# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences.
# This journal is © The Royal Society of Chemistry and Owner Societies 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_VBT4Pyr7

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 VBT-4Pyr
;
_chemical_name_common            VBT-4Pyr
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H17 N3 O2'
_chemical_formula_sum            'C19 H17 N3 O2'
_chemical_formula_weight         319.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   16.482(3)
_cell_length_b                   4.9600(10)
_cell_length_c                   18.568(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.72(3)
_cell_angle_gamma                90.00
_cell_volume                     1517.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9816
_exptl_absorpt_correction_T_max  0.9991
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71082
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'MX1 Beamline Australian Synchrotron'
_diffrn_radiation_monochromator  'silicon double crystal'
_diffrn_measurement_device_type  'φ goniostat with quantum 210r detector'
_diffrn_measurement_method       'f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9341
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2650
_reflns_number_gt                2082
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Blu Ice'
_computing_cell_refinement       XDS
_computing_data_reduction        XDS
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  CIFTAB

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0701P)²+0.8106P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.129(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2650
_refine_ls_number_parameters     269
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1355
_refine_ls_wR_factor_gt          0.1252
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.006

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
O7 O 0.38610(9) 0.0509(3) 0.74705(8) 0.0244(4) Uani 1 1 d . . .
N1 N 0.38626(10) -0.3063(3) 0.82422(9) 0.0170(4) Uani 1 1 d . . .
O8 O 0.62966(8) -0.2604(3) 0.83300(8) 0.0278(4) Uani 1 1 d . . .
C11 C 0.26581(12) -0.0946(4) 0.87810(10) 0.0164(5) Uani 1 1 d . . .
N3 N 0.50729(10) -0.1207(4) 0.78742(9) 0.0192(4) Uani 1 1 d . . .
N22 N 0.07960(11) 1.2395(4) 1.19493(10) 0.0280(5) Uani 1 1 d D . .
C2 C 0.42412(12) -0.1141(4) 0.78337(10) 0.0172(5) Uani 1 1 d . . .
C10 C 0.29750(11) -0.3032(4) 0.82649(11) 0.0171(5) Uani 1 1 d . . .
H10A H 0.2783 -0.4837 0.8411 0.021 Uiso 1 1 calc R . .
H10B H 0.2748 -0.2660 0.7775 0.021 Uiso 1 1 calc R . .
C9 C 0.55924(14) -0.6716(5) 0.92061(12) 0.0284(5) Uani 1 1 d . . .
H9A H 0.5220 -0.7968 0.9436 0.043 Uiso 1 1 calc R . .
H9B H 0.5892 -0.5682 0.9577 0.043 Uiso 1 1 calc R . .
H9C H 0.5976 -0.7735 0.8919 0.043 Uiso 1 1 calc R . .
C6 C 0.43086(12) -0.4837(4) 0.86673(10) 0.0185(5) Uani 1 1 d . . .
H6 H 0.4023 -0.6145 0.8934 0.022 Uiso 1 1 calc R . .
C5 C 0.51175(12) -0.4826(4) 0.87264(11) 0.0195(5) Uani 1 1 d . . .
C12 C 0.30783(13) -0.0251(4) 0.94129(11) 0.0232(5) Uani 1 1 d . . .
H12 H 0.3585 -0.1083 0.9528 0.028 Uiso 1 1 calc R . .
C16 C 0.19171(12) 0.0277(4) 0.86333(11) 0.0225(5) Uani 1 1 d . . .
H16 H 0.1613 -0.0208 0.8210 0.027 Uiso 1 1 calc R . .
C4 C 0.55566(12) -0.2863(4) 0.83083(11) 0.0196(5) Uani 1 1 d . . .
C14 C 0.20283(17) 0.2931(4) 0.97228(13) 0.0386(7) Uani 1 1 d D . .
C15 C 0.16146(15) 0.2197(4) 0.90932(13) 0.0334(6) Uani 1 1 d . A .
H15 H 0.1110 0.3035 0.8974 0.040 Uiso 1 1 calc R . .
C13 C 0.27641(17) 0.1658(5) 0.98791(12) 0.0357(7) Uani 1 1 d . A .
H13 H 0.3058 0.2096 1.0311 0.043 Uiso 1 1 calc R . .
C23 C 0.1590(5) 1.190(3) 1.2001(12) 0.024(2) Uani 0.510(6) 1 d PD A 1
H23 H 0.1914 1.2958 1.2325 0.029 Uiso 0.510(6) 1 calc PR A 1
C19 C 0.1525(4) 0.8361(12) 1.1136(3) 0.0259(9) Uani 0.510(6) 1 d PD A 1
C24 C 0.1962(7) 0.995(2) 1.1614(7) 0.0271(18) Uani 0.510(6) 1 d PD A 1
H24 H 0.2530 0.9681 1.1675 0.033 Uiso 0.510(6) 1 calc PR A 1
C20 C 0.0705(4) 0.9006(15) 1.1054(4) 0.0240(16) Uani 0.510(6) 1 d PD A 1
H20 H 0.0382 0.8122 1.0694 0.029 Uiso 0.510(6) 1 calc PR A 1
C21 C 0.0356(5) 1.0919(10) 1.1491(4) 0.0259(9) Uani 0.510(6) 1 d PD A 1
H21 H -0.0215 1.1179 1.1460 0.031 Uiso 0.510(6) 1 calc PR A 1
H3 H 0.5310(15) 0.004(5) 0.7585(14) 0.037(7) Uiso 1 1 d . . .
C17 C 0.1532(3) 0.5036(11) 1.0103(3) 0.0126(11) Uani 0.510(6) 1 d PD A 1
H17 H 0.0998 0.5492 0.9939 0.015 Uiso 0.510(6) 1 calc PR A 1
C18 C 0.1891(2) 0.6264(8) 1.0702(2) 0.0117(11) Uani 0.510(6) 1 d PD A 1
H18 H 0.2423 0.5692 1.0841 0.014 Uiso 0.510(6) 1 calc PR A 1
C23B C 0.1765(7) 0.937(2) 1.1439(6) 0.038(3) Uani 0.490(6) 1 d PD A 2
H23B H 0.2305 0.8689 1.1455 0.046 Uiso 0.490(6) 1 calc PR A 2
C20B C 0.0413(5) 0.9565(16) 1.0927(5) 0.0326(19) Uani 0.490(6) 1 d PD A 2
H20B H -0.0003 0.8965 1.0600 0.039 Uiso 0.490(6) 1 calc PR A 2
C22B C 0.1526(6) 1.125(4) 1.1922(12) 0.033(4) Uani 0.490(6) 1 d PD A 2
H22B H 0.1919 1.1801 1.2276 0.040 Uiso 0.490(6) 1 calc PR A 2
C21B C 0.0264(5) 1.1569(11) 1.1433(4) 0.0259(9) Uani 0.49 1 d PD A 2
H21B H -0.0253 1.2417 1.1410 0.031 Uiso 0.490(6) 1 calc PR A 2
C17B C 0.1941(5) 0.4914(12) 1.0327(4) 0.0318(15) Uani 0.490(6) 1 d PD A 2
H17B H 0.2347 0.5041 1.0700 0.038 Uiso 0.490(6) 1 calc PR A 2
C18B C 0.1332(4) 0.6387(13) 1.0334(4) 0.0428(19) Uani 0.490(6) 1 d PD A 2
H18B H 0.0933 0.6205 0.9956 0.051 Uiso 0.490(6) 1 calc PR A 2
C19B C 0.1197(4) 0.8458(11) 1.0917(3) 0.0259(9) Uani 0.49 1 d PD A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O7 C2 1.221(2) . ?
N1 C2 1.379(3) . ?
N1 C6 1.379(3) . ?
N1 C10 1.465(2) . ?
O8 C4 1.226(2) . ?
C11 C16 1.384(3) . ?
C11 C12 1.388(3) . ?
C11 C10 1.514(3) . ?
N3 C2 1.371(3) . ?
N3 C4 1.386(3) . ?
N22 C21 1.323(7) . ?
N22 C23 1.333(8) . ?
N22 C22B 1.333(8) . ?
N22 C21B 1.344(7) . ?
C9 C5 1.497(3) . ?
C6 C5 1.334(3) . ?
C5 C4 1.452(3) . ?
C12 C13 1.393(3) . ?
C16 C15 1.382(3) . ?
C14 C15 1.384(4) . ?
C14 C13 1.390(4) . ?
C14 C17B 1.503(7) . ?
C14 C17 1.514(6) . ?
C23 C24 1.362(9) . ?
C19 C24 1.373(7) . ?
C19 C20 1.392(6) . ?
C19 C18 1.458(7) . ?
C20 C21 1.385(6) . ?
C17 C18 1.384(8) . ?
C23B C22B 1.361(9) . ?
C23B C19B 1.402(8) . ?
C20B C21B 1.394(7) . ?
C20B C19B 1.405(6) . ?
C17B C18B 1.242(11) . ?
C18B C19B 1.514(8) . ?

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 N1 C6 120.89(17) . . ?
C2 N1 C10 118.53(17) . . ?
C6 N1 C10 120.37(16) . . ?
C16 C11 C12 118.26(19) . . ?
C16 C11 C10 119.57(18) . . ?
C12 C11 C10 122.15(19) . . ?
C2 N3 C4 127.05(17) . . ?
C21 N22 C23 117.5(6) . . ?
C21 N22 C22B 102.5(6) . . ?
C23 N22 C22B 15.9(10) . . ?
C21 N22 C21B 16.0(4) . . ?
C23 N22 C21B 127.8(8) . . ?
C22B N22 C21B 114.4(7) . . ?
O7 C2 N3 122.79(18) . . ?
O7 C2 N1 122.26(18) . . ?
N3 C2 N1 114.94(18) . . ?
N1 C10 C11 112.90(16) . . ?
C5 C6 N1 123.96(18) . . ?
C6 C5 C4 118.12(19) . . ?
C6 C5 C9 123.33(19) . . ?
C4 C5 C9 118.54(18) . . ?
C11 C12 C13 120.6(2) . . ?
C15 C16 C11 120.8(2) . . ?
O8 C4 N3 120.75(19) . . ?
O8 C4 C5 124.3(2) . . ?
N3 C4 C5 114.91(17) . . ?
C15 C14 C13 117.5(2) . . ?
C15 C14 C17B 138.4(4) . . ?
C13 C14 C17B 104.1(4) . . ?
C15 C14 C17 108.4(3) . . ?
C13 C14 C17 134.1(3) . . ?
C17B C14 C17 30.1(3) . . ?
C16 C15 C14 121.7(2) . . ?
C14 C13 C12 121.2(2) . . ?
N22 C23 C24 123.3(11) . . ?
C24 C19 C20 115.3(7) . . ?
C24 C19 C18 123.2(8) . . ?
C20 C19 C18 121.3(5) . . ?
C23 C24 C19 120.8(11) . . ?
C21 C20 C19 120.8(6) . . ?
N22 C21 C20 121.8(6) . . ?
C18 C17 C14 117.0(5) . . ?
C17 C18 C19 125.7(5) . . ?
C22B C23B C19B 118.4(10) . . ?
C21B C20B C19B 118.0(6) . . ?
N22 C22B C23B 126.7(12) . . ?
N22 C21B C20B 125.0(7) . . ?
C18B C17B C14 119.1(9) . . ?
C17B C18B C19B 122.8(8) . . ?
C23B C19B C20B 117.4(6) . . ?
C23B C19B C18B 127.2(7) . . ?
C20B C19B C18B 115.4(6) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.057
_database_code_depnum_ccdc_archive 'CCDC 984307'
#######################################################################
#
#                 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_190912A_VBT3Pyr_8

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 VBT3Pyr
;
_chemical_name_common            VBT3Pyr
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H17 N3 O2'
_chemical_formula_sum            'C19 H17 N3 O2'
_chemical_formula_weight         319.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   4.8700(10)
_cell_length_b                   10.620(2)
_cell_length_c                   15.260(3)
_cell_angle_alpha                100.47(3)
_cell_angle_beta                 94.59(3)
_cell_angle_gamma                93.98(3)
_cell_volume                     770.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.00
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9982
_exptl_absorpt_correction_T_max  0.9998
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'MX1 Beamline, Australian Synchrotron'
_diffrn_radiation_monochromator  'silicon double crystal'
_diffrn_measurement_device_type  'φ goniostat with quantum 210r detector'
_diffrn_measurement_method       'f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9756
_diffrn_reflns_av_R_equivalents  0.1189
_diffrn_reflns_av_sigmaI/netI    0.1010
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2562
_reflns_number_gt                1684
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Blu Ice'
_computing_cell_refinement       XDS
_computing_data_reduction        XDS
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  CIFTAB

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1203P)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       0.32(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2562
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0746
_refine_ls_wR_factor_ref         0.2111
_refine_ls_wR_factor_gt          0.1907
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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
N3 N 0.2107(4) 0.4545(2) 0.40568(14) 0.0394(6) Uani 1 1 d . . .
H3 H 0.0854 0.5073 0.4228 0.047 Uiso 1 1 calc R . .
O7 O 0.2427(4) 0.5418(2) 0.28117(12) 0.0481(6) Uani 1 1 d . . .
O8 O 0.1786(4) 0.3763(2) 0.53350(12) 0.0460(6) Uani 1 1 d . . .
N1 N 0.5030(4) 0.3768(2) 0.30025(14) 0.0416(7) Uani 1 1 d . . .
C6 C 0.5818(5) 0.2907(3) 0.35268(18) 0.0441(8) Uani 1 1 d . . .
H6 H 0.7131 0.2329 0.3320 0.053 Uiso 1 1 calc R . .
C5 C 0.4830(5) 0.2840(3) 0.43193(18) 0.0418(7) Uani 1 1 d . . .
C2 C 0.3161(5) 0.4629(3) 0.32553(17) 0.0396(7) Uani 1 1 d . . .
C4 C 0.2828(5) 0.3710(3) 0.46172(18) 0.0396(7) Uani 1 1 d . . .
C9 C 0.5705(6) 0.1912(3) 0.4892(2) 0.0523(9) Uani 1 1 d . . .
H9A H 0.7130 0.1411 0.4615 0.078 Uiso 1 1 calc R . .
H9B H 0.4106 0.1331 0.4953 0.078 Uiso 1 1 calc R . .
H9C H 0.6451 0.2385 0.5485 0.078 Uiso 1 1 calc R . .
C10 C 0.6099(6) 0.3759(3) 0.21261(18) 0.0499(8) Uani 1 1 d . A .
H10A H 0.7646 0.3201 0.2069 0.060 Uiso 1 1 calc R . .
H10B H 0.6837 0.4641 0.2095 0.060 Uiso 1 1 calc R . .
N23 N -0.9365(6) -0.0309(3) -0.27356(19) 0.0660(9) Uani 1 1 d . . .
C11 C 0.3928(6) 0.3289(4) 0.1358(2) 0.0539(9) Uani 1 1 d . . .
C22 C -1.0125(7) 0.0471(4) -0.3250(2) 0.0571(9) Uani 1 1 d . A .
H22 H -1.1674 0.0202 -0.3679 0.069 Uiso 1 1 calc R . .
C19 C -0.5839(7) 0.1320(4) -0.1992(2) 0.0664(11) Uani 1 1 d . . .
C12A C 0.220(7) 0.206(3) 0.1384(16) 0.048(4) Uani 0.546(14) 1 d P A 1
H12A H 0.2394 0.1673 0.1896 0.058 Uiso 0.546(14) 1 calc PR A 1
C24 C -0.7296(8) 0.0124(4) -0.2105(2) 0.0726(11) Uani 1 1 d . A .
H24 H -0.6781 -0.0425 -0.1704 0.087 Uiso 1 1 calc R . .
C20 C -0.6694(8) 0.2094(4) -0.2585(3) 0.0759(12) Uani 1 1 d . A .
H20 H -0.5784 0.2925 -0.2550 0.091 Uiso 1 1 calc R . .
C21 C -0.8814(7) 0.1662(4) -0.3208(2) 0.0727(11) Uani 1 1 d . . .
H21 H -0.9402 0.2183 -0.3619 0.087 Uiso 1 1 calc R A .
C14A C -0.0282(7) 0.2189(4) -0.0028(2) 0.047(3) Uani 0.546(14) 1 d PR A 1
C13A C 0.032(2) 0.1506(11) 0.0667(8) 0.054(3) Uani 0.546(14) 1 d P A 1
H13A H -0.0555 0.0671 0.0641 0.065 Uiso 0.546(14) 1 calc PR A 1
C18A C -0.3454(17) 0.2004(11) -0.1410(6) 0.055(3) Uani 0.546(14) 1 d P A 1
H18A H -0.2544 0.2758 -0.1544 0.066 Uiso 0.546(14) 1 calc PR A 1
C18B C -0.386(2) 0.1418(11) -0.1133(7) 0.041(2) Uani 0.454(14) 1 d P A 2
H18B H -0.4020 0.0803 -0.0755 0.050 Uiso 0.454(14) 1 calc PR A 2
C17A C -0.2625(17) 0.1562(9) -0.0716(6) 0.056(3) Uani 0.546(14) 1 d P A 1
H17A H -0.3547 0.0784 -0.0626 0.067 Uiso 0.546(14) 1 calc PR A 1
C17B C -0.1914(15) 0.2405(9) -0.0946(5) 0.040(3) Uani 0.454(14) 1 d P A 2
H17B H -0.1866 0.2953 -0.1373 0.048 Uiso 0.454(14) 1 calc PR A 2
C14B C 0.009(3) 0.2747(12) -0.0194(8) 0.050(4) Uani 0.454(14) 1 d P A 2
C13B C 0.031(3) 0.1964(11) 0.0455(10) 0.043(3) Uani 0.454(14) 1 d P A 2
H13B H -0.0977 0.1234 0.0409 0.052 Uiso 0.454(14) 1 calc PR A 2
C12B C 0.249(9) 0.226(4) 0.120(2) 0.055(7) Uani 0.454(14) 1 d P A 2
H12B H 0.2796 0.1641 0.1571 0.066 Uiso 0.454(14) 1 calc PR A 2
C16A C 0.313(3) 0.3815(15) 0.0716(11) 0.055(3) Uani 0.546(14) 1 d P A 1
H16A H 0.4010 0.4639 0.0709 0.065 Uiso 0.546(14) 1 calc PR A 1
C15B C 0.199(3) 0.3799(17) -0.0080(13) 0.061(4) Uani 0.454(14) 1 d P A 2
H15B H 0.2016 0.4287 -0.0543 0.073 Uiso 0.454(14) 1 calc PR A 2
C15A C 0.111(2) 0.3329(15) 0.0020(10) 0.065(5) Uani 0.546(14) 1 d P A 1
H15A H 0.0713 0.3818 -0.0431 0.078 Uiso 0.546(14) 1 calc PR A 1
C16B C 0.383(4) 0.4184(17) 0.0661(14) 0.050(3) Uani 0.454(14) 1 d P A 2
H16B H 0.4996 0.4960 0.0744 0.060 Uiso 0.454(14) 1 calc PR A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 C2 1.379(4) . ?
N3 C4 1.382(4) . ?
O7 C2 1.223(3) . ?
O8 C4 1.238(3) . ?
N1 C2 1.363(4) . ?
N1 C6 1.374(4) . ?
N1 C10 1.472(4) . ?
C6 C5 1.349(4) . ?
C5 C4 1.433(4) . ?
C5 C9 1.493(4) . ?
C10 C11 1.503(4) . ?
N23 C22 1.293(4) . ?
N23 C24 1.331(4) . ?
C11 C12B 1.23(4) . ?
C11 C16A 1.261(16) . ?
C11 C12A 1.51(3) . ?
C11 C16B 1.550(17) . ?
C22 C21 1.365(5) . ?
C19 C24 1.386(6) . ?
C19 C20 1.388(6) . ?
C19 C18A 1.466(8) . ?
C19 C18B 1.546(10) . ?
C12A C13A 1.38(3) . ?
C20 C21 1.341(5) . ?
C14A C15A 1.333(15) . ?
C14A C13A 1.412(11) . ?
C14A C17A 1.515(9) . ?
C18A C17A 1.283(17) . ?
C18B C17B 1.338(17) . ?
C17B C14B 1.424(13) . ?
C14B C15B 1.37(2) . ?
C14B C13B 1.405(15) . ?
C13B C12B 1.47(4) . ?
C16A C15A 1.39(2) . ?
C15B C16B 1.37(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
C2 N3 C4 126.2(3) . . ?
C2 N1 C6 121.6(3) . . ?
C2 N1 C10 117.4(3) . . ?
C6 N1 C10 121.0(3) . . ?
C5 C6 N1 123.6(3) . . ?
C6 C5 C4 117.5(3) . . ?
C6 C5 C9 123.5(3) . . ?
C4 C5 C9 118.9(3) . . ?
O7 C2 N1 123.5(3) . . ?
O7 C2 N3 121.5(3) . . ?
N1 C2 N3 114.9(3) . . ?
O8 C4 N3 119.7(3) . . ?
O8 C4 C5 124.2(3) . . ?
N3 C4 C5 116.1(3) . . ?
N1 C10 C11 112.6(2) . . ?
C22 N23 C24 116.9(3) . . ?
C12B C11 C16A 102.7(16) . . ?
C12B C11 C10 127.3(16) . . ?
C16A C11 C10 130.0(6) . . ?
C12B C11 C12A 12(2) . . ?
C16A C11 C12A 112.9(11) . . ?
C10 C11 C12A 116.7(10) . . ?
C12B C11 C16B 119.6(15) . . ?
C16A C11 C16B 18.1(8) . . ?
C10 C11 C16B 112.8(6) . . ?
C12A C11 C16B 130.5(11) . . ?
N23 C22 C21 123.3(3) . . ?
C24 C19 C20 115.5(3) . . ?
C24 C19 C18A 136.3(6) . . ?
C20 C19 C18A 108.2(6) . . ?
C24 C19 C18B 105.1(5) . . ?
C20 C19 C18B 139.0(6) . . ?
C18A C19 C18B 32.0(3) . . ?
C13A C12A C11 120.3(16) . . ?
N23 C24 C19 124.7(4) . . ?
C21 C20 C19 119.5(4) . . ?
C20 C21 C22 119.9(4) . . ?
C15A C14A C13A 117.7(7) . . ?
C15A C14A C17A 127.4(7) . . ?
C13A C14A C17A 114.8(6) . . ?
C12A C13A C14A 119.5(13) . . ?
C17A C18A C19 118.4(11) . . ?
C17B C18B C19 117.1(10) . . ?
C18A C17A C14A 124.8(10) . . ?
C18B C17B C14B 128.8(11) . . ?
C15B C14B C13B 116.6(12) . . ?
C15B C14B C17B 122.9(12) . . ?
C13B C14B C17B 120.4(12) . . ?
C14B C13B C12B 120.9(15) . . ?
C11 C12B C13B 121(2) . . ?
C11 C16A C15A 127.5(10) . . ?
C16B C15B C14B 123.8(14) . . ?
C14A C15A C16A 121.2(11) . . ?
C15B C16B C11 116.6(10) . . ?

_diffrn_measured_fraction_theta_max 0.938
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.938
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.060
_database_code_depnum_ccdc_archive 'CCDC 984308'
#######################################################################
#
#                 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_VBMT4Pyr7

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 VBMT4Pyr
;
_chemical_name_common            VBMT4Pyr
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H19 N3 O2'
_chemical_formula_sum            'C20 H19 N3 O2'
_chemical_formula_weight         333.38

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   13.101(3)
_cell_length_b                   14.414(3)
_cell_length_c                   8.9980(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.68(3)
_cell_angle_gamma                90.00
_cell_volume                     1651.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9956
_exptl_absorpt_correction_T_max  0.9991
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'MX1 Beamline, Australian Synchrotron'
_diffrn_radiation_monochromator  'silicon double crystal'
_diffrn_measurement_device_type  'φ goniostat with quantum 210r detector'
_diffrn_measurement_method       'f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20365
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2866
_reflns_number_gt                2536
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Blu Ice'
_computing_cell_refinement       XDS
_computing_data_reduction        XDS
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  CIFTAB

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0637P)²+0.8659P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr.
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2866
_refine_ls_number_parameters     273
_refine_ls_number_restraints     102
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1263
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.74154(11) 0.48675(9) 0.15669(14) 0.0439(4) Uani 1 1 d . . .
N2 N 0.62155(11) 0.38319(10) 0.02606(16) 0.0322(3) Uani 1 1 d . . .
O3 O 0.51141(10) 0.27606(9) -0.11494(15) 0.0409(3) Uani 1 1 d . . .
N4 N 0.62838(11) 0.53497(10) -0.06256(15) 0.0318(3) Uani 1 1 d . . .
N5 N 1.23469(12) 0.61463(10) -0.78427(17) 0.0369(4) Uani 1 1 d D B .
C6 C 0.76184(13) 0.63256(11) -0.13882(19) 0.0311(4) Uani 1 1 d . B .
C7 C 0.55210(13) 0.51240(12) -0.19063(19) 0.0337(4) Uani 1 1 d . . .
H7 H 0.5280 0.5594 -0.2646 0.040 Uiso 1 1 calc R . .
C8 C 0.67748(15) 0.62770(12) -0.0502(2) 0.0373(4) Uani 1 1 d . . .
H8A H 0.7086 0.6419 0.0588 0.045 Uiso 1 1 calc R . .
H8B H 0.6230 0.6750 -0.0899 0.045 Uiso 1 1 calc R . .
C9 C 0.86070(14) 0.59492(12) -0.0788(2) 0.0380(4) Uani 1 1 d . . .
H9 H 0.8768 0.5706 0.0223 0.046 Uiso 1 1 calc R . .
C10 C 0.50989(13) 0.42727(13) -0.21650(19) 0.0340(4) Uani 1 1 d . . .
C11 C 1.25126(15) 0.58044(13) -0.6429(2) 0.0404(4) Uani 1 1 d D . .
H11 H 1.3160 0.5504 -0.5998 0.049 Uiso 1 1 calc R A 1
C12 C 0.54560(13) 0.35600(12) -0.10275(19) 0.0327(4) Uani 1 1 d . . .
C13 C 0.66951(13) 0.46958(12) 0.04676(19) 0.0332(4) Uani 1 1 d . . .
C14 C 1.1762(4) 0.5876(6) -0.5570(6) 0.0339(12) Uani 0.791(9) 1 d PD B 1
H14 H 1.1919 0.5633 -0.4561 0.041 Uiso 0.791(9) 1 calc PR B 1
C15 C 1.0622(3) 0.6634(4) -0.7610(5) 0.0346(9) Uani 0.791(9) 1 d PDU B 1
H15 H 0.9973 0.6916 -0.8096 0.042 Uiso 0.791(9) 1 calc PR B 1
C16 C 0.91512(15) 0.62633(13) -0.3101(2) 0.0442(5) Uani 1 1 d D . .
C17 C 1.14299(14) 0.65560(12) -0.8369(2) 0.0392(4) Uani 1 1 d D . .
H17 H 1.1310 0.6823 -0.9361 0.047 Uiso 1 1 calc R B 1
C18 C 1.0011(2) 0.61477(17) -0.3892(4) 0.0327(9) Uani 0.791(9) 1 d PDU B 1
H18 H 1.0647 0.5872 -0.3342 0.039 Uiso 0.791(9) 1 calc PR B 1
C19 C 0.74085(14) 0.67042(12) -0.2845(2) 0.0358(4) Uani 1 1 d . . .
H19 H 0.6747 0.6985 -0.3262 0.043 Uiso 1 1 calc R B .
C20 C 1.0782(4) 0.6296(6) -0.6140(5) 0.0346(10) Uani 0.791(9) 1 d PDU B 1
C21 C 0.81691(17) 0.66722(13) -0.3696(2) 0.0436(5) Uani 1 1 d . B .
H21 H 0.8019 0.6932 -0.4695 0.052 Uiso 1 1 calc R . .
C22 C 0.93532(15) 0.59224(13) -0.1629(2) 0.0425(5) Uani 1 1 d . B .
H22 H 1.0023 0.5663 -0.1188 0.051 Uiso 1 1 calc R . .
C23 C 0.9944(2) 0.64096(16) -0.5339(4) 0.0336(9) Uani 0.791(9) 1 d PDU B 1
H23 H 0.9308 0.6688 -0.5881 0.040 Uiso 0.791(9) 1 calc PR B 1
C24 C 0.66454(16) 0.31223(14) 0.1407(2) 0.0440(5) Uani 1 1 d . . .
H24A H 0.6249 0.2544 0.1151 0.066 Uiso 0.50 1 calc PR . .
H24B H 0.6590 0.3336 0.2418 0.066 Uiso 0.50 1 calc PR . .
H24C H 0.7385 0.3012 0.1416 0.066 Uiso 0.50 1 calc PR . .
H24D H 0.7234 0.3384 0.2173 0.066 Uiso 0.50 1 calc PR . .
H24E H 0.6893 0.2593 0.0905 0.066 Uiso 0.50 1 calc PR . .
H24F H 0.6097 0.2916 0.1907 0.066 Uiso 0.50 1 calc PR . .
C25 C 0.42832(16) 0.40164(15) -0.3565(2) 0.0461(5) Uani 1 1 d . . .
H25A H 0.4110 0.4560 -0.4230 0.069 Uiso 1 1 calc R . .
H25B H 0.3650 0.3799 -0.3270 0.069 Uiso 1 1 calc R . .
H25C H 0.4553 0.3522 -0.4113 0.069 Uiso 1 1 calc R . .
C14B C 1.2012(18) 0.576(3) -0.526(2) 0.037(5) Uani 0.209(9) 1 d PD B 2
H14B H 1.2262 0.5488 -0.4278 0.044 Uiso 0.209(9) 1 calc PR B 2
C15B C 1.0868(14) 0.661(2) -0.7243(18) 0.064(7) Uani 0.209(9) 1 d PDU B 2
H15B H 1.0258 0.6990 -0.7484 0.076 Uiso 0.209(9) 1 calc PR B 2
C20B C 1.1066(18) 0.619(2) -0.582(2) 0.045(5) Uani 0.209(9) 1 d PDU B 2
C18B C 0.9508(10) 0.6427(7) -0.4615(13) 0.036(3) Uani 0.209(9) 1 d PDU B 2
H18B H 0.9083 0.6715 -0.5495 0.043 Uiso 0.209(9) 1 calc PR B 2
C23B C 1.0474(11) 0.6118(7) -0.4532(13) 0.039(3) Uani 0.209(9) 1 d PDU B 2
H23B H 1.0830 0.5829 -0.3606 0.047 Uiso 0.209(9) 1 calc PR B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.220(2) . ?
N2 C13 1.387(2) . ?
N2 C12 1.393(2) . ?
N2 C24 1.467(2) . ?
O3 C12 1.232(2) . ?
N4 C7 1.374(2) . ?
N4 C13 1.377(2) . ?
N4 C8 1.476(2) . ?
N5 C17 1.322(2) . ?
N5 C11 1.333(2) . ?
C6 C19 1.386(2) . ?
C6 C9 1.390(2) . ?
C6 C8 1.510(2) . ?
C7 C10 1.343(3) . ?
C9 C22 1.371(3) . ?
C10 C12 1.448(2) . ?
C10 C25 1.493(3) . ?
C11 C14B 1.367(10) . ?
C11 C14 1.391(4) . ?
C14 C20 1.402(5) . ?
C15 C20 1.378(5) . ?
C15 C17 1.394(4) . ?
C16 C22 1.379(3) . ?
C16 C21 1.401(3) . ?
C16 C18 1.477(4) . ?
C16 C18B 1.559(11) . ?
C17 C15B 1.389(10) . ?
C18 C23 1.339(6) . ?
C19 C21 1.394(3) . ?
C20 C23 1.458(5) . ?
C14B C20B 1.374(9) . ?
C15B C20B 1.381(10) . ?
C20B C23B 1.545(14) . ?
C18B C23B 1.33(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
C13 N2 C12 125.16(14) . . ?
C13 N2 C24 116.42(15) . . ?
C12 N2 C24 117.94(15) . . ?
C7 N4 C13 121.42(15) . . ?
C7 N4 C8 119.70(14) . . ?
C13 N4 C8 118.42(15) . . ?
C17 N5 C11 115.86(16) . . ?
C19 C6 C9 118.66(16) . . ?
C19 C6 C8 120.76(16) . . ?
C9 C6 C8 120.50(16) . . ?
C10 C7 N4 123.34(16) . . ?
N4 C8 C6 111.24(13) . . ?
C22 C9 C6 121.11(18) . . ?
C7 C10 C12 118.34(16) . . ?
C7 C10 C25 123.74(17) . . ?
C12 C10 C25 117.92(17) . . ?
N5 C11 C14B 138.9(9) . . ?
N5 C11 C14 121.7(3) . . ?
C14B C11 C14 17.2(9) . . ?
O3 C12 N2 120.69(16) . . ?
O3 C12 C10 123.44(16) . . ?
N2 C12 C10 115.87(15) . . ?
O1 C13 N4 122.51(16) . . ?
O1 C13 N2 121.99(16) . . ?
N4 C13 N2 115.48(15) . . ?
C11 C14 C20 122.4(4) . . ?
C20 C15 C17 118.7(4) . . ?
C22 C16 C21 117.87(17) . . ?
C22 C16 C18 115.3(2) . . ?
C21 C16 C18 126.8(2) . . ?
C22 C16 C18B 149.8(6) . . ?
C21 C16 C18B 92.3(5) . . ?
C18 C16 C18B 34.5(5) . . ?
N5 C17 C15B 110.9(9) . . ?
N5 C17 C15 126.3(3) . . ?
C15B C17 C15 16.7(9) . . ?
C23 C18 C16 123.7(3) . . ?
C6 C19 C21 119.93(17) . . ?
C15 C20 C14 115.0(3) . . ?
C15 C20 C23 118.2(4) . . ?
C14 C20 C23 126.8(4) . . ?
C19 C21 C16 120.99(18) . . ?
C9 C22 C16 121.36(18) . . ?
C18 C23 C20 124.4(3) . . ?
C11 C14B C20B 104.4(12) . . ?
C20B C15B C17 129.4(14) . . ?
C14B C20B C15B 119.7(13) . . ?
C14B C20B C23B 105.1(11) . . ?
C15B C20B C23B 135.0(14) . . ?
C23B C18B C16 112.3(12) . . ?
C18B C23B C20B 125.2(14) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.039
_database_code_depnum_ccdc_archive 'CCDC 984309'
#######################################################################
#
#                 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_190912_VBMT3Pyr_5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 VBMT3Pyr
;
_chemical_name_common            VBMT3Pyr
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H19 N3 O2'
_chemical_formula_sum            'C20 H19 N3 O2'
_chemical_formula_weight         333.38

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   30.165(6)
_cell_length_b                   4.4000(9)
_cell_length_c                   24.600(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.83(3)
_cell_angle_gamma                90.00
_cell_volume                     3257.7(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9823
_exptl_absorpt_correction_T_max  0.9998
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'MX1 Beamline, Australian Synchrotron'
_diffrn_radiation_monochromator  'silicon double crystal'
_diffrn_measurement_device_type  'φ goniostat with quantum 210r detector'
_diffrn_measurement_method       'f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9932
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_av_sigmaI/netI    0.0529
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.35
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2833
_reflns_number_gt                2268
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Blu Ice'
_computing_cell_refinement       XDS
_computing_data_reduction        XDS
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  CIFTAB

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0684P)²+2.2617P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2833
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1322
_refine_ls_wR_factor_gt          0.1232
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
N1 N 0.11525(5) 0.7081(3) 0.41136(6) 0.0256(4) Uani 1 1 d . . .
O2 O 0.12988(4) 0.6870(3) 0.50334(5) 0.0329(3) Uani 1 1 d . . .
O3 O 0.01415(4) 0.1296(3) 0.42774(5) 0.0361(4) Uani 1 1 d . . .
N4 N 0.07143(5) 0.4126(3) 0.46589(6) 0.0265(4) Uani 1 1 d . . .
C5 C 0.05611(6) 0.4163(4) 0.36829(7) 0.0268(4) Uani 1 1 d . . .
C6 C 0.04454(5) 0.3048(4) 0.42136(7) 0.0268(4) Uani 1 1 d . . .
C7 C 0.25837(6) 0.4112(4) 0.43123(7) 0.0275(4) Uani 1 1 d . . .
H7 H 0.2769 0.3454 0.4617 0.033 Uiso 1 1 calc R . .
C8 C 0.26803(5) 0.3166(4) 0.37896(7) 0.0252(4) Uani 1 1 d . . .
C9 C 0.30558(6) 0.1127(4) 0.37237(7) 0.0265(4) Uani 1 1 d . . .
H9 H 0.3244 0.0699 0.4039 0.032 Uiso 1 1 calc R . .
C10 C 0.19512(5) 0.7007(4) 0.39565(7) 0.0251(4) Uani 1 1 d . . .
C11 C 0.22265(6) 0.5978(4) 0.43951(7) 0.0274(4) Uani 1 1 d . . .
H11 H 0.2168 0.6565 0.4755 0.033 Uiso 1 1 calc R . .
C12 C 0.31561(6) -0.0181(4) 0.32594(7) 0.0270(4) Uani 1 1 d . . .
H12 H 0.2967 0.0283 0.2946 0.032 Uiso 1 1 calc R . .
C13 C 0.10701(6) 0.6088(4) 0.46305(7) 0.0261(4) Uani 1 1 d . . .
N14 N 0.38778(5) -0.5452(4) 0.25328(6) 0.0323(4) Uani 1 1 d . . .
C15 C 0.20479(6) 0.6141(4) 0.34352(7) 0.0272(4) Uani 1 1 d . . .
H15 H 0.1867 0.6857 0.3131 0.033 Uiso 1 1 calc R . .
C16 C 0.09014(6) 0.6091(4) 0.36582(7) 0.0266(4) Uani 1 1 d . . .
H16 H 0.0974 0.6814 0.3311 0.032 Uiso 1 1 calc R . .
C17 C 0.15500(5) 0.8948(4) 0.40473(7) 0.0283(4) Uani 1 1 d . . .
H17A H 0.1611 1.0209 0.4377 0.034 Uiso 1 1 calc R . .
H17B H 0.1493 1.0333 0.3733 0.034 Uiso 1 1 calc R . .
C18 C 0.38523(6) -0.3039(4) 0.35820(7) 0.0280(4) Uani 1 1 d . . .
H18 H 0.3843 -0.2259 0.3941 0.034 Uiso 1 1 calc R . .
C19 C 0.41889(6) -0.4967(4) 0.34523(7) 0.0288(4) Uani 1 1 d . . .
H19 H 0.4418 -0.5504 0.3718 0.035 Uiso 1 1 calc R . .
C20 C 0.35598(6) -0.3539(4) 0.26656(7) 0.0281(4) Uani 1 1 d . . .
H20 H 0.3339 -0.3014 0.2388 0.034 Uiso 1 1 calc R . .
C21 C 0.35235(6) -0.2243(4) 0.31784(7) 0.0257(4) Uani 1 1 d . . .
C22 C 0.24028(6) 0.4253(4) 0.33526(7) 0.0274(4) Uani 1 1 d . . .
H22 H 0.2460 0.3678 0.2992 0.033 Uiso 1 1 calc R . .
C23 C 0.02786(6) 0.3138(5) 0.31958(7) 0.0330(4) Uani 1 1 d . . .
H23A H 0.0399 0.3951 0.2865 0.050 Uiso 1 1 calc R . .
H23B H -0.0026 0.3879 0.3222 0.050 Uiso 1 1 calc R . .
H23C H 0.0277 0.0913 0.3180 0.050 Uiso 1 1 calc R . .
C24 C 0.06182(6) 0.3117(5) 0.52089(7) 0.0338(5) Uani 1 1 d . . .
H24A H 0.0888 0.2272 0.5394 0.051 Uiso 1 1 calc R . .
H24B H 0.0386 0.1556 0.5182 0.051 Uiso 1 1 calc R . .
H24C H 0.0516 0.4852 0.5417 0.051 Uiso 1 1 calc R . .
C25 C 0.41882(6) -0.6109(4) 0.29287(7) 0.0311(4) Uani 1 1 d . . .
H25 H 0.4422 -0.7441 0.2845 0.037 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C16 1.380(2) . ?
N1 C13 1.383(2) . ?
N1 C17 1.472(2) . ?
O2 C13 1.219(2) . ?
O3 C6 1.216(2) . ?
N4 C13 1.383(2) . ?
N4 C6 1.402(2) . ?
N4 C24 1.471(2) . ?
C5 C16 1.336(3) . ?
C5 C6 1.459(3) . ?
C5 C23 1.493(2) . ?
C7 C11 1.380(3) . ?
C7 C8 1.401(2) . ?
C8 C22 1.402(2) . ?
C8 C9 1.463(3) . ?
C9 C12 1.332(3) . ?
C10 C15 1.387(2) . ?
C10 C11 1.393(2) . ?
C10 C17 1.510(2) . ?
C12 C21 1.456(3) . ?
N14 C20 1.333(2) . ?
N14 C25 1.337(2) . ?
C15 C22 1.381(3) . ?
C18 C19 1.377(3) . ?
C18 C21 1.400(2) . ?
C19 C25 1.382(3) . ?
C20 C21 1.395(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
C16 N1 C13 121.61(15) . . ?
C16 N1 C17 119.56(14) . . ?
C13 N1 C17 118.43(14) . . ?
C13 N4 C6 125.63(15) . . ?
C13 N4 C24 115.85(14) . . ?
C6 N4 C24 118.52(15) . . ?
C16 C5 C6 118.98(16) . . ?
C16 C5 C23 123.67(16) . . ?
C6 C5 C23 117.33(16) . . ?
O3 C6 N4 121.04(16) . . ?
O3 C6 C5 123.79(16) . . ?
N4 C6 C5 115.17(15) . . ?
C11 C7 C8 121.63(16) . . ?
C7 C8 C22 116.91(16) . . ?
C7 C8 C9 119.61(15) . . ?
C22 C8 C9 123.48(16) . . ?
C12 C9 C8 125.59(16) . . ?
C15 C10 C11 118.38(16) . . ?
C15 C10 C17 120.81(15) . . ?
C11 C10 C17 120.78(16) . . ?
C7 C11 C10 120.67(16) . . ?
C9 C12 C21 127.24(16) . . ?
O2 C13 N4 122.30(16) . . ?
O2 C13 N1 122.14(16) . . ?
N4 C13 N1 115.55(15) . . ?
C20 N14 C25 116.00(15) . . ?
C22 C15 C10 120.95(16) . . ?
C5 C16 N1 123.04(16) . . ?
N1 C17 C10 111.56(15) . . ?
C19 C18 C21 119.22(16) . . ?
C18 C19 C25 118.99(16) . . ?
N14 C20 C21 125.51(16) . . ?
C20 C21 C18 116.37(16) . . ?
C20 C21 C12 118.99(15) . . ?
C18 C21 C12 124.64(16) . . ?
C15 C22 C8 121.43(16) . . ?
N14 C25 C19 123.89(17) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.045
_database_code_depnum_ccdc_archive 'CCDC 984310'
#######################################################################
#
#                 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_VMT4PyrDimer4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 VMT4PyrDimer
;
_chemical_name_common            VMT4PyrDimer
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H38 N6 O4'
_chemical_formula_sum            'C40 H38 N6 O4'
_chemical_formula_weight         666.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   8.1880(16)
_cell_length_b                   12.063(2)
_cell_length_c                   17.140(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.02(3)
_cell_angle_gamma                90.00
_cell_volume                     1649.4(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.00
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9991
_exptl_absorpt_correction_T_max  0.9999
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'MX1 Beamline, Australian Synchrotron'
_diffrn_radiation_monochromator  'silicon double crystal'
_diffrn_measurement_device_type  'φ goniostat with quantum 210r detector'
_diffrn_measurement_method       'f scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20998
_diffrn_reflns_av_R_equivalents  0.2321
_diffrn_reflns_av_sigmaI/netI    0.1185
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2915
_reflns_number_gt                1663
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Blu Ice'
_computing_cell_refinement       XDS
_computing_data_reduction        XDS
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  CIFTAB

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1642P)²+3.5350P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.058(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2915
_refine_ls_number_parameters     237
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.1733
_refine_ls_R_factor_gt           0.1105
_refine_ls_wR_factor_ref         0.3284
_refine_ls_wR_factor_gt          0.2746
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.043
_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
O1 O 0.8157(5) 0.2722(3) -0.0058(2) 0.0395(11) Uani 1 1 d . . .
N1 N 0.9289(5) 0.1354(4) 0.0818(2) 0.0304(11) Uani 1 1 d . . .
C1 C 0.9271(7) 0.2042(5) 0.0175(3) 0.0317(13) Uani 1 1 d . . .
O2 O 1.3092(5) 0.1181(4) -0.0307(2) 0.0447(12) Uani 1 1 d . . .
N2 N 1.0582(6) 0.1913(4) -0.0202(2) 0.0335(12) Uani 1 1 d . . .
C2 C 1.0550(8) 0.2619(6) -0.0906(3) 0.0468(16) Uani 1 1 d . . .
H2A H 0.9405 0.2653 -0.1235 0.070 Uiso 1 1 calc R . .
H2B H 1.1296 0.2306 -0.1223 0.070 Uiso 1 1 calc R . .
H2C H 1.0929 0.3367 -0.0730 0.070 Uiso 1 1 calc R . .
N3 N 1.3256(10) -0.1368(6) 0.2974(3) 0.070(2) Uani 1 1 d . . .
C3 C 1.1957(6) 0.1196(5) 0.0051(3) 0.0323(13) Uani 1 1 d . . .
C4 C 1.1897(7) 0.0506(5) 0.0736(3) 0.0311(13) Uani 1 1 d . . .
C5 C 1.3342(7) -0.0240(5) 0.1048(3) 0.0392(14) Uani 1 1 d . . .
H5A H 1.4336 0.0205 0.1276 0.059 Uiso 1 1 calc R . .
H5B H 1.3562 -0.0697 0.0611 0.059 Uiso 1 1 calc R . .
H5C H 1.3080 -0.0721 0.1465 0.059 Uiso 1 1 calc R . .
C6 C 1.0575(6) 0.0616(5) 0.1077(3) 0.0303(12) Uani 1 1 d . . .
H6 H 1.0529 0.0156 0.1522 0.036 Uiso 1 1 calc R . .
C7 C 0.7807(7) 0.1411(6) 0.1173(3) 0.0444(16) Uani 1 1 d . . .
H7A H 0.6933 0.0905 0.0875 0.053 Uiso 1 1 calc R . .
H7B H 0.7350 0.2174 0.1110 0.053 Uiso 1 1 calc R . .
C8 C 0.8189(6) 0.1103(5) 0.2048(3) 0.0318(13) Uani 1 1 d . . .
C9 C 0.7623(7) 0.0111(5) 0.2293(4) 0.0407(15) Uani 1 1 d . . .
H9 H 0.7038 -0.0390 0.1900 0.049 Uiso 1 1 calc R . .
C10 C 0.9052(7) 0.1828(5) 0.2621(3) 0.0395(14) Uani 1 1 d . . .
H10 H 0.9449 0.2519 0.2472 0.047 Uiso 1 1 calc R . .
C11 C 0.7876(8) -0.0167(7) 0.3073(4) 0.0544(19) Uani 1 1 d D . .
H11 H 0.7466 -0.0858 0.3215 0.065 Uiso 1 1 calc R . .
C12 C 0.9330(8) 0.1505(7) 0.3443(4) 0.063(2) Uani 1 1 d . . .
H12 H 0.9952 0.1975 0.3847 0.076 Uiso 1 1 calc R . .
C13 C 0.8692(9) 0.0505(7) 0.3655(4) 0.057(2) Uani 1 1 d U . .
C16 C 1.1615(8) -0.0917(6) 0.4197(3) 0.0419(16) Uani 1 1 d U . .
C17 C 1.2754(9) -0.0208(6) 0.4016(4) 0.0569(19) Uani 1 1 d . . .
H17 H 1.3014 0.0463 0.4307 0.068 Uiso 1 1 calc R . .
C18 C 1.1279(8) -0.1872(6) 0.3756(3) 0.0489(17) Uani 1 1 d D . .
H18 H 1.0488 -0.2395 0.3861 0.059 Uiso 1 1 calc R . .
C19 C 1.3522(10) -0.0462(7) 0.3416(5) 0.071(2) Uani 1 1 d . . .
H19 H 1.4317 0.0053 0.3306 0.085 Uiso 1 1 calc R . .
C20 C 1.2114(11) -0.2053(6) 0.3157(4) 0.059(2) Uani 1 1 d . . .
H20 H 1.1862 -0.2712 0.2850 0.071 Uiso 1 1 calc R . .
C21 C 0.8907(10) 0.0013(7) 0.4496(4) 0.061(2) Uani 1 1 d DU . .
C14 C 1.0528(12) -0.0746(9) 0.4792(4) 0.080(3) Uani 1 1 d DU . .
H14 H 1.027(12) -0.1376(15) 0.508(3) 0.11(3) Uiso 1 1 d D . .
H21 H 0.791(6) -0.029(9) 0.4625(8) 0.13(4) Uiso 1 1 d 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
O1 C1 1.225(6) . ?
N1 C6 1.374(7) . ?
N1 C1 1.377(6) . ?
N1 C7 1.476(7) . ?
C1 N2 1.381(7) . ?
O2 C3 1.224(6) . ?
N2 C3 1.408(7) . ?
N2 C2 1.473(7) . ?
N3 C19 1.319(10) . ?
N3 C20 1.337(10) . ?
C3 C4 1.449(7) . ?
C4 C6 1.348(7) . ?
C4 C5 1.487(7) . ?
C7 C8 1.508(7) . ?
C8 C10 1.383(8) . ?
C8 C9 1.383(8) . ?
C9 C11 1.349(8) . ?
C10 C12 1.430(9) . ?
C11 C13 1.340(11) . ?
C12 C13 1.395(11) . ?
C13 C21 1.534(9) . ?
C16 C17 1.352(10) . ?
C16 C18 1.372(9) . ?
C16 C14 1.511(9) . ?
C17 C19 1.355(10) . ?
C18 C20 1.373(10) . ?
C21 C14 1.493(12) 3_756 ?
C21 C14 1.597(10) . ?
C14 C21 1.493(12) 3_756 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C1 121.2(4) . . ?
C6 N1 C7 122.5(4) . . ?
C1 N1 C7 116.1(4) . . ?
O1 C1 N1 122.5(5) . . ?
O1 C1 N2 121.6(5) . . ?
N1 C1 N2 115.9(5) . . ?
C1 N2 C3 125.2(4) . . ?
C1 N2 C2 116.5(5) . . ?
C3 N2 C2 118.2(5) . . ?
C19 N3 C20 114.3(6) . . ?
O2 C3 N2 120.0(5) . . ?
O2 C3 C4 124.5(5) . . ?
N2 C3 C4 115.6(4) . . ?
C6 C4 C3 118.2(5) . . ?
C6 C4 C5 123.7(5) . . ?
C3 C4 C5 118.0(5) . . ?
C4 C6 N1 123.7(5) . . ?
N1 C7 C8 113.1(4) . . ?
C10 C8 C9 119.0(5) . . ?
C10 C8 C7 120.6(6) . . ?
C9 C8 C7 120.4(5) . . ?
C11 C9 C8 121.9(7) . . ?
C8 C10 C12 118.0(6) . . ?
C13 C11 C9 121.7(7) . . ?
C13 C12 C10 120.4(6) . . ?
C11 C13 C12 118.9(6) . . ?
C11 C13 C21 113.4(7) . . ?
C12 C13 C21 127.6(8) . . ?
C17 C16 C18 117.9(6) . . ?
C17 C16 C14 127.6(7) . . ?
C18 C16 C14 114.3(7) . . ?
C16 C17 C19 119.5(7) . . ?
C16 C18 C20 118.3(7) . . ?
N3 C19 C17 125.3(8) . . ?
N3 C20 C18 124.7(7) . . ?
C14 C21 C13 119.2(8) 3_756 . ?
C14 C21 C14 89.9(6) 3_756 . ?
C13 C21 C14 115.5(6) . . ?
C21 C14 C16 120.8(9) 3_756 . ?
C21 C14 C21 90.1(6) 3_756 . ?
C16 C14 C21 116.0(6) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.537
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.114
_database_code_depnum_ccdc_archive 'CCDC 984311'
