#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:15:22 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223464 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/29/7232942.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_7232942
loop_
_publ_author_name
'Barton, Benita'
'de Jager, Lize'
'Hosten, Eric C.'
_publ_section_title
;
 Comparing the host behaviour of
 N,N′-bis(9-phenyl-9-thioxanthenyl)ethylenediamine and
 N,N′-bis(9-phenyl-9-xanthenyl)ethylenediamine in the presence of
 various alkylated aromatic and aniline guests: crystal engineering
 considerations
;
_journal_issue                   29
_journal_name_full               CrystEngComm
_journal_page_first              4387
_journal_paper_doi               10.1039/C9CE00823C
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C40 H32 N2 O2, C9 H12'
_chemical_formula_sum            'C49 H44 N2 O2'
_chemical_formula_weight         692.86
_chemical_melting_point          488.15
_chemical_name_common
'N,N-bis(9-phenyl-9-xanthenyl)ethylenediamine: cumene (1:1)'
_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
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-03-27 deposited with the CCDC.    2019-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                109.272(2)
_cell_angle_beta                 92.888(2)
_cell_angle_gamma                97.644(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1545(5)
_cell_length_b                   14.6714(7)
_cell_length_c                   15.1254(8)
_cell_measurement_reflns_used    9736
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.19
_cell_measurement_theta_min      2.26
_cell_volume                     1890.93(17)
_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-2018/2 (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 0.989
_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  0.0217
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            53340
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.364
_diffrn_reflns_theta_min         2.256
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9487
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.582
_exptl_crystal_size_mid          0.241
_exptl_crystal_size_min          0.154
_refine_diff_density_max         0.843
_refine_diff_density_min         -0.683
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         9360
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0667
_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)+(0.1016P)²+1.1407P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1855
_refine_ls_wR_factor_ref         0.2038
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7030
_reflns_number_total             9360
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce00823c2.cif
_cod_data_source_block           ia252
_cod_depositor_comments
'Adding full bibliography for 7232939--7232944.cif.'
_cod_original_cell_volume        1890.92(17)
_cod_database_code               7232942
_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   0.958
_shelx_estimated_absorpt_t_max   0.989
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 0.66551(15) 0.04462(11) 0.31756(12) 0.0441(4) Uani 1 1 d . . . . .
O2 O 0.12076(16) 0.55203(11) 0.22432(11) 0.0479(4) Uani 1 1 d . . . . .
N1 N 0.47200(17) 0.10617(11) 0.10316(10) 0.0290(3) Uani 1 1 d . . . . .
N2 N -0.04498(18) 0.60699(12) 0.47092(12) 0.0311(3) Uani 1 1 d . . . . .
C11 C 0.50798(18) 0.14042(12) 0.20640(11) 0.0255(3) Uani 1 1 d . . . . .
C12 C 0.5257(2) 0.01546(13) 0.05197(12) 0.0309(4) Uani 1 1 d . . . . .
H12A H 0.487351 -0.036667 0.076766 0.037 Uiso 1 1 calc R U . . .
H12B H 0.635270 0.025683 0.061107 0.037 Uiso 1 1 calc R U . . .
C21 C -0.02331(18) 0.64721(12) 0.39420(12) 0.0264(3) Uani 1 1 d . . . . .
C22 C 0.0229(2) 0.52031(14) 0.46205(15) 0.0372(4) Uani 1 1 d . . . . .
H22A H 0.132110 0.537610 0.468119 0.045 Uiso 1 1 calc R U . . .
H22B H -0.008934 0.470275 0.399294 0.045 Uiso 1 1 calc R U . . .
C111 C 0.43427(19) 0.06315(12) 0.24392(11) 0.0264(3) Uani 1 1 d . . . . .
C112 C 0.5141(2) 0.02092(13) 0.29558(13) 0.0316(4) Uani 1 1 d . . . . .
C113 C 0.4456(2) -0.05043(15) 0.32840(15) 0.0403(4) Uani 1 1 d . . . . .
H113 H 0.502472 -0.078013 0.364340 0.048 Uiso 1 1 calc R U . . .
C114 C 0.2954(2) -0.08080(14) 0.30854(15) 0.0402(4) Uani 1 1 d . . . . .
H114 H 0.248247 -0.129918 0.330332 0.048 Uiso 1 1 calc R U . . .
C115 C 0.2126(2) -0.04002(14) 0.25692(14) 0.0374(4) Uani 1 1 d . . . . .
H115 H 0.108746 -0.060969 0.243140 0.045 Uiso 1 1 calc R U . . .
C116 C 0.2819(2) 0.03131(13) 0.22552(13) 0.0325(4) Uani 1 1 d . . . . .
H116 H 0.224253 0.059421 0.190513 0.039 Uiso 1 1 calc R U . . .
C121 C 0.67499(19) 0.15911(12) 0.23288(11) 0.0269(3) Uani 1 1 d . . . . .
C122 C 0.74272(19) 0.11125(12) 0.28421(13) 0.0301(4) Uani 1 1 d . . . . .
C123 C 0.8956(2) 0.12935(14) 0.30737(15) 0.0382(4) Uani 1 1 d . . . . .
H123 H 0.939872 0.095150 0.342284 0.046 Uiso 1 1 calc R U . . .
C124 C 0.9821(2) 0.19699(16) 0.27941(15) 0.0410(4) Uani 1 1 d . . . . .
H124 H 1.086391 0.209374 0.294651 0.049 Uiso 1 1 calc R U . . .
C125 C 0.9168(2) 0.24698(17) 0.22904(16) 0.0467(5) Uani 1 1 d . . . . .
H125 H 0.975935 0.294176 0.210054 0.056 Uiso 1 1 calc R U . . .
C126 C 0.7652(2) 0.22792(16) 0.20651(15) 0.0400(4) Uani 1 1 d . . . . .
H126 H 0.721236 0.262718 0.172080 0.048 Uiso 1 1 calc R U . . .
C131 C 0.4468(2) 0.23609(13) 0.25070(13) 0.0322(4) Uani 1 1 d . . . . .
C132 C 0.4867(3) 0.28853(16) 0.34524(16) 0.0537(6) Uani 1 1 d . . . . .
H132 H 0.551525 0.265052 0.380674 0.064 Uiso 1 1 calc R U . . .
C133 C 0.4334(4) 0.37467(19) 0.3889(2) 0.0727(9) Uani 1 1 d . . . . .
H133 H 0.460309 0.409104 0.454130 0.087 Uiso 1 1 calc R U . . .
C134 C 0.3418(3) 0.41047(18) 0.3382(2) 0.0694(9) Uani 1 1 d . . . . .
H134 H 0.307176 0.470399 0.367774 0.083 Uiso 1 1 calc R U . . .
C135 C 0.3008(3) 0.35940(17) 0.2450(2) 0.0600(7) Uani 1 1 d . . . . .
H135 H 0.236858 0.383817 0.209877 0.072 Uiso 1 1 calc R U . . .
C136 C 0.3520(2) 0.27158(15) 0.20080(18) 0.0428(5) Uani 1 1 d . . . . .
H136 H 0.321510 0.236105 0.136169 0.051 Uiso 1 1 calc R U . . .
C211 C 0.14073(19) 0.67122(13) 0.38168(13) 0.0282(3) Uani 1 1 d . . . . .
C212 C 0.2017(2) 0.62323(13) 0.30096(14) 0.0334(4) Uani 1 1 d . . . . .
C213 C 0.3525(2) 0.64397(16) 0.29177(17) 0.0443(5) Uani 1 1 d . . . . .
H213 H 0.392158 0.609397 0.235781 0.053 Uiso 1 1 calc R U . . .
C214 C 0.4430(2) 0.71438(16) 0.36382(17) 0.0444(5) Uani 1 1 d . . . . .
H214 H 0.545630 0.728711 0.357927 0.053 Uiso 1 1 calc R U . . .
C215 C 0.3847(2) 0.76442(17) 0.44497(16) 0.0436(5) Uani 1 1 d . . . . .
H215 H 0.446887 0.813580 0.494892 0.052 Uiso 1 1 calc R U . . .
C216 C 0.2352(2) 0.74272(15) 0.45337(14) 0.0374(4) Uani 1 1 d . . . . .
H216 H 0.196158 0.777525 0.509512 0.045 Uiso 1 1 calc R U . . .
C221 C -0.10359(19) 0.57312(12) 0.30347(13) 0.0291(4) Uani 1 1 d . . . . .
C222 C -0.0301(2) 0.53126(13) 0.22596(14) 0.0345(4) Uani 1 1 d . . . . .
C223 C -0.1048(3) 0.46389(15) 0.14300(16) 0.0457(5) Uani 1 1 d . . . . .
H223 H -0.051950 0.435773 0.090903 0.055 Uiso 1 1 calc R U . . .
C224 C -0.2559(3) 0.43839(15) 0.13712(17) 0.0484(5) Uani 1 1 d . . . . .
H224 H -0.308067 0.393363 0.080306 0.058 Uiso 1 1 calc R U . . .
C225 C -0.3326(2) 0.47820(16) 0.21392(18) 0.0481(5) Uani 1 1 d . . . . .
H225 H -0.436931 0.460034 0.210175 0.058 Uiso 1 1 calc R U . . .
C226 C -0.2564(2) 0.54412(14) 0.29539(16) 0.0399(4) Uani 1 1 d . . . . .
H226 H -0.309507 0.570742 0.347830 0.048 Uiso 1 1 calc R U . . .
C231 C -0.09191(18) 0.74170(12) 0.41806(12) 0.0261(3) Uani 1 1 d . . . . .
C232 C -0.0707(2) 0.79947(14) 0.36163(15) 0.0373(4) Uani 1 1 d . . . . .
H232 H -0.016578 0.779169 0.308427 0.045 Uiso 1 1 calc R U . . .
C233 C -0.1272(2) 0.88589(15) 0.38200(17) 0.0451(5) Uani 1 1 d . . . . .
H233 H -0.113377 0.923924 0.342106 0.054 Uiso 1 1 calc R U . . .
C234 C -0.2039(2) 0.91750(14) 0.46014(16) 0.0406(5) Uani 1 1 d . . . . .
H234 H -0.239037 0.978387 0.475635 0.049 Uiso 1 1 calc R U . . .
C235 C -0.2286(2) 0.85997(14) 0.51510(14) 0.0352(4) Uani 1 1 d . . . . .
H235 H -0.283119 0.880539 0.568047 0.042 Uiso 1 1 calc R U . . .
C236 C -0.17428(19) 0.77167(13) 0.49379(13) 0.0302(4) Uani 1 1 d . . . . .
H236 H -0.193909 0.731768 0.531476 0.036 Uiso 1 1 calc R U . . .
H1 H 0.517(3) 0.159(2) 0.089(2) 0.075(9) Uiso 1 1 d . . . . .
H2 H -0.006(3) 0.6535(19) 0.5258(19) 0.047(7) Uiso 1 1 d . . . . .
C31 C 0.8664(4) 0.7513(4) 0.0805(3) 0.0920(9) Uani 0.648(7) 1 d DG . P A 1
C32 C 0.8804(5) 0.8266(4) 0.0434(3) 0.0920(9) Uani 0.648(7) 1 d DG . P A 1
H32 H 0.796618 0.855705 0.034605 0.110 Uiso 0.648(7) 1 calc R U P A 1
C33 C 1.0170(6) 0.8594(3) 0.0191(3) 0.0920(9) Uani 0.648(7) 1 d DG . P A 1
H33 H 1.026555 0.910876 -0.006239 0.110 Uiso 0.648(7) 1 calc R U P A 1
C34 C 1.1396(4) 0.8168(4) 0.0320(3) 0.0920(9) Uani 0.648(7) 1 d DG . P A 1
H34 H 1.232967 0.839233 0.015394 0.110 Uiso 0.648(7) 1 calc R U P A 1
C35 C 1.1256(4) 0.7415(4) 0.0691(3) 0.0920(9) Uani 0.648(7) 1 d DG . P A 1
H35 H 1.209442 0.712418 0.077872 0.110 Uiso 0.648(7) 1 calc R U P A 1
C36 C 0.9891(5) 0.7087(3) 0.0934(3) 0.0920(9) Uani 0.648(7) 1 d DG . P A 1
H36 H 0.979505 0.657246 0.118717 0.110 Uiso 0.648(7) 1 calc R U P A 1
C37 C 0.7200(7) 0.7096(4) 0.1071(4) 0.0920(9) Uani 0.648(7) 1 d D . P A 1
H37 H 0.741754 0.688751 0.162342 0.110 Uiso 0.648(7) 1 calc R U P A 1
C38 C 0.6364(8) 0.6268(5) 0.0326(4) 0.0920(9) Uani 0.648(7) 1 d D . P A 1
H38A H 0.608039 0.647092 -0.020555 0.138 Uiso 0.648(7) 1 calc R U P A 1
H38B H 0.547106 0.602037 0.055998 0.138 Uiso 0.648(7) 1 calc R U P A 1
H38C H 0.697487 0.575022 0.011861 0.138 Uiso 0.648(7) 1 calc R U P A 1
C39 C 0.6231(7) 0.7948(5) 0.1383(4) 0.0920(9) Uani 0.648(7) 1 d D . P A 1
H39A H 0.591768 0.811449 0.083335 0.138 Uiso 0.648(7) 1 calc R U P A 1
H39B H 0.682073 0.852544 0.185565 0.138 Uiso 0.648(7) 1 calc R U P A 1
H39C H 0.535489 0.773022 0.165125 0.138 Uiso 0.648(7) 1 calc R U P A 1
C41 C 0.8720(6) 0.7497(6) 0.0665(5) 0.0744(14) Uani 0.352(7) 1 d DG . P A 2
C42 C 0.9293(8) 0.8152(5) 0.0236(5) 0.0744(14) Uani 0.352(7) 1 d DG . P A 2
H42 H 0.865100 0.849129 -0.000485 0.089 Uiso 0.352(7) 1 calc R U P A 2
C43 C 1.0805(8) 0.8311(5) 0.0161(5) 0.0744(14) Uani 0.352(7) 1 d DG . P A 2
H43 H 1.119696 0.875887 -0.013255 0.089 Uiso 0.352(7) 1 calc R U P A 2
C44 C 1.1745(6) 0.7815(6) 0.0514(5) 0.0744(14) Uani 0.352(7) 1 d DG . P A 2
H44 H 1.277844 0.792323 0.046171 0.089 Uiso 0.352(7) 1 calc R U P A 2
C45 C 1.1172(7) 0.7159(5) 0.0942(5) 0.0744(14) Uani 0.352(7) 1 d DG . P A 2
H45 H 1.181399 0.682001 0.118368 0.089 Uiso 0.352(7) 1 calc R U P A 2
C46 C 0.9660(8) 0.7000(5) 0.1018(5) 0.0744(14) Uani 0.352(7) 1 d DG . P A 2
H46 H 0.926804 0.655241 0.131139 0.089 Uiso 0.352(7) 1 calc R U P A 2
C47 C 0.7016(10) 0.7300(6) 0.0589(6) 0.0744(14) Uani 0.352(7) 1 d D . P A 2
H47 H 0.659458 0.769088 0.023773 0.089 Uiso 0.352(7) 1 calc R U P A 2
C48 C 0.6593(13) 0.6154(7) -0.0001(6) 0.0744(14) Uani 0.352(7) 1 d D . P A 2
H48A H 0.640193 0.606155 -0.067036 0.112 Uiso 0.352(7) 1 calc R U P A 2
H48B H 0.570390 0.588213 0.021861 0.112 Uiso 0.352(7) 1 calc R U P A 2
H48C H 0.741613 0.581892 0.008975 0.112 Uiso 0.352(7) 1 calc R U P A 2
C49 C 0.6377(12) 0.7510(7) 0.1572(6) 0.0744(14) Uani 0.352(7) 1 d D . P A 2
H49A H 0.673301 0.819052 0.196793 0.112 Uiso 0.352(7) 1 calc R U P A 2
H49B H 0.670867 0.707126 0.188047 0.112 Uiso 0.352(7) 1 calc R U P A 2
H49C H 0.529235 0.739945 0.147916 0.112 Uiso 0.352(7) 1 calc R U P 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 0.0000 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
C122 O1 C112 118.82(14) . .
C212 O2 C222 118.48(14) . .
C12 N1 C11 114.62(13) . .
C12 N1 H1 112(2) . .
C11 N1 H1 101(2) . .
C22 N2 C21 115.00(14) . .
C22 N2 H2 107.8(16) . .
C21 N2 H2 108.6(16) . .
N1 C11 C111 108.71(13) . .
N1 C11 C121 111.26(13) . .
C111 C11 C121 109.91(13) . .
N1 C11 C131 109.06(14) . .
C111 C11 C131 109.09(13) . .
C121 C11 C131 108.78(14) . .
N1 C12 C12 109.76(18) . 2_655
N1 C12 H12A 109.7 . .
C12 C12 H12A 109.7 2_655 .
N1 C12 H12B 109.7 . .
C12 C12 H12B 109.7 2_655 .
H12A C12 H12B 108.2 . .
N2 C21 C221 108.56(14) . .
N2 C21 C211 112.36(14) . .
C221 C21 C211 109.76(14) . .
N2 C21 C231 108.15(13) . .
C221 C21 C231 109.19(13) . .
C211 C21 C231 108.77(13) . .
N2 C22 C22 109.57(18) . 2_566
N2 C22 H22A 109.8 . .
C22 C22 H22A 109.8 2_566 .
N2 C22 H22B 109.8 . .
C22 C22 H22B 109.8 2_566 .
H22A C22 H22B 108.2 . .
C112 C111 C116 117.44(16) . .
C112 C111 C11 122.17(15) . .
C116 C111 C11 120.38(15) . .
O1 C112 C111 123.38(16) . .
O1 C112 C113 115.03(16) . .
C111 C112 C113 121.58(17) . .
C114 C113 C112 119.61(18) . .
C114 C113 H113 120.2 . .
C112 C113 H113 120.2 . .
C113 C114 C115 120.13(18) . .
C113 C114 H114 119.9 . .
C115 C114 H114 119.9 . .
C116 C115 C114 119.60(18) . .
C116 C115 H115 120.2 . .
C114 C115 H115 120.2 . .
C115 C116 C111 121.63(17) . .
C115 C116 H116 119.2 . .
C111 C116 H116 119.2 . .
C122 C121 C126 117.38(16) . .
C122 C121 C11 122.65(15) . .
C126 C121 C11 119.96(16) . .
O1 C122 C121 123.01(16) . .
O1 C122 C123 115.35(16) . .
C121 C122 C123 121.63(17) . .
C124 C123 C122 119.67(19) . .
C124 C123 H123 120.2 . .
C122 C123 H123 120.2 . .
C123 C124 C125 119.87(18) . .
C123 C124 H124 120.1 . .
C125 C124 H124 120.1 . .
C126 C125 C124 119.67(19) . .
C126 C125 H125 120.2 . .
C124 C125 H125 120.2 . .
C125 C126 C121 121.77(19) . .
C125 C126 H126 119.1 . .
C121 C126 H126 119.1 . .
C136 C131 C132 118.40(19) . .
C136 C131 C11 122.97(18) . .
C132 C131 C11 118.62(18) . .
C131 C132 C133 121.0(3) . .
C131 C132 H132 119.5 . .
C133 C132 H132 119.5 . .
C134 C133 C132 120.2(3) . .
C134 C133 H133 119.9 . .
C132 C133 H133 119.9 . .
C135 C134 C133 119.6(2) . .
C135 C134 H134 120.2 . .
C133 C134 H134 120.2 . .
C134 C135 C136 120.6(3) . .
C134 C135 H135 119.7 . .
C136 C135 H135 119.7 . .
C131 C136 C135 120.3(2) . .
C131 C136 H136 119.9 . .
C135 C136 H136 119.9 . .
C212 C211 C216 117.23(17) . .
C212 C211 C21 122.38(16) . .
C216 C211 C21 120.38(16) . .
O2 C212 C211 123.27(16) . .
O2 C212 C213 115.06(17) . .
C211 C212 C213 121.67(19) . .
C214 C213 C212 119.8(2) . .
C214 C213 H213 120.1 . .
C212 C213 H213 120.1 . .
C213 C214 C215 119.82(19) . .
C213 C214 H214 120.1 . .
C215 C214 H214 120.1 . .
C214 C215 C216 119.8(2) . .
C214 C215 H215 120.1 . .
C216 C215 H215 120.1 . .
C215 C216 C211 121.69(19) . .
C215 C216 H216 119.2 . .
C211 C216 H216 119.2 . .
C222 C221 C226 117.13(17) . .
C222 C221 C21 122.30(16) . .
C226 C221 C21 120.57(16) . .
O2 C222 C221 123.45(17) . .
O2 C222 C223 114.70(17) . .
C221 C222 C223 121.85(18) . .
C224 C223 C222 119.4(2) . .
C224 C223 H223 120.3 . .
C222 C223 H223 120.3 . .
C223 C224 C225 120.2(2) . .
C223 C224 H224 119.9 . .
C225 C224 H224 119.9 . .
C226 C225 C224 119.4(2) . .
C226 C225 H225 120.3 . .
C224 C225 H225 120.3 . .
C225 C226 C221 122.01(19) . .
C225 C226 H226 119.0 . .
C221 C226 H226 119.0 . .
C236 C231 C232 118.47(16) . .
C236 C231 C21 122.51(15) . .
C232 C231 C21 119.02(15) . .
C233 C232 C231 120.79(18) . .
C233 C232 H232 119.6 . .
C231 C232 H232 119.6 . .
C232 C233 C234 120.40(19) . .
C232 C233 H233 119.8 . .
C234 C233 H233 119.8 . .
C235 C234 C233 119.32(17) . .
C235 C234 H234 120.3 . .
C233 C234 H234 120.3 . .
C234 C235 C236 120.50(18) . .
C234 C235 H235 119.8 . .
C236 C235 H235 119.8 . .
C231 C236 C235 120.44(17) . .
C231 C236 H236 119.8 . .
C235 C236 H236 119.8 . .
C32 C31 C36 120.0 . .
C32 C31 C37 123.3(4) . .
C36 C31 C37 116.7(4) . .
C33 C32 C31 120.0 . .
C33 C32 H32 120.0 . .
C31 C32 H32 120.0 . .
C34 C33 C32 120.0 . .
C34 C33 H33 120.0 . .
C32 C33 H33 120.0 . .
C33 C34 C35 120.0 . .
C33 C34 H34 120.0 . .
C35 C34 H34 120.0 . .
C34 C35 C36 120.0 . .
C34 C35 H35 120.0 . .
C36 C35 H35 120.0 . .
C35 C36 C31 120.0 . .
C35 C36 H36 120.0 . .
C31 C36 H36 120.0 . .
C38 C37 C31 114.3(5) . .
C38 C37 C39 109.5(6) . .
C31 C37 C39 107.9(5) . .
C38 C37 H37 108.3 . .
C31 C37 H37 108.3 . .
C39 C37 H37 108.3 . .
C37 C38 H38A 109.5 . .
C37 C38 H38B 109.5 . .
H38A C38 H38B 109.5 . .
C37 C38 H38C 109.5 . .
H38A C38 H38C 109.5 . .
H38B C38 H38C 109.5 . .
C37 C39 H39A 109.5 . .
C37 C39 H39B 109.5 . .
H39A C39 H39B 109.5 . .
C37 C39 H39C 109.5 . .
H39A C39 H39C 109.5 . .
H39B C39 H39C 109.5 . .
C42 C41 C46 120.0 . .
C42 C41 C47 114.1(6) . .
C46 C41 C47 125.4(6) . .
C41 C42 C43 120.0 . .
C41 C42 H42 120.0 . .
C43 C42 H42 120.0 . .
C44 C43 C42 120.0 . .
C44 C43 H43 120.0 . .
C42 C43 H43 120.0 . .
C43 C44 C45 120.0 . .
C43 C44 H44 120.0 . .
C45 C44 H44 120.0 . .
C46 C45 C44 120.0 . .
C46 C45 H45 120.0 . .
C44 C45 H45 120.0 . .
C45 C46 C41 120.0 . .
C45 C46 H46 120.0 . .
C41 C46 H46 120.0 . .
C41 C47 C49 113.3(7) . .
C41 C47 C48 104.2(8) . .
C49 C47 C48 108.8(7) . .
C41 C47 H47 110.1 . .
C49 C47 H47 110.1 . .
C48 C47 H47 110.1 . .
C47 C48 H48A 109.5 . .
C47 C48 H48B 109.5 . .
H48A C48 H48B 109.5 . .
C47 C48 H48C 109.5 . .
H48A C48 H48C 109.5 . .
H48B C48 H48C 109.5 . .
C47 C49 H49A 109.5 . .
C47 C49 H49B 109.5 . .
H49A C49 H49B 109.5 . .
C47 C49 H49C 109.5 . .
H49A C49 H49C 109.5 . .
H49B C49 H49C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C122 1.374(2) .
O1 C112 1.379(2) .
O2 C212 1.376(2) .
O2 C222 1.378(2) .
N1 C12 1.464(2) .
N1 C11 1.478(2) .
N1 H1 0.92(3) .
N2 C22 1.458(2) .
N2 C21 1.476(2) .
N2 H2 0.90(3) .
C11 C111 1.524(2) .
C11 C121 1.526(2) .
C11 C131 1.536(2) .
C12 C12 1.515(3) 2_655
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C21 C221 1.519(2) .
C21 C211 1.532(2) .
C21 C231 1.540(2) .
C22 C22 1.511(3) 2_566
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C111 C112 1.382(2) .
C111 C116 1.394(2) .
C112 C113 1.391(3) .
C113 C114 1.374(3) .
C113 H113 0.9500 .
C114 C115 1.382(3) .
C114 H114 0.9500 .
C115 C116 1.380(3) .
C115 H115 0.9500 .
C116 H116 0.9500 .
C121 C122 1.381(2) .
C121 C126 1.392(2) .
C122 C123 1.394(3) .
C123 C124 1.375(3) .
C123 H123 0.9500 .
C124 C125 1.384(3) .
C124 H124 0.9500 .
C125 C126 1.381(3) .
C125 H125 0.9500 .
C126 H126 0.9500 .
C131 C136 1.381(3) .
C131 C132 1.384(3) .
C132 C133 1.384(3) .
C132 H132 0.9500 .
C133 C134 1.373(5) .
C133 H133 0.9500 .
C134 C135 1.366(5) .
C134 H134 0.9500 .
C135 C136 1.397(3) .
C135 H135 0.9500 .
C136 H136 0.9500 .
C211 C212 1.380(3) .
C211 C216 1.392(3) .
C212 C213 1.397(3) .
C213 C214 1.371(3) .
C213 H213 0.9500 .
C214 C215 1.381(3) .
C214 H214 0.9500 .
C215 C216 1.385(3) .
C215 H215 0.9500 .
C216 H216 0.9500 .
C221 C222 1.385(3) .
C221 C226 1.394(3) .
C222 C223 1.391(3) .
C223 C224 1.375(3) .
C223 H223 0.9500 .
C224 C225 1.388(3) .
C224 H224 0.9500 .
C225 C226 1.374(3) .
C225 H225 0.9500 .
C226 H226 0.9500 .
C231 C236 1.385(2) .
C231 C232 1.391(2) .
C232 C233 1.380(3) .
C232 H232 0.9500 .
C233 C234 1.383(3) .
C233 H233 0.9500 .
C234 C235 1.373(3) .
C234 H234 0.9500 .
C235 C236 1.393(2) .
C235 H235 0.9500 .
C236 H236 0.9500 .
C31 C32 1.3900 .
C31 C36 1.3900 .
C31 C37 1.527(6) .
C32 C33 1.3900 .
C32 H32 0.9500 .
C33 C34 1.3900 .
C33 H33 0.9500 .
C34 C35 1.3900 .
C34 H34 0.9500 .
C35 C36 1.3900 .
C35 H35 0.9500 .
C36 H36 0.9500 .
C37 C38 1.448(7) .
C37 C39 1.587(8) .
C37 H37 1.0000 .
C38 H38A 0.9800 .
C38 H38B 0.9800 .
C38 H38C 0.9800 .
C39 H39A 0.9800 .
C39 H39B 0.9800 .
C39 H39C 0.9800 .
C41 C42 1.3900 .
C41 C46 1.3900 .
C41 C47 1.539(9) .
C42 C43 1.3900 .
C42 H42 0.9500 .
C43 C44 1.3900 .
C43 H43 0.9500 .
C44 C45 1.3900 .
C44 H44 0.9500 .
C45 C46 1.3900 .
C45 H45 0.9500 .
C46 H46 0.9500 .
C47 C49 1.575(11) .
C47 C48 1.604(11) .
C47 H47 1.0000 .
C48 H48A 0.9800 .
C48 H48B 0.9800 .
C48 H48C 0.9800 .
C49 H49A 0.9800 .
C49 H49B 0.9800 .
C49 H49C 0.9800 .
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
C136 H136 N1 0.95 2.43 2.790(3) 102 yes
C236 H236 N2 0.95 2.39 2.758(2) 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_4
C12 N1 C11 C111 -61.74(18) .
C12 N1 C11 C121 59.43(19) .
C12 N1 C11 C131 179.42(14) .
C11 N1 C12 C12 176.55(17) 2_655
C22 N2 C21 C221 65.6(2) .
C22 N2 C21 C211 -56.0(2) .
C22 N2 C21 C231 -176.08(16) .
C21 N2 C22 C22 -173.2(2) 2_566
N1 C11 C111 C112 123.24(17) .
C121 C11 C111 C112 1.2(2) .
C131 C11 C111 C112 -117.94(18) .
N1 C11 C111 C116 -55.73(19) .
C121 C11 C111 C116 -177.73(15) .
C131 C11 C111 C116 63.1(2) .
C122 O1 C112 C111 -2.2(3) .
C122 O1 C112 C113 177.10(17) .
C116 C111 C112 O1 179.03(17) .
C11 C111 C112 O1 0.0(3) .
C116 C111 C112 C113 -0.2(3) .
C11 C111 C112 C113 -179.18(17) .
O1 C112 C113 C114 -178.62(18) .
C111 C112 C113 C114 0.6(3) .
C112 C113 C114 C115 -0.5(3) .
C113 C114 C115 C116 0.0(3) .
C114 C115 C116 C111 0.5(3) .
C112 C111 C116 C115 -0.4(3) .
C11 C111 C116 C115 178.62(16) .
N1 C11 C121 C122 -121.00(17) .
C111 C11 C121 C122 -0.5(2) .
C131 C11 C121 C122 118.84(17) .
N1 C11 C121 C126 60.1(2) .
C111 C11 C121 C126 -179.43(16) .
C131 C11 C121 C126 -60.1(2) .
C112 O1 C122 C121 2.9(3) .
C112 O1 C122 C123 -178.38(17) .
C126 C121 C122 O1 177.40(17) .
C11 C121 C122 O1 -1.5(3) .
C126 C121 C122 C123 -1.2(3) .
C11 C121 C122 C123 179.83(16) .
O1 C122 C123 C124 -178.19(18) .
C121 C122 C123 C124 0.5(3) .
C122 C123 C124 C125 0.4(3) .
C123 C124 C125 C126 -0.5(3) .
C124 C125 C126 C121 -0.2(3) .
C122 C121 C126 C125 1.1(3) .
C11 C121 C126 C125 -179.97(19) .
N1 C11 C131 C136 10.3(2) .
C111 C11 C131 C136 -108.27(19) .
C121 C11 C131 C136 131.85(18) .
N1 C11 C131 C132 -170.64(18) .
C111 C11 C131 C132 70.8(2) .
C121 C11 C131 C132 -49.1(2) .
C136 C131 C132 C133 -0.2(3) .
C11 C131 C132 C133 -179.3(2) .
C131 C132 C133 C134 -1.2(4) .
C132 C133 C134 C135 1.5(4) .
C133 C134 C135 C136 -0.4(4) .
C132 C131 C136 C135 1.3(3) .
C11 C131 C136 C135 -179.66(18) .
C134 C135 C136 C131 -1.0(3) .
N2 C21 C211 C212 115.50(18) .
C221 C21 C211 C212 -5.4(2) .
C231 C21 C211 C212 -124.80(17) .
N2 C21 C211 C216 -63.6(2) .
C221 C21 C211 C216 175.49(15) .
C231 C21 C211 C216 56.1(2) .
C222 O2 C212 C211 3.7(3) .
C222 O2 C212 C213 -176.48(18) .
C216 C211 C212 O2 -179.11(17) .
C21 C211 C212 O2 1.7(3) .
C216 C211 C212 C213 1.1(3) .
C21 C211 C212 C213 -178.05(17) .
O2 C212 C213 C214 179.45(19) .
C211 C212 C213 C214 -0.7(3) .
C212 C213 C214 C215 -0.1(3) .
C213 C214 C215 C216 0.4(3) .
C214 C215 C216 C211 0.0(3) .
C212 C211 C216 C215 -0.7(3) .
C21 C211 C216 C215 178.46(17) .
N2 C21 C221 C222 -118.90(17) .
C211 C21 C221 C222 4.3(2) .
C231 C21 C221 C222 123.41(17) .
N2 C21 C221 C226 60.8(2) .
C211 C21 C221 C226 -176.02(16) .
C231 C21 C221 C226 -56.9(2) .
C212 O2 C222 C221 -4.9(3) .
C212 O2 C222 C223 175.30(18) .
C226 C221 C222 O2 -179.13(18) .
C21 C221 C222 O2 0.6(3) .
C226 C221 C222 C223 0.6(3) .
C21 C221 C222 C223 -179.63(17) .
O2 C222 C223 C224 -179.7(2) .
C221 C222 C223 C224 0.5(3) .
C222 C223 C224 C225 -1.2(3) .
C223 C224 C225 C226 0.7(3) .
C224 C225 C226 C221 0.4(3) .
C222 C221 C226 C225 -1.1(3) .
C21 C221 C226 C225 179.16(18) .
N2 C21 C231 C236 -7.3(2) .
C221 C21 C231 C236 110.63(18) .
C211 C21 C231 C236 -129.61(17) .
N2 C21 C231 C232 172.67(16) .
C221 C21 C231 C232 -69.4(2) .
C211 C21 C231 C232 50.4(2) .
C236 C231 C232 C233 1.6(3) .
C21 C231 C232 C233 -178.39(18) .
C231 C232 C233 C234 1.2(3) .
C232 C233 C234 C235 -2.7(3) .
C233 C234 C235 C236 1.4(3) .
C232 C231 C236 C235 -2.9(3) .
C21 C231 C236 C235 177.11(16) .
C234 C235 C236 C231 1.4(3) .
C36 C31 C32 C33 0.0 .
C37 C31 C32 C33 -178.7(5) .
C31 C32 C33 C34 0.0 .
C32 C33 C34 C35 0.0 .
C33 C34 C35 C36 0.0 .
C34 C35 C36 C31 0.0 .
C32 C31 C36 C35 0.0 .
C37 C31 C36 C35 178.8(5) .
C32 C31 C37 C38 91.8(6) .
C36 C31 C37 C38 -86.9(6) .
C32 C31 C37 C39 -30.2(6) .
C36 C31 C37 C39 151.0(4) .
C46 C41 C42 C43 0.0 .
C47 C41 C42 C43 -172.8(7) .
C41 C42 C43 C44 0.0 .
C42 C43 C44 C45 0.0 .
C43 C44 C45 C46 0.0 .
C44 C45 C46 C41 0.0 .
C42 C41 C46 C45 0.0 .
C47 C41 C46 C45 171.9(7) .
C42 C41 C47 C49 -124.2(8) .
C46 C41 C47 C49 63.5(9) .
C42 C41 C47 C48 117.7(7) .
C46 C41 C47 C48 -54.7(8) .
