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

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

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            "Urea : 4,4'bipyridine Form I"
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H12 N4 O'
_chemical_formula_weight         216.25

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   ' C 2/c '

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

_cell_length_a                   14.999(3)
_cell_length_b                   4.6030(9)
_cell_length_c                   16.068(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.53(3)
_cell_angle_gamma                90.00
_cell_volume                     1051.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1356
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.093
# Permitted for _exptl_absorpt_correction_type :
# analytical     'analytical from crystal shape'
#                Example: de Meulenaer&Tompa: ABST
# cylinder       'cylindrical'
# gaussian       'Gaussian from crystal shape'
#                Example: PLATON/ABSG
# integration    'integration from crystal shape'
# multi-scan     'symmetry-related measurements'
#                Example: SADABS, MULABS
# none           'no absorption corr. applied'
# numerical      'numerical from crystal shape'
# psi-scan       'psi-scan corrections'
#                Example: PLATON/ABSP
# refdelf        'refined from delta-F'
#                Example: SHELXA,
# sphere         'spherical'
#                Example: PLATON/ABSS
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_min  0.9726
_exptl_absorpt_correction_T_max  0.9907
#===============================================================================

# 7. EXPERIMENTAL DATA

_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       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5213
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1195
_reflns_number_gt                1066
_reflns_threshold_expression     >2σ(I)


_computing_data_collection       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0860P)²+0.3329P] 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         1195
_refine_ls_number_parameters     98
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1566
_refine_ls_wR_factor_gt          0.1373
_refine_ls_goodness_of_fit_ref   1.254
_refine_ls_restrained_S_all      1.254
_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
H6 H 0.5439(13) 0.158(4) 0.7061(12) 0.030(4) Uiso 1 1 d . . .
H5 H 0.5716(13) 0.453(5) 0.6720(13) 0.035(5) Uiso 1 1 d . . .
H4 H 0.7574(16) 0.673(5) 0.2913(15) 0.043(5) Uiso 1 1 d . . .
H3 H 0.6756(16) 0.337(5) 0.3489(15) 0.046(6) Uiso 1 1 d . . .
H2 H 0.8897(13) 0.458(4) 0.5904(13) 0.038(5) Uiso 1 1 d . . .
H1 H 0.9583(16) 0.787(4) 0.5202(14) 0.048(6) Uiso 1 1 d . . .
O1 O 0.5000 0.7744(3) 0.7500 0.0325(4) Uani 1 2 d S . .
N1 N 0.54467(9) 0.3504(3) 0.70351(9) 0.0275(4) Uani 1 1 d . . .
C6 C 0.5000 0.5029(4) 0.7500 0.0221(4) Uani 1 2 d S . .
N2 N 0.86340(9) 0.7596(3) 0.39902(9) 0.0329(4) Uani 1 1 d . . .
C5 C 0.89852(11) 0.6908(4) 0.48389(11) 0.0343(4) Uani 1 1 d . . .
C2 C 0.73725(10) 0.4249(3) 0.39000(9) 0.0299(4) Uani 1 1 d . . .
C4 C 0.85743(10) 0.4934(3) 0.52627(10) 0.0304(4) Uani 1 1 d . . .
C3 C 0.77404(9) 0.3550(3) 0.47882(9) 0.0221(4) Uani 1 1 d . . .
C1 C 0.78395(12) 0.6244(3) 0.35383(10) 0.0339(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0484(9) 0.0154(7) 0.0405(9) 0.000 0.0237(7) 0.000
N1 0.0377(7) 0.0176(7) 0.0343(7) -0.0018(4) 0.0215(5) -0.0028(5)
C6 0.0256(9) 0.0176(9) 0.0223(8) 0.000 0.0066(7) 0.000
N2 0.0409(8) 0.0255(7) 0.0416(8) 0.0038(5) 0.0263(6) 0.0001(5)
C5 0.0328(8) 0.0315(8) 0.0420(9) 0.0022(6) 0.0167(7) -0.0059(6)
C2 0.0332(8) 0.0308(8) 0.0263(7) 0.0042(6) 0.0104(6) -0.0021(6)
C4 0.0312(8) 0.0303(8) 0.0301(8) 0.0035(6) 0.0104(6) -0.0035(6)
C3 0.0246(7) 0.0188(7) 0.0260(7) 0.0019(5) 0.0126(5) 0.0037(5)
C1 0.0460(9) 0.0315(8) 0.0287(8) 0.0058(6) 0.0183(7) 0.0005(6)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.250(2) . ?
N1 C6 1.3480(15) . ?
N1 H6 0.88(2) . ?
N1 H5 0.88(2) . ?
C6 N1 1.3480(16) 2_656 ?
N2 C5 1.334(2) . ?
N2 C1 1.336(2) . ?
C5 C4 1.391(2) . ?
C5 H1 1.00(2) . ?
C2 C1 1.390(2) . ?
C2 C3 1.3942(19) . ?
C2 H3 1.03(2) . ?
C4 C3 1.395(2) . ?
C4 H2 1.00(2) . ?
C3 C3 1.493(2) 7_656 ?
C1 H4 0.98(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
C6 N1 H6 118.5(12) . . ?
C6 N1 H5 116.2(13) . . ?
H6 N1 H5 125.2(19) . . ?
O1 C6 N1 121.36(9) . 2_656 ?
O1 C6 N1 121.36(9) . . ?
N1 C6 N1 117.28(17) 2_656 . ?
C5 N2 C1 116.04(13) . . ?
N2 C5 C4 124.26(14) . . ?
N2 C5 H1 118.6(13) . . ?
C4 C5 H1 117.1(13) . . ?
C1 C2 C3 119.50(14) . . ?
C1 C2 H3 117.4(13) . . ?
C3 C2 H3 123.1(13) . . ?
C5 C4 C3 119.36(14) . . ?
C5 C4 H2 117.8(11) . . ?
C3 C4 H2 122.9(11) . . ?
C2 C3 C4 116.66(13) . . ?
C2 C3 C3 121.64(15) . 7_656 ?
C4 C3 C3 121.70(15) . 7_656 ?
N2 C1 C2 124.18(14) . . ?
N2 C1 H4 116.8(13) . . ?
C2 C1 H4 119.0(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N2 C5 C4 -0.5(2) . . . . ?
N2 C5 C4 C3 0.0(2) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C1 C2 C3 C3 179.19(15) . . . 7_656 ?
C5 C4 C3 C2 0.4(2) . . . . ?
C5 C4 C3 C3 -178.98(15) . . . 7_656 ?
C5 N2 C1 C2 0.7(2) . . . . ?
C3 C2 C1 N2 -0.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.072
_database_code_depnum_ccdc_archive 'CCDC 984585'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_datam

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            "Urea : 4,4'bipyridine Form II"
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H12 N4 O'
_chemical_formula_weight         216.25

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           Orthorhombic
_symmetry_space_group_name_H-M   'P n m a'

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

_cell_length_a                   25.070(4)
_cell_length_b                   9.1849(15)
_cell_length_c                   4.5943(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1057.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8192
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            'colour less'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.093
# Permitted for _exptl_absorpt_correction_type :
# analytical     'analytical from crystal shape'
#                Example: de Meulenaer&Tompa: ABST
# cylinder       'cylindrical'
# gaussian       'Gaussian from crystal shape'
#                Example: PLATON/ABSG
# integration    'integration from crystal shape'
# multi-scan     'symmetry-related measurements'
#                Example: SADABS, MULABS
# none           'no absorption corr. applied'
# numerical      'numerical from crystal shape'
# psi-scan       'psi-scan corrections'
#                Example: PLATON/ABSP
# refdelf        'refined from delta-F'
#                Example: SHELXA,
# sphere         'spherical'
#                Example: PLATON/ABSS
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_min  0.9639
_exptl_absorpt_correction_T_max  0.9817
#===============================================================================

# 7. EXPERIMENTAL DATA

_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       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9326
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         3.25
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1274
_reflns_number_gt                1019
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0568P)²+0.3486P] 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         1274
_refine_ls_number_parameters     113
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1371
_refine_ls_wR_factor_gt          0.1310
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_restrained_S_all      1.141
_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
C1 C 0.45936(8) 0.1275(2) 1.1994(4) 0.0481(5) Uani 1 1 d . . .
C2 C 0.41743(7) 0.1220(2) 1.0030(4) 0.0421(5) Uani 1 1 d . . .
C3 C 0.39560(8) 0.2500 0.8979(4) 0.0279(5) Uani 1 2 d S . .
C4 C 0.35062(8) 0.2500 0.6861(4) 0.0263(5) Uani 1 2 d S . .
C5 C 0.32868(7) 0.1216(2) 0.5814(4) 0.0383(4) Uani 1 1 d . . .
C6 C 0.28781(7) 0.1278(2) 0.3785(4) 0.0442(5) Uani 1 1 d . . .
N1 N 0.48055(7) 0.2500 1.2993(5) 0.0445(6) Uani 1 2 d S . .
N2 N 0.26708(7) 0.2500 0.2732(4) 0.0414(6) Uani 1 2 d S . .
H1 H 0.4751(8) 0.036(3) 1.271(5) 0.069(7) Uiso 1 1 d . . .
H2 H 0.4055(8) 0.028(3) 0.928(5) 0.061(6) Uiso 1 1 d . . .
H5 H 0.3426(8) 0.028(2) 0.642(4) 0.052(6) Uiso 1 1 d . . .
H6 H 0.2737(7) 0.039(3) 0.307(5) 0.055(6) Uiso 1 1 d . . .
C7 C 0.12570(8) 0.2500 -0.0127(5) 0.0285(5) Uani 1 2 d S . .
N3 N 0.17178(8) 0.2500 -0.1612(5) 0.0358(5) Uani 1 2 d S . .
N4 N 0.08040(8) 0.2500 -0.1684(4) 0.0355(5) Uani 1 2 d S . .
O1 O 0.12500(6) 0.2500 0.2579(3) 0.0453(5) Uani 1 2 d S . .
H3A H 0.2016(11) 0.2500 -0.060(6) 0.038(7) Uiso 1 2 d S . .
H3B H 0.1718(10) 0.2500 -0.352(7) 0.041(7) Uiso 1 2 d S . .
H4A H 0.0491(12) 0.2500 -0.075(7) 0.050(8) Uiso 1 2 d S . .
H4B H 0.0816(10) 0.2500 -0.362(6) 0.038(7) Uiso 1 2 d S . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0434(11) 0.0567(14) 0.0441(11) 0.0017(9) -0.0138(8) 0.0107(9)
C2 0.0428(10) 0.0429(11) 0.0407(10) 0.0001(8) -0.0118(8) 0.0048(8)
C3 0.0220(10) 0.0411(13) 0.0208(10) 0.000 0.0006(8) 0.000
C4 0.0210(10) 0.0353(12) 0.0227(10) 0.000 0.0016(8) 0.000
C5 0.0376(9) 0.0389(10) 0.0385(10) -0.0004(7) -0.0077(7) -0.0017(7)
C6 0.0375(10) 0.0568(13) 0.0382(10) -0.0046(9) -0.0075(8) -0.0103(8)
N1 0.0266(10) 0.0746(17) 0.0324(11) 0.000 -0.0056(8) 0.000
N2 0.0258(10) 0.0688(16) 0.0295(11) 0.000 -0.0023(8) 0.000
C7 0.0310(11) 0.0332(11) 0.0213(10) 0.000 0.0022(8) 0.000
N3 0.0270(10) 0.0587(14) 0.0217(10) 0.000 0.0012(8) 0.000
N4 0.0266(10) 0.0597(14) 0.0203(10) 0.000 0.0020(7) 0.000
O1 0.0380(9) 0.0802(14) 0.0177(8) 0.000 0.0021(7) 0.000

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.326(2) . ?
C1 C2 1.386(2) . ?
C1 H1 0.98(2) . ?
C2 C3 1.384(2) . ?
C2 H2 0.97(2) . ?
C3 C2 1.384(2) 7_565 ?
C3 C4 1.489(3) . ?
C4 C5 1.388(2) 7_565 ?
C4 C5 1.388(2) . ?
C5 C6 1.386(2) . ?
C5 H5 0.97(2) . ?
C6 N2 1.328(2) . ?
C6 H6 0.94(2) . ?
N1 C1 1.326(2) 7_565 ?
N2 C6 1.328(2) 7_565 ?
C7 O1 1.244(3) . ?
C7 N3 1.342(3) . ?
C7 N4 1.342(3) . ?
N3 H3A 0.88(3) . ?
N3 H3B 0.88(3) . ?
N4 H4A 0.89(3) . ?
N4 H4B 0.89(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
N1 C1 C2 124.1(2) . . ?
N1 C1 H1 116.6(13) . . ?
C2 C1 H1 119.4(13) . . ?
C3 C2 C1 119.74(19) . . ?
C3 C2 H2 120.3(13) . . ?
C1 C2 H2 119.8(13) . . ?
C2 C3 C2 116.3(2) 7_565 . ?
C2 C3 C4 121.83(11) 7_565 . ?
C2 C3 C4 121.83(11) . . ?
C5 C4 C5 116.4(2) 7_565 . ?
C5 C4 C3 121.78(10) 7_565 . ?
C5 C4 C3 121.78(10) . . ?
C6 C5 C4 119.41(18) . . ?
C6 C5 H5 119.8(12) . . ?
C4 C5 H5 120.7(12) . . ?
N2 C6 C5 124.68(19) . . ?
N2 C6 H6 116.9(13) . . ?
C5 C6 H6 118.4(13) . . ?
C1 N1 C1 116.1(2) 7_565 . ?
C6 N2 C6 115.4(2) 7_565 . ?
O1 C7 N3 121.4(2) . . ?
O1 C7 N4 121.4(2) . . ?
N3 C7 N4 117.2(2) . . ?
C7 N3 H3A 117.5(18) . . ?
C7 N3 H3B 120.5(18) . . ?
H3A N3 H3B 122(3) . . ?
C7 N4 H4A 119.0(19) . . ?
C7 N4 H4B 120.3(17) . . ?
H4A N4 H4B 121(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.6(3) . . . . ?
C1 C2 C3 C2 -0.9(3) . . . 7_565 ?
C1 C2 C3 C4 179.85(19) . . . . ?
C2 C3 C4 C5 0.6(3) 7_565 . . 7_565 ?
C2 C3 C4 C5 179.85(19) . . . 7_565 ?
C2 C3 C4 C5 -179.85(19) 7_565 . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C5 C4 C5 C6 1.3(3) 7_565 . . . ?
C3 C4 C5 C6 -178.25(18) . . . . ?
C4 C5 C6 N2 -0.3(3) . . . . ?
C2 C1 N1 C1 -0.2(4) . . . 7_565 ?
C5 C6 N2 C6 -0.8(4) . . . 7_565 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 984586'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_platon

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            "salicylic acid:4,4'-bipyridine Form I"
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 N2 O6'
_chemical_formula_weight         432.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 '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                   7.860(8)
_cell_length_b                   8.308(8)
_cell_length_c                   8.547(8)
_cell_angle_alpha                87.812(14)
_cell_angle_beta                 82.149(3)
_cell_angle_gamma                65.900(14)
_cell_volume                     504.6(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1567
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      27.5

_exptl_crystal_description       needle
_exptl_crystal_colour            'colour less'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             226
_exptl_absorpt_coefficient_mu    0.104
# Permitted for _exptl_absorpt_correction_type :
# analytical     'analytical from crystal shape'
#                Example: de Meulenaer&Tompa: ABST
# cylinder       'cylindrical'
# gaussian       'Gaussian from crystal shape'
#                Example: PLATON/ABSG
# integration    'integration from crystal shape'
# multi-scan     'symmetry-related measurements'
#                Example: SADABS, MULABS
# none           'no absorption corr. applied'
# numerical      'numerical from crystal shape'
# psi-scan       'psi-scan corrections'
#                Example: PLATON/ABSP
# refdelf        'refined from delta-F'
#                Example: SHELXA,
# sphere         'spherical'
#                Example: PLATON/ABSS
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_min  0.9597
_exptl_absorpt_correction_T_max  0.9796
#===============================================================================

# 7. EXPERIMENTAL DATA

_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       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5358
_diffrn_reflns_av_R_equivalents  0.0700
_diffrn_reflns_av_sigmaI/netI    0.0612
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2291
_reflns_number_gt                2045
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0610P)²+0.0518P] 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         2291
_refine_ls_number_parameters     153
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1228
_refine_ls_wR_factor_gt          0.1194
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.004
_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 0.56977(13) 0.56164(12) 0.23766(10) 0.0264(2) Uani 1 1 d . . .
C1 C 0.90999(14) 0.51237(13) 0.04989(11) 0.0216(2) Uani 1 1 d . . .
C3 C 0.82830(18) 0.64365(16) 0.16744(13) 0.0301(3) Uani 1 1 d . . .
H12 H 0.8879 0.7189 0.1860 0.036 Uiso 1 1 calc R . .
C4 C 0.81583(17) 0.40603(15) 0.03085(13) 0.0277(3) Uani 1 1 d . . .
H13 H 0.8659 0.3145 -0.0473 0.033 Uiso 1 1 calc R . .
C5 C 0.66009(18) 0.66375(15) 0.25693(13) 0.0310(3) Uani 1 1 d . . .
H11 H 0.6062 0.7545 0.3358 0.037 Uiso 1 1 calc R . .
C7 C 0.64859(16) 0.43416(15) 0.12639(13) 0.0285(3) Uani 1 1 d . . .
O1 O -0.32013(11) 0.18901(11) 0.45776(9) 0.0298(2) Uani 1 1 d . . .
O2 O -0.23948(11) 0.36207(11) 0.59838(9) 0.0302(2) Uani 1 1 d . . .
H2 H -0.3602 0.3889 0.6416 0.045 Uiso 1 1 d R . .
O3 O -0.09072(13) 0.00602(11) 0.22322(10) 0.0339(2) Uani 1 1 d . . .
C18 C 0.02781(16) 0.07621(14) 0.25877(12) 0.0249(3) Uani 1 1 d . . .
C19 C -0.01924(15) 0.19468(13) 0.38705(11) 0.0217(2) Uani 1 1 d . . .
C20 C 0.32489(17) 0.09881(16) 0.19702(13) 0.0326(3) Uani 1 1 d . . .
H4 H 0.4424 0.0663 0.1320 0.039 Uiso 1 1 calc R . .
C21 C 0.10892(16) 0.26222(14) 0.41787(12) 0.0258(3) Uani 1 1 d . . .
H6 H 0.0776 0.3421 0.5044 0.031 Uiso 1 1 calc R . .
C22 C 0.20071(18) 0.03030(15) 0.16352(13) 0.0309(3) Uani 1 1 d . . .
H3 H 0.2327 -0.0481 0.0757 0.037 Uiso 1 1 calc R . .
C23 C -0.20563(15) 0.24794(14) 0.48457(12) 0.0231(2) Uani 1 1 d . . .
C24 C 0.28106(17) 0.21482(16) 0.32445(14) 0.0312(3) Uani 1 1 d . . .
H5 H 0.3679 0.2607 0.3469 0.037 Uiso 1 1 calc R . .
H22 H 0.579(2) 0.3624(18) 0.1147(16) 0.035(4) Uiso 1 1 d . . .
H1 H -0.203(3) 0.057(2) 0.303(2) 0.065(5) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0236(5) 0.0300(5) 0.0227(4) 0.0027(4) -0.0015(3) -0.0088(4)
C1 0.0235(6) 0.0224(5) 0.0178(5) 0.0040(4) -0.0034(4) -0.0084(4)
C3 0.0336(6) 0.0316(6) 0.0282(5) -0.0050(4) 0.0048(4) -0.0187(5)
C4 0.0269(6) 0.0299(6) 0.0264(5) -0.0041(4) -0.0003(4) -0.0121(5)
C5 0.0321(6) 0.0308(6) 0.0276(5) -0.0060(4) 0.0047(4) -0.0123(5)
C7 0.0262(6) 0.0324(6) 0.0288(5) -0.0002(4) -0.0029(4) -0.0139(5)
O1 0.0255(5) 0.0352(5) 0.0322(4) -0.0003(3) -0.0037(3) -0.0159(4)
O2 0.0249(4) 0.0353(5) 0.0302(4) -0.0090(3) 0.0030(3) -0.0134(4)
O3 0.0399(6) 0.0358(5) 0.0329(4) -0.0074(4) -0.0035(4) -0.0223(4)
C18 0.0301(6) 0.0238(5) 0.0230(5) 0.0026(4) -0.0063(4) -0.0125(4)
C19 0.0227(6) 0.0219(5) 0.0201(5) 0.0028(4) -0.0044(4) -0.0085(4)
C20 0.0274(6) 0.0367(6) 0.0296(6) -0.0013(5) 0.0046(4) -0.0115(5)
C21 0.0254(6) 0.0289(5) 0.0241(5) -0.0030(4) -0.0034(4) -0.0117(5)
C22 0.0361(7) 0.0296(6) 0.0241(5) -0.0054(4) 0.0024(4) -0.0118(5)
C23 0.0234(5) 0.0238(5) 0.0221(5) 0.0041(4) -0.0050(4) -0.0094(4)
C24 0.0256(6) 0.0381(6) 0.0329(6) -0.0020(5) -0.0019(4) -0.0164(5)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.3361(18) . ?
N1 C7 1.3380(17) . ?
C1 C4 1.3902(18) . ?
C1 C3 1.3953(18) . ?
C1 C1 1.489(2) 2_765 ?
C3 C5 1.384(2) . ?
C3 H12 0.9500 . ?
C4 C7 1.386(2) . ?
C4 H13 0.9500 . ?
C5 H11 0.9500 . ?
C7 H22 0.978(15) . ?
O1 C23 1.2357(16) . ?
O2 C23 1.3076(16) . ?
O2 H2 0.9082 . ?
O3 C18 1.3546(17) . ?
O3 H1 0.99(2) . ?
C18 C22 1.398(2) . ?
C18 C19 1.4078(17) . ?
C19 C21 1.3944(18) . ?
C19 C23 1.4839(19) . ?
C20 C22 1.379(2) . ?
C20 C24 1.3930(19) . ?
C20 H4 0.9500 . ?
C21 C24 1.385(2) . ?
C21 H6 0.9500 . ?
C22 H3 0.9500 . ?
C24 H5 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C7 117.43(11) . . ?
C4 C1 C3 116.91(11) . . ?
C4 C1 C1 121.78(12) . 2_765 ?
C3 C1 C1 121.31(12) . 2_765 ?
C5 C3 C1 119.71(11) . . ?
C5 C3 H12 120.1 . . ?
C1 C3 H12 120.1 . . ?
C7 C4 C1 119.72(11) . . ?
C7 C4 H13 120.1 . . ?
C1 C4 H13 120.1 . . ?
N1 C5 C3 123.13(11) . . ?
N1 C5 H11 118.4 . . ?
C3 C5 H11 118.4 . . ?
N1 C7 C4 123.10(11) . . ?
N1 C7 H22 115.4(8) . . ?
C4 C7 H22 121.5(8) . . ?
C23 O2 H2 105.3 . . ?
C18 O3 H1 105.0(11) . . ?
O3 C18 C22 118.56(11) . . ?
O3 C18 C19 121.94(11) . . ?
C22 C18 C19 119.50(11) . . ?
C21 C19 C18 119.26(11) . . ?
C21 C19 C23 121.38(11) . . ?
C18 C19 C23 119.35(10) . . ?
C22 C20 C24 121.17(11) . . ?
C22 C20 H4 119.4 . . ?
C24 C20 H4 119.4 . . ?
C24 C21 C19 121.11(12) . . ?
C24 C21 H6 119.4 . . ?
C19 C21 H6 119.4 . . ?
C20 C22 C18 119.98(12) . . ?
C20 C22 H3 120.0 . . ?
C18 C22 H3 120.0 . . ?
O1 C23 O2 123.03(10) . . ?
O1 C23 C19 121.76(11) . . ?
O2 C23 C19 115.21(10) . . ?
C21 C24 C20 118.97(11) . . ?
C21 C24 H5 120.5 . . ?
C20 C24 H5 120.5 . . ?

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
C4 C1 C3 C5 -0.73(16) . . . . ?
C1 C1 C3 C5 179.44(11) 2_765 . . . ?
C3 C1 C4 C7 0.23(15) . . . . ?
C1 C1 C4 C7 -179.93(11) 2_765 . . . ?
C7 N1 C5 C3 0.32(17) . . . . ?
C1 C3 C5 N1 0.48(18) . . . . ?
C5 N1 C7 C4 -0.85(16) . . . . ?
C1 C4 C7 N1 0.58(17) . . . . ?
O3 C18 C19 C21 179.87(9) . . . . ?
C22 C18 C19 C21 -0.85(15) . . . . ?
O3 C18 C19 C23 -1.39(15) . . . . ?
C22 C18 C19 C23 177.89(9) . . . . ?
C18 C19 C21 C24 0.06(16) . . . . ?
C23 C19 C21 C24 -178.65(9) . . . . ?
C24 C20 C22 C18 -0.39(18) . . . . ?
O3 C18 C22 C20 -179.68(10) . . . . ?
C19 C18 C22 C20 1.01(17) . . . . ?
C21 C19 C23 O1 179.82(9) . . . . ?
C18 C19 C23 O1 1.10(15) . . . . ?
C21 C19 C23 O2 0.56(14) . . . . ?
C18 C19 C23 O2 -178.16(8) . . . . ?
C19 C21 C24 C20 0.56(17) . . . . ?
C22 C20 C24 C21 -0.40(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.049
_database_code_depnum_ccdc_archive 'CCDC 984587'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_datam

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            "salicylic acid:4,4'-bipyridine Form II"
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 N2 O6'
_chemical_formula_weight         432.42

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 '

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                   9.920(9)
_cell_length_b                   4.919(4)
_cell_length_c                   23.046(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.28(3)
_cell_angle_gamma                90.00
_cell_volume                     1025.1(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2472
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            'colour less'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_absorpt_coefficient_mu    0.102
# Permitted for _exptl_absorpt_correction_type :
# analytical     'analytical from crystal shape'
#                Example: de Meulenaer&Tompa: ABST
# cylinder       'cylindrical'
# gaussian       'Gaussian from crystal shape'
#                Example: PLATON/ABSG
# integration    'integration from crystal shape'
# multi-scan     'symmetry-related measurements'
#                Example: SADABS, MULABS
# none           'no absorption corr. applied'
# numerical      'numerical from crystal shape'
# psi-scan       'psi-scan corrections'
#                Example: PLATON/ABSP
# refdelf        'refined from delta-F'
#                Example: SHELXA,
# sphere         'spherical'
#                Example: PLATON/ABSS
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_absorpt_correction_T_min  0.9799
_exptl_absorpt_correction_T_max  0.9899

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

# 7. EXPERIMENTAL DATA

_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       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10221
_diffrn_reflns_av_R_equivalents  0.1281
_diffrn_reflns_av_sigmaI/netI    0.0840
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         27.47
_reflns_number_total             2348
_reflns_number_gt                1930
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0942P)²+0.0000P] 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         2348
_refine_ls_number_parameters     149
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.1660
_refine_ls_wR_factor_gt          0.1461
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.002

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
N2 N 0.74414(13) 0.4907(2) 0.41264(6) 0.0316(3) Uani 1 1 d . . .
C8 C 0.95318(17) 0.7695(3) 0.42859(7) 0.0348(4) Uani 1 1 d . . .
H8 H 1.0282 0.8198 0.4151 0.042 Uiso 1 1 calc R . .
C9 C 0.83333(16) 0.8075(3) 0.49813(8) 0.0361(4) Uani 1 1 d . . .
H9 H 0.8230 0.8862 0.5337 0.043 Uiso 1 1 calc R . .
C10 C 0.73645(17) 0.6081(3) 0.46308(8) 0.0356(4) Uani 1 1 d . . .
H10 H 0.6607 0.5521 0.4756 0.043 Uiso 1 1 calc R . .
C11 C 0.85103(18) 0.5731(3) 0.39581(8) 0.0376(4) Uani 1 1 d . . .
H11 H 0.8571 0.4927 0.3595 0.045 Uiso 1 1 calc R . .
C12 C 0.94605(14) 0.8937(2) 0.48146(6) 0.0264(3) Uani 1 1 d . . .
O1 O 0.50957(12) -0.0933(2) 0.57137(5) 0.0369(3) Uani 1 1 d . . .
O2 O 0.44074(12) -0.1198(2) 0.65193(5) 0.0357(3) Uani 1 1 d D . .
O3 O 0.70838(13) 0.2537(3) 0.57701(6) 0.0494(4) Uani 1 1 d . . .
H3 H 0.6294 0.1246 0.5615 0.074 Uiso 1 1 d R . .
C1 C 0.62771(14) 0.1915(3) 0.66141(6) 0.0262(3) Uani 1 1 d . . .
C2 C 0.71727(15) 0.3181(3) 0.63568(7) 0.0323(4) Uani 1 1 d . . .
C3 C 0.64152(16) 0.2690(3) 0.72176(7) 0.0327(4) Uani 1 1 d . . .
H3A H 0.5810 0.1853 0.7396 0.039 Uiso 1 1 calc R . .
C4 C 0.83056(17) 0.5877(3) 0.72999(8) 0.0386(4) Uani 1 1 d . . .
H4 H 0.9003 0.7222 0.7536 0.046 Uiso 1 1 calc R . .
C5 C 0.52148(15) -0.0201(3) 0.62444(7) 0.0284(3) Uani 1 1 d . . .
C6 C 0.81818(17) 0.5153(3) 0.67051(8) 0.0389(4) Uani 1 1 d . . .
H6 H 0.8790 0.6007 0.6531 0.047 Uiso 1 1 calc R . .
C7 C 0.74180(18) 0.4656(3) 0.75590(7) 0.0395(4) Uani 1 1 d . . .
H7 H 0.7501 0.5173 0.7970 0.047 Uiso 1 1 calc R . .
H2 H 0.374(3) -0.253(4) 0.6262(11) 0.083(8) Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N2 0.0274(6) 0.0302(6) 0.0298(6) 0.0044(5) 0.0041(5) -0.0027(5)
C8 0.0318(8) 0.0397(8) 0.0328(8) -0.0020(6) 0.0132(7) -0.0089(6)
C9 0.0317(8) 0.0398(8) 0.0381(8) -0.0064(6) 0.0155(7) -0.0073(6)
C10 0.0277(7) 0.0381(8) 0.0401(8) 0.0008(6) 0.0129(7) -0.0051(6)
C11 0.0371(8) 0.0400(8) 0.0335(8) -0.0050(6) 0.0123(7) -0.0075(6)
C12 0.0215(7) 0.0250(6) 0.0271(7) 0.0049(5) 0.0043(6) 0.0013(5)
O1 0.0353(6) 0.0454(6) 0.0303(6) -0.0114(4) 0.0136(5) -0.0070(5)
O2 0.0367(6) 0.0405(6) 0.0302(6) -0.0047(4) 0.0141(5) -0.0131(4)
O3 0.0460(7) 0.0713(8) 0.0437(7) -0.0166(6) 0.0313(6) -0.0201(6)
C1 0.0221(7) 0.0288(6) 0.0260(7) -0.0008(5) 0.0081(6) 0.0010(5)
C2 0.0264(7) 0.0397(7) 0.0332(8) -0.0023(6) 0.0147(6) 0.0001(6)
C3 0.0331(8) 0.0355(7) 0.0282(7) -0.0015(6) 0.0113(6) -0.0037(6)
C4 0.0292(8) 0.0355(8) 0.0428(9) -0.0065(6) 0.0063(7) -0.0058(6)
C5 0.0238(7) 0.0320(7) 0.0280(7) -0.0002(5) 0.0090(6) 0.0012(5)
C6 0.0292(8) 0.0426(8) 0.0477(9) -0.0024(7) 0.0188(7) -0.0068(6)
C7 0.0415(9) 0.0431(8) 0.0294(8) -0.0080(6) 0.0101(7) -0.0043(7)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C10 1.328(2) . ?
N2 C11 1.333(2) . ?
C8 C11 1.379(2) . ?
C8 C12 1.391(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.378(2) . ?
C9 C12 1.390(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C12 1.489(3) 3_776 ?
O1 C5 1.2330(19) . ?
O2 C5 1.3040(18) . ?
O2 H2 0.944(17) . ?
O3 C2 1.356(2) . ?
O3 H3 0.9562 . ?
C1 C3 1.393(2) . ?
C1 C2 1.401(2) . ?
C1 C5 1.477(2) . ?
C2 C6 1.388(2) . ?
C3 C7 1.379(2) . ?
C3 H3A 0.9500 . ?
C4 C6 1.372(3) . ?
C4 C7 1.388(2) . ?
C4 H4 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N2 C11 117.46(13) . . ?
C11 C8 C12 119.82(14) . . ?
C11 C8 H8 120.1 . . ?
C12 C8 H8 120.1 . . ?
C10 C9 C12 120.10(15) . . ?
C10 C9 H9 120.0 . . ?
C12 C9 H9 120.0 . . ?
N2 C10 C9 123.05(14) . . ?
N2 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
N2 C11 C8 123.16(15) . . ?
N2 C11 H11 118.4 . . ?
C8 C11 H11 118.4 . . ?
C8 C12 C9 116.41(13) . . ?
C8 C12 C12 121.86(16) . 3_776 ?
C9 C12 C12 121.73(17) . 3_776 ?
C5 O2 H2 111.4(16) . . ?
C2 O3 H3 103.6 . . ?
C3 C1 C2 118.80(13) . . ?
C3 C1 C5 121.51(13) . . ?
C2 C1 C5 119.69(14) . . ?
O3 C2 C6 118.41(14) . . ?
O3 C2 C1 121.72(14) . . ?
C6 C2 C1 119.87(15) . . ?
C7 C3 C1 120.89(14) . . ?
C7 C3 H3A 119.6 . . ?
C1 C3 H3A 119.6 . . ?
C6 C4 C7 120.39(14) . . ?
C6 C4 H4 119.8 . . ?
C7 C4 H4 119.8 . . ?
O1 C5 O2 123.01(14) . . ?
O1 C5 C1 122.18(13) . . ?
O2 C5 C1 114.81(13) . . ?
C4 C6 C2 120.41(14) . . ?
C4 C6 H6 119.8 . . ?
C2 C6 H6 119.8 . . ?
C3 C7 C4 119.64(15) . . ?
C3 C7 H7 120.2 . . ?
C4 C7 H7 120.2 . . ?

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
C11 N2 C10 C9 -0.2(2) . . . . ?
C12 C9 C10 N2 -0.3(2) . . . . ?
C10 N2 C11 C8 0.8(2) . . . . ?
C12 C8 C11 N2 -0.9(2) . . . . ?
C11 C8 C12 C9 0.3(2) . . . . ?
C11 C8 C12 C12 179.86(15) . . . 3_776 ?
C10 C9 C12 C8 0.3(2) . . . . ?
C10 C9 C12 C12 -179.31(16) . . . 3_776 ?
C3 C1 C2 O3 -179.43(13) . . . . ?
C5 C1 C2 O3 0.7(2) . . . . ?
C3 C1 C2 C6 0.5(2) . . . . ?
C5 C1 C2 C6 -179.41(13) . . . . ?
C2 C1 C3 C7 -0.3(2) . . . . ?
C5 C1 C3 C7 179.58(13) . . . . ?
C3 C1 C5 O1 -178.99(13) . . . . ?
C2 C1 C5 O1 0.9(2) . . . . ?
C3 C1 C5 O2 1.87(19) . . . . ?
C2 C1 C5 O2 -178.24(12) . . . . ?
C7 C4 C6 C2 -0.3(3) . . . . ?
O3 C2 C6 C4 179.76(14) . . . . ?
C1 C2 C6 C4 -0.2(2) . . . . ?
C1 C3 C7 C4 -0.2(2) . . . . ?
C6 C4 C7 C3 0.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.115
_database_code_depnum_ccdc_archive 'CCDC 984588'
