#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/52/2235228.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_2235228
loop_
_publ_author_name
'Yousuf, Sammer'
'Arshad, Muhammad'
'Butt, Hafiza Madiha'
'Saeed, Sumayya'
'Basha, Fatima Z.'
_publ_section_title
;
 2-Azido-1-(4-nitrophenyl)ethanone
;
_journal_coeditor_code           RZ2752
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1952
_journal_paper_doi               10.1107/S1600536812021241
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C8 H6 N4 O3'
_chemical_formula_moiety         'C8 H6 N4 O3'
_chemical_formula_sum            'C8 H6 N4 O3'
_chemical_formula_weight         206.17
_chemical_name_systematic
;
2-Azido-1-(4-nitrophenyl)ethanone
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6307(5)
_cell_length_b                   9.5168(6)
_cell_length_c                   12.4097(8)
_cell_measurement_reflns_used    1557
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.22
_cell_measurement_theta_min      3.28
_cell_volume                     901.19(10)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON
(Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
;
Bruker SMART APEX CCD area-detector
;
_diffrn_measurement_method       'ω 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  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4914
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.9869
_exptl_absorpt_correction_T_min  0.9422
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colourles
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.107
_refine_ls_abs_structure_details 'Flack (1983), 767 Friedel pairs'
_refine_ls_abs_structure_Flack   0.2(14)
_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     136
_refine_ls_number_reflns         1649
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0318
_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)+(0.0342P)²+0.0663P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0703
_refine_ls_wR_factor_ref         0.0740
_reflns_number_gt                1461
_reflns_number_total             1649
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2752.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     'P 2c 2ac'
_cod_database_code               2235228
_cod_database_fobs_code          2235228
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'
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_symmetry_multiplicity
O O1 0.9428(3) 1.19359(17) 0.40028(13) 0.0815(5) Uani d . 1 1
O O2 0.9798(2) 1.30833(17) 0.54808(15) 0.0744(5) Uani d . 1 1
O O3 0.6676(2) 0.72287(15) 0.81581(12) 0.0673(4) Uani d . 1 1
N N1 0.9448(2) 1.20158(19) 0.49879(14) 0.0553(5) Uani d . 1 1
N N2 0.7720(3) 0.45389(18) 0.76819(14) 0.0603(5) Uani d . 1 1
N N3 0.8183(2) 0.45144(17) 0.86298(15) 0.0553(4) Uani d . 1 1
N N4 0.8503(3) 0.4344(2) 0.95022(17) 0.0740(6) Uani d . 1 1
C C1 0.9238(2) 0.9459(2) 0.51250(14) 0.0478(5) Uani d . 1 1
H H1A 0.9657 0.9388 0.4423 0.057 Uiso calc R 1 1
C C2 0.8824(3) 0.8273(2) 0.57102(15) 0.0472(5) Uani d . 1 1
H H2B 0.8991 0.7389 0.5407 0.057 Uiso calc R 1 1
C C3 0.8160(2) 0.83847(19) 0.67466(14) 0.0418(4) Uani d . 1 1
C C4 0.7943(2) 0.9715(2) 0.71966(14) 0.0474(5) Uani d . 1 1
H H4A 0.7489 0.9796 0.7889 0.057 Uiso calc R 1 1
C C5 0.8386(2) 1.0906(2) 0.66373(16) 0.0482(4) Uani d . 1 1
H H5A 0.8264 1.1791 0.6946 0.058 Uiso calc R 1 1
C C6 0.9017(2) 1.0752(2) 0.56038(14) 0.0438(4) Uani d . 1 1
C C7 0.7632(3) 0.7125(2) 0.73869(14) 0.0459(4) Uani d . 1 1
C C8 0.8367(3) 0.57217(19) 0.70483(15) 0.0520(5) Uani d . 1 1
H H8A 0.8079 0.5563 0.6297 0.062 Uiso calc R 1 1
H H8B 0.9634 0.5754 0.7107 0.062 Uiso calc R 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.1121(14) 0.0726(11) 0.0598(10) -0.0001(10) 0.0104(9) 0.0177(8)
O2 0.0870(11) 0.0473(9) 0.0889(12) -0.0090(8) -0.0091(10) 0.0089(9)
O3 0.0804(11) 0.0609(9) 0.0606(8) -0.0032(7) 0.0250(8) 0.0022(7)
N1 0.0540(10) 0.0514(12) 0.0607(12) 0.0034(8) -0.0015(9) 0.0086(9)
N2 0.0725(12) 0.0476(10) 0.0607(10) -0.0110(9) -0.0118(9) 0.0040(8)
N3 0.0606(11) 0.0435(9) 0.0617(11) -0.0068(8) -0.0014(9) 0.0033(8)
N4 0.0883(14) 0.0733(14) 0.0603(11) -0.0078(11) -0.0024(11) 0.0088(10)
C1 0.0507(10) 0.0538(13) 0.0390(9) 0.0025(9) 0.0020(8) -0.0012(9)
C2 0.0520(10) 0.0424(11) 0.0472(10) 0.0023(9) 0.0000(9) -0.0059(8)
C3 0.0402(9) 0.0447(11) 0.0406(9) -0.0012(8) -0.0020(8) -0.0021(8)
C4 0.0498(10) 0.0512(12) 0.0413(9) -0.0013(9) 0.0033(8) -0.0052(9)
C5 0.0510(10) 0.0419(11) 0.0516(10) 0.0002(8) -0.0032(9) -0.0080(9)
C6 0.0399(9) 0.0439(11) 0.0475(9) -0.0005(8) -0.0050(8) 0.0046(9)
C7 0.0460(9) 0.0490(11) 0.0426(9) -0.0047(9) -0.0030(9) -0.0025(8)
C8 0.0594(12) 0.0456(12) 0.0510(10) -0.0008(10) -0.0012(10) 0.0031(9)
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
O2 N1 O1 123.83(18)
O2 N1 C6 118.28(16)
O1 N1 C6 117.89(18)
N3 N2 C8 115.67(17)
N4 N3 N2 171.7(2)
C6 C1 C2 118.44(17)
C6 C1 H1A 120.8
C2 C1 H1A 120.8
C1 C2 C3 120.62(18)
C1 C2 H2B 119.7
C3 C2 H2B 119.7
C2 C3 C4 119.02(17)
C2 C3 C7 122.04(17)
C4 C3 C7 118.93(15)
C5 C4 C3 121.25(16)
C5 C4 H4A 119.4
C3 C4 H4A 119.4
C4 C5 C6 118.00(18)
C4 C5 H5A 121.0
C6 C5 H5A 121.0
C1 C6 C5 122.64(18)
C1 C6 N1 118.80(16)
C5 C6 N1 118.55(18)
O3 C7 C3 121.29(19)
O3 C7 C8 121.17(19)
C3 C7 C8 117.52(15)
N2 C8 C7 114.03(16)
N2 C8 H8A 108.7
C7 C8 H8A 108.7
N2 C8 H8B 108.7
C7 C8 H8B 108.7
H8A C8 H8B 107.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.225(2)
O2 N1 1.216(2)
O3 C7 1.207(2)
N1 C6 1.462(2)
N2 N3 1.229(2)
N2 C8 1.459(2)
N3 N4 1.122(2)
C1 C6 1.377(3)
C1 C2 1.379(3)
C1 H1A 0.9300
C2 C3 1.386(2)
C2 H2B 0.9300
C3 C4 1.393(3)
C3 C7 1.493(3)
C4 C5 1.372(3)
C4 H4A 0.9300
C5 C6 1.378(3)
C5 H5A 0.9300
C7 C8 1.508(3)
C8 H8A 0.9700
C8 H8B 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
C8 H8B N2 4_565 0.9700 2.4800 3.422(3) 165.00 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
C8 N2 N3 N4 -176.5(17)
C6 C1 C2 C3 1.5(3)
C1 C2 C3 C4 -1.0(3)
C1 C2 C3 C7 177.54(16)
C2 C3 C4 C5 -0.6(3)
C7 C3 C4 C5 -179.14(16)
C3 C4 C5 C6 1.5(3)
C2 C1 C6 C5 -0.6(3)
C2 C1 C6 N1 -179.83(16)
C4 C5 C6 C1 -0.9(3)
C4 C5 C6 N1 178.33(16)
O2 N1 C6 C1 -156.72(18)
O1 N1 C6 C1 23.6(2)
O2 N1 C6 C5 24.0(2)
O1 N1 C6 C5 -155.73(18)
C2 C3 C7 O3 -161.46(19)
C4 C3 C7 O3 17.1(3)
C2 C3 C7 C8 19.8(2)
C4 C3 C7 C8 -161.67(16)
N3 N2 C8 C7 -67.2(3)
O3 C7 C8 N2 4.1(3)
C3 C7 C8 N2 -177.17(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10202641
