#------------------------------------------------------------------------------
#$Date: 2026-03-05 13:32:13 +0100 (Thu 05 de Mar de 2026) $
#$Revision: 304888 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/65/1576597.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_1576597
loop_
_publ_author_name
'Liu, Yang'
'Xie, Zi-Yi'
'Kloene, Lennard'
'Xu, Cong-Lun'
'Tai, Jian-Peng'
'Zhu, Yu'
'Cai, Bao-Gui'
'Pan, Chongqing'
'Koenigs, Rene M.'
'Xuan, Jun'
_publ_section_title
;
 Visible light-induced 1,2-alkoxy shift of α-diazoacetates for Wolff
 rearrangements - access to oxyketenes.
;
_journal_issue                   7
_journal_name_full               'Chemical science'
_journal_page_first              3587
_journal_page_last               3592
_journal_paper_doi               10.1039/d5sc08263c
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety         'C19 H18 N2 O3'
_chemical_formula_sum            'C19 H18 N2 O3'
_chemical_formula_weight         322.35
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2022-03-29
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2025-03-10 deposited with the CCDC.	2025-12-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.483(7)
_cell_angle_beta                 97.956(7)
_cell_angle_gamma                100.119(6)
_cell_formula_units_Z            4
_cell_length_a                   9.5496(7)
_cell_length_b                   10.1080(8)
_cell_length_c                   17.3620(16)
_cell_measurement_reflns_used    3870
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      26.9130
_cell_measurement_theta_min      2.0750
_cell_volume                     1633.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      179.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  85.00   1.00    6.00    --   11.90  57.00  60.00   99
  2  ω     35.00  61.00   1.00    6.00    --   11.90 178.00-120.00   26
  3  ω    -14.00  78.00   1.00    6.00    --   11.90  77.00-180.00   92
  4  ω    -55.00  38.00   1.00    6.00    --   11.90 -57.00 -90.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0205972000
_diffrn_orient_matrix_UB_12      -0.0155691000
_diffrn_orient_matrix_UB_13      0.0370504000
_diffrn_orient_matrix_UB_21      0.0537493000
_diffrn_orient_matrix_UB_22      0.0534923000
_diffrn_orient_matrix_UB_23      0.0173014000
_diffrn_orient_matrix_UB_31      -0.0499669000
_diffrn_orient_matrix_UB_32      0.0445295000
_diffrn_orient_matrix_UB_33      -0.0056093000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.1252
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            5743
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.039
_diffrn_reflns_theta_max         25.039
_diffrn_reflns_theta_min         2.048
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         5743
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.1432
_refine_ls_R_factor_gt           0.1126
_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)+(0.1342P)²+2.2491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2851
_refine_ls_wR_factor_ref         0.3080
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3953
_reflns_number_total             5743
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc08263c2.cif
_cod_data_source_block           409
_cod_depositor_comments
'Adding full bibliography for 1576597--1576598.cif.'
_cod_database_code               1576597
_shelx_shelxl_version_number     2017/1
_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.
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.679(7)
 0.321(7)
2. 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
3.a Ternary CH refined with riding coordinates:
 C35(H35), C9(H9), C34(H34), C10(H10)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C26(H26A,H26B), C37(H37A,H37B), C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C6(H6), C17(H17), C2(H2), C25(H25), C24(H24), C23(H23), C14(H14),
 C32(H32), C31(H31), C22(H22), C30(H30), C29(H29), C16(H16), C15(H15), C4(H4),
 C5(H5), C3(H3)
3.d Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C19(H19A,H19B,H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.566
_oxdiff_exptl_absorpt_empirical_full_min 0.644
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
O4 O 1.1351(4) 0.7676(4) 0.7110(2) 0.0408(9) Uani 1 1 d . . . . .
O6 O 1.1072(4) 1.0044(4) 0.4383(2) 0.0451(10) Uani 1 1 d . . . . .
O5 O 1.3710(4) 1.0061(4) 0.5862(2) 0.0391(9) Uani 1 1 d . . . . .
O1 O 0.4834(4) 0.7439(4) 0.2155(2) 0.0457(10) Uani 1 1 d . . . . .
O3 O 0.1798(4) 0.5103(4) 0.0812(2) 0.0391(9) Uani 1 1 d . . . . .
N1 N 0.6077(4) 0.8536(4) 0.1244(2) 0.0301(9) Uani 1 1 d . . . . .
N4 N 1.1008(4) 0.7991(4) 0.5027(2) 0.0295(9) Uani 1 1 d . . . . .
N2 N 0.4092(4) 0.7179(4) 0.0063(2) 0.0316(10) Uani 1 1 d . . . . .
N3 N 0.9650(4) 0.6589(4) 0.6153(2) 0.0301(10) Uani 1 1 d . . . . .
O2 O 0.3635(5) 0.5164(4) -0.0688(2) 0.0514(11) Uani 1 1 d . . . . .
C12 C 0.5248(5) 0.8116(5) -0.0154(3) 0.0310(11) Uani 1 1 d . . . . .
C33 C 1.0912(5) 0.7441(5) 0.6420(3) 0.0307(11) Uani 1 1 d . . . . .
C27 C 0.9079(5) 0.6324(5) 0.5346(3) 0.0286(11) Uani 1 1 d . . . . .
C20 C 0.7490(5) 0.6341(5) 0.6852(3) 0.0298(11) Uani 1 1 d . . . . .
C1 C 0.8567(5) 0.8687(5) 0.1969(3) 0.0299(11) Uani 1 1 d . . . . .
C7 C 0.7175(5) 0.9226(5) 0.1870(3) 0.0327(11) Uani 1 1 d . . . . .
H7A H 0.678207 0.914720 0.235672 0.039 Uiso 1 1 calc R U . . .
H7B H 0.738194 1.017434 0.176044 0.039 Uiso 1 1 calc R U . . .
C8 C 0.4931(5) 0.7685(5) 0.1473(3) 0.0303(11) Uani 1 1 d . . . . .
C35 C 1.2216(5) 0.9564(5) 0.5759(3) 0.0354(12) Uani 1 1 d . . . . .
H35 H 1.172537 1.004404 0.610171 0.042 Uiso 1 1 calc R U . . .
C21 C 0.6520(6) 0.5543(6) 0.7254(3) 0.0382(13) Uani 1 1 d . . . . .
H21 H 0.671123 0.471662 0.742832 0.046 Uiso 1 1 calc R U . . .
C6 C 0.9824(6) 0.9484(5) 0.2336(3) 0.0338(12) Uani 1 1 d . . . . .
H6 H 0.981022 1.036002 0.249886 0.041 Uiso 1 1 calc R U . . .
C17 C 0.5405(6) 0.8327(5) -0.0925(3) 0.0386(13) Uani 1 1 d . . . . .
H17 H 0.471850 0.788202 -0.131816 0.046 Uiso 1 1 calc R U . . .
C9 C 0.3705(6) 0.7111(5) 0.0848(3) 0.0347(12) Uani 1 1 d . . . . .
H9 H 0.286973 0.753947 0.088009 0.042 Uiso 1 1 calc R U . . .
C26 C 0.8875(6) 0.5864(5) 0.6740(3) 0.0353(12) Uani 1 1 d . . . . .
H26A H 0.950375 0.596083 0.723424 0.042 Uiso 1 1 calc R U . . .
H26B H 0.865022 0.491552 0.659172 0.042 Uiso 1 1 calc R U . . .
C13 C 0.6244(5) 0.8787(5) 0.0453(3) 0.0304(11) Uani 1 1 d . . . . .
C2 C 0.8624(6) 0.7380(5) 0.1725(3) 0.0407(13) Uani 1 1 d . . . . .
H2 H 0.779901 0.682532 0.147914 0.049 Uiso 1 1 calc R U . . .
C36 C 1.1378(6) 0.9352(5) 0.4932(3) 0.0371(12) Uani 1 1 d . . . . .
C34 C 1.1805(6) 0.8036(5) 0.5818(3) 0.0330(12) Uani 1 1 d . . . . .
H34 H 1.265231 0.761051 0.582189 0.040 Uiso 1 1 calc R U . . .
C25 C 0.7174(6) 0.7556(5) 0.6575(3) 0.0378(13) Uani 1 1 d . . . . .
H25 H 0.780484 0.809625 0.629621 0.045 Uiso 1 1 calc R U . . .
C24 C 0.5910(6) 0.7961(6) 0.6715(3) 0.0428(14) Uani 1 1 d . . . . .
H24 H 0.569876 0.877482 0.653114 0.051 Uiso 1 1 calc R U . . .
C23 C 0.4966(6) 0.7158(6) 0.7129(3) 0.0392(13) Uani 1 1 d . . . . .
H23 H 0.412521 0.743532 0.722276 0.047 Uiso 1 1 calc R U . . .
C28 C 0.9761(5) 0.7038(5) 0.4765(3) 0.0293(11) Uani 1 1 d . . . . .
C14 C 0.7426(6) 0.9656(5) 0.0252(3) 0.0391(13) Uani 1 1 d . . . . .
H14 H 0.811224 1.011302 0.064081 0.047 Uiso 1 1 calc R U . . .
C11 C 0.3638(6) 0.5826(6) -0.0105(3) 0.0381(13) Uani 1 1 d . . . . .
C32 C 0.7841(6) 0.5415(5) 0.5112(3) 0.0396(13) Uani 1 1 d . . . . .
H32 H 0.737445 0.492386 0.548204 0.048 Uiso 1 1 calc R U . . .
C31 C 0.7274(6) 0.5218(5) 0.4327(3) 0.0421(13) Uani 1 1 d . . . . .
H31 H 0.641796 0.462031 0.417972 0.050 Uiso 1 1 calc R U . . .
C10 C 0.3247(6) 0.5591(5) 0.0720(3) 0.0377(12) Uani 1 1 d . . . . .
H10 H 0.390913 0.509982 0.103203 0.045 Uiso 1 1 calc R U . . .
C22 C 0.5267(6) 0.5956(6) 0.7399(3) 0.0425(14) Uani 1 1 d . . . . .
H22 H 0.463598 0.541905 0.767904 0.051 Uiso 1 1 calc R U . . .
C30 C 0.7966(6) 0.5897(6) 0.3773(3) 0.0430(14) Uani 1 1 d . . . . .
H30 H 0.759514 0.573606 0.324940 0.052 Uiso 1 1 calc R U . . .
C29 C 0.9229(6) 0.6832(5) 0.3985(3) 0.0354(12) Uani 1 1 d . . . . .
H29 H 0.969841 0.730462 0.360998 0.042 Uiso 1 1 calc R U . . .
C16 C 0.6595(7) 0.9208(6) -0.1111(3) 0.0437(14) Uani 1 1 d . . . . .
H16 H 0.670993 0.936042 -0.162800 0.052 Uiso 1 1 calc R U . . .
C15 C 0.7594(7) 0.9847(5) -0.0522(4) 0.0444(14) Uani 1 1 d . . . . .
H15 H 0.840090 1.042159 -0.064375 0.053 Uiso 1 1 calc R U . . .
C4 C 1.1144(7) 0.7704(6) 0.2212(3) 0.0449(14) Uani 1 1 d . . . . .
H4 H 1.200513 0.738156 0.228993 0.054 Uiso 1 1 calc R U . . .
C5 C 1.1096(6) 0.8985(6) 0.2461(3) 0.0426(14) Uani 1 1 d . . . . .
H5 H 1.192435 0.952303 0.271653 0.051 Uiso 1 1 calc R U . . .
C3 C 0.9930(7) 0.6908(6) 0.1850(4) 0.0509(16) Uani 1 1 d . . . . .
H3 H 0.996576 0.603898 0.168447 0.061 Uiso 1 1 calc R U . . .
C37 C 1.4013(7) 1.1497(6) 0.5821(5) 0.0553(17) Uani 1 1 d . . . . .
H37A H 1.367182 1.190354 0.625103 0.066 Uiso 1 1 calc R U . . .
H37B H 1.351743 1.177029 0.533932 0.066 Uiso 1 1 calc R U . . .
C18 C 0.1472(8) 0.3652(6) 0.0683(5) 0.068(2) Uani 1 1 d . . . . .
H18A H 0.160603 0.342595 0.015715 0.082 Uiso 1 1 calc R U . . .
H18B H 0.212313 0.323558 0.104180 0.082 Uiso 1 1 calc R U . . .
C38 C 1.5550(9) 1.1949(8) 0.5857(6) 0.079(2) Uani 1 1 d . . . . .
H38A H 1.587032 1.159817 0.540942 0.118 Uiso 1 1 calc R U . . .
H38B H 1.603963 1.163304 0.632084 0.118 Uiso 1 1 calc R U . . .
H38C H 1.575721 1.291329 0.586385 0.118 Uiso 1 1 calc R U . . .
C19 C 0.0006(10) 0.3146(8) 0.0797(6) 0.086(3) Uani 1 1 d . . . . .
H19A H -0.010515 0.331470 0.132829 0.129 Uiso 1 1 calc R U . . .
H19B H -0.021726 0.219569 0.068072 0.129 Uiso 1 1 calc R U . . .
H19C H -0.063235 0.359074 0.045854 0.129 Uiso 1 1 calc R U . . .
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
C35 O5 C37 111.5(4) . . ?
C10 O3 C18 109.9(5) . . ?
C8 N1 C7 116.7(4) . . ?
C8 N1 C13 124.0(4) . . ?
C13 N1 C7 119.4(4) . . ?
C36 N4 C34 94.2(4) . . ?
C36 N4 C28 132.9(4) . . ?
C28 N4 C34 123.7(4) . . ?
C12 N2 C9 123.8(4) . . ?
C11 N2 C12 132.1(4) . . ?
C11 N2 C9 94.4(4) . . ?
C33 N3 C27 124.5(4) . . ?
C33 N3 C26 116.9(4) . . ?
C27 N3 C26 118.6(4) . . ?
C17 C12 N2 121.7(5) . . ?
C17 C12 C13 121.7(5) . . ?
C13 C12 N2 116.6(4) . . ?
O4 C33 N3 123.1(5) . . ?
O4 C33 C34 119.9(5) . . ?
N3 C33 C34 116.8(4) . . ?
C28 C27 N3 120.3(4) . . ?
C32 C27 N3 122.0(4) . . ?
C32 C27 C28 117.7(5) . . ?
C21 C20 C26 118.7(4) . . ?
C21 C20 C25 119.0(5) . . ?
C25 C20 C26 122.3(4) . . ?
C6 C1 C7 119.9(4) . . ?
C6 C1 C2 118.3(5) . . ?
C2 C1 C7 121.7(4) . . ?
N1 C7 C1 114.3(4) . . ?
N1 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C1 C7 H7A 108.7 . . ?
C1 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
O1 C8 N1 123.0(5) . . ?
O1 C8 C9 119.5(4) . . ?
N1 C8 C9 117.3(4) . . ?
O5 C35 H35 111.5 . . ?
O5 C35 C36 119.6(4) . . ?
O5 C35 C34 114.6(4) . . ?
C36 C35 H35 111.5 . . ?
C34 C35 H35 111.5 . . ?
C34 C35 C36 85.6(4) . . ?
C20 C21 H21 119.5 . . ?
C20 C21 C22 121.1(5) . . ?
C22 C21 H21 119.5 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.7(5) . . ?
C5 C6 H6 119.7 . . ?
C12 C17 H17 120.1 . . ?
C12 C17 C16 119.7(5) . . ?
C16 C17 H17 120.1 . . ?
N2 C9 C8 113.7(4) . . ?
N2 C9 H9 110.7 . . ?
N2 C9 C10 88.7(4) . . ?
C8 C9 H9 110.7 . . ?
C8 C9 C10 120.4(5) . . ?
C10 C9 H9 110.7 . . ?
N3 C26 C20 114.3(4) . . ?
N3 C26 H26A 108.7 . . ?
N3 C26 H26B 108.7 . . ?
C20 C26 H26A 108.7 . . ?
C20 C26 H26B 108.7 . . ?
H26A C26 H26B 107.6 . . ?
C12 C13 N1 120.8(4) . . ?
C14 C13 N1 121.8(5) . . ?
C14 C13 C12 117.4(5) . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.8(5) . . ?
C3 C2 H2 120.1 . . ?
O6 C36 N4 130.7(5) . . ?
O6 C36 C35 137.5(5) . . ?
N4 C36 C35 91.7(4) . . ?
N4 C34 C33 114.1(4) . . ?
N4 C34 C35 88.4(4) . . ?
N4 C34 H34 110.5 . . ?
C33 C34 C35 120.8(5) . . ?
C33 C34 H34 110.5 . . ?
C35 C34 H34 110.5 . . ?
C20 C25 H25 120.1 . . ?
C20 C25 C24 119.8(5) . . ?
C24 C25 H25 120.1 . . ?
C25 C24 H24 119.8 . . ?
C23 C24 C25 120.3(5) . . ?
C23 C24 H24 119.8 . . ?
C24 C23 H23 119.9 . . ?
C22 C23 C24 120.2(5) . . ?
C22 C23 H23 119.9 . . ?
C27 C28 N4 116.2(4) . . ?
C29 C28 N4 121.8(4) . . ?
C29 C28 C27 122.0(5) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.8(5) . . ?
C15 C14 H14 119.6 . . ?
N2 C11 C10 91.3(4) . . ?
O2 C11 N2 130.7(5) . . ?
O2 C11 C10 137.9(5) . . ?
C27 C32 H32 119.5 . . ?
C27 C32 C31 120.9(5) . . ?
C31 C32 H32 119.5 . . ?
C32 C31 H31 119.8 . . ?
C30 C31 C32 120.5(5) . . ?
C30 C31 H31 119.8 . . ?
O3 C10 C9 114.2(5) . . ?
O3 C10 C11 119.2(4) . . ?
O3 C10 H10 111.8 . . ?
C9 C10 C11 85.5(4) . . ?
C9 C10 H10 111.8 . . ?
C11 C10 H10 111.8 . . ?
C21 C22 H22 120.2 . . ?
C23 C22 C21 119.7(5) . . ?
C23 C22 H22 120.2 . . ?
C31 C30 H30 119.8 . . ?
C31 C30 C29 120.5(5) . . ?
C29 C30 H30 119.8 . . ?
C28 C29 C30 118.4(5) . . ?
C28 C29 H29 120.8 . . ?
C30 C29 H29 120.8 . . ?
C17 C16 H16 120.5 . . ?
C15 C16 C17 119.1(5) . . ?
C15 C16 H16 120.5 . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.3(5) . . ?
C16 C15 H15 119.4 . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(5) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.5(5) . . ?
C4 C5 H5 119.7 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(5) . . ?
C4 C3 H3 119.6 . . ?
O5 C37 H37A 109.8 . . ?
O5 C37 H37B 109.8 . . ?
O5 C37 C38 109.6(6) . . ?
H37A C37 H37B 108.2 . . ?
C38 C37 H37A 109.8 . . ?
C38 C37 H37B 109.8 . . ?
O3 C18 H18A 109.7 . . ?
O3 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
C19 C18 O3 110.0(6) . . ?
C19 C18 H18A 109.7 . . ?
C19 C18 H18B 109.7 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
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
O4 C33 1.221(6) . ?
O6 C36 1.219(6) . ?
O5 C35 1.413(6) . ?
O5 C37 1.433(7) . ?
O1 C8 1.225(6) . ?
O3 C10 1.416(6) . ?
O3 C18 1.453(7) . ?
N1 C7 1.477(6) . ?
N1 C8 1.375(6) . ?
N1 C13 1.424(6) . ?
N4 C36 1.377(7) . ?
N4 C34 1.472(6) . ?
N4 C28 1.412(6) . ?
N2 C12 1.418(6) . ?
N2 C9 1.460(6) . ?
N2 C11 1.377(7) . ?
N3 C33 1.372(7) . ?
N3 C27 1.436(6) . ?
N3 C26 1.468(6) . ?
O2 C11 1.208(7) . ?
C12 C17 1.382(7) . ?
C12 C13 1.400(7) . ?
C33 C34 1.502(7) . ?
C27 C28 1.411(7) . ?
C27 C32 1.374(7) . ?
C20 C21 1.386(7) . ?
C20 C26 1.520(7) . ?
C20 C25 1.389(7) . ?
C1 C7 1.511(7) . ?
C1 C6 1.391(7) . ?
C1 C2 1.397(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.510(7) . ?
C35 H35 0.9800 . ?
C35 C36 1.539(8) . ?
C35 C34 1.534(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.388(8) . ?
C6 H6 0.9300 . ?
C6 C5 1.387(8) . ?
C17 H17 0.9300 . ?
C17 C16 1.393(8) . ?
C9 H9 0.9800 . ?
C9 C10 1.527(7) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C13 C14 1.390(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.402(8) . ?
C34 H34 0.9800 . ?
C25 H25 0.9300 . ?
C25 C24 1.392(8) . ?
C24 H24 0.9300 . ?
C24 C23 1.385(8) . ?
C23 H23 0.9300 . ?
C23 C22 1.369(8) . ?
C28 C29 1.379(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(8) . ?
C11 C10 1.539(8) . ?
C32 H32 0.9300 . ?
C32 C31 1.395(8) . ?
C31 H31 0.9300 . ?
C31 C30 1.364(8) . ?
C10 H10 0.9800 . ?
C22 H22 0.9300 . ?
C30 H30 0.9300 . ?
C30 C29 1.398(8) . ?
C29 H29 0.9300 . ?
C16 H16 0.9300 . ?
C16 C15 1.369(9) . ?
C15 H15 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.372(9) . ?
C4 C3 1.360(9) . ?
C5 H5 0.9300 . ?
C3 H3 0.9300 . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C37 C38 1.451(10) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.445(11) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
O4 C33 C34 N4 -164.0(4) . . . . ?
O4 C33 C34 C35 -60.6(7) . . . . ?
O5 C35 C36 O6 -64.3(9) . . . . ?
O5 C35 C36 N4 117.5(5) . . . . ?
O5 C35 C34 N4 -122.1(5) . . . . ?
O5 C35 C34 C33 120.5(5) . . . . ?
O1 C8 C9 N2 -165.0(5) . . . . ?
O1 C8 C9 C10 -61.8(7) . . . . ?
N1 C8 C9 N2 19.0(7) . . . . ?
N1 C8 C9 C10 122.2(5) . . . . ?
N1 C13 C14 C15 177.6(5) . . . . ?
N4 C28 C29 C30 -178.3(5) . . . . ?
N2 C12 C17 C16 -176.9(5) . . . . ?
N2 C12 C13 N1 -0.6(7) . . . . ?
N2 C12 C13 C14 176.6(4) . . . . ?
N2 C9 C10 O3 -122.4(5) . . . . ?
N2 C9 C10 C11 -2.3(4) . . . . ?
N2 C11 C10 O3 117.7(5) . . . . ?
N2 C11 C10 C9 2.5(4) . . . . ?
N3 C33 C34 N4 19.2(6) . . . . ?
N3 C33 C34 C35 122.6(5) . . . . ?
N3 C27 C28 N4 0.4(6) . . . . ?
N3 C27 C28 C29 -178.6(5) . . . . ?
N3 C27 C32 C31 177.2(5) . . . . ?
O2 C11 C10 O3 -64.6(9) . . . . ?
O2 C11 C10 C9 -179.8(7) . . . . ?
C12 N2 C9 C8 -23.8(7) . . . . ?
C12 N2 C9 C10 -146.6(5) . . . . ?
C12 N2 C11 O2 -35.5(9) . . . . ?
C12 N2 C11 C10 142.5(5) . . . . ?
C12 C17 C16 C15 0.3(8) . . . . ?
C12 C13 C14 C15 0.4(8) . . . . ?
C33 N3 C27 C28 -5.2(7) . . . . ?
C33 N3 C27 C32 177.1(5) . . . . ?
C33 N3 C26 C20 109.1(5) . . . . ?
C27 N3 C33 O4 177.9(4) . . . . ?
C27 N3 C33 C34 -5.5(7) . . . . ?
C27 N3 C26 C20 -73.4(6) . . . . ?
C27 C28 C29 C30 0.7(8) . . . . ?
C27 C32 C31 C30 2.1(9) . . . . ?
C20 C21 C22 C23 1.4(8) . . . . ?
C20 C25 C24 C23 -0.1(8) . . . . ?
C1 C6 C5 C4 1.3(8) . . . . ?
C1 C2 C3 C4 0.3(9) . . . . ?
C7 N1 C8 O1 -3.6(7) . . . . ?
C7 N1 C8 C9 172.3(4) . . . . ?
C7 N1 C13 C12 177.9(4) . . . . ?
C7 N1 C13 C14 0.8(7) . . . . ?
C7 C1 C6 C5 177.3(5) . . . . ?
C7 C1 C2 C3 -178.0(5) . . . . ?
C8 N1 C7 C1 106.5(5) . . . . ?
C8 N1 C13 C12 -2.7(7) . . . . ?
C8 N1 C13 C14 -179.8(5) . . . . ?
C8 C9 C10 O3 120.7(5) . . . . ?
C8 C9 C10 C11 -119.2(5) . . . . ?
C35 O5 C37 C38 -174.7(6) . . . . ?
C21 C20 C26 N3 165.5(5) . . . . ?
C21 C20 C25 C24 1.2(8) . . . . ?
C6 C1 C7 N1 158.6(4) . . . . ?
C6 C1 C2 C3 -0.2(8) . . . . ?
C17 C12 C13 N1 -178.8(5) . . . . ?
C17 C12 C13 C14 -1.6(7) . . . . ?
C17 C16 C15 C14 -1.4(9) . . . . ?
C9 N2 C12 C17 -167.0(5) . . . . ?
C9 N2 C12 C13 14.8(7) . . . . ?
C9 N2 C11 O2 179.4(6) . . . . ?
C9 N2 C11 C10 -2.6(4) . . . . ?
C26 N3 C33 O4 -4.8(7) . . . . ?
C26 N3 C33 C34 171.9(4) . . . . ?
C26 N3 C27 C28 177.5(4) . . . . ?
C26 N3 C27 C32 -0.2(7) . . . . ?
C26 C20 C21 C22 177.4(5) . . . . ?
C26 C20 C25 C24 -178.0(5) . . . . ?
C13 N1 C7 C1 -74.1(6) . . . . ?
C13 N1 C8 O1 177.0(5) . . . . ?
C13 N1 C8 C9 -7.1(7) . . . . ?
C13 C12 C17 C16 1.2(8) . . . . ?
C13 C14 C15 C16 1.1(9) . . . . ?
C2 C1 C7 N1 -23.6(7) . . . . ?
C2 C1 C6 C5 -0.6(7) . . . . ?
C36 N4 C34 C33 125.0(5) . . . . ?
C36 N4 C34 C35 1.7(4) . . . . ?
C36 N4 C28 C27 -122.2(6) . . . . ?
C36 N4 C28 C29 56.9(8) . . . . ?
C36 C35 C34 N4 -1.5(4) . . . . ?
C36 C35 C34 C33 -118.9(5) . . . . ?
C34 N4 C36 O6 -180.0(6) . . . . ?
C34 N4 C36 C35 -1.7(4) . . . . ?
C34 N4 C28 C27 15.5(7) . . . . ?
C34 N4 C28 C29 -165.4(5) . . . . ?
C34 C35 C36 O6 179.7(7) . . . . ?
C34 C35 C36 N4 1.6(4) . . . . ?
C25 C20 C21 C22 -1.8(8) . . . . ?
C25 C20 C26 N3 -15.4(7) . . . . ?
C25 C24 C23 C22 -0.3(8) . . . . ?
C24 C23 C22 C21 -0.4(8) . . . . ?
C28 N4 C36 O6 -34.2(10) . . . . ?
C28 N4 C36 C35 144.2(5) . . . . ?
C28 N4 C34 C33 -25.4(7) . . . . ?
C28 N4 C34 C35 -148.7(5) . . . . ?
C28 C27 C32 C31 -0.7(8) . . . . ?
C11 N2 C12 C17 56.4(8) . . . . ?
C11 N2 C12 C13 -121.8(6) . . . . ?
C11 N2 C9 C8 125.5(5) . . . . ?
C11 N2 C9 C10 2.6(4) . . . . ?
C32 C27 C28 N4 178.3(4) . . . . ?
C32 C27 C28 C29 -0.7(7) . . . . ?
C32 C31 C30 C29 -2.1(9) . . . . ?
C31 C30 C29 C28 0.7(8) . . . . ?
C10 O3 C18 C19 178.5(6) . . . . ?
C5 C4 C3 C2 0.3(9) . . . . ?
C3 C4 C5 C6 -1.1(8) . . . . ?
C37 O5 C35 C36 82.2(6) . . . . ?
C37 O5 C35 C34 -178.4(5) . . . . ?
C18 O3 C10 C9 -179.7(5) . . . . ?
C18 O3 C10 C11 81.5(6) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.679(7)
2 0.321(7)
