# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics
# This journal is © The 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
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_BpzXyPhOH

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N4 O'
_chemical_formula_sum            'C22 H18 N4 O'
_chemical_formula_weight         354.40

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   'P2(1)   '
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   6.03460(10)
_cell_length_b                   19.3933(4)
_cell_length_c                   7.4728(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.9310(10)
_cell_angle_gamma                90.00
_cell_volume                     871.31(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9918
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      30.00


_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6841
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            38039
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         30.10
_reflns_number_total             5107
_reflns_number_gt                4877
_reflns_threshold_expression     >2sigma(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 F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
In the absence of significant anomalous scattering, the absolute structure 
was assigned arbitrarily. Indeed, the Flack parameter was found to be 
meaningless (0.1(15)) here and was removed from the cif file.
All non-hydrogens were refined anisotropically. 
Hydrogen atoms were assigned to ideal positions and refined isotropically using a riding model. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0633P)^2^+0.1874P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         5107
_refine_ls_number_parameters     247
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.052
_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 1.2363(2) 0.63331(7) 1.06177(18) 0.0187(2) Uani 1 1 d . . .
H1 H 1.3767 0.6340 1.1236 0.022 Uiso 1 1 calc R . .
C2 C 1.0578(2) 0.66037(7) 1.14493(18) 0.0176(2) Uani 1 1 d . . .
H2 H 1.0817 0.6790 1.2596 0.021 Uiso 1 1 calc R . .
C3 C 0.8267(2) 0.63140(7) 0.89840(18) 0.0179(2) Uani 1 1 d . . .
H3 H 0.6853 0.6291 0.8385 0.022 Uiso 1 1 calc R . .
C4 C 1.0078(2) 0.60485(7) 0.81511(17) 0.0146(2) Uani 1 1 d . . .
C5 C 0.9774(2) 0.57178(7) 0.63673(17) 0.0146(2) Uani 1 1 d . . .
C6 C 0.7447(2) 0.52021(7) 0.42010(18) 0.0179(2) Uani 1 1 d . . .
H6 H 0.6021 0.5088 0.3722 0.022 Uiso 1 1 calc R . .
C7 C 0.9274(2) 0.49878(7) 0.32825(17) 0.0148(2) Uani 1 1 d . . .
C8 C 1.1582(2) 0.55458(7) 0.54021(17) 0.0153(2) Uani 1 1 d . . .
H8 H 1.2997 0.5689 0.5837 0.018 Uiso 1 1 calc R . .
C9 C 0.8909(2) 0.45383(6) 0.16833(17) 0.0149(2) Uani 1 1 d . . .
C10 C 1.0314(2) 0.39806(7) 0.13501(17) 0.0160(2) Uani 1 1 d . . .
C11 C 0.9683(2) 0.35575(7) -0.01207(18) 0.0164(2) Uani 1 1 d . . .
H11 H 1.0597 0.3188 -0.0359 0.020 Uiso 1 1 calc R . .
C12 C 0.7747(2) 0.36629(6) -0.12479(17) 0.0150(2) Uani 1 1 d . . .
C13 C 0.6373(2) 0.42255(7) -0.09370(17) 0.0153(2) Uani 1 1 d . . .
C14 C 0.6988(2) 0.46532(7) 0.05167(17) 0.0161(2) Uani 1 1 d . . .
H14 H 0.6093 0.5030 0.0726 0.019 Uiso 1 1 calc R . .
C15 C 1.2411(2) 0.37990(8) 0.25033(19) 0.0204(3) Uani 1 1 d . . .
H15A H 1.2852 0.3337 0.2238 0.031 Uiso 1 1 calc R . .
H15B H 1.2139 0.3831 0.3748 0.031 Uiso 1 1 calc R . .
H15C H 1.3575 0.4114 0.2257 0.031 Uiso 1 1 calc R . .
C16 C 0.4282(2) 0.43632(7) -0.21210(18) 0.0193(3) Uani 1 1 d . . .
H16A H 0.3240 0.3996 -0.1992 0.029 Uiso 1 1 calc R . .
H16B H 0.4625 0.4390 -0.3350 0.029 Uiso 1 1 calc R . .
H16C H 0.3643 0.4792 -0.1779 0.029 Uiso 1 1 calc R . .
C17 C 0.7193(2) 0.31853(7) -0.27855(17) 0.0155(2) Uani 1 1 d . . .
C18 C 0.5431(2) 0.27156(7) -0.27660(17) 0.0167(2) Uani 1 1 d . . .
C19 C 0.4912(2) 0.22738(7) -0.42179(19) 0.0194(2) Uani 1 1 d . . .
H19 H 0.3724 0.1969 -0.4204 0.023 Uiso 1 1 calc R . .
C20 C 0.6181(3) 0.22929(8) -0.56845(19) 0.0228(3) Uani 1 1 d . . .
H20 H 0.5841 0.1997 -0.6649 0.027 Uiso 1 1 calc R . .
C21 C 0.7950(3) 0.27481(8) -0.5723(2) 0.0258(3) Uani 1 1 d . . .
H21 H 0.8802 0.2757 -0.6703 0.031 Uiso 1 1 calc R . .
C22 C 0.8434(3) 0.31917(8) -0.42718(19) 0.0225(3) Uani 1 1 d . . .
H22 H 0.9614 0.3499 -0.4298 0.027 Uiso 1 1 calc R . .
N1 N 1.21426(18) 0.60650(6) 0.89761(15) 0.0170(2) Uani 1 1 d . . .
N2 N 0.85185(19) 0.65988(6) 1.06178(16) 0.0184(2) Uani 1 1 d . . .
N3 N 0.76791(18) 0.55607(6) 0.57250(15) 0.0182(2) Uani 1 1 d . . .
N4 N 1.13458(17) 0.51825(6) 0.38753(15) 0.0154(2) Uani 1 1 d . . .
O1 O 0.43217(17) 0.26953(6) -0.12551(15) 0.0231(2) Uani 1 1 d . . .
H1A H 0.3595 0.2338 -0.1245 0.035 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0144(5) 0.0215(6) 0.0198(6) -0.0035(5) -0.0006(4) 0.0004(5)
C2 0.0180(6) 0.0185(6) 0.0163(6) -0.0022(5) 0.0008(4) -0.0003(5)
C3 0.0135(5) 0.0217(6) 0.0185(5) -0.0014(5) 0.0004(4) 0.0031(5)
C4 0.0143(5) 0.0146(5) 0.0151(5) 0.0000(4) 0.0019(4) 0.0009(4)
C5 0.0142(5) 0.0141(5) 0.0155(5) -0.0010(4) 0.0002(4) 0.0007(4)
C6 0.0129(5) 0.0216(6) 0.0191(6) -0.0040(5) 0.0004(4) -0.0008(5)
C7 0.0148(5) 0.0150(5) 0.0145(5) 0.0005(4) 0.0008(4) -0.0008(4)
C8 0.0133(5) 0.0165(6) 0.0160(5) -0.0009(4) 0.0007(4) -0.0004(4)
C9 0.0151(5) 0.0152(6) 0.0146(5) -0.0008(4) 0.0021(4) -0.0018(4)
C10 0.0136(5) 0.0171(6) 0.0176(6) 0.0000(5) 0.0025(4) -0.0011(4)
C11 0.0147(5) 0.0154(5) 0.0195(5) -0.0018(4) 0.0031(4) 0.0003(4)
C12 0.0164(5) 0.0144(6) 0.0146(5) -0.0006(4) 0.0030(4) -0.0033(4)
C13 0.0160(5) 0.0151(6) 0.0147(5) 0.0002(4) 0.0005(4) -0.0021(4)
C14 0.0172(5) 0.0153(6) 0.0160(5) -0.0010(4) 0.0020(4) 0.0003(4)
C15 0.0145(5) 0.0230(6) 0.0230(6) -0.0034(5) -0.0015(4) 0.0019(5)
C16 0.0198(6) 0.0186(6) 0.0189(6) -0.0005(5) -0.0028(5) 0.0010(5)
C17 0.0170(5) 0.0152(5) 0.0144(5) -0.0016(4) 0.0011(4) -0.0009(4)
C18 0.0164(5) 0.0156(6) 0.0183(6) 0.0004(5) 0.0021(4) 0.0003(5)
C19 0.0174(5) 0.0177(6) 0.0226(6) -0.0020(5) -0.0016(5) -0.0022(5)
C20 0.0305(7) 0.0204(6) 0.0169(6) -0.0040(5) -0.0016(5) -0.0007(5)
C21 0.0358(8) 0.0248(7) 0.0180(6) -0.0034(5) 0.0088(6) -0.0053(6)
C22 0.0268(7) 0.0217(6) 0.0200(6) -0.0022(5) 0.0073(5) -0.0062(5)
N1 0.0139(5) 0.0180(5) 0.0189(5) -0.0028(4) 0.0002(4) 0.0002(4)
N2 0.0170(5) 0.0190(5) 0.0193(5) -0.0013(4) 0.0029(4) 0.0027(4)
N3 0.0132(5) 0.0227(6) 0.0184(5) -0.0036(4) 0.0003(4) 0.0005(4)
N4 0.0139(5) 0.0157(5) 0.0166(5) -0.0009(4) 0.0016(4) -0.0014(4)
O1 0.0227(5) 0.0202(5) 0.0279(5) -0.0036(4) 0.0109(4) -0.0057(4)

_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 1.3285(17) . ?
C1 C2 1.3914(18) . ?
C1 H1 0.9300 . ?
C2 N2 1.3411(17) . ?
C2 H2 0.9300 . ?
C3 N2 1.3367(17) . ?
C3 C4 1.4013(16) . ?
C3 H3 0.9300 . ?
C4 N1 1.3424(16) . ?
C4 C5 1.4764(17) . ?
C5 N3 1.3478(16) . ?
C5 C8 1.3991(17) . ?
C6 N3 1.3315(17) . ?
C6 C7 1.4100(17) . ?
C6 H6 0.9300 . ?
C7 N4 1.3444(16) . ?
C7 C9 1.4802(17) . ?
C8 N4 1.3380(16) . ?
C8 H8 0.9300 . ?
C9 C14 1.4070(17) . ?
C9 C10 1.4097(18) . ?
C10 C11 1.3980(18) . ?
C10 C15 1.5101(17) . ?
C11 C12 1.3953(18) . ?
C11 H11 0.9300 . ?
C12 C13 1.4020(18) . ?
C12 C17 1.4913(17) . ?
C13 C14 1.3916(17) . ?
C13 C16 1.5016(18) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C22 1.3922(18) . ?
C17 C18 1.4012(17) . ?
C18 O1 1.3616(15) . ?
C18 C19 1.3967(18) . ?
C19 C20 1.390(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.388(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.395(2) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
O1 H1A 0.8200 . ?

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 122.69(12) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
N2 C2 C1 120.83(12) . . ?
N2 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
N2 C3 C4 121.71(12) . . ?
N2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
N1 C4 C3 121.06(11) . . ?
N1 C4 C5 117.61(10) . . ?
C3 C4 C5 121.30(11) . . ?
N3 C5 C8 120.77(11) . . ?
N3 C5 C4 117.37(11) . . ?
C8 C5 C4 121.81(11) . . ?
N3 C6 C7 122.78(11) . . ?
N3 C6 H6 118.6 . . ?
C7 C6 H6 118.6 . . ?
N4 C7 C6 120.03(11) . . ?
N4 C7 C9 120.07(11) . . ?
C6 C7 C9 119.89(11) . . ?
N4 C8 C5 122.32(11) . . ?
N4 C8 H8 118.8 . . ?
C5 C8 H8 118.8 . . ?
C14 C9 C10 119.22(11) . . ?
C14 C9 C7 117.67(11) . . ?
C10 C9 C7 122.99(11) . . ?
C11 C10 C9 117.51(11) . . ?
C11 C10 C15 118.04(12) . . ?
C9 C10 C15 124.43(12) . . ?
C12 C11 C10 123.09(12) . . ?
C12 C11 H11 118.5 . . ?
C10 C11 H11 118.5 . . ?
C11 C12 C13 119.37(11) . . ?
C11 C12 C17 119.66(11) . . ?
C13 C12 C17 120.95(11) . . ?
C14 C13 C12 118.12(11) . . ?
C14 C13 C16 120.55(12) . . ?
C12 C13 C16 121.32(11) . . ?
C13 C14 C9 122.65(12) . . ?
C13 C14 H14 118.7 . . ?
C9 C14 H14 118.7 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C17 C18 118.36(12) . . ?
C22 C17 C12 120.58(11) . . ?
C18 C17 C12 121.06(11) . . ?
O1 C18 C19 122.21(12) . . ?
O1 C18 C17 117.06(11) . . ?
C19 C18 C17 120.69(11) . . ?
C20 C19 C18 119.61(12) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C21 C20 C19 120.68(13) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 119.08(13) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C17 C22 C21 121.57(13) . . ?
C17 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C1 N1 C4 116.66(11) . . ?
C3 N2 C2 117.01(11) . . ?
C6 N3 C5 116.68(11) . . ?
C8 N4 C7 117.17(11) . . ?
C18 O1 H1A 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.10
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 951403'