#------------------------------------------------------------------------------
#$Date: 2024-09-06 02:08:36 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294412 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/33/7133360.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_7133360
loop_
_publ_author_name
'Omura, Takumi'
'Morisako, Shogo'
'Isoda, Kyosuke'
_publ_section_title
;
 Amino acid-appended pyromellitic diimide liquid materials, their
 photoluminescence, and the thermal response that turns the
 photoluminescence off.
;
_journal_issue                   70
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9352
_journal_page_last               9355
_journal_paper_doi               10.1039/d4cc02229g
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C20 H20 N2 O8, C10 H8'
_chemical_formula_sum            'C30 H28 N2 O8'
_chemical_formula_weight         544.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-27
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-05-08 deposited with the CCDC.	2024-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.9480(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.55420(10)
_cell_length_b                   7.02420(10)
_cell_length_c                   24.7028(3)
_cell_measurement_reflns_used    16994
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.8730
_cell_measurement_theta_min      3.6060
_cell_volume                     1301.16(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -92.00  35.00   0.50    2.00    --    0.00 -32.00-166.00  254
  2  ω    -30.00 140.00   0.50    2.00    --   57.86  32.00  -6.00  340
  3  ω   -177.00 -23.00   0.50    2.00    -- -106.00 -32.00-166.00  308
  4  ω     28.00 178.00   0.50    2.00    --  115.73  32.00  -6.00  300
  5  ω    -33.00  83.00   0.50    2.00    --    0.00  32.00  -6.00  232
  6  ω     -1.00  58.00   0.50    2.00    --    0.00 -99.00-180.00  118
  7  ω    -86.00 -13.00   0.50    2.00    --  -57.86 125.00   0.00  146
  8  ω    -14.00  25.00   0.50    2.00    --  -57.86  15.00-180.00   78
  9  ω    -30.00  25.00   0.50    2.00    --  -57.86  30.00 120.00  110
 10  ω   -143.00 -73.00   0.50    2.00    --  -57.86-125.00 -90.00  140
 11  ω    -34.00  35.00   0.50    2.00    --   57.86 -32.00-166.00  138
 12  ω      1.00  31.00   0.50    2.00    --   57.86  95.00  40.23   60
 13  ω      1.00  31.00   0.50    2.00    --   57.86  95.00 -98.66   60
 14  ω      0.00  27.00   0.50    2.00    --   57.86  98.00   0.64   54
 15  ω      0.00  27.00   0.50    2.00    --   57.86  98.00 173.04   54
 16  ω      1.00  28.00   0.50    2.00    --   57.86  97.00 106.20   54
 17  ω     10.00 140.00   0.50    2.00    --   57.86  77.00  60.00  260
 18  ω      1.00  28.00   0.50    2.00    --   57.86  97.00 -36.49   54
 19  ω    -29.00  51.00   0.50    2.00    --   57.86 -45.00  60.00  160
 20  ω   -177.00 -58.00   0.50    2.00    -- -106.00 -77.00 150.00  238
 21  ω   -177.00 -59.00   0.50    2.00    -- -106.00 -75.00  63.83  236
 22  ω   -177.00 -58.00   0.50    2.00    -- -106.00 -77.00 120.00  238
 23  ω   -177.00 -58.00   0.50    2.00    -- -106.00 -77.00  90.00  238
 24  ω   -177.00 -59.00   0.50    2.00    -- -106.00 -76.00  96.31  236
 25  ω   -177.00 -58.00   0.50    2.00    -- -106.00 -77.00 129.81  238
 26  ω   -177.00 -58.00   0.50    2.00    -- -106.00 -77.00  60.00  238
 27  ω   -177.00 -61.00   0.50    2.00    -- -106.00 -72.00  68.99  232
 28  ω   -177.00 -59.00   0.50    2.00    -- -106.00 -75.00  44.95  236
 29  ω    -55.00 -23.00   0.50    2.00    -- -106.00  50.00   0.00   64
 30  ω   -177.00 -62.00   0.50    2.00    -- -106.00 -68.00 129.19  230
 31  ω   -177.00 -58.00   0.50    2.00    -- -106.00 -77.00 108.06  238
 32  ω   -177.00 -34.00   0.50    2.00    -- -106.00 -37.00  90.00  286
 33  ω    -55.00 -23.00   0.50    2.00    -- -106.00  50.00-180.00   64
 34  ω     27.00 108.00   0.50    2.00    --  115.73-111.00  60.00  162
 35  ω     42.00 178.00   0.50    2.00    --  115.73  37.00  60.00  272
 36  ω     74.00 178.00   0.50    2.00    --  115.73  63.00  60.00  208
 37  ω     19.00 164.00   0.50    2.00    --  115.73   0.00-180.00  290
 38  ω     44.00  85.00   0.50    2.00    --  115.73  37.00  60.00   82
 39  ω    129.00 168.00   0.50    2.00    --  115.73  77.00  30.00   78
 40  ω     76.00 106.00   0.50    2.00    --  115.73  77.00  30.00   60
 41  ω     31.00  56.00   0.50    2.00    --  115.73 -50.00   0.00   50
 42  ω     82.00 108.00   0.50    2.00    --  115.73-111.00-180.00   52
 43  ω    112.00 157.00   0.50    2.00    --  115.73 111.00-120.00   90
 44  ω     39.00  78.00   0.50    2.00    --  115.73 -63.00  60.00   78
 45  ω     40.00  66.00   0.50    2.00    --  115.73-111.00-180.00   52
 46  ω     30.00  78.00   0.50    2.00    --  115.73 -63.00 -60.00   96
 47  ω     31.00  57.00   0.50    2.00    --  115.73 -50.00  30.00   52
 48  ω     78.00 143.00   0.50    2.00    --  115.73  77.00  90.00  130
 49  ω    107.00 174.00   0.50    2.00    --  115.73   0.00 -90.00  134
 50  ω    140.00 178.00   0.50    2.00    --  115.73  77.00 120.00   76
 51  ω     82.00 125.00   0.50    2.00    --  115.73  77.00 120.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0974066000
_diffrn_orient_matrix_UB_12      -0.0053931000
_diffrn_orient_matrix_UB_13      0.0585352000
_diffrn_orient_matrix_UB_21      0.1661009000
_diffrn_orient_matrix_UB_22      0.0894564000
_diffrn_orient_matrix_UB_23      -0.0202927000
_diffrn_orient_matrix_UB_31      -0.0716694000
_diffrn_orient_matrix_UB_32      0.2000193000
_diffrn_orient_matrix_UB_33      0.0106621000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            19042
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.906
_diffrn_reflns_theta_min         3.605
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              PhotonJet-S
_exptl_absorpt_coefficient_mu    0.844
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.70a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       plate
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 2196 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5020
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0257
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0466P)²+0.1896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0698
_refine_ls_wR_factor_ref         0.0701
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                4953
_reflns_number_total             5020
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc02229g2.cif
_cod_data_source_block           omr003_2_autored
_cod_depositor_comments
'Adding full bibliography for 7133359--7133360.cif.'
_cod_database_code               7133360
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C30 H28 N2 O8'
_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_max   0.983
_shelx_estimated_absorpt_t_min   0.849
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C13(H13), C16(H16), C18(H18)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26),
 C27(H27), C28(H28)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
2.d Idealised tetrahedral OH refined as rotating group:
 O6(H6), O8(H8)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.358
_oxdiff_exptl_absorpt_empirical_full_min 0.690
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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 0.53828(15) 0.49483(19) 0.81645(5) 0.0243(3) Uani 1 1 d . . . . .
O2 O 1.09200(15) 0.34992(18) 0.90331(4) 0.0220(3) Uani 1 1 d . . . . .
O3 O 1.36723(14) 0.27046(18) 0.68571(4) 0.0218(3) Uani 1 1 d . . . . .
O4 O 0.81656(15) 0.42585(19) 0.59864(4) 0.0229(3) Uani 1 1 d . . . . .
O5 O 0.92986(16) 0.48132(18) 1.00600(5) 0.0224(3) Uani 1 1 d . . . . .
O6 O 0.84678(17) 0.71771(19) 0.94814(5) 0.0259(3) Uani 1 1 d . . . . .
H6 H 0.923360 0.779046 0.968626 0.039 Uiso 1 1 calc R U . . .
O7 O 1.00960(17) 0.25447(17) 0.49352(5) 0.0222(3) Uani 1 1 d . . . . .
O8 O 1.13530(17) 0.05822(17) 0.55797(5) 0.0233(3) Uani 1 1 d . . . . .
H8 H 1.084935 -0.024943 0.537049 0.035 Uiso 1 1 calc R U . . .
N1 N 0.79653(17) 0.4169(2) 0.87218(5) 0.0174(3) Uani 1 1 d . . . . .
N2 N 1.11216(17) 0.3683(2) 0.62946(5) 0.0161(3) Uani 1 1 d . . . . .
C1 C 0.7764(2) 0.4275(2) 0.72352(6) 0.0176(3) Uani 1 1 d . . . . .
H1 H 0.660668 0.455116 0.705722 0.021 Uiso 1 1 calc R U . . .
C2 C 0.81540(19) 0.4184(2) 0.77984(6) 0.0163(3) Uani 1 1 d . . . . .
C3 C 0.9844(2) 0.3753(2) 0.80611(6) 0.0160(3) Uani 1 1 d . . . . .
C4 C 1.1292(2) 0.3391(2) 0.77794(6) 0.0162(3) Uani 1 1 d . . . . .
H4 H 1.244779 0.310332 0.795697 0.019 Uiso 1 1 calc R U . . .
C5 C 1.0906(2) 0.3486(2) 0.72163(6) 0.0158(3) Uani 1 1 d . . . . .
C6 C 0.9218(2) 0.3924(2) 0.69556(6) 0.0161(3) Uani 1 1 d . . . . .
C7 C 0.6936(2) 0.4501(2) 0.82215(6) 0.0174(3) Uani 1 1 d . . . . .
C8 C 0.9753(2) 0.3761(2) 0.86620(6) 0.0170(3) Uani 1 1 d . . . . .
C9 C 1.2139(2) 0.3219(2) 0.67909(6) 0.0164(3) Uani 1 1 d . . . . .
C10 C 0.9326(2) 0.3996(2) 0.63606(6) 0.0170(3) Uani 1 1 d . . . . .
C11 C 0.7224(2) 0.4181(2) 0.92445(6) 0.0183(3) Uani 1 1 d . . . . .
H11 H 0.604264 0.483945 0.918518 0.022 Uiso 1 1 calc R U . . .
C12 C 0.8459(2) 0.5386(2) 0.96445(6) 0.0175(3) Uani 1 1 d . . . . .
C13 C 0.6899(2) 0.2153(3) 0.94410(6) 0.0205(3) Uani 1 1 d . . . . .
H13 H 0.806617 0.146566 0.949478 0.025 Uiso 1 1 calc R U . . .
C14 C 0.6096(3) 0.2149(3) 0.99835(7) 0.0295(4) Uani 1 1 d . . . . .
H14A H 0.679286 0.299324 1.024372 0.044 Uiso 1 1 calc R U . . .
H14B H 0.612218 0.085263 1.013088 0.044 Uiso 1 1 calc R U . . .
H14C H 0.485955 0.259847 0.992185 0.044 Uiso 1 1 calc R U . . .
C15 C 0.5638(2) 0.1078(3) 0.90150(7) 0.0245(4) Uani 1 1 d . . . . .
H15A H 0.445915 0.167857 0.897882 0.037 Uiso 1 1 calc R U . . .
H15B H 0.553675 -0.024838 0.913032 0.037 Uiso 1 1 calc R U . . .
H15C H 0.611247 0.111528 0.866295 0.037 Uiso 1 1 calc R U . . .
C16 C 1.1650(2) 0.3922(2) 0.57454(6) 0.0167(3) Uani 1 1 d . . . . .
H16 H 1.102000 0.508725 0.559011 0.020 Uiso 1 1 calc R U . . .
C17 C 1.0949(2) 0.2280(2) 0.53802(6) 0.0168(3) Uani 1 1 d . . . . .
C18 C 1.36554(19) 0.4287(2) 0.57295(6) 0.0176(3) Uani 1 1 d . . . . .
H18 H 1.435902 0.322137 0.591796 0.021 Uiso 1 1 calc R U . . .
C19 C 1.4046(2) 0.4401(3) 0.51346(7) 0.0227(3) Uani 1 1 d . . . . .
H19A H 1.368861 0.320722 0.494725 0.034 Uiso 1 1 calc R U . . .
H19B H 1.532464 0.461024 0.512562 0.034 Uiso 1 1 calc R U . . .
H19C H 1.337335 0.545987 0.495112 0.034 Uiso 1 1 calc R U . . .
C20 C 1.4180(2) 0.6158(3) 0.60207(7) 0.0204(3) Uani 1 1 d . . . . .
H20A H 1.349684 0.720522 0.583483 0.031 Uiso 1 1 calc R U . . .
H20B H 1.545685 0.638659 0.601462 0.031 Uiso 1 1 calc R U . . .
H20C H 1.392150 0.608328 0.639945 0.031 Uiso 1 1 calc R U . . .
C21 C -0.0649(3) 0.8894(3) 0.82108(7) 0.0269(4) Uani 1 1 d . . . . .
H21 H -0.158806 0.905854 0.842988 0.032 Uiso 1 1 calc R U . . .
C22 C 0.1040(3) 0.8588(3) 0.84549(7) 0.0315(4) Uani 1 1 d . . . . .
H22 H 0.127001 0.855659 0.884151 0.038 Uiso 1 1 calc R U . . .
C23 C 0.2449(3) 0.8318(3) 0.81384(8) 0.0320(4) Uani 1 1 d . . . . .
H23 H 0.362434 0.810855 0.831251 0.038 Uiso 1 1 calc R U . . .
C24 C 0.2134(2) 0.8355(3) 0.75800(8) 0.0274(4) Uani 1 1 d . . . . .
H24 H 0.309158 0.815194 0.737030 0.033 Uiso 1 1 calc R U . . .
C25 C 0.0025(2) 0.8770(3) 0.67356(7) 0.0262(4) Uani 1 1 d . . . . .
H25 H 0.096232 0.857675 0.651740 0.031 Uiso 1 1 calc R U . . .
C26 C -0.1663(3) 0.9119(3) 0.64908(7) 0.0300(4) Uani 1 1 d . . . . .
H26 H -0.189147 0.916182 0.610430 0.036 Uiso 1 1 calc R U . . .
C27 C -0.3074(2) 0.9417(3) 0.68090(8) 0.0304(4) Uani 1 1 d . . . . .
H27 H -0.424235 0.967259 0.663596 0.036 Uiso 1 1 calc R U . . .
C28 C -0.2759(2) 0.9338(3) 0.73652(8) 0.0270(4) Uani 1 1 d . . . . .
H28 H -0.371678 0.953273 0.757521 0.032 Uiso 1 1 calc R U . . .
C29 C -0.1031(2) 0.8971(2) 0.76335(7) 0.0221(3) Uani 1 1 d . . . . .
C30 C 0.0394(2) 0.8695(2) 0.73123(7) 0.0212(3) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_publ_flag
C12 O6 H6 109.5 . . ?
C17 O8 H8 109.5 . . ?
C7 N1 C8 112.33(12) . . ?
C7 N1 C11 123.09(13) . . ?
C8 N1 C11 124.55(13) . . ?
C9 N2 C16 130.63(13) . . ?
C10 N2 C9 111.70(12) . . ?
C10 N2 C16 117.65(12) . . ?
C2 C1 H1 123.0 . . ?
C2 C1 C6 113.93(14) . . ?
C6 C1 H1 123.0 . . ?
C1 C2 C3 123.23(14) . . ?
C1 C2 C7 128.45(14) . . ?
C3 C2 C7 108.32(13) . . ?
C2 C3 C8 108.18(13) . . ?
C4 C3 C2 122.62(14) . . ?
C4 C3 C8 129.20(14) . . ?
C3 C4 H4 122.9 . . ?
C5 C4 C3 114.22(14) . . ?
C5 C4 H4 122.9 . . ?
C4 C5 C6 122.99(14) . . ?
C4 C5 C9 128.58(14) . . ?
C6 C5 C9 108.41(13) . . ?
C1 C6 C5 122.99(14) . . ?
C1 C6 C10 128.95(14) . . ?
C5 C6 C10 108.03(13) . . ?
O1 C7 N1 125.16(14) . . ?
O1 C7 C2 129.14(14) . . ?
N1 C7 C2 105.70(12) . . ?
O2 C8 N1 125.05(14) . . ?
O2 C8 C3 129.56(14) . . ?
N1 C8 C3 105.39(13) . . ?
O3 C9 N2 127.12(14) . . ?
O3 C9 C5 127.68(14) . . ?
N2 C9 C5 105.19(13) . . ?
O4 C10 N2 123.83(14) . . ?
O4 C10 C6 129.94(14) . . ?
N2 C10 C6 106.23(12) . . ?
N1 C11 H11 107.6 . . ?
N1 C11 C12 107.65(13) . . ?
N1 C11 C13 111.45(13) . . ?
C12 C11 H11 107.6 . . ?
C12 C11 C13 114.69(13) . . ?
C13 C11 H11 107.6 . . ?
O5 C12 O6 123.66(15) . . ?
O5 C12 C11 125.52(15) . . ?
O6 C12 C11 110.81(13) . . ?
C11 C13 H13 108.6 . . ?
C11 C13 C14 111.90(14) . . ?
C14 C13 H13 108.6 . . ?
C15 C13 C11 110.52(13) . . ?
C15 C13 H13 108.6 . . ?
C15 C13 C14 108.68(14) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16 106.1 . . ?
N2 C16 C17 110.31(13) . . ?
N2 C16 C18 114.86(12) . . ?
C17 C16 H16 106.1 . . ?
C17 C16 C18 112.61(12) . . ?
C18 C16 H16 106.1 . . ?
O7 C17 O8 123.42(15) . . ?
O7 C17 C16 121.87(15) . . ?
O8 C17 C16 114.71(13) . . ?
C16 C18 H18 109.4 . . ?
C19 C18 C16 109.65(12) . . ?
C19 C18 H18 109.4 . . ?
C20 C18 C16 109.32(12) . . ?
C20 C18 H18 109.4 . . ?
C20 C18 C19 109.69(14) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 H21 119.5 . . ?
C22 C21 C29 121.09(16) . . ?
C29 C21 H21 119.5 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.43(17) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.35(18) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C30 120.69(17) . . ?
C30 C24 H24 119.7 . . ?
C26 C25 H25 119.6 . . ?
C26 C25 C30 120.70(17) . . ?
C30 C25 H25 119.6 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.44(17) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 120.0 . . ?
C28 C27 C26 120.08(17) . . ?
C28 C27 H27 120.0 . . ?
C27 C28 H28 119.4 . . ?
C27 C28 C29 121.15(17) . . ?
C29 C28 H28 119.4 . . ?
C21 C29 C30 118.54(15) . . ?
C28 C29 C21 122.76(16) . . ?
C28 C29 C30 118.70(16) . . ?
C24 C30 C25 122.20(16) . . ?
C24 C30 C29 118.88(15) . . ?
C25 C30 C29 118.92(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.206(2) . ?
O2 C8 1.207(2) . ?
O3 C9 1.205(2) . ?
O4 C10 1.2085(19) . ?
O5 C12 1.208(2) . ?
O6 H6 0.8400 . ?
O6 C12 1.322(2) . ?
O7 C17 1.219(2) . ?
O8 H8 0.8400 . ?
O8 C17 1.312(2) . ?
N1 C7 1.3978(19) . ?
N1 C8 1.4055(19) . ?
N1 C11 1.4686(18) . ?
N2 C9 1.4044(19) . ?
N2 C10 1.4033(19) . ?
N2 C16 1.4694(18) . ?
C1 H1 0.9500 . ?
C1 C2 1.388(2) . ?
C1 C6 1.389(2) . ?
C2 C3 1.394(2) . ?
C2 C7 1.490(2) . ?
C3 C4 1.389(2) . ?
C3 C8 1.494(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(2) . ?
C5 C6 1.391(2) . ?
C5 C9 1.498(2) . ?
C6 C10 1.483(2) . ?
C11 H11 1.0000 . ?
C11 C12 1.530(2) . ?
C11 C13 1.534(2) . ?
C13 H13 1.0000 . ?
C13 C14 1.536(2) . ?
C13 C15 1.530(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16 1.0000 . ?
C16 C17 1.520(2) . ?
C16 C18 1.541(2) . ?
C18 H18 1.0000 . ?
C18 C19 1.536(2) . ?
C18 C20 1.527(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C22 1.361(3) . ?
C21 C29 1.421(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.408(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.371(3) . ?
C24 H24 0.9500 . ?
C24 C30 1.418(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.366(3) . ?
C25 C30 1.419(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.414(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.367(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.414(2) . ?
C29 C30 1.426(2) . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C11 C12 O5 -116.98(17) . . . . ?
N1 C11 C12 O6 64.24(17) . . . . ?
N1 C11 C13 C14 -179.12(14) . . . . ?
N1 C11 C13 C15 -57.85(17) . . . . ?
N2 C16 C17 O7 128.29(15) . . . . ?
N2 C16 C17 O8 -52.48(17) . . . . ?
N2 C16 C18 C19 176.93(14) . . . . ?
N2 C16 C18 C20 -62.78(17) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C1 C2 C3 C8 -179.28(15) . . . . ?
C1 C2 C7 O1 -2.2(3) . . . . ?
C1 C2 C7 N1 177.74(16) . . . . ?
C1 C6 C10 O4 -5.0(3) . . . . ?
C1 C6 C10 N2 175.20(16) . . . . ?
C2 C1 C6 C5 1.2(2) . . . . ?
C2 C1 C6 C10 -176.57(15) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C2 C3 C8 O2 -178.31(18) . . . . ?
C2 C3 C8 N1 1.14(18) . . . . ?
C3 C2 C7 O1 177.94(18) . . . . ?
C3 C2 C7 N1 -2.16(18) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C3 C4 C5 C9 178.59(16) . . . . ?
C4 C3 C8 O2 1.9(3) . . . . ?
C4 C3 C8 N1 -178.65(16) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
C4 C5 C6 C10 177.04(15) . . . . ?
C4 C5 C9 O3 7.2(3) . . . . ?
C4 C5 C9 N2 -173.30(16) . . . . ?
C5 C6 C10 O4 176.99(18) . . . . ?
C5 C6 C10 N2 -2.83(17) . . . . ?
C6 C1 C2 C3 -0.9(2) . . . . ?
C6 C1 C2 C7 179.22(16) . . . . ?
C6 C5 C9 O3 -174.63(17) . . . . ?
C6 C5 C9 N2 4.92(17) . . . . ?
C7 N1 C8 O2 176.85(17) . . . . ?
C7 N1 C8 C3 -2.62(18) . . . . ?
C7 N1 C11 C12 -132.91(15) . . . . ?
C7 N1 C11 C13 100.50(18) . . . . ?
C7 C2 C3 C4 -179.58(15) . . . . ?
C7 C2 C3 C8 0.62(18) . . . . ?
C8 N1 C7 O1 -177.10(16) . . . . ?
C8 N1 C7 C2 2.99(18) . . . . ?
C8 N1 C11 C12 49.5(2) . . . . ?
C8 N1 C11 C13 -77.12(19) . . . . ?
C8 C3 C4 C5 179.43(16) . . . . ?
C9 N2 C10 O4 -173.62(16) . . . . ?
C9 N2 C10 C6 6.22(17) . . . . ?
C9 N2 C16 C17 108.94(18) . . . . ?
C9 N2 C16 C18 -19.6(2) . . . . ?
C9 C5 C6 C1 -179.46(15) . . . . ?
C9 C5 C6 C10 -1.29(17) . . . . ?
C10 N2 C9 O3 172.64(17) . . . . ?
C10 N2 C9 C5 -6.91(17) . . . . ?
C10 N2 C16 C17 -72.80(17) . . . . ?
C10 N2 C16 C18 158.64(14) . . . . ?
C11 N1 C7 O1 5.0(3) . . . . ?
C11 N1 C7 C2 -174.89(14) . . . . ?
C11 N1 C8 O2 -5.3(3) . . . . ?
C11 N1 C8 C3 175.22(14) . . . . ?
C12 C11 C13 C14 58.25(18) . . . . ?
C12 C11 C13 C15 179.52(13) . . . . ?
C13 C11 C12 O5 7.7(2) . . . . ?
C13 C11 C12 O6 -171.09(13) . . . . ?
C16 N2 C9 O3 -9.0(3) . . . . ?
C16 N2 C9 C5 171.43(15) . . . . ?
C16 N2 C10 O4 7.8(2) . . . . ?
C16 N2 C10 C6 -172.36(13) . . . . ?
C17 C16 C18 C19 49.53(18) . . . . ?
C17 C16 C18 C20 169.82(13) . . . . ?
C18 C16 C17 O7 -101.94(17) . . . . ?
C18 C16 C17 O8 77.29(16) . . . . ?
C21 C22 C23 C24 -0.2(3) . . . . ?
C21 C29 C30 C24 0.0(2) . . . . ?
C21 C29 C30 C25 -179.95(17) . . . . ?
C22 C21 C29 C28 -178.20(18) . . . . ?
C22 C21 C29 C30 0.8(3) . . . . ?
C22 C23 C24 C30 1.0(3) . . . . ?
C23 C24 C30 C25 179.06(18) . . . . ?
C23 C24 C30 C29 -0.9(3) . . . . ?
C25 C26 C27 C28 -0.7(3) . . . . ?
C26 C25 C30 C24 -179.34(18) . . . . ?
C26 C25 C30 C29 0.6(3) . . . . ?
C26 C27 C28 C29 0.4(3) . . . . ?
C27 C28 C29 C21 179.45(18) . . . . ?
C27 C28 C29 C30 0.4(3) . . . . ?
C28 C29 C30 C24 179.03(17) . . . . ?
C28 C29 C30 C25 -0.9(2) . . . . ?
C29 C21 C22 C23 -0.7(3) . . . . ?
C30 C25 C26 C27 0.2(3) . . . . ?
