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#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/58/7205833.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_7205833
loop_
_publ_author_name
'Bushmarinov, Ivan S.'
'Nabiev, Orudzh G.'
'Kostyanovsky, Remir G.'
'Antipin, Mikhail Yu.'
'Lyssenko, Konstantin A.'
_publ_section_title
;
 The azide anion as a building block in crystal engineering from a
 charge density point of view
;
_journal_issue                   8
_journal_name_full               CrystEngComm
_journal_page_first              2930
_journal_paper_doi               10.1039/c0ce00859a
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C12 H28 N2 O4, 2(N3)'
_chemical_formula_sum            'C12 H28 N8 O4'
_chemical_formula_weight         348.42
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.3164(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.60360(10)
_cell_length_b                   8.54800(10)
_cell_length_c                   13.8275(2)
_cell_measurement_reflns_used    394
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      55
_cell_measurement_theta_min      3
_cell_volume                     898.71(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector''
_diffrn_measurement_method       'omega 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  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            75866
_diffrn_reflns_theta_full        55.73
_diffrn_reflns_theta_max         55.73
_diffrn_reflns_theta_min         2.68
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         11838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0606P)²+0.0335P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1222
_reflns_number_gt                7780
_reflns_number_total             11838
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c0ce00859a.txt
_cod_data_source_block           DCDA
_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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7205833
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
O1 O 0.31963(4) -0.31889(4) 1.00989(2) 0.01617(4) Uani 1 1 d . . .
O2 O 0.26702(4) -0.08387(3) 1.16192(2) 0.01601(4) Uani 1 1 d . . .
N1 N 0.57709(4) -0.21303(4) 0.88934(2) 0.01370(4) Uani 1 1 d . . .
H2N H 0.5029(12) -0.1363(11) 0.8729(6) 0.025(2) Uiso 1 1 d . . .
H1N H 0.6016(13) -0.2053(11) 0.9528(7) 0.029(2) Uiso 1 1 d . . .
N2 N 0.30236(5) -0.00334(4) 0.83374(3) 0.01854(5) Uani 1 1 d . . .
N3 N 0.28833(4) 0.11346(4) 0.87837(2) 0.01362(4) Uani 1 1 d . . .
N4 N 0.27126(6) 0.23159(5) 0.92141(3) 0.02207(6) Uani 1 1 d . . .
C1 C 0.48924(5) -0.36689(4) 0.87039(3) 0.01595(5) Uani 1 1 d . . .
H1B H 0.5585(11) -0.4485(9) 0.9026(6) 0.0187(17) Uiso 1 1 d . . .
H1A H 0.4878(12) -0.3842(10) 0.8004(6) 0.0222(19) Uiso 1 1 d . . .
C2 C 0.30547(5) -0.36514(4) 0.91125(3) 0.01621(5) Uani 1 1 d . . .
H2B H 0.2532(11) -0.4681(10) 0.9053(6) 0.0218(19) Uiso 1 1 d . . .
H2A H 0.2332(11) -0.2894(10) 0.8773(6) 0.0200(18) Uiso 1 1 d . . .
C3 C 0.15350(5) -0.28859(5) 1.05163(3) 0.01708(5) Uani 1 1 d . . .
H3B H 0.0881(12) -0.2123(10) 1.0124(6) 0.0216(19) Uiso 1 1 d . . .
H3A H 0.0829(13) -0.3839(11) 1.0559(7) 0.028(2) Uiso 1 1 d . . .
C4 C 0.17961(5) -0.23113(5) 1.15413(3) 0.01699(5) Uani 1 1 d . . .
H4B H 0.2536(12) -0.3052(10) 1.1890(6) 0.024(2) Uiso 1 1 d . . .
H4A H 0.0634(12) -0.2267(10) 1.1846(6) 0.0224(19) Uiso 1 1 d . . .
C5 C 0.16048(5) 0.04500(5) 1.13465(3) 0.01917(6) Uani 1 1 d . . .
H5B H 0.0452(12) 0.0369(11) 1.1666(7) 0.028(2) Uiso 1 1 d . . .
H5A H 0.1369(12) 0.0421(11) 1.0636(7) 0.028(2) Uiso 1 1 d . . .
C6 C 0.25481(5) 0.19353(5) 1.16411(3) 0.01921(6) Uani 1 1 d . . .
H6B H 0.1804(12) 0.2823(11) 1.1503(7) 0.026(2) Uiso 1 1 d . . .
H6A H 0.2844(13) 0.1932(11) 1.2343(7) 0.028(2) Uiso 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
_geom_angle_publ_flag
C3 O1 C2 112.24(3) . . ?
C5 O2 C4 113.59(3) . . ?
C6 N1 C1 113.24(3) 3_657 . ?
C6 N1 H2N 109.5(6) 3_657 . ?
C1 N1 H2N 108.6(6) . . ?
C6 N1 H1N 107.6(6) 3_657 . ?
C1 N1 H1N 109.0(6) . . ?
H2N N1 H1N 108.8(8) . . ?
N2 N3 N4 178.36(4) . . ?
N1 C1 C2 109.79(3) . . ?
N1 C1 H1B 107.9(5) . . ?
C2 C1 H1B 109.4(5) . . ?
N1 C1 H1A 108.0(5) . . ?
C2 C1 H1A 111.5(5) . . ?
H1B C1 H1A 110.2(7) . . ?
O1 C2 C1 107.22(3) . . ?
O1 C2 H2B 111.3(5) . . ?
C1 C2 H2B 109.8(5) . . ?
O1 C2 H2A 108.6(5) . . ?
C1 C2 H2A 110.4(5) . . ?
H2B C2 H2A 109.5(7) . . ?
O1 C3 C4 109.20(3) . . ?
O1 C3 H3B 110.3(5) . . ?
C4 C3 H3B 111.5(5) . . ?
O1 C3 H3A 111.3(6) . . ?
C4 C3 H3A 106.4(5) . . ?
H3B C3 H3A 108.1(8) . . ?
O2 C4 C3 114.58(3) . . ?
O2 C4 H4B 105.6(5) . . ?
C3 C4 H4B 109.0(5) . . ?
O2 C4 H4A 110.7(5) . . ?
C3 C4 H4A 107.5(5) . . ?
H4B C4 H4A 109.4(7) . . ?
O2 C5 C6 108.13(3) . . ?
O2 C5 H5B 109.5(5) . . ?
C6 C5 H5B 111.1(6) . . ?
O2 C5 H5A 110.0(5) . . ?
C6 C5 H5A 111.6(5) . . ?
H5B C5 H5A 106.5(8) . . ?
N1 C6 C5 111.54(3) 3_657 . ?
N1 C6 H6B 108.5(6) 3_657 . ?
C5 C6 H6B 109.3(6) . . ?
N1 C6 H6A 107.1(6) 3_657 . ?
C5 C6 H6A 111.4(5) . . ?
H6B C6 H6A 108.9(8) . . ?
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
O1 C3 1.4156(5) . ?
O1 C2 1.4235(5) . ?
O2 C5 1.4172(5) . ?
O2 C4 1.4273(5) . ?
N1 C6 1.4894(5) 3_657 ?
N1 C1 1.4976(5) . ?
N1 H2N 0.893(9) . ?
N1 H1N 0.899(9) . ?
N2 N3 1.1789(5) . ?
N3 N4 1.1797(5) . ?
C1 C2 1.5102(6) . ?
C1 H1B 0.980(8) . ?
C1 H1A 0.978(9) . ?
C2 H2B 0.969(9) . ?
C2 H2A 0.969(9) . ?
C3 C4 1.5121(6) . ?
C3 H3B 0.981(9) . ?
C3 H3A 0.978(9) . ?
C4 H4B 0.973(9) . ?
C4 H4A 0.981(9) . ?
C5 C6 1.5130(6) . ?
C5 H5B 0.987(9) . ?
C5 H5A 0.998(9) . ?
C6 N1 1.4894(5) 3_657 ?
C6 H6B 0.964(10) . ?
C6 H6A 0.995(9) . ?
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 H2N N2 0.893(9) 1.975(9) 2.8548(5) 167.8(9) .
N1 H1N N4 0.899(9) 1.998(9) 2.8581(5) 159.9(9) 3_657
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
C6 N1 C1 C2 -169.22(3) 3_657 . . . ?
C3 O1 C2 C1 170.46(3) . . . . ?
N1 C1 C2 O1 -52.82(4) . . . . ?
C2 O1 C3 C4 -176.68(3) . . . . ?
C5 O2 C4 C3 73.60(4) . . . . ?
O1 C3 C4 O2 65.16(4) . . . . ?
C4 O2 C5 C6 169.29(3) . . . . ?
O2 C5 C6 N1 64.11(5) . . . 3_657 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168354020
