#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/07/7100749.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_7100749
loop_
_publ_author_name
'Evans, Louise S.'
'Gale, Philip A.'
'Light, Mark E.'
'Quesada, Roberto'
_publ_section_title
;
 Pyrrolylamidourea based anion receptors
;
_journal_issue                   7
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1019
_journal_paper_doi               10.1039/b603223k
_journal_volume                  30
_journal_year                    2006
_chemical_compound_source        'Roberto Quesada'
_chemical_formula_sum            'C25 H21 N5 O4'
_chemical_formula_weight         455.47
_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                 115.5230(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.0210(4)
_cell_length_b                   8.0777(2)
_cell_length_c                   16.7769(4)
_cell_measurement_reflns_used    5221
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     2203.86(9)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 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, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker-Nonius CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans to fill the asymmetric unit'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_sigmaI/netI    0.0527
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20202
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.35
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9905
_exptl_absorpt_correction_T_min  0.9711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0040(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         5054
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0398P)²+1.7264P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1352
_reflns_number_gt                3604
_reflns_number_total             5054
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b603223k.txt
_cod_data_source_block           2005sot1106
_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      P2(1)/c
_cod_database_code               7100749
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 0.19166(13) 0.5659(3) 0.75439(14) 0.0382(6) Uani 1 1 d . . .
H1A H 0.1881 0.6857 0.7615 0.057 Uiso 1 1 calc R . .
H1B H 0.2386 0.5212 0.8058 0.057 Uiso 1 1 calc R . .
H1C H 0.1409 0.5130 0.7494 0.057 Uiso 1 1 calc R . .
C2 C 0.20293(12) 0.5323(3) 0.67272(13) 0.0273(4) Uani 1 1 d . . .
C3 C 0.27310(11) 0.4962(2) 0.66105(12) 0.0235(4) Uani 1 1 d . . .
C4 C 0.24714(11) 0.4633(2) 0.56971(12) 0.0216(4) Uani 1 1 d . . .
C5 C 0.16224(11) 0.4825(2) 0.52913(12) 0.0230(4) Uani 1 1 d . . .
C6 C 0.09928(11) 0.4647(2) 0.43898(13) 0.0242(4) Uani 1 1 d . . .
C7 C 0.02539(11) 0.4637(2) 0.22808(12) 0.0234(4) Uani 1 1 d . . .
C8 C -0.08900(12) 0.4478(2) 0.07686(12) 0.0249(4) Uani 1 1 d . . .
C9 C -0.06303(12) 0.5718(3) 0.03730(13) 0.0279(4) Uani 1 1 d . . .
H9 H -0.0141 0.6318 0.0710 0.033 Uiso 1 1 calc R . .
C10 C -0.10872(13) 0.6079(3) -0.05138(13) 0.0293(5) Uani 1 1 d . . .
H10 H -0.0910 0.6915 -0.0791 0.035 Uiso 1 1 calc R . .
C11 C -0.18004(14) 0.5210(3) -0.09885(13) 0.0330(5) Uani 1 1 d . . .
C12 C -0.20890(14) 0.4024(3) -0.06026(14) 0.0378(5) Uani 1 1 d . . .
H12 H -0.2590 0.3460 -0.0939 0.045 Uiso 1 1 calc R . .
C13 C -0.16350(13) 0.3669(3) 0.02825(13) 0.0313(5) Uani 1 1 d . . .
H13 H -0.1831 0.2871 0.0562 0.038 Uiso 1 1 calc R . .
C14 C 0.35847(11) 0.4863(3) 0.73121(12) 0.0242(4) Uani 1 1 d . . .
C15 C 0.38992(12) 0.6064(3) 0.79703(13) 0.0308(5) Uani 1 1 d . . .
H15 H 0.3562 0.6968 0.7971 0.037 Uiso 1 1 calc R . .
C16 C 0.46975(13) 0.5956(3) 0.86236(14) 0.0381(5) Uani 1 1 d . . .
H16 H 0.4901 0.6781 0.9070 0.046 Uiso 1 1 calc R . .
C17 C 0.51984(13) 0.4662(3) 0.86301(15) 0.0390(6) Uani 1 1 d . . .
H17 H 0.5746 0.4596 0.9078 0.047 Uiso 1 1 calc R . .
C18 C 0.49000(13) 0.3466(3) 0.79838(14) 0.0368(5) Uani 1 1 d . . .
H18 H 0.5243 0.2572 0.7986 0.044 Uiso 1 1 calc R . .
C19 C 0.40990(12) 0.3560(3) 0.73284(13) 0.0299(5) Uani 1 1 d . . .
H19 H 0.3899 0.2727 0.6886 0.036 Uiso 1 1 calc R . .
C20 C 0.29993(11) 0.4278(3) 0.52414(12) 0.0244(4) Uani 1 1 d . . .
C21 C 0.34593(12) 0.5543(3) 0.51140(15) 0.0391(6) Uani 1 1 d . . .
H21 H 0.3455 0.6615 0.5346 0.047 Uiso 1 1 calc R . .
C22 C 0.39228(16) 0.5253(5) 0.4652(2) 0.0641(9) Uani 1 1 d . . .
H22 H 0.4233 0.6129 0.4568 0.077 Uiso 1 1 calc R . .
C23 C 0.39395(16) 0.3720(6) 0.43153(17) 0.0688(11) Uani 1 1 d . . .
H23 H 0.4254 0.3538 0.3992 0.083 Uiso 1 1 calc R . .
C24 C 0.35021(15) 0.2450(4) 0.44450(15) 0.0575(9) Uani 1 1 d . . .
H24 H 0.3521 0.1380 0.4219 0.069 Uiso 1 1 calc R . .
C25 C 0.30284(13) 0.2716(3) 0.49078(14) 0.0366(5) Uani 1 1 d . . .
H25 H 0.2725 0.1829 0.4995 0.044 Uiso 1 1 calc R . .
N1 N 0.13752(10) 0.5245(2) 0.59302(10) 0.0273(4) Uani 1 1 d . . .
H1 H 0.0863 0.5437 0.5835 0.033 Uiso 1 1 calc R . .
N2 N 0.12423(9) 0.4233(2) 0.37536(10) 0.0260(4) Uani 1 1 d . . .
H2 H 0.1756 0.4365 0.3839 0.031 Uiso 1 1 calc R . .
N3 N 0.06552(10) 0.3598(2) 0.29693(10) 0.0262(4) Uani 1 1 d . . .
H3 H 0.0543 0.2532 0.2917 0.031 Uiso 1 1 calc R . .
N4 N -0.04240(9) 0.3910(2) 0.16352(10) 0.0257(4) Uani 1 1 d . . .
H4 H -0.0588 0.2977 0.1779 0.031 Uiso 1 1 calc R . .
N5 N -0.22617(14) 0.5535(3) -0.19385(13) 0.0455(5) Uani 1 1 d . . .
O1 O 0.02553(8) 0.4847(2) 0.41911(9) 0.0337(4) Uani 1 1 d . . .
O2 O 0.04831(8) 0.60601(17) 0.22444(9) 0.0278(3) Uani 1 1 d . . .
O3 O -0.29204(16) 0.4822(3) -0.23275(13) 0.0960(10) Uani 1 1 d . . .
O4 O -0.19717(11) 0.6503(2) -0.22886(10) 0.0476(5) 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
N1 C2 C3 108.02(17) . . ?
N1 C2 C1 120.74(17) . . ?
C3 C2 C1 131.15(18) . . ?
C2 C3 C4 107.10(16) . . ?
C2 C3 C14 126.50(17) . . ?
C4 C3 C14 126.35(17) . . ?
C5 C4 C3 106.79(16) . . ?
C5 C4 C20 125.77(17) . . ?
C3 C4 C20 127.29(16) . . ?
N1 C5 C4 107.76(16) . . ?
N1 C5 C6 117.87(16) . . ?
C4 C5 C6 134.36(17) . . ?
O1 C6 N2 119.99(17) . . ?
O1 C6 C5 122.32(18) . . ?
N2 C6 C5 117.69(16) . . ?
O2 C7 N3 123.54(17) . . ?
O2 C7 N4 124.46(18) . . ?
N3 C7 N4 111.99(17) . . ?
C9 C8 C13 119.67(18) . . ?
C9 C8 N4 123.71(17) . . ?
C13 C8 N4 116.55(18) . . ?
C10 C9 C8 119.84(19) . . ?
C11 C10 C9 119.2(2) . . ?
C10 C11 C12 122.00(19) . . ?
C10 C11 N5 119.2(2) . . ?
C12 C11 N5 118.8(2) . . ?
C11 C12 C13 118.7(2) . . ?
C12 C13 C8 120.4(2) . . ?
C15 C14 C19 118.02(18) . . ?
C15 C14 C3 121.31(18) . . ?
C19 C14 C3 120.67(17) . . ?
C16 C15 C14 120.8(2) . . ?
C17 C16 C15 120.5(2) . . ?
C18 C17 C16 119.6(2) . . ?
C17 C18 C19 120.3(2) . . ?
C18 C19 C14 120.78(19) . . ?
C21 C20 C25 118.5(2) . . ?
C21 C20 C4 119.66(19) . . ?
C25 C20 C4 121.81(19) . . ?
C22 C21 C20 120.4(3) . . ?
C23 C22 C21 120.8(3) . . ?
C24 C23 C22 119.8(2) . . ?
C23 C24 C25 120.3(3) . . ?
C20 C25 C24 120.1(2) . . ?
C2 N1 C5 110.32(16) . . ?
C6 N2 N3 117.35(15) . . ?
C7 N3 N2 119.25(16) . . ?
C7 N4 C8 127.62(17) . . ?
O4 N5 O3 124.2(2) . . ?
O4 N5 C11 118.4(2) . . ?
O3 N5 C11 117.4(2) . . ?
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 1.494(3) . ?
C2 N1 1.350(2) . ?
C2 C3 1.391(3) . ?
C3 C4 1.421(3) . ?
C3 C14 1.483(3) . ?
C4 C5 1.390(3) . ?
C4 C20 1.483(3) . ?
C5 N1 1.369(2) . ?
C5 C6 1.455(3) . ?
C6 O1 1.234(2) . ?
C6 N2 1.366(2) . ?
C7 O2 1.231(2) . ?
C7 N3 1.357(2) . ?
C7 N4 1.368(2) . ?
C8 C9 1.390(3) . ?
C8 C13 1.397(3) . ?
C8 N4 1.406(2) . ?
C9 C10 1.386(3) . ?
C10 C11 1.377(3) . ?
C11 C12 1.378(3) . ?
C11 N5 1.469(3) . ?
C12 C13 1.382(3) . ?
C14 C15 1.394(3) . ?
C14 C19 1.395(3) . ?
C15 C16 1.385(3) . ?
C16 C17 1.378(3) . ?
C17 C18 1.377(3) . ?
C18 C19 1.389(3) . ?
C20 C21 1.389(3) . ?
C20 C25 1.390(3) . ?
C21 C22 1.382(4) . ?
C22 C23 1.367(5) . ?
C23 C24 1.367(5) . ?
C24 C25 1.396(3) . ?
N2 N3 1.384(2) . ?
N5 O4 1.222(3) . ?
N5 O3 1.224(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
N1 H1 O1 0.88 2.01 2.857(2) 161.3 3_566
N3 H3 O2 0.88 2.12 2.811(2) 135.5 2_545
N4 H4 O2 0.88 2.20 3.003(2) 151.0 2_545
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21141753
