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

#\#CIF_1.1

#  CIF produced by WinGX routine CIF_UPDATE
#  Created on 2012-07-11 at 12:09:02
#  Using CIFtbx version 2.6.2 16 Jun 1998

#  Dictionary name : cif_core.dic
#  Dictionary vers : 2.3
#  Request file    : c:\wingx\files\archive.reqdat
#  CIF files read  : nath2c nath2c_

#------------------ SECTION 1. GLOBAL INFORMATION ---------------------------#

data_global

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2012-07-11
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_update_record             ?

#==============================================================================
#
# SUBMISSION DETAILS

_publ_contact_author_name        'Conan, Francoise'
_publ_contact_author_address     
;
Universite de Brest
UMR 6521 Laboratoire de chimie,
electrochimie moleculaire et chimie analytique 
6, avenue Victor Le Gorgeu
CS 93837
F-29238 BREST cedex 3
FRANCE 
;
_publ_contact_author_email       Francoise.conan@univ-brest.fr
loop_
_publ_author_name
_publ_author_address
'Cosquer, Nathalie'
;
Universite de Brest
UMR 6521 Laboratoire de chimie,
electrochimie moleculaire et chimie analytique 
6, avenue Victor Le Gorgeu
CS 93837
F-29238 BREST cedex 3
FRANCE 
;
'Conan, Francoise'
;
Universite de Brest
UMR 6521 Laboratoire de chimie,
electrochimie moleculaire et chimie analytique 
6, avenue Victor Le Gorgeu
CS 93837
F-29238 BREST cedex 3
FRANCE 
;

_journal_name_full               'private communication'
_journal_volume                  ?
_journal_page_first              ?
_journal_page_last               ?
_journal_year                    ?
_publ_section_references         
;
Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler,
M. (2004). J. Appl. Cryst. 37, 335-338.

Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999). J. Appl. Cryst. 32, 115-119

Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.

Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.

Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED system softwares,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET). 
Oxford Diffraction Ltd, Yarnton, England.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

Spek, A. L. (1990). Acta Cryst. A46, C-34.Acta Cryst. A46, C34.

Spek, A. L. (1998). PLATON, A Multipurpose Crystallographic Tool,
Utrecht University, Utrecht, The Netherlands.

Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
;


_publ_section_exptl_prep         
;
;


_publ_contact_letter             
;
 Submission dated :2013-06-20
 
Please consider this CIF for submission to the Cambridge Crystallographic
Data Centre. I certify that all authors have seen and approved of this
submission, that all have made significant scientific contributions to the
work reported, and that all share responsibility and accountability for
the results.
 
This CIF  is submitted as a personal communication
 
This CIF is submitted as part of a journal submission
<Insert Journal details here>
 
;

#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------#

data_nath2c

_audit_creation_date             2012-07-11T12:09:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H20 Cu N4 O, 2(C F3 O3 S)'
_chemical_formula_sum            'C20 H20 Cu F6 N4 O7 S2'
_chemical_formula_weight         670.06

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  -P2ac2ab
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.9351(7)
_cell_length_b                   15.2381(7)
_cell_length_c                   23.2704(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5295.9(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    170(2)
_cell_measurement_theta_min      2.8594
_cell_measurement_theta_max      27.2829

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       
;
truncated bipyramid
slopes {112}, truncates {001}
;
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.29046
_exptl_crystal_size_mid          0.20388
_exptl_crystal_size_min          0.10894
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2712
_exptl_crystal_recrystallization_method 
;
?
;
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.073
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++)
        (compiled Nov 14 2003,14:35:41)
Analytical numeric absorption correction using a multifaceted crystal
        model based on expressions derived by R.C. Clark & J.S. Reid.
;
_exptl_absorpt_correction_T_min  0.69049
_exptl_absorpt_correction_T_max  0.77736

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      170(2)
_diffrn_source                   'sealed X-ray tube'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_orient_matrix_ub_11      -0.0024007221
_diffrn_orient_matrix_ub_12      0.0460642819
_diffrn_orient_matrix_ub_13      -0.0040654077
_diffrn_orient_matrix_ub_21      -0.0370106504
_diffrn_orient_matrix_ub_22      -0.0057016654
_diffrn_orient_matrix_ub_23      -0.0187282406
_diffrn_orient_matrix_ub_31      -0.0296680706
_diffrn_orient_matrix_ub_32      0.0033821844
_diffrn_orient_matrix_ub_33      0.0237077674
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_av_unetI/netI     0.021
_diffrn_reflns_number            32177
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_detector                 'CCD plate'
_diffrn_measurement_device       'Kappa-geometry diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
crystal-detector distance: 60 mm
#__ type_ start__ end____ width___ exp.time_
  1 omega  -54.00   60.75   0.7500   15.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       25.0000  -79.0000    0.0000    0.0000    0.0000 153

#__ type_ start__ end____ width___ exp.time_
  2 omega  -54.00   60.75   0.7500   15.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       25.0000  -79.0000   90.0000    0.0000    0.0000 153

#__ type_ start__ end____ width___ exp.time_
  3 omega  -54.00   60.75   0.7500   15.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       25.0000  -79.0000  180.0000    0.0000    0.0000 153

#__ type_ start__ end____ width___ exp.time_
  4 omega  -54.00   60.75   0.7500   15.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       25.0000  -79.0000  270.0000    0.0000    0.0000 153
;
_reflns_number_total             5343
_reflns_number_gt                4350
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++)
        (compiled Nov 14 2003,14:35:41)
;
_computing_cell_refinement       
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++)
        (compiled Nov 14 2003,14:35:41)
;
_computing_data_reduction        
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.13 beta (release 14.11.2003 CrysAlis171 VC++)
        (compiled Nov 14 2003,14:35:41)
;
_computing_structure_solution    'SIR-92 (Altomare et al., 1992)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
WinGX (Farrugia, 1999)
PLATON (Spek, 1990-2003)
enCIFer (Allen et al., 2004)
;
#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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 > 2σ(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)+(0.0739P)²+0.2016P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5343
_refine_ls_number_parameters     367
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1121
_refine_ls_wR_factor_gt          0.1065
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.035
_refine_diff_density_min         -0.44
_refine_diff_density_rms         0.077

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'

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
C1 C 0.51820(16) 0.11590(16) 0.71128(10) 0.0290(5) Uani 1 1 d . . .
H1 H 0.5354 0.1714 0.7262 0.035 Uiso 1 1 calc R . .
C2 C 0.51649(17) 0.10517(18) 0.65304(11) 0.0339(6) Uani 1 1 d . . .
H2 H 0.5322 0.1522 0.6282 0.041 Uiso 1 1 calc R . .
C3 C 0.49136(16) 0.02435(18) 0.63081(11) 0.0347(6) Uani 1 1 d . . .
H3 H 0.4887 0.0152 0.5905 0.042 Uiso 1 1 calc R . .
C4 C 0.47036(18) -0.04256(16) 0.66843(10) 0.0313(6) Uani 1 1 d . . .
H4 H 0.4538 -0.0987 0.6542 0.038 Uiso 1 1 calc R . .
C5 C 0.47358(15) -0.02756(15) 0.72674(10) 0.0245(5) Uani 1 1 d . . .
C6 C 0.44700(16) -0.09476(14) 0.77060(9) 0.0274(5) Uani 1 1 d . . .
H6A H 0.3811 -0.0945 0.7752 0.033 Uiso 1 1 calc R . .
H6B H 0.4652 -0.1538 0.7572 0.033 Uiso 1 1 calc R . .
C7 C 0.65580(17) 0.08087(17) 0.91588(10) 0.0347(6) Uani 1 1 d . . .
H7 H 0.6338 0.1379 0.9243 0.042 Uiso 1 1 calc R . .
C8 C 0.73621(18) 0.05469(18) 0.93947(11) 0.0394(6) Uani 1 1 d . . .
H8 H 0.7695 0.0935 0.9632 0.047 Uiso 1 1 calc R . .
C9 C 0.76741(17) -0.0282(2) 0.92821(11) 0.0409(6) Uani 1 1 d . . .
H9 H 0.8224 -0.0475 0.9443 0.049 Uiso 1 1 calc R . .
C10 C 0.71830(16) -0.08326(18) 0.89325(11) 0.0353(6) Uani 1 1 d . . .
H10 H 0.7387 -0.141 0.8852 0.042 Uiso 1 1 calc R . .
C11 C 0.63883(15) -0.05285(15) 0.87008(10) 0.0275(5) Uani 1 1 d . . .
C12 C 0.58456(15) -0.10542(15) 0.82787(10) 0.0289(5) Uani 1 1 d . . .
H12A H 0.6107 -0.0991 0.789 0.035 Uiso 1 1 calc R . .
H12B H 0.5869 -0.1683 0.8385 0.035 Uiso 1 1 calc R . .
C13 C 0.30556(16) 0.08718(16) 0.89052(10) 0.0307(5) Uani 1 1 d . . .
H13 H 0.3152 0.1481 0.8843 0.037 Uiso 1 1 calc R . .
C14 C 0.22421(17) 0.06003(17) 0.91217(11) 0.0360(6) Uani 1 1 d . . .
H14 H 0.1789 0.1015 0.9212 0.043 Uiso 1 1 calc R . .
C15 C 0.20996(17) -0.02837(18) 0.92046(11) 0.0378(6) Uani 1 1 d . . .
H15 H 0.1541 -0.0487 0.9348 0.045 Uiso 1 1 calc R . .
C16 C 0.27760(16) -0.08741(18) 0.90782(11) 0.0349(6) Uani 1 1 d . . .
H16 H 0.2689 -0.1486 0.9132 0.042 Uiso 1 1 calc R . .
C17 C 0.35784(15) -0.05558(15) 0.88725(10) 0.0271(5) Uani 1 1 d . . .
C18 C 0.43722(16) -0.11327(14) 0.87490(10) 0.0289(5) Uani 1 1 d . . .
H18A H 0.4752 -0.1179 0.9097 0.035 Uiso 1 1 calc R . .
H18B H 0.4165 -0.1729 0.8645 0.035 Uiso 1 1 calc R . .
N1 N 0.49678(11) 0.05188(11) 0.74845(9) 0.0233(4) Uani 1 1 d . . .
N2 N 0.60750(12) 0.02824(13) 0.88127(8) 0.0274(4) Uani 1 1 d . . .
N3 N 0.37142(12) 0.03084(12) 0.87801(8) 0.0261(4) Uani 1 1 d . . .
N4 N 0.49015(12) -0.07576(13) 0.82698(8) 0.0241(4) Uani 1 1 d . . .
O7 O 0.49097(12) 0.18271(12) 0.84145(8) 0.0301(4) Uani 1 1 d D . .
Cu1 Cu 0.490983(18) 0.055229(17) 0.836667(12) 0.02260(11) Uani 1 1 d . . .
H7A H 0.5085(15) 0.2079(15) 0.8694(9) 0.027 Uiso 1 1 d D . .
H7B H 0.4516(14) 0.2087(15) 0.8269(9) 0.027 Uiso 1 1 d D . .
C19 C 0.43163(19) 0.24688(17) 1.00026(12) 0.0411(6) Uani 1 1 d . . .
O1 O 0.59616(14) 0.26226(14) 1.02746(9) 0.0543(6) Uani 1 1 d . . .
O2 O 0.51776(18) 0.39342(13) 0.99676(10) 0.0653(7) Uani 1 1 d . . .
O3 O 0.55535(14) 0.28128(12) 0.92768(7) 0.0442(5) Uani 1 1 d . . .
F1 F 0.36737(12) 0.27461(13) 0.96518(9) 0.0718(6) Uani 1 1 d . . .
F2 F 0.43882(12) 0.16043(10) 0.99255(7) 0.0527(4) Uani 1 1 d . . .
F3 F 0.40371(12) 0.25916(12) 1.05426(8) 0.0653(5) Uani 1 1 d . . .
S1 S 0.53719(5) 0.30227(4) 0.98699(3) 0.03556(18) Uani 1 1 d . . .
C20 C 0.73873(19) 0.6719(2) 0.77729(13) 0.0494(8) Uani 1 1 d . . .
O4 O 0.75599(12) 0.83812(15) 0.76448(9) 0.0521(5) Uani 1 1 d . . .
O5 O 0.63549(12) 0.76609(12) 0.71517(8) 0.0443(5) Uani 1 1 d . . .
O6 O 0.78926(13) 0.74358(12) 0.68339(8) 0.0439(5) Uani 1 1 d . . .
F4 F 0.71314(16) 0.59800(12) 0.75138(10) 0.0798(6) Uani 1 1 d . . .
F5 F 0.82135(12) 0.66180(17) 0.79524(9) 0.0912(8) Uani 1 1 d . . .
F6 F 0.68701(12) 0.68304(14) 0.82362(8) 0.0700(6) Uani 1 1 d . . .
S2 S 0.72990(4) 0.76544(4) 0.72948(3) 0.03284(17) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.343(3) . ?
C1 C2 1.365(3) . ?
C1 H1 0.95 . ?
C2 C3 1.388(4) . ?
C2 H2 0.95 . ?
C3 C4 1.380(4) . ?
C3 H3 0.95 . ?
C4 C5 1.377(3) . ?
C4 H4 0.95 . ?
C5 N1 1.357(3) . ?
C5 C6 1.499(3) . ?
C6 N4 1.490(3) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 N2 1.346(3) . ?
C7 C8 1.380(4) . ?
C7 H7 0.95 . ?
C8 C9 1.371(4) . ?
C8 H8 0.95 . ?
C9 C10 1.380(4) . ?
C9 H9 0.95 . ?
C10 C11 1.384(3) . ?
C10 H10 0.95 . ?
C11 N2 1.347(3) . ?
C11 C12 1.504(3) . ?
C12 N4 1.481(3) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 N3 1.338(3) . ?
C13 C14 1.379(3) . ?
C13 H13 0.95 . ?
C14 C15 1.377(4) . ?
C14 H14 0.95 . ?
C15 C16 1.384(4) . ?
C15 H15 0.95 . ?
C16 C17 1.379(3) . ?
C16 H16 0.95 . ?
C17 N3 1.350(3) . ?
C17 C18 1.504(3) . ?
C18 N4 1.482(3) . ?
C18 H18A 0.99 . ?
C18 H18B 0.99 . ?
N1 Cu1 2.055(2) . ?
N2 Cu1 2.0675(19) . ?
N3 Cu1 2.0621(19) . ?
N4 Cu1 2.009(2) . ?
O7 Cu1 1.9458(18) . ?
O7 H7A 0.800(16) . ?
O7 H7B 0.786(16) . ?
C19 F1 1.329(3) . ?
C19 F2 1.334(3) . ?
C19 F3 1.337(3) . ?
C19 S1 1.815(3) . ?
O1 S1 1.426(2) . ?
O2 S1 1.437(2) . ?
O3 S1 1.4425(18) . ?
C20 F5 1.312(3) . ?
C20 F4 1.334(4) . ?
C20 F6 1.337(3) . ?
C20 S2 1.813(3) . ?
O4 S2 1.429(2) . ?
O5 S2 1.4488(18) . ?
O6 S2 1.4309(19) . ?

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
N1 C1 C2 123.2(2) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C1 C2 C3 118.8(2) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 118.7(2) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N1 C5 C4 121.6(2) . . ?
N1 C5 C6 115.1(2) . . ?
C4 C5 C6 123.2(2) . . ?
N4 C6 C5 110.62(18) . . ?
N4 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
N4 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
N2 C7 C8 122.2(2) . . ?
N2 C7 H7 118.9 . . ?
C8 C7 H7 118.9 . . ?
C9 C8 C7 119.1(2) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 119.5(2) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C9 C10 C11 118.8(2) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
N2 C11 C10 122.0(2) . . ?
N2 C11 C12 115.3(2) . . ?
C10 C11 C12 122.6(2) . . ?
N4 C12 C11 111.08(19) . . ?
N4 C12 H12A 109.4 . . ?
C11 C12 H12A 109.4 . . ?
N4 C12 H12B 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108 . . ?
N3 C13 C14 122.3(2) . . ?
N3 C13 H13 118.8 . . ?
C14 C13 H13 118.8 . . ?
C15 C14 C13 118.7(2) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 119.5(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 118.7(2) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
N3 C17 C16 122.0(2) . . ?
N3 C17 C18 114.93(19) . . ?
C16 C17 C18 123.1(2) . . ?
N4 C18 C17 109.81(18) . . ?
N4 C18 H18A 109.7 . . ?
C17 C18 H18A 109.7 . . ?
N4 C18 H18B 109.7 . . ?
C17 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
C1 N1 C5 118.0(2) . . ?
C1 N1 Cu1 129.46(16) . . ?
C5 N1 Cu1 112.54(15) . . ?
C7 N2 C11 118.4(2) . . ?
C7 N2 Cu1 129.26(17) . . ?
C11 N2 Cu1 112.20(15) . . ?
C13 N3 C17 118.7(2) . . ?
C13 N3 Cu1 128.52(16) . . ?
C17 N3 Cu1 112.35(15) . . ?
C12 N4 C18 112.32(18) . . ?
C12 N4 C6 111.40(18) . . ?
C18 N4 C6 110.92(18) . . ?
C12 N4 Cu1 107.20(14) . . ?
C18 N4 Cu1 107.58(14) . . ?
C6 N4 Cu1 107.13(13) . . ?
Cu1 O7 H7A 121.7(18) . . ?
Cu1 O7 H7B 118.6(18) . . ?
H7A O7 H7B 111(2) . . ?
O7 Cu1 N4 176.82(8) . . ?
O7 Cu1 N1 94.70(7) . . ?
N4 Cu1 N1 82.15(7) . . ?
O7 Cu1 N3 98.81(8) . . ?
N4 Cu1 N3 82.41(7) . . ?
N1 Cu1 N3 119.87(7) . . ?
O7 Cu1 N2 99.78(7) . . ?
N4 Cu1 N2 82.18(8) . . ?
N1 Cu1 N2 117.45(7) . . ?
N3 Cu1 N2 117.31(8) . . ?
F1 C19 F2 106.8(2) . . ?
F1 C19 F3 107.9(2) . . ?
F2 C19 F3 106.8(2) . . ?
F1 C19 S1 112.0(2) . . ?
F2 C19 S1 111.50(19) . . ?
F3 C19 S1 111.45(19) . . ?
O1 S1 O2 115.69(14) . . ?
O1 S1 O3 114.88(13) . . ?
O2 S1 O3 113.81(12) . . ?
O1 S1 C19 103.02(12) . . ?
O2 S1 C19 104.31(14) . . ?
O3 S1 C19 102.89(12) . . ?
F5 C20 F4 108.3(3) . . ?
F5 C20 F6 107.5(2) . . ?
F4 C20 F6 107.8(3) . . ?
F5 C20 S2 110.9(2) . . ?
F4 C20 S2 111.5(2) . . ?
F6 C20 S2 110.7(2) . . ?
O4 S2 O6 116.03(11) . . ?
O4 S2 O5 113.03(12) . . ?
O6 S2 O5 115.61(12) . . ?
O4 S2 C20 103.86(15) . . ?
O6 S2 C20 103.41(12) . . ?
O5 S2 C20 102.55(12) . . ?


loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7A O3 0.800(16) 1.891(17) 2.685(2) 171(3) .
O7 H7B O5 0.786(16) 1.847(16) 2.630(2) 174(3) 4_646


#----------------------------------------------------------------------------#
#                   SHELXL.RES FILE                                          #
#----------------------------------------------------------------------------#

_iucr_refine_instruction_details 
;
TITL NATH2C in Pbca at 170 K
CELL  0.71073  14.9351  15.2381  23.2704   90.000   90.000   90.000
ZERR     8.00   0.0007   0.0007   0.0010    0.000    0.000    0.000
LATT   1
SYMM   1/2 - X, - Y, 1/2 + Z
SYMM   1/2 + X, 1/2 - Y, - Z
SYMM   - X, 1/2 + Y, 1/2 - Z
SFAC   C    H    N    O    F    S    CU
UNIT   160  160  32   56   48   16   8
MERG   2
SHEL   13 0.8
DFIX   0.82 0.02  O7 H7A  O7  H7B
DANG   1.30  0.04  H7A H7B
FMAP   2
PLAN   25
ACTA
BOND   $H
EQIV   $1   -x+1, y-1/2, -z+3/2
HTAB   O7  O3
HTAB   O7  O5_$1
L.S.   4
TEMP  -103.00
WGHT    0.073900    0.201800
FVAR       1.36910
MOLE    1
C1    1    0.518196    0.115904    0.711278    11.00000    0.03031    0.02808 =
         0.02847    0.00256   -0.00021   -0.00166
AFIX  43
H1    2    0.535383    0.171414    0.726235    11.00000   -1.20000
AFIX   0
C2    1    0.516491    0.105175    0.653043    11.00000    0.03600    0.03652 =
         0.02913    0.00680    0.00583    0.00086
AFIX  43
H2    2    0.532220    0.152178    0.628196    11.00000   -1.20000
AFIX   0
C3    1    0.491359    0.024346    0.630814    11.00000    0.03675    0.04712 =
         0.02033   -0.00358    0.00011    0.00287
AFIX  43
H3    2    0.488662    0.015242    0.590465    11.00000   -1.20000
AFIX   0
C4    1    0.470359   -0.042557    0.668434    11.00000    0.03454    0.03056 =
         0.02875   -0.01082   -0.00309   -0.00022
AFIX  43
H4    2    0.453769   -0.098667    0.654177    11.00000   -1.20000
AFIX   0
C5    1    0.473576   -0.027563    0.726745    11.00000    0.02131    0.02637 =
         0.02573   -0.00435   -0.00229    0.00054
C6    1    0.447000   -0.094756    0.770596    11.00000    0.03160    0.02428 =
         0.02645   -0.00264   -0.00155   -0.00417
AFIX  23
H6A   2    0.381102   -0.094516    0.775189    11.00000   -1.20000
H6B   2    0.465214   -0.153798    0.757235    11.00000   -1.20000
AFIX   0
C7    1    0.655797    0.080875    0.915878    11.00000    0.03952    0.03533 =
         0.02911   -0.00130   -0.00632   -0.00310
AFIX  43
H7    2    0.633784    0.137924    0.924329    11.00000   -1.20000
AFIX   0
C8    1    0.736212    0.054686    0.939473    11.00000    0.03557    0.05026 =
         0.03228    0.00235   -0.01224   -0.00494
AFIX  43
H8    2    0.769510    0.093527    0.963200    11.00000   -1.20000
AFIX   0
C9    1    0.767414   -0.028155    0.928210    11.00000    0.02897    0.05880 =
         0.03506    0.00709   -0.00686    0.00260
AFIX  43
H9    2    0.822418   -0.047482    0.944341    11.00000   -1.20000
AFIX   0
C10   1    0.718295   -0.083264    0.893254    11.00000    0.02982    0.04092 =
         0.03504    0.00404   -0.00049    0.00752
AFIX  43
H10   2    0.738687   -0.141038    0.885249    11.00000   -1.20000
AFIX   0
C11   1    0.638827   -0.052850    0.870082    11.00000    0.02468    0.03101 =
         0.02685    0.00370    0.00180    0.00027
C12   1    0.584561   -0.105415    0.827873    11.00000    0.02774    0.02779 =
         0.03127   -0.00113    0.00147    0.00553
AFIX  23
H12A  2    0.610676   -0.099074    0.788992    11.00000   -1.20000
H12B  2    0.586909   -0.168270    0.838531    11.00000   -1.20000
AFIX   0
C13   1    0.305556    0.087182    0.890523    11.00000    0.03141    0.03314 =
         0.02764   -0.00021   -0.00021    0.00623
AFIX  43
H13   2    0.315171    0.148065    0.884270    11.00000   -1.20000
AFIX   0
C14   1    0.224215    0.060031    0.912171    11.00000    0.02841    0.04912 =
         0.03039   -0.00027    0.00270    0.00888
AFIX  43
H14   2    0.178858    0.101509    0.921198    11.00000   -1.20000
AFIX   0
C15   1    0.209958   -0.028374    0.920463    11.00000    0.02752    0.05300 =
         0.03301    0.00528    0.00522   -0.00256
AFIX  43
H15   2    0.154099   -0.048690    0.934760    11.00000   -1.20000
AFIX   0
C16   1    0.277595   -0.087407    0.907817    11.00000    0.03143    0.04168 =
         0.03154    0.00563    0.00359   -0.00344
AFIX  43
H16   2    0.268894   -0.148615    0.913201    11.00000   -1.20000
AFIX   0
C17   1    0.357839   -0.055575    0.887250    11.00000    0.02596    0.03294 =
         0.02231    0.00332   -0.00084   -0.00132
C18   1    0.437221   -0.113267    0.874904    11.00000    0.03315    0.02528 =
         0.02818    0.00636    0.00202   -0.00063
AFIX  23
H18A  2    0.475161   -0.117928    0.909656    11.00000   -1.20000
H18B  2    0.416519   -0.172916    0.864525    11.00000   -1.20000
AFIX   0
N1    3    0.496782    0.051878    0.748453    11.00000    0.02370    0.02413 =
         0.02209   -0.00176   -0.00096   -0.00125
N2    3    0.607500    0.028239    0.881272    11.00000    0.02868    0.03085 =
         0.02277    0.00110   -0.00209   -0.00055
N3    3    0.371423    0.030845    0.878009    11.00000    0.02581    0.02830 =
         0.02406   -0.00038   -0.00045    0.00184
N4    3    0.490154   -0.075760    0.826978    11.00000    0.02287    0.02512 =
         0.02418    0.00203   -0.00056    0.00039
O7    4    0.490972    0.182711    0.841453    11.00000    0.03556    0.02365 =
         0.03120   -0.00695   -0.01007    0.00527
CU1   7    0.490983    0.055229    0.836667    11.00000    0.02432    0.02110 =
         0.02239   -0.00131   -0.00117    0.00022
H7A   2    0.508522    0.207882    0.869434    11.00000   -1.20000
H7B   2    0.451608    0.208744    0.826863    11.00000   -1.20000
MOLE    2
C19   1    0.431626    0.246878    1.000264    11.00000    0.04416    0.04153 =
         0.03769    0.00128   -0.00896    0.00623
O1    4    0.596158    0.262257    1.027456    11.00000    0.05151    0.06563 =
         0.04571    0.01785   -0.01935   -0.01543
O2    4    0.517759    0.393418    0.996764    11.00000    0.12019    0.02952 =
         0.04629   -0.00634    0.00979   -0.00598
O3    4    0.555353    0.281282    0.927682    11.00000    0.06512    0.03846 =
         0.02896   -0.00697   -0.00305   -0.00728
F1    5    0.367375    0.274611    0.965178    11.00000    0.05449    0.07873 =
         0.08224    0.00839   -0.02980    0.01695
F2    5    0.438824    0.160427    0.992552    11.00000    0.05623    0.03527 =
         0.06666    0.00222   -0.01139   -0.01150
F3    5    0.403714    0.259158    1.054255    11.00000    0.06149    0.08136 =
         0.05297   -0.00609    0.01308   -0.00517
S1    6    0.537187    0.302271    0.986994    11.00000    0.05708    0.02573 =
         0.02386   -0.00106   -0.00681   -0.00643
MOLE    3
C20   1    0.738732    0.671925    0.777290    11.00000    0.03115    0.07457 =
         0.04240    0.01340    0.00752    0.00561
O4    4    0.755990    0.838123    0.764482    11.00000    0.03431    0.06213 =
         0.05998   -0.03057    0.01042   -0.01849
O5    4    0.635494    0.766094    0.715167    11.00000    0.03653    0.04096 =
         0.05541   -0.00335   -0.01586   -0.00179
O6    4    0.789258    0.743582    0.683386    11.00000    0.05664    0.04117 =
         0.03398   -0.00402    0.01057   -0.00607
F4    5    0.713137    0.597996    0.751383    11.00000    0.09649    0.04572 =
         0.09729    0.02208    0.01956    0.00636
F5    5    0.821345    0.661799    0.795240    11.00000    0.03745    0.17017 =
         0.06597    0.05023    0.00300    0.03246
F6    5    0.687015    0.683036    0.823621    11.00000    0.04840    0.11072 =
         0.05087    0.02877    0.02121    0.01155
S2    6    0.729897    0.765444    0.729479    11.00000    0.02827    0.03800 =
         0.03225   -0.00466    0.00041   -0.00573
HKLF    4
 
REM  NATH2C in Pbca at 170 K
REM R1 =  0.0394 for   4350 Fo > 4sig(Fo)  and  0.0499 for all   5343 data
REM    367 parameters refined using      3 restraints
 
END
 
WGHT      0.0739      0.2018
REM Highest difference peak  1.035,  deepest hole -0.440,  1-sigma level  0.077
Q1    1   0.4774  0.2976  0.9898  11.00000  0.05    0.62
Q2    1   0.7651  0.7697  0.7701  11.00000  0.05    0.43
Q3    1   0.6935  0.6232  0.8199  11.00000  0.05    0.41
Q4    1   0.5401  0.3798  0.9997  11.00000  0.05    0.41
Q5    1   0.4608  0.3878  1.0047  11.00000  0.05    0.38
Q6    1   0.4946  0.4477  0.9897  11.00000  0.05    0.37
Q7    1   0.7600  0.8419  0.7328  11.00000  0.05    0.36
Q8    1   0.5787  0.2831  0.9286  11.00000  0.05    0.36
Q9    1   0.6014  0.2604  1.0418  11.00000  0.05    0.33
Q10   1   0.4923 -0.0277  0.8302  11.00000  0.05    0.31
Q11   1   0.7609  0.6188  0.7620  11.00000  0.05    0.31
Q12   1   0.6800  0.6914  0.8354  11.00000  0.05    0.30
Q13   1   0.4261  0.2559  1.0587  11.00000  0.05    0.29
Q14   1   0.5333  0.1924  0.8419  11.00000  0.05    0.29
Q15   1   0.4705 -0.0625  0.7496  11.00000  0.05    0.29
Q16   1   0.4822  0.0022  0.7320  11.00000  0.05    0.28
Q17   1   0.4835  0.0584  0.7820  11.00000  0.05    0.28
Q18   1   0.8210  0.6410  0.7926  11.00000  0.05    0.27
Q19   1   0.2724  0.2376  1.0536  11.00000  0.05    0.27
Q20   1   0.6370  0.7417  0.6996  11.00000  0.05    0.26
Q21   1   0.3204  0.2517  0.9817  11.00000  0.05    0.26
Q22   1   0.5011  0.0576  0.9205  11.00000  0.05    0.26
Q23   1   0.4972  0.1345  0.8351  11.00000  0.05    0.26
Q24   1   0.4456 -0.1049  0.8870  11.00000  0.05    0.26
Q25   1   0.5044  0.0466  0.5804  11.00000  0.05    0.25

;


# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
#----------------------------------------------------------------------------#
#                   END OF CIF                                               #
#----------------------------------------------------------------------------#

_database_code_depnum_ccdc_archive 'CCDC 946244'
