#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:01:27 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179609 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/73/4507359.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_4507359
loop_
_publ_author_name
'Chutia, Romen'
'Dey, Sandeep Kumar'
'Das, Gopal'
_publ_section_title
;
 Positional Isomeric Effect in Nitrophenyl Functionalized Tripodal Urea
 Receptors toward Binding and Encapsulation of Anions
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              883
_journal_paper_doi               10.1021/cg3015749
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         '2(C27 H30 N10 O9), 2(C8 H20 N), C O3'
_chemical_formula_sum            'C71 H100 N22 O21'
_chemical_formula_weight         1597.73
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 105.138(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.6830(7)
_cell_length_b                   21.3607(5)
_cell_length_c                   17.8940(8)
_cell_measurement_reflns_used    5865
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.65
_cell_measurement_theta_min      3.87
_cell_volume                     8369.2(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            41828
_diffrn_reflns_theta_full        28.65
_diffrn_reflns_theta_max         28.65
_diffrn_reflns_theta_min         3.87
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9720
_exptl_absorpt_correction_T_min  0.9503
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3392
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     519
_refine_ls_number_reflns         10505
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.194
_refine_ls_R_factor_all          0.1107
_refine_ls_R_factor_gt           0.0624
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.3215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1779
_refine_ls_wR_factor_ref         0.2082
_reflns_number_gt                6075
_reflns_number_total             10505
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3015749_si_002.cif
_cod_data_source_block           p-urea_co3
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4507359
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'
'-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_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
N1 N 0.32004(6) 0.24668(6) 0.65072(8) 0.0390(3) Uani 1 1 d .
C24 C 0.63543(10) 0.02234(10) 0.65552(14) 0.0612(5) Uani 1 1 d .
H24 H 0.6760 0.0340 0.6755 0.073 Uiso 1 1 calc R
C25 C 0.62111(10) -0.03299(10) 0.61615(15) 0.0622(6) Uani 1 1 d .
C4 C 0.54023(9) 0.43993(9) 0.65720(11) 0.0505(4) Uani 1 1 d .
C3 C 0.43963(9) 0.38986(9) 0.59971(12) 0.0529(5) Uani 1 1 d .
C7 C 0.63164(10) 0.52861(10) 0.67822(14) 0.0598(5) Uani 1 1 d .
C1 C 0.30487(9) 0.30659(9) 0.60907(12) 0.0543(5) Uani 1 1 d .
H1A H 0.3051 0.3395 0.6465 0.065 Uiso 1 1 calc R
H1B H 0.2638 0.3039 0.5754 0.065 Uiso 1 1 calc R
C2 C 0.34805(9) 0.32471(11) 0.56083(12) 0.0584(5) Uani 1 1 d .
H2A H 0.3498 0.2910 0.5251 0.070 Uiso 1 1 calc R
H2B H 0.3324 0.3616 0.5305 0.070 Uiso 1 1 calc R
C9 C 0.59383(9) 0.43350(10) 0.71548(14) 0.0611(5) Uani 1 1 d .
H9 H 0.5989 0.3987 0.7478 0.073 Uiso 1 1 calc R
C8 C 0.63966(10) 0.47752(11) 0.72654(15) 0.0654(6) Uani 1 1 d .
H8 H 0.6754 0.4728 0.7659 0.079 Uiso 1 1 calc R
C5 C 0.53301(11) 0.49262(11) 0.60955(15) 0.0712(6) Uani 1 1 d .
H5 H 0.4972 0.4982 0.5705 0.085 Uiso 1 1 calc R
C6 C 0.57918(12) 0.53642(11) 0.62054(16) 0.0738(7) Uani 1 1 d .
H6 H 0.5746 0.5714 0.5886 0.089 Uiso 1 1 calc R
N2 N 0.40919(7) 0.33753(8) 0.60821(10) 0.0555(4) Uani 1 1 d .
H2N H 0.4265 0.3107 0.6429 0.067 Uiso 1 1 calc R
N3 N 0.49716(7) 0.39267(8) 0.64936(10) 0.0540(4) Uani 1 1 d .
H3N H 0.5078 0.3610 0.6795 0.065 Uiso 1 1 calc R
N4 N 0.68044(10) 0.57465(10) 0.68751(15) 0.0759(6) Uani 1 1 d .
O1 O 0.41799(8) 0.43065(8) 0.55290(11) 0.0847(6) Uani 1 1 d .
O3 O 0.72757(9) 0.56695(11) 0.73709(16) 0.1139(8) Uani 1 1 d .
O2 O 0.67172(11) 0.62062(11) 0.64590(17) 0.1172(8) Uani 1 1 d .
C12 C 0.38978(8) 0.27924(10) 0.89525(11) 0.0516(4) Uani 1 1 d .
C11 C 0.30638(9) 0.28360(11) 0.77783(12) 0.0564(5) Uani 1 1 d .
H11A H 0.3046 0.3269 0.7611 0.068 Uiso 1 1 calc R
H11B H 0.2800 0.2791 0.8123 0.068 Uiso 1 1 calc R
C10 C 0.28352(9) 0.24182(10) 0.70818(12) 0.0557(5) Uani 1 1 d .
H10A H 0.2841 0.1987 0.7255 0.067 Uiso 1 1 calc R
H10B H 0.2415 0.2527 0.6832 0.067 Uiso 1 1 calc R
C13 C 0.48562(9) 0.26897(10) 0.99935(12) 0.0532(5) Uani 1 1 d .
C18 C 0.53975(9) 0.23470(11) 1.02088(13) 0.0597(5) Uani 1 1 d .
H18 H 0.5504 0.2087 0.9848 0.072 Uiso 1 1 calc R
C17 C 0.57778(10) 0.23856(12) 1.09459(15) 0.0693(6) Uani 1 1 d .
H17 H 0.6138 0.2156 1.1084 0.083 Uiso 1 1 calc R
C16 C 0.56140(10) 0.27709(14) 1.14738(14) 0.0752(7) Uani 1 1 d .
C14 C 0.47117(11) 0.30839(14) 1.05418(15) 0.0781(7) Uani 1 1 d .
H14 H 0.4356 0.3322 1.0409 0.094 Uiso 1 1 calc R
C15 C 0.50928(12) 0.31229(16) 1.12802(16) 0.0902(9) Uani 1 1 d .
H15 H 0.4996 0.3387 1.1644 0.108 Uiso 1 1 calc R
N6 N 0.44980(7) 0.26230(8) 0.92416(10) 0.0543(4) Uani 1 1 d .
H6N H 0.4672 0.2456 0.8918 0.065 Uiso 1 1 calc R
N5 N 0.36826(7) 0.26843(9) 0.81922(10) 0.0582(4) Uani 1 1 d .
H5N H 0.3921 0.2519 0.7943 0.070 Uiso 1 1 calc R
N7 N 0.60147(12) 0.28052(19) 1.22648(15) 0.1070(9) Uani 1 1 d .
O4 O 0.35767(7) 0.30042(9) 0.93489(9) 0.0771(5) Uani 1 1 d .
O6 O 0.64291(12) 0.24224(15) 1.24583(14) 0.1231(9) Uani 1 1 d .
O5 O 0.59200(12) 0.3231(2) 1.26875(16) 0.1559(13) Uani 1 1 d .
C20 C 0.32628(9) 0.13171(9) 0.62522(15) 0.0600(5) Uani 1 1 d .
H20A H 0.3138 0.1224 0.6719 0.072 Uiso 1 1 calc R
H20B H 0.3089 0.1000 0.5870 0.072 Uiso 1 1 calc R
C19 C 0.30179(9) 0.19450(9) 0.59522(13) 0.0546(5) Uani 1 1 d .
H19A H 0.3154 0.2039 0.5494 0.066 Uiso 1 1 calc R
H19B H 0.2575 0.1922 0.5796 0.066 Uiso 1 1 calc R
C23 C 0.58907(9) 0.06024(10) 0.66509(13) 0.0586(5) Uani 1 1 d .
H23 H 0.5987 0.0981 0.6911 0.070 Uiso 1 1 calc R
C22 C 0.52794(9) 0.04339(9) 0.63674(14) 0.0576(5) Uani 1 1 d .
C21 C 0.42168(9) 0.07910(9) 0.62584(14) 0.0587(5) Uani 1 1 d .
C27 C 0.51499(11) -0.01388(12) 0.5989(2) 0.1033(12) Uani 1 1 d .
H27 H 0.4746 -0.0267 0.5804 0.124 Uiso 1 1 calc R
C26 C 0.56163(12) -0.05179(13) 0.5886(2) 0.1039(12) Uani 1 1 d .
H26 H 0.5527 -0.0899 0.5630 0.125 Uiso 1 1 calc R
N8 N 0.39238(7) 0.12909(7) 0.64234(11) 0.0567(4) Uani 1 1 d .
H8N H 0.4133 0.1609 0.6639 0.068 Uiso 1 1 calc R
N9 N 0.48441(7) 0.08526(7) 0.64694(12) 0.0606(5) Uani 1 1 d .
H9N H 0.4982 0.1198 0.6695 0.073 Uiso 1 1 calc R
N10 N 0.66967(9) -0.07237(10) 0.60210(14) 0.0730(6) Uani 1 1 d .
O7 O 0.39554(7) 0.03232(8) 0.59374(15) 0.0977(7) Uani 1 1 d .
O9 O 0.72214(9) -0.05430(10) 0.62580(15) 0.1010(7) Uani 1 1 d .
O8 O 0.65577(10) -0.12112(10) 0.56501(17) 0.1113(8) Uani 1 1 d .
N11 N 0.28229(9) 0.10877(8) 0.03097(12) 0.0640(5) Uani 1 1 d .
C29 C 0.34784(14) 0.10043(16) 0.0261(2) 0.1018(11) Uani 1 1 d .
H29A H 0.3649 0.0641 0.0567 0.122 Uiso 1 1 calc R
H29B H 0.3470 0.0914 -0.0273 0.122 Uiso 1 1 calc R
C30 C 0.38990(18) 0.1548(3) 0.0526(4) 0.174(3) Uani 1 1 d .
H30A H 0.3742 0.1910 0.0220 0.261 Uiso 1 1 calc R
H30B H 0.4297 0.1449 0.0466 0.261 Uiso 1 1 calc R
H30C H 0.3927 0.1633 0.1061 0.261 Uiso 1 1 calc R
C35 C 0.25203(13) 0.16286(12) -0.01968(17) 0.0793(7) Uani 1 1 d .
H35A H 0.2115 0.1689 -0.0123 0.095 Uiso 1 1 calc R
H35B H 0.2753 0.2006 -0.0021 0.095 Uiso 1 1 calc R
C31 C 0.28084(15) 0.12629(14) 0.11238(17) 0.0883(8) Uani 1 1 d .
H31A H 0.3023 0.1656 0.1258 0.106 Uiso 1 1 calc R
H31B H 0.2387 0.1331 0.1130 0.106 Uiso 1 1 calc R
C33 C 0.25061(18) 0.04865(14) 0.0081(2) 0.1073(11) Uani 1 1 d .
H33A H 0.2715 0.0163 0.0432 0.129 Uiso 1 1 calc R
H33B H 0.2535 0.0379 -0.0434 0.129 Uiso 1 1 calc R
C32 C 0.3085(2) 0.0787(2) 0.1739(2) 0.1507(19) Uani 1 1 d .
H32A H 0.2885 0.0391 0.1607 0.226 Uiso 1 1 calc R
H32B H 0.3035 0.0925 0.2229 0.226 Uiso 1 1 calc R
H32C H 0.3513 0.0742 0.1772 0.226 Uiso 1 1 calc R
C36 C 0.2463(2) 0.1552(2) -0.1041(2) 0.1389(16) Uani 1 1 d .
H36A H 0.2862 0.1514 -0.1126 0.208 Uiso 1 1 calc R
H36B H 0.2260 0.1911 -0.1315 0.208 Uiso 1 1 calc R
H36C H 0.2229 0.1183 -0.1226 0.208 Uiso 1 1 calc R
C34 C 0.1833(2) 0.0491(3) 0.0085(4) 0.180(2) Uani 1 1 d .
H34A H 0.1795 0.0645 0.0574 0.269 Uiso 1 1 calc R
H34B H 0.1673 0.0073 0.0006 0.269 Uiso 1 1 calc R
H34C H 0.1608 0.0757 -0.0323 0.269 Uiso 1 1 calc R
C28 C 0.5000 0.23304(10) 0.7500 0.0369(5) Uani 1 2 d S
O10 O 0.5000 0.29123(9) 0.7500 0.0771(7) Uani 1 2 d S
O11 O 0.52030(10) 0.20292(7) 0.70235(11) 0.0925(7) 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_3
C1 N1 C19 109.09(15) .
C1 N1 C10 108.18(14) .
C19 N1 C10 107.69(14) .
C25 C24 C23 119.1(2) .
C26 C25 C24 121.10(19) .
C26 C25 N10 119.1(2) .
C24 C25 N10 119.8(2) .
N3 C4 C9 117.41(17) .
N3 C4 C5 123.94(19) .
C9 C4 C5 118.64(18) .
O1 C3 N2 123.08(19) .
O1 C3 N3 123.82(18) .
N2 C3 N3 113.10(16) .
C6 C7 C8 121.21(19) .
C6 C7 N4 119.3(2) .
C8 C7 N4 119.5(2) .
N1 C1 C2 114.15(16) .
N2 C2 C1 112.14(17) .
C8 C9 C4 121.41(19) .
C7 C8 C9 118.7(2) .
C6 C5 C4 119.8(2) .
C7 C6 C5 120.2(2) .
C3 N2 C2 122.16(16) .
C3 N3 C4 128.47(16) .
O3 N4 O2 122.0(2) .
O3 N4 C7 119.4(2) .
O2 N4 C7 118.5(2) .
O4 C12 N5 122.42(18) .
O4 C12 N6 123.99(18) .
N5 C12 N6 113.55(16) .
N5 C11 C10 111.68(16) .
N1 C10 C11 113.40(16) .
N6 C13 C18 117.71(18) .
N6 C13 C14 123.99(19) .
C18 C13 C14 118.3(2) .
C17 C18 C13 121.3(2) .
C16 C17 C18 118.7(2) .
C15 C16 C17 121.7(2) .
C15 C16 N7 119.5(3) .
C17 C16 N7 118.8(2) .
C15 C14 C13 120.4(2) .
C16 C15 C14 119.6(2) .
C12 N6 C13 127.67(16) .
C12 N5 C11 122.01(15) .
O6 N7 O5 124.1(3) .
O6 N7 C16 118.3(3) .
O5 N7 C16 117.6(3) .
N8 C20 C19 112.13(16) .
N1 C19 C20 114.97(17) .
C24 C23 C22 121.6(2) .
N9 C22 C27 124.53(19) .
N9 C22 C23 117.58(18) .
C27 C22 C23 117.88(19) .
O7 C21 N8 123.34(19) .
O7 C21 N9 122.95(18) .
N8 C21 N9 113.69(16) .
C26 C27 C22 120.5(2) .
C25 C26 C27 119.7(2) .
C21 N8 C20 122.16(16) .
C22 N9 C21 128.67(16) .
O9 N10 O8 123.1(2) .
O9 N10 C25 118.1(2) .
O8 N10 C25 118.8(2) .
C33 N11 C31 110.5(2) .
C33 N11 C35 112.7(2) .
C31 N11 C35 105.47(18) .
C33 N11 C29 107.1(2) .
C31 N11 C29 110.6(2) .
C35 N11 C29 110.53(18) .
C30 C29 N11 116.2(3) .
C36 C35 N11 115.4(2) .
C32 C31 N11 115.2(3) .
N11 C33 C34 114.1(3) .
O10 C28 O11 121.03(11) .
O10 C28 O11 121.03(11) 2_656
O11 C28 O11 117.9(2) 2_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.476(2) .
N1 C19 1.478(2) .
N1 C10 1.483(2) .
C24 C25 1.371(3) .
C24 C23 1.373(3) .
C25 C26 1.370(3) .
C25 N10 1.459(3) .
C4 N3 1.386(2) .
C4 C9 1.387(3) .
C4 C5 1.396(3) .
C3 O1 1.219(2) .
C3 N2 1.343(2) .
C3 N3 1.375(3) .
C7 C6 1.367(3) .
C7 C8 1.375(3) .
C7 N4 1.458(3) .
C1 C2 1.515(3) .
C2 N2 1.450(3) .
C9 C8 1.377(3) .
C5 C6 1.380(3) .
N4 O3 1.209(3) .
N4 O2 1.217(3) .
C12 O4 1.228(2) .
C12 N5 1.340(3) .
C12 N6 1.373(2) .
C11 N5 1.442(3) .
C11 C10 1.510(3) .
C13 N6 1.386(3) .
C13 C18 1.395(3) .
C13 C14 1.395(3) .
C18 C17 1.377(3) .
C17 C16 1.375(4) .
C16 C15 1.367(4) .
C16 N7 1.471(4) .
C14 C15 1.380(4) .
N7 O6 1.226(4) .
N7 O5 1.237(4) .
C20 N8 1.451(2) .
C20 C19 1.497(3) .
C23 C22 1.393(3) .
C22 N9 1.379(2) .
C22 C27 1.392(3) .
C21 O7 1.226(2) .
C21 N8 1.331(2) .
C21 N9 1.380(2) .
C27 C26 1.382(3) .
N10 O9 1.217(3) .
N10 O8 1.231(3) .
N11 C33 1.476(4) .
N11 C31 1.513(3) .
N11 C35 1.518(3) .
N11 C29 1.523(3) .
C29 C30 1.499(6) .
C35 C36 1.491(5) .
C31 C32 1.510(5) .
C33 C34 1.528(6) .
C28 O10 1.243(3) .
C28 O11 1.2481(19) .
C28 O11 1.2481(19) 2_656
