#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:47:15 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223607 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/25/7232599.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_7232599
loop_
_publ_author_name
'Barton, Benita'
'de Jager, Lize'
'Hosten, Eric C.'
_publ_section_title
;
 Minor modifications afford improved host selectivities in xanthenyl-type
 host systems
;
_journal_issue                   19
_journal_name_full               CrystEngComm
_journal_page_first              3000
_journal_paper_doi               10.1039/C9CE00265K
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C40 H32 N2 O2, C7 H8 O, 0.22(O)'
_chemical_formula_sum            'C47 H40 N2 O3.22'
_chemical_formula_weight         684.34
_chemical_melting_point          488.15
_chemical_name_common
N,N-bis(9-phenyl-9-xanthenyl)ethylenediamine:anisole:water
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-02-05 deposited with the CCDC.    2019-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                91.979(2)
_cell_angle_beta                 107.947(2)
_cell_angle_gamma                111.131(2)
_cell_formula_units_Z            1
_cell_length_a                   8.9207(4)
_cell_length_b                   9.1082(4)
_cell_length_c                   12.6652(6)
_cell_measurement_reflns_used    9844
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.58
_cell_volume                     900.79(7)
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2011.4.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'
_computing_structure_refinement
'SHELXL-2018/3 (Sheldrick, 2015) and ShelXle (Hübschle, 2011)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            36003
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.331
_diffrn_reflns_theta_min         1.713
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9582
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             362
_exptl_crystal_size_max          0.529
_exptl_crystal_size_mid          0.334
_exptl_crystal_size_min          0.319
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4480
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0414
_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)+(0.0565P)²+0.2347P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1141
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3831
_reflns_number_total             4480
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce00265k2.cif
_cod_data_source_block           ia124
_cod_depositor_comments
'Adding full bibliography for 7232597--7232602.cif.'
_cod_database_code               7232599
_shelx_shelxl_version_number     2018/3
_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   0.960
_shelx_estimated_absorpt_t_max   0.975
loop_
_space_group_symop_operation_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_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
O1 O 0.59591(11) 0.48550(9) 0.86180(8) 0.0381(2) Uani 1 1 d . . . . .
N1 N 0.69025(10) 0.66199(9) 0.60465(7) 0.02369(18) Uani 1 1 d . . . . .
H1 H 0.670983 0.746319 0.577410 0.037(3) Uiso 1 1 d R . . . .
C1 C 0.76654(11) 0.70365(10) 0.72888(8) 0.02053(18) Uani 1 1 d . . . . .
C2 C 0.52486(12) 0.52563(11) 0.56281(8) 0.0251(2) Uani 1 1 d . . . . .
H2A H 0.436090 0.555666 0.577509 0.030 Uiso 1 1 calc R U . . .
H2B H 0.532728 0.435740 0.602808 0.030 Uiso 1 1 calc R U . . .
C11 C 0.81392(12) 0.56771(11) 0.77444(8) 0.0240(2) Uani 1 1 d . . . . .
C12 C 0.72744(14) 0.46780(12) 0.83507(9) 0.0288(2) Uani 1 1 d . . . . .
C13 C 0.76763(18) 0.33983(14) 0.87258(11) 0.0414(3) Uani 1 1 d . . . . .
H13 H 0.705588 0.272036 0.913160 0.050 Uiso 1 1 calc R U . . .
C14 C 0.89749(18) 0.31262(14) 0.85042(12) 0.0446(3) Uani 1 1 d . . . . .
H14 H 0.924967 0.225248 0.875209 0.054 Uiso 1 1 calc R U . . .
C15 C 0.98840(16) 0.41234(15) 0.79199(12) 0.0436(3) Uani 1 1 d . . . . .
H15 H 1.079465 0.394514 0.777720 0.052 Uiso 1 1 calc R U . . .
C16 C 0.94640(14) 0.53812(13) 0.75439(11) 0.0344(2) Uani 1 1 d . . . . .
H16 H 1.009183 0.605686 0.714071 0.041 Uiso 1 1 calc R U . . .
C21 C 0.64225(11) 0.72894(11) 0.78065(8) 0.02236(19) Uani 1 1 d . . . . .
C22 C 0.56248(13) 0.61977(12) 0.83988(9) 0.0269(2) Uani 1 1 d . . . . .
C23 C 0.44198(14) 0.63895(14) 0.88143(10) 0.0347(2) Uani 1 1 d . . . . .
H23 H 0.389672 0.562875 0.922084 0.042 Uiso 1 1 calc R U . . .
C24 C 0.39946(14) 0.76910(15) 0.86304(10) 0.0375(3) Uani 1 1 d . . . . .
H24 H 0.316877 0.782778 0.890650 0.045 Uiso 1 1 calc R U . . .
C25 C 0.47699(15) 0.88048(15) 0.80421(10) 0.0371(3) Uani 1 1 d . . . . .
H25 H 0.447581 0.970348 0.791577 0.044 Uiso 1 1 calc R U . . .
C26 C 0.59717(14) 0.86036(13) 0.76400(9) 0.0303(2) Uani 1 1 d . . . . .
H26 H 0.650144 0.937537 0.724250 0.036 Uiso 1 1 calc R U . . .
C31 C 0.92887(11) 0.85749(11) 0.76114(8) 0.0227(2) Uani 1 1 d . . . . .
C32 C 0.98219(14) 0.94715(12) 0.68355(10) 0.0314(2) Uani 1 1 d . . . . .
H32 H 0.917862 0.913168 0.605553 0.038 Uiso 1 1 calc R U . . .
C33 C 1.13023(15) 1.08742(13) 0.71959(12) 0.0391(3) Uani 1 1 d . . . . .
H33 H 1.164781 1.148744 0.665804 0.047 Uiso 1 1 calc R U . . .
C34 C 1.22633(14) 1.13753(13) 0.83199(12) 0.0390(3) Uani 1 1 d . . . . .
H34 H 1.327432 1.232290 0.855785 0.047 Uiso 1 1 calc R U . . .
C35 C 1.17460(14) 1.04886(14) 0.91009(11) 0.0376(3) Uani 1 1 d . . . . .
H35 H 1.240296 1.082678 0.987903 0.045 Uiso 1 1 calc R U . . .
C36 C 1.02677(13) 0.91046(13) 0.87493(9) 0.0306(2) Uani 1 1 d . . . . .
H36 H 0.991711 0.850840 0.929278 0.037 Uiso 1 1 calc R U . . .
C41 C 0.65457(18) 0.06509(15) 0.48211(12) 0.0464(3) Uani 1 1 d . . . . .
H41 H 0.760618 0.109584 0.469777 0.056 Uiso 0.5 1 calc R U P A 1
O4 O 0.7994(3) 0.1190(2) 0.46352(16) 0.0465(4) Uani 0.5 1 d . . P B 2
C44 C 0.9062(4) 0.2842(4) 0.4949(3) 0.0546(7) Uani 0.5 1 d . . P B 2
H44A H 0.838751 0.347143 0.464387 0.082 Uiso 0.5 1 calc R U P B 2
H44B H 0.999689 0.307512 0.464761 0.082 Uiso 0.5 1 calc R U P B 2
H44C H 0.953740 0.311803 0.577101 0.082 Uiso 0.5 1 calc R U P B 2
C43 C 0.45992(18) 0.08953(15) 0.56910(12) 0.0471(3) Uani 1 1 d . . . . .
H43 H 0.431731 0.150470 0.616506 0.057 Uiso 1 1 calc R U . . .
C42 C 0.61280(18) 0.15427(15) 0.55155(12) 0.0461(3) Uani 1 1 d . . . . .
H42 H 0.690357 0.259862 0.586660 0.055 Uiso 1 1 calc R U . . .
O9 O 1.0836(15) 0.3767(17) 0.5259(10) 0.077(5) Uani 0.110(5) 1 d . . P C -1
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'
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
C12 O1 C22 118.53(8) . .
C2 N1 C1 114.51(7) . .
C2 N1 H1 106.3 . .
C1 N1 H1 108.1 . .
N1 C1 C11 108.21(7) . .
N1 C1 C21 111.75(7) . .
C11 C1 C21 109.33(8) . .
N1 C1 C31 109.21(7) . .
C11 C1 C31 109.35(7) . .
C21 C1 C31 108.97(7) . .
N1 C2 C2 109.87(10) . 2_666
N1 C2 H2A 109.7 . .
C2 C2 H2A 109.7 2_666 .
N1 C2 H2B 109.7 . .
C2 C2 H2B 109.7 2_666 .
H2A C2 H2B 108.2 . .
C12 C11 C16 117.42(9) . .
C12 C11 C1 122.24(9) . .
C16 C11 C1 120.34(9) . .
O1 C12 C11 123.14(9) . .
O1 C12 C13 115.15(10) . .
C11 C12 C13 121.71(11) . .
C14 C13 C12 119.51(11) . .
C14 C13 H13 120.2 . .
C12 C13 H13 120.2 . .
C13 C14 C15 120.07(11) . .
C13 C14 H14 120.0 . .
C15 C14 H14 120.0 . .
C14 C15 C16 119.88(12) . .
C14 C15 H15 120.1 . .
C16 C15 H15 120.1 . .
C15 C16 C11 121.39(11) . .
C15 C16 H16 119.3 . .
C11 C16 H16 119.3 . .
C22 C21 C26 117.33(9) . .
C22 C21 C1 122.19(9) . .
C26 C21 C1 120.38(8) . .
O1 C22 C21 122.88(9) . .
O1 C22 C23 115.19(9) . .
C21 C22 C23 121.93(10) . .
C24 C23 C22 119.36(10) . .
C24 C23 H23 120.3 . .
C22 C23 H23 120.3 . .
C23 C24 C25 120.12(10) . .
C23 C24 H24 119.9 . .
C25 C24 H24 119.9 . .
C26 C25 C24 119.87(11) . .
C26 C25 H25 120.1 . .
C24 C25 H25 120.1 . .
C25 C26 C21 121.37(10) . .
C25 C26 H26 119.3 . .
C21 C26 H26 119.3 . .
C32 C31 C36 118.34(9) . .
C32 C31 C1 123.63(9) . .
C36 C31 C1 118.03(9) . .
C31 C32 C33 120.31(11) . .
C31 C32 H32 119.8 . .
C33 C32 H32 119.8 . .
C34 C33 C32 120.73(11) . .
C34 C33 H33 119.6 . .
C32 C33 H33 119.6 . .
C33 C34 C35 119.45(10) . .
C33 C34 H34 120.3 . .
C35 C34 H34 120.3 . .
C34 C35 C36 120.07(11) . .
C34 C35 H35 120.0 . .
C36 C35 H35 120.0 . .
C35 C36 C31 121.09(10) . .
C35 C36 H36 119.5 . .
C31 C36 H36 119.5 . .
O4 C41 C43 117.48(16) . 2_656
O4 C41 C42 122.85(15) . .
C43 C41 C42 119.66(14) 2_656 .
C43 C41 H41 120.2 2_656 .
C42 C41 H41 120.2 . .
C41 O4 C44 119.87(19) . .
O4 C44 H44A 109.5 . .
O4 C44 H44B 109.5 . .
H44A C44 H44B 109.5 . .
O4 C44 H44C 109.5 . .
H44A C44 H44C 109.5 . .
H44B C44 H44C 109.5 . .
C42 C43 C41 120.42(14) . 2_656
C42 C43 H43 119.8 . .
C41 C43 H43 119.8 2_656 .
C43 C42 C41 119.92(13) . .
C43 C42 H42 120.0 . .
C41 C42 H42 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C12 1.3765(14) .
O1 C22 1.3774(13) .
N1 C2 1.4669(12) .
N1 C1 1.4817(12) .
N1 H1 0.9031 .
C1 C11 1.5234(13) .
C1 C21 1.5276(13) .
C1 C31 1.5363(12) .
C2 C2 1.5201(19) 2_666
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C11 C12 1.3857(14) .
C11 C16 1.3942(15) .
C12 C13 1.3955(15) .
C13 C14 1.373(2) .
C13 H13 0.9500 .
C14 C15 1.384(2) .
C14 H14 0.9500 .
C15 C16 1.3845(16) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C21 C22 1.3886(14) .
C21 C26 1.3969(14) .
C22 C23 1.3931(15) .
C23 C24 1.3756(18) .
C23 H23 0.9500 .
C24 C25 1.3880(18) .
C24 H24 0.9500 .
C25 C26 1.3834(15) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C31 C32 1.3864(14) .
C31 C36 1.3946(14) .
C32 C33 1.3987(15) .
C32 H32 0.9500 .
C33 C34 1.3751(19) .
C33 H33 0.9500 .
C34 C35 1.3825(19) .
C34 H34 0.9500 .
C35 C36 1.3883(14) .
C35 H35 0.9500 .
C36 H36 0.9500 .
C41 O4 1.305(2) .
C41 C43 1.3924(18) 2_656
C41 C42 1.394(2) .
C41 H41 0.9500 .
O4 C44 1.421(3) .
C44 H44A 0.9800 .
C44 H44B 0.9800 .
C44 H44C 0.9800 .
C43 C42 1.369(2) .
C43 H43 0.9500 .
C42 H42 0.9500 .
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_publ_flag
C32 H32 N1 0.95 2.45 2.8048(13) 102 yes
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 N1 C1 C11 66.76(10) . .
C2 N1 C1 C21 -53.66(10) . .
C2 N1 C1 C31 -174.30(8) . .
C1 N1 C2 C2 -169.44(10) . 2_666
N1 C1 C11 C12 -110.47(10) . .
C21 C1 C11 C12 11.45(12) . .
C31 C1 C11 C12 130.68(9) . .
N1 C1 C11 C16 68.49(11) . .
C21 C1 C11 C16 -169.59(9) . .
C31 C1 C11 C16 -50.36(12) . .
C22 O1 C12 C11 -8.41(15) . .
C22 O1 C12 C13 172.20(10) . .
C16 C11 C12 O1 179.11(10) . .
C1 C11 C12 O1 -1.90(15) . .
C16 C11 C12 C13 -1.54(16) . .
C1 C11 C12 C13 177.45(10) . .
O1 C12 C13 C14 -179.76(11) . .
C11 C12 C13 C14 0.84(18) . .
C12 C13 C14 C15 0.47(19) . .
C13 C14 C15 C16 -1.0(2) . .
C14 C15 C16 C11 0.27(19) . .
C12 C11 C16 C15 0.99(16) . .
C1 C11 C16 C15 -178.02(10) . .
N1 C1 C21 C22 107.48(10) . .
C11 C1 C21 C22 -12.28(12) . .
C31 C1 C21 C22 -131.74(9) . .
N1 C1 C21 C26 -68.77(11) . .
C11 C1 C21 C26 171.47(8) . .
C31 C1 C21 C26 52.00(11) . .
C12 O1 C22 C21 7.50(15) . .
C12 O1 C22 C23 -172.54(9) . .
C26 C21 C22 O1 -179.99(9) . .
C1 C21 C22 O1 3.65(15) . .
C26 C21 C22 C23 0.06(15) . .
C1 C21 C22 C23 -176.31(9) . .
O1 C22 C23 C24 -179.59(10) . .
C21 C22 C23 C24 0.36(16) . .
C22 C23 C24 C25 -0.40(17) . .
C23 C24 C25 C26 0.03(18) . .
C24 C25 C26 C21 0.41(17) . .
C22 C21 C26 C25 -0.44(15) . .
C1 C21 C26 C25 175.99(9) . .
N1 C1 C31 C32 5.30(13) . .
C11 C1 C31 C32 123.53(10) . .
C21 C1 C31 C32 -117.02(10) . .
N1 C1 C31 C36 -175.39(8) . .
C11 C1 C31 C36 -57.17(11) . .
C21 C1 C31 C36 62.29(11) . .
C36 C31 C32 C33 -0.30(16) . .
C1 C31 C32 C33 179.00(10) . .
C31 C32 C33 C34 0.86(18) . .
C32 C33 C34 C35 -0.70(18) . .
C33 C34 C35 C36 0.00(18) . .
C34 C35 C36 C31 0.56(17) . .
C32 C31 C36 C35 -0.40(16) . .
C1 C31 C36 C35 -179.74(10) . .
C43 C41 O4 C44 167.8(2) 2_656 .
C42 C41 O4 C44 -13.3(3) . .
C41 C43 C42 C41 -0.1(2) 2_656 .
O4 C41 C42 C43 -178.84(15) . .
C43 C41 C42 C43 0.1(2) 2_656 .
