#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/42/7204220.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_7204220
loop_
_publ_author_name
'Thorfinnur Gunnlaugsson'
'Mark Nieuwenhuyzen'
'Ludovic Richard'
'Vera Thoss'
_publ_section_title
;
 Novel sodium-selective fluorescent PET and optically based
 chemosensors: towards Na+ determination in serum
;
_journal_issue                   1
_journal_name_full               'J. Chem. Soc., Perkin Trans. 2'
_journal_page_first              141
_journal_page_last               150
_journal_paper_doi               10.1039/b106474f
_journal_year                    2002
_chemical_formula_sum            'C23 H31 F6 N4 O7 P'
_chemical_formula_weight         620.49
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 102.167(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.543(4)
_cell_length_b                   25.740(12)
_cell_length_c                   14.221(6)
_cell_measurement_reflns_used    1030
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      21
_cell_measurement_theta_min      2.2
_cell_volume                     2699(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      153(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_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  0.0927
_diffrn_reflns_av_sigmaI/netI    0.1583
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8768
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'Pale Orange'
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         4523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.944
_refine_ls_R_factor_all          0.1528
_refine_ls_R_factor_gt           0.0671
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1051P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1561
_refine_ls_wR_factor_ref         0.2227
_reflns_number_gt                2066
_reflns_number_total             4523
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b106474f.txt
_cod_data_source_block           thorrnam
_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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7204220
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.6357(2) 0.60757(7) 0.72266(12) 0.0335(5) Uani 1 1 d . . .
F11 F 0.8319(5) 0.59423(16) 0.7049(3) 0.0541(12) Uani 1 1 d . . .
F12 F 0.4410(6) 0.6207(2) 0.7408(3) 0.0732(15) Uani 1 1 d . . .
F13 F 0.6663(6) 0.66691(15) 0.6994(3) 0.0630(13) Uani 1 1 d . . .
F14 F 0.7228(5) 0.61783(14) 0.8338(3) 0.0447(10) Uani 1 1 d . . .
F15 F 0.6092(7) 0.54802(15) 0.7461(3) 0.0638(14) Uani 1 1 d . . .
F16 F 0.5506(5) 0.59811(15) 0.6122(2) 0.0476(11) Uani 1 1 d . . .
O1 O 0.4331(6) 0.44186(18) 0.7700(3) 0.0430(13) Uani 1 1 d . . .
O2 O 0.2281(7) 0.49228(18) 0.6842(3) 0.0449(13) Uani 1 1 d . . .
N3 N 0.3124(8) 0.4747(2) 0.7619(4) 0.0373(14) Uani 1 1 d . . .
C4 C 0.2647(8) 0.4942(2) 0.8490(4) 0.0264(14) Uani 1 1 d . . .
C5 C 0.3178(8) 0.4648(2) 0.9335(4) 0.0268(15) Uani 1 1 d . . .
H5A H 0.3810 0.4329 0.9335 0.032 Uiso 1 1 calc R . .
C6 C 0.2746(8) 0.4840(2) 1.0165(5) 0.0312(15) Uani 1 1 d . . .
H6A H 0.3034 0.4644 1.0743 0.037 Uiso 1 1 calc R . .
C7 C 0.1895(8) 0.5318(2) 1.0161(4) 0.0276(15) Uani 1 1 d . . .
C8 C 0.1363(8) 0.5605(2) 0.9327(5) 0.0320(16) Uani 1 1 d . . .
H8A H 0.0768 0.5929 0.9337 0.038 Uiso 1 1 calc R . .
C9 C 0.1717(8) 0.5408(2) 0.8463(4) 0.0288(15) Uani 1 1 d . . .
H9A H 0.1327 0.5590 0.7874 0.035 Uiso 1 1 calc R . .
N10 N 0.1619(7) 0.54893(19) 1.1078(3) 0.0265(12) Uani 1 1 d . . .
N11 N 0.1307(7) 0.59655(19) 1.1126(3) 0.0272(12) Uani 1 1 d . . .
C12 C 0.1051(8) 0.6124(2) 1.2063(5) 0.0305(15) Uani 1 1 d . . .
C13 C 0.0474(8) 0.6625(2) 1.2146(5) 0.0301(15) Uani 1 1 d . . .
H13A H 0.0288 0.6849 1.1603 0.036 Uiso 1 1 calc R . .
C14 C 0.0163(8) 0.6804(2) 1.3006(4) 0.0260(14) Uani 1 1 d . . .
H14A H -0.0283 0.7146 1.3057 0.031 Uiso 1 1 calc R . .
C15 C 0.0515(8) 0.6476(2) 1.3800(4) 0.0264(15) Uani 1 1 d . . .
C16 C 0.1173(8) 0.5972(2) 1.3733(4) 0.0266(14) Uani 1 1 d . . .
C17 C 0.1407(8) 0.5790(2) 1.2840(4) 0.0255(14) Uani 1 1 d . . .
H17A H 0.1803 0.5445 1.2770 0.031 Uiso 1 1 calc R . .
O18 O 0.1492(6) 0.56865(15) 1.4541(3) 0.0338(11) Uani 1 1 d . . .
C19 C 0.2273(10) 0.5179(2) 1.4503(5) 0.0452(19) Uani 1 1 d . . .
H19A H 0.2630 0.5039 1.5156 0.068 Uiso 1 1 calc R . .
H19B H 0.3344 0.5205 1.4217 0.068 Uiso 1 1 calc R . .
H19C H 0.1379 0.4949 1.4111 0.068 Uiso 1 1 calc R . .
N20 N 0.0061(7) 0.66773(19) 1.4680(3) 0.0267(12) Uani 1 1 d . . .
H20 H -0.056(7) 0.706(2) 1.445(4) 0.020(14) Uiso 1 1 d . . .
C21 C 0.1700(8) 0.6749(2) 1.5506(4) 0.0303(15) Uani 1 1 d . . .
H21A H 0.1310 0.6923 1.6049 0.036 Uiso 1 1 calc R . .
H21B H 0.2194 0.6404 1.5731 0.036 Uiso 1 1 calc R . .
C22 C 0.3167(8) 0.7067(2) 1.5209(4) 0.0314(15) Uani 1 1 d . . .
H22A H 0.4044 0.7183 1.5791 0.038 Uiso 1 1 calc R . .
H22B H 0.3828 0.6848 1.4825 0.038 Uiso 1 1 calc R . .
O23 O 0.2445(6) 0.75084(17) 1.4658(3) 0.0389(12) Uani 1 1 d . . .
C24 C 0.1919(9) 0.7925(3) 1.5206(5) 0.0418(18) Uani 1 1 d . . .
H24A H 0.2819 0.8210 1.5273 0.050 Uiso 1 1 calc R . .
H24B H 0.1851 0.7802 1.5857 0.050 Uiso 1 1 calc R . .
C25 C 0.0088(10) 0.8116(2) 1.4682(5) 0.0433(18) Uani 1 1 d . . .
H25A H -0.0258 0.8428 1.5011 0.052 Uiso 1 1 calc R . .
H25B H 0.0146 0.8215 1.4017 0.052 Uiso 1 1 calc R . .
O26 O -0.1229(6) 0.77221(15) 1.4660(3) 0.0296(10) Uani 1 1 d . . .
C27 C -0.3033(8) 0.7908(2) 1.4405(4) 0.0330(16) Uani 1 1 d . . .
H27A H -0.3159 0.8211 1.4814 0.040 Uiso 1 1 calc R . .
H27B H -0.3861 0.7633 1.4543 0.040 Uiso 1 1 calc R . .
C28 C -0.3625(9) 0.8067(2) 1.3351(4) 0.0345(16) Uani 1 1 d . . .
H28A H -0.4844 0.8227 1.3254 0.041 Uiso 1 1 calc R . .
H28B H -0.2779 0.8336 1.3210 0.041 Uiso 1 1 calc R . .
O29 O -0.3686(6) 0.76507(16) 1.2678(3) 0.0345(11) Uani 1 1 d . . .
C30 C -0.5212(9) 0.7312(2) 1.2609(5) 0.0369(17) Uani 1 1 d . . .
H30A H -0.5928 0.7311 1.1940 0.044 Uiso 1 1 calc R . .
H30B H -0.6002 0.7439 1.3034 0.044 Uiso 1 1 calc R . .
C31 C -0.4586(9) 0.6773(2) 1.2896(5) 0.0380(17) Uani 1 1 d . . .
H31A H -0.5645 0.6538 1.2829 0.046 Uiso 1 1 calc R . .
H31B H -0.3800 0.6644 1.2469 0.046 Uiso 1 1 calc R . .
O32 O -0.3609(6) 0.67747(15) 1.3862(3) 0.0335(11) Uani 1 1 d . . .
C33 C -0.2941(9) 0.6281(2) 1.4249(4) 0.0315(16) Uani 1 1 d . . .
H33A H -0.2567 0.6068 1.3744 0.038 Uiso 1 1 calc R . .
H33B H -0.3904 0.6092 1.4485 0.038 Uiso 1 1 calc R . .
C34 C -0.1376(9) 0.6372(2) 1.5047(4) 0.0311(16) Uani 1 1 d . . .
H34A H -0.0869 0.6036 1.5315 0.037 Uiso 1 1 calc R . .
H34B H -0.1769 0.6569 1.5566 0.037 Uiso 1 1 calc R . .
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'
P P 0.1023 0.0942 '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
F12 P1 F16 89.9(2) . . ?
F12 P1 F13 90.6(3) . . ?
F16 P1 F13 89.3(2) . . ?
F12 P1 F15 90.5(3) . . ?
F16 P1 F15 91.0(2) . . ?
F13 P1 F15 178.9(3) . . ?
F12 P1 F11 179.7(3) . . ?
F16 P1 F11 90.3(2) . . ?
F13 P1 F11 89.6(2) . . ?
F15 P1 F11 89.3(3) . . ?
F12 P1 F14 90.3(2) . . ?
F16 P1 F14 179.2(2) . . ?
F13 P1 F14 90.0(2) . . ?
F15 P1 F14 89.8(2) . . ?
F11 P1 F14 89.5(2) . . ?
O1 N3 O2 124.4(5) . . ?
O1 N3 C4 118.0(6) . . ?
O2 N3 C4 117.6(6) . . ?
C9 C4 C5 122.8(5) . . ?
C9 C4 N3 119.4(6) . . ?
C5 C4 N3 117.8(5) . . ?
C6 C5 C4 117.5(6) . . ?
C5 C6 C7 120.4(6) . . ?
C8 C7 C6 121.8(6) . . ?
C8 C7 N10 123.1(6) . . ?
C6 C7 N10 115.1(6) . . ?
C7 C8 C9 118.9(6) . . ?
C4 C9 C8 118.4(6) . . ?
N11 N10 C7 114.5(5) . . ?
N10 N11 C12 112.9(5) . . ?
C13 C12 C17 121.8(6) . . ?
C13 C12 N11 116.7(6) . . ?
C17 C12 N11 121.5(5) . . ?
C14 C13 C12 120.6(6) . . ?
C13 C14 C15 118.7(6) . . ?
C14 C15 C16 121.2(5) . . ?
C14 C15 N20 116.2(5) . . ?
C16 C15 N20 122.5(5) . . ?
O18 C16 C17 124.1(5) . . ?
O18 C16 C15 116.8(5) . . ?
C17 C16 C15 119.1(6) . . ?
C12 C17 C16 118.6(6) . . ?
C16 O18 C19 117.8(5) . . ?
C15 N20 C34 115.2(5) . . ?
C15 N20 C21 113.9(5) . . ?
C34 N20 C21 108.6(5) . . ?
C22 C21 N20 111.9(5) . . ?
O23 C22 C21 111.7(5) . . ?
C22 O23 C24 114.6(5) . . ?
O23 C24 C25 107.8(5) . . ?
O26 C25 C24 110.0(5) . . ?
C27 O26 C25 113.3(5) . . ?
O26 C27 C28 114.2(5) . . ?
O29 C28 C27 114.6(5) . . ?
C30 O29 C28 114.5(5) . . ?
O29 C30 C31 110.1(5) . . ?
O32 C31 C30 109.4(5) . . ?
C31 O32 C33 116.0(4) . . ?
O32 C33 C34 108.3(5) . . ?
C33 C34 N20 109.4(5) . . ?
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
P1 F12 1.580(4) . ?
P1 F16 1.586(4) . ?
P1 F13 1.590(4) . ?
P1 F15 1.590(4) . ?
P1 F11 1.591(4) . ?
P1 F14 1.601(4) . ?
O1 N3 1.230(6) . ?
O2 N3 1.239(7) . ?
N3 C4 1.450(7) . ?
C4 C9 1.386(8) . ?
C4 C5 1.405(8) . ?
C5 C6 1.382(8) . ?
C6 C7 1.387(8) . ?
C7 C8 1.382(8) . ?
C7 N10 1.432(7) . ?
C8 C9 1.405(8) . ?
N10 N11 1.253(6) . ?
N11 C12 1.445(7) . ?
C12 C13 1.374(8) . ?
C12 C17 1.379(8) . ?
C13 C14 1.373(8) . ?
C14 C15 1.390(8) . ?
C15 C16 1.400(8) . ?
C15 N20 1.460(7) . ?
C16 O18 1.342(6) . ?
C16 C17 1.399(8) . ?
O18 C19 1.438(7) . ?
N20 C34 1.518(7) . ?
N20 C21 1.527(7) . ?
C21 C22 1.507(8) . ?
C22 O23 1.423(7) . ?
O23 C24 1.431(7) . ?
C24 C25 1.506(9) . ?
C25 O26 1.416(7) . ?
O26 C27 1.415(7) . ?
C27 C28 1.527(8) . ?
C28 O29 1.432(7) . ?
O29 C30 1.431(7) . ?
C30 C31 1.495(8) . ?
C31 O32 1.416(7) . ?
O32 C33 1.433(7) . ?
C33 C34 1.474(9) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21189783
