# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Edwin Weber'
_publ_contact_author_email       EDWIN.WEBER@CHEMIE.TU-FREIBERG.DE

_publ_section_title              
;
Competitive interactions in crystalline
9-pyridyl-9-fluorenols: Crossover from O-H...O to O-H...N hydrogen
bonding to construct intra- and intermolecular, helical and linear
contact modes
;
loop_
_publ_author_name
'Edwin Weber'
'Rahmam Hosseinzadeh'
'Z Lasemi'
'Wilhelm Seichter'

data_hoss_24a_0m
_database_code_depnum_ccdc_archive 'CCDC 712757'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 N O'
_chemical_formula_sum            'C18 H13 N O'
_chemical_formula_weight         259.29

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/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                   12.9969(3)
_cell_length_b                   7.6546(2)
_cell_length_c                   13.4691(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.859(2)
_cell_angle_gamma                90.00
_cell_volume                     1320.20(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3367
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      26.55

_exptl_crystal_description       column
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.9368
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_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_%        <1%
_diffrn_reflns_number            14541
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         27.80
_reflns_number_total             3112
_reflns_number_gt                2356
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Kappa APEX 2 (Bruker AXS, 2004)'
_computing_cell_refinement       'SAINT-NT (Sheldrick, 2008)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia)'
_computing_publication_material  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)+(0.0477P)²+0.2827P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3112
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1115
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.40533(7) -0.00751(11) 0.83639(8) 0.0411(3) Uani 1 1 d . . .
H1 H 0.4017 -0.1096 0.8539 0.062 Uiso 1 1 calc R . .
N1 N 0.39889(10) 0.63541(14) 0.88818(9) 0.0444(3) Uani 1 1 d . . .
C1 C 0.27961(10) 0.01611(15) 0.95287(10) 0.0332(3) Uani 1 1 d . . .
C2 C 0.33527(11) -0.00978(18) 1.04814(11) 0.0435(3) Uani 1 1 d . . .
H2 H 0.4052 0.0223 1.0639 0.052 Uiso 1 1 calc R . .
C3 C 0.28451(14) -0.0850(2) 1.12010(12) 0.0530(4) Uani 1 1 d . . .
H3 H 0.3211 -0.1045 1.1848 0.064 Uiso 1 1 calc R . .
C4 C 0.18034(13) -0.1314(2) 1.09709(12) 0.0528(4) Uani 1 1 d . . .
H4 H 0.1477 -0.1814 1.1465 0.063 Uiso 1 1 calc R . .
C5 C 0.12422(11) -0.10459(18) 1.00187(12) 0.0453(3) Uani 1 1 d . . .
H5 H 0.0541 -0.1354 0.9868 0.054 Uiso 1 1 calc R . .
C6 C 0.17440(10) -0.03063(16) 0.92872(10) 0.0354(3) Uani 1 1 d . . .
C7 C 0.13779(10) 0.00557(16) 0.82152(11) 0.0372(3) Uani 1 1 d . . .
C8 C 0.04017(11) -0.01501(19) 0.76171(12) 0.0490(4) Uani 1 1 d . . .
H8 H -0.0156 -0.0601 0.7886 0.059 Uiso 1 1 calc R . .
C9 C 0.02776(13) 0.0331(2) 0.66135(13) 0.0580(4) Uani 1 1 d . . .
H9 H -0.0373 0.0215 0.6207 0.070 Uiso 1 1 calc R . .
C10 C 0.11033(13) 0.0980(2) 0.62073(12) 0.0564(4) Uani 1 1 d . . .
H10 H 0.1003 0.1288 0.5530 0.068 Uiso 1 1 calc R . .
C11 C 0.20801(12) 0.11802(19) 0.67951(11) 0.0465(4) Uani 1 1 d . . .
H11 H 0.2636 0.1619 0.6520 0.056 Uiso 1 1 calc R . .
C12 C 0.22107(10) 0.07134(16) 0.77990(10) 0.0358(3) Uani 1 1 d . . .
C13 C 0.31913(9) 0.08692(15) 0.86048(10) 0.0325(3) Uani 1 1 d . . .
C14 C 0.35086(9) 0.27845(15) 0.87332(9) 0.0324(3) Uani 1 1 d . . .
C15 C 0.28370(12) 0.39872(18) 0.90397(13) 0.0535(4) Uani 1 1 d . . .
H15 H 0.2203 0.3623 0.9201 0.064 Uiso 1 1 calc R . .
C16 C 0.31059(14) 0.57232(19) 0.91059(14) 0.0579(5) Uani 1 1 d . . .
H16 H 0.2641 0.6503 0.9321 0.069 Uiso 1 1 calc R . .
C17 C 0.46422(11) 0.51924(17) 0.86120(12) 0.0442(3) Uani 1 1 d . . .
H17 H 0.5276 0.5593 0.8469 0.053 Uiso 1 1 calc R . .
C18 C 0.44405(10) 0.34141(16) 0.85297(11) 0.0411(3) Uani 1 1 d . . .
H18 H 0.4931 0.2656 0.8339 0.049 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.4168(14) . ?
O1 H1 0.8200 . ?
N1 C17 1.3226(18) . ?
N1 C16 1.3268(19) . ?
C1 C2 1.3753(19) . ?
C1 C6 1.3969(18) . ?
C1 C13 1.5248(18) . ?
C2 C3 1.388(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.3917(18) . ?
C5 H5 0.9300 . ?
C6 C7 1.4671(19) . ?
C7 C8 1.391(2) . ?
C7 C12 1.3953(18) . ?
C8 C9 1.384(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.385(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.5306(18) . ?
C13 C14 1.5248(16) . ?
C14 C18 1.3740(17) . ?
C14 C15 1.3796(18) . ?
C15 C16 1.373(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.3871(18) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O1 H1 109.5 . . ?
C17 N1 C16 116.03(12) . . ?
C2 C1 C6 121.20(13) . . ?
C2 C1 C13 128.01(12) . . ?
C6 C1 C13 110.74(11) . . ?
C1 C2 C3 118.32(14) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 120.97(15) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 120.81(14) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 118.83(14) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 119.87(13) . . ?
C5 C6 C7 131.40(12) . . ?
C1 C6 C7 108.68(11) . . ?
C8 C7 C12 120.11(14) . . ?
C8 C7 C6 131.20(13) . . ?
C12 C7 C6 108.69(11) . . ?
C9 C8 C7 118.56(15) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C10 C9 C8 121.03(15) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 120.85(15) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 118.58(14) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C11 C12 C7 120.87(13) . . ?
C11 C12 C13 128.47(12) . . ?
C7 C12 C13 110.62(12) . . ?
O1 C13 C14 107.90(9) . . ?
O1 C13 C1 113.31(10) . . ?
C14 C13 C1 111.82(10) . . ?
O1 C13 C12 113.14(10) . . ?
C14 C13 C12 109.36(10) . . ?
C1 C13 C12 101.25(10) . . ?
C18 C14 C15 116.75(12) . . ?
C18 C14 C13 123.04(11) . . ?
C15 C14 C13 120.19(11) . . ?
C16 C15 C14 119.88(13) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
N1 C16 C15 123.91(13) . . ?
N1 C16 H16 118.0 . . ?
C15 C16 H16 118.0 . . ?
N1 C17 C18 124.07(13) . . ?
N1 C17 H17 118.0 . . ?
C18 C17 H17 118.0 . . ?
C14 C18 C17 119.29(12) . . ?
C14 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?

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
C6 C1 C2 C3 0.5(2) . . . . ?
C13 C1 C2 C3 -176.56(12) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
C4 C5 C6 C7 176.65(13) . . . . ?
C2 C1 C6 C5 0.09(19) . . . . ?
C13 C1 C6 C5 177.57(11) . . . . ?
C2 C1 C6 C7 -177.66(11) . . . . ?
C13 C1 C6 C7 -0.17(14) . . . . ?
C5 C6 C7 C8 3.7(2) . . . . ?
C1 C6 C7 C8 -178.87(13) . . . . ?
C5 C6 C7 C12 -176.33(13) . . . . ?
C1 C6 C7 C12 1.06(14) . . . . ?
C12 C7 C8 C9 -0.8(2) . . . . ?
C6 C7 C8 C9 179.09(13) . . . . ?
C7 C8 C9 C10 0.8(2) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
C10 C11 C12 C7 -0.1(2) . . . . ?
C10 C11 C12 C13 -177.61(13) . . . . ?
C8 C7 C12 C11 0.46(19) . . . . ?
C6 C7 C12 C11 -179.48(12) . . . . ?
C8 C7 C12 C13 178.41(11) . . . . ?
C6 C7 C12 C13 -1.52(14) . . . . ?
C2 C1 C13 O1 55.13(17) . . . . ?
C6 C1 C13 O1 -122.13(11) . . . . ?
C2 C1 C13 C14 -67.07(16) . . . . ?
C6 C1 C13 C14 115.66(11) . . . . ?
C2 C1 C13 C12 176.59(12) . . . . ?
C6 C1 C13 C12 -0.67(13) . . . . ?
C11 C12 C13 O1 -59.32(17) . . . . ?
C7 C12 C13 O1 122.92(11) . . . . ?
C11 C12 C13 C14 60.97(17) . . . . ?
C7 C12 C13 C14 -116.79(11) . . . . ?
C11 C12 C13 C1 179.10(13) . . . . ?
C7 C12 C13 C1 1.34(12) . . . . ?
O1 C13 C14 C18 6.33(17) . . . . ?
C1 C13 C14 C18 131.58(13) . . . . ?
C12 C13 C14 C18 -117.11(14) . . . . ?
O1 C13 C14 C15 -175.54(13) . . . . ?
C1 C13 C14 C15 -50.29(17) . . . . ?
C12 C13 C14 C15 61.01(16) . . . . ?
C18 C14 C15 C16 1.5(2) . . . . ?
C13 C14 C15 C16 -176.79(15) . . . . ?
C17 N1 C16 C15 -2.2(3) . . . . ?
C14 C15 C16 N1 0.6(3) . . . . ?
C16 N1 C17 C18 1.8(2) . . . . ?
C15 C14 C18 C17 -1.8(2) . . . . ?
C13 C14 C18 C17 176.36(13) . . . . ?
N1 C17 C18 C14 0.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.80
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.033

data_hoss_25_0m
_database_code_depnum_ccdc_archive 'CCDC 712758'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 N O'
_chemical_formula_sum            'C18 H13 N O'
_chemical_formula_weight         259.29

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/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                   12.7369(2)
_cell_length_b                   7.93760(10)
_cell_length_c                   13.0497(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.9350(10)
_cell_angle_gamma                90.00
_cell_volume                     1309.68(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6165
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      30.92

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.9381
_exptl_absorpt_correction_T_max  0.9919
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_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_%        <1%
_diffrn_reflns_number            21936
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         28.95
_reflns_number_total             3461
_reflns_number_gt                2509
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Kappa APEX 2 (Bruker AXS, 2004)'
_computing_cell_refinement       'SAINT-NT (Sheldrick, 2008)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia)'
_computing_publication_material  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)+(0.0756P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3461
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1223
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.40016(6) -0.01993(10) 0.32226(7) 0.0381(2) Uani 1 1 d . . .
H1 H 0.4142 0.0066 0.2647 0.057 Uiso 1 1 calc R . .
N1 N 0.48548(9) 0.48267(12) 0.34626(8) 0.0409(3) Uani 1 1 d . . .
C1 C 0.21818(9) 0.07664(14) 0.27479(9) 0.0324(3) Uani 1 1 d . . .
C2 C 0.20230(10) 0.12871(16) 0.17318(10) 0.0426(3) Uani 1 1 d . . .
H2 H 0.2570 0.1775 0.1423 0.051 Uiso 1 1 calc R . .
C3 C 0.10346(11) 0.10689(19) 0.11824(11) 0.0508(4) Uani 1 1 d . . .
H3 H 0.0918 0.1403 0.0495 0.061 Uiso 1 1 calc R . .
C4 C 0.02179(11) 0.03618(19) 0.16413(12) 0.0518(4) Uani 1 1 d . . .
H4 H -0.0444 0.0239 0.1261 0.062 Uiso 1 1 calc R . .
C5 C 0.03693(10) -0.01658(17) 0.26565(11) 0.0456(3) Uani 1 1 d . . .
H5 H -0.0181 -0.0653 0.2961 0.055 Uiso 1 1 calc R . .
C6 C 0.13578(9) 0.00450(14) 0.32125(10) 0.0346(3) Uani 1 1 d . . .
C7 C 0.17566(9) -0.03724(14) 0.42904(9) 0.0338(3) Uani 1 1 d . . .
C8 C 0.12742(10) -0.11330(16) 0.50671(10) 0.0435(3) Uani 1 1 d . . .
H8 H 0.0568 -0.1456 0.4950 0.052 Uiso 1 1 calc R . .
C9 C 0.18542(11) -0.14057(17) 0.60164(10) 0.0469(3) Uani 1 1 d . . .
H9 H 0.1537 -0.1923 0.6540 0.056 Uiso 1 1 calc R . .
C10 C 0.29020(11) -0.09155(17) 0.61955(10) 0.0449(3) Uani 1 1 d . . .
H10 H 0.3282 -0.1102 0.6840 0.054 Uiso 1 1 calc R . .
C11 C 0.33933(10) -0.01475(15) 0.54247(10) 0.0379(3) Uani 1 1 d . . .
H11 H 0.4098 0.0184 0.5547 0.046 Uiso 1 1 calc R . .
C12 C 0.28174(9) 0.01131(13) 0.44756(9) 0.0310(3) Uani 1 1 d . . .
C13 C 0.31889(8) 0.08639(13) 0.35074(9) 0.0296(2) Uani 1 1 d . . .
C14 C 0.35677(8) 0.26798(13) 0.36661(8) 0.0293(2) Uani 1 1 d . . .
C15 C 0.29771(10) 0.38527(15) 0.41339(10) 0.0414(3) Uani 1 1 d . . .
H15 H 0.2337 0.3541 0.4353 0.050 Uiso 1 1 calc R . .
C16 C 0.33363(12) 0.54750(16) 0.42742(11) 0.0475(3) Uani 1 1 d . . .
H16 H 0.2949 0.6268 0.4596 0.057 Uiso 1 1 calc R . .
C17 C 0.42797(10) 0.59092(15) 0.39309(10) 0.0418(3) Uani 1 1 d . . .
H17 H 0.4524 0.7008 0.4032 0.050 Uiso 1 1 calc R . .
C18 C 0.44955(9) 0.32389(15) 0.33450(9) 0.0353(3) Uani 1 1 d . . .
H18 H 0.4900 0.2469 0.3026 0.042 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C13 1.4195(13) . ?
O1 H1 0.8200 . ?
N1 C17 1.3253(17) . ?
N1 C18 1.3433(15) . ?
C1 C2 1.3803(17) . ?
C1 C6 1.3966(16) . ?
C1 C13 1.5254(16) . ?
C2 C3 1.3823(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.3854(18) . ?
C5 H5 0.9300 . ?
C6 C7 1.4744(17) . ?
C7 C8 1.3856(17) . ?
C7 C12 1.3977(16) . ?
C8 C9 1.3807(18) . ?
C8 H8 0.9300 . ?
C9 C10 1.3826(19) . ?
C9 H9 0.9300 . ?
C10 C11 1.3882(18) . ?
C10 H10 0.9300 . ?
C11 C12 1.3768(17) . ?
C11 H11 0.9300 . ?
C12 C13 1.5230(16) . ?
C13 C14 1.5261(15) . ?
C14 C18 1.3742(15) . ?
C14 C15 1.3843(15) . ?
C15 C16 1.3714(18) . ?
C15 H15 0.9300 . ?
C16 C17 1.3760(19) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O1 H1 109.5 . . ?
C17 N1 C18 117.47(11) . . ?
C2 C1 C6 120.61(11) . . ?
C2 C1 C13 128.55(10) . . ?
C6 C1 C13 110.84(10) . . ?
C1 C2 C3 118.64(12) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 120.84(13) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 120.95(12) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 118.60(13) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C5 C6 C1 120.35(12) . . ?
C5 C6 C7 131.24(12) . . ?
C1 C6 C7 108.42(10) . . ?
C8 C7 C12 119.90(11) . . ?
C8 C7 C6 131.58(11) . . ?
C12 C7 C6 108.51(10) . . ?
C9 C8 C7 119.22(12) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 120.57(12) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C11 120.76(12) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 118.69(11) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C11 C12 C7 120.86(11) . . ?
C11 C12 C13 128.31(10) . . ?
C7 C12 C13 110.80(10) . . ?
O1 C13 C12 107.10(8) . . ?
O1 C13 C1 112.48(9) . . ?
C12 C13 C1 101.42(8) . . ?
O1 C13 C14 111.62(8) . . ?
C12 C13 C14 112.45(9) . . ?
C1 C13 C14 111.30(9) . . ?
C18 C14 C15 116.76(10) . . ?
C18 C14 C13 122.21(10) . . ?
C15 C14 C13 121.02(9) . . ?
C16 C15 C14 120.00(11) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 118.82(12) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
N1 C17 C16 122.74(11) . . ?
N1 C17 H17 118.6 . . ?
C16 C17 H17 118.6 . . ?
N1 C18 C14 124.19(11) . . ?
N1 C18 H18 117.9 . . ?
C14 C18 H18 117.9 . . ?

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
C6 C1 C2 C3 -0.45(18) . . . . ?
C13 C1 C2 C3 179.82(11) . . . . ?
C1 C2 C3 C4 0.7(2) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C4 C5 C6 C1 -0.44(19) . . . . ?
C4 C5 C6 C7 179.58(12) . . . . ?
C2 C1 C6 C5 0.33(17) . . . . ?
C13 C1 C6 C5 -179.89(10) . . . . ?
C2 C1 C6 C7 -179.68(11) . . . . ?
C13 C1 C6 C7 0.09(13) . . . . ?
C5 C6 C7 C8 1.6(2) . . . . ?
C1 C6 C7 C8 -178.36(12) . . . . ?
C5 C6 C7 C12 -179.47(12) . . . . ?
C1 C6 C7 C12 0.55(13) . . . . ?
C12 C7 C8 C9 -0.21(18) . . . . ?
C6 C7 C8 C9 178.59(12) . . . . ?
C7 C8 C9 C10 0.5(2) . . . . ?
C8 C9 C10 C11 -0.3(2) . . . . ?
C9 C10 C11 C12 -0.19(19) . . . . ?
C10 C11 C12 C7 0.47(18) . . . . ?
C10 C11 C12 C13 -177.57(11) . . . . ?
C8 C7 C12 C11 -0.28(18) . . . . ?
C6 C7 C12 C11 -179.33(10) . . . . ?
C8 C7 C12 C13 178.08(10) . . . . ?
C6 C7 C12 C13 -0.97(13) . . . . ?
C11 C12 C13 O1 61.12(14) . . . . ?
C7 C12 C13 O1 -117.08(10) . . . . ?
C11 C12 C13 C1 179.17(11) . . . . ?
C7 C12 C13 C1 0.97(11) . . . . ?
C11 C12 C13 C14 -61.85(15) . . . . ?
C7 C12 C13 C14 119.95(10) . . . . ?
C2 C1 C13 O1 -66.78(15) . . . . ?
C6 C1 C13 O1 113.47(10) . . . . ?
C2 C1 C13 C12 179.13(11) . . . . ?
C6 C1 C13 C12 -0.63(11) . . . . ?
C2 C1 C13 C14 59.33(15) . . . . ?
C6 C1 C13 C14 -120.42(10) . . . . ?
O1 C13 C14 C18 13.32(15) . . . . ?
C12 C13 C14 C18 133.72(11) . . . . ?
C1 C13 C14 C18 -113.26(12) . . . . ?
O1 C13 C14 C15 -167.49(10) . . . . ?
C12 C13 C14 C15 -47.09(14) . . . . ?
C1 C13 C14 C15 65.93(14) . . . . ?
C18 C14 C15 C16 -1.18(18) . . . . ?
C13 C14 C15 C16 179.59(12) . . . . ?
C14 C15 C16 C17 0.8(2) . . . . ?
C18 N1 C17 C16 -1.31(19) . . . . ?
C15 C16 C17 N1 0.5(2) . . . . ?
C17 N1 C18 C14 0.91(18) . . . . ?
C15 C14 C18 N1 0.32(18) . . . . ?
C13 C14 C18 N1 179.53(11) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.95
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.056


