#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:12:35 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180293 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/07/7150753.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_7150753
loop_
_publ_author_name
'Plietzsch, Oliver'
'Schilling, Christine Inge'
'Tolev, Mariyan'
'Nieger, Martin'
'Richert, Clemens'
'Muller, Thierry'
'Bräse, Stefan'
_publ_section_title
;
 Four-fold click reactions: Generation of tetrahedral methane- and
 adamantane-based building blocks for higher-order molecular assemblies
;
_journal_issue                   22
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              4734
_journal_page_last               4743
_journal_paper_doi               10.1039/b912189g
_journal_volume                  7
_journal_year                    2009
_chemical_formula_moiety         'C25 H16 N12'
_chemical_formula_sum            'C25 H16 N12'
_chemical_formula_weight         484.50
_chemical_name_common            Tetrakis(4-azidophenyl)methane
_chemical_name_systematic
;
Tetrakis(4-azidophenyl)methane
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 111.37(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.728(1)
_cell_length_b                   7.137(1)
_cell_length_c                   18.265(1)
_cell_measurement_reflns_used    62
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      1
_cell_volume                     2273.5(4)
_computing_cell_refinement       'EVALCCD (Duisenberg et al., 2003)'
_computing_data_collection       'Collect (Nonius, 1998)'
_computing_data_reduction        'EVALCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    XP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'rotation in phi and omega, 2 deg.'
_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  0.0460
_diffrn_reflns_av_sigmaI/netI    0.0626
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8191
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rods
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2578
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0510
_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)+(0.0482P)²+1.3862P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1161
_reflns_number_gt                1710
_reflns_number_total             2578
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b912189g.txt
_cod_data_source_block           sb091_hy_compound_7
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7150753
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C1 C 0.5000 0.4620(3) 0.2500 0.0169(5) Uani 1 2 d S . .
C11 C 0.43869(11) 0.3324(2) 0.19220(10) 0.0184(4) Uani 1 1 d . . .
C12 C 0.36075(11) 0.3430(2) 0.17843(11) 0.0209(4) Uani 1 1 d . . .
H12 H 0.3429 0.4349 0.2053 0.025 Uiso 1 1 calc R . .
C13 C 0.30808(11) 0.2216(2) 0.12605(11) 0.0218(4) Uani 1 1 d . . .
H13 H 0.2550 0.2313 0.1174 0.026 Uiso 1 1 calc R . .
C14 C 0.33384(11) 0.0866(2) 0.08672(11) 0.0203(4) Uani 1 1 d . . .
C15 C 0.41151(11) 0.0720(2) 0.10059(11) 0.0219(4) Uani 1 1 d . . .
H15 H 0.4295 -0.0207 0.0742 0.026 Uiso 1 1 calc R . .
C16 C 0.46262(11) 0.1928(2) 0.15302(11) 0.0209(4) Uani 1 1 d . . .
H16 H 0.5158 0.1803 0.1626 0.025 Uiso 1 1 calc R . .
N11 N 0.28518(9) -0.0456(2) 0.03277(10) 0.0265(4) Uani 1 1 d . . .
N12 N 0.21563(10) -0.0327(2) 0.02104(10) 0.0251(4) Uani 1 1 d . . .
N13 N 0.15144(11) -0.0360(2) 0.00541(11) 0.0366(5) Uani 1 1 d . . .
C21 C 0.53677(10) 0.5945(2) 0.20621(11) 0.0180(4) Uani 1 1 d . . .
C22 C 0.52105(11) 0.5879(3) 0.12594(11) 0.0220(4) Uani 1 1 d . . .
H22 H 0.4885 0.4922 0.0952 0.026 Uiso 1 1 calc R . .
C23 C 0.55213(11) 0.7189(3) 0.08967(12) 0.0248(4) Uani 1 1 d . . .
H23 H 0.5402 0.7133 0.0345 0.030 Uiso 1 1 calc R . .
C24 C 0.60021(11) 0.8570(2) 0.13376(12) 0.0230(4) Uani 1 1 d . . .
C25 C 0.61804(11) 0.8642(2) 0.21427(11) 0.0214(4) Uani 1 1 d . . .
H25 H 0.6521 0.9572 0.2451 0.026 Uiso 1 1 calc R . .
C26 C 0.58588(11) 0.7352(2) 0.24925(11) 0.0204(4) Uani 1 1 d . . .
H26 H 0.5975 0.7424 0.3043 0.025 Uiso 1 1 calc R . .
N21 N 0.62729(11) 0.9898(2) 0.09128(11) 0.0333(4) Uani 1 1 d . . .
N22 N 0.67104(11) 1.1132(3) 0.13145(11) 0.0350(5) Uani 1 1 d . . .
N23 N 0.71085(13) 1.2327(3) 0.16039(13) 0.0548(6) 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'
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
_geom_angle_publ_flag
C11 C1 C11 106.76(19) . 2_655 ?
C11 C1 C21 111.71(9) . . ?
C11 C1 C21 110.89(9) 2_655 . ?
C11 C1 C21 110.89(9) . 2_655 ?
C11 C1 C21 111.71(9) 2_655 2_655 ?
C21 C1 C21 104.96(19) . 2_655 ?
C12 C11 C16 117.33(16) . . ?
C12 C11 C1 123.99(15) . . ?
C16 C11 C1 118.66(15) . . ?
C11 C12 C13 121.56(17) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C12 119.51(17) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C13 119.79(17) . . ?
C15 C14 N11 116.08(16) . . ?
C13 C14 N11 124.11(17) . . ?
C16 C15 C14 119.69(17) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C11 122.10(17) . . ?
C15 C16 H16 118.9 . . ?
C11 C16 H16 118.9 . . ?
N12 N11 C14 115.76(16) . . ?
N13 N12 N11 173.01(19) . . ?
C22 C21 C26 117.55(17) . . ?
C22 C21 C1 124.12(15) . . ?
C26 C21 C1 118.26(15) . . ?
C21 C22 C23 121.09(18) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C24 C23 C22 119.99(19) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.01(17) . . ?
C23 C24 N21 116.23(18) . . ?
C25 C24 N21 123.74(17) . . ?
C26 C25 C24 119.36(17) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C25 C26 C21 121.98(18) . . ?
C25 C26 H26 119.0 . . ?
C21 C26 H26 119.0 . . ?
N22 N21 C24 115.90(17) . . ?
N23 N22 N21 172.5(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C11 1.551(2) . ?
C1 C11 1.551(2) 2_655 ?
C1 C21 1.552(2) . ?
C1 C21 1.552(2) 2_655 ?
C11 C12 1.390(2) . ?
C11 C16 1.393(2) . ?
C12 C13 1.397(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(3) . ?
C14 N11 1.428(2) . ?
C15 C16 1.382(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
N11 N12 1.244(2) . ?
N12 N13 1.130(2) . ?
C21 C22 1.387(3) . ?
C21 C26 1.395(3) . ?
C22 C23 1.390(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.379(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.385(3) . ?
C24 N21 1.430(2) . ?
C25 C26 1.378(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
N21 N22 1.244(2) . ?
N22 N23 1.130(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
C22 H22 N13 0.95 2.61 3.268(3) 126.3 7
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 C1 C11 C12 125.63(19) 2_655 . . . ?
C21 C1 C11 C12 -112.98(17) . . . . ?
C21 C1 C11 C12 3.7(2) 2_655 . . . ?
C11 C1 C11 C16 -52.43(13) 2_655 . . . ?
C21 C1 C11 C16 69.0(2) . . . . ?
C21 C1 C11 C16 -174.34(15) 2_655 . . . ?
C16 C11 C12 C13 -1.5(3) . . . . ?
C1 C11 C12 C13 -179.54(16) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C12 C13 C14 N11 179.22(17) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
N11 C14 C15 C16 -178.96(16) . . . . ?
C14 C15 C16 C11 -0.9(3) . . . . ?
C12 C11 C16 C15 1.9(3) . . . . ?
C1 C11 C16 C15 -179.94(16) . . . . ?
C15 C14 N11 N12 179.46(17) . . . . ?
C13 C14 N11 N12 1.1(3) . . . . ?
C14 N11 N12 N13 -179(100) . . . . ?
C11 C1 C21 C22 -4.6(2) . . . . ?
C11 C1 C21 C22 114.32(17) 2_655 . . . ?
C21 C1 C21 C22 -124.89(19) 2_655 . . . ?
C11 C1 C21 C26 172.07(15) . . . . ?
C11 C1 C21 C26 -69.0(2) 2_655 . . . ?
C21 C1 C21 C26 51.83(13) 2_655 . . . ?
C26 C21 C22 C23 -1.1(3) . . . . ?
C1 C21 C22 C23 175.64(16) . . . . ?
C21 C22 C23 C24 0.8(3) . . . . ?
C22 C23 C24 C25 0.5(3) . . . . ?
C22 C23 C24 N21 -177.78(17) . . . . ?
C23 C24 C25 C26 -1.5(3) . . . . ?
N21 C24 C25 C26 176.65(18) . . . . ?
C24 C25 C26 C21 1.2(3) . . . . ?
C22 C21 C26 C25 0.1(3) . . . . ?
C1 C21 C26 C25 -176.87(16) . . . . ?
C23 C24 N21 N22 -179.52(18) . . . . ?
C25 C24 N21 N22 2.2(3) . . . . ?
C24 N21 N22 N23 -179(100) . . . . ?
