#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/04/7150465.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7150465
loop_
_publ_author_name
'Camiolo, Salvatore'
'Gale, Philip A.'
'Hursthouse, Michael B.'
'Light, Mark E.'
_publ_section_title
;
 Nitrophenyl derivatives of pyrrole 2,5-diamides: structural behaviour,
 anion binding and colour change signalled deprotonationElectronic
 supplementary information (ESI) available: 1H NMR, 13C NMR and mass
 spectra for compounds 2 and 3, NMR anion titration profiles in
 DMSO-d6--0.5% water. See http://www.rsc.org/suppdata/ob/b2/b210848h/
;
_journal_issue                   4
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              741
_journal_paper_doi               10.1039/b210848h
_journal_volume                  1
_journal_year                    2003
_chemical_formula_sum            'C30 H19 N7 O10'
_chemical_formula_weight         637.52
_chemical_name_systematic
; 
? 
;
_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                 104.057(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.3034(11)
_cell_length_b                   10.1636(5)
_cell_length_c                   13.4570(6)
_cell_measurement_reflns_used    17978
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      3.04
_cell_volume                     2693.8(2)
_computing_cell_refinement
;
DENZO (Otwinowski and MInor, 1997), COLLECT (Hooft, 1998)
;
_computing_data_collection
;
DENZO (Otwinowski and Minor, 1997), COLLECT (Hooft, 1998)
;
_computing_data_reduction
;
DENZO (Otwinowski and MInor, 1997), COLLECT (Hooft, 1998),
MAXUS (Mackay et al., 1998)
;
_computing_molecular_graphics    'CAMERON (Watkin, et al., 1993)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean '9.091 pixels mm^1^'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Nonius Kappa CCD Area detector'
_diffrn_measurement_method       'φ and ω scans to fill the asymmetric unit'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0965
_diffrn_reflns_av_sigmaI/netI    0.1142
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17978
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.9964
_exptl_absorpt_correction_T_min  0.9879
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Prism
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Colourless
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.0021(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         4716
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.1256
_refine_ls_R_factor_gt           0.0550
_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)+(0.0563P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1308
_reflns_number_gt                2684
_reflns_number_total             4716
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b210848h.txt
_cod_data_source_block           compound3
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7150465
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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.40669(14) 1.0375(3) -0.2050(2) 0.0270(7) Uani 1 1 d . . .
H1 H -0.4151 0.9783 -0.2613 0.032 Uiso 1 1 calc R . .
C2 C -0.43992(15) 1.1556(3) -0.2127(2) 0.0278(7) Uani 1 1 d . . .
C3 C -0.42798(15) 1.2483(3) -0.1355(2) 0.0294(8) Uani 1 1 d . . .
H3 H -0.4497 1.3318 -0.1433 0.035 Uiso 1 1 calc R . .
C4 C -0.38242(15) 1.2116(3) -0.0466(2) 0.0279(7) Uani 1 1 d . . .
C5 C -0.34863(14) 1.0928(3) -0.0319(2) 0.0261(7) Uani 1 1 d . . .
H5 H -0.3184 1.0716 0.0319 0.031 Uiso 1 1 calc R . .
C6 C -0.36028(14) 1.0051(3) -0.1136(2) 0.0270(7) Uani 1 1 d . . .
C7 C -0.26762(15) 0.8457(3) -0.0489(2) 0.0256(7) Uani 1 1 d . . .
C8 C -0.24326(14) 0.7157(3) -0.0705(2) 0.0240(7) Uani 1 1 d . . .
C9 C -0.26185(14) 0.6255(3) -0.1505(2) 0.0257(7) Uani 1 1 d . . .
C10 C -0.21605(14) 0.5188(3) -0.1269(2) 0.0249(7) Uani 1 1 d . . .
C11 C -0.17056(15) 0.5484(3) -0.0348(2) 0.0260(7) Uani 1 1 d . . .
C12 C -0.10639(15) 0.4869(3) 0.0234(2) 0.0288(8) Uani 1 1 d . . .
C13 C -0.02639(15) 0.3073(3) 0.0031(2) 0.0266(7) Uani 1 1 d . . .
C14 C 0.01781(14) 0.3106(3) 0.1000(2) 0.0266(7) Uani 1 1 d . . .
H14 H 0.0121 0.3732 0.1497 0.032 Uiso 1 1 calc R . .
C15 C 0.06985(14) 0.2206(3) 0.1217(2) 0.0254(7) Uani 1 1 d . . .
C16 C 0.08126(14) 0.1269(3) 0.0543(2) 0.0266(7) Uani 1 1 d . . .
H16 H 0.1180 0.0665 0.0718 0.032 Uiso 1 1 calc R . .
C17 C 0.03604(15) 0.1260(3) -0.0405(2) 0.0266(7) Uani 1 1 d . . .
C18 C -0.01630(15) 0.2143(3) -0.0679(2) 0.0292(7) Uani 1 1 d . . .
H18 H -0.0455 0.2120 -0.1348 0.035 Uiso 1 1 calc R . .
C19 C -0.31778(14) 0.6361(3) -0.2445(2) 0.0259(7) Uani 1 1 d . . .
C20 C -0.36823(15) 0.5396(3) -0.2666(2) 0.0293(8) Uani 1 1 d . . .
H20 H -0.3667 0.4674 -0.2213 0.035 Uiso 1 1 calc R . .
C21 C -0.42029(15) 0.5487(3) -0.3540(2) 0.0324(8) Uani 1 1 d . . .
H21 H -0.4542 0.4824 -0.3686 0.039 Uiso 1 1 calc R . .
C22 C -0.42343(16) 0.6531(3) -0.4199(2) 0.0334(8) Uani 1 1 d . . .
H22 H -0.4596 0.6589 -0.4796 0.040 Uiso 1 1 calc R . .
C23 C -0.37428(15) 0.7490(3) -0.3996(2) 0.0307(8) Uani 1 1 d . . .
H23 H -0.3767 0.8214 -0.4450 0.037 Uiso 1 1 calc R . .
C24 C -0.32138(15) 0.7402(3) -0.3130(2) 0.0280(7) Uani 1 1 d . . .
H24 H -0.2871 0.8059 -0.3001 0.034 Uiso 1 1 calc R . .
C25 C -0.21548(14) 0.3967(3) -0.1873(2) 0.0259(7) Uani 1 1 d . . .
C26 C -0.22702(14) 0.2750(3) -0.1461(2) 0.0283(8) Uani 1 1 d . . .
H26 H -0.2393 0.2722 -0.0824 0.034 Uiso 1 1 calc R . .
C27 C -0.22091(15) 0.1589(3) -0.1963(2) 0.0325(8) Uani 1 1 d . . .
H27 H -0.2284 0.0769 -0.1669 0.039 Uiso 1 1 calc R . .
C28 C -0.20386(15) 0.1627(3) -0.2897(2) 0.0346(8) Uani 1 1 d . . .
H28 H -0.1991 0.0831 -0.3243 0.042 Uiso 1 1 calc R . .
C29 C -0.19366(16) 0.2824(3) -0.3328(2) 0.0347(8) Uani 1 1 d . . .
H29 H -0.1827 0.2849 -0.3976 0.042 Uiso 1 1 calc R . .
C30 C -0.19938(14) 0.3985(3) -0.2816(2) 0.0310(8) Uani 1 1 d . . .
H30 H -0.1922 0.4803 -0.3115 0.037 Uiso 1 1 calc R . .
N1 N -0.49155(13) 1.1836(3) -0.3074(2) 0.0348(7) Uani 1 1 d . . .
N2 N -0.37043(13) 1.3051(3) 0.0394(2) 0.0383(7) Uani 1 1 d . . .
N3 N -0.32903(12) 0.8820(2) -0.10999(18) 0.0275(6) Uani 1 1 d . . .
H3A H -0.3513 0.8213 -0.1515 0.033 Uiso 1 1 calc R . .
N4 N -0.18831(12) 0.6659(2) -0.00170(18) 0.0269(6) Uani 1 1 d . . .
H4 H -0.1674 0.7045 0.0559 0.032 Uiso 1 1 calc R . .
N5 N -0.08228(12) 0.3901(2) -0.02924(18) 0.0305(6) Uani 1 1 d . . .
H5A H -0.1055 0.3784 -0.0929 0.037 Uiso 1 1 calc R . .
N6 N 0.11675(13) 0.2197(2) 0.2247(2) 0.0287(6) Uani 1 1 d . . .
N7 N 0.04281(14) 0.0217(2) -0.1136(2) 0.0311(6) Uani 1 1 d . . .
O1 O -0.50316(11) 1.0999(2) -0.37534(17) 0.0428(6) Uani 1 1 d . . .
O2 O -0.52156(11) 1.2890(2) -0.31318(17) 0.0433(6) Uani 1 1 d . . .
O3 O -0.36997(14) 1.4222(2) 0.01907(19) 0.0594(8) Uani 1 1 d . . .
O4 O -0.36157(11) 1.2602(2) 0.12555(19) 0.0436(6) Uani 1 1 d . . .
O5 O -0.23393(10) 0.9170(2) 0.01782(16) 0.0350(6) Uani 1 1 d . . .
O6 O -0.07720(10) 0.5250(2) 0.10779(16) 0.0363(6) Uani 1 1 d . . .
O7 O 0.10674(10) 0.2968(2) 0.28898(16) 0.0369(6) Uani 1 1 d . . .
O8 O 0.16390(10) 0.1413(2) 0.24050(16) 0.0366(6) Uani 1 1 d . . .
O9 O 0.08917(11) -0.0576(2) -0.08543(16) 0.0377(6) Uani 1 1 d . . .
O10 O 0.00039(11) 0.0177(2) -0.19608(17) 0.0367(6) Uani 1 1 d . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.3(3) . . ?
C1 C2 C3 123.3(3) . . ?
C1 C2 N1 118.1(3) . . ?
C3 C2 N1 118.6(3) . . ?
C4 C3 C2 115.3(3) . . ?
C3 C4 C5 124.7(3) . . ?
C3 C4 N2 117.2(3) . . ?
C5 C4 N2 118.1(3) . . ?
C4 C5 C6 117.7(3) . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 N3 123.9(3) . . ?
C1 C6 N3 116.5(3) . . ?
O5 C7 N3 123.1(3) . . ?
O5 C7 C8 121.6(3) . . ?
N3 C7 C8 115.3(3) . . ?
N4 C8 C9 107.7(2) . . ?
N4 C8 C7 117.4(3) . . ?
C9 C8 C7 134.8(3) . . ?
C8 C9 C10 106.9(3) . . ?
C8 C9 C19 128.2(3) . . ?
C10 C9 C19 124.9(3) . . ?
C11 C10 C9 107.1(3) . . ?
C11 C10 C25 125.3(2) . . ?
C9 C10 C25 127.6(3) . . ?
N4 C11 C10 108.2(2) . . ?
N4 C11 C12 117.8(3) . . ?
C10 C11 C12 133.6(3) . . ?
O6 C12 N5 124.0(3) . . ?
O6 C12 C11 121.9(3) . . ?
N5 C12 C11 114.0(3) . . ?
C14 C13 N5 124.6(3) . . ?
C14 C13 C18 119.3(3) . . ?
N5 C13 C18 116.0(3) . . ?
C15 C14 C13 118.1(3) . . ?
C16 C15 C14 124.4(3) . . ?
C16 C15 N6 116.2(3) . . ?
C14 C15 N6 119.3(3) . . ?
C15 C16 C17 115.8(3) . . ?
C18 C17 C16 122.9(3) . . ?
C18 C17 N7 118.8(3) . . ?
C16 C17 N7 118.2(3) . . ?
C17 C18 C13 119.5(3) . . ?
C24 C19 C20 118.3(3) . . ?
C24 C19 C9 121.7(3) . . ?
C20 C19 C9 120.0(3) . . ?
C21 C20 C19 120.3(3) . . ?
C22 C21 C20 120.5(3) . . ?
C21 C22 C23 120.1(3) . . ?
C22 C23 C24 120.0(3) . . ?
C23 C24 C19 120.8(3) . . ?
C30 C25 C26 118.3(3) . . ?
C30 C25 C10 121.7(3) . . ?
C26 C25 C10 119.8(3) . . ?
C27 C26 C25 121.2(3) . . ?
C26 C27 C28 119.6(3) . . ?
C27 C28 C29 120.1(3) . . ?
C28 C29 C30 120.0(3) . . ?
C29 C30 C25 120.8(3) . . ?
O2 N1 O1 123.7(3) . . ?
O2 N1 C2 117.6(3) . . ?
O1 N1 C2 118.6(3) . . ?
O4 N2 O3 124.8(3) . . ?
O4 N2 C4 117.7(3) . . ?
O3 N2 C4 117.5(3) . . ?
C7 N3 C6 127.0(2) . . ?
C11 N4 C8 110.1(2) . . ?
C12 N5 C13 129.6(3) . . ?
O7 N6 O8 123.6(3) . . ?
O7 N6 C15 118.7(2) . . ?
O8 N6 C15 117.7(3) . . ?
O9 N7 O10 125.0(2) . . ?
O9 N7 C17 117.0(3) . . ?
O10 N7 C17 117.9(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.368(4) . ?
C1 C6 1.395(4) . ?
C2 C3 1.380(4) . ?
C2 N1 1.468(4) . ?
C3 C4 1.375(4) . ?
C4 C5 1.379(4) . ?
C4 N2 1.471(4) . ?
C5 C6 1.391(4) . ?
C6 N3 1.399(3) . ?
C7 O5 1.225(3) . ?
C7 N3 1.367(4) . ?
C7 C8 1.464(4) . ?
C8 N4 1.362(3) . ?
C8 C9 1.395(4) . ?
C9 C10 1.413(4) . ?
C9 C19 1.485(4) . ?
C10 C11 1.387(4) . ?
C10 C25 1.486(4) . ?
C11 N4 1.354(3) . ?
C11 C12 1.485(4) . ?
C12 O6 1.209(3) . ?
C12 N5 1.371(4) . ?
C13 C14 1.392(4) . ?
C13 N5 1.395(4) . ?
C13 C18 1.395(4) . ?
C14 C15 1.374(4) . ?
C15 C16 1.374(4) . ?
C15 N6 1.478(4) . ?
C16 C17 1.379(4) . ?
C17 C18 1.371(4) . ?
C17 N7 1.475(4) . ?
C19 C24 1.394(4) . ?
C19 C20 1.397(4) . ?
C20 C21 1.380(4) . ?
C21 C22 1.374(4) . ?
C22 C23 1.374(4) . ?
C23 C24 1.382(4) . ?
C25 C30 1.385(4) . ?
C25 C26 1.399(4) . ?
C26 C27 1.380(4) . ?
C27 C28 1.383(4) . ?
C28 C29 1.385(4) . ?
C29 C30 1.385(4) . ?
N1 O2 1.226(3) . ?
N1 O1 1.229(3) . ?
N2 O4 1.218(3) . ?
N2 O3 1.222(3) . ?
N6 O7 1.220(3) . ?
N6 O8 1.224(3) . ?
N7 O9 1.227(3) . ?
N7 O10 1.229(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A O2 0.88 2.53 3.105(3) 123.6 2_444
N4 H4 O7 0.88 2.35 3.225(3) 176.5 2
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21141565
