# 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_temps6tt

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         N-(3-Pyridyl)-Benzamide
_chemical_formula_sum            'C12 H10 N2 O'
_chemical_formula_weight         198.22

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                   3.9459(2)
_cell_length_b                   22.7301(8)
_cell_length_c                   11.1951(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.725(4)
_cell_angle_gamma                90.00
_cell_volume                     956.43(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    16060
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      27.7

_exptl_crystal_description       'Irregular blocks'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.090
_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      200(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-2'
_diffrn_measurement_method       'Omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14064
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         27.33
_reflns_number_total             2138
_reflns_number_gt                1828
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area (STOE & CIE)'
_computing_cell_refinement       'X-Area (STOE & CIE)'
_computing_data_reduction        'X-Area (STOE & CIE)'
_computing_structure_solution    'SHELXS-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 > 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)+(0.0542P)²+0.1575P] 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     SHELXL
_refine_ls_extinction_coef       0.043(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2138
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1101
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4884(4) 0.64234(5) 0.62165(12) 0.0428(3) Uani 1 1 d . . .
O1 O 0.4087(3) 0.64294(5) 0.50702(9) 0.0636(4) Uani 1 1 d . . .
N1 N 0.6626(3) 0.68768(4) 0.69455(9) 0.0400(3) Uani 1 1 d . . .
H1 H 0.7000 0.6843 0.7759 0.048 Uiso 1 1 calc R . .
C2 C 0.7890(3) 0.73935(5) 0.65330(11) 0.0374(3) Uani 1 1 d . . .
C3 C 0.7481(4) 0.75233(5) 0.52785(12) 0.0424(3) Uani 1 1 d . . .
H3 H 0.6273 0.7248 0.4657 0.051 Uiso 1 1 calc R . .
N2 N 0.8714(3) 0.80185(5) 0.49105(10) 0.0460(3) Uani 1 1 d . . .
C4 C 1.0414(4) 0.84021(6) 0.57906(12) 0.0459(3) Uani 1 1 d . . .
H4 H 1.1284 0.8755 0.5536 0.055 Uiso 1 1 calc R . .
C5 C 1.0968(4) 0.83100(6) 0.70571(12) 0.0448(3) Uani 1 1 d . . .
H5 H 1.2209 0.8592 0.7658 0.054 Uiso 1 1 calc R . .
C6 C 0.9687(4) 0.78015(5) 0.74295(12) 0.0420(3) Uani 1 1 d . . .
H6 H 1.0028 0.7729 0.8294 0.050 Uiso 1 1 calc R . .
C7 C 0.4026(3) 0.59012(5) 0.68873(12) 0.0403(3) Uani 1 1 d . . .
C8 C 0.3665(4) 0.59180(5) 0.80833(12) 0.0426(3) Uani 1 1 d . . .
H8 H 0.3956 0.6279 0.8532 0.051 Uiso 1 1 calc R . .
C9 C 0.2878(4) 0.54063(6) 0.86200(13) 0.0482(3) Uani 1 1 d . . .
H9 H 0.2601 0.5419 0.9433 0.058 Uiso 1 1 calc R . .
C10 C 0.2495(4) 0.48792(6) 0.79821(14) 0.0514(4) Uani 1 1 d . . .
H10 H 0.2005 0.4529 0.8364 0.062 Uiso 1 1 calc R . .
C11 C 0.2824(4) 0.48594(6) 0.67899(14) 0.0536(4) Uani 1 1 d . . .
H11 H 0.2552 0.4497 0.6348 0.064 Uiso 1 1 calc R . .
C12 C 0.3551(4) 0.53695(6) 0.62421(13) 0.0486(3) Uani 1 1 d . . .
H12 H 0.3728 0.5357 0.5415 0.058 Uiso 1 1 calc R . .

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 0.0505(7) 0.0399(6) 0.0361(6) -0.0002(5) 0.0103(5) 0.0019(5)
O1 0.0967(9) 0.0540(6) 0.0346(5) -0.0021(4) 0.0118(5) -0.0168(5)
N1 0.0506(6) 0.0366(5) 0.0324(5) 0.0018(4) 0.0122(4) 0.0011(4)
C2 0.0417(6) 0.0354(6) 0.0359(6) 0.0021(5) 0.0128(5) 0.0061(5)
C3 0.0537(7) 0.0388(6) 0.0344(6) 0.0009(5) 0.0128(5) 0.0020(5)
N2 0.0606(7) 0.0410(6) 0.0380(6) 0.0035(4) 0.0174(5) 0.0032(5)
C4 0.0599(8) 0.0379(6) 0.0424(7) 0.0027(5) 0.0194(6) 0.0009(5)
C5 0.0556(8) 0.0396(6) 0.0392(7) -0.0020(5) 0.0142(6) -0.0005(5)
C6 0.0502(7) 0.0418(6) 0.0334(6) 0.0011(5) 0.0119(5) 0.0029(5)
C7 0.0429(7) 0.0374(6) 0.0389(6) -0.0003(5) 0.0097(5) 0.0020(5)
C8 0.0494(7) 0.0372(6) 0.0402(7) -0.0026(5) 0.0119(5) 0.0004(5)
C9 0.0559(8) 0.0451(7) 0.0438(7) 0.0020(5) 0.0157(6) -0.0012(6)
C10 0.0580(8) 0.0393(7) 0.0545(8) 0.0042(6) 0.0135(6) -0.0043(6)
C11 0.0654(9) 0.0370(7) 0.0550(8) -0.0066(6) 0.0134(7) -0.0016(6)
C12 0.0587(8) 0.0423(7) 0.0439(7) -0.0050(5) 0.0146(6) 0.0016(6)

_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
C1 O1 1.2249(16) . ?
C1 N1 1.3635(16) . ?
C1 C7 1.4975(18) . ?
N1 C2 1.4077(16) . ?
C2 C6 1.3918(17) . ?
C2 C3 1.3955(17) . ?
C3 N2 1.3400(17) . ?
N2 C4 1.3336(17) . ?
C4 C5 1.3830(18) . ?
C5 C6 1.3761(18) . ?
C7 C8 1.3894(18) . ?
C7 C12 1.3911(17) . ?
C8 C9 1.3870(18) . ?
C9 C10 1.379(2) . ?
C10 C11 1.380(2) . ?
C11 C12 1.382(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
O1 C1 N1 122.72(12) . . ?
O1 C1 C7 120.60(11) . . ?
N1 C1 C7 116.66(11) . . ?
C1 N1 C2 126.77(11) . . ?
C6 C2 C3 117.53(11) . . ?
C6 C2 N1 118.23(11) . . ?
C3 C2 N1 124.23(11) . . ?
N2 C3 C2 123.06(12) . . ?
C4 N2 C3 118.03(11) . . ?
N2 C4 C5 123.06(12) . . ?
C6 C5 C4 118.66(12) . . ?
C5 C6 C2 119.66(12) . . ?
C8 C7 C12 119.16(12) . . ?
C8 C7 C1 124.51(11) . . ?
C12 C7 C1 116.33(12) . . ?
C9 C8 C7 119.76(12) . . ?
C10 C9 C8 120.52(13) . . ?
C9 C10 C11 120.07(13) . . ?
C10 C11 C12 119.67(13) . . ?
C11 C12 C7 120.79(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
C7 N1 C1 C2 -175.93(11) . . . . ?

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
N1 H1 N2 0.88 2.32 3.1762(15) 165.3 4_576

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.33
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.030
_database_code_depnum_ccdc_archive 'CCDC 989630'
#######################################################################
#
#                 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_temps6rt

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            N-(3-Pyridyl)-Benzamide
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 N2 O'
_chemical_formula_weight         198.22

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                   4.0274(3)
_cell_length_b                   22.7050(16)
_cell_length_c                   11.2415(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.874(7)
_cell_angle_gamma                90.00
_cell_volume                     978.33(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7622
_cell_measurement_theta_min      4.6
_cell_measurement_theta_max      25.7

_exptl_crystal_description       'Irregular blocks'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.088
_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      293(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-1'
_diffrn_measurement_method       'Phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9370
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.30
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2091
_reflns_number_gt                1531
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area (STOE & CIE)'
_computing_cell_refinement       'X-Area (STOE & CIE)'
_computing_data_reduction        'X-Area (STOE & CIE)'
_computing_structure_solution    'SHELXS-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 > 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)+(0.0656P)²+0.0997P] 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         2091
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1167
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.4954(4) 0.64203(6) 0.62232(12) 0.0451(3) Uani 1 1 d . . .
O1 O 0.4212(4) 0.64240(6) 0.50855(10) 0.0773(4) Uani 1 1 d . . .
N1 N 0.6660(3) 0.68751(5) 0.69511(10) 0.0405(3) Uani 1 1 d . . .
H1 H 0.6997 0.6844 0.7742 0.049 Uiso 1 1 calc R . .
C2 C 0.7925(3) 0.73898(5) 0.65441(11) 0.0367(3) Uani 1 1 d . . .
C3 C 0.7515(4) 0.75217(6) 0.52936(12) 0.0453(3) Uani 1 1 d . . .
H3 H 0.6330 0.7254 0.4685 0.054 Uiso 1 1 calc R . .
N2 N 0.8746(4) 0.80150(5) 0.49291(11) 0.0510(3) Uani 1 1 d . . .
C4 C 1.0460(5) 0.83942(6) 0.58092(14) 0.0510(4) Uani 1 1 d . . .
H4 H 1.1325 0.8738 0.5564 0.061 Uiso 1 1 calc R . .
C5 C 1.1010(4) 0.83003(6) 0.70666(13) 0.0490(4) Uani 1 1 d . . .
H5 H 1.2224 0.8574 0.7654 0.059 Uiso 1 1 calc R . .
C6 C 0.9732(4) 0.77946(6) 0.74355(12) 0.0437(3) Uani 1 1 d . . .
H6 H 1.0074 0.7723 0.8279 0.052 Uiso 1 1 calc R . .
C7 C 0.4062(4) 0.59007(6) 0.68913(12) 0.0417(3) Uani 1 1 d . . .
C8 C 0.3701(4) 0.59212(6) 0.80778(13) 0.0458(3) Uani 1 1 d . . .
H8 H 0.4002 0.6275 0.8514 0.055 Uiso 1 1 calc R . .
C9 C 0.2892(5) 0.54143(7) 0.86120(15) 0.0553(4) Uani 1 1 d . . .
H9 H 0.2630 0.5430 0.9405 0.066 Uiso 1 1 calc R . .
C10 C 0.2472(5) 0.48867(7) 0.79809(17) 0.0606(5) Uani 1 1 d . . .
H10 H 0.1967 0.4547 0.8353 0.073 Uiso 1 1 calc R . .
C11 C 0.2797(5) 0.48621(7) 0.67999(17) 0.0645(5) Uani 1 1 d . . .
H11 H 0.2508 0.4506 0.6371 0.077 Uiso 1 1 calc R . .
C12 C 0.3556(5) 0.53687(7) 0.62538(15) 0.0556(4) Uani 1 1 d . . .
H12 H 0.3730 0.5353 0.5448 0.067 Uiso 1 1 calc R . .

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 0.0569(8) 0.0455(7) 0.0295(6) -0.0019(5) 0.0081(6) 0.0033(6)
O1 0.1263(12) 0.0681(8) 0.0291(6) -0.0045(5) 0.0117(6) -0.0250(7)
N1 0.0549(7) 0.0404(6) 0.0246(5) 0.0016(4) 0.0099(5) 0.0027(5)
C2 0.0432(7) 0.0384(6) 0.0278(6) 0.0030(5) 0.0099(5) 0.0095(5)
C3 0.0622(9) 0.0450(7) 0.0268(6) 0.0011(5) 0.0109(6) 0.0048(6)
N2 0.0749(9) 0.0483(7) 0.0309(6) 0.0058(5) 0.0182(6) 0.0052(6)
C4 0.0731(10) 0.0432(7) 0.0398(8) 0.0050(6) 0.0220(7) 0.0024(7)
C5 0.0655(9) 0.0450(7) 0.0355(7) -0.0028(6) 0.0140(7) -0.0014(6)
C6 0.0567(8) 0.0470(7) 0.0259(6) 0.0014(5) 0.0104(6) 0.0032(6)
C7 0.0452(7) 0.0423(7) 0.0341(6) -0.0018(5) 0.0067(6) 0.0039(5)
C8 0.0554(8) 0.0425(7) 0.0373(7) -0.0036(6) 0.0108(6) 0.0005(6)
C9 0.0676(10) 0.0538(9) 0.0445(8) 0.0019(6) 0.0172(7) -0.0031(7)
C10 0.0703(11) 0.0457(8) 0.0607(10) 0.0059(7) 0.0126(8) -0.0074(7)
C11 0.0830(12) 0.0417(8) 0.0626(11) -0.0109(7) 0.0132(9) -0.0026(8)
C12 0.0736(11) 0.0479(8) 0.0437(8) -0.0091(6) 0.0156(7) 0.0016(7)

_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
C1 O1 1.2209(17) . ?
C1 N1 1.3650(17) . ?
C1 C7 1.500(2) . ?
N1 C2 1.4064(17) . ?
C2 C6 1.3893(19) . ?
C2 C3 1.3966(18) . ?
C3 N2 1.3389(19) . ?
N2 C4 1.333(2) . ?
C4 C5 1.378(2) . ?
C5 C6 1.374(2) . ?
C7 C8 1.386(2) . ?
C7 C12 1.387(2) . ?
C8 C9 1.383(2) . ?
C9 C10 1.376(2) . ?
C10 C11 1.375(3) . ?
C11 C12 1.381(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
O1 C1 N1 122.62(14) . . ?
O1 C1 C7 120.71(13) . . ?
N1 C1 C7 116.66(11) . . ?
C1 N1 C2 126.85(11) . . ?
C6 C2 C3 117.27(13) . . ?
C6 C2 N1 118.47(11) . . ?
C3 C2 N1 124.25(12) . . ?
N2 C3 C2 123.15(13) . . ?
C4 N2 C3 117.98(12) . . ?
N2 C4 C5 123.00(14) . . ?
C6 C5 C4 118.80(13) . . ?
C5 C6 C2 119.80(12) . . ?
C8 C7 C12 118.95(14) . . ?
C8 C7 C1 124.56(12) . . ?
C12 C7 C1 116.48(13) . . ?
C9 C8 C7 119.89(13) . . ?
C10 C9 C8 120.59(16) . . ?
C11 C10 C9 120.02(15) . . ?
C10 C11 C12 119.67(15) . . ?
C11 C12 C7 120.86(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
C7 N1 C1 C2 -176.25(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N2 0.86 2.36 3.2014(16) 165.1 4_576

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.030
_database_code_depnum_ccdc_archive 'CCDC 989631'
#######################################################################
#
#                 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_temps5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            N-(3-Pyridyl)-Benzamide
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 N2 O'
_chemical_formula_weight         198.22

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'

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

_cell_length_a                   5.2575(6)
_cell_length_b                   22.8695(16)
_cell_length_c                   7.9917(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.610(13)
_cell_angle_gamma                90.00
_cell_volume                     960.84(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.090
_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      200(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-1'
_diffrn_measurement_method       'Phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6380
_diffrn_reflns_av_R_equivalents  0.0689
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1736
_reflns_number_gt                1538
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area (STOE & CIE)'
_computing_cell_refinement       'X-Area (STOE & CIE)'
_computing_data_reduction        'X-Area (STOE & CIE)'
_computing_structure_solution    'SHELXS-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 > 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)+(0.0903P)²+0.5671P] 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     SHELXL
_refine_ls_extinction_coef       0.050(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(3)
_refine_ls_number_reflns         1736
_refine_ls_number_parameters     273
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.1591
_refine_ls_wR_factor_gt          0.1514
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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 0.5922(10) 0.2470(2) 0.5598(6) 0.0290(11) Uani 1 1 d . . .
O1 O 0.3747(7) 0.22981(18) 0.5858(6) 0.0416(10) Uani 1 1 d . . .
N1 N 0.7997(8) 0.21220(17) 0.5820(5) 0.0267(9) Uani 1 1 d . . .
H1 H 0.9496 0.2276 0.5621 0.032 Uiso 1 1 calc R . .
C2 C 0.7936(9) 0.1531(2) 0.6347(6) 0.0247(10) Uani 1 1 d . . .
C3 C 0.6034(10) 0.1145(2) 0.5853(7) 0.0315(12) Uani 1 1 d . . .
H3 H 0.4695 0.1290 0.5162 0.038 Uiso 1 1 calc R . .
N2 N 0.5978(8) 0.05856(19) 0.6291(6) 0.0354(11) Uani 1 1 d . . .
C4 C 0.7901(11) 0.0393(2) 0.7288(7) 0.0362(13) Uani 1 1 d . . .
H4 H 0.7888 -0.0005 0.7634 0.043 Uiso 1 1 calc R . .
C5 C 0.9856(10) 0.0741(2) 0.7820(7) 0.0315(12) Uani 1 1 d . . .
H5 H 1.1176 0.0585 0.8508 0.038 Uiso 1 1 calc R . .
C6 C 0.9896(10) 0.1317(2) 0.7350(6) 0.0287(11) Uani 1 1 d . . .
H6 H 1.1244 0.1565 0.7705 0.034 Uiso 1 1 calc R . .
C7 C 0.6426(9) 0.3082(2) 0.5065(6) 0.0253(10) Uani 1 1 d . . .
C8 C 0.8490(9) 0.3246(2) 0.4083(6) 0.0277(11) Uani 1 1 d . . .
H8 H 0.9700 0.2961 0.3754 0.033 Uiso 1 1 calc R . .
C9 C 0.8783(10) 0.3821(2) 0.3588(7) 0.0326(12) Uani 1 1 d . . .
H9 H 1.0183 0.3926 0.2909 0.039 Uiso 1 1 calc R . .
C10 C 0.7077(10) 0.4241(2) 0.4065(7) 0.0325(12) Uani 1 1 d . . .
H10 H 0.7307 0.4636 0.3729 0.039 Uiso 1 1 calc R . .
C11 C 0.5009(11) 0.4087(2) 0.5043(7) 0.0323(12) Uani 1 1 d . . .
H11 H 0.3826 0.4376 0.5382 0.039 Uiso 1 1 calc R . .
C12 C 0.4684(10) 0.3513(2) 0.5518(6) 0.0288(11) Uani 1 1 d . . .
H12 H 0.3248 0.3408 0.6165 0.035 Uiso 1 1 calc R . .
C21 C 0.1012(9) 0.2485(2) 0.0447(6) 0.0271(11) Uani 1 1 d . . .
O21 O -0.1195(6) 0.22980(16) 0.0512(5) 0.0337(9) Uani 1 1 d . . .
N21 N 0.3053(8) 0.21463(17) 0.0820(5) 0.0281(9) Uani 1 1 d . . .
H21 H 0.4571 0.2304 0.0724 0.034 Uiso 1 1 calc R . .
C22 C 0.2924(9) 0.1557(2) 0.1354(6) 0.0260(10) Uani 1 1 d . . .
C23 C 0.4875(9) 0.1181(2) 0.0866(7) 0.0310(11) Uani 1 1 d . . .
H23 H 0.6183 0.1329 0.0174 0.037 Uiso 1 1 calc R . .
N22 N 0.4974(9) 0.0623(2) 0.1334(6) 0.0382(11) Uani 1 1 d . . .
C24 C 0.3143(11) 0.0425(2) 0.2303(7) 0.0352(13) Uani 1 1 d . . .
H24 H 0.3220 0.0029 0.2659 0.042 Uiso 1 1 calc R . .
C25 C 0.1122(10) 0.0763(2) 0.2825(7) 0.0343(12) Uani 1 1 d . . .
H25 H -0.0177 0.0598 0.3494 0.041 Uiso 1 1 calc R . .
C26 C 0.1019(10) 0.1341(2) 0.2363(7) 0.0309(11) Uani 1 1 d . . .
H26 H -0.0325 0.1586 0.2727 0.037 Uiso 1 1 calc R . .
C27 C 0.1529(9) 0.3102(2) -0.0051(6) 0.0254(11) Uani 1 1 d . . .
C28 C 0.3626(9) 0.3422(2) 0.0518(6) 0.0269(11) Uani 1 1 d . . .
H28 H 0.4891 0.3237 0.1189 0.032 Uiso 1 1 calc R . .
C29 C 0.3879(10) 0.4005(2) 0.0117(6) 0.0316(12) Uani 1 1 d . . .
H29 H 0.5292 0.4221 0.0531 0.038 Uiso 1 1 calc R . .
C30 C 0.2056(10) 0.4276(2) -0.0900(6) 0.0306(12) Uani 1 1 d . . .
H30 H 0.2223 0.4677 -0.1185 0.037 Uiso 1 1 calc R . .
C31 C -0.0001(10) 0.3955(2) -0.1490(7) 0.0313(11) Uani 1 1 d . . .
H31 H -0.1231 0.4135 -0.2201 0.038 Uiso 1 1 calc R . .
C32 C -0.0268(9) 0.3381(2) -0.1054(6) 0.0279(11) Uani 1 1 d . . .
H32 H -0.1710 0.3169 -0.1444 0.033 Uiso 1 1 calc R . .

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 0.026(3) 0.027(3) 0.034(3) -0.004(2) -0.003(2) 0.001(2)
O1 0.0223(19) 0.0294(19) 0.073(3) 0.0098(19) 0.0046(18) -0.0019(16)
N1 0.026(2) 0.021(2) 0.033(2) 0.0008(17) -0.0014(16) -0.0031(16)
C2 0.028(2) 0.022(2) 0.024(2) -0.0038(18) 0.0011(19) -0.001(2)
C3 0.032(3) 0.021(2) 0.042(3) -0.002(2) -0.006(2) 0.002(2)
N2 0.032(2) 0.024(2) 0.050(3) 0.000(2) -0.002(2) -0.0023(19)
C4 0.045(3) 0.023(3) 0.041(3) 0.005(2) 0.007(3) 0.002(2)
C5 0.034(3) 0.029(3) 0.032(3) 0.003(2) -0.001(2) 0.001(2)
C6 0.029(3) 0.027(3) 0.030(3) -0.001(2) 0.001(2) -0.002(2)
C7 0.024(2) 0.026(2) 0.026(2) -0.0007(19) -0.003(2) -0.001(2)
C8 0.025(2) 0.026(3) 0.033(3) -0.001(2) -0.0015(19) 0.001(2)
C9 0.035(3) 0.031(3) 0.032(3) 0.004(2) 0.001(2) -0.003(2)
C10 0.039(3) 0.022(3) 0.036(3) 0.004(2) -0.005(2) -0.001(2)
C11 0.034(3) 0.024(3) 0.039(3) -0.004(2) -0.006(2) 0.006(2)
C12 0.028(3) 0.026(3) 0.031(3) 0.000(2) -0.001(2) 0.002(2)
C21 0.023(2) 0.030(3) 0.029(2) -0.003(2) -0.0017(19) 0.000(2)
O21 0.0245(18) 0.0256(17) 0.051(2) 0.0052(16) -0.0016(16) -0.0023(15)
N21 0.025(2) 0.022(2) 0.037(2) 0.0017(17) -0.0005(17) 0.0005(17)
C22 0.027(2) 0.024(2) 0.026(2) -0.0003(19) -0.0087(19) -0.006(2)
C23 0.024(2) 0.024(3) 0.045(3) -0.002(2) 0.001(2) -0.0018(19)
N22 0.036(2) 0.029(2) 0.050(3) -0.001(2) 0.003(2) 0.000(2)
C24 0.040(3) 0.024(3) 0.041(3) 0.006(2) -0.010(2) -0.004(2)
C25 0.034(3) 0.036(3) 0.034(3) 0.007(2) -0.005(2) -0.006(2)
C26 0.030(3) 0.033(3) 0.030(3) 0.003(2) -0.001(2) 0.002(2)
C27 0.024(2) 0.023(2) 0.030(3) -0.003(2) -0.002(2) 0.002(2)
C28 0.024(2) 0.029(3) 0.028(2) 0.002(2) -0.0049(19) 0.002(2)
C29 0.033(3) 0.029(3) 0.033(3) -0.008(2) 0.002(2) -0.003(2)
C30 0.037(3) 0.022(3) 0.032(3) 0.004(2) 0.004(2) 0.001(2)
C31 0.029(3) 0.029(3) 0.037(3) 0.004(2) -0.001(2) 0.007(2)
C32 0.024(2) 0.030(3) 0.030(3) -0.004(2) -0.0043(19) 0.004(2)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.229(6) . ?
C1 N1 1.361(7) . ?
C1 C7 1.487(7) . ?
N1 C2 1.416(6) . ?
C2 C3 1.388(7) . ?
C2 C6 1.388(7) . ?
C3 N2 1.327(7) . ?
N2 C4 1.354(8) . ?
C4 C5 1.364(8) . ?
C5 C6 1.370(7) . ?
C7 C12 1.396(7) . ?
C7 C8 1.398(7) . ?
C8 C9 1.382(7) . ?
C9 C10 1.372(8) . ?
C10 C11 1.391(8) . ?
C11 C12 1.378(7) . ?
C21 O21 1.238(6) . ?
C21 N21 1.354(6) . ?
C21 C27 1.493(7) . ?
N21 C22 1.416(6) . ?
C22 C26 1.384(7) . ?
C22 C23 1.397(7) . ?
C23 N22 1.330(7) . ?
N22 C24 1.322(7) . ?
C24 C25 1.382(8) . ?
C25 C26 1.373(8) . ?
C27 C32 1.387(7) . ?
C27 C28 1.396(7) . ?
C28 C29 1.376(7) . ?
C29 C30 1.395(8) . ?
C30 C31 1.386(8) . ?
C31 C32 1.366(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 122.5(4) . . ?
O1 C1 C7 121.2(4) . . ?
N1 C1 C7 116.3(4) . . ?
C1 N1 C2 125.2(4) . . ?
C3 C2 C6 117.9(4) . . ?
C3 C2 N1 122.7(5) . . ?
C6 C2 N1 119.3(4) . . ?
N2 C3 C2 123.8(5) . . ?
C3 N2 C4 116.8(5) . . ?
N2 C4 C5 123.3(5) . . ?
C4 C5 C6 119.3(5) . . ?
C5 C6 C2 119.0(5) . . ?
C12 C7 C8 118.2(5) . . ?
C12 C7 C1 118.1(4) . . ?
C8 C7 C1 123.7(5) . . ?
C9 C8 C7 120.4(5) . . ?
C10 C9 C8 120.8(5) . . ?
C9 C10 C11 119.7(5) . . ?
C12 C11 C10 119.8(5) . . ?
C11 C12 C7 121.2(5) . . ?
O21 C21 N21 122.3(4) . . ?
O21 C21 C27 120.7(4) . . ?
N21 C21 C27 117.0(4) . . ?
C21 N21 C22 124.8(4) . . ?
C26 C22 C23 118.7(5) . . ?
C26 C22 N21 123.6(5) . . ?
C23 C22 N21 117.7(4) . . ?
N22 C23 C22 122.6(5) . . ?
C24 N22 C23 117.8(5) . . ?
N22 C24 C25 123.5(5) . . ?
C26 C25 C24 119.0(5) . . ?
C25 C26 C22 118.3(5) . . ?
C32 C27 C28 118.6(5) . . ?
C32 C27 C21 117.6(4) . . ?
C28 C27 C21 123.7(4) . . ?
C29 C28 C27 120.6(5) . . ?
C28 C29 C30 119.9(5) . . ?
C31 C30 C29 119.4(5) . . ?
C32 C31 C30 120.3(5) . . ?
C31 C32 C27 121.2(5) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 989632'
#######################################################################
#
#                 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_temps4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            N-(3-Pyridyl)-Benzamide
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 N2 O'
_chemical_formula_weight         198.22

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                   24.078(2)
_cell_length_b                   5.2381(2)
_cell_length_c                   15.9279(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.382(9)
_cell_angle_gamma                90.00
_cell_volume                     1895.0(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    7777
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      26.8

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.091
_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      200(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-1'
_diffrn_measurement_method       'Phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8132
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         26.85
_reflns_number_total             2042
_reflns_number_gt                1568
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area (STOE & CIE)'
_computing_cell_refinement       'X-Area (STOE & CIE)'
_computing_data_reduction        'X-Area (STOE & CIE)'
_computing_structure_solution    'SHELXS-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 > 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)+(0.0770P)²+0.3003P] 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     SHELXL
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2042
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1214
_refine_ls_wR_factor_gt          0.1109
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.52255(6) 0.4050(3) 0.63491(9) 0.0232(3) Uani 1 1 d . . .
O1 O 0.50703(5) 0.6271(2) 0.63864(8) 0.0353(3) Uani 1 1 d . . .
N1 N 0.48626(5) 0.2022(2) 0.63022(8) 0.0233(3) Uani 1 1 d . . .
H1 H 0.5012 0.0486 0.6308 0.028 Uiso 1 1 calc R . .
C2 C 0.42650(6) 0.2192(3) 0.62450(9) 0.0211(3) Uani 1 1 d . . .
C3 C 0.40278(6) 0.0233(3) 0.66088(10) 0.0250(3) Uani 1 1 d . . .
H3 H 0.4282 -0.1105 0.6912 0.030 Uiso 1 1 calc R . .
N2 N 0.34623(5) 0.0129(2) 0.65553(9) 0.0297(3) Uani 1 1 d . . .
C4 C 0.31180(6) 0.2058(3) 0.61397(10) 0.0282(3) Uani 1 1 d . . .
H4 H 0.2716 0.2031 0.6102 0.034 Uiso 1 1 calc R . .
C5 C 0.33135(6) 0.4088(3) 0.57617(10) 0.0262(3) Uani 1 1 d . . .
H5 H 0.3051 0.5417 0.5474 0.031 Uiso 1 1 calc R . .
C6 C 0.38987(6) 0.4166(3) 0.58062(9) 0.0240(3) Uani 1 1 d . . .
H6 H 0.4044 0.5528 0.5544 0.029 Uiso 1 1 calc R . .
C7 C 0.58305(6) 0.3413(3) 0.63514(9) 0.0210(3) Uani 1 1 d . . .
C8 C 0.62849(6) 0.5080(3) 0.67894(10) 0.0244(3) Uani 1 1 d . . .
H8 H 0.6206 0.6527 0.7092 0.029 Uiso 1 1 calc R . .
C9 C 0.68497(6) 0.4635(3) 0.67856(10) 0.0281(3) Uani 1 1 d . . .
H9 H 0.7159 0.5764 0.7093 0.034 Uiso 1 1 calc R . .
C10 C 0.69671(6) 0.2551(3) 0.63358(9) 0.0272(4) Uani 1 1 d . . .
H10 H 0.7355 0.2264 0.6327 0.033 Uiso 1 1 calc R . .
C11 C 0.65157(6) 0.0886(3) 0.58986(10) 0.0278(4) Uani 1 1 d . . .
H11 H 0.6595 -0.0546 0.5590 0.033 Uiso 1 1 calc R . .
C12 C 0.59512(6) 0.1301(3) 0.59103(9) 0.0245(3) Uani 1 1 d . . .
H12 H 0.5645 0.0142 0.5616 0.029 Uiso 1 1 calc R . .

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 0.0251(7) 0.0187(7) 0.0264(7) -0.0004(5) 0.0093(5) 0.0000(5)
O1 0.0286(6) 0.0164(6) 0.0633(8) -0.0045(5) 0.0183(5) -0.0002(4)
N1 0.0220(6) 0.0165(6) 0.0328(6) 0.0008(5) 0.0108(5) 0.0006(4)
C2 0.0218(7) 0.0197(7) 0.0217(6) -0.0037(5) 0.0070(5) -0.0021(5)
C3 0.0274(7) 0.0196(7) 0.0281(7) 0.0004(5) 0.0095(6) -0.0002(5)
N2 0.0300(7) 0.0248(7) 0.0386(7) -0.0011(5) 0.0169(6) -0.0034(5)
C4 0.0238(7) 0.0279(8) 0.0351(8) -0.0054(6) 0.0128(6) -0.0019(6)
C5 0.0237(7) 0.0249(8) 0.0285(7) -0.0019(6) 0.0067(6) 0.0021(6)
C6 0.0256(7) 0.0212(7) 0.0254(7) 0.0005(5) 0.0089(6) -0.0024(5)
C7 0.0226(7) 0.0186(7) 0.0222(6) 0.0037(5) 0.0079(5) 0.0007(5)
C8 0.0285(7) 0.0208(7) 0.0252(7) -0.0028(5) 0.0105(6) -0.0017(5)
C9 0.0246(7) 0.0308(8) 0.0273(7) -0.0002(6) 0.0065(6) -0.0060(6)
C10 0.0223(7) 0.0320(8) 0.0282(7) 0.0073(6) 0.0097(6) 0.0047(6)
C11 0.0316(8) 0.0235(8) 0.0308(8) -0.0002(6) 0.0137(6) 0.0045(6)
C12 0.0268(7) 0.0203(7) 0.0255(7) -0.0018(5) 0.0075(5) -0.0023(5)

_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
C1 O1 1.2291(17) . ?
C1 N1 1.3618(18) . ?
C1 C7 1.4931(18) . ?
N1 C2 1.4141(17) . ?
C2 C6 1.3878(19) . ?
C2 C3 1.3910(19) . ?
C3 N2 1.3368(18) . ?
N2 C4 1.335(2) . ?
C4 C5 1.380(2) . ?
C5 C6 1.3877(19) . ?
C7 C12 1.392(2) . ?
C7 C8 1.393(2) . ?
C8 C9 1.382(2) . ?
C9 C10 1.385(2) . ?
C10 C11 1.388(2) . ?
C11 C12 1.383(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
O1 C1 N1 122.75(13) . . ?
O1 C1 C7 121.56(12) . . ?
N1 C1 C7 115.69(12) . . ?
C1 N1 C2 125.11(12) . . ?
C6 C2 C3 118.64(13) . . ?
C6 C2 N1 122.85(12) . . ?
C3 C2 N1 118.45(12) . . ?
N2 C3 C2 123.63(13) . . ?
C4 N2 C3 116.91(12) . . ?
N2 C4 C5 123.65(13) . . ?
C4 C5 C6 119.20(13) . . ?
C5 C6 C2 117.95(13) . . ?
C12 C7 C8 119.36(13) . . ?
C12 C7 C1 122.90(12) . . ?
C8 C7 C1 117.69(12) . . ?
C9 C8 C7 120.18(13) . . ?
C8 C9 C10 120.34(13) . . ?
C9 C10 C11 119.66(13) . . ?
C12 C11 C10 120.27(14) . . ?
C11 C12 C7 120.18(14) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.85
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 989633'
#######################################################################
#
#                 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_temps4rt

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            N-(3-Pyridyl)-Benzamide
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 N2 O'
_chemical_formula_weight         198.22

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                   24.1282(15)
_cell_length_b                   5.2571(2)
_cell_length_c                   16.1250(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.197(5)
_cell_angle_gamma                90.00
_cell_volume                     1931.63(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    8132
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      26.8

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.089
_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      200(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-2'
_diffrn_measurement_method       'Omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11244
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         26.77
_reflns_number_total             2060
_reflns_number_gt                1639
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area (STOE & CIE)'
_computing_cell_refinement       'X-Area (STOE & CIE)'
_computing_data_reduction        'X-Area (STOE & CIE)'
_computing_structure_solution    'SHELXS-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 > 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)+(0.0372P)²+0.9485P] 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         2060
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1119
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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 0.52240(7) 0.4048(3) 0.63436(12) 0.0451(4) Uani 1 1 d . . .
O1 O 0.50688(6) 0.6257(2) 0.63779(11) 0.0639(4) Uani 1 1 d . . .
N1 N 0.48623(6) 0.2035(3) 0.62990(10) 0.0458(4) Uani 1 1 d . . .
H1 H 0.5012 0.0505 0.6306 0.055 Uiso 1 1 calc R . .
C2 C 0.42663(7) 0.2190(3) 0.62422(11) 0.0408(4) Uani 1 1 d . . .
C3 C 0.40326(8) 0.0252(3) 0.66070(13) 0.0487(4) Uani 1 1 d . . .
H3 H 0.4287 -0.1071 0.6911 0.058 Uiso 1 1 calc R . .
N2 N 0.34697(7) 0.0141(3) 0.65549(12) 0.0565(4) Uani 1 1 d . . .
C4 C 0.31264(8) 0.2054(4) 0.61414(13) 0.0537(5) Uani 1 1 d . . .
H4 H 0.2725 0.2024 0.6104 0.064 Uiso 1 1 calc R . .
C5 C 0.33198(7) 0.4067(4) 0.57656(12) 0.0504(4) Uani 1 1 d . . .
H5 H 0.3057 0.5388 0.5480 0.061 Uiso 1 1 calc R . .
C6 C 0.38989(7) 0.4141(3) 0.58087(12) 0.0468(4) Uani 1 1 d . . .
H6 H 0.4043 0.5497 0.5548 0.056 Uiso 1 1 calc R . .
C7 C 0.58289(7) 0.3417(3) 0.63496(11) 0.0409(4) Uani 1 1 d . . .
C8 C 0.62816(7) 0.5061(3) 0.67854(12) 0.0477(4) Uani 1 1 d . . .
H8 H 0.6203 0.6501 0.7085 0.057 Uiso 1 1 calc R . .
C9 C 0.68447(8) 0.4611(4) 0.67843(13) 0.0528(5) Uani 1 1 d . . .
H9 H 0.7153 0.5729 0.7091 0.063 Uiso 1 1 calc R . .
C10 C 0.69613(8) 0.2550(4) 0.63412(12) 0.0524(5) Uani 1 1 d . . .
H10 H 0.7349 0.2258 0.6336 0.063 Uiso 1 1 calc R . .
C11 C 0.65147(8) 0.0911(4) 0.59055(13) 0.0529(5) Uani 1 1 d . . .
H11 H 0.6595 -0.0510 0.5599 0.063 Uiso 1 1 calc R . .
C12 C 0.59503(8) 0.1330(3) 0.59129(12) 0.0474(4) Uani 1 1 d . . .
H12 H 0.5645 0.0184 0.5618 0.057 Uiso 1 1 calc R . .

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 0.0463(9) 0.0355(8) 0.0553(10) -0.0007(8) 0.0193(8) -0.0014(7)
O1 0.0521(7) 0.0323(6) 0.1127(12) -0.0058(7) 0.0346(8) -0.0005(6)
N1 0.0428(7) 0.0332(7) 0.0636(9) 0.0003(7) 0.0206(6) -0.0002(6)
C2 0.0401(8) 0.0374(8) 0.0459(9) -0.0038(7) 0.0154(7) -0.0013(7)
C3 0.0512(10) 0.0373(9) 0.0602(11) 0.0015(8) 0.0217(8) 0.0000(7)
N2 0.0555(9) 0.0473(9) 0.0744(11) 0.0005(8) 0.0316(8) -0.0046(7)
C4 0.0435(9) 0.0523(10) 0.0705(12) -0.0082(10) 0.0258(9) -0.0040(8)
C5 0.0454(9) 0.0447(9) 0.0608(11) -0.0009(9) 0.0168(8) 0.0023(8)
C6 0.0450(9) 0.0406(9) 0.0561(10) 0.0021(8) 0.0183(8) -0.0022(7)
C7 0.0428(8) 0.0362(8) 0.0451(9) 0.0034(7) 0.0163(7) 0.0001(7)
C8 0.0493(9) 0.0430(9) 0.0530(10) -0.0053(8) 0.0200(8) -0.0064(8)
C9 0.0432(9) 0.0563(11) 0.0573(11) -0.0018(9) 0.0143(8) -0.0100(8)
C10 0.0430(9) 0.0592(12) 0.0581(11) 0.0101(9) 0.0207(8) 0.0067(8)
C11 0.0575(11) 0.0446(10) 0.0619(11) -0.0006(9) 0.0268(9) 0.0069(8)
C12 0.0475(9) 0.0397(9) 0.0560(10) -0.0033(8) 0.0183(8) -0.0033(7)

_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
C1 O1 1.227(2) . ?
C1 N1 1.359(2) . ?
C1 C7 1.494(2) . ?
N1 C2 1.413(2) . ?
C2 C6 1.385(2) . ?
C2 C3 1.386(2) . ?
C3 N2 1.334(2) . ?
N2 C4 1.334(2) . ?
C4 C5 1.375(3) . ?
C5 C6 1.377(2) . ?
C7 C12 1.386(2) . ?
C7 C8 1.389(2) . ?
C8 C9 1.380(2) . ?
C9 C10 1.377(3) . ?
C10 C11 1.378(3) . ?
C11 C12 1.383(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
O1 C1 N1 122.65(16) . . ?
O1 C1 C7 121.47(15) . . ?
N1 C1 C7 115.88(14) . . ?
C1 N1 C2 125.51(14) . . ?
C6 C2 C3 118.47(15) . . ?
C6 C2 N1 122.96(15) . . ?
C3 C2 N1 118.52(15) . . ?
N2 C3 C2 123.59(17) . . ?
C4 N2 C3 116.78(16) . . ?
N2 C4 C5 123.76(16) . . ?
C4 C5 C6 119.03(17) . . ?
C5 C6 C2 118.35(16) . . ?
C12 C7 C8 119.15(15) . . ?
C12 C7 C1 122.82(15) . . ?
C8 C7 C1 117.98(15) . . ?
C9 C8 C7 120.24(17) . . ?
C10 C9 C8 120.32(17) . . ?
C9 C10 C11 119.84(16) . . ?
C10 C11 C12 120.20(17) . . ?
C11 C12 C7 120.24(17) . . ?

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
C7 N1 C1 C2 176.73(14) . . . . ?

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
N1 H1 O1 0.88 2.24 3.0740(19) 158.5 1_545

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        26.77
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.027
_database_code_depnum_ccdc_archive 'CCDC 989634'
