#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/18/2201822.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_2201822
loop_
_publ_author_name
'Simon, Monika'
'Csunderlik, Carol'
'Jones, Peter G.'
'Neda, Ion'
'Fischer, Axel K.'
_publ_section_title
;
 A second polymorph of bis(o-nitrophenyl) carbonate
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o688
_journal_page_last               o690
_journal_paper_doi               10.1107/S1600536803007487
_journal_volume                  59
_journal_year                    2003
_chemical_formula_sum            'C13 H8 N2 O7'
_chemical_formula_weight         304.21
_chemical_name_systematic
;
 Bis(o-nitrophenyl) carbonate
;
_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                 92.128(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9789(12)
_cell_length_b                   11.9076(12)
_cell_length_c                   9.1495(11)
_cell_measurement_reflns_used    4316
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      27.0
_cell_measurement_theta_min      2.4
_cell_volume                     1304.2(2)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       ω-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  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9339
_diffrn_reflns_theta_full        28.50
_diffrn_reflns_theta_max         28.50
_diffrn_reflns_theta_min         1.70
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0343
_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)+(0.0503P)²+0.1183P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0970
_reflns_number_gt                2594
_reflns_number_total             3286
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6262.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (5 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (5
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (5 times).

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               2201822
_cod_database_fobs_code          2201822
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_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
_atom_site_type_symbol
O1 0.29019(6) 0.17099(7) 0.42919(9) 0.0307(2) Uani d . 1 . . O
O2 0.21681(6) 0.05444(7) 0.59648(9) 0.03015(19) Uani d . 1 . . O
O3 0.16596(6) 0.22750(6) 0.59518(8) 0.02762(19) Uani d . 1 . . O
O4 0.50500(10) -0.00622(11) 0.83351(13) 0.0684(4) Uani d . 1 . . O
O5 0.39845(9) 0.12506(8) 0.74522(11) 0.0464(3) Uani d . 1 . . O
O6 -0.07112(8) 0.29780(8) 0.27643(12) 0.0465(3) Uani d . 1 . . O
O7 0.03683(7) 0.16887(7) 0.36686(11) 0.0400(2) Uani d . 1 . . O
C1 0.23182(9) 0.15314(9) 0.52819(12) 0.0246(2) Uani d . 1 . . C
C11 0.28894(9) -0.03163(9) 0.55776(12) 0.0263(2) Uani d . 1 . . C
C12 0.38995(9) -0.05030(10) 0.63448(12) 0.0278(2) Uani d . 1 . . C
C13 0.45412(10) -0.14359(10) 0.60383(14) 0.0338(3) Uani d . 1 . . C
H13 0.5216 -0.1577 0.6586 0.041 Uiso calc R 1 . . H
C14 0.41949(11) -0.21607(10) 0.49325(15) 0.0382(3) Uani d . 1 . . C
H14 0.4636 -0.2797 0.4710 0.046 Uiso calc R 1 . . H
C15 0.32031(11) -0.19585(11) 0.41487(15) 0.0393(3) Uani d . 1 . . C
H15 0.2975 -0.2447 0.3373 0.047 Uiso calc R 1 . . H
C16 0.25427(10) -0.10472(10) 0.44916(14) 0.0344(3) Uani d . 1 . . C
H16 0.1850 -0.0928 0.3975 0.041 Uiso calc R 1 . . H
C21 0.16043(9) 0.33294(9) 0.52775(12) 0.0244(2) Uani d . 1 . . C
C22 0.08447(9) 0.35544(9) 0.41232(12) 0.0246(2) Uani d . 1 . . C
C23 0.07547(9) 0.46284(9) 0.35468(12) 0.0273(2) Uani d . 1 . . C
H23 0.0230 0.4783 0.2769 0.033 Uiso calc R 1 . . H
C24 0.14357(10) 0.54725(10) 0.41140(13) 0.0299(3) Uani d . 1 . . C
H24 0.1385 0.6209 0.3718 0.036 Uiso calc R 1 . . H
C25 0.21931(10) 0.52451(10) 0.52598(13) 0.0326(3) Uani d . 1 . . C
H25 0.2662 0.5827 0.5642 0.039 Uiso calc R 1 . . H
C26 0.22705(10) 0.41741(10) 0.58515(13) 0.0303(3) Uani d . 1 . . C
H26 0.2780 0.4025 0.6648 0.036 Uiso calc R 1 . . H
N1 0.43350(9) 0.02891(10) 0.74587(12) 0.0368(3) Uani d . 1 . . N
N2 0.01200(8) 0.26778(8) 0.34831(11) 0.0295(2) Uani d . 1 . . N
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_publ_flag
C1 O2 C11 115.40(8) y
C1 O3 C21 114.06(8) y
O1 C1 O2 127.21(10) y
O1 C1 O3 127.02(10) y
O2 C1 O3 105.77(9) y
C16 C11 C12 119.78(10) ?
C16 C11 O2 118.41(10) ?
C12 C11 O2 121.58(10) ?
C13 C12 C11 120.25(11) ?
C13 C12 N1 118.00(10) ?
C11 C12 N1 121.73(10) ?
C14 C13 C12 119.68(11) ?
C14 C13 H13 120.2 ?
C12 C13 H13 120.2 ?
C13 C14 C15 119.91(11) ?
C13 C14 H14 120.0 ?
C15 C14 H14 120.0 ?
C14 C15 C16 120.30(12) ?
C14 C15 H15 119.8 ?
C16 C15 H15 119.8 ?
C11 C16 C15 120.01(11) ?
C11 C16 H16 120.0 ?
C15 C16 H16 120.0 ?
C26 C21 C22 120.11(10) ?
C26 C21 O3 118.06(9) ?
C22 C21 O3 121.68(9) ?
C23 C22 C21 120.32(10) ?
C23 C22 N2 117.94(10) ?
C21 C22 N2 121.74(10) ?
C24 C23 C22 119.42(10) ?
C24 C23 H23 120.3 ?
C22 C23 H23 120.3 ?
C23 C24 C25 120.11(11) ?
C23 C24 H24 119.9 ?
C25 C24 H24 119.9 ?
C26 C25 C24 120.44(11) ?
C26 C25 H25 119.8 ?
C24 C25 H25 119.8 ?
C21 C26 C25 119.58(10) ?
C21 C26 H26 120.2 ?
C25 C26 H26 120.2 ?
O5 N1 O4 123.79(12) ?
O5 N1 C12 119.06(10) ?
O4 N1 C12 117.14(11) ?
O7 N2 O6 122.88(10) ?
O7 N2 C22 119.48(9) ?
O6 N2 C22 117.63(9) ?
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
O1 C1 . 1.1839(13) y
O2 C1 . 1.3462(13) y
O2 C11 . 1.3947(13) y
O3 C1 . 1.3483(13) y
O3 C21 . 1.3994(13) y
O4 N1 . 1.2250(14) ?
O5 N1 . 1.2194(14) ?
O6 N2 . 1.2260(12) ?
O7 N2 . 1.2250(13) ?
C11 C16 . 1.3736(17) ?
C11 C12 . 1.3939(15) ?
C12 C13 . 1.3855(16) ?
C12 N1 . 1.4700(15) ?
C13 C14 . 1.3819(19) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.3858(18) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.3858(18) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C21 C26 . 1.3760(16) ?
C21 C22 . 1.3942(15) ?
C22 C23 . 1.3860(15) ?
C22 N2 . 1.4658(14) ?
C23 C24 . 1.3833(16) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.3875(16) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.3871(17) ?
C25 H25 . 0.9500 ?
C26 H26 . 0.9500 ?
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
C13 H13 O1 3_656 0.95 2.43 3.1060(14) 128.3
C26 H26 O1 4_566 0.95 2.57 3.3782(15) 142.9
C16 H16 O6 2_545 0.95 2.44 3.1756(15) 134.6
C24 H24 O6 2 0.95 2.62 3.5351(15) 162.8
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_publ_flag
C11 O2 C1 O1 8.87(16) y
C11 O2 C1 O3 -171.56(8) y
C21 O3 C1 O1 6.62(15) y
C21 O3 C1 O2 -172.96(8) y
C1 O2 C11 C16 -93.99(12) ?
C1 O2 C11 C12 91.49(13) y
C16 C11 C12 C13 -1.47(17) ?
O2 C11 C12 C13 172.98(10) ?
C16 C11 C12 N1 176.54(11) ?
O2 C11 C12 N1 -9.02(17) ?
C11 C12 C13 C14 2.25(18) ?
N1 C12 C13 C14 -175.82(11) ?
C12 C13 C14 C15 -0.74(19) ?
C13 C14 C15 C16 -1.6(2) ?
C12 C11 C16 C15 -0.84(18) ?
O2 C11 C16 C15 -175.46(11) ?
C14 C15 C16 C11 2.4(2) ?
C1 O3 C21 C26 -98.63(12) ?
C1 O3 C21 C22 85.88(12) y
C26 C21 C22 C23 -0.02(16) ?
O3 C21 C22 C23 175.37(10) ?
C26 C21 C22 N2 -179.94(10) ?
O3 C21 C22 N2 -4.55(16) ?
C21 C22 C23 C24 0.84(16) ?
N2 C22 C23 C24 -179.24(9) ?
C22 C23 C24 C25 -0.65(17) ?
C23 C24 C25 C26 -0.36(18) ?
C22 C21 C26 C25 -0.99(17) ?
O3 C21 C26 C25 -176.55(10) ?
C24 C25 C26 C21 1.18(18) ?
C13 C12 N1 O5 158.34(12) ?
C11 C12 N1 O5 -19.71(17) ?
C13 C12 N1 O4 -20.65(17) ?
C11 C12 N1 O4 161.30(12) ?
C23 C22 N2 O7 160.35(11) ?
C21 C22 N2 O7 -19.73(16) ?
C23 C22 N2 O6 -18.87(15) ?
C21 C22 N2 O6 161.05(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 235221
