#------------------------------------------------------------------------------
#$Date: 2016-03-26 19:27:03 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180435 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/04/7210426.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_7210426
loop_
_publ_author_name
'Bučar, Dejan-Krešimir'
'Filip, Stefan'
'Arhangelskis, Mihails'
'Lloyd, Gareth O.'
'Jones, William'
_publ_section_title
;
 Advantages of mechanochemical cocrystallisation in the solid-state
 chemistry of pigments: colour-tuned fluorescein cocrystals
;
_journal_issue                   32
_journal_name_full               CrystEngComm
_journal_page_first              6289
_journal_paper_doi               10.1039/c3ce41013g
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C40 H24 O10, C4 H4 N2, 2(C H4 O)'
_chemical_formula_sum            'C46 H36 N2 O12'
_chemical_formula_weight         808.76
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-10-26T18:34:44-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                115.965(7)
_cell_angle_beta                 93.139(5)
_cell_angle_gamma                92.811(6)
_cell_formula_units_Z            1
_cell_length_a                   7.6060(4)
_cell_length_b                   11.1161(9)
_cell_length_c                   12.0927(8)
_cell_measurement_reflns_used    4217
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      1.00
_cell_volume                     914.80(12)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Mercury (Macrae, 2008)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5815
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         3.25
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.8965
_exptl_absorpt_correction_T_min  0.6860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements Sortav (Blessing 1995)
;
_exptl_crystal_colour            'pale orange'
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             422
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         3211
_refine_ls_number_restraints     32
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0870P)²+0.0911P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1496
_reflns_number_gt                2457
_reflns_number_total             3211
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c3ce41013g.txt
_cod_data_source_block           8
_cod_original_cell_volume        914.80(11)
_cod_database_code               7210426
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O3 O 0.3322(2) 0.11388(17) 0.22871(15) 0.0321(4) Uani 1 1 d . . .
H3O H 0.3696 0.1129 0.2932 0.048 Uiso 1 1 calc R . .
O1 O 0.16389(19) 0.66891(16) 0.25554(14) 0.0234(4) Uani 1 1 d . . .
O5 O 0.1486(3) 0.98605(19) 0.82636(16) 0.0407(5) Uani 1 1 d . . .
H5O H 0.2086 0.9576 0.8668 0.061 Uiso 1 1 calc R . .
O2 O 0.1310(2) 0.74866(19) 0.11535(16) 0.0332(5) Uani 1 1 d . . .
O4 O 0.2634(2) 0.56548(16) 0.50578(15) 0.0277(4) Uani 1 1 d . . .
N1 N 0.4571(2) 0.0600(2) 0.42246(19) 0.0280(5) Uani 1 1 d . . .
C2 C -0.1222(3) 0.6592(2) 0.1789(2) 0.0235(5) Uani 1 1 d . . .
C7 C -0.1315(3) 0.6008(2) 0.2581(2) 0.0214(5) Uani 1 1 d . . .
C14 C 0.2235(3) 0.4629(2) 0.3893(2) 0.0225(5) Uani 1 1 d . . .
C12 C 0.2645(3) 0.2334(2) 0.2545(2) 0.0253(5) Uani 1 1 d . . .
C9 C 0.1176(3) 0.4758(2) 0.2985(2) 0.0209(5) Uani 1 1 d . . .
C15 C 0.1766(3) 0.6819(2) 0.5400(2) 0.0230(5) Uani 1 1 d . . .
C5 C -0.4419(3) 0.5570(2) 0.2089(2) 0.0269(6) Uani 1 1 d . . .
H5 H -0.5506 0.5201 0.216 0.032 Uiso 1 1 calc R . .
C1 C 0.0640(3) 0.6990(2) 0.1759(2) 0.0229(5) Uani 1 1 d . . .
C19 C -0.0084(3) 0.8285(2) 0.5026(2) 0.0256(5) Uani 1 1 d . . .
H19 H -0.0809 0.8482 0.4492 0.031 Uiso 1 1 calc R . .
C6 C -0.2922(3) 0.5461(2) 0.2739(2) 0.0243(5) Uani 1 1 d . . .
H6 H -0.2986 0.5043 0.3256 0.029 Uiso 1 1 calc R . .
C8 C 0.0501(3) 0.6091(2) 0.3213(2) 0.0214(5) Uani 1 1 d . . .
C11 C 0.1597(3) 0.2435(2) 0.1605(2) 0.0262(5) Uani 1 1 d . . .
H11 H 0.1388 0.1703 0.0832 0.031 Uiso 1 1 calc R . .
C10 C 0.0875(3) 0.3631(2) 0.1836(2) 0.0231(5) Uani 1 1 d . . .
H10 H 0.017 0.369 0.1212 0.028 Uiso 1 1 calc R . .
C13 C 0.2973(3) 0.3433(2) 0.3688(2) 0.0243(5) Uani 1 1 d . . .
H13 H 0.3679 0.3374 0.4312 0.029 Uiso 1 1 calc R . .
C4 C -0.4334(3) 0.6220(3) 0.1332(2) 0.0288(6) Uani 1 1 d . . .
H4 H -0.5369 0.6313 0.094 0.035 Uiso 1 1 calc R . .
C16 C 0.2061(3) 0.7727(2) 0.6636(2) 0.0268(5) Uani 1 1 d . . .
H16 H 0.2781 0.753 0.7172 0.032 Uiso 1 1 calc R . .
C20 C 0.0695(3) 0.7059(2) 0.4562(2) 0.0220(5) Uani 1 1 d . . .
C3 C -0.2730(3) 0.6729(3) 0.1157(2) 0.0287(6) Uani 1 1 d . . .
H3 H -0.2662 0.7146 0.0639 0.034 Uiso 1 1 calc R . .
C17 C 0.1274(3) 0.8927(2) 0.7065(2) 0.0292(6) Uani 1 1 d . . .
C21 C 0.4428(3) -0.0730(3) 0.3822(2) 0.0299(6) Uani 1 1 d . . .
H21 H 0.4034 -0.1276 0.3001 0.036 Uiso 1 1 calc R . .
C22 C 0.5152(3) 0.1319(3) 0.5413(2) 0.0318(6) Uani 1 1 d . . .
H22 H 0.5278 0.225 0.5735 0.038 Uiso 1 1 calc R . .
C18 C 0.0191(3) 0.9204(3) 0.6246(2) 0.0294(6) Uani 1 1 d . . .
H18 H -0.0341 1.0009 0.6526 0.035 Uiso 1 1 calc R . .
O6A O 0.2729(4) 0.8836(3) 0.9763(3) 0.0484(9) Uani 0.713(5) 1 d PDU A 1
H6AO H 0.1975 0.8459 0.9988 0.073 Uiso 0.713(5) 1 calc PR A 1
C23A C 0.4152(5) 0.8374(5) 0.9793(4) 0.0839(12) Uani 0.713(5) 1 d PDU A 1
H23A H 0.487 0.8479 0.9208 0.126 Uiso 0.713(5) 1 calc PR A 1
H23B H 0.3957 0.7438 0.9589 0.126 Uiso 0.713(5) 1 calc PR A 1
H23C H 0.4743 0.8844 1.0607 0.126 Uiso 0.713(5) 1 calc PR A 1
O6B O 0.3731(11) 0.9466(6) 0.9804(7) 0.0469(17) Uani 0.287(5) 1 d PDU A 2
H6BO H 0.353 0.999 1.0506 0.07 Uiso 0.287(5) 1 calc PR A 2
C23B C 0.4152(5) 0.8374(5) 0.9793(4) 0.0839(12) Uani 0.287(5) 1 d PDU A 2
H23D H 0.3718 0.764 0.9019 0.126 Uiso 0.287(5) 1 calc PR A 2
H23E H 0.3642 0.8263 1.0454 0.126 Uiso 0.287(5) 1 calc PR A 2
H23F H 0.5415 0.8392 0.9898 0.126 Uiso 0.287(5) 1 calc PR A 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 0 '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 0.006 '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
C12 O3 H3O 109.5 . .
C1 O1 C8 111.32(16) . .
C17 O5 H5O 109.5 . .
C14 O4 C15 118.68(17) . .
C21 N1 C22 115.6(2) . .
C7 C2 C3 121.8(2) . .
C7 C2 C1 108.60(19) . .
C3 C2 C1 129.6(2) . .
C2 C7 C6 121.2(2) . .
C2 C7 C8 110.35(19) . .
C6 C7 C8 128.4(2) . .
O4 C14 C9 123.2(2) . .
O4 C14 C13 114.75(19) . .
C9 C14 C13 122.1(2) . .
O3 C12 C13 122.2(2) . .
O3 C12 C11 117.7(2) . .
C13 C12 C11 120.0(2) . .
C14 C9 C10 117.3(2) . .
C14 C9 C8 120.5(2) . .
C10 C9 C8 122.01(19) . .
C16 C15 O4 115.0(2) . .
C16 C15 C20 122.7(2) . .
O4 C15 C20 122.3(2) . .
C6 C5 C4 121.7(2) . .
C6 C5 H5 119.2 . .
C4 C5 H5 119.2 . .
O2 C1 O1 121.2(2) . .
O2 C1 C2 130.3(2) . .
O1 C1 C2 108.57(19) . .
C18 C19 C20 122.0(2) . .
C18 C19 H19 119 . .
C20 C19 H19 119 . .
C5 C6 C7 117.0(2) . .
C5 C6 H6 121.5 . .
C7 C6 H6 121.5 . .
C20 C8 C9 111.73(18) . .
C20 C8 C7 113.77(18) . .
C9 C8 C7 114.95(19) . .
C20 C8 O1 107.21(17) . .
C9 C8 O1 107.18(16) . .
C7 C8 O1 100.88(16) . .
C10 C11 C12 119.4(2) . .
C10 C11 H11 120.3 . .
C12 C11 H11 120.3 . .
C11 C10 C9 121.9(2) . .
C11 C10 H10 119.1 . .
C9 C10 H10 119.1 . .
C12 C13 C14 119.4(2) . .
C12 C13 H13 120.3 . .
C14 C13 H13 120.3 . .
C3 C4 C5 120.9(2) . .
C3 C4 H4 119.6 . .
C5 C4 H4 119.6 . .
C17 C16 C15 119.4(2) . .
C17 C16 H16 120.3 . .
C15 C16 H16 120.3 . .
C15 C20 C19 116.5(2) . .
C15 C20 C8 121.1(2) . .
C19 C20 C8 122.2(2) . .
C4 C3 C2 117.4(2) . .
C4 C3 H3 121.3 . .
C2 C3 H3 121.3 . .
O5 C17 C16 122.9(2) . .
O5 C17 C18 117.6(2) . .
C16 C17 C18 119.5(2) . .
N1 C21 C22 121.9(2) . 2_656
N1 C21 H21 119 . .
C22 C21 H21 119 2_656 .
N1 C22 C21 122.4(2) . 2_656
N1 C22 H22 118.8 . .
C21 C22 H22 118.8 2_656 .
C19 C18 C17 119.9(2) . .
C19 C18 H18 120 . .
C17 C18 H18 120 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O3 C12 1.360(3) .
O3 H3O 0.82 .
O1 C1 1.358(3) .
O1 C8 1.518(3) .
O5 C17 1.359(3) .
O5 H5O 0.82 .
O2 C1 1.212(3) .
O4 C14 1.374(3) .
O4 C15 1.388(3) .
N1 C21 1.335(3) .
N1 C22 1.338(3) .
C2 C7 1.376(3) .
C2 C3 1.395(3) .
C2 C1 1.470(3) .
C7 C6 1.398(3) .
C7 C8 1.519(3) .
C14 C9 1.388(3) .
C14 C13 1.393(3) .
C12 C13 1.385(3) .
C12 C11 1.401(3) .
C9 C10 1.402(3) .
C9 C8 1.507(3) .
C15 C16 1.386(3) .
C15 C20 1.389(3) .
C5 C6 1.389(3) .
C5 C4 1.394(3) .
C5 H5 0.93 .
C19 C18 1.374(3) .
C19 C20 1.404(3) .
C19 H19 0.93 .
C6 H6 0.93 .
C8 C20 1.504(3) .
C11 C10 1.382(3) .
C11 H11 0.93 .
C10 H10 0.93 .
C13 H13 0.93 .
C4 C3 1.385(4) .
C4 H4 0.93 .
C16 C17 1.384(3) .
C16 H16 0.93 .
C3 H3 0.93 .
C17 C18 1.399(4) .
C21 C22 1.381(4) 2_656
C21 H21 0.93 .
C22 C21 1.381(4) 2_656
C22 H22 0.93 .
C18 H18 0.93 .
O6A C23A 1.226(4) .
O6A H6AO 0.82 .
C23A H23A 0.96 .
C23A H23B 0.96 .
C23A H23C 0.96 .
O6B H6BO 0.82 .
