# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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.
#
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#  fide research purposes only. It may contain copyright material
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#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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data_28

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; methyl 6-methyl-2-(6-methylpyridin-2-ylcarbamoyl)nicotinate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 N3 O3'
_chemical_formula_sum            'C15 H15 N3 O3'
_chemical_formula_weight         285.30

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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 a 21'

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

_cell_length_a                   11.7899(6)
_cell_length_b                   15.7680(7)
_cell_length_c                   15.2980(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2843.9(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5353
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      25.17

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 0.00 0.0250
0.00 -1.00 0.00 0.0250
3.00 -1.00 -1.00 0.1600
-3.00 3.00 -1.00 0.1600
0.00 1.00 -2.00 0.1250
0.00 -1.00 2.00 0.1250

_exptl_special_details           
;The data collection nominally covered full sphere of reciprocal
space, by a combination of 3 runs of narrow-frame \w-scans (scan
width 0.3\% \w, 30s exposure), every run at a different \f angle.
Crystal to detector distance 4.85 cm. 4992 unique reflections before
merging Friedel equivalents.
;

_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  'Bruker SMART 6000 CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 5.6
_diffrn_standards_number         0
_diffrn_reflns_number            24307
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2598
_reflns_number_gt                2098
_reflns_threshold_expression     I>2\s(I)
_reflns_Friedel_coverage         0.92

_computing_data_collection       'SMART version 5.625 (Bruker, 2001)'
_computing_cell_refinement       'SAINT version 6.45A (Bruker, 2003)'
_computing_data_reduction        'SAINT version 6.45A (Bruker, 2003)'
_computing_structure_solution    
'XS, G.M.Sheldrick, Acta Cryst. (2008) A64, 112-122'
_computing_structure_refinement  
'SHELXTL 6.12, G.M.Sheldrick, Acta Cryst. (2008) A64, 112-122'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. The C(15')H~3~
group was treated as ideally disordered, other methyl groups as rigid bodies
rotating around C---C bonds, with a common refined U for each group. Amino
H atoms - N---H bond distances fixed but their directions refined. Other H
atoms: riding model.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0638P)^2^+0.9697P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
'undeterminable, all \Df" set to 0, Friedel equivalents merged'
_refine_ls_number_reflns         2598
_refine_ls_number_parameters     390
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1198
_refine_ls_wR_factor_gt          0.1025
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
O1 O 0.4571(3) 0.09575(17) 0.2066(2) 0.0512(8) Uani 1 1 d . . .
O2 O 0.3236(2) 0.04966(17) 0.36840(19) 0.0435(7) Uani 1 1 d . . .
O3 O 0.1979(3) 0.05474(17) 0.2591(2) 0.0510(8) Uani 1 1 d . . .
N1 N 0.3838(3) 0.3077(2) 0.2559(2) 0.0376(9) Uani 1 1 d . . .
N2 N 0.5348(3) 0.2227(2) 0.1654(2) 0.0365(7) Uani 1 1 d . . .
H2 H 0.5298 0.2782 0.1699 0.044 Uiso 1 1 d R . .
N3 N 0.6828(3) 0.2652(2) 0.0801(3) 0.0361(9) Uani 1 1 d . . .
C1 C 0.4592(3) 0.1733(2) 0.2081(3) 0.0354(9) Uani 1 1 d . . .
C2 C 0.3722(4) 0.2234(3) 0.2579(3) 0.0342(9) Uani 1 1 d . . .
C3 C 0.2826(4) 0.1827(3) 0.3007(3) 0.0374(9) Uani 1 1 d . . .
C4 C 0.2009(4) 0.2349(3) 0.3383(4) 0.0406(12) Uani 1 1 d . . .
H4 H 0.1367 0.2105 0.3660 0.049 Uiso 1 1 d R . .
C5 C 0.2127(4) 0.3206(3) 0.3357(3) 0.0447(11) Uani 1 1 d . . .
H5 H 0.1566 0.3559 0.3615 0.054 Uiso 1 1 d R . .
C6 C 0.3062(4) 0.3567(3) 0.2951(3) 0.0401(10) Uani 1 1 d . . .
C7 C 0.3277(4) 0.4502(3) 0.2945(3) 0.0538(12) Uani 1 1 d . . .
H7A H 0.3262 0.4709 0.2342 0.092(11) Uiso 1 1 d R . .
H7B H 0.2686 0.4789 0.3285 0.092(11) Uiso 1 1 d R . .
H7C H 0.4020 0.4621 0.3205 0.092(11) Uiso 1 1 d R . .
C8 C 0.2741(3) 0.0885(3) 0.3126(3) 0.0367(9) Uani 1 1 d . . .
C9 C 0.1777(4) -0.0351(3) 0.2709(3) 0.0583(13) Uani 1 1 d . . .
H9A H 0.1610 -0.0466 0.3325 0.074(9) Uiso 1 1 d R . .
H9B H 0.1131 -0.0527 0.2348 0.074(9) Uiso 1 1 d R . .
H9C H 0.2453 -0.0670 0.2533 0.074(9) Uiso 1 1 d R . .
C10 C 0.6256(3) 0.1986(2) 0.1111(3) 0.0345(8) Uani 1 1 d . . .
C11 C 0.6532(3) 0.1154(3) 0.0917(3) 0.0422(10) Uani 1 1 d . . .
H11 H 0.6111 0.0695 0.1155 0.051 Uiso 1 1 d R . .
C12 C 0.7431(4) 0.1016(3) 0.0367(3) 0.0481(10) Uani 1 1 d . . .
H12 H 0.7637 0.0455 0.0207 0.058 Uiso 1 1 d R . .
C13 C 0.8043(4) 0.1707(3) 0.0042(3) 0.0462(12) Uani 1 1 d . . .
H13 H 0.8675 0.1623 -0.0333 0.055 Uiso 1 1 d R . .
C14 C 0.7722(5) 0.2514(2) 0.0281(4) 0.0378(13) Uani 1 1 d . . .
C15 C 0.8345(4) 0.3286(3) -0.0042(4) 0.0508(13) Uani 1 1 d . . .
H15G H 0.7988 0.3494 -0.0580 0.121(14) Uiso 1 1 d R . .
H15H H 0.8324 0.3732 0.0404 0.121(14) Uiso 1 1 d R . .
H15I H 0.9137 0.3134 -0.0164 0.121(14) Uiso 1 1 d R . .
O1' O 0.2081(3) 0.09472(17) 0.6229(2) 0.0514(8) Uani 1 1 d . . .
O2' O 0.0621(3) 0.05559(19) 0.4571(2) 0.0517(8) Uani 1 1 d . . .
O3' O -0.0432(3) 0.05458(18) 0.5783(2) 0.0566(9) Uani 1 1 d . . .
N1' N 0.1370(3) 0.3080(2) 0.5792(2) 0.0360(8) Uani 1 1 d . . .
N2' N 0.2845(3) 0.2202(2) 0.6694(2) 0.0374(8) Uani 1 1 d . . .
H2' H 0.2738 0.2753 0.6661 0.045 Uiso 1 1 d R . .
N3' N 0.4321(3) 0.2615(2) 0.7554(3) 0.0391(10) Uani 1 1 d . . .
C1' C 0.2092(3) 0.1723(2) 0.6246(3) 0.0353(9) Uani 1 1 d . . .
C2' C 0.1227(3) 0.2236(3) 0.5769(3) 0.0325(9) Uani 1 1 d . . .
C3' C 0.0326(3) 0.1848(3) 0.5328(3) 0.0348(9) Uani 1 1 d . . .
C4' C -0.0474(4) 0.2375(3) 0.4940(4) 0.0444(13) Uani 1 1 d . . .
H4' H -0.1113 0.2140 0.4650 0.053 Uiso 1 1 d R . .
C5' C -0.0334(4) 0.3244(3) 0.4979(3) 0.0461(11) Uani 1 1 d . . .
H5' H -0.0882 0.3610 0.4725 0.055 Uiso 1 1 d R . .
C6' C 0.0615(4) 0.3581(3) 0.5389(3) 0.0410(10) Uani 1 1 d . . .
C7' C 0.0858(4) 0.4514(3) 0.5401(4) 0.0555(12) Uani 1 1 d . . .
H7'A H 0.0311 0.4809 0.5026 0.100(12) Uiso 1 1 d R . .
H7'B H 0.0794 0.4728 0.6000 0.100(12) Uiso 1 1 d R . .
H7'C H 0.1628 0.4615 0.5183 0.100(12) Uiso 1 1 d R . .
C8' C 0.0224(3) 0.0919(3) 0.5194(3) 0.0379(9) Uani 1 1 d . . .
C9' C -0.0613(5) -0.0355(3) 0.5667(4) 0.0688(16) Uani 1 1 d . . .
H9'A H -0.1224 -0.0544 0.6055 0.091(11) Uiso 1 1 d R . .
H9'B H -0.0823 -0.0471 0.5059 0.091(11) Uiso 1 1 d R . .
H9'C H 0.0086 -0.0660 0.5810 0.091(11) Uiso 1 1 d R . .
C10' C 0.3771(3) 0.1955(2) 0.7216(2) 0.0345(8) Uani 1 1 d . . .
C11' C 0.4073(3) 0.1120(2) 0.7356(3) 0.0415(9) Uani 1 1 d . . .
H11' H 0.3663 0.0667 0.7096 0.050 Uiso 1 1 d R . .
C12' C 0.5004(4) 0.0971(3) 0.7889(3) 0.0496(11) Uani 1 1 d . . .
H12' H 0.5239 0.0406 0.8004 0.060 Uiso 1 1 d R . .
C13' C 0.5584(4) 0.1643(3) 0.8249(3) 0.0469(12) Uani 1 1 d . . .
H13' H 0.6217 0.1547 0.8620 0.056 Uiso 1 1 d R . .
C14' C 0.5222(5) 0.2463(3) 0.8062(4) 0.0393(13) Uani 1 1 d . . .
C15' C 0.5820(5) 0.3226(3) 0.8425(4) 0.0550(14) Uani 1 1 d . . .
H15A H 0.5442 0.3743 0.8219 0.056(12) Uiso 0.50 1 d PR A 1
H15B H 0.6611 0.3227 0.8227 0.056(12) Uiso 0.50 1 d PR A 1
H15C H 0.5798 0.3208 0.9065 0.056(12) Uiso 0.50 1 d PR A 1
H15D H 0.5290 0.3558 0.8780 0.056(12) Uiso 0.50 1 d PR A 2
H15E H 0.6459 0.3042 0.8788 0.056(12) Uiso 0.50 1 d PR A 2
H15F H 0.6103 0.3577 0.7943 0.056(12) Uiso 0.50 1 d PR A 2

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 0.0646(19) 0.0304(16) 0.0585(19) -0.0030(13) 0.0209(16) -0.0065(14)
O2 0.0502(16) 0.0395(15) 0.0409(17) 0.0037(13) -0.0065(14) -0.0028(13)
O3 0.064(2) 0.0433(16) 0.0453(17) 0.0057(14) -0.0158(15) -0.0158(14)
N1 0.044(2) 0.0344(19) 0.0348(19) 0.0023(16) -0.0009(16) 0.0028(15)
N2 0.0374(19) 0.0273(17) 0.045(2) 0.0002(15) 0.0061(16) -0.0018(15)
N3 0.035(2) 0.0390(18) 0.035(2) 0.0024(16) -0.0010(19) -0.0018(15)
C1 0.042(2) 0.034(2) 0.031(2) 0.0007(16) 0.0005(18) -0.0038(17)
C2 0.035(2) 0.038(2) 0.029(2) 0.001(2) -0.0050(17) -0.002(2)
C3 0.039(2) 0.041(2) 0.032(2) 0.0031(19) -0.0052(19) -0.0026(18)
C4 0.035(3) 0.049(2) 0.038(3) 0.000(2) 0.003(2) 0.0006(19)
C5 0.046(3) 0.049(3) 0.040(2) 0.002(2) 0.002(2) 0.0117(19)
C6 0.049(3) 0.038(2) 0.033(2) 0.0026(19) -0.0021(19) 0.0069(19)
C7 0.068(3) 0.037(2) 0.056(3) 0.002(2) -0.001(3) 0.011(2)
C8 0.038(2) 0.041(2) 0.031(2) -0.0007(18) 0.0015(18) -0.0056(18)
C9 0.074(3) 0.047(3) 0.054(3) 0.004(2) -0.015(3) -0.020(2)
C10 0.0334(19) 0.034(2) 0.036(2) -0.0012(17) 0.0002(16) 0.0013(16)
C11 0.045(2) 0.036(2) 0.046(3) -0.0006(18) 0.0008(19) -0.0005(18)
C12 0.052(2) 0.043(2) 0.049(2) -0.005(2) 0.006(2) 0.0064(19)
C13 0.043(3) 0.051(3) 0.045(3) -0.005(2) 0.006(2) 0.002(2)
C14 0.036(3) 0.043(3) 0.035(3) 0.0014(16) 0.001(3) -0.0033(15)
C15 0.044(3) 0.052(3) 0.056(3) 0.008(2) 0.003(2) -0.011(2)
O1' 0.0623(19) 0.0333(17) 0.0585(19) 0.0016(14) -0.0219(17) -0.0028(13)
O2' 0.062(2) 0.0504(18) 0.0431(17) -0.0101(15) 0.0114(15) -0.0009(14)
O3' 0.073(2) 0.0432(17) 0.0529(19) -0.0116(15) 0.0266(17) -0.0190(15)
N1' 0.0411(19) 0.0330(19) 0.0339(19) 0.0001(15) 0.0015(16) 0.0024(15)
N2' 0.0401(19) 0.0296(19) 0.0426(19) -0.0014(16) -0.0055(16) 0.0015(15)
N3' 0.036(2) 0.044(2) 0.037(2) 0.0006(17) -0.001(2) -0.0012(15)
C1' 0.037(2) 0.032(2) 0.038(2) 0.0010(17) -0.0022(18) -0.0020(16)
C2' 0.035(2) 0.039(2) 0.024(2) 0.001(2) 0.0017(17) -0.004(2)
C3' 0.036(2) 0.042(2) 0.026(2) 0.0010(19) 0.0021(18) -0.0022(17)
C4' 0.042(3) 0.056(3) 0.035(3) -0.003(2) -0.006(2) 0.000(2)
C5' 0.049(3) 0.050(3) 0.039(2) 0.001(2) -0.004(2) 0.015(2)
C6' 0.049(3) 0.042(2) 0.032(2) 0.000(2) 0.002(2) 0.009(2)
C7' 0.072(3) 0.034(2) 0.060(3) 0.002(2) -0.006(3) 0.008(2)
C8' 0.034(2) 0.044(2) 0.035(2) -0.0013(19) -0.0009(18) -0.0027(18)
C9' 0.089(4) 0.040(3) 0.078(4) -0.017(2) 0.033(3) -0.021(3)
C10' 0.036(2) 0.036(2) 0.032(2) 0.0009(17) -0.0002(17) 0.0011(17)
C11' 0.045(2) 0.037(2) 0.042(2) -0.0008(18) -0.0010(19) 0.0015(18)
C12' 0.052(2) 0.041(2) 0.056(3) 0.003(2) -0.005(2) 0.011(2)
C13' 0.041(3) 0.058(3) 0.042(3) 0.000(2) -0.008(2) 0.008(2)
C14' 0.036(3) 0.047(3) 0.035(3) -0.0012(17) 0.000(3) 0.0002(16)
C15' 0.051(3) 0.060(3) 0.054(3) -0.011(2) -0.009(2) -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
O1 C1 1.223(5) . ?
O2 C8 1.201(5) . ?
O3 C8 1.328(5) . ?
O3 C9 1.448(5) . ?
N1 C2 1.337(5) . ?
N1 C6 1.338(5) . ?
N2 C1 1.351(5) . ?
N2 C10 1.407(5) . ?
N2 H2 0.8800 . ?
N3 C10 1.336(5) . ?
N3 C14 1.338(7) . ?
C1 C2 1.503(6) . ?
C2 C3 1.399(6) . ?
C3 C4 1.392(7) . ?
C3 C8 1.500(6) . ?
C4 C5 1.359(6) . ?
C4 H4 0.9497 . ?
C5 C6 1.387(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.497(6) . ?
C7 H7A 0.9799 . ?
C7 H7B 0.9799 . ?
C7 H7C 0.9802 . ?
C9 H9A 0.9801 . ?
C9 H9B 0.9802 . ?
C9 H9C 0.9801 . ?
C10 C11 1.383(5) . ?
C11 C12 1.370(6) . ?
C11 H11 0.9507 . ?
C12 C13 1.398(7) . ?
C12 H12 0.9502 . ?
C13 C14 1.377(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.505(6) . ?
C15 H15G 0.9802 . ?
C15 H15H 0.9801 . ?
C15 H15I 0.9808 . ?
O1' C1' 1.223(4) . ?
O2' C8' 1.206(5) . ?
O3' C8' 1.325(5) . ?
O3' C9' 1.447(5) . ?
N1' C6' 1.341(5) . ?
N1' C2' 1.343(5) . ?
N2' C1' 1.353(5) . ?
N2' C10' 1.407(5) . ?
N2' H2' 0.8799 . ?
N3' C10' 1.330(5) . ?
N3' C14' 1.338(7) . ?
C1' C2' 1.492(6) . ?
C2' C3' 1.399(6) . ?
C3' C4' 1.391(7) . ?
C3' C8' 1.484(6) . ?
C4' C5' 1.381(6) . ?
C4' H4' 0.9500 . ?
C5' C6' 1.388(6) . ?
C5' H5' 0.9500 . ?
C6' C7' 1.499(6) . ?
C7' H7'A 0.9808 . ?
C7' H7'B 0.9800 . ?
C7' H7'C 0.9799 . ?
C9' H9'A 0.9805 . ?
C9' H9'B 0.9799 . ?
C9' H9'C 0.9797 . ?
C10' C11' 1.382(5) . ?
C11' C12' 1.387(6) . ?
C11' H11' 0.9500 . ?
C12' C13' 1.376(7) . ?
C12' H12' 0.9498 . ?
C13' C14' 1.391(6) . ?
C13' H13' 0.9499 . ?
C14' C15' 1.502(7) . ?
C15' H15A 0.9800 . ?
C15' H15B 0.9799 . ?
C15' H15C 0.9800 . ?
C15' H15D 0.9801 . ?
C15' H15E 0.9800 . ?
C15' H15F 0.9799 . ?

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
C8 O3 C9 115.2(3) . . ?
C2 N1 C6 119.5(4) . . ?
C1 N2 C10 129.1(4) . . ?
C1 N2 H2 119.4 . . ?
C10 N2 H2 111.4 . . ?
C10 N3 C14 118.7(4) . . ?
O1 C1 N2 125.5(4) . . ?
O1 C1 C2 121.4(4) . . ?
N2 C1 C2 113.1(3) . . ?
N1 C2 C3 123.0(4) . . ?
N1 C2 C1 116.2(3) . . ?
C3 C2 C1 120.7(4) . . ?
C4 C3 C2 116.4(4) . . ?
C4 C3 C8 119.3(4) . . ?
C2 C3 C8 124.2(4) . . ?
C5 C4 C3 120.4(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.1(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 120.0 . . ?
N1 C6 C5 120.5(4) . . ?
N1 C6 C7 116.8(4) . . ?
C5 C6 C7 122.7(4) . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.7 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 O3 124.2(4) . . ?
O2 C8 C3 124.0(4) . . ?
O3 C8 C3 111.5(3) . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.4 . . ?
N3 C10 C11 123.4(4) . . ?
N3 C10 N2 112.4(4) . . ?
C11 C10 N2 124.2(4) . . ?
C12 C11 C10 117.7(4) . . ?
C12 C11 H11 121.2 . . ?
C10 C11 H11 121.1 . . ?
C11 C12 C13 119.6(4) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 119.0(5) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.7 . . ?
N3 C14 C13 121.6(4) . . ?
N3 C14 C15 116.6(4) . . ?
C13 C14 C15 121.7(5) . . ?
C14 C15 H15G 109.6 . . ?
C14 C15 H15H 109.7 . . ?
H15G C15 H15H 109.5 . . ?
C14 C15 H15I 109.2 . . ?
H15G C15 H15I 109.4 . . ?
H15H C15 H15I 109.4 . . ?
C8' O3' C9' 116.0(3) . . ?
C6' N1' C2' 119.2(4) . . ?
C1' N2' C10' 130.0(4) . . ?
C1' N2' H2' 115.3 . . ?
C10' N2' H2' 114.6 . . ?
C10' N3' C14' 118.2(4) . . ?
O1' C1' N2' 125.2(4) . . ?
O1' C1' C2' 121.6(4) . . ?
N2' C1' C2' 113.2(3) . . ?
N1' C2' C3' 122.8(4) . . ?
N1' C2' C1' 116.0(3) . . ?
C3' C2' C1' 121.2(4) . . ?
C4' C3' C2' 117.3(4) . . ?
C4' C3' C8' 118.5(4) . . ?
C2' C3' C8' 124.0(4) . . ?
C5' C4' C3' 119.6(5) . . ?
C5' C4' H4' 120.1 . . ?
C3' C4' H4' 120.3 . . ?
C4' C5' C6' 119.7(4) . . ?
C4' C5' H5' 120.2 . . ?
C6' C5' H5' 120.0 . . ?
N1' C6' C5' 121.2(4) . . ?
N1' C6' C7' 116.4(4) . . ?
C5' C6' C7' 122.4(4) . . ?
C6' C7' H7'A 109.4 . . ?
C6' C7' H7'B 109.6 . . ?
H7'A C7' H7'B 109.4 . . ?
C6' C7' H7'C 109.4 . . ?
H7'A C7' H7'C 109.5 . . ?
H7'B C7' H7'C 109.5 . . ?
O2' C8' O3' 123.6(4) . . ?
O2' C8' C3' 123.1(4) . . ?
O3' C8' C3' 113.0(3) . . ?
O3' C9' H9'A 109.4 . . ?
O3' C9' H9'B 109.7 . . ?
H9'A C9' H9'B 109.5 . . ?
O3' C9' H9'C 109.3 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
N3' C10' C11' 124.0(4) . . ?
N3' C10' N2' 112.5(4) . . ?
C11' C10' N2' 123.4(4) . . ?
C10' C11' C12' 117.2(4) . . ?
C10' C11' H11' 121.4 . . ?
C12' C11' H11' 121.5 . . ?
C13' C12' C11' 119.9(4) . . ?
C13' C12' H12' 120.2 . . ?
C11' C12' H12' 119.9 . . ?
C12' C13' C14' 118.7(5) . . ?
C12' C13' H13' 120.5 . . ?
C14' C13' H13' 120.8 . . ?
N3' C14' C13' 122.0(5) . . ?
N3' C14' C15' 116.4(4) . . ?
C13' C14' C15' 121.6(5) . . ?
C14' C15' H15A 109.5 . . ?
C14' C15' H15B 109.5 . . ?
H15A C15' H15B 109.5 . . ?
C14' C15' H15C 109.4 . . ?
H15A C15' H15C 109.5 . . ?
H15B C15' H15C 109.5 . . ?
C14' C15' H15D 109.4 . . ?
H15A C15' H15D 56.2 . . ?
H15B C15' H15D 141.0 . . ?
H15C C15' H15D 56.2 . . ?
C14' C15' H15E 109.5 . . ?
H15A C15' H15E 141.0 . . ?
H15B C15' H15E 56.2 . . ?
H15C C15' H15E 56.2 . . ?
H15D C15' H15E 109.5 . . ?
C14' C15' H15F 109.5 . . ?
H15A C15' H15F 56.2 . . ?
H15B C15' H15F 56.3 . . ?
H15C C15' H15F 141.0 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?

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
N1 C2 C1 N2 -2.4(5) . . . . ?
C2 C1 N2 C10 -178.4(4) . . . . ?
C1 N2 C10 N3 -179.8(4) . . . . ?
C2 C3 C8 O2 80.5(6) . . . . ?
N1' C2' C1' N2' 5.2(5) . . . . ?
C2' C1' N2' C10' 180.0(4) . . . . ?
C1' N2' C10' N3' 179.9(4) . . . . ?
C2' C3' C8' O2' -89.0(5) . . . . ?

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
N2 H2 N1 0.88 2.22 2.623(5) 107.9 .
N2' H2' N1' 0.88 2.15 2.617(5) 112.4 .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.046

#===END


_database_code_depnum_ccdc_archive 'CCDC 928417'