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_7037824
_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(C26 H21 N5 O2), 4(C16 H36 N), 4(H2 O4 P), 0.5(H2 O)'
_chemical_formula_sum            'C116 H195 N14 O20.5 P4'
_chemical_formula_weight         2237.73
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-11-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_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                   16.1474(7)
_cell_length_b                   28.4487(12)
_cell_length_c                   26.5040(9)
_cell_measurement_reflns_used    40997
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.1
_cell_volume                     12175.2(8)
_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, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
 scan: Number of images: 180 Slice: -106.0000 - 74.0000 
 Image width: 1.0000 Exp time: 10.0000 Rotation axis: Omega 
 Omega: 0.0000 Kappa: 8.0000 Phi: 147.0000 XTD: 44.8780 2theta: -15.8125

 scan: Number of images: 104 Slice: -81.0000 - 23.0000
 Image width: 1.0000 Exp time: 10.0000 Rotation axis: Omega
 Omega: 0.0000 Kappa: -72.0000 Phi: 16.0000 XTD: 44.8780 2theta: -15.8125

 scan: Number of images: 75 Slice: -69.0000 - 6.0000
 Image width: 1.0000 Exp time: 10.0000 Rotation axis: Omega
 Omega: 0.0000 Kappa: -56.0000 Phi: 147.0000 XTD: 44.8780 2theta: -15.8125

 scan: Number of images: 10 Slice: 26.0000 - 36.0000
 Image width: 1.0000 Exp time: 10.0000 Rotation axis: Omega
 Omega: 0.0000 Kappa: 24.0000 Phi: -50.0000 XTD: 44.8780 2theta: -15.8125
;
_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      0.012440
_diffrn_orient_matrix_UB_12      0.049073
_diffrn_orient_matrix_UB_13      0.035671
_diffrn_orient_matrix_UB_21      0.033827
_diffrn_orient_matrix_UB_22      -0.014551
_diffrn_orient_matrix_UB_23      0.008220
_diffrn_orient_matrix_UB_31      0.013877
_diffrn_orient_matrix_UB_32      0.016614
_diffrn_orient_matrix_UB_33      -0.027695
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            106562
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.503
_diffrn_reflns_theta_min         2.113
_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    0.133
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.688
_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    1.221
_exptl_crystal_description       Prism
_exptl_crystal_F_000             4852
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.733
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 9739 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1712
_refine_ls_number_reflns         27595
_refine_ls_number_restraints     1341
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0679P)^2^+3.8744P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1355
_reflns_Friedel_coverage         0.934
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                23980
_reflns_number_total             27595
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5dt04497a2.cif
_cod_data_source_block           L2_H2PO4
_cod_depositor_comments
'Adding full bibliography for 7037824--7037825.cif.'
_cod_original_formula_sum        'C116 H195 N14 O20.50 P4'
_cod_database_code               7037824
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.969
_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,
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 C47A-N32
 1.4 with sigma of 0.02
 C3-C4
 1.4 with sigma of 0.01
 N61-C73 \\sim N61-C73A
 with sigma of 0.02
 C74-C73 \\sim C74A-C73A
 with sigma of 0.02
 C74-C75 \\sim C74A-C75A
 with sigma of 0.02
 C76-C75 \\sim C76A-C75A
 with sigma of 0.02
 N101-C101 \\sim N101-C201
 with sigma of 0.02
3. 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
4. Same fragment restrains
{C101, C102, C103, C104} sigma for 1-2: 0.02, 1-3: 0.04
as
{C201, C202, C203, C204}
5. Others
 Sof(H93C)=Sof(H93D)=Sof(C94A)=Sof(H94C)=Sof(H94D)=Sof(C95A)=Sof(H95C)=
 Sof(H95D)=Sof(C96A)=Sof(H96D)=Sof(H96E)=Sof(H96F)=1-FVAR(1)
 Sof(H93A)=Sof(H93B)=Sof(C94)=Sof(H94A)=Sof(H94B)=Sof(C95)=Sof(H95A)=Sof(H95B)=
 Sof(C96)=Sof(H96A)=Sof(H96B)=Sof(H96C)=FVAR(1)
 Sof(C73A)=Sof(H73C)=Sof(H73D)=Sof(C74A)=Sof(H74C)=Sof(H74D)=Sof(C75A)=
 Sof(H75C)=Sof(H75D)=1-FVAR(2)
 Sof(C73)=Sof(H73A)=Sof(H73B)=Sof(C74)=Sof(H74A)=Sof(H74B)=Sof(C75)=Sof(H75A)=
 Sof(H75B)=FVAR(2)
 Sof(C76A)=Sof(H76D)=Sof(H76E)=Sof(H76F)=1-FVAR(3)
 Sof(C76)=Sof(H76A)=Sof(H76B)=Sof(H76C)=FVAR(3)
 Sof(H11N)=Sof(H11O)=Sof(C116)=Sof(H11S)=Sof(H11T)=Sof(H11U)=1-FVAR(4)
 Sof(H11L)=Sof(H11M)=Sof(C117)=Sof(H11P)=Sof(H11Q)=Sof(H11R)=FVAR(4)
 Sof(H32A)=Sof(H35A)=Sof(N31A)=Sof(H31A)=Sof(C31A)=Sof(C32A)=Sof(H32C)=
 Sof(C33A)=Sof(H33B)=Sof(C34A)=Sof(C35A)=Sof(H35C)=Sof(C36A)=Sof(H36A)=
 Sof(C37A)=Sof(H37A)=Sof(C38A)=Sof(C47A)=Sof(C48A)=Sof(H48A)=Sof(C49A)=
 Sof(H49A)=Sof(C50A)=Sof(H50A)=Sof(C51A)=Sof(C52A)=Sof(H52A)=Sof(C53A)=
 Sof(H53A)=Sof(C54A)=Sof(H54A)=Sof(C55A)=Sof(H55A)=Sof(C56A)=1-FVAR(5)
 Sof(H32)=Sof(H35)=Sof(N31)=Sof(H31)=Sof(C31)=Sof(C32)=Sof(H32B)=Sof(C33)=
 Sof(H33A)=Sof(C34)=Sof(C35)=Sof(H35B)=Sof(C36)=Sof(H36)=Sof(C37)=Sof(H37)=
 Sof(C38)=Sof(C47)=Sof(C48)=Sof(H48)=Sof(C49)=Sof(H49)=Sof(C50)=Sof(H50)=
 Sof(C51)=Sof(C52)=Sof(H52)=Sof(C53)=Sof(H53)=Sof(C54)=Sof(H54)=Sof(C55)=
 Sof(H55)=Sof(C56)=FVAR(5)
 Sof(C201)=Sof(H20A)=Sof(H20B)=Sof(C202)=Sof(H20C)=Sof(H20D)=Sof(C203)=
 Sof(H20E)=Sof(H20F)=Sof(C204)=Sof(H20G)=Sof(H20H)=Sof(H20I)=1-FVAR(6)
 Sof(C101)=Sof(H10A)=Sof(H10B)=Sof(C102)=Sof(H10C)=Sof(H10D)=Sof(C103)=
 Sof(H10E)=Sof(H10F)=Sof(C104)=Sof(H10G)=Sof(H10H)=Sof(H10I)=FVAR(6)
 Fixed Sof: O201(0.5) H20J(0.5) H20K(0.5)
6.a Free rotating group:
 O201(H20J,H20K)
6.b Secondary CH2 refined with riding coordinates:
 C81(H81A,H81B), C82(H82A,H82B), C83(H83A,H83B), C85(H85A,H85B), C86(H86A,
 H86B), C87(H87A,H87B), C89(H89A,H89B), C90(H90A,H90B), C91(H91A,H91B),
 C93(H93A,H93B), C93(H93C,H93D), C94(H94A,H94B), C94A(H94C,H94D), C95(H95A,
 H95B), C95A(H95C,H95D), C61(H61A,H61B), C62(H62A,H62B), C63(H63A,H63B),
 C65(H65A,H65B), C66(H66A,H66B), C67(H67A,H67B), C69(H69A,H69B), C70(H70A,H70B),
  C71(H71A,H71B), C73(H73A,H73B), C73A(H73C,H73D), C74(H74A,H74B), C74A(H74C,
 H74D), C75(H75A,H75B), C75A(H75C,H75D), C101(H10A,H10B), C102(H10C,H10D),
 C103(H10E,H10F), C105(H10J,H10K), C106(H10L,H10M), C107(H10N,H10O), C109(H10S,
 H10T), C110(H11A,H11B), C111(H11C,H11D), C113(H11H,H11I), C114(H11J,H11K),
 C115(H11N,H11O), C115(H11L,H11M), C201(H20A,H20B), C202(H20C,H20D), C203(H20E,
 H20F), C121(H12A,H12B), C122(H12C,H12D), C123(H12E,H12F), C125(H12J,H12K),
 C126(H12L,H12M), C127(H12N,H12O), C129(H12S,H12T), C130(H13A,H13B), C131(H13C,
 H13D), C133(H13H,H13I), C134(H13J,H13K), C135(H13L,H13M)
6.c Aromatic/amide H refined with riding coordinates:
 N32(H32), N32(H32A), N33(H33), N34(H34), N35(H35), N35(H35A), C41(H41),
 C42(H42), C43(H43), C45(H45), N31(H31), C32(H32B), C33(H33A), C35(H35B),
 C36(H36), C37(H37), C48(H48), C49(H49), C50(H50), C52(H52), C53(H53), C54(H54),
  C55(H55), N31A(H31A), C32A(H32C), C33A(H33B), C35A(H35C), C36A(H36A),
 C37A(H37A), C48A(H48A), C49A(H49A), C50A(H50A), C52A(H52A), C53A(H53A),
 C54A(H54A), C55A(H55A), N1(H1), N2(H2), N3(H3), N4(H4), N5(H5), C2(H2A),
 C3(H3A), C5(H5A), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C15(H15),
 C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25)
6.d Idealised Me refined as rotating group:
 C84(H84A,H84B,H84C), C88(H88A,H88B,H88C), C92(H92A,H92B,H92C), C96(H96A,H96B,
 H96C), C96A(H96D,H96E,H96F), C64(H64A,H64B,H64C), C68(H68A,H68B,H68C),
 C72(H72A,H72B,H72C), C76(H76A,H76B,H76C), C76A(H76D,H76E,H76F), C104(H10G,H10H,
 H10I), C108(H10P,H10Q,H10R), C112(H11E,H11F,H11G), C117(H11P,H11Q,H11R),
 C116(H11S,H11T,H11U), C204(H20G,H20H,H20I), C124(H12G,H12H,H12I), C128(H12P,
 H12Q,H12R), C132(H13E,H13F,H13G), C136(H13N,H13O,H13P)
6.e Idealised tetrahedral OH refined as rotating group:
 O47(H47), O48(H48B), O43(H43A), O44(H44), O53(H53B), O54(H54B), O57(H57),
 O58(H58)
;
_shelx_res_checksum              17477
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 30/10/14
_olex2_submission_special_instructions 'No special instructions were received'