#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:20:33 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180073 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/19/7051902.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_7051902
loop_
_publ_author_name
'Gassensmith, Jeremiah J.'
'Lee, Jung-Jae'
'Noll, Bruce C.'
'Smith, Bradley D.'
_publ_section_title
;
 Crossing the threshold from accelerated substitution to elimination
 with a bifunctional macrocycle
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              843
_journal_paper_doi               10.1039/b719658j
_journal_volume                  32
_journal_year                    2008
_chemical_compound_source        synthesized
_chemical_formula_moiety         'C27 H30 N3 O4 +, Cl -'
_chemical_formula_sum            'C27 H30 Cl N3 O4'
_chemical_formula_weight         495.99
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.027(1)
_cell_angle_beta                 104.128(1)
_cell_angle_gamma                102.882(1)
_cell_formula_units_Z            4
_cell_length_a                   11.0581(3)
_cell_length_b                   13.2036(3)
_cell_length_c                   18.3085(5)
_cell_measurement_reflns_used    9338
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.38
_cell_measurement_theta_min      2.35
_cell_volume                     2463.12(11)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004; Sheldrick, 2003)'
_computing_molecular_graphics    'XP (Sheldrick, 1998)'
_computing_publication_material  'XCIF (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            65637
_diffrn_reflns_theta_full        31.51
_diffrn_reflns_theta_max         31.51
_diffrn_reflns_theta_min         1.18
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Siemens KFFMO2K-90'
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_T_max  0.9677
_exptl_absorpt_correction_T_min  0.9211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Blessing, R. H. (1995) Acta Cryst. A51, 33-38.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.840
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     731
_refine_ls_number_reflns         16272
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0639
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0614P)²+3.5500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1718
_refine_ls_wR_factor_ref         0.1765
_reflns_number_gt                13611
_reflns_number_total             16272
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b719658j.txt
_cod_data_source_block           bcn116noh
_cod_database_code               7051902
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.36235(4) 0.14884(4) 1.06498(3) 0.02250(10) Uani 1 1 d . . .
N1 N 0.36443(17) -0.14047(16) 0.86159(11) 0.0257(4) Uani 1 1 d . . .
H1N H 0.452(3) -0.144(3) 0.8821(19) 0.039(8) Uiso 1 1 d . . .
N2 N 0.31441(17) 0.35299(13) 0.99101(10) 0.0206(3) Uani 1 1 d . . .
H2N H 0.322(3) 0.299(2) 1.0109(16) 0.021(6) Uiso 1 1 d . . .
N3 N 0.08730(16) 0.06546(13) 1.10808(10) 0.0180(3) Uani 1 1 d . . .
H3N H 0.153(3) 0.091(2) 1.0922(16) 0.025(7) Uiso 1 1 d . . .
O1 O 0.40544(17) 0.07913(13) 0.81244(9) 0.0281(3) Uani 1 1 d . . .
O2 O 0.2106(2) -0.23275(17) 0.96788(13) 0.0293(6) Uani 0.845(6) 1 d P A 1
C24 C 0.1976(4) -0.2685(3) 1.0345(2) 0.0300(7) Uani 0.845(6) 1 d P A 1
H24A H 0.2844 -0.2594 1.0702 0.036 Uiso 0.845(6) 1 calc PR A 1
H24B H 0.1507 -0.3452 1.0204 0.036 Uiso 0.845(6) 1 calc PR A 1
C25 C 0.2830(3) -0.2835(2) 0.9277(2) 0.0253(6) Uani 0.845(6) 1 d P A 1
H25A H 0.2471 -0.3619 0.9164 0.030 Uiso 0.845(6) 1 calc PR A 1
H25B H 0.3745 -0.2650 0.9595 0.030 Uiso 0.845(6) 1 calc PR A 1
O2' O 0.2913(11) -0.1995(8) 1.0085(7) 0.024(3) Uani 0.155(6) 1 d P A 2
C24' C 0.237(2) -0.2464(19) 1.0418(16) 0.0300(7) Uani 0.155(6) 1 d P A 2
H24C H 0.3027 -0.2531 1.0873 0.036 Uiso 0.155(6) 1 calc PR A 2
H24D H 0.1962 -0.3191 1.0090 0.036 Uiso 0.155(6) 1 calc PR A 2
C25' C 0.3468(18) -0.2587(13) 0.9607(10) 0.025(3) Uani 0.155(6) 1 d P A 2
H25C H 0.3288 -0.3335 0.9662 0.030 Uiso 0.155(6) 1 calc PR A 2
H25D H 0.4419 -0.2278 0.9761 0.030 Uiso 0.155(6) 1 calc PR A 2
O3 O 0.23712(19) 0.49985(13) 0.99722(12) 0.0351(4) Uani 1 1 d . . .
O4 O -0.04209(14) 0.11604(12) 1.17929(9) 0.0228(3) Uani 1 1 d . . .
C1 C 0.3465(3) -0.1107(3) 0.78498(15) 0.0242(5) Uani 0.826(5) 1 d P A 1
H1A H 0.2584 -0.1011 0.7680 0.029 Uiso 0.826(5) 1 calc PR A 1
H1B H 0.3511 -0.1708 0.7469 0.029 Uiso 0.826(5) 1 calc PR A 1
C2 C 0.4428(3) -0.0115(2) 0.78345(15) 0.0262(6) Uani 0.826(5) 1 d P A 1
H2A H 0.5302 -0.0087 0.8156 0.031 Uiso 0.826(5) 1 calc PR A 1
H2B H 0.4462 -0.0122 0.7298 0.031 Uiso 0.826(5) 1 calc PR A 1
C1' C 0.3660(14) -0.0575(11) 0.8949(9) 0.0242(5) Uani 0.174(5) 1 d P A 2
H1'1 H 0.3925 -0.0555 0.9510 0.029 Uiso 0.174(5) 1 calc PR A 2
H1'2 H 0.2766 -0.0499 0.8813 0.029 Uiso 0.174(5) 1 calc PR A 2
C2' C 0.4535(11) 0.0359(9) 0.8801(6) 0.020(2) Uani 0.174(5) 1 d P A 2
H2'1 H 0.4800 0.0945 0.9266 0.024 Uiso 0.174(5) 1 calc PR A 2
H2'2 H 0.5328 0.0158 0.8753 0.024 Uiso 0.174(5) 1 calc PR A 2
C3 C 0.4782(2) 0.1713(2) 0.79642(15) 0.0323(5) Uani 1 1 d . A .
H3A H 0.4550 0.1656 0.7399 0.039 Uiso 1 1 calc R . .
H3B H 0.5718 0.1765 0.8150 0.039 Uiso 1 1 calc R . .
C4 C 0.4519(2) 0.27016(17) 0.83532(12) 0.0238(4) Uani 1 1 d . . .
C5 C 0.4859(2) 0.36459(19) 0.81062(13) 0.0285(4) Uani 1 1 d . A .
H5 H 0.5254 0.3662 0.7700 0.034 Uiso 1 1 calc R . .
C6 C 0.4620(2) 0.45502(18) 0.84534(13) 0.0281(4) Uani 1 1 d . . .
H6 H 0.4855 0.5189 0.8282 0.034 Uiso 1 1 calc R A .
C7 C 0.4043(2) 0.45575(16) 0.90515(13) 0.0249(4) Uani 1 1 d . A .
H7 H 0.3886 0.5191 0.9285 0.030 Uiso 1 1 calc R . .
C8 C 0.37010(19) 0.36130(15) 0.93012(11) 0.0203(3) Uani 1 1 d . . .
C9 C 0.3944(2) 0.26895(16) 0.89483(12) 0.0218(4) Uani 1 1 d . A .
H9 H 0.3714 0.2048 0.9117 0.026 Uiso 1 1 calc R . .
C10 C 0.2493(2) 0.41883(15) 1.01911(13) 0.0228(4) Uani 1 1 d . . .
C11 C 0.19245(19) 0.38591(15) 1.08110(12) 0.0214(4) Uani 1 1 d . A .
C12 C 0.1855(2) 0.46529(16) 1.13870(14) 0.0274(4) Uani 1 1 d . . .
H12 H 0.2158 0.5382 1.1378 0.033 Uiso 1 1 calc R A .
C13 C 0.1344(2) 0.43825(17) 1.19745(14) 0.0295(4) Uani 1 1 d . A .
H13 H 0.1311 0.4927 1.2370 0.035 Uiso 1 1 calc R . .
C14 C 0.0882(2) 0.33150(16) 1.19856(12) 0.0238(4) Uani 1 1 d . . .
H14 H 0.0536 0.3132 1.2389 0.029 Uiso 1 1 calc R A .
C15 C 0.09268(17) 0.25141(14) 1.14053(11) 0.0177(3) Uani 1 1 d . A .
C16 C 0.14341(18) 0.27894(14) 1.08168(11) 0.0183(3) Uani 1 1 d . . .
H16 H 0.1448 0.2245 1.0415 0.022 Uiso 1 1 calc R A .
C17 C 0.03864(17) 0.13810(15) 1.14411(11) 0.0173(3) Uani 1 1 d . . .
C18 C 0.06256(18) -0.04483(14) 1.10670(11) 0.0180(3) Uani 1 1 d . . .
C19 C -0.0335(2) -0.10053(16) 1.13375(12) 0.0223(4) Uani 1 1 d . A .
H19 H -0.0910 -0.0661 1.1517 0.027 Uiso 1 1 calc R . .
C20 C -0.0440(2) -0.20766(17) 1.13414(13) 0.0261(4) Uani 1 1 d . . .
H20 H -0.1066 -0.2451 1.1549 0.031 Uiso 1 1 calc R A .
C21 C 0.0348(2) -0.26046(16) 1.10494(12) 0.0258(4) Uani 1 1 d . A .
H21 H 0.0273 -0.3332 1.1064 0.031 Uiso 1 1 calc R . .
C22 C 0.1248(2) -0.20645(17) 1.07352(12) 0.0242(4) Uani 1 1 d . . .
C23 C 0.1403(2) -0.09858(16) 1.07542(12) 0.0219(4) Uani 1 1 d . A .
H23 H 0.2040 -0.0612 1.0554 0.026 Uiso 1 1 calc R . .
C26 C 0.2750(4) -0.2464(3) 0.8538(2) 0.0226(7) Uani 0.845(6) 1 d P A 1
H26A H 0.2936 -0.2998 0.8169 0.027 Uiso 0.845(6) 1 calc PR A 1
H26B H 0.1851 -0.2437 0.8314 0.027 Uiso 0.845(6) 1 calc PR A 1
C26' C 0.291(2) -0.2549(16) 0.8808(12) 0.022(4) Uani 0.155(6) 1 d P A 2
H26C H 0.1970 -0.2606 0.8714 0.026 Uiso 0.155(6) 1 calc PR A 2
H26D H 0.2997 -0.3161 0.8458 0.026 Uiso 0.155(6) 1 calc PR A 2
C27 C 0.3495(2) -0.0522(2) 0.92163(17) 0.0215(5) Uani 0.826(5) 1 d P A 1
H27A H 0.2597 -0.0480 0.9078 0.032 Uiso 0.826(5) 1 calc PR A 1
H27B H 0.4076 0.0163 0.9226 0.032 Uiso 0.826(5) 1 calc PR A 1
H27C H 0.3718 -0.0686 0.9728 0.032 Uiso 0.826(5) 1 calc PR A 1
C27' C 0.3235(14) -0.1723(13) 0.7664(7) 0.029(3) Uani 0.174(5) 1 d P A 2
H27D H 0.2290 -0.1912 0.7456 0.044 Uiso 0.174(5) 1 calc PR A 2
H27E H 0.3550 -0.2331 0.7497 0.044 Uiso 0.174(5) 1 calc PR A 2
H27F H 0.3623 -0.1113 0.7473 0.044 Uiso 0.174(5) 1 calc PR A 2
Cl2 Cl 0.78094(4) 0.11372(4) 0.41665(3) 0.02128(10) Uani 1 1 d . . .
N4 N 0.97666(17) -0.05555(14) 0.61039(10) 0.0220(3) Uani 1 1 d . . .
H4N H 1.043(3) -0.074(3) 0.5909(19) 0.040(8) Uiso 1 1 d . . .
N5 N 0.80437(17) 0.36465(13) 0.49645(10) 0.0214(3) Uani 1 1 d . B .
H5N H 0.790(3) 0.300(2) 0.4782(17) 0.029(7) Uiso 1 1 d . . .
N6 N 0.45407(17) 0.00817(14) 0.37887(11) 0.0242(3) Uani 1 1 d . B .
H6N H 0.532(3) 0.038(2) 0.3985(16) 0.024(7) Uiso 1 1 d . . .
O5 O 1.0724(2) 0.19426(14) 0.66726(13) 0.0226(7) Uani 0.813(8) 1 d P B 1
O5' O 1.1327(13) 0.2071(11) 0.6474(6) 0.043(4) Uani 0.187(8) 1 d P B 2
C30' C 1.110(2) 0.284(2) 0.7004(12) 0.060(6) Uani 0.187(8) 1 d P B 2
H30C H 1.1855 0.3124 0.7470 0.072 Uiso 0.187(8) 1 calc PR B 2
H30D H 1.0325 0.2531 0.7162 0.072 Uiso 0.187(8) 1 calc PR B 2
O6 O 0.70664(16) -0.20608(12) 0.51582(10) 0.0285(3) Uani 1 1 d . . .
O7 O 0.72901(19) 0.51035(13) 0.48177(13) 0.0422(5) Uani 1 1 d . B .
O8 O 0.26338(14) 0.02017(13) 0.30195(10) 0.0284(3) Uani 1 1 d . B .
C28 C 1.0418(2) 0.01836(18) 0.68861(12) 0.0248(4) Uani 1 1 d . B .
H28A H 0.9743 0.0390 0.7098 0.030 Uiso 1 1 calc R . .
H28B H 1.0855 -0.0210 0.7236 0.030 Uiso 1 1 calc R . .
C29 C 1.1393(2) 0.11771(18) 0.68914(13) 0.0285(4) Uani 1 1 d . . .
H29A H 1.2013 0.1467 0.7414 0.034 Uiso 1 1 calc R B 1
H29B H 1.1886 0.1015 0.6524 0.034 Uiso 1 1 calc R B 1
C30 C 1.1590(3) 0.2978(2) 0.68635(18) 0.0217(6) Uani 0.813(8) 1 d P B 1
H30A H 1.2317 0.2965 0.6640 0.026 Uiso 0.813(8) 1 calc PR B 1
H30B H 1.1951 0.3221 0.7432 0.026 Uiso 0.813(8) 1 calc PR B 1
C31 C 1.0868(2) 0.37327(17) 0.65470(12) 0.0245(4) Uani 1 1 d . . .
C32 C 1.1365(2) 0.48225(18) 0.68678(13) 0.0287(4) Uani 1 1 d . B .
H32 H 1.2108 0.5077 0.7306 0.034 Uiso 1 1 calc R . .
C33 C 1.0773(2) 0.55337(18) 0.65449(15) 0.0317(5) Uani 1 1 d . . .
H33 H 1.1128 0.6277 0.6759 0.038 Uiso 1 1 calc R B .
C34 C 0.9669(2) 0.51815(17) 0.59130(14) 0.0279(4) Uani 1 1 d . B .
H34 H 0.9269 0.5676 0.5698 0.033 Uiso 1 1 calc R . .
C35 C 0.91571(19) 0.40866(16) 0.55995(12) 0.0209(3) Uani 1 1 d . . .
C36 C 0.9766(2) 0.33708(16) 0.59172(12) 0.0234(4) Uani 1 1 d . B .
H36 H 0.9421 0.2628 0.5700 0.028 Uiso 1 1 calc R . .
C37 C 0.7173(2) 0.41491(16) 0.46343(13) 0.0257(4) Uani 1 1 d . . .
C38 C 0.6026(2) 0.34364(16) 0.39998(12) 0.0228(4) Uani 1 1 d . B .
C39 C 0.5459(2) 0.3866(2) 0.33952(16) 0.0325(5) Uani 1 1 d . . .
H39 H 0.5810 0.4590 0.3391 0.039 Uiso 1 1 calc R B .
C40 C 0.4386(2) 0.3237(2) 0.28020(15) 0.0344(5) Uani 1 1 d . B .
H40 H 0.4008 0.3529 0.2390 0.041 Uiso 1 1 calc R . .
C41 C 0.3861(2) 0.2181(2) 0.28089(13) 0.0277(4) Uani 1 1 d . . .
H41 H 0.3131 0.1751 0.2400 0.033 Uiso 1 1 calc R B .
C42 C 0.44064(18) 0.17520(16) 0.34175(11) 0.0202(3) Uani 1 1 d . B .
C43 C 0.54892(18) 0.23836(15) 0.40140(11) 0.0190(3) Uani 1 1 d . . .
H43 H 0.5859 0.2094 0.4430 0.023 Uiso 1 1 calc R B .
C44 C 0.37736(18) 0.06130(16) 0.33925(12) 0.0214(4) Uani 1 1 d . . .
C45 C 0.42383(19) -0.10229(16) 0.37729(12) 0.0230(4) Uani 1 1 d . . .
C46 C 0.3040(2) -0.17392(18) 0.33577(14) 0.0292(4) Uani 1 1 d . B .
H46 H 0.2360 -0.1496 0.3077 0.035 Uiso 1 1 calc R . .
C47 C 0.2861(2) -0.28132(18) 0.33623(15) 0.0318(5) Uani 1 1 d . . .
H47 H 0.2048 -0.3304 0.3083 0.038 Uiso 1 1 calc R B .
C48 C 0.3840(2) -0.31874(17) 0.37644(14) 0.0294(4) Uani 1 1 d . B .
H48 H 0.3696 -0.3926 0.3758 0.035 Uiso 1 1 calc R . .
C49 C 0.5036(2) -0.24745(16) 0.41773(13) 0.0246(4) Uani 1 1 d . . .
C50 C 0.5229(2) -0.13943(16) 0.41821(12) 0.0230(4) Uani 1 1 d . B .
H50 H 0.6042 -0.0905 0.4466 0.028 Uiso 1 1 calc R . .
C51 C 0.6096(2) -0.28998(17) 0.45967(14) 0.0292(4) Uani 1 1 d . B .
H51A H 0.5729 -0.3451 0.4852 0.035 Uiso 1 1 calc R . .
H51B H 0.6483 -0.3234 0.4222 0.035 Uiso 1 1 calc R . .
C52 C 0.8187(2) -0.23833(18) 0.54910(15) 0.0312(5) Uani 1 1 d . . .
H52A H 0.8697 -0.2442 0.5118 0.037 Uiso 1 1 calc R . .
H52B H 0.7920 -0.3091 0.5609 0.037 Uiso 1 1 calc R . .
C53 C 0.9009(2) -0.15794(17) 0.62218(14) 0.0271(4) Uani 1 1 d . . .
H53A H 0.8439 -0.1412 0.6537 0.033 Uiso 1 1 calc R . .
H53B H 0.9624 -0.1910 0.6522 0.033 Uiso 1 1 calc R . .
C54 C 0.8975(2) -0.00466(16) 0.55712(12) 0.0224(4) Uani 1 1 d . . .
H54A H 0.8278 0.0106 0.5776 0.034 Uiso 1 1 calc R . .
H54B H 0.8598 -0.0531 0.5060 0.034 Uiso 1 1 calc R . .
H54C H 0.9527 0.0620 0.5527 0.030(7) Uiso 1 1 calc R . .
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'
Cl Cl 0.1484 0.1585 '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
C1' N1 C26 128.8(8) . . ?
C1' N1 C1 94.8(8) . . ?
C26 N1 C1 110.4(2) . . ?
C1' N1 C27 17.9(8) . . ?
C26 N1 C27 113.0(2) . . ?
C1 N1 C27 110.35(19) . . ?
C1' N1 C27' 121.7(9) . . ?
C26 N1 C27' 84.9(6) . . ?
C1 N1 C27' 28.5(5) . . ?
C27 N1 C27' 134.8(6) . . ?
C1' N1 C26' 122.3(11) . . ?
C26 N1 C26' 17.5(6) . . ?
C1 N1 C26' 127.7(7) . . ?
C27 N1 C26' 104.6(8) . . ?
C27' N1 C26' 101.2(9) . . ?
C1' N1 H1N 103(2) . . ?
C26 N1 H1N 108.2(19) . . ?
C1 N1 H1N 110.6(19) . . ?
C27 N1 H1N 104(2) . . ?
C27' N1 H1N 109(2) . . ?
C26' N1 H1N 97(2) . . ?
C10 N2 C8 127.00(17) . . ?
C10 N2 H2N 118.8(18) . . ?
C8 N2 H2N 114.2(18) . . ?
C17 N3 C18 128.06(16) . . ?
C17 N3 H3N 116.6(19) . . ?
C18 N3 H3N 114.0(18) . . ?
C3 O1 C2 109.94(18) . . ?
C3 O1 C2' 123.1(5) . . ?
C2 O1 C2' 74.2(4) . . ?
C24 O2 C25 114.5(2) . . ?
O2 C24 C22 109.6(3) . . ?
O2 C24 H24A 109.7 . . ?
C22 C24 H24A 109.7 . . ?
O2 C24 H24B 109.7 . . ?
C22 C24 H24B 109.7 . . ?
H24A C24 H24B 108.2 . . ?
O2 C25 C26 108.1(2) . . ?
O2 C25 H25A 110.1 . . ?
C26 C25 H25A 110.1 . . ?
O2 C25 H25B 110.1 . . ?
C26 C25 H25B 110.1 . . ?
H25A C25 H25B 108.4 . . ?
C24' O2' C25' 114.8(16) . . ?
O2' C24' C22 120.9(19) . . ?
O2' C24' H24C 107.1 . . ?
C22 C24' H24C 107.1 . . ?
O2' C24' H24D 107.1 . . ?
C22 C24' H24D 107.1 . . ?
H24C C24' H24D 106.8 . . ?
O2' C25' C26' 108.6(14) . . ?
O2' C25' H25C 110.0 . . ?
C26' C25' H25C 110.0 . . ?
O2' C25' H25D 110.0 . . ?
C26' C25' H25D 110.0 . . ?
H25C C25' H25D 108.4 . . ?
N1 C1 C2 115.3(2) . . ?
N1 C1 H1A 108.4 . . ?
C2 C1 H1A 108.4 . . ?
N1 C1 H1B 108.4 . . ?
C2 C1 H1B 108.4 . . ?
H1A C1 H1B 107.5 . . ?
O1 C2 C1 109.3(2) . . ?
O1 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
O1 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
N1 C1' C2' 115.4(13) . . ?
N1 C1' H1'1 108.4 . . ?
C2' C1' H1'1 108.4 . . ?
N1 C1' H1'2 108.4 . . ?
C2' C1' H1'2 108.4 . . ?
H1'1 C1' H1'2 107.5 . . ?
O1 C2' C1' 119.0(9) . . ?
O1 C2' H2'1 107.6 . . ?
C1' C2' H2'1 107.6 . . ?
O1 C2' H2'2 107.6 . . ?
C1' C2' H2'2 107.6 . . ?
H2'1 C2' H2'2 107.0 . . ?
O1 C3 C4 110.66(17) . . ?
O1 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
O1 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C9 C4 C5 119.6(2) . . ?
C9 C4 C3 121.36(19) . . ?
C5 C4 C3 119.05(19) . . ?
C6 C5 C4 119.6(2) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C7 121.83(19) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C6 C7 C8 118.7(2) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C7 C8 C9 119.53(18) . . ?
C7 C8 N2 123.86(18) . . ?
C9 C8 N2 116.59(17) . . ?
C4 C9 C8 120.68(18) . . ?
C4 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
O3 C10 N2 124.02(19) . . ?
O3 C10 C11 120.84(19) . . ?
N2 C10 C11 115.14(17) . . ?
C12 C11 C16 119.25(19) . . ?
C12 C11 C10 118.46(18) . . ?
C16 C11 C10 122.27(17) . . ?
C13 C12 C11 120.29(19) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.13(19) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 120.08(19) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 119.55(17) . . ?
C16 C15 C17 123.01(16) . . ?
C14 C15 C17 117.43(17) . . ?
C15 C16 C11 120.66(17) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
O4 C17 N3 124.24(17) . . ?
O4 C17 C15 120.44(16) . . ?
N3 C17 C15 115.30(16) . . ?
C19 C18 C23 119.74(18) . . ?
C19 C18 N3 123.81(17) . . ?
C23 C18 N3 116.45(17) . . ?
C18 C19 C20 118.95(19) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C21 C20 C19 121.35(19) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C22 119.48(19) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C21 C22 C23 119.97(19) . . ?
C21 C22 C24 118.2(2) . . ?
C23 C22 C24 121.8(2) . . ?
C21 C22 C24' 129.4(8) . . ?
C23 C22 C24' 110.1(8) . . ?
C24 C22 C24' 15.3(8) . . ?
C22 C23 C18 120.31(18) . . ?
C22 C23 H23 119.8 . . ?
C18 C23 H23 119.8 . . ?
N1 C26 C25 115.0(3) . . ?
N1 C26 H26A 108.5 . . ?
C25 C26 H26A 108.5 . . ?
N1 C26 H26B 108.5 . . ?
C25 C26 H26B 108.5 . . ?
H26A C26 H26B 107.5 . . ?
C25' C26' N1 110.8(14) . . ?
C25' C26' H26C 109.5 . . ?
N1 C26' H26C 109.5 . . ?
C25' C26' H26D 109.5 . . ?
N1 C26' H26D 109.5 . . ?
H26C C26' H26D 108.1 . . ?
N1 C27 H27A 109.5 . . ?
N1 C27 H27B 109.5 . . ?
N1 C27 H27C 109.5 . . ?
N1 C27' H27D 109.5 . . ?
N1 C27' H27E 109.5 . . ?
H27D C27' H27E 109.5 . . ?
N1 C27' H27F 109.5 . . ?
H27D C27' H27F 109.5 . . ?
H27E C27' H27F 109.5 . . ?
C54 N4 C53 113.93(16) . . ?
C54 N4 C28 111.25(16) . . ?
C53 N4 C28 107.75(17) . . ?
C54 N4 H4N 111(2) . . ?
C53 N4 H4N 105(2) . . ?
C28 N4 H4N 107(2) . . ?
C37 N5 C35 127.66(17) . . ?
C37 N5 H5N 117(2) . . ?
C35 N5 H5N 115(2) . . ?
C44 N6 C45 127.27(18) . . ?
C44 N6 H6N 119.1(19) . . ?
C45 N6 H6N 112.1(19) . . ?
C30 O5 C29 111.1(2) . . ?
C30' O5' C29 102.7(14) . . ?
O5' C30' C31 103.9(16) . . ?
O5' C30' H30C 111.0 . . ?
C31 C30' H30C 111.0 . . ?
O5' C30' H30D 111.0 . . ?
C31 C30' H30D 111.0 . . ?
H30C C30' H30D 109.0 . . ?
C51 O6 C52 112.45(17) . . ?
C29 C28 N4 114.93(18) . . ?
C29 C28 H28A 108.5 . . ?
N4 C28 H28A 108.5 . . ?
C29 C28 H28B 108.5 . . ?
N4 C28 H28B 108.5 . . ?
H28A C28 H28B 107.5 . . ?
O5 C29 C28 108.65(19) . . ?
O5 C29 O5' 32.8(5) . . ?
C28 C29 O5' 133.5(6) . . ?
O5 C29 H29A 110.0 . . ?
C28 C29 H29A 110.0 . . ?
O5' C29 H29A 109.2 . . ?
O5 C29 H29B 110.0 . . ?
C28 C29 H29B 110.0 . . ?
O5' C29 H29B 79.9 . . ?
H29A C29 H29B 108.3 . . ?
O5 C30 C31 109.1(2) . . ?
O5 C30 H30A 109.9 . . ?
C31 C30 H30A 109.9 . . ?
O5 C30 H30B 109.9 . . ?
C31 C30 H30B 109.9 . . ?
H30A C30 H30B 108.3 . . ?
C36 C31 C32 119.5(2) . . ?
C36 C31 C30 121.4(2) . . ?
C32 C31 C30 119.0(2) . . ?
C36 C31 C30' 112.3(9) . . ?
C32 C31 C30' 124.1(9) . . ?
C30 C31 C30' 24.5(9) . . ?
C33 C32 C31 119.8(2) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C32 C33 C34 121.3(2) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 H33 119.4 . . ?
C33 C34 C35 118.9(2) . . ?
C33 C34 H34 120.5 . . ?
C35 C34 H34 120.5 . . ?
C36 C35 C34 119.80(19) . . ?
C36 C35 N5 116.69(17) . . ?
C34 C35 N5 123.51(19) . . ?
C31 C36 C35 120.72(19) . . ?
C31 C36 H36 119.6 . . ?
C35 C36 H36 119.6 . . ?
O7 C37 N5 124.5(2) . . ?
O7 C37 C38 120.75(19) . . ?
N5 C37 C38 114.75(17) . . ?
C43 C38 C39 119.7(2) . . ?
C43 C38 C37 121.92(18) . . ?
C39 C38 C37 118.34(19) . . ?
C40 C39 C38 120.1(2) . . ?
C40 C39 H39 119.9 . . ?
C38 C39 H39 119.9 . . ?
C41 C40 C39 120.2(2) . . ?
C41 C40 H40 119.9 . . ?
C39 C40 H40 119.9 . . ?
C40 C41 C42 120.0(2) . . ?
C40 C41 H41 120.0 . . ?
C42 C41 H41 120.0 . . ?
C41 C42 C43 119.82(19) . . ?
C41 C42 C44 116.97(18) . . ?
C43 C42 C44 123.21(18) . . ?
C38 C43 C42 120.09(18) . . ?
C38 C43 H43 120.0 . . ?
C42 C43 H43 120.0 . . ?
O8 C44 N6 123.6(2) . . ?
O8 C44 C42 120.24(19) . . ?
N6 C44 C42 116.18(17) . . ?
C46 C45 C50 119.87(19) . . ?
C46 C45 N6 123.6(2) . . ?
C50 C45 N6 116.55(18) . . ?
C47 C46 C45 118.8(2) . . ?
C47 C46 H46 120.6 . . ?
C45 C46 H46 120.6 . . ?
C48 C47 C46 121.7(2) . . ?
C48 C47 H47 119.2 . . ?
C46 C47 H47 119.2 . . ?
C47 C48 C49 119.6(2) . . ?
C47 C48 H48 120.2 . . ?
C49 C48 H48 120.2 . . ?
C50 C49 C48 119.4(2) . . ?
C50 C49 C51 121.74(19) . . ?
C48 C49 C51 118.81(19) . . ?
C49 C50 C45 120.63(19) . . ?
C49 C50 H50 119.7 . . ?
C45 C50 H50 119.7 . . ?
O6 C51 C49 110.04(17) . . ?
O6 C51 H51A 109.7 . . ?
C49 C51 H51A 109.7 . . ?
O6 C51 H51B 109.7 . . ?
C49 C51 H51B 109.7 . . ?
H51A C51 H51B 108.2 . . ?
O6 C52 C53 109.86(18) . . ?
O6 C52 H52A 109.7 . . ?
C53 C52 H52A 109.7 . . ?
O6 C52 H52B 109.7 . . ?
C53 C52 H52B 109.7 . . ?
H52A C52 H52B 108.2 . . ?
N4 C53 C52 115.17(19) . . ?
N4 C53 H53A 108.5 . . ?
C52 C53 H53A 108.5 . . ?
N4 C53 H53B 108.5 . . ?
C52 C53 H53B 108.5 . . ?
H53A C53 H53B 107.5 . . ?
N4 C54 H54A 109.5 . . ?
N4 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
N4 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
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
N1 C1' 1.161(14) . ?
N1 C26 1.486(5) . ?
N1 C1 1.494(3) . ?
N1 C27 1.538(3) . ?
N1 C27' 1.649(12) . ?
N1 C26' 1.68(2) . ?
N1 H1N 0.97(3) . ?
N2 C10 1.364(3) . ?
N2 C8 1.406(3) . ?
N2 H2N 0.87(3) . ?
N3 C17 1.360(2) . ?
N3 C18 1.416(2) . ?
N3 H3N 0.87(3) . ?
O1 C3 1.416(3) . ?
O1 C2 1.419(3) . ?
O1 C2' 1.477(11) . ?
O2 C24 1.403(4) . ?
O2 C25 1.416(3) . ?
C24 C22 1.490(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.498(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
O2' C24' 1.11(3) . ?
O2' C25' 1.420(15) . ?
C24' C22 1.65(2) . ?
C24' H24C 0.9900 . ?
C24' H24D 0.9900 . ?
C25' C26' 1.46(2) . ?
C25' H25C 0.9900 . ?
C25' H25D 0.9900 . ?
O3 C10 1.223(2) . ?
O4 C17 1.233(2) . ?
C1 C2 1.502(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C1' C2' 1.494(19) . ?
C1' H1'1 0.9900 . ?
C1' H1'2 0.9900 . ?
C2' H2'1 0.9900 . ?
C2' H2'2 0.9900 . ?
C3 C4 1.509(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C9 1.389(3) . ?
C4 C5 1.397(3) . ?
C5 C6 1.372(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.400(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.400(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.501(3) . ?
C11 C12 1.395(3) . ?
C11 C16 1.398(3) . ?
C12 C13 1.389(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.393(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.395(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(3) . ?
C15 C17 1.500(3) . ?
C16 H16 0.9500 . ?
C18 C19 1.392(3) . ?
C18 C23 1.399(3) . ?
C19 C20 1.394(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.387(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.390(3) . ?
C23 H23 0.9500 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26' H26C 0.9900 . ?
C26' H26D 0.9900 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C27' H27D 0.9800 . ?
C27' H27E 0.9800 . ?
C27' H27F 0.9800 . ?
N4 C54 1.490(3) . ?
N4 C53 1.500(3) . ?
N4 C28 1.505(3) . ?
N4 H4N 0.95(3) . ?
N5 C37 1.363(3) . ?
N5 C35 1.405(3) . ?
N5 H5N 0.83(3) . ?
N6 C44 1.365(3) . ?
N6 C45 1.416(3) . ?
N6 H6N 0.83(3) . ?
O5 C30 1.418(3) . ?
O5 C29 1.430(3) . ?
O5' C30' 1.40(2) . ?
O5' C29 1.509(12) . ?
C30' C31 1.58(3) . ?
C30' H30C 0.9900 . ?
C30' H30D 0.9900 . ?
O6 C51 1.417(3) . ?
O6 C52 1.427(3) . ?
O7 C37 1.221(3) . ?
O8 C44 1.228(2) . ?
C28 C29 1.498(3) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.508(4) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C36 1.388(3) . ?
C31 C32 1.394(3) . ?
C32 C33 1.385(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.391(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.399(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.396(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.500(3) . ?
C38 C43 1.391(3) . ?
C38 C39 1.399(3) . ?
C39 C40 1.388(4) . ?
C39 H39 0.9500 . ?
C40 C41 1.388(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.396(3) . ?
C41 H41 0.9500 . ?
C42 C43 1.397(3) . ?
C42 C44 1.499(3) . ?
C43 H43 0.9500 . ?
C45 C46 1.397(3) . ?
C45 C50 1.399(3) . ?
C46 C47 1.389(3) . ?
C46 H46 0.9500 . ?
C47 C48 1.386(4) . ?
C47 H47 0.9500 . ?
C48 C49 1.393(3) . ?
C48 H48 0.9500 . ?
C49 C50 1.393(3) . ?
C49 C51 1.506(3) . ?
C50 H50 0.9500 . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C52 C53 1.508(3) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
