#------------------------------------------------------------------------------
#$Date: 2016-03-25 23:32:07 +0200 (Fri, 25 Mar 2016) $
#$Revision: 180043 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/37/7033742.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_7033742
loop_
_publ_author_name
'Olivari, Martina'
'Montis, Riccardo'
'Karagiannidis, Louise E.'
'Horton, Peter N.'
'Mapp, Lucy K.'
'Coles, Simon J.'
'Light, Mark E.'
'Gale, Philip A.'
'Caltagirone, Claudia'
_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         'C25 H17 F12 N5 O2'
_chemical_formula_sum            'C25 H17 F12 N5 O2'
_chemical_formula_weight         647.43
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-11-10 deposited with the CCDC.
2014-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.463(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.4364(9)
_cell_length_b                   12.8183(10)
_cell_length_c                   9.0313(7)
_cell_measurement_reflns_used    8813
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.4
_cell_volume                     1301.93(18)
_computing_cell_refinement
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)
;
_computing_data_collection
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)
;
_computing_data_reduction
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)
;
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_radiation_collimation    'Confocal mirrors, VHF Varimax '
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9371
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.467
_diffrn_reflns_theta_min         3.092
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2012)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_description       Rod
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2968
_refine_ls_number_restraints     204
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0381
_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/[σ²(Fo²)+(0.0523P)²+0.5947P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1025
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2493
_reflns_number_total             2968
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4dt02893g2.cif
_cod_data_source_block           L4-A
_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               7033742
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.964
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2013-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0000 0.91595(17) 0.2500 0.0264(4) Uani 1 2 d S T P . .
H1 H 0.0000 0.9901 0.2500 0.032 Uiso 1 2 calc R U P . .
C2 C 0.03605(13) 0.86129(11) 0.38276(16) 0.0234(3) Uani 1 1 d . . . . .
H2 H 0.0618 0.8971 0.4750 0.028 Uiso 1 1 calc R U . . .
C3 C 0.03373(11) 0.75291(11) 0.37820(15) 0.0188(3) Uani 1 1 d . . . . .
C4 C 0.06760(13) 0.68983(11) 0.52125(15) 0.0213(3) Uani 1 1 d . . . . .
H4A H 0.1276 0.7285 0.5935 0.026 Uiso 1 1 calc R U . . .
H4B H -0.0034 0.6793 0.5681 0.026 Uiso 1 1 calc R U . . .
C5 C 0.16763(11) 0.52695(11) 0.60118(14) 0.0179(3) Uani 1 1 d . . . . .
C6 C 0.27000(12) 0.35702(11) 0.64300(14) 0.0186(3) Uani 1 1 d . . . . .
C7 C 0.33220(12) 0.37067(11) 0.78992(15) 0.0197(3) Uani 1 1 d . . . . .
H7 H 0.3435 0.4385 0.8325 0.024 Uiso 1 1 calc R U . . .
C8 C 0.37735(12) 0.28340(11) 0.87309(15) 0.0210(3) Uani 1 1 d . . . . .
C9 C 0.36402(13) 0.18366(11) 0.81355(16) 0.0221(3) Uani 1 1 d . . . . .
H9 H 0.3940 0.1248 0.8724 0.027 Uiso 1 1 calc R U . . .
C10 C 0.30552(12) 0.17172(11) 0.66511(16) 0.0214(3) Uani 1 1 d . . . . .
C11 C 0.25943(12) 0.25697(11) 0.58034(15) 0.0206(3) Uani 1 1 d . . . . .
H11 H 0.2204 0.2475 0.4790 0.025 Uiso 1 1 calc R U . . .
C12 C 0.43984(14) 0.29880(12) 1.03301(16) 0.0264(3) Uani 1 1 d D U . . .
C13 C 0.29437(14) 0.06480(12) 0.59624(17) 0.0270(3) Uani 1 1 d D U . . .
F1 F 0.36481(11) 0.31294(17) 1.12721(11) 0.0423(5) Uani 0.906(5) 1 d D U P A 1
F2 F 0.51108(14) 0.38431(9) 1.04728(13) 0.0409(5) Uani 0.906(5) 1 d D U P A 1
F3 F 0.5098(2) 0.21843(18) 1.0838(2) 0.0305(4) Uani 0.906(5) 1 d D U P A 1
F4 F 0.25836(16) -0.00608(9) 0.68500(16) 0.0445(4) Uani 0.924(4) 1 d D U P B 1
F5 F 0.39460(11) 0.03154(10) 0.5591(2) 0.0516(5) Uani 0.924(4) 1 d D U P B 1
F6 F 0.21186(14) 0.06170(9) 0.46835(13) 0.0429(4) Uani 0.924(4) 1 d D U P B 1
N1 N 0.0000 0.69939(13) 0.2500 0.0187(3) Uani 1 2 d S T P . .
N2 N 0.11539(10) 0.58988(9) 0.48896(12) 0.0190(2) Uani 1 1 d . . . . .
H2A H 0.1103 0.5698 0.3948 0.023 Uiso 1 1 calc R U . . .
N3 N 0.22006(11) 0.44004(9) 0.55236(12) 0.0213(3) Uani 1 1 d . . . . .
H3 H 0.2224 0.4363 0.4557 0.026 Uiso 1 1 calc R U . . .
O1 O 0.16809(9) 0.54648(8) 0.73531(10) 0.0210(2) Uani 1 1 d . . . . .
F21 F 0.3475(10) 0.2572(13) 1.1136(16) 0.041(4) Uiso 0.094(5) 1 d D U P A 2
F22 F 0.4483(13) 0.3909(7) 1.0816(13) 0.038(3) Uiso 0.094(5) 1 d D U P A 2
F23 F 0.5296(16) 0.2376(16) 1.085(3) 0.039(7) Uiso 0.094(5) 1 d D U P A 2
F24 F 0.216(2) 0.002(2) 0.634(3) 0.096(9) Uiso 0.076(4) 1 d D U P B 2
F25 F 0.4002(12) 0.0121(14) 0.650(2) 0.057(5) Uiso 0.076(4) 1 d D U P B 2
F26 F 0.2857(16) 0.0632(12) 0.4513(12) 0.042(4) Uiso 0.076(4) 1 d D U P B 2
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'
F F 0.0171 0.0103 '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'
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
C2 C1 C2 119.23(19) . 2
C2 C1 H1 120.4 . .
C2 C1 H1 120.4 2 .
C1 C2 C3 118.60(14) . .
C1 C2 H2 120.7 . .
C3 C2 H2 120.7 . .
N1 C3 C2 122.55(13) . .
N1 C3 C4 116.91(13) . .
C2 C3 C4 120.53(12) . .
N2 C4 C3 110.45(11) . .
N2 C4 H4A 109.6 . .
C3 C4 H4A 109.6 . .
N2 C4 H4B 109.6 . .
C3 C4 H4B 109.6 . .
H4A C4 H4B 108.1 . .
O1 C5 N2 122.58(13) . .
O1 C5 N3 123.63(12) . .
N2 C5 N3 113.80(11) . .
C7 C6 C11 119.38(12) . .
C7 C6 N3 122.91(13) . .
C11 C6 N3 117.68(12) . .
C8 C7 C6 119.09(13) . .
C8 C7 H7 120.5 . .
C6 C7 H7 120.5 . .
C9 C8 C7 121.87(13) . .
C9 C8 C12 119.60(13) . .
C7 C8 C12 118.51(13) . .
C8 C9 C10 118.34(13) . .
C8 C9 H9 120.8 . .
C10 C9 H9 120.8 . .
C11 C10 C9 120.93(13) . .
C11 C10 C13 119.81(13) . .
C9 C10 C13 119.26(13) . .
C10 C11 C6 120.31(12) . .
C10 C11 H11 119.8 . .
C6 C11 H11 119.8 . .
F22 C12 F23 115.7(12) . .
F1 C12 F3 107.61(16) . .
F1 C12 F2 106.01(14) . .
F3 C12 F2 106.18(17) . .
F22 C12 F21 100.5(8) . .
F23 C12 F21 101.1(12) . .
F22 C12 C8 116.8(5) . .
F23 C12 C8 117.9(13) . .
F1 C12 C8 112.60(13) . .
F3 C12 C8 112.33(15) . .
F2 C12 C8 111.69(13) . .
F21 C12 C8 99.6(6) . .
F26 C13 F24 108.9(14) . .
F5 C13 F4 108.15(15) . .
F5 C13 F6 106.03(14) . .
F4 C13 F6 104.54(14) . .
F26 C13 F25 104.4(10) . .
F24 C13 F25 101.8(14) . .
F26 C13 C10 114.7(7) . .
F24 C13 C10 118.2(15) . .
F5 C13 C10 112.79(13) . .
F4 C13 C10 112.80(13) . .
F6 C13 C10 111.98(13) . .
F25 C13 C10 107.1(8) . .
C3 N1 C3 118.44(17) 2 .
C5 N2 C4 120.79(11) . .
C5 N2 H2A 119.6 . .
C4 N2 H2A 119.6 . .
C5 N3 C6 125.72(11) . .
C5 N3 H3 117.1 . .
C6 N3 H3 117.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3852(18) .
C1 C2 1.3852(18) 2
C1 H1 0.9500 .
C2 C3 1.390(2) .
C2 H2 0.9500 .
C3 N1 1.3408(16) .
C3 C4 1.5137(19) .
C4 N2 1.4433(18) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 O1 1.2360(16) .
C5 N2 1.3472(17) .
C5 N3 1.3752(18) .
C6 C7 1.3980(18) .
C6 C11 1.398(2) .
C6 N3 1.3996(17) .
C7 C8 1.393(2) .
C7 H7 0.9500 .
C8 C9 1.385(2) .
C8 C12 1.5035(19) .
C9 C10 1.394(2) .
C9 H9 0.9500 .
C10 C11 1.383(2) .
C10 C13 1.501(2) .
C11 H11 0.9500 .
C12 F22 1.257(9) .
C12 F23 1.309(13) .
C12 F1 1.3259(19) .
C12 F3 1.334(2) .
C12 F2 1.358(2) .
C12 F21 1.486(10) .
C13 F26 1.294(11) .
C13 F24 1.299(14) .
C13 F5 1.3221(19) .
C13 F4 1.3257(19) .
C13 F6 1.3529(19) .
C13 F25 1.395(12) .
N1 C3 1.3408(16) 2
N2 H2A 0.8800 .
N3 H3 0.8800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O1 0.88 2.25 3.0278(14) 146.7 4_565
N3 H3 O1 0.88 1.99 2.8220(14) 158.1 4_565
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C2 C1 C2 C3 -0.58(9) 2 .
C1 C2 C3 N1 1.22(19) . .
C1 C2 C3 C4 -177.55(11) . .
N1 C3 C4 N2 29.58(15) . .
C2 C3 C4 N2 -151.59(13) . .
C11 C6 C7 C8 -3.1(2) . .
N3 C6 C7 C8 178.96(13) . .
C6 C7 C8 C9 1.1(2) . .
C6 C7 C8 C12 -177.61(13) . .
C7 C8 C9 C10 1.2(2) . .
C12 C8 C9 C10 179.87(13) . .
C8 C9 C10 C11 -1.5(2) . .
C8 C9 C10 C13 177.55(13) . .
C9 C10 C11 C6 -0.5(2) . .
C13 C10 C11 C6 -179.57(13) . .
C7 C6 C11 C10 2.8(2) . .
N3 C6 C11 C10 -179.08(12) . .
C9 C8 C12 F22 -179.3(8) . .
C7 C8 C12 F22 -0.6(8) . .
C9 C8 C12 F23 35.8(12) . .
C7 C8 C12 F23 -145.5(12) . .
C9 C8 C12 F1 -100.57(18) . .
C7 C8 C12 F1 78.1(2) . .
C9 C8 C12 F3 21.1(2) . .
C7 C8 C12 F3 -160.20(18) . .
C9 C8 C12 F2 140.29(15) . .
C7 C8 C12 F2 -41.02(19) . .
C9 C8 C12 F21 -72.2(6) . .
C7 C8 C12 F21 106.5(6) . .
C11 C10 C13 F26 26.2(9) . .
C9 C10 C13 F26 -152.8(9) . .
C11 C10 C13 F24 -104.3(15) . .
C9 C10 C13 F24 76.6(15) . .
C11 C10 C13 F5 103.19(18) . .
C9 C10 C13 F5 -75.86(19) . .
C11 C10 C13 F4 -133.91(16) . .
C9 C10 C13 F4 47.0(2) . .
C11 C10 C13 F6 -16.3(2) . .
C9 C10 C13 F6 164.63(14) . .
C11 C10 C13 F25 141.6(9) . .
C9 C10 C13 F25 -37.4(10) . .
C2 C3 N1 C3 -0.62(10) . 2
C4 C3 N1 C3 178.19(13) . 2
O1 C5 N2 C4 6.6(2) . .
N3 C5 N2 C4 -173.24(12) . .
C3 C4 N2 C5 170.10(12) . .
O1 C5 N3 C6 6.9(2) . .
N2 C5 N3 C6 -173.32(13) . .
C7 C6 N3 C5 -36.7(2) . .
C11 C6 N3 C5 145.29(14) . .
