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#$Revision: 301777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/52/04/1520404.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_1520404
loop_
_publ_author_name
'Wirth, Thomas'
'Callear, Samantha K.'
'Hursthouse, Michael B.'
_publ_section_title
;
 C15H24N2O2
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              633
_journal_year                    2009
_chemical_formula_sum            'C15 H24 N2 O2'
_chemical_formula_weight         264.36
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 102.352(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.4770(5)
_cell_length_b                   11.2719(4)
_cell_length_c                   9.0254(3)
_cell_measurement_reflns_used    12305
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1438.70(9)
_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_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.1104
_diffrn_reflns_av_sigmaI/netI    0.0993
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15666
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.40
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9992
_exptl_absorpt_correction_T_min  0.9871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.1550
_refine_ls_R_factor_gt           0.0838
_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)+(0.0000P)²+2.3107P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1255
_refine_ls_wR_factor_ref         0.1525
_reflns_number_gt                2051
_reflns_number_total             3269
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            eCrystal-633.cif
_cod_data_source_block           2008src1307p21c
_cod_depositor_comments
;
Citation :
Wirth, Thomas and Callear, Samantha K. and 
Hursthouse, Michael B. (2009) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/633)

More at:
http://ecrystals.chem.soton.ac.uk/633/
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1520404
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'
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
C2 C -0.22094(19) 0.0150(3) 0.9945(3) 0.0211(6) Uani 1 1 d . . .
H2A H -0.2152 0.0893 0.9387 0.025 Uiso 1 1 calc R . .
H2B H -0.2457 0.0360 1.0853 0.025 Uiso 1 1 calc R . .
C3 C -0.29226(19) -0.0669(2) 0.8926(3) 0.0181(6) Uani 1 1 d . . .
C4 C -0.39049(19) -0.0107(3) 0.8811(3) 0.0222(6) Uani 1 1 d . . .
H4A H -0.4029 -0.0023 0.9843 0.027 Uiso 1 1 calc R . .
H4B H -0.3907 0.0697 0.8369 0.027 Uiso 1 1 calc R . .
C5 C -0.4694(2) -0.0839(3) 0.7841(3) 0.0281(7) Uani 1 1 d . . .
H5A H -0.4584 -0.0919 0.6800 0.034 Uiso 1 1 calc R . .
H5B H -0.5310 -0.0438 0.7779 0.034 Uiso 1 1 calc R . .
C6 C -0.4713(2) -0.2068(3) 0.8558(4) 0.0329(8) Uani 1 1 d . . .
H6A H -0.4892 -0.1987 0.9552 0.039 Uiso 1 1 calc R . .
H6B H -0.5196 -0.2565 0.7898 0.039 Uiso 1 1 calc R . .
C7 C -0.3756(2) -0.2675(3) 0.8779(3) 0.0266(7) Uani 1 1 d . . .
H7A H -0.3630 -0.2880 0.7773 0.032 Uiso 1 1 calc R . .
H7B H -0.3774 -0.3423 0.9346 0.032 Uiso 1 1 calc R . .
C8 C -0.2947(2) -0.1901(3) 0.9636(3) 0.0217(6) Uani 1 1 d . . .
H8A H -0.2339 -0.2307 0.9653 0.026 Uiso 1 1 calc R . .
H8B H -0.3015 -0.1809 1.0698 0.026 Uiso 1 1 calc R . .
C10 C -0.2580(2) -0.0040(2) 0.6345(3) 0.0193(6) Uani 1 1 d . . .
C11 C -0.1912(2) -0.0242(3) 0.5457(3) 0.0226(6) Uani 1 1 d . . .
H11 H -0.1488 -0.0892 0.5692 0.027 Uiso 1 1 calc R . .
C12 C -0.1855(2) 0.0485(3) 0.4246(3) 0.0277(7) Uani 1 1 d . . .
H12 H -0.1395 0.0325 0.3662 0.033 Uiso 1 1 calc R . .
C13 C -0.2461(2) 0.1446(3) 0.3872(3) 0.0277(7) Uani 1 1 d . . .
H13 H -0.2430 0.1940 0.3031 0.033 Uiso 1 1 calc R . .
C14 C -0.3108(2) 0.1661(3) 0.4757(3) 0.0277(7) Uani 1 1 d . . .
H14 H -0.3518 0.2325 0.4532 0.033 Uiso 1 1 calc R . .
C15 C -0.3177(2) 0.0935(3) 0.5966(3) 0.0262(7) Uani 1 1 d . . .
H15 H -0.3637 0.1104 0.6545 0.031 Uiso 1 1 calc R . .
N1 N -0.12533(16) -0.0384(2) 1.0446(3) 0.0211(5) Uani 1 1 d . . .
H1A H -0.1280 -0.0985 1.1110 0.032 Uiso 1 1 calc R . .
H1B H -0.0840 0.0179 1.0909 0.032 Uiso 1 1 calc R . .
H1C H -0.1055 -0.0675 0.9626 0.032 Uiso 1 1 calc R . .
N9 N -0.26540(17) -0.0875(2) 0.7458(2) 0.0192(5) Uani 1 1 d . . .
H9 H -0.222(2) -0.144(3) 0.753(3) 0.023 Uiso 1 1 d . . .
C21 C -0.0535(2) 0.2884(3) 0.2501(3) 0.0293(7) Uani 1 1 d . . .
H21A H -0.0587 0.2653 0.3527 0.044 Uiso 1 1 calc R . .
H21B H -0.1113 0.2655 0.1777 0.044 Uiso 1 1 calc R . .
H21C H -0.0450 0.3745 0.2462 0.044 Uiso 1 1 calc R . .
C22 C 0.0303(2) 0.2269(3) 0.2098(3) 0.0206(6) Uani 1 1 d . . .
O23 O 0.01653(14) 0.12661(18) 0.1454(2) 0.0253(5) Uani 1 1 d . . .
O24 O 0.11002(14) 0.27643(18) 0.2435(2) 0.0239(5) 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
N1 C2 C3 113.6(2) . .
N1 C2 H2A 108.8 . .
C3 C2 H2A 108.8 . .
N1 C2 H2B 108.8 . .
C3 C2 H2B 108.8 . .
H2A C2 H2B 107.7 . .
N9 C3 C8 105.5(2) . .
N9 C3 C2 111.1(2) . .
C8 C3 C2 111.5(2) . .
N9 C3 C4 114.9(2) . .
C8 C3 C4 107.3(2) . .
C2 C3 C4 106.6(2) . .
C5 C4 C3 112.6(2) . .
C5 C4 H4A 109.1 . .
C3 C4 H4A 109.1 . .
C5 C4 H4B 109.1 . .
C3 C4 H4B 109.1 . .
H4A C4 H4B 107.8 . .
C4 C5 C6 109.0(2) . .
C4 C5 H5A 109.9 . .
C6 C5 H5A 109.9 . .
C4 C5 H5B 109.9 . .
C6 C5 H5B 109.9 . .
H5A C5 H5B 108.3 . .
C7 C6 C5 111.4(2) . .
C7 C6 H6A 109.4 . .
C5 C6 H6A 109.4 . .
C7 C6 H6B 109.4 . .
C5 C6 H6B 109.4 . .
H6A C6 H6B 108.0 . .
C6 C7 C8 112.8(3) . .
C6 C7 H7A 109.0 . .
C8 C7 H7A 109.0 . .
C6 C7 H7B 109.0 . .
C8 C7 H7B 109.0 . .
H7A C7 H7B 107.8 . .
C7 C8 C3 112.9(2) . .
C7 C8 H8A 109.0 . .
C3 C8 H8A 109.0 . .
C7 C8 H8B 109.0 . .
C3 C8 H8B 109.0 . .
H8A C8 H8B 107.8 . .
C15 C10 N9 124.6(3) . .
C15 C10 C11 117.1(3) . .
N9 C10 C11 118.1(3) . .
C12 C11 C10 121.4(3) . .
C12 C11 H11 119.3 . .
C10 C11 H11 119.3 . .
C11 C12 C13 120.8(3) . .
C11 C12 H12 119.6 . .
C13 C12 H12 119.6 . .
C14 C13 C12 117.9(3) . .
C14 C13 H13 121.0 . .
C12 C13 H13 121.0 . .
C13 C14 C15 121.8(3) . .
C13 C14 H14 119.1 . .
C15 C14 H14 119.1 . .
C14 C15 C10 120.9(3) . .
C14 C15 H15 119.6 . .
C10 C15 H15 119.6 . .
C2 N1 H1A 109.5 . .
C2 N1 H1B 109.5 . .
H1A N1 H1B 109.5 . .
C2 N1 H1C 109.5 . .
H1A N1 H1C 109.5 . .
H1B N1 H1C 109.5 . .
C10 N9 C3 127.9(2) . .
C10 N9 H9 112.2(19) . .
C3 N9 H9 111.2(19) . .
C22 C21 H21A 109.5 . .
C22 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C22 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
O24 C22 O23 123.5(3) . .
O24 C22 C21 118.7(3) . .
O23 C22 C21 117.7(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C2 N1 1.489(3) .
C2 C3 1.536(4) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 N9 1.477(3) .
C3 C8 1.532(4) .
C3 C4 1.540(4) .
C4 C5 1.525(4) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.532(4) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C7 1.520(4) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.531(4) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C10 C15 1.395(4) .
C10 N9 1.397(3) .
C10 C11 1.401(4) .
C11 C12 1.382(4) .
C11 H11 0.9500 .
C12 C13 1.390(4) .
C12 H12 0.9500 .
C13 C14 1.376(4) .
C13 H13 0.9500 .
C14 C15 1.385(4) .
C14 H14 0.9500 .
C15 H15 0.9500 .
N1 H1A 0.9100 .
N1 H1B 0.9100 .
N1 H1C 0.9100 .
N9 H9 0.89(3) .
C21 C22 1.508(4) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 O24 1.260(3) .
C22 O23 1.267(3) .
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 H1A O24 0.91 1.91 2.807(3) 169.9 2_546
N1 H1B O23 0.91 1.89 2.776(3) 165.4 1_556
N9 H9 O24 0.89(3) 2.20(3) 3.084(3) 175(3) 3_556
N1 H1C O23 0.91 1.90 2.751(3) 155.8 3_556
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139045547
