#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:33:26 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179535 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/04/4500496.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_4500496
loop_
_publ_author_name
'Marivel, S.'
'Arunachalam, M.'
'Ghosh, Pradyut'
_publ_section_title
;
 Binding of Polyatomic Anions with Protonated Ureido-pyridyl Ligands
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1642
_journal_paper_doi               10.1021/cg101595n
_journal_volume                  11
_journal_year                    2011
_chemical_formula_sum            'C14 H10 F5 N3 O3'
_chemical_formula_weight         363.25
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.956(1)
_cell_length_b                   17.701(1)
_cell_length_c                   7.498(1)
_cell_measurement_temperature    100(2)
_cell_volume                     1454.1(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    PLATON
_computing_publication_material  'MERCURY 2.2'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            12548
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.9811
_exptl_absorpt_correction_T_min  0.9657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         2514
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0239
_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)+(0.0399P)²+0.1397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0609
_refine_ls_wR_factor_ref         0.0618
_reflns_number_gt                2411
_reflns_number_total             2514
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg101595n_si_002.cif
_cod_data_source_block           Complex5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               4500496
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'
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
F1 F 1.15450(9) 0.49342(5) 0.21083(14) 0.0232(2) Uani 1 1 d
F2 F 1.28568(8) 0.61699(6) 0.27673(15) 0.0283(3) Uani 1 1 d
F3 F 1.17689(9) 0.74187(5) 0.41787(17) 0.0333(3) Uani 1 1 d
F4 F 0.93674(9) 0.73917(5) 0.49876(16) 0.0328(3) Uani 1 1 d
F5 F 0.80343(8) 0.61348(5) 0.43928(15) 0.0258(2) Uani 1 1 d
O1 O 1.03313(10) 0.40765(6) 0.45334(15) 0.0193(3) Uani 1 1 d
N1 N 0.87163(12) 0.13565(8) 0.4970(2) 0.0217(3) Uani 1 1 d
H1A H 0.8637(19) 0.0836(12) 0.541(3) 0.043(6) Uiso 1 1 d
N2 N 0.85690(12) 0.35867(7) 0.33585(19) 0.0183(3) Uani 1 1 d
H2A H 0.788(2) 0.3710(12) 0.280(3) 0.039(6) Uiso 1 1 d
N3 N 0.90441(13) 0.48355(8) 0.2974(2) 0.0176(3) Uani 1 1 d
H3A H 0.8393(19) 0.4889(11) 0.245(3) 0.028(5) Uiso 1 1 d
C1 C 0.96298(16) 0.18172(9) 0.5439(3) 0.0243(4) Uani 1 1 d
H1 H 1.0284(19) 0.1603(11) 0.617(3) 0.034(5) Uiso 1 1 d
C2 C 0.96508(16) 0.25580(9) 0.4929(2) 0.0206(4) Uani 1 1 d
H2 H 1.0275(19) 0.2825(11) 0.528(3) 0.026(5) Uiso 1 1 d
C3 C 0.86867(14) 0.28488(8) 0.3908(2) 0.0181(3) Uani 1 1 d
C4 C 0.77568(16) 0.23493(9) 0.3405(3) 0.0229(4) Uani 1 1 d
H4 H 0.7147(18) 0.2520(9) 0.276(3) 0.020(5) Uiso 1 1 d
C5 C 0.78037(15) 0.16142(9) 0.3944(3) 0.0245(4) Uani 1 1 d
H5 H 0.7226(17) 0.1260(10) 0.372(2) 0.017(4) Uiso 1 1 d
C6 C 0.93925(14) 0.41581(9) 0.3690(2) 0.0164(3) Uani 1 1 d
C7 C 0.97516(14) 0.54795(8) 0.3316(2) 0.0165(3) Uani 1 1 d
C8 C 1.09914(15) 0.55115(9) 0.2920(2) 0.0182(3) Uani 1 1 d
C9 C 1.16665(15) 0.61553(10) 0.3229(2) 0.0208(4) Uani 1 1 d
C10 C 1.11268(15) 0.67859(9) 0.3926(2) 0.0223(4) Uani 1 1 d
C11 C 0.98958(15) 0.67731(8) 0.4318(2) 0.0219(4) Uani 1 1 d
C12 C 0.92275(14) 0.61292(9) 0.4012(2) 0.0194(3) Uani 1 1 d
O2 O 0.63272(10) 0.38411(6) 0.2056(2) 0.0302(3) Uani 1 1 d
O3 O 0.67463(10) 0.50109(6) 0.12185(18) 0.0232(3) Uani 1 1 d
C13 C 0.60380(15) 0.44473(9) 0.1330(2) 0.0203(4) Uani 1 1 d
C14 C 0.47633(18) 0.45187(12) 0.0576(3) 0.0329(5) Uani 1 1 d
H14B H 0.472(3) 0.4831(17) -0.037(5) 0.079(10) Uiso 1 1 d
H14A H 0.431(2) 0.4085(15) 0.052(4) 0.068(8) Uiso 1 1 d
H14C H 0.425(3) 0.4780(18) 0.140(5) 0.085(10) Uiso 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'
F F 0.0171 0.0103 '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
C1 N1 C5 120.07(15)
C1 N1 H1A 123.3(13)
C5 N1 H1A 116.4(13)
C3 N2 C6 125.56(14)
C3 N2 H2A 116.9(14)
C6 N2 H2A 117.4(13)
C6 N3 C7 119.12(14)
C6 N3 H3A 122.1(14)
C7 N3 H3A 118.3(14)
N1 C1 C2 121.58(17)
N1 C1 H1 117.4(12)
C2 C1 H1 121.1(12)
C1 C2 C3 119.51(16)
C1 C2 H2 116.7(13)
C3 C2 H2 123.7(13)
N2 C3 C4 116.79(15)
N2 C3 C2 125.63(15)
C4 C3 C2 117.58(15)
C5 C4 C3 119.68(17)
C5 C4 H4 121.4(11)
C3 C4 H4 119.0(11)
N1 C5 C4 121.51(16)
N1 C5 H5 113.1(11)
C4 C5 H5 125.3(11)
O1 C6 N3 122.96(14)
O1 C6 N2 124.08(14)
N3 C6 N2 112.96(13)
C12 C7 C8 116.78(14)
C12 C7 N3 120.92(13)
C8 C7 N3 122.26(14)
F1 C8 C9 117.74(15)
F1 C8 C7 120.63(14)
C9 C8 C7 121.46(15)
F2 C9 C10 120.02(15)
F2 C9 C8 119.45(15)
C10 C9 C8 120.47(15)
F3 C10 C9 120.73(15)
F3 C10 C11 119.86(14)
C9 C10 C11 119.38(14)
F4 C11 C12 120.77(15)
F4 C11 C10 119.32(14)
C12 C11 C10 119.91(14)
F5 C12 C11 118.60(14)
F5 C12 C7 119.40(14)
C11 C12 C7 122.00(14)
O2 C13 O3 123.52(15)
O2 C13 C14 118.10(15)
O3 C13 C14 118.37(15)
C13 C14 H14B 113(2)
C13 C14 H14A 116.4(17)
H14B C14 H14A 117(3)
C13 C14 H14C 110(2)
H14B C14 H14C 100(3)
H14A C14 H14C 97(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C8 1.3353(18)
F2 C9 1.3494(19)
F3 C10 1.3363(18)
F4 C11 1.3365(19)
F5 C12 1.3381(19)
O1 C6 1.2162(19)
N1 C1 1.338(2)
N1 C5 1.341(2)
N1 H1A 0.98(2)
N2 C3 1.376(2)
N2 C6 1.378(2)
N2 H2A 0.89(2)
N3 C6 1.368(2)
N3 C7 1.402(2)
N3 H3A 0.82(2)
C1 C2 1.366(2)
C1 H1 0.98(2)
C2 C3 1.402(2)
C2 H2 0.87(2)
C3 C4 1.401(2)
C4 C5 1.363(2)
C4 H4 0.88(2)
C5 H5 0.907(18)
C7 C12 1.387(2)
C7 C8 1.391(2)
C8 C9 1.378(2)
C9 C10 1.367(2)
C10 C11 1.380(2)
C11 C12 1.374(2)
O2 C13 1.244(2)
O3 C13 1.2668(19)
C13 C14 1.512(2)
C14 H14B 0.90(4)
C14 H14A 0.91(3)
C14 H14C 0.95(4)
