#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/19/2101929.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_2101929
loop_
_publ_author_name
'Zaderenko, Paula'
'Gil, Ma. Soledad'
'López, Pilar'
'Ballesteros, Paloma'
'Fonseca, Isabel'
'Albert, Armando'
_publ_section_title
;
 Diethyl 2-Benzimidazol-1-ylsuccinate--Picric Acid (1/1) -- An
 Inclusion Molecular Complex
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              961
_journal_page_last               967
_journal_paper_doi               10.1107/S0108768197008562
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C15 H18 N2 O4 , C6 H3 N3 O7 '
_chemical_formula_sum            'C21 H21 N5 O11'
_chemical_formula_weight         519.43
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3100(10)
_cell_length_b                   23.183(4)
_cell_length_c                   9.4620(10)
_cell_measurement_reflns_used    53
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     2480.9(5)
_computing_cell_refinement       'LSUCRE (Appleman, unpublished, 1996)'
_computing_data_collection       'Philips PW1100'
_computing_data_reduction
'XRAY80 System (Stewart, Kundell & Baldwin, 1980)'
_computing_molecular_graphics    'XTAL3.0 (Hall & Stewart, 1990)'
_computing_publication_material  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1992)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Philips PW1100'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2241
_diffrn_reflns_theta_max         64.80
_diffrn_reflns_theta_min         4.35
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  90
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.985
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.224
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.5(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.135
_refine_ls_goodness_of_fit_obs   1.177
_refine_ls_hydrogen_treatment    'H atoms refined isotropically'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         2241
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.134
_refine_ls_restrained_S_obs      1.176
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_obs          0.0785
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0844P)²+2.4124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2160
_refine_ls_wR_factor_obs         0.1889
_reflns_number_observed          1683
_reflns_number_total             2241
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            bm0007.cif
_cod_data_source_block           mo461
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w =
1/[\s^2^(Fo^2^)+(0.0844P)^2^+2.4124P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0844P)^2^+2.4124P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2101929
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, 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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
N1 0.3805(5) 0.1876(2) 0.2515(7) 0.067(2) Uani d . 1 N
C2 0.4632(6) 0.1737(4) 0.1549(10) 0.081(2) Uani d . 1 C
H2 0.4914(6) 0.1366(4) 0.1392(10) 0.098 Uiso calc R 1 H
N3 0.4984(5) 0.2199(3) 0.0859(8) 0.075(2) Uani d . 1 N
C3A 0.4368(6) 0.2667(3) 0.1362(8) 0.064(2) Uani d . 1 C
C4 0.4405(7) 0.3243(4) 0.1026(10) 0.080(2) Uani d . 1 C
H4 0.4912(7) 0.3383(4) 0.0332(10) 0.096 Uiso calc R 1 H
C5 0.3664(9) 0.3602(4) 0.1753(13) 0.097(3) Uani d . 1 C
H5 0.3666(9) 0.3994(4) 0.1540(13) 0.116 Uiso calc R 1 H
C6 0.2905(8) 0.3399(4) 0.2808(13) 0.092(3) Uani d . 1 C
H6 0.2429(8) 0.3661(4) 0.3290(13) 0.111 Uiso calc R 1 H
C7 0.2845(6) 0.2830(3) 0.3149(10) 0.071(2) Uani d . 1 C
H7 0.2315(6) 0.2694(3) 0.3822(10) 0.086 Uiso calc R 1 H
C7A 0.3614(6) 0.2461(3) 0.2444(8) 0.060(2) Uani d . 1 C
C8 0.3217(6) 0.1469(3) 0.3491(8) 0.067(2) Uani d . 1 C
H8 0.2910(6) 0.1704(3) 0.4269(8) 0.081 Uiso calc R 1 H
C9 0.4130(7) 0.1063(3) 0.4155(9) 0.071(2) Uani d . 1 C
O10 0.3597(5) 0.0636(2) 0.4778(7) 0.078(2) Uani d . 1 O
O11 0.5177(5) 0.1150(3) 0.4116(9) 0.107(2) Uani d . 1 O
C12 0.4322(8) 0.0236(4) 0.5540(13) 0.096(3) Uani d . 1 C
H12A 0.4914(8) 0.0441(4) 0.6086(13) 0.115 Uiso calc R 1 H
H12B 0.4724(8) -0.0020(4) 0.4888(13) 0.115 Uiso calc R 1 H
C13 0.3553(11) -0.0093(5) 0.6477(17) 0.135(5) Uani d . 1 C
H13A 0.4017(11) -0.0366(5) 0.7002(17) 0.203 Uiso calc R 1 H
H13B 0.2973(11) -0.0296(5) 0.5926(17) 0.203 Uiso calc R 1 H
H13C 0.3162(11) 0.0164(5) 0.7119(17) 0.203 Uiso calc R 1 H
C14 0.2145(6) 0.1183(3) 0.2821(9) 0.068(2) Uani d . 1 C
H14A 0.1683(6) 0.0997(3) 0.3556(9) 0.082 Uiso calc R 1 H
H14B 0.1654(6) 0.1478(3) 0.2392(9) 0.082 Uiso calc R 1 H
C15 0.2458(8) 0.0742(3) 0.1719(10) 0.077(2) Uani d . 1 C
O16 0.3450(5) 0.0584(3) 0.1428(8) 0.093(2) Uani d . 1 O
O17 0.1485(5) 0.0544(3) 0.1104(8) 0.092(2) Uani d . 1 O
C18 0.1642(12) 0.0135(5) -0.0073(14) 0.126(4) Uani d . 1 C
H18A 0.2196(12) 0.0289(5) -0.0758(14) 0.151 Uiso calc R 1 H
H18B 0.1951(12) -0.0229(5) 0.0277(14) 0.151 Uiso calc R 1 H
C19 0.0503(14) 0.0046(9) -0.072(3) 0.219(10) Uani d . 1 C
H19A 0.0581(14) -0.0220(9) -0.150(3) 0.329 Uiso calc R 1 H
H19B 0.0207(14) 0.0407(9) -0.107(3) 0.329 Uiso calc R 1 H
H19C -0.0038(14) -0.0108(9) -0.004(3) 0.329 Uiso calc R 1 H
C30 0.7343(7) 0.2293(4) -0.1756(9) 0.077(2) Uani d . 1 C
O31 0.6424(6) 0.2454(3) -0.1127(9) 0.119(3) Uani d . 1 O
H31 0.6032(6) 0.2172(3) -0.0901(9) 0.179 Uiso calc R 1 H
C32 0.8189(8) 0.2693(4) -0.2270(10) 0.078(2) Uani d . 1 C
N33 0.8015(9) 0.3293(5) -0.1937(12) 0.113(3) Uani d . 1 N
O34 0.7640(12) 0.3424(5) -0.0828(16) 0.182(5) Uani d . 1 O
O35 0.8283(17) 0.3646(5) -0.2773(17) 0.251(8) Uani d . 1 O
C36 0.9142(8) 0.2550(5) -0.3086(10) 0.091(3) Uani d . 1 C
H36 0.9645(8) 0.2834(5) -0.3433(10) 0.109 Uiso calc R 1 H
C37 0.9338(8) 0.1989(5) -0.3379(11) 0.095(3) Uani d . 1 C
N38 1.0375(9) 0.1848(8) -0.4251(14) 0.149(5) Uani d . 1 N
O39 1.0977(8) 0.2213(6) -0.4701(12) 0.190(6) Uani d . 1 O
O40 1.0544(11) 0.1308(7) -0.4420(16) 0.216(7) Uani d . 1 O
C41 0.8596(8) 0.1575(5) -0.2951(11) 0.098(3) Uani d . 1 C
H41 0.8738(8) 0.1193(5) -0.3199(11) 0.118 Uiso calc R 1 H
C42 0.7626(7) 0.1712(4) -0.2149(10) 0.080(2) Uani d . 1 C
N43 0.6905(9) 0.1237(4) -0.1679(12) 0.121(3) Uani d . 1 N
O44 0.7135(11) 0.0752(4) -0.2028(18) 0.224(7) Uani d . 1 O
O45 0.6048(9) 0.1325(4) -0.0927(13) 0.171(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
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2 N1 C7A 108.1(6) yes
C2 N1 C8 125.7(6) ?
C7A N1 C8 126.2(6) ?
N3 C2 N1 110.7(7) yes
C2 N3 C3A 108.5(6) yes
C4 C3A N3 132.2(7) ?
C4 C3A C7A 121.0(7) ?
N3 C3A C7A 106.8(6) yes
C5 C4 C3A 117.2(8) ?
C4 C5 C6 122.1(8) ?
C7 C6 C5 121.7(9) ?
C6 C7 C7A 116.9(8) ?
N1 C7A C7 132.9(7) ?
N1 C7A C3A 106.0(6) yes
C7 C7A C3A 121.0(7) ?
N1 C8 C14 112.1(6) ?
N1 C8 C9 110.2(6) ?
C14 C8 C9 116.2(6) ?
O11 C9 O10 126.7(8) ?
O11 C9 C8 123.3(7) ?
O10 C9 C8 109.9(6) ?
C9 O10 C12 117.1(6) ?
O10 C12 C13 107.7(8) ?
C15 C14 C8 113.4(6) ?
O16 C15 O17 124.3(8) ?
O16 C15 C14 125.6(9) ?
O17 C15 C14 110.1(7) ?
C15 O17 C18 117.0(8) ?
C19 C18 O17 107.9(11) ?
O31 C30 C32 121.7(8) ?
O31 C30 C42 126.1(8) ?
C32 C30 C42 112.0(7) ?
C36 C32 C30 124.6(8) ?
C36 C32 N33 117.7(8) ?
C30 C32 N33 117.7(8) ?
O34 N33 O35 121.0(13) yes
O34 N33 C32 119.7(11) ?
O35 N33 C32 119.3(11) ?
C37 C36 C32 118.6(8) ?
C41 C37 C36 121.8(8) ?
C41 C37 N38 120.7(12) ?
C36 C37 N38 117.4(11) ?
O39 N38 O40 125.3(11) yes
O39 N38 C37 120.6(15) ?
O40 N38 C37 114.0(13) ?
C37 C41 C42 120.1(10) ?
C41 C42 C30 122.8(8) ?
C41 C42 N43 116.5(9) ?
C30 C42 N43 120.7(8) ?
O44 N43 O45 119.2(10) yes
O44 N43 C42 120.5(10) ?
O45 N43 C42 120.2(10) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.347(9) yes
N1 C7A 1.375(9) yes
N1 C8 1.478(9) ?
C2 N3 1.316(10) yes
N3 C3A 1.376(9) yes
C3A C4 1.373(10) ?
C3A C7A 1.415(10) yes
C4 C5 1.367(13) ?
C5 C6 1.398(14) ?
C6 C7 1.361(11) ?
C7 C7A 1.391(10) ?
C8 C14 1.521(10) ?
C8 C9 1.531(11) ?
C9 O11 1.202(9) ?
C9 O10 1.300(9) ?
O10 C12 1.433(10) yes
C12 C13 1.458(15) yes
C14 C15 1.501(11) ?
C15 O16 1.212(9) ?
C15 O17 1.327(10) ?
O17 C18 1.474(12) yes
C18 C19 1.44(2) yes
C30 O31 1.255(9) ?
C30 C32 1.419(11) ?
C30 C42 1.432(13) ?
C32 C36 1.367(12) ?
C32 N33 1.440(13) yes
N33 O34 1.171(15) yes
N33 O35 1.179(13) yes
C36 C37 1.348(13) ?
C37 C41 1.338(14) ?
C37 N38 1.471(12) yes
N38 O39 1.17(2) yes
N38 O40 1.28(2) yes
C41 C42 1.371(12) ?
C42 N43 1.441(12) yes
N43 O44 1.202(11) yes
N43 O45 1.220(11) 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
C7A N1 C2 N3 0.0(9)
C8 N1 C2 N3 -179.4(7)
N1 C2 N3 C3A -0.6(10)
C2 N3 C3A C4 179.0(9)
C2 N3 C3A C7A 1.0(9)
N3 C3A C4 C5 -179.3(9)
C7A C3A C4 C5 -1.6(13)
C3A C4 C5 C6 0.6(15)
C4 C5 C6 C7 -1.3(16)
C5 C6 C7 C7A 2.9(14)
C2 N1 C7A C7 177.6(9)
C8 N1 C7A C7 -3.0(13)
C2 N1 C7A C3A 0.6(8)
C8 N1 C7A C3A -180.0(7)
C6 C7 C7A N1 179.6(9)
C6 C7 C7A C3A -3.8(12)
C4 C3A C7A N1 -179.3(7)
N3 C3A C7A N1 -1.0(8)
C4 C3A C7A C7 3.3(12)
N3 C3A C7A C7 -178.4(7)
C2 N1 C8 C14 -86.0(9)
C7A N1 C8 C14 94.8(8)
C2 N1 C8 C9 45.1(10)
C7A N1 C8 C9 -134.2(8)
N1 C8 C9 O11 14.7(12)
C14 C8 C9 O11 143.7(9)
N1 C8 C9 O10 -167.1(7)
C14 C8 C9 O10 -38.2(9)
O11 C9 O10 C12 2.2(14)
C8 C9 O10 C12 -175.8(8)
C9 O10 C12 C13 163.4(9)
N1 C8 C14 C15 72.5(8)
C9 C8 C14 C15 -55.5(9)
C8 C14 C15 O16 5.3(12)
C8 C14 C15 O17 -175.1(7)
O16 C15 O17 C18 -4.3(13)
C14 C15 O17 C18 176.1(8)
C15 O17 C18 C19 -171.1(13)
O31 C30 C32 C36 -173.0(10)
C42 C30 C32 C36 2.2(12)
O31 C30 C32 N33 5.4(14)
C42 C30 C32 N33 -179.4(8)
C36 C32 N33 O34 -144.2(14)
C30 C32 N33 O34 37.3(17)
C36 C32 N33 O35 33.7(17)
C30 C32 N33 O35 -144.8(15)
C30 C32 C36 C37 -3.3(14)
N33 C32 C36 C37 178.3(10)
C32 C36 C37 C41 3.3(16)
C32 C36 C37 N38 -179.6(9)
C41 C37 N38 O39 174.9(13)
C36 C37 N38 O39 -2.2(19)
C41 C37 N38 O40 -6.6(19)
C36 C37 N38 O40 176.3(13)
C36 C37 C41 C42 -2.4(16)
N38 C37 C41 C42 -179.4(10)
C37 C41 C42 C30 1.3(15)
C37 C41 C42 N43 -177.1(10)
O31 C30 C42 C41 173.8(10)
C32 C30 C42 C41 -1.1(13)
O31 C30 C42 N43 -7.8(15)
C32 C30 C42 N43 177.3(9)
C41 C42 N43 O44 -2.6(19)
C30 C42 N43 O44 178.9(13)
C41 C42 N43 O45 177.9(12)
C30 C42 N43 O45 -0.6(17)
