#------------------------------------------------------------------------------
#$Date: 2024-05-07 01:38:37 +0200 (Tue 07 de May de 2024) $
#$Revision: 291745 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/85/7248593.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_7248593
loop_
_publ_author_name
'Mele, Francesco'
'Constantin, Ana Maria'
'Sacchelli, Filippo'
'Schiroli, Debora'
'Mazzeo, Paolo Pio'
'Maestri, Giovanni'
'Motti, Elena'
'Maggi, Raimondo'
'Mancuso, Raffaella'
'Gabriele, Bartolo'
'Pancrazzi, francesco'
'Della Ca', Nicola'
_publ_section_title
;
 Sequential Glaser reaction-diastereoselective cyclocarboxylation of
 propargylamines with CO2: A green catalytic access to
 bis-oxazolidinonedienes and their topochemical polymerization
;
_journal_name_full               'Green Chemistry'
_journal_paper_doi               10.1039/D4GC00818A
_journal_year                    2024
_chemical_formula_moiety         'C36 H36 N3 O9'
_chemical_formula_sum            'C36 H36 N3 O9'
_chemical_formula_weight         654.68
_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   geom
_audit_creation_date             2024-02-10
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-02-10 deposited with the CCDC.	2024-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                97.433(5)
_cell_angle_beta                 91.503(4)
_cell_angle_gamma                92.772(4)
_cell_formula_units_Z            2
_cell_length_a                   6.0202(3)
_cell_length_b                   13.4077(7)
_cell_length_c                   19.4725(12)
_cell_measurement_reflns_used    4278
_cell_measurement_temperature    293.00(10)
_cell_measurement_theta_max      66.5710
_cell_measurement_theta_min      4.5500
_cell_volume                     1555.89(15)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (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 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ   -349.73  10.27   0.80   80.00 -97.45-107.50 -31.50    --   450
  2  ω    212.57 326.97   0.80   80.00    -- -107.50  89.85  47.34  143
  3  ω    212.57 326.97   0.80   80.00    -- -107.50  89.85-112.66  143
  4  φ    -10.27 349.73   0.80   56.00  37.96  48.14  31.50    --   450
  5  ω    212.57 326.97   0.80   80.00    -- -107.50  89.85 167.34  143
  6  ω     -7.25  87.95   0.80   56.00    --   48.14 -89.85  83.67  119
  7  ω    212.57 326.97   0.80   80.00    -- -107.50  89.85 -32.67  143
  8  φ    -10.27 349.73   0.80   80.00 -21.69-107.50  31.50    --   450
  9  φ   -339.92  20.08   0.80   64.00 -55.51 -77.50 -59.25    --   450
 10  ω    212.57 326.97   0.80   80.00    -- -107.50  89.85 -72.67  143
 11  φ   -339.92  20.08   0.80   80.00 -85.51-107.50 -59.25    --   450
 12  ω    212.57 326.97   0.80   80.00    -- -107.50  89.85 127.33  143
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1104
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            27348
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         3.329
_exptl_absorpt_coefficient_mu    0.837
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.397
_exptl_crystal_description       needle
_exptl_crystal_F_000             690
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         5448
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1246
_refine_ls_R_factor_gt           0.0919
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1682P)²+0.6499P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2498
_refine_ls_wR_factor_ref         0.2952
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3461
_reflns_number_total             5448
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4gc00818a2.cif
_cod_data_source_block           5b
_cod_database_code               7248593
_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   0.975
_shelx_estimated_absorpt_t_min   0.850
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O48B-C49B
 1.4 with sigma of 0.02
 C41B-C42A \\sim C41B-C42B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C49B) = Uanis(O48B) = Uanis(C45B) = Uanis(C44B) = Uanis(C43B) =
Uanis(C42B) = Uanis(C47B) = Uanis(C46B)
4. Others
 Fixed Sof: H41A(0.85) H41B(0.85) H41C(0.15) H41D(0.15) O48A(0.85) C42A(0.85)
 C43A(0.85) H43A(0.85) C49A(0.85) H49A(0.85) H49B(0.85) H49C(0.85) C45A(0.85)
 C44A(0.85) H44A(0.85) C46A(0.85) H46A(0.85) C47A(0.85) H47A(0.85) O48B(0.15)
 C43B(0.15) H43B(0.15) C44B(0.15) H44B(0.15) C45B(0.15) C46B(0.15) H46B(0.15)
 C47B(0.15) H47B(0.15) C42B(0.15) C49B(0.15) H49D(0.15) H49E(0.15) H49F(0.15)
5.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C22(H22A,H22B), C40(H40A,H40B), C24(H24A,H24B), C9(H9A,H9B),
 C41B(H41A,H41B), C41B(H41C,H41D)
5.b Aromatic/amide H refined with riding coordinates:
 C34(H34), C17(H17), C33(H33), C5(H5), C26(H26), C30(H30), C4(H4), C27(H27),
 C29(H29), C8(H8), C7(H7), C43A(H43A), C44A(H44A), C46A(H46A), C47A(H47A),
 C43B(H43B), C44B(H44B), C46B(H46B), C47B(H47B)
5.c Fitted hexagon refined as free rotating group:
 C43B(C44B,C45B,C46B,C47B,C42B)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C32(H32A,H32B,H32C), C49A(H49A,H49B,H49C), C49B(H49D,H49E,
 H49F)
;
_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
- Detector area scaling
;
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
O31 O 0.0924(5) 0.9248(3) 0.07218(16) 0.0700(9) Uani 1 1 d . . . . .
O2 O 0.5623(5) 0.7364(3) 0.92837(17) 0.0709(9) Uani 1 1 d . . . . .
O15 O 0.0901(3) 0.84200(15) 0.55604(12) 0.0342(5) Uani 1 1 d . . . . .
O18 O 0.5770(3) 0.82471(15) 0.44754(11) 0.0341(5) Uani 1 1 d . . . . .
O36 O 0.2529(3) 0.49338(15) 0.44993(12) 0.0352(6) Uani 1 1 d . . . . .
O38 O 0.3773(4) 0.39166(19) 0.35963(14) 0.0546(7) Uani 1 1 d . . . . .
O20 O 0.6857(4) 0.71967(19) 0.35701(14) 0.0511(7) Uani 1 1 d . . . . .
O12 O -0.0205(4) 0.94895(19) 0.64549(14) 0.0511(7) Uani 1 1 d . . . . .
N10 N 0.3381(4) 0.8978(2) 0.63977(15) 0.0397(7) Uani 1 1 d . . . . .
N21 N 0.3272(4) 0.7705(2) 0.36379(15) 0.0399(7) Uani 1 1 d . . . . .
N39 N 0.0170(5) 0.4417(2) 0.36214(15) 0.0434(7) Uani 1 1 d . . . . .
C34 C 0.0717(5) 0.6425(2) 0.49792(17) 0.0334(7) Uani 1 1 d . . . . .
H34 H -0.0549 0.6778 0.5084 0.040 Uiso 1 1 calc R U . . .
C19 C 0.5395(5) 0.7660(2) 0.38478(17) 0.0358(7) Uani 1 1 d . . . . .
C17 C 0.4031(5) 0.9745(2) 0.49677(17) 0.0325(7) Uani 1 1 d . . . . .
H17 H 0.2774 1.0099 0.5085 0.039 Uiso 1 1 calc R U . . .
C33 C 0.2657(5) 0.6921(2) 0.50685(16) 0.0334(7) Uani 1 1 d . . . . .
H33 H 0.3919 0.6562 0.4971 0.040 Uiso 1 1 calc R U . . .
C16 C 0.3691(4) 0.8642(2) 0.47206(16) 0.0305(7) Uani 1 1 d . . . . .
C11 C 0.1255(5) 0.9017(2) 0.61853(18) 0.0359(7) Uani 1 1 d . . . . .
C13 C 0.4588(5) 0.8259(2) 0.59525(17) 0.0343(7) Uani 1 1 d . . . . .
H13A H 0.4833 0.7658 0.6167 0.041 Uiso 1 1 calc R U . . .
H13B H 0.6007 0.8551 0.5831 0.041 Uiso 1 1 calc R U . . .
C37 C 0.2276(5) 0.4373(2) 0.38592(18) 0.0379(8) Uani 1 1 d . . . . .
C35 C 0.0415(4) 0.5317(2) 0.47164(17) 0.0318(7) Uani 1 1 d . . . . .
C14 C 0.2985(4) 0.8032(2) 0.53185(16) 0.0308(7) Uani 1 1 d . . . . .
C22 C 0.2060(5) 0.8416(2) 0.40904(17) 0.0345(7) Uani 1 1 d . . . . .
H22A H 0.0652 0.8117 0.4215 0.041 Uiso 1 1 calc R U . . .
H22B H 0.1794 0.9018 0.3880 0.041 Uiso 1 1 calc R U . . .
C40 C -0.1109(5) 0.5112(2) 0.40590(17) 0.0349(7) Uani 1 1 d . . . . .
H40A H -0.2543 0.4808 0.4155 0.042 Uiso 1 1 calc R U . . .
H40B H -0.1329 0.5723 0.3854 0.042 Uiso 1 1 calc R U . . .
C6 C 0.4729(6) 0.8965(3) 0.76147(18) 0.0445(8) Uani 1 1 d . . . . .
C24 C 0.2300(6) 0.7121(3) 0.30112(19) 0.0483(9) Uani 1 1 d . . . . .
H24A H 0.0859 0.6834 0.3117 0.058 Uiso 1 1 calc R U . . .
H24B H 0.3239 0.6568 0.2872 0.058 Uiso 1 1 calc R U . . .
C9 C 0.4354(6) 0.9565(3) 0.70212(19) 0.0472(9) Uani 1 1 d . . . . .
H9A H 0.3385 1.0103 0.7170 0.057 Uiso 1 1 calc R U . . .
H9B H 0.5769 0.9873 0.6911 0.057 Uiso 1 1 calc R U . . .
C25 C 0.2004(6) 0.7709(3) 0.24102(19) 0.0482(9) Uani 1 1 d . . . . .
C41B C -0.0644(7) 0.3858(3) 0.2971(2) 0.0537(10) Uani 1 1 d D . . . .
H41A H -0.2222 0.3691 0.3001 0.064 Uiso 0.85 1 calc R U P A 1
H41B H 0.0108 0.3231 0.2893 0.064 Uiso 0.85 1 calc R U P A 1
H41C H -0.1895 0.3423 0.3073 0.064 Uiso 0.15 1 calc R U P B 2
H41D H 0.0517 0.3421 0.2802 0.064 Uiso 0.15 1 calc R U P B 2
C3 C 0.5451(7) 0.7902(3) 0.8727(2) 0.0540(10) Uani 1 1 d . . . . .
C5 C 0.6809(6) 0.8947(3) 0.7917(2) 0.0626(11) Uani 1 1 d . . . . .
H5 H 0.8000 0.9292 0.7742 0.075 Uiso 1 1 calc R U . . .
C28 C 0.1392(7) 0.8743(3) 0.1281(2) 0.0562(10) Uani 1 1 d . . . . .
C26 C 0.0009(7) 0.8147(3) 0.2296(2) 0.0611(11) Uani 1 1 d . . . . .
H26 H -0.1139 0.8092 0.2601 0.073 Uiso 1 1 calc R U . . .
C1 C 0.7644(10) 0.7440(5) 0.9670(3) 0.0945(17) Uani 1 1 d . . . . .
H1A H 0.8829 0.7245 0.9369 0.142 Uiso 1 1 calc R U . . .
H1B H 0.7547 0.7005 1.0024 0.142 Uiso 1 1 calc R U . . .
H1C H 0.7935 0.8123 0.9881 0.142 Uiso 1 1 calc R U . . .
C32 C 0.2621(11) 0.9346(5) 0.0251(3) 0.102(2) Uani 1 1 d . . . . .
H32A H 0.2141 0.9750 -0.0092 0.153 Uiso 1 1 calc R U . . .
H32B H 0.2956 0.8692 0.0029 0.153 Uiso 1 1 calc R U . . .
H32C H 0.3929 0.9664 0.0495 0.153 Uiso 1 1 calc R U . . .
C30 C 0.3663(7) 0.7811(3) 0.1962(2) 0.0628(11) Uani 1 1 d . . . . .
H30 H 0.5013 0.7526 0.2035 0.075 Uiso 1 1 calc R U . . .
C4 C 0.7175(7) 0.8425(4) 0.8477(3) 0.0683(12) Uani 1 1 d . . . . .
H4 H 0.8592 0.8433 0.8681 0.082 Uiso 1 1 calc R U . . .
C27 C -0.0297(7) 0.8663(4) 0.1736(2) 0.0651(12) Uani 1 1 d . . . . .
H27 H -0.1640 0.8955 0.1666 0.078 Uiso 1 1 calc R U . . .
C29 C 0.3379(7) 0.8340(4) 0.1391(2) 0.0681(12) Uani 1 1 d . . . . .
H29 H 0.4537 0.8413 0.1091 0.082 Uiso 1 1 calc R U . . .
C8 C 0.3368(7) 0.7876(4) 0.8421(3) 0.0669(12) Uani 1 1 d . . . . .
H8 H 0.2200 0.7499 0.8581 0.080 Uiso 1 1 calc R U . . .
C7 C 0.3020(7) 0.8414(3) 0.7872(2) 0.0634(11) Uani 1 1 d . . . . .
H7 H 0.1600 0.8405 0.7671 0.076 Uiso 1 1 calc R U . . .
O48A O 0.0558(6) 0.6019(3) 0.0667(2) 0.0714(10) Uani 0.85 1 d . . P C 1
C42A C -0.0282(7) 0.4438(3) 0.2360(2) 0.0480(11) Uani 0.85 1 d D . P C 1
C43A C 0.1667(7) 0.4370(4) 0.1995(3) 0.0553(11) Uani 0.85 1 d . . P C 1
H43A H 0.2759 0.3961 0.2130 0.066 Uiso 0.85 1 calc R U P C 1
C49A C 0.2518(10) 0.5943(5) 0.0281(3) 0.0830(17) Uani 0.85 1 d . . P C 1
H49A H 0.2382 0.6312 -0.0107 0.124 Uiso 0.85 1 calc R U P C 1
H49B H 0.2728 0.5248 0.0119 0.124 Uiso 0.85 1 calc R U P C 1
H49C H 0.3773 0.6218 0.0571 0.124 Uiso 0.85 1 calc R U P C 1
C45A C 0.0397(8) 0.5490(4) 0.1225(3) 0.0528(11) Uani 0.85 1 d . . P C 1
C44A C 0.2032(8) 0.4894(4) 0.1435(3) 0.0593(12) Uani 0.85 1 d . . P C 1
H44A H 0.3362 0.4845 0.1204 0.071 Uiso 0.85 1 calc R U P C 1
C46A C -0.1538(8) 0.5571(4) 0.1586(3) 0.0653(14) Uani 0.85 1 d . . P C 1
H46A H -0.2636 0.5974 0.1448 0.078 Uiso 0.85 1 calc R U P C 1
C47A C -0.1868(7) 0.5067(4) 0.2144(3) 0.0590(12) Uani 0.85 1 d . . P C 1
H47A H -0.3175 0.5145 0.2384 0.071 Uiso 0.85 1 calc R U P C 1
O48B O -0.235(4) 0.594(2) 0.0694(13) 0.101(5) Uani 0.15 1 d D . P C 2
C43B C 0.044(4) 0.473(3) 0.2030(14) 0.101(5) Uani 0.15 1 d G . P C 2
H43B H 0.1874 0.4592 0.2164 0.121 Uiso 0.15 1 calc R U P C 2
C44B C 0.010(4) 0.527(3) 0.1476(14) 0.101(5) Uani 0.15 1 d G . P C 2
H44B H 0.1306 0.5490 0.1238 0.121 Uiso 0.15 1 calc R U P C 2
C45B C -0.205(5) 0.547(2) 0.1276(13) 0.101(5) Uani 0.15 1 d G . P C 2
C46B C -0.386(4) 0.514(3) 0.1631(13) 0.101(5) Uani 0.15 1 d G . P C 2
H46B H -0.5292 0.5276 0.1498 0.121 Uiso 0.15 1 calc R U P C 2
C47B C -0.352(4) 0.460(2) 0.2186(12) 0.101(5) Uani 0.15 1 d G . P C 2
H47B H -0.4724 0.4378 0.2423 0.121 Uiso 0.15 1 calc R U P C 2
C42B C -0.137(5) 0.440(2) 0.2385(12) 0.101(5) Uani 0.15 1 d DG . P C 2
C49B C -0.440(5) 0.600(4) 0.0350(18) 0.101(5) Uani 0.15 1 d D . P C 2
H49D H -0.4739 0.5380 0.0047 0.151 Uiso 0.15 1 calc R U P C 2
H49E H -0.4335 0.6550 0.0083 0.151 Uiso 0.15 1 calc R U P C 2
H49F H -0.5543 0.6093 0.0684 0.151 Uiso 0.15 1 calc R U P C 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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
C28 O31 C32 117.2(4) . . ?
C3 O2 C1 118.6(4) . . ?
C11 O15 C14 109.7(2) . . ?
C19 O18 C16 109.5(2) . . ?
C37 O36 C35 110.0(2) . . ?
C11 N10 C13 112.7(3) . . ?
C11 N10 C9 123.8(3) . . ?
C13 N10 C9 123.4(3) . . ?
C19 N21 C22 112.9(3) . . ?
C19 N21 C24 123.5(3) . . ?
C22 N21 C24 123.5(3) . . ?
C37 N39 C40 113.2(3) . . ?
C37 N39 C41B 122.2(3) . . ?
C40 N39 C41B 124.6(3) . . ?
C33 C34 H34 118.0 . . ?
C33 C34 C35 124.0(3) . . ?
C35 C34 H34 118.0 . . ?
O20 C19 O18 121.0(3) . . ?
O20 C19 N21 129.4(3) . . ?
N21 C19 O18 109.6(3) . . ?
C17 C17 H17 117.4 2_676 . ?
C17 C17 C16 125.2(3) 2_676 . ?
C16 C17 H17 117.4 . . ?
C34 C33 H33 117.7 . . ?
C34 C33 C14 124.7(3) . . ?
C14 C33 H33 117.7 . . ?
O18 C16 C17 109.6(2) . . ?
O18 C16 C14 106.2(2) . . ?
O18 C16 C22 104.6(2) . . ?
C17 C16 C14 111.8(3) . . ?
C17 C16 C22 112.8(2) . . ?
C22 C16 C14 111.4(2) . . ?
O12 C11 O15 121.3(3) . . ?
O12 C11 N10 129.3(3) . . ?
N10 C11 O15 109.3(3) . . ?
N10 C13 H13A 111.5 . . ?
N10 C13 H13B 111.5 . . ?
N10 C13 C14 101.5(2) . . ?
H13A C13 H13B 109.3 . . ?
C14 C13 H13A 111.5 . . ?
C14 C13 H13B 111.5 . . ?
O38 C37 O36 121.8(3) . . ?
O38 C37 N39 129.1(3) . . ?
N39 C37 O36 109.1(3) . . ?
O36 C35 C34 109.7(2) . . ?
O36 C35 C35 106.6(3) . 2_566 ?
O36 C35 C40 104.5(2) . . ?
C34 C35 C35 112.5(3) . 2_566 ?
C34 C35 C40 112.2(2) . . ?
C40 C35 C35 110.9(3) . 2_566 ?
O15 C14 C33 109.6(2) . . ?
O15 C14 C16 106.2(2) . . ?
O15 C14 C13 104.3(2) . . ?
C33 C14 C16 111.6(3) . . ?
C33 C14 C13 112.8(2) . . ?
C13 C14 C16 111.8(2) . . ?
N21 C22 C16 101.2(2) . . ?
N21 C22 H22A 111.5 . . ?
N21 C22 H22B 111.5 . . ?
C16 C22 H22A 111.5 . . ?
C16 C22 H22B 111.5 . . ?
H22A C22 H22B 109.3 . . ?
N39 C40 C35 101.1(2) . . ?
N39 C40 H40A 111.5 . . ?
N39 C40 H40B 111.5 . . ?
C35 C40 H40A 111.5 . . ?
C35 C40 H40B 111.5 . . ?
H40A C40 H40B 109.4 . . ?
C5 C6 C9 120.6(3) . . ?
C5 C6 C7 117.6(4) . . ?
C7 C6 C9 121.8(3) . . ?
N21 C24 H24A 108.6 . . ?
N21 C24 H24B 108.6 . . ?
N21 C24 C25 114.7(3) . . ?
H24A C24 H24B 107.6 . . ?
C25 C24 H24A 108.6 . . ?
C25 C24 H24B 108.6 . . ?
N10 C9 C6 114.2(3) . . ?
N10 C9 H9A 108.7 . . ?
N10 C9 H9B 108.7 . . ?
C6 C9 H9A 108.7 . . ?
C6 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C26 C25 C24 120.6(3) . . ?
C30 C25 C24 121.0(4) . . ?
C30 C25 C26 118.4(4) . . ?
N39 C41B H41A 109.1 . . ?
N39 C41B H41B 109.1 . . ?
N39 C41B H41C 107.2 . . ?
N39 C41B H41D 107.2 . . ?
N39 C41B C42A 112.7(3) . . ?
N39 C41B C42B 120.5(14) . . ?
H41A C41B H41B 107.8 . . ?
H41C C41B H41D 106.8 . . ?
C42A C41B H41A 109.1 . . ?
C42A C41B H41B 109.1 . . ?
C42B C41B H41C 107.2 . . ?
C42B C41B H41D 107.2 . . ?
C4 C3 O2 124.5(4) . . ?
C4 C3 C8 120.3(4) . . ?
C8 C3 O2 115.2(4) . . ?
C6 C5 H5 119.3 . . ?
C6 C5 C4 121.5(4) . . ?
C4 C5 H5 119.3 . . ?
C27 C28 O31 116.0(4) . . ?
C29 C28 O31 123.6(4) . . ?
C29 C28 C27 120.4(4) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 C25 121.0(4) . . ?
C27 C26 H26 119.5 . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O31 C32 H32A 109.5 . . ?
O31 C32 H32B 109.5 . . ?
O31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C25 C30 H30 119.4 . . ?
C25 C30 C29 121.2(4) . . ?
C29 C30 H30 119.4 . . ?
C3 C4 C5 119.6(4) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C28 C27 C26 119.7(4) . . ?
C28 C27 H27 120.1 . . ?
C26 C27 H27 120.1 . . ?
C28 C29 C30 119.2(4) . . ?
C28 C29 H29 120.4 . . ?
C30 C29 H29 120.4 . . ?
C3 C8 H8 120.3 . . ?
C3 C8 C7 119.4(4) . . ?
C7 C8 H8 120.3 . . ?
C6 C7 C8 121.6(4) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C45A O48A C49A 117.8(4) . . ?
C43A C42A C41B 121.0(4) . . ?
C43A C42A C47A 117.1(5) . . ?
C47A C42A C41B 122.0(4) . . ?
C42A C43A H43A 119.0 . . ?
C42A C43A C44A 121.9(4) . . ?
C44A C43A H43A 119.0 . . ?
O48A C49A H49A 109.5 . . ?
O48A C49A H49B 109.5 . . ?
O48A C49A H49C 109.5 . . ?
H49A C49A H49B 109.5 . . ?
H49A C49A H49C 109.5 . . ?
H49B C49A H49C 109.5 . . ?
O48A C45A C44A 124.2(4) . . ?
O48A C45A C46A 116.5(4) . . ?
C46A C45A C44A 119.3(5) . . ?
C43A C44A H44A 120.3 . . ?
C45A C44A C43A 119.4(4) . . ?
C45A C44A H44A 120.3 . . ?
C45A C46A H46A 119.5 . . ?
C47A C46A C45A 121.0(5) . . ?
C47A C46A H46A 119.5 . . ?
C42A C47A H47A 119.3 . . ?
C46A C47A C42A 121.3(4) . . ?
C46A C47A H47A 119.3 . . ?
C45B O48B C49B 124(3) . . ?
C44B C43B H43B 120.0 . . ?
C44B C43B C42B 120.0 . . ?
C42B C43B H43B 120.0 . . ?
C43B C44B H44B 120.0 . . ?
C43B C44B C45B 120.0 . . ?
C45B C44B H44B 120.0 . . ?
O48B C45B C44B 119(2) . . ?
O48B C45B C46B 121(2) . . ?
C46B C45B C44B 120.0 . . ?
C45B C46B H46B 120.0 . . ?
C45B C46B C47B 120.0 . . ?
C47B C46B H46B 120.0 . . ?
C46B C47B H47B 120.0 . . ?
C42B C47B C46B 120.0 . . ?
C42B C47B H47B 120.0 . . ?
C43B C42B C41B 111.6(17) . . ?
C47B C42B C41B 128.4(16) . . ?
C47B C42B C43B 120.0 . . ?
O48B C49B H49D 109.5 . . ?
O48B C49B H49E 109.5 . . ?
O48B C49B H49F 109.5 . . ?
H49D C49B H49E 109.5 . . ?
H49D C49B H49F 109.5 . . ?
H49E C49B H49F 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
O31 C28 1.384(5) . ?
O31 C32 1.403(6) . ?
O2 C3 1.382(5) . ?
O2 C1 1.406(6) . ?
O15 C11 1.373(4) . ?
O15 C14 1.449(3) . ?
O18 C19 1.373(4) . ?
O18 C16 1.450(3) . ?
O36 C37 1.371(4) . ?
O36 C35 1.448(3) . ?
O38 C37 1.202(4) . ?
O20 C19 1.201(4) . ?
O12 C11 1.201(4) . ?
N10 C11 1.340(4) . ?
N10 C13 1.447(4) . ?
N10 C9 1.452(5) . ?
N21 C19 1.338(4) . ?
N21 C22 1.449(4) . ?
N21 C24 1.454(5) . ?
N39 C37 1.345(4) . ?
N39 C40 1.444(4) . ?
N39 C41B 1.447(5) . ?
C34 H34 0.9300 . ?
C34 C33 1.312(5) . ?
C34 C35 1.508(4) . ?
C17 C17 1.318(6) 2_676 ?
C17 H17 0.9300 . ?
C17 C16 1.498(4) . ?
C33 H33 0.9300 . ?
C33 C14 1.508(4) . ?
C16 C14 1.563(4) . ?
C16 C22 1.541(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.536(4) . ?
C35 C35 1.556(6) 2_566 ?
C35 C40 1.543(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C6 C9 1.510(5) . ?
C6 C5 1.372(5) . ?
C6 C7 1.379(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.504(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C25 C26 1.388(6) . ?
C25 C30 1.357(6) . ?
C41B H41A 0.9700 . ?
C41B H41B 0.9700 . ?
C41B H41C 0.9700 . ?
C41B H41D 0.9700 . ?
C41B C42A 1.518(6) . ?
C41B C42B 1.493(13) . ?
C3 C4 1.360(6) . ?
C3 C8 1.371(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.389(6) . ?
C28 C27 1.375(6) . ?
C28 C29 1.360(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.377(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C30 H30 0.9300 . ?
C30 C29 1.406(6) . ?
C4 H4 0.9300 . ?
C27 H27 0.9300 . ?
C29 H29 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.382(6) . ?
C7 H7 0.9300 . ?
O48A C49A 1.416(7) . ?
O48A C45A 1.374(6) . ?
C42A C43A 1.388(6) . ?
C42A C47A 1.396(6) . ?
C43A H43A 0.9300 . ?
C43A C44A 1.388(7) . ?
C49A H49A 0.9600 . ?
C49A H49B 0.9600 . ?
C49A H49C 0.9600 . ?
C45A C44A 1.384(7) . ?
C45A C46A 1.378(7) . ?
C44A H44A 0.9300 . ?
C46A H46A 0.9300 . ?
C46A C47A 1.364(7) . ?
C47A H47A 0.9300 . ?
O48B C45B 1.38(2) . ?
O48B C49B 1.401(19) . ?
C43B H43B 0.9300 . ?
C43B C44B 1.3900 . ?
C43B C42B 1.3900 . ?
C44B H44B 0.9300 . ?
C44B C45B 1.3900 . ?
C45B C46B 1.3900 . ?
C46B H46B 0.9300 . ?
C46B C47B 1.3900 . ?
C47B H47B 0.9300 . ?
C47B C42B 1.3900 . ?
C49B H49D 0.9600 . ?
C49B H49E 0.9600 . ?
C49B H49F 0.9600 . ?
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
O31 C28 C27 C26 178.2(4) . . . . ?
O31 C28 C29 C30 -177.9(4) . . . . ?
O2 C3 C4 C5 -179.5(4) . . . . ?
O2 C3 C8 C7 178.2(4) . . . . ?
O18 C16 C14 O15 -179.6(2) . . . . ?
O18 C16 C14 C33 -60.2(3) . . . . ?
O18 C16 C14 C13 67.2(3) . . . . ?
O18 C16 C22 N21 14.0(3) . . . . ?
O36 C35 C40 N39 14.3(3) . . . . ?
N10 C13 C14 O15 -15.1(3) . . . . ?
N10 C13 C14 C33 -133.9(2) . . . . ?
N10 C13 C14 C16 99.3(3) . . . . ?
N21 C24 C25 C26 -93.1(4) . . . . ?
N21 C24 C25 C30 87.8(5) . . . . ?
N39 C41B C42A C43A 89.3(5) . . . . ?
N39 C41B C42A C47A -90.1(5) . . . . ?
N39 C41B C42B C43B 79.8(19) . . . . ?
N39 C41B C42B C47B -99(2) . . . . ?
C34 C33 C14 O15 10.2(5) . . . . ?
C34 C33 C14 C16 -107.2(4) . . . . ?
C34 C33 C14 C13 125.9(3) . . . . ?
C34 C35 C40 N39 133.0(2) . . . . ?
C19 O18 C16 C17 -133.3(3) . . . . ?
C19 O18 C16 C14 105.7(3) . . . . ?
C19 O18 C16 C22 -12.1(3) . . . . ?
C19 N21 C22 C16 -12.2(3) . . . . ?
C19 N21 C24 C25 -103.2(4) . . . . ?
C17 C17 C16 O18 -7.6(5) 2_676 . . . ?
C17 C17 C16 C14 109.8(4) 2_676 . . . ?
C17 C17 C16 C22 -123.8(4) 2_676 . . . ?
C17 C16 C14 O15 60.9(3) . . . . ?
C17 C16 C14 C33 -179.7(2) . . . . ?
C17 C16 C14 C13 -52.3(3) . . . . ?
C17 C16 C22 N21 133.1(2) . . . . ?
C33 C34 C35 O36 -7.3(4) . . . . ?
C33 C34 C35 C35 111.1(4) . . . 2_566 ?
C33 C34 C35 C40 -122.9(3) . . . . ?
C16 O18 C19 O20 -174.7(3) . . . . ?
C16 O18 C19 N21 4.9(3) . . . . ?
C11 O15 C14 C33 134.0(3) . . . . ?
C11 O15 C14 C16 -105.3(3) . . . . ?
C11 O15 C14 C13 13.0(3) . . . . ?
C11 N10 C13 C14 13.2(3) . . . . ?
C11 N10 C9 C6 105.4(4) . . . . ?
C13 N10 C11 O15 -5.7(4) . . . . ?
C13 N10 C11 O12 175.8(3) . . . . ?
C13 N10 C9 C6 -72.2(4) . . . . ?
C37 O36 C35 C34 -132.3(3) . . . . ?
C37 O36 C35 C35 105.7(3) . . . 2_566 ?
C37 O36 C35 C40 -11.8(3) . . . . ?
C37 N39 C40 C35 -13.1(3) . . . . ?
C37 N39 C41B C42A -88.8(4) . . . . ?
C37 N39 C41B C42B -115.7(13) . . . . ?
C35 O36 C37 O38 -174.4(3) . . . . ?
C35 O36 C37 N39 4.0(3) . . . . ?
C35 C34 C33 C14 178.9(3) . . . . ?
C35 C35 C40 N39 -100.2(3) 2_566 . . . ?
C14 O15 C11 O12 173.4(3) . . . . ?
C14 O15 C11 N10 -5.2(3) . . . . ?
C14 C16 C22 N21 -100.3(3) . . . . ?
C22 N21 C19 O18 5.3(4) . . . . ?
C22 N21 C19 O20 -175.2(3) . . . . ?
C22 N21 C24 C25 75.1(4) . . . . ?
C22 C16 C14 O15 -66.3(3) . . . . ?
C22 C16 C14 C33 53.1(3) . . . . ?
C22 C16 C14 C13 -179.5(2) . . . . ?
C40 N39 C37 O36 6.4(4) . . . . ?
C40 N39 C37 O38 -175.3(3) . . . . ?
C40 N39 C41B C42A 87.6(4) . . . . ?
C40 N39 C41B C42B 60.7(14) . . . . ?
C6 C5 C4 C3 1.3(7) . . . . ?
C24 N21 C19 O18 -176.3(3) . . . . ?
C24 N21 C19 O20 3.2(5) . . . . ?
C24 N21 C22 C16 169.4(3) . . . . ?
C24 C25 C26 C27 -178.2(4) . . . . ?
C24 C25 C30 C29 178.6(4) . . . . ?
C9 N10 C11 O15 176.5(3) . . . . ?
C9 N10 C11 O12 -2.1(6) . . . . ?
C9 N10 C13 C14 -169.0(3) . . . . ?
C9 C6 C5 C4 177.9(4) . . . . ?
C9 C6 C7 C8 -179.2(4) . . . . ?
C25 C26 C27 C28 0.2(7) . . . . ?
C25 C30 C29 C28 -0.9(7) . . . . ?
C41B N39 C37 O36 -176.8(3) . . . . ?
C41B N39 C37 O38 1.4(6) . . . . ?
C41B N39 C40 C35 170.3(3) . . . . ?
C41B C42A C43A C44A -180.0(4) . . . . ?
C41B C42A C47A C46A -178.8(5) . . . . ?
C3 C8 C7 C6 1.2(7) . . . . ?
C5 C6 C9 N10 123.4(4) . . . . ?
C5 C6 C7 C8 1.1(6) . . . . ?
C26 C25 C30 C29 -0.5(6) . . . . ?
C1 O2 C3 C4 7.1(7) . . . . ?
C1 O2 C3 C8 -173.4(5) . . . . ?
C32 O31 C28 C27 179.7(5) . . . . ?
C32 O31 C28 C29 -0.4(7) . . . . ?
C30 C25 C26 C27 0.9(7) . . . . ?
C4 C3 C8 C7 -2.3(7) . . . . ?
C27 C28 C29 C30 2.1(7) . . . . ?
C29 C28 C27 C26 -1.7(7) . . . . ?
C8 C3 C4 C5 1.1(7) . . . . ?
C7 C6 C9 N10 -56.3(5) . . . . ?
C7 C6 C5 C4 -2.3(6) . . . . ?
O48A C45A C44A C43A -178.2(4) . . . . ?
O48A C45A C46A C47A 179.4(5) . . . . ?
C42A C43A C44A C45A -1.1(8) . . . . ?
C43A C42A C47A C46A 1.8(7) . . . . ?
C49A O48A C45A C44A 0.4(7) . . . . ?
C49A O48A C45A C46A -179.4(5) . . . . ?
C45A C46A C47A C42A -1.3(8) . . . . ?
C44A C45A C46A C47A -0.5(8) . . . . ?
C46A C45A C44A C43A 1.6(8) . . . . ?
C47A C42A C43A C44A -0.6(7) . . . . ?
O48B C45B C46B C47B 175(3) . . . . ?
C43B C44B C45B O48B -175(3) . . . . ?
C43B C44B C45B C46B 0.0 . . . . ?
C44B C43B C42B C41B -179(3) . . . . ?
C44B C43B C42B C47B 0.0 . . . . ?
C44B C45B C46B C47B 0.0 . . . . ?
C45B C46B C47B C42B 0.0 . . . . ?
C46B C47B C42B C41B 178(3) . . . . ?
C46B C47B C42B C43B 0.0 . . . . ?
C42B C43B C44B C45B 0.0 . . . . ?
C49B O48B C45B C44B 165(3) . . . . ?
C49B O48B C45B C46B -10(5) . . . . ?
