#------------------------------------------------------------------------------
#$Date: 2020-09-06 13:22:45 +0300 (Sun, 06 Sep 2020) $
#$Revision: 256182 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/76/7157671.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_7157671
loop_
_publ_author_name
'Luo, Yan-Long'
'Liu, Yu-Feng'
'Guan, Bing-Tao'
_publ_section_title
;
 Alkyl lithium-catalyzed benzylic C-H bond addition of alkyl pyridines to
 α-alkenes.
;
_journal_issue                   34
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6622
_journal_page_last               6626
_journal_paper_doi               10.1039/d0ob01499k
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C7 H3 N2 O6, C7 H4 N2 O6, C12 H18 N'
_chemical_formula_sum            'C26 H25 N5 O12'
_chemical_formula_weight         599.51
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-11 deposited with the CCDC.	2020-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                108.0000(10)
_cell_angle_beta                 99.4130(10)
_cell_angle_gamma                106.6790(10)
_cell_formula_units_Z            2
_cell_length_a                   10.03310(10)
_cell_length_b                   11.89880(10)
_cell_length_c                   13.4124(2)
_cell_measurement_reflns_used    19514
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      79.0890
_cell_measurement_theta_min      4.1980
_cell_volume                     1401.73(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      294.15
_diffrn_detector                 PILT
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  94.00   0.50    0.50    --    5.00  57.00-120.00  236
  2  ω    -84.00  39.00   0.50    0.50    --  -50.10  72.00  30.00  246
  3  ω    -82.00  39.00   0.50    0.50    --  -50.10  38.00-120.00  242
  4  ω   -140.00 -21.00   0.50    0.50    --  -50.10 -52.00  51.64  238
  5  ω   -140.00 -17.00   0.50    0.50    --  -50.10 -72.00 120.00  246
  6  ω   -140.00 -17.00   0.50    0.50    --  -50.10 -33.00 -50.17  246
  7  ω   -199.00 -81.00   0.50    0.50    -- -110.00 -57.00 -90.00  236
  8  ω   -143.00 -21.00   0.50    0.50    -- -110.00  72.00  60.00  244
  9  ω   -161.00 -21.00   0.50    0.50    -- -110.00  19.00  60.00  280
 10  ω   -143.00 -21.00   0.50    0.50    -- -110.00  72.00 -60.00  244
 11  ω   -143.00 -21.00   0.50    0.50    -- -110.00  72.00  90.00  244
 12  ω   -199.00 -80.00   0.50    0.50    -- -110.00 -64.00  64.12  238
 13  ω   -139.00 -21.00   0.50    0.50    -- -110.00  57.00 120.00  236
 14  ω   -143.00 -21.00   0.50    0.50    -- -110.00  72.00-150.00  244
 15  ω   -143.00 -21.00   0.50    0.50    -- -110.00  72.00-180.00  244
 16  ω   -199.00 -59.00   0.50    0.50    -- -110.00 -19.00 -30.00  280
 17  ω   -143.00 -21.00   0.50    0.50    -- -110.00  72.00 -90.00  244
 18  ω   -143.00 -21.00   0.50    0.50    -- -110.00  72.00   0.00  244
 19  ω   -139.00 -21.00   0.50    0.50    -- -110.00  57.00-180.00  236
 20  ω   -143.00 -21.00   0.50    0.50    -- -110.00  72.00 -30.00  244
 21  ω   -199.00 -81.00   0.50    0.50    -- -110.00 -46.00-113.60  236
 22  ω   -143.00 -21.00   0.50    0.50    -- -110.00  72.00 120.00  244
 23  ω   -199.00 -79.00   0.50    0.50    -- -110.00 -67.00 152.66  240
 24  ω   -140.00 -20.00   0.50    0.50    --  -50.10 -63.00 147.48  240
 25  ω    -80.00  39.00   0.50    0.50    --  -50.10  57.00 -30.00  238
 26  ω   -140.00 -21.00   0.50    0.50    --  -50.10 -57.00-150.00  238
 27  ω   -140.00 -21.00   0.50    0.50    --  -50.10 -60.00 -74.49  238
 28  ω   -199.00 -79.00   0.50    0.50    -- -110.00 -38.00-180.00  240
 29  ω   -199.00-146.00   0.50    0.50    -- -110.00 -38.00 -60.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0428342000
_diffrn_orient_matrix_UB_12      0.0385680000
_diffrn_orient_matrix_UB_13      -0.0931590000
_diffrn_orient_matrix_UB_21      0.0740172000
_diffrn_orient_matrix_UB_22      0.1389523000
_diffrn_orient_matrix_UB_23      0.0798995000
_diffrn_orient_matrix_UB_31      0.1432261000
_diffrn_orient_matrix_UB_32      -0.0222050000
_diffrn_orient_matrix_UB_33      0.0271012000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34190
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.542
_diffrn_reflns_theta_min         3.606
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.980
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0052(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         5893
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0572
_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)+(0.0970P)²+0.2560P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1780
_refine_ls_wR_factor_ref         0.1816
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5241
_reflns_number_total             5893
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob01499k2.cif
_cod_data_source_block           p20190605b
_cod_depositor_comments          'Adding full bibliography for 7157671.cif.'
_cod_database_code               7157671
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C19H21N3O6
_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   0.843
_shelx_estimated_absorpt_t_min   0.771
_reflns_odcompleteness_completeness 97.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,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:
 C6(H6), C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C17(H17), C19(H19), C22(H22),
 C24(H24), C26(H26)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O7(H7A)
;
_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 3.109
_oxdiff_exptl_absorpt_empirical_full_min 0.648
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 0.30768(15) 0.31261(14) 0.36741(11) 0.0756(4) Uani 1 1 d . . . . .
O2 O 0.34737(14) 0.43911(12) 0.53986(11) 0.0687(3) Uani 1 1 d . . . . .
O3 O 0.6658(3) 0.3891(2) 0.82849(14) 0.1172(7) Uani 1 1 d . . . . .
O4 O 0.7501(3) 0.2435(3) 0.79015(18) 0.1539(11) Uani 1 1 d . . . . .
O5 O 0.68938(18) -0.00687(15) 0.41849(17) 0.0978(5) Uani 1 1 d . . . . .
O6 O 0.5520(3) 0.0105(3) 0.29198(18) 0.1405(9) Uani 1 1 d . . . . .
O7 O 0.18918(13) 0.55116(12) 0.48826(10) 0.0634(3) Uani 1 1 d . . . . .
H7A H 0.238950 0.515010 0.509980 0.095 Uiso 1 1 calc GR . . . .
O8 O 0.19672(19) 0.63298(17) 0.66343(12) 0.0909(5) Uani 1 1 d . . . . .
O9 O -0.0058(2) 0.9659(2) 0.77162(13) 0.1105(6) Uani 1 1 d . . . . .
O10 O -0.1238(2) 1.01249(16) 0.65181(14) 0.0958(5) Uani 1 1 d . . . . .
O11 O -0.2062(2) 0.7727(2) 0.26972(14) 0.1144(7) Uani 1 1 d . . . . .
O12 O -0.0915(2) 0.64873(18) 0.22309(12) 0.1023(6) Uani 1 1 d . . . . .
N1 N 0.17638(17) 0.33487(14) 0.19138(11) 0.0602(3) Uani 1 1 d . . . . .
N2 N 0.6812(2) 0.30231(19) 0.76347(15) 0.0834(5) Uani 1 1 d . . . . .
N3 N 0.60945(19) 0.04042(16) 0.38571(17) 0.0754(5) Uani 1 1 d . . . . .
N4 N -0.05371(19) 0.95291(15) 0.67827(14) 0.0727(4) Uani 1 1 d . . . . .
N5 N -0.1250(2) 0.72070(17) 0.29126(13) 0.0742(4) Uani 1 1 d . . . . .
C1 C 0.2047(2) 0.29429(18) 0.09525(13) 0.0660(4) Uani 1 1 d . . . . .
C2 C 0.1170(3) 0.2986(3) 0.00737(16) 0.0893(7) Uani 1 1 d . . . . .
H2 H 0.132756 0.271490 -0.061046 0.107 Uiso 1 1 calc R . . . .
C3 C 0.0064(3) 0.3429(3) 0.02022(19) 0.0981(8) Uani 1 1 d . . . . .
H3 H -0.052021 0.346133 -0.039493 0.118 Uiso 1 1 calc R . . . .
C4 C -0.0190(3) 0.3825(2) 0.1210(2) 0.0877(6) Uani 1 1 d . . . . .
H4 H -0.094842 0.411284 0.129865 0.105 Uiso 1 1 calc R . . . .
C5 C 0.0694(2) 0.37858(19) 0.20660(17) 0.0730(5) Uani 1 1 d . . . . .
H5 H 0.055758 0.406117 0.275732 0.088 Uiso 1 1 calc R . . . .
C6 C 0.3249(2) 0.2431(2) 0.08894(16) 0.0792(6) Uani 1 1 d . . . . .
H6 H 0.372410 0.254481 0.163128 0.095 Uiso 1 1 calc R . . . .
C7 C 0.4415(3) 0.3094(3) 0.0432(2) 0.0965(7) Uani 1 1 d . . . . .
H7 H 0.393304 0.328537 -0.015718 0.116 Uiso 1 1 calc R . . . .
C8 C 0.4935(5) 0.2013(4) -0.0078(4) 0.1577(16) Uani 1 1 d . . . . .
H8A H 0.535407 0.214267 -0.065488 0.189 Uiso 1 1 calc R . . . .
H8B H 0.565966 0.196801 0.046804 0.189 Uiso 1 1 calc R . . . .
C9 C 0.3682(7) 0.0877(4) -0.0509(5) 0.186(2) Uani 1 1 d . . . . .
H9A H 0.396517 0.015984 -0.052202 0.223 Uiso 1 1 calc R . . . .
H9B H 0.319749 0.073102 -0.125007 0.223 Uiso 1 1 calc R . . . .
C10 C 0.2696(4) 0.1010(3) 0.0185(3) 0.1068(8) Uani 1 1 d . . . . .
H10 H 0.173532 0.079239 -0.029389 0.128 Uiso 1 1 calc R . . . .
C11 C 0.5580(4) 0.4268(4) 0.1207(4) 0.1497(14) Uani 1 1 d . . . . .
H11A H 0.520590 0.494068 0.139061 0.225 Uiso 1 1 calc GR . . . .
H11B H 0.634833 0.448724 0.087985 0.225 Uiso 1 1 calc GR . . . .
H11C H 0.594428 0.414347 0.185660 0.225 Uiso 1 1 calc GR . . . .
C12 C 0.2553(8) 0.0179(5) 0.0783(5) 0.215(3) Uani 1 1 d . . . . .
H12A H 0.348948 0.033218 0.122657 0.322 Uiso 1 1 calc GR . . . .
H12B H 0.214164 -0.068643 0.027919 0.322 Uiso 1 1 calc GR . . . .
H12C H 0.193213 0.033772 0.124103 0.322 Uiso 1 1 calc GR . . . .
C13 C 0.36472(16) 0.35328(15) 0.46668(13) 0.0543(4) Uani 1 1 d . . . . .
C14 C 0.46231(15) 0.29042(14) 0.50513(12) 0.0499(3) Uani 1 1 d . . . . .
C15 C 0.52549(17) 0.32582(15) 0.61517(13) 0.0546(4) Uani 1 1 d . . . . .
H15 H 0.508595 0.388956 0.666972 0.066 Uiso 1 1 calc R . . . .
C16 C 0.61415(17) 0.26576(16) 0.64684(14) 0.0589(4) Uani 1 1 d . . . . .
C17 C 0.64322(17) 0.17185(16) 0.57373(15) 0.0597(4) Uani 1 1 d . . . . .
H17 H 0.703149 0.132503 0.596598 0.072 Uiso 1 1 calc R . . . .
C18 C 0.57915(17) 0.13966(15) 0.46571(15) 0.0564(4) Uani 1 1 d . . . . .
C19 C 0.48901(17) 0.19575(15) 0.42943(13) 0.0541(4) Uani 1 1 d . . . . .
H19 H 0.446676 0.170462 0.355223 0.065 Uiso 1 1 calc R . . . .
C20 C 0.16224(18) 0.62464(16) 0.57080(15) 0.0596(4) Uani 1 1 d . . . . .
C21 C 0.07660(16) 0.69983(14) 0.53927(13) 0.0527(3) Uani 1 1 d . . . . .
C22 C 0.05374(17) 0.79144(15) 0.62058(14) 0.0553(4) Uani 1 1 d . . . . .
H22 H 0.093095 0.808084 0.693677 0.066 Uiso 1 1 calc R . . . .
C23 C -0.02802(17) 0.85743(15) 0.59162(14) 0.0553(4) Uani 1 1 d . . . . .
C24 C -0.08849(17) 0.83726(15) 0.48524(14) 0.0567(4) Uani 1 1 d . . . . .
H24 H -0.143838 0.882528 0.467242 0.068 Uiso 1 1 calc R . . . .
C25 C -0.06262(17) 0.74614(15) 0.40651(13) 0.0552(4) Uani 1 1 d . . . . .
C26 C 0.01852(17) 0.67751(14) 0.43089(13) 0.0543(4) Uani 1 1 d . . . . .
H26 H 0.034078 0.617139 0.375485 0.065 Uiso 1 1 calc R . . . .
H1 H 0.230(3) 0.331(2) 0.251(2) 0.085(7) Uiso 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
C20 O7 H7A 109.5 . . ?
C1 N1 C5 124.30(16) . . ?
C1 N1 H1 119.7(15) . . ?
C5 N1 H1 116.0(15) . . ?
O3 N2 O4 122.3(2) . . ?
O3 N2 C16 119.17(18) . . ?
O4 N2 C16 118.5(2) . . ?
O5 N3 C18 118.7(2) . . ?
O6 N3 O5 123.5(2) . . ?
O6 N3 C18 117.80(18) . . ?
O9 N4 O10 124.07(17) . . ?
O9 N4 C23 117.75(16) . . ?
O10 N4 C23 118.17(17) . . ?
O11 N5 O12 123.58(18) . . ?
O11 N5 C25 118.39(17) . . ?
O12 N5 C25 118.02(16) . . ?
N1 C1 C2 116.88(18) . . ?
N1 C1 C6 118.74(16) . . ?
C2 C1 C6 124.35(17) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.26(19) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.5(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.3(2) . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C4 119.71(19) . . ?
N1 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C1 C6 H6 107.7 . . ?
C1 C6 C7 114.43(19) . . ?
C1 C6 C10 112.6(2) . . ?
C7 C6 H6 107.7 . . ?
C10 C6 H6 107.7 . . ?
C10 C6 C7 106.6(2) . . ?
C6 C7 H7 108.2 . . ?
C8 C7 C6 100.7(2) . . ?
C8 C7 H7 108.2 . . ?
C11 C7 C6 117.0(3) . . ?
C11 C7 H7 108.2 . . ?
C11 C7 C8 114.2(3) . . ?
C7 C8 H8A 110.5 . . ?
C7 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
C9 C8 C7 106.1(3) . . ?
C9 C8 H8A 110.5 . . ?
C9 C8 H8B 110.5 . . ?
C8 C9 H9A 109.9 . . ?
C8 C9 H9B 109.9 . . ?
C8 C9 C10 108.8(3) . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 H9A 109.9 . . ?
C10 C9 H9B 109.9 . . ?
C6 C10 H10 107.5 . . ?
C9 C10 C6 105.1(3) . . ?
C9 C10 H10 107.5 . . ?
C12 C10 C6 115.3(3) . . ?
C12 C10 C9 113.7(3) . . ?
C12 C10 H10 107.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 O2 127.15(15) . . ?
O1 C13 C14 116.79(15) . . ?
O2 C13 C14 116.02(14) . . ?
C15 C14 C13 120.78(14) . . ?
C15 C14 C19 119.45(14) . . ?
C19 C14 C13 119.77(14) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 C14 118.89(15) . . ?
C16 C15 H15 120.6 . . ?
C15 C16 N2 119.31(17) . . ?
C17 C16 N2 117.64(16) . . ?
C17 C16 C15 123.05(16) . . ?
C16 C17 H17 121.8 . . ?
C18 C17 C16 116.37(15) . . ?
C18 C17 H17 121.8 . . ?
C17 C18 N3 117.53(16) . . ?
C17 C18 C19 123.09(15) . . ?
C19 C18 N3 119.38(17) . . ?
C14 C19 H19 120.4 . . ?
C18 C19 C14 119.15(15) . . ?
C18 C19 H19 120.4 . . ?
O7 C20 C21 113.27(15) . . ?
O8 C20 O7 125.74(16) . . ?
O8 C20 C21 120.97(16) . . ?
C22 C21 C20 119.12(15) . . ?
C26 C21 C20 121.28(14) . . ?
C26 C21 C22 119.59(14) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 C21 119.07(15) . . ?
C23 C22 H22 120.5 . . ?
C22 C23 N4 118.72(16) . . ?
C24 C23 N4 118.19(15) . . ?
C24 C23 C22 123.08(15) . . ?
C23 C24 H24 121.9 . . ?
C23 C24 C25 116.28(15) . . ?
C25 C24 H24 121.9 . . ?
C24 C25 N5 118.51(15) . . ?
C26 C25 N5 118.45(15) . . ?
C26 C25 C24 123.04(16) . . ?
C21 C26 H26 120.5 . . ?
C25 C26 C21 118.93(15) . . ?
C25 C26 H26 120.5 . . ?
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 C13 1.236(2) . ?
O2 C13 1.255(2) . ?
O3 N2 1.196(3) . ?
O4 N2 1.203(3) . ?
O5 N3 1.204(2) . ?
O6 N3 1.186(3) . ?
O7 H7A 0.8200 . ?
O7 C20 1.303(2) . ?
O8 C20 1.199(2) . ?
O9 N4 1.210(2) . ?
O10 N4 1.218(2) . ?
O11 N5 1.206(2) . ?
O12 N5 1.210(2) . ?
N1 C1 1.338(2) . ?
N1 C5 1.339(2) . ?
N1 H1 0.91(3) . ?
N2 C16 1.468(2) . ?
N3 C18 1.472(2) . ?
N4 C23 1.469(2) . ?
N5 C25 1.469(2) . ?
C1 C2 1.375(3) . ?
C1 C6 1.501(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.371(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.353(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9800 . ?
C6 C7 1.540(3) . ?
C6 C10 1.537(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.534(4) . ?
C7 C11 1.472(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.430(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.474(5) . ?
C10 H10 0.9800 . ?
C10 C12 1.446(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.509(2) . ?
C14 C15 1.384(2) . ?
C14 C19 1.388(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.382(2) . ?
C16 C17 1.378(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.367(3) . ?
C18 C19 1.380(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.508(2) . ?
C21 C22 1.386(2) . ?
C21 C26 1.385(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.376(2) . ?
C23 C24 1.372(2) . ?
C24 H24 0.9300 . ?
C24 C25 1.379(2) . ?
C25 C26 1.377(2) . ?
C26 H26 0.9300 . ?
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
O1 C13 C14 C15 -177.03(15) . . . . ?
O1 C13 C14 C19 2.8(2) . . . . ?
O2 C13 C14 C15 1.0(2) . . . . ?
O2 C13 C14 C19 -179.10(14) . . . . ?
O3 N2 C16 C15 -5.0(3) . . . . ?
O3 N2 C16 C17 175.1(2) . . . . ?
O4 N2 C16 C15 175.0(2) . . . . ?
O4 N2 C16 C17 -4.9(3) . . . . ?
O5 N3 C18 C17 -0.6(3) . . . . ?
O5 N3 C18 C19 179.32(16) . . . . ?
O6 N3 C18 C17 178.6(2) . . . . ?
O6 N3 C18 C19 -1.5(3) . . . . ?
O7 C20 C21 C22 -173.23(14) . . . . ?
O7 C20 C21 C26 7.9(2) . . . . ?
O8 C20 C21 C22 8.3(3) . . . . ?
O8 C20 C21 C26 -170.58(17) . . . . ?
O9 N4 C23 C22 -2.6(3) . . . . ?
O9 N4 C23 C24 176.59(19) . . . . ?
O10 N4 C23 C22 178.57(17) . . . . ?
O10 N4 C23 C24 -2.2(3) . . . . ?
O11 N5 C25 C24 -6.1(3) . . . . ?
O11 N5 C25 C26 173.65(19) . . . . ?
O12 N5 C25 C24 173.71(18) . . . . ?
O12 N5 C25 C26 -6.5(3) . . . . ?
N1 C1 C2 C3 -0.1(4) . . . . ?
N1 C1 C6 C7 -124.4(2) . . . . ?
N1 C1 C6 C10 113.8(2) . . . . ?
N2 C16 C17 C18 179.92(15) . . . . ?
N3 C18 C19 C14 -179.16(14) . . . . ?
N4 C23 C24 C25 -179.50(14) . . . . ?
N5 C25 C26 C21 -179.35(14) . . . . ?
C1 N1 C5 C4 0.5(3) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C1 C6 C7 C8 -151.4(3) . . . . ?
C1 C6 C7 C11 84.2(3) . . . . ?
C1 C6 C10 C9 134.9(3) . . . . ?
C1 C6 C10 C12 -99.1(4) . . . . ?
C2 C1 C6 C7 58.0(3) . . . . ?
C2 C1 C6 C10 -63.9(3) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C3 C4 C5 N1 -1.1(4) . . . . ?
C5 N1 C1 C2 0.1(3) . . . . ?
C5 N1 C1 C6 -177.76(19) . . . . ?
C6 C1 C2 C3 177.6(2) . . . . ?
C6 C7 C8 C9 35.7(5) . . . . ?
C7 C6 C10 C9 8.7(4) . . . . ?
C7 C6 C10 C12 134.6(4) . . . . ?
C7 C8 C9 C10 -32.4(6) . . . . ?
C8 C9 C10 C6 14.5(5) . . . . ?
C8 C9 C10 C12 -112.4(5) . . . . ?
C10 C6 C7 C8 -26.3(3) . . . . ?
C10 C6 C7 C11 -150.7(3) . . . . ?
C11 C7 C8 C9 161.9(4) . . . . ?
C13 C14 C15 C16 179.99(14) . . . . ?
C13 C14 C19 C18 179.61(13) . . . . ?
C14 C15 C16 N2 -179.76(15) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C15 C14 C19 C18 -0.5(2) . . . . ?
C15 C16 C17 C18 0.0(3) . . . . ?
C16 C17 C18 N3 179.43(14) . . . . ?
C16 C17 C18 C19 -0.5(2) . . . . ?
C17 C18 C19 C14 0.7(2) . . . . ?
C19 C14 C15 C16 0.1(2) . . . . ?
C20 C21 C22 C23 -178.12(14) . . . . ?
C20 C21 C26 C25 177.99(14) . . . . ?
C21 C22 C23 N4 179.02(14) . . . . ?
C21 C22 C23 C24 -0.2(2) . . . . ?
C22 C21 C26 C25 -0.9(2) . . . . ?
C22 C23 C24 C25 -0.3(2) . . . . ?
C23 C24 C25 N5 179.95(14) . . . . ?
C23 C24 C25 C26 0.2(2) . . . . ?
C24 C25 C26 C21 0.4(2) . . . . ?
C26 C21 C22 C23 0.8(2) . . . . ?
