# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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 
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data_CuFmIm
_database_code_depnum_ccdc_archive 'CCDC 1492387'
_audit_update_record             
;
2017-01-25 deposited with the CCDC.
2017-03-08 downloaded from the CCDC.
;

_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H19 Cu2 N8 O6, N O3'
_chemical_formula_sum            'C15 H19 Cu2 N9 O9'
_chemical_formula_weight         596.46
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   9.3812(2)
_cell_length_b                   12.9376(3)
_cell_length_c                   18.1801(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2206.52(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2876
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_exptl_absorpt_coefficient_mu    1.99
_exptl_absorpt_correction_T_max  1.16
_exptl_absorpt_correction_T_min  1.00
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_diffrn    1.796
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.074
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_min         2.443
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       ω
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.02139
_diffrn_orient_matrix_UB_12      -0.10246
_diffrn_orient_matrix_UB_13      0.02018
_diffrn_orient_matrix_UB_21      0.02974
_diffrn_orient_matrix_UB_22      -0.00776
_diffrn_orient_matrix_UB_23      -0.07092
_diffrn_orient_matrix_UB_31      0.04956
_diffrn_orient_matrix_UB_32      0.01413
_diffrn_orient_matrix_UB_33      0.01923
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_d_resolution_high        0.62
_reflns_d_resolution_low         1.93
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_limit_h_max              12
_reflns_limit_h_min              0
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_diffrn_reflns_number            36934
_reflns_number_gt                1998
_reflns_number_total             2637
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I> 3.00 sigma(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Dolomanov et al., 2009)'
_refine_diff_density_max         1.747
_refine_diff_density_min         -2.485
_refine_diff_density_rms         0.482
_refine_ls_abs_structure_details 
;
;
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2637
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1005
_refine_ls_R_factor_gt           0.0718
_refine_ls_restrained_S_all      1.160
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1342P)²+7.0370P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2031
_refine_ls_wR_factor_ref         0.2334
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 C6-H6A
 0.93 with sigma of 0.01
3. Others
 Fixed Sof: O9(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C1(H1), C9(H9), C8(H8), C7(H7), C2(H2), C5(H5), N5(H5A),
 N2(H2A)

5. The minimum electron density difference is 0.87 A from the Cu atom" 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C6 C 0.0426(9) 0.2500 0.4865(5) 0.0281(19) Uani 1 2 d DS T P . .
H6A H 0.053(11) 0.2500 0.4355(10) 0.034 Uiso 1 2 d DRS T P . .
C4 C -0.0015(9) 0.2500 0.9734(5) 0.0292(19) Uani 1 2 d S T P . .
H4 H -0.0635 0.2500 1.0133 0.035 Uiso 1 2 calc RS T P . .
C3 C 0.3356(8) 0.0307(5) 0.8704(4) 0.0332(14) Uani 1 1 d . . . . .
H3 H 0.4317 0.0478 0.8675 0.040 Uiso 1 1 calc R . . . .
C1 C 0.1376(7) -0.0578(5) 0.8686(3) 0.0312(14) Uani 1 1 d . . . . .
H1 H 0.0726 -0.1117 0.8643 0.037 Uiso 1 1 calc R . . . .
C9 C 0.2137(8) 0.5663(5) 0.6592(4) 0.0340(15) Uani 1 1 d . . . . .
H9 H 0.2135 0.6242 0.6895 0.041 Uiso 1 1 calc R . . . .
C8 C 0.2173(8) 0.4674(5) 0.5625(4) 0.0335(15) Uani 1 1 d . . . . .
H8 H 0.2212 0.4451 0.5139 0.040 Uiso 1 1 calc R . . . .
C7 C 0.2057(8) 0.4672(5) 0.6802(4) 0.0344(15) Uani 1 1 d . . . . .
H7 H 0.2008 0.4453 0.7288 0.041 Uiso 1 1 calc R . . . .
C2 C 0.1074(7) 0.0409(5) 0.8844(4) 0.0340(15) Uani 1 1 d . . . . .
H2 H 0.0166 0.0669 0.8933 0.041 Uiso 1 1 calc R . . . .
C5 C 0.3752(9) 0.2500 0.7540(4) 0.0226(16) Uani 1 2 d S T P . .
H5 H 0.4500 0.2500 0.7205 0.027 Uiso 1 2 calc RS T P . .
N5 N 0.2224(8) 0.5648(5) 0.5835(4) 0.0445(16) Uani 1 1 d . . . . .
H5A H 0.2298 0.6177 0.5552 0.053 Uiso 1 1 calc R . . . .
N3 N 0.2295(5) 0.0971(4) 0.8854(3) 0.0256(11) Uani 1 1 d . . . . .
N4 N 0.2057(5) 0.4041(4) 0.6219(3) 0.0241(10) Uani 1 1 d . . . . .
N2 N 0.2814(7) -0.0642(5) 0.8601(3) 0.0419(15) Uani 1 1 d . . . . .
H2A H 0.3290 -0.1191 0.8500 0.050 Uiso 1 1 calc R . . . .
O9 O -0.0699(10) 0.2197(7) 0.5179(5) 0.041(3) Uani 0.5 1 d . . . . .
O6 O 0.4058(6) 0.2500 0.8223(3) 0.0245(12) Uani 1 2 d S T P . .
O7 O 0.2507(6) 0.2500 0.7293(3) 0.0237(13) Uani 1 2 d S T P . .
O4 O -0.0550(6) 0.2500 0.9117(3) 0.0241(12) Uani 1 2 d S T P . .
O8 O 0.1615(7) 0.2500 0.5141(3) 0.0303(14) Uani 1 2 d S T P . .
O5 O 0.1295(7) 0.2500 0.9872(3) 0.0329(15) Uani 1 2 d S T P . .
Cu2 Cu 0.20840(11) 0.2500 0.62076(5) 0.0211(3) Uani 1 2 d S T P . .
Cu1 Cu 0.25153(10) 0.2500 0.89760(5) 0.0214(3) Uani 1 2 d S T P . .
N1 N -0.0134(18) -0.2500 0.7627(9) 0.086(4) Uiso 1 2 d S T P . .
O1 O -0.0397(18) -0.2500 0.8284(9) 0.118(5) Uiso 1 2 d S T P . .
O2 O 0.134(2) -0.2500 0.7643(9) 0.138(6) Uiso 1 2 d S T P . .
O3 O -0.034(3) -0.2500 0.7096(16) 0.214(11) Uiso 1 2 d S T P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C6 0.023(4) 0.038(5) 0.023(4) 0.000 -0.002(3) 0.000
C4 0.023(4) 0.030(5) 0.034(5) 0.000 0.009(4) 0.000
C3 0.029(3) 0.029(3) 0.042(3) 0.003(3) 0.003(3) 0.005(3)
C1 0.035(4) 0.026(3) 0.033(3) 0.001(2) 0.003(3) -0.005(3)
C9 0.049(4) 0.021(3) 0.032(3) -0.006(3) -0.003(3) 0.004(3)
C8 0.046(4) 0.026(3) 0.029(3) 0.004(3) 0.004(3) 0.002(3)
C7 0.049(4) 0.028(3) 0.026(3) 0.001(3) -0.003(3) 0.003(3)
C2 0.025(3) 0.031(3) 0.047(4) -0.005(3) 0.000(3) 0.000(3)
C5 0.021(4) 0.024(4) 0.023(4) 0.000 0.003(3) 0.000
N5 0.062(4) 0.029(3) 0.043(3) 0.011(3) 0.007(3) 0.007(3)
N3 0.022(3) 0.026(3) 0.029(3) 0.004(2) 0.0009(18) -0.001(2)
N4 0.020(2) 0.026(3) 0.026(2) 0.000(2) -0.0013(18) 0.001(2)
N2 0.048(4) 0.037(3) 0.041(3) 0.002(3) -0.001(3) 0.013(3)
O9 0.035(5) 0.046(8) 0.041(5) -0.005(4) 0.015(4) 0.000(4)
O6 0.020(3) 0.031(3) 0.023(3) 0.000 0.003(2) 0.000
O7 0.024(3) 0.022(3) 0.025(3) 0.000 0.002(2) 0.000
O4 0.022(3) 0.029(3) 0.022(3) 0.000 -0.002(2) 0.000
O8 0.026(3) 0.037(3) 0.028(3) 0.000 -0.008(2) 0.000
O5 0.023(3) 0.055(4) 0.021(3) 0.000 -0.002(2) 0.000
Cu2 0.0207(6) 0.0192(5) 0.0235(5) 0.000 -0.0032(4) 0.000
Cu1 0.0173(5) 0.0257(6) 0.0213(5) 0.000 0.0006(3) 0.000

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C6 H6A 0.933(10) . ?
C6 O9 1.263(12) . ?
C6 O9 1.263(12) 8_565 ?
C6 O8 1.222(11) . ?
C4 H4 0.9300 . ?
C4 O4 1.228(11) . ?
C4 O5 1.254(11) . ?
C3 H3 0.9300 . ?
C3 N3 1.344(8) . ?
C3 N2 1.342(10) . ?
C1 H1 0.9300 . ?
C1 C2 1.338(9) . ?
C1 N2 1.360(10) . ?
C9 H9 0.9300 . ?
C9 C7 1.339(10) . ?
C9 N5 1.379(10) . ?
C8 H8 0.9300 . ?
C8 N5 1.318(10) . ?
C8 N4 1.361(8) . ?
C7 H7 0.9300 . ?
C7 N4 1.338(8) . ?
C2 H2 0.9300 . ?
C2 N3 1.357(8) . ?
C5 H5 0.9300 . ?
C5 O6 1.275(10) . ?
C5 O7 1.251(10) . ?
N5 H5A 0.8600 . ?
N3 Cu1 2.001(6) . ?
N4 Cu2 1.993(5) . ?
N2 H2A 0.8600 . ?
O9 O9 0.785(17) 8_565 ?
O9 Cu1 2.306(8) 6_557 ?
O6 Cu1 1.992(5) . ?
O7 Cu2 2.013(6) . ?
O4 Cu2 2.297(6) 6_557 ?
O8 Cu2 1.989(6) . ?
O5 Cu1 1.991(6) . ?
Cu2 N4 1.993(5) 8_565 ?
Cu2 O4 2.297(6) 6_657 ?
Cu1 N3 2.001(6) 8_565 ?
Cu1 O9 2.306(9) 3_556 ?
Cu1 O9 2.306(9) 6_657 ?
N1 O1 1.22(2) . ?
N1 O2 1.38(2) . ?
N1 O3 0.99(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O9 C6 H6A 122(6) . . ?
O9 C6 H6A 122(6) 8_565 . ?
O8 C6 H6A 108(7) . . ?
O8 C6 O9 125.3(8) . . ?
O8 C6 O9 125.3(8) . 8_565 ?
O4 C4 H4 117.2 . . ?
O4 C4 O5 125.7(8) . . ?
O5 C4 H4 117.2 . . ?
N3 C3 H3 125.3 . . ?
N2 C3 H3 125.3 . . ?
N2 C3 N3 109.4(6) . . ?
C2 C1 H1 126.5 . . ?
C2 C1 N2 107.0(6) . . ?
N2 C1 H1 126.5 . . ?
C7 C9 H9 127.1 . . ?
C7 C9 N5 105.9(6) . . ?
N5 C9 H9 127.1 . . ?
N5 C8 H8 124.8 . . ?
N5 C8 N4 110.3(6) . . ?
N4 C8 H8 124.8 . . ?
C9 C7 H7 124.5 . . ?
N4 C7 C9 111.1(6) . . ?
N4 C7 H7 124.5 . . ?
C1 C2 H2 125.2 . . ?
C1 C2 N3 109.6(6) . . ?
N3 C2 H2 125.2 . . ?
O6 C5 H5 118.0 . . ?
O7 C5 H5 118.0 . . ?
O7 C5 O6 124.1(7) . . ?
C9 N5 H5A 126.2 . . ?
C8 N5 C9 107.6(6) . . ?
C8 N5 H5A 126.2 . . ?
C3 N3 C2 106.2(6) . . ?
C3 N3 Cu1 125.3(4) . . ?
C2 N3 Cu1 128.2(4) . . ?
C8 N4 Cu2 126.3(4) . . ?
C7 N4 C8 105.1(6) . . ?
C7 N4 Cu2 128.3(4) . . ?
C3 N2 C1 107.7(6) . . ?
C3 N2 H2A 126.1 . . ?
C1 N2 H2A 126.1 . . ?
C6 O9 Cu1 148.8(6) . 6_557 ?
C5 O6 Cu1 120.4(5) . . ?
C5 O7 Cu2 122.4(5) . . ?
C4 O4 Cu2 129.0(6) . 6_557 ?
C6 O8 Cu2 127.0(6) . . ?
C4 O5 Cu1 113.5(6) . . ?
N4 Cu2 N4 178.1(3) . 8_565 ?
N4 Cu2 O7 89.55(14) . . ?
N4 Cu2 O7 89.54(14) 8_565 . ?
N4 Cu2 O4 90.87(15) . 6_657 ?
N4 Cu2 O4 90.87(15) 8_565 6_657 ?
O7 Cu2 O4 93.5(2) . 6_657 ?
O8 Cu2 N4 90.43(14) . . ?
O8 Cu2 N4 90.43(14) . 8_565 ?
O8 Cu2 O7 178.6(2) . . ?
O8 Cu2 O4 87.9(2) . 6_657 ?
N3 Cu1 N3 162.6(3) . 8_565 ?
N3 Cu1 O9 108.5(3) . 3_556 ?
N3 Cu1 O9 108.5(3) 8_565 6_657 ?
N3 Cu1 O9 88.9(3) 8_565 3_556 ?
N3 Cu1 O9 88.9(3) . 6_657 ?
O6 Cu1 N3 89.96(15) . 8_565 ?
O6 Cu1 N3 89.96(15) . . ?
O6 Cu1 O9 86.0(3) . 3_556 ?
O6 Cu1 O9 86.0(3) . 6_657 ?
O5 Cu1 N3 91.76(15) . 8_565 ?
O5 Cu1 N3 91.77(15) . . ?
O5 Cu1 O9 82.7(3) . 6_657 ?
O5 Cu1 O9 82.7(3) . 3_556 ?
O5 Cu1 O6 168.5(2) . . ?
O1 N1 O2 100.5(16) . . ?
O3 N1 O1 157(3) . . ?
O3 N1 O2 103(3) . . ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 N3 C3 -0.4(7) . . . . ?
C1 C2 N3 Cu1 174.6(4) . . . . ?
C9 C7 N4 C8 1.3(8) . . . . ?
C9 C7 N4 Cu2 175.6(5) . . . . ?
C7 C9 N5 C8 0.9(9) . . . . ?
C2 C1 N2 C3 -0.4(8) . . . . ?
N5 C9 C7 N4 -1.4(9) . . . . ?
N5 C8 N4 C7 -0.8(8) . . . . ?
N5 C8 N4 Cu2 -175.2(5) . . . . ?
N3 C3 N2 C1 0.2(8) . . . . ?
N4 C8 N5 C9 -0.1(8) . . . . ?
N2 C3 N3 C2 0.1(7) . . . . ?
N2 C3 N3 Cu1 -175.0(4) . . . . ?
N2 C1 C2 N3 0.5(8) . . . . ?
O9 C6 O8 Cu2 22.4(6) 8_565 . . . ?
O9 C6 O8 Cu2 -22.4(6) . . . . ?
O6 C5 O7 Cu2 180.000(3) . . . . ?
O7 C5 O6 Cu1 0.000(3) . . . . ?
O4 C4 O5 Cu1 0.000(4) . . . . ?
O8 C6 O9 O9 103.4(5) . . . 8_565 ?
O8 C6 O9 Cu1 75.7(14) . . . 6_557 ?
O5 C4 O4 Cu2 180.000(4) . . . 6_557 ?

_shelx_res_file                  
;
    shelx.res created by SHELXL-2014/7

TITL SIR92 run in space group P n m a
CELL 0.71073 9.3812 12.9376 18.1801 90 90 90
ZERR 4 0.0002 0.0003 0.0004 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,0.5-Z
SYMM -X,0.5+Y,-Z
SFAC C N O Cu H
UNIT 60 36 36 8 76
DFIX 0.93 0.01 C6 H6A

L.S. 10
PLAN  25
BOND $H
CONF
MORE -1
fmap 2
acta
MERG 2
REM <olex2.extras>
REM <HklSrc "%./shelx.hkl">
REM </olex2.extras>

WGHT    0.134200    7.037000
FVAR       0.18795
C6    1    0.042618    0.250000    0.486532    10.50000    0.02286    0.03842 =
         0.02296    0.00000   -0.00212    0.00000
H6A   5    0.052620    0.250000    0.435459    10.50000   -1.20000
C4    1   -0.001503    0.250000    0.973391    10.50000    0.02304    0.03020 =
         0.03433    0.00000    0.00884    0.00000
AFIX  43
H4    5   -0.063515    0.250000    1.013302    10.50000   -1.20000
AFIX   0
C3    1    0.335618    0.030714    0.870403    11.00000    0.02896    0.02851 =
         0.04216    0.00329    0.00274    0.00487
AFIX  43
H3    5    0.431744    0.047826    0.867546    11.00000   -1.20000
AFIX   0
C1    1    0.137581   -0.057761    0.868646    11.00000    0.03470    0.02632 =
         0.03265    0.00076    0.00267   -0.00476
AFIX  43
H1    5    0.072585   -0.111697    0.864316    11.00000   -1.20000
AFIX   0
C9    1    0.213743    0.566295    0.659240    11.00000    0.04896    0.02100 =
         0.03202   -0.00626   -0.00332    0.00431
AFIX  43
H9    5    0.213502    0.624222    0.689530    11.00000   -1.20000
AFIX   0
C8    1    0.217342    0.467358    0.562463    11.00000    0.04617    0.02584 =
         0.02860    0.00405    0.00424    0.00203
AFIX  43
H8    5    0.221184    0.445062    0.513872    11.00000   -1.20000
AFIX   0
C7    1    0.205726    0.467248    0.680185    11.00000    0.04915    0.02781 =
         0.02620    0.00099   -0.00344    0.00322
AFIX  43
H7    5    0.200841    0.445271    0.728825    11.00000   -1.20000
AFIX   0
C2    1    0.107397    0.040890    0.884427    11.00000    0.02450    0.03075 =
         0.04672   -0.00456    0.00048   -0.00022
AFIX  43
H2    5    0.016613    0.066911    0.893334    11.00000   -1.20000
AFIX   0
C5    1    0.375169    0.250000    0.754018    10.50000    0.02144    0.02372 =
         0.02267    0.00000    0.00301    0.00000
AFIX  43
H5    5    0.449999    0.250000    0.720464    10.50000   -1.20000
AFIX   0
N5    2    0.222432    0.564769    0.583526    11.00000    0.06196    0.02901 =
         0.04261    0.01100    0.00653    0.00708
AFIX  43
H5A   5    0.229826    0.617741    0.555204    11.00000   -1.20000
AFIX   0
N3    2    0.229453    0.097144    0.885447    11.00000    0.02180    0.02571 =
         0.02934    0.00381    0.00085   -0.00070
N4    2    0.205665    0.404053    0.621934    11.00000    0.01988    0.02616 =
         0.02623    0.00040   -0.00130    0.00121
N2    2    0.281362   -0.064153    0.860144    11.00000    0.04832    0.03660 =
         0.04075    0.00170   -0.00052    0.01316
AFIX  43
H2A   5    0.328965   -0.119148    0.850009    11.00000   -1.20000
AFIX   0
O9    3   -0.069944    0.219676    0.517929    10.50000    0.03479    0.04634 =
         0.04149   -0.00531    0.01546   -0.00049
O6    3    0.405800    0.250000    0.822317    10.50000    0.01968    0.03060 =
         0.02309    0.00000    0.00255    0.00000
O7    3    0.250684    0.250000    0.729294    10.50000    0.02396    0.02249 =
         0.02470    0.00000    0.00151    0.00000
O4    3   -0.054991    0.250000    0.911728    10.50000    0.02172    0.02857 =
         0.02196    0.00000   -0.00181    0.00000
O8    3    0.161453    0.250000    0.514067    10.50000    0.02585    0.03687 =
         0.02828    0.00000   -0.00807    0.00000
O5    3    0.129483    0.250000    0.987212    10.50000    0.02253    0.05523 =
         0.02094    0.00000   -0.00250    0.00000
CU2   4    0.208405    0.250000    0.620763    10.50000    0.02069    0.01919 =
         0.02352    0.00000   -0.00323    0.00000
CU1   4    0.251530    0.250000    0.897599    10.50000    0.01729    0.02574 =
         0.02126    0.00000    0.00063    0.00000

N1    2   -0.013410   -0.250000    0.762741    10.50000    0.08563
O1    3   -0.039697   -0.250000    0.828371    10.50000    0.11805
O2    3    0.133627   -0.250000    0.764270    10.50000    0.13781
O3    3   -0.034473   -0.250000    0.709595    10.50000    0.21434
HKLF 4

REM  SIR92 run in space group P n m a
REM R1 =  0.0718 for    1998 Fo > 4sig(Fo)  and  0.1005 for all    2637 data
REM    174 parameters refined using      1 restraints

END

WGHT      0.1342      7.0370

REM Highest difference peak  1.747,  deepest hole -2.485,  1-sigma level  0.482
Q1    1   0.3043 -0.2500  0.7516  10.50000  0.05    1.75
Q2    1  -0.0327 -0.1590  0.7404  11.00000  0.05    1.66
Q3    1   0.0120  0.2500  0.4262  10.50000  0.05    1.38
Q4    1   0.4458  0.0663  0.7564  11.00000  0.05    0.96
Q5    1  -0.0249  0.0301  1.0004  11.00000  0.05    0.95
Q6    1  -0.0324 -0.2500  0.6884  10.50000  0.05    0.95
Q7    1   0.0314  0.5296  0.5078  11.00000  0.05    0.95
Q8    1   0.4473  0.4461  0.7288  11.00000  0.05    0.91
Q9    1  -0.0138  0.5021  0.7592  11.00000  0.05    0.91
Q10   1  -0.0069 -0.0672  0.9684  11.00000  0.05    0.89
Q11   1   0.0134  0.4495  0.7384  11.00000  0.05    0.88
Q12   1   0.1755 -0.0572  0.8599  11.00000  0.05    0.86
Q13   1   0.5203  0.1301  0.7423  11.00000  0.05    0.86
Q14   1   0.3852  0.0526  0.7686  11.00000  0.05    0.86
Q15   1   0.5487  0.2500  0.7495  10.50000  0.05    0.86
Q16   1   0.0888  0.0035  0.9815  11.00000  0.05    0.84
Q17   1  -0.0419 -0.0351  0.9635  11.00000  0.05    0.82
Q18   1   0.0978  0.4370  0.4689  11.00000  0.05    0.81
Q19   1   0.3530  0.4606  0.4973  11.00000  0.05    0.80
Q20   1   0.3889  0.4530  0.4903  11.00000  0.05    0.80
Q21   1   0.4127  0.2500  0.7733  10.50000  0.05    0.79
Q22   1   0.4915  0.2500  0.7026  10.50000  0.05    0.79
Q23   1   0.4802 -0.0602  0.9336  11.00000  0.05    0.78
Q24   1   0.1867  0.4626  0.4975  11.00000  0.05    0.74
Q25   1   0.1264  0.4501  0.7229  11.00000  0.05    0.73
;
_shelx_res_checksum              59027
_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_CuFmNO3
_database_code_depnum_ccdc_archive 'CCDC 1492388'
_audit_update_record             
;
2017-01-25 deposited with the CCDC.
2017-03-08 downloaded from the CCDC.
;

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H7 Cu N3 O5'
_chemical_formula_sum            'C H7 Cu N3 O5'
_chemical_formula_weight         204.64
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P m n b'
_space_group_name_Hall           '-P 2bc 2a'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'x+1/2, -y, -z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x-1/2, y, z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.1767(3)
_cell_length_b                   7.3661(4)
_cell_length_c                   12.3418(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     652.44(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    904
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_exptl_absorpt_coefficient_mu    3.321
_exptl_absorpt_correction_T_max  1.048
_exptl_absorpt_correction_T_min  1.000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark blue'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    2.083
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             412
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.057
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            9265
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.528
_diffrn_reflns_theta_min         3.221
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       Area
_diffrn_measurement_method       ω
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.030886
_diffrn_orient_matrix_UB_12      -0.023129
_diffrn_orient_matrix_UB_13      0.077795
_diffrn_orient_matrix_UB_21      0.082449
_diffrn_orient_matrix_UB_22      -0.109437
_diffrn_orient_matrix_UB_23      -0.000521
_diffrn_orient_matrix_UB_31      0.107999
_diffrn_orient_matrix_UB_32      0.076932
_diffrn_orient_matrix_UB_33      0.022646
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                604
_reflns_number_total             814
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Dolomanov et al., 2009)'
_refine_diff_density_max         1.181
_refine_diff_density_min         -1.734
_refine_diff_density_rms         0.386
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     59
_refine_ls_number_reflns         814
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0496
_refine_ls_restrained_S_all      1.205
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1125P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1872
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1)
2.b Idealised Me refined as rotating group:
 N4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.7500 0.31543(12) 0.37513(7) 0.0149(4) Uani 1 2 d S T P . .
O1 O 0.7500 0.0350(9) 0.6717(5) 0.0302(14) Uani 1 2 d S T P . .
O4 O 0.7500 0.5801(7) 0.4255(4) 0.0188(12) Uani 1 2 d S T P . .
O3 O 0.7500 0.0786(10) 0.4979(5) 0.0335(15) Uani 1 2 d S T P . .
N1 N 0.7500 0.1411(10) 0.5936(6) 0.0216(15) Uani 1 2 d S T P . .
C1 C 0.7500 0.6851(11) 0.3448(7) 0.0198(17) Uani 1 2 d S T P . .
H1 H 0.7500 0.8096 0.3573 0.024 Uiso 1 2 calc RS T P . .
N2 N 0.4767(7) 0.3146(6) 0.3722(3) 0.0182(11) Uani 1 1 d . . . . .
H2A H 0.4369 0.3800 0.3161 0.022 Uiso 1 1 calc GR . . . .
H2B H 0.4332 0.3624 0.4334 0.022 Uiso 1 1 calc GR . . . .
H2C H 0.4359 0.2010 0.3657 0.022 Uiso 1 1 calc GR . . . .
O5 O 0.7500 0.6307(8) 0.2498(4) 0.0176(12) Uani 1 2 d S T P . .
O2 O 0.7500 0.3041(9) 0.6076(6) 0.060(3) Uani 1 2 d S T P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0136(6) 0.0151(6) 0.0160(6) -0.0017(3) 0.000 0.000
O1 0.051(4) 0.023(3) 0.017(3) 0.003(3) 0.000 0.000
O4 0.026(3) 0.017(3) 0.014(3) 0.000(2) 0.000 0.000
O3 0.050(4) 0.034(4) 0.017(3) 0.001(3) 0.000 0.000
N1 0.029(4) 0.017(3) 0.019(3) 0.001(3) 0.000 0.000
C1 0.021(4) 0.015(4) 0.023(4) 0.000(3) 0.000 0.000
N2 0.014(2) 0.020(3) 0.021(3) -0.0037(17) 0.0027(17) 0.0014(17)
O5 0.025(3) 0.015(3) 0.013(3) 0.004(2) 0.000 0.000
O2 0.126(9) 0.014(4) 0.039(4) -0.002(3) 0.000 0.000

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O4 2.046(6) . ?
Cu1 O3 2.311(7) . ?
Cu1 N2 1.962(5) . ?
Cu1 N2 1.962(5) 7_755 ?
Cu1 O5 2.057(5) 6_556 ?
O1 N1 1.241(10) . ?
O4 C1 1.260(10) . ?
O3 N1 1.268(9) . ?
N1 O2 1.213(10) . ?
C1 H1 0.9300 . ?
C1 O5 1.239(10) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
O5 Cu1 2.057(5) 6_566 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Cu1 O3 121.4(2) . . ?
O4 Cu1 O5 149.1(2) . 6_556 ?
N2 Cu1 O4 90.49(12) . . ?
N2 Cu1 O4 90.49(12) 7_755 . ?
N2 Cu1 O3 90.56(12) 7_755 . ?
N2 Cu1 O3 90.56(12) . . ?
N2 Cu1 N2 177.8(2) . 7_755 ?
N2 Cu1 O5 89.09(11) . 6_556 ?
N2 Cu1 O5 89.09(11) 7_755 6_556 ?
O5 Cu1 O3 89.5(2) 6_556 . ?
C1 O4 Cu1 110.2(5) . . ?
N1 O3 Cu1 109.7(6) . . ?
O1 N1 O3 119.6(7) . . ?
O2 N1 O1 120.9(8) . . ?
O2 N1 O3 119.5(8) . . ?
O4 C1 H1 118.4 . . ?
O5 C1 O4 123.3(7) . . ?
O5 C1 H1 118.4 . . ?
Cu1 N2 H2A 109.5 . . ?
Cu1 N2 H2B 109.5 . . ?
Cu1 N2 H2C 109.5 . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C1 O5 Cu1 119.7(5) . 6_566 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O4 C1 O5 0.000(3) . . . . ?
Cu1 O3 N1 O1 180.000(2) . . . . ?
Cu1 O3 N1 O2 0.000(2) . . . . ?
O4 C1 O5 Cu1 180.000(2) . . . 6_566 ?

_iucr_refine_instructions_details 
;

    shelx.res created by SHELXL-2014/7

TITL
CELL 0.71073 7.1767 7.3661 12.3418 90 90 90
ZERR 4 0.0003 0.0004 0.0007 0 0 0
LATT 1
SYMM -X,0.5-Y,0.5+Z
SYMM 0.5+X,-Y,-Z
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H Cu N O
UNIT 4 28 4 12 20
 
L.S. 4
PLAN  20
MORE -1
BOND $H
CONF
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%./shelx.hkl">
REM </olex2.extras>
 
WGHT    0.112500
FVAR       0.25555
CU1   3    0.750000    0.315435    0.375135    10.50000    0.01363    0.01509 =
         0.01598   -0.00168    0.00000    0.00000
O1    5    0.750000    0.034956    0.671665    10.50000    0.05111    0.02300 =
         0.01660    0.00334    0.00000    0.00000
O4    5    0.750000    0.580092    0.425457    10.50000    0.02596    0.01678 =
         0.01356   -0.00031    0.00000    0.00000
O3    5    0.750000    0.078559    0.497928    10.50000    0.04994    0.03389 =
         0.01675    0.00085    0.00000    0.00000
N1    4    0.750000    0.141118    0.593625    10.50000    0.02900    0.01724 =
         0.01853    0.00080    0.00000    0.00000
C1    1    0.750000    0.685070    0.344827    10.50000    0.02102    0.01534 =
         0.02313    0.00007    0.00000    0.00000
AFIX  43
H1    2    0.750000    0.809595    0.357252    10.50000   -1.20000
AFIX   0
N2    4    0.476676    0.314603    0.372188    11.00000    0.01426    0.01952 =
         0.02078   -0.00373    0.00273    0.00139
AFIX 137
H2A   2    0.436908    0.380036    0.316150    11.00000   -1.20000
H2B   2    0.433226    0.362375    0.433417    11.00000   -1.20000
H2C   2    0.435903    0.201022    0.365662    11.00000   -1.20000
AFIX   0
O5    5    0.750000    0.630666    0.249810    10.50000    0.02463    0.01533 =
         0.01272    0.00393    0.00000    0.00000
O2    5    0.750000    0.304144    0.607606    10.50000    0.12620    0.01376 =
         0.03906   -0.00197    0.00000    0.00000
HKLF 4
 
REM
REM R1 =  0.0496 for     604 Fo > 4sig(Fo)  and  0.0734 for all     814 data
REM     59 parameters refined using      0 restraints
 
END  
     
WGHT      0.1125      0.0000 

REM Highest difference peak  1.181,  deepest hole -1.734,  1-sigma level  0.386
Q1    1   0.2500  0.1787  0.3744  10.50000  0.05    1.18
Q2    1   0.7500  0.8022  0.4386  10.50000  0.05    0.84
Q3    1   0.7500  0.9153  0.4454  10.50000  0.05    0.76
Q4    1   0.7500  0.3253  0.5840  10.50000  0.05    0.70
Q5    1   0.7500 -0.1454  0.5382  10.50000  0.05    0.69
Q6    1   0.2500  0.2360  0.4621  10.50000  0.05    0.69
Q7    1   0.8528  0.8176  0.4830  11.00000  0.05    0.69
Q8    1   0.7500  0.6863  0.4791  10.50000  0.05    0.65
Q9    1   0.7500  0.5846  0.4553  10.50000  0.05    0.65
Q10   1   0.9190  0.8426  0.4278  11.00000  0.05    0.63
Q11   1   0.7500  0.3263  0.6720  10.50000  0.05    0.62
Q12   1   0.2500  0.3568  0.3318  10.50000  0.05    0.62
Q13   1   0.3670  0.2004  0.4385  11.00000  0.05    0.61
Q14   1   0.9069 -0.0002  0.6101  11.00000  0.05    0.59
Q15   1   0.8995  0.3197  0.7211  11.00000  0.05    0.59
Q16   1   0.7500 -0.1307  0.7046  10.50000  0.05    0.57
Q17   1   0.8821  0.7243  0.4301  11.00000  0.05    0.55
Q18   1   0.3458  0.1869  0.3111  11.00000  0.05    0.55
Q19   1   0.7500  0.4184  0.7088  10.50000  0.05    0.54
Q20   1   0.4016  0.3225  0.2097  11.00000  0.05    0.54

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0496 for 604 Fo > 4sig(Fo) and 0.0734 for all 916 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 1.18, deepest hole -1.73
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0734
  REM R1_gt = 0.0496
  REM wR_ref = 0.1872
  REM GOOF = 1.205
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 916
  REM Reflections_gt = 604
  REM Parameters = n/a
  REM Hole = -1.73
  REM Peak = 1.18
  REM Flack = n/a

  
;
_olex2_submission_original_sample_id CuFmNO3
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_CuFmClO4
_database_code_depnum_ccdc_archive 'CCDC 1492389'
_audit_update_record             
;
2017-01-25 deposited with the CCDC.
2017-03-08 downloaded from the CCDC.
;

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H7 Cl Cu N2 O6'
_chemical_formula_sum            'C H7 Cl Cu N2 O6'
_chemical_formula_weight         242.08
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   7.4087(6)
_cell_length_b                   7.8568(7)
_cell_length_c                   12.3745(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     720.30(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    941
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_exptl_absorpt_coefficient_mu    3.392
_exptl_absorpt_correction_T_max  1.148
_exptl_absorpt_correction_T_min  1.00
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            'dark blue'
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_density_diffrn    2.232
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.052
_diffrn_reflns_av_unetI/netI     0.0835
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4581
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_min         3.071
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_device       Area
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_method       ω
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      -0.04874
_diffrn_orient_matrix_UB_12      0.03084
_diffrn_orient_matrix_UB_13      -0.12203
_diffrn_orient_matrix_UB_21      0.11506
_diffrn_orient_matrix_UB_22      -0.01939
_diffrn_orient_matrix_UB_23      -0.05086
_diffrn_orient_matrix_UB_31      -0.01851
_diffrn_orient_matrix_UB_32      -0.07770
_diffrn_orient_matrix_UB_33      -0.01225
_reflns_d_resolution_high        0.62
_reflns_d_resolution_low         1.43
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                584
_reflns_number_total             879
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.764
_refine_diff_density_min         -1.634
_refine_diff_density_rms         0.481
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     62
_refine_ls_number_reflns         879
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0534
_refine_ls_restrained_S_all      1.177
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1145P)²+0.7763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1266
_refine_ls_wR_factor_ref         0.2140
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1)
2.b Idealised Me refined as rotating group:
 N4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.16818(18) 0.2500 0.35646(11) 0.0144(5) Uani 1 2 d S T P . .
Cl1 Cl 0.3442(3) 0.2500 0.6032(2) 0.0142(6) Uani 1 2 d S T P . .
O4 O 0.3560(11) 0.2500 0.2402(6) 0.0149(16) Uani 1 2 d S T P . .
N1 N 0.1751(8) 0.5032(9) 0.3670(5) 0.0177(14) Uani 1 1 d . . . . .
H1A H 0.0886 0.5474 0.3257 0.021 Uiso 1 1 calc GR . . . .
H1B H 0.2821 0.5408 0.3446 0.021 Uiso 1 1 calc GR . . . .
H1C H 0.1576 0.5344 0.4353 0.021 Uiso 1 1 calc GR . . . .
C1 C 0.3116(15) 0.2500 0.1383(9) 0.015(2) Uani 1 2 d S T P . .
H1 H 0.1900 0.2500 0.1197 0.018 Uiso 1 2 calc RS T P . .
O5 O 0.4264(10) 0.2500 0.0655(5) 0.0159(16) Uani 1 2 d S T P . .
O1 O 0.4941(11) 0.2500 0.6762(6) 0.0230(18) Uani 1 2 d S T P . .
O2 O 0.2391(9) 0.1010(8) 0.6192(5) 0.0277(14) Uani 1 1 d . . . . .
O3 O 0.4135(12) 0.2500 0.4943(6) 0.0242(19) Uani 1 2 d S T P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0158(8) 0.0149(7) 0.0126(7) 0.000 0.0013(5) 0.000
Cl1 0.0156(14) 0.0141(12) 0.0128(12) 0.000 0.0003(9) 0.000
O4 0.017(4) 0.015(4) 0.012(4) 0.000 0.000(3) 0.000
N1 0.013(3) 0.019(3) 0.021(3) 0.006(3) 0.002(3) 0.000(3)
C1 0.010(5) 0.018(5) 0.018(5) 0.000 -0.005(4) 0.000
O5 0.020(4) 0.017(4) 0.011(3) 0.000 0.004(3) 0.000
O1 0.014(4) 0.038(5) 0.018(4) 0.000 -0.007(3) 0.000
O2 0.028(3) 0.023(3) 0.032(3) 0.002(3) -0.003(3) -0.011(3)
O3 0.018(4) 0.043(5) 0.012(4) 0.000 -0.001(3) 0.000

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O4 2.001(7) . ?
Cu1 N1 1.994(7) 8_565 ?
Cu1 N1 1.994(7) . ?
Cu1 O5 2.035(8) 6_556 ?
Cl1 O1 1.432(8) . ?
Cl1 O2 1.420(6) . ?
Cl1 O2 1.420(6) 8_565 ?
Cl1 O3 1.442(8) . ?
O4 C1 1.303(12) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C1 H1 0.9300 . ?
C1 O5 1.238(13) . ?
O5 Cu1 2.035(8) 6_656 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Cu1 O5 162.4(3) . 6_556 ?
N1 Cu1 O4 91.67(18) 8_565 . ?
N1 Cu1 O4 91.67(18) . . ?
N1 Cu1 N1 172.0(4) 8_565 . ?
N1 Cu1 O5 89.52(18) . 6_556 ?
N1 Cu1 O5 89.52(18) 8_565 6_556 ?
O1 Cl1 O3 108.3(5) . . ?
O2 Cl1 O1 109.7(3) 8_565 . ?
O2 Cl1 O1 109.7(3) . . ?
O2 Cl1 O2 111.0(6) . 8_565 ?
O2 Cl1 O3 109.0(3) . . ?
O2 Cl1 O3 109.0(3) 8_565 . ?
C1 O4 Cu1 121.3(7) . . ?
Cu1 N1 H1A 109.5 . . ?
Cu1 N1 H1B 109.5 . . ?
Cu1 N1 H1C 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
O4 C1 H1 119.0 . . ?
O5 C1 O4 122.1(10) . . ?
O5 C1 H1 119.0 . . ?
C1 O5 Cu1 105.0(6) . 6_656 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O4 C1 O5 180.000(1) . . . . ?
O4 C1 O5 Cu1 0.000(1) . . . 6_656 ?

_iucr_refine_instructions_details 
;

    shelx.res created by SHELXL-2014/7

TITL shelx in Pnma #62
REM reset to Pnma #62
CELL 0.71073 7.4087 7.8568 12.3745 90 90 90
ZERR 4 0.0006 0.0007 0.001 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,0.5-Z
SYMM -X,0.5+Y,-Z
SFAC C H Cl Cu N O
UNIT 4 28 4 4 8 24
 
L.S. 10
PLAN  25
BOND
MORE -1
BOND $H
CONF
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%./shelx.hkl">
REM </olex2.extras>
 
WGHT    0.114500    0.776300
FVAR       0.15918
CU1   4    0.168182    0.250000    0.356462    10.50000    0.01580    0.01486 =
         0.01262    0.00000    0.00128    0.00000
CL1   3    0.344241    0.250000    0.603154    10.50000    0.01559    0.01410 =
         0.01285    0.00000    0.00026    0.00000
O4    6    0.356015    0.250000    0.240245    10.50000    0.01729    0.01543 =
         0.01199    0.00000    0.00024    0.00000
N1    5    0.175086    0.503189    0.366989    11.00000    0.01344    0.01887 =
         0.02077    0.00558    0.00184    0.00040
AFIX 137
H1A   2    0.088612    0.547397    0.325702    11.00000   -1.20000
H1B   2    0.282089    0.540753    0.344633    11.00000   -1.20000
H1C   2    0.157637    0.534416    0.435331    11.00000   -1.20000
AFIX   0
C1    1    0.311641    0.250000    0.138342    10.50000    0.00969    0.01776 =
         0.01819    0.00000   -0.00544    0.00000
AFIX  43
H1    2    0.190035    0.250000    0.119701    10.50000   -1.20000
AFIX   0
O5    6    0.426352    0.250000    0.065547    10.50000    0.02015    0.01696 =
         0.01063    0.00000    0.00359    0.00000
 
O1    6    0.494134    0.250000    0.676183    10.50000    0.01362    0.03776 =
         0.01761    0.00000   -0.00723    0.00000
O2    6    0.239078    0.101033    0.619162    11.00000    0.02840    0.02258 =
         0.03212    0.00240   -0.00307   -0.01062
O3    6    0.413549    0.250000    0.494288    10.50000    0.01770    0.04252 =
         0.01223    0.00000   -0.00147    0.00000
HKLF 4
 
REM  shelx in Pnma #62
REM R1 =  0.0534 for     584 Fo > 4sig(Fo)  and  0.0969 for all     879 data
REM     62 parameters refined using      0 restraints
 
END  
     
WGHT      0.1144      0.7763 

REM Highest difference peak  1.764,  deepest hole -1.634,  1-sigma level  0.481
Q1    1   0.6644  0.2500  0.5632  10.50000  0.05    1.76
Q2    1   0.2648  0.7500  0.4488  10.50000  0.05    1.69
Q3    1   0.3191  0.2500 -0.0201  10.50000  0.05    1.57
Q4    1   0.2206  0.2500  0.0520  10.50000  0.05    1.49
Q5    1   0.2118  0.7500  0.3947  10.50000  0.05    1.25
Q6    1   0.3647  0.2500  0.1039  10.50000  0.05    1.16
Q7    1   0.5463  0.2500  0.6177  10.50000  0.05    1.14
Q8    1   0.2218  0.7500  0.3431  10.50000  0.05    1.12
Q9    1   0.0210  0.7500  0.3997  10.50000  0.05    1.10
Q10   1   0.5089  0.2500  0.7026  10.50000  0.05    1.06
Q11   1   0.4362  0.2500  0.0196  10.50000  0.05    1.01
Q12   1   0.0099  0.2500  0.1403  10.50000  0.05    1.00
Q13   1   0.2276  0.1249  0.0646  11.00000  0.05    1.00
Q14   1   0.1072  0.7500  0.3317  10.50000  0.05    0.90
Q15   1   0.4717  0.2500  0.0766  10.50000  0.05    0.85
Q16   1   0.2208  0.1017  0.6477  11.00000  0.05    0.84
Q17   1   0.1886  0.6427  0.3509  11.00000  0.05    0.78
Q18   1   0.3342  0.6181  0.3709  11.00000  0.05    0.74
Q19   1   0.3158  0.6949  0.3128  11.00000  0.05    0.70
Q20   1   0.6377  0.2500  0.7608  10.50000  0.05    0.64
Q21   1   0.4128  0.2500  0.2388  10.50000  0.05    0.62
Q22   1   0.4016 -0.0415  0.5299  11.00000  0.05    0.56
Q23   1   0.4717  0.1314  0.6611  11.00000  0.05    0.49
Q24   1   0.3526  0.2500  0.7093  10.50000  0.05    0.47
Q25   1   0.1381  0.1274  0.7309  11.00000  0.05    0.47

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0534 for 584 Fo > 4sig(Fo) and 0.0969 for all 988 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 1.76, deepest hole -1.63
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0969
  REM R1_gt = 0.0534
  REM wR_ref = 0.2140
  REM GOOF = 1.177
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 988
  REM Reflections_gt = 584
  REM Parameters = n/a
  REM Hole = -1.63
  REM Peak = 1.76
  REM Flack = n/a

  
;
_olex2_submission_special_instructions 'No special instructions were received'
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# END of CIF
