#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:50:43 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178408 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/29/4022961.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_4022961
loop_
_publ_author_name
'Dimitri M. Khramov'
'Christopher W. Bielawski'
_publ_section_title
;
 Donor-Acceptor Triazenes: Synthesis, Characterization,
 and Study of Their Electronic and Thermal Properties
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9407
_journal_page_last               9417
_journal_paper_doi               10.1021/jo070789x
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C17 H18 N6 O4'
_chemical_formula_weight         370.37
_chemical_name_systematic
; 
 ? 
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.197(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9005(4)
_cell_length_b                   7.5544(3)
_cell_length_c                   25.4468(12)
_cell_measurement_reflns_used    3204
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      1
_cell_volume                     1710.98(13)
_computing_cell_refinement       'Collect software, Nonius B.V. 1998'
_computing_data_collection       'Collect software, Nonius B.V. 1998'
_computing_data_reduction
;
DENZO and Scalepack (Otwinoski and Minor, 1997)
;
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1049
_diffrn_reflns_av_sigmaI/netI    0.1719
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            5428
_diffrn_reflns_theta_full        24.95
_diffrn_reflns_theta_max         24.95
_diffrn_reflns_theta_min         2.81
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            plates
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ' dark orange '
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2978
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1916
_refine_ls_R_factor_gt           0.0527
_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)+(0.0200P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.1060
_reflns_number_gt                1205
_reflns_number_total             2978
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070789xsi20070418_070137_2.cif
_cod_data_source_block           2meono2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4022961
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
O1 O 0.8751(2) 0.8959(3) 0.53162(8) 0.0445(8) Uani 1 1 d .
O2 O 1.0163(2) 0.8901(3) 0.61844(8) 0.0402(7) Uani 1 1 d .
O3 O -0.4425(2) 0.2452(4) 0.54439(10) 0.0562(9) Uani 1 1 d .
O4 O -0.5316(3) 0.1339(4) 0.61665(9) 0.0556(9) Uani 1 1 d .
N1 N 0.4477(3) 0.6106(4) 0.62082(10) 0.0320(8) Uani 1 1 d .
N2 N 0.5705(3) 0.6026(4) 0.69633(10) 0.0286(8) Uani 1 1 d .
N3 N 0.3313(3) 0.4779(4) 0.70066(10) 0.0326(8) Uani 1 1 d .
N4 N 0.2098(3) 0.4390(4) 0.67118(11) 0.0321(8) Uani 1 1 d .
N5 N 0.1085(3) 0.3609(4) 0.69873(10) 0.0340(8) Uani 1 1 d .
N6 N -0.4296(3) 0.2057(4) 0.59111(13) 0.0431(9) Uani 1 1 d .
C1 C 0.4392(4) 0.5604(5) 0.67223(13) 0.0316(10) Uani 1 1 d .
C2 C 0.5889(3) 0.6886(5) 0.61309(13) 0.0304(10) Uani 1 1 d .
C3 C 0.6516(3) 0.7596(5) 0.56766(13) 0.0344(10) Uani 1 1 d .
H3 H 0.5973 0.7635 0.5350 0.041 Uiso 1 1 d R
C4 C 0.7967(4) 0.8228(5) 0.57222(13) 0.0367(10) Uani 1 1 d .
C5 C 0.8747(4) 0.8186(5) 0.62060(13) 0.0321(10) Uani 1 1 d .
C6 C 0.8096(3) 0.7511(5) 0.66541(13) 0.0346(10) Uani 1 1 d .
H6 H 0.8609 0.7497 0.6987 0.042 Uiso 1 1 d R
C7 C 0.6640(4) 0.6845(5) 0.65980(12) 0.0287(9) Uani 1 1 d .
C8 C 0.3343(3) 0.5936(5) 0.57918(11) 0.0435(12) Uani 1 1 d .
H8A H 0.3095 0.4683 0.5741 0.065 Uiso 1 1 calc R
H8B H 0.3740 0.6425 0.5464 0.065 Uiso 1 1 calc R
H8C H 0.2435 0.6586 0.5892 0.065 Uiso 1 1 calc R
C9 C 0.7995(4) 0.9129(5) 0.48208(12) 0.0466(12) Uani 1 1 d .
H9A H 0.7712 0.7953 0.4692 0.070 Uiso 1 1 calc R
H9B H 0.8666 0.9697 0.4567 0.070 Uiso 1 1 calc R
H9C H 0.7090 0.9852 0.4865 0.070 Uiso 1 1 calc R
C10 C 1.1042(3) 0.8880(5) 0.66567(12) 0.0412(11) Uani 1 1 d .
H10A H 1.0502 0.9509 0.6935 0.062 Uiso 1 1 calc R
H10B H 1.2007 0.9465 0.6593 0.062 Uiso 1 1 calc R
H10C H 1.1219 0.7653 0.6765 0.062 Uiso 1 1 calc R
C11 C 0.6114(3) 0.5574(5) 0.75027(11) 0.0350(10) Uani 1 1 d .
H11A H 0.6119 0.6649 0.7718 0.053 Uiso 1 1 calc R
H11B H 0.7117 0.5037 0.7508 0.053 Uiso 1 1 calc R
H11C H 0.5382 0.4733 0.7644 0.053 Uiso 1 1 calc R
C12 C -0.0215(4) 0.3223(5) 0.66852(13) 0.0325(10) Uani 1 1 d .
C13 C -0.1372(4) 0.2344(5) 0.69434(12) 0.0340(10) Uani 1 1 d .
H13 H -0.1235 0.2040 0.7307 0.041 Uiso 1 1 d R
C14 C -0.2696(3) 0.1937(5) 0.66933(13) 0.0347(10) Uani 1 1 d .
H14 H -0.3490 0.1326 0.6873 0.042 Uiso 1 1 d R
C15 C -0.2880(3) 0.2416(5) 0.61811(13) 0.0313(9) Uani 1 1 d .
C16 C -0.1761(4) 0.3256(5) 0.58997(13) 0.0373(11) Uani 1 1 d .
H16 H -0.1912 0.3535 0.5535 0.045 Uiso 1 1 d R
C17 C -0.0430(4) 0.3668(5) 0.61557(12) 0.0353(10) Uani 1 1 d .
H17 H 0.0361 0.4276 0.5974 0.042 Uiso 1 1 d R
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
C4 O1 C9 117.5(3)
C5 O2 C10 117.5(2)
C1 N1 C2 107.7(3)
C1 N1 C8 128.9(3)
C2 N1 C8 123.4(3)
C1 N2 C7 108.6(3)
C1 N2 C11 125.6(3)
C7 N2 C11 125.7(3)
N4 N3 C1 111.8(3)
N5 N4 N3 111.1(3)
N4 N5 C12 111.8(3)
O3 N6 O4 123.0(3)
O3 N6 C15 119.2(3)
O4 N6 C15 117.8(3)
N3 C1 N2 118.5(3)
N3 C1 N1 132.9(3)
N2 C1 N1 108.5(3)
C7 C2 C3 122.4(3)
C7 C2 N1 107.8(3)
C3 C2 N1 129.8(3)
C4 C3 C2 116.2(3)
C4 C3 H3 122.0
C2 C3 H3 121.8
O1 C4 C3 123.8(3)
O1 C4 C5 114.7(3)
C3 C4 C5 121.5(3)
O2 C5 C6 124.6(3)
O2 C5 C4 113.9(3)
C6 C5 C4 121.5(3)
C5 C6 C7 116.2(3)
C5 C6 H6 122.2
C7 C6 H6 121.7
C2 C7 N2 107.4(3)
C2 C7 C6 122.2(3)
N2 C7 C6 130.3(3)
N1 C8 H8A 109.5
N1 C8 H8B 109.5
H8A C8 H8B 109.5
N1 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O1 C9 H9A 109.5
O1 C9 H9B 109.5
H9A C9 H9B 109.5
O1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
O2 C10 H10A 109.5
O2 C10 H10B 109.5
H10A C10 H10B 109.5
O2 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
N2 C11 H11A 109.5
N2 C11 H11B 109.5
H11A C11 H11B 109.5
N2 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C13 C12 C17 118.0(3)
C13 C12 N5 116.5(3)
C17 C12 N5 125.5(3)
C14 C13 C12 121.6(3)
C14 C13 H13 119.9
C12 C13 H13 118.5
C15 C14 C13 119.0(3)
C15 C14 H14 119.7
C13 C14 H14 121.3
C14 C15 C16 122.2(3)
C14 C15 N6 120.2(3)
C16 C15 N6 117.7(3)
C15 C16 C17 118.4(3)
C15 C16 H16 120.1
C17 C16 H16 121.5
C16 C17 C12 120.8(3)
C16 C17 H17 120.6
C12 C17 H17 118.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.365(4)
O1 C9 1.433(3)
O2 C5 1.373(3)
O2 C10 1.432(3)
O3 N6 1.231(3)
O4 N6 1.242(3)
N1 C1 1.365(4)
N1 C2 1.403(4)
N1 C8 1.467(3)
N2 C1 1.356(4)
N2 C7 1.394(4)
N2 C11 1.459(3)
N3 N4 1.347(3)
N3 C1 1.356(4)
N4 N5 1.287(3)
N5 C12 1.417(4)
N6 C15 1.458(4)
C2 C7 1.362(4)
C2 C3 1.393(4)
C3 C4 1.381(4)
C3 H3 0.9601
C4 C5 1.411(4)
C5 C6 1.379(4)
C6 C7 1.397(4)
C6 H6 0.9600
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 C13 1.392(4)
C12 C17 1.401(4)
C13 C14 1.373(4)
C13 H13 0.9601
C14 C15 1.362(4)
C14 H14 0.9600
C15 C16 1.383(4)
C16 C17 1.386(4)
C16 H16 0.9600
C17 H17 0.9600
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
C3 H3 O3 0.96 2.44 3.400(4) 174.8 3_566
C8 H8B O3 0.98 2.54 3.510(4) 172.0 3_566
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C1 N3 N4 N5 -180.0(3)
N3 N4 N5 C12 178.8(3)
N4 N3 C1 N2 -177.9(3)
N4 N3 C1 N1 0.2(5)
C7 N2 C1 N3 179.6(3)
C11 N2 C1 N3 4.0(5)
C7 N2 C1 N1 1.1(4)
C11 N2 C1 N1 -174.5(3)
C2 N1 C1 N3 -178.9(4)
C8 N1 C1 N3 2.1(6)
C2 N1 C1 N2 -0.7(4)
C8 N1 C1 N2 -179.7(3)
C1 N1 C2 C7 0.1(4)
C8 N1 C2 C7 179.2(3)
C1 N1 C2 C3 179.6(4)
C8 N1 C2 C3 -1.3(6)
C7 C2 C3 C4 1.4(5)
N1 C2 C3 C4 -178.1(4)
C9 O1 C4 C3 2.2(5)
C9 O1 C4 C5 -176.7(3)
C2 C3 C4 O1 179.7(3)
C2 C3 C4 C5 -1.4(5)
C10 O2 C5 C6 2.5(5)
C10 O2 C5 C4 -178.8(3)
O1 C4 C5 O2 0.3(5)
C3 C4 C5 O2 -178.6(3)
O1 C4 C5 C6 179.1(3)
C3 C4 C5 C6 0.1(6)
O2 C5 C6 C7 179.8(3)
C4 C5 C6 C7 1.2(5)
C3 C2 C7 N2 -179.0(3)
N1 C2 C7 N2 0.6(4)
C3 C2 C7 C6 -0.1(6)
N1 C2 C7 C6 179.5(3)
C1 N2 C7 C2 -1.0(4)
C11 N2 C7 C2 174.6(3)
C1 N2 C7 C6 -179.8(4)
C11 N2 C7 C6 -4.2(6)
C5 C6 C7 C2 -1.2(5)
C5 C6 C7 N2 177.4(3)
N4 N5 C12 C13 178.8(3)
N4 N5 C12 C17 -1.9(5)
C17 C12 C13 C14 -0.8(5)
N5 C12 C13 C14 178.6(3)
C12 C13 C14 C15 -0.4(5)
C13 C14 C15 C16 1.8(5)
C13 C14 C15 N6 -177.8(3)
O3 N6 C15 C14 -177.9(3)
O4 N6 C15 C14 1.3(5)
O3 N6 C15 C16 2.5(5)
O4 N6 C15 C16 -178.4(3)
C14 C15 C16 C17 -2.0(6)
N6 C15 C16 C17 177.6(3)
C15 C16 C17 C12 0.8(5)
C13 C12 C17 C16 0.5(5)
N5 C12 C17 C16 -178.7(4)
