#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/04/1520417.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_1520417
loop_
_publ_author_name
'Spencer, John'
'Patel, Hiren'
'Callear, Samantha K.'
_publ_section_title
;
 C16H23N4O
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              646
_journal_year                    2009
_chemical_formula_sum            'C16 H23 N4 O'
_chemical_formula_weight         287.38
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 94.292(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5278(5)
_cell_length_b                   5.3937(2)
_cell_length_c                   27.1476(14)
_cell_measurement_reflns_used    19693
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1537.22(12)
_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 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            14555
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9960
_exptl_absorpt_correction_T_min  0.9857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3462
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0782
_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)+(0.0315P)²+2.2327P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1535
_refine_ls_wR_factor_ref         0.1734
_reflns_number_gt                2524
_reflns_number_total             3462
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            eCrystal-646.cif
_cod_data_source_block           2009src0112
_cod_depositor_comments
;
Citation :
Spencer, John and Patel, Hiren and Callear, Samantha K. (2009) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/646)

More at:
http://ecrystals.chem.soton.ac.uk/646/
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1520417
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C14A C 0.6963(6) -0.2818(16) 0.0784(3) 0.0302(16) Uani 0.546(3) 1 d P A 1
C15A C 0.8347(4) -0.3509(9) 0.07472(16) 0.0330(11) Uani 0.546(3) 1 d P A 1
H15A H 0.8431 -0.5335 0.0732 0.040 Uiso 0.546(3) 1 calc PR A 1
H15B H 0.8861 -0.2915 0.1044 0.040 Uiso 0.546(3) 1 calc PR A 1
C16A C 0.8843(5) -0.2341(10) 0.0284(2) 0.0394(13) Uani 0.546(3) 1 d P A 1
H16A H 0.8796 -0.0513 0.0308 0.047 Uiso 0.546(3) 1 calc PR A 1
H16B H 0.9748 -0.2804 0.0263 0.047 Uiso 0.546(3) 1 calc PR A 1
C17A C 0.8077(6) -0.3189(14) -0.0181(2) 0.0379(14) Uani 0.546(3) 1 d P A 1
H17A H 0.8187 -0.4997 -0.0224 0.045 Uiso 0.546(3) 1 calc PR A 1
H17B H 0.8393 -0.2345 -0.0472 0.045 Uiso 0.546(3) 1 calc PR A 1
C18A C 0.6649(4) -0.2594(10) -0.01507(16) 0.0380(12) Uani 0.546(3) 1 d P A 1
H18A H 0.6527 -0.0774 -0.0159 0.046 Uiso 0.546(3) 1 calc PR A 1
H18B H 0.6157 -0.3307 -0.0442 0.046 Uiso 0.546(3) 1 calc PR A 1
C19A C 0.6133(5) -0.3635(10) 0.03224(19) 0.0338(11) Uani 0.546(3) 1 d P A 1
H19A H 0.5250 -0.3047 0.0347 0.041 Uiso 0.546(3) 1 calc PR A 1
H19B H 0.6116 -0.5468 0.0305 0.041 Uiso 0.546(3) 1 calc PR A 1
C14B C 0.6623(7) -0.3315(17) 0.0632(3) 0.0230(17) Uani 0.454(3) 1 d P A 2
C15B C 0.7581(5) -0.1198(9) 0.06940(19) 0.0292(12) Uani 0.454(3) 1 d P A 2
H15C H 0.8301 -0.1714 0.0927 0.035 Uiso 0.454(3) 1 calc PR A 2
H15D H 0.7167 0.0251 0.0839 0.035 Uiso 0.454(3) 1 calc PR A 2
C16B C 0.8096(5) -0.0431(10) 0.0198(2) 0.0334(13) Uani 0.454(3) 1 d P A 2
H16C H 0.7394 0.0280 -0.0021 0.040 Uiso 0.454(3) 1 calc PR A 2
H16D H 0.8756 0.0864 0.0258 0.040 Uiso 0.454(3) 1 calc PR A 2
C17B C 0.8666(7) -0.2637(14) -0.0058(3) 0.0342(17) Uani 0.454(3) 1 d P A 2
H17C H 0.9439 -0.3207 0.0141 0.041 Uiso 0.454(3) 1 calc PR A 2
H17D H 0.8923 -0.2117 -0.0386 0.041 Uiso 0.454(3) 1 calc PR A 2
C18B C 0.7716(5) -0.4780(13) -0.0122(2) 0.0324(13) Uani 0.454(3) 1 d P A 2
H18C H 0.6983 -0.4268 -0.0349 0.039 Uiso 0.454(3) 1 calc PR A 2
H18D H 0.8130 -0.6215 -0.0271 0.039 Uiso 0.454(3) 1 calc PR A 2
C19B C 0.7244(5) -0.5541(9) 0.0373(2) 0.0287(12) Uani 0.454(3) 1 d P A 2
H19C H 0.7968 -0.6181 0.0590 0.034 Uiso 0.454(3) 1 calc PR A 2
H19D H 0.6612 -0.6892 0.0321 0.034 Uiso 0.454(3) 1 calc PR A 2
C2 C -0.0176(2) 0.1123(5) 0.16817(10) 0.0375(6) Uani 1 1 d . . .
H2 H -0.0573 0.2573 0.1544 0.045 Uiso 1 1 calc R . .
C3 C -0.0877(2) -0.0383(5) 0.19684(9) 0.0323(6) Uani 1 1 d . . .
C4 C -0.0294(3) -0.2533(5) 0.21401(11) 0.0437(7) Uani 1 1 d . . .
H4 H -0.0751 -0.3674 0.2326 0.052 Uiso 1 1 calc R . .
C5 C 0.0951(2) -0.3045(5) 0.20436(11) 0.0421(7) Uani 1 1 d . . .
H5 H 0.1351 -0.4531 0.2162 0.051 Uiso 1 1 calc R . .
C6 C 0.1607(2) -0.1367(5) 0.17725(9) 0.0328(6) Uani 1 1 d . . .
C8 C 0.3528(2) -0.3928(6) 0.18611(10) 0.0412(7) Uani 1 1 d . . .
H8A H 0.3231 -0.5302 0.1640 0.049 Uiso 1 1 calc R . .
H8B H 0.3292 -0.4325 0.2198 0.049 Uiso 1 1 calc R . .
C9 C 0.4965(2) -0.3698(7) 0.18636(10) 0.0511(8) Uani 1 1 d . . .
H9A H 0.5273 -0.2479 0.2118 0.061 Uiso 1 1 calc R . .
H9B H 0.5362 -0.5319 0.1951 0.061 Uiso 1 1 calc R . .
C11 C 0.4721(3) -0.0634(5) 0.12134(16) 0.0651(11) Uani 1 1 d . . .
H11A H 0.4952 -0.0252 0.0875 0.078 Uiso 1 1 calc R . .
H11B H 0.5013 0.0755 0.1432 0.078 Uiso 1 1 calc R . .
C12 C 0.3284(3) -0.0900(5) 0.12143(11) 0.0463(8) Uani 1 1 d . . .
H12A H 0.2875 0.0702 0.1121 0.056 Uiso 1 1 calc R . .
H12B H 0.2983 -0.2150 0.0965 0.056 Uiso 1 1 calc R . .
C13 C 0.6342(2) -0.4054(5) 0.11897(11) 0.0396(7) Uani 1 1 d . . .
N1 N 0.1040(2) 0.0666(4) 0.15842(9) 0.0420(6) Uani 1 1 d . . .
N3 N -0.2097(2) 0.0300(5) 0.20977(9) 0.0388(6) Uani 1 1 d D . .
N7 N 0.29113(19) -0.1647(4) 0.16951(8) 0.0366(5) Uani 1 1 d . . .
N10 N 0.5347(2) -0.2911(4) 0.13846(9) 0.0416(6) Uani 1 1 d . A .
O12 O 0.68528(17) -0.5884(4) 0.13863(7) 0.0420(5) Uani 1 1 d . A .
H3A H -0.247(2) 0.140(5) 0.1890(9) 0.042(8) Uiso 1 1 d D . .
H3B H -0.255(3) -0.101(4) 0.2195(11) 0.055(9) Uiso 1 1 d 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
C13 C14A C15A 114.7(6) . .
C13 C14A C19A 102.8(5) . .
C15A C14A C19A 111.5(6) . .
C14A C15A C16A 110.0(5) . .
C14A C15A H15A 109.7 . .
C16A C15A H15A 109.7 . .
C14A C15A H15B 109.7 . .
C16A C15A H15B 109.7 . .
H15A C15A H15B 108.2 . .
C17A C16A C15A 111.5(4) . .
C17A C16A H16A 109.3 . .
C15A C16A H16A 109.3 . .
C17A C16A H16B 109.3 . .
C15A C16A H16B 109.3 . .
H16A C16A H16B 108.0 . .
C16A C17A C18A 110.6(4) . .
C16A C17A H17A 109.5 . .
C18A C17A H17A 109.5 . .
C16A C17A H17B 109.5 . .
C18A C17A H17B 109.5 . .
H17A C17A H17B 108.1 . .
C19A C18A C17A 112.0(4) . .
C19A C18A H18A 109.2 . .
C17A C18A H18A 109.2 . .
C19A C18A H18B 109.2 . .
C17A C18A H18B 109.2 . .
H18A C18A H18B 107.9 . .
C14A C19A C18A 111.2(5) . .
C14A C19A H19A 109.4 . .
C18A C19A H19A 109.4 . .
C14A C19A H19B 109.4 . .
C18A C19A H19B 109.4 . .
H19A C19A H19B 108.0 . .
C15B C14B C19B 109.3(6) . .
C15B C14B C13 104.3(5) . .
C19B C14B C13 110.1(6) . .
C14B C15B C16B 112.1(5) . .
C14B C15B H15C 109.2 . .
C16B C15B H15C 109.2 . .
C14B C15B H15D 109.2 . .
C16B C15B H15D 109.2 . .
H15C C15B H15D 107.9 . .
C17B C16B C15B 111.3(5) . .
C17B C16B H16C 109.4 . .
C15B C16B H16C 109.4 . .
C17B C16B H16D 109.4 . .
C15B C16B H16D 109.4 . .
H16C C16B H16D 108.0 . .
C16B C17B C18B 111.4(5) . .
C16B C17B H17C 109.3 . .
C18B C17B H17C 109.3 . .
C16B C17B H17D 109.3 . .
C18B C17B H17D 109.3 . .
H17C C17B H17D 108.0 . .
C19B C18B C17B 110.9(5) . .
C19B C18B H18C 109.5 . .
C17B C18B H18C 109.5 . .
C19B C18B H18D 109.5 . .
C17B C18B H18D 109.5 . .
H18C C18B H18D 108.1 . .
C18B C19B C14B 111.4(5) . .
C18B C19B H19C 109.3 . .
C14B C19B H19C 109.3 . .
C18B C19B H19D 109.3 . .
C14B C19B H19D 109.3 . .
H19C C19B H19D 108.0 . .
N1 C2 C3 124.0(3) . .
N1 C2 H2 118.0 . .
C3 C2 H2 118.0 . .
C4 C3 C2 116.4(2) . .
C4 C3 N3 121.9(2) . .
C2 C3 N3 121.7(2) . .
C3 C4 C5 120.6(2) . .
C3 C4 H4 119.7 . .
C5 C4 H4 119.7 . .
C6 C5 C4 119.2(3) . .
C6 C5 H5 120.4 . .
C4 C5 H5 120.4 . .
N1 C6 C5 121.0(2) . .
N1 C6 N7 116.3(2) . .
C5 C6 N7 122.6(2) . .
N7 C8 C9 110.9(2) . .
N7 C8 H8A 109.5 . .
C9 C8 H8A 109.5 . .
N7 C8 H8B 109.5 . .
C9 C8 H8B 109.5 . .
H8A C8 H8B 108.1 . .
N10 C9 C8 111.2(2) . .
N10 C9 H9A 109.4 . .
C8 C9 H9A 109.4 . .
N10 C9 H9B 109.4 . .
C8 C9 H9B 109.4 . .
H9A C9 H9B 108.0 . .
N10 C11 C12 110.3(2) . .
N10 C11 H11A 109.6 . .
C12 C11 H11A 109.6 . .
N10 C11 H11B 109.6 . .
C12 C11 H11B 109.6 . .
H11A C11 H11B 108.1 . .
N7 C12 C11 111.4(3) . .
N7 C12 H12A 109.3 . .
C11 C12 H12A 109.3 . .
N7 C12 H12B 109.4 . .
C11 C12 H12B 109.4 . .
H12A C12 H12B 108.0 . .
O12 C13 N10 121.5(2) . .
O12 C13 C14A 118.8(4) . .
N10 C13 C14A 118.8(4) . .
O12 C13 C14B 120.1(4) . .
N10 C13 C14B 117.0(4) . .
C14A C13 C14B 21.5(3) . .
C6 N1 C2 118.7(2) . .
C3 N3 H3A 112.7(18) . .
C3 N3 H3B 112(2) . .
H3A N3 H3B 119(3) . .
C6 N7 C8 117.6(2) . .
C6 N7 C12 115.9(2) . .
C8 N7 C12 111.80(19) . .
C13 N10 C9 119.3(2) . .
C13 N10 C11 127.2(2) . .
C9 N10 C11 112.6(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C14A C13 1.481(9) .
C14A C15A 1.514(8) .
C14A C19A 1.537(7) .
C15A C16A 1.534(6) .
C15A H15A 0.9900 .
C15A H15B 0.9900 .
C16A C17A 1.517(8) .
C16A H16A 0.9900 .
C16A H16B 0.9900 .
C17A C18A 1.546(7) .
C17A H17A 0.9900 .
C17A H17B 0.9900 .
C18A C19A 1.537(6) .
C18A H18A 0.9900 .
C18A H18B 0.9900 .
C19A H19A 0.9900 .
C19A H19B 0.9900 .
C14B C15B 1.525(9) .
C14B C19B 1.558(10) .
C14B C13 1.615(9) .
C15B C16B 1.546(7) .
C15B H15C 0.9900 .
C15B H15D 0.9900 .
C16B C17B 1.523(9) .
C16B H16C 0.9900 .
C16B H16D 0.9900 .
C17B C18B 1.530(8) .
C17B H17C 0.9900 .
C17B H17D 0.9900 .
C18B C19B 1.524(8) .
C18B H18C 0.9900 .
C18B H18D 0.9900 .
C19B H19C 0.9900 .
C19B H19D 0.9900 .
C2 N1 1.349(3) .
C2 C3 1.377(3) .
C2 H2 0.9500 .
C3 C4 1.377(4) .
C3 N3 1.406(3) .
C4 C5 1.384(3) .
C4 H4 0.9500 .
C5 C6 1.383(3) .
C5 H5 0.9500 .
C6 N1 1.332(3) .
C6 N7 1.413(3) .
C8 N7 1.448(4) .
C8 C9 1.517(3) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 N10 1.453(3) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C11 N10 1.454(4) .
C11 C12 1.519(4) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 N7 1.448(3) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 O12 1.227(3) .
C13 N10 1.357(3) .
N3 H3A 0.890(17) .
N3 H3B 0.903(18) .
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
N3 H3A O12 0.890(17) 2.092(18) 2.978(3) 174(3) 1_465
