#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2001545.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_2001545
loop_
_publ_author_name
'Schouten, A.'
'Kanters, J. A.'
'Poonia, N. S.'
_publ_contact_author
;
     A. Schouten
     Department of Crystal and Structural Chemistry
     Bijvoet Center for Biomolecular Research
     University of Utrecht
     Padualaan 8
     3584 CH Utrecht, The Netherlands.
;
_publ_section_title
;
 Structure of the benzo-15-crown-5--3,5-dinitrobenzoic acid--water
 (1/1/1) complex
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1376
_journal_page_last               1378
_journal_volume                  49
_journal_year                    1993
_chemical_formula_moiety         'C7 H4 N2 O6, C14 H20 O5, H2 O'
_chemical_formula_sum            'C21 H26 N2 O12'
_chemical_formula_weight         498.44
_chemical_melting_point          373.0(5)
_chemical_name_systematic
;
(3,5-dinitrobenzoic acid)(benzo-15-crown-5)monohydrate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_method           'PLATON_TABLE_ACC option'
_cell_angle_alpha                90
_cell_angle_beta                 106.916(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.0711(4)
_cell_length_b                   15.0900(10)
_cell_length_c                   11.1925(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    100
_cell_measurement_theta_max      17.51
_cell_measurement_theta_min      10.62
_cell_volume                     1142.60(12)
_computing_cell_refinement       'SET4 (de Boer & Duisenberg, 1984)'
_computing_data_collection       'CAD4 software (Enraf-Nonius, 1985)'
_computing_data_reduction        'HELENA (Spek, 1990)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELX76 (Sheldrick, 1976)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_measurement_device       'Enraf-Nonius CAD-4 diffractometer'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6772
_diffrn_reflns_theta_max         30.26
_diffrn_reflns_theta_min         1.35
_diffrn_standards_decay_%        2.3
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       rod
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.26
_refine_ls_abs_structure_details
;
;
_refine_ls_extinction_coef       0.0016
_refine_ls_extinction_method     SHELX76
_refine_ls_goodness_of_fit_obs   1.49
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         2992
_refine_ls_R_factor_obs          0.0332
_refine_ls_shift/esd_max         0.037
_refine_ls_shift/esd_mean        0.0050
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      'w = 1/[\s^2^(F)]'
_refine_ls_wR_factor_obs         0.0297
_reflns_number_observed          2992
_reflns_number_total             3413
_reflns_observed_criterion       >2.5sigma(I)
_[local]_cod_data_source_file    ha1021.cif
_[local]_cod_data_source_block   default
_[local]_cod_cif_authors_sg_H-M  'P 21'
_cod_database_code               2001545
loop_
_symmetry_equiv_pos_as_xyz
'+x,    +y, +z'
'-x, 1/2+y, -z'
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
O7 0.0240(8) 0.0125(7) 0.0146(7) 0.0023(6) 0.0081(6) 0.0007(5)
O8 0.0202(8) 0.0234(8) 0.0165(7) -0.0012(6) 0.0052(6) 0.0028(6)
O9 0.0184(8) 0.0270(8) 0.0213(8) -0.0005(7) 0.0060(6) -0.0009(6)
O10 0.0204(8) 0.0204(7) 0.0196(7) 0.0008(6) 0.0048(6) -0.0042(6)
O11 0.0233(8) 0.0116(7) 0.0161(6) 0.0004(6) 0.0072(6) -0.0007(5)
C8 0.0140(10) 0.0210(10) 0.0166(9) -0.0004(8) 0.0039(8) -0.0031(8)
C9 0.0127(9) 0.0180(10) 0.0129(9) -0.0007(8) 0.0023(8) 0.0000(7)
C10 0.0131(9) 0.0180(10) 0.0126(9) -0.0009(8) 0.0041(7) -0.0014(7)
C11 0.0170(10) 0.0220(10) 0.0169(9) -0.0010(9) 0.0027(8) 0.0021(9)
C12 0.0160(10) 0.0330(10) 0.0112(9) -0.0034(9) 0.0044(8) 0.0035(8)
C13 0.0160(10) 0.0320(10) 0.0141(9) -0.0012(9) 0.0058(8) -0.0061(9)
C14 0.0240(10) 0.0130(10) 0.0190(10) 0.0013(8) 0.0053(9) 0.0000(7)
C15 0.0230(10) 0.0160(10) 0.0210(10) -0.0028(9) 0.0062(9) 0.0038(8)
C16 0.0270(10) 0.0280(10) 0.0140(9) -0.0030(10) 0.0060(9) 0.0038(9)
C17 0.0200(10) 0.0320(10) 0.0159(9) -0.0060(10) 0.0066(9) 0.0014(9)
C18 0.0220(10) 0.0350(10) 0.0190(10) 0.0040(10) 0.0090(9) -0.0011(9)
C19 0.0260(10) 0.0260(10) 0.0180(10) 0.0040(10) 0.0046(9) -0.0073(9)
C20 0.0270(10) 0.0140(10) 0.0240(10) 0.0040(9) 0.0065(9) -0.0027(8)
C21 0.0240(10) 0.0130(10) 0.0220(10) -0.0006(9) 0.0065(9) 0.0007(8)
O1 0.0400(10) 0.0390(10) 0.0296(9) -0.0029(9) 0.0137(8) -0.0160(8)
O2 0.0430(10) 0.0189(8) 0.0430(10) 0.0027(8) 0.0102(9) -0.0077(8)
O3 0.0224(8) 0.0245(8) 0.0232(7) 0.0015(7) 0.0052(6) 0.0068(6)
O4 0.0231(8) 0.0234(8) 0.0183(7) -0.0008(6) 0.0091(6) 0.0003(6)
O5 0.085(2) 0.0203(9) 0.0470(10) 0.0130(10) 0.0390(10) 0.0099(8)
O6 0.0430(10) 0.0288(9) 0.0212(8) -0.0069(8) 0.0084(7) 0.0054(7)
N1 0.0185(9) 0.0250(10) 0.0340(10) -0.0026(8) 0.0051(8) -0.0138(9)
N2 0.0290(10) 0.0201(9) 0.0280(10) -0.0018(8) 0.0113(8) 0.0054(8)
C1 0.0140(10) 0.0250(10) 0.0178(9) -0.0048(8) 0.0048(8) -0.0024(8)
C2 0.0150(10) 0.0180(10) 0.0250(10) -0.0009(8) 0.0051(8) -0.0063(8)
C3 0.0130(10) 0.0150(10) 0.0250(10) -0.0013(8) 0.0035(8) 0.0009(8)
C4 0.0120(10) 0.0164(9) 0.0178(9) -0.0019(8) 0.0033(8) 0.0004(8)
C5 0.0140(10) 0.0160(10) 0.0200(10) -0.0011(8) 0.0050(8) -0.0022(8)
C6 0.0170(10) 0.0170(10) 0.0230(10) -0.0018(8) 0.0065(8) 0.0038(8)
C7 0.0110(10) 0.0220(10) 0.0180(10) -0.0017(8) 0.0022(8) 0.0011(8)
O22 0.0218(9) 0.0254(9) 0.0273(8) -0.0037(8) 0.0121(7) -0.0036(7)
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
O7 0.7759(2) 0.1483(2) 0.85950(10) 0.0165(4) Uani
O8 0.9036(2) 0.0920(2) 1.10660(10) 0.0201(4) Uani
O9 0.7704(2) 0.2561(2) 1.20360(10) 0.0222(5) Uani
O10 0.8236(2) 0.4062(2) 1.05740(10) 0.0203(4) Uani
O11 0.7285(2) 0.3141(2) 0.83120(10) 0.0167(4) Uani
C8 0.8208(3) 0.1279(2) 0.6531(2) 0.0173(6) Uani
C9 0.7891(3) 0.1795(2) 0.7476(2) 0.0148(5) Uani
C10 0.7624(3) 0.2714(2) 0.7320(2) 0.0145(5) Uani
C11 0.7659(3) 0.3108(2) 0.6204(2) 0.0191(6) Uani
C12 0.7939(3) 0.2578(2) 0.5236(2) 0.0200(6) Uani
C13 0.8213(3) 0.1683(2) 0.5400(2) 0.0204(6) Uani
C14 0.8237(3) 0.0574(2) 0.8892(2) 0.0189(6) Uani
C15 0.7750(3) 0.0410(2) 1.0091(2) 0.0200(6) Uani
C16 0.8293(4) 0.1011(2) 1.2125(2) 0.0230(6) Uani
C17 0.6742(3) 0.1724(2) 1.1962(2) 0.0223(6) Uani
C18 0.6354(3) 0.3284(2) 1.1757(2) 0.0247(6) Uani
C19 0.7501(4) 0.4103(2) 1.1639(2) 0.0237(6) Uani
C20 0.6815(4) 0.4375(2) 0.9465(2) 0.0219(6) Uani
C21 0.7379(3) 0.4089(2) 0.8334(2) 0.0197(6) Uani
O1 1.3613(3) 0.0807(2) 0.3648(2) 0.0354(6) Uani
O2 1.3940(3) 0.0041(2) 0.5335(2) 0.0355(5) Uani
O3 1.2881(2) 0.1395(2) 0.90410(10) 0.0237(4) Uani
O4 1.2216(2) 0.2852(2) 0.89890(10) 0.0209(4) Uani
O5 1.1720(3) 0.4538(2) 0.5268(2) 0.0466(8) Uani
O6 1.2328(3) 0.3946(2) 0.36590(10) 0.0312(5) Uani
N1 1.3635(3) 0.0736(2) 0.4745(2) 0.0264(6) Uani
N2 1.2203(3) 0.3911(2) 0.4725(2) 0.0251(6) Uani
C1 1.2955(3) 0.23311 0.4740(2) 0.0189(6) Uani
C2 1.3267(3) 0.1542(2) 0.5389(2) 0.0195(6) Uani
C3 1.3228(3) 0.1465(2) 0.6614(2) 0.0181(6) Uani
C4 1.2849(3) 0.2215(2) 0.7227(2) 0.0156(5) Uani
C5 1.2533(3) 0.3026(2) 0.6615(2) 0.0167(6) Uani
C6 1.2602(3) 0.3060(2) 0.5391(2) 0.0189(6) Uani
C7 1.2673(3) 0.2111(2) 0.8522(2) 0.0174(6) Uani
O22 1.1016(2) 0.2578(2) 1.0873(2) 0.0238(5) Uani
H81 0.841(3) 0.066(2) 0.669(2) 0.015(5) Uiso
H111 0.748(3) 0.3730(10) 0.613(2) 0.013(5) Uiso
H121 0.791(4) 0.285(2) 0.452(2) 0.024(6) Uiso
H131 0.843(3) 0.131(2) 0.476(2) 0.024(6) Uiso
H141 0.968(3) 0.0500(10) 0.896(2) 0.016(6) Uiso
H142 0.751(4) 0.021(2) 0.826(2) 0.021(6) Uiso
H151 0.793(3) -0.019(2) 1.028(2) 0.022(6) Uiso
H152 0.637(3) 0.0600(10) 1.001(2) 0.010(5) Uiso
H161 0.770(4) 0.046(2) 1.231(2) 0.024(6) Uiso
H162 0.940(4) 0.112(2) 1.278(2) 0.020(6) Uiso
H171 0.574(3) 0.1650(10) 1.115(2) 0.016(5) Uiso
H172 0.611(4) 0.171(2) 1.267(2) 0.029(6) Uiso
H181 0.526(3) 0.314(2) 1.091(2) 0.021(6) Uiso
H182 0.576(3) 0.337(2) 1.243(2) 0.027(6) Uiso
H191 0.863(4) 0.414(2) 1.233(2) 0.029(7) Uiso
H192 0.679(3) 0.461(2) 1.160(2) 0.015(6) Uiso
H201 0.675(3) 0.503(2) 0.949(2) 0.018(6) Uiso
H202 0.548(3) 0.410(2) 0.939(2) 0.021(6) Uiso
H211 0.868(4) 0.426(2) 0.836(2) 0.021(6) Uiso
H212 0.641(3) 0.4350(10) 0.759(2) 0.016(6) Uiso
H11 1.293(3) 0.237(2) 0.386(2) 0.021(6) Uiso
H31 1.341(3) 0.091(2) 0.703(2) 0.011(5) Uiso
H41 1.187(4) 0.272(2) 0.960(2) 0.029(7) Uiso
H51 1.222(3) 0.355(2) 0.699(2) 0.022(6) Uiso
H221 1.009(4) 0.294(2) 1.084(2) 0.039(8) Uiso
H222 1.044(5) 0.212(3) 1.083(3) 0.060(10) Uiso
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.002 0.002 International_Tables_Vol_IV_Table_2.2B
H 0 0 International_Tables_Vol_IV_Table_2.2B
N 0.004 0.003 International_Tables_Vol_IV_Table_2.2B
O 0.008 0.006 International_Tables_Vol_IV_Table_2.2B
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 2 2
-2 1 0
-1 0 -2
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
C9 O7 C14 118.0(2) yes
C15 O8 C16 112.2(2) yes
C17 O9 C18 112.8(2) yes
C19 O10 C20 112.0(2) yes
C10 O11 C21 117.9(2) yes
C9 C8 C13 119.2(3) yes
O7 C9 C8 125.2(3) yes
O7 C9 C10 114.3(2) yes
C8 C9 C10 120.5(2) yes
O11 C10 C9 114.5(2) yes
O11 C10 C11 125.6(3) yes
C9 C10 C11 119.8(2) yes
C10 C11 C12 119.5(3) yes
C11 C12 C13 120.3(2) yes
C8 C13 C12 120.7(2) yes
O7 C14 C15 105.4(2) yes
O8 C15 C14 109.5(2) yes
O8 C16 C17 113.3(2) yes
O9 C17 C16 107.9(2) yes
O9 C18 C19 107.7(2) yes
O10 C19 C18 111.9(2) yes
O10 C20 C21 110.2(2) yes
O11 C21 C20 106.3(2) yes
C9 C8 H81 117.0(10) no
C13 C8 H81 124.0(10) no
C10 C11 H111 118.0(10) no
C12 C11 H111 123.0(10) no
C11 C12 H121 117(2) no
C13 C12 H121 123(2) no
C8 C13 H131 117(2) no
C12 C13 H131 122(2) no
O7 C14 H141 106.9(9) no
O7 C14 H142 111(2) no
C15 C14 H141 114.0(10) no
C15 C14 H142 111(2) no
H141 C14 H142 109(2) no
O8 C15 H151 110.0(10) no
O8 C15 H152 108.0(10) no
C14 C15 H151 108.0(10) no
C14 C15 H152 110.0(10) no
H151 C15 H152 112(2) no
O8 C16 H161 112.0(10) no
O8 C16 H162 104(2) no
C17 C16 H161 107(2) no
C17 C16 H162 113(2) no
H161 C16 H162 108(2) no
O9 C17 H171 111.0(10) no
O9 C17 H172 106(2) no
C16 C17 H171 110.0(10) no
C16 C17 H172 111(2) no
H171 C17 H172 111(2) no
O9 C18 H181 108(2) no
O9 C18 H182 110(2) no
C19 C18 H181 111(2) no
C19 C18 H182 109(2) no
H181 C18 H182 111(2) no
O10 C19 H191 105(2) no
O10 C19 H192 109.0(10) no
C18 C19 H191 109(2) no
C18 C19 H192 113(2) no
H191 C19 H192 108(2) no
O10 C20 H201 109.0(10) no
O10 C20 H202 110.0(10) no
C21 C20 H201 110.0(10) no
C21 C20 H202 106.0(10) no
H201 C20 H202 111(2) no
O11 C21 H211 108(2) no
O11 C21 H212 111.0(10) no
C20 C21 H211 113.0(10) no
C20 C21 H212 108.0(10) no
H211 C21 H212 110(2) no
O1 N1 O2 124.3(3) yes
O1 N1 C2 117.6(3) yes
O2 N1 C2 118.1(2) yes
O5 N2 O6 124.1(3) yes
O5 N2 C6 117.6(2) yes
O6 N2 C6 118.3(3) yes
C2 C1 C6 115.8(2) yes
N1 C2 C1 118.6(2) yes
N1 C2 C3 118.2(3) yes
C1 C2 C3 123.2(2) yes
C2 C3 C4 118.9(3) yes
C3 C4 C5 120.1(2) yes
C3 C4 C7 118.3(2) yes
C5 C4 C7 121.5(2) yes
C4 C5 C6 118.3(3) yes
N2 C6 C1 117.7(2) yes
N2 C6 C5 118.5(2) yes
C1 C6 C5 123.7(3) yes
O3 C7 O4 125.2(2) yes
O3 C7 C4 121.5(2) yes
O4 C7 C4 113.3(2) yes
C7 O4 H41 107(2) no
C2 C1 H11 122(2) no
C6 C1 H11 122(2) no
C2 C3 H31 121.0(10) no
C4 C3 H31 120.0(10) no
C4 C5 H51 123.0(10) no
C6 C5 H51 119.0(10) no
H221 O22 H222 100(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O7 C9 1.366(3) yes
O7 C14 1.429(4) yes
O8 C15 1.426(3) yes
O8 C16 1.436(3) yes
O9 C17 1.426(4) yes
O9 C18 1.423(4) yes
O10 C19 1.434(3) yes
O10 C20 1.431(3) yes
O11 C10 1.364(3) yes
O11 C21 1.432(4) yes
C8 C9 1.383(3) yes
C8 C13 1.406(3) yes
C9 C10 1.404(4) yes
C10 C11 1.390(3) yes
C11 C12 1.406(3) yes
C12 C13 1.369(4) yes
C14 C15 1.500(3) yes
C16 C17 1.509(4) yes
C18 C19 1.505(4) yes
C20 C21 1.497(3) yes
C8 H81 0.95(3) no
C11 H111 0.95(2) no
C12 H121 0.90(2) no
C13 H131 0.96(3) no
C14 H141 1.01(2) no
C14 H142 0.92(3) no
C15 H151 0.93(3) no
C15 H152 1.00(2) no
C16 H161 0.98(3) no
C16 H162 0.92(3) no
C17 H171 0.98(2) no
C17 H172 1.02(3) no
C18 H181 1.06(2) no
C18 H182 0.97(2) no
C19 H191 0.94(2) no
C19 H192 0.91(3) no
C20 H201 0.99(3) no
C20 H202 1.01(2) no
C21 H211 0.95(3) no
C21 H212 0.99(2) no
O1 N1 1.228(3) yes
O2 N1 1.225(4) yes
O3 C7 1.215(4) yes
O4 C7 1.314(4) yes
O5 N2 1.226(4) yes
O6 N2 1.223(3) yes
N1 C2 1.475(4) yes
N2 C6 1.470(4) yes
C1 C2 1.379(3) yes
C1 C6 1.382(3) yes
C2 C3 1.384(3) yes
C3 C4 1.389(4) yes
C4 C5 1.388(4) yes
C4 C7 1.499(3) yes
C5 C6 1.386(3) yes
O4 H41 0.82(2) no
C1 H11 0.98(2) no
C3 H31 0.95(3) no
C5 H51 0.95(3) no
O22 H221 0.85(3) no
O22 H222 0.80(4) no