0.1(9) no . . . .
C7 C2 C3 C4 -1.9(9) no . . . .
C2 C3 C4 C5 1.6(9) no . . . .
C3 C4 C5 Cl1 -179.6(5) no . . . .
C3 C4 C5 C6 0.8(9) no . . . .
Cl1 C5 C6 C7 177.6(4) no . . . .
C4 C5 C6 C7 -2.7(9) no . . . .
C5 C6 C7 C2 2.3(9) no . . . .
N1 C8 C9 C10 2.4(6) no . . . .
C8 C9 C10 C11 -0.9(6) no . . . .
C9 C10 C11 C12 0.1(6) no . . . .
C10 C11 C12 N1 -0.7(6) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Cu1 O2 3.130(3) no . .
Cu1 O2 3.130(3) no . 2_656
Cu1 C1 2.834(4) no . 2_656
Cu1 C8 2.932(6) no . 2_656
Cu1 C12 2.970(6) no . 2_656
O1 C3 3.582(5) no . .
O1 C7 2.777(5) no . .
O1 C8 3.128(7) no . .
O1 C12 3.312(7) no . 2_656
O2 N1 3.371(5) no . .
O2 C3 2.871(4) no . .
O2 C12 3.440(7) no . 2_656
O3 C8 3.283(6) no . .
O3 C8 3.283(6) no . 2_656
N1 C1 3.211(6) no . .
N1 C1 3.586(7) no . 2_656
N1 C10 2.776(8) no . .
C1 C8 3.595(8) no . .
C2 C5 2.771(5) no . .
C3 C6 2.776(8) no . .
C4 C7 2.795(6) no . .
C8 C11 2.733(7) no . .
C9 C12 2.718(8) no . .
Cl1 C10 3.450(5) no . 4_657
Cl1 C11 3.498(4) no . 4_657
O1 C10 3.567(7) no . 3_555
O1 C11 3.557(7) no . 3_555
O2 O3 2.785(4) no . 1_545
O2 C10 3.231(7) no . 3_545
O3 O2 2.785(4) no . 1_565
O3 O2 2.785(4) no . 2_666
O3 C12 3.433(6) no . 1_565
O3 C12 3.433(6) no . 2_666
N1 C11 3.567(5) no . 4_556
C3 C6 3.500(8) no . 1_545
C4 C4 3.583(8) no . 2_757
C4 C6 3.530(9) no . 4_647
C6 C3 3.500(8) no . 1_565
C6 C4 3.530(9) no . 4_657
C10 Cl1 3.450(5) no . 4_647
C10 O1 3.567(7) no . 3_445
C10 O2 3.231(7) no . 3_455
C11 Cl1 3.498(4) no . 4_647
C11 O1 3.557(7) no . 3_445
C11 N1 3.567(5) no . 4_546
C12 O3 3.433(6) no . 1_545
Cu1 H8 2.9620 no . .
Cu1 H8 2.9620 no . 2_656
Cu1 H12 3.0146 no . .
Cu1 H12 3.0146 no . 2_656
Cl1 H4 2.8271 no . .
Cl1 H6 2.7974 no . .
O1 H3 2.6509 no . 2_656
O1 H7 2.5013 no . .
O1 H8 2.8516 no . .
O1 H12 3.1444 no . 2_656
O2 H3A 2.5995 no . .
O2 H12 2.6916 no . 2_656
O3 H8 2.7603 no . .
O3 H8 2.7603 no . 2_656
N1 H3 3.5381 no . .
N1 H3 3.5188 no . 2_656
N1 H9 3.2447 no . .
N1 H11 3.2468 no . .
C1 H3A 2.6676 no . .
C1 H7 2.6654 no . .
C1 H8 3.5138 no . .
C1 H12 3.1180 no . 2_656
C2 H4 3.2831 no . .
C2 H6 3.2792 no . .
C3 H7 3.2590 no . .
C4 H6 3.2814 no . .
C5 H3A 3.2437 no . .
C5 H7 3.2524 no . .
C6 H4 3.2825 no . .
C7 H3A 3.2551 no . .
C8 H3 3.3756 no . 2_656
C8 H10 3.2573 no . .
C8 H12 3.1734 no . .
C9 H11 3.2374 no . .
C10 H8 3.2472 no . .
C10 H12 3.2268 no . .
C11 H9 3.2364 no . .
C12 H8 3.1773 no . .
C12 H10 3.2374 no . .
H3 H7 3.3916 no . 2_656
H3 H8 3.2354 no . .
H3 H8 2.6709 no . 2_656
H3A H4 2.3390 no . .
H6 H7 2.3540 no . .
H7 H8 2.9767 no . .
H8 H9 2.3399 no . .
H9 H10 2.3378 no . .
H10 H11 2.3375 no . .
H11 H12 2.3170 no . .
Cu1 H3 3.4174 no . 1_545
Cu1 H3 3.4174 no . 2_646
Cl1 H7 3.5243 no . 4_647
Cl1 H8 3.1173 no . 4_647
Cl1 H9 3.0576 no . 4_647
O1 H10 2.9374 no . 3_555
O1 H11 2.9158 no . 3_555
O2 H3 3.3595 no . 1_545
O2 H3 1.9850 no . 2_646
O2 H7 2.9230 no . 1_545
O2 H8 3.4327 no . 1_545
O2 H9 3.4158 no . 3_545
O2 H10 2.5779 no . 3_545
O3 H12 2.6940 no . 1_565
O3 H12 2.6940 no . 2_666
N1 H11 2.7974 no . 4_556
C1 H3 3.0912 no . 2_646
C1 H9 3.2977 no . 3_545
C1 H10 3.3318 no . 3_545
C1 H10 3.5894 no . 3_555
C1 H11 3.4133 no . 3_555
C2 H6 3.2891 no . 4_647
C2 H9 3.2193 no . 3_545
C2 H10 3.4457 no . 3_555
C3 H6 2.9176 no . 1_545
C3 H6 3.2558 no . 4_647
C3 H7 3.3619 no . 1_545
C3 H9 2.8844 no . 3_545
C3 H10 3.2832 no . 3_545
C4 H4 3.2159 no . 2_757
C4 H6 2.9922 no . 1_545
C4 H6 3.1954 no . 4_647
C5 H6 3.1057 no . 4_647
C5 H7 3.5248 no . 4_647
C6 H3A 2.8756 no . 1_565
C6 H4 3.3760 no . 1_565
C6 H6 3.0970 no . 4_647
C7 H3A 2.9486 no . 1_565
C7 H6 3.2059 no . 4_647
C7 H10 3.0481 no . 3_555
C8 H11 3.5916 no . 1_565
C8 H11 3.1129 no . 4_556
C8 H12 3.5839 no . 1_565
C9 H3A 3.1522 no . 3_455
C9 H11 3.3672 no . 1_565
C9 H11 3.3864 no . 4_556
C9 H12 3.3010 no . 4_556
C10 H3 3.5830 no . 4_546
C10 H3A 3.0865 no . 3_455
C10 H11 3.3907 no . 4_556
C10 H12 2.9865 no . 4_556
C11 H9 3.5371 no . 1_545
C11 H11 3.1034 no . 4_556
C11 H12 3.3627 no . 4_556
C12 H3 3.2311 no . 1_545
C12 H3 3.4723 no . 2_646
C12 H8 3.4431 no . 1_545
C12 H11 2.7906 no . 4_556
H3 Cu1 3.4174 no . 1_565
H3 O2 3.3595 no . 1_565
H3 O2 1.9850 no . 2_666
H3 C1 3.0912 no . 2_666
H3 C10 3.5830 no . 4_556
H3 C12 3.2311 no . 1_565
H3 C12 3.4723 no . 2_666
H3 H10 3.0436 no . 4_556
H3 H12 2.3829 no . 1_565
H3 H12 2.9178 no . 2_666
H3A C6 2.8756 no . 1_545
H3A C7 2.9486 no . 1_545
H3A C9 3.1522 no . 3_545
H3A C10 3.0865 no . 3_545
H3A H6 2.5172 no . 1_545
H3A H7 2.6241 no . 1_545
H3A H9 2.6001 no . 3_545
H3A H10 2.4607 no . 3_545
H4 C4 3.2159 no . 2_757
H4 C6 3.3760 no . 1_545
H4 H4 2.8300 no . 2_757
H4 H6 2.6949 no . 1_545
H4 H9 3.1522 no . 4_647
H6 C2 3.2891 no . 4_657
H6 C3 2.9176 no . 1_565
H6 C3 3.2558 no . 4_657
H6 C4 2.9922 no . 1_565
H6 C4 3.1954 no . 4_657
H6 C5 3.1057 no . 4_657
H6 C6 3.0970 no . 4_657
H6 C7 3.2059 no . 4_657
H6 H3A 2.5172 no . 1_565
H6 H4 2.6949 no . 1_565
H6 H6 3.5492 no . 4_647
H6 H6 3.5492 no . 4_657
H7 Cl1 3.5243 no . 4_657
H7 O2 2.9230 no . 1_565
H7 C3 3.3619 no . 1_565
H7 C5 3.5248 no . 4_657
H7 H3A 2.6241 no . 1_565
H7 H10 2.7532 no . 3_555
H8 Cl1 3.1173 no . 4_657
H8 O2 3.4327 no . 1_565
H8 C12 3.4431 no . 1_565
H8 H11 3.4692 no . 1_565
H8 H12 3.1143 no . 1_565
H9 Cl1 3.0576 no . 4_657
H9 O2 3.4158 no . 3_455
H9 C1 3.2977 no . 3_455
H9 C2 3.2193 no . 3_455
H9 C3 2.8844 no . 3_455
H9 C11 3.5371 no . 1_565
H9 H3A 2.6001 no . 3_455
H9 H4 3.1522 no . 4_657
H9 H11 3.0464 no . 1_565
H9 H12 3.5642 no . 4_556
H10 O1 2.9374 no . 3_445
H10 O2 2.5779 no . 3_455
H10 C1 3.5894 no . 3_445
H10 C1 3.3318 no . 3_455
H10 C2 3.4457 no . 3_445
H10 C3 3.2832 no . 3_455
H10 C7 3.0481 no . 3_445
H10 H3 3.0436 no . 4_546
H10 H3A 2.4607 no . 3_455
H10 H7 2.7532 no . 3_445
H10 H12 3.0704 no . 4_556
H11 O1 2.9158 no . 3_445
H11 N1 2.7974 no . 4_546
H11 C1 3.4133 no . 3_445
H11 C8 3.5916 no . 1_545
H11 C8 3.1129 no . 4_546
H11 C9 3.3672 no . 1_545
H11 C9 3.3864 no . 4_546
H11 C10 3.3907 no . 4_546
H11 C11 3.1034 no . 4_546
H11 C12 2.7906 no . 4_546
H11 H8 3.4692 no . 1_545
H11 H9 3.0464 no . 1_545
H11 H12 3.1689 no . 4_546
H12 O3 2.6940 no . 1_545
H12 C8 3.5839 no . 1_545
H12 C9 3.3010 no . 4_546
H12 C10 2.9865 no . 4_546
H12 C11 3.3627 no . 4_546
H12 H3 2.3829 no . 1_545
H12 H3 2.9178 no . 2_646
H12 H8 3.1143 no . 1_545
H12 H9 3.5642 no . 4_546
H12 H10 3.0704 no . 4_546
H12 H11 3.1689 no . 4_556

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H3 O2 . . 2_666 2.785(4) 0.840 1.985 159.0 no
O3 H3 O2 . 2_656 1_565 2.785(4) 0.840 1.985 159.0 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_Crystal3
_database_code_depnum_ccdc_archive 'CCDC 1442112'
_audit_update_record             
;
2016-01-06 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;
_audit_creation_method           'by CrystalStructure 4.0'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C24 H20 Br2 Cu N2 O5'
_chemical_formula_moiety         'C24 H20 Br2 Cu N2 O5'
_chemical_formula_weight         639.79
_chemical_melting_point          ?
_chemical_absolute_configuration ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_Int_Tables_number      5
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,+Y,-Z
3 1/2+X,1/2+Y,+Z
4 1/2-X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   15.8100(3)
_cell_length_b                   5.83189(11)
_cell_length_c                   14.8160(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 121.1004(8)
_cell_angle_gamma                90.0000
_cell_volume                     1169.72(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4386
_cell_measurement_theta_min      3.48
_cell_measurement_theta_max      68.19
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.816
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             634.00
_exptl_absorpt_coefficient_mu    5.664
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.505
_exptl_absorpt_correction_T_max  0.945

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            6300
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_theta_max         68.18
_diffrn_reflns_theta_full        68.19
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2047
_reflns_number_gt                1847
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1080
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2047
_refine_ls_number_parameters     156
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0461P)²+0.5115P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.590
_refine_diff_density_min         -0.670
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  868 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.01(4)

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cu Cu -1.9646 0.5888
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Br Br -0.6763 1.2805
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Br2 Br 0.97869(4) 0.55748(15) 1.15382(4) 0.0299(2) Uani 1.0 4 d . . .
Cu1 Cu 0.5000 0.4564(2) 0.5000 0.0172(3) Uani 1.0 2 d . . .
O1 O 0.6193(3) 0.4773(8) 0.6384(3) 0.0179(10) Uani 1.0 4 d . . .
O2 O 0.6314(3) 0.0983(8) 0.6736(3) 0.0224(11) Uani 1.0 4 d . . .
O3 O 0.5000 0.8370(11) 0.5000 0.0229(15) Uani 1.0 2 d . . .
N1 N 0.4215(4) 0.4052(10) 0.5712(4) 0.0187(12) Uani 1.0 4 d . . .
C1 C 0.6552(5) 0.3023(13) 0.7005(5) 0.0183(14) Uani 1.0 4 d . . .
C2 C 0.7312(5) 0.3622(11) 0.8112(5) 0.0172(14) Uani 1.0 4 d . . .
C3 C 0.7338(4) 0.5808(14) 0.8521(4) 0.0211(14) Uani 1.0 4 d . . .
C4 C 0.8055(4) 0.6344(12) 0.9555(4) 0.0196(14) Uani 1.0 4 d . . .
C5 C 0.8762(4) 0.4711(14) 1.0166(5) 0.0223(15) Uani 1.0 4 d . . .
C6 C 0.8756(5) 0.2542(12) 0.9779(5) 0.0228(15) Uani 1.0 4 d . . .
C7 C 0.8017(4) 0.1976(12) 0.8759(4) 0.0196(14) Uani 1.0 4 d . . .
C8 C 0.4236(4) 0.5626(14) 0.6384(4) 0.0198(12) Uani 1.0 4 d . . .
C9 C 0.3677(4) 0.5397(16) 0.6854(5) 0.0232(14) Uani 1.0 4 d . . .
C10 C 0.3092(5) 0.3500(12) 0.6641(5) 0.0210(15) Uani 1.0 4 d . . .
C11 C 0.3075(4) 0.1828(13) 0.5958(4) 0.0198(13) Uani 1.0 4 d . . .
C12 C 0.3646(4) 0.2186(11) 0.5510(5) 0.0180(13) Uani 1.0 4 d . . .
H3 H 0.4702 0.8850 0.4376 0.0274 Uiso 1.0 4 calc R . .
H3A H 0.6862 0.6927 0.8091 0.0253 Uiso 1.0 4 calc R . .
H4 H 0.8062 0.7809 0.9840 0.0236 Uiso 1.0 4 calc R . .
H6 H 0.9252 0.1456 1.0205 0.0273 Uiso 1.0 4 calc R . .
H7 H 0.7987 0.0471 0.8499 0.0235 Uiso 1.0 4 calc R . .
H8 H 0.4646 0.6937 0.6543 0.0238 Uiso 1.0 4 calc R . .
H9 H 0.3699 0.6546 0.7320 0.0279 Uiso 1.0 4 calc R . .
H10 H 0.2702 0.3326 0.6955 0.0251 Uiso 1.0 4 calc R . .
H11 H 0.2683 0.0485 0.5806 0.0238 Uiso 1.0 4 calc R . .
H12 H 0.3635 0.1063 0.5040 0.0216 Uiso 1.0 4 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Br2 C5 1.900(5) yes . .
Cu1 O1 1.945(3) yes . .
Cu1 O1 1.945(3) yes . 2_656
Cu1 O3 2.220(7) yes . .
Cu1 N1 2.024(7) yes . .
Cu1 N1 2.024(7) yes . 2_656
O1 C1 1.292(8) yes . .
O2 C1 1.249(9) yes . .
N1 C8 1.342(9) yes . .
N1 C12 1.343(8) yes . .
C1 C2 1.491(8) yes . .
C2 C3 1.403(11) yes . .
C2 C7 1.407(8) yes . .
C3 C4 1.391(7) yes . .
C4 C5 1.390(9) yes . .
C5 C6 1.387(11) yes . .
C6 C7 1.390(8) yes . .
C8 C9 1.384(11) yes . .
C9 C10 1.370(11) yes . .
C10 C11 1.395(10) yes . .
C11 C12 1.386(11) yes . .
O3 H3 0.840 no . .
O3 H3 0.840 no . 2_656
C3 H3A 0.950 no . .
C4 H4 0.950 no . .
C6 H6 0.950 no . .
C7 H7 0.950 no . .
C8 H8 0.950 no . .
C9 H9 0.950 no . .
C10 H10 0.950 no . .
C11 H11 0.950 no . .
C12 H12 0.950 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
O1 Cu1 O1 172.8(2) yes . . 2_656
O1 Cu1 O3 86.41(14) yes . . .
O1 Cu1 N1 88.94(19) yes . . .
O1 Cu1 N1 92.12(19) yes . . 2_656
O1 Cu1 O3 86.41(14) yes 2_656 . .
O1 Cu1 N1 92.12(19) yes 2_656 . .
O1 Cu1 N1 88.94(19) yes 2_656 . 2_656
O3 Cu1 N1 98.48(16) yes . . .
O3 Cu1 N1 98.48(16) yes . . 2_656
N1 Cu1 N1 163.0(3) yes . . 2_656
Cu1 O1 C1 122.1(4) yes . . .
Cu1 N1 C8 119.9(5) yes . . .
Cu1 N1 C12 121.6(5) yes . . .
C8 N1 C12 118.5(7) yes . . .
O1 C1 O2 125.2(5) yes . . .
O1 C1 C2 113.9(6) yes . . .
O2 C1 C2 120.8(6) yes . . .
C1 C2 C3 121.0(5) yes . . .
C1 C2 C7 119.6(6) yes . . .
C3 C2 C7 119.3(5) yes . . .
C2 C3 C4 120.3(6) yes . . .
C3 C4 C5 119.1(7) yes . . .
Br2 C5 C4 118.0(6) yes . . .
Br2 C5 C6 120.3(5) yes . . .
C4 C5 C6 121.6(5) yes . . .
C5 C6 C7 119.2(6) yes . . .
C2 C7 C6 120.3(7) yes . . .
N1 C8 C9 121.9(7) yes . . .
C8 C9 C10 119.5(8) yes . . .
C9 C10 C11 119.3(8) yes . . .
C10 C11 C12 117.9(7) yes . . .
N1 C12 C11 122.8(7) yes . . .
Cu1 O3 H3 109.453 no . . .
Cu1 O3 H3 109.453 no . . 2_656
H3 O3 H3 141.094 no . . 2_656
C2 C3 H3A 119.828 no . . .
C4 C3 H3A 119.837 no . . .
C3 C4 H4 120.432 no . . .
C5 C4 H4 120.425 no . . .
C5 C6 H6 120.395 no . . .
C7 C6 H6 120.395 no . . .
C2 C7 H7 119.865 no . . .
C6 C7 H7 119.869 no . . .
N1 C8 H8 119.037 no . . .
C9 C8 H8 119.049 no . . .
C8 C9 H9 120.231 no . . .
C10 C9 H9 120.237 no . . .
C9 C10 H10 120.357 no . . .
C11 C10 H10 120.354 no . . .
C10 C11 H11 121.027 no . . .
C12 C11 H11 121.045 no . . .
N1 C12 H12 118.578 no . . .
C11 C12 H12 118.573 no . . .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O3 Cu1 O1 C1 166.7(4) no . . . .
O1 Cu1 N1 C8 58.3(3) no . . . .
O1 Cu1 N1 C12 -123.3(3) no . . . .
N1 Cu1 O1 C1 68.1(4) no . . . .
O1 Cu1 N1 C8 -114.6(3) no . . 2_656 2_656
O1 Cu1 N1 C12 63.7(4) no . . 2_656 2_656
N1 Cu1 O1 C1 -94.9(4) no 2_656 . . .
O3 Cu1 O1 C1 166.7(4) no . . 2_656 2_656
O1 Cu1 N1 C8 -114.6(3) no 2_656 . . .
O1 Cu1 N1 C12 63.7(4) no 2_656 . . .
N1 Cu1 O1 C1 -94.9(4) no . . 2_656 2_656
O1 Cu1 N1 C8 58.3(3) no 2_656 . 2_656 2_656
O1 Cu1 N1 C12 -123.3(3) no 2_656 . 2_656 2_656
N1 Cu1 O1 C1 68.1(4) no 2_656 . 2_656 2_656
O3 Cu1 N1 C8 -27.9(3) no . . . .
O3 Cu1 N1 C12 150.4(3) no . . . .
O3 Cu1 N1 C8 -27.9(3) no . . 2_656 2_656
O3 Cu1 N1 C12 150.4(3) no . . 2_656 2_656
Cu1 O1 C1 O2 14.7(11) no . . . .
Cu1 O1 C1 C2 -166.0(4) no . . . .
Cu1 N1 C8 C9 177.1(3) no . . . .
Cu1 N1 C12 C11 -177.8(3) no . . . .
C8 N1 C12 C11 0.6(7) no . . . .
C12 N1 C8 C9 -1.3(7) no . . . .
O1 C1 C2 C3 24.0(11) no . . . .
O1 C1 C2 C7 -155.9(6) no . . . .
O2 C1 C2 C3 -156.6(7) no . . . .
O2 C1 C2 C7 23.4(11) no . . . .
C1 C2 C3 C4 -179.6(7) no . . . .
C1 C2 C7 C6 177.2(7) no . . . .
C3 C2 C7 C6 -2.8(11) no . . . .
C7 C2 C3 C4 0.3(11) no . . . .
C2 C3 C4 C5 1.8(11) no . . . .
C3 C4 C5 Br2 175.5(6) no . . . .
C3 C4 C5 C6 -1.5(11) no . . . .
Br2 C5 C6 C7 -177.9(5) no . . . .
C4 C5 C6 C7 -1.0(12) no . . . .
C5 C6 C7 C2 3.1(12) no . . . .
N1 C8 C9 C10 0.8(8) no . . . .
C8 C9 C10 C11 0.3(8) no . . . .
C9 C10 C11 C12 -1.0(8) no . . . .
C10 C11 C12 N1 0.5(8) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Cu1 O2 3.127(4) no . .
Cu1 O2 3.127(4) no . 2_656
Cu1 C1 2.850(6) no . 2_656
Cu1 C8 2.935(7) no . 2_656
Cu1 C12 2.958(8) no . 2_656
O1 C3 2.783(7) no . .
O1 C7 3.588(6) no . .
O1 C8 3.135(8) no . .
O1 C12 3.310(9) no . 2_656
O2 N1 3.365(7) no . .
O2 C7 2.868(6) no . .
O2 C12 3.434(9) no . 2_656
O3 C8 3.284(8) no . .
O3 C8 3.284(8) no . 2_656
N1 C1 3.220(8) no . .
N1 C10 2.769(11) no . .
C2 C5 2.777(8) no . .
C3 C6 2.795(9) no . .
C4 C7 2.795(10) no . .
C8 C11 2.735(10) no . .
C9 C12 2.714(11) no . .
Br2 C10 3.477(6) no . 4_657
Br2 C11 3.573(5) no . 4_657
O1 C10 3.564(9) no . 3_555
O1 C11 3.553(9) no . 3_555
O2 O3 2.781(5) no . 1_545
O2 C10 3.229(9) no . 3_545
O3 O2 2.781(5) no . 1_565
O3 O2 2.781(5) no . 2_666
O3 C12 3.432(9) no . 1_565
O3 C12 3.432(9) no . 2_666
N1 C11 3.548(7) no . 4_556
C4 C6 3.548(11) no . 4_657
C4 C7 3.479(10) no . 1_565
C6 C4 3.548(11) no . 4_647
C7 C4 3.479(10) no . 1_545
C7 C9 3.599(11) no . 3_545
C8 C11 3.575(6) no . 4_556
C9 C7 3.599(11) no . 3_455
C10 Br2 3.477(6) no . 4_647
C10 O1 3.564(9) no . 3_445
C10 O2 3.229(9) no . 3_455
C11 Br2 3.573(5) no . 4_647
C11 O1 3.553(9) no . 3_445
C11 N1 3.548(7) no . 4_546
C11 C8 3.575(6) no . 4_546
C12 O3 3.432(9) no . 1_545
Br2 H4 2.8944 no . .
Br2 H6 2.9432 no . .
Cu1 H8 2.9619 no . .
Cu1 H8 2.9619 no . 2_656
Cu1 H12 2.9935 no . .
Cu1 H12 2.9935 no . 2_656
O1 H3 3.5804 no . .
O1 H3 2.6975 no . 2_656
O1 H3A 2.5150 no . .
O1 H8 2.8676 no . .
O1 H12 3.1302 no . 2_656
O2 H7 2.6010 no . .
O2 H12 2.6745 no . 2_656
O3 H8 2.7491 no . .
O3 H8 2.7491 no . 2_656
N1 H3 3.3184 no . 2_656
N1 H9 3.2336 no . .
N1 H11 3.2487 no . .
C1 H3A 2.6829 no . .
C1 H7 2.6595 no . .
C1 H8 3.5534 no . .
C1 H12 3.1055 no . 2_656
C2 H4 3.2837 no . .
C2 H6 3.2850 no . .
C3 H7 3.2828 no . .
C4 H6 3.2792 no . .
C5 H3A 3.2568 no . .
C5 H7 3.2543 no . .
C6 H4 3.2790 no . .
C7 H3A 3.2834 no . .
C8 H3 3.0951 no . 2_656
C8 H10 3.2419 no . .
C8 H12 3.1619 no . .
C9 H11 3.2501 no . .
C10 H8 3.2319 no . .
C10 H12 3.2385 no . .
C11 H9 3.2490 no . .
C12 H8 3.1649 no . .
C12 H10 3.2477 no . .
H3 H3A 3.3748 no . 2_656
H3 H8 3.4425 no . .
H3 H8 2.3685 no . 2_656
H3A H4 2.3454 no . .
H3A H8 3.0389 no . .
H6 H7 2.3445 no . .
H8 H9 2.3238 no . .
H9 H10 2.3286 no . .
H10 H11 2.3647 no . .
H11 H12 2.3300 no . .
Br2 H8 3.2798 no . 4_647
Br2 H9 3.1512 no . 4_647
Cu1 H3 3.4254 no . 1_545
Cu1 H3 3.4254 no . 2_646
O1 H10 2.9354 no . 3_555
O1 H11 2.9230 no . 3_555
O2 H3 3.3270 no . 1_545
O2 H3 2.0270 no . 2_646
O2 H3A 2.9282 no . 1_545
O2 H8 3.4387 no . 1_545
O2 H9 3.4209 no . 3_545
O2 H10 2.5661 no . 3_545
O3 H12 2.6943 no . 1_565
O3 H12 2.6943 no . 2_666
N1 H3 3.5199 no . 2_646
N1 H11 2.7905 no . 4_556
C1 H3 3.1377 no . 2_646
C1 H9 3.2934 no . 3_545
C1 H10 3.3095 no . 3_545
C1 H11 3.4207 no . 3_555
C2 H4 3.4112 no . 4_647
C2 H9 3.2115 no . 3_545
C2 H10 3.4552 no . 3_555
C3 H4 3.3072 no . 4_647
C3 H7 2.9135 no . 1_565
C3 H10 3.0430 no . 3_555
C4 H4 3.1324 no . 4_647
C4 H6 3.3924 no . 1_565
C4 H7 2.8425 no . 1_565
C5 H3A 3.5938 no . 4_647
C5 H4 3.0857 no . 4_647
C6 H4 2.9888 no . 1_545
C6 H4 3.2075 no . 4_647
C6 H6 3.2000 no . 2_757
C7 H3A 3.3339 no . 1_545
C7 H4 2.8903 no . 1_545
C7 H4 3.3332 no . 4_647
C7 H9 2.8554 no . 3_545
C7 H10 3.2485 no . 3_545
C8 H11 3.5519 no . 1_565
C8 H11 3.0933 no . 4_556
C9 H7 3.1432 no . 3_455
C9 H11 3.3416 no . 1_565
C9 H11 3.3757 no . 4_556
C9 H12 3.2845 no . 4_556
C10 H7 3.0654 no . 3_455
C10 H11 3.3750 no . 4_556
C10 H12 2.9774 no . 4_556
C11 H8 3.5830 no . 1_545
C11 H9 3.5321 no . 1_545
C11 H11 3.0951 no . 4_556
C11 H12 3.3858 no . 4_556
C12 H3 3.5065 no . 1_545
C12 H3 3.1914 no . 2_646
C12 H8 3.4226 no . 1_545
C12 H11 2.7723 no . 4_556
H3 Cu1 3.4254 no . 1_565
H3 O2 3.3270 no . 1_565
H3 O2 2.0270 no . 2_666
H3 N1 3.5199 no . 2_666
H3 C1 3.1377 no . 2_666
H3 C12 3.5065 no . 1_565
H3 C12 3.1914 no . 2_666
H3 H10 3.2682 no . 4_556
H3 H12 2.6819 no . 1_565
H3 H12 2.6420 no . 2_666
H3A O2 2.9282 no . 1_565
H3A C5 3.5938 no . 4_657
H3A C7 3.3339 no . 1_565
H3A H7 2.5864 no . 1_565
H3A H10 2.7510 no . 3_555
H4 C2 3.4112 no . 4_657
H4 C3 3.3072 no . 4_657
H4 C4 3.1324 no . 4_657
H4 C5 3.0857 no . 4_657
H4 C6 2.9888 no . 1_565
H4 C6 3.2075 no . 4_657
H4 C7 2.8903 no . 1_565
H4 C7 3.3332 no . 4_657
H4 H4 3.5721 no . 4_647
H4 H4 3.5721 no . 4_657
H4 H6 2.7022 no . 1_565
H4 H7 2.4756 no . 1_565
H6 C4 3.3924 no . 1_545
H6 C6 3.2000 no . 2_757
H6 H4 2.7022 no . 1_545
H6 H6 2.7294 no . 2_757
H6 H9 3.4168 no . 4_647
H7 C3 2.9135 no . 1_545
H7 C4 2.8425 no . 1_545
H7 C9 3.1432 no . 3_545
H7 C10 3.0654 no . 3_545
H7 H3A 2.5864 no . 1_545
H7 H4 2.4756 no . 1_545
H7 H9 2.5966 no . 3_545
H7 H10 2.4364 no . 3_545
H8 Br2 3.2798 no . 4_657
H8 O2 3.4387 no . 1_565
H8 C11 3.5830 no . 1_565
H8 C12 3.4226 no . 1_565
H8 H11 3.4068 no . 1_565
H8 H12 3.1028 no . 1_565
H9 Br2 3.1512 no . 4_657
H9 O2 3.4209 no . 3_455
H9 C1 3.2934 no . 3_455
H9 C2 3.2115 no . 3_455
H9 C7 2.8554 no . 3_455
H9 C11 3.5321 no . 1_565
H9 H6 3.4168 no . 4_657
H9 H7 2.5966 no . 3_455
H9 H11 3.0280 no . 1_565
H9 H12 3.5483 no . 4_556
H10 O1 2.9354 no . 3_445
H10 O2 2.5661 no . 3_455
H10 C1 3.3095 no . 3_455
H10 C2 3.4552 no . 3_445
H10 C3 3.0430 no . 3_445
H10 C7 3.2485 no . 3_455
H10 H3 3.2682 no . 4_546
H10 H3A 2.7510 no . 3_445
H10 H7 2.4364 no . 3_455
H10 H12 3.0490 no . 4_556
H11 O1 2.9230 no . 3_445
H11 N1 2.7905 no . 4_546
H11 C1 3.4207 no . 3_445
H11 C8 3.5519 no . 1_545
H11 C8 3.0933 no . 4_546
H11 C9 3.3416 no . 1_545
H11 C9 3.3757 no . 4_546
H11 C10 3.3750 no . 4_546
H11 C11 3.0951 no . 4_546
H11 C12 2.7723 no . 4_546
H11 H8 3.4068 no . 1_545
H11 H9 3.0280 no . 1_545
H11 H12 3.1410 no . 4_546
H12 O3 2.6943 no . 1_545
H12 C9 3.2845 no . 4_546
H12 C10 2.9774 no . 4_546
H12 C11 3.3858 no . 4_546
H12 H3 2.6819 no . 1_545
H12 H3 2.6420 no . 2_646
H12 H8 3.1028 no . 1_545
H12 H9 3.5483 no . 4_546
H12 H10 3.0490 no . 4_546
H12 H11 3.1410 no . 4_556

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H3 O2 . . 2_666 2.781(5) 0.840 2.027 149.1 no
O3 H3 O2 . 2_656 1_565 2.781(5) 0.840 2.027 149.1 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_Crystal4
_database_code_depnum_ccdc_archive 'CCDC 1442113'
_audit_update_record             
;
2016-01-06 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;
_audit_creation_method           'by CrystalStructure 4.1'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C24 H20 Cu I2 N2 O5'
_chemical_formula_moiety         'C24 H20 Cu I2 N2 O5'
_chemical_formula_weight         733.79
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
_space_group_IT_number           5
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,+Y,-Z
3 1/2+X,1/2+Y,1/2+Z
4 1/2-X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   15.4024(7)
_cell_length_b                   5.8321(3)
_cell_length_c                   15.4255(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 118.750(4)
_cell_angle_gamma                90.0000
_cell_volume                     1214.84(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2242
_cell_measurement_theta_min      3.33
_cell_measurement_theta_max      68.06
_cell_measurement_temperature    100
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    2.006
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             706.00
_exptl_absorpt_coefficient_mu    21.547
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.379
_exptl_absorpt_correction_T_max  0.806

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            6044
_diffrn_reflns_av_R_equivalents  0.1283
_diffrn_reflns_theta_max         68.158
_diffrn_reflns_theta_min         3.332
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).

    Following restrains were applied to correct unnatural ADPs of 
    atoms in phenyl- and pyridyl-rings.
     DELU C2 C3 C4 C5 C6 C7
     SIMU C2 C3 C4
     DELU N1 C8 C9 C10 C11 C12
     DELU Cu1 N1
;
_reflns_number_total             2090
_reflns_number_gt                1471
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0945
_refine_ls_wR_factor_ref         0.2522
_refine_ls_wR_factor_gt          0.2231
_refine_ls_number_restraints     38
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2090
_refine_ls_number_parameters     155
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1271P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         2.27
_refine_diff_density_min         -2.89
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 387 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.01(2)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cu Cu -1.9646 0.5888
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
I I -0.3257 6.8362
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.67031(12) 0.0548(5) 0.02568(10) 0.0484(6) Uani 1 4 d . . .
Cu1 Cu 0.5 0.1699(10) 0.5 0.0359(13) Uani 1 2 d . . .
O1 O 0.5117(13) 0.148(3) 0.3796(12) 0.035(4) Uani 1 4 d . . .
O2 O 0.5405(13) 0.533(4) 0.3714(11) 0.041(5) Uani 1 4 d . . .
O3 O 0.5 -0.209(5) 0.5 0.037(6) Uani 1 2 d . . .
N1 N 0.3543(16) 0.217(4) 0.4204(14) 0.034(4) Uani 1 4 d . . .
C1 C 0.537(2) 0.331(6) 0.346(2) 0.046(8) Uani 1 4 d . . .
C2 C 0.575(2) 0.259(5) 0.275(2) 0.037(5) Uani 1 4 d . . .
C3 C 0.6093(19) 0.048(6) 0.2721(17) 0.039(5) Uani 1 4 d . . .
C4 C 0.6407(19) -0.010(4) 0.2045(19) 0.039(6) Uani 1 4 d . . .
C5 C 0.633(2) 0.153(5) 0.1344(18) 0.039(6) Uani 1 4 d . . .
C6 C 0.5938(19) 0.376(5) 0.1328(19) 0.034(5) Uani 1 4 d . . .
C7 C 0.5670(19) 0.421(5) 0.2042(18) 0.038(6) Uani 1 4 d . . .
C8 C 0.2891(17) 0.067(7) 0.4219(16) 0.038(5) Uani 1 4 d . . .
C9 C 0.1868(18) 0.088(5) 0.3650(18) 0.038(6) Uani 1 4 d . . .
C10 C 0.150(2) 0.280(6) 0.3075(17) 0.042(6) Uani 1 4 d . . .
C11 C 0.212(2) 0.436(5) 0.306(2) 0.042(6) Uani 1 4 d . . .
C12 C 0.313(2) 0.417(5) 0.3651(16) 0.040(6) Uani 1 4 d . . .
H3A H 0.49529 -0.25684 0.54891 0.0444 Uiso 1 4 calc R . .
H3 H 0.61199 -0.06459 0.31786 0.0468 Uiso 1 4 calc R . .
H4 H 0.66696 -0.15785 0.2056 0.0467 Uiso 1 4 calc R . .
H6 H 0.58653 0.48675 0.08478 0.0413 Uiso 1 4 calc R . .
H7 H 0.54179 0.56901 0.2056 0.0459 Uiso 1 4 calc R . .
H8 H 0.3143 -0.06198 0.46455 0.0460 Uiso 1 4 calc R . .
H9 H 0.14376 -0.0275 0.36591 0.0451 Uiso 1 4 calc R . .
H10 H 0.08022 0.30188 0.26897 0.0509 Uiso 1 4 calc R . .
H11 H 0.18675 0.56424 0.26333 0.0508 Uiso 1 4 calc R . .
H12 H 0.3547 0.53967 0.36846 0.0480 Uiso 1 4 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
I1 C5 2.09(3) yes . .
Cu1 O1 1.95(2) yes . .
Cu1 O1 1.95(2) yes . 2_656
Cu1 O3 2.21(3) yes . .
Cu1 N1 1.99(2) yes . .
Cu1 N1 1.99(2) yes . 2_656
O1 C1 1.32(4) yes . .
O2 C1 1.24(4) yes . .
N1 C8 1.34(4) yes . .
N1 C12 1.40(3) yes . .
C1 C2 1.52(6) yes . .
C2 C3 1.35(5) yes . .
C2 C7 1.40(4) yes . .
C3 C4 1.39(5) yes . .
C4 C5 1.40(4) yes . .
C5 C6 1.43(4) yes . .
C6 C7 1.38(5) yes . .
C8 C9 1.39(3) yes . .
C9 C10 1.37(4) yes . .
C10 C11 1.33(5) yes . .
C11 C12 1.37(4) yes . .
O3 H3A 0.840 no . .
O3 H3A 0.840 no . 2_656
C3 H3 0.950 no . .
C4 H4 0.950 no . .
C6 H6 0.950 no . .
C7 H7 0.950 no . .
C8 H8 0.950 no . .
C9 H9 0.950 no . .
C10 H10 0.950 no . .
C11 H11 0.950 no . .
C12 H12 0.950 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
O1 Cu1 O1 172.5(9) yes . . 2_656
O1 Cu1 O3 86.2(6) yes . . .
O1 Cu1 N1 90.8(9) yes . . .
O1 Cu1 N1 90.2(9) yes . . 2_656
O1 Cu1 O3 86.2(6) yes 2_656 . .
O1 Cu1 N1 90.2(9) yes 2_656 . .
O1 Cu1 N1 90.8(9) yes 2_656 . 2_656
O3 Cu1 N1 97.9(6) yes . . .
O3 Cu1 N1 97.9(6) yes . . 2_656
N1 Cu1 N1 164.1(9) yes . . 2_656
Cu1 O1 C1 119.9(19) yes . . .
Cu1 N1 C8 122.0(17) yes . . .
Cu1 N1 C12 122.6(19) yes . . .
C8 N1 C12 115(2) yes . . .
O1 C1 O2 128(3) yes . . .
O1 C1 C2 110(3) yes . . .
O2 C1 C2 121(3) yes . . .
C1 C2 C3 124(3) yes . . .
C1 C2 C7 117(3) yes . . .
C3 C2 C7 119(3) yes . . .
C2 C3 C4 122(3) yes . . .
C3 C4 C5 119(3) yes . . .
I1 C5 C4 119(2) yes . . .
I1 C5 C6 121(2) yes . . .
C4 C5 C6 120(3) yes . . .
C5 C6 C7 117(3) yes . . .
C2 C7 C6 123(3) yes . . .
N1 C8 C9 124(3) yes . . .
C8 C9 C10 118(3) yes . . .
C9 C10 C11 119(3) yes . . .
C10 C11 C12 122(3) yes . . .
N1 C12 C11 121(3) yes . . .
Cu1 O3 H3A 109.409 no . . .
Cu1 O3 H3A 109.409 no . . 2_656
H3A O3 H3A 141.183 no . . 2_656
C2 C3 H3 118.999 no . . .
C4 C3 H3 118.975 no . . .
C3 C4 H4 120.456 no . . .
C5 C4 H4 120.435 no . . .
C5 C6 H6 121.584 no . . .
C7 C6 H6 121.590 no . . .
C2 C7 H7 118.481 no . . .
C6 C7 H7 118.474 no . . .
N1 C8 H8 117.942 no . . .
C9 C8 H8 117.942 no . . .
C8 C9 H9 120.882 no . . .
C10 C9 H9 120.878 no . . .
C9 C10 H10 120.423 no . . .
C11 C10 H10 120.432 no . . .
C10 C11 H11 119.029 no . . .
C12 C11 H11 119.035 no . . .
N1 C12 H12 119.640 no . . .
C11 C12 H12 119.642 no . . .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O3 Cu1 O1 C1 -165.4(12) no . . . .
O1 Cu1 N1 C8 116.5(17) no . . . .
O1 Cu1 N1 C12 -68.6(17) no . . . .
N1 Cu1 O1 C1 96.7(13) no . . . .
O1 Cu1 N1 C8 -56.1(17) no . . 2_656 2_656
O1 Cu1 N1 C12 118.9(17) no . . 2_656 2_656
N1 Cu1 O1 C1 -67.5(13) no 2_656 . . .
O3 Cu1 O1 C1 -165.4(12) no . . 2_656 2_656
O1 Cu1 N1 C8 -56.1(17) no 2_656 . . .
O1 Cu1 N1 C12 118.9(17) no 2_656 . . .
N1 Cu1 O1 C1 -67.5(13) no . . 2_656 2_656
O1 Cu1 N1 C8 116.5(17) no 2_656 . 2_656 2_656
O1 Cu1 N1 C12 -68.6(17) no 2_656 . 2_656 2_656
N1 Cu1 O1 C1 96.7(13) no 2_656 . 2_656 2_656
O3 Cu1 N1 C8 30.2(17) no . . . .
O3 Cu1 N1 C12 -154.9(15) no . . . .
O3 Cu1 N1 C8 30.2(17) no . . 2_656 2_656
O3 Cu1 N1 C12 -154.9(15) no . . 2_656 2_656
Cu1 O1 C1 O2 -13(4) no . . . .
Cu1 O1 C1 C2 161.2(11) no . . . .
Cu1 N1 C8 C9 -177.6(18) no . . . .
Cu1 N1 C12 C11 175.7(17) no . . . .
C8 N1 C12 C11 -9(4) no . . . .
C12 N1 C8 C9 7(4) no . . . .
O1 C1 C2 C3 -21(3) no . . . .
O1 C1 C2 C7 154.6(19) no . . . .
O2 C1 C2 C3 154(2) no . . . .
O2 C1 C2 C7 -31(3) no . . . .
C1 C2 C3 C4 179(2) no . . . .
C1 C2 C7 C6 -177(2) no . . . .
C3 C2 C7 C6 -1(4) no . . . .
C7 C2 C3 C4 3(4) no . . . .
C2 C3 C4 C5 -2(3) no . . . .
C3 C4 C5 I1 -175.1(18) no . . . .
C3 C4 C5 C6 0(3) no . . . .
I1 C5 C6 C7 176.8(14) no . . . .
C4 C5 C6 C7 2(3) no . . . .
C5 C6 C7 C2 -1(3) no . . . .
N1 C8 C9 C10 -4(5) no . . . .
C8 C9 C10 C11 2(4) no . . . .
C9 C10 C11 C12 -4(5) no . . . .
C10 C11 C12 N1 8(5) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Cu1 O2 3.16(2) no . .
Cu1 O2 3.16(2) no . 2_656
Cu1 C1 2.86(4) no . 2_656
Cu1 C8 2.93(3) no . 2_656
Cu1 C12 2.99(3) no . 2_656
O1 C3 2.78(4) no . .
O1 C7 3.58(4) no . .
O1 C8 3.16(2) no . 2_656
O1 C12 3.35(4) no . .
O2 N1 3.37(3) no . 2_656
O2 C7 2.87(4) no . .
O2 C12 3.53(4) no . .
O3 C8 3.29(3) no . .
O3 C8 3.29(3) no . 2_656
N1 C1 3.58(5) no . .
N1 C1 3.23(3) no . 2_656
N1 C10 2.80(3) no . .
C2 C5 2.79(5) no . .
C3 C6 2.80(4) no . .
C4 C7 2.76(4) no . .
C8 C11 2.68(4) no . .
C9 C12 2.73(4) no . .
O1 C10 3.49(3) no . 4_545
O1 C11 3.48(3) no . 4_545
O2 O3 2.79(3) no . 1_565
O2 C10 3.24(3) no . 4_555
O3 O2 2.79(3) no . 1_545
O3 O2 2.79(3) no . 2_646
O3 C12 3.41(3) no . 1_545
O3 C12 3.41(3) no . 2_646
N1 C11 3.54(4) no . 4_545
C4 C7 3.51(4) no . 1_545
C7 C4 3.51(4) no . 1_565
C8 C11 3.59(5) no . 4_545
C10 O1 3.49(3) no . 4_555
C10 O2 3.24(3) no . 4_545
C11 O1 3.48(3) no . 4_555
C11 N1 3.54(4) no . 4_555
C11 C8 3.59(5) no . 4_555
C12 O3 3.41(3) no . 1_565
I1 H4 3.0629 no . .
I1 H6 3.1581 no . .
Cu1 H8 2.9672 no . .
Cu1 H8 2.9672 no . 2_656
Cu1 H12 3.0672 no . .
Cu1 H12 3.0672 no . 2_656
O1 H3A 2.6296 no . 2_656
O1 H3 2.4986 no . .
O1 H8 2.8743 no . 2_656
O1 H12 3.2709 no . .
O2 H7 2.5759 no . .
O2 H12 2.8410 no . .
O2 H12 3.5320 no . 2_656
O3 H8 2.7768 no . .
O3 H8 2.7768 no . 2_656
N1 H3A 3.4849 no . .
N1 H3A 3.4893 no . 2_656
N1 H9 3.2614 no . .
N1 H11 3.2580 no . .
C1 H3 2.7029 no . .
C1 H7 2.6040 no . .
C1 H8 3.5447 no . 2_656
C1 H12 3.2338 no . .
C2 H4 3.2458 no . .
C2 H6 3.3015 no . .
C3 H7 3.2157 no . .
C4 H6 3.3182 no . .
C5 H3 3.2588 no . .
C5 H7 3.2495 no . .
C6 H4 3.3149 no . .
C7 H3 3.2264 no . .
C8 H3A 3.3918 no . .
C8 H10 3.2392 no . .
C8 H12 3.1789 no . .
C9 H11 3.1890 no . .
C10 H8 3.2205 no . .
C10 H12 3.2074 no . .
C11 H9 3.1949 no . .
C12 H8 3.1796 no . .
C12 H10 3.2199 no . .
H3A H3 3.3879 no . 2_656
H3A H8 2.6956 no . .
H3A H8 3.2437 no . 2_656
H3 H4 2.3285 no . .
H3 H8 2.9815 no . 2_656
H6 H7 2.3268 no . .
H8 H9 2.3261 no . .
H9 H10 2.3401 no . .
H10 H11 2.2756 no . .
H11 H12 2.3036 no . .
I1 H8 3.5797 no . 3_554
I1 H9 3.3474 no . 3_554
Cu1 H3A 3.4358 no . 1_565
Cu1 H3A 3.4358 no . 2_666
O1 H10 2.8650 no . 4_545
O1 H11 2.8214 no . 4_545
O2 H3A 3.3638 no . 1_565
O2 H3A 1.9915 no . 2_666
O2 H3 2.8760 no . 1_565
O2 H8 3.3959 no . 2_666
O2 H9 3.4045 no . 4_555
O2 H10 2.5944 no . 4_555
O3 H12 2.6279 no . 1_545
O3 H12 2.6279 no . 2_646
N1 H11 2.7390 no . 4_545
C1 H3A 3.0731 no . 2_666
C1 H9 3.2245 no . 4_555
C1 H10 3.5856 no . 4_545
C1 H10 3.3012 no . 4_555
C1 H11 3.4035 no . 4_545
C2 H9 3.2519 no . 4_555
C2 H10 3.4260 no . 4_545
C3 H7 2.9853 no . 1_545
C3 H10 3.0336 no . 4_545
C4 H4 3.3105 no . 4_655
C4 H6 3.3534 no . 1_545
C4 H7 2.8951 no . 1_545
C5 H4 3.0771 no . 4_655
C6 H4 2.9527 no . 1_565
C6 H4 3.3150 no . 4_655
C6 H6 3.2305 no . 2_655
C7 H3 3.3735 no . 1_565
C7 H4 2.8931 no . 1_565
C7 H9 2.9011 no . 4_555
C7 H10 3.3381 no . 4_555
C8 H11 3.0541 no . 4_545
C8 H12 3.4581 no . 1_545
C9 H7 3.1469 no . 4_545
C9 H11 3.4338 no . 1_545
C9 H11 3.3823 no . 4_545
C9 H12 3.3526 no . 4_545
C10 H3A 3.5332 no . 3_454
C10 H7 3.1120 no . 4_545
C10 H11 3.4306 no . 4_545
C10 H12 3.0262 no . 4_545
C11 H9 3.5626 no . 1_565
C11 H11 3.1414 no . 4_545
C11 H12 3.3157 no . 4_545
C12 H3A 3.4499 no . 1_565
C12 H3A 3.2177 no . 2_666
C12 H8 3.4012 no . 1_565
C12 H11 2.8567 no . 4_545
H3A Cu1 3.4358 no . 1_545
H3A O2 3.3638 no . 1_545
H3A O2 1.9915 no . 2_646
H3A C1 3.0731 no . 2_646
H3A C10 3.5332 no . 3_545
H3A C12 3.4499 no . 1_545
H3A C12 3.2177 no . 2_646
H3A H10 3.0133 no . 3_545
H3A H12 2.8368 no . 1_545
H3A H12 2.3534 no . 2_646
H3 O2 2.8760 no . 1_545
H3 C7 3.3735 no . 1_545
H3 H7 2.6330 no . 1_545
H3 H10 2.7112 no . 4_545
H4 C4 3.3105 no . 4_645
H4 C5 3.0771 no . 4_645
H4 C6 2.9527 no . 1_545
H4 C6 3.3150 no . 4_645
H4 C7 2.8931 no . 1_545
H4 H6 2.6615 no . 1_545
H4 H7 2.5009 no . 1_545
H6 C4 3.3534 no . 1_565
H6 C6 3.2305 no . 2_655
H6 H4 2.6615 no . 1_565
H6 H6 2.6906 no . 2_655
H7 C3 2.9853 no . 1_565
H7 C4 2.8951 no . 1_565
H7 C9 3.1469 no . 4_555
H7 C10 3.1121 no . 4_555
H7 H3 2.6330 no . 1_565
H7 H4 2.5009 no . 1_565
H7 H9 2.5824 no . 4_555
H7 H10 2.4978 no . 4_555
H8 I1 3.5797 no . 3_445
H8 O2 3.3959 no . 2_646
H8 C12 3.4012 no . 1_545
H8 H11 3.5185 no . 1_545
H8 H11 3.5838 no . 4_545
H8 H12 2.9781 no . 1_545
H9 I1 3.3474 no . 3_445
H9 O2 3.4045 no . 4_545
H9 C1 3.2245 no . 4_545
H9 C2 3.2519 no . 4_545
H9 C7 2.9011 no . 4_545
H9 C11 3.5626 no . 1_545
H9 H7 2.5824 no . 4_545
H9 H11 3.1015 no . 1_545
H10 O1 2.8650 no . 4_555
H10 O2 2.5944 no . 4_545
H10 C1 3.3012 no . 4_545
H10 C1 3.5856 no . 4_555
H10 C2 3.4260 no . 4_555
H10 C3 3.0336 no . 4_555
H10 C7 3.3381 no . 4_545
H10 H3A 3.0133 no . 3_454
H10 H3 2.7112 no . 4_555
H10 H7 2.4978 no . 4_545
H10 H12 3.1435 no . 4_545
H11 O1 2.8214 no . 4_555
H11 N1 2.7390 no . 4_555
H11 C1 3.4035 no . 4_555
H11 C8 3.0541 no . 4_555
H11 C9 3.4338 no . 1_565
H11 C9 3.3823 no . 4_555
H11 C10 3.4306 no . 4_555
H11 C11 3.1414 no . 4_555
H11 C12 2.8567 no . 4_555
H11 H8 3.5185 no . 1_565
H11 H8 3.5838 no . 4_555
H11 H9 3.1015 no . 1_565
H11 H12 3.5569 no . 4_545
H11 H12 3.3136 no . 4_555
H12 O3 2.6279 no . 1_565
H12 C8 3.4581 no . 1_565
H12 C9 3.3526 no . 4_555
H12 C10 3.0262 no . 4_555
H12 C11 3.3157 no . 4_555
H12 H3A 2.8368 no . 1_565
H12 H3A 2.3534 no . 2_666
H12 H8 2.9781 no . 1_565
H12 H10 3.1435 no . 4_555
H12 H11 3.3136 no . 4_545
H12 H11 3.5569 no . 4_555

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H3A O2 . . 2_646 2.79(3) 0.840 1.992 158.1 no
O3 H3A O2 . 2_656 1_545 2.79(3) 0.840 1.992 158.1 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_Crystal5
_database_code_depnum_ccdc_archive 'CCDC 1442114'
_audit_update_record             
;
2016-01-06 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;
_audit_creation_method           'by CrystalStructure 4.0'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C26 H26 Cu N2 O5'
_chemical_formula_moiety         'C26 H26 Cu N2 O5'
_chemical_formula_weight         510.05
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-Y,1/2+Z
5 1/2+X,1/2+Y,+Z
6 1/2-X,1/2+Y,1/2-Z
7 1/2-X,1/2-Y,-Z
8 1/2+X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   15.5909(8)
_cell_length_b                   6.0458(4)
_cell_length_c                   25.4000(14)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.280(3)
_cell_angle_gamma                90.0000
_cell_volume                     2394.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1679
_cell_measurement_theta_min      3.48
_cell_measurement_theta_max      67.58
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1060.00
_exptl_absorpt_coefficient_mu    1.620
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_T_max  0.968

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      223
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            8789
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_theta_max         68.19
_diffrn_reflns_theta_full        68.19
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2173
_reflns_number_gt                1101
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0736
_refine_ls_wR_factor_ref         0.2230
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2173
_refine_ls_number_parameters     155
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1061P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.940
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cu Cu -1.9646 0.5888
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.1931(2) 0.7500 0.0510(5) Uani 1.0 4 d . . .
O1 O 0.4455(3) 0.2038(7) 0.68151(14) 0.0550(11) Uani 1.0 8 d . . .
O2 O 0.4605(3) -0.1608(8) 0.66467(14) 0.0639(12) Uani 1.0 8 d . . .
O3 O 0.5000 0.5711(10) 0.7500 0.0619(16) Uani 1.0 4 d . . .
N1 N 0.6139(3) 0.1543(9) 0.71393(16) 0.0492(13) Uani 1.0 8 d . . .
C1 C 0.4439(4) 0.0346(14) 0.6511(3) 0.0555(16) Uani 1.0 8 d . . .
C2 C 0.4214(4) 0.0838(11) 0.5944(2) 0.0516(15) Uani 1.0 8 d . . .
C3 C 0.4276(4) 0.2969(12) 0.5747(3) 0.0644(18) Uani 1.0 8 d . . .
C4 C 0.4071(5) 0.3389(13) 0.5227(3) 0.076(2) Uani 1.0 8 d . . .
C5 C 0.3782(5) 0.1764(13) 0.4889(3) 0.0640(18) Uani 1.0 8 d . . .
C6 C 0.3713(5) -0.0340(14) 0.5092(3) 0.080(3) Uani 1.0 8 d . . .
C7 C 0.3936(5) -0.0813(12) 0.5612(3) 0.0690(19) Uani 1.0 8 d . . .
C8 C 0.3548(6) 0.2268(15) 0.4328(3) 0.095(3) Uani 1.0 8 d . . .
C9 C 0.6444(4) 0.3044(11) 0.6808(3) 0.0565(16) Uani 1.0 8 d . . .
C10 C 0.7234(4) 0.2867(13) 0.6574(3) 0.0670(19) Uani 1.0 8 d . . .
C11 C 0.7724(4) 0.1009(13) 0.6671(3) 0.067(2) Uani 1.0 8 d . . .
C12 C 0.7410(4) -0.0594(12) 0.7002(3) 0.0613(17) Uani 1.0 8 d . . .
C13 C 0.6618(4) -0.0286(12) 0.7227(2) 0.0565(16) Uani 1.0 8 d . . .
H3 H 0.4458 0.4129 0.5968 0.0772 Uiso 1.0 8 calc R . .
H3A H 0.5184 0.6168 0.7787 0.0743 Uiso 1.0 8 calc R . .
H4 H 0.4131 0.4839 0.5099 0.0915 Uiso 1.0 8 calc R . .
H6 H 0.3509 -0.1486 0.4875 0.0963 Uiso 1.0 8 calc R . .
H7 H 0.3897 -0.2273 0.5737 0.0828 Uiso 1.0 8 calc R . .
H8A H 0.4067 0.2503 0.4126 0.1145 Uiso 1.0 8 calc R . .
H8B H 0.3197 0.3591 0.4315 0.1145 Uiso 1.0 8 calc R . .
H8C H 0.3230 0.1035 0.4180 0.1145 Uiso 1.0 8 calc R . .
H9 H 0.6104 0.4287 0.6730 0.0678 Uiso 1.0 8 calc R . .
H10 H 0.7437 0.3992 0.6351 0.0804 Uiso 1.0 8 calc R . .
H11 H 0.8264 0.0842 0.6513 0.0803 Uiso 1.0 8 calc R . .
H12 H 0.7731 -0.1877 0.7073 0.0736 Uiso 1.0 8 calc R . .
H13 H 0.6402 -0.1391 0.7450 0.0678 Uiso 1.0 8 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Cu1 O1 1.933(4) yes . .
Cu1 O1 1.933(4) yes . 2_656
Cu1 N1 2.016(5) yes . .
Cu1 N1 2.016(5) yes . 2_656
O1 C1 1.282(9) yes . .
O2 C1 1.257(10) yes . .
N1 C9 1.327(8) yes . .
N1 C13 1.352(8) yes . .
C1 C2 1.509(8) yes . .
C2 C3 1.386(10) yes . .
C2 C7 1.376(9) yes . .
C3 C4 1.382(9) yes . .
C4 C5 1.379(10) yes . .
C5 C6 1.377(11) yes . .
C5 C8 1.500(9) yes . .
C6 C7 1.394(9) yes . .
C9 C10 1.374(9) yes . .
C10 C11 1.380(10) yes . .
C11 C12 1.374(10) yes . .
C12 C13 1.376(8) yes . .
O3 H3A 0.830 no . .
O3 H3A 0.830 no . 2_656
C3 H3 0.940 no . .
C4 H4 0.940 no . .
C6 H6 0.940 no . .
C7 H7 0.940 no . .
C8 H8A 0.970 no . .
C8 H8B 0.970 no . .
C8 H8C 0.970 no . .
C9 H9 0.940 no . .
C10 H10 0.940 no . .
C11 H11 0.940 no . .
C12 H12 0.940 no . .
C13 H13 0.940 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
O1 Cu1 O1 176.2(2) yes . . 2_656
O1 Cu1 N1 88.81(16) yes . . .
O1 Cu1 N1 91.64(16) yes . . 2_656
O1 Cu1 N1 91.64(16) yes 2_656 . .
O1 Cu1 N1 88.81(16) yes 2_656 . 2_656
N1 Cu1 N1 166.6(3) yes . . 2_656
Cu1 O1 C1 121.5(4) yes . . .
Cu1 N1 C9 121.9(4) yes . . .
Cu1 N1 C13 120.5(4) yes . . .
C9 N1 C13 117.6(5) yes . . .
O1 C1 O2 125.5(6) yes . . .
O1 C1 C2 114.9(7) yes . . .
O2 C1 C2 119.6(6) yes . . .
C1 C2 C3 120.7(6) yes . . .
C1 C2 C7 120.8(6) yes . . .
C3 C2 C7 118.4(6) yes . . .
C2 C3 C4 120.0(7) yes . . .
C3 C4 C5 122.6(7) yes . . .
C4 C5 C6 116.8(6) yes . . .
C4 C5 C8 121.6(7) yes . . .
C6 C5 C8 121.6(7) yes . . .
C5 C6 C7 121.6(7) yes . . .
C2 C7 C6 120.6(7) yes . . .
N1 C9 C10 123.1(6) yes . . .
C9 C10 C11 118.8(7) yes . . .
C10 C11 C12 119.0(6) yes . . .
C11 C12 C13 118.8(7) yes . . .
N1 C13 C12 122.6(6) yes . . .
H3A O3 H3A 141.089 no . . 2_656
C2 C3 H3 120.025 no . . .
C4 C3 H3 120.011 no . . .
C3 C4 H4 118.718 no . . .
C5 C4 H4 118.727 no . . .
C5 C6 H6 119.186 no . . .
C7 C6 H6 119.169 no . . .
C2 C7 H7 119.713 no . . .
C6 C7 H7 119.710 no . . .
C5 C8 H8A 109.473 no . . .
C5 C8 H8B 109.464 no . . .
C5 C8 H8C 109.459 no . . .
H8A C8 H8B 109.477 no . . .
H8A C8 H8C 109.483 no . . .
H8B C8 H8C 109.472 no . . .
N1 C9 H9 118.445 no . . .
C10 C9 H9 118.447 no . . .
C9 C10 H10 120.597 no . . .
C11 C10 H10 120.582 no . . .
C10 C11 H11 120.488 no . . .
C12 C11 H11 120.489 no . . .
C11 C12 H12 120.601 no . . .
C13 C12 H12 120.609 no . . .
N1 C13 H13 118.718 no . . .
C12 C13 H13 118.724 no . . .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O1 Cu1 N1 C9 60.0(4) no . . . .
O1 Cu1 N1 C13 -119.6(4) no . . . .
N1 Cu1 O1 C1 66.4(3) no . . . .
O1 Cu1 N1 C9 -116.2(4) no . . 2_656 2_656
O1 Cu1 N1 C13 64.2(4) no . . 2_656 2_656
N1 Cu1 O1 C1 -100.3(3) no 2_656 . . .
O1 Cu1 N1 C9 -116.2(4) no 2_656 . . .
O1 Cu1 N1 C13 64.2(4) no 2_656 . . .
N1 Cu1 O1 C1 -100.3(3) no . . 2_656 2_656
O1 Cu1 N1 C9 60.0(4) no 2_656 . 2_656 2_656
O1 Cu1 N1 C13 -119.6(4) no 2_656 . 2_656 2_656
N1 Cu1 O1 C1 66.4(3) no 2_656 . 2_656 2_656
Cu1 O1 C1 O2 14.8(7) no . . . .
Cu1 O1 C1 C2 -164.1(3) no . . . .
Cu1 N1 C9 C10 177.2(4) no . . . .
Cu1 N1 C13 C12 -178.1(4) no . . . .
C9 N1 C13 C12 2.3(8) no . . . .
C13 N1 C9 C10 -3.2(8) no . . . .
O1 C1 C2 C3 18.2(7) no . . . .
O1 C1 C2 C7 -161.4(5) no . . . .
O2 C1 C2 C3 -160.7(5) no . . . .
O2 C1 C2 C7 19.7(8) no . . . .
C1 C2 C3 C4 179.7(5) no . . . .
C1 C2 C7 C6 178.7(5) no . . . .
C3 C2 C7 C6 -0.9(9) no . . . .
C7 C2 C3 C4 -0.7(9) no . . . .
C2 C3 C4 C5 1.5(10) no . . . .
C3 C4 C5 C6 -0.6(10) no . . . .
C3 C4 C5 C8 178.9(6) no . . . .
C4 C5 C6 C7 -1.0(10) no . . . .
C8 C5 C6 C7 179.5(6) no . . . .
C5 C6 C7 C2 1.8(11) no . . . .
N1 C9 C10 C11 2.3(9) no . . . .
C9 C10 C11 C12 -0.6(9) no . . . .
C10 C11 C12 C13 -0.2(9) no . . . .
C11 C12 C13 N1 -0.6(9) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Cu1 O2 3.105(5) no . .
Cu1 O2 3.105(5) no . 2_656
Cu1 C1 2.824(6) no . 2_656
Cu1 C9 2.941(6) no . 2_656
Cu1 C13 2.943(6) no . 2_656
O1 C3 2.782(8) no . .
O1 C7 3.597(8) no . .
O1 C9 3.161(7) no . .
O1 C13 3.276(7) no . 2_656
O2 N1 3.299(7) no . .
O2 C7 2.863(7) no . .
O2 C13 3.551(7) no . .
O2 C13 3.538(7) no . 2_656
N1 C1 3.171(7) no . .
N1 C11 2.767(8) no . .
C2 C5 2.816(8) no . .
C3 C6 2.744(10) no . .
C4 C7 2.731(11) no . .
C9 C12 2.709(10) no . .
C10 C13 2.706(10) no . .
Cu1 O3 2.285(7) no . .
O1 O3 2.944(6) no . .
O1 C12 3.529(7) no . 5_455
O2 O3 2.773(6) no . 1_545
O2 C11 3.269(8) no . 5_445
O3 Cu1 2.285(7) no . .
O3 O1 2.944(6) no . .
O3 O1 2.944(6) no . 2_656
O3 O2 2.773(6) no . 1_565
O3 O2 2.773(6) no . 2_666
O3 N1 3.218(7) no . .
O3 N1 3.218(7) no . 2_656
O3 C9 3.286(7) no . .
O3 C9 3.286(7) no . 2_656
O3 C13 3.566(8) no . 1_565
O3 C13 3.566(8) no . 2_666
N1 O3 3.218(7) no . .
N1 C12 3.582(8) no . 6_656
C9 O3 3.286(7) no . .
C9 C12 3.599(9) no . 6_656
C11 O2 3.269(8) no . 5_555
C12 O1 3.529(7) no . 5_545
C12 N1 3.582(8) no . 6_646
C12 C9 3.599(9) no . 6_646
C13 O3 3.566(8) no . 1_545
Cu1 H9 2.9745 no . .
Cu1 H9 2.9745 no . 2_656
Cu1 H13 2.9710 no . .
Cu1 H13 2.9710 no . 2_656
O1 H3 2.4964 no . .
O1 H9 2.9177 no . .
O1 H13 3.0959 no . 2_656
O2 H7 2.5880 no . .
O2 H13 3.4599 no . .
O2 H13 2.7887 no . 2_656
N1 H10 3.2146 no . .
N1 H12 3.2354 no . .
C1 H3 2.6714 no . .
C1 H7 2.6589 no . .
C1 H9 3.5657 no . .
C1 H13 3.1330 no . 2_656
C2 H4 3.2367 no . .
C2 H6 3.2449 no . .
C3 H7 3.2243 no . .
C4 H6 3.2012 no . .
C4 H8A 2.8481 no . .
C4 H8B 2.6840 no . .
C4 H8C 3.2837 no . .
C5 H3 3.2609 no . .
C5 H7 3.2591 no . .
C6 H4 3.1983 no . .
C6 H8A 3.0493 no . .
C6 H8B 3.1893 no . .
C6 H8C 2.5702 no . .
C7 H3 3.2247 no . .
C8 H4 2.6561 no . .
C8 H6 2.6616 no . .
C9 H11 3.2254 no . .
C9 H13 3.1393 no . .
C10 H12 3.2287 no . .
C11 H9 3.2138 no . .
C11 H13 3.2116 no . .
C12 H10 3.2278 no . .
C13 H9 3.1414 no . .
C13 H11 3.2225 no . .
H3 H4 2.3036 no . .
H3 H9 3.2091 no . .
H4 H8A 2.8473 no . .
H4 H8B 2.5726 no . .
H4 H8C 3.5597 no . .
H6 H7 2.3177 no . .
H6 H8A 3.1950 no . .
H6 H8B 3.4160 no . .
H6 H8C 2.3701 no . .
H9 H10 2.3009 no . .
H10 H11 2.3351 no . .
H11 H12 2.3297 no . .
H12 H13 2.3066 no . .
Cu1 H3A 3.5709 no . 1_545
Cu1 H3A 2.6786 no . .
Cu1 H3A 3.5709 no . 2_646
Cu1 H3A 2.6786 no . 2_656
O1 H3A 2.7511 no . 2_656
O1 H11 3.0521 no . 5_455
O1 H12 2.8464 no . 5_455
O2 H3 3.1088 no . 1_545
O2 H3A 3.3146 no . 1_545
O2 H3A 1.9945 no . 2_646
O2 H8A 2.9103 no . 3_656
O2 H9 3.4146 no . 1_545
O2 H10 3.4789 no . 5_445
O2 H11 2.6190 no . 5_445
O3 H9 2.7496 no . .
O3 H9 2.7496 no . 2_656
O3 H13 2.8043 no . 1_565
O3 H13 2.8043 no . 2_666
N1 H3A 3.5730 no . .
N1 H3A 3.4806 no . 2_656
N1 H12 2.8266 no . 6_656
C1 H3A 3.1454 no . 2_646
C1 H8A 3.3236 no . 3_656
C1 H10 3.2508 no . 5_445
C1 H11 3.2818 no . 5_445
C1 H12 3.4624 no . 5_455
C2 H8A 3.3626 no . 3_656
C2 H10 3.1654 no . 5_445
C3 H4 3.5483 no . 3_666
C3 H7 2.9364 no . 1_565
C3 H11 3.0528 no . 5_455
C4 H4 3.1161 no . 3_666
C4 H6 3.3408 no . 1_565
C4 H7 2.9376 no . 1_565
C6 H4 2.9868 no . 1_545
C6 H8B 3.5058 no . 7_556
C7 H3 3.2897 no . 1_545
C7 H4 2.9508 no . 1_545
C7 H8A 3.3410 no . 3_656
C7 H8B 3.5927 no . 7_556
C7 H10 3.0083 no . 5_445
C7 H11 3.2324 no . 5_445
C8 H9 3.4456 no . 3_666
C8 H10 3.2285 no . 3_666
C9 H3A 3.3311 no . 2_656
C9 H8B 3.5517 no . 3_666
C9 H8C 3.5572 no . 3_656
C9 H12 3.1144 no . 6_656
C10 H7 3.3629 no . 5_555
C10 H8B 3.1818 no . 3_666
C10 H8C 3.1214 no . 3_656
C10 H12 3.5063 no . 1_565
C10 H12 3.4413 no . 6_656
C10 H13 3.2893 no . 6_656
C11 H3 3.4413 no . 5_545
C11 H3A 3.5356 no . 6_646
C11 H7 3.1779 no . 5_555
C11 H8C 2.8947 no . 3_656
C11 H12 3.5131 no . 6_656
C11 H13 3.0470 no . 6_656
C12 H8C 3.1703 no . 3_656
C12 H12 3.2603 no . 6_656
C12 H13 3.4352 no . 6_656
C13 H3A 3.4127 no . 1_545
C13 H3A 3.5342 no . 2_646
C13 H12 2.9028 no . 6_656
H3 O2 3.1088 no . 1_565
H3 C7 3.2897 no . 1_565
H3 C11 3.4413 no . 5_455
H3 H3A 3.4375 no . 2_656
H3 H4 3.5526 no . 3_666
H3 H7 2.4155 no . 1_565
H3 H8A 3.0818 no . 3_666
H3 H11 2.5463 no . 5_455
H3A Cu1 2.6786 no . .
H3A Cu1 3.5709 no . 1_565
H3A O1 2.7511 no . 2_656
H3A O2 3.3146 no . 1_565
H3A O2 1.9945 no . 2_666
H3A N1 3.5730 no . .
H3A N1 3.4806 no . 2_656
H3A C1 3.1454 no . 2_666
H3A C9 3.3311 no . 2_656
H3A C11 3.5356 no . 6_656
H3A C13 3.4127 no . 1_565
H3A C13 3.5342 no . 2_666
H3A H3 3.4375 no . 2_656
H3A H9 3.2548 no . .
H3A H9 2.6184 no . 2_656
H3A H11 3.0021 no . 6_656
H3A H13 2.5548 no . 1_565
H3A H13 2.9395 no . 2_666
H4 C3 3.5483 no . 3_666
H4 C4 3.1161 no . 3_666
H4 C6 2.9868 no . 1_565
H4 C7 2.9508 no . 1_565
H4 H3 3.5526 no . 3_666
H4 H4 2.7649 no . 3_666
H4 H6 2.4889 no . 1_565
H4 H7 2.4112 no . 1_565
H6 C4 3.3408 no . 1_545
H6 H4 2.4889 no . 1_545
H6 H6 3.4394 no . 7_546
H6 H8B 3.3331 no . 1_545
H7 C3 2.9364 no . 1_545
H7 C4 2.9376 no . 1_545
H7 C10 3.3629 no . 5_445
H7 C11 3.1779 no . 5_445
H7 H3 2.4155 no . 1_545
H7 H4 2.4112 no . 1_545
H7 H8A 3.1950 no . 3_656
H7 H10 2.8711 no . 5_445
H7 H11 2.4859 no . 5_445
H8A O2 2.9103 no . 3_656
H8A C1 3.3236 no . 3_656
H8A C2 3.3626 no . 3_656
H8A C7 3.3410 no . 3_656
H8A H3 3.0818 no . 3_666
H8A H7 3.1950 no . 3_656
H8A H9 2.9257 no . 3_666
H8A H10 3.3797 no . 3_666
H8B C6 3.5058 no . 7_556
H8B C7 3.5927 no . 7_556
H8B C9 3.5517 no . 3_666
H8B C10 3.1818 no . 3_666
H8B H6 3.3331 no . 1_565
H8B H9 3.1493 no . 3_666
H8B H10 2.4420 no . 3_666
H8C C9 3.5572 no . 3_656
H8C C10 3.1214 no . 3_656
H8C C11 2.8947 no . 3_656
H8C C12 3.1703 no . 3_656
H8C H10 3.4824 no . 3_656
H8C H10 3.4540 no . 3_666
H8C H11 3.1262 no . 3_656
H8C H12 3.5478 no . 3_656
H9 O2 3.4146 no . 1_565
H9 O3 2.7496 no . .
H9 C8 3.4456 no . 3_666
H9 H3A 3.2548 no . .
H9 H3A 2.6184 no . 2_656
H9 H8A 2.9257 no . 3_666
H9 H8B 3.1493 no . 3_666
H9 H12 3.5420 no . 1_565
H9 H13 3.2219 no . 1_565
H10 O2 3.4789 no . 5_555
H10 C1 3.2508 no . 5_555
H10 C2 3.1654 no . 5_555
H10 C7 3.0083 no . 5_555
H10 C8 3.2285 no . 3_666
H10 H7 2.8711 no . 5_555
H10 H8A 3.3797 no . 3_666
H10 H8B 2.4420 no . 3_666
H10 H8C 3.4824 no . 3_656
H10 H8C 3.4540 no . 3_666
H10 H12 3.1302 no . 1_565
H10 H13 3.5418 no . 6_656
H11 O1 3.0521 no . 5_545
H11 O2 2.6190 no . 5_555
H11 C1 3.2818 no . 5_555
H11 C3 3.0528 no . 5_545
H11 C7 3.2324 no . 5_555
H11 H3 2.5463 no . 5_545
H11 H3A 3.0021 no . 6_646
H11 H7 2.4859 no . 5_555
H11 H8C 3.1262 no . 3_656
H11 H13 3.1608 no . 6_656
H12 O1 2.8464 no . 5_545
H12 N1 2.8266 no . 6_646
H12 C1 3.4624 no . 5_545
H12 C9 3.1144 no . 6_646
H12 C10 3.5063 no . 1_545
H12 C10 3.4413 no . 6_646
H12 C11 3.5131 no . 6_646
H12 C12 3.2603 no . 6_646
H12 C13 2.9028 no . 6_646
H12 H8C 3.5478 no . 3_656
H12 H9 3.5420 no . 1_545
H12 H10 3.1302 no . 1_545
H12 H13 3.2754 no . 6_646
H13 O3 2.8043 no . 1_545
H13 C10 3.2893 no . 6_646
H13 C11 3.0470 no . 6_646
H13 C12 3.4352 no . 6_646
H13 H3A 2.5548 no . 1_545
H13 H3A 2.9395 no . 2_646
H13 H9 3.2219 no . 1_545
H13 H10 3.5418 no . 6_646
H13 H11 3.1608 no . 6_646
H13 H12 3.2754 no . 6_656

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H3A O2 . . 2_666 2.773(6) 0.830 1.995 155.9 no
O3 H3A O2 . 2_656 1_565 2.773(6) 0.830 1.995 155.9 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_Crystal6
_database_code_depnum_ccdc_archive 'CCDC 1442115'
_audit_update_record             
;
2016-01-06 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;

_audit_creation_method           'by CrystalStructure 4.0'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C26 H26 Cu N2 O7'
_chemical_formula_moiety         'C26 H26 Cu N2 O7'
_chemical_formula_weight         542.05
_chemical_melting_point          ?
_chemical_absolute_configuration ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'I 1 2 1'
_symmetry_space_group_name_Hall  'I 2y'
_symmetry_Int_Tables_number      5
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,+Y,-Z
3 1/2+X,1/2+Y,1/2+Z
4 1/2-X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   14.9535(3)
_cell_length_b                   6.02142(11)
_cell_length_c                   15.2932(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 116.8850(10)
_cell_angle_gamma                90.0000
_cell_volume                     1228.19(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5671
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      68.19
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             562.00
_exptl_absorpt_coefficient_mu    1.678
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.863
_exptl_absorpt_correction_T_max  0.920

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      223
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            6664
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_theta_max         68.19
_diffrn_reflns_theta_full        68.19
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).

    Following restrains were applied to correct unnatural bond length.
     SADI C1 C2A C1 C2B

    AFIX 66 were used to make a shape of phenyl ring stabilized.
     AFIX 66 C2A C3A C4A C5A C6A C7A
;
_reflns_number_total             2203
_reflns_number_gt                2159
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0676
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2203
_refine_ls_number_parameters     224
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0405P)²+0.4018P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.280
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  966 Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.01(3)

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cu Cu -1.9646 0.5888
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.89219(2) 1.0000 0.03046(13) Uani 1.0 2 d . . .
O1 O 0.01336(10) 0.8933(5) 0.87836(9) 0.0401(3) Uani 1.0 4 d . . .
O2 O 0.05105(16) 0.5360(4) 0.88646(17) 0.0628(6) Uani 1.0 4 d . . .
O3A O 0.1725(13) 0.7893(17) 0.5613(12) 0.051(3) Uani 0.5000 4 d . . .
O3B O 0.1626(13) 0.8604(17) 0.5476(12) 0.050(3) Uani 0.5000 4 d . . .
O4 O 0.0000 1.2647(4) 1.0000 0.0515(7) Uani 1.0 2 d . . .
N1 N -0.15058(12) 0.8604(4) 0.92322(11) 0.0334(5) Uani 1.0 4 d . . .
C1 C 0.04484(16) 0.7214(4) 0.85206(17) 0.0366(6) Uani 1.0 4 d . . .
C2A C 0.0783(4) 0.7373(7) 0.7766(3) 0.048(5) Uani 0.5000 4 d . . .
C2B C 0.0728(6) 0.7689(16) 0.7696(5) 0.023(3) Uani 0.5000 4 d . . .
C3A C 0.0585(3) 0.9334(6) 0.7232(3) 0.0334(12) Uani 0.5000 4 d . . .
C3B C 0.1070(4) 0.9805(10) 0.7554(4) 0.0324(12) Uani 0.5000 4 d . . .
C4A C 0.0868(4) 0.9551(6) 0.6486(3) 0.0382(12) Uani 0.5000 4 d . . .
C4B C 0.1415(4) 1.0176(9) 0.6839(4) 0.0370(11) Uani 0.5000 4 d . . .
C5A C 0.1348(5) 0.7807(7) 0.6275(4) 0.029(3) Uani 0.5000 4 d . . .
C5B C 0.1376(7) 0.8517(17) 0.6237(6) 0.0338(18) Uani 0.5000 4 d . . .
C6A C 0.1546(4) 0.5846(5) 0.6810(3) 0.0405(11) Uani 0.5000 4 d . . .
C6B C 0.1022(5) 0.6405(12) 0.6322(5) 0.0399(11) Uani 0.5000 4 d . . .
C7A C 0.1263(3) 0.5629(5) 0.7556(3) 0.0348(10) Uani 0.5000 4 d . . .
C7B C 0.0725(4) 0.6033(8) 0.7045(4) 0.0361(10) Uani 0.5000 4 d . . .
C8A C 0.1566(7) 0.9903(17) 0.5071(7) 0.0547(18) Uani 0.5000 4 d . . .
C8B C 0.1929(6) 1.0709(14) 0.5292(6) 0.0505(16) Uani 0.5000 4 d . . .
C9 C -0.21142(16) 1.0059(5) 0.93551(17) 0.0416(6) Uani 1.0 4 d . . .
C10 C -0.31504(18) 0.9976(6) 0.8793(2) 0.0534(7) Uani 1.0 4 d . . .
C11 C -0.35519(19) 0.8346(6) 0.81017(19) 0.0580(10) Uani 1.0 4 d . . .
C12 C -0.2929(2) 0.6795(6) 0.79894(19) 0.0535(7) Uani 1.0 4 d . . .
C13 C -0.19070(19) 0.6993(4) 0.85700(17) 0.0428(6) Uani 1.0 4 d . . .
H3A H 0.0260 1.0513 0.7374 0.0401 Uiso 0.5000 4 calc R . .
H3B H 0.1067 1.1001 0.7948 0.0389 Uiso 0.5000 4 calc R . .
H4A H 0.0734 1.0877 0.6124 0.0458 Uiso 0.5000 4 calc R . .
H4B H 0.1668 1.1573 0.6789 0.0443 Uiso 0.5000 4 calc R . .
H4 H 0.0004 1.3107 1.0513 0.0618 Uiso 1.0 4 calc R . .
H6A H 0.1871 0.4667 0.6667 0.0485 Uiso 0.5000 4 calc R . .
H6B H 0.0987 0.5257 0.5892 0.0478 Uiso 0.5000 4 calc R . .
H7A H 0.1397 0.4303 0.7917 0.0418 Uiso 0.5000 4 calc R . .
H7B H 0.0510 0.4599 0.7105 0.0433 Uiso 0.5000 4 calc R . .
H8A1 H 0.1825 0.9745 0.4597 0.0657 Uiso 0.5000 4 calc R . .
H8A2 H 0.1910 1.1112 0.5516 0.0657 Uiso 0.5000 4 calc R . .
H8A3 H 0.0853 1.0222 0.4733 0.0657 Uiso 0.5000 4 calc R . .
H8B1 H 0.2129 1.0575 0.4772 0.0606 Uiso 0.5000 4 calc R . .
H8B2 H 0.2490 1.1247 0.5883 0.0606 Uiso 0.5000 4 calc R . .
H8B3 H 0.1375 1.1746 0.5093 0.0606 Uiso 0.5000 4 calc R . .
H9 H -0.1835 1.1170 0.9835 0.0499 Uiso 1.0 4 calc R . .
H10 H -0.3566 1.1021 0.8886 0.0641 Uiso 1.0 4 calc R . .
H11 H -0.4249 0.8278 0.7704 0.0696 Uiso 1.0 4 calc R . .
H12 H -0.3194 0.5637 0.7531 0.0642 Uiso 1.0 4 calc R . .
H13 H -0.1478 0.5952 0.8495 0.0513 Uiso 1.0 4 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'


#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Cu1 O1 1.9587(16) yes . .
Cu1 O1 1.9587(16) yes . 2_557
Cu1 O4 2.243(3) yes . .
Cu1 N1 2.0234(16) yes . .
Cu1 N1 2.0234(16) yes . 2_557
O1 C1 1.275(4) yes . .
O2 C1 1.220(4) yes . .
O3A C5A 1.36(3) yes . .
O3A C8A 1.425(17) yes . .
O3B C5B 1.37(3) yes . .
O3B C8B 1.417(16) yes . .
N1 C9 1.336(4) yes . .
N1 C13 1.333(3) yes . .
C1 C2A 1.453(7) yes . .
C1 C2B 1.523(9) yes . .
C2A C3A 1.390(6) yes . .
C2A C7A 1.390(7) yes . .
C2B C3B 1.426(11) yes . .
C2B C7B 1.408(11) yes . .
C3A C4A 1.390(8) yes . .
C3B C4B 1.422(10) yes . .
C4A C5A 1.390(7) yes . .
C4B C5B 1.342(12) yes . .
C5A C6A 1.390(6) yes . .
C5B C6B 1.406(13) yes . .
C6A C7A 1.390(8) yes . .
C6B C7B 1.383(10) yes . .
C9 C10 1.392(3) yes . .
C10 C11 1.366(5) yes . .
C11 C12 1.383(5) yes . .
C12 C13 1.382(4) yes . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
O1 Cu1 O1 179.60(12) yes . . 2_557
O1 Cu1 O4 89.80(8) yes . . .
O1 Cu1 N1 90.79(7) yes . . .
O1 Cu1 N1 89.24(7) yes . . 2_557
O1 Cu1 O4 89.80(8) yes 2_557 . .
O1 Cu1 N1 89.24(7) yes 2_557 . .
O1 Cu1 N1 90.79(7) yes 2_557 . 2_557
O4 Cu1 N1 95.43(7) yes . . .
O4 Cu1 N1 95.43(7) yes . . 2_557
N1 Cu1 N1 169.15(9) yes . . 2_557
Cu1 O1 C1 120.50(19) yes . . .
C5A O3A C8A 116.6(12) yes . . .
C5B O3B C8B 115.9(12) yes . . .
Cu1 N1 C9 120.41(15) yes . . .
Cu1 N1 C13 120.67(18) yes . . .
C9 N1 C13 118.87(19) yes . . .
O1 C1 O2 125.0(3) yes . . .
O1 C1 C2A 120.4(3) yes . . .
O1 C1 C2B 112.8(4) yes . . .
O2 C1 C2A 114.6(3) yes . . .
O2 C1 C2B 122.2(5) yes . . .
C1 C2A C3A 117.7(4) yes . . .
C1 C2A C7A 122.3(4) yes . . .
C3A C2A C7A 120.0(5) yes . . .
C1 C2B C3B 123.1(7) yes . . .
C1 C2B C7B 122.5(7) yes . . .
C3B C2B C7B 114.3(7) yes . . .
C2A C3A C4A 120.0(4) yes . . .
C2B C3B C4B 122.5(6) yes . . .
C3A C4A C5A 120.0(4) yes . . .
C3B C4B C5B 119.5(7) yes . . .
O3A C5A C4A 125.0(6) yes . . .
O3A C5A C6A 114.8(7) yes . . .
C4A C5A C6A 120.0(6) yes . . .
O3B C5B C4B 127.5(10) yes . . .
O3B C5B C6B 111.8(9) yes . . .
C4B C5B C6B 120.7(9) yes . . .
C5A C6A C7A 120.0(5) yes . . .
C5B C6B C7B 119.4(7) yes . . .
C2A C7A C6A 120.0(4) yes . . .
C2B C7B C6B 123.4(6) yes . . .
N1 C9 C10 121.9(3) yes . . .
C9 C10 C11 118.7(3) yes . . .
C10 C11 C12 119.7(3) yes . . .
C11 C12 C13 118.2(3) yes . . .
N1 C13 C12 122.5(3) yes . . .



#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
