#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/70/2017083.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2017083
loop_
_publ_author_name
'Wieland, Marcel'
'Su, Kuan-Jen'
'Wagner, Gerald'
'Brinker, Udo H.'
'Arion, Vladimir B.'
_publ_section_title
;
 1,2,4,5-Tetrakis(diazidomethyl)benzene
;
_journal_coeditor_code           DN3112
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o240
_journal_page_last               o242
_journal_paper_doi               10.1107/S0108270109013894
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C10 H6 N24'
_chemical_formula_moiety         'C10 H6 N24'
_chemical_formula_sum            'C10 H6 N24'
_chemical_formula_weight         462.39
_chemical_name_systematic
;
1,2,4,5-Tetrakis(diazidomethyl)benzene
;
_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                 107.069(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.2393(9)
_cell_length_b                   14.3799(13)
_cell_length_c                   7.5145(5)
_cell_measurement_reflns_used    341
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.72
_cell_measurement_theta_min      2.36
_cell_volume                     954.40(14)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker X8 APEXII CCD diffractometer'
_diffrn_measurement_method       φ-scan
_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  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0580
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            7716
_diffrn_reflns_theta_full        30.05
_diffrn_reflns_theta_max         30.05
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.236
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2788
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0439
_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)+(0.0522P)²+0.0067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1098
_reflns_number_gt                2019
_reflns_number_total             2788
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn3112.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               2017083
_cod_database_fobs_code          2017083
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.91528(14) 1.03914(9) 0.63096(17) 0.0163(3) Uani d . 1 . .
N N2 0.88647(13) 1.05589(9) 0.78078(17) 0.0164(3) Uani d . 1 . .
N N3 0.87172(16) 1.06764(10) 0.92248(18) 0.0240(3) Uani d . 1 . .
N N4 0.78004(14) 1.16851(8) 0.44179(17) 0.0161(3) Uani d . 1 . .
N N5 0.88280(14) 1.19971(8) 0.38321(16) 0.0154(3) Uani d . 1 . .
N N6 0.97109(16) 1.23620(10) 0.3324(2) 0.0249(3) Uani d . 1 . .
N N7 0.68467(15) 0.89448(9) 0.17263(17) 0.0185(3) Uani d . 1 . .
N N8 0.55155(17) 0.89239(10) 0.06836(18) 0.0229(3) Uani d . 1 . .
N N9 0.43738(19) 0.89170(12) -0.0393(2) 0.0361(4) Uani d . 1 . .
N N10 0.64911(14) 0.77746(8) 0.39227(17) 0.0155(3) Uani d . 1 . .
N N11 0.73079(13) 0.71714(8) 0.35134(15) 0.0125(2) Uani d . 1 . .
N N12 0.79319(15) 0.65477(9) 0.32048(17) 0.0183(3) Uani d . 1 . .
C C1 0.78768(15) 1.06633(10) 0.46406(19) 0.0127(3) Uani d . 1 . .
H H1 0.8061 1.0383 0.3508 0.015 Uiso calc R 1 . .
C C2 0.63676(15) 1.03210(10) 0.47805(17) 0.0112(3) Uani d . 1 . .
C C3 0.59506(15) 0.93873(10) 0.44106(18) 0.0103(3) Uani d . 1 . .
C C4 0.69454(16) 0.87371(9) 0.36956(19) 0.0117(3) Uani d . 1 . .
H H4 0.8019 0.8823 0.4473 0.014 Uiso calc R 1 . .
C C5 0.54181(15) 1.09201(10) 0.53764(18) 0.0112(3) Uani d . 1 . .
H H5 0.5710 1.1550 0.5642 0.013 Uiso calc R 1 . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C1 . . 112.27(11) no
N3 N2 N1 . . 174.32(15) no
N5 N4 C1 . . 112.53(12) no
N6 N5 N4 . . 173.42(15) no
N8 N7 C4 . . 112.39(12) no
N9 N8 N7 . . 173.37(16) no
N11 N10 C4 . . 114.35(11) no
N12 N11 N10 . . 171.35(14) no
N4 C1 N1 . . 110.71(11) no
N4 C1 C2 . . 108.50(11) no
N1 C1 C2 . . 111.84(11) no
N4 C1 H1 . . 108.6 no
N1 C1 H1 . . 108.6 no
C2 C1 H1 . . 108.6 no
C5 C2 C3 . . 119.56(12) y
C5 C2 C1 . . 120.11(12) y
C3 C2 C1 . . 120.24(12) y
C5 C3 C2 3_676 . 119.16(12) y
C5 C3 C4 3_676 . 120.70(12) y
C2 C3 C4 . . 120.07(12) y
N10 C4 N7 . . 111.63(11) no
N10 C4 C3 . . 108.42(11) no
N7 C4 C3 . . 111.26(11) no
N10 C4 H4 . . 108.5 no
N7 C4 H4 . . 108.5 no
C3 C4 H4 . . 108.5 no
C3 C5 C2 3_676 . 121.28(13) no
C3 C5 H5 3_676 . 119.4 no
C2 C5 H5 . . 119.4 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 N2 . 1.2539(17) no
N1 C1 . 1.4992(18) no
N2 N3 . 1.1253(17) no
N4 N5 . 1.2417(17) no
N4 C1 . 1.4782(19) no
N5 N6 . 1.1267(17) no
N7 N8 . 1.2497(19) no
N7 C4 . 1.4860(18) no
N8 N9 . 1.125(2) no
N10 N11 . 1.2461(16) no
N10 C4 . 1.4706(18) no
N11 N12 . 1.1265(16) no
C1 C2 . 1.5111(19) no
C1 H1 . 1.0000 no
C2 C5 . 1.3939(19) y
C2 C3 . 1.4020(19) y
C3 C5 3_676 1.3924(18) y
C3 C4 . 1.5158(18) no
C4 H4 . 1.0000 no
C5 C3 3_676 1.3924(18) no
C5 H5 . 0.9500 no
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N5 N4 C1 N1 . . . . 73.87(15) no
N5 N4 C1 C2 . . . . -163.05(12) no
N2 N1 C1 N4 . . . . 73.98(14) no
N2 N1 C1 C2 . . . . -47.14(16) no
N4 C1 C2 C5 . . . . -23.77(17) no
N1 C1 C2 C5 . . . . 98.62(15) no
N4 C1 C2 C3 . . . . 159.73(12) no
N1 C1 C2 C3 . . . . -77.88(15) no
C5 C2 C3 C5 . . . 3_676 0.8(2) no
C1 C2 C3 C5 . . . 3_676 177.37(12) no
C5 C2 C3 C4 . . . . 177.80(12) no
C1 C2 C3 C4 . . . . -5.68(19) no
N11 N10 C4 N7 . . . . 62.33(16) no
N11 N10 C4 C3 . . . . -174.76(11) no
N8 N7 C4 N10 . . . . 65.81(15) no
N8 N7 C4 C3 . . . . -55.45(16) no
C5 C3 C4 N10 3_676 . . . -18.62(17) no
C2 C3 C4 N10 . . . . 164.47(12) no
C5 C3 C4 N7 3_676 . . . 104.51(14) no
C2 C3 C4 N7 . . . . -72.40(16) no
C3 C2 C5 C3 . . . 3_676 -0.9(2) no
C1 C2 C5 C3 . . . 3_676 -177.39(12) no
