#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/84/2208410.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_2208410
loop_
_publ_author_name
'Xiao-Ru Zhang'
'Shu-Sheng Zhang'
'Min-Hua Xu'
'Xue-Mei Li'
_publ_section_title
;
 Bis(2-azidoethyl) isophthalate
;
_journal_coeditor_code           RZ6169
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1040
_journal_page_last               o1041
_journal_paper_doi               10.1107/S1600536806004909
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C12 H12 N6 O4'
_chemical_formula_moiety         'C12 H12 N6 O4'
_chemical_formula_sum            'C12 H12 N6 O4'
_chemical_formula_weight         304.28
_chemical_name_systematic
;
Bis(2-azidoethyl) isophthalate
;
_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                 119.164(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.616(3)
_cell_length_b                   7.2262(19)
_cell_length_c                   21.640(5)
_cell_measurement_reflns_used    1426
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.4
_cell_measurement_theta_min      3.0
_cell_volume                     1449.6(7)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
;
Siemens SMART 1000 CCD area-detector
;
_diffrn_measurement_method       ω
_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  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8307
_diffrn_reflns_theta_full        25.76
_diffrn_reflns_theta_max         25.76
_diffrn_reflns_theta_min         2.16
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_correction_T_min  0.9682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.171
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2756
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0874
_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)+(0.0614P)²+0.2657P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1416
_reflns_number_gt                1767
_reflns_number_total             2756
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz6169.cif
_cod_data_source_block           I
_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 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2208410
_cod_database_fobs_code          2208410
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
O O1 0.47069(16) -0.3537(2) -0.12170(7) 0.0575(5) Uani d . 1
O O2 0.23135(18) -0.3548(3) -0.16842(9) 0.0809(6) Uani d . 1
O O3 0.70533(19) -0.0966(3) 0.19206(8) 0.0786(6) Uani d . 1
O O4 0.78910(16) -0.2251(2) 0.12540(7) 0.0577(5) Uani d . 1
N N1 0.8921(3) -0.1779(4) -0.14579(19) 0.1210(11) Uani d . 1
N N2 0.7776(3) -0.2100(3) -0.15997(11) 0.0716(6) Uani d . 1
N N3 0.6510(2) -0.2255(3) -0.17660(11) 0.0657(6) Uani d . 1
N N4 1.0498(3) -0.2841(4) 0.11207(14) 0.0952(8) Uani d . 1
N N5 0.9523(3) -0.3200(4) 0.05241(16) 0.0977(9) Uani d . 1
N N6 0.8699(4) -0.3471(6) -0.00540(16) 0.1541(16) Uani d . 1
C C1 0.5993(3) -0.4182(4) -0.18273(13) 0.0651(7) Uani d . 1
H H1A 0.5948 -0.4766 -0.2241 0.066(7) Uiso d R 1
H H1B 0.6648 -0.4888 -0.1413 0.078(8) Uiso d R 1
C C2 0.4539(3) -0.4135(4) -0.18909(12) 0.0678(7) Uani d . 1
H H2A 0.4104 -0.5355 -0.2009 0.075(8) Uiso d R 1
H H2B 0.3921 -0.3282 -0.2262 0.072(8) Uiso d R 1
C C3 0.3497(2) -0.3285(3) -0.11872(12) 0.0527(6) Uani d . 1
C C4 0.3784(2) -0.2632(3) -0.04763(11) 0.0483(5) Uani d . 1
C C5 0.2617(3) -0.2129(4) -0.03903(14) 0.0650(7) Uani d . 1
H H5A 0.1686 -0.2238 -0.0769 0.075(8) Uiso d R 1
C C6 0.2824(3) -0.1472(4) 0.02484(15) 0.0737(8) Uani d . 1
H H6A 0.2036 -0.1134 0.0301 0.080(8) Uiso d R 1
C C7 0.4191(3) -0.1316(3) 0.08072(14) 0.0631(7) Uani d . 1
H H7A 0.4326 -0.0860 0.1237 0.079(8) Uiso d R 1
C C8 0.5382(2) -0.1829(3) 0.07405(11) 0.0471(5) Uani d . 1
C C9 0.5170(2) -0.2492(3) 0.00925(10) 0.0439(5) Uani d . 1
H H9A 0.5956 -0.2843 0.0041 0.043(6) Uiso d R 1
C C10 0.6838(3) -0.1622(3) 0.13653(11) 0.0521(6) Uani d . 1
C C11 0.9336(3) -0.2180(4) 0.18482(11) 0.0668(7) Uani d . 1
H H11A 0.9713 -0.0930 0.1911 0.075(8) Uiso d R 1
H H11B 0.9332 -0.2549 0.2278 0.083(8) Uiso d R 1
C C12 1.0251(3) -0.3468(4) 0.16984(13) 0.0736(8) Uani d . 1
H H12A 0.9792 -0.4674 0.1578 0.089(10) Uiso d R 1
H H12B 1.1175 -0.3607 0.2124 0.094(9) Uiso d 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'
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
C3 O1 C2 116.26(17)
C10 O4 C11 116.58(17)
N1 N2 N3 173.3(3)
N2 N3 C1 115.0(2)
N5 N4 C12 114.9(2)
N6 N5 N4 173.5(3)
N3 C1 C2 108.1(2)
N3 C1 H1A 110.0
C2 C1 H1A 110.1
N3 C1 H1B 110.2
C2 C1 H1B 110.0
H1A C1 H1B 108.4
O1 C2 C1 107.58(19)
O1 C2 H2A 110.2
C1 C2 H2A 110.2
O1 C2 H2B 110.2
C1 C2 H2B 110.2
H2A C2 H2B 108.5
O2 C3 O1 123.1(2)
O2 C3 C4 124.7(2)
O1 C3 C4 112.15(18)
C5 C4 C9 119.5(2)
C5 C4 C3 118.3(2)
C9 C4 C3 122.2(2)
C6 C5 C4 120.6(2)
C6 C5 H5A 119.7
C4 C5 H5A 119.7
C7 C6 C5 119.9(2)
C7 C6 H6A 120.0
C5 C6 H6A 120.1
C6 C7 C8 120.8(2)
C6 C7 H7A 119.6
C8 C7 H7A 119.6
C7 C8 C9 119.1(2)
C7 C8 C10 118.3(2)
C9 C8 C10 122.55(19)
C4 C9 C8 120.0(2)
C4 C9 H9A 120.0
C8 C9 H9A 120.0
O3 C10 O4 123.1(2)
O3 C10 C8 123.7(2)
O4 C10 C8 113.19(18)
O4 C11 C12 107.83(19)
O4 C11 H11A 110.1
C12 C11 H11A 110.1
O4 C11 H11B 110.2
C12 C11 H11B 110.2
H11A C11 H11B 108.4
N4 C12 C11 113.5(2)
N4 C12 H12A 108.9
C11 C12 H12A 108.9
N4 C12 H12B 108.9
C11 C12 H12B 108.8
H12A C12 H12B 107.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C3 1.330(3) yes
O1 C2 1.446(3) yes
O2 C3 1.206(3) yes
O3 C10 1.206(2) yes
O4 C10 1.333(3) yes
O4 C11 1.445(3) yes
N1 N2 1.123(3) yes
N2 N3 1.215(3) yes
N3 C1 1.479(3) ?
N4 N5 1.226(3) yes
N4 C12 1.469(3) ?
N5 N6 1.141(4) yes
C1 C2 1.482(3) ?
C1 H1A 0.9698 ?
C1 H1B 0.9700 ?
C2 H2A 0.9700 ?
C2 H2B 0.9700 ?
C3 C4 1.492(3) ?
C4 C5 1.387(3) ?
C4 C9 1.388(3) ?
C5 C6 1.374(4) ?
C5 H5A 0.9300 ?
C6 C7 1.368(3) ?
C6 H6A 0.9300 ?
C7 C8 1.391(3) ?
C7 H7A 0.9300 ?
C8 C9 1.392(3) ?
C8 C10 1.484(3) ?
C9 H9A 0.9299 ?
C11 C12 1.491(3) ?
C11 H11A 0.9700 ?
C11 H11B 0.9699 ?
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C5 H5A N1 1_455 0.93 2.58 3.459(5) 157 yes
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
N2 N3 C1 C2 169.0(2)
C3 O1 C2 C1 175.4(2)
N3 C1 C2 O1 -69.0(3)
C2 O1 C3 O2 0.7(3)
C2 O1 C3 C4 -178.80(19)
O2 C3 C4 C5 -6.0(3)
O1 C3 C4 C5 173.5(2)
O2 C3 C4 C9 174.8(2)
O1 C3 C4 C9 -5.7(3)
C9 C4 C5 C6 0.9(4)
C3 C4 C5 C6 -178.3(2)
C4 C5 C6 C7 -0.2(4)
C5 C6 C7 C8 -0.5(4)
C6 C7 C8 C9 0.6(3)
C6 C7 C8 C10 179.9(2)
C5 C4 C9 C8 -0.8(3)
C3 C4 C9 C8 178.32(19)
C7 C8 C9 C4 0.1(3)
C10 C8 C9 C4 -179.1(2)
C11 O4 C10 O3 2.4(3)
C11 O4 C10 C8 -177.1(2)
C7 C8 C10 O3 -3.0(4)
C9 C8 C10 O3 176.2(2)
C7 C8 C10 O4 176.45(19)
C9 C8 C10 O4 -4.3(3)
C10 O4 C11 C12 161.6(2)
N5 N4 C12 C11 -82.3(3)
O4 C11 C12 N4 68.8(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21126323
