#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/59/2205919.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_2205919
loop_
_publ_author_name
'Jin Longfei'
'Xiao Fengping'
_publ_section_title
;
 Propyl 3,5-dinitrobenzoate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1826
_journal_page_last               o1827
_journal_paper_doi               10.1107/S160053680501528X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C10 H10 N2 O6'
_chemical_formula_moiety         'C10 H10 N2 O6'
_chemical_formula_sum            'C10 H10 N2 O6'
_chemical_formula_weight         254.20
_chemical_name_systematic
;
Propyl 3,5-dinitrobenzoate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                117.554(2)
_cell_angle_beta                 99.937(3)
_cell_angle_gamma                102.830(2)
_cell_formula_units_Z            4
_cell_length_a                   11.0566(16)
_cell_length_b                   11.3596(17)
_cell_length_c                   11.4916(17)
_cell_measurement_reflns_used    2196
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      25.59
_cell_measurement_theta_min      2.15
_cell_volume                     1182.7(3)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL 97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7233
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.99
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.9648
_exptl_absorpt_correction_T_min  0.9314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         4995
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0557
_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)+(0.0774P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1515
_reflns_number_gt                3237
_reflns_number_total             4995
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6511.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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_database_code               2205919
_cod_database_fobs_code          2205919
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 0.10136(16) 0.15092(17) 0.22934(17) 0.0519(4) Uani d . 1 . . C
C2 -0.02385(17) 0.05093(18) 0.16164(17) 0.0558(4) Uani d . 1 . . C
H2 -0.0361 -0.0452 0.1162 0.067 Uiso calc R 1 . . H
C3 -0.12955(17) 0.09589(19) 0.16263(18) 0.0559(4) Uani d . 1 . . C
C4 -0.11654(18) 0.23630(19) 0.22678(17) 0.0586(5) Uani d . 1 . . C
H4 -0.1891 0.2648 0.2257 0.070 Uiso calc R 1 . . H
C5 0.00843(18) 0.33267(18) 0.29255(17) 0.0551(4) Uani d . 1 . . C
C6 0.11736(18) 0.29327(18) 0.29548(17) 0.0550(4) Uani d . 1 . . C
H6 0.2007 0.3615 0.3413 0.066 Uiso calc R 1 . . H
C7 0.21360(18) 0.0984(2) 0.22367(19) 0.0574(4) Uani d . 1 . . C
C8 0.44448(19) 0.1649(2) 0.2969(2) 0.0802(6) Uani d . 1 . . C
H8A 0.4434 0.1038 0.2033 0.096 Uiso calc R 1 . . H
H8B 0.4480 0.1146 0.3457 0.096 Uiso calc R 1 . . H
C9 0.5596(2) 0.2971(3) 0.3688(3) 0.0986(8) Uani d . 1 . . C
H9A 0.5576 0.3569 0.4614 0.118 Uiso calc R 1 . . H
H9B 0.6383 0.2732 0.3781 0.118 Uiso calc R 1 . . H
C10 0.5682(3) 0.3778(4) 0.3003(4) 0.1364(12) Uani d . 1 . . C
H10A 0.5699 0.3197 0.2083 0.205 Uiso calc R 1 . . H
H10B 0.6467 0.4595 0.3518 0.205 Uiso calc R 1 . . H
H10C 0.4936 0.4075 0.2958 0.205 Uiso calc R 1 . . H
C11 0.87794(17) 0.77412(18) 0.32113(18) 0.0555(4) Uani d . 1 . . C
C12 0.99764(18) 0.82857(18) 0.42156(18) 0.0577(4) Uani d . 1 . . C
H12 1.0035 0.8692 0.5145 0.069 Uiso calc R 1 . . H
C13 1.10736(17) 0.82199(18) 0.38264(19) 0.0566(4) Uani d . 1 . . C
C14 1.10438(18) 0.76247(17) 0.24677(18) 0.0565(4) Uani d . 1 . . C
H14 1.1799 0.7588 0.2221 0.068 Uiso calc R 1 . . H
C15 0.98382(18) 0.70866(17) 0.14915(18) 0.0533(4) Uani d . 1 . . C
C16 0.87092(17) 0.71341(17) 0.18268(18) 0.0547(4) Uani d . 1 . . C
H16 0.7913 0.6767 0.1140 0.066 Uiso calc R 1 . . H
C17 0.7603(2) 0.7821(2) 0.3671(2) 0.0648(5) Uani d . 1 B . C
C18 0.5304(2) 0.7199(3) 0.2948(3) 0.1046(9) Uani d . 1 B . C
H18A 0.5324 0.8167 0.3458 0.125 Uiso calc R 1 . . H
H18B 0.5194 0.6786 0.3514 0.125 Uiso calc R 1 . . H
C19 0.4207(3) 0.6364(3) 0.1612(4) 0.1295(12) Uani d . 1 . . C
H19A 0.4246 0.5420 0.1111 0.155 Uiso calc R 1 A 1 H
H19B 0.3391 0.6272 0.1823 0.155 Uiso calc R 1 A 1 H
C20 0.4161(5) 0.6916(14) 0.0687(11) 0.136(3) Uani d P 0.83(2) B 1 C
H20A 0.4148 0.7862 0.1171 0.203 Uiso calc PR 0.83(2) B 1 H
H20B 0.3385 0.6325 -0.0102 0.203 Uiso calc PR 0.83(2) B 1 H
H20C 0.4918 0.6922 0.0386 0.203 Uiso calc PR 0.83(2) B 1 H
C20' 0.441(3) 0.771(3) 0.154(5) 0.114(11) Uani d P 0.17(2) B 2 C
H20D 0.3828 0.7478 0.0677 0.171 Uiso calc PR 0.17(2) B 2 H
H20E 0.5295 0.8083 0.1592 0.171 Uiso calc PR 0.17(2) B 2 H
H20F 0.4217 0.8399 0.2294 0.171 Uiso calc PR 0.17(2) B 2 H
N1 -0.26240(16) -0.01140(19) 0.08969(18) 0.0702(4) Uani d . 1 . . N
N2 0.0260(2) 0.48426(18) 0.36093(17) 0.0689(4) Uani d . 1 . . N
N3 1.23439(17) 0.88002(18) 0.48991(19) 0.0717(5) Uani d . 1 . . N
N4 0.97630(18) 0.64307(16) 0.00267(17) 0.0650(4) Uani d . 1 . . N
O1 0.32750(12) 0.20410(14) 0.29437(14) 0.0678(4) Uani d . 1 . . O
O2 0.20064(13) -0.02444(14) 0.16060(15) 0.0743(4) Uani d . 1 . . O
O3 -0.27129(15) -0.13506(17) 0.03185(18) 0.0956(5) Uani d . 1 . . O
O4 -0.35441(14) 0.02940(18) 0.09045(18) 0.0964(5) Uani d . 1 . . O
O5 -0.07121(17) 0.51671(15) 0.36373(18) 0.0953(5) Uani d . 1 . . O
O6 0.13675(17) 0.56839(15) 0.41178(17) 0.0954(5) Uani d . 1 . . O
O7 0.65180(14) 0.71664(17) 0.26076(15) 0.0840(5) Uani d . 1 . . O
O8 0.76574(15) 0.84170(17) 0.48646(16) 0.0853(5) Uani d . 1 . . O
O9 1.23669(15) 0.93416(18) 0.61045(16) 0.0901(5) Uani d . 1 . . O
O10 1.33013(15) 0.87096(19) 0.45355(17) 0.0995(5) Uani d . 1 . . O
O11 1.07182(15) 0.61953(15) -0.02844(14) 0.0790(4) Uani d . 1 . . O
O12 0.87385(18) 0.6129(2) -0.08120(16) 0.1002(5) Uani d . 1 . . O
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
C6 C1 C2 119.49(16) ?
C6 C1 C7 122.87(16) ?
C2 C1 C7 117.62(16) yes
C3 C2 C1 119.07(17) ?
C3 C2 H2 120.5 ?
C1 C2 H2 120.5 ?
C4 C3 C2 122.67(17) ?
C4 C3 N1 118.68(17) ?
C2 C3 N1 118.64(17) ?
C5 C4 C3 116.93(16) ?
C5 C4 H4 121.5 ?
C3 C4 H4 121.5 ?
C4 C5 C6 122.68(16) ?
C4 C5 N2 118.38(16) ?
C6 C5 N2 118.93(17) ?
C5 C6 C1 119.15(16) ?
C5 C6 H6 120.4 ?
C1 C6 H6 120.4 ?
O2 C7 O1 125.02(17) yes
O2 C7 C1 123.28(17) yes
O1 C7 C1 111.69(15) ?
O1 C8 C9 107.66(19) ?
O1 C8 H8A 110.2 ?
C9 C8 H8A 110.2 ?
O1 C8 H8B 110.2 ?
C9 C8 H8B 110.2 ?
H8A C8 H8B 108.5 ?
C10 C9 C8 115.0(2) ?
C10 C9 H9A 108.5 ?
C8 C9 H9A 108.5 ?
C10 C9 H9B 108.5 ?
C8 C9 H9B 108.5 ?
H9A C9 H9B 107.5 ?
C9 C10 H10A 109.5 ?
C9 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
C9 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
C12 C11 C16 119.60(16) ?
C12 C11 C17 117.89(17) yes
C16 C11 C17 122.51(17) ?
C13 C12 C11 119.30(17) ?
C13 C12 H12 120.4 ?
C11 C12 H12 120.4 ?
C12 C13 C14 122.83(17) ?
C12 C13 N3 119.05(17) ?
C14 C13 N3 118.11(17) ?
C13 C14 C15 116.54(17) ?
C13 C14 H14 121.7 ?
C15 C14 H14 121.7 ?
C16 C15 C14 122.96(17) ?
C16 C15 N4 118.82(17) ?
C14 C15 N4 118.22(16) ?
C15 C16 C11 118.77(16) ?
C15 C16 H16 120.6 ?
C11 C16 H16 120.6 ?
O8 C17 O7 125.14(18) yes
O8 C17 C11 123.25(19) yes
O7 C17 C11 111.61(17) ?
O7 C18 C19 107.1(2) ?
O7 C18 H18A 110.3 ?
C19 C18 H18A 110.3 ?
O7 C18 H18B 110.3 ?
C19 C18 H18B 110.3 ?
H18A C18 H18B 108.5 ?
C20 C19 C18 117.3(4) ?
C18 C19 C20' 89.1(19) ?
C20 C19 H19A 108.0 ?
C18 C19 H19A 108.0 ?
C20' C19 H19A 140.6 ?
C20 C19 H19B 108.0 ?
C18 C19 H19B 108.0 ?
C20' C19 H19B 100.3 ?
H19A C19 H19B 107.2 ?
C19 C20 H20A 109.5 ?
C19 C20 H20B 109.5 ?
C19 C20 H20C 109.5 ?
C19 C20' H20D 109.5 ?
C19 C20' H20E 109.5 ?
H20D C20' H20E 109.5 ?
C19 C20' H20F 109.5 ?
H20D C20' H20F 109.5 ?
H20E C20' H20F 109.5 ?
O4 N1 O3 124.55(17) ?
O4 N1 C3 118.02(18) ?
O3 N1 C3 117.42(17) ?
O6 N2 O5 124.34(17) ?
O6 N2 C5 117.91(17) ?
O5 N2 C5 117.74(18) ?
O10 N3 O9 123.93(18) ?
O10 N3 C13 118.23(18) ?
O9 N3 C13 117.83(18) ?
O12 N4 O11 123.55(17) ?
O12 N4 C15 117.95(17) ?
O11 N4 C15 118.49(17) ?
C7 O1 C8 116.43(15) yes
C17 O7 C18 115.95(17) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 1.383(2) ?
C1 C2 1.387(2) ?
C1 C7 1.490(2) yes
C2 C3 1.375(2) ?
C2 H2 0.9300 ?
C3 C4 1.372(2) ?
C3 N1 1.477(2) ?
C4 C5 1.372(2) ?
C4 H4 0.9300 ?
C5 C6 1.375(2) ?
C5 N2 1.472(2) ?
C6 H6 0.9300 ?
C7 O2 1.197(2) yes
C7 O1 1.327(2) yes
C8 O1 1.458(2) yes
C8 C9 1.483(3) ?
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C9 C10 1.458(4) ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 H10A 0.9600 ?
C10 H10B 0.9600 ?
C10 H10C 0.9600 ?
C11 C12 1.384(2) ?
C11 C16 1.390(2) ?
C11 C17 1.492(3) yes
C12 C13 1.369(2) ?
C12 H12 0.9300 ?
C13 C14 1.375(2) ?
C13 N3 1.472(2) ?
C14 C15 1.377(2) ?
C14 H14 0.9300 ?
C15 C16 1.373(2) ?
C15 N4 1.469(2) ?
C16 H16 0.9300 ?
C17 O8 1.199(2) yes
C17 O7 1.320(2) yes
C18 O7 1.465(2) yes
C18 C19 1.492(4) ?
C18 H18A 0.9700 ?
C18 H18B 0.9700 ?
C19 C20 1.461(6) ?
C19 C20' 1.54(2) ?
C19 H19A 0.9700 ?
C19 H19B 0.9700 ?
C20 H20A 0.9600 ?
C20 H20B 0.9600 ?
C20 H20C 0.9600 ?
C20' H20D 0.9600 ?
C20' H20E 0.9600 ?
C20' H20F 0.9600 ?
N1 O4 1.208(2) ?
N1 O3 1.215(2) ?
N2 O6 1.212(2) ?
N2 O5 1.213(2) ?
N3 O10 1.211(2) ?
N3 O9 1.221(2) ?
N4 O12 1.214(2) ?
N4 O11 1.2173(19) ?
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
C6 C1 C2 C3 -0.4(3) ?
C7 C1 C2 C3 -178.76(15) ?
C1 C2 C3 C4 0.7(3) ?
C1 C2 C3 N1 179.71(15) ?
C2 C3 C4 C5 -0.6(3) ?
N1 C3 C4 C5 -179.55(16) ?
C3 C4 C5 C6 0.1(3) ?
C3 C4 C5 N2 179.21(16) ?
C4 C5 C6 C1 0.2(3) ?
N2 C5 C6 C1 -178.89(15) ?
C2 C1 C6 C5 -0.1(3) ?
C7 C1 C6 C5 178.20(16) ?
C6 C1 C7 O2 -175.97(18) yes
C2 C1 C7 O2 2.3(3) ?
C6 C1 C7 O1 2.9(2) ?
C2 C1 C7 O1 -178.80(15) ?
O1 C8 C9 C10 -62.9(3) ?
C16 C11 C12 C13 0.2(3) ?
C17 C11 C12 C13 179.54(15) ?
C11 C12 C13 C14 -0.3(3) ?
C11 C12 C13 N3 -179.97(15) ?
C12 C13 C14 C15 0.1(2) ?
N3 C13 C14 C15 179.71(14) ?
C13 C14 C15 C16 0.4(2) ?
C13 C14 C15 N4 -179.49(14) ?
C14 C15 C16 C11 -0.5(2) ?
N4 C15 C16 C11 179.32(15) ?
C12 C11 C16 C15 0.2(2) ?
C17 C11 C16 C15 -179.09(15) ?
C12 C11 C17 O8 5.4(3) ?
C16 C11 C17 O8 -175.27(19) yes
C12 C11 C17 O7 -174.98(16) ?
C16 C11 C17 O7 4.4(2) ?
O7 C18 C19 C20 -65.2(6) ?
O7 C18 C19 C20' -86.9(7) ?
C4 C3 N1 O4 -0.5(3) ?
C2 C3 N1 O4 -179.47(17) ?
C4 C3 N1 O3 178.88(18) ?
C2 C3 N1 O3 -0.1(3) yes
C4 C5 N2 O6 -175.77(17) ?
C6 C5 N2 O6 3.4(3) ?
C4 C5 N2 O5 4.9(3) yes
C6 C5 N2 O5 -175.95(17) ?
C12 C13 N3 O10 178.63(17) ?
C14 C13 N3 O10 -1.0(3) ?
C12 C13 N3 O9 -1.2(3) yes
C14 C13 N3 O9 179.18(16) ?
C16 C15 N4 O12 9.7(2) ?
C14 C15 N4 O12 -170.40(17) ?
C16 C15 N4 O11 -168.93(15) ?
C14 C15 N4 O11 10.9(2) yes
O2 C7 O1 C8 -1.7(3) ?
C1 C7 O1 C8 179.48(15) ?
C9 C8 O1 C7 174.60(18) yes
O8 C17 O7 C18 0.4(3) ?
C11 C17 O7 C18 -179.20(18) ?
C19 C18 O7 C17 -178.0(2) yes
