# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_kp-mof-72m2-sr

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            UHM-31
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H10 Cu3 F2 O15, 4(C4 H9 N O)'
_chemical_formula_sum            'C34 H37 Cu3 F2 O19'
_chemical_formula_weight         978.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           cubic
_symmetry_space_group_name_H-M   'F m -3 m'

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

_cell_length_a                   26.31360(10)
_cell_length_b                   26.31360(10)
_cell_length_c                   26.31360(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     18219.68(12)
_cell_formula_units_Z            16
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    5487
_cell_measurement_theta_min      4.5
_cell_measurement_theta_max      69.0

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             7968
_exptl_absorpt_coefficient_mu    2.306
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8021
_exptl_absorpt_correction_T_max  0.8552
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            908
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0036
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       2
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         4.75
_diffrn_reflns_theta_max         68.74
_reflns_number_total             908
_reflns_number_gt                732
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury Win 3.3, 2014'
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
 SQUEEZE/PLATON was used in order to account for the electron density 
 from the 4 disordered DMA solvent molecules, which could not resolved.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1211P)²+22.4921P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         908
_refine_ls_number_parameters     42
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.2212
_refine_ls_wR_factor_gt          0.2127
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.146
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.21448(2) 0.21448(2) 0.1233(7) Uani 1 4 d S . .
O1 O 0.05191(13) 0.18253(13) 0.25688(12) 0.1438(13) Uani 1 1 d . . .
O2 O 0.0000 0.15792(18) 0.15792(18) 0.265(6) Uani 1 4 d S . .
C1 C 0.0680(3) 0.2030(2) 0.2970(2) 0.132(2) Uani 1 2 d S . .
C2 C 0.1116(3) 0.1778(2) 0.3222(2) 0.137(2) Uani 1 2 d S . .
C3 C 0.13415(18) 0.1995(3) 0.36585(18) 0.136(2) Uani 1 2 d S A 1
H3 H 0.1197 0.2292 0.3803 0.163 Uiso 0.67 2 calc SPR A 1
F1 F 0.1096(3) 0.2477(4) 0.3904(3) 0.153(4) Uani 0.33 2 d SP B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.954(3) 115 ?
Cu1 O1 1.954(3) 18 ?
Cu1 O1 1.954(3) 100 ?
Cu1 O1 1.954(3) . ?
Cu1 O2 2.105(7) . ?
Cu1 Cu1 2.6439(17) 121 ?
O1 C1 1.259(4) . ?
C1 O1 1.259(4) 138 ?
C1 C2 1.479(10) . ?
C2 C3 1.414(5) . ?
C2 C3 1.414(5) 56 ?
C3 C2 1.414(5) 35 ?
C3 H3 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 88.7(2) 115 18 ?
O1 Cu1 O1 168.57(17) 115 100 ?
O1 Cu1 O1 90.2(2) 18 100 ?
O1 Cu1 O1 90.2(2) 115 . ?
O1 Cu1 O1 168.57(17) 18 . ?
O1 Cu1 O1 88.7(2) 100 . ?
O1 Cu1 O2 95.72(9) 115 . ?
O1 Cu1 O2 95.72(9) 18 . ?
O1 Cu1 O2 95.72(9) 100 . ?
O1 Cu1 O2 95.71(9) . . ?
O1 Cu1 Cu1 84.28(9) 115 121 ?
O1 Cu1 Cu1 84.28(9) 18 121 ?
O1 Cu1 Cu1 84.28(9) 100 121 ?
O1 Cu1 Cu1 84.29(9) . 121 ?
O2 Cu1 Cu1 180.00(18) . 121 ?
C1 O1 Cu1 122.0(4) . . ?
O1 C1 O1 127.2(7) . 138 ?
O1 C1 C2 116.4(3) . . ?
O1 C1 C2 116.4(3) 138 . ?
C3 C2 C3 118.6(8) . 56 ?
C3 C2 C1 120.6(4) . . ?
C3 C2 C1 120.6(4) 56 . ?
C2 C3 C2 121.4(8) 35 . ?
C2 C3 H3 119.3 35 . ?
C2 C3 H3 119.3 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        68.74
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.049

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.012 -0.038 -0.013 10870 2334 '4 DMA '
_platon_squeeze_details          
;
The contributions of 2334 electrons were removed from the unit-cell
contents. In space group Fm-3m 2334/192 = 12.2  electrons were removed
from the asymmetric unit. With Z being 16, 194 electrons would be
associated with one formula unit, consistent with 4 DMA solvent
molecules per formula unit.
All level A alarms in CIFCHECK are being produced because the
cell contents from UNIT instruction and atom list do not agree.
(This was the wish of the crystallographic reviewer).
;


# start Validation Reply Form
_vrf_CHEMW03_kp-mof-72m2-sr      
;
PROBLEM: ALERT: The ratio of given/expected molecular weight as
RESPONSE: The cell contents from UNIT instruction 
and atom list do not agree because the crystallographic 
reviewer wanted to specify these values according to the
UNSQUEEZED structure, although this CIF is the SQUEEZED
version.
;
_vrf_PLAT051_kp-mof-72m2-sr      
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      10.17 %     
RESPONSE:The cell contents from UNIT instruction 
and atom list do not agree because the crystallographic 
reviewer wanted to specify these values according to the
UNSQUEEZED structure, although this CIF is the SQUEEZED
version. ...
;
# end Validation Reply Form
_database_code_depnum_ccdc_archive 'CCDC 986518'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_kp-mof-72-2m1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            UHM-32
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H21 Cu2 F N2 O9'
_chemical_formula_weight         543.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   10.83040(10)
_cell_length_b                   11.99850(10)
_cell_length_c                   15.4960(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.2270(10)
_cell_angle_gamma                90.00
_cell_volume                     2005.31(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    1145
_cell_measurement_theta_min      4.5
_cell_measurement_theta_max      75.0

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    3.204
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.5667
_exptl_absorpt_correction_T_max  0.6998
_exptl_absorpt_process_details   
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
 (compiled Oct 27 2011,15:02:11)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            36617
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.67
_diffrn_reflns_theta_max         76.39
_reflns_number_total             4186
_reflns_number_gt                3907
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalMaker Win 2.6.4, 2013'
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0519P)²+6.9019P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4186
_refine_ls_number_parameters     289
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1168
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.52377(4) 0.87118(4) 0.15866(3) 0.02132(14) Uani 1 1 d . . .
Cu2 Cu 0.63630(4) 0.99621(3) -0.00584(3) 0.01630(13) Uani 1 1 d . . .
O1 O 0.50620(17) 0.89828(17) 0.03375(13) 0.0166(4) Uani 1 1 d . . .
H1 H 0.4968 0.8277 -0.0005 0.020 Uiso 1 1 calc R . .
O2 O 0.77990(18) 0.9303(2) 0.06303(15) 0.0251(5) Uani 1 1 d . . .
O3 O 0.6959(2) 0.8287(2) 0.16388(16) 0.0291(5) Uani 1 1 d . . .
O4 O 1.23872(18) 0.90366(18) 0.04642(14) 0.0203(4) Uani 1 1 d . . .
O5 O 1.34843(19) 0.8466(2) 0.16878(15) 0.0304(5) Uani 1 1 d . . .
O6 O 0.9493(2) 0.5490(2) 0.32584(18) 0.0359(6) Uani 1 1 d . . .
O7 O 1.14024(19) 0.60289(19) 0.37613(14) 0.0240(5) Uani 1 1 d . . .
C1 C 0.7849(3) 0.8655(2) 0.12622(19) 0.0179(6) Uani 1 1 d . A .
C2 C 0.9109(3) 0.8233(3) 0.16028(19) 0.0197(6) Uani 1 1 d . . .
C3 C 0.9217(3) 0.7445(3) 0.2266(2) 0.0207(6) Uani 1 1 d . A 1
H3 H 0.8490 0.7197 0.2508 0.025 Uiso 0.68 1 calc PR A 1
F3 F 0.8223(5) 0.7147(5) 0.2682(4) 0.0251(12) Uiso 0.32 1 d P B 2
C4 C 1.2502(3) 0.8596(3) 0.1202(2) 0.0200(6) Uani 1 1 d . A .
C5 C 1.0361(3) 0.7014(3) 0.2584(2) 0.0218(6) Uani 1 1 d . . .
C6 C 1.1414(3) 0.7396(3) 0.2226(2) 0.0231(6) Uani 1 1 d . A 1
H6 H 1.2202 0.7114 0.2441 0.028 Uiso 0.50 1 calc PR A 1
F6 F 1.2498(4) 0.6849(3) 0.2421(3) 0.0307(8) Uiso 0.50 1 d P C 2
C7 C 1.0429(3) 0.6111(3) 0.3264(2) 0.0238(6) Uani 1 1 d . A .
C8 C 1.1344(3) 0.8183(3) 0.1560(2) 0.0201(6) Uani 1 1 d . . .
C9 C 1.0180(3) 0.8587(3) 0.1248(2) 0.0196(6) Uani 1 1 d . A 1
H9 H 1.0116 0.9111 0.0786 0.023 Uiso 0.82 1 calc PR A 1
F9 F 1.0115(10) 0.9347(9) 0.0618(7) 0.028(2) Uiso 0.18 1 d P D 2
O8 O 0.5408(3) 0.8171(4) 0.28064(19) 0.0702(13) Uani 1 1 d . . .
C10 C 0.4773(4) 0.7830(8) 0.3371(3) 0.131(5) Uani 1 1 d D . .
C11 C 0.3377(4) 0.8031(4) 0.4512(3) 0.0421(9) Uani 1 1 d . . .
H11A H 0.3675 0.8406 0.5053 0.063 Uiso 1 1 calc R . .
H11B H 0.3404 0.7222 0.4599 0.063 Uiso 1 1 calc R . .
H11C H 0.2522 0.8261 0.4339 0.063 Uiso 1 1 calc R . .
C12 C 0.4768(5) 0.6554(5) 0.3670(4) 0.0645(14) Uani 1 1 d D . .
H12A H 0.5259 0.6474 0.4229 0.097 Uiso 1 1 calc R . .
H12B H 0.5128 0.6090 0.3236 0.097 Uiso 1 1 calc R . .
H12C H 0.3913 0.6316 0.3726 0.097 Uiso 1 1 calc R . .
N1 N 0.4157(4) 0.8330(6) 0.3840(3) 0.089(2) Uani 1 1 d . . .
C13 C 0.4169(6) 0.9644(4) 0.3586(4) 0.0614(13) Uani 1 1 d . . .
H13A H 0.4927 0.9814 0.3310 0.092 Uiso 1 1 calc R . .
H13B H 0.4146 1.0095 0.4111 0.092 Uiso 1 1 calc R . .
H13C H 0.3444 0.9814 0.3183 0.092 Uiso 1 1 calc R . .
O9 O 0.5011(2) 0.3118(2) 0.04151(17) 0.0337(6) Uani 1 1 d . . .
C14 C 0.5902(4) 0.3676(3) 0.0750(2) 0.0341(8) Uani 1 1 d . . .
N2 N 0.5733(3) 0.4614(3) 0.1180(2) 0.0352(7) Uani 1 1 d . . .
C15 C 0.4469(4) 0.4978(3) 0.1280(3) 0.0397(9) Uani 1 1 d . . .
H15A H 0.3898 0.4626 0.0834 0.059 Uiso 1 1 calc R . .
H15B H 0.4417 0.5790 0.1219 0.059 Uiso 1 1 calc R . .
H15C H 0.4242 0.4762 0.1855 0.059 Uiso 1 1 calc R . .
C16 C 0.7222(4) 0.3310(4) 0.0661(3) 0.0476(11) Uani 1 1 d . . .
H16A H 0.7216 0.2598 0.0351 0.071 Uiso 1 1 calc R . .
H16B H 0.7662 0.3221 0.1238 0.071 Uiso 1 1 calc R . .
H16C H 0.7643 0.3875 0.0337 0.071 Uiso 1 1 calc R . .
C17 C 0.6740(4) 0.5288(4) 0.1600(3) 0.0475(10) Uani 1 1 d . . .
H17A H 0.7533 0.4911 0.1550 0.071 Uiso 1 1 calc R . .
H17B H 0.6613 0.5386 0.2213 0.071 Uiso 1 1 calc R . .
H17C H 0.6749 0.6018 0.1318 0.071 Uiso 1 1 calc R . .


_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 O3 1.928(2) . ?
Cu1 O5 1.942(2) 1_455 ?
Cu1 O1 1.955(2) . ?
Cu1 O8 1.991(3) . ?
Cu1 O6 2.164(3) 2_655 ?
Cu2 O4 1.956(2) 3_775 ?
Cu2 O2 1.970(2) . ?
Cu2 O1 1.975(2) . ?
Cu2 O1 2.012(2) 3_675 ?
Cu2 O7 2.185(2) 4_575 ?
Cu2 Cu2 2.9758(8) 3_675 ?
O1 Cu2 2.013(2) 3_675 ?
O1 H1 1.0000 . ?
O2 C1 1.247(4) . ?
O3 C1 1.252(4) . ?
O4 C4 1.255(4) . ?
O4 Cu2 1.956(2) 3_775 ?
O5 C4 1.255(4) . ?
O5 Cu1 1.942(2) 1_655 ?
O6 C7 1.258(4) . ?
O6 Cu1 2.164(3) 2_645 ?
O7 C7 1.251(4) . ?
O7 Cu2 2.185(2) 4_676 ?
C1 C2 1.506(4) . ?
C2 C3 1.393(4) . ?
C2 C9 1.395(4) . ?
C3 C5 1.392(4) . ?
C3 H3 0.9500 . ?
C4 C8 1.501(4) . ?
C5 C6 1.389(4) . ?
C5 C7 1.509(4) . ?
C6 C8 1.397(4) . ?
C6 H6 0.9500 . ?
C8 C9 1.395(4) . ?
C9 H9 0.9500 . ?
O8 C10 1.232(6) . ?
C10 N1 1.192(9) . ?
C10 C12 1.599(8) . ?
C11 N1 1.444(6) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N1 C13 1.626(9) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
O9 C14 1.248(5) . ?
C14 N2 1.328(5) . ?
C14 C16 1.514(5) . ?
N2 C15 1.459(5) . ?
N2 C17 1.462(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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
O3 Cu1 O5 154.92(11) . 1_455 ?
O3 Cu1 O1 95.28(9) . . ?
O5 Cu1 O1 95.60(9) 1_455 . ?
O3 Cu1 O8 82.42(11) . . ?
O5 Cu1 O8 83.16(10) 1_455 . ?
O1 Cu1 O8 170.55(16) . . ?
O3 Cu1 O6 97.81(10) . 2_655 ?
O5 Cu1 O6 105.28(11) 1_455 2_655 ?
O1 Cu1 O6 86.90(10) . 2_655 ?
O8 Cu1 O6 102.48(16) . 2_655 ?
O4 Cu2 O2 83.42(9) 3_775 . ?
O4 Cu2 O1 178.27(8) 3_775 . ?
O2 Cu2 O1 98.24(9) . . ?
O4 Cu2 O1 94.82(8) 3_775 3_675 ?
O2 Cu2 O1 157.08(10) . 3_675 ?
O1 Cu2 O1 83.46(9) . 3_675 ?
O4 Cu2 O7 89.90(9) 3_775 4_575 ?
O2 Cu2 O7 99.23(9) . 4_575 ?
O1 Cu2 O7 90.30(8) . 4_575 ?
O1 Cu2 O7 103.62(8) 3_675 4_575 ?
O4 Cu2 Cu2 136.07(7) 3_775 3_675 ?
O2 Cu2 Cu2 135.89(7) . 3_675 ?
O1 Cu2 Cu2 42.22(6) . 3_675 ?
O1 Cu2 Cu2 41.25(6) 3_675 3_675 ?
O7 Cu2 Cu2 99.36(6) 4_575 3_675 ?
Cu1 O1 Cu2 113.50(9) . . ?
Cu1 O1 Cu2 108.72(9) . 3_675 ?
Cu2 O1 Cu2 96.54(9) . 3_675 ?
Cu1 O1 H1 112.4 . . ?
Cu2 O1 H1 112.4 . . ?
Cu2 O1 H1 112.4 3_675 . ?
C1 O2 Cu2 130.61(19) . . ?
C1 O3 Cu1 132.0(2) . . ?
C4 O4 Cu2 122.48(19) . 3_775 ?
C4 O5 Cu1 135.6(2) . 1_655 ?
C7 O6 Cu1 118.8(2) . 2_645 ?
C7 O7 Cu2 118.6(2) . 4_676 ?
O2 C1 O3 127.3(3) . . ?
O2 C1 C2 117.3(3) . . ?
O3 C1 C2 115.4(3) . . ?
C3 C2 C9 118.7(3) . . ?
C3 C2 C1 119.9(3) . . ?
C9 C2 C1 121.3(3) . . ?
C5 C3 C2 121.7(3) . . ?
C5 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
O4 C4 O5 127.4(3) . . ?
O4 C4 C8 117.3(3) . . ?
O5 C4 C8 115.4(3) . . ?
C6 C5 C3 118.2(3) . . ?
C6 C5 C7 121.7(3) . . ?
C3 C5 C7 120.0(3) . . ?
C5 C6 C8 121.8(3) . . ?
C5 C6 H6 119.1 . . ?
C8 C6 H6 119.1 . . ?
O7 C7 O6 126.3(3) . . ?
O7 C7 C5 118.1(3) . . ?
O6 C7 C5 115.6(3) . . ?
C9 C8 C6 118.5(3) . . ?
C9 C8 C4 121.1(3) . . ?
C6 C8 C4 120.4(3) . . ?
C2 C9 C8 121.0(3) . . ?
C2 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C10 O8 Cu1 140.7(3) . . ?
N1 C10 O8 130.3(9) . . ?
N1 C10 C12 106.8(5) . . ?
O8 C10 C12 122.7(7) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 N1 C11 135.3(7) . . ?
C10 N1 C13 108.8(6) . . ?
C11 N1 C13 115.7(5) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O9 C14 N2 121.8(4) . . ?
O9 C14 C16 120.5(4) . . ?
N2 C14 C16 117.7(3) . . ?
C14 N2 C15 118.7(3) . . ?
C14 N2 C17 124.1(4) . . ?
C15 N2 C17 117.1(3) . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        76.39
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.368
_refine_diff_density_min         -0.951
_refine_diff_density_rms         0.101
_database_code_depnum_ccdc_archive 'CCDC 986519'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_kp-mof-65m1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            UHM-33
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H21 Cu F N2 O8'
_chemical_formula_weight         463.90

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   11.89060(10)
_cell_length_b                   11.62620(10)
_cell_length_c                   14.50100(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.6710(10)
_cell_angle_gamma                90.00
_cell_volume                     2003.80(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    869
_cell_measurement_theta_min      4.5
_cell_measurement_theta_max      75.0

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             956
_exptl_absorpt_coefficient_mu    2.054
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6842
_exptl_absorpt_correction_T_max  0.8210
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            39591
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0086
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.72
_diffrn_reflns_theta_max         76.31
_reflns_number_total             4185
_reflns_number_gt                4105
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury Win 3.3, 2014'
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0503P)²+3.2973P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4185
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.58211(3) 0.57841(3) 0.00879(2) 0.01966(11) Uani 1 1 d . . .
O1 O 0.48816(14) 0.63209(15) 0.10949(13) 0.0328(4) Uani 1 1 d . . .
O2 O 0.34600(14) 0.96523(15) 0.40731(12) 0.0309(4) Uani 1 1 d . . .
O3 O 0.48490(16) 0.83608(16) 0.42165(14) 0.0402(5) Uani 1 1 d . . .
O4 O 0.35051(16) 0.50292(17) 0.09452(12) 0.0378(4) Uani 1 1 d . . .
O5 O -0.0005(2) 0.6731(4) 0.3766(2) 0.1126(16) Uani 1 1 d . . .
H5A H -0.0599 0.6359 0.3848 0.169 Uiso 0.50 1 calc PR . .
O6 O -0.00043(19) 0.5671(2) 0.2538(2) 0.0592(6) Uani 1 1 d . . .
H6A H -0.0560 0.5377 0.2794 0.089 Uiso 0.50 1 calc PR . .
F1 F 0.4923(3) 0.7704(4) 0.2433(3) 0.0344(9) Uani 0.34 1 d P A 2
F2 F 0.1621(2) 0.8121(3) 0.41070(19) 0.0329(6) Uani 0.50 1 d P B 2
F3 F 0.1573(8) 0.5574(8) 0.1660(6) 0.035(2) Uani 0.16 1 d P C 2
C1 C 0.39560(18) 0.58971(18) 0.13016(14) 0.0221(4) Uani 1 1 d . D .
C2 C 0.33282(18) 0.64931(19) 0.20438(14) 0.0231(4) Uani 1 1 d . . .
C3 C 0.2208(2) 0.6229(2) 0.21948(16) 0.0270(5) Uani 1 1 d . D 1
H3 H 0.1841 0.5662 0.1823 0.032 Uiso 0.66 1 calc PR D 1
C4 C 0.1613(2) 0.6779(2) 0.28813(16) 0.0288(5) Uani 1 1 d . . .
C5 C 0.21635(19) 0.7620(2) 0.34150(16) 0.0271(5) Uani 1 1 d . D 1
H5B H 0.1761 0.8019 0.3872 0.033 Uiso 0.50 1 calc PR D 1
C6 C 0.32887(19) 0.78837(19) 0.32900(15) 0.0234(4) Uani 1 1 d . . .
C7 C 0.38545(18) 0.7316(2) 0.26025(15) 0.0235(4) Uani 1 1 d . D 1
H7 H 0.4623 0.7495 0.2510 0.028 Uiso 0.84 1 calc PR D 1
C8 C 0.39189(18) 0.87047(19) 0.39118(14) 0.0228(4) Uani 1 1 d . D .
C9 C 0.0432(2) 0.6399(3) 0.30546(19) 0.0435(7) Uani 1 1 d . D .
C10 C 0.8798(2) 0.6094(3) 0.0132(2) 0.0412(6) Uani 1 1 d . . .
H10A H 0.8325 0.5531 -0.0199 0.062 Uiso 1 1 calc R . .
H10B H 0.9172 0.5723 0.0665 0.062 Uiso 1 1 calc R . .
H10C H 0.9366 0.6393 -0.0281 0.062 Uiso 1 1 calc R . .
C11 C -0.2848(3) 0.6492(3) 0.3040(3) 0.0572(9) Uani 1 1 d . E .
H11A H -0.3232 0.6252 0.2465 0.086 Uiso 1 1 calc R . .
H11B H -0.2131 0.6859 0.2900 0.086 Uiso 1 1 calc R . .
H11C H -0.3323 0.7040 0.3364 0.086 Uiso 1 1 calc R . .
O7 O 0.70336(14) 0.70829(14) 0.03079(13) 0.0313(4) Uani 1 1 d . . .
C12 C 0.8080(2) 0.7066(2) 0.04572(17) 0.0313(5) Uani 1 1 d . . .
N1 N 0.8571(2) 0.7921(2) 0.0921(2) 0.0495(7) Uani 1 1 d . . .
C13 C 0.7887(3) 0.8858(3) 0.1280(4) 0.0850(17) Uani 1 1 d . . .
H13A H 0.7984 0.9547 0.0902 0.128 Uiso 1 1 calc R . .
H13B H 0.8125 0.9023 0.1919 0.128 Uiso 1 1 calc R . .
H13C H 0.7093 0.8630 0.1260 0.128 Uiso 1 1 calc R . .
C14 C 0.9792(3) 0.8056(3) 0.1045(3) 0.0617(10) Uani 1 1 d . . .
H14A H 1.0160 0.7315 0.0941 0.093 Uiso 1 1 calc R . .
H14B H 0.9970 0.8321 0.1674 0.093 Uiso 1 1 calc R . .
H14C H 1.0061 0.8622 0.0601 0.093 Uiso 1 1 calc R . .
O8A O -0.1678(3) 0.5413(3) 0.4186(3) 0.0411(11) Uani 0.576(6) 1 d P E 1
O8B O -0.1728(4) 0.4806(5) 0.3356(5) 0.062(2) Uani 0.424(6) 1 d P E 2
C15 C -0.2630(3) 0.5453(3) 0.3644(4) 0.0762(14) Uani 1 1 d . . .
N2 N -0.34431(19) 0.4833(2) 0.39213(16) 0.0357(5) Uani 1 1 d . E .
C16 C -0.3239(3) 0.3836(2) 0.4508(2) 0.0423(6) Uani 1 1 d . . .
H16A H -0.2547 0.3450 0.4326 0.063 Uiso 1 1 calc R E .
H16B H -0.3873 0.3301 0.4442 0.063 Uiso 1 1 calc R . .
H16C H -0.3159 0.4084 0.5153 0.063 Uiso 1 1 calc R . .
C17A C -0.4567(6) 0.4992(7) 0.3545(5) 0.0493(16) Uani 0.576(6) 1 d P E 1
H17A H -0.4877 0.5713 0.3778 0.074 Uiso 0.576(6) 1 calc PR E 1
H17B H -0.5042 0.4348 0.3732 0.074 Uiso 0.576(6) 1 calc PR E 1
H17C H -0.4548 0.5022 0.2871 0.074 Uiso 0.576(6) 1 calc PR E 1
C17B C -0.4566(10) 0.5398(11) 0.3968(9) 0.068(3) Uani 0.424(6) 1 d P E 2
H17D H -0.4524 0.6033 0.4412 0.101 Uiso 0.424(6) 1 calc PR E 2
H17E H -0.5123 0.4835 0.4166 0.101 Uiso 0.424(6) 1 calc PR E 2
H17F H -0.4788 0.5696 0.3358 0.101 Uiso 0.424(6) 1 calc PR E 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O3 1.9585(17) 4_575 ?
Cu1 O4 1.9622(17) 3_665 ?
Cu1 O1 1.9659(17) . ?
Cu1 O2 1.9701(16) 2_645 ?
Cu1 O7 2.1057(16) . ?
Cu1 Cu1 2.6781(6) 3_665 ?
O1 C1 1.250(3) . ?
O2 C8 1.254(3) . ?
O2 Cu1 1.9702(16) 2_655 ?
O3 C8 1.245(3) . ?
O3 Cu1 1.9586(17) 4_576 ?
O4 C1 1.248(3) . ?
O4 Cu1 1.9621(17) 3_665 ?
O5 C9 1.231(4) . ?
O5 H5A 0.8400 . ?
O6 C9 1.234(4) . ?
O6 H6A 0.8400 . ?
C1 C2 1.498(3) . ?
C2 C3 1.390(3) . ?
C2 C7 1.391(3) . ?
C3 C4 1.394(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(3) . ?
C4 C9 1.501(3) . ?
C5 C6 1.390(3) . ?
C5 H5B 0.9500 . ?
C6 C7 1.386(3) . ?
C6 C8 1.499(3) . ?
C7 H7 0.9500 . ?
C10 C12 1.500(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C15 1.510(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
O7 C12 1.257(3) . ?
C12 N1 1.327(3) . ?
N1 C13 1.464(5) . ?
N1 C14 1.466(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O8A C15 1.361(5) . ?
O8B C15 1.385(7) . ?
C15 N2 1.279(4) . ?
N2 C17A 1.441(7) . ?
N2 C16 1.455(4) . ?
N2 C17B 1.491(10) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?
C17B H17F 0.9800 . ?

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
O3 Cu1 O4 89.91(9) 4_575 3_665 ?
O3 Cu1 O1 88.89(9) 4_575 . ?
O4 Cu1 O1 166.80(7) 3_665 . ?
O3 Cu1 O2 167.09(7) 4_575 2_645 ?
O4 Cu1 O2 88.29(8) 3_665 2_645 ?
O1 Cu1 O2 89.95(8) . 2_645 ?
O3 Cu1 O7 97.02(7) 4_575 . ?
O4 Cu1 O7 99.68(7) 3_665 . ?
O1 Cu1 O7 93.51(7) . . ?
O2 Cu1 O7 95.88(7) 2_645 . ?
O3 Cu1 Cu1 82.49(5) 4_575 3_665 ?
O4 Cu1 Cu1 84.96(5) 3_665 3_665 ?
O1 Cu1 Cu1 81.85(5) . 3_665 ?
O2 Cu1 Cu1 84.62(5) 2_645 3_665 ?
O7 Cu1 Cu1 175.34(5) . 3_665 ?
C1 O1 Cu1 125.19(15) . . ?
C8 O2 Cu1 121.22(14) . 2_655 ?
C8 O3 Cu1 124.57(15) . 4_576 ?
C1 O4 Cu1 121.72(15) . 3_665 ?
C9 O5 H5A 109.5 . . ?
C9 O6 H6A 109.5 . . ?
O4 C1 O1 126.2(2) . . ?
O4 C1 C2 117.0(2) . . ?
O1 C1 C2 116.79(19) . . ?
C3 C2 C7 118.5(2) . . ?
C3 C2 C1 120.7(2) . . ?
C7 C2 C1 120.8(2) . . ?
C2 C3 C4 121.3(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 118.5(2) . . ?
C3 C4 C9 118.8(2) . . ?
C5 C4 C9 122.6(2) . . ?
C6 C5 C4 121.3(2) . . ?
C6 C5 H5B 119.4 . . ?
C4 C5 H5B 119.4 . . ?
C7 C6 C5 118.6(2) . . ?
C7 C6 C8 119.4(2) . . ?
C5 C6 C8 121.9(2) . . ?
C6 C7 C2 121.8(2) . . ?
C6 C7 H7 119.1 . . ?
C2 C7 H7 119.1 . . ?
O3 C8 O2 127.1(2) . . ?
O3 C8 C6 115.6(2) . . ?
O2 C8 C6 117.32(19) . . ?
O5 C9 O6 122.9(3) . . ?
O5 C9 C4 117.9(3) . . ?
O6 C9 C4 118.7(3) . . ?
C12 C10 H10A 109.5 . . ?
C12 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C12 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C15 C11 H11A 109.5 . . ?
C15 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C15 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 O7 Cu1 133.21(16) . . ?
O7 C12 N1 119.6(2) . . ?
O7 C12 C10 121.8(2) . . ?
N1 C12 C10 118.6(2) . . ?
C12 N1 C13 119.8(2) . . ?
C12 N1 C14 124.1(3) . . ?
C13 N1 C14 115.9(3) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 O8A 115.0(4) . . ?
N2 C15 O8B 112.8(4) . . ?
O8A C15 O8B 61.1(3) . . ?
N2 C15 C11 120.9(3) . . ?
O8A C15 C11 119.2(3) . . ?
O8B C15 C11 112.4(4) . . ?
C15 N2 C17A 120.7(4) . . ?
C15 N2 C16 121.2(3) . . ?
C17A N2 C16 117.4(4) . . ?
C15 N2 C17B 116.9(5) . . ?
C17A N2 C17B 30.5(5) . . ?
C16 N2 C17B 117.3(5) . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17A H17A 109.5 . . ?
N2 C17A H17B 109.5 . . ?
N2 C17A H17C 109.5 . . ?
N2 C17B H17D 109.5 . . ?
N2 C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
N2 C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        76.31
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.744
_refine_diff_density_min         -0.932
_refine_diff_density_rms         0.070
_database_code_depnum_ccdc_archive 'CCDC 986520'
