# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Cristina Puigjaner'
_publ_contact_author_email       CRIS@SCT.UB.ES

_publ_section_title              
;
New polymorphic hydrogen bonding donor-acceptor system
with two temperature coincident solid-solid transitions
;
loop_
_publ_author_name
'Cristina Puigjaner'
'Rafael Barbas'
'Dario Braga'
'Marco Polito'
'Anna Portell'
'Rafel Prohens'

# Attachment 'formA.cif'

data_c2
_database_code_depnum_ccdc_archive 'CCDC 676071'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2

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

_cell_length_a                   11.403(2)
_cell_length_b                   4.4101(10)
_cell_length_c                   30.270(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.807(5)
_cell_angle_gamma                90.00
_cell_volume                     1495.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7998
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         0.68
_diffrn_reflns_theta_max         26.73
_reflns_number_total             1803
_reflns_number_gt                1422
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1169P)²+0.0843P] 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       0.028(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1803
_refine_ls_number_parameters     201
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.1776
_refine_ls_wR_factor_gt          0.1533
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_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
C19 C 0.7329(4) 0.2341(11) 0.62372(15) 0.0452(11) Uani 1 1 d . . .
C20 C 0.8215(5) 0.3444(18) 0.60204(18) 0.0621(15) Uani 1 1 d . . .
H30 H 0.9013 0.3043 0.6139 0.074 Uiso 1 1 calc R . .
C21 C 0.7926(6) 0.5111(19) 0.56339(19) 0.0718(18) Uani 1 1 d . . .
H29 H 0.8530 0.5798 0.5491 0.086 Uiso 1 1 calc R . .
C22 C 0.6772(8) 0.5780(19) 0.54559(19) 0.081(2) Uani 1 1 d . . .
H28 H 0.6584 0.6919 0.5193 0.097 Uiso 1 1 calc R . .
C23 C 0.5870(6) 0.473(2) 0.5672(2) 0.079(2) Uani 1 1 d . . .
H27 H 0.5076 0.5197 0.5556 0.094 Uiso 1 1 calc R . .
C24 C 0.6156(5) 0.3011(17) 0.60590(18) 0.0614(15) Uani 1 1 d . . .
H26 H 0.5552 0.2298 0.6200 0.074 Uiso 1 1 calc R . .
C25 C 0.7640(5) 0.0412(13) 0.66595(15) 0.0512(12) Uani 1 1 d . . .
H32A H 0.7191 -0.1466 0.6614 0.061 Uiso 1 1 calc R . .
H32B H 0.8482 -0.0097 0.6708 0.061 Uiso 1 1 calc R . .
C26 C 0.8120(4) 0.3812(11) 0.73035(16) 0.0409(11) Uani 1 1 d . . .
C27 C 0.9347(4) 0.4842(13) 0.73038(16) 0.0478(12) Uani 1 1 d . . .
C28 C 0.9283(4) 0.6753(12) 0.76953(17) 0.0454(11) Uani 1 1 d . . .
C29 C 0.8066(4) 0.5606(11) 0.76864(15) 0.0399(10) Uani 1 1 d . . .
C30 C 0.7414(4) 0.8133(12) 0.83196(14) 0.0479(12) Uani 1 1 d . . .
H37A H 0.6697 0.9317 0.8320 0.057 Uiso 1 1 calc R . .
H37B H 0.8063 0.9530 0.8306 0.057 Uiso 1 1 calc R . .
C31 C 0.7697(4) 0.6311(11) 0.87481(16) 0.0454(11) Uani 1 1 d . . .
C32 C 0.8855(5) 0.5562(18) 0.89420(19) 0.0648(17) Uani 1 1 d . . .
H40 H 0.9475 0.6200 0.8804 0.078 Uiso 1 1 calc R . .
C33 C 0.9122(6) 0.391(2) 0.9332(2) 0.081(2) Uani 1 1 d . . .
H100 H 0.9911 0.3442 0.9456 0.097 Uiso 1 1 calc R . .
C34 C 0.8201(8) 0.294(2) 0.95394(18) 0.083(2) Uani 1 1 d . . .
H101 H 0.8367 0.1827 0.9804 0.100 Uiso 1 1 calc R . .
C35 C 0.7040(6) 0.365(2) 0.93497(19) 0.077(2) Uani 1 1 d . . .
H112 H 0.6420 0.2996 0.9487 0.093 Uiso 1 1 calc R . .
C36 C 0.6793(5) 0.529(2) 0.89643(17) 0.0641(17) Uani 1 1 d . . .
H39 H 0.6003 0.5738 0.8841 0.077 Uiso 1 1 calc R . .
N3 N 0.7387(3) 0.1916(11) 0.70569(13) 0.0477(10) Uani 1 1 d . . .
H3 H 0.6715 0.1543 0.7136 0.057 Uiso 1 1 calc R . .
N4 N 0.7235(3) 0.6161(10) 0.79218(12) 0.0468(10) Uani 1 1 d . . .
H4 H 0.6548 0.5323 0.7839 0.056 Uiso 1 1 calc R . .
O1 O 0.9964(3) 0.8568(10) 0.79325(11) 0.0587(10) Uani 1 1 d . . .
O2 O 1.0096(3) 0.4379(11) 0.70623(12) 0.0610(11) Uani 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
C19 0.039(2) 0.044(3) 0.053(3) -0.010(2) 0.0101(19) -0.005(2)
C20 0.047(3) 0.074(4) 0.070(3) -0.012(4) 0.025(2) -0.014(3)
C21 0.071(4) 0.083(5) 0.066(3) 0.001(4) 0.026(3) -0.022(4)
C22 0.112(6) 0.077(5) 0.053(3) 0.006(3) 0.015(3) -0.015(5)
C23 0.063(4) 0.091(5) 0.078(4) 0.003(4) 0.003(3) 0.010(4)
C24 0.045(3) 0.070(4) 0.069(3) 0.000(3) 0.011(2) -0.001(3)
C25 0.044(3) 0.044(3) 0.064(3) -0.004(3) 0.007(2) -0.003(2)
C26 0.0254(19) 0.038(2) 0.059(3) 0.007(2) 0.0065(18) -0.0091(19)
C27 0.025(2) 0.051(3) 0.066(3) 0.007(2) 0.006(2) -0.009(2)
C28 0.027(2) 0.045(2) 0.064(3) 0.006(2) 0.0058(19) -0.015(2)
C29 0.0235(19) 0.043(2) 0.052(2) 0.006(2) 0.0037(18) -0.0056(18)
C30 0.035(2) 0.046(3) 0.063(3) -0.004(3) 0.012(2) -0.003(2)
C31 0.035(2) 0.048(3) 0.055(3) -0.012(2) 0.011(2) -0.004(2)
C32 0.035(2) 0.084(4) 0.075(4) 0.006(4) 0.010(2) -0.002(3)
C33 0.059(4) 0.109(6) 0.072(3) 0.009(5) 0.002(3) 0.007(5)
C34 0.109(6) 0.089(5) 0.049(3) 0.003(4) 0.011(3) -0.020(5)
C35 0.072(4) 0.102(6) 0.062(3) -0.012(4) 0.023(3) -0.034(4)
C36 0.046(3) 0.090(5) 0.059(3) -0.013(4) 0.016(2) -0.015(3)
N3 0.0299(18) 0.052(2) 0.061(2) 0.001(2) 0.0073(17) -0.014(2)
N4 0.0299(17) 0.050(2) 0.061(2) -0.002(2) 0.0097(17) -0.0093(19)
O1 0.0362(17) 0.063(2) 0.075(2) -0.007(2) 0.0065(16) -0.0241(19)
O2 0.0266(15) 0.082(3) 0.078(2) -0.004(2) 0.0188(16) -0.0121(19)

_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
C19 C24 1.377(7) . ?
C19 C20 1.392(7) . ?
C19 C25 1.521(7) . ?
C20 C21 1.369(9) . ?
C20 H30 0.9300 . ?
C21 C22 1.358(10) . ?
C21 H29 0.9300 . ?
C22 C23 1.398(10) . ?
C22 H28 0.9300 . ?
C23 C24 1.382(9) . ?
C23 H27 0.9300 . ?
C24 H26 0.9300 . ?
C25 N3 1.449(7) . ?
C25 H32A 0.9700 . ?
C25 H32B 0.9700 . ?
C26 N3 1.312(6) . ?
C26 C29 1.414(7) . ?
C26 C27 1.471(5) . ?
C27 O2 1.241(6) . ?
C27 C28 1.467(7) . ?
C28 O1 1.245(6) . ?
C28 C29 1.473(5) . ?
C29 N4 1.311(6) . ?
C30 N4 1.468(6) . ?
C30 C31 1.509(6) . ?
C30 H37A 0.9700 . ?
C30 H37B 0.9700 . ?
C31 C32 1.381(7) . ?
C31 C36 1.396(7) . ?
C32 C33 1.373(9) . ?
C32 H40 0.9300 . ?
C33 C34 1.388(11) . ?
C33 H100 0.9300 . ?
C34 C35 1.376(10) . ?
C34 H101 0.9300 . ?
C35 C36 1.356(10) . ?
C35 H112 0.9300 . ?
C36 H39 0.9300 . ?
N3 H3 0.8600 . ?
N4 H4 0.8600 . ?

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
C24 C19 C20 118.6(5) . . ?
C24 C19 C25 120.4(5) . . ?
C20 C19 C25 121.1(5) . . ?
C21 C20 C19 120.7(6) . . ?
C21 C20 H30 119.7 . . ?
C19 C20 H30 119.7 . . ?
C22 C21 C20 121.1(6) . . ?
C22 C21 H29 119.4 . . ?
C20 C21 H29 119.4 . . ?
C21 C22 C23 119.1(6) . . ?
C21 C22 H28 120.5 . . ?
C23 C22 H28 120.5 . . ?
C24 C23 C22 120.1(6) . . ?
C24 C23 H27 120.0 . . ?
C22 C23 H27 120.0 . . ?
C19 C24 C23 120.5(6) . . ?
C19 C24 H26 119.8 . . ?
C23 C24 H26 119.8 . . ?
N3 C25 C19 113.0(5) . . ?
N3 C25 H32A 109.0 . . ?
C19 C25 H32A 109.0 . . ?
N3 C25 H32B 109.0 . . ?
C19 C25 H32B 109.0 . . ?
H32A C25 H32B 107.8 . . ?
N3 C26 C29 134.6(4) . . ?
N3 C26 C27 134.5(5) . . ?
C29 C26 C27 90.8(4) . . ?
O2 C27 C28 135.6(5) . . ?
O2 C27 C26 135.1(5) . . ?
C28 C27 C26 89.2(4) . . ?
O1 C28 C27 135.7(4) . . ?
O1 C28 C29 135.6(5) . . ?
C27 C28 C29 88.7(4) . . ?
N4 C29 C26 134.1(4) . . ?
N4 C29 C28 134.5(5) . . ?
C26 C29 C28 91.3(4) . . ?
N4 C30 C31 111.3(4) . . ?
N4 C30 H37A 109.4 . . ?
C31 C30 H37A 109.4 . . ?
N4 C30 H37B 109.4 . . ?
C31 C30 H37B 109.4 . . ?
H37A C30 H37B 108.0 . . ?
C32 C31 C36 117.1(5) . . ?
C32 C31 C30 121.8(5) . . ?
C36 C31 C30 121.1(5) . . ?
C33 C32 C31 122.2(6) . . ?
C33 C32 H40 118.9 . . ?
C31 C32 H40 118.9 . . ?
C32 C33 C34 119.2(6) . . ?
C32 C33 H100 120.4 . . ?
C34 C33 H100 120.4 . . ?
C35 C34 C33 119.5(6) . . ?
C35 C34 H101 120.3 . . ?
C33 C34 H101 120.3 . . ?
C36 C35 C34 120.5(6) . . ?
C36 C35 H112 119.7 . . ?
C34 C35 H112 119.7 . . ?
C35 C36 C31 121.5(6) . . ?
C35 C36 H39 119.2 . . ?
C31 C36 H39 119.2 . . ?
C26 N3 C25 124.0(4) . . ?
C26 N3 H3 118.0 . . ?
C25 N3 H3 118.0 . . ?
C29 N4 C30 123.6(4) . . ?
C29 N4 H4 118.2 . . ?
C30 N4 H4 118.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 O2 0.86 2.05 2.845(5) 152.7 3_445
N4 H4 O1 0.86 2.03 2.837(5) 155.1 3_445

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.114

# Attachment 'formC.cif'

data_new
_database_code_depnum_ccdc_archive 'CCDC 686074'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33

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                   30.4956(18)
_cell_length_b                   6.0254(3)
_cell_length_c                   8.1984(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.760(6)
_cell_angle_gamma                90.00
_cell_volume                     1495.97(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10891
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         29.14
_reflns_number_total             1775
_reflns_number_gt                1155
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0900P)²+0.6010P] 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         1775
_refine_ls_number_parameters     104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1277
_refine_ls_R_factor_gt           0.0760
_refine_ls_wR_factor_ref         0.1971
_refine_ls_wR_factor_gt          0.1771
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.37528(8) 0.2731(4) 0.0596(3) 0.0446(6) Uani 1 1 d . . .
C2 C 0.36165(10) 0.0927(5) 0.1456(4) 0.0603(8) Uani 1 1 d . . .
H2 H 0.3801 -0.0298 0.1643 0.072 Uiso 1 1 calc R . .
C3 C 0.32140(11) 0.0930(6) 0.2032(4) 0.0730(9) Uani 1 1 d . . .
H3 H 0.3128 -0.0282 0.2621 0.088 Uiso 1 1 calc R . .
C4 C 0.29384(11) 0.2698(7) 0.1749(4) 0.0809(11) Uani 1 1 d . . .
H4 H 0.2662 0.2684 0.2124 0.097 Uiso 1 1 calc R . .
C5 C 0.30681(11) 0.4483(6) 0.0915(5) 0.0856(11) Uani 1 1 d . . .
H5 H 0.2880 0.5694 0.0725 0.103 Uiso 1 1 calc R . .
C6 C 0.34743(10) 0.4517(5) 0.0349(4) 0.0643(8) Uani 1 1 d . . .
H6 H 0.3561 0.5759 -0.0205 0.077 Uiso 1 1 calc R . .
C7 C 0.41913(9) 0.2695(4) -0.0072(3) 0.0527(7) Uani 1 1 d . . .
H7A H 0.4235 0.1238 -0.0530 0.063 Uiso 1 1 calc R . .
H7B H 0.4184 0.3764 -0.0960 0.063 Uiso 1 1 calc R . .
C8 C 0.48131(8) 0.1649(3) 0.1915(3) 0.0408(6) Uani 1 1 d . . .
C9 C 0.48074(8) -0.0777(4) 0.1869(3) 0.0443(6) Uani 1 1 d . . .
N1 N 0.45642(7) 0.3196(3) 0.1134(3) 0.0477(6) Uani 1 1 d . . .
O1 O 0.45749(6) -0.2192(3) 0.1111(2) 0.0566(6) Uani 1 1 d . . .
H100 H 0.4653(10) 0.458(5) 0.143(4) 0.068(9) 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
C1 0.0526(14) 0.0400(14) 0.0398(13) -0.0055(10) -0.0006(11) -0.0008(11)
C2 0.0627(18) 0.0487(17) 0.0688(18) 0.0068(13) 0.0052(15) -0.0031(13)
C3 0.0632(19) 0.080(2) 0.075(2) 0.0084(17) 0.0058(16) -0.0159(18)
C4 0.0536(18) 0.109(3) 0.082(2) -0.008(2) 0.0139(17) -0.006(2)
C5 0.068(2) 0.082(2) 0.105(3) -0.005(2) 0.003(2) 0.026(2)
C6 0.0723(19) 0.0472(16) 0.0726(19) 0.0037(14) 0.0050(16) 0.0081(15)
C7 0.0677(17) 0.0414(15) 0.0506(15) -0.0005(11) 0.0134(13) 0.0023(13)
C8 0.0496(13) 0.0239(11) 0.0530(14) -0.0005(10) 0.0233(10) 0.0006(10)
C9 0.0575(15) 0.0243(12) 0.0561(15) -0.0017(10) 0.0267(11) -0.0017(10)
N1 0.0527(13) 0.0263(11) 0.0666(14) -0.0026(10) 0.0172(11) -0.0006(10)
O1 0.0742(13) 0.0262(9) 0.0713(13) -0.0069(8) 0.0168(10) -0.0050(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
C1 C6 1.371(4) . ?
C1 C2 1.386(4) . ?
C1 C7 1.504(4) . ?
C2 C3 1.366(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.360(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.358(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.448(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.319(3) . ?
C8 C8 1.401(5) 2_655 ?
C8 C9 1.462(3) . ?
C9 O1 1.230(3) . ?
C9 C9 1.471(6) 2_655 ?
N1 H100 0.90(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
C6 C1 C2 118.2(3) . . ?
C6 C1 C7 121.3(2) . . ?
C2 C1 C7 120.4(2) . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 120.4(3) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
N1 C7 C1 114.1(2) . . ?
N1 C7 H7A 108.7 . . ?
C1 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C1 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
N1 C8 C8 135.05(14) . 2_655 ?
N1 C8 C9 133.6(2) . . ?
C8 C8 C9 91.36(15) 2_655 . ?
O1 C9 C8 135.3(3) . . ?
O1 C9 C9 136.10(14) . 2_655 ?
C8 C9 C9 88.62(15) . 2_655 ?
C8 N1 C7 123.0(2) . . ?
C8 N1 H100 113(2) . . ?
C7 N1 H100 124(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H100 O1 0.90(3) 1.97(3) 2.779(3) 148(3) 1_565

_diffrn_measured_fraction_theta_max 0.880
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.047


