#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007145.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_2007145
loop_
_publ_author_name
'Fitzgerald, L. J.'
'Gerkin, R. E.'
_publ_section_title
;
 Phenolphthalein and 3',3''-Dinitrophenolphthalein
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              535
_journal_page_last               539
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C20 H12 N2 O8'
_chemical_formula_sum            'C20 H12 N2 O8'
_chemical_formula_weight         408.32
_chemical_name_common            3',3''-dinitrophenolphthalein
_chemical_name_systematic        ' ?'
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.634(2)
_cell_length_b                   8.122(4)
_cell_length_c                   15.741(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      14.9
_cell_measurement_theta_min      11.6
_cell_volume                     3533.0(19)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
1988)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1989)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  TEXSAN
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      296
_diffrn_measurement_device_type  AFC5S
_diffrn_measurement_method       '\w scans '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4602
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.0
_diffrn_standards_decay_%
'no decay: variation =  +-2.0 (ave. max. rel. intensity)'
_diffrn_standards_interval_count 150
_diffrn_standards_number         6
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_meas      none
_exptl_crystal_description       'cut column'
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.61
_refine_diff_density_min         -0.56
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.10
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4069
_refine_ls_R_factor_gt           0.050
_refine_ls_shift/su_max          '< 0.01'
_refine_ls_structure_factor_coef F^2^
_refine_ls_weighting_scheme      'w = 1/\s^2^(F^2^)'
_refine_ls_wR_factor_ref         0.122
_reflns_number_gt                1780
_reflns_number_total             4602
_reflns_threshold_expression     'I > 2\s~I~'
_[local]_cod_data_source_file    bk1369.cif
_[local]_cod_data_source_block   II
_cod_original_cell_volume        3533.1(16)
_cod_database_code               2007145
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
1/2-x,1/2-y,1/2+z
'1/2+x,1/2-y,   -z'
'   -x,   +y,1/2-z'
'   -x,   -y,   -z'
1/2+x,1/2+y,1/2-z
'1/2-x,1/2+y,   +z'
'   +x,   -y,1/2+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
O1 0.13116(6) 0.1237(2) 0.37740(10) 0.0394(5) Uij
O2 0.11216(8) 0.0935(3) 0.24020(10) 0.0598(7) Uij
O3A* 0.21115(10) 0.1406(5) 0.7280(2) 0.1250(10) Uij
O3B* 0.28492(9) 0.2065(5) 0.7170(2) 0.1170(10) Uij
O3A# 0.06260(8) -0.2600(3) 0.5667(2) 0.0654(8) Uij
O3B# 0.00412(9) -0.1968(3) 0.6501(2) 0.0753(8) Uij
O4* 0.32170(7) 0.3065(3) 0.5755(2) 0.0698(8) Uij
O4# -0.02499(8) 0.1028(4) 0.6639(2) 0.0692(8) Uij
N3* 0.24434(10) 0.1917(4) 0.6866(2) 0.0760(10) Uij
N3# 0.03691(9) -0.1587(3) 0.6002(2) 0.0500(8) Uij
C1 0.13136(9) 0.2561(3) 0.4422(2) 0.0363(8) Uij
C1* 0.18147(9) 0.2607(3) 0.4823(2) 0.0371(8) Uij
C1# 0.09026(9) 0.2156(3) 0.5037(2) 0.0332(7) Uij
C2 0.12234(9) 0.4086(3) 0.3887(2) 0.0351(8) Uij
C2* 0.19018(10) 0.2249(4) 0.5661(2) 0.0432(9) Uij
C2# 0.08224(10) 0.0548(4) 0.5269(2) 0.0394(9) Uij
C3 0.11314(9) 0.3628(3) 0.3064(2) 0.0381(8) Uij
C3* 0.23705(10) 0.2375(4) 0.5986(2) 0.0465(9) Uij
C3# 0.04403(9) 0.0151(3) 0.5802(2) 0.0377(8) Uij
C4 0.11752(10) 0.1844(4) 0.2994(2) 0.0428(9) Uij
C4* 0.27581(10) 0.2882(4) 0.5487(2) 0.0485(9) Uij
C4# 0.01321(10) 0.1340(4) 0.6133(2) 0.0450(9) Uij
C5 0.12533(10) 0.5734(4) 0.4109(2) 0.0429(9) Uij
C5* 0.26640(10) 0.3228(4) 0.4641(2) 0.0536(10) Uij
C5# 0.02170(10) 0.2972(4) 0.5906(2) 0.0517(10) Uij
C6 0.11780(10) 0.6875(4) 0.3477(2) 0.0500(10) Uij
C6* 0.22060(10) 0.3087(4) 0.4319(2) 0.0500(10) Uij
C6# 0.05940(10) 0.3358(4) 0.5364(2) 0.0461(9) Uij
C7 0.10690(10) 0.6408(4) 0.2654(2) 0.0560(10) Uij
C8 0.10450(10) 0.4771(4) 0.2433(2) 0.0530(10) Uij
H2* 0.1670(9) 0.187(3) 0.603(2) 0.046(8) Uiso
H2# 0.1025(9) -0.030(3) 0.507(2) 0.051(9) Uiso
H4* 0.321(2) 0.267(6) 0.633(3) 0.15(2) Uiso
H4# -0.025(2) -0.025(6) 0.677(3) 0.15(2) Uiso
H5 0.1331(10) 0.601(3) 0.470(2) 0.061(9) Uiso
H5* 0.2950(10) 0.355(4) 0.431(2) 0.080(10) Uiso
H5# -0.0010(10) 0.394(3) 0.622(2) 0.064(9) Uiso
H6 0.1180(10) 0.800(4) 0.363(2) 0.070(10) Uiso
H6* 0.2163(8) 0.338(3) 0.375(2) 0.035(7) Uiso
H6# 0.0635(10) 0.446(4) 0.520(2) 0.060(10) Uiso
H7 0.1020(10) 0.717(3) 0.223(2) 0.055(9) Uiso
H8 0.0980(9) 0.443(3) 0.186(2) 0.051(8) Uiso
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 0.0480(10) 0.0370(10) 0.0334(10) 0.0031(9) -0.0004(9) -0.0039(9)
O2 0.086(2) 0.0540(10) 0.0390(10) 0.0020(10) -0.0110(10) -0.0110(10)
OA* 0.067(2) 0.251(4) 0.056(2) -0.035(2) -0.0100(10) 0.057(2)
O3B* 0.060(2) 0.237(4) 0.055(2) -0.025(2) -0.0240(10) 0.031(2)
O3A# 0.077(2) 0.0480(10) 0.071(2) 0.0010(10) 0.0100(10) 0.0020(10)
O3B# 0.067(2) 0.078(2) 0.081(2) -0.0110(10) 0.0210(10) 0.0210(10)
O4* 0.0320(10) 0.116(2) 0.0610(10) -0.0050(10) -0.0070(10) 0.008(2)
O4# 0.0490(10) 0.090(2) 0.069(2) -0.0020(10) 0.0230(10) -0.0020(10)
N3* 0.049(2) 0.136(3) 0.0420(10) -0.006(2) -0.0090(10) 0.013(2)
N3# 0.044(2) 0.061(2) 0.045(2) -0.0070(10) -0.0030(10) 0.0070(10)
C1 0.038(2) 0.041(2) 0.0300(10) 0.0020(10) 0.0020(10) -0.0060(10)
C1* 0.0350(10) 0.041(2) 0.0350(10) 0.0030(10) 0.0010(10) -0.0010(10)
C1# 0.0310(10) 0.039(2) 0.0300(10) 0.0020(10) -0.0050(10) 0.0000(10)
C2 0.0300(10) 0.038(2) 0.037(2) 0.0010(10) -0.0020(10) 0.0000(10)
C2* 0.034(2) 0.060(2) 0.035(2) -0.003(2) 0.0040(10) 0.005(2)
C2# 0.034(2) 0.048(2) 0.036(2) 0.0080(10) -0.0020(10) 0.000(2)
C3 0.038(2) 0.041(2) 0.035(2) 0.0010(10) -0.0030(10) 0.0000(10)
C3* 0.039(2) 0.068(2) 0.033(2) 0.002(2) -0.0050(10) -0.001(2)
C3# 0.0340(10) 0.044(2) 0.036(2) -0.0030(10) -0.0070(10) 0.0060(10)
C4 0.041(2) 0.051(2) 0.036(2) 0.0010(10) -0.0020(10) -0.001(2)
C4* 0.035(2) 0.064(2) 0.047(2) 0.002(2) -0.0040(10) -0.004(2)
C4# 0.033(2) 0.063(2) 0.040(2) -0.004(2) 0.0020(10) -0.006(2)
C5 0.043(2) 0.042(2) 0.043(2) 0.0020(10) -0.0020(10) -0.003(2)
C5* 0.035(2) 0.079(3) 0.047(2) -0.002(2) 0.0030(10) 0.009(2)
C5# 0.048(2) 0.057(2) 0.050(2) 0.004(2) 0.009(2) -0.011(2)
C6 0.054(2) 0.036(2) 0.062(2) 0.005(2) -0.001(2) 0.000(2)
C6* 0.045(2) 0.073(2) 0.032(2) 0.003(2) -0.0010(10) 0.004(2)
C6# 0.048(2) 0.041(2) 0.049(2) 0.001(2) 0.0010(10) -0.006(2)
C7 0.068(2) 0.049(2) 0.052(2) 0.007(2) -0.007(2) 0.013(2)
C8 0.065(2) 0.057(2) 0.036(2) 0.006(2) -0.008(2) 0.002(2)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H 0 0 'Stewart, Davidson & Simpson (1965)'
C .002 .002 'Cromer & Waber (1974)'
O .008 .006 'Cromer & Waber (1974)'
N .004 .003 'Cromer & Waber (1974)'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 C4 ? 110.8(2) yes
C4* O4* H4* ? 103(2) no
C4# O4# H4# ? 107(2) no
O3A* N3* O3B* ? 121.4(3) yes
O3A* N3* C3* ? 120.2(3) yes
O3B* N3* C3* ? 118.4(3) yes
O3A# N3# O3B# ? 122.4(3) yes
O3A# N3# C3# ? 119.0(2) yes
O3B# N3# C3# ? 118.5(3) yes
O1 C1 C1* ? 107.9(2) no
O1 C1 C1# ? 106.1(2) no
O1 C1 C2 ? 102.1(2) yes
C1* C1 C1# ? 114.7(2) no
C1* C1 C2 ? 111.1(2) no
C1# C1 C2 ? 113.9(2) no
C1 C1* C2* ? 123.6(2) no
C1 C1* C6* ? 118.4(2) no
C2* C1* C6* ? 118.0(3) no
C1 C1# C2# ? 119.5(2) no
C1 C1# C6# ? 122.5(3) no
C2# C1# C6# ? 117.9(3) no
C1 C2 C3 ? 109.5(2) yes
C1 C2 C5 ? 129.6(2) no
C3 C2 C5 ? 120.7(3) no
C1* C2* C3* ? 119.9(3) no
C1* C2* H2* ? 124.0(10) no
C3* C2* H2* ? 115.0(10) no
C1# C2# C3# ? 120.3(3) no
C1# C2# H2# ? 120.0(10) no
C3# C2# H2# ? 119.0(10) no
C2 C3 C4 ? 109.0(2) yes
C2 C3 C8 ? 122.0(3) no
C4 C3 C8 ? 128.9(3) no
N3* C3* C2* ? 117.4(3) no
N3* C3* C4* ? 120.6(2) no
C2* C3* C4* ? 122.0(3) no
N3# C3# C2# ? 117.3(3) no
N3# C3# C4# ? 120.6(3) no
C2# C3# C4# ? 122.1(3) no
O1 C4 O2 ? 120.5(3) yes
O1 C4 C3 ? 108.1(2) yes
O2 C4 C3 ? 131.3(3) no
O4* C4* C3* ? 125.6(3) no
O4* C4* C5* ? 117.1(3) no
C3* C4* C5* ? 117.3(3) no
O4# C4# C3# ? 124.9(3) no
O4# C4# C5# ? 117.5(3) no
C3# C4# C5# ? 117.6(3) no
C2 C5 C6 ? 117.3(3) no
C2 C5 H5 ? 118.0(10) no
C6 C5 H5 ? 124.0(10) no
C4* C5* C6* ? 120.9(3) no
C4* C5* H5* ? 114.0(10) no
C6* C5* H5* ? 124.0(10) no
C6# C5# H5# ? 122.0(10) no
C4# C5# H5# ? 117.0(10) no
C4# C5# C6# ? 120.0(3) no
C5 C6 C7 ? 121.7(3) no
C5 C6 H6 ? 117.0(10) no
C7 C6 H6 ? 120.0(10) no
C1* C6* C5* ? 121.9(3) no
C1* C6* H6* ? 121.0(10) no
C5* C6* H6* ? 117.0(10) no
C1# C6# C5# ? 122.0(3) no
C1# C6# H6# ? 119.0(10) no
C5# C6# H6# ? 118.0(10) no
C6 C7 C8 ? 120.8(3) no
C6 C7 H7 ? 121.0(10) no
C8 C7 H7 ? 117.0(10) no
C3 C8 C7 ? 117.3(3) no
C3 C8 H8 ? 120.0(10) no
C7 C8 H8 ? 121.0(10) no
O4* H4* O3B* ? 146(3) no
O4* H4* O2 2_555 115(3) no
O4# H4# O3B# ? 141(4) no
O4# H4# O2 5_556 107(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.482(3) yes
O1 C4 1.375(3) yes
O2 C4 1.198(3) yes
O3A* N3* 1.200(3) yes
O3B* N3* 1.226(3) yes
O3A# N3# 1.207(3) yes
O3B# N3# 1.239(3) yes
O4* C4* 1.345(3) yes
O4* H4* 0.96(4) no
O4# C4# 1.347(3) yes
O4# H4# 1.06(5) no
N3* C3* 1.448(3) yes
N3# C3# 1.460(4) yes
C1 C1* 1.523(3) yes
C1 C1# 1.529(3) yes
C1 C2 1.518(3) yes
C1* C2* 1.372(3) no
C1* C6* 1.398(4) no
C1# C2# 1.374(4) no
C1# C6# 1.395(4) no
C2 C3 1.372(3) yes
C2 C5 1.386(4) no
C2* C3* 1.396(4) no
C2* H2* 0.92(2) no
C2# C3# 1.386(4) no
C2# H2# 0.94(3) no
C3 C4 1.458(4) yes
C3 C8 1.381(4) nos
C3* C4* 1.390(4) no
C3# C4# 1.389(4) no
C4* C5* 1.385(4) no
C4# C5# 1.392(4) no
C5 C6 1.376(4) no
C5 H5 0.98(3) no
C5* C6* 1.368(4) no
C5* H5* 0.98(3) no
C5# C6# 1.383(4) no
C5# H5# 1.12(3) no
C6 C7 1.383(4) no
C6 H6 0.95(3) no
C6* H6* 0.94(2) no
C6# H6# 0.94(3) no
C7 C8 1.376(4) no
C7 H7 0.92(3) no
C8 H8 0.95(3) no
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
O4# H4# O3B# ? 1.06(5) 1.67(5) 2.572(4) 141(4) yes
O4# H4# O2 5_556 1.06(5) 2.80(4) 3.259(3) 107(3) yes
O4* H4* O3B* ? 0.96(4) 1.73(5) 2.580(3) 146(4) yes
O4* H4* O2 2_555 0.96(4) 2.75(4) 3.274(3) 115(3) yes
C2# H2# O1 ? 0.94(3) 2.52(3) 2.771(3) 96(2) yes
C2# H2# O3A# ? 0.94(3) 2.37(3) 2.688(4) 100(2) yes
C2* H2* O3A* ? 0.92(2) 2.34(2) 2.702(4) 103(2) yes
C5 H5 O4* 7_555 0.98(3) 2.67(3) 3.527(4) 147(2) yes
C6 H6 O1 1_565 0.95(3) 2.66(3) 3.593(4) 167(2) yes
C6 H6 O4# 5_566 0.95(3) 2.72(3) 3.084(4) 104(2) yes
C6# H6# O3A# 1_565 0.94(3) 2.50(3) 3.319(4) 146(2) yes
C6* H6* O3B* 2_554 0.94(3) 2.51(2) 3.388(4) 156(2) yes
C8 H8 O3A# 8_554 0.95(3) 2.59(3) 3.489(4) 157(2) yes