# Electronic Supplementary Material (ESI) for ChemComm.
# 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_mhpr121130

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 N3 O2'
_chemical_formula_sum            'C15 H17 N3 O2'
_chemical_formula_weight         271.32
_chemical_absolute_configuration rm

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           Monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   7.0231(8)
_cell_length_b                   10.3536(6)
_cell_length_c                   9.2156(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.182(4)
_cell_angle_gamma                90.00
_cell_volume                     669.07(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3658
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4161
_diffrn_reflns_av_R_equivalents  0.1056
_diffrn_reflns_av_sigmaI/netI    0.0837
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         27.47
_reflns_number_total             1605
_reflns_number_gt                1199
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0705P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   10(10)
_refine_ls_number_reflns         1605
_refine_ls_number_parameters     182
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1395
_refine_ls_wR_factor_gt          0.1239
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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 0.0047(5) 0.0537(3) 0.7023(4) 0.0372(9) Uani 1 1 d . . .
H1 H 0.0493 0.0185 0.6153 0.045 Uiso 1 1 calc R . .
C2 C 0.0127(5) -0.0202(4) 0.8276(4) 0.0416(9) Uani 1 1 d . . .
H2 H 0.0608 -0.1059 0.8255 0.050 Uiso 1 1 calc R . .
C3 C -0.0486(5) 0.0298(4) 0.9556(4) 0.0436(10) Uani 1 1 d . . .
H3 H -0.0440 -0.0214 1.0414 0.052 Uiso 1 1 calc R . .
C4 C -0.1162(5) 0.1539(4) 0.9580(4) 0.0411(9) Uani 1 1 d . . .
H4 H -0.1561 0.1894 1.0464 0.049 Uiso 1 1 calc R . .
C5 C -0.1269(5) 0.2282(4) 0.8322(4) 0.0360(8) Uani 1 1 d . . .
H5 H -0.1752 0.3138 0.8353 0.043 Uiso 1 1 calc R . .
C6 C -0.0676(4) 0.1785(3) 0.7019(4) 0.0319(8) Uani 1 1 d . . .
C7 C -0.0797(5) 0.2578(4) 0.5655(4) 0.0367(9) Uani 1 1 d . . .
H7A H -0.1738 0.2173 0.4955 0.044 Uiso 1 1 calc R . .
H7B H -0.1281 0.3447 0.5889 0.044 Uiso 1 1 calc R . .
C8 C 0.1388(5) 0.1945(3) 0.3815(4) 0.0340(8) Uani 1 1 d . . .
C9 C 0.3747(5) 0.4125(3) 0.4589(4) 0.0333(8) Uani 1 1 d . . .
C10 C 0.2504(5) 0.3528(3) 0.5673(4) 0.0318(8) Uani 1 1 d . . .
H10 H 0.1855 0.4247 0.6176 0.038 Uiso 1 1 calc R . .
C11 C 0.3757(6) 0.2815(4) 0.6819(4) 0.0409(9) Uani 1 1 d . . .
H11A H 0.2962 0.2480 0.7575 0.061 Uiso 1 1 calc R . .
H11B H 0.4709 0.3411 0.7256 0.061 Uiso 1 1 calc R . .
H11C H 0.4405 0.2096 0.6362 0.061 Uiso 1 1 calc R . .
C12 C 0.3918(6) 0.1373(4) 0.2148(4) 0.0417(9) Uani 1 1 d . . .
H12A H 0.3167 0.0566 0.2044 0.050 Uiso 1 1 calc R . .
H12B H 0.5212 0.1150 0.2550 0.050 Uiso 1 1 calc R . .
C13 C 0.4051(5) 0.2001(3) 0.0676(4) 0.0377(9) Uani 1 1 d . . .
H13A H 0.4880 0.1479 0.0068 0.045 Uiso 1 1 calc R . .
H13B H 0.2769 0.2053 0.0175 0.045 Uiso 1 1 calc R . .
C14 C 0.4863(5) 0.3324(4) 0.0884(4) 0.0393(9) Uani 1 1 d . . .
H14 H 0.5436 0.3730 0.0093 0.047 Uiso 1 1 calc R . .
C15 C 0.4811(5) 0.3952(4) 0.2137(4) 0.0366(9) Uani 1 1 d . . .
H15 H 0.5396 0.4778 0.2223 0.044 Uiso 1 1 calc R . .
N1 N 0.1012(4) 0.2724(3) 0.4952(3) 0.0325(7) Uani 1 1 d . . .
N2 N 0.3011(5) 0.2244(3) 0.3136(3) 0.0384(8) Uani 1 1 d . . .
N3 N 0.3928(4) 0.3443(3) 0.3336(3) 0.0326(7) Uani 1 1 d . . .
O1 O 0.0398(4) 0.1011(2) 0.3420(3) 0.0460(7) Uani 1 1 d . . .
O2 O 0.4545(4) 0.5163(3) 0.4798(3) 0.0497(8) Uani 1 1 d . . .


_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 C2 1.384(5) . ?
C1 C6 1.388(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.379(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.371(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.500(5) . ?
C7 N1 1.466(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O1 1.234(4) . ?
C8 N1 1.359(5) . ?
C8 N2 1.366(4) . ?
C9 O2 1.223(4) . ?
C9 N3 1.365(4) . ?
C9 C10 1.496(5) . ?
C10 N1 1.468(4) . ?
C10 C11 1.527(5) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N2 1.453(4) . ?
C12 C13 1.512(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.492(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.328(5) . ?
C14 H14 0.9500 . ?
C15 N3 1.400(4) . ?
C15 H15 0.9500 . ?
N2 N3 1.406(4) . ?

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
C2 C1 C6 121.0(3) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 119.4(4) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.6(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 117.9(3) . . ?
C1 C6 C7 121.1(3) . . ?
C5 C6 C7 121.0(3) . . ?
N1 C7 C6 114.6(3) . . ?
N1 C7 H7A 108.6 . . ?
C6 C7 H7A 108.6 . . ?
N1 C7 H7B 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
O1 C8 N1 124.2(3) . . ?
O1 C8 N2 120.9(3) . . ?
N1 C8 N2 114.9(3) . . ?
O2 C9 N3 121.6(3) . . ?
O2 C9 C10 122.5(3) . . ?
N3 C9 C10 115.9(3) . . ?
N1 C10 C9 111.1(3) . . ?
N1 C10 C11 114.1(3) . . ?
C9 C10 C11 109.1(3) . . ?
N1 C10 H10 107.4 . . ?
C9 C10 H10 107.4 . . ?
C11 C10 H10 107.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C13 110.3(3) . . ?
N2 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
N2 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 108.8(3) . . ?
C14 C13 H13A 109.9 . . ?
C12 C13 H13A 109.9 . . ?
C14 C13 H13B 109.9 . . ?
C12 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
C15 C14 C13 122.2(3) . . ?
C15 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
C14 C15 N3 122.5(3) . . ?
C14 C15 H15 118.7 . . ?
N3 C15 H15 118.7 . . ?
C8 N1 C7 119.3(3) . . ?
C8 N1 C10 121.4(3) . . ?
C7 N1 C10 118.2(3) . . ?
C8 N2 N3 121.8(3) . . ?
C8 N2 C12 123.5(3) . . ?
N3 N2 C12 114.6(3) . . ?
C9 N3 C15 122.6(3) . . ?
C9 N3 N2 120.3(3) . . ?
C15 N3 N2 116.6(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
C6 C1 C2 C3 -1.0(6) . . . . ?
C1 C2 C3 C4 -0.5(6) . . . . ?
C2 C3 C4 C5 1.3(6) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C2 C1 C6 C5 1.7(5) . . . . ?
C2 C1 C6 C7 -178.9(3) . . . . ?
C4 C5 C6 C1 -0.9(5) . . . . ?
C4 C5 C6 C7 179.7(3) . . . . ?
C1 C6 C7 N1 -55.3(4) . . . . ?
C5 C6 C7 N1 124.1(3) . . . . ?
O2 C9 C10 N1 150.7(3) . . . . ?
N3 C9 C10 N1 -28.9(4) . . . . ?
O2 C9 C10 C11 -82.7(4) . . . . ?
N3 C9 C10 C11 97.8(3) . . . . ?
N2 C12 C13 C14 48.9(4) . . . . ?
C12 C13 C14 C15 -21.1(5) . . . . ?
C13 C14 C15 N3 -2.6(6) . . . . ?
O1 C8 N1 C7 -8.5(5) . . . . ?
N2 C8 N1 C7 173.3(3) . . . . ?
O1 C8 N1 C10 159.5(3) . . . . ?
N2 C8 N1 C10 -18.7(5) . . . . ?
C6 C7 N1 C8 98.2(4) . . . . ?
C6 C7 N1 C10 -70.2(4) . . . . ?
C9 C10 N1 C8 40.8(4) . . . . ?
C11 C10 N1 C8 -83.0(4) . . . . ?
C9 C10 N1 C7 -151.1(3) . . . . ?
C11 C10 N1 C7 85.1(4) . . . . ?
O1 C8 N2 N3 165.7(3) . . . . ?
N1 C8 N2 N3 -16.1(5) . . . . ?
O1 C8 N2 C12 -13.7(5) . . . . ?
N1 C8 N2 C12 164.6(3) . . . . ?
C13 C12 N2 C8 121.8(4) . . . . ?
C13 C12 N2 N3 -57.6(4) . . . . ?
O2 C9 N3 C15 -8.8(5) . . . . ?
C10 C9 N3 C15 170.7(3) . . . . ?
O2 C9 N3 N2 179.2(3) . . . . ?
C10 C9 N3 N2 -1.3(4) . . . . ?
C14 C15 N3 C9 -174.9(3) . . . . ?
C14 C15 N3 N2 -2.7(5) . . . . ?
C8 N2 N3 C9 26.6(5) . . . . ?
C12 N2 N3 C9 -154.0(3) . . . . ?
C8 N2 N3 C15 -145.8(3) . . . . ?
C12 N2 N3 C15 33.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.080
_database_code_depnum_ccdc_archive 'CCDC 1001769'
#######################################################################
#
#                 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_shelx

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H13 N3 O3'
_chemical_formula_sum            'C10 H13 N3 O3'
_chemical_formula_weight         223.23

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.7486(5)
_cell_length_b                   7.2000(5)
_cell_length_c                   8.8891(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.796(2)
_cell_angle_gamma                90
_cell_volume                     490.09(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2108
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      29.93

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_F_000             236
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.114
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6901
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  triumph
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4338
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0146
_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       12
_diffrn_reflns_theta_min         2.318
_diffrn_reflns_theta_max         30.013
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.960
_reflns_number_total             2637
_reflns_number_gt                2386
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_max     0.837
_reflns_Friedel_fraction_full    0.915

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0532P)²+0.0370P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 948 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.8(4)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2637
_refine_ls_number_parameters     149
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0873
_refine_ls_wR_factor_gt          0.0835
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5046(2) 0.1812(3) 0.3179(2) 0.0232(4) Uani 1 1 d . . . . .
H1A H 0.5124 0.3183 0.3131 0.028 Uiso 1 1 calc R U . . .
H1B H 0.3940 0.1467 0.3535 0.028 Uiso 1 1 calc R U . . .
C2 C 0.5163(2) 0.0931(3) 0.1612(2) 0.0233(4) Uani 1 1 d . . . . .
H2 H 0.4936 0.1909 0.0808 0.028 Uiso 1 1 calc R U . . .
C3 C 0.7071(2) 0.0292(3) 0.1743(2) 0.0224(4) Uani 1 1 d . . . . .
H3A H 0.7191 -0.0749 0.1038 0.027 Uiso 1 1 calc R U . . .
H3B H 0.7840 0.1324 0.1526 0.027 Uiso 1 1 calc R U . . .
C4 C 0.7495(2) -0.0328(2) 0.33906(19) 0.0172(3) Uani 1 1 d . . . . .
H4 H 0.7010 -0.1597 0.3508 0.021 Uiso 1 1 calc R U . . .
C5 C 0.9408(2) -0.0282(2) 0.4065(2) 0.0189(3) Uani 1 1 d . . . . .
C6 C 0.6722(2) 0.1014(2) 0.5716(2) 0.0178(3) Uani 1 1 d . . . . .
C7 C 1.1314(2) 0.0087(2) 0.6492(2) 0.0214(4) Uani 1 1 d . . . . .
H7 H 1.2310 -0.0031 0.5996 0.026 Uiso 1 1 calc R U . . .
C8 C 1.1550(2) 0.0419(3) 0.7976(2) 0.0243(4) Uani 1 1 d . . . . .
H8 H 1.2707 0.0541 0.8503 0.029 Uiso 1 1 calc R U . . .
C9 C 1.0058(3) 0.0608(3) 0.8845(2) 0.0258(4) Uani 1 1 d . . . . .
H9A H 0.9761 0.1936 0.8941 0.031 Uiso 1 1 calc R U . . .
H9B H 1.0383 0.0088 0.9881 0.031 Uiso 1 1 calc R U . . .
C10 C 0.8490(3) -0.0439(3) 0.8001(2) 0.0235(4) Uani 1 1 d . . . . .
H10A H 0.8701 -0.1793 0.8105 0.028 Uiso 1 1 calc R U . . .
H10B H 0.7439 -0.0141 0.8462 0.028 Uiso 1 1 calc R U . . .
N1 N 0.65602(19) 0.1033(2) 0.41861(17) 0.0188(3) Uani 1 1 d . . . . .
N2 N 0.96408(18) -0.0099(2) 0.56200(17) 0.0190(3) Uani 1 1 d . . . . .
N3 N 0.81828(19) 0.0058(2) 0.63882(17) 0.0206(3) Uani 1 1 d . . . . .
O1 O 0.39627(19) -0.0553(2) 0.12444(17) 0.0302(4) Uani 1 1 d . . . . .
O2 O 1.06219(18) -0.0345(2) 0.33405(17) 0.0309(3) Uani 1 1 d . . . . .
O3 O 0.56497(17) 0.1681(2) 0.64587(15) 0.0243(3) Uani 1 1 d . . . . .
H1C H 0.408(4) -0.132(5) 0.199(4) 0.049(9) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.473(2) . ?
C1 C2 1.545(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 O1 1.422(2) . ?
C2 C3 1.536(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.518(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N1 1.464(2) . ?
C4 C5 1.512(2) . ?
C4 H4 1.0000 . ?
C5 O2 1.220(2) . ?
C5 N2 1.373(2) . ?
C6 O3 1.235(2) . ?
C6 N1 1.346(2) . ?
C6 N3 1.380(2) . ?
C7 C8 1.326(3) . ?
C7 N2 1.411(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.491(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.527(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N3 1.461(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
N2 N3 1.411(2) . ?
O1 H1C 0.86(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 103.91(15) . . ?
N1 C1 H1A 111.0 . . ?
C2 C1 H1A 111.0 . . ?
N1 C1 H1B 111.0 . . ?
C2 C1 H1B 111.0 . . ?
H1A C1 H1B 109.0 . . ?
O1 C2 C3 112.35(17) . . ?
O1 C2 C1 112.91(16) . . ?
C3 C2 C1 104.09(14) . . ?
O1 C2 H2 109.1 . . ?
C3 C2 H2 109.1 . . ?
C1 C2 H2 109.1 . . ?
C4 C3 C2 102.98(14) . . ?
C4 C3 H3A 111.2 . . ?
C2 C3 H3A 111.2 . . ?
C4 C3 H3B 111.2 . . ?
C2 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
N1 C4 C5 108.75(14) . . ?
N1 C4 C3 102.68(14) . . ?
C5 C4 C3 115.49(14) . . ?
N1 C4 H4 109.9 . . ?
C5 C4 H4 109.9 . . ?
C3 C4 H4 109.9 . . ?
O2 C5 N2 122.82(16) . . ?
O2 C5 C4 125.34(16) . . ?
N2 C5 C4 111.81(14) . . ?
O3 C6 N1 124.72(16) . . ?
O3 C6 N3 122.45(16) . . ?
N1 C6 N3 112.72(15) . . ?
C8 C7 N2 122.65(17) . . ?
C8 C7 H7 118.7 . . ?
N2 C7 H7 118.7 . . ?
C7 C8 C9 122.12(16) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 H8 118.9 . . ?
C8 C9 C10 108.79(16) . . ?
C8 C9 H9A 109.9 . . ?
C10 C9 H9A 109.9 . . ?
C8 C9 H9B 109.9 . . ?
C10 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
N3 C10 C9 111.08(15) . . ?
N3 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
N3 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C6 N1 C4 120.29(14) . . ?
C6 N1 C1 124.08(15) . . ?
C4 N1 C1 111.60(14) . . ?
C5 N2 N3 120.21(13) . . ?
C5 N2 C7 122.05(15) . . ?
N3 N2 C7 117.55(15) . . ?
C6 N3 N2 119.63(14) . . ?
C6 N3 C10 123.14(15) . . ?
N2 N3 C10 115.65(14) . . ?
C2 O1 H1C 108(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
N1 C1 C2 O1 102.41(18) . . . . ?
N1 C1 C2 C3 -19.71(19) . . . . ?
O1 C2 C3 C4 -87.01(18) . . . . ?
C1 C2 C3 C4 35.48(19) . . . . ?
C2 C3 C4 N1 -37.38(17) . . . . ?
C2 C3 C4 C5 -155.57(16) . . . . ?
N1 C4 C5 O2 -137.86(19) . . . . ?
C3 C4 C5 O2 -23.1(3) . . . . ?
N1 C4 C5 N2 40.18(19) . . . . ?
C3 C4 C5 N2 154.93(15) . . . . ?
N2 C7 C8 C9 0.5(3) . . . . ?
C7 C8 C9 C10 24.7(3) . . . . ?
C8 C9 C10 N3 -49.1(2) . . . . ?
O3 C6 N1 C4 -157.30(17) . . . . ?
N3 C6 N1 C4 19.0(2) . . . . ?
O3 C6 N1 C1 -1.8(3) . . . . ?
N3 C6 N1 C1 174.47(17) . . . . ?
C5 C4 N1 C6 -52.6(2) . . . . ?
C3 C4 N1 C6 -175.42(15) . . . . ?
C5 C4 N1 C1 149.11(15) . . . . ?
C3 C4 N1 C1 26.27(19) . . . . ?
C2 C1 N1 C6 -161.36(17) . . . . ?
C2 C1 N1 C4 -4.0(2) . . . . ?
O2 C5 N2 N3 176.85(19) . . . . ?
C4 C5 N2 N3 -1.2(2) . . . . ?
O2 C5 N2 C7 1.9(3) . . . . ?
C4 C5 N2 C7 -176.16(16) . . . . ?
C8 C7 N2 C5 174.23(17) . . . . ?
C8 C7 N2 N3 -0.8(3) . . . . ?
O3 C6 N3 N2 -157.68(17) . . . . ?
N1 C6 N3 N2 25.9(2) . . . . ?
O3 C6 N3 C10 7.4(3) . . . . ?
N1 C6 N3 C10 -169.02(16) . . . . ?
C5 N2 N3 C6 -35.7(2) . . . . ?
C7 N2 N3 C6 139.43(17) . . . . ?
C5 N2 N3 C10 158.16(15) . . . . ?
C7 N2 N3 C10 -26.7(2) . . . . ?
C9 C10 N3 C6 -113.3(2) . . . . ?
C9 C10 N3 N2 52.3(2) . . . . ?

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
O1 H1C O3 0.86(3) 1.98(4) 2.835(2) 173(3) 2_646

_refine_diff_density_max         0.286
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.041

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1001770'
#######################################################################
#
#                 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_mhpr121113

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H19 N3 O2'
_chemical_formula_sum            'C16 H19 N3 O2'
_chemical_formula_weight         285.34
_chemical_absolute_configuration rm

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 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   7.9124(2)
_cell_length_b                   9.5931(3)
_cell_length_c                   19.4561(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1476.80(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7512
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11494
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         27.47
_reflns_number_total             1952
_reflns_number_gt                1721
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0736P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.089(8)
_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   10(10)
_refine_ls_number_reflns         1952
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1247
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   1.212
_refine_ls_restrained_S_all      1.212
_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 0.9980(3) 0.9253(2) 0.37965(13) 0.0340(5) Uani 1 1 d . . .
H1 H 1.0616 1.0088 0.3753 0.041 Uiso 1 1 calc R . .
C2 C 0.9830(3) 0.8611(3) 0.44340(14) 0.0446(6) Uani 1 1 d . . .
H2 H 1.0374 0.9004 0.4824 0.053 Uiso 1 1 calc R . .
C3 C 0.8896(4) 0.7409(3) 0.45035(16) 0.0560(8) Uani 1 1 d . . .
H3 H 0.8775 0.6985 0.4942 0.067 Uiso 1 1 calc R . .
C4 C 0.8138(4) 0.6820(3) 0.39344(16) 0.0582(8) Uani 1 1 d . . .
H4 H 0.7518 0.5977 0.3979 0.070 Uiso 1 1 calc R . .
C5 C 0.8278(3) 0.7458(3) 0.32969(14) 0.0425(6) Uani 1 1 d . . .
H5 H 0.7736 0.7058 0.2909 0.051 Uiso 1 1 calc R . .
C6 C 0.9204(3) 0.8677(2) 0.32219(12) 0.0293(5) Uani 1 1 d . . .
C7 C 0.9436(3) 0.9363(3) 0.25295(13) 0.0383(6) Uani 1 1 d . . .
H7A H 0.9653 1.0370 0.2598 0.046 Uiso 1 1 calc R . .
H7B H 1.0440 0.8957 0.2302 0.046 Uiso 1 1 calc R . .
C8 C 0.8069(2) 0.8405(3) 0.14985(11) 0.0302(5) Uani 1 1 d . . .
C9 C 0.4939(3) 0.9487(2) 0.20151(11) 0.0293(5) Uani 1 1 d . . .
C10 C 0.6601(3) 1.0208(2) 0.21416(13) 0.0356(5) Uani 1 1 d . . .
H10 H 0.6594 1.0555 0.2626 0.043 Uiso 1 1 calc R . .
C11 C 0.6814(4) 1.1471(3) 0.16695(19) 0.0541(7) Uani 1 1 d . . .
H11A H 0.6766 1.1168 0.1189 0.081 Uiso 1 1 calc R . .
H11B H 0.7908 1.1914 0.1759 0.081 Uiso 1 1 calc R . .
H11C H 0.5904 1.2141 0.1758 0.081 Uiso 1 1 calc R . .
C12 C 0.6461(3) 0.7863(2) 0.04419(11) 0.0341(5) Uani 1 1 d . . .
H12A H 0.7477 0.8211 0.0199 0.041 Uiso 1 1 calc R . .
H12B H 0.5461 0.8307 0.0229 0.041 Uiso 1 1 calc R . .
C13 C 0.6342(3) 0.6288(3) 0.03431(13) 0.0415(6) Uani 1 1 d . . .
H13A H 0.7493 0.5885 0.0335 0.050 Uiso 1 1 calc R . .
H13B H 0.5799 0.6086 -0.0104 0.050 Uiso 1 1 calc R . .
C14 C 0.5318(4) 0.5605(3) 0.09195(14) 0.0512(7) Uani 1 1 d . . .
H14A H 0.5030 0.4639 0.0783 0.061 Uiso 1 1 calc R . .
H14B H 0.6024 0.5555 0.1339 0.061 Uiso 1 1 calc R . .
C15 C 0.3724(3) 0.6376(3) 0.10819(12) 0.0419(6) Uani 1 1 d . . .
H15 H 0.2690 0.5912 0.0985 0.050 Uiso 1 1 calc R . .
C16 C 0.3618(3) 0.7640(3) 0.13473(11) 0.0337(5) Uani 1 1 d . . .
H16 H 0.2520 0.7994 0.1440 0.040 Uiso 1 1 calc R . .
N1 N 0.7972(2) 0.9196(2) 0.20804(10) 0.0320(5) Uani 1 1 d . . .
N2 N 0.6555(2) 0.8285(2) 0.11616(9) 0.0335(5) Uani 1 1 d . . .
N3 N 0.50110(19) 0.8512(2) 0.15054(9) 0.0298(4) Uani 1 1 d . . .
O1 O 0.9361(2) 0.7867(2) 0.12727(9) 0.0428(5) Uani 1 1 d . . .
O2 O 0.36530(19) 0.9712(2) 0.23434(9) 0.0412(5) Uani 1 1 d . . .


_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 C6 1.390(3) . ?
C1 C2 1.390(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.376(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.510(3) . ?
C7 N1 1.460(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O1 1.227(3) . ?
C8 N1 1.365(3) . ?
C8 N2 1.370(3) . ?
C9 O2 1.220(3) . ?
C9 N3 1.364(3) . ?
C9 C10 1.506(3) . ?
C10 N1 1.460(3) . ?
C10 C11 1.530(4) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N2 1.459(3) . ?
C12 C13 1.527(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.530(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.496(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.321(4) . ?
C15 H15 0.9500 . ?
C16 N3 1.417(3) . ?
C16 H16 0.9500 . ?
N2 N3 1.410(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 C1 C2 120.3(2) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 118.9(2) . . ?
C5 C6 C7 121.7(2) . . ?
C1 C6 C7 119.4(2) . . ?
N1 C7 C6 112.94(17) . . ?
N1 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
O1 C8 N1 125.3(2) . . ?
O1 C8 N2 121.5(2) . . ?
N1 C8 N2 113.24(18) . . ?
O2 C9 N3 122.4(2) . . ?
O2 C9 C10 124.2(2) . . ?
N3 C9 C10 113.38(18) . . ?
N1 C10 C9 109.32(17) . . ?
N1 C10 C11 113.3(2) . . ?
C9 C10 C11 111.2(2) . . ?
N1 C10 H10 107.6 . . ?
C9 C10 H10 107.6 . . ?
C11 C10 H10 107.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C13 113.46(19) . . ?
N2 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
N2 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 C14 111.4(2) . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C15 C14 C13 112.9(2) . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C16 C15 C14 126.2(2) . . ?
C16 C15 H15 116.9 . . ?
C14 C15 H15 116.9 . . ?
C15 C16 N3 125.3(2) . . ?
C15 C16 H16 117.4 . . ?
N3 C16 H16 117.4 . . ?
C8 N1 C7 120.86(19) . . ?
C8 N1 C10 118.59(18) . . ?
C7 N1 C10 117.90(18) . . ?
C8 N2 N3 121.16(16) . . ?
C8 N2 C12 121.80(18) . . ?
N3 N2 C12 116.99(18) . . ?
C9 N3 N2 119.15(17) . . ?
C9 N3 C16 122.00(18) . . ?
N2 N3 C16 118.64(18) . . ?

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
C6 C1 C2 C3 -0.7(4) . . . . ?
C1 C2 C3 C4 1.5(4) . . . . ?
C2 C3 C4 C5 -1.7(5) . . . . ?
C3 C4 C5 C6 1.1(5) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C4 C5 C6 C7 177.5(3) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
C2 C1 C6 C7 -177.8(2) . . . . ?
C5 C6 C7 N1 33.6(3) . . . . ?
C1 C6 C7 N1 -148.5(2) . . . . ?
O2 C9 C10 N1 139.5(2) . . . . ?
N3 C9 C10 N1 -38.6(3) . . . . ?
O2 C9 C10 C11 -94.7(3) . . . . ?
N3 C9 C10 C11 87.2(2) . . . . ?
N2 C12 C13 C14 34.7(3) . . . . ?
C12 C13 C14 C15 45.1(3) . . . . ?
C13 C14 C15 C16 -66.0(3) . . . . ?
C14 C15 C16 N3 2.1(4) . . . . ?
O1 C8 N1 C7 -5.8(4) . . . . ?
N2 C8 N1 C7 176.0(2) . . . . ?
O1 C8 N1 C10 155.4(2) . . . . ?
N2 C8 N1 C10 -22.8(3) . . . . ?
C6 C7 N1 C8 -112.6(2) . . . . ?
C6 C7 N1 C10 86.1(3) . . . . ?
C9 C10 N1 C8 52.9(3) . . . . ?
C11 C10 N1 C8 -71.8(3) . . . . ?
C9 C10 N1 C7 -145.4(2) . . . . ?
C11 C10 N1 C7 90.0(3) . . . . ?
O1 C8 N2 N3 160.3(2) . . . . ?
N1 C8 N2 N3 -21.4(3) . . . . ?
O1 C8 N2 C12 -17.2(4) . . . . ?
N1 C8 N2 C12 161.1(2) . . . . ?
C13 C12 N2 C8 89.1(3) . . . . ?
C13 C12 N2 N3 -88.5(3) . . . . ?
O2 C9 N3 N2 -178.2(2) . . . . ?
C10 C9 N3 N2 -0.1(3) . . . . ?
O2 C9 N3 C16 -3.4(3) . . . . ?
C10 C9 N3 C16 174.7(2) . . . . ?
C8 N2 N3 C9 33.8(3) . . . . ?
C12 N2 N3 C9 -148.6(2) . . . . ?
C8 N2 N3 C16 -141.2(2) . . . . ?
C12 N2 N3 C16 36.5(3) . . . . ?
C15 C16 N3 C9 -151.8(2) . . . . ?
C15 C16 N3 N2 23.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.149
_database_code_depnum_ccdc_archive 'CCDC 1001771'
#######################################################################
#
#                 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_mhpr130206

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H21 N3 O3'
_chemical_formula_sum            'C16 H21 N3 O3'
_chemical_formula_weight         303.36
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'
_symmetry_space_group_name_Hall  'C 2y'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   10.6284(6)
_cell_length_b                   11.6932(6)
_cell_length_c                   25.7411(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.369(3)
_cell_angle_gamma                90.00
_cell_volume                     3136.3(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9906
_cell_measurement_theta_min      5.69
_cell_measurement_theta_max      66.67

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    0.735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7574
_exptl_absorpt_correction_T_max  0.8375
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13001
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         5.69
_diffrn_reflns_theta_max         66.67
_reflns_number_total             4347
_reflns_number_gt                4276
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0418P)²+0.7289P] 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       0.0035(2)
_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   -0.08(14)
_refine_ls_number_reflns         4347
_refine_ls_number_parameters     402
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0770
_refine_ls_wR_factor_gt          0.0766
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.16367(14) 0.81730(14) 0.82945(6) 0.0264(3) Uani 1 1 d . . .
C2 C 0.04215(16) 0.84923(17) 0.80332(7) 0.0367(4) Uani 1 1 d . . .
H2 H 0.0327 0.9111 0.7789 0.044 Uiso 1 1 calc R . .
C3 C -0.06559(16) 0.7923(2) 0.81229(8) 0.0448(5) Uani 1 1 d . . .
H3 H -0.1483 0.8144 0.7937 0.054 Uiso 1 1 calc R . .
C4 C -0.05329(18) 0.7031(2) 0.84824(8) 0.0445(5) Uani 1 1 d . . .
H4 H -0.1271 0.6635 0.8543 0.053 Uiso 1 1 calc R . .
C5 C 0.06697(19) 0.67233(18) 0.87519(8) 0.0437(4) Uani 1 1 d . . .
H5 H 0.0761 0.6125 0.9006 0.052 Uiso 1 1 calc R . .
C6 C 0.17518(16) 0.72848(16) 0.86537(6) 0.0336(4) Uani 1 1 d . . .
H6 H 0.2579 0.7055 0.8836 0.040 Uiso 1 1 calc R . .
C7 C 0.27709(15) 0.88102(15) 0.81646(7) 0.0315(4) Uani 1 1 d . . .
H7A H 0.2724 0.8778 0.7777 0.038 Uiso 1 1 calc R . .
H7B H 0.2709 0.9624 0.8263 0.038 Uiso 1 1 calc R . .
C8 C 0.45107(14) 0.87425(14) 0.89345(6) 0.0263(3) Uani 1 1 d . . .
C9 C 0.58527(14) 0.71816(14) 0.83857(6) 0.0258(3) Uani 1 1 d . . .
C10 C 0.49343(15) 0.80586(14) 0.80966(6) 0.0284(3) Uani 1 1 d . . .
H10 H 0.4442 0.7689 0.7768 0.034 Uiso 1 1 calc R . .
C11 C 0.56350(19) 0.90886(18) 0.79270(8) 0.0418(4) Uani 1 1 d . . .
H11A H 0.5007 0.9643 0.7746 0.063 Uiso 1 1 calc R . .
H11B H 0.6188 0.8838 0.7686 0.063 Uiso 1 1 calc R . .
H11C H 0.6160 0.9447 0.8240 0.063 Uiso 1 1 calc R . .
C12 C 0.65670(16) 0.88142(16) 0.95795(7) 0.0360(4) Uani 1 1 d . . .
H12A H 0.6114 0.9381 0.9762 0.043 Uiso 1 1 calc R . .
H12B H 0.7208 0.9227 0.9418 0.043 Uiso 1 1 calc R . .
C13 C 0.7242(2) 0.79552(19) 0.99778(7) 0.0454(5) Uani 1 1 d . . .
H13A H 0.6621 0.7623 1.0176 0.054 Uiso 1 1 calc R . .
H13B H 0.7925 0.8344 1.0234 0.054 Uiso 1 1 calc R . .
C14 C 0.78309(17) 0.70033(19) 0.96982(7) 0.0424(4) Uani 1 1 d . . .
H14A H 0.8510 0.7324 0.9527 0.051 Uiso 1 1 calc R . .
H14B H 0.8229 0.6425 0.9961 0.051 Uiso 1 1 calc R . .
C15 C 0.68110(16) 0.64430(16) 0.92846(6) 0.0320(3) Uani 1 1 d . . .
H15 H 0.7216 0.5863 0.9084 0.038 Uiso 1 1 calc R . .
C16 C 0.5044(2) 0.5192(2) 0.92270(9) 0.0550(5) Uani 1 1 d . . .
H16A H 0.4508 0.5657 0.8953 0.082 Uiso 1 1 calc R . .
H16B H 0.4502 0.4818 0.9443 0.082 Uiso 1 1 calc R . .
H16C H 0.5495 0.4610 0.9059 0.082 Uiso 1 1 calc R . .
C17 C 0.34139(15) 0.66069(15) 0.67723(6) 0.0296(3) Uani 1 1 d . . .
C18 C 0.30617(18) 0.74979(17) 0.64226(7) 0.0402(4) Uani 1 1 d . . .
H18 H 0.3635 0.7753 0.6207 0.048 Uiso 1 1 calc R . .
C19 C 0.1873(2) 0.8025(2) 0.63834(9) 0.0537(5) Uani 1 1 d . . .
H19 H 0.1632 0.8628 0.6136 0.064 Uiso 1 1 calc R . .
C20 C 0.10432(19) 0.7675(2) 0.67026(10) 0.0601(7) Uani 1 1 d . . .
H20 H 0.0233 0.8037 0.6678 0.072 Uiso 1 1 calc R . .
C21 C 0.1400(2) 0.6796(2) 0.70567(10) 0.0555(6) Uani 1 1 d . . .
H21 H 0.0835 0.6555 0.7279 0.067 Uiso 1 1 calc R . .
C22 C 0.25688(17) 0.62622(18) 0.70917(8) 0.0419(4) Uani 1 1 d . . .
H22 H 0.2800 0.5653 0.7336 0.050 Uiso 1 1 calc R . .
C23 C 0.46538(15) 0.59550(15) 0.68151(6) 0.0314(3) Uani 1 1 d . . .
H23A H 0.5053 0.5871 0.7195 0.038 Uiso 1 1 calc R . .
H23B H 0.4458 0.5178 0.6668 0.038 Uiso 1 1 calc R . .
C24 C 0.55905(14) 0.61621(13) 0.60329(6) 0.0260(3) Uani 1 1 d . . .
C25 C 0.73707(14) 0.77847(14) 0.65837(6) 0.0266(3) Uani 1 1 d . . .
C26 C 0.68094(15) 0.68467(15) 0.68670(6) 0.0287(3) Uani 1 1 d . . .
H26 H 0.6631 0.7170 0.7205 0.034 Uiso 1 1 calc R . .
C27 C 0.77497(18) 0.58729(18) 0.70076(8) 0.0440(4) Uani 1 1 d . . .
H27A H 0.7353 0.5263 0.7181 0.066 Uiso 1 1 calc R . .
H27B H 0.8521 0.6150 0.7248 0.066 Uiso 1 1 calc R . .
H27C H 0.7985 0.5574 0.6684 0.066 Uiso 1 1 calc R . .
C28 C 0.70191(19) 0.61716(17) 0.53849(7) 0.0388(4) Uani 1 1 d . . .
H28A H 0.6408 0.5600 0.5196 0.047 Uiso 1 1 calc R . .
H28B H 0.7816 0.5767 0.5550 0.047 Uiso 1 1 calc R . .
C29 C 0.7319(2) 0.7050(2) 0.49945(8) 0.0483(5) Uani 1 1 d . . .
H29A H 0.6509 0.7376 0.4793 0.058 Uiso 1 1 calc R . .
H29B H 0.7775 0.6677 0.4740 0.058 Uiso 1 1 calc R . .
C30 C 0.8149(2) 0.80038(19) 0.52843(8) 0.0461(5) Uani 1 1 d . . .
H30A H 0.8992 0.7688 0.5457 0.055 Uiso 1 1 calc R . .
H30B H 0.8299 0.8591 0.5026 0.055 Uiso 1 1 calc R . .
C31 C 0.75118(16) 0.85493(15) 0.56964(7) 0.0339(4) Uani 1 1 d . . .
H31 H 0.8106 0.9119 0.5906 0.041 Uiso 1 1 calc R . .
C32 C 0.5761(2) 0.9753(2) 0.57607(9) 0.0557(5) Uani 1 1 d . . .
H32A H 0.5429 0.9239 0.6003 0.084 Uiso 1 1 calc R . .
H32B H 0.5048 1.0173 0.5544 0.084 Uiso 1 1 calc R . .
H32C H 0.6365 1.0296 0.5966 0.084 Uiso 1 1 calc R . .
N1 N 0.40159(12) 0.83673(13) 0.84309(5) 0.0281(3) Uani 1 1 d . . .
N2 N 0.56456(13) 0.82428(12) 0.91646(5) 0.0299(3) Uani 1 1 d . . .
N3 N 0.61579(12) 0.73205(12) 0.89165(5) 0.0276(3) Uani 1 1 d . . .
N4 N 0.55840(11) 0.64933(12) 0.65398(5) 0.0270(3) Uani 1 1 d . . .
N5 N 0.64611(12) 0.67291(12) 0.57970(5) 0.0291(3) Uani 1 1 d . . .
N6 N 0.71861(13) 0.76517(11) 0.60530(5) 0.0277(3) Uani 1 1 d . . .
O1 O 0.39848(11) 0.94536(10) 0.91697(5) 0.0345(3) Uani 1 1 d . . .
O2 O 0.62679(11) 0.63973(11) 0.81525(4) 0.0352(3) Uani 1 1 d . . .
O3 O 0.59490(13) 0.58990(12) 0.95519(5) 0.0424(3) Uani 1 1 d . . .
O4 O 0.48775(11) 0.54269(11) 0.57928(5) 0.0366(3) Uani 1 1 d . . .
O5 O 0.79447(12) 0.85989(11) 0.68197(5) 0.0392(3) Uani 1 1 d . . .
O6 O 0.63997(13) 0.91051(12) 0.54276(5) 0.0437(3) Uani 1 1 d . . .


_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 C6 1.380(2) . ?
C1 C2 1.385(2) . ?
C1 C7 1.510(2) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.460(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O1 1.2263(19) . ?
C8 N2 1.366(2) . ?
C8 N1 1.372(2) . ?
C9 O2 1.225(2) . ?
C9 N3 1.350(2) . ?
C9 C10 1.507(2) . ?
C10 N1 1.4677(19) . ?
C10 C11 1.524(2) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N2 1.461(2) . ?
C12 C13 1.512(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.525(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.511(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 O3 1.402(2) . ?
C15 N3 1.474(2) . ?
C15 H15 1.0000 . ?
C16 O3 1.411(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.380(3) . ?
C17 C22 1.391(2) . ?
C17 C23 1.508(2) . ?
C18 C19 1.391(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.381(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.376(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.377(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 N4 1.4670(19) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 O4 1.229(2) . ?
C24 N4 1.362(2) . ?
C24 N5 1.373(2) . ?
C25 O5 1.225(2) . ?
C25 N6 1.350(2) . ?
C25 C26 1.504(2) . ?
C26 N4 1.4642(19) . ?
C26 C27 1.511(3) . ?
C26 H26 1.0000 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 N5 1.466(2) . ?
C28 C29 1.514(3) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.523(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.508(3) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 O6 1.406(2) . ?
C31 N6 1.479(2) . ?
C31 H31 1.0000 . ?
C32 O6 1.414(3) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
N2 N3 1.4158(18) . ?
N5 N6 1.4113(18) . ?

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 C1 C2 118.65(15) . . ?
C6 C1 C7 123.42(14) . . ?
C2 C1 C7 117.92(15) . . ?
C3 C2 C1 120.85(18) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.17(17) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 119.35(17) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.28(18) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 120.67(16) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
N1 C7 C1 114.22(13) . . ?
N1 C7 H7A 108.7 . . ?
C1 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C1 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
O1 C8 N2 121.71(14) . . ?
O1 C8 N1 123.81(14) . . ?
N2 C8 N1 114.48(13) . . ?
O2 C9 N3 123.22(15) . . ?
O2 C9 C10 121.90(13) . . ?
N3 C9 C10 114.87(13) . . ?
N1 C10 C9 108.59(12) . . ?
N1 C10 C11 113.11(14) . . ?
C9 C10 C11 111.93(14) . . ?
N1 C10 H10 107.7 . . ?
C9 C10 H10 107.7 . . ?
C11 C10 H10 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C13 110.62(15) . . ?
N2 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 C14 110.42(15) . . ?
C12 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C15 C14 C13 110.18(15) . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
O3 C15 N3 111.15(13) . . ?
O3 C15 C14 107.36(14) . . ?
N3 C15 C14 109.43(15) . . ?
O3 C15 H15 109.6 . . ?
N3 C15 H15 109.6 . . ?
C14 C15 H15 109.6 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 118.72(17) . . ?
C18 C17 C23 123.40(15) . . ?
C22 C17 C23 117.85(16) . . ?
C17 C18 C19 120.52(19) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 120.2(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 119.41(19) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C20 C21 C22 120.56(19) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C21 C22 C17 120.6(2) . . ?
C21 C22 H22 119.7 . . ?
C17 C22 H22 119.7 . . ?
N4 C23 C17 114.23(14) . . ?
N4 C23 H23A 108.7 . . ?
C17 C23 H23A 108.7 . . ?
N4 C23 H23B 108.7 . . ?
C17 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
O4 C24 N4 124.16(14) . . ?
O4 C24 N5 121.17(14) . . ?
N4 C24 N5 114.67(13) . . ?
O5 C25 N6 123.36(15) . . ?
O5 C25 C26 122.17(14) . . ?
N6 C25 C26 114.47(13) . . ?
N4 C26 C25 108.64(12) . . ?
N4 C26 C27 113.35(15) . . ?
C25 C26 C27 111.03(13) . . ?
N4 C26 H26 107.9 . . ?
C25 C26 H26 107.9 . . ?
C27 C26 H26 107.9 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N5 C28 C29 110.28(15) . . ?
N5 C28 H28A 109.6 . . ?
C29 C28 H28A 109.6 . . ?
N5 C28 H28B 109.6 . . ?
C29 C28 H28B 109.6 . . ?
H28A C28 H28B 108.1 . . ?
C28 C29 C30 110.44(16) . . ?
C28 C29 H29A 109.6 . . ?
C30 C29 H29A 109.6 . . ?
C28 C29 H29B 109.6 . . ?
C30 C29 H29B 109.6 . . ?
H29A C29 H29B 108.1 . . ?
C31 C30 C29 110.91(15) . . ?
C31 C30 H30A 109.5 . . ?
C29 C30 H30A 109.5 . . ?
C31 C30 H30B 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 108.0 . . ?
O6 C31 N6 110.89(13) . . ?
O6 C31 C30 107.45(14) . . ?
N6 C31 C30 109.20(15) . . ?
O6 C31 H31 109.8 . . ?
N6 C31 H31 109.8 . . ?
C30 C31 H31 109.8 . . ?
O6 C32 H32A 109.5 . . ?
O6 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O6 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C8 N1 C7 118.26(13) . . ?
C8 N1 C10 117.22(12) . . ?
C7 N1 C10 117.26(12) . . ?
C8 N2 N3 121.04(12) . . ?
C8 N2 C12 121.92(14) . . ?
N3 N2 C12 114.60(13) . . ?
C9 N3 N2 120.73(13) . . ?
C9 N3 C15 123.74(13) . . ?
N2 N3 C15 114.48(12) . . ?
C24 N4 C26 117.35(12) . . ?
C24 N4 C23 118.16(13) . . ?
C26 N4 C23 116.80(12) . . ?
C24 N5 N6 121.06(12) . . ?
C24 N5 C28 120.60(14) . . ?
N6 N5 C28 114.59(13) . . ?
C25 N6 N5 121.16(12) . . ?
C25 N6 C31 122.74(13) . . ?
N5 N6 C31 115.19(12) . . ?
C15 O3 C16 114.20(14) . . ?
C31 O6 C32 113.99(14) . . ?

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
C6 C1 C2 C3 -1.0(3) . . . . ?
C7 C1 C2 C3 178.19(16) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -1.6(3) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
C7 C1 C6 C5 -179.29(17) . . . . ?
C4 C5 C6 C1 1.4(3) . . . . ?
C6 C1 C7 N1 3.1(2) . . . . ?
C2 C1 C7 N1 -176.03(15) . . . . ?
O2 C9 C10 N1 143.67(15) . . . . ?
N3 C9 C10 N1 -35.29(19) . . . . ?
O2 C9 C10 C11 -90.75(19) . . . . ?
N3 C9 C10 C11 90.28(17) . . . . ?
N2 C12 C13 C14 53.4(2) . . . . ?
C12 C13 C14 C15 -56.2(2) . . . . ?
C13 C14 C15 O3 -65.47(19) . . . . ?
C13 C14 C15 N3 55.27(19) . . . . ?
C22 C17 C18 C19 -1.3(3) . . . . ?
C23 C17 C18 C19 176.60(18) . . . . ?
C17 C18 C19 C20 1.3(3) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C19 C20 C21 C22 -0.5(3) . . . . ?
C20 C21 C22 C17 0.4(3) . . . . ?
C18 C17 C22 C21 0.4(3) . . . . ?
C23 C17 C22 C21 -177.57(17) . . . . ?
C18 C17 C23 N4 12.5(2) . . . . ?
C22 C17 C23 N4 -169.58(15) . . . . ?
O5 C25 C26 N4 142.20(15) . . . . ?
N6 C25 C26 N4 -37.72(18) . . . . ?
O5 C25 C26 C27 -92.50(19) . . . . ?
N6 C25 C26 C27 87.58(17) . . . . ?
N5 C28 C29 C30 53.5(2) . . . . ?
C28 C29 C30 C31 -56.2(2) . . . . ?
C29 C30 C31 O6 -66.2(2) . . . . ?
C29 C30 C31 N6 54.1(2) . . . . ?
O1 C8 N1 C7 -2.1(2) . . . . ?
N2 C8 N1 C7 176.81(14) . . . . ?
O1 C8 N1 C10 147.35(15) . . . . ?
N2 C8 N1 C10 -33.7(2) . . . . ?
C1 C7 N1 C8 -84.88(18) . . . . ?
C1 C7 N1 C10 125.69(15) . . . . ?
C9 C10 N1 C8 54.86(19) . . . . ?
C11 C10 N1 C8 -70.02(19) . . . . ?
C9 C10 N1 C7 -155.38(14) . . . . ?
C11 C10 N1 C7 79.73(18) . . . . ?
O1 C8 N2 N3 171.80(14) . . . . ?
N1 C8 N2 N3 -7.1(2) . . . . ?
O1 C8 N2 C12 -26.9(2) . . . . ?
N1 C8 N2 C12 154.16(14) . . . . ?
C13 C12 N2 C8 145.26(16) . . . . ?
C13 C12 N2 N3 -52.32(19) . . . . ?
O2 C9 N3 N2 -179.84(15) . . . . ?
C10 C9 N3 N2 -0.9(2) . . . . ?
O2 C9 N3 C15 -12.2(2) . . . . ?
C10 C9 N3 C15 166.73(14) . . . . ?
C8 N2 N3 C9 25.2(2) . . . . ?
C12 N2 N3 C9 -137.34(15) . . . . ?
C8 N2 N3 C15 -143.46(15) . . . . ?
C12 N2 N3 C15 53.96(18) . . . . ?
O3 C15 N3 C9 -104.31(17) . . . . ?
C14 C15 N3 C9 137.29(15) . . . . ?
O3 C15 N3 N2 64.01(18) . . . . ?
C14 C15 N3 N2 -54.39(17) . . . . ?
O4 C24 N4 C26 147.38(16) . . . . ?
N5 C24 N4 C26 -33.4(2) . . . . ?
O4 C24 N4 C23 -1.1(2) . . . . ?
N5 C24 N4 C23 178.13(13) . . . . ?
C25 C26 N4 C24 55.12(19) . . . . ?
C27 C26 N4 C24 -68.81(18) . . . . ?
C25 C26 N4 C23 -155.97(14) . . . . ?
C27 C26 N4 C23 80.10(18) . . . . ?
C17 C23 N4 C24 -93.53(18) . . . . ?
C17 C23 N4 C26 117.82(16) . . . . ?
O4 C24 N5 N6 173.48(14) . . . . ?
N4 C24 N5 N6 -5.8(2) . . . . ?
O4 C24 N5 C28 -29.5(2) . . . . ?
N4 C24 N5 C28 151.27(15) . . . . ?
C29 C28 N5 C24 149.11(16) . . . . ?
C29 C28 N5 N6 -52.4(2) . . . . ?
O5 C25 N6 N5 -176.69(15) . . . . ?
C26 C25 N6 N5 3.2(2) . . . . ?
O5 C25 N6 C31 -8.1(2) . . . . ?
C26 C25 N6 C31 171.79(14) . . . . ?
C24 N5 N6 C25 21.3(2) . . . . ?
C28 N5 N6 C25 -136.99(16) . . . . ?
C24 N5 N6 C31 -148.03(14) . . . . ?
C28 N5 N6 C31 53.63(19) . . . . ?
O6 C31 N6 C25 -104.17(17) . . . . ?
C30 C31 N6 C25 137.62(16) . . . . ?
O6 C31 N6 N5 65.02(18) . . . . ?
C30 C31 N6 N5 -53.19(18) . . . . ?
N3 C15 O3 C16 69.31(19) . . . . ?
C14 C15 O3 C16 -171.04(16) . . . . ?
N6 C31 O6 C32 66.5(2) . . . . ?
C30 C31 O6 C32 -174.21(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        66.67
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.034
_database_code_depnum_ccdc_archive 'CCDC 1001772'
#######################################################################
#
#                 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_mhpr140428

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H22 N4 O6'
_chemical_formula_sum            'C18 H22 N4 O6'
_chemical_formula_weight         390.39

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.9428(4)
_cell_length_b                   10.4945(4)
_cell_length_c                   21.4599(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1788.81(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6090
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8526
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.898
_diffrn_reflns_theta_max         27.456
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4012
_reflns_number_gt                3296
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_max     0.957
_reflns_Friedel_fraction_full    0.985

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0628P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.065(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1231 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.4(6)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4012
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1180
_refine_ls_wR_factor_gt          0.0994
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8573(3) 0.2741(3) 0.91656(13) 0.0277(6) Uani 1 1 d . . . . .
H1A H 0.8486 0.3386 0.9500 0.033 Uiso 1 1 calc R U . . .
H1B H 0.7761 0.2952 0.8831 0.033 Uiso 1 1 calc R U . . .
C2 C 1.0369(3) 0.2665(3) 0.89110(12) 0.0277(6) Uani 1 1 d . . . . .
H2 H 1.0990 0.3477 0.8994 0.033 Uiso 1 1 calc R U . . .
C3 C 1.1180(3) 0.1560(3) 0.92590(12) 0.0274(6) Uani 1 1 d . . . . .
H3A H 1.1636 0.1843 0.9665 0.033 Uiso 1 1 calc R U . . .
H3B H 1.2100 0.1177 0.9011 0.033 Uiso 1 1 calc R U . . .
C4 C 0.9740(3) 0.0618(3) 0.93485(11) 0.0230(6) Uani 1 1 d . . . . .
H4 H 0.9621 0.0067 0.8971 0.028 Uiso 1 1 calc R U . . .
C5 C 0.9882(3) -0.0201(2) 0.99270(12) 0.0246(6) Uani 1 1 d . . . . .
C6 C 0.6748(3) 0.0989(3) 0.95638(11) 0.0240(6) Uani 1 1 d . . . . .
C7 C 0.8221(4) -0.1049(3) 1.08142(12) 0.0258(6) Uani 1 1 d . . . . .
H7 H 0.9306 -0.1473 1.0928 0.031 Uiso 1 1 calc R U . . .
C8 C 0.6815(4) -0.2017(3) 1.08492(13) 0.0305(6) Uani 1 1 d . . . . .
H8A H 0.6635 -0.2261 1.1290 0.037 Uiso 1 1 calc R U . . .
H8B H 0.7152 -0.2792 1.0618 0.037 Uiso 1 1 calc R U . . .
C9 C 0.5170(4) -0.1512(3) 1.05803(13) 0.0294(6) Uani 1 1 d . . . . .
H9A H 0.4749 -0.0801 1.0840 0.035 Uiso 1 1 calc R U . . .
H9B H 0.4311 -0.2195 1.0580 0.035 Uiso 1 1 calc R U . . .
C10 C 0.5470(3) -0.1050(3) 0.99165(12) 0.0285(6) Uani 1 1 d . . . . .
H10A H 0.5779 -0.1779 0.9647 0.034 Uiso 1 1 calc R U . . .
H10B H 0.4427 -0.0663 0.9749 0.034 Uiso 1 1 calc R U . . .
C11 C 0.9216(4) 0.0813(3) 1.13330(14) 0.0369(7) Uani 1 1 d . . . . .
H11A H 0.9334 0.1329 1.0955 0.055 Uiso 1 1 calc R U . . .
H11B H 1.0269 0.0353 1.1412 0.055 Uiso 1 1 calc R U . . .
H11C H 0.8965 0.1369 1.1688 0.055 Uiso 1 1 calc R U . . .
C12 C 0.9994(4) 0.3399(4) 0.78629(14) 0.0424(8) Uani 1 1 d . . . . .
H12A H 1.0850 0.3464 0.7529 0.051 Uiso 1 1 calc R U . . .
H12B H 1.0044 0.4194 0.8110 0.051 Uiso 1 1 calc R U . . .
C13 C 0.8279(4) 0.3296(3) 0.75681(12) 0.0309(7) Uani 1 1 d . . . . .
C14 C 0.7316(4) 0.2202(3) 0.76169(12) 0.0329(7) Uani 1 1 d . . . . .
H14 H 0.7733 0.1494 0.7846 0.039 Uiso 1 1 calc R U . . .
C15 C 0.5755(4) 0.2129(3) 0.73359(13) 0.0326(7) Uani 1 1 d . . . . .
H15 H 0.5091 0.1380 0.7370 0.039 Uiso 1 1 calc R U . . .
C16 C 0.5179(4) 0.3168(3) 0.70050(12) 0.0334(7) Uani 1 1 d . . . . .
C17 C 0.6110(4) 0.4270(3) 0.69392(12) 0.0367(7) Uani 1 1 d . . . . .
H17 H 0.5690 0.4971 0.6706 0.044 Uiso 1 1 calc R U . . .
C18 C 0.7671(4) 0.4323(3) 0.72221(12) 0.0348(7) Uani 1 1 d . . . . .
H18 H 0.8340 0.5068 0.7180 0.042 Uiso 1 1 calc R U . . .
N1 N 0.8277(3) 0.1454(2) 0.94090(10) 0.0258(5) Uani 1 1 d . . . . .
N2 N 0.8360(3) -0.0534(2) 1.01775(10) 0.0248(5) Uani 1 1 d . . . . .
N3 N 0.6827(3) -0.0108(2) 0.99140(10) 0.0267(5) Uani 1 1 d . . . . .
N4 N 0.3485(4) 0.3107(4) 0.67311(11) 0.0453(7) Uani 1 1 d . . . . .
O1 O 1.1224(2) -0.05131(19) 1.01604(9) 0.0320(5) Uani 1 1 d . . . . .
O2 O 0.5401(2) 0.1484(2) 0.94206(9) 0.0322(5) Uani 1 1 d . . . . .
O3 O 0.7879(2) -0.00795(19) 1.12522(8) 0.0278(5) Uani 1 1 d . . . . .
O4 O 1.0414(3) 0.2355(2) 0.82562(8) 0.0336(5) Uani 1 1 d . . . . .
O5 O 0.2765(4) 0.2072(3) 0.67143(13) 0.0659(8) Uani 1 1 d . . . . .
O6 O 0.2853(3) 0.4098(3) 0.65420(12) 0.0659(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.467(4) . ?
C1 C2 1.529(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 O4 1.443(3) . ?
C2 C3 1.523(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.524(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N1 1.461(3) . ?
C4 C5 1.514(4) . ?
C4 H4 1.0000 . ?
C5 O1 1.222(3) . ?
C5 N2 1.369(3) . ?
C6 O2 1.228(3) . ?
C6 N1 1.350(4) . ?
C6 N3 1.377(4) . ?
C7 O3 1.412(3) . ?
C7 N2 1.473(3) . ?
C7 C8 1.512(4) . ?
C7 H7 1.0000 . ?
C8 C9 1.524(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.524(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N3 1.462(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O3 1.427(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O4 1.423(4) . ?
C12 C13 1.506(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.384(4) . ?
C13 C18 1.395(4) . ?
C14 C15 1.381(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(4) . ?
C16 N4 1.470(4) . ?
C17 C18 1.382(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
N2 N3 1.415(3) . ?
N4 O6 1.224(4) . ?
N4 O5 1.228(4) . ?

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 103.2(2) . . ?
N1 C1 H1A 111.1 . . ?
C2 C1 H1A 111.1 . . ?
N1 C1 H1B 111.1 . . ?
C2 C1 H1B 111.1 . . ?
H1A C1 H1B 109.1 . . ?
O4 C2 C3 107.2(2) . . ?
O4 C2 C1 112.5(2) . . ?
C3 C2 C1 105.0(2) . . ?
O4 C2 H2 110.7 . . ?
C3 C2 H2 110.7 . . ?
C1 C2 H2 110.7 . . ?
C2 C3 C4 103.8(2) . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
C4 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
N1 C4 C5 109.1(2) . . ?
N1 C4 C3 102.6(2) . . ?
C5 C4 C3 114.5(2) . . ?
N1 C4 H4 110.1 . . ?
C5 C4 H4 110.1 . . ?
C3 C4 H4 110.1 . . ?
O1 C5 N2 122.7(2) . . ?
O1 C5 C4 123.6(2) . . ?
N2 C5 C4 113.6(2) . . ?
O2 C6 N1 124.7(2) . . ?
O2 C6 N3 122.0(2) . . ?
N1 C6 N3 113.3(2) . . ?
O3 C7 N2 111.6(2) . . ?
O3 C7 C8 108.0(2) . . ?
N2 C7 C8 110.3(2) . . ?
O3 C7 H7 109.0 . . ?
N2 C7 H7 109.0 . . ?
C8 C7 H7 109.0 . . ?
C7 C8 C9 112.4(2) . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C10 109.3(2) . . ?
C8 C9 H9A 109.8 . . ?
C10 C9 H9A 109.8 . . ?
C8 C9 H9B 109.8 . . ?
C10 C9 H9B 109.8 . . ?
H9A C9 H9B 108.3 . . ?
N3 C10 C9 109.5(2) . . ?
N3 C10 H10A 109.8 . . ?
C9 C10 H10A 109.8 . . ?
N3 C10 H10B 109.8 . . ?
C9 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 C13 114.0(3) . . ?
O4 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
O4 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C18 119.3(3) . . ?
C14 C13 C12 121.8(3) . . ?
C18 C13 C12 118.8(3) . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 118.6(3) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C15 C16 C17 122.5(3) . . ?
C15 C16 N4 118.4(3) . . ?
C17 C16 N4 119.1(3) . . ?
C16 C17 C18 118.0(3) . . ?
C16 C17 H17 121.0 . . ?
C18 C17 H17 121.0 . . ?
C17 C18 C13 120.9(3) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
C6 N1 C4 121.3(2) . . ?
C6 N1 C1 124.3(2) . . ?
C4 N1 C1 113.2(2) . . ?
C5 N2 N3 121.5(2) . . ?
C5 N2 C7 121.6(2) . . ?
N3 N2 C7 115.0(2) . . ?
C6 N3 N2 121.5(2) . . ?
C6 N3 C10 122.3(2) . . ?
N2 N3 C10 114.8(2) . . ?
O6 N4 O5 123.4(3) . . ?
O6 N4 C16 118.1(3) . . ?
O5 N4 C16 118.4(3) . . ?
C7 O3 C11 114.2(2) . . ?
C12 O4 C2 113.5(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
N1 C1 C2 O4 93.5(3) . . . . ?
N1 C1 C2 C3 -22.7(3) . . . . ?
O4 C2 C3 C4 -85.3(3) . . . . ?
C1 C2 C3 C4 34.5(3) . . . . ?
C2 C3 C4 N1 -32.2(2) . . . . ?
C2 C3 C4 C5 -150.3(2) . . . . ?
N1 C4 C5 O1 -144.0(3) . . . . ?
C3 C4 C5 O1 -29.7(4) . . . . ?
N1 C4 C5 N2 34.4(3) . . . . ?
C3 C4 C5 N2 148.7(2) . . . . ?
O3 C7 C8 C9 71.3(3) . . . . ?
N2 C7 C8 C9 -50.9(3) . . . . ?
C7 C8 C9 C10 54.9(3) . . . . ?
C8 C9 C10 N3 -55.3(3) . . . . ?
O4 C12 C13 C14 -8.0(4) . . . . ?
O4 C12 C13 C18 173.9(2) . . . . ?
C18 C13 C14 C15 -1.1(4) . . . . ?
C12 C13 C14 C15 -179.3(3) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C14 C15 C16 C17 0.7(4) . . . . ?
C14 C15 C16 N4 -177.3(2) . . . . ?
C15 C16 C17 C18 -0.5(4) . . . . ?
N4 C16 C17 C18 177.4(2) . . . . ?
C16 C17 C18 C13 -0.6(4) . . . . ?
C14 C13 C18 C17 1.3(4) . . . . ?
C12 C13 C18 C17 179.6(3) . . . . ?
O2 C6 N1 C4 -153.4(3) . . . . ?
N3 C6 N1 C4 27.5(3) . . . . ?
O2 C6 N1 C1 13.6(4) . . . . ?
N3 C6 N1 C1 -165.5(2) . . . . ?
C5 C4 N1 C6 -50.9(3) . . . . ?
C3 C4 N1 C6 -172.7(2) . . . . ?
C5 C4 N1 C1 140.8(2) . . . . ?
C3 C4 N1 C1 19.0(3) . . . . ?
C2 C1 N1 C6 -165.7(2) . . . . ?
C2 C1 N1 C4 2.2(3) . . . . ?
O1 C5 N2 N3 176.9(3) . . . . ?
C4 C5 N2 N3 -1.4(4) . . . . ?
O1 C5 N2 C7 13.6(4) . . . . ?
C4 C5 N2 C7 -164.7(2) . . . . ?
O3 C7 N2 C5 94.0(3) . . . . ?
C8 C7 N2 C5 -146.0(3) . . . . ?
O3 C7 N2 N3 -70.4(3) . . . . ?
C8 C7 N2 N3 49.7(3) . . . . ?
O2 C6 N3 N2 -167.6(2) . . . . ?
N1 C6 N3 N2 11.5(4) . . . . ?
O2 C6 N3 C10 27.1(4) . . . . ?
N1 C6 N3 C10 -153.8(2) . . . . ?
C5 N2 N3 C6 -24.7(4) . . . . ?
C7 N2 N3 C6 139.6(2) . . . . ?
C5 N2 N3 C10 141.6(2) . . . . ?
C7 N2 N3 C10 -54.1(3) . . . . ?
C9 C10 N3 C6 -137.9(3) . . . . ?
C9 C10 N3 N2 55.9(3) . . . . ?
C15 C16 N4 O6 166.5(3) . . . . ?
C17 C16 N4 O6 -11.5(4) . . . . ?
C15 C16 N4 O5 -12.2(4) . . . . ?
C17 C16 N4 O5 169.8(3) . . . . ?
N2 C7 O3 C11 -66.8(3) . . . . ?
C8 C7 O3 C11 171.8(2) . . . . ?
C13 C12 O4 C2 -106.7(3) . . . . ?
C3 C2 O4 C12 -168.7(2) . . . . ?
C1 C2 O4 C12 76.4(3) . . . . ?

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.135

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1001773'
#######################################################################
#
#                 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_mhpr140304

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H22 N4 O5'
_chemical_formula_sum            'C17 H22 N4 O5'
_chemical_formula_weight         362.38

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.3044(4)
_cell_length_b                   10.8929(5)
_cell_length_c                   9.6338(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.2690(10)
_cell_angle_gamma                90
_cell_volume                     871.45(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3122
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      28.98

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6819
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7024
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.114
_diffrn_reflns_theta_max         29.010
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_point_group_measured_fraction_full 0.883
_reflns_number_total             3903
_reflns_number_gt                3533
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.602
_reflns_Friedel_fraction_max     0.666
_reflns_Friedel_fraction_full    0.751

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0533P)²+0.0742P] 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_abs_structure_details 
;
 Flack x determined using 1264 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.6(4)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3903
_refine_ls_number_parameters     237
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0873
_refine_ls_wR_factor_gt          0.0835
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3256(2) 0.57753(18) 0.91802(18) 0.0201(3) Uani 1 1 d . . . . .
C2 C 0.1937(2) 0.33435(18) 0.93751(18) 0.0209(4) Uani 1 1 d . . . . .
C3 C 0.2935(2) 0.39109(17) 1.05305(19) 0.0220(4) Uani 1 1 d . . . . .
H3 H 0.3639 0.3258 1.0938 0.026 Uiso 1 1 calc R U . . .
C4 C 0.1821(3) 0.4395(2) 1.1678(2) 0.0315(5) Uani 1 1 d . . . . .
H4A H 0.2473 0.4741 1.2433 0.047 Uiso 1 1 calc R U . . .
H4B H 0.1164 0.3719 1.2037 0.047 Uiso 1 1 calc R U . . .
H4C H 0.1116 0.5034 1.1296 0.047 Uiso 1 1 calc R U . . .
C5 C 0.0762(2) 0.63225(19) 0.7926(2) 0.0247(4) Uani 1 1 d . . . . .
H5A H 0.0775 0.7074 0.8504 0.030 Uiso 1 1 calc R U . . .
H5B H -0.0347 0.5989 0.7931 0.030 Uiso 1 1 calc R U . . .
C6 C 0.1224(3) 0.6655(2) 0.6443(2) 0.0289(4) Uani 1 1 d . . . . .
H6A H 0.0591 0.7381 0.6150 0.035 Uiso 1 1 calc R U . . .
H6B H 0.2376 0.6889 0.6429 0.035 Uiso 1 1 calc R U . . .
C7 C 0.0952(3) 0.5629(2) 0.5394(2) 0.0319(5) Uani 1 1 d . . . . .
H7A H 0.1384 0.5894 0.4486 0.038 Uiso 1 1 calc R U . . .
H7B H -0.0222 0.5503 0.5279 0.038 Uiso 1 1 calc R U . . .
C8 C 0.1729(3) 0.4402(2) 0.5790(2) 0.0292(4) Uani 1 1 d . . . . .
H8A H 0.1710 0.3860 0.4964 0.035 Uiso 1 1 calc R U . . .
H8B H 0.2873 0.4554 0.6030 0.035 Uiso 1 1 calc R U . . .
C9 C 0.0946(2) 0.37183(19) 0.69948(19) 0.0236(4) Uani 1 1 d . . . . .
H9 H 0.1236 0.2830 0.6915 0.028 Uiso 1 1 calc R U . . .
C10 C -0.1629(3) 0.3101(2) 0.7799(3) 0.0404(6) Uani 1 1 d . . . . .
H10A H -0.1297 0.2240 0.7722 0.061 Uiso 1 1 calc R U . . .
H10B H -0.2782 0.3170 0.7590 0.061 Uiso 1 1 calc R U . . .
H10C H -0.1421 0.3394 0.8744 0.061 Uiso 1 1 calc R U . . .
C11 C 0.5632(2) 0.49881(19) 1.04160(19) 0.0225(4) Uani 1 1 d . . . . .
H11A H 0.6169 0.5635 0.9864 0.027 Uiso 1 1 calc R U . . .
H11B H 0.6211 0.4208 1.0248 0.027 Uiso 1 1 calc R U . . .
C12 C 0.5772(2) 0.53105(18) 1.19400(18) 0.0207(4) Uani 1 1 d . . . . .
C13 C 0.6326(3) 0.4435(2) 1.2874(2) 0.0274(4) Uani 1 1 d . . . . .
H13 H 0.6617 0.3642 1.2549 0.033 Uiso 1 1 calc R U . . .
C14 C 0.6459(3) 0.4709(2) 1.4284(2) 0.0299(4) Uani 1 1 d . . . . .
H14 H 0.6828 0.4112 1.4930 0.036 Uiso 1 1 calc R U . . .
C15 C 0.6037(2) 0.5873(2) 1.47105(19) 0.0258(4) Uani 1 1 d . . . . .
C16 C 0.5503(2) 0.6768(2) 1.3807(2) 0.0277(4) Uani 1 1 d . . . . .
H16 H 0.5238 0.7566 1.4133 0.033 Uiso 1 1 calc R U . . .
C17 C 0.5361(2) 0.64753(19) 1.2411(2) 0.0252(4) Uani 1 1 d . . . . .
H17 H 0.4980 0.7074 1.1772 0.030 Uiso 1 1 calc R U . . .
N1 N 0.1864(2) 0.54134(14) 0.85317(16) 0.0218(3) Uani 1 1 d . . . . .
N2 N 0.14985(19) 0.41589(14) 0.83594(16) 0.0210(3) Uani 1 1 d . . . . .
N3 N 0.39681(19) 0.48587(15) 0.99288(16) 0.0214(3) Uani 1 1 d . . . . .
N4 N 0.6197(2) 0.6167(2) 1.61938(19) 0.0364(5) Uani 1 1 d . . . . .
O1 O 0.37535(18) 0.68344(13) 0.90973(15) 0.0279(3) Uani 1 1 d . . . . .
O2 O 0.15954(18) 0.22545(13) 0.93246(15) 0.0282(3) Uani 1 1 d . . . . .
O3 O -0.07389(18) 0.38248(14) 0.68387(15) 0.0317(3) Uani 1 1 d . . . . .
O4 O 0.6419(3) 0.7239(2) 1.6515(2) 0.0632(6) Uani 1 1 d . . . . .
O5 O 0.6079(3) 0.5330(2) 1.70289(17) 0.0557(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.228(2) . ?
C1 N3 1.365(2) . ?
C1 N1 1.369(2) . ?
C2 O2 1.221(2) . ?
C2 N2 1.370(2) . ?
C2 C3 1.516(3) . ?
C3 N3 1.464(2) . ?
C3 C4 1.538(3) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 N1 1.467(2) . ?
C5 C6 1.525(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.522(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.532(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.527(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O3 1.412(2) . ?
C9 N2 1.471(2) . ?
C9 H9 1.0000 . ?
C10 O3 1.425(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 N3 1.464(2) . ?
C11 C12 1.513(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.388(3) . ?
C12 C17 1.391(3) . ?
C13 C14 1.395(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.379(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(3) . ?
C15 N4 1.470(2) . ?
C16 C17 1.387(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
N1 N2 1.409(2) . ?
N4 O5 1.220(3) . ?
N4 O4 1.221(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
O1 C1 N3 125.18(17) . . ?
O1 C1 N1 121.64(17) . . ?
N3 C1 N1 113.16(16) . . ?
O2 C2 N2 122.73(17) . . ?
O2 C2 C3 123.47(17) . . ?
N2 C2 C3 113.75(16) . . ?
N3 C3 C2 108.42(15) . . ?
N3 C3 C4 113.48(16) . . ?
C2 C3 C4 109.83(16) . . ?
N3 C3 H3 108.3 . . ?
C2 C3 H3 108.3 . . ?
C4 C3 H3 108.3 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C6 111.95(17) . . ?
N1 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
N1 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C5 114.23(18) . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C6 C7 C8 114.48(17) . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C7 115.72(17) . . ?
C9 C8 H8A 108.4 . . ?
C7 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
C7 C8 H8B 108.4 . . ?
H8A C8 H8B 107.4 . . ?
O3 C9 N2 111.92(15) . . ?
O3 C9 C8 107.73(16) . . ?
N2 C9 C8 112.84(16) . . ?
O3 C9 H9 108.1 . . ?
N2 C9 H9 108.1 . . ?
C8 C9 H9 108.1 . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 C12 113.64(15) . . ?
N3 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
N3 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C17 119.77(17) . . ?
C13 C12 C11 119.53(18) . . ?
C17 C12 C11 120.70(17) . . ?
C12 C13 C14 120.60(19) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 117.89(19) . . ?
C15 C14 H14 121.1 . . ?
C13 C14 H14 121.1 . . ?
C16 C15 C14 122.93(18) . . ?
C16 C15 N4 119.1(2) . . ?
C14 C15 N4 117.92(19) . . ?
C15 C16 C17 118.36(19) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
C16 C17 C12 120.44(18) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
C1 N1 N2 120.92(15) . . ?
C1 N1 C5 120.70(16) . . ?
N2 N1 C5 118.29(15) . . ?
C2 N2 N1 119.22(15) . . ?
C2 N2 C9 120.51(16) . . ?
N1 N2 C9 119.19(14) . . ?
C1 N3 C3 118.14(16) . . ?
C1 N3 C11 120.34(16) . . ?
C3 N3 C11 119.67(15) . . ?
O5 N4 O4 124.0(2) . . ?
O5 N4 C15 118.1(2) . . ?
O4 N4 C15 117.9(2) . . ?
C9 O3 C10 113.74(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C2 C3 N3 142.99(18) . . . . ?
N2 C2 C3 N3 -34.8(2) . . . . ?
O2 C2 C3 C4 -92.5(2) . . . . ?
N2 C2 C3 C4 89.71(19) . . . . ?
N1 C5 C6 C7 69.6(2) . . . . ?
C5 C6 C7 C8 -52.7(3) . . . . ?
C6 C7 C8 C9 71.2(2) . . . . ?
C7 C8 C9 O3 41.1(2) . . . . ?
C7 C8 C9 N2 -83.0(2) . . . . ?
N3 C11 C12 C13 108.5(2) . . . . ?
N3 C11 C12 C17 -71.9(2) . . . . ?
C17 C12 C13 C14 0.6(3) . . . . ?
C11 C12 C13 C14 -179.75(19) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C13 C14 C15 N4 -179.22(19) . . . . ?
C14 C15 C16 C17 1.0(3) . . . . ?
N4 C15 C16 C17 179.93(18) . . . . ?
C15 C16 C17 C12 -0.9(3) . . . . ?
C13 C12 C17 C16 0.1(3) . . . . ?
C11 C12 C17 C16 -179.50(18) . . . . ?
O1 C1 N1 N2 165.10(17) . . . . ?
N3 C1 N1 N2 -16.4(2) . . . . ?
O1 C1 N1 C5 -11.3(3) . . . . ?
N3 C1 N1 C5 167.20(16) . . . . ?
C6 C5 N1 C1 86.6(2) . . . . ?
C6 C5 N1 N2 -89.8(2) . . . . ?
O2 C2 N2 N1 176.57(17) . . . . ?
C3 C2 N2 N1 -5.6(2) . . . . ?
O2 C2 N2 C9 -15.4(3) . . . . ?
C3 C2 N2 C9 162.44(16) . . . . ?
C1 N1 N2 C2 35.3(2) . . . . ?
C5 N1 N2 C2 -148.28(17) . . . . ?
C1 N1 N2 C9 -132.95(17) . . . . ?
C5 N1 N2 C9 43.5(2) . . . . ?
O3 C9 N2 C2 104.50(19) . . . . ?
C8 C9 N2 C2 -133.78(18) . . . . ?
O3 C9 N2 N1 -87.4(2) . . . . ?
C8 C9 N2 N1 34.3(2) . . . . ?
O1 C1 N3 C3 148.51(19) . . . . ?
N1 C1 N3 C3 -29.9(2) . . . . ?
O1 C1 N3 C11 -16.0(3) . . . . ?
N1 C1 N3 C11 165.63(15) . . . . ?
C2 C3 N3 C1 55.6(2) . . . . ?
C4 C3 N3 C1 -66.7(2) . . . . ?
C2 C3 N3 C11 -139.81(17) . . . . ?
C4 C3 N3 C11 97.9(2) . . . . ?
C12 C11 N3 C1 102.5(2) . . . . ?
C12 C11 N3 C3 -61.7(2) . . . . ?
C16 C15 N4 O5 153.3(2) . . . . ?
C14 C15 N4 O5 -27.7(3) . . . . ?
C16 C15 N4 O4 -25.7(3) . . . . ?
C14 C15 N4 O4 153.3(2) . . . . ?
N2 C9 O3 C10 -62.7(2) . . . . ?
C8 C9 O3 C10 172.67(18) . . . . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1001774'
#######################################################################
#
#                 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_mhpr130813

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 N6 O2'
_chemical_formula_sum            'C15 H18 N6 O2'
_chemical_formula_weight         314.35
_chemical_absolute_configuration rm

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           Monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   7.9768(4)
_cell_length_b                   24.4818(12)
_cell_length_c                   8.0015(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.8230(10)
_cell_angle_gamma                90.00
_cell_volume                     1548.04(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3841
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      27.42

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9722
_exptl_absorpt_correction_T_max  0.9813
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  triumph
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11455
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         28.00
_reflns_number_total             3825
_reflns_number_gt                3359
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0468P)²+0.5604P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(10)
_refine_ls_number_reflns         3825
_refine_ls_number_parameters     411
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1030
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.7011(3) 0.37614(11) 0.0713(3) 0.0256(5) Uani 1 1 d . . .
C2 C 0.6223(4) 0.35821(16) -0.0839(4) 0.0411(7) Uani 1 1 d . . .
H2 H 0.6855 0.3392 -0.1577 0.049 Uiso 1 1 calc R . .
C3 C 0.4519(5) 0.36799(19) -0.1315(5) 0.0549(10) Uani 1 1 d . . .
H3 H 0.3985 0.3550 -0.2374 0.066 Uiso 1 1 calc R . .
C4 C 0.3584(4) 0.39629(15) -0.0277(5) 0.0464(9) Uani 1 1 d . . .
H4 H 0.2413 0.4028 -0.0613 0.056 Uiso 1 1 calc R . .
C5 C 0.4366(4) 0.41494(14) 0.1252(5) 0.0401(7) Uani 1 1 d . . .
H5 H 0.3739 0.4352 0.1967 0.048 Uiso 1 1 calc R . .
C6 C 0.6070(4) 0.40427(12) 0.1758(4) 0.0323(6) Uani 1 1 d . . .
H6 H 0.6592 0.4164 0.2831 0.039 Uiso 1 1 calc R . .
C7 C 0.8854(3) 0.36139(12) 0.1242(3) 0.0278(6) Uani 1 1 d . . .
H7A H 0.8944 0.3214 0.1416 0.033 Uiso 1 1 calc R . .
H7B H 0.9507 0.3710 0.0317 0.033 Uiso 1 1 calc R . .
C8 C 1.0195(3) 0.44061(11) 0.2648(3) 0.0232(5) Uani 1 1 d . . .
C9 C 1.0239(3) 0.38621(11) 0.5828(3) 0.0234(5) Uani 1 1 d . . .
C10 C 1.0323(3) 0.35514(11) 0.4210(3) 0.0251(5) Uani 1 1 d . . .
H10 H 0.9589 0.3221 0.4229 0.030 Uiso 1 1 calc R . .
C11 C 1.2120(4) 0.33533(14) 0.4069(4) 0.0353(7) Uani 1 1 d . . .
H11A H 1.2135 0.3172 0.2979 0.053 Uiso 1 1 calc R . .
H11B H 1.2482 0.3095 0.4982 0.053 Uiso 1 1 calc R . .
H11C H 1.2893 0.3666 0.4157 0.053 Uiso 1 1 calc R . .
C12 C 1.2019(4) 0.50894(12) 0.4324(4) 0.0306(6) Uani 1 1 d . . .
H12A H 1.2024 0.5270 0.3219 0.037 Uiso 1 1 calc R . .
H12B H 1.3151 0.4927 0.4664 0.037 Uiso 1 1 calc R . .
C13 C 1.1657(4) 0.55091(13) 0.5628(4) 0.0400(7) Uani 1 1 d . . .
H13A H 1.2587 0.5780 0.5796 0.048 Uiso 1 1 calc R . .
H13B H 1.0595 0.5706 0.5220 0.048 Uiso 1 1 calc R . .
C14 C 1.1492(4) 0.52291(13) 0.7293(4) 0.0379(7) Uani 1 1 d . . .
H14A H 1.1190 0.5503 0.8113 0.045 Uiso 1 1 calc R . .
H14B H 1.2591 0.5064 0.7756 0.045 Uiso 1 1 calc R . .
C15 C 1.0142(4) 0.47876(12) 0.7047(4) 0.0283(6) Uani 1 1 d . . .
H15 H 1.0130 0.4582 0.8126 0.034 Uiso 1 1 calc R . .
C16 C -0.1983(3) 0.22355(12) 0.4856(4) 0.0280(6) Uani 1 1 d . . .
C17 C -0.1153(4) 0.19300(13) 0.3776(4) 0.0371(7) Uani 1 1 d . . .
H17 H -0.0162 0.1732 0.4202 0.045 Uiso 1 1 calc R . .
C18 C -0.1764(6) 0.19114(16) 0.2057(4) 0.0528(10) Uani 1 1 d . . .
H18 H -0.1212 0.1690 0.1323 0.063 Uiso 1 1 calc R . .
C19 C -0.3174(5) 0.22149(19) 0.1420(5) 0.0560(11) Uani 1 1 d . . .
H19 H -0.3589 0.2203 0.0250 0.067 Uiso 1 1 calc R . .
C20 C -0.3970(4) 0.25340(19) 0.2488(5) 0.0543(10) Uani 1 1 d . . .
H20 H -0.4918 0.2750 0.2047 0.065 Uiso 1 1 calc R . .
C21 C -0.3404(4) 0.25426(16) 0.4186(4) 0.0423(8) Uani 1 1 d . . .
H21 H -0.3979 0.2758 0.4915 0.051 Uiso 1 1 calc R . .
C22 C -0.1451(3) 0.22597(13) 0.6734(4) 0.0289(6) Uani 1 1 d . . .
H22A H -0.1348 0.2648 0.7082 0.035 Uiso 1 1 calc R . .
H22B H -0.2354 0.2094 0.7304 0.035 Uiso 1 1 calc R . .
C23 C 0.0105(3) 0.14608(11) 0.7904(3) 0.0233(5) Uani 1 1 d . . .
C24 C 0.3205(3) 0.20320(11) 0.7722(3) 0.0247(5) Uani 1 1 d . . .
C25 C 0.1600(3) 0.23277(11) 0.7953(4) 0.0257(5) Uani 1 1 d . . .
H25 H 0.1539 0.2667 0.7252 0.031 Uiso 1 1 calc R . .
C26 C 0.1604(4) 0.24953(14) 0.9778(4) 0.0378(7) Uani 1 1 d . . .
H26A H 0.0514 0.2662 0.9914 0.057 Uiso 1 1 calc R . .
H26B H 0.2515 0.2759 1.0097 0.057 Uiso 1 1 calc R . .
H26C H 0.1786 0.2172 1.0504 0.057 Uiso 1 1 calc R . .
C27 C 0.1917(4) 0.07966(13) 0.9651(4) 0.0335(6) Uani 1 1 d . . .
H27A H 0.0839 0.0601 0.9704 0.040 Uiso 1 1 calc R . .
H27B H 0.2270 0.0970 1.0760 0.040 Uiso 1 1 calc R . .
C28 C 0.3254(4) 0.03966(14) 0.9271(5) 0.0434(8) Uani 1 1 d . . .
H28A H 0.2841 0.0191 0.8230 0.052 Uiso 1 1 calc R . .
H28B H 0.3483 0.0132 1.0209 0.052 Uiso 1 1 calc R . .
C29 C 0.4885(4) 0.06966(14) 0.9041(5) 0.0403(7) Uani 1 1 d . . .
H29A H 0.5363 0.0870 1.0119 0.048 Uiso 1 1 calc R . .
H29B H 0.5725 0.0432 0.8722 0.048 Uiso 1 1 calc R . .
C30 C 0.4551(3) 0.11277(12) 0.7693(4) 0.0297(6) Uani 1 1 d . . .
H30 H 0.5599 0.1351 0.7679 0.036 Uiso 1 1 calc R . .
N1 N 0.9606(3) 0.38883(10) 0.2778(3) 0.0257(5) Uani 1 1 d . . .
N2 N 1.0734(3) 0.46588(9) 0.4172(3) 0.0267(5) Uani 1 1 d . . .
N3 N 1.0483(3) 0.44103(9) 0.5713(3) 0.0237(4) Uani 1 1 d . . .
N4 N 0.8499(3) 0.50724(12) 0.6594(4) 0.0393(6) Uani 1 1 d . . .
N5 N 0.7279(3) 0.47672(12) 0.6271(3) 0.0404(6) Uani 1 1 d . . .
N6 N 0.6061(4) 0.45297(18) 0.5904(5) 0.0719(11) Uani 1 1 d . . .
N7 N 0.0147(3) 0.19826(9) 0.7317(3) 0.0248(5) Uani 1 1 d . . .
N8 N 0.1669(3) 0.12189(9) 0.8327(3) 0.0261(5) Uani 1 1 d . . .
N9 N 0.3173(2) 0.14874(9) 0.8020(3) 0.0238(5) Uani 1 1 d . . .
N10 N 0.4150(4) 0.08440(12) 0.6046(4) 0.0420(7) Uani 1 1 d . . .
N11 N 0.3742(6) 0.11506(17) 0.4855(5) 0.0745(8) Uani 1 1 d . . .
N12 N 0.3289(6) 0.13984(17) 0.3686(5) 0.0745(8) Uani 1 1 d . . .
O1 O 1.0243(2) 0.46450(9) 0.1306(2) 0.0311(4) Uani 1 1 d . . .
O2 O 0.9938(3) 0.36407(9) 0.7121(2) 0.0323(4) Uani 1 1 d . . .
O3 O -0.1200(2) 0.12114(8) 0.8061(3) 0.0331(5) Uani 1 1 d . . .
O4 O 0.4444(2) 0.22623(9) 0.7313(3) 0.0349(5) Uani 1 1 d . . .


_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 C6 1.381(4) . ?
C1 C2 1.385(4) . ?
C1 C7 1.517(4) . ?
C2 C3 1.382(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.376(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.373(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.457(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O1 1.228(3) . ?
C8 N1 1.361(4) . ?
C8 N2 1.383(3) . ?
C9 O2 1.221(3) . ?
C9 N3 1.361(3) . ?
C9 C10 1.511(4) . ?
C10 N1 1.464(3) . ?
C10 C11 1.532(4) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N2 1.464(4) . ?
C12 C13 1.520(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.520(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.520(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 N3 1.465(3) . ?
C15 N4 1.485(4) . ?
C15 H15 1.0000 . ?
C16 C17 1.379(4) . ?
C16 C21 1.405(4) . ?
C16 C22 1.506(4) . ?
C17 C18 1.395(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.386(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.375(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.372(5) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 N7 1.463(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 O3 1.228(3) . ?
C23 N7 1.363(4) . ?
C23 N8 1.381(3) . ?
C24 O4 1.221(3) . ?
C24 N9 1.355(4) . ?
C24 C25 1.504(4) . ?
C25 N7 1.468(3) . ?
C25 C26 1.517(4) . ?
C25 H25 1.0000 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 N8 1.474(4) . ?
C27 C28 1.509(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.527(5) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.506(4) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 N9 1.459(3) . ?
C30 N10 1.486(4) . ?
C30 H30 1.0000 . ?
N2 N3 1.414(3) . ?
N4 N5 1.227(4) . ?
N5 N6 1.135(5) . ?
N8 N9 1.419(3) . ?
N10 N11 1.222(5) . ?
N11 N12 1.132(5) . ?

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 C1 C2 118.9(3) . . ?
C6 C1 C7 122.4(2) . . ?
C2 C1 C7 118.6(3) . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 120.6(3) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
N1 C7 C1 113.4(2) . . ?
N1 C7 H7A 108.9 . . ?
C1 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
C1 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
O1 C8 N1 124.3(3) . . ?
O1 C8 N2 121.0(3) . . ?
N1 C8 N2 114.7(2) . . ?
O2 C9 N3 122.8(2) . . ?
O2 C9 C10 122.7(2) . . ?
N3 C9 C10 114.5(2) . . ?
N1 C10 C9 109.2(2) . . ?
N1 C10 C11 113.0(2) . . ?
C9 C10 C11 111.9(2) . . ?
N1 C10 H10 107.5 . . ?
C9 C10 H10 107.5 . . ?
C11 C10 H10 107.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C13 110.3(2) . . ?
N2 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
N2 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 110.1(3) . . ?
C14 C13 H13A 109.6 . . ?
C12 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 C15 110.6(3) . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
N3 C15 N4 111.3(2) . . ?
N3 C15 C14 110.1(2) . . ?
N4 C15 C14 106.5(2) . . ?
N3 C15 H15 109.6 . . ?
N4 C15 H15 109.6 . . ?
C14 C15 H15 109.6 . . ?
C17 C16 C21 118.9(3) . . ?
C17 C16 C22 123.6(3) . . ?
C21 C16 C22 117.6(3) . . ?
C16 C17 C18 120.1(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C19 C18 C17 120.1(4) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 119.7(3) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C21 C20 C19 120.4(4) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C16 120.6(4) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
N7 C22 C16 114.5(2) . . ?
N7 C22 H22A 108.6 . . ?
C16 C22 H22A 108.6 . . ?
N7 C22 H22B 108.6 . . ?
C16 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
O3 C23 N7 124.2(2) . . ?
O3 C23 N8 120.8(2) . . ?
N7 C23 N8 115.0(2) . . ?
O4 C24 N9 122.5(2) . . ?
O4 C24 C25 123.0(2) . . ?
N9 C24 C25 114.6(2) . . ?
N7 C25 C24 109.0(2) . . ?
N7 C25 C26 112.8(2) . . ?
C24 C25 C26 111.0(2) . . ?
N7 C25 H25 108.0 . . ?
C24 C25 H25 108.0 . . ?
C26 C25 H25 108.0 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N8 C27 C28 109.9(2) . . ?
N8 C27 H27A 109.7 . . ?
C28 C27 H27A 109.7 . . ?
N8 C27 H27B 109.7 . . ?
C28 C27 H27B 109.7 . . ?
H27A C27 H27B 108.2 . . ?
C27 C28 C29 110.4(3) . . ?
C27 C28 H28A 109.6 . . ?
C29 C28 H28A 109.6 . . ?
C27 C28 H28B 109.6 . . ?
C29 C28 H28B 109.6 . . ?
H28A C28 H28B 108.1 . . ?
C30 C29 C28 110.7(3) . . ?
C30 C29 H29A 109.5 . . ?
C28 C29 H29A 109.5 . . ?
C30 C29 H29B 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 108.1 . . ?
N9 C30 N10 111.4(2) . . ?
N9 C30 C29 111.0(2) . . ?
N10 C30 C29 107.6(3) . . ?
N9 C30 H30 108.9 . . ?
N10 C30 H30 108.9 . . ?
C29 C30 H30 108.9 . . ?
C8 N1 C7 118.1(2) . . ?
C8 N1 C10 118.9(2) . . ?
C7 N1 C10 118.2(2) . . ?
C8 N2 N3 120.9(2) . . ?
C8 N2 C12 121.7(2) . . ?
N3 N2 C12 114.7(2) . . ?
C9 N3 N2 121.5(2) . . ?
C9 N3 C15 122.0(2) . . ?
N2 N3 C15 115.3(2) . . ?
N5 N4 C15 114.5(3) . . ?
N6 N5 N4 173.0(4) . . ?
C23 N7 C22 118.9(2) . . ?
C23 N7 C25 118.4(2) . . ?
C22 N7 C25 117.1(2) . . ?
C23 N8 N9 121.1(2) . . ?
C23 N8 C27 120.4(2) . . ?
N9 N8 C27 114.5(2) . . ?
C24 N9 N8 121.5(2) . . ?
C24 N9 C30 122.0(2) . . ?
N8 N9 C30 115.3(2) . . ?
N11 N10 C30 114.0(3) . . ?
N12 N11 N10 174.2(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
C6 C1 C2 C3 -0.7(5) . . . . ?
C7 C1 C2 C3 176.0(3) . . . . ?
C1 C2 C3 C4 1.1(6) . . . . ?
C2 C3 C4 C5 0.0(6) . . . . ?
C3 C4 C5 C6 -1.4(5) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
C7 C1 C6 C5 -177.2(3) . . . . ?
C4 C5 C6 C1 1.8(5) . . . . ?
C6 C1 C7 N1 -11.7(4) . . . . ?
C2 C1 C7 N1 171.8(3) . . . . ?
O2 C9 C10 N1 143.1(2) . . . . ?
N3 C9 C10 N1 -35.3(3) . . . . ?
O2 C9 C10 C11 -91.1(3) . . . . ?
N3 C9 C10 C11 90.6(3) . . . . ?
N2 C12 C13 C14 54.2(3) . . . . ?
C12 C13 C14 C15 -55.9(3) . . . . ?
C13 C14 C15 N3 53.5(3) . . . . ?
C13 C14 C15 N4 -67.2(3) . . . . ?
C21 C16 C17 C18 -2.5(5) . . . . ?
C22 C16 C17 C18 177.4(3) . . . . ?
C16 C17 C18 C19 2.2(5) . . . . ?
C17 C18 C19 C20 -0.1(6) . . . . ?
C18 C19 C20 C21 -1.7(6) . . . . ?
C19 C20 C21 C16 1.4(6) . . . . ?
C17 C16 C21 C20 0.8(5) . . . . ?
C22 C16 C21 C20 -179.2(3) . . . . ?
C17 C16 C22 N7 6.9(4) . . . . ?
C21 C16 C22 N7 -173.2(3) . . . . ?
O4 C24 C25 N7 142.1(3) . . . . ?
N9 C24 C25 N7 -38.5(3) . . . . ?
O4 C24 C25 C26 -93.1(3) . . . . ?
N9 C24 C25 C26 86.3(3) . . . . ?
N8 C27 C28 C29 54.7(4) . . . . ?
C27 C28 C29 C30 -55.6(4) . . . . ?
C28 C29 C30 N9 52.4(3) . . . . ?
C28 C29 C30 N10 -69.7(3) . . . . ?
O1 C8 N1 C7 -5.3(4) . . . . ?
N2 C8 N1 C7 173.8(2) . . . . ?
O1 C8 N1 C10 149.9(2) . . . . ?
N2 C8 N1 C10 -31.1(3) . . . . ?
C1 C7 N1 C8 -83.0(3) . . . . ?
C1 C7 N1 C10 121.7(3) . . . . ?
C9 C10 N1 C8 52.3(3) . . . . ?
C11 C10 N1 C8 -73.0(3) . . . . ?
C9 C10 N1 C7 -152.6(2) . . . . ?
C11 C10 N1 C7 82.1(3) . . . . ?
O1 C8 N2 N3 172.0(2) . . . . ?
N1 C8 N2 N3 -7.1(3) . . . . ?
O1 C8 N2 C12 -27.7(4) . . . . ?
N1 C8 N2 C12 153.2(2) . . . . ?
C13 C12 N2 C8 145.8(3) . . . . ?
C13 C12 N2 N3 -52.7(3) . . . . ?
O2 C9 N3 N2 -176.4(2) . . . . ?
C10 C9 N3 N2 2.0(3) . . . . ?
O2 C9 N3 C15 -9.8(4) . . . . ?
C10 C9 N3 C15 168.6(2) . . . . ?
C8 N2 N3 C9 21.9(4) . . . . ?
C12 N2 N3 C9 -139.7(3) . . . . ?
C8 N2 N3 C15 -145.5(2) . . . . ?
C12 N2 N3 C15 52.9(3) . . . . ?
N4 C15 N3 C9 -101.5(3) . . . . ?
C14 C15 N3 C9 140.6(3) . . . . ?
N4 C15 N3 N2 65.8(3) . . . . ?
C14 C15 N3 N2 -52.0(3) . . . . ?
N3 C15 N4 N5 56.6(3) . . . . ?
C14 C15 N4 N5 176.6(3) . . . . ?
O3 C23 N7 C22 -3.9(4) . . . . ?
N8 C23 N7 C22 176.1(2) . . . . ?
O3 C23 N7 C25 149.0(3) . . . . ?
N8 C23 N7 C25 -31.0(3) . . . . ?
C16 C22 N7 C23 -96.5(3) . . . . ?
C16 C22 N7 C25 110.3(3) . . . . ?
C24 C25 N7 C23 52.8(3) . . . . ?
C26 C25 N7 C23 -70.9(3) . . . . ?
C24 C25 N7 C22 -153.8(2) . . . . ?
C26 C25 N7 C22 82.5(3) . . . . ?
O3 C23 N8 N9 174.7(2) . . . . ?
N7 C23 N8 N9 -5.2(3) . . . . ?
O3 C23 N8 C27 -29.0(4) . . . . ?
N7 C23 N8 C27 151.0(2) . . . . ?
C28 C27 N8 C23 149.2(3) . . . . ?
C28 C27 N8 N9 -53.1(3) . . . . ?
O4 C24 N9 N8 -173.6(2) . . . . ?
C25 C24 N9 N8 7.0(3) . . . . ?
O4 C24 N9 C30 -6.8(4) . . . . ?
C25 C24 N9 C30 173.7(2) . . . . ?
C23 N8 N9 C24 17.4(4) . . . . ?
C27 N8 N9 C24 -140.2(3) . . . . ?
C23 N8 N9 C30 -150.2(2) . . . . ?
C27 N8 N9 C30 52.3(3) . . . . ?
N10 C30 N9 C24 -98.6(3) . . . . ?
C29 C30 N9 C24 141.5(3) . . . . ?
N10 C30 N9 N8 68.9(3) . . . . ?
C29 C30 N9 N8 -51.0(3) . . . . ?
N9 C30 N10 N11 53.4(4) . . . . ?
C29 C30 N10 N11 175.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.748
_refine_diff_density_min         -0.718
_refine_diff_density_rms         0.041
_database_code_depnum_ccdc_archive 'CCDC 1001775'
#######################################################################
#
#                 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_mhpmr130321

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N4 O2'
_chemical_formula_sum            'C16 H18 N4 O2'
_chemical_formula_weight         298.34
_chemical_absolute_configuration rm

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 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   7.6663(3)
_cell_length_b                   13.8258(10)
_cell_length_c                   14.6694(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1554.85(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4261
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8305
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_av_sigmaI/netI    0.0806
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         27.40
_reflns_number_total             2022
_reflns_number_gt                1288
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0706P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   10(10)
_refine_ls_number_reflns         2022
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1397
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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 0.8556(5) 0.3466(3) 0.1454(3) 0.0329(9) Uani 1 1 d . . .
C2 C 0.9147(5) 0.2600(3) 0.1821(3) 0.0367(10) Uani 1 1 d . . .
H2 H 0.9982 0.2612 0.2300 0.044 Uiso 1 1 calc R . .
C3 C 0.8543(5) 0.1723(3) 0.1504(3) 0.0430(11) Uani 1 1 d . . .
H3 H 0.8963 0.1138 0.1762 0.052 Uiso 1 1 calc R . .
C4 C 0.7337(6) 0.1698(3) 0.0816(4) 0.0525(13) Uani 1 1 d . . .
H4 H 0.6935 0.1095 0.0588 0.063 Uiso 1 1 calc R . .
C5 C 0.6709(6) 0.2547(4) 0.0456(3) 0.0560(12) Uani 1 1 d . . .
H5 H 0.5852 0.2528 -0.0011 0.067 Uiso 1 1 calc R . .
C6 C 0.7312(5) 0.3426(3) 0.0766(3) 0.0428(11) Uani 1 1 d . . .
H6 H 0.6875 0.4008 0.0509 0.051 Uiso 1 1 calc R . .
C7 C 0.9279(5) 0.4418(3) 0.1790(3) 0.0394(10) Uani 1 1 d . . .
H7A H 0.9861 0.4317 0.2385 0.047 Uiso 1 1 calc R . .
H7B H 1.0164 0.4656 0.1353 0.047 Uiso 1 1 calc R . .
C8 C 0.8101(5) 0.6049(3) 0.1542(3) 0.0298(9) Uani 1 1 d . . .
C9 C 0.4859(5) 0.5332(2) 0.2214(3) 0.0297(9) Uani 1 1 d . . .
C10 C 0.6579(4) 0.4996(2) 0.2599(3) 0.0317(9) Uani 1 1 d . . .
H10 H 0.6490 0.4284 0.2713 0.038 Uiso 1 1 calc R . .
C11 C 0.7028(5) 0.5484(3) 0.3503(3) 0.0435(11) Uani 1 1 d . . .
H11A H 0.8138 0.5230 0.3731 0.065 Uiso 1 1 calc R . .
H11B H 0.6104 0.5353 0.3948 0.065 Uiso 1 1 calc R . .
H11C H 0.7129 0.6184 0.3410 0.065 Uiso 1 1 calc R . .
C12 C 0.6628(4) 0.7663(2) 0.1631(3) 0.0330(9) Uani 1 1 d . . .
H12A H 0.7808 0.7907 0.1483 0.040 Uiso 1 1 calc R . .
H12B H 0.6318 0.7888 0.2250 0.040 Uiso 1 1 calc R . .
C13 C 0.5323(4) 0.8052(3) 0.0947(3) 0.0313(9) Uani 1 1 d . . .
H13A H 0.5718 0.7896 0.0322 0.038 Uiso 1 1 calc R . .
H13B H 0.5253 0.8764 0.1003 0.038 Uiso 1 1 calc R . .
C14 C 0.3534(4) 0.7615(3) 0.1108(3) 0.0328(9) Uani 1 1 d . . .
H14A H 0.2734 0.7820 0.0614 0.039 Uiso 1 1 calc R . .
H14B H 0.3060 0.7856 0.1693 0.039 Uiso 1 1 calc R . .
C15 C 0.3636(4) 0.6508(3) 0.1132(3) 0.0304(9) Uani 1 1 d . . .
H15 H 0.2483 0.6251 0.1338 0.036 Uiso 1 1 calc R . .
C16 C 0.4035(5) 0.6092(3) 0.0220(3) 0.0370(10) Uani 1 1 d . . .
N1 N 0.7907(4) 0.5148(2) 0.1893(2) 0.0330(8) Uani 1 1 d . . .
N2 N 0.6626(3) 0.66100(19) 0.1605(2) 0.0314(8) Uani 1 1 d . . .
N3 N 0.4971(3) 0.6193(2) 0.1777(2) 0.0305(8) Uani 1 1 d . . .
N4 N 0.4384(5) 0.5766(3) -0.0473(3) 0.0569(11) Uani 1 1 d . . .
O1 O 0.9451(3) 0.63742(19) 0.12107(18) 0.0370(7) Uani 1 1 d . . .
O2 O 0.3501(3) 0.48747(18) 0.2266(2) 0.0432(8) Uani 1 1 d . . .


_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 C2 1.389(5) . ?
C1 C6 1.390(5) . ?
C1 C7 1.511(5) . ?
C2 C3 1.379(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.369(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.374(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.466(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O1 1.228(4) . ?
C8 N1 1.356(5) . ?
C8 N2 1.375(4) . ?
C9 O2 1.220(4) . ?
C9 N3 1.355(4) . ?
C9 C10 1.508(5) . ?
C10 N1 1.468(5) . ?
C10 C11 1.527(5) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N2 1.456(4) . ?
C12 C13 1.515(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.517(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.534(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 N3 1.460(4) . ?
C15 C16 1.487(6) . ?
C15 H15 1.0000 . ?
C16 N4 1.143(5) . ?
N2 N3 1.416(4) . ?

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
C2 C1 C6 118.2(4) . . ?
C2 C1 C7 120.3(3) . . ?
C6 C1 C7 121.5(3) . . ?
C3 C2 C1 121.1(4) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.9(4) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.6(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 120.3(4) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
N1 C7 C1 111.7(3) . . ?
N1 C7 H7A 109.3 . . ?
C1 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
C1 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
O1 C8 N1 125.4(3) . . ?
O1 C8 N2 120.9(3) . . ?
N1 C8 N2 113.7(3) . . ?
O2 C9 N3 122.6(3) . . ?
O2 C9 C10 124.3(3) . . ?
N3 C9 C10 113.1(3) . . ?
N1 C10 C9 107.3(3) . . ?
N1 C10 C11 113.2(3) . . ?
C9 C10 C11 112.7(3) . . ?
N1 C10 H10 107.8 . . ?
C9 C10 H10 107.8 . . ?
C11 C10 H10 107.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C13 109.7(3) . . ?
N2 C12 H12A 109.7 . . ?
C13 C12 H12A 109.7 . . ?
N2 C12 H12B 109.7 . . ?
C13 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C12 C13 C14 110.7(3) . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 C15 110.8(3) . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
N3 C15 C16 108.9(3) . . ?
N3 C15 C14 110.4(3) . . ?
C16 C15 C14 112.1(3) . . ?
N3 C15 H15 108.5 . . ?
C16 C15 H15 108.5 . . ?
C14 C15 H15 108.5 . . ?
N4 C16 C15 178.2(4) . . ?
C8 N1 C7 121.0(3) . . ?
C8 N1 C10 118.4(3) . . ?
C7 N1 C10 118.1(3) . . ?
C8 N2 N3 121.3(3) . . ?
C8 N2 C12 124.4(3) . . ?
N3 N2 C12 113.8(3) . . ?
C9 N3 N2 119.9(3) . . ?
C9 N3 C15 121.6(3) . . ?
N2 N3 C15 113.0(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
C6 C1 C2 C3 1.1(5) . . . . ?
C7 C1 C2 C3 -177.9(4) . . . . ?
C1 C2 C3 C4 -0.2(6) . . . . ?
C2 C3 C4 C5 -1.2(6) . . . . ?
C3 C4 C5 C6 1.5(7) . . . . ?
C4 C5 C6 C1 -0.5(7) . . . . ?
C2 C1 C6 C5 -0.8(6) . . . . ?
C7 C1 C6 C5 178.3(4) . . . . ?
C2 C1 C7 N1 -138.5(4) . . . . ?
C6 C1 C7 N1 42.4(5) . . . . ?
O2 C9 C10 N1 133.3(4) . . . . ?
N3 C9 C10 N1 -45.0(4) . . . . ?
O2 C9 C10 C11 -101.4(4) . . . . ?
N3 C9 C10 C11 80.3(4) . . . . ?
N2 C12 C13 C14 54.3(4) . . . . ?
C12 C13 C14 C15 -52.8(4) . . . . ?
C13 C14 C15 N3 52.1(4) . . . . ?
C13 C14 C15 C16 -69.4(4) . . . . ?
O1 C8 N1 C7 -8.5(6) . . . . ?
N2 C8 N1 C7 172.9(3) . . . . ?
O1 C8 N1 C10 153.3(4) . . . . ?
N2 C8 N1 C10 -25.2(5) . . . . ?
C1 C7 N1 C8 -131.4(4) . . . . ?
C1 C7 N1 C10 66.7(5) . . . . ?
C9 C10 N1 C8 55.9(4) . . . . ?
C11 C10 N1 C8 -69.1(4) . . . . ?
C9 C10 N1 C7 -141.7(3) . . . . ?
C11 C10 N1 C7 93.3(4) . . . . ?
O1 C8 N2 N3 164.7(3) . . . . ?
N1 C8 N2 N3 -16.7(5) . . . . ?
O1 C8 N2 C12 -24.2(6) . . . . ?
N1 C8 N2 C12 154.4(4) . . . . ?
C13 C12 N2 C8 131.0(4) . . . . ?
C13 C12 N2 N3 -57.3(4) . . . . ?
O2 C9 N3 N2 -169.2(4) . . . . ?
C10 C9 N3 N2 9.1(5) . . . . ?
O2 C9 N3 C15 -17.1(5) . . . . ?
C10 C9 N3 C15 161.2(3) . . . . ?
C8 N2 N3 C9 25.1(5) . . . . ?
C12 N2 N3 C9 -146.9(3) . . . . ?
C8 N2 N3 C15 -129.3(3) . . . . ?
C12 N2 N3 C15 58.7(4) . . . . ?
C16 C15 N3 C9 -85.0(4) . . . . ?
C14 C15 N3 C9 151.6(3) . . . . ?
C16 C15 N3 N2 68.9(4) . . . . ?
C14 C15 N3 N2 -54.5(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.40
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.070
_database_code_depnum_ccdc_archive 'CCDC 1001776'
