#------------------------------------------------------------------------------
#$Date: 2015-05-21 10:12:06 +0300 (Thu, 21 May 2015) $
#$Revision: 137103 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/98/1519801.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_1519801
loop_
_publ_author_name
'Spencer, John'
'Male, Louise'
'Hursthouse, Michael B.'
_publ_section_title
;
 C11H11N1O1
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              348
_journal_year                    2007
_chemical_formula_sum            'C11 H11 N O'
_chemical_formula_weight         173.21
_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                95.766(2)
_cell_angle_beta                 107.842(2)
_cell_angle_gamma                96.617(2)
_cell_formula_units_Z            6
_cell_length_a                   9.7504(3)
_cell_length_b                   10.2281(3)
_cell_length_c                   14.0530(5)
_cell_measurement_reflns_used    16164
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1311.46(8)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0592
_diffrn_reflns_av_sigmaI/netI    0.0674
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21390
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9966
_exptl_absorpt_correction_T_min  0.9750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            'Pale Orange'
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         5972
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0788
_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)+(0.0214P)²+2.3310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1445
_refine_ls_wR_factor_ref         0.1681
_reflns_number_gt                4122
_reflns_number_total             5972
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-348.cif
_cod_data_source_block           2007src1054
_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/348)

More at:
http://ecrystals.chem.soton.ac.uk/348/

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               1519801
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 0.9147(3) 0.0015(2) 0.3484(2) 0.0191(5) Uani 1 1 d . . .
C2 C 0.8145(3) 0.0030(2) 0.24248(19) 0.0185(5) Uani 1 1 d . . .
C3 C 0.6692(3) 0.0080(2) 0.25253(19) 0.0185(5) Uani 1 1 d . . .
C4 C 0.6851(3) 0.0091(2) 0.3554(2) 0.0198(6) Uani 1 1 d . . .
C5 C 0.5695(3) 0.0098(3) 0.3926(2) 0.0250(6) Uani 1 1 d . . .
H5 H 0.5836 0.0113 0.4626 0.030 Uiso 1 1 calc R . .
C6 C 0.4314(3) 0.0084(3) 0.3239(2) 0.0277(6) Uani 1 1 d . . .
H6 H 0.3497 0.0088 0.3471 0.033 Uiso 1 1 calc R . .
C7 C 0.4125(3) 0.0065(3) 0.2220(2) 0.0266(6) Uani 1 1 d . . .
H7 H 0.3175 0.0049 0.1762 0.032 Uiso 1 1 calc R . .
C8 C 0.5304(3) 0.0068(3) 0.1855(2) 0.0240(6) Uani 1 1 d . . .
H8 H 0.5159 0.0062 0.1154 0.029 Uiso 1 1 calc R . .
C9 C 0.8559(3) 0.0002(2) 0.1591(2) 0.0214(6) Uani 1 1 d . . .
C10 C 0.7509(3) 0.0086(3) 0.0571(2) 0.0263(6) Uani 1 1 d . . .
H10A H 0.6692 -0.0646 0.0396 0.040 Uiso 1 1 calc R . .
H10B H 0.8008 0.0021 0.0064 0.040 Uiso 1 1 calc R . .
H10C H 0.7140 0.0936 0.0587 0.040 Uiso 1 1 calc R . .
C11 C 1.0083(3) -0.0114(3) 0.1595(2) 0.0293(7) Uani 1 1 d . . .
H11A H 1.0706 -0.0132 0.2288 0.044 Uiso 1 1 calc R . .
H11B H 1.0465 0.0650 0.1333 0.044 Uiso 1 1 calc R . .
H11C H 1.0072 -0.0937 0.1168 0.044 Uiso 1 1 calc R . .
N1 N 0.8302(2) 0.0067(2) 0.40969(17) 0.0210(5) Uani 1 1 d . . .
H1 H 0.8635 0.0083 0.4756 0.025 Uiso 1 1 calc R . .
O1 O 1.0469(2) -0.00082(18) 0.37839(14) 0.0229(4) Uani 1 1 d . . .
C101 C 1.1804(3) 0.3134(2) 0.67501(19) 0.0190(5) Uani 1 1 d . . .
C102 C 1.0822(3) 0.3172(2) 0.5693(2) 0.0193(5) Uani 1 1 d . . .
C103 C 0.9363(3) 0.3213(2) 0.57864(19) 0.0192(6) Uani 1 1 d . . .
C104 C 0.9502(3) 0.3190(2) 0.6811(2) 0.0212(6) Uani 1 1 d . . .
C105 C 0.8340(3) 0.3202(3) 0.7174(2) 0.0257(6) Uani 1 1 d . . .
H105 H 0.8472 0.3190 0.7871 0.031 Uiso 1 1 calc R . .
C106 C 0.6973(3) 0.3231(3) 0.6493(2) 0.0280(6) Uani 1 1 d . . .
H106 H 0.6155 0.3240 0.6724 0.034 Uiso 1 1 calc R . .
C107 C 0.6796(3) 0.3249(3) 0.5477(2) 0.0291(6) Uani 1 1 d . . .
H107 H 0.5854 0.3269 0.5019 0.035 Uiso 1 1 calc R . .
C108 C 0.7983(3) 0.3238(3) 0.5115(2) 0.0268(6) Uani 1 1 d . . .
H108 H 0.7848 0.3247 0.4417 0.032 Uiso 1 1 calc R . .
C109 C 1.1276(3) 0.3190(2) 0.4874(2) 0.0213(6) Uani 1 1 d . . .
C110 C 1.0276(3) 0.3347(3) 0.3856(2) 0.0314(7) Uani 1 1 d . . .
H11D H 0.9703 0.2482 0.3516 0.047 Uiso 1 1 calc R . .
H11E H 1.0855 0.3687 0.3448 0.047 Uiso 1 1 calc R . .
H11F H 0.9618 0.3973 0.3937 0.047 Uiso 1 1 calc R . .
C111 C 1.2798(3) 0.3054(3) 0.4896(2) 0.0290(7) Uani 1 1 d . . .
H11G H 1.3339 0.2812 0.5549 0.043 Uiso 1 1 calc R . .
H11H H 1.3284 0.3901 0.4802 0.043 Uiso 1 1 calc R . .
H11I H 1.2766 0.2360 0.4353 0.043 Uiso 1 1 calc R . .
N101 N 1.0952(2) 0.3153(2) 0.73532(17) 0.0216(5) Uani 1 1 d . . .
H101 H 1.1277 0.3143 0.8009 0.026 Uiso 1 1 calc R . .
O101 O 1.3130(2) 0.31170(18) 0.70609(14) 0.0242(4) Uani 1 1 d . . .
C201 C 0.3470(3) 0.3250(2) -0.0211(2) 0.0202(6) Uani 1 1 d . . .
C202 C 0.4479(3) 0.3417(2) 0.0863(2) 0.0194(5) Uani 1 1 d . . .
C203 C 0.5959(3) 0.3479(2) 0.0787(2) 0.0200(6) Uani 1 1 d . . .
C204 C 0.5804(3) 0.3330(2) -0.0249(2) 0.0202(6) Uani 1 1 d . . .
C205 C 0.6974(3) 0.3345(3) -0.0603(2) 0.0243(6) Uani 1 1 d . . .
H205 H 0.6835 0.3230 -0.1307 0.029 Uiso 1 1 calc R . .
C206 C 0.8367(3) 0.3533(3) 0.0099(2) 0.0258(6) Uani 1 1 d . . .
H206 H 0.9194 0.3558 -0.0125 0.031 Uiso 1 1 calc R . .
C207 C 0.8552(3) 0.3686(3) 0.1127(2) 0.0279(6) Uani 1 1 d . . .
H207 H 0.9509 0.3813 0.1598 0.033 Uiso 1 1 calc R . .
C208 C 0.7363(3) 0.3658(3) 0.1479(2) 0.0246(6) Uani 1 1 d . . .
H208 H 0.7506 0.3759 0.2183 0.030 Uiso 1 1 calc R . .
C209 C 0.4052(3) 0.3485(2) 0.1693(2) 0.0204(6) Uani 1 1 d . . .
C210 C 0.5128(3) 0.3655(3) 0.2744(2) 0.0283(6) Uani 1 1 d . . .
H21A H 0.5684 0.2911 0.2811 0.043 Uiso 1 1 calc R . .
H21B H 0.4603 0.3674 0.3237 0.043 Uiso 1 1 calc R . .
H21C H 0.5797 0.4492 0.2867 0.043 Uiso 1 1 calc R . .
C211 C 0.2486(3) 0.3408(3) 0.1650(2) 0.0288(6) Uani 1 1 d . . .
H21D H 0.1857 0.3261 0.0944 0.043 Uiso 1 1 calc R . .
H21E H 0.2346 0.4243 0.1990 0.043 Uiso 1 1 calc R . .
H21F H 0.2232 0.2670 0.1990 0.043 Uiso 1 1 calc R . .
N201 N 0.4328(2) 0.3184(2) -0.08114(17) 0.0212(5) Uani 1 1 d . . .
H201 H 0.3992 0.3063 -0.1476 0.025 Uiso 1 1 calc R . .
O201 O 0.2127(2) 0.31515(18) -0.05334(14) 0.0236(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
O1 C1 N1 124.2(2) . .
O1 C1 C2 129.4(2) . .
N1 C1 C2 106.4(2) . .
C9 C2 C3 129.6(2) . .
C9 C2 C1 125.2(2) . .
C3 C2 C1 105.3(2) . .
C8 C3 C4 118.2(2) . .
C8 C3 C2 134.9(2) . .
C4 C3 C2 106.8(2) . .
C5 C4 N1 127.3(2) . .
C5 C4 C3 123.0(3) . .
N1 C4 C3 109.8(2) . .
C4 C5 C6 117.7(3) . .
C4 C5 H5 121.1 . .
C6 C5 H5 121.1 . .
C7 C6 C5 120.5(3) . .
C7 C6 H6 119.8 . .
C5 C6 H6 119.8 . .
C6 C7 C8 121.2(3) . .
C6 C7 H7 119.4 . .
C8 C7 H7 119.4 . .
C3 C8 C7 119.4(3) . .
C3 C8 H8 120.3 . .
C7 C8 H8 120.3 . .
C2 C9 C11 123.7(3) . .
C2 C9 C10 121.9(3) . .
C11 C9 C10 114.4(2) . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C9 C11 H11A 109.5 . .
C9 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C9 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C1 N1 C4 111.7(2) . .
C1 N1 H1 124.1 . .
C4 N1 H1 124.1 . .
O101 C101 N101 123.8(2) . .
O101 C101 C102 129.5(2) . .
N101 C101 C102 106.7(2) . .
C109 C102 C103 130.4(3) . .
C109 C102 C101 124.5(2) . .
C103 C102 C101 105.1(2) . .
C108 C103 C104 118.0(2) . .
C108 C103 C102 135.0(2) . .
C104 C103 C102 107.0(2) . .
C105 C104 N101 127.7(3) . .
C105 C104 C103 123.0(3) . .
N101 C104 C103 109.3(2) . .
C104 C105 C106 118.2(3) . .
C104 C105 H105 120.9 . .
C106 C105 H105 120.9 . .
C107 C106 C105 120.4(3) . .
C107 C106 H106 119.8 . .
C105 C106 H106 119.8 . .
C106 C107 C108 121.0(3) . .
C106 C107 H107 119.5 . .
C108 C107 H107 119.5 . .
C103 C108 C107 119.4(3) . .
C103 C108 H108 120.3 . .
C107 C108 H108 120.3 . .
C102 C109 C111 123.7(3) . .
C102 C109 C110 122.2(3) . .
C111 C109 C110 114.1(2) . .
C109 C110 H11D 109.5 . .
C109 C110 H11E 109.5 . .
H11D C110 H11E 109.5 . .
C109 C110 H11F 109.5 . .
H11D C110 H11F 109.5 . .
H11E C110 H11F 109.5 . .
C109 C111 H11G 109.5 . .
C109 C111 H11H 109.5 . .
H11G C111 H11H 109.5 . .
C109 C111 H11I 109.5 . .
H11G C111 H11I 109.5 . .
H11H C111 H11I 109.5 . .
C101 N101 C104 112.0(2) . .
C101 N101 H101 124.0 . .
C104 N101 H101 124.0 . .
O201 C201 N201 124.0(2) . .
O201 C201 C202 129.6(2) . .
N201 C201 C202 106.4(2) . .
C209 C202 C203 129.5(3) . .
C209 C202 C201 125.1(2) . .
C203 C202 C201 105.4(2) . .
C208 C203 C204 118.2(2) . .
C208 C203 C202 135.0(2) . .
C204 C203 C202 106.8(2) . .
C205 C204 N201 127.9(2) . .
C205 C204 C203 122.8(3) . .
N201 C204 C203 109.3(2) . .
C204 C205 C206 118.2(3) . .
C204 C205 H205 120.9 . .
C206 C205 H205 120.9 . .
C207 C206 C205 120.2(3) . .
C207 C206 H206 119.9 . .
C205 C206 H206 119.9 . .
C206 C207 C208 121.3(3) . .
C206 C207 H207 119.4 . .
C208 C207 H207 119.4 . .
C207 C208 C203 119.4(3) . .
C207 C208 H208 120.3 . .
C203 C208 H208 120.3 . .
C202 C209 C211 123.4(3) . .
C202 C209 C210 122.0(3) . .
C211 C209 C210 114.6(2) . .
C209 C210 H21A 109.5 . .
C209 C210 H21B 109.5 . .
H21A C210 H21B 109.5 . .
C209 C210 H21C 109.5 . .
H21A C210 H21C 109.5 . .
H21B C210 H21C 109.5 . .
C209 C211 H21D 109.5 . .
C209 C211 H21E 109.5 . .
H21D C211 H21E 109.5 . .
C209 C211 H21F 109.5 . .
H21D C211 H21F 109.5 . .
H21E C211 H21F 109.5 . .
C201 N201 C204 112.0(2) . .
C201 N201 H201 124.0 . .
C204 N201 H201 124.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.232(3) .
C1 N1 1.363(3) .
C1 C2 1.512(4) .
C2 C9 1.351(4) .
C2 C3 1.472(4) .
C3 C8 1.390(4) .
C3 C4 1.404(3) .
C4 C5 1.381(4) .
C4 N1 1.391(3) .
C5 C6 1.393(4) .
C5 H5 0.9500 .
C6 C7 1.384(4) .
C6 H6 0.9500 .
C7 C8 1.395(4) .
C7 H7 0.9500 .
C8 H8 0.9500 .
C9 C11 1.502(4) .
C9 C10 1.502(4) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
N1 H1 0.8800 .
C101 O101 1.234(3) .
C101 N101 1.357(3) .
C101 C102 1.508(4) .
C102 C109 1.355(4) .
C102 C103 1.473(4) .
C103 C108 1.391(4) .
C103 C104 1.407(4) .
C104 C105 1.378(4) .
C104 N101 1.393(3) .
C105 C106 1.388(4) .
C105 H105 0.9500 .
C106 C107 1.386(4) .
C106 H106 0.9500 .
C107 C108 1.401(4) .
C107 H107 0.9500 .
C108 H108 0.9500 .
C109 C111 1.497(4) .
C109 C110 1.500(4) .
C110 H11D 0.9800 .
C110 H11E 0.9800 .
C110 H11F 0.9800 .
C111 H11G 0.9800 .
C111 H11H 0.9800 .
C111 H11I 0.9800 .
N101 H101 0.8800 .
C201 O201 1.235(3) .
C201 N201 1.360(3) .
C201 C202 1.509(4) .
C202 C209 1.351(4) .
C202 C203 1.474(4) .
C203 C208 1.394(4) .
C203 C204 1.408(4) .
C204 C205 1.376(4) .
C204 N201 1.396(3) .
C205 C206 1.390(4) .
C205 H205 0.9500 .
C206 C207 1.390(4) .
C206 H206 0.9500 .
C207 C208 1.391(4) .
C207 H207 0.9500 .
C208 H208 0.9500 .
C209 C211 1.502(4) .
C209 C210 1.507(4) .
C210 H21A 0.9800 .
C210 H21B 0.9800 .
C210 H21C 0.9800 .
C211 H21D 0.9800 .
C211 H21E 0.9800 .
C211 H21F 0.9800 .
N201 H201 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 1.98 2.859(3) 174.2 2_756
N101 H101 O201 0.88 1.96 2.837(3) 176.3 1_656
N201 H201 O101 0.88 1.98 2.848(3) 169.5 1_454
