Fluorescent asymmetric bis-ureas for pyrophosphate recognition in pure water.
Casula, Arianna; Bazzicalupi, Carla; Bettoschi, Alexandre; Cadoni, Enzo; Coles, Simon J.; Horton, Peter N.; Isaia, Francesco; Lippolis, Vito; Mapp, Lucy K.; Marini, Giada M.; Montis, Riccardo; Scorciapino, Mariano Andrea; Caltagirone, Claudia; Dalton transactions (Cambridge, England : 2003) 45 (2016) 3078–3085; doi:10.1039/c5dt04497a

data_7037825
_publ_section_title
;
 Fluorescent asymmetric bis-ureas for pyrophosphate recognition in pure
 water.
;
_journal_issue                   7
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3078
_journal_page_last               3085
_journal_paper_doi               10.1039/c5dt04497a
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         '2(C16 H36 N), C26 H21 N5 O2, H2 O7 P2'
_chemical_formula_sum            'C58 H95 N7 O9 P2'
_chemical_formula_weight         1096.34
_chemical_name_systematic        Ac20_5
_space_group_crystal_system      orthorhombic
_space_group_IT_number           50
_space_group_name_Hall           '-P 2ab 2b'
_space_group_name_H-M_alt        'P b a n'
_symmetry_space_group_name_Hall  '-P 2ab 2b'
_symmetry_space_group_name_H-M   'P b a n :2'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-07-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-11-09 deposited with the CCDC.
2015-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.394(12)
_cell_length_b                   16.369(8)
_cell_length_c                   17.539(10)
_cell_measurement_reflns_used    7392
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.9
_cell_volume                     6429(6)
_computing_cell_refinement
'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_data_collection
'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction
'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
scan:
    Number of images: 108
               Slice: -35.0000 - 73.0000
         Image width: 1.0000
            Exp time: 50.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 72.0000
                 Phi: 60.0000
                 XTD: 45.0363
              2theta: -17.0575
scan:
    Number of images: 91
               Slice: -69.0000 - 22.0000
         Image width: 1.0000
            Exp time: 50.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: -60.0000
                 XTD: 45.0363
              2theta: -17.0575
scan:
    Number of images: 93
               Slice: -71.0000 - 22.0000
         Image width: 1.0000
            Exp time: 50.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: 120.0000
                 XTD: 45.0363
              2theta: -17.0575
scan:
    Number of images: 76
               Slice: -34.0000 - 42.0000
         Image width: 1.0000
            Exp time: 50.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 8.0000
                 Phi: -120.0000
                 XTD: 45.0363
              2theta: -17.0575
scan:
    Number of images: 17
               Slice: -31.0000 - -14.0000
         Image width: 1.0000
            Exp time: 50.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 56.0000
                 Phi: -90.0000
                 XTD: 45.0363
              2theta: -17.0575
scan:
    Number of images: 104
               Slice: -31.0000 - 73.0000
         Image width: 1.0000
            Exp time: 50.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 72.0000
                 Phi: 0.0000
                 XTD: 45.0363
              2theta: -17.0575
scan:
    Number of images: 69
               Slice: -69.0000 - 0.0000
         Image width: 1.0000
            Exp time: 50.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: -120.0000
                 XTD: 45.0363
              2theta: -17.0575
;
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.052315
_diffrn_orient_matrix_UB_12      0.019257
_diffrn_orient_matrix_UB_13      0.024993
_diffrn_orient_matrix_UB_21      -0.022654
_diffrn_orient_matrix_UB_22      0.016298
_diffrn_orient_matrix_UB_23      0.034861
_diffrn_orient_matrix_UB_31      0.005309
_diffrn_orient_matrix_UB_32      -0.050025
_diffrn_orient_matrix_UB_33      0.026838
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5686
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.158
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_description       plate
_exptl_crystal_F_000             2376
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     878
_refine_ls_number_reflns         5685
_refine_ls_number_restraints     1691
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1566
_refine_ls_R_factor_gt           0.0839
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1747P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2651
_refine_ls_wR_factor_ref         0.3026
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2485
_reflns_number_total             5685
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5dt04497a2.cif
_cod_data_source_block           L2_HPPi
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7037824--7037825.cif.
;
_cod_database_code               7037825
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.990
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 P21-O24 = P22-O24 = P11-O14 = P11-O14
 1.61 with sigma of 0.01
 P11-O12 = P12-O16 = P21-O23 = P22-O27
 1.55 with sigma of 0.02
 P21-O21 = P21-O22 = P22-O25 = P22-O26
 1.48 with sigma of 0.02
 P11-O11 = P11-O13 = P12-O15 = P12-O17
 1.48 with sigma of 0.02
 O22-O12 = O27-O13 = O26-O16 = O23-O17
 2.8 with sigma of 0.03
 H23A-O17 = H12-O22 = H16-O26 = H27-O13
 1.7 with sigma of 0.02
 C36-C37 \\sim C36-C37A \\sim C40-C41A \\sim C44-C45A
 with sigma of 0.02
 C7-O1 \\sim C16-O2
 with sigma of 0.02
 O1-N1 \\sim O1-N2 \\sim O2-N3 \\sim O2-N4
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.015 and
sigma for terminal atoms of 0.03
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{C35, C36, C37, C38} sigma for 1-2: 0.02, 1-3: 0.04
as
{C31, C32, C33, C34}
{C35, C36, C37, C38} sigma for 1-2: 0.02, 1-3: 0.04
as
{C39, C40, C41, C42}
{C35, C36, C37, C38} sigma for 1-2: 0.02, 1-3: 0.04
as
{C43, C44, C45, C46}
{O1, O2, N1, N2, N3, N4, N5, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12,
C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26} sigma for
1-2: 0.02, 1-3: 0.04
as
{O51, O52, N51, N52, N53, N54, N55, C51, C52, C53, C54, C55, C56, C57, C58,
C59, C60, C61, C62, C63, C64, C65, C66, C67, C68, C69, C70, C71, C72, C73, C74,
C75, C76}
6. Others
 Sof(H36C)=Sof(H36D)=Sof(C37A)=Sof(H37C)=Sof(H37D)=Sof(C38A)=Sof(H38D)=
 Sof(H38E)=Sof(H38F)=1-FVAR(1)
 Sof(H36A)=Sof(H36B)=Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(C38)=Sof(H38A)=Sof(H38B)=
 Sof(H38C)=FVAR(1)
 Sof(H40C)=Sof(H40D)=Sof(C41A)=Sof(H41C)=Sof(H41D)=Sof(C42A)=Sof(H42D)=
 Sof(H42E)=Sof(H42F)=1-FVAR(2)
 Sof(H40A)=Sof(H40B)=Sof(C41)=Sof(H41A)=Sof(H41B)=Sof(C42)=Sof(H42A)=Sof(H42B)=
 Sof(H42C)=FVAR(2)
 Sof(H44C)=Sof(H44D)=Sof(C45A)=Sof(H45C)=Sof(H45D)=Sof(C46A)=Sof(H46D)=
 Sof(H46E)=Sof(H46F)=1-FVAR(3)
 Sof(H44A)=Sof(H44B)=Sof(C45)=Sof(H45A)=Sof(H45B)=Sof(C46)=Sof(H46A)=Sof(H46B)=
 Sof(H46C)=FVAR(3)
 Fixed Sof: O1(0.25) O2(0.25) N1(0.25) H1(0.25) N2(0.25) H2(0.25) N3(0.25)
 H3(0.25) N4(0.25) H4(0.25) N5(0.25) H5(0.25) C1(0.25) H1A(0.25) C2(0.25)
 C3(0.25) H3A(0.25) C4(0.25) H4A(0.25) C5(0.25) H5A(0.25) C6(0.25) C7(0.25)
 C8(0.25) C9(0.25) H9(0.25) C10(0.25) H10(0.25) C11(0.25) H11(0.25) C12(0.25)
 C13(0.25) C14(0.25) H14(0.25) C15(0.25) H15(0.25) C16(0.25) C17(0.25)
 C18(0.25) H18(0.25) C19(0.25) H19(0.25) C20(0.25) H20(0.25) C21(0.25)
 C22(0.25) C23(0.25) H23(0.25) C24(0.25) H24(0.25) C25(0.25) H25(0.25)
 C26(0.25) H26(0.25) P11(0.25) P12(0.25) O11(0.25) O12(0.25) H12(0.25)
 O13(0.25) O14(0.25) O15(0.25) O16(0.25) H16(0.25) O17(0.25) P21(0.25)
 P22(0.25) O21(0.25) O22(0.25) O23(0.25) H23A(0.25) O24(0.25) O25(0.25)
 O26(0.25) O27(0.25) H27(0.25) O51(0.25) O52(0.25) N51(0.25) H51(0.25)
 N52(0.25) H52(0.25) N53(0.25) H53(0.25) N54(0.25) H54(0.25) N55(0.25)
 H55(0.25) C51(0.25) H51A(0.25) C52(0.25) C53(0.25) H53A(0.25) C54(0.25)
 H54A(0.25) C55(0.25) H55A(0.25) C56(0.25) C57(0.25) C58(0.25) C59(0.25)
 H59(0.25) C60(0.25) H60(0.25) C61(0.25) H61(0.25) C62(0.25) C63(0.25)
 C64(0.25) H64(0.25) C65(0.25) H65(0.25) C66(0.25) C67(0.25) C68(0.25)
 H68(0.25) C69(0.25) H69(0.25) C70(0.25) H70(0.25) C71(0.25) C72(0.25)
 C73(0.25) H73(0.25) C74(0.25) H74(0.25) C75(0.25) H75(0.25) C76(0.25) H76(0.25)
7.a Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C35(H35A,H35B), C36(H36A,
 H36B), C36(H36C,H36D), C37(H37A,H37B), C39(H39A,H39B), C40(H40A,H40B),
 C40(H40C,H40D), C41(H41A,H41B), C43(H43A,H43B), C44(H44A,H44B), C44(H44C,H44D),
  C45(H45A,H45B), C37A(H37C,H37D), C41A(H41C,H41D), C45A(H45C,H45D)
7.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), N4(H4), N5(H5), C1(H1A), C3(H3A), C4(H4A), C5(H5A),
 C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C18(H18), C19(H19), C20(H20),
 C23(H23), C24(H24), C25(H25), C26(H26), N51(H51), N52(H52), N53(H53), N54(H54),
  N55(H55), C51(H51A), C53(H53A), C54(H54A), C55(H55A), C59(H59), C60(H60),
 C61(H61), C64(H64), C65(H65), C68(H68), C69(H69), C70(H70), C73(H73), C74(H74),
  C75(H75), C76(H76)
7.c Fitted hexagon refined as free rotating group:
 C1(C2,C3,C4,C5,C6), C8(C9,C10,C11,C12,C13), C51(C52,C53,C54,C55,C56), C58(C59,
 C60,C61,C62,C63)
7.d Tetrahedral OH refined with riding coordinates:
 O12(H12), O16(H16), O23(H23A), O27(H27)
7.e Naphthalene refined as free rotating group:
 C17(C18,C19,C20,C21,C22,C23,C24,C25,C26), C67(C68,C69,C70,C71,C72,C73,C74,C75,
 C76)
7.f Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C38(H38A,H38B,H38C), C42(H42A,H42B,H42C), C46(H46A,H46B,
 H46C), C38A(H38D,H38E,H38F), C42A(H42D,H42E,H42F), C46A(H46D,H46E,H46F)
;
_shelx_res_checksum              60162
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'