# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Dr Sylvia M Draper'
_publ_contact_author_email       smdraper@tcd.ie

_publ_section_title              
;
Supramolecular luminescent system based
on 2-cyano-3(4-(diphenylamino)phenyl) acrylic acid:
Chiral luminescent host for selective CH3CN sensor

;
loop_
_publ_author_name
S.Anthony
C.Delaney
S.Varughese
L.Wang
S.Draper

data_CDPA-DMAP-cif
_database_code_depnum_ccdc_archive 'CCDC 797566'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            CDPA-DMAP
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H15 N2 O2, C7 H11 N2'
_chemical_formula_sum            'C29 H26 N4 O2'
_chemical_formula_weight         462.54

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   7.6459(15)
_cell_length_b                   27.929(6)
_cell_length_c                   11.311(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.84(3)
_cell_angle_gamma                90.00
_cell_volume                     2414.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2638
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      47.89

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9838
_exptl_absorpt_correction_T_max  0.9927
_exptl_absorpt_process_details   'SADABS; Sheldrick, 1997'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD Area Detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18765
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_sigmaI/netI    0.0593
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         25.25
_reflns_number_total             4341
_reflns_number_gt                3723
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SMART
_computing_cell_refinement       SAINTPLUS
_computing_data_reduction        SAINTPLUS
_computing_structure_solution    'SHELXTL (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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.
;

_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^)+(0.0791P)^2^+0.3354P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4341
_refine_ls_number_parameters     320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1637
_refine_ls_wR_factor_gt          0.1498
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_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
N90 N 1.2613(2) 0.25147(6) 0.67687(15) 0.0251(4) Uani 1 1 d . . .
N96 N 0.8202(2) 0.31940(6) 0.79269(16) 0.0272(4) Uani 1 1 d . . .
C91 C 1.2408(3) 0.25952(7) 0.79335(18) 0.0247(5) Uani 1 1 d . . .
H91 H 1.3302 0.2495 0.8482 0.030 Uiso 1 1 calc R . .
C92 C 1.0962(3) 0.28148(7) 0.83470(18) 0.0230(5) Uani 1 1 d . . .
H92 H 1.0861 0.2868 0.9172 0.028 Uiso 1 1 calc R . .
C93 C 0.9609(3) 0.29643(7) 0.75483(18) 0.0218(4) Uani 1 1 d . . .
C94 C 0.9857(3) 0.28656(7) 0.63362(18) 0.0244(5) Uani 1 1 d . . .
H94 H 0.8973 0.2950 0.5765 0.029 Uiso 1 1 calc R . .
C95 C 1.1345(3) 0.26509(7) 0.59836(18) 0.0248(5) Uani 1 1 d . . .
H95 H 1.1497 0.2595 0.5165 0.030 Uiso 1 1 calc R . .
C97 C 0.8069(3) 0.33542(9) 0.9142(2) 0.0349(6) Uani 1 1 d . . .
H97B H 0.9112 0.3253 0.9602 0.052 Uiso 1 1 calc R . .
H97C H 0.7026 0.3213 0.9484 0.052 Uiso 1 1 calc R . .
H97A H 0.7979 0.3704 0.9159 0.052 Uiso 1 1 calc R . .
C98 C 0.6731(3) 0.33151(9) 0.7140(2) 0.0353(6) Uani 1 1 d . . .
H98B H 0.6937 0.3189 0.6348 0.053 Uiso 1 1 calc R . .
H98A H 0.6604 0.3664 0.7101 0.053 Uiso 1 1 calc R . .
H98C H 0.5660 0.3174 0.7441 0.053 Uiso 1 1 calc R . .
H90 H 1.373(3) 0.2356(9) 0.651(2) 0.049(8) Uiso 1 1 d . . .
O1A O 0.06148(19) 0.28914(5) 0.12387(12) 0.0278(4) Uani 1 1 d . . .
O1B O 0.1142(2) 0.28735(5) 0.32005(13) 0.0324(4) Uani 1 1 d . . .
N3 N 0.3666(3) 0.35683(8) -0.01404(17) 0.0411(5) Uani 1 1 d . . .
N5 N 1.0701(2) 0.43663(6) 0.34897(15) 0.0251(4) Uani 1 1 d . . .
C1 C 0.1497(3) 0.29919(7) 0.21782(18) 0.0236(5) Uani 1 1 d . . .
C2 C 0.3134(3) 0.32827(7) 0.19949(18) 0.0225(5) Uani 1 1 d . . .
C3 C 0.3434(3) 0.34385(8) 0.08081(19) 0.0270(5) Uani 1 1 d . . .
C4 C 0.4219(3) 0.33856(7) 0.29196(18) 0.0219(4) Uani 1 1 d . . .
H4 H 0.3833 0.3270 0.3656 0.026 Uiso 1 1 calc R . .
C6 C 0.9089(3) 0.41287(7) 0.33385(18) 0.0217(5) Uani 1 1 d . . .
C7 C 0.8037(3) 0.40278(7) 0.42972(18) 0.0238(5) Uani 1 1 d . . .
H7 H 0.8399 0.4126 0.5071 0.029 Uiso 1 1 calc R . .
C8 C 0.6483(3) 0.37879(7) 0.41227(18) 0.0228(5) Uani 1 1 d . . .
H8 H 0.5796 0.3718 0.4786 0.027 Uiso 1 1 calc R . .
C9 C 0.5879(3) 0.36424(7) 0.29995(18) 0.0211(4) Uani 1 1 d . . .
C10 C 0.6922(3) 0.37504(7) 0.20497(19) 0.0263(5) Uani 1 1 d . . .
H10 H 0.6542 0.3660 0.1274 0.032 Uiso 1 1 calc R . .
C11 C 0.8494(3) 0.39858(7) 0.22119(19) 0.0258(5) Uani 1 1 d . . .
H11 H 0.9185 0.4052 0.1548 0.031 Uiso 1 1 calc R . .
C12 C 1.1291(3) 0.46763(7) 0.25781(18) 0.0243(5) Uani 1 1 d . . .
C13 C 1.0193(3) 0.50293(8) 0.2104(2) 0.0375(6) Uani 1 1 d . . .
H13 H 0.9037 0.5064 0.2375 0.045 Uiso 1 1 calc R . .
C14 C 1.0799(3) 0.53302(9) 0.1230(3) 0.0476(7) Uani 1 1 d . . .
H14 H 1.0044 0.5568 0.0896 0.057 Uiso 1 1 calc R . .
C15 C 1.2473(3) 0.52891(9) 0.0841(2) 0.0386(6) Uani 1 1 d . . .
H15 H 1.2879 0.5499 0.0249 0.046 Uiso 1 1 calc R . .
C16 C 1.3561(3) 0.49403(8) 0.1318(2) 0.0305(5) Uani 1 1 d . . .
H16 H 1.4723 0.4911 0.1054 0.037 Uiso 1 1 calc R . .
C17 C 1.2972(3) 0.46322(7) 0.21786(19) 0.0256(5) Uani 1 1 d . . .
H17 H 1.3725 0.4390 0.2495 0.031 Uiso 1 1 calc R . .
C18 C 1.1683(3) 0.43416(7) 0.45758(18) 0.0225(4) Uani 1 1 d . . .
C19 C 1.2581(3) 0.47392(7) 0.50063(19) 0.0269(5) Uani 1 1 d . . .
H19 H 1.2532 0.5031 0.4576 0.032 Uiso 1 1 calc R . .
C20 C 1.3549(3) 0.47132(8) 0.6061(2) 0.0298(5) Uani 1 1 d . . .
H20 H 1.4183 0.4986 0.6338 0.036 Uiso 1 1 calc R . .
C21 C 1.3602(3) 0.42941(8) 0.6714(2) 0.0291(5) Uani 1 1 d . . .
H21 H 1.4244 0.4279 0.7446 0.035 Uiso 1 1 calc R . .
C22 C 1.2700(3) 0.38943(8) 0.62822(19) 0.0279(5) Uani 1 1 d . . .
H22 H 1.2718 0.3606 0.6728 0.034 Uiso 1 1 calc R . .
C23 C 1.1780(3) 0.39124(7) 0.52134(19) 0.0250(5) Uani 1 1 d . . .
H23 H 1.1212 0.3634 0.4910 0.030 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
N90 0.0256(10) 0.0275(9) 0.0224(10) 0.0001(7) 0.0017(8) 0.0030(8)
N96 0.0226(10) 0.0366(10) 0.0222(10) 0.0037(7) -0.0007(8) 0.0059(8)
C91 0.0238(11) 0.0301(11) 0.0200(11) 0.0023(8) -0.0020(9) 0.0000(9)
C92 0.0221(11) 0.0281(10) 0.0186(10) 0.0006(8) -0.0025(9) -0.0007(8)
C93 0.0211(11) 0.0199(10) 0.0243(11) 0.0022(8) 0.0007(9) -0.0023(8)
C94 0.0242(11) 0.0269(10) 0.0218(11) 0.0005(8) -0.0041(9) 0.0007(9)
C95 0.0305(12) 0.0234(10) 0.0204(11) 0.0004(8) -0.0023(9) 0.0002(9)
C97 0.0370(13) 0.0437(13) 0.0244(12) 0.0021(10) 0.0055(10) 0.0130(11)
C98 0.0251(12) 0.0436(14) 0.0369(14) 0.0054(10) -0.0054(10) 0.0082(10)
O1A 0.0250(8) 0.0395(9) 0.0188(8) -0.0010(6) -0.0023(6) -0.0086(7)
O1B 0.0327(9) 0.0452(9) 0.0191(8) 0.0047(6) -0.0011(7) -0.0150(7)
N3 0.0385(12) 0.0591(13) 0.0255(11) 0.0051(10) -0.0016(9) -0.0169(10)
N5 0.0240(9) 0.0281(9) 0.0232(10) 0.0056(7) -0.0020(7) -0.0065(7)
C1 0.0225(11) 0.0262(10) 0.0221(11) -0.0015(8) -0.0002(9) -0.0015(9)
C2 0.0219(11) 0.0246(10) 0.0210(11) -0.0014(8) 0.0010(9) -0.0006(8)
C3 0.0227(11) 0.0344(11) 0.0238(12) -0.0015(9) -0.0007(9) -0.0082(9)
C4 0.0220(11) 0.0241(10) 0.0197(11) -0.0010(8) 0.0004(8) 0.0004(8)
C6 0.0189(10) 0.0210(10) 0.0250(11) 0.0019(8) -0.0007(9) 0.0013(8)
C7 0.0245(11) 0.0274(10) 0.0192(11) -0.0001(8) -0.0019(9) 0.0016(9)
C8 0.0217(11) 0.0277(10) 0.0192(11) 0.0019(8) 0.0025(9) -0.0007(8)
C9 0.0194(10) 0.0218(10) 0.0221(10) -0.0005(8) -0.0011(8) 0.0023(8)
C10 0.0238(11) 0.0344(12) 0.0206(11) -0.0037(9) -0.0004(9) -0.0002(9)
C11 0.0239(11) 0.0334(11) 0.0203(11) 0.0006(8) 0.0042(9) -0.0027(9)
C12 0.0268(11) 0.0248(10) 0.0213(11) 0.0016(8) 0.0009(9) -0.0018(9)
C13 0.0273(12) 0.0383(13) 0.0473(15) 0.0152(11) 0.0069(11) 0.0047(10)
C14 0.0388(15) 0.0457(15) 0.0585(18) 0.0270(13) 0.0042(13) 0.0064(12)
C15 0.0383(14) 0.0412(13) 0.0366(14) 0.0138(10) 0.0060(11) -0.0049(11)
C16 0.0276(12) 0.0376(12) 0.0268(12) -0.0001(9) 0.0074(10) -0.0019(10)
C17 0.0253(11) 0.0268(10) 0.0248(11) -0.0003(8) 0.0009(9) 0.0000(9)
C18 0.0178(10) 0.0280(10) 0.0216(11) 0.0006(8) 0.0011(8) -0.0006(8)
C19 0.0284(12) 0.0269(11) 0.0255(12) -0.0009(8) 0.0040(9) -0.0026(9)
C20 0.0268(12) 0.0336(12) 0.0291(12) -0.0071(9) 0.0020(10) -0.0040(9)
C21 0.0228(11) 0.0370(12) 0.0274(12) -0.0025(9) -0.0024(9) 0.0020(9)
C22 0.0218(11) 0.0333(12) 0.0285(12) 0.0043(9) -0.0015(9) 0.0031(9)
C23 0.0192(10) 0.0261(10) 0.0294(12) 0.0004(8) -0.0018(9) -0.0020(8)

_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
N90 C95 1.348(3) . ?
N90 C91 1.351(3) . ?
N90 H90 1.02(3) . ?
N96 C93 1.335(3) . ?
N96 C98 1.451(3) . ?
N96 C97 1.452(3) . ?
C91 C92 1.360(3) . ?
C91 H91 0.9500 . ?
C92 C93 1.414(3) . ?
C92 H92 0.9500 . ?
C93 C94 1.417(3) . ?
C94 C95 1.358(3) . ?
C94 H94 0.9500 . ?
C95 H95 0.9500 . ?
C97 H97B 0.9800 . ?
C97 H97C 0.9800 . ?
C97 H97A 0.9800 . ?
C98 H98B 0.9800 . ?
C98 H98A 0.9800 . ?
C98 H98C 0.9800 . ?
O1A C1 1.272(2) . ?
O1B C1 1.241(2) . ?
N3 C3 1.152(3) . ?
N5 C6 1.405(3) . ?
N5 C18 1.421(3) . ?
N5 C12 1.430(3) . ?
C1 C2 1.512(3) . ?
C2 C4 1.345(3) . ?
C2 C3 1.437(3) . ?
C4 C9 1.459(3) . ?
C4 H4 0.9500 . ?
C6 C11 1.398(3) . ?
C6 C7 1.400(3) . ?
C7 C8 1.372(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.398(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(3) . ?
C10 C11 1.377(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C17 1.381(3) . ?
C12 C13 1.391(3) . ?
C13 C14 1.388(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.371(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.386(3) . ?
C18 C23 1.400(3) . ?
C19 C20 1.385(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.384(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.392(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.380(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

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
C95 N90 C91 119.49(19) . . ?
C95 N90 H90 121.8(14) . . ?
C91 N90 H90 118.8(14) . . ?
C93 N96 C98 122.13(19) . . ?
C93 N96 C97 122.22(18) . . ?
C98 N96 C97 115.61(18) . . ?
N90 C91 C92 122.1(2) . . ?
N90 C91 H91 118.9 . . ?
C92 C91 H91 118.9 . . ?
C91 C92 C93 119.95(19) . . ?
C91 C92 H92 120.0 . . ?
C93 C92 H92 120.0 . . ?
N96 C93 C92 121.16(19) . . ?
N96 C93 C94 122.53(19) . . ?
C92 C93 C94 116.29(19) . . ?
C95 C94 C93 120.6(2) . . ?
C95 C94 H94 119.7 . . ?
C93 C94 H94 119.7 . . ?
N90 C95 C94 121.5(2) . . ?
N90 C95 H95 119.2 . . ?
C94 C95 H95 119.2 . . ?
N96 C97 H97B 109.5 . . ?
N96 C97 H97C 109.5 . . ?
H97B C97 H97C 109.5 . . ?
N96 C97 H97A 109.5 . . ?
H97B C97 H97A 109.5 . . ?
H97C C97 H97A 109.5 . . ?
N96 C98 H98B 109.5 . . ?
N96 C98 H98A 109.5 . . ?
H98B C98 H98A 109.5 . . ?
N96 C98 H98C 109.5 . . ?
H98B C98 H98C 109.5 . . ?
H98A C98 H98C 109.5 . . ?
C6 N5 C18 121.28(16) . . ?
C6 N5 C12 119.58(17) . . ?
C18 N5 C12 118.87(16) . . ?
O1B C1 O1A 126.41(19) . . ?
O1B C1 C2 118.54(18) . . ?
O1A C1 C2 115.05(17) . . ?
C4 C2 C3 123.32(19) . . ?
C4 C2 C1 120.05(19) . . ?
C3 C2 C1 116.63(18) . . ?
N3 C3 C2 179.2(3) . . ?
C2 C4 C9 131.85(19) . . ?
C2 C4 H4 114.1 . . ?
C9 C4 H4 114.1 . . ?
C11 C6 C7 118.07(19) . . ?
C11 C6 N5 120.28(18) . . ?
C7 C6 N5 121.65(19) . . ?
C8 C7 C6 120.23(19) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 122.11(19) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 H8 118.9 . . ?
C10 C9 C8 117.26(19) . . ?
C10 C9 C4 125.30(19) . . ?
C8 C9 C4 117.43(18) . . ?
C11 C10 C9 121.3(2) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C6 121.0(2) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
C17 C12 C13 119.5(2) . . ?
C17 C12 N5 119.99(18) . . ?
C13 C12 N5 120.45(19) . . ?
C14 C13 C12 119.5(2) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 119.4(2) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C17 120.5(2) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C12 C17 C16 120.1(2) . . ?
C12 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C23 119.2(2) . . ?
C19 C18 N5 120.47(18) . . ?
C23 C18 N5 120.33(18) . . ?
C20 C19 C18 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 120.6(2) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 119.0(2) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C23 C22 C21 120.7(2) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C18 120.00(19) . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?

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
C95 N90 C91 C92 -0.6(3) . . . . ?
N90 C91 C92 C93 0.4(3) . . . . ?
C98 N96 C93 C92 -174.70(19) . . . . ?
C97 N96 C93 C92 7.6(3) . . . . ?
C98 N96 C93 C94 6.7(3) . . . . ?
C97 N96 C93 C94 -171.03(19) . . . . ?
C91 C92 C93 N96 -177.87(18) . . . . ?
C91 C92 C93 C94 0.8(3) . . . . ?
N96 C93 C94 C95 176.91(18) . . . . ?
C92 C93 C94 C95 -1.8(3) . . . . ?
C91 N90 C95 C94 -0.4(3) . . . . ?
C93 C94 C95 N90 1.6(3) . . . . ?
O1B C1 C2 C4 3.6(3) . . . . ?
O1A C1 C2 C4 -176.16(18) . . . . ?
O1B C1 C2 C3 -176.03(19) . . . . ?
O1A C1 C2 C3 4.2(3) . . . . ?
C4 C2 C3 N3 -80(22) . . . . ?
C1 C2 C3 N3 99(22) . . . . ?
C3 C2 C4 C9 -2.3(4) . . . . ?
C1 C2 C4 C9 178.10(19) . . . . ?
C18 N5 C6 C11 -153.49(19) . . . . ?
C12 N5 C6 C11 32.6(3) . . . . ?
C18 N5 C6 C7 26.5(3) . . . . ?
C12 N5 C6 C7 -147.41(19) . . . . ?
C11 C6 C7 C8 1.1(3) . . . . ?
N5 C6 C7 C8 -178.87(17) . . . . ?
C6 C7 C8 C9 -1.0(3) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C7 C8 C9 C4 179.39(17) . . . . ?
C2 C4 C9 C10 -15.6(3) . . . . ?
C2 C4 C9 C8 165.1(2) . . . . ?
C8 C9 C10 C11 0.8(3) . . . . ?
C4 C9 C10 C11 -178.54(19) . . . . ?
C9 C10 C11 C6 -0.6(3) . . . . ?
C7 C6 C11 C10 -0.3(3) . . . . ?
N5 C6 C11 C10 179.64(18) . . . . ?
C6 N5 C12 C17 -130.9(2) . . . . ?
C18 N5 C12 C17 55.1(3) . . . . ?
C6 N5 C12 C13 50.3(3) . . . . ?
C18 N5 C12 C13 -123.7(2) . . . . ?
C17 C12 C13 C14 0.4(4) . . . . ?
N5 C12 C13 C14 179.2(2) . . . . ?
C12 C13 C14 C15 -1.0(4) . . . . ?
C13 C14 C15 C16 0.7(4) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
C13 C12 C17 C16 0.5(3) . . . . ?
N5 C12 C17 C16 -178.31(19) . . . . ?
C15 C16 C17 C12 -0.8(3) . . . . ?
C6 N5 C18 C19 -142.0(2) . . . . ?
C12 N5 C18 C19 31.9(3) . . . . ?
C6 N5 C18 C23 39.2(3) . . . . ?
C12 N5 C18 C23 -146.92(19) . . . . ?
C23 C18 C19 C20 -0.6(3) . . . . ?
N5 C18 C19 C20 -179.45(19) . . . . ?
C18 C19 C20 C21 -1.5(3) . . . . ?
C19 C20 C21 C22 1.5(3) . . . . ?
C20 C21 C22 C23 0.6(3) . . . . ?
C21 C22 C23 C18 -2.8(3) . . . . ?
C19 C18 C23 C22 2.8(3) . . . . ?
N5 C18 C23 C22 -178.40(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.056

# Attachment '- Propylamine amine-CCDC-797567.CIF'

data_l
_database_code_depnum_ccdc_archive 'CCDC 797567'
#TrackingRef '- Propylamine amine-CCDC-797567.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            CDPA-Propylamine
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H26.50 N3.50 O2'
_chemical_formula_weight         420.01

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)/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                   20.497(8)
_cell_length_b                   6.687(3)
_cell_length_c                   20.628(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.114(7)
_cell_angle_gamma                90.00
_cell_volume                     2493.8(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             892
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9871
_exptl_absorpt_correction_T_max  0.9943
_exptl_absorpt_process_details   'blessing, Acta Cryst. 1995(A51) 33-38'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(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  'CCD area detector'
_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            24686
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_sigmaI/netI    0.0586
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4375
_reflns_number_gt                3394
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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.
;

_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^)+(0.1132P)^2^+2.6919P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4375
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0834
_refine_ls_wR_factor_ref         0.2298
_refine_ls_wR_factor_gt          0.2160
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.002
_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
N80 N 0.0455(5) 0.918(2) 0.6084(6) 0.133(5) Uani 0.50 1 d P A 1
C81 C 0.0212(5) 0.8195(16) 0.5693(7) 0.071(3) Uani 0.50 1 d P A 1
C82 C -0.0141(8) 0.681(3) 0.5095(9) 0.150(7) Uani 0.50 1 d P A 1
H82A H -0.0462 0.7543 0.4644 0.224 Uiso 0.50 1 calc PR A 1
H82B H -0.0438 0.5859 0.5206 0.224 Uiso 0.50 1 calc PR A 1
H82C H 0.0237 0.6084 0.5025 0.224 Uiso 0.50 1 calc PR A 1
O1A O 0.05855(13) 0.5410(3) 0.38204(13) 0.0495(7) Uani 1 1 d . B 2
O1B O 0.06604(14) 0.8342(4) 0.33592(12) 0.0526(7) Uani 1 1 d . B 2
N3 N 0.18058(19) 1.1508(4) 0.47543(16) 0.0543(9) Uani 1 1 d . B 2
N5 N 0.39231(13) 0.7411(4) 0.81356(12) 0.0321(6) Uani 1 1 d . B 2
C1 C 0.08362(16) 0.7130(5) 0.38703(16) 0.0315(7) Uani 1 1 d . B 2
C2 C 0.14247(15) 0.7790(4) 0.46216(15) 0.0272(7) Uani 1 1 d . B 2
C3 C 0.16298(17) 0.9863(5) 0.47040(15) 0.0338(7) Uani 1 1 d . B 2
C4 C 0.17737(15) 0.6444(4) 0.51530(15) 0.0284(7) Uani 1 1 d . B 2
H4 H 0.1634 0.5091 0.5018 0.034 Uiso 1 1 calc R B 2
C6 C 0.34083(15) 0.7189(4) 0.73903(15) 0.0272(6) Uani 1 1 d . B 2
C7 C 0.34086(17) 0.5517(5) 0.69909(16) 0.0350(7) Uani 1 1 d . B 2
H7 H 0.3781 0.4526 0.7217 0.042 Uiso 1 1 calc R B 2
C8 C 0.28751(17) 0.5280(4) 0.62707(16) 0.0327(7) Uani 1 1 d . B 2
H8 H 0.2869 0.4097 0.6013 0.039 Uiso 1 1 calc R B 2
C9 C 0.23396(15) 0.6765(4) 0.59120(15) 0.0274(7) Uani 1 1 d . B 2
C10 C 0.23522(15) 0.8459(4) 0.63109(15) 0.0272(6) Uani 1 1 d . B 2
H10 H 0.1998 0.9488 0.6078 0.033 Uiso 1 1 calc R B 2
C11 C 0.28722(15) 0.8660(4) 0.70385(15) 0.0283(7) Uani 1 1 d . B 2
H11 H 0.2866 0.9815 0.7304 0.034 Uiso 1 1 calc R B 2
C12 C 0.46267(15) 0.6430(4) 0.84356(15) 0.0278(7) Uani 1 1 d . B 2
C13 C 0.50912(17) 0.6767(5) 0.81344(18) 0.0360(7) Uani 1 1 d . B 2
H13 H 0.4944 0.7644 0.7727 0.043 Uiso 1 1 calc R B 2
C14 C 0.57752(18) 0.5818(5) 0.8428(2) 0.0414(8) Uani 1 1 d . B 2
H14 H 0.6091 0.6035 0.8215 0.050 Uiso 1 1 calc R B 2
C15 C 0.59972(17) 0.4568(5) 0.90246(18) 0.0397(8) Uani 1 1 d . B 2
H15 H 0.6468 0.3937 0.9229 0.048 Uiso 1 1 calc R B 2
C16 C 0.5531(2) 0.4239(5) 0.93220(17) 0.0438(9) Uani 1 1 d . B 2
H16 H 0.5681 0.3374 0.9733 0.053 Uiso 1 1 calc R B 2
C17 C 0.48453(18) 0.5159(5) 0.90274(16) 0.0362(8) Uani 1 1 d . B 2
H17 H 0.4525 0.4912 0.9234 0.043 Uiso 1 1 calc R B 2
C18 C 0.37087(15) 0.8378(4) 0.86168(15) 0.0284(7) Uani 1 1 d . B 2
C19 C 0.30626(19) 0.7850(6) 0.86223(19) 0.0487(9) Uani 1 1 d . B 2
H19 H 0.2764 0.6807 0.8311 0.058 Uiso 1 1 calc R B 2
C20 C 0.2849(2) 0.8823(8) 0.9075(2) 0.0678(14) Uani 1 1 d . B 2
H20 H 0.2398 0.8462 0.9070 0.081 Uiso 1 1 calc R B 2
C21 C 0.3279(3) 1.0319(8) 0.9536(2) 0.0667(14) Uani 1 1 d . B 2
H21 H 0.3126 1.0995 0.9847 0.080 Uiso 1 1 calc R B 2
C22 C 0.3928(2) 1.0822(6) 0.95421(19) 0.0554(11) Uani 1 1 d . B 2
H22 H 0.4232 1.1838 0.9865 0.066 Uiso 1 1 calc R B 2
C23 C 0.41477(19) 0.9863(5) 0.90803(17) 0.0391(8) Uani 1 1 d . B 2
H23 H 0.4597 1.0227 0.9084 0.047 Uiso 1 1 calc R B 2
N90 N 0.05817(17) 0.2328(5) 0.29661(16) 0.0468(8) Uani 1 1 d . C 2
C91 C 0.1216(3) 0.2762(6) 0.2863(2) 0.0633(12) Uani 1 1 d . C 2
H91A H 0.1664 0.2843 0.3347 0.076 Uiso 1 1 calc R C 2
H91B H 0.1147 0.4071 0.2615 0.076 Uiso 1 1 calc R C 2
C92 C 0.1317(3) 0.1152(7) 0.2403(3) 0.0727(13) Uani 1 1 d . C 2
H92A H 0.1433 -0.0129 0.2676 0.087 Uiso 1 1 calc R C 2
H92B H 0.0848 0.0977 0.1943 0.087 Uiso 1 1 calc R C 2
C93 C 0.1913(3) 0.1638(9) 0.2222(4) 0.0947(18) Uani 1 1 d . C 2
H93A H 0.1960 0.0557 0.1927 0.142 Uiso 1 1 calc R C 2
H93B H 0.2380 0.1790 0.2677 0.142 Uiso 1 1 calc R C 2
H93C H 0.1795 0.2890 0.1943 0.142 Uiso 1 1 calc R C 2
H90A H 0.051(2) 0.332(6) 0.328(2) 0.053(11) Uiso 1 1 d . D 2
H90B H 0.063(2) 0.089(7) 0.318(2) 0.056(11) Uiso 1 1 d . E 2
H90C H 0.013(2) 0.243(6) 0.251(3) 0.063(12) Uiso 1 1 d . F 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N80 0.036(4) 0.236(15) 0.112(8) -0.097(9) 0.022(5) -0.003(6)
C81 0.044(5) 0.093(7) 0.098(8) -0.041(6) 0.050(5) -0.021(5)
C82 0.112(11) 0.25(2) 0.143(13) -0.027(14) 0.106(11) -0.045(13)
O1A 0.0443(14) 0.0303(13) 0.0418(14) -0.0114(10) -0.0062(11) -0.0030(10)
O1B 0.0595(16) 0.0501(15) 0.0207(11) -0.0005(11) -0.0038(11) -0.0141(12)
N3 0.070(2) 0.0273(16) 0.0334(16) -0.0006(12) -0.0017(15) -0.0010(14)
N5 0.0260(13) 0.0447(16) 0.0180(12) -0.0025(11) 0.0040(10) 0.0111(11)
C1 0.0273(15) 0.0308(17) 0.0239(15) -0.0079(13) 0.0018(12) 0.0044(13)
C2 0.0272(15) 0.0246(15) 0.0216(14) -0.0073(12) 0.0047(12) 0.0016(12)
C3 0.0368(17) 0.0279(17) 0.0166(14) -0.0017(12) -0.0041(12) 0.0058(13)
C4 0.0282(15) 0.0238(15) 0.0256(15) -0.0055(12) 0.0062(12) -0.0005(12)
C6 0.0235(14) 0.0318(16) 0.0201(14) 0.0015(12) 0.0051(11) 0.0031(12)
C7 0.0347(17) 0.0308(16) 0.0266(15) 0.0021(13) 0.0039(13) 0.0109(13)
C8 0.0380(17) 0.0230(15) 0.0259(15) -0.0020(12) 0.0059(13) 0.0052(13)
C9 0.0263(14) 0.0264(15) 0.0214(14) -0.0006(12) 0.0044(12) 0.0012(12)
C10 0.0242(14) 0.0285(15) 0.0232(14) 0.0001(12) 0.0064(12) 0.0060(12)
C11 0.0275(15) 0.0291(15) 0.0227(14) -0.0050(12) 0.0072(12) 0.0028(12)
C12 0.0248(14) 0.0294(15) 0.0196(14) -0.0035(12) 0.0025(12) 0.0032(12)
C13 0.0338(17) 0.0334(17) 0.0391(17) 0.0109(14) 0.0159(14) 0.0075(14)
C14 0.0350(17) 0.0327(17) 0.058(2) 0.0036(16) 0.0236(16) 0.0060(14)
C15 0.0278(16) 0.0349(18) 0.0393(18) -0.0067(14) 0.0016(14) 0.0105(13)
C16 0.051(2) 0.0420(19) 0.0259(16) 0.0086(14) 0.0083(15) 0.0214(16)
C17 0.0418(18) 0.0385(18) 0.0263(15) 0.0040(13) 0.0144(14) 0.0103(14)
C18 0.0274(15) 0.0340(16) 0.0190(13) 0.0065(12) 0.0069(12) 0.0098(12)
C19 0.0376(19) 0.072(3) 0.0352(18) 0.0015(18) 0.0164(15) -0.0053(18)
C20 0.046(2) 0.125(4) 0.042(2) 0.010(3) 0.0281(19) 0.017(3)
C21 0.071(3) 0.100(4) 0.034(2) 0.013(2) 0.030(2) 0.052(3)
C22 0.072(3) 0.049(2) 0.0307(18) -0.0065(16) 0.0125(18) 0.021(2)
C23 0.0395(18) 0.0426(19) 0.0297(16) -0.0042(14) 0.0118(14) -0.0001(15)
N90 0.0464(18) 0.0416(18) 0.0251(14) -0.0044(13) -0.0058(14) 0.0103(14)
C91 0.078(3) 0.050(2) 0.047(2) 0.0096(19) 0.017(2) 0.013(2)
C92 0.069(3) 0.062(3) 0.081(3) 0.011(2) 0.030(3) 0.004(2)
C93 0.088(4) 0.089(4) 0.117(5) 0.021(4) 0.056(4) 0.007(3)

_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
N80 C81 0.978(12) . ?
C81 C82 1.436(18) . ?
C82 H82A 0.9800 . ?
C82 H82B 0.9800 . ?
C82 H82C 0.9800 . ?
O1A C1 1.244(4) . ?
O1B C1 1.241(4) . ?
N3 C3 1.148(4) . ?
N5 C6 1.404(4) . ?
N5 C18 1.417(4) . ?
N5 C12 1.432(4) . ?
C1 C2 1.513(4) . ?
C2 C4 1.336(4) . ?
C2 C3 1.435(4) . ?
C4 C9 1.460(4) . ?
C4 H4 0.9500 . ?
C6 C7 1.389(4) . ?
C6 C11 1.397(4) . ?
C7 C8 1.377(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.404(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.393(4) . ?
C10 C11 1.378(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C17 1.378(4) . ?
C12 C13 1.379(4) . ?
C13 C14 1.391(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.376(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.375(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.376(5) . ?
C18 C23 1.378(5) . ?
C19 C20 1.368(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.376(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.368(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(5) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
N90 C91 1.442(6) . ?
N90 H90A 0.99(4) . ?
N90 H90B 1.05(4) . ?
N90 H90C 0.95(5) . ?
C91 C92 1.511(6) . ?
C91 H91A 0.9900 . ?
C91 H91B 0.9900 . ?
C92 C93 1.472(7) . ?
C92 H92A 0.9900 . ?
C92 H92B 0.9900 . ?
C93 H93A 0.9800 . ?
C93 H93B 0.9800 . ?
C93 H93C 0.9800 . ?

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
N80 C81 C82 177.2(17) . . ?
C6 N5 C18 119.6(2) . . ?
C6 N5 C12 120.6(2) . . ?
C18 N5 C12 119.2(2) . . ?
O1B C1 O1A 126.2(3) . . ?
O1B C1 C2 116.9(3) . . ?
O1A C1 C2 116.9(3) . . ?
C4 C2 C3 122.7(3) . . ?
C4 C2 C1 120.3(3) . . ?
C3 C2 C1 116.8(2) . . ?
N3 C3 C2 177.5(4) . . ?
C2 C4 C9 129.0(3) . . ?
C2 C4 H4 115.5 . . ?
C9 C4 H4 115.5 . . ?
C7 C6 C11 118.6(3) . . ?
C7 C6 N5 121.6(3) . . ?
C11 C6 N5 119.7(3) . . ?
C8 C7 C6 120.7(3) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.9(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 118.1(3) . . ?
C10 C9 C4 122.5(3) . . ?
C8 C9 C4 119.3(3) . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C6 120.8(3) . . ?
C10 C11 H11 119.6 . . ?
C6 C11 H11 119.6 . . ?
C17 C12 C13 119.6(3) . . ?
C17 C12 N5 120.4(3) . . ?
C13 C12 N5 120.0(3) . . ?
C12 C13 C14 119.9(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 119.3(3) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 120.6(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C12 C17 C16 120.1(3) . . ?
C12 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C23 119.7(3) . . ?
C19 C18 N5 120.4(3) . . ?
C23 C18 N5 119.9(3) . . ?
C20 C19 C18 120.2(4) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 120.8(4) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C22 C21 C20 119.2(4) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C21 C22 C23 120.6(4) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C18 C23 C22 119.5(3) . . ?
C18 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C91 N90 H90A 113(2) . . ?
C91 N90 H90B 110(2) . . ?
H90A N90 H90B 110(3) . . ?
C91 N90 H90C 111(2) . . ?
H90A N90 H90C 103(3) . . ?
H90B N90 H90C 110(3) . . ?
N90 C91 C92 110.4(4) . . ?
N90 C91 H91A 109.6 . . ?
C92 C91 H91A 109.6 . . ?
N90 C91 H91B 109.6 . . ?
C92 C91 H91B 109.6 . . ?
H91A C91 H91B 108.1 . . ?
C93 C92 C91 112.2(4) . . ?
C93 C92 H92A 109.2 . . ?
C91 C92 H92A 109.2 . . ?
C93 C92 H92B 109.2 . . ?
C91 C92 H92B 109.2 . . ?
H92A C92 H92B 107.9 . . ?
C92 C93 H93A 109.5 . . ?
C92 C93 H93B 109.5 . . ?
H93A C93 H93B 109.5 . . ?
C92 C93 H93C 109.5 . . ?
H93A C93 H93C 109.5 . . ?
H93B C93 H93C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1B C1 C2 C4 -163.4(3) . . . . ?
O1A C1 C2 C4 15.2(4) . . . . ?
O1B C1 C2 C3 10.9(4) . . . . ?
O1A C1 C2 C3 -170.6(3) . . . . ?
C4 C2 C3 N3 104(8) . . . . ?
C1 C2 C3 N3 -70(8) . . . . ?
C3 C2 C4 C9 7.7(5) . . . . ?
C1 C2 C4 C9 -178.4(3) . . . . ?
C18 N5 C6 C7 -145.6(3) . . . . ?
C12 N5 C6 C7 25.6(4) . . . . ?
C18 N5 C6 C11 33.4(4) . . . . ?
C12 N5 C6 C11 -155.5(3) . . . . ?
C11 C6 C7 C8 -2.3(5) . . . . ?
N5 C6 C7 C8 176.7(3) . . . . ?
C6 C7 C8 C9 3.1(5) . . . . ?
C7 C8 C9 C10 -1.6(5) . . . . ?
C7 C8 C9 C4 -178.8(3) . . . . ?
C2 C4 C9 C10 33.5(5) . . . . ?
C2 C4 C9 C8 -149.5(3) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C4 C9 C10 C11 176.6(3) . . . . ?
C9 C10 C11 C6 1.2(5) . . . . ?
C7 C6 C11 C10 0.2(4) . . . . ?
N5 C6 C11 C10 -178.8(3) . . . . ?
C6 N5 C12 C17 -123.5(3) . . . . ?
C18 N5 C12 C17 47.6(4) . . . . ?
C6 N5 C12 C13 56.8(4) . . . . ?
C18 N5 C12 C13 -132.0(3) . . . . ?
C17 C12 C13 C14 0.2(5) . . . . ?
N5 C12 C13 C14 179.8(3) . . . . ?
C12 C13 C14 C15 -1.0(5) . . . . ?
C13 C14 C15 C16 1.0(5) . . . . ?
C14 C15 C16 C17 -0.2(5) . . . . ?
C13 C12 C17 C16 0.6(5) . . . . ?
N5 C12 C17 C16 -179.0(3) . . . . ?
C15 C16 C17 C12 -0.6(5) . . . . ?
C6 N5 C18 C19 48.3(4) . . . . ?
C12 N5 C18 C19 -122.9(3) . . . . ?
C6 N5 C18 C23 -131.4(3) . . . . ?
C12 N5 C18 C23 57.4(4) . . . . ?
C23 C18 C19 C20 1.4(5) . . . . ?
N5 C18 C19 C20 -178.3(3) . . . . ?
C18 C19 C20 C21 -0.9(6) . . . . ?
C19 C20 C21 C22 -0.3(6) . . . . ?
C20 C21 C22 C23 1.1(6) . . . . ?
C19 C18 C23 C22 -0.6(5) . . . . ?
N5 C18 C23 C22 179.1(3) . . . . ?
C21 C22 C23 C18 -0.6(5) . . . . ?
N90 C91 C92 C93 174.3(4) . . . . ?

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
N90 H90A O1A 0.99(4) 1.74(4) 2.709(4) 164(3) .
N90 H90B O1B 1.05(4) 1.74(4) 2.769(4) 168(3) 1_545
N90 H90C O1B 0.95(5) 1.87(5) 2.803(4) 165(4) 2_545

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.074