#------------------------------------------------------------------------------
#$Date: 2025-07-30 08:51:54 +0300 (Wed, 30 Jul 2025) $
#$Revision: 301408 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038336.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_4038336
loop_
_publ_author_name
'Schmidt, Elena Yu'
'Tatarinova, Inna V.'
'Ushakov, Igor A.'
'Vashchenko, Alexander Valentine'
'Trofimov, Boris A.'
_publ_section_title
;
 Oxaazabicyclooctene Oxides, Another Type of Bridgehead Nitrones:
 Diastereoselective Assembly from Acetylene gas, Ketones and Hydroxyl
 Amine.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00742
_journal_year                    2020
_chemical_formula_moiety         'C25 H23 N O2, 0.5(H2 O)'
_chemical_formula_sum            'C25 H24 N O2.5'
_chemical_formula_weight         378.45
_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
;
2019-06-05 # Formatted by publCIF

;
_cell_angle_alpha                102.72(2)
_cell_angle_beta                 92.22(4)
_cell_angle_gamma                109.91(3)
_cell_formula_units_Z            4
_cell_length_a                   10.384(8)
_cell_length_b                   10.986(8)
_cell_length_c                   19.425(14)
_cell_measurement_reflns_used    871
_cell_measurement_temperature    293
_cell_measurement_theta_max      24.5
_cell_measurement_theta_min      2.5
_cell_volume                     2017(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measurement_device_type  'Bruker  D8 Venture'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  No
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            71221
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.170
_diffrn_reflns_theta_min         2.166
_diffrn_source                   IuS
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0970 before and 0.0566 after correction.
The Ratio of minimum to maximum transmission is 0.9222.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_description       prism
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     519
_refine_ls_number_reflns         8164
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0539
_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)+(0.0476P)²+0.7664P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1309
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5200
_reflns_number_total             8164
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00742_si_002.cif
_cod_data_source_block           a_a
_cod_depositor_comments
;

2025-07-29
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C50 H48 N2 O5'
_cod_original_formula_weight         756.90
_cod_original_formula_moiety         '2(C25 H23 N O2), H2 O'
_cod_original_formula_units_Z            2
_cod_database_code               4038336
_shelx_shelxl_version_number     2014/7
_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   0.990
_shelx_estimated_absorpt_t_min   0.985
_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,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b Ternary CH refined with riding coordinates:
 C12(H12), C40(H40)
2.c Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C39(H39A,H39B), C41(H41A,H41B)
2.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26),
  C27(H27), C28(H28), C33(H33), C34(H34), C35(H35), C37(H37), C38(H38),
 C43(H43), C44(H44), C45(H45), C46(H46), C47(H47), C49(H49), C50(H50)
2.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C48(H48A,H48B,H48C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.62038(12) 0.68423(12) 0.03052(6) 0.0339(3) Uani 1 1 d . . . . .
O2 O 0.93694(14) 0.85034(14) 0.13628(7) 0.0466(4) Uani 1 1 d . . . . .
O3 O 0.60182(13) 0.63786(13) 0.47308(7) 0.0352(3) Uani 1 1 d . . . . .
O4 O 0.74066(16) 0.72203(16) 0.32265(8) 0.0536(4) Uani 1 1 d . . . . .
O5 O 0.97201(19) 0.7248(2) 0.24598(11) 0.0772(6) Uani 1 1 d . . . . .
H5A H 0.9617 0.7609 0.2127 0.116 Uiso 1 1 d G . . . .
H5B H 0.9041 0.7240 0.2692 0.116 Uiso 1 1 d G . . . .
N1 N 0.80587(16) 0.79854(15) 0.11244(8) 0.0350(4) Uani 1 1 d . . . . .
N2 N 0.72412(17) 0.69791(16) 0.38485(9) 0.0382(4) Uani 1 1 d . . . . .
C1 C 0.9937(3) 0.7391(3) -0.12156(13) 0.0684(8) Uani 1 1 d . . . . .
H1 H 1.0468 0.7528 -0.1586 0.082 Uiso 1 1 calc R . . . .
C2 C 0.9448(2) 0.8357(3) -0.08818(13) 0.0599(7) Uani 1 1 d . . . . .
H2 H 0.9641 0.9147 -0.1026 0.072 Uiso 1 1 calc R . . . .
C3 C 0.8670(2) 0.8143(2) -0.03318(11) 0.0475(5) Uani 1 1 d . . . . .
H3 H 0.8336 0.8793 -0.0107 0.057 Uiso 1 1 calc R . . . .
C4 C 0.83762(19) 0.6976(2) -0.01065(10) 0.0372(5) Uani 1 1 d . . . . .
C5 C 0.75116(19) 0.67885(18) 0.04948(10) 0.0327(4) Uani 1 1 d . . . . .
C6 C 0.5716(2) 0.72300(19) 0.09781(10) 0.0334(4) Uani 1 1 d . . . . .
C7 C 0.4569(2) 0.77423(19) 0.08555(11) 0.0367(5) Uani 1 1 d . . . . .
C8 C 0.4418(2) 0.8181(2) 0.02577(12) 0.0506(6) Uani 1 1 d . . . . .
H8 H 0.5063 0.8217 -0.0063 0.061 Uiso 1 1 calc R . . . .
C9 C 0.3314(3) 0.8571(3) 0.01284(14) 0.0670(7) Uani 1 1 d . . . . .
H9 H 0.3225 0.8861 -0.0280 0.080 Uiso 1 1 calc R . . . .
C10 C 0.2356(3) 0.8534(3) 0.05932(17) 0.0679(8) Uani 1 1 d . . . . .
H10 H 0.1606 0.8778 0.0499 0.081 Uiso 1 1 calc R . . . .
C11 C 0.7306(2) 0.55481(19) 0.07681(10) 0.0367(5) Uani 1 1 d . . . . .
H11A H 0.8200 0.5525 0.0914 0.044 Uiso 1 1 calc R . . . .
H11B H 0.6835 0.4758 0.0387 0.044 Uiso 1 1 calc R . . . .
C12 C 0.6456(2) 0.55275(19) 0.14022(10) 0.0358(5) Uani 1 1 d . . . . .
H12 H 0.7070 0.6188 0.1813 0.043 Uiso 1 1 calc R . . . .
C13 C 0.5257(2) 0.59892(19) 0.12766(11) 0.0374(5) Uani 1 1 d . . . . .
H13A H 0.4890 0.6193 0.1722 0.045 Uiso 1 1 calc R . . . .
H13B H 0.4527 0.5273 0.0945 0.045 Uiso 1 1 calc R . . . .
C14 C 0.3613(3) 0.7746(3) 0.13290(15) 0.0624(7) Uani 1 1 d . . . . .
H14 H 0.3709 0.7482 0.1745 0.075 Uiso 1 1 calc R . . . .
C15 C 0.2515(3) 0.8136(3) 0.11963(18) 0.0737(8) Uani 1 1 d . . . . .
H15 H 0.1879 0.8125 0.1522 0.088 Uiso 1 1 calc R . . . .
C16 C 0.7045(2) 0.82456(19) 0.14053(10) 0.0351(5) Uani 1 1 d . . . . .
C17 C 0.7217(3) 0.9218(2) 0.20854(12) 0.0540(6) Uani 1 1 d . . . . .
H17A H 0.8147 0.9850 0.2180 0.081 Uiso 1 1 calc GR . . . .
H17B H 0.7032 0.8760 0.2459 0.081 Uiso 1 1 calc GR . . . .
H17C H 0.6586 0.9678 0.2063 0.081 Uiso 1 1 calc GR . . . .
C18 C 0.6031(2) 0.4182(2) 0.15908(10) 0.0389(5) Uani 1 1 d . . . . .
C19 C 0.4689(2) 0.3279(2) 0.14641(12) 0.0488(6) Uani 1 1 d . . . . .
H19 H 0.3999 0.3487 0.1254 0.059 Uiso 1 1 calc R . . . .
C20 C 0.4359(3) 0.2070(2) 0.16452(13) 0.0611(7) Uani 1 1 d . . . . .
H20 H 0.3450 0.1475 0.1554 0.073 Uiso 1 1 calc R . . . .
C21 C 0.5350(3) 0.1743(3) 0.19553(14) 0.0675(8) Uani 1 1 d . . . . .
H21 H 0.5123 0.0928 0.2076 0.081 Uiso 1 1 calc R . . . .
C22 C 0.6694(3) 0.2630(3) 0.20885(13) 0.0628(7) Uani 1 1 d . . . . .
H22 H 0.7375 0.2409 0.2299 0.075 Uiso 1 1 calc R . . . .
C23 C 0.7040(3) 0.3850(2) 0.19117(12) 0.0507(6) Uani 1 1 d . . . . .
H23 H 0.7949 0.4445 0.2008 0.061 Uiso 1 1 calc R . . . .
C24 C 0.8867(2) 0.6012(2) -0.04494(12) 0.0518(6) Uani 1 1 d . . . . .
H24 H 0.8675 0.5220 -0.0308 0.062 Uiso 1 1 calc R . . . .
C25 C 0.9642(3) 0.6225(3) -0.10025(13) 0.0685(8) Uani 1 1 d . . . . .
H25 H 0.9967 0.5571 -0.1233 0.082 Uiso 1 1 calc R . . . .
C26 C 0.8439(3) 0.9072(3) 0.70820(13) 0.0649(7) Uani 1 1 d . . . . .
H26 H 0.8659 0.9611 0.7544 0.078 Uiso 1 1 calc R . . . .
C27 C 0.8159(3) 0.9563(2) 0.65264(14) 0.0615(7) Uani 1 1 d . . . . .
H27 H 0.8174 1.0435 0.6612 0.074 Uiso 1 1 calc R . . . .
C28 C 0.7855(2) 0.8770(2) 0.58439(12) 0.0494(6) Uani 1 1 d . . . . .
H28 H 0.7663 0.9113 0.5471 0.059 Uiso 1 1 calc R . . . .
C29 C 0.7830(2) 0.7473(2) 0.57018(11) 0.0379(5) Uani 1 1 d . . . . .
C30 C 0.74587(19) 0.66251(19) 0.49482(10) 0.0349(5) Uani 1 1 d . . . . .
C31 C 0.5872(2) 0.60222(19) 0.39798(10) 0.0344(4) Uani 1 1 d . . . . .
C32 C 0.4656(2) 0.6272(2) 0.36875(11) 0.0384(5) Uani 1 1 d . . . . .
C33 C 0.4185(2) 0.7199(2) 0.40945(13) 0.0526(6) Uani 1 1 d . . . . .
H33 H 0.4656 0.7698 0.4540 0.063 Uiso 1 1 calc R . . . .
C34 C 0.3030(3) 0.7389(3) 0.38482(16) 0.0683(7) Uani 1 1 d . . . . .
H34 H 0.2714 0.8001 0.4133 0.082 Uiso 1 1 calc R . . . .
C35 C 0.2337(3) 0.6688(3) 0.31879(17) 0.0701(8) Uani 1 1 d . . . . .
H35 H 0.1559 0.6825 0.3021 0.084 Uiso 1 1 calc R . . . .
C36 C 0.8147(2) 0.73201(19) 0.43992(11) 0.0377(5) Uani 1 1 d . . . . .
C37 C 0.3953(2) 0.5571(2) 0.30236(12) 0.0534(6) Uani 1 1 d . . . . .
H37 H 0.4255 0.4949 0.2739 0.064 Uiso 1 1 calc R . . . .
C38 C 0.2802(3) 0.5788(3) 0.27778(14) 0.0656(7) Uani 1 1 d . . . . .
H38 H 0.2340 0.5313 0.2327 0.079 Uiso 1 1 calc R . . . .
C39 C 0.5879(2) 0.46145(19) 0.37293(11) 0.0401(5) Uani 1 1 d . . . . .
H39A H 0.5816 0.4378 0.3214 0.048 Uiso 1 1 calc R . . . .
H39B H 0.5075 0.3993 0.3866 0.048 Uiso 1 1 calc R . . . .
C40 C 0.7191(2) 0.44797(19) 0.40455(11) 0.0394(5) Uani 1 1 d . . . . .
H40 H 0.7942 0.4889 0.3784 0.047 Uiso 1 1 calc R . . . .
C41 C 0.7602(2) 0.52563(19) 0.48309(11) 0.0390(5) Uani 1 1 d . . . . .
H41A H 0.7017 0.4746 0.5123 0.047 Uiso 1 1 calc R . . . .
H41B H 0.8550 0.5373 0.4976 0.047 Uiso 1 1 calc R . . . .
C42 C 0.7096(2) 0.3046(2) 0.39708(11) 0.0418(5) Uani 1 1 d . . . . .
C43 C 0.5880(3) 0.2033(2) 0.39905(16) 0.0698(8) Uani 1 1 d . . . . .
H43 H 0.5071 0.2217 0.4030 0.084 Uiso 1 1 calc R . . . .
C44 C 0.5841(3) 0.0750(3) 0.39519(17) 0.0822(9) Uani 1 1 d . . . . .
H44 H 0.5012 0.0082 0.3971 0.099 Uiso 1 1 calc R . . . .
C45 C 0.7014(3) 0.0457(3) 0.38857(13) 0.0664(7) Uani 1 1 d . . . . .
H45 H 0.6987 -0.0407 0.3862 0.080 Uiso 1 1 calc R . . . .
C46 C 0.8220(3) 0.1435(3) 0.38553(14) 0.0654(7) Uani 1 1 d . . . . .
H46 H 0.9020 0.1239 0.3805 0.078 Uiso 1 1 calc R . . . .
C47 C 0.8261(2) 0.2715(2) 0.38985(13) 0.0562(6) Uani 1 1 d . . . . .
H47 H 0.9096 0.3375 0.3879 0.067 Uiso 1 1 calc R . . . .
C48 C 0.9615(2) 0.8066(3) 0.44052(14) 0.0603(7) Uani 1 1 d . . . . .
H48A H 1.0027 0.7493 0.4127 0.090 Uiso 1 1 calc GR . . . .
H48B H 1.0063 0.8377 0.4886 0.090 Uiso 1 1 calc GR . . . .
H48C H 0.9720 0.8816 0.4207 0.090 Uiso 1 1 calc GR . . . .
C49 C 0.8101(2) 0.6986(2) 0.62689(12) 0.0500(6) Uani 1 1 d . . . . .
H49 H 0.8086 0.6115 0.6189 0.060 Uiso 1 1 calc R . . . .
C50 C 0.8393(3) 0.7787(3) 0.69510(13) 0.0659(7) Uani 1 1 d . . . . .
H50 H 0.8560 0.7445 0.7328 0.079 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'
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
C5 O1 C6 104.62(14) . . ?
C31 O3 C30 104.80(14) . . ?
H5A O5 H5B 104.5 . . ?
O2 N1 C5 120.79(15) . . ?
C16 N1 O2 128.73(17) . . ?
C16 N1 C5 109.92(16) . . ?
O4 N2 C31 120.52(16) . . ?
C36 N2 O4 129.29(17) . . ?
C36 N2 C31 109.68(16) . . ?
C2 C1 H1 120.0 . . ?
C25 C1 H1 120.0 . . ?
C25 C1 C2 120.0(2) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.3(2) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.3(2) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 119.08(18) . . ?
C24 C4 C3 118.7(2) . . ?
C24 C4 C5 122.18(19) . . ?
O1 C5 N1 100.36(14) . . ?
O1 C5 C4 109.58(15) . . ?
O1 C5 C11 109.09(15) . . ?
N1 C5 C11 107.57(16) . . ?
C4 C5 N1 111.21(16) . . ?
C4 C5 C11 117.62(16) . . ?
O1 C6 C7 109.12(15) . . ?
O1 C6 C13 106.37(15) . . ?
O1 C6 C16 100.51(15) . . ?
C7 C6 C13 113.42(16) . . ?
C7 C6 C16 116.42(17) . . ?
C16 C6 C13 109.76(16) . . ?
C8 C7 C6 121.17(18) . . ?
C8 C7 C14 117.7(2) . . ?
C14 C7 C6 121.10(19) . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.7(2) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.5 . . ?
C15 C10 C9 119.1(2) . . ?
C15 C10 H10 120.5 . . ?
C5 C11 H11A 109.3 . . ?
C5 C11 H11B 109.3 . . ?
C5 C11 C12 111.56(15) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C11 C12 H12 106.6 . . ?
C13 C12 C11 110.97(16) . . ?
C13 C12 H12 106.6 . . ?
C18 C12 C11 111.57(16) . . ?
C18 C12 H12 106.6 . . ?
C18 C12 C13 114.01(17) . . ?
C6 C13 H13A 109.4 . . ?
C6 C13 H13B 109.4 . . ?
C12 C13 C6 111.31(16) . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C7 C14 H14 119.4 . . ?
C7 C14 C15 121.2(2) . . ?
C15 C14 H14 119.4 . . ?
C10 C15 C14 120.5(2) . . ?
C10 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
N1 C16 C6 107.78(17) . . ?
N1 C16 C17 123.37(19) . . ?
C17 C16 C6 128.10(18) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C12 123.37(19) . . ?
C19 C18 C23 118.2(2) . . ?
C23 C18 C12 118.4(2) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.0(2) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.6(3) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 120.3 . . ?
C20 C21 C22 119.4(2) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 H22 119.7 . . ?
C21 C22 C23 120.7(2) . . ?
C23 C22 H22 119.7 . . ?
C18 C23 H23 120.0 . . ?
C22 C23 C18 120.1(2) . . ?
C22 C23 H23 120.0 . . ?
C4 C24 H24 120.0 . . ?
C25 C24 C4 120.0(2) . . ?
C25 C24 H24 120.0 . . ?
C1 C25 C24 120.6(2) . . ?
C1 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C27 C26 H26 120.3 . . ?
C50 C26 H26 120.3 . . ?
C50 C26 C27 119.3(2) . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.2(2) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 119.4 . . ?
C27 C28 C29 121.1(2) . . ?
C29 C28 H28 119.4 . . ?
C28 C29 C30 119.48(18) . . ?
C28 C29 C49 118.1(2) . . ?
C49 C29 C30 122.42(19) . . ?
O3 C30 C29 107.86(15) . . ?
O3 C30 C36 100.88(15) . . ?
O3 C30 C41 106.60(15) . . ?
C29 C30 C36 114.79(17) . . ?
C29 C30 C41 115.72(17) . . ?
C36 C30 C41 109.59(16) . . ?
O3 C31 N2 100.27(15) . . ?
O3 C31 C32 109.97(15) . . ?
O3 C31 C39 108.90(15) . . ?
C32 C31 N2 112.63(16) . . ?
C32 C31 C39 116.36(17) . . ?
C39 C31 N2 107.47(16) . . ?
C33 C32 C31 120.1(2) . . ?
C37 C32 C31 121.67(19) . . ?
C37 C32 C33 118.2(2) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 C32 120.7(2) . . ?
C34 C33 H33 119.6 . . ?
C33 C34 H34 119.7 . . ?
C35 C34 C33 120.7(3) . . ?
C35 C34 H34 119.7 . . ?
C34 C35 H35 120.4 . . ?
C38 C35 C34 119.2(2) . . ?
C38 C35 H35 120.4 . . ?
N2 C36 C30 107.90(17) . . ?
N2 C36 C48 123.30(19) . . ?
C48 C36 C30 128.05(19) . . ?
C32 C37 H37 119.8 . . ?
C32 C37 C38 120.4(2) . . ?
C38 C37 H37 119.8 . . ?
C35 C38 C37 120.8(3) . . ?
C35 C38 H38 119.6 . . ?
C37 C38 H38 119.6 . . ?
C31 C39 H39A 109.2 . . ?
C31 C39 H39B 109.2 . . ?
C31 C39 C40 112.01(17) . . ?
H39A C39 H39B 107.9 . . ?
C40 C39 H39A 109.2 . . ?
C40 C39 H39B 109.2 . . ?
C39 C40 H40 107.1 . . ?
C41 C40 C39 111.33(16) . . ?
C41 C40 H40 107.1 . . ?
C42 C40 C39 114.11(17) . . ?
C42 C40 H40 107.1 . . ?
C42 C40 C41 109.65(16) . . ?
C30 C41 C40 111.15(16) . . ?
C30 C41 H41A 109.4 . . ?
C30 C41 H41B 109.4 . . ?
C40 C41 H41A 109.4 . . ?
C40 C41 H41B 109.4 . . ?
H41A C41 H41B 108.0 . . ?
C43 C42 C40 122.6(2) . . ?
C43 C42 C47 117.1(2) . . ?
C47 C42 C40 120.3(2) . . ?
C42 C43 H43 119.5 . . ?
C42 C43 C44 121.1(2) . . ?
C44 C43 H43 119.5 . . ?
C43 C44 H44 119.8 . . ?
C45 C44 C43 120.4(3) . . ?
C45 C44 H44 119.8 . . ?
C44 C45 H45 120.2 . . ?
C46 C45 C44 119.5(2) . . ?
C46 C45 H45 120.2 . . ?
C45 C46 H46 119.9 . . ?
C45 C46 C47 120.2(2) . . ?
C47 C46 H46 119.9 . . ?
C42 C47 H47 119.1 . . ?
C46 C47 C42 121.7(2) . . ?
C46 C47 H47 119.1 . . ?
C36 C48 H48A 109.5 . . ?
C36 C48 H48B 109.5 . . ?
C36 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C29 C49 H49 119.9 . . ?
C50 C49 C29 120.3(2) . . ?
C50 C49 H49 119.9 . . ?
C26 C50 C49 121.1(2) . . ?
C26 C50 H50 119.5 . . ?
C49 C50 H50 119.5 . . ?
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 C5 1.417(2) . ?
O1 C6 1.449(2) . ?
O2 N1 1.303(2) . ?
O3 C30 1.454(2) . ?
O3 C31 1.412(2) . ?
O4 N2 1.298(2) . ?
O5 H5A 0.8501 . ?
O5 H5B 0.8499 . ?
N1 C5 1.509(3) . ?
N1 C16 1.292(3) . ?
N2 C31 1.523(3) . ?
N2 C36 1.295(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.377(4) . ?
C1 C25 1.372(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(3) . ?
C4 C5 1.508(3) . ?
C4 C24 1.381(3) . ?
C5 C11 1.521(3) . ?
C6 C7 1.511(3) . ?
C6 C13 1.533(3) . ?
C6 C16 1.514(3) . ?
C7 C8 1.375(3) . ?
C7 C14 1.380(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.385(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.365(4) . ?
C10 H10 0.9300 . ?
C10 C15 1.361(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.542(3) . ?
C12 H12 0.9800 . ?
C12 C13 1.526(3) . ?
C12 C18 1.523(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14 0.9300 . ?
C14 C15 1.381(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.465(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.382(3) . ?
C18 C23 1.390(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.382(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.361(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.378(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.388(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C24 C25 1.381(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C26 C27 1.371(4) . ?
C26 C50 1.361(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.374(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.382(3) . ?
C29 C30 1.507(3) . ?
C29 C49 1.384(3) . ?
C30 C36 1.509(3) . ?
C30 C41 1.529(3) . ?
C31 C32 1.498(3) . ?
C31 C39 1.518(3) . ?
C32 C33 1.384(3) . ?
C32 C37 1.377(3) . ?
C33 H33 0.9300 . ?
C33 C34 1.372(3) . ?
C34 H34 0.9300 . ?
C34 C35 1.368(4) . ?
C35 H35 0.9300 . ?
C35 C38 1.361(4) . ?
C36 C48 1.462(3) . ?
C37 H37 0.9300 . ?
C37 C38 1.383(3) . ?
C38 H38 0.9300 . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C39 C40 1.539(3) . ?
C40 H40 0.9800 . ?
C40 C41 1.538(3) . ?
C40 C42 1.518(3) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 C43 1.379(3) . ?
C42 C47 1.380(3) . ?
C43 H43 0.9300 . ?
C43 C44 1.382(4) . ?
C44 H44 0.9300 . ?
C44 C45 1.365(4) . ?
C45 H45 0.9300 . ?
C45 C46 1.358(4) . ?
C46 H46 0.9300 . ?
C46 C47 1.376(3) . ?
C47 H47 0.9300 . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C49 H49 0.9300 . ?
C49 C50 1.377(3) . ?
C50 H50 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 C5 C11 C12 -57.0(2) . . . . ?
O1 C6 C7 C8 -20.5(3) . . . . ?
O1 C6 C7 C14 157.5(2) . . . . ?
O1 C6 C13 C12 61.0(2) . . . . ?
O1 C6 C16 N1 -23.66(19) . . . . ?
O1 C6 C16 C17 166.18(19) . . . . ?
O2 N1 C5 O1 -163.36(14) . . . . ?
O2 N1 C5 C4 -47.5(2) . . . . ?
O2 N1 C5 C11 82.64(19) . . . . ?
O2 N1 C16 C6 -171.52(16) . . . . ?
O2 N1 C16 C17 -0.8(3) . . . . ?
O3 C30 C36 N2 -23.22(19) . . . . ?
O3 C30 C36 C48 166.6(2) . . . . ?
O3 C30 C41 C40 59.8(2) . . . . ?
O3 C31 C32 C33 23.9(3) . . . . ?
O3 C31 C32 C37 -154.20(19) . . . . ?
O3 C31 C39 C40 -56.7(2) . . . . ?
O4 N2 C31 O3 -163.03(15) . . . . ?
O4 N2 C31 C32 -46.2(2) . . . . ?
O4 N2 C31 C39 83.3(2) . . . . ?
O4 N2 C36 C30 -172.02(18) . . . . ?
O4 N2 C36 C48 -1.2(3) . . . . ?
N1 C5 C11 C12 51.1(2) . . . . ?
N2 C31 C32 C33 -87.0(2) . . . . ?
N2 C31 C32 C37 94.9(2) . . . . ?
N2 C31 C39 C40 51.1(2) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C1 C25 C24 -0.6(4) . . . . ?
C2 C3 C4 C5 -179.6(2) . . . . ?
C2 C3 C4 C24 -0.7(3) . . . . ?
C3 C4 C5 O1 59.5(2) . . . . ?
C3 C4 C5 N1 -50.5(2) . . . . ?
C3 C4 C5 C11 -175.15(18) . . . . ?
C3 C4 C24 C25 0.4(3) . . . . ?
C4 C5 C11 C12 177.50(16) . . . . ?
C4 C24 C25 C1 0.2(4) . . . . ?
C5 O1 C6 C7 162.15(15) . . . . ?
C5 O1 C6 C13 -75.15(17) . . . . ?
C5 O1 C6 C16 39.24(17) . . . . ?
C5 N1 C16 C6 -0.2(2) . . . . ?
C5 N1 C16 C17 170.57(18) . . . . ?
C5 C4 C24 C25 179.3(2) . . . . ?
C5 C11 C12 C13 41.5(2) . . . . ?
C5 C11 C12 C18 169.79(16) . . . . ?
C6 O1 C5 N1 -39.04(16) . . . . ?
C6 O1 C5 C4 -156.13(15) . . . . ?
C6 O1 C5 C11 73.79(17) . . . . ?
C6 C7 C8 C9 176.0(2) . . . . ?
C6 C7 C14 C15 -175.9(2) . . . . ?
C7 C6 C13 C12 -179.04(16) . . . . ?
C7 C6 C16 N1 -141.32(17) . . . . ?
C7 C6 C16 C17 48.5(3) . . . . ?
C7 C8 C9 C10 0.3(4) . . . . ?
C7 C14 C15 C10 -0.4(4) . . . . ?
C8 C7 C14 C15 2.1(4) . . . . ?
C8 C9 C10 C15 1.4(4) . . . . ?
C9 C10 C15 C14 -1.4(4) . . . . ?
C11 C12 C13 C6 -44.2(2) . . . . ?
C11 C12 C18 C19 -108.8(2) . . . . ?
C11 C12 C18 C23 71.7(2) . . . . ?
C12 C18 C19 C20 179.9(2) . . . . ?
C12 C18 C23 C22 -179.69(19) . . . . ?
C13 C6 C7 C8 -138.8(2) . . . . ?
C13 C6 C7 C14 39.1(3) . . . . ?
C13 C6 C16 N1 88.14(19) . . . . ?
C13 C6 C16 C17 -82.0(2) . . . . ?
C13 C12 C18 C19 17.8(3) . . . . ?
C13 C12 C18 C23 -161.65(18) . . . . ?
C14 C7 C8 C9 -2.1(3) . . . . ?
C16 N1 C5 O1 24.48(19) . . . . ?
C16 N1 C5 C4 140.36(17) . . . . ?
C16 N1 C5 C11 -89.51(18) . . . . ?
C16 C6 C7 C8 92.4(2) . . . . ?
C16 C6 C7 C14 -89.7(2) . . . . ?
C16 C6 C13 C12 -46.9(2) . . . . ?
C18 C12 C13 C6 -171.17(16) . . . . ?
C18 C19 C20 C21 0.2(4) . . . . ?
C19 C18 C23 C22 0.8(3) . . . . ?
C19 C20 C21 C22 0.0(4) . . . . ?
C20 C21 C22 C23 0.2(4) . . . . ?
C21 C22 C23 C18 -0.6(4) . . . . ?
C23 C18 C19 C20 -0.6(3) . . . . ?
C24 C4 C5 O1 -119.3(2) . . . . ?
C24 C4 C5 N1 130.6(2) . . . . ?
C24 C4 C5 C11 6.0(3) . . . . ?
C25 C1 C2 C3 0.4(4) . . . . ?
C26 C27 C28 C29 -0.2(4) . . . . ?
C27 C26 C50 C49 1.6(4) . . . . ?
C27 C28 C29 C30 178.6(2) . . . . ?
C27 C28 C29 C49 0.9(3) . . . . ?
C28 C29 C30 O3 -66.8(2) . . . . ?
C28 C29 C30 C36 44.7(3) . . . . ?
C28 C29 C30 C41 173.96(18) . . . . ?
C28 C29 C49 C50 -0.4(3) . . . . ?
C29 C30 C36 N2 -138.87(18) . . . . ?
C29 C30 C36 C48 50.9(3) . . . . ?
C29 C30 C41 C40 179.77(16) . . . . ?
C29 C49 C50 C26 -0.9(4) . . . . ?
C30 O3 C31 N2 -38.60(16) . . . . ?
C30 O3 C31 C32 -157.40(15) . . . . ?
C30 O3 C31 C39 74.01(18) . . . . ?
C30 C29 C49 C50 -177.9(2) . . . . ?
C31 O3 C30 C29 159.68(15) . . . . ?
C31 O3 C30 C36 38.98(17) . . . . ?
C31 O3 C30 C41 -75.45(17) . . . . ?
C31 N2 C36 C30 -0.3(2) . . . . ?
C31 N2 C36 C48 170.47(19) . . . . ?
C31 C32 C33 C34 -176.7(2) . . . . ?
C31 C32 C37 C38 177.6(2) . . . . ?
C31 C39 C40 C41 40.4(2) . . . . ?
C31 C39 C40 C42 165.14(16) . . . . ?
C32 C31 C39 C40 178.42(16) . . . . ?
C32 C33 C34 C35 -1.5(4) . . . . ?
C32 C37 C38 C35 -0.4(4) . . . . ?
C33 C32 C37 C38 -0.5(3) . . . . ?
C33 C34 C35 C38 0.5(4) . . . . ?
C34 C35 C38 C37 0.5(4) . . . . ?
C36 N2 C31 O3 24.41(19) . . . . ?
C36 N2 C31 C32 141.25(18) . . . . ?
C36 N2 C31 C39 -89.30(19) . . . . ?
C36 C30 C41 C40 -48.5(2) . . . . ?
C37 C32 C33 C34 1.5(3) . . . . ?
C39 C31 C32 C33 148.3(2) . . . . ?
C39 C31 C32 C37 -29.8(3) . . . . ?
C39 C40 C41 C30 -42.7(2) . . . . ?
C39 C40 C42 C43 -33.0(3) . . . . ?
C39 C40 C42 C47 148.7(2) . . . . ?
C40 C42 C43 C44 -177.2(2) . . . . ?
C40 C42 C47 C46 177.6(2) . . . . ?
C41 C30 C36 N2 88.9(2) . . . . ?
C41 C30 C36 C48 -81.3(3) . . . . ?
C41 C40 C42 C43 92.6(3) . . . . ?
C41 C40 C42 C47 -85.6(2) . . . . ?
C42 C40 C41 C30 -169.89(16) . . . . ?
C42 C43 C44 C45 -0.7(5) . . . . ?
C43 C42 C47 C46 -0.7(4) . . . . ?
C43 C44 C45 C46 -0.3(5) . . . . ?
C44 C45 C46 C47 0.7(4) . . . . ?
C45 C46 C47 C42 -0.2(4) . . . . ?
C47 C42 C43 C44 1.1(4) . . . . ?
C49 C29 C30 O3 110.7(2) . . . . ?
C49 C29 C30 C36 -137.7(2) . . . . ?
C49 C29 C30 C41 -8.5(3) . . . . ?
C50 C26 C27 C28 -1.0(4) . . . . ?
