 
data_2007src1055
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Dr John Spencer
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C14 H15 N O'
_chemical_formula_weight          213.27
 
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'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    5.37320(10)
_cell_length_b                    13.4962(4)
_cell_length_c                    15.8088(5)
_cell_angle_alpha                 95.3890(10)
_cell_angle_beta                  98.498(2)
_cell_angle_gamma                 101.201(2)
_cell_volume                      1103.32(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     12338
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        Needle
_exptl_crystal_colour             'Pale Brown'
_exptl_crystal_size_max           0.85
_exptl_crystal_size_mid           0.08
_exptl_crystal_size_min           0.06
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.284
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              456
_exptl_absorpt_coefficient_mu     0.081
_exptl_absorpt_correction_type    Multi-scan
_exptl_absorpt_correction_T_min   0.9346
_exptl_absorpt_correction_T_max   0.9952
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'

 
_exptl_special_details
;
 SADABS was used to perform the Absorption correction
Parameter refinement on 15813 reflections reduced R(int) from 0.1450 to 0.05861
Ratio of minimum to maximum apparent transmission: 0.870535
The given Tmin and Tmax were generated using the SHELX SIZE command.

The crystals were long needles which shattered when cut. Thus is was necessary
to mount a much longer crystal than would be ideal.
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_measurement_device_type   
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             18503
_diffrn_reflns_av_R_equivalents   0.0589
_diffrn_reflns_av_sigmaI/netI     0.0577
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -17
_diffrn_reflns_limit_k_max        17
_diffrn_reflns_limit_l_min        -20
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          3.10
_diffrn_reflns_theta_max          27.48
_reflns_number_total              4997
_reflns_number_gt                 3778
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' 
_computing_structure_solution    
;
Sir2004 (Burla, M.C., Caliandro, R., Camalli, M., Carrozzini, B., 
Cascarano, G., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R., 
2004)
;
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     
;
PLATON/PLUTON (Spek, A. L., 1998) & 
Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., 
Shields, G. P., Taylor, R., Towler, M. and van de Streek, J., 2006 
;
_computing_publication_material   'WinGX (Farrugia, 1999)'

 
_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)+(0.0082P)²+1.5131P] 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          4997
_refine_ls_number_parameters      289
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0940
_refine_ls_R_factor_gt            0.0660
_refine_ls_wR_factor_ref          0.1360
_refine_ls_wR_factor_gt           0.1210
_refine_ls_goodness_of_fit_ref    1.066
_refine_ls_restrained_S_all       1.066
_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 0.8711(4) 0.67744(17) 0.93277(14) 0.0219(5) Uani 1 1 d . . .
C2 C 0.8665(5) 0.77804(18) 0.95546(15) 0.0265(5) Uani 1 1 d . . .
H2 H 0.7470 0.7966 0.9895 0.032 Uiso 1 1 calc R . .
C3 C 1.0434(5) 0.85178(18) 0.92673(15) 0.0273(5) Uani 1 1 d . . .
H3 H 1.0441 0.9218 0.9408 0.033 Uiso 1 1 calc R . .
C4 C 1.2174(5) 0.82392(18) 0.87799(15) 0.0274(5) Uani 1 1 d . . .
H4 H 1.3377 0.8751 0.8593 0.033 Uiso 1 1 calc R . .
C5 C 1.2189(4) 0.72166(18) 0.85580(15) 0.0256(5) Uani 1 1 d . . .
H5 H 1.3419 0.7036 0.8231 0.031 Uiso 1 1 calc R . .
C6 C 1.0410(4) 0.64590(17) 0.88130(14) 0.0215(5) Uani 1 1 d . . .
C7 C 0.9830(4) 0.53302(17) 0.87054(13) 0.0197(4) Uani 1 1 d . . .
C8 C 0.7733(4) 0.50402(18) 0.92281(13) 0.0215(5) Uani 1 1 d . . .
C9 C 1.0746(4) 0.46493(17) 0.82191(14) 0.0218(5) Uani 1 1 d . . .
C10 C 1.2587(5) 0.49496(19) 0.76111(16) 0.0296(5) Uani 1 1 d . . .
H10A H 1.4183 0.4699 0.7776 0.035 Uiso 1 1 calc R . .
H10B H 1.3053 0.5701 0.7650 0.035 Uiso 1 1 calc R . .
C11 C 1.1348(5) 0.44981(18) 0.66825(15) 0.0264(5) Uani 1 1 d . . .
H11A H 0.9827 0.4790 0.6504 0.032 Uiso 1 1 calc R . .
H11B H 1.2594 0.4682 0.6291 0.032 Uiso 1 1 calc R . .
C12 C 1.0526(4) 0.33451(17) 0.66081(15) 0.0242(5) Uani 1 1 d . . .
H12A H 1.2067 0.3047 0.6728 0.029 Uiso 1 1 calc R . .
H12B H 0.9640 0.3074 0.6013 0.029 Uiso 1 1 calc R . .
C13 C 0.8725(4) 0.30380(17) 0.72426(15) 0.0243(5) Uani 1 1 d . . .
H13A H 0.8319 0.2287 0.7215 0.029 Uiso 1 1 calc R . .
H13B H 0.7093 0.3262 0.7076 0.029 Uiso 1 1 calc R . .
C14 C 0.9936(4) 0.35115(17) 0.81742(15) 0.0241(5) Uani 1 1 d . . .
H14A H 0.8671 0.3342 0.8562 0.029 Uiso 1 1 calc R . .
H14B H 1.1452 0.3224 0.8369 0.029 Uiso 1 1 calc R . .
N1 N 0.7145(4) 0.59196(14) 0.95540(12) 0.0234(4) Uani 1 1 d . . .
H1 H 0.5931 0.5947 0.9868 0.028 Uiso 1 1 calc R . .
O1 O 0.6621(3) 0.41878(12) 0.93482(10) 0.0255(4) Uani 1 1 d . . .
C101 C 0.3433(4) 1.03585(17) 0.68803(15) 0.0220(5) Uani 1 1 d . . .
C102 C 0.3134(5) 1.10715(18) 0.75219(16) 0.0271(5) Uani 1 1 d . . .
H102 H 0.1802 1.1441 0.7436 0.033 Uiso 1 1 calc R . .
C103 C 0.4843(5) 1.12313(18) 0.82969(16) 0.0295(5) Uani 1 1 d . . .
H103 H 0.4669 1.1710 0.8753 0.035 Uiso 1 1 calc R . .
C104 C 0.6804(5) 1.06953(18) 0.84088(15) 0.0281(5) Uani 1 1 d . . .
H104 H 0.7982 1.0823 0.8937 0.034 Uiso 1 1 calc R . .
C105 C 0.7069(4) 0.99718(17) 0.77556(15) 0.0246(5) Uani 1 1 d . . .
H105 H 0.8425 0.9614 0.7838 0.030 Uiso 1 1 calc R . .
C106 C 0.5342(4) 0.97786(16) 0.69860(14) 0.0211(5) Uani 1 1 d . . .
C107 C 0.5070(4) 0.91114(16) 0.61599(14) 0.0203(5) Uani 1 1 d . . .
C108 C 0.2948(4) 0.94109(16) 0.55680(15) 0.0208(5) Uani 1 1 d . . .
C109 C 0.6251(4) 0.83466(16) 0.59497(14) 0.0211(5) Uani 1 1 d . . .
C110 C 0.8034(5) 0.79459(17) 0.66032(16) 0.0269(5) Uani 1 1 d . . .
H11C H 0.7984 0.8262 0.7190 0.032 Uiso 1 1 calc R . .
H11D H 0.9821 0.8138 0.6493 0.032 Uiso 1 1 calc R . .
C111 C 0.7261(5) 0.67880(17) 0.65562(15) 0.0270(5) Uani 1 1 d . . .
H11E H 0.8552 0.6544 0.6952 0.032 Uiso 1 1 calc R . .
H11F H 0.5579 0.6604 0.6750 0.032 Uiso 1 1 calc R . .
C112 C 0.7062(5) 0.62613(17) 0.56464(15) 0.0263(5) Uani 1 1 d . . .
H11G H 0.6492 0.5516 0.5635 0.032 Uiso 1 1 calc R . .
H11H H 0.8774 0.6395 0.5468 0.032 Uiso 1 1 calc R . .
C113 C 0.5144(4) 0.66527(17) 0.50198(15) 0.0239(5) Uani 1 1 d . . .
H11I H 0.3404 0.6466 0.5171 0.029 Uiso 1 1 calc R . .
H11J H 0.5082 0.6327 0.4427 0.029 Uiso 1 1 calc R . .
C114 C 0.5914(4) 0.78096(17) 0.50518(14) 0.0225(5) Uani 1 1 d . . .
H11K H 0.7546 0.7986 0.4826 0.027 Uiso 1 1 calc R . .
H11L H 0.4572 0.8049 0.4674 0.027 Uiso 1 1 calc R . .
N101 N 0.2030(3) 1.01058(14) 0.60457(12) 0.0236(4) Uani 1 1 d . . .
H101 H 0.0707 1.0365 0.5852 0.028 Uiso 1 1 calc R . .
O101 O 0.2059(3) 0.90924(12) 0.48031(10) 0.0256(4) Uani 1 1 d . . .
 
 
_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 C2 1.377(3) . ?
C1 N1 1.399(3) . ?
C1 C6 1.408(3) . ?
C2 C3 1.395(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.483(3) . ?
C7 C9 1.354(3) . ?
C7 C8 1.507(3) . ?
C8 O1 1.234(3) . ?
C8 N1 1.361(3) . ?
C9 C14 1.504(3) . ?
C9 C10 1.505(3) . ?
C10 C11 1.535(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.521(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.524(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.543(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
N1 H1 0.8800 . ?
C101 C102 1.381(3) . ?
C101 N101 1.395(3) . ?
C101 C106 1.407(3) . ?
C102 C103 1.390(3) . ?
C102 H102 0.9500 . ?
C103 C104 1.389(3) . ?
C103 H103 0.9500 . ?
C104 C105 1.396(3) . ?
C104 H104 0.9500 . ?
C105 C106 1.386(3) . ?
C105 H105 0.9500 . ?
C106 C107 1.486(3) . ?
C107 C109 1.353(3) . ?
C107 C108 1.508(3) . ?
C108 O101 1.236(3) . ?
C108 N101 1.360(3) . ?
C109 C114 1.501(3) . ?
C109 C110 1.514(3) . ?
C110 C111 1.529(3) . ?
C110 H11C 0.9900 . ?
C110 H11D 0.9900 . ?
C111 C112 1.523(3) . ?
C111 H11E 0.9900 . ?
C111 H11F 0.9900 . ?
C112 C113 1.527(3) . ?
C112 H11G 0.9900 . ?
C112 H11H 0.9900 . ?
C113 C114 1.530(3) . ?
C113 H11I 0.9900 . ?
C113 H11J 0.9900 . ?
C114 H11K 0.9900 . ?
C114 H11L 0.9900 . ?
N101 H101 0.8800 . ?
 
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
C2 C1 N1 127.1(2) . . ?
C2 C1 C6 123.4(2) . . ?
N1 C1 C6 109.48(19) . . ?
C1 C2 C3 117.6(2) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 117.2(2) . . ?
C5 C6 C7 135.8(2) . . ?
C1 C6 C7 106.94(19) . . ?
C9 C7 C6 131.1(2) . . ?
C9 C7 C8 124.0(2) . . ?
C6 C7 C8 104.83(18) . . ?
O1 C8 N1 123.3(2) . . ?
O1 C8 C7 129.5(2) . . ?
N1 C8 C7 107.13(19) . . ?
C7 C9 C14 124.7(2) . . ?
C7 C9 C10 123.3(2) . . ?
C14 C9 C10 111.85(19) . . ?
C9 C10 C11 110.14(19) . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C12 C11 C10 110.90(19) . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C13 110.63(19) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 C14 111.61(19) . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C9 C14 C13 110.24(18) . . ?
C9 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
C9 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C8 N1 C1 111.54(18) . . ?
C8 N1 H1 124.2 . . ?
C1 N1 H1 124.2 . . ?
C102 C101 N101 127.8(2) . . ?
C102 C101 C106 122.9(2) . . ?
N101 C101 C106 109.2(2) . . ?
C101 C102 C103 117.9(2) . . ?
C101 C102 H102 121.1 . . ?
C103 C102 H102 121.1 . . ?
C102 C103 C104 120.4(2) . . ?
C102 C103 H103 119.8 . . ?
C104 C103 H103 119.8 . . ?
C103 C104 C105 120.9(2) . . ?
C103 C104 H104 119.5 . . ?
C105 C104 H104 119.5 . . ?
C106 C105 C104 119.7(2) . . ?
C106 C105 H105 120.2 . . ?
C104 C105 H105 120.2 . . ?
C105 C106 C101 118.1(2) . . ?
C105 C106 C107 134.7(2) . . ?
C101 C106 C107 107.05(19) . . ?
C109 C107 C106 130.7(2) . . ?
C109 C107 C108 124.5(2) . . ?
C106 C107 C108 104.66(18) . . ?
O101 C108 N101 123.7(2) . . ?
O101 C108 C107 129.4(2) . . ?
N101 C108 C107 106.85(19) . . ?
C107 C109 C114 123.5(2) . . ?
C107 C109 C110 123.0(2) . . ?
C114 C109 C110 113.48(19) . . ?
C109 C110 C111 111.26(19) . . ?
C109 C110 H11C 109.4 . . ?
C111 C110 H11C 109.4 . . ?
C109 C110 H11D 109.4 . . ?
C111 C110 H11D 109.4 . . ?
H11C C110 H11D 108.0 . . ?
C112 C111 C110 111.86(19) . . ?
C112 C111 H11E 109.2 . . ?
C110 C111 H11E 109.2 . . ?
C112 C111 H11F 109.2 . . ?
C110 C111 H11F 109.2 . . ?
H11E C111 H11F 107.9 . . ?
C111 C112 C113 110.08(19) . . ?
C111 C112 H11G 109.6 . . ?
C113 C112 H11G 109.6 . . ?
C111 C112 H11H 109.6 . . ?
C113 C112 H11H 109.6 . . ?
H11G C112 H11H 108.2 . . ?
C112 C113 C114 110.81(19) . . ?
C112 C113 H11I 109.5 . . ?
C114 C113 H11I 109.5 . . ?
C112 C113 H11J 109.5 . . ?
C114 C113 H11J 109.5 . . ?
H11I C113 H11J 108.1 . . ?
C109 C114 C113 112.15(18) . . ?
C109 C114 H11K 109.2 . . ?
C113 C114 H11K 109.2 . . ?
C109 C114 H11L 109.2 . . ?
C113 C114 H11L 109.2 . . ?
H11K C114 H11L 107.9 . . ?
C108 N101 C101 111.99(18) . . ?
C108 N101 H101 124.0 . . ?
C101 N101 H101 124.0 . . ?
 
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 H1 O1  0.88 1.97 2.846(2) 170.5 2_667
N101 H101 O101  0.88 1.98 2.850(2) 169.0 2_576
 
_diffrn_measured_fraction_theta_max    0.992
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.992
_refine_diff_density_max    0.328
_refine_diff_density_min   -0.235
_refine_diff_density_rms    0.058
