Anion complexation, transport and structural studies of a series of bis-methylurea compounds.
Olivari, Martina; Montis, Riccardo; Karagiannidis, Louise E.; Horton, Peter N.; Mapp, Lucy K.; Coles, Simon J.; Light, Mark E.; Gale, Philip A.; Caltagirone, Claudia; Dalton transactions (Cambridge, England : 2003) 44 (2015) 2138–2149; doi:10.1039/c4dt02893g

data_7033748
_publ_section_title
;
 Anion complexation, transport and structural studies of a series of
 bis-methylurea compounds.
;
_journal_issue                   5
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2138
_journal_page_last               2149
_journal_paper_doi               10.1039/c4dt02893g
_journal_volume                  44
_journal_year                    2015
_chemical_formula_moiety         '3(C23 H19 F6 N5 O2), 2(C16 H36 N), O4 S, H2 O'
_chemical_formula_sum            'C101 H131 F18 N17 O11 S'
_chemical_formula_weight         2133.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2014-07-09
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_audit_update_record
;
2014-11-10 deposited with the CCDC.
2014-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.087(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   29.281(6)
_cell_length_b                   14.001(2)
_cell_length_c                   28.838(6)
_cell_measurement_reflns_used    17376
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.4
_cell_volume                     10876(4)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (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    'ShelXD (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 0.967
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
scan:
    Number of images: 109
               Slice: -87.0000 - 22.0000
         Image width: 1.0000
            Exp time: 25.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: 150.0000
                 XTD: 45.0760
              2theta: -17.2654
scan:
    Number of images: 91
               Slice: -18.0000 - 73.0000
         Image width: 1.0000
            Exp time: 25.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 54.0000
                 Phi: -90.0000
                 XTD: 45.0760
              2theta: -17.2654
scan:
    Number of images: 43
               Slice: -42.0000 - 1.0000
         Image width: 1.0000
            Exp time: 25.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: 18.0000
                 Phi: -90.0000
                 XTD: 45.0760
              2theta: -17.2654
scan:
    Number of images: 20
               Slice: -62.0000 - -42.0000
         Image width: 1.0000
            Exp time: 25.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -72.0000
                 Phi: 120.0000
                 XTD: 45.0760
              2theta: -17.2654
scan:
    Number of images: 28
               Slice: -107.0000 - -79.0000
         Image width: 1.0000
            Exp time: 25.0000
       Rotation axis: Omega
               Omega: 0.0000
               Kappa: -18.0000
                 Phi: 90.0000
                 XTD: 45.0760
              2theta: -17.2654
;
_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      -0.032355
_diffrn_orient_matrix_UB_12      -0.018798
_diffrn_orient_matrix_UB_13      -0.004553
_diffrn_orient_matrix_UB_21      -0.011719
_diffrn_orient_matrix_UB_22      0.003124
_diffrn_orient_matrix_UB_23      0.070384
_diffrn_orient_matrix_UB_31      -0.029099
_diffrn_orient_matrix_UB_32      0.022305
_diffrn_orient_matrix_UB_33      -0.005835
_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  0.0862
_diffrn_reflns_av_unetI/netI     0.0820
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            64072
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.081
_diffrn_reflns_theta_min         2.430
_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    0.125
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.574
_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    1.303
_exptl_crystal_description       Chip
_exptl_crystal_F_000             4488
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.00043(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1709
_refine_ls_number_reflns         19019
_refine_ls_number_restraints     2570
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1533
_refine_ls_R_factor_gt           0.1074
_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^)+(0.0817P)^2^+36.2933P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2640
_refine_ls_wR_factor_ref         0.2878
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11124
_reflns_number_total             19019
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4dt02893g2.cif
_cod_data_source_block           L2-SO42-(3:1)
_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 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               7033748
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(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,H) groups
2. Restrained distances
 N105-C137 = N105-C117
 1.43 with sigma of 0.02
 N4-H4 = N2-H2 = N3-H3 = N104-H104 = N103-H103 = N102-H102 = N203-H203 = N202-
 H202 = N204-H204 = N205-H205
 0.88 with sigma of 0.002
 H104-H105
 1.93 with sigma of 0.02
 N401-C401 \\sim N401-C405 \\sim N401-C425 \\sim N401-C409 \\sim N401-C429
\\sim N401-C413 \\sim N401-
 C433
 with sigma of 0.02
 N5-C17 \\sim N5-C17A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N401 \\sim C401 \\sim C405 \\sim C409 \\sim C413 \\sim C425 \\sim C429 \\sim
C433 \\sim C402 \\sim C406 \\sim C410 \\sim C414 \\sim C426 \\sim C430 \\sim
C434 \\sim C403 \\sim C407 \\sim C411 \\sim C415 \\sim C427 \\sim C431 \\sim
C435 \\sim C404 \\sim C408 \\sim C412 \\sim C416 \\sim C428 \\sim C432 \\sim
C436: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
C17A \\sim C22A \\sim C21A \\sim C20A \\sim C19A \\sim C18A \\sim C18 \\sim C17
\\sim C22 \\sim C21 \\sim C20 \\sim C19 \\sim C23A \\sim C23 \\sim F4 \\sim F4A
\\sim F5A \\sim F6A \\sim F5 \\sim F6: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08
N105 \\sim C137 \\sim C142 \\sim C122 \\sim C141 \\sim C121 \\sim C140 \\sim
C120 \\sim C139 \\sim C119 \\sim C118 \\sim C138 \\sim C117 \\sim C143 \\sim
C123 \\sim F104 \\sim F105 \\sim F114 \\sim F106 \\sim F115 \\sim F116: within
1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
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
{C8, C9, C10, C11, C12, C13, C14, F1, F2, F3}
as
{C17, C18, C19, C20, C21, C22, C23, F4, F5, F6}
{C8, C9, C10, C11, C12, C13, C14, F1, F2, F3}
as
{C17A, C18A, C19A, C20A, C21A, C22A, C23A, F4A, F5A, F6A}
{C8, C9, C10, C11, C12, C13, C14, F1, F2, F3}
as
{C117, C118, C119, C120, C121, C122, C123, F104, F105, F106}
{C8, C9, C10, C11, C12, C13, C14, F1, F2, F3}
as
{C137, C138, C139, C140, C141, C142, C143, F114, F115, F116}
{C8, C9, C10, C11, C12, C13, C14, F1, F2, F3}
as
{C208, C209, C210, C211, C212, C213, C214, F201, F202, F203}
{C405, C406, C407, C408}
as
{C425, C426, C427, C428}
{C409, C410, C411, C412}
as
{C429, C430, C431, C432}
{C413, C414, C415, C416}
as
{C433, C434, C435, C436}
6. Others
 Sof(H10A)=Sof(C137)=Sof(C138)=Sof(H138)=Sof(C139)=Sof(H139)=Sof(C140)=
 Sof(C141)=Sof(H141)=Sof(C142)=Sof(H142)=Sof(C143)=Sof(F114)=Sof(F115)=
 Sof(F116)=1-FVAR(1)
 Sof(H105)=Sof(C117)=Sof(C118)=Sof(H118)=Sof(C119)=Sof(H119)=Sof(C120)=
 Sof(C121)=Sof(H121)=Sof(C122)=Sof(H122)=Sof(C123)=Sof(F104)=Sof(F105)=
 Sof(F106)=FVAR(1)
 Sof(C425)=Sof(H42A)=Sof(H42B)=Sof(C426)=Sof(H42C)=Sof(H42D)=Sof(C427)=
 Sof(H42E)=Sof(H42F)=Sof(C428)=Sof(H42G)=Sof(H42H)=Sof(H42I)=Sof(C429)=
 Sof(H42J)=Sof(H42K)=Sof(C430)=Sof(H43A)=Sof(H43B)=Sof(C431)=Sof(H43C)=
 Sof(H43D)=Sof(C432)=Sof(H43E)=Sof(H43F)=Sof(H43G)=Sof(C433)=Sof(H43H)=
 Sof(H43I)=Sof(C434)=Sof(H43J)=Sof(H43K)=Sof(C435)=Sof(H43L)=Sof(H43M)=
 Sof(C436)=Sof(H43N)=Sof(H43O)=Sof(H43P)=Sof(O611)=Sof(H61A)=Sof(H61B)=1-FVAR(2)
 Sof(C405)=Sof(H40J)=Sof(H40K)=Sof(C406)=Sof(H40L)=Sof(H40M)=Sof(C407)=
 Sof(H40N)=Sof(H40O)=Sof(C408)=Sof(H40P)=Sof(H40Q)=Sof(H40R)=Sof(C409)=
 Sof(H40S)=Sof(H40T)=Sof(C410)=Sof(H41A)=Sof(H41B)=Sof(C411)=Sof(H41C)=
 Sof(H41D)=Sof(C412)=Sof(H41E)=Sof(H41F)=Sof(H41G)=Sof(C413)=Sof(H41H)=
 Sof(H41I)=Sof(C414)=Sof(H41J)=Sof(H41K)=Sof(C415)=Sof(H41L)=Sof(H41M)=
 Sof(C416)=Sof(H41N)=Sof(H41O)=Sof(H41P)=Sof(O601)=Sof(H60A)=Sof(H60B)=FVAR(2)
 Sof(H5B)=Sof(C17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=
 Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=1-
 FVAR(3)
 Sof(H5A)=Sof(C17)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(C21)=
 Sof(H21)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(3)
 Sof(F212)=Sof(F213)=Sof(F214)=1-FVAR(4)
 Sof(F201)=Sof(F202)=Sof(F203)=FVAR(4)
7.a Free rotating group:
 O601(H60A,H60B), O611(H61A,H61B)
7.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C15(H15A,H15B), C106(H10E,H10F), C115(H11A,H11B), C206(H20D,
 H20E), C215(H21B,H21C), C301(H30A,H30B), C302(H30C,H30D), C303(H30E,H30F),
 C305(H30J,H30K), C306(H30L,H30M), C307(H30N,H30O), C309(H30S,H30T), C310(H31A,
 H31B), C311(H31C,H31D), C313(H31H,H31I), C314(H31J,H31K), C315(H31L,H31M),
 C401(H40A,H40B), C402(H40C,H40D), C403(H40E,H40F), C405(H40J,H40K), C406(H40L,
 H40M), C407(H40N,H40O), C409(H40S,H40T), C410(H41A,H41B), C411(H41C,H41D),
 C413(H41H,H41I), C414(H41J,H41K), C415(H41L,H41M), C425(H42A,H42B), C426(H42C,
 H42D), C427(H42E,H42F), C429(H42J,H42K), C430(H43A,H43B), C431(H43C,H43D),
 C433(H43H,H43I), C434(H43J,H43K), C435(H43L,H43M)
7.c Aromatic/amide H refined with riding coordinates:
 N5(H5A), N5(H5B), C2(H2A), C3(H3A), C4(H4A), C9(H9), C10(H10), C12(H12),
 C13(H13), C18(H18), C19(H19), C21(H21), C22(H22), C18A(H18A), C19A(H19A),
 C21A(H21A), C22A(H22A), N105(H105), N105(H10A), C102(H10B), C103(H10C),
 C104(H10D), C109(H109), C110(H110), C112(H112), C113(H113), C118(H118),
 C119(H119), C121(H121), C122(H122), C138(H138), C139(H139), C141(H141),
 C142(H142), C202(H20A), C203(H20B), C204(H20C), C209(H209), C210(H210),
 C212(H212), C213(H213), C218(H218), C219(H219), C221(H221), C222(H222)
7.d Idealised Me refined as rotating group:
 C304(H30G,H30H,H30I), C308(H30P,H30Q,H30R), C312(H31E,H31F,H31G), C316(H31N,
 H31O,H31P), C404(H40G,H40H,H40I), C408(H40P,H40Q,H40R), C412(H41E,H41F,H41G),
 C416(H41N,H41O,H41P), C428(H42G,H42H,H42I), C432(H43E,H43F,H43G), C436(H43N,
 H43O,H43P)
;
_shelx_res_checksum              29360
_shelx_hkl_checksum              1951
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'ShelXD (Sheldrick, 2008)'
_olex2_submission_special_instructions 'No special instructions were received'