#------------------------------------------------------------------------------
#$Date: 2015-05-21 10:12:39 +0300 (Thu, 21 May 2015) $
#$Revision: 137104 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/98/1519802.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1519802
loop_
_publ_author_name
'Spencer, John'
'Male, Louise'
'Hursthouse, Michael B.'
_publ_section_title
;
 C14H15NO
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              351
_journal_year                    2007
_chemical_formula_sum            'C14 H15 N O'
_chemical_formula_weight         213.27
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                95.3890(10)
_cell_angle_beta                 98.498(2)
_cell_angle_gamma                101.201(2)
_cell_formula_units_Z            4
_cell_length_a                   5.37320(10)
_cell_length_b                   13.4962(4)
_cell_length_c                   15.8088(5)
_cell_measurement_reflns_used    12338
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1103.32(5)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_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)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)
;
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_sigmaI/netI    0.0577
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18503
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_correction_T_min  0.9346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            'Pale Brown'
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.85
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4997
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0660
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0082P)²+1.5131P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1360
_reflns_number_gt                3778
_reflns_number_total             4997
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-351.cif
_cod_data_source_block           2007src1055
_cod_depositor_comments
;
Citation :
Spencer, John and Male, Louise and Hursthouse, Michael B. (2007) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/351)

More at:
http://ecrystals.chem.soton.ac.uk/351/

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 3392 2015-05-12 13:50:21Z andrius 
;
_cod_database_code               1519802
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 . . .
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'
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
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
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_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
