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

####################################################################### 
# 
# 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/. 
# 
# 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_c:\docume~1\chp3wa~1\mydocu~1\brockp~2\jw07bjc
_database_code_depnum_ccdc_archive 'CCDC 972052'
_audit_update_record             
;
2013-11-14 deposited with the CCDC.
2014-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
6-(2'-Pyridyl)-6,7-dihydro-5H-dipyrido[3,2-d:2',3'-f][1,3]diazepine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 N5'
_chemical_formula_weight         275.31

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8020(15)
_cell_length_b                   11.0335(17)
_cell_length_c                   12.7221(15)
_cell_angle_alpha                87.172(7)
_cell_angle_beta                 84.520(7)
_cell_angle_gamma                85.678(7)
_cell_volume                     1364.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1673
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      23.51

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.650
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   Bruker-SADABS

_exptl_special_details           
; 
 ? 
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14185
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_sigmaI/netI    0.1058
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         28.37
_reflns_number_total             6646
_reflns_number_gt                3569
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_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)+(0.0412P)²+0.3307P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6648
_refine_ls_number_parameters     483
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1280
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1338
_refine_ls_wR_factor_gt          0.1008
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_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
N1 N 0.1984(2) 0.16757(19) 0.22120(14) 0.0284(5) Uani 1 1 d . . .
N2 N 0.3528(2) 0.3411(2) 0.14715(14) 0.0311(5) Uani 1 1 d . . .
N3 N 0.3503(2) 0.18944(18) 0.47542(15) 0.0256(5) Uani 1 1 d . . .
N4 N 0.3501(2) 0.40531(19) 0.42832(14) 0.0256(5) Uani 1 1 d . . .
N5 N 0.6453(2) 0.37737(19) 0.43558(15) 0.0296(5) Uani 1 1 d . . .
N21 N 0.3707(2) 0.15337(18) 0.70509(14) 0.0296(5) Uani 1 1 d . . .
N22 N 0.1156(2) 0.22032(19) 0.65414(14) 0.0295(5) Uani 1 1 d . . .
N23 N 0.2203(2) 0.21104(19) 0.97791(15) 0.0291(5) Uani 1 1 d . . .
N24 N 0.1307(2) 0.39571(19) 0.88985(14) 0.0268(5) Uani 1 1 d . . .
N25 N -0.1158(2) 0.34982(18) 1.05724(15) 0.0299(5) Uani 1 1 d . . .
C1 C 0.1248(3) 0.0732(2) 0.24688(19) 0.0318(6) Uani 1 1 d . . .
C2 C 0.1148(3) 0.0187(2) 0.3477(2) 0.0331(6) Uani 1 1 d . . .
C3 C 0.1885(3) 0.0620(2) 0.42170(19) 0.0296(6) Uani 1 1 d . . .
C4 C 0.2721(2) 0.1600(2) 0.39736(17) 0.0237(5) Uani 1 1 d . . .
C5 C 0.2707(2) 0.2144(2) 0.29395(16) 0.0230(5) Uani 1 1 d . . .
C6 C 0.3368(2) 0.3273(2) 0.25376(17) 0.0244(5) Uani 1 1 d . . .
C7 C 0.3666(2) 0.4201(2) 0.31817(17) 0.0246(5) Uani 1 1 d . . .
C8 C 0.4061(3) 0.5300(2) 0.2696(2) 0.0332(6) Uani 1 1 d . . .
C9 C 0.4138(3) 0.5460(3) 0.1612(2) 0.0406(7) Uani 1 1 d . . .
C10 C 0.3889(3) 0.4479(3) 0.1035(2) 0.0389(7) Uani 1 1 d . . .
C11 C 0.4231(2) 0.2974(2) 0.47550(17) 0.0246(5) Uani 1 1 d . . .
C12 C 0.5721(2) 0.2808(2) 0.42759(16) 0.0241(5) Uani 1 1 d . . .
C13 C 0.6278(3) 0.1758(2) 0.38066(19) 0.0321(6) Uani 1 1 d . . .
C14 C 0.7635(3) 0.1702(3) 0.3387(2) 0.0368(7) Uani 1 1 d . . .
C15 C 0.8393(3) 0.2694(3) 0.3455(2) 0.0367(7) Uani 1 1 d . . .
C16 C 0.7766(3) 0.3703(3) 0.39441(19) 0.0353(6) Uani 1 1 d . . .
C21 C 0.4916(3) 0.0996(2) 0.7266(2) 0.0343(6) Uani 1 1 d . . .
C22 C 0.5283(3) 0.0823(3) 0.8290(2) 0.0361(7) Uani 1 1 d . . .
C23 C 0.4369(3) 0.1229(2) 0.9102(2) 0.0332(6) Uani 1 1 d . . .
C24 C 0.3089(2) 0.1814(2) 0.89096(17) 0.0237(5) Uani 1 1 d . . .
C25 C 0.2794(2) 0.1947(2) 0.78367(16) 0.0228(5) Uani 1 1 d . . .
C26 C 0.1524(2) 0.2577(2) 0.74552(16) 0.0230(5) Uani 1 1 d . . .
C27 C 0.0852(2) 0.3588(2) 0.79557(17) 0.0250(5) Uani 1 1 d . . .
C28 C -0.0192(3) 0.4250(2) 0.74593(19) 0.0323(6) Uani 1 1 d . . .
C29 C -0.0523(3) 0.3892(3) 0.6494(2) 0.0377(7) Uani 1 1 d . . .
C30 C 0.0154(3) 0.2864(3) 0.60772(19) 0.0343(6) Uani 1 1 d . . .
C31 C 0.1167(3) 0.3122(2) 0.98232(18) 0.0273(6) Uani 1 1 d . . .
C32 C -0.0262(3) 0.2693(2) 1.00701(17) 0.0258(5) Uani 1 1 d . . .
C33 C -0.0640(3) 0.1564(2) 0.9811(2) 0.0338(6) Uani 1 1 d . . .
C34 C -0.1961(3) 0.1247(3) 1.0108(2) 0.0410(7) Uani 1 1 d . . .
C35 C -0.2877(3) 0.2061(3) 1.0653(2) 0.0398(7) Uani 1 1 d . . .
C36 C -0.2439(3) 0.3179(3) 1.0854(2) 0.0355(6) Uani 1 1 d . . .
H1 H 0.075(2) 0.034(2) 0.1886(18) 0.031(6) Uiso 1 1 d . . .
H2 H 0.058(3) -0.045(2) 0.3641(18) 0.034(7) Uiso 1 1 d . . .
H3 H 0.185(2) 0.024(2) 0.4953(17) 0.026(6) Uiso 1 1 d . . .
H3A H 0.318(3) 0.160(2) 0.541(2) 0.038(7) Uiso 1 1 d . . .
H4A H 0.369(3) 0.472(3) 0.462(2) 0.046(8) Uiso 1 1 d . . .
H8 H 0.424(2) 0.598(2) 0.3146(18) 0.036(7) Uiso 1 1 d . . .
H9 H 0.443(3) 0.626(3) 0.1269(19) 0.045(8) Uiso 1 1 d . . .
H10 H 0.392(3) 0.451(2) 0.024(2) 0.047(8) Uiso 1 1 d . . .
H11 H 0.424(2) 0.310(2) 0.5539(17) 0.025(6) Uiso 1 1 d . . .
H13 H 0.572(2) 0.105(2) 0.3809(17) 0.030(7) Uiso 1 1 d . . .
H14 H 0.804(2) 0.097(2) 0.3034(18) 0.036(7) Uiso 1 1 d . . .
H15 H 0.931(3) 0.267(2) 0.3164(19) 0.043(8) Uiso 1 1 d . . .
H16 H 0.825(3) 0.440(2) 0.4032(19) 0.039(8) Uiso 1 1 d . . .
H21 H 0.567(3) 0.076(2) 0.6623(19) 0.040(7) Uiso 1 1 d . . .
H22 H 0.616(3) 0.044(2) 0.8404(18) 0.038(7) Uiso 1 1 d . . .
H23 H 0.456(2) 0.111(2) 0.981(2) 0.036(7) Uiso 1 1 d . . .
H23A H 0.259(3) 0.203(3) 1.036(2) 0.050(9) Uiso 1 1 d . . .
H24A H 0.098(3) 0.477(3) 0.908(2) 0.052(9) Uiso 1 1 d . . .
H28 H -0.064(2) 0.500(2) 0.7792(17) 0.031(7) Uiso 1 1 d . . .
H29 H -0.116(3) 0.435(2) 0.6129(19) 0.042(8) Uiso 1 1 d . . .
H30 H -0.007(3) 0.249(3) 0.541(2) 0.054(8) Uiso 1 1 d . . .
H31 H 0.134(2) 0.360(2) 1.0444(16) 0.020(6) Uiso 1 1 d . . .
H33 H 0.005(3) 0.098(2) 0.9418(19) 0.039(7) Uiso 1 1 d . . .
H34 H -0.224(3) 0.041(2) 0.9933(19) 0.042(7) Uiso 1 1 d . . .
H35 H -0.379(3) 0.183(2) 1.0936(19) 0.048(8) Uiso 1 1 d . . .
H36 H -0.302(3) 0.376(2) 1.1264(18) 0.033(7) Uiso 1 1 d . . .


_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
N1 C1 1.322(3) . ?
N1 C5 1.361(3) . ?
N2 C10 1.335(3) . ?
N2 C6 1.353(3) . ?
N3 C4 1.376(3) . ?
N3 C11 1.433(3) . ?
N3 H3A 0.92(2) . ?
N4 C7 1.398(3) . ?
N4 C11 1.474(3) . ?
N4 H4A 0.92(3) . ?
N5 C16 1.340(3) . ?
N5 C12 1.341(3) . ?
N21 C21 1.331(3) . ?
N21 C25 1.349(3) . ?
N22 C26 1.342(3) . ?
N22 C30 1.344(3) . ?
N23 C24 1.376(3) . ?
N23 C31 1.451(3) . ?
N23 H23A 0.86(3) . ?
N24 C27 1.408(3) . ?
N24 C31 1.460(3) . ?
N24 H24A 0.96(3) . ?
N25 C36 1.341(3) . ?
N25 C32 1.342(3) . ?
C1 C2 1.387(3) . ?
C1 H1 1.05(2) . ?
C2 C3 1.365(3) . ?
C2 H2 0.93(3) . ?
C3 C4 1.411(3) . ?
C3 H3 1.00(2) . ?
C4 C5 1.419(3) . ?
C5 C6 1.493(3) . ?
C6 C7 1.407(3) . ?
C7 C8 1.398(3) . ?
C8 C9 1.377(3) . ?
C8 H8 1.00(2) . ?
C9 C10 1.387(4) . ?
C9 H9 1.02(3) . ?
C10 H10 1.01(3) . ?
C11 C12 1.530(3) . ?
C11 H11 1.01(2) . ?
C12 C13 1.381(3) . ?
C13 C14 1.383(4) . ?
C13 H13 0.99(2) . ?
C14 C15 1.379(4) . ?
C14 H14 0.98(3) . ?
C15 C16 1.377(4) . ?
C15 H15 0.93(3) . ?
C16 H16 0.95(3) . ?
C21 C22 1.385(3) . ?
C21 H21 1.08(2) . ?
C22 C23 1.370(3) . ?
C22 H22 0.95(3) . ?
C23 C24 1.404(3) . ?
C23 H23 0.94(2) . ?
C24 C25 1.420(3) . ?
C25 C26 1.490(3) . ?
C26 C27 1.401(3) . ?
C27 C28 1.395(3) . ?
C28 C29 1.383(4) . ?
C28 H28 1.00(2) . ?
C29 C30 1.374(4) . ?
C29 H29 0.92(3) . ?
C30 H30 1.01(3) . ?
C31 C32 1.513(3) . ?
C31 H31 1.01(2) . ?
C32 C33 1.390(3) . ?
C33 C34 1.379(4) . ?
C33 H33 1.01(3) . ?
C34 C35 1.385(4) . ?
C34 H34 1.02(3) . ?
C35 C36 1.379(4) . ?
C35 H35 0.98(3) . ?
C36 H36 0.97(2) . ?

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
C1 N1 C5 120.4(2) . . ?
C10 N2 C6 118.8(2) . . ?
C4 N3 C11 125.52(19) . . ?
C4 N3 H3A 112.4(16) . . ?
C11 N3 H3A 114.8(16) . . ?
C7 N4 C11 116.67(19) . . ?
C7 N4 H4A 113.5(17) . . ?
C11 N4 H4A 108.6(17) . . ?
C16 N5 C12 117.6(2) . . ?
C21 N21 C25 120.5(2) . . ?
C26 N22 C30 118.2(2) . . ?
C24 N23 C31 125.5(2) . . ?
C24 N23 H23A 112.9(19) . . ?
C31 N23 H23A 110.2(19) . . ?
C27 N24 C31 117.3(2) . . ?
C27 N24 H24A 114.0(17) . . ?
C31 N24 H24A 110.5(16) . . ?
C36 N25 C32 118.4(2) . . ?
N1 C1 C2 122.6(2) . . ?
N1 C1 H1 119.8(13) . . ?
C2 C1 H1 117.6(13) . . ?
C3 C2 C1 118.2(2) . . ?
C3 C2 H2 121.4(15) . . ?
C1 C2 H2 120.4(15) . . ?
C2 C3 C4 121.3(2) . . ?
C2 C3 H3 120.5(13) . . ?
C4 C3 H3 118.2(13) . . ?
N3 C4 C3 116.2(2) . . ?
N3 C4 C5 127.1(2) . . ?
C3 C4 C5 116.7(2) . . ?
N1 C5 C4 120.6(2) . . ?
N1 C5 C6 112.81(19) . . ?
C4 C5 C6 126.5(2) . . ?
N2 C6 C7 121.1(2) . . ?
N2 C6 C5 114.2(2) . . ?
C7 C6 C5 124.31(19) . . ?
C8 C7 N4 120.6(2) . . ?
C8 C7 C6 118.4(2) . . ?
N4 C7 C6 120.9(2) . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 120.5(14) . . ?
C7 C8 H8 119.3(14) . . ?
C8 C9 C10 117.7(3) . . ?
C8 C9 H9 119.2(14) . . ?
C10 C9 H9 123.0(14) . . ?
N2 C10 C9 123.8(2) . . ?
N2 C10 H10 112.9(15) . . ?
C9 C10 H10 123.3(15) . . ?
N3 C11 N4 113.18(19) . . ?
N3 C11 C12 113.3(2) . . ?
N4 C11 C12 111.53(18) . . ?
N3 C11 H11 102.3(12) . . ?
N4 C11 H11 107.7(12) . . ?
C12 C11 H11 108.2(12) . . ?
N5 C12 C13 122.5(2) . . ?
N5 C12 C11 114.1(2) . . ?
C13 C12 C11 123.4(2) . . ?
C12 C13 C14 119.0(3) . . ?
C12 C13 H13 119.5(14) . . ?
C14 C13 H13 121.4(14) . . ?
C15 C14 C13 119.0(3) . . ?
C15 C14 H14 121.1(15) . . ?
C13 C14 H14 119.9(15) . . ?
C16 C15 C14 118.5(3) . . ?
C16 C15 H15 122.1(17) . . ?
C14 C15 H15 119.4(17) . . ?
N5 C16 C15 123.4(3) . . ?
N5 C16 H16 114.9(16) . . ?
C15 C16 H16 121.7(16) . . ?
N21 C21 C22 122.0(2) . . ?
N21 C21 H21 119.2(13) . . ?
C22 C21 H21 118.5(13) . . ?
C23 C22 C21 118.5(3) . . ?
C23 C22 H22 122.5(14) . . ?
C21 C22 H22 119.0(14) . . ?
C22 C23 C24 121.3(2) . . ?
C22 C23 H23 121.8(15) . . ?
C24 C23 H23 116.9(15) . . ?
N23 C24 C23 117.0(2) . . ?
N23 C24 C25 126.4(2) . . ?
C23 C24 C25 116.4(2) . . ?
N21 C25 C24 121.2(2) . . ?
N21 C25 C26 113.52(19) . . ?
C24 C25 C26 125.2(2) . . ?
N22 C26 C27 122.0(2) . . ?
N22 C26 C25 115.8(2) . . ?
C27 C26 C25 121.7(2) . . ?
C28 C27 C26 118.4(2) . . ?
C28 C27 N24 121.9(2) . . ?
C26 C27 N24 119.5(2) . . ?
C29 C28 C27 119.1(2) . . ?
C29 C28 H28 122.0(13) . . ?
C27 C28 H28 118.7(13) . . ?
C30 C29 C28 118.6(3) . . ?
C30 C29 H29 120.8(17) . . ?
C28 C29 H29 120.6(17) . . ?
N22 C30 C29 123.5(2) . . ?
N22 C30 H30 111.8(16) . . ?
C29 C30 H30 124.6(16) . . ?
N23 C31 N24 112.67(19) . . ?
N23 C31 C32 111.6(2) . . ?
N24 C31 C32 114.0(2) . . ?
N23 C31 H31 106.0(12) . . ?
N24 C31 H31 106.0(12) . . ?
C32 C31 H31 105.8(12) . . ?
N25 C32 C33 121.8(2) . . ?
N25 C32 C31 114.3(2) . . ?
C33 C32 C31 123.9(2) . . ?
C34 C33 C32 119.1(3) . . ?
C34 C33 H33 120.7(15) . . ?
C32 C33 H33 120.2(15) . . ?
C33 C34 C35 119.2(3) . . ?
C33 C34 H34 119.7(14) . . ?
C35 C34 H34 121.0(14) . . ?
C36 C35 C34 118.3(3) . . ?
C36 C35 H35 120.7(16) . . ?
C34 C35 H35 120.9(16) . . ?
N25 C36 C35 123.0(3) . . ?
N25 C36 H36 115.1(15) . . ?
C35 C36 H36 121.7(15) . . ?

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
C5 N1 C1 C2 1.3(4) . . . . ?
N1 C1 C2 C3 -2.7(4) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C11 N3 C4 C3 -168.3(2) . . . . ?
C11 N3 C4 C5 14.4(4) . . . . ?
C2 C3 C4 N3 -174.9(2) . . . . ?
C2 C3 C4 C5 2.7(4) . . . . ?
C1 N1 C5 C4 2.2(3) . . . . ?
C1 N1 C5 C6 -174.7(2) . . . . ?
N3 C4 C5 N1 173.2(2) . . . . ?
C3 C4 C5 N1 -4.1(3) . . . . ?
N3 C4 C5 C6 -10.3(4) . . . . ?
C3 C4 C5 C6 172.4(2) . . . . ?
C10 N2 C6 C7 -4.4(3) . . . . ?
C10 N2 C6 C5 168.7(2) . . . . ?
N1 C5 C6 N2 -20.5(3) . . . . ?
C4 C5 C6 N2 162.7(2) . . . . ?
N1 C5 C6 C7 152.3(2) . . . . ?
C4 C5 C6 C7 -24.5(4) . . . . ?
C11 N4 C7 C8 -128.4(2) . . . . ?
C11 N4 C7 C6 55.0(3) . . . . ?
N2 C6 C7 C8 3.4(3) . . . . ?
C5 C6 C7 C8 -168.9(2) . . . . ?
N2 C6 C7 N4 -179.9(2) . . . . ?
C5 C6 C7 N4 7.8(3) . . . . ?
N4 C7 C8 C9 -176.0(2) . . . . ?
C6 C7 C8 C9 0.7(4) . . . . ?
C7 C8 C9 C10 -3.6(4) . . . . ?
C6 N2 C10 C9 1.3(4) . . . . ?
C8 C9 C10 N2 2.7(4) . . . . ?
C4 N3 C11 N4 35.6(3) . . . . ?
C4 N3 C11 C12 -92.6(3) . . . . ?
C7 N4 C11 N3 -83.0(2) . . . . ?
C7 N4 C11 C12 46.2(3) . . . . ?
C16 N5 C12 C13 1.1(3) . . . . ?
C16 N5 C12 C11 -179.3(2) . . . . ?
N3 C11 C12 N5 -174.31(18) . . . . ?
N4 C11 C12 N5 56.6(3) . . . . ?
N3 C11 C12 C13 5.3(3) . . . . ?
N4 C11 C12 C13 -123.8(2) . . . . ?
N5 C12 C13 C14 -1.0(4) . . . . ?
C11 C12 C13 C14 179.4(2) . . . . ?
C12 C13 C14 C15 0.3(4) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C12 N5 C16 C15 -0.4(4) . . . . ?
C14 C15 C16 N5 -0.3(4) . . . . ?
C25 N21 C21 C22 0.8(4) . . . . ?
N21 C21 C22 C23 -0.4(4) . . . . ?
C21 C22 C23 C24 -0.4(4) . . . . ?
C31 N23 C24 C23 151.2(2) . . . . ?
C31 N23 C24 C25 -34.6(4) . . . . ?
C22 C23 C24 N23 175.5(2) . . . . ?
C22 C23 C24 C25 0.7(4) . . . . ?
C21 N21 C25 C24 -0.4(4) . . . . ?
C21 N21 C25 C26 177.2(2) . . . . ?
N23 C24 C25 N21 -174.6(2) . . . . ?
C23 C24 C25 N21 -0.3(3) . . . . ?
N23 C24 C25 C26 8.1(4) . . . . ?
C23 C24 C25 C26 -177.6(2) . . . . ?
C30 N22 C26 C27 3.2(3) . . . . ?
C30 N22 C26 C25 -169.6(2) . . . . ?
N21 C25 C26 N22 28.9(3) . . . . ?
C24 C25 C26 N22 -153.6(2) . . . . ?
N21 C25 C26 C27 -144.0(2) . . . . ?
C24 C25 C26 C27 33.5(4) . . . . ?
N22 C26 C27 C28 -2.8(3) . . . . ?
C25 C26 C27 C28 169.7(2) . . . . ?
N22 C26 C27 N24 -178.3(2) . . . . ?
C25 C26 C27 N24 -5.8(3) . . . . ?
C31 N24 C27 C28 119.4(3) . . . . ?
C31 N24 C27 C26 -65.3(3) . . . . ?
C26 C27 C28 C29 -0.3(4) . . . . ?
N24 C27 C28 C29 175.1(2) . . . . ?
C27 C28 C29 C30 2.6(4) . . . . ?
C26 N22 C30 C29 -0.7(4) . . . . ?
C28 C29 C30 N22 -2.2(4) . . . . ?
C24 N23 C31 N24 -10.6(3) . . . . ?
C24 N23 C31 C32 119.1(2) . . . . ?
C27 N24 C31 N23 76.5(3) . . . . ?
C27 N24 C31 C32 -51.9(3) . . . . ?
C36 N25 C32 C33 1.9(3) . . . . ?
C36 N25 C32 C31 -177.9(2) . . . . ?
N23 C31 C32 N25 151.8(2) . . . . ?
N24 C31 C32 N25 -79.2(3) . . . . ?
N23 C31 C32 C33 -28.0(3) . . . . ?
N24 C31 C32 C33 101.0(3) . . . . ?
N25 C32 C33 C34 -2.1(4) . . . . ?
C31 C32 C33 C34 177.7(2) . . . . ?
C32 C33 C34 C35 0.1(4) . . . . ?
C33 C34 C35 C36 1.8(4) . . . . ?
C32 N25 C36 C35 0.2(4) . . . . ?
C34 C35 C36 N25 -2.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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/. 
# 
# 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_roge25
_database_code_depnum_ccdc_archive 'CCDC 972053'
_audit_update_record             
;
2013-11-14 deposited with the CCDC.
2014-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
E,E-N3,N3'-Bis(2-pyridylmethylene)-(2,2'-bipyridine)-3,3'-diamine 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H16 N6'
_chemical_formula_weight         364.41

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   10.9614(6)
_cell_length_b                   20.1743(11)
_cell_length_c                   8.7356(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.490(3)
_cell_angle_gamma                90.00
_cell_volume                     1893.06(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    7161
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      26.82

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9399
_exptl_absorpt_correction_T_max  0.9960
_exptl_absorpt_process_details   Bruker-SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29931
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.77
_diffrn_reflns_theta_max         28.55
_reflns_number_total             4286
_reflns_number_gt                3043
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_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)+(0.0307P)²+1.0044P] 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         4286
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.0994
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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
N1 N 1.06593(12) 0.13997(7) 0.79286(18) 0.0275(3) Uani 1 1 d . . .
N2 N 0.99479(12) 0.12317(7) 0.44700(17) 0.0274(3) Uani 1 1 d . . .
N3 N 0.73880(12) 0.18151(7) 0.63579(17) 0.0270(3) Uani 1 1 d . . .
N4 N 0.79719(12) 0.02659(7) 0.65840(17) 0.0256(3) Uani 1 1 d . . .
N5 N 0.51098(13) -0.03990(8) 0.71968(19) 0.0356(4) Uani 1 1 d . . .
N6 N 0.42067(13) 0.15530(8) 0.6494(2) 0.0370(4) Uani 1 1 d . . .
C1 C 1.08460(16) 0.17445(9) 0.9264(2) 0.0316(4) Uani 1 1 d . . .
H1 H 1.1640 0.1741 0.9888 0.038 Uiso 1 1 calc R . .
C2 C 0.99349(17) 0.21049(9) 0.9771(2) 0.0340(4) Uani 1 1 d . . .
H2 H 1.0110 0.2331 1.0718 0.041 Uiso 1 1 calc R . .
C3 C 0.87574(16) 0.21246(9) 0.8848(2) 0.0314(4) Uani 1 1 d . . .
H3 H 0.8126 0.2367 0.9156 0.038 Uiso 1 1 calc R . .
C4 C 0.85334(15) 0.17764(8) 0.7453(2) 0.0244(4) Uani 1 1 d . . .
C5 C 0.95118(14) 0.14149(8) 0.7032(2) 0.0227(4) Uani 1 1 d . . .
C6 C 0.93098(14) 0.10314(8) 0.5545(2) 0.0230(4) Uani 1 1 d . . .
C7 C 0.84868(14) 0.04914(9) 0.5316(2) 0.0241(4) Uani 1 1 d . . .
C8 C 0.83280(16) 0.01547(9) 0.3900(2) 0.0309(4) Uani 1 1 d . . .
H8 H 0.7793 -0.0207 0.3707 0.037 Uiso 1 1 calc R . .
C9 C 0.89763(16) 0.03646(10) 0.2787(2) 0.0333(4) Uani 1 1 d . . .
H9 H 0.8879 0.0150 0.1828 0.040 Uiso 1 1 calc R . .
C10 C 0.97711(16) 0.08975(10) 0.3122(2) 0.0312(4) Uani 1 1 d . . .
H10 H 1.0209 0.1032 0.2368 0.037 Uiso 1 1 calc R . .
C11 C 0.63932(15) 0.16876(9) 0.6837(2) 0.0291(4) Uani 1 1 d . . .
H11 H 0.6450 0.1554 0.7868 0.035 Uiso 1 1 calc R . .
C12 C 0.51501(15) 0.17431(9) 0.5818(2) 0.0303(4) Uani 1 1 d . . .
C13 C 0.49848(17) 0.19722(11) 0.4303(3) 0.0435(5) Uani 1 1 d . . .
H13 H 0.5666 0.2097 0.3883 0.052 Uiso 1 1 calc R . .
C14 C 0.37894(19) 0.20130(12) 0.3416(3) 0.0518(6) Uani 1 1 d . . .
H14 H 0.3651 0.2161 0.2387 0.062 Uiso 1 1 calc R . .
C15 C 0.28095(17) 0.18280(10) 0.4100(3) 0.0422(5) Uani 1 1 d . . .
H15 H 0.1994 0.1855 0.3544 0.051 Uiso 1 1 calc R . .
C16 C 0.30564(17) 0.16035(10) 0.5614(3) 0.0405(5) Uani 1 1 d . . .
H16 H 0.2387 0.1479 0.6057 0.049 Uiso 1 1 calc R . .
C17 C 0.68520(15) 0.00581(9) 0.6322(2) 0.0267(4) Uani 1 1 d . . .
H17 H 0.6360 0.0103 0.5329 0.032 Uiso 1 1 calc R . .
C18 C 0.63293(15) -0.02521(9) 0.7574(2) 0.0269(4) Uani 1 1 d . . .
C19 C 0.70666(16) -0.04053(9) 0.9014(2) 0.0310(4) Uani 1 1 d . . .
H19 H 0.7907 -0.0294 0.9234 0.037 Uiso 1 1 calc R . .
C20 C 0.65370(18) -0.07252(10) 1.0115(2) 0.0363(5) Uani 1 1 d . . .
H20 H 0.7011 -0.0832 1.1090 0.044 Uiso 1 1 calc R . .
C21 C 0.52906(18) -0.08839(11) 0.9740(3) 0.0419(5) Uani 1 1 d . . .
H21 H 0.4908 -0.1104 1.0453 0.050 Uiso 1 1 calc R . .
C22 C 0.46240(17) -0.07101(11) 0.8291(3) 0.0445(6) Uani 1 1 d . . .
H22 H 0.3781 -0.0815 0.8055 0.053 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
N1 C1 1.339(2) . ?
N1 C5 1.343(2) . ?
N2 C10 1.337(2) . ?
N2 C6 1.340(2) . ?
N3 C11 1.270(2) . ?
N3 C4 1.421(2) . ?
N4 C17 1.274(2) . ?
N4 C7 1.415(2) . ?
N5 C22 1.339(2) . ?
N5 C18 1.345(2) . ?
N6 C16 1.343(2) . ?
N6 C12 1.345(2) . ?
C1 C2 1.378(3) . ?
C2 C3 1.380(3) . ?
C3 C4 1.386(3) . ?
C4 C5 1.405(2) . ?
C5 C6 1.490(2) . ?
C6 C7 1.403(2) . ?
C7 C8 1.391(3) . ?
C8 C9 1.380(3) . ?
C9 C10 1.378(3) . ?
C11 C12 1.476(2) . ?
C12 C13 1.379(3) . ?
C13 C14 1.386(3) . ?
C14 C15 1.381(3) . ?
C15 C16 1.373(3) . ?
C17 C18 1.472(2) . ?
C18 C19 1.388(3) . ?
C19 C20 1.379(3) . ?
C20 C21 1.378(3) . ?
C21 C22 1.375(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
C1 N1 C5 117.34(15) . . ?
C10 N2 C6 117.43(15) . . ?
C11 N3 C4 117.94(15) . . ?
C17 N4 C7 119.03(15) . . ?
C22 N5 C18 116.46(17) . . ?
C16 N6 C12 116.32(18) . . ?
N1 C1 C2 124.02(16) . . ?
C1 C2 C3 118.75(18) . . ?
C2 C3 C4 118.74(16) . . ?
C3 C4 C5 118.85(15) . . ?
C3 C4 N3 122.83(15) . . ?
C5 C4 N3 118.08(15) . . ?
N1 C5 C4 122.29(16) . . ?
N1 C5 C6 117.12(14) . . ?
C4 C5 C6 120.59(14) . . ?
N2 C6 C7 122.99(16) . . ?
N2 C6 C5 116.53(14) . . ?
C7 C6 C5 120.48(15) . . ?
C8 C7 C6 117.97(16) . . ?
C8 C7 N4 122.71(15) . . ?
C6 C7 N4 118.89(16) . . ?
C9 C8 C7 119.06(17) . . ?
C10 C9 C8 118.82(18) . . ?
N2 C10 C9 123.72(17) . . ?
N3 C11 C12 122.39(17) . . ?
N6 C12 C13 123.45(17) . . ?
N6 C12 C11 114.31(17) . . ?
C13 C12 C11 122.24(16) . . ?
C12 C13 C14 119.05(19) . . ?
C15 C14 C13 118.2(2) . . ?
C16 C15 C14 119.02(18) . . ?
N6 C16 C15 123.96(18) . . ?
N4 C17 C18 120.67(16) . . ?
N5 C18 C19 122.96(16) . . ?
N5 C18 C17 115.25(16) . . ?
C19 C18 C17 121.73(15) . . ?
C20 C19 C18 119.11(17) . . ?
C21 C20 C19 118.57(19) . . ?
C22 C21 C20 118.66(18) . . ?
N5 C22 C21 124.23(18) . . ?

_diffrn_measured_fraction_theta_max 0.891
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.042


####################################################################### 
# 
# 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/. 
# 
# 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_mel-7bd
_database_code_depnum_ccdc_archive 'CCDC 972054'
_audit_update_record             
;
2013-11-14 deposited with the CCDC.
2014-12-09 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
[6-(2'-Pyridyl)-6,7-dihydro-5H-dipyrido[3,2-d:2',3'-f][1,3]diazepine]
copper(II)(hfac)(triflate) 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H14 Cu F9 N5 O4'
_chemical_formula_sum            'C23 H14 Cu F9 N5 O4'
_chemical_formula_weight         658.93

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   8.2407(9)
_cell_length_b                   10.3017(11)
_cell_length_c                   15.4495(16)
_cell_angle_alpha                103.709(12)
_cell_angle_beta                 98.082(12)
_cell_angle_gamma                101.143(13)
_cell_volume                     1226.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7527
_cell_measurement_theta_min      2.00
_cell_measurement_theta_max      25.85

_exptl_crystal_description       plate
_exptl_crystal_colour            green-blue
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.785
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             658
_exptl_absorpt_coefficient_mu    1.002
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7296
_exptl_absorpt_correction_T_max  0.8287
_exptl_absorpt_process_details   'MULscanABS in PLATON (Spek, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       'phi rotation'
_diffrn_detector_area_resol_mean 0.81\%A
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9628
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0616
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         25.91
_reflns_number_total             4451
_reflns_number_gt                3236
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'EXPOSE (Stoe IPDS Software, 2000)'
_computing_cell_refinement       'CELL (Stoe IPDS Software, 2000)'
_computing_data_reduction        'INTEGRATE (Stoe IPDS Software, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL-97

_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)+(0.0734P)²+0.1019P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4451
_refine_ls_number_parameters     396
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1305
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
Cu1 Cu Uani 0.78614(5) 0.17806(4) 0.31654(3) 1.000 0.0260(2) . .
F1 F Uani 0.9278(4) -0.2395(2) 0.16345(18) 1.000 0.0525(9) . .
F2 F Uani 0.6731(4) -0.2848(3) 0.0962(3) 1.000 0.0815(13) . .
F3 F Uani 0.8703(5) -0.2101(3) 0.03264(19) 1.000 0.0761(13) . .
F4 F Uani 0.7184(6) 0.1715(3) -0.02813(19) 1.000 0.0907(16) . .
F5 F Uani 0.5973(5) 0.2924(4) 0.0601(2) 1.000 0.0907(16) . .
F6 F Uani 0.8590(5) 0.3507(4) 0.0711(3) 1.000 0.0954(16) . .
F11 F Uani 0.3241(5) 0.1412(4) 0.1370(2) 0.800 0.0653(14) . .
F12 F Uani 0.1735(5) 0.2132(4) 0.2281(3) 0.800 0.0753(16) . .
F13 F Uani 0.1991(4) 0.0027(3) 0.2032(3) 0.800 0.0475(13) . .
O1 O Uani 0.8240(3) -0.0203(2) 0.23974(17) 1.000 0.0303(8) . .
O2 O Uani 0.7659(3) 0.2360(3) 0.20557(18) 1.000 0.0331(8) . .
O3 O Uani 0.5360(3) 0.0948(3) 0.2806(2) 1.000 0.0362(9) . .
O4 O Uani 0.4644(5) 0.2872(3) 0.3476(2) 1.000 0.0607(11) . .
N1 N Uani 0.8263(4) 0.1411(3) 0.4351(2) 1.000 0.0254(9) . .
N2 N Uani 0.9886(4) 0.3292(3) 0.3766(2) 1.000 0.0243(9) . .
N3 N Uani 1.1535(4) 0.2571(3) 0.6435(2) 1.000 0.0357(11) . .
N4 N Uani 1.2947(4) 0.4415(3) 0.5926(2) 1.000 0.0333(11) . .
N5 N Uani 1.5296(4) 0.2512(3) 0.7016(2) 1.000 0.0358(11) . .
C1 C Uani 0.7184(5) 0.0435(3) 0.4558(3) 1.000 0.0278(11) . .
C2 C Uani 0.7470(5) 0.0173(4) 0.5392(3) 1.000 0.0304(11) . .
C3 C Uani 0.8938(5) 0.0889(4) 0.5995(3) 1.000 0.0287(11) . .
C4 C Uani 1.0105(4) 0.1889(3) 0.5784(2) 1.000 0.0244(10) . .
C5 C Uani 0.9709(4) 0.2178(3) 0.4941(2) 1.000 0.0221(10) . .
C6 C Uani 1.0645(4) 0.3279(3) 0.4608(2) 1.000 0.0233(10) . .
C7 C Uani 1.2078(4) 0.4326(3) 0.5075(2) 1.000 0.0245(11) . .
C8 C Uani 1.2638(5) 0.5365(4) 0.4666(3) 1.000 0.0278(11) . .
C9 C Uani 1.1824(5) 0.5356(4) 0.3839(3) 1.000 0.0290(11) . .
C10 C Uani 1.0435(5) 0.4281(4) 0.3389(3) 1.000 0.0286(11) . .
C11 C Uani 1.3090(5) 0.3211(4) 0.6206(3) 1.000 0.0311(11) . .
C12 C Uani 1.4492(5) 0.3520(4) 0.7015(3) 1.000 0.0288(11) . .
C13 C Uani 1.4901(6) 0.4736(4) 0.7710(3) 1.000 0.0434(16) . .
C14 C Uani 1.6228(6) 0.4931(5) 0.8412(3) 1.000 0.0490(16) . .
C15 C Uani 1.7067(6) 0.3894(4) 0.8425(3) 1.000 0.0433(14) . .
C16 C Uani 1.6530(5) 0.2707(4) 0.7720(3) 1.000 0.0403(14) . .
C17 C Uani 0.8066(4) -0.0505(4) 0.1555(3) 1.000 0.0289(11) . .
C18 C Uani 0.7738(5) 0.0298(4) 0.0972(3) 1.000 0.0357(12) . .
C19 C Uani 0.7577(5) 0.1634(4) 0.1261(3) 1.000 0.0304(12) . .
C20 C Uani 0.8197(5) -0.1972(4) 0.1110(3) 1.000 0.0365(12) . .
C21 C Uani 0.7315(7) 0.2423(5) 0.0560(3) 1.000 0.0479(17) . .
C22 C Uani 0.4430(5) 0.1782(4) 0.2908(3) 1.000 0.0294(11) . .
C23 C Uani 0.2821(5) 0.1341(4) 0.2179(3) 1.000 0.0333(13) . .
F15 F Uani 0.239(2) 0.2197(19) 0.1918(14) 0.200 0.0753(16) . .
F16 F Uani 0.1645(19) 0.1228(18) 0.2805(9) 0.200 0.0653(14) . .
F14 F Uani 0.2407(18) 0.0264(16) 0.1709(12) 0.200 0.0475(13) . .
H3 H Uiso 1.163(6) 0.215(4) 0.685(2) 1.000 0.051(14) . .
H3A H Uiso 0.91640 0.07010 0.65670 1.000 0.0340 calc R
H8A H Uiso 1.36010 0.60840 0.49730 1.000 0.0340 calc R
H9A H Uiso 1.21940 0.60710 0.35690 1.000 0.0350 calc R
H4 H Uiso 1.377(3) 0.510(3) 0.612(2) 1.000 0.019(9) . .
H11A H Uiso 1.33440 0.25360 0.56910 1.000 0.0370 calc R
H13A H Uiso 1.42760 0.54190 0.77000 1.000 0.0520 calc R
H14A H Uiso 1.65640 0.57680 0.88830 1.000 0.0590 calc R
H15A H Uiso 1.79830 0.39970 0.89030 1.000 0.0520 calc R
H16A H Uiso 1.70790 0.19810 0.77400 1.000 0.0490 calc R
H18A H Uiso 0.76170 -0.00970 0.03380 1.000 0.0420 calc R
H10A H Uiso 0.98720 0.42560 0.28030 1.000 0.0340 calc R
H1A H Uiso 0.62040 -0.00870 0.41220 1.000 0.0330 calc R
H2A H Uiso 0.66710 -0.04870 0.55470 1.000 0.0360 calc R


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 2.210(2) . . yes
Cu1 O2 1.941(3) . . yes
Cu1 O3 2.016(3) . . yes
Cu1 N1 1.954(3) . . yes
Cu1 N2 1.986(3) . . yes
F1 C20 1.325(5) . . yes
F2 C20 1.315(5) . . yes
F3 C20 1.321(5) . . yes
F4 C21 1.309(5) . . yes
F5 C21 1.311(7) . . yes
F6 C21 1.327(7) . . yes
F11 C23 1.357(5) . . yes
F12 C23 1.323(6) . . yes
F13 C23 1.343(5) . . yes
F14 C23 1.130(18) . . yes
F15 C23 1.15(2) . . yes
F16 C23 1.470(16) . . yes
O1 C17 1.245(5) . . yes
O2 C19 1.262(5) . . yes
O3 C22 1.255(5) . . yes
O4 C22 1.215(5) . . yes
N1 C1 1.338(5) . . yes
N1 C5 1.365(4) . . yes
N2 C10 1.326(5) . . yes
N2 C6 1.366(4) . . yes
N3 C4 1.381(4) . . yes
N3 C11 1.454(5) . . yes
N4 C7 1.379(4) . . yes
N4 C11 1.427(5) . . yes
N5 C16 1.328(5) . . yes
N5 C12 1.336(5) . . yes
N3 H3 0.86(4) . . no
N4 H4 0.84(3) . . no
C1 C2 1.376(6) . . no
C2 C3 1.374(6) . . no
C3 C4 1.399(5) . . no
C4 C5 1.412(4) . . no
C5 C6 1.482(4) . . no
C6 C7 1.406(5) . . no
C7 C8 1.403(5) . . no
C8 C9 1.354(6) . . no
C9 C10 1.393(6) . . no
C11 C12 1.504(6) . . no
C12 C13 1.390(6) . . no
C13 C14 1.375(7) . . no
C14 C15 1.383(7) . . no
C15 C16 1.379(6) . . no
C17 C18 1.393(6) . . no
C17 C20 1.536(6) . . no
C18 C19 1.381(6) . . no
C19 C21 1.516(7) . . no
C22 C23 1.529(6) . . no
C1 H1A 0.9500 . . no
C2 H2A 0.9500 . . no
C3 H3A 0.9500 . . no
C8 H8A 0.9500 . . no
C9 H9A 0.9500 . . no
C10 H10A 0.9500 . . no
C11 H11A 1.0000 . . no
C13 H13A 0.9500 . . no
C14 H14A 0.9500 . . no
C15 H15A 0.9500 . . no
C16 H16A 0.9500 . . no
C18 H18A 0.9500 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O2 89.39(11) . . . yes
O1 Cu1 O3 87.73(11) . . . yes
O1 Cu1 N1 95.10(11) . . . yes
O1 Cu1 N2 118.18(12) . . . yes
O2 Cu1 O3 86.86(12) . . . yes
O2 Cu1 N1 173.03(13) . . . yes
O2 Cu1 N2 92.33(12) . . . yes
O3 Cu1 N1 98.63(13) . . . yes
O3 Cu1 N2 154.08(13) . . . yes
N1 Cu1 N2 80.85(13) . . . yes
Cu1 O1 C17 120.9(2) . . . yes
Cu1 O2 C19 127.1(3) . . . yes
Cu1 O3 C22 115.8(3) . . . yes
Cu1 N1 C1 121.2(3) . . . yes
Cu1 N1 C5 116.5(2) . . . yes
C1 N1 C5 122.3(3) . . . yes
Cu1 N2 C6 115.8(2) . . . yes
Cu1 N2 C10 122.2(3) . . . yes
C6 N2 C10 121.9(3) . . . yes
C4 N3 C11 122.3(3) . . . yes
C7 N4 C11 121.2(3) . . . yes
C12 N5 C16 117.2(3) . . . yes
C11 N3 H3 117(3) . . . no
C4 N3 H3 110(3) . . . no
C11 N4 H4 117(2) . . . no
C7 N4 H4 113(2) . . . no
N1 C1 C2 121.1(4) . . . yes
C1 C2 C3 118.4(4) . . . no
C2 C3 C4 121.4(4) . . . no
C3 C4 C5 118.1(3) . . . no
N3 C4 C5 124.4(3) . . . yes
N3 C4 C3 117.5(3) . . . yes
N1 C5 C6 113.5(3) . . . yes
C4 C5 C6 128.0(3) . . . no
N1 C5 C4 118.5(3) . . . yes
N2 C6 C5 112.8(3) . . . yes
N2 C6 C7 118.8(3) . . . yes
C5 C6 C7 128.2(3) . . . no
N4 C7 C8 117.7(3) . . . yes
C6 C7 C8 118.4(3) . . . no
N4 C7 C6 123.8(3) . . . yes
C7 C8 C9 120.8(4) . . . no
C8 C9 C10 118.9(4) . . . no
N2 C10 C9 121.1(4) . . . yes
N4 C11 C12 111.8(3) . . . yes
N3 C11 N4 111.8(3) . . . yes
N3 C11 C12 108.3(3) . . . yes
N5 C12 C13 122.8(4) . . . yes
C11 C12 C13 123.2(4) . . . no
N5 C12 C11 114.1(4) . . . yes
C12 C13 C14 118.7(4) . . . no
C13 C14 C15 119.2(4) . . . no
C14 C15 C16 117.8(4) . . . no
N5 C16 C15 124.3(4) . . . yes
O1 C17 C20 114.8(4) . . . yes
C18 C17 C20 116.6(4) . . . no
O1 C17 C18 128.6(4) . . . yes
C17 C18 C19 123.9(4) . . . no
C18 C19 C21 118.6(4) . . . no
O2 C19 C21 111.9(4) . . . yes
O2 C19 C18 129.5(4) . . . yes
F1 C20 F3 106.2(4) . . . yes
F1 C20 C17 111.9(3) . . . yes
F2 C20 F3 107.6(4) . . . yes
F2 C20 C17 110.7(3) . . . yes
F1 C20 F2 106.6(4) . . . yes
F3 C20 C17 113.4(4) . . . yes
F5 C21 C19 111.8(4) . . . yes
F6 C21 C19 110.9(4) . . . yes
F5 C21 F6 105.2(4) . . . yes
F4 C21 F5 107.5(4) . . . yes
F4 C21 F6 106.0(4) . . . yes
F4 C21 C19 114.8(4) . . . yes
O4 C22 C23 117.0(4) . . . yes
O3 C22 O4 129.8(4) . . . yes
O3 C22 C23 113.2(4) . . . yes
F11 C23 F13 104.5(4) . . . yes
F11 C23 C22 108.9(4) . . . yes
F12 C23 F13 108.8(4) . . . yes
F12 C23 C22 116.1(4) . . . yes
F16 C23 C22 96.0(6) . . . yes
F14 C23 F15 117.2(14) . . . yes
F14 C23 F16 99.6(11) . . . yes
F15 C23 F16 97.2(12) . . . yes
F13 C23 C22 114.0(4) . . . yes
F14 C23 C22 121.3(9) . . . yes
F15 C23 C22 116.4(10) . . . yes
F11 C23 F12 103.4(4) . . . yes
N1 C1 H1A 120.00 . . . no
C2 C1 H1A 119.00 . . . no
C1 C2 H2A 121.00 . . . no
C3 C2 H2A 121.00 . . . no
C2 C3 H3A 119.00 . . . no
C4 C3 H3A 119.00 . . . no
C7 C8 H8A 120.00 . . . no
C9 C8 H8A 120.00 . . . no
C8 C9 H9A 121.00 . . . no
C10 C9 H9A 120.00 . . . no
N2 C10 H10A 119.00 . . . no
C9 C10 H10A 119.00 . . . no
N3 C11 H11A 108.00 . . . no
N4 C11 H11A 108.00 . . . no
C12 C11 H11A 108.00 . . . no
C12 C13 H13A 121.00 . . . no
C14 C13 H13A 121.00 . . . no
C13 C14 H14A 120.00 . . . no
C15 C14 H14A 120.00 . . . no
C14 C15 H15A 121.00 . . . no
C16 C15 H15A 121.00 . . . no
N5 C16 H16A 118.00 . . . no
C15 C16 H16A 118.00 . . . no
C17 C18 H18A 118.00 . . . no
C19 C18 H18A 118.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Cu1 O1 C17 -7.4(3) . . . . no
O3 Cu1 O1 C17 79.5(3) . . . . no
N1 Cu1 O1 C17 178.0(3) . . . . no
N2 Cu1 O1 C17 -99.7(3) . . . . no
O1 Cu1 O2 C19 8.0(3) . . . . no
O3 Cu1 O2 C19 -79.8(3) . . . . no
N2 Cu1 O2 C19 126.2(3) . . . . no
O1 Cu1 O3 C22 -164.3(3) . . . . no
O2 Cu1 O3 C22 -74.8(3) . . . . no
N1 Cu1 O3 C22 100.9(3) . . . . no
N2 Cu1 O3 C22 14.1(5) . . . . no
O1 Cu1 N1 C1 -67.8(3) . . . . no
O1 Cu1 N1 C5 110.9(3) . . . . no
O3 Cu1 N1 C1 20.7(3) . . . . no
O3 Cu1 N1 C5 -160.6(3) . . . . no
N2 Cu1 N1 C1 174.5(3) . . . . no
N2 Cu1 N1 C5 -6.9(3) . . . . no
O1 Cu1 N2 C6 -84.7(3) . . . . no
O1 Cu1 N2 C10 97.6(3) . . . . no
O2 Cu1 N2 C6 -175.3(3) . . . . no
O2 Cu1 N2 C10 7.1(3) . . . . no
O3 Cu1 N2 C6 97.1(4) . . . . no
O3 Cu1 N2 C10 -80.6(4) . . . . no
N1 Cu1 N2 C6 6.2(3) . . . . no
N1 Cu1 N2 C10 -171.5(3) . . . . no
Cu1 O1 C17 C18 4.4(5) . . . . no
Cu1 O1 C17 C20 -174.2(2) . . . . no
Cu1 O2 C19 C18 -5.6(6) . . . . no
Cu1 O2 C19 C21 176.4(3) . . . . no
Cu1 O3 C22 O4 -32.7(6) . . . . no
Cu1 O3 C22 C23 145.5(3) . . . . no
Cu1 N1 C1 C2 179.8(3) . . . . no
C5 N1 C1 C2 1.2(6) . . . . no
Cu1 N1 C5 C4 -176.1(2) . . . . no
Cu1 N1 C5 C6 6.3(4) . . . . no
C1 N1 C5 C4 2.5(5) . . . . no
C1 N1 C5 C6 -175.0(3) . . . . no
Cu1 N2 C6 C5 -4.5(4) . . . . no
Cu1 N2 C6 C7 -179.5(2) . . . . no
C10 N2 C6 C5 173.2(3) . . . . no
C10 N2 C6 C7 -1.8(5) . . . . no
Cu1 N2 C10 C9 177.7(3) . . . . no
C6 N2 C10 C9 0.2(6) . . . . no
C11 N3 C4 C3 155.9(4) . . . . no
C11 N3 C4 C5 -27.2(5) . . . . no
C4 N3 C11 N4 71.3(5) . . . . no
C4 N3 C11 C12 -165.1(3) . . . . no
C11 N4 C7 C6 33.4(5) . . . . no
C11 N4 C7 C8 -148.4(4) . . . . no
C7 N4 C11 N3 -75.9(4) . . . . no
C7 N4 C11 C12 162.5(3) . . . . no
C16 N5 C12 C11 -178.8(4) . . . . no
C16 N5 C12 C13 0.1(6) . . . . no
C12 N5 C16 C15 -2.5(6) . . . . no
N1 C1 C2 C3 -3.3(6) . . . . no
C1 C2 C3 C4 1.6(6) . . . . no
C2 C3 C4 N3 179.1(4) . . . . no
C2 C3 C4 C5 2.0(6) . . . . no
N3 C4 C5 N1 179.0(3) . . . . no
N3 C4 C5 C6 -3.8(6) . . . . no
C3 C4 C5 N1 -4.1(5) . . . . no
C3 C4 C5 C6 173.1(3) . . . . no
N1 C5 C6 N2 -1.1(4) . . . . no
N1 C5 C6 C7 173.4(3) . . . . no
C4 C5 C6 N2 -178.4(3) . . . . no
C4 C5 C6 C7 -3.9(6) . . . . no
N2 C6 C7 N4 -179.9(3) . . . . no
N2 C6 C7 C8 1.9(5) . . . . no
C5 C6 C7 N4 6.0(6) . . . . no
C5 C6 C7 C8 -172.3(3) . . . . no
N4 C7 C8 C9 -178.7(4) . . . . no
C6 C7 C8 C9 -0.4(6) . . . . no
C7 C8 C9 C10 -1.3(6) . . . . no
C8 C9 C10 N2 1.4(6) . . . . no
N3 C11 C12 N5 91.2(4) . . . . no
N3 C11 C12 C13 -87.8(5) . . . . no
N4 C11 C12 N5 -145.3(4) . . . . no
N4 C11 C12 C13 35.8(6) . . . . no
N5 C12 C13 C14 2.4(7) . . . . no
C11 C12 C13 C14 -178.7(4) . . . . no
C12 C13 C14 C15 -2.6(7) . . . . no
C13 C14 C15 C16 0.5(7) . . . . no
C14 C15 C16 N5 2.2(7) . . . . no
O1 C17 C18 C19 1.2(7) . . . . no
C20 C17 C18 C19 179.8(4) . . . . no
O1 C17 C20 F1 -33.4(5) . . . . no
O1 C17 C20 F2 85.5(4) . . . . no
O1 C17 C20 F3 -153.6(4) . . . . no
C18 C17 C20 F1 147.9(4) . . . . no
C18 C17 C20 F2 -93.3(5) . . . . no
C18 C17 C20 F3 27.7(5) . . . . no
C17 C18 C19 O2 -1.2(7) . . . . no
C17 C18 C19 C21 176.7(4) . . . . no
O2 C19 C21 F4 -178.6(4) . . . . no
O2 C19 C21 F5 -55.9(5) . . . . no
O2 C19 C21 F6 61.2(5) . . . . no
C18 C19 C21 F4 3.2(7) . . . . no
C18 C19 C21 F5 125.9(4) . . . . no
C18 C19 C21 F6 -117.0(5) . . . . no
O3 C22 C23 F11 -68.1(5) . . . . no
O3 C22 C23 F12 175.8(4) . . . . no
O3 C22 C23 F13 48.2(5) . . . . no
O4 C22 C23 F11 110.4(5) . . . . no
O4 C22 C23 F12 -5.8(6) . . . . no
O4 C22 C23 F13 -133.4(4) . . . . no


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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N3 H3 F1 0.86(4) 2.53(4) 3.186(4) 134(4) 2_756 yes
N3 H3 O1 0.86(4) 2.56(4) 3.377(4) 160(3) 2_756 yes
N4 H4 O4 0.84(3) 2.14(3) 2.953(5) 165(3) 2_766 yes
C1 H1A O3 0.95 2.58 3.116(5) 116 . yes
C8 H8A O4 0.95 2.49 3.272(5) 140 2_766 yes
C10 H10A O2 0.95 2.33 2.896(5) 118 . yes
C16 H16A F13 0.95 2.42 3.357(5) 168 2_756 yes
C18 H18A F3 0.95 2.40 2.748(5) 101 . yes
C18 H18A F4 0.95 2.35 2.727(5) 103 . yes







_diffrn_measured_fraction_theta_max 0.932
_diffrn_reflns_theta_full        25.91
_diffrn_measured_fraction_theta_full 0.932
_refine_diff_density_max         0.701
_refine_diff_density_min         -0.922
_refine_diff_density_rms         0.098


_vrf_PLAT029_mel-7bd             
; 
PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.93 
RESPONSE: ...With the Stoe IPDS I machine for the triclinic system only 
ca. 93% of the Ewald sphere is accessible 
[_diffrn_measured_fraction_theta_max    0.932]. 
This has a negligible effect on the bond distances and angles.
;

#====================================
####################################################################### 
# 
# 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/. 
# 
# 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_imine-gb
_database_code_depnum_ccdc_archive 'CCDC 972055'
_audit_update_record             
;
2013-11-14 deposited with the CCDC.
2014-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
N3,N3-Bis(Methoxy(pyridin-2-yl)methyl)-2,2-bipyridine-3,3-diamine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H24 N6 O2'
_chemical_formula_sum            'C24 H24 N6 O2'
_chemical_formula_weight         428.49

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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   4.9022(6)
_cell_length_b                   13.8842(15)
_cell_length_c                   15.385(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.095(16)
_cell_angle_gamma                90.00
_cell_volume                     1034.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3905
_cell_measurement_theta_min      1.95
_cell_measurement_theta_max      25.70

_exptl_crystal_description       rod
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       'phi rotation'
_diffrn_detector_area_resol_mean 0.81\%A
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            1884
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0705
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         26.00
_reflns_number_total             1884
_reflns_number_gt                1154
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'EXPOSE (Stoe, 2000)'
_computing_cell_refinement       'CELL (Stoe, 2000)'
_computing_data_reduction        'INTEGRATE (Stoe, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL-97

_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)+(0.0465P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1884
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0833
_refine_ls_wR_factor_gt          0.0728
_refine_ls_goodness_of_fit_ref   0.826
_refine_ls_restrained_S_all      0.826
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001



#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O Uani 0.7430(3) 0.34489(9) 0.26017(8) 1.000 0.0313(5) . .
N1A N Uani 1.033(2) 0.5665(8) 0.2918(8) 0.500 0.034(3) . .
N1B N Uani 0.934(2) 0.5901(8) 0.2905(8) 0.500 0.038(3) . .
N2 N Uani 0.8647(4) 0.45940(13) 0.15600(11) 1.000 0.0291(7) . .
N3 N Uani 0.8059(4) 0.42608(12) -0.08407(11) 1.000 0.0280(6) . .
C1A C Uani 1.099(4) 0.6302(9) 0.3540(12) 0.500 0.041(4) . .
C1B C Uani 1.015(3) 0.6526(9) 0.3599(11) 0.500 0.038(4) . .
C2 C Uani 0.9520(6) 0.64361(19) 0.4313(2) 1.000 0.0507(11) . .
C3A C Uani 0.7133(14) 0.5986(5) 0.4232(4) 0.500 0.045(3) . .
C3B C Uani 0.8125(14) 0.5544(4) 0.4567(4) 0.500 0.043(2) . .
C4A C Uani 0.6381(13) 0.5295(4) 0.3586(4) 0.500 0.035(2) . .
C4B C Uani 0.7291(15) 0.4908(4) 0.3887(4) 0.500 0.041(2) . .
C5 C Uani 0.7996(5) 0.51376(14) 0.30042(14) 1.000 0.0297(8) . .
C6 C Uani 0.7135(5) 0.44145(13) 0.22666(12) 1.000 0.0272(7) . .
C7 C Uani 0.7778(5) 0.42659(13) 0.07134(13) 1.000 0.0242(7) . .
C8 C Uani 0.5723(5) 0.35605(14) 0.05471(13) 1.000 0.0281(7) . .
C9 C Uani 0.4863(5) 0.32243(15) -0.02970(13) 1.000 0.0317(8) . .
C10 C Uani 0.6099(5) 0.35811(14) -0.09715(13) 1.000 0.0300(7) . .
C11 C Uani 0.8925(5) 0.46187(13) -0.00267(12) 1.000 0.0236(7) . .
C12 C Uani 1.0227(6) 0.31926(16) 0.29458(15) 1.000 0.0423(9) . .
H1A H Uiso 1.25170 0.67110 0.34980 0.500 0.0490 calc .
H1B H Uiso 1.12840 0.70580 0.35020 0.500 0.0460 calc .
H2 H Uiso 0.999(7) 0.511(2) 0.1569(17) 1.000 0.068(9) . .
H2A H Uiso 1.02410 0.68100 0.48140 1.000 0.0610 calc R
H3A H Uiso 0.58880 0.61380 0.46270 0.500 0.0540 calc .
H3B H Uiso 0.78350 0.54240 0.51530 0.500 0.0520 calc .
H4A H Uiso 0.47130 0.49410 0.35680 0.500 0.0410 calc .
H4B H Uiso 0.62970 0.43400 0.39800 0.500 0.0490 calc .
H6 H Uiso 0.51340 0.45230 0.20380 1.000 0.0330 calc R
H8 H Uiso 0.49080 0.33100 0.10200 1.000 0.0340 calc R
H9 H Uiso 0.34420 0.27550 -0.04090 1.000 0.0380 calc R
H10 H Uiso 0.55460 0.33380 -0.15490 1.000 0.0360 calc R
H12A H Uiso 1.08930 0.35940 0.34590 1.000 0.0630 calc R
H12B H Uiso 1.13950 0.32950 0.24930 1.000 0.0630 calc R
H12C H Uiso 1.03040 0.25130 0.31210 1.000 0.0630 calc R


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.435(2) . . ?
O1 C12 1.434(3) . . ?
N1A N1B 0.583(15) . . ?
N1A C1A 1.31(2) . . ?
N1A C1B 1.601(19) . . ?
N1A C5 1.382(11) . . ?
N1B C1A 1.29(2) . . ?
N1B C1B 1.384(19) . . ?
N1B C5 1.270(11) . . ?
N2 C6 1.431(3) . . ?
N2 C7 1.382(3) . . ?
N3 C10 1.339(3) . . ?
N3 C11 1.352(2) . . ?
N2 H2 0.97(3) . . no
C1A C1B 0.54(2) . . no
C1A C2 1.496(19) . . no
C1B C2 1.194(17) . . no
C2 C3A 1.315(8) . . no
C2 C3B 1.496(7) . . no
C3A C4A 1.389(9) . . no
C3A C4B 1.594(9) . . no
C3A C3B 0.894(9) . . no
C3B C4A 1.649(9) . . no
C3B C4B 1.381(8) . . no
C4A C4B 0.798(9) . . no
C4A C5 1.304(7) . . no
C4B C5 1.488(7) . . no
C5 C6 1.524(3) . . no
C7 C8 1.399(3) . . no
C7 C11 1.434(3) . . no
C8 C9 1.382(3) . . no
C9 C10 1.374(3) . . no
C11 C11 1.487(3) . 3_765 no
C1A H1A 0.9500 . . no
C1A H1B 1.0600 . . no
C1B H1A 1.2200 . . no
C1B H1B 0.9500 . . no
C2 H2A 0.9500 . . no
C3A H3A 0.9500 . . no
C3B H3A 1.3900 . . no
C3B H3B 0.9500 . . no
C4A H4A 0.9500 . . no
C4B H4A 1.2800 . . no
C4B H4B 0.9500 . . no
C6 H6 1.0000 . . no
C8 H8 0.9500 . . no
C9 H9 0.9500 . . no
C10 H10 0.9500 . . no
C12 H12A 0.9800 . . no
C12 H12B 0.9800 . . no
C12 H12C 0.9800 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 C12 113.60(16) . . . ?
N1B N1A C1A 75.7(18) . . . ?
N1B N1A C1B 58.1(16) . . . ?
N1B N1A C5 66.7(14) . . . ?
C1A N1A C1B 17.8(10) . . . ?
C1A N1A C5 113.7(12) . . . ?
C1B N1A C5 101.6(8) . . . ?
N1A N1B C1A 78.4(18) . . . ?
N1A N1B C1B 101.0(18) . . . ?
N1A N1B C5 88.4(16) . . . ?
C1A N1B C1B 22.7(10) . . . ?
C1A N1B C5 122.9(12) . . . ?
C1B N1B C5 121.4(11) . . . ?
C6 N2 C7 122.62(19) . . . ?
C10 N3 C11 120.74(18) . . . ?
C6 N2 H2 123.3(16) . . . no
C7 N2 H2 111.3(15) . . . no
N1A C1A N1B 26.0(7) . . . ?
N1B C1A C1B 88(3) . . . ?
N1B C1A C2 109.4(14) . . . ?
C1B C1A C2 47(2) . . . no
N1A C1A C2 124.9(14) . . . ?
N1A C1A C1B 114(3) . . . ?
N1A C1B C1A 48(2) . . . ?
N1A C1B N1B 21.0(6) . . . ?
N1B C1B C2 124.0(12) . . . ?
N1A C1B C2 125.0(11) . . . ?
N1B C1B C1A 69(2) . . . ?
C1A C1B C2 114(3) . . . no
C1A C2 C3A 113.5(7) . . . no
C1A C2 C3B 113.7(6) . . . no
C1B C2 C3B 121.5(7) . . . no
C3A C2 C3B 36.4(4) . . . no
C1B C2 C3A 108.6(8) . . . no
C1A C2 C1B 19.0(9) . . . no
C2 C3A C4B 112.9(5) . . . no
C3B C3A C4A 89.8(7) . . . no
C3B C3A C4B 59.8(6) . . . no
C4A C3A C4B 30.0(4) . . . no
C2 C3A C4A 121.9(6) . . . no
C2 C3A C3B 82.9(7) . . . no
C2 C3B C4A 97.3(4) . . . no
C2 C3B C3A 60.7(6) . . . no
C3A C3B C4B 86.2(7) . . . no
C4A C3B C4B 28.8(3) . . . no
C2 C3B C4B 115.1(5) . . . no
C3A C3B C4A 57.3(6) . . . no
C3A C4A C5 119.1(5) . . . no
C3A C4A C3B 32.8(4) . . . no
C3A C4A C4B 89.4(7) . . . no
C4B C4A C5 86.6(7) . . . no
C3B C4A C5 112.4(5) . . . no
C3B C4A C4B 56.6(6) . . . no
C3A C4B C4A 60.6(6) . . . no
C3A C4B C5 97.7(4) . . . no
C3B C4B C5 118.1(5) . . . no
C4A C4B C5 61.0(6) . . . no
C3B C4B C4A 94.6(7) . . . no
C3A C4B C3B 34.0(4) . . . no
N1A C5 C4B 121.1(6) . . . ?
N1A C5 C6 114.4(5) . . . ?
N1B C5 C4A 109.0(6) . . . ?
N1B C5 C4B 119.2(6) . . . ?
N1B C5 C6 123.3(6) . . . ?
N1A C5 N1B 25.0(6) . . . ?
N1A C5 C4A 125.4(6) . . . ?
C4B C5 C6 117.5(3) . . . no
C4A C5 C6 119.7(3) . . . no
C4A C5 C4B 32.4(4) . . . no
O1 C6 C5 110.34(15) . . . ?
O1 C6 N2 113.62(17) . . . ?
N2 C6 C5 109.58(18) . . . ?
N2 C7 C11 122.33(19) . . . ?
N2 C7 C8 120.58(19) . . . ?
C8 C7 C11 117.09(18) . . . no
C7 C8 C9 120.8(2) . . . no
C8 C9 C10 118.9(2) . . . no
N3 C10 C9 122.15(19) . . . ?
C7 C11 C11 124.26(17) . . 3_765 no
N3 C11 C7 120.34(19) . . . ?
N3 C11 C11 115.40(17) . . 3_765 ?
N1A C1A H1A 117.00 . . . no
N1A C1A H1B 130.00 . . . no
N1B C1A H1A 128.00 . . . no
N1B C1A H1B 117.00 . . . no
C1B C1A H1A 107.00 . . . no
C1B C1A H1B 63.00 . . . no
C2 C1A H1A 118.00 . . . no
C2 C1A H1B 90.00 . . . no
H1A C1A H1B 45.00 . . . no
N1A C1B H1A 86.00 . . . no
N1A C1B H1B 113.00 . . . no
N1B C1B H1A 101.00 . . . no
N1B C1B H1B 118.00 . . . no
C1A C1B H1A 48.00 . . . no
C1A C1B H1B 87.00 . . . no
C2 C1B H1A 122.00 . . . no
C2 C1B H1B 118.00 . . . no
H1A C1B H1B 39.00 . . . no
C1A C2 H2A 123.00 . . . no
C1B C2 H2A 125.00 . . . no
C3A C2 H2A 123.00 . . . no
C3B C2 H2A 112.00 . . . no
C2 C3A H3A 119.00 . . . no
C3B C3A H3A 97.00 . . . no
C4A C3A H3A 119.00 . . . no
C4B C3A H3A 119.00 . . . no
C2 C3B H3A 86.00 . . . no
C2 C3B H3B 122.00 . . . no
C3A C3B H3A 43.00 . . . no
C3A C3B H3B 121.00 . . . no
C4A C3B H3A 83.00 . . . no
C4A C3B H3B 134.00 . . . no
C4B C3B H3A 107.00 . . . no
C4B C3B H3B 122.00 . . . no
H3A C3B H3B 79.00 . . . no
C3A C4A H4A 121.00 . . . no
C3B C4A H4A 117.00 . . . no
C4B C4A H4A 94.00 . . . no
C5 C4A H4A 120.00 . . . no
C3A C4B H4A 90.00 . . . no
C3A C4B H4B 133.00 . . . no
C3B C4B H4A 115.00 . . . no
C3B C4B H4B 121.00 . . . no
C4A C4B H4A 48.00 . . . no
C4A C4B H4B 113.00 . . . no
C5 C4B H4A 90.00 . . . no
C5 C4B H4B 121.00 . . . no
H4A C4B H4B 66.00 . . . no
O1 C6 H6 108.00 . . . no
N2 C6 H6 108.00 . . . no
C5 C6 H6 108.00 . . . no
C7 C8 H8 120.00 . . . no
C9 C8 H8 120.00 . . . no
C8 C9 H9 121.00 . . . no
C10 C9 H9 121.00 . . . no
N3 C10 H10 119.00 . . . no
C9 C10 H10 119.00 . . . no
O1 C12 H12A 109.00 . . . no
O1 C12 H12B 109.00 . . . no
O1 C12 H12C 109.00 . . . no
H12A C12 H12B 109.00 . . . no
H12A C12 H12C 109.00 . . . no
H12B C12 H12C 109.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 O1 C6 N2 60.3(2) . . . . no
C12 O1 C6 C5 -63.3(2) . . . . no
C1A N1A N1B C1B -2.4(11) . . . . no
C1A N1A N1B C5 -124.1(11) . . . . no
C1B N1A N1B C1A 2.4(11) . . . . no
C1B N1A N1B C5 -121.7(13) . . . . no
C5 N1A N1B C1A 124.1(11) . . . . no
C5 N1A N1B C1B 121.7(13) . . . . no
N1B N1A C1A C1B 7(3) . . . . no
N1B N1A C1A C2 60(2) . . . . no
C1B N1A C1A N1B -7(3) . . . . no
C1B N1A C1A C2 53(3) . . . . no
C5 N1A C1A N1B -56.1(15) . . . . no
C5 N1A C1A C1B -49(3) . . . . no
C5 N1A C1A C2 3.4(19) . . . . no
N1B N1A C1B C1A -172(4) . . . . no
N1B N1A C1B C2 95(2) . . . . no
C1A N1A C1B N1B 172(4) . . . . no
C1A N1A C1B C2 -93(3) . . . . no
C5 N1A C1B N1B -52.9(16) . . . . no
C5 N1A C1B C1A 135(3) . . . . no
C5 N1A C1B C2 41.9(16) . . . . no
N1B N1A C5 C4A -54.6(19) . . . . no
N1B N1A C5 C4B -93.2(17) . . . . no
N1B N1A C5 C6 116.8(16) . . . . no
C1A N1A C5 N1B 61.1(18) . . . . no
C1A N1A C5 C4A 6.5(14) . . . . no
C1A N1A C5 C4B -32.1(13) . . . . no
C1A N1A C5 C6 178.0(9) . . . . no
C1B N1A C5 N1B 47.5(16) . . . . no
C1B N1A C5 C4A -7.1(11) . . . . no
C1B N1A C5 C4B -45.7(10) . . . . no
C1B N1A C5 C6 164.3(7) . . . . no
N1A N1B C1A C1B -174(3) . . . . no
N1A N1B C1A C2 -131.5(17) . . . . no
C1B N1B C1A N1A 174(3) . . . . no
C1B N1B C1A C2 42(2) . . . . no
C5 N1B C1A N1A 80.3(18) . . . . no
C5 N1B C1A C1B -94(2) . . . . no
C5 N1B C1A C2 -51.2(15) . . . . no
N1A N1B C1B C1A 6(3) . . . . no
N1A N1B C1B C2 -100(2) . . . . no
C1A N1B C1B N1A -6(3) . . . . no
C1A N1B C1B C2 -106(3) . . . . no
C5 N1B C1B N1A 95(2) . . . . no
C5 N1B C1B C1A 101(3) . . . . no
C5 N1B C1B C2 -4.9(19) . . . . no
N1A N1B C5 C4A 135.3(16) . . . . no
N1A N1B C5 C4B 101.5(17) . . . . no
N1A N1B C5 C6 -76.3(18) . . . . no
C1A N1B C5 N1A -75(2) . . . . no
C1A N1B C5 C4A 60.3(14) . . . . no
C1A N1B C5 C4B 26.5(15) . . . . no
C1A N1B C5 C6 -151.3(11) . . . . no
C1B N1B C5 N1A -102(2) . . . . no
C1B N1B C5 C4A 33.5(12) . . . . no
C1B N1B C5 C4B -0.3(13) . . . . no
C1B N1B C5 C6 -178.2(9) . . . . no
C7 N2 C6 O1 76.0(2) . . . . no
C7 N2 C6 C5 -160.08(19) . . . . no
C6 N2 C7 C8 -14.7(3) . . . . no
C6 N2 C7 C11 165.8(2) . . . . no
C11 N3 C10 C9 0.7(3) . . . . no
C10 N3 C11 C7 0.8(3) . . . . no
C10 N3 C11 C11 -179.00(19) . . . 3_765 no
N1A C1A C1B N1B -2.9(14) . . . . no
N1A C1A C1B C2 116(2) . . . . no
N1B C1A C1B N1A 2.9(14) . . . . no
N1B C1A C1B C2 118.9(17) . . . . no
C2 C1A C1B N1A -116(2) . . . . no
C2 C1A C1B N1B -118.9(17) . . . . no
N1A C1A C2 C1B -92(3) . . . . no
N1A C1A C2 C3A -12.9(17) . . . . no
N1A C1A C2 C3B 26.9(18) . . . . no
N1B C1A C2 C1B -68(3) . . . . no
N1B C1A C2 C3A 10.6(13) . . . . no
N1B C1A C2 C3B 50.4(12) . . . . no
C1B C1A C2 C3A 79(3) . . . . no
C1B C1A C2 C3B 119(3) . . . . no
N1A C1B C2 C1A 55(2) . . . . no
N1A C1B C2 C3A -53.8(14) . . . . no
N1A C1B C2 C3B -16.0(17) . . . . no
N1B C1B C2 C1A 80(3) . . . . no
N1B C1B C2 C3A -28.3(15) . . . . no
N1B C1B C2 C3B 9.5(17) . . . . no
C1A C1B C2 C3A -109(3) . . . . no
C1A C1B C2 C3B -71(3) . . . . no
C1A C2 C3A C3B 98.6(8) . . . . no
C1A C2 C3A C4A 13.2(10) . . . . no
C1A C2 C3A C4B 45.6(8) . . . . no
C1B C2 C3A C3B 118.2(9) . . . . no
C1B C2 C3A C4A 32.9(10) . . . . no
C1B C2 C3A C4B 65.3(8) . . . . no
C3B C2 C3A C4A -85.4(8) . . . . no
C3B C2 C3A C4B -53.0(6) . . . . no
C1A C2 C3B C3A -97.9(10) . . . . no
C1A C2 C3B C4A -52.0(9) . . . . no
C1A C2 C3B C4B -28.3(10) . . . . no
C1B C2 C3B C3A -78.3(11) . . . . no
C1B C2 C3B C4A -32.4(10) . . . . no
C1B C2 C3B C4B -8.7(11) . . . . no
C3A C2 C3B C4A 45.9(6) . . . . no
C3A C2 C3B C4B 69.7(7) . . . . no
C2 C3A C3B C4A -122.2(5) . . . . no
C2 C3A C3B C4B -121.7(5) . . . . no
C4A C3A C3B C2 122.2(5) . . . . no
C4A C3A C3B C4B 0.5(5) . . . . no
C4B C3A C3B C2 121.7(5) . . . . no
C4B C3A C3B C4A -0.5(5) . . . . no
C2 C3A C4A C3B 81.6(8) . . . . no
C2 C3A C4A C4B 80.7(9) . . . . no
C2 C3A C4A C5 -5.1(9) . . . . no
C3B C3A C4A C4B -0.8(9) . . . . no
C3B C3A C4A C5 -86.6(8) . . . . no
C4B C3A C4A C3B 0.8(9) . . . . no
C4B C3A C4A C5 -85.8(8) . . . . no
C2 C3A C4B C3B 66.4(7) . . . . no
C2 C3A C4B C4A -114.5(8) . . . . no
C2 C3A C4B C5 -64.1(6) . . . . no
C3B C3A C4B C4A 179.1(11) . . . . no
C3B C3A C4B C5 -130.5(8) . . . . no
C4A C3A C4B C3B -179.1(11) . . . . no
C4A C3A C4B C5 50.4(6) . . . . no
C2 C3B C4A C3A -48.1(6) . . . . no
C2 C3B C4A C4B 130.9(8) . . . . no
C2 C3B C4A C5 61.3(5) . . . . no
C3A C3B C4A C4B 179.0(11) . . . . no
C3A C3B C4A C5 109.4(8) . . . . no
C4B C3B C4A C3A -179.0(11) . . . . no
C4B C3B C4A C5 -69.6(8) . . . . no
C2 C3B C4B C3A -55.1(6) . . . . no
C2 C3B C4B C4A -55.9(9) . . . . no
C2 C3B C4B C5 3.6(8) . . . . no
C3A C3B C4B C4A -0.8(9) . . . . no
C3A C3B C4B C5 58.6(8) . . . . no
C4A C3B C4B C3A 0.8(9) . . . . no
C4A C3B C4B C5 59.5(6) . . . . no
C3A C4A C4B C3B 0.5(6) . . . . no
C3A C4A C4B C5 -119.2(5) . . . . no
C3B C4A C4B C3A -0.5(6) . . . . no
C3B C4A C4B C5 -119.7(5) . . . . no
C5 C4A C4B C3A 119.2(5) . . . . no
C5 C4A C4B C3B 119.7(5) . . . . no
C3A C4A C5 N1A -6.2(9) . . . . no
C3A C4A C5 N1B -27.5(8) . . . . no
C3A C4A C5 C4B 87.4(8) . . . . no
C3A C4A C5 C6 -177.2(4) . . . . no
C3B C4A C5 N1A -42.0(8) . . . . no
C3B C4A C5 N1B -63.3(7) . . . . no
C3B C4A C5 C4B 51.6(6) . . . . no
C3B C4A C5 C6 147.0(3) . . . . no
C4B C4A C5 N1A -93.6(9) . . . . no
C4B C4A C5 N1B -114.9(8) . . . . no
C4B C4A C5 C6 95.4(7) . . . . no
C3A C4B C5 N1A 58.0(7) . . . . no
C3A C4B C5 N1B 29.2(8) . . . . no
C3A C4B C5 C4A -50.1(6) . . . . no
C3A C4B C5 C6 -152.9(3) . . . . no
C3B C4B C5 N1A 29.2(9) . . . . no
C3B C4B C5 N1B 0.3(9) . . . . no
C3B C4B C5 C4A -79.0(7) . . . . no
C3B C4B C5 C6 178.3(5) . . . . no
C4A C4B C5 N1A 108.1(8) . . . . no
C4A C4B C5 N1B 79.3(9) . . . . no
C4A C4B C5 C6 -102.8(6) . . . . no
N1A C5 C6 O1 114.0(5) . . . . no
N1A C5 C6 N2 -11.8(6) . . . . no
N1B C5 C6 O1 140.8(6) . . . . no
N1B C5 C6 N2 15.0(6) . . . . no
C4A C5 C6 O1 -74.0(4) . . . . no
C4A C5 C6 N2 160.2(3) . . . . no
C4B C5 C6 O1 -37.1(4) . . . . no
C4B C5 C6 N2 -162.9(3) . . . . no
N2 C7 C8 C9 -179.5(2) . . . . no
C11 C7 C8 C9 0.1(3) . . . . no
N2 C7 C11 N3 178.4(2) . . . . no
N2 C7 C11 C11 -1.8(3) . . . 3_765 no
C8 C7 C11 N3 -1.2(3) . . . . no
C8 C7 C11 C11 178.6(2) . . . 3_765 no
C7 C8 C9 C10 1.3(3) . . . . no
C8 C9 C10 N3 -1.7(3) . . . . no
N3 C11 C11 N3 -180.0(2) . . 3_765 3_765 no
N3 C11 C11 C7 -0.2(3) . . 3_765 3_765 no
C7 C11 C11 N3 0.2(3) . . 3_765 3_765 no
C7 C11 C11 C7 180.0(2) . . 3_765 3_765 no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C8 3.143(2) . . no
O1 H4B 2.5900 . . no
O1 H8 2.5600 . . no
O1 H1B 2.7100 . 2_745 no
N1A N2 2.591(12) . . no
N1A C4A 3.026(12) . 1_655 no
N1A C12 3.434(11) . . no
N1B N2 2.733(12) . . no
N2 N1B 2.733(12) . . no
N2 N3 2.632(3) . 3_765 no
N2 N1A 2.591(12) . . no
N3 N2 2.632(3) . 3_765 no
N1A H2 2.20(3) . . no
N1A H4A 2.4400 . 1_655 no
N1B H12C 2.7600 . 2_755 no
N1B H2 2.40(3) . . no
N2 H12B 2.5500 . . no
N3 H2 1.81(3) . 3_765 no
N3 H6 2.7900 . 3_665 no
C1A C3A 3.06(2) . 1_655 no
C1A C4A 2.98(2) . 1_655 no
C1A C12 3.470(15) . 2_755 no
C1B C8 3.600(14) . 2_755 no
C1B C12 3.301(15) . 2_755 no
C1B C3A 3.489(16) . 1_655 no
C1B C4A 3.503(16) . 1_655 no
C2 C4B 3.497(7) . 3_766 no
C2 C3B 3.351(6) . 3_766 no
C3A C1A 3.06(2) . 1_455 no
C3A C1B 3.489(16) . 1_455 no
C3B C2 3.351(6) . 3_766 no
C4A C1B 3.503(16) . 1_455 no
C4A N1A 3.026(12) . 1_455 no
C4A C1A 2.98(2) . 1_455 no
C4B C12 3.240(7) . . no
C4B C2 3.497(7) . 3_766 no
C7 C10 3.598(3) . 3_665 no
C8 C11 3.413(3) . 3_665 no
C8 C1B 3.600(14) . 2_745 no
C8 O1 3.143(2) . . no
C9 C11 3.600(3) . 3_665 no
C9 C11 3.575(3) . 1_455 no
C10 C7 3.598(3) . 3_665 no
C11 C9 3.575(3) . 1_655 no
C11 C9 3.600(3) . 3_665 no
C11 C8 3.413(3) . 3_665 no
C12 C4B 3.240(7) . . no
C12 N1A 3.434(11) . . no
C12 C1B 3.301(15) . 2_745 no
C12 C1A 3.470(15) . 2_745 no
C1A H3A 2.7100 . 1_655 no
C1A H12C 3.0400 . 2_755 no
C1A H4A 2.6200 . 1_655 no
C1B H12C 2.9600 . 2_755 no
C1B H3A 3.0500 . 1_655 no
C1B H12B 3.0000 . 2_755 no
C2 H3B 2.9500 . 3_766 no
C2 H9 3.0100 . 2_655 no
C3A H9 3.0900 . 2_655 no
C3A H1A 2.5700 . 1_455 no
C4A H1A 2.7200 . 1_455 no
C4B H12A 2.6900 . . no
C5 H12A 2.6000 . . no
C6 H8 2.5600 . . no
C8 H1A 3.0200 . 2_745 no
C8 H6 2.7100 . . no
C8 H1B 2.8200 . 2_745 no
C9 H2A 3.1000 . 2_745 no
C10 H12C 3.0700 . 4_554 no
C10 H2 2.90(3) . 3_765 no
C11 H2 2.54(3) . 3_765 no
C12 H1B 2.7300 . 2_745 no
C12 H9 3.0600 . 4_655 no
H1A C3A 2.5700 . 1_655 no
H1A C4A 2.7200 . 1_655 no
H1A H3A 2.3400 . 1_655 no
H1A C8 3.0200 . 2_755 no
H1B O1 2.7100 . 2_755 no
H1B C8 2.8200 . 2_755 no
H1B C12 2.7300 . 2_755 no
H1B H8 2.5700 . 2_755 no
H1B H12B 2.5300 . 2_755 no
H1B H12C 2.5700 . 2_755 no
H2 N1A 2.20(3) . . no
H2 N1B 2.40(3) . . no
H2 N3 1.81(3) . 3_765 no
H2 C10 2.90(3) . 3_765 no
H2 C11 2.54(3) . 3_765 no
H2A C9 3.1000 . 2_755 no
H2A H9 2.5200 . 2_655 no
H3A C1A 2.7100 . 1_455 no
H3A C1B 3.0500 . 1_455 no
H3A H1A 2.3400 . 1_455 no
H3A H9 2.5400 . 2_655 no
H3B C2 2.9500 . 3_766 no
H3B H12A 2.5300 . 3_766 no
H4A N1A 2.4400 . 1_455 no
H4A C1A 2.6200 . 1_455 no
H4A H6 2.4600 . . no
H4B O1 2.5900 . . no
H6 C8 2.7100 . . no
H6 H4A 2.4600 . . no
H6 H8 2.2900 . . no
H6 N3 2.7900 . 3_665 no
H8 O1 2.5600 . . no
H8 C6 2.5600 . . no
H8 H6 2.2900 . . no
H8 H1B 2.5700 . 2_745 no
H9 C2 3.0100 . 2_645 no
H9 C3A 3.0900 . 2_645 no
H9 H2A 2.5200 . 2_645 no
H9 H3A 2.5400 . 2_645 no
H9 C12 3.0600 . 4_454 no
H9 H12C 2.5500 . 4_454 no
H12A C4B 2.6900 . . no
H12A C5 2.6000 . . no
H12A H3B 2.5300 . 3_766 no
H12B N2 2.5500 . . no
H12B C1B 3.0000 . 2_745 no
H12B H1B 2.5300 . 2_745 no
H12C N1B 2.7600 . 2_745 no
H12C C1A 3.0400 . 2_745 no
H12C C1B 2.9600 . 2_745 no
H12C H1B 2.5700 . 2_745 no
H12C C10 3.0700 . 4_555 no
H12C H9 2.5500 . 4_655 no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
N2 H2 N1A 0.97(3) 2.20(3) 2.591(12) 103(2) . ?
N2 H2 N1B 0.97(3) 2.40(3) 2.733(12) 100(2) . ?
N2 H2 N3 0.97(3) 1.81(3) 2.632(3) 140(2) 3_765 ?
C4A H4A N1A 0.95 2.44 3.026(12) 120 1_455 ?
C8 H8 O1 0.95 2.56 3.143(2) 120 . ?
C12 H12B N2 0.98 2.55 2.900(3) 101 . ?


_diffrn_measured_fraction_theta_max 0.934
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.945
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.044
_vrf_PLAT029_imine-gb            
; 
PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.93 
RESPONSE: ...With the Stoe IPDS I machine for the triclinic system only 
ca. 93% of the Ewald sphere is accessible 
[_diffrn_measured_fraction_theta_max    0.932]. 
This has a negligible effect on the bond distances and angles.
;
_vrf_PLAT770_imine-gb            
; 
PROBLEM: Suspect C-H Bond in CIF:   C3B    --  H3A     ..       1.39 Ang      

RESPONSE: The terminal pyridine ring is disordered, and these two atoms
belong to different orientiations of the ring, so this is not a real 
bond length.
;
####################################################################### 
# 
# 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/. 
# 
# 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_mel-7jw
_database_code_depnum_ccdc_archive 'CCDC 972056'
_audit_update_record             
;
2013-11-14 deposited with the CCDC.
2014-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
[5-(2'-Pyridinoyl)-6-(pyrid-2-yl)-5H-dipyrido[3,2-d:2',3'-f][1,3]diazepine]
complex with Zn(hfac)2
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H16 F12 N6 O5 Zn'
_chemical_formula_sum            'C32 H16 F12 N6 O5 Zn'
_chemical_formula_weight         857.88

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'
F F 0.0171 0.0103 '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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5227(8)
_cell_length_b                   12.9131(11)
_cell_length_c                   13.7732(11)
_cell_angle_alpha                80.759(10)
_cell_angle_beta                 80.757(10)
_cell_angle_gamma                84.987(10)
_cell_volume                     1646.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7409
_cell_measurement_theta_min      2.00
_cell_measurement_theta_max      25.85

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.725
_exptl_absorpt_correction_T_max  0.836
_exptl_absorpt_process_details   'MULscanABS in PLATON; Spek, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       'phi oscillation'
_diffrn_detector_area_resol_mean 0.81\%A
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10520
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_sigmaI/netI    0.0828
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         25.95
_reflns_number_total             5992
_reflns_number_gt                3851
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'EXPOSE (Stoe, 2000)'
_computing_cell_refinement       'CELL (Stoe, 2000)'
_computing_data_reduction        'INTEGRATE (Stoe, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL-97

_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)+(0.0766P)²] 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         5992
_refine_ls_number_parameters     505
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1291
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   0.902
_refine_ls_restrained_S_all      0.902
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001


#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
Zn1 Zn Uani 0.48481(5) 0.31754(3) 0.29469(3) 1.000 0.0250(1) . .
F1 F Uani 0.0748(3) 0.1971(3) 0.5568(3) 1.000 0.0781(13) . .
F2 F Uani 0.1311(4) 0.0484(3) 0.5165(4) 1.000 0.1133(19) . .
F3 F Uani 0.0506(4) 0.1670(4) 0.4156(3) 1.000 0.1108(19) . .
F4 F Uani 0.6005(4) 0.2368(3) 0.6310(2) 1.000 0.0700(14) . .
F5 F Uani 0.5855(4) 0.0728(3) 0.6328(3) 1.000 0.0926(16) . .
F6 F Uani 0.7539(3) 0.1536(3) 0.5377(2) 1.000 0.0785(13) . .
F7 F Uani 0.6323(3) 0.0286(2) 0.1252(3) 1.000 0.0718(13) . .
F8 F Uani 0.7409(4) -0.0055(2) 0.2510(3) 1.000 0.0799(13) . .
F9 F Uani 0.8525(3) 0.0491(2) 0.1095(3) 1.000 0.0724(13) . .
F10 F Uani 1.0482(3) 0.3397(2) 0.1781(3) 1.000 0.0667(13) . .
F11 F Uani 0.9425(3) 0.4216(3) 0.2927(3) 1.000 0.0748(14) . .
F12 F Uani 0.9243(3) 0.4813(2) 0.1428(3) 1.000 0.0763(13) . .
O1 O Uani 0.3053(3) 0.2321(2) 0.3588(2) 1.000 0.0309(9) . .
O2 O Uani 0.5805(3) 0.2472(2) 0.4159(2) 1.000 0.0347(9) . .
O3 O Uani 0.5647(3) 0.19734(18) 0.2125(2) 1.000 0.0300(9) . .
O4 O Uani 0.6808(3) 0.38746(18) 0.2406(2) 1.000 0.0300(9) . .
O5 O Uani 0.3960(3) 0.7539(2) 0.0524(2) 1.000 0.0463(10) . .
N1 N Uani 0.3826(3) 0.4455(2) 0.3682(2) 1.000 0.0264(10) . .
N2 N Uani 0.3729(3) 0.4047(2) 0.1831(2) 1.000 0.0247(9) . .
N3 N Uani 0.0700(3) 0.6267(2) 0.3170(2) 1.000 0.0293(10) . .
N4 N Uani 0.2216(3) 0.6784(2) 0.1657(2) 1.000 0.0281(10) . .
N5 N Uani -0.0171(4) 0.7525(3) 0.0844(3) 1.000 0.0400(12) . .
N6 N Uani 0.1396(4) 0.8742(2) 0.2246(3) 1.000 0.0332(11) . .
C1 C Uani 0.3718(4) 0.4477(3) 0.4658(3) 1.000 0.0333(12) . .
C2 C Uani 0.2708(5) 0.5126(3) 0.5154(3) 1.000 0.0422(16) . .
C3 C Uani 0.1749(5) 0.5732(3) 0.4637(3) 1.000 0.0378(14) . .
C4 C Uani 0.1844(4) 0.5736(3) 0.3615(3) 1.000 0.0293(11) . .
C5 C Uani 0.2934(4) 0.5096(3) 0.3143(3) 1.000 0.0244(11) . .
C6 C Uani 0.3115(4) 0.4985(3) 0.2086(3) 1.000 0.0223(11) . .
C7 C Uani 0.2686(4) 0.5770(3) 0.1366(3) 1.000 0.0261(11) . .
C8 C Uani 0.2743(4) 0.5563(3) 0.0393(3) 1.000 0.0298(12) . .
C9 C Uani 0.3305(4) 0.4598(3) 0.0168(3) 1.000 0.0307(12) . .
C10 C Uani 0.3830(4) 0.3872(3) 0.0901(3) 1.000 0.0281(11) . .
C11 C Uani 0.0864(4) 0.6752(3) 0.2296(3) 1.000 0.0285(11) . .
C12 C Uani -0.0425(4) 0.7192(3) 0.1813(3) 1.000 0.0308(13) . .
C13 C Uani -0.1764(5) 0.7174(3) 0.2365(3) 1.000 0.0391(14) . .
C14 C Uani -0.2943(5) 0.7515(3) 0.1880(4) 1.000 0.0457(14) . .
C15 C Uani -0.2690(5) 0.7860(3) 0.0871(4) 1.000 0.0402(14) . .
C16 C Uani -0.1302(5) 0.7864(4) 0.0409(4) 1.000 0.0454(17) . .
C17 C Uani 0.2937(4) 0.7643(3) 0.1179(3) 1.000 0.0320(12) . .
C18 C Uani 0.2545(4) 0.8679(3) 0.1534(3) 1.000 0.0293(11) . .
C19 C Uani 0.3395(5) 0.9501(3) 0.1158(3) 1.000 0.0390(14) . .
C20 C Uani 0.3059(5) 1.0441(3) 0.1514(4) 1.000 0.0416(16) . .
C21 C Uani 0.1890(5) 1.0536(3) 0.2215(3) 1.000 0.0350(14) . .
C22 C Uani 0.1088(5) 0.9674(3) 0.2564(3) 1.000 0.0368(14) . .
C23 C Uani 0.2869(4) 0.1818(3) 0.4454(3) 1.000 0.0322(14) . .
C24 C Uani 0.3860(5) 0.1550(3) 0.5106(3) 1.000 0.0410(16) . .
C25 C Uani 0.5230(4) 0.1886(3) 0.4915(3) 1.000 0.0330(12) . .
C26 C Uani 0.1358(5) 0.1494(4) 0.4828(4) 1.000 0.0435(17) . .
C27 C Uani 0.6169(5) 0.1612(4) 0.5723(4) 1.000 0.0481(17) . .
C28 C Uani 0.6951(4) 0.1725(3) 0.1920(3) 1.000 0.0250(11) . .
C29 C Uani 0.8102(4) 0.2330(3) 0.1924(3) 1.000 0.0283(11) . .
C30 C Uani 0.7938(4) 0.3343(3) 0.2152(3) 1.000 0.0245(11) . .
C31 C Uani 0.7296(4) 0.0607(3) 0.1689(3) 1.000 0.0333(14) . .
C32 C Uani 0.9286(4) 0.3941(3) 0.2067(3) 1.000 0.0348(14) . .
H1A H Uiso 0.43570 0.40310 0.50260 1.000 0.0400 calc R
H2A H Uiso 0.26850 0.51470 0.58430 1.000 0.0510 calc R
H3A H Uiso 0.10170 0.61500 0.49730 1.000 0.0450 calc R
H8A H Uiso 0.24020 0.60800 -0.01020 1.000 0.0350 calc R
H9A H Uiso 0.33330 0.44300 -0.04820 1.000 0.0360 calc R
H10A H Uiso 0.42780 0.32260 0.07290 1.000 0.0340 calc R
H13A H Uiso -0.18860 0.69340 0.30610 1.000 0.0470 calc R
H14A H Uiso -0.38850 0.75100 0.22340 1.000 0.0550 calc R
H15A H Uiso -0.34540 0.80880 0.05060 1.000 0.0480 calc R
H16A H Uiso -0.11390 0.81310 -0.02810 1.000 0.0550 calc R
H19A H Uiso 0.41990 0.94210 0.06630 1.000 0.0470 calc R
H20A H Uiso 0.36360 1.10190 0.12730 1.000 0.0500 calc R
H21A H Uiso 0.16290 1.11830 0.24610 1.000 0.0420 calc R
H22A H Uiso 0.02770 0.97470 0.30560 1.000 0.0440 calc R
H24A H Uiso 0.35810 0.11110 0.57180 1.000 0.0490 calc R
H29A H Uiso 0.90410 0.20290 0.17630 1.000 0.0340 calc R


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.110(3) . . yes
Zn1 O2 2.074(3) . . yes
Zn1 O3 2.086(3) . . yes
Zn1 O4 2.118(3) . . yes
Zn1 N1 2.155(3) . . yes
Zn1 N2 2.127(3) . . yes
F1 C26 1.306(7) . . yes
F2 C26 1.314(7) . . yes
F3 C26 1.307(6) . . yes
F4 C27 1.348(6) . . yes
F5 C27 1.327(7) . . yes
F6 C27 1.316(6) . . yes
F7 C31 1.311(5) . . yes
F8 C31 1.317(5) . . yes
F9 C31 1.328(5) . . yes
F10 C32 1.323(5) . . yes
F11 C32 1.319(6) . . yes
F12 C32 1.315(5) . . yes
O1 C23 1.257(5) . . yes
O2 C25 1.262(5) . . yes
O3 C28 1.254(5) . . yes
O4 C30 1.256(5) . . yes
O5 C17 1.231(5) . . yes
N1 C1 1.336(5) . . yes
N1 C5 1.357(5) . . yes
N2 C6 1.371(5) . . yes
N2 C10 1.323(5) . . yes
N3 C4 1.408(5) . . yes
N3 C11 1.257(5) . . yes
N4 C7 1.444(5) . . yes
N4 C11 1.438(5) . . yes
N4 C17 1.374(5) . . yes
N5 C12 1.325(6) . . yes
N5 C16 1.323(6) . . yes
N6 C18 1.353(6) . . yes
N6 C22 1.339(5) . . yes
C1 C2 1.388(6) . . no
C2 C3 1.363(6) . . no
C3 C4 1.395(6) . . no
C4 C5 1.410(6) . . no
C5 C6 1.467(6) . . no
C6 C7 1.383(6) . . no
C7 C8 1.400(6) . . no
C8 C9 1.375(6) . . no
C9 C10 1.387(6) . . no
C11 C12 1.514(6) . . no
C12 C13 1.376(6) . . no
C13 C14 1.400(7) . . no
C14 C15 1.379(8) . . no
C15 C16 1.372(7) . . no
C17 C18 1.494(6) . . no
C18 C19 1.374(6) . . no
C19 C20 1.374(6) . . no
C20 C21 1.362(7) . . no
C21 C22 1.383(6) . . no
C23 C24 1.390(6) . . no
C23 C26 1.519(6) . . no
C24 C25 1.383(6) . . no
C25 C27 1.517(6) . . no
C28 C29 1.402(6) . . no
C28 C31 1.525(6) . . no
C29 C30 1.384(6) . . no
C30 C32 1.534(6) . . no
C1 H1A 0.9500 . . no
C2 H2A 0.9500 . . no
C3 H3A 0.9500 . . no
C8 H8A 0.9500 . . no
C9 H9A 0.9500 . . no
C10 H10A 0.9500 . . no
C13 H13A 0.9500 . . no
C14 H14A 0.9500 . . no
C15 H15A 0.9500 . . no
C16 H16A 0.9500 . . no
C19 H19A 0.9500 . . no
C20 H20A 0.9500 . . no
C21 H21A 0.9500 . . no
C22 H22A 0.9500 . . no
C24 H24A 0.9500 . . no
C29 H29A 0.9500 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O2 87.21(11) . . . yes
O1 Zn1 O3 90.39(11) . . . yes
O1 Zn1 O4 172.51(11) . . . yes
O1 Zn1 N1 87.22(11) . . . yes
O1 Zn1 N2 91.79(11) . . . yes
O2 Zn1 O3 92.43(11) . . . yes
O2 Zn1 O4 86.05(11) . . . yes
O2 Zn1 N1 93.93(10) . . . yes
O2 Zn1 N2 172.16(11) . . . yes
O3 Zn1 O4 86.63(10) . . . yes
O3 Zn1 N1 173.09(11) . . . yes
O3 Zn1 N2 95.35(10) . . . yes
O4 Zn1 N1 96.51(10) . . . yes
O4 Zn1 N2 95.34(11) . . . yes
N1 Zn1 N2 78.25(10) . . . yes
Zn1 O1 C23 125.2(3) . . . yes
Zn1 O2 C25 126.6(3) . . . yes
Zn1 O3 C28 123.4(2) . . . yes
Zn1 O4 C30 122.3(2) . . . yes
Zn1 N1 C1 124.4(2) . . . yes
Zn1 N1 C5 113.5(2) . . . yes
C1 N1 C5 119.5(3) . . . yes
Zn1 N2 C6 112.7(2) . . . yes
Zn1 N2 C10 126.2(2) . . . yes
C6 N2 C10 119.5(3) . . . yes
C4 N3 C11 122.4(3) . . . yes
C7 N4 C11 111.6(3) . . . yes
C7 N4 C17 118.3(3) . . . yes
C11 N4 C17 129.0(3) . . . yes
C12 N5 C16 116.0(4) . . . yes
C18 N6 C22 116.3(3) . . . yes
N1 C1 C2 122.5(4) . . . yes
C1 C2 C3 118.9(4) . . . no
C2 C3 C4 119.9(4) . . . no
N3 C4 C3 115.8(3) . . . yes
N3 C4 C5 124.9(3) . . . yes
C3 C4 C5 118.6(4) . . . no
N1 C5 C4 120.5(4) . . . yes
N1 C5 C6 115.0(3) . . . yes
C4 C5 C6 124.3(4) . . . no
N2 C6 C5 116.8(3) . . . yes
N2 C6 C7 120.3(4) . . . yes
C5 C6 C7 122.9(4) . . . no
N4 C7 C6 117.7(3) . . . yes
N4 C7 C8 122.8(3) . . . yes
C6 C7 C8 119.5(4) . . . no
C7 C8 C9 118.7(4) . . . no
C8 C9 C10 119.2(4) . . . no
N2 C10 C9 122.4(4) . . . yes
N3 C11 N4 123.2(3) . . . yes
N3 C11 C12 119.9(3) . . . yes
N4 C11 C12 116.2(3) . . . yes
N5 C12 C11 115.7(4) . . . yes
N5 C12 C13 124.1(4) . . . yes
C11 C12 C13 120.1(4) . . . no
C12 C13 C14 118.6(4) . . . no
C13 C14 C15 117.7(4) . . . no
C14 C15 C16 118.1(5) . . . no
N5 C16 C15 125.4(5) . . . yes
O5 C17 N4 120.2(3) . . . yes
O5 C17 C18 120.7(3) . . . yes
N4 C17 C18 118.8(3) . . . yes
N6 C18 C17 117.7(3) . . . yes
N6 C18 C19 123.4(4) . . . yes
C17 C18 C19 118.9(4) . . . no
C18 C19 C20 118.6(4) . . . no
C19 C20 C21 119.4(4) . . . no
C20 C21 C22 118.9(4) . . . no
N6 C22 C21 123.4(4) . . . yes
O1 C23 C24 128.1(4) . . . yes
O1 C23 C26 114.9(4) . . . yes
C24 C23 C26 117.0(4) . . . no
C23 C24 C25 123.7(4) . . . no
O2 C25 C24 128.2(4) . . . yes
O2 C25 C27 113.1(4) . . . yes
C24 C25 C27 118.5(4) . . . no
F1 C26 F2 105.5(5) . . . yes
F1 C26 F3 106.6(4) . . . yes
F1 C26 C23 112.1(4) . . . yes
F2 C26 F3 104.9(5) . . . yes
F2 C26 C23 112.5(4) . . . yes
F3 C26 C23 114.5(4) . . . yes
F4 C27 F5 105.6(4) . . . yes
F4 C27 F6 105.6(4) . . . yes
F4 C27 C25 110.4(4) . . . yes
F5 C27 F6 107.7(4) . . . yes
F5 C27 C25 113.4(4) . . . yes
F6 C27 C25 113.5(4) . . . yes
O3 C28 C29 127.9(4) . . . yes
O3 C28 C31 114.7(3) . . . yes
C29 C28 C31 117.4(3) . . . no
C28 C29 C30 123.2(4) . . . no
O4 C30 C29 128.8(4) . . . yes
O4 C30 C32 113.4(3) . . . yes
C29 C30 C32 117.8(3) . . . no
F7 C31 F8 108.0(4) . . . yes
F7 C31 F9 106.1(4) . . . yes
F7 C31 C28 112.6(3) . . . yes
F8 C31 F9 105.8(3) . . . yes
F8 C31 C28 110.6(3) . . . yes
F9 C31 C28 113.4(3) . . . yes
F10 C32 F11 106.2(3) . . . yes
F10 C32 F12 106.9(3) . . . yes
F10 C32 C30 114.0(3) . . . yes
F11 C32 F12 106.7(4) . . . yes
F11 C32 C30 111.3(3) . . . yes
F12 C32 C30 111.3(3) . . . yes
N1 C1 H1A 119.00 . . . no
C2 C1 H1A 119.00 . . . no
C1 C2 H2A 121.00 . . . no
C3 C2 H2A 121.00 . . . no
C2 C3 H3A 120.00 . . . no
C4 C3 H3A 120.00 . . . no
C7 C8 H8A 121.00 . . . no
C9 C8 H8A 121.00 . . . no
C8 C9 H9A 120.00 . . . no
C10 C9 H9A 120.00 . . . no
N2 C10 H10A 119.00 . . . no
C9 C10 H10A 119.00 . . . no
C12 C13 H13A 121.00 . . . no
C14 C13 H13A 121.00 . . . no
C13 C14 H14A 121.00 . . . no
C15 C14 H14A 121.00 . . . no
C14 C15 H15A 121.00 . . . no
C16 C15 H15A 121.00 . . . no
N5 C16 H16A 117.00 . . . no
C15 C16 H16A 117.00 . . . no
C18 C19 H19A 121.00 . . . no
C20 C19 H19A 121.00 . . . no
C19 C20 H20A 120.00 . . . no
C21 C20 H20A 120.00 . . . no
C20 C21 H21A 121.00 . . . no
C22 C21 H21A 120.00 . . . no
N6 C22 H22A 118.00 . . . no
C21 C22 H22A 118.00 . . . no
C23 C24 H24A 118.00 . . . no
C25 C24 H24A 118.00 . . . no
C28 C29 H29A 118.00 . . . no
C30 C29 H29A 118.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Zn1 O1 C23 10.7(3) . . . . no
O3 Zn1 O1 C23 103.1(3) . . . . no
N1 Zn1 O1 C23 -83.4(3) . . . . no
N2 Zn1 O1 C23 -161.5(3) . . . . no
O1 Zn1 O2 C25 -5.9(3) . . . . no
O3 Zn1 O2 C25 -96.1(3) . . . . no
O4 Zn1 O2 C25 177.4(3) . . . . no
N1 Zn1 O2 C25 81.2(3) . . . . no
O1 Zn1 O3 C28 -145.6(3) . . . . no
O2 Zn1 O3 C28 -58.4(3) . . . . no
O4 Zn1 O3 C28 27.5(3) . . . . no
N2 Zn1 O3 C28 122.5(3) . . . . no
O2 Zn1 O4 C30 66.2(3) . . . . no
O3 Zn1 O4 C30 -26.5(3) . . . . no
N1 Zn1 O4 C30 159.7(3) . . . . no
N2 Zn1 O4 C30 -121.6(3) . . . . no
O1 Zn1 N1 C1 74.0(3) . . . . no
O1 Zn1 N1 C5 -87.4(3) . . . . no
O2 Zn1 N1 C1 -13.1(3) . . . . no
O2 Zn1 N1 C5 -174.4(3) . . . . no
O4 Zn1 N1 C1 -99.5(3) . . . . no
O4 Zn1 N1 C5 99.1(3) . . . . no
N2 Zn1 N1 C1 166.4(3) . . . . no
N2 Zn1 N1 C5 5.0(2) . . . . no
O1 Zn1 N2 C6 94.0(2) . . . . no
O1 Zn1 N2 C10 -100.5(3) . . . . no
O3 Zn1 N2 C6 -175.4(2) . . . . no
O3 Zn1 N2 C10 -9.9(3) . . . . no
O4 Zn1 N2 C6 -88.3(2) . . . . no
O4 Zn1 N2 C10 77.2(3) . . . . no
N1 Zn1 N2 C6 7.2(2) . . . . no
N1 Zn1 N2 C10 172.7(3) . . . . no
Zn1 O1 C23 C24 -12.5(6) . . . . no
Zn1 O1 C23 C26 165.8(3) . . . . no
Zn1 O2 C25 C24 2.0(6) . . . . no
Zn1 O2 C25 C27 -172.8(3) . . . . no
Zn1 O3 C28 C29 -19.7(6) . . . . no
Zn1 O3 C28 C31 157.1(2) . . . . no
Zn1 O4 C30 C29 18.0(6) . . . . no
Zn1 O4 C30 C32 -163.7(2) . . . . no
Zn1 N1 C1 C2 -159.5(3) . . . . no
C5 N1 C1 C2 0.8(6) . . . . no
Zn1 N1 C5 C4 158.6(3) . . . . no
Zn1 N1 C5 C6 -15.8(4) . . . . no
C1 N1 C5 C4 -3.8(5) . . . . no
C1 N1 C5 C6 -178.2(3) . . . . no
Zn1 N2 C6 C5 -18.1(4) . . . . no
Zn1 N2 C6 C7 162.5(3) . . . . no
C10 N2 C6 C5 175.3(3) . . . . no
C10 N2 C6 C7 -4.1(5) . . . . no
Zn1 N2 C10 C9 -166.1(3) . . . . no
C6 N2 C10 C9 -1.5(6) . . . . no
C11 N3 C4 C3 146.6(4) . . . . no
C11 N3 C4 C5 -43.3(6) . . . . no
C4 N3 C11 N4 2.1(6) . . . . no
C4 N3 C11 C12 172.4(3) . . . . no
C11 N4 C7 C6 -70.6(4) . . . . no
C11 N4 C7 C8 110.5(4) . . . . no
C17 N4 C7 C6 120.4(4) . . . . no
C17 N4 C7 C8 -58.6(5) . . . . no
C7 N4 C11 N3 68.8(5) . . . . no
C7 N4 C11 C12 -101.8(4) . . . . no
C17 N4 C11 N3 -123.6(4) . . . . no
C17 N4 C11 C12 65.8(5) . . . . no
C7 N4 C17 O5 -0.3(5) . . . . no
C7 N4 C17 C18 -174.6(3) . . . . no
C11 N4 C17 O5 -167.3(4) . . . . no
C11 N4 C17 C18 18.5(6) . . . . no
C16 N5 C12 C11 176.9(4) . . . . no
C16 N5 C12 C13 0.6(6) . . . . no
C12 N5 C16 C15 -2.5(7) . . . . no
C22 N6 C18 C17 178.7(4) . . . . no
C22 N6 C18 C19 1.6(6) . . . . no
C18 N6 C22 C21 -1.2(6) . . . . no
N1 C1 C2 C3 2.9(6) . . . . no
C1 C2 C3 C4 -3.5(6) . . . . no
C2 C3 C4 N3 171.5(4) . . . . no
C2 C3 C4 C5 0.7(6) . . . . no
N3 C4 C5 N1 -166.9(3) . . . . no
N3 C4 C5 C6 7.0(6) . . . . no
C3 C4 C5 N1 3.0(6) . . . . no
C3 C4 C5 C6 176.9(4) . . . . no
N1 C5 C6 N2 23.2(5) . . . . no
N1 C5 C6 C7 -157.4(4) . . . . no
C4 C5 C6 N2 -151.0(4) . . . . no
C4 C5 C6 C7 28.4(6) . . . . no
N2 C6 C7 N4 -172.3(3) . . . . no
N2 C6 C7 C8 6.7(6) . . . . no
C5 C6 C7 N4 8.4(6) . . . . no
C5 C6 C7 C8 -172.7(4) . . . . no
N4 C7 C8 C9 175.2(3) . . . . no
C6 C7 C8 C9 -3.7(6) . . . . no
C7 C8 C9 C10 -1.7(6) . . . . no
C8 C9 C10 N2 4.4(6) . . . . no
N3 C11 C12 N5 -168.6(4) . . . . no
N3 C11 C12 C13 7.8(6) . . . . no
N4 C11 C12 N5 2.3(5) . . . . no
N4 C11 C12 C13 178.7(3) . . . . no
N5 C12 C13 C14 0.8(6) . . . . no
C11 C12 C13 C14 -175.3(4) . . . . no
C12 C13 C14 C15 -0.5(6) . . . . no
C13 C14 C15 C16 -1.0(6) . . . . no
C14 C15 C16 N5 2.7(7) . . . . no
O5 C17 C18 N6 179.1(4) . . . . no
O5 C17 C18 C19 -3.7(6) . . . . no
N4 C17 C18 N6 -6.7(5) . . . . no
N4 C17 C18 C19 170.5(4) . . . . no
N6 C18 C19 C20 -0.6(7) . . . . no
C17 C18 C19 C20 -177.6(4) . . . . no
C18 C19 C20 C21 -0.9(7) . . . . no
C19 C20 C21 C22 1.3(7) . . . . no
C20 C21 C22 N6 -0.2(7) . . . . no
O1 C23 C24 C25 5.5(7) . . . . no
C26 C23 C24 C25 -172.8(4) . . . . no
O1 C23 C26 F1 -113.7(5) . . . . no
O1 C23 C26 F2 127.6(5) . . . . no
O1 C23 C26 F3 8.0(6) . . . . no
C24 C23 C26 F1 64.9(5) . . . . no
C24 C23 C26 F2 -53.8(6) . . . . no
C24 C23 C26 F3 -173.5(4) . . . . no
C23 C24 C25 O2 0.5(7) . . . . no
C23 C24 C25 C27 175.1(4) . . . . no
O2 C25 C27 F4 85.6(5) . . . . no
O2 C25 C27 F5 -156.2(4) . . . . no
O2 C25 C27 F6 -32.8(6) . . . . no
C24 C25 C27 F4 -89.8(5) . . . . no
C24 C25 C27 F5 28.5(6) . . . . no
C24 C25 C27 F6 151.8(4) . . . . no
O3 C28 C29 C30 -1.1(7) . . . . no
C31 C28 C29 C30 -177.9(4) . . . . no
O3 C28 C31 F7 32.9(5) . . . . no
O3 C28 C31 F8 -88.0(4) . . . . no
O3 C28 C31 F9 153.3(4) . . . . no
C29 C28 C31 F7 -149.9(4) . . . . no
C29 C28 C31 F8 89.2(4) . . . . no
C29 C28 C31 F9 -29.5(5) . . . . no
C28 C29 C30 O4 1.8(7) . . . . no
C28 C29 C30 C32 -176.4(4) . . . . no
O4 C30 C32 F10 -178.7(4) . . . . no
O4 C30 C32 F11 61.2(5) . . . . no
O4 C30 C32 F12 -57.7(5) . . . . no
C29 C30 C32 F10 -0.3(5) . . . . no
C29 C30 C32 F11 -120.4(4) . . . . no
C29 C30 C32 F12 120.7(4) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
F1 N3 3.170(5) . 2_566 no
F2 F6 2.902(6) . 2_656 no
F2 F2 3.016(6) . 2_556 no
F3 F6 3.051(5) . 1_455 no
F3 C21 3.289(6) . 1_545 no
F3 O1 2.596(5) . . no
F4 C4 3.351(5) . 2_666 no
F4 C3 3.360(6) . 2_666 no
F4 O2 2.980(4) . . no
F5 C21 3.320(6) . 2_666 no
F6 F3 3.051(5) . 1_655 no
F6 F2 2.902(6) . 2_656 no
F6 O2 2.625(4) . . no
F7 C15 3.291(5) . 1_645 no
F7 O3 2.637(4) . . no
F7 C19 3.077(6) . 1_545 no
F7 C20 3.064(6) . 1_545 no
F7 C19 3.256(6) . 2_665 no
F8 O3 3.005(4) . . no
F10 C10 3.297(5) . 1_655 no
F11 N3 3.095(5) . 1_655 no
F11 O4 2.791(4) . . no
F11 C2 3.245(6) . 2_666 no
F12 O4 2.761(4) . . no
F12 C12 3.250(5) . 1_655 no
F1 H24A 2.8500 . . no
F1 H22A 2.8100 . 2_566 no
F2 H22A 2.6500 . 2_566 no
F2 H24A 2.6300 . . no
F3 H21A 2.5600 . 1_545 no
F4 H14A 2.6200 . 2_566 no
F5 H24A 2.4300 . . no
F7 H20A 2.6500 . 1_545 no
F7 H19A 2.7200 . 2_665 no
F7 H19A 2.6900 . 1_545 no
F8 H24A 2.6700 . 2_656 no
F9 H29A 2.4400 . . no
F10 H29A 2.3400 . . no
F11 H3A 2.8200 . 2_666 no
F11 H2A 2.5800 . 2_666 no
O1 F3 2.596(5) . . no
O1 O2 2.885(4) . . no
O1 O3 2.977(4) . . no
O1 N1 2.941(4) . . no
O1 N2 3.042(4) . . no
O1 C25 2.939(5) . . no
O2 C1 3.219(5) . . no
O2 F4 2.980(4) . . no
O2 F6 2.625(4) . . no
O2 O1 2.885(4) . . no
O2 O3 3.003(4) . . no
O2 O4 2.860(4) . . no
O2 N1 3.091(4) . . no
O2 C30 3.260(5) . . no
O2 C23 2.938(5) . . no
O2 C28 3.365(5) . . no
O3 O2 3.003(4) . . no
O3 C10 3.273(5) . . no
O3 F7 2.637(4) . . no
O3 F8 3.005(4) . . no
O3 O1 2.977(4) . . no
O3 O4 2.884(4) . . no
O3 N2 3.115(4) . . no
O3 C30 2.934(5) . . no
O4 F11 2.791(4) . . no
O4 N1 3.188(4) . . no
O4 N2 3.138(4) . . no
O4 C28 2.945(5) . . no
O4 O3 2.884(4) . . no
O4 F12 2.761(4) . . no
O4 O2 2.860(4) . . no
O5 C15 3.371(6) . 1_655 no
O5 C8 2.936(5) . . no
O5 C10 3.279(5) . 2_665 no
O1 H21A 2.8600 . 1_545 no
O2 H1A 2.6700 . . no
O3 H20A 2.8600 . 1_545 no
O3 H10A 2.7300 . . no
O5 H15A 2.6200 . 1_655 no
O5 H19A 2.5000 . . no
O5 H8A 2.8100 . . no
O5 H10A 2.4700 . 2_665 no
N1 O1 2.941(4) . . no
N1 O2 3.091(4) . . no
N1 O4 3.188(4) . . no
N1 N2 2.702(4) . . no
N1 C6 2.382(5) . . no
N2 O1 3.042(4) . . no
N2 O3 3.115(4) . . no
N2 O4 3.138(4) . . no
N2 N1 2.702(4) . . no
N2 C5 2.417(5) . . no
N3 F11 3.095(5) . 1_455 no
N3 F1 3.170(5) . 2_566 no
N4 N6 2.788(4) . . no
N4 N5 2.726(5) . . no
N5 C18 3.425(6) . . no
N5 N4 2.726(5) . . no
N5 N6 3.277(5) . . no
N5 C17 3.088(5) . . no
N6 C11 2.650(5) . . no
N6 N4 2.788(4) . . no
N6 N5 3.277(5) . . no
N6 C12 2.948(5) . . no
N3 H13A 2.5600 . . no
C1 C25 3.512(6) . . no
C1 C1 3.225(6) . 2_666 no
C1 C2 3.542(6) . 2_666 no
C2 F11 3.245(6) . 2_666 no
C2 C1 3.542(6) . 2_666 no
C3 F4 3.360(6) . 2_666 no
C4 F4 3.351(5) . 2_666 no
C8 C10 3.534(6) . 2_665 no
C8 O5 2.936(5) . . no
C9 C10 3.497(6) . 2_665 no
C9 C9 3.415(6) . 2_665 no
C10 C9 3.497(6) . 2_665 no
C10 F10 3.297(5) . 1_455 no
C10 O5 3.279(5) . 2_665 no
C10 C8 3.534(6) . 2_665 no
C11 N6 2.650(5) . . no
C12 C18 3.492(6) . . no
C12 F12 3.250(5) . 1_455 no
C12 N6 2.948(5) . . no
C15 F7 3.291(5) . 1_465 no
C15 O5 3.371(6) . 1_455 no
C17 N5 3.088(5) . . no
C18 N5 3.425(6) . . no
C18 C12 3.492(6) . . no
C19 F7 3.256(6) . 2_665 no
C19 F7 3.078(6) . 1_565 no
C20 F7 3.064(6) . 1_565 no
C21 F5 3.320(6) . 2_666 no
C21 F3 3.289(6) . 1_565 no
C25 C1 3.512(6) . . no
C1 H1A 2.9000 . 2_666 no
C2 H1A 3.0500 . 2_666 no
C17 H8A 3.0100 . . no
C20 H16A 3.0000 . 2_575 no
C20 H15A 3.1000 . 2_575 no
C21 H16A 3.0800 . 2_575 no
C25 H1A 2.8400 . . no
C29 H8A 3.0500 . 2_665 no
C30 H8A 2.8600 . 2_665 no
H1A O2 2.6700 . . no
H1A C25 2.8400 . . no
H1A C1 2.9000 . 2_666 no
H1A C2 3.0500 . 2_666 no
H2A F11 2.5800 . 2_666 no
H3A F11 2.8200 . 2_666 no
H8A O5 2.8100 . . no
H8A C17 3.0100 . . no
H8A C29 3.0500 . 2_665 no
H8A C30 2.8600 . 2_665 no
H10A O3 2.7300 . . no
H10A O5 2.4700 . 2_665 no
H13A N3 2.5600 . . no
H14A F4 2.6200 . 2_566 no
H15A O5 2.6200 . 1_455 no
H15A C20 3.1000 . 2_575 no
H15A H20A 2.5600 . 2_575 no
H16A C20 3.0000 . 2_575 no
H16A C21 3.0800 . 2_575 no
H19A F7 2.6900 . 1_565 no
H19A O5 2.5000 . . no
H19A F7 2.7200 . 2_665 no
H19A H19A 2.5500 . 2_675 no
H20A F7 2.6500 . 1_565 no
H20A O3 2.8600 . 1_565 no
H20A H15A 2.5600 . 2_575 no
H21A F3 2.5600 . 1_565 no
H21A O1 2.8600 . 1_565 no
H22A F1 2.8100 . 2_566 no
H22A F2 2.6500 . 2_566 no
H24A F1 2.8500 . . no
H24A F2 2.6300 . . no
H24A F5 2.4300 . . no
H24A F8 2.6700 . 2_656 no
H29A F9 2.4400 . . no
H29A F10 2.3400 . . no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C10 H10A O5 0.95 2.47 3.279(5) 143 2_665 yes
C24 H24A F5 0.95 2.43 2.769(6) 101 . yes
C29 H29A F9 0.95 2.44 2.768(5) 100 . yes
C29 H29A F10 0.95 2.34 2.718(5) 103 . yes



_diffrn_measured_fraction_theta_max 0.931
_diffrn_reflns_theta_full        25.95
_diffrn_measured_fraction_theta_full 0.931
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.849
_refine_diff_density_rms         0.099
_vrf_PLAT029_mel-7jw             
; 
PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.93 
RESPONSE: ...With the Stoe IPDS I machine for the triclinic system only 
ca. 93% of the Ewald sphere is accessible 
[_diffrn_measured_fraction_theta_max    0.932]. 
This has a negligible effect on the bond distances and angles.
;
_vrf_PLAT242_mel-7jw             
; 
PROBLEM: Check Low       Ueq as Compared to Neighbors for        C26 
RESPONSE: ...this is part of a -CF3 group which may be disordered
;
