# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  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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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_ae2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          451(2)
_chemical_formula_moiety         'C26 H32 N4, 2(H2 O)'
_chemical_formula_sum            'C26 H36 N4 O2'
_chemical_formula_weight         436.59

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   '
_symmetry_space_group_name_Hall  -P1

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

_cell_length_a                   10.054(2)
_cell_length_b                   10.073(2)
_cell_length_c                   12.755(3)
_cell_angle_alpha                107.386(3)
_cell_angle_beta                 97.437(3)
_cell_angle_gamma                96.535(2)
_cell_volume                     1206.4(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7492
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   'Bruker AXS SADABS program'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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            12064
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         26.40
_reflns_number_total             4859
_reflns_number_gt                4297
_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 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)+(0.0844P)²+0.3542P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4859
_refine_ls_number_parameters     323
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1517
_refine_ls_wR_factor_gt          0.1479
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.114
_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
N1 N 0.36794(13) 0.00103(15) 0.78512(10) 0.0184(3) Uani 1 1 d . . .
N2 N 0.05296(13) 0.14503(14) 0.77365(11) 0.0191(3) Uani 1 1 d . . .
N4 N 0.57487(12) 0.24965(14) 0.72558(11) 0.0188(3) Uani 1 1 d . . .
N3 N 0.24375(13) 0.35298(14) 0.66470(11) 0.0196(3) Uani 1 1 d . . .
C21 C 0.58360(14) 0.24641(18) 0.83355(12) 0.0203(3) Uani 1 1 d . . .
C10 C 0.08886(15) 0.28702(17) 0.82918(12) 0.0190(3) Uani 1 1 d . . .
C6 C 0.06788(16) -0.08795(18) 0.80251(14) 0.0239(4) Uani 1 1 d . . .
H9 H -0.0312 -0.1215 0.7800 0.029 Uiso 1 1 calc R . .
H10 H 0.1003 -0.1221 0.8649 0.029 Uiso 1 1 calc R . .
C22 C 0.61076(15) 0.11636(17) 0.86281(12) 0.0208(3) Uani 1 1 d . . .
C1 C 0.50396(15) -0.00896(17) 0.79579(12) 0.0191(3) Uani 1 1 d . . .
C18 C 0.55480(15) 0.38043(17) 0.72157(13) 0.0207(3) Uani 1 1 d . . .
C12 C 0.11129(15) 0.37281(17) 0.66783(12) 0.0195(3) Uani 1 1 d . . .
C11 C 0.05327(15) 0.39540(17) 0.77457(12) 0.0199(3) Uani 1 1 d . . .
C3 C 0.37877(16) -0.22223(18) 0.70229(13) 0.0240(3) Uani 1 1 d . . .
H6 H 0.3548 -0.3201 0.6627 0.029 Uiso 1 1 calc R . .
C19 C 0.54897(16) 0.46188(19) 0.82760(13) 0.0242(4) Uani 1 1 d . . .
H25 H 0.5353 0.5574 0.8500 0.029 Uiso 1 1 calc R . .
C16 C 0.41053(15) 0.31797(18) 0.53067(12) 0.0224(3) Uani 1 1 d . . .
H21 H 0.4138 0.3305 0.4569 0.027 Uiso 1 1 calc R . .
H22 H 0.4169 0.2181 0.5225 0.027 Uiso 1 1 calc R . .
C20 C 0.56715(16) 0.37704(19) 0.89820(13) 0.0245(4) Uani 1 1 d . . .
H26 H 0.5678 0.4059 0.9763 0.029 Uiso 1 1 calc R . .
C17 C 0.53553(16) 0.41107(18) 0.61338(13) 0.0232(4) Uani 1 1 d . . .
H24 H 0.6177 0.3962 0.5790 0.028 Uiso 1 1 calc R . .
H23 H 0.5254 0.5113 0.6282 0.028 Uiso 1 1 calc R . .
C15 C 0.27623(16) 0.34663(17) 0.56209(12) 0.0210(3) Uani 1 1 d . . .
C4 C 0.29054(15) -0.12898(17) 0.72904(12) 0.0196(3) Uani 1 1 d . . .
C7 C 0.09235(15) 0.06875(18) 0.84255(13) 0.0209(3) Uani 1 1 d . . .
C5 C 0.13877(15) -0.15268(17) 0.70329(13) 0.0216(3) Uani 1 1 d . . .
H7 H 0.1059 -0.2555 0.6743 0.026 Uiso 1 1 calc R . .
H8 H 0.1108 -0.1131 0.6431 0.026 Uiso 1 1 calc R . .
C14 C 0.16152(16) 0.36114(18) 0.49829(13) 0.0236(4) Uani 1 1 d . . .
H20 H 0.1529 0.3604 0.4231 0.028 Uiso 1 1 calc R . .
C13 C 0.05748(16) 0.37753(18) 0.56495(13) 0.0234(4) Uani 1 1 d . . .
H19 H -0.0329 0.3896 0.5422 0.028 Uiso 1 1 calc R . .
C9 C 0.15413(16) 0.30183(18) 0.93427(13) 0.0237(4) Uani 1 1 d . . .
H12 H 0.1914 0.3882 0.9912 0.028 Uiso 1 1 calc R . .
C8 C 0.15584(16) 0.16476(19) 0.94252(13) 0.0253(4) Uani 1 1 d . . .
H11 H 0.1943 0.1431 1.0063 0.030 Uiso 1 1 calc R . .
C2 C 0.51302(16) -0.14656(19) 0.74428(13) 0.0243(4) Uani 1 1 d . . .
H5 H 0.5947 -0.1851 0.7376 0.029 Uiso 1 1 calc R . .
C23 C 0.75165(16) 0.0841(2) 0.84005(15) 0.0283(4) Uani 1 1 d . . .
H31 H 0.7705 0.0025 0.8629 0.042 Uiso 1 1 calc R . .
H30 H 0.8206 0.1660 0.8825 0.042 Uiso 1 1 calc R . .
H32 H 0.7539 0.0632 0.7602 0.042 Uiso 1 1 calc R . .
C24 C 0.60901(17) 0.14430(19) 0.98810(13) 0.0274(4) Uani 1 1 d . . .
H27 H 0.5197 0.1656 1.0044 0.041 Uiso 1 1 calc R . .
H28 H 0.6792 0.2246 1.0316 0.041 Uiso 1 1 calc R . .
H29 H 0.6270 0.0605 1.0081 0.041 Uiso 1 1 calc R . .
C25 C -0.10164(16) 0.38474(19) 0.74750(14) 0.0262(4) Uani 1 1 d . . .
H13 H -0.1405 0.2920 0.6937 0.039 Uiso 1 1 calc R . .
H15 H -0.1234 0.4584 0.7155 0.039 Uiso 1 1 calc R . .
H14 H -0.1399 0.3970 0.8160 0.039 Uiso 1 1 calc R . .
C26 C 0.11354(18) 0.54305(18) 0.85458(14) 0.0278(4) Uani 1 1 d . . .
H16 H 0.0751 0.5593 0.9233 0.042 Uiso 1 1 calc R . .
H17 H 0.0917 0.6137 0.8192 0.042 Uiso 1 1 calc R . .
H18 H 0.2125 0.5506 0.8724 0.042 Uiso 1 1 calc R . .
H3 H 0.304(2) 0.351(2) 0.7215(17) 0.033 Uiso 1 1 d . . .
H2 H 0.002(2) 0.105(2) 0.7057(18) 0.033 Uiso 1 1 d . . .
H4 H 0.591(2) 0.180(2) 0.6662(17) 0.033 Uiso 1 1 d . . .
H1 H 0.337(2) 0.079(2) 0.8154(17) 0.033 Uiso 1 1 d . . .
O1 O 0.36735(12) 0.93076(13) 0.49894(9) 0.0278(3) Uani 1 1 d D . .
H33 H 0.3698(19) 0.889(2) 0.5578(14) 0.042 Uiso 1 1 d D . .
H34A H 0.4611(15) 0.981(4) 0.510(3) 0.042 Uiso 0.50 1 d PD . .
H34B H 0.2700(11) 0.933(4) 0.478(3) 0.042 Uiso 0.50 1 d PD . .
O2 O 0.11726(11) 0.02275(13) 0.45482(9) 0.0267(3) Uani 1 1 d D . .
H35 H 0.1355(19) 0.1241(10) 0.4693(17) 0.040 Uiso 1 1 d D . .
H36A H 0.0257(17) 0.008(3) 0.475(3) 0.040 Uiso 0.50 1 d PD . .
H36B H 0.2101(14) -0.001(3) 0.466(3) 0.040 Uiso 0.50 1 d PD . .

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
N1 0.0179(6) 0.0199(7) 0.0174(6) 0.0065(5) 0.0024(5) 0.0022(5)
N2 0.0165(6) 0.0216(7) 0.0194(6) 0.0082(5) 0.0018(5) 0.0011(5)
N4 0.0181(6) 0.0220(7) 0.0177(6) 0.0085(5) 0.0042(5) 0.0023(5)
N3 0.0175(6) 0.0259(8) 0.0177(6) 0.0107(5) 0.0025(5) 0.0031(5)
C21 0.0137(7) 0.0300(9) 0.0180(7) 0.0104(6) 0.0022(5) -0.0009(6)
C10 0.0152(7) 0.0214(8) 0.0216(7) 0.0078(6) 0.0061(6) 0.0021(6)
C6 0.0195(7) 0.0267(9) 0.0290(8) 0.0142(7) 0.0052(6) 0.0019(6)
C22 0.0174(7) 0.0272(9) 0.0189(7) 0.0111(6) 0.0020(6) -0.0005(6)
C1 0.0182(7) 0.0264(9) 0.0157(7) 0.0111(6) 0.0042(5) 0.0030(6)
C18 0.0147(7) 0.0249(9) 0.0243(8) 0.0114(6) 0.0033(6) 0.0010(6)
C12 0.0163(7) 0.0208(8) 0.0221(7) 0.0089(6) 0.0024(6) 0.0004(6)
C11 0.0177(7) 0.0217(8) 0.0216(7) 0.0085(6) 0.0048(6) 0.0023(6)
C3 0.0256(8) 0.0222(9) 0.0219(7) 0.0044(6) 0.0018(6) 0.0046(7)
C19 0.0215(8) 0.0244(9) 0.0260(8) 0.0067(7) 0.0034(6) 0.0047(6)
C16 0.0236(8) 0.0291(9) 0.0196(7) 0.0133(7) 0.0065(6) 0.0059(7)
C20 0.0226(8) 0.0320(10) 0.0178(7) 0.0064(7) 0.0040(6) 0.0037(7)
C17 0.0201(7) 0.0282(9) 0.0278(8) 0.0167(7) 0.0081(6) 0.0044(6)
C15 0.0233(8) 0.0232(9) 0.0196(7) 0.0116(6) 0.0044(6) 0.0026(6)
C4 0.0214(8) 0.0223(8) 0.0155(7) 0.0079(6) 0.0022(6) 0.0013(6)
C7 0.0168(7) 0.0275(9) 0.0229(7) 0.0127(7) 0.0070(6) 0.0047(6)
C5 0.0201(8) 0.0217(8) 0.0225(7) 0.0084(6) 0.0001(6) 0.0014(6)
C14 0.0246(8) 0.0288(9) 0.0193(7) 0.0119(7) 0.0016(6) 0.0033(7)
C13 0.0198(8) 0.0279(9) 0.0243(8) 0.0124(7) 0.0011(6) 0.0034(6)
C9 0.0235(8) 0.0270(9) 0.0197(7) 0.0067(6) 0.0034(6) 0.0026(7)
C8 0.0258(8) 0.0333(10) 0.0204(7) 0.0130(7) 0.0041(6) 0.0069(7)
C2 0.0203(8) 0.0307(9) 0.0231(8) 0.0083(7) 0.0055(6) 0.0077(7)
C23 0.0192(8) 0.0353(10) 0.0369(9) 0.0223(8) 0.0040(7) 0.0028(7)
C24 0.0297(9) 0.0315(10) 0.0180(7) 0.0108(7) -0.0017(6) -0.0086(7)
C25 0.0205(8) 0.0318(10) 0.0313(8) 0.0159(7) 0.0072(6) 0.0063(7)
C26 0.0331(9) 0.0240(9) 0.0264(8) 0.0087(7) 0.0067(7) 0.0012(7)
O1 0.0265(6) 0.0349(7) 0.0252(6) 0.0135(5) 0.0052(5) 0.0062(5)
O2 0.0231(6) 0.0276(7) 0.0285(6) 0.0096(5) 0.0019(5) 0.0018(5)

_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 C1 1.375(2) . ?
N1 C4 1.377(2) . ?
N2 C10 1.374(2) . ?
N2 C7 1.3792(19) . ?
N4 C18 1.370(2) . ?
N4 C21 1.3790(19) . ?
N3 C12 1.373(2) . ?
N3 C15 1.3744(19) . ?
C21 C20 1.369(2) . ?
C21 C22 1.509(2) . ?
C10 C9 1.371(2) . ?
C10 C11 1.511(2) . ?
C6 C7 1.487(2) . ?
C6 C5 1.543(2) . ?
C22 C1 1.512(2) . ?
C22 C23 1.533(2) . ?
C22 C24 1.541(2) . ?
C1 C2 1.364(2) . ?
C18 C19 1.369(2) . ?
C18 C17 1.495(2) . ?
C12 C13 1.370(2) . ?
C12 C11 1.515(2) . ?
C11 C26 1.532(2) . ?
C11 C25 1.535(2) . ?
C3 C4 1.365(2) . ?
C3 C2 1.423(2) . ?
C19 C20 1.424(2) . ?
C16 C15 1.492(2) . ?
C16 C17 1.539(2) . ?
C15 C14 1.371(2) . ?
C4 C5 1.495(2) . ?
C7 C8 1.371(2) . ?
C14 C13 1.425(2) . ?
C9 C8 1.418(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
C1 N1 C4 110.49(14) . . ?
C10 N2 C7 110.27(13) . . ?
C18 N4 C21 110.16(14) . . ?
C12 N3 C15 110.65(12) . . ?
C20 C21 N4 106.97(14) . . ?
C20 C21 C22 131.59(13) . . ?
N4 C21 C22 121.42(14) . . ?
C9 C10 N2 107.28(14) . . ?
C9 C10 C11 131.24(15) . . ?
N2 C10 C11 121.47(13) . . ?
C7 C6 C5 113.65(12) . . ?
C21 C22 C1 110.76(12) . . ?
C21 C22 C23 109.96(12) . . ?
C1 C22 C23 109.53(14) . . ?
C21 C22 C24 108.82(14) . . ?
C1 C22 C24 109.45(12) . . ?
C23 C22 C24 108.27(13) . . ?
C2 C1 N1 106.82(14) . . ?
C2 C1 C22 131.77(14) . . ?
N1 C1 C22 121.23(14) . . ?
C19 C18 N4 107.57(13) . . ?
C19 C18 C17 131.06(16) . . ?
N4 C18 C17 121.26(14) . . ?
C13 C12 N3 107.05(13) . . ?
C13 C12 C11 131.55(14) . . ?
N3 C12 C11 121.21(13) . . ?
C10 C11 C12 110.33(13) . . ?
C10 C11 C26 109.15(13) . . ?
C12 C11 C26 108.93(12) . . ?
C10 C11 C25 110.26(12) . . ?
C12 C11 C25 109.14(12) . . ?
C26 C11 C25 109.00(14) . . ?
C4 C3 C2 107.76(15) . . ?
C18 C19 C20 107.39(15) . . ?
C15 C16 C17 115.38(14) . . ?
C21 C20 C19 107.89(14) . . ?
C18 C17 C16 112.83(12) . . ?
C14 C15 N3 106.84(14) . . ?
C14 C15 C16 129.59(14) . . ?
N3 C15 C16 123.42(13) . . ?
C3 C4 N1 106.90(14) . . ?
C3 C4 C5 129.69(15) . . ?
N1 C4 C5 123.39(14) . . ?
C8 C7 N2 106.70(15) . . ?
C8 C7 C6 131.89(14) . . ?
N2 C7 C6 121.38(14) . . ?
C4 C5 C6 115.25(13) . . ?
C15 C14 C13 107.80(13) . . ?
C12 C13 C14 107.65(14) . . ?
C10 C9 C8 107.53(14) . . ?
C7 C8 C9 108.21(14) . . ?
C1 C2 C3 108.02(14) . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        26.40
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.064
_database_code_depnum_ccdc_archive 'CCDC 1007110'
#######################################################################
#
#                 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_monp

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          381(2)
_chemical_formula_moiety         'C10 H12 N2'
_chemical_formula_sum            'C10 H12 N2'
_chemical_formula_weight         160.22

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   5.2963(10)
_cell_length_b                   7.4802(14)
_cell_length_c                   11.401(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.512(3)
_cell_angle_gamma                90.00
_cell_volume                     445.48(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1855
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             172
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'Bruker AXS SADABS program'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            4171
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         26.16
_reflns_number_total             889
_reflns_number_gt                777
_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 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)+(0.2000P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         889
_refine_ls_number_parameters     67
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1278
_refine_ls_R_factor_gt           0.1198
_refine_ls_wR_factor_ref         0.3593
_refine_ls_wR_factor_gt          0.3460
_refine_ls_goodness_of_fit_ref   1.581
_refine_ls_restrained_S_all      1.581
_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
N1 N 0.9266(6) 1.0610(4) 0.7549(3) 0.0602(11) Uani 1 1 d . . .
C3 C 0.6259(6) 0.8810(4) 0.7855(3) 0.0604(11) Uani 1 1 d . . .
C4 C 0.8094(7) 0.9895(4) 0.8412(3) 0.0568(11) Uani 1 1 d . . .
C2 C 0.6226(7) 0.8898(5) 0.6654(3) 0.0652(12) Uani 1 1 d . . .
C5 C 0.8696(8) 1.0337(6) 0.9715(4) 0.0744(14) Uani 1 1 d . . .
H5A H 0.7402 0.9810 1.0118 0.089 Uiso 1 1 calc R . .
H5B H 0.8632 1.1623 0.9814 0.089 Uiso 1 1 calc R . .
C1 C 0.8145(8) 1.0023(5) 0.6479(3) 0.0657(12) Uani 1 1 d . . .
H1 H 1.041(10) 1.124(7) 0.763(4) 0.079 Uiso 1 1 d . . .
H4 H 0.493(8) 0.822(6) 0.835(3) 0.079 Uiso 1 1 d . . .
H2 H 0.866(10) 1.042(6) 0.599(5) 0.079 Uiso 1 1 d . . .
H3 H 0.532(8) 0.818(6) 0.608(4) 0.079 Uiso 1 1 d . . .

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
N1 0.0556(17) 0.0544(18) 0.066(2) 0.0057(12) -0.0023(13) -0.0123(12)
C3 0.052(2) 0.055(2) 0.072(2) -0.0013(15) 0.0036(15) -0.0033(13)
C4 0.065(2) 0.0492(18) 0.0504(19) 0.0043(12) -0.0065(14) 0.0031(14)
C2 0.063(2) 0.054(2) 0.069(2) -0.0131(15) -0.0176(15) 0.0075(15)
C5 0.067(2) 0.088(3) 0.066(2) -0.0092(19) 0.0055(17) 0.0204(19)
C1 0.082(3) 0.064(2) 0.052(2) 0.0116(15) 0.0133(17) 0.0202(18)

_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 C1 1.340(5) . ?
N1 C4 1.357(5) . ?
C3 C4 1.342(5) . ?
C3 C2 1.369(5) . ?
C4 C5 1.503(5) . ?
C2 C1 1.360(6) . ?
C5 C5 1.512(8) 3_777 ?

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
C1 N1 C4 110.1(3) . . ?
C4 C3 C2 109.5(3) . . ?
C3 C4 N1 106.1(3) . . ?
C3 C4 C5 128.3(4) . . ?
N1 C4 C5 125.6(3) . . ?
C1 C2 C3 106.9(3) . . ?
C4 C5 C5 112.4(4) . 3_777 ?
N1 C1 C2 107.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.16
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.768
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.099
_database_code_depnum_ccdc_archive 'CCDC 1007111'
