#------------------------------------------------------------------------------
#$Date: 2023-11-06 08:48:05 +0200 (Mon, 06 Nov 2023) $
#$Revision: 287302 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/01/1570131.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_1570131
loop_
_publ_author_name
'Zhang, Mengchu'
'Zhang, Tianyuan'
'Yu, Sifan'
'Qiu, Huang'
'Yusuf, Abdulla'
'Xu, Xinfang'
'Qian, Yu'
'Hu, Wenhao'
_publ_section_title
;
 Construction of 4-hydroxycoumarin derivatives with adjacent quaternary
 and tertiary stereocenters via ternary catalysis.
;
_journal_issue                   42
_journal_name_full               'Chemical science'
_journal_page_first              11850
_journal_page_last               11857
_journal_paper_doi               10.1039/d3sc03452f
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C34 H29 N O4'
_chemical_formula_sum            'C34 H29 N O4'
_chemical_formula_weight         515.58
_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     dual
_audit_creation_date             2023-05-06
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-05-22 deposited with the CCDC.	2023-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                95.502(3)
_cell_angle_beta                 95.621(3)
_cell_angle_gamma                113.780(4)
_cell_formula_units_Z            2
_cell_length_a                   8.5398(3)
_cell_length_b                   10.1848(5)
_cell_length_c                   16.9463(5)
_cell_measurement_reflns_used    10809
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.5330
_cell_measurement_theta_min      2.6470
_cell_volume                     1327.39(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     70.00 101.00   0.50    0.08    --   44.84-150.00  80.00   62
  2  ω    104.00 129.00   0.50    0.16    --  105.85-150.00  80.00   50
  3  ω     72.00  98.00   0.50    0.16    --  105.85-150.00  80.00   52
  4  ω     39.00  65.00   0.50    0.16    --  105.85-150.00  80.00   52
  5  ω     37.00  63.00   0.50    0.16    --  105.85-125.00   0.00   52
  6  ω     71.00 112.00   0.50    0.16    --  105.85-125.00   0.00   82
  7  ω     46.00 111.00   0.50    0.16    --  105.85-125.00 -60.00  130
  8  ω     55.00 111.00   0.50    0.16    --  105.85-125.00 -90.00  112
  9  ω     73.00  98.00   0.50    0.16    --  105.85-123.00-117.00   50
 10  ω     30.00  93.00   0.50    0.08    --   44.84-123.00-117.00  126
 11  ω     81.00 106.00   0.50    0.16    --  105.85 -94.00  60.00   50
 12  ω     33.00  66.00   0.50    0.16    --  105.85 -94.00  60.00   66
 13  ω     38.00  63.00   0.50    0.16    --  105.85 -77.00 120.00   50
 14  ω     71.00 106.00   0.50    0.16    --  105.85 -77.00 120.00   70
 15  ω     45.00  71.00   0.50    0.16    --  105.85 -77.00  60.00   52
 16  ω     34.00  71.00   0.50    0.16    --  105.85 -61.00 -90.00   74
 17  ω     90.00 116.00   0.50    0.16    --  105.85  15.00 -30.00   52
 18  ω    133.00 176.00   0.50    0.16    --  105.85  15.00 -30.00   86
 19  ω     82.00 174.00   0.50    0.16    --  105.85  77.00  30.00  184
 20  ω     89.00 137.00   0.50    0.16    --  105.85  61.00-150.00   96
 21  ω    152.00 177.00   0.50    0.16    --  105.85  61.00-150.00   50
 22  ω     98.00 132.00   0.50    0.16    --  105.85 123.00 -36.00   68
 23  ω     62.00 116.00   0.50    0.08    --   44.84 150.00 125.00  108
 24  ω     91.00 116.00   0.50    0.16    --  105.85 150.00 125.00   50
 25  ω     81.00 125.00   0.50    0.16    --  105.85 125.00 -90.00   88
 26  ω    142.00 175.00   0.50    0.16    --  105.85 125.00 -90.00   66
 27  ω    -24.00  29.00   0.50    0.08    --  -44.84  19.00-120.00  106
 28  ω    -24.00  13.00   0.50    0.08    --  -44.84  19.00-150.00   74
 29  ω    -20.00   6.00   0.50    0.08    --  -44.84  19.00 -60.00   52
 30  ω    -23.00  32.00   0.50    0.08    --  -44.84  19.00 -30.00  110
 31  ω   -110.00 -31.00   0.50    0.16    -- -100.00 123.00 -36.00  158
 32  ω    -57.00 -30.00   0.50    0.08    --  -44.84 123.00 -36.00   54
 33  ω    -72.00 -27.00   0.50    0.16    -- -100.00 150.00 125.00   90
 34  ω   -129.00 -77.00   0.50    0.16    -- -100.00 150.00 125.00  104
 35  ω    -92.00 -67.00   0.50    0.08    --  -44.84 150.00 125.00   50
 36  ω    -66.00 -34.00   0.50    0.16    -- -100.00  77.00 120.00   64
 37  ω    -65.00 -26.00   0.50    0.16    -- -100.00  61.00 120.00   78
 38  ω   -102.00 -74.00   0.50    0.16    -- -100.00  77.00 120.00   56
 39  ω    -79.00 -27.00   0.50    0.16    -- -100.00  77.00 -30.00  104
 40  ω    -69.00 -26.00   0.50    0.16    -- -100.00  61.00-180.00   86
 41  ω   -118.00 -82.00   0.50    0.16    -- -100.00 -30.00-120.00   72
 42  ω   -174.00-130.00   0.50    0.16    -- -100.00 -30.00-120.00   88
 43  ω   -174.00-108.00   0.50    0.16    -- -100.00 -30.00 -30.00  132
 44  ω   -171.00 -82.00   0.50    0.16    -- -100.00 -30.00 120.00  178
 45  ω    -66.00 -28.00   0.50    0.08    --  -44.84 -77.00 -90.00   76
 46  ω   -117.00 -74.00   0.50    0.08    --  -44.84 -77.00 -90.00   86
 47  ω   -147.00-122.00   0.50    0.16    -- -100.00-123.00-117.00   50
 48  ω    -95.00 -57.00   0.50    0.08    --  -44.84-150.00  80.00   76
 49  ω   -135.00-110.00   0.50    0.16    -- -100.00-150.00  80.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1847117000
_diffrn_orient_matrix_UB_12      -0.0536598000
_diffrn_orient_matrix_UB_13      0.0214061000
_diffrn_orient_matrix_UB_21      -0.0736240000
_diffrn_orient_matrix_UB_22      -0.0225356000
_diffrn_orient_matrix_UB_23      -0.0893951000
_diffrn_orient_matrix_UB_31      -0.0147533000
_diffrn_orient_matrix_UB_32      -0.1566918000
_diffrn_orient_matrix_UB_33      -0.0091220000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14703
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         4.798
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53515
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
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    1.290
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         4700
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0619
_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)+(0.1273P)²+0.2312P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1675
_refine_ls_wR_factor_ref         0.1720
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4201
_reflns_number_total             4700
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc03452f2.cif
_cod_data_source_block           20230504-zmc0751-1_auto
_cod_depositor_comments
'Adding full bibliography for 1570130--1570133.cif.'
_cod_database_code               1570131
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O N'
_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   0.936
_shelx_estimated_absorpt_t_min   0.877
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C27(H27A,H27B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2A), C4(H4), C3(H3), C22(H22), C14(H14), C33(H33), C29(H29),
 C18(H18), C15(H15), C30(H30), C31(H31), C32(H32), C25(H25), C16(H16), C23(H23),
  C17(H17), C24(H24)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.085
_oxdiff_exptl_absorpt_empirical_full_min 0.290
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
O3 O 0.74744(14) 0.10999(11) 0.37289(7) 0.0250(3) Uani 1 1 d . . . . .
O2 O 0.57113(15) 0.36476(12) 0.50768(7) 0.0246(3) Uani 1 1 d . . . . .
H2 H 0.5498 0.3331 0.5512 0.037 Uiso 1 1 calc R U . . .
O1 O 0.55279(14) 0.69310(12) 0.35661(7) 0.0256(3) Uani 1 1 d . . . . .
O4 O 0.71730(15) 0.21060(12) 0.26675(7) 0.0280(3) Uani 1 1 d . . . . .
N1 N 0.74504(17) 0.73133(14) 0.26754(8) 0.0241(3) Uani 1 1 d . . . . .
C1 C 0.73982(19) 0.09644(17) 0.45197(10) 0.0230(4) Uani 1 1 d . . . . .
C7 C 0.63143(19) 0.28380(16) 0.46467(9) 0.0209(3) Uani 1 1 d . . . . .
C9 C 0.70477(19) 0.21146(17) 0.33700(10) 0.0221(3) Uani 1 1 d . . . . .
C8 C 0.64817(19) 0.30322(16) 0.38672(9) 0.0211(3) Uani 1 1 d . . . . .
C6 C 0.68313(19) 0.18022(16) 0.50116(10) 0.0217(4) Uani 1 1 d . . . . .
C5 C 0.6851(2) 0.16335(17) 0.58244(10) 0.0238(4) Uani 1 1 d . . . . .
H5 H 0.6491 0.2206 0.6175 0.029 Uiso 1 1 calc R U . . .
C34 C 0.6677(2) 0.66874(16) 0.32888(9) 0.0221(3) Uani 1 1 d . . . . .
C2 C 0.7917(2) -0.00561(17) 0.48067(11) 0.0259(4) Uani 1 1 d . . . . .
H2A H 0.8270 -0.0637 0.4457 0.031 Uiso 1 1 calc R U . . .
C21 C 0.8776(2) 0.58280(17) 0.29936(10) 0.0249(4) Uani 1 1 d . . . . .
C28 C 0.5778(2) 0.78131(18) 0.15285(10) 0.0253(4) Uani 1 1 d . . . . .
C10 C 0.59464(19) 0.41314(16) 0.35088(9) 0.0220(4) Uani 1 1 d . . . . .
H10 H 0.5128 0.4277 0.3854 0.026 Uiso 1 1 calc R U . . .
C4 C 0.7392(2) 0.06374(17) 0.61190(10) 0.0262(4) Uani 1 1 d . . . . .
H4 H 0.7407 0.0534 0.6671 0.031 Uiso 1 1 calc R U . . .
C26 C 0.8714(2) 0.68124(17) 0.24866(10) 0.0254(4) Uani 1 1 d . . . . .
C3 C 0.7912(2) -0.02115(17) 0.56082(11) 0.0271(4) Uani 1 1 d . . . . .
H3 H 0.8266 -0.0902 0.5811 0.032 Uiso 1 1 calc R U . . .
C13 C 0.2209(2) 0.19467(17) 0.17746(10) 0.0251(4) Uani 1 1 d . . . . .
C11 C 0.4933(2) 0.36356(17) 0.26559(9) 0.0238(4) Uani 1 1 d . . . . .
H11A H 0.5733 0.3598 0.2278 0.029 Uiso 1 1 calc R U . . .
H11B H 0.4509 0.4369 0.2516 0.029 Uiso 1 1 calc R U . . .
C20 C 0.8395(2) 0.62814(17) 0.44366(10) 0.0258(4) Uani 1 1 d . . . . .
H20A H 0.9265 0.7276 0.4458 0.039 Uiso 1 1 calc R U . . .
H20B H 0.8961 0.5675 0.4621 0.039 Uiso 1 1 calc R U . . .
H20C H 0.7541 0.6280 0.4783 0.039 Uiso 1 1 calc R U . . .
C19 C 0.7483(2) 0.56739(16) 0.35696(9) 0.0224(4) Uani 1 1 d . . . . .
C22 C 0.9995(2) 0.52676(18) 0.29435(11) 0.0300(4) Uani 1 1 d . . . . .
H22 H 1.0081 0.4617 0.3293 0.036 Uiso 1 1 calc R U . . .
C14 C 0.0605(2) 0.20018(17) 0.17845(10) 0.0271(4) Uani 1 1 d . . . . .
H14 H 0.0196 0.2074 0.2281 0.033 Uiso 1 1 calc R U . . .
C33 C 0.5082(2) 0.63620(18) 0.11826(10) 0.0273(4) Uani 1 1 d . . . . .
H33 H 0.5421 0.5696 0.1427 0.033 Uiso 1 1 calc R U . . .
C29 C 0.5281(2) 0.87786(18) 0.11591(11) 0.0289(4) Uani 1 1 d . . . . .
H29 H 0.5744 0.9770 0.1392 0.035 Uiso 1 1 calc R U . . .
C27 C 0.7059(2) 0.83948(18) 0.22997(10) 0.0278(4) Uani 1 1 d . . . . .
H27A H 0.8152 0.9142 0.2185 0.033 Uiso 1 1 calc R U . . .
H27B H 0.6594 0.8879 0.2688 0.033 Uiso 1 1 calc R U . . .
C18 C 0.2763(2) 0.18169(18) 0.10332(11) 0.0296(4) Uani 1 1 d . . . . .
H18 H 0.3841 0.1758 0.1013 0.035 Uiso 1 1 calc R U . . .
C15 C -0.0400(2) 0.19525(19) 0.10774(11) 0.0314(4) Uani 1 1 d . . . . .
H15 H -0.1491 0.1988 0.1094 0.038 Uiso 1 1 calc R U . . .
C12 C 0.3384(2) 0.21477(18) 0.25407(10) 0.0271(4) Uani 1 1 d . . . . .
H12A H 0.3802 0.1371 0.2521 0.033 Uiso 1 1 calc R U . . .
H12B H 0.2736 0.2080 0.3000 0.033 Uiso 1 1 calc R U . . .
C30 C 0.4116(2) 0.83015(19) 0.04527(11) 0.0319(4) Uani 1 1 d . . . . .
H30 H 0.3795 0.8970 0.0201 0.038 Uiso 1 1 calc R U . . .
C31 C 0.3416(2) 0.6852(2) 0.01111(11) 0.0321(4) Uani 1 1 d . . . . .
H31 H 0.2616 0.6525 -0.0372 0.039 Uiso 1 1 calc R U . . .
C32 C 0.3895(2) 0.5884(2) 0.04812(11) 0.0311(4) Uani 1 1 d . . . . .
H32 H 0.3408 0.4889 0.0254 0.037 Uiso 1 1 calc R U . . .
C25 C 0.9791(2) 0.7227(2) 0.19117(11) 0.0335(4) Uani 1 1 d . . . . .
H25 H 0.9714 0.7887 0.1566 0.040 Uiso 1 1 calc R U . . .
C16 C 0.0175(2) 0.18523(19) 0.03520(11) 0.0336(4) Uani 1 1 d . . . . .
H16 H -0.0507 0.1837 -0.0130 0.040 Uiso 1 1 calc R U . . .
C23 C 1.1102(2) 0.5674(2) 0.23693(12) 0.0361(4) Uani 1 1 d . . . . .
H23 H 1.1939 0.5288 0.2326 0.043 Uiso 1 1 calc R U . . .
C17 C 0.1761(2) 0.17733(19) 0.03279(11) 0.0330(4) Uani 1 1 d . . . . .
H17 H 0.2155 0.1690 -0.0172 0.040 Uiso 1 1 calc R U . . .
C24 C 1.0992(2) 0.6632(2) 0.18628(12) 0.0381(5) Uani 1 1 d . . . . .
H24 H 1.1752 0.6888 0.1474 0.046 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 0.0181 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
C1 O3 C9 122.46(12) . . ?
C7 O2 H2 109.5 . . ?
C34 N1 C26 110.62(13) . . ?
C34 N1 C27 123.50(14) . . ?
C26 N1 C27 125.82(13) . . ?
O3 C1 C6 121.66(14) . . ?
O3 C1 C2 116.50(14) . . ?
C6 C1 C2 121.83(15) . . ?
O2 C7 C8 118.38(14) . . ?
O2 C7 C6 120.45(13) . . ?
C8 C7 C6 121.14(14) . . ?
O3 C9 C8 117.62(13) . . ?
O4 C9 O3 114.99(14) . . ?
O4 C9 C8 127.38(15) . . ?
C7 C8 C9 119.72(14) . . ?
C7 C8 C10 119.74(14) . . ?
C9 C8 C10 120.38(13) . . ?
C1 C6 C7 117.21(14) . . ?
C1 C6 C5 118.10(14) . . ?
C5 C6 C7 124.66(15) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.51(15) . . ?
C4 C5 H5 119.7 . . ?
O1 C34 N1 123.72(15) . . ?
O1 C34 C19 126.92(14) . . ?
N1 C34 C19 109.35(13) . . ?
C1 C2 H2A 120.5 . . ?
C3 C2 C1 119.00(15) . . ?
C3 C2 H2A 120.5 . . ?
C26 C21 C19 109.01(14) . . ?
C22 C21 C26 119.22(15) . . ?
C22 C21 C19 131.57(16) . . ?
C33 C28 C29 119.19(16) . . ?
C33 C28 C27 122.64(15) . . ?
C29 C28 C27 118.16(15) . . ?
C8 C10 H10 105.4 . . ?
C8 C10 C11 115.74(13) . . ?
C8 C10 C19 113.51(12) . . ?
C11 C10 H10 105.4 . . ?
C11 C10 C19 110.46(12) . . ?
C19 C10 H10 105.4 . . ?
C5 C4 H4 119.9 . . ?
C5 C4 C3 120.11(15) . . ?
C3 C4 H4 119.9 . . ?
C21 C26 N1 109.62(14) . . ?
C25 C26 N1 127.44(16) . . ?
C25 C26 C21 122.92(16) . . ?
C2 C3 C4 120.42(15) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C14 C13 C18 118.24(16) . . ?
C14 C13 C12 121.17(15) . . ?
C18 C13 C12 120.39(15) . . ?
C10 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
C10 C11 C12 114.31(13) . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
C34 C19 C10 106.51(12) . . ?
C21 C19 C34 101.38(12) . . ?
C21 C19 C10 116.68(13) . . ?
C21 C19 C20 111.40(13) . . ?
C20 C19 C34 108.01(13) . . ?
C20 C19 C10 111.85(12) . . ?
C21 C22 H22 120.6 . . ?
C21 C22 C23 118.89(17) . . ?
C23 C22 H22 120.6 . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.82(15) . . ?
C15 C14 H14 119.6 . . ?
C28 C33 H33 119.9 . . ?
C32 C33 C28 120.20(16) . . ?
C32 C33 H33 119.9 . . ?
C28 C29 H29 119.8 . . ?
C30 C29 C28 120.40(16) . . ?
C30 C29 H29 119.8 . . ?
N1 C27 C28 115.23(13) . . ?
N1 C27 H27A 108.5 . . ?
N1 C27 H27B 108.5 . . ?
C28 C27 H27A 108.5 . . ?
C28 C27 H27B 108.5 . . ?
H27A C27 H27B 107.5 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.88(16) . . ?
C17 C18 H18 119.6 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.38(16) . . ?
C16 C15 H15 119.8 . . ?
C13 C12 C11 109.97(13) . . ?
C13 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
C11 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C29 C30 H30 119.8 . . ?
C29 C30 C31 120.32(16) . . ?
C31 C30 H30 119.8 . . ?
C30 C31 H31 120.3 . . ?
C32 C31 C30 119.45(16) . . ?
C32 C31 H31 120.3 . . ?
C33 C32 H32 119.8 . . ?
C31 C32 C33 120.43(16) . . ?
C31 C32 H32 119.8 . . ?
C26 C25 H25 121.5 . . ?
C26 C25 C24 116.91(18) . . ?
C24 C25 H25 121.5 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.70(17) . . ?
C17 C16 H16 120.2 . . ?
C22 C23 H23 119.6 . . ?
C24 C23 C22 120.76(17) . . ?
C24 C23 H23 119.6 . . ?
C18 C17 C16 119.97(16) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C25 C24 H24 119.4 . . ?
C23 C24 C25 121.27(17) . . ?
C23 C24 H24 119.4 . . ?
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
O3 C1 1.366(2) . ?
O3 C9 1.3969(19) . ?
O2 H2 0.8400 . ?
O2 C7 1.3330(19) . ?
O1 C34 1.2285(19) . ?
O4 C9 1.205(2) . ?
N1 C34 1.358(2) . ?
N1 C26 1.417(2) . ?
N1 C27 1.456(2) . ?
C1 C6 1.390(2) . ?
C1 C2 1.393(2) . ?
C7 C8 1.367(2) . ?
C7 C6 1.462(2) . ?
C9 C8 1.453(2) . ?
C8 C10 1.523(2) . ?
C6 C5 1.404(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.386(2) . ?
C34 C19 1.539(2) . ?
C2 H2A 0.9500 . ?
C2 C3 1.383(3) . ?
C21 C26 1.395(2) . ?
C21 C19 1.516(2) . ?
C21 C22 1.380(2) . ?
C28 C33 1.392(2) . ?
C28 C29 1.393(2) . ?
C28 C27 1.518(2) . ?
C10 H10 1.0000 . ?
C10 C11 1.535(2) . ?
C10 C19 1.575(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.392(3) . ?
C26 C25 1.384(2) . ?
C3 H3 0.9500 . ?
C13 C14 1.394(2) . ?
C13 C18 1.398(2) . ?
C13 C12 1.504(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.537(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 C19 1.537(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.397(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(3) . ?
C33 H33 0.9500 . ?
C33 C32 1.390(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.387(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C18 H18 0.9500 . ?
C18 C17 1.386(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.378(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C30 H30 0.9500 . ?
C30 C31 1.389(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.387(3) . ?
C32 H32 0.9500 . ?
C25 H25 0.9500 . ?
C25 C24 1.391(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.393(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.384(3) . ?
C17 H17 0.9500 . ?
C24 H24 0.9500 . ?
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
O3 C1 C6 C7 0.1(2) . . . . ?
O3 C1 C6 C5 -177.74(13) . . . . ?
O3 C1 C2 C3 178.24(13) . . . . ?
O3 C9 C8 C7 -2.8(2) . . . . ?
O3 C9 C8 C10 -178.22(12) . . . . ?
O2 C7 C8 C9 -176.75(13) . . . . ?
O2 C7 C8 C10 -1.3(2) . . . . ?
O2 C7 C6 C1 178.10(13) . . . . ?
O2 C7 C6 C5 -4.2(2) . . . . ?
O1 C34 C19 C21 179.27(15) . . . . ?
O1 C34 C19 C10 56.8(2) . . . . ?
O1 C34 C19 C20 -63.5(2) . . . . ?
O4 C9 C8 C7 176.01(15) . . . . ?
O4 C9 C8 C10 0.6(2) . . . . ?
N1 C34 C19 C21 -1.45(16) . . . . ?
N1 C34 C19 C10 -123.96(13) . . . . ?
N1 C34 C19 C20 115.73(14) . . . . ?
N1 C26 C25 C24 176.97(16) . . . . ?
C1 O3 C9 O4 -179.84(13) . . . . ?
C1 O3 C9 C8 -0.9(2) . . . . ?
C1 C6 C5 C4 -1.2(2) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C7 C8 C10 C11 -137.18(14) . . . . ?
C7 C8 C10 C19 93.55(16) . . . . ?
C7 C6 C5 C4 -178.86(13) . . . . ?
C9 O3 C1 C6 2.2(2) . . . . ?
C9 O3 C1 C2 -177.81(12) . . . . ?
C9 C8 C10 C11 38.26(19) . . . . ?
C9 C8 C10 C19 -91.00(16) . . . . ?
C8 C7 C6 C1 -3.8(2) . . . . ?
C8 C7 C6 C5 173.88(14) . . . . ?
C8 C10 C11 C12 50.26(19) . . . . ?
C8 C10 C19 C34 -172.52(12) . . . . ?
C8 C10 C19 C21 75.19(17) . . . . ?
C8 C10 C19 C20 -54.72(17) . . . . ?
C6 C1 C2 C3 -1.8(2) . . . . ?
C6 C7 C8 C9 5.1(2) . . . . ?
C6 C7 C8 C10 -179.40(12) . . . . ?
C6 C5 C4 C3 -0.3(2) . . . . ?
C5 C4 C3 C2 0.9(2) . . . . ?
C34 N1 C26 C21 -0.15(18) . . . . ?
C34 N1 C26 C25 -178.42(16) . . . . ?
C34 N1 C27 C28 -97.60(18) . . . . ?
C2 C1 C6 C7 -179.88(13) . . . . ?
C2 C1 C6 C5 2.3(2) . . . . ?
C21 C26 C25 C24 -1.1(3) . . . . ?
C21 C22 C23 C24 0.6(3) . . . . ?
C28 C33 C32 C31 1.2(3) . . . . ?
C28 C29 C30 C31 0.7(2) . . . . ?
C10 C11 C12 C13 164.39(14) . . . . ?
C26 N1 C34 O1 -179.64(14) . . . . ?
C26 N1 C34 C19 1.06(17) . . . . ?
C26 N1 C27 C28 85.24(19) . . . . ?
C26 C21 C19 C34 1.35(16) . . . . ?
C26 C21 C19 C10 116.54(15) . . . . ?
C26 C21 C19 C20 -113.34(15) . . . . ?
C26 C21 C22 C23 -1.8(2) . . . . ?
C26 C25 C24 C23 -0.2(3) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C13 C18 C17 C16 -0.3(3) . . . . ?
C11 C10 C19 C34 55.59(16) . . . . ?
C11 C10 C19 C21 -56.70(18) . . . . ?
C11 C10 C19 C20 173.38(13) . . . . ?
C19 C21 C26 N1 -0.83(18) . . . . ?
C19 C21 C26 C25 177.52(15) . . . . ?
C19 C21 C22 C23 -176.00(16) . . . . ?
C19 C10 C11 C12 -179.01(13) . . . . ?
C22 C21 C26 N1 -176.27(14) . . . . ?
C22 C21 C26 C25 2.1(2) . . . . ?
C22 C21 C19 C34 176.03(17) . . . . ?
C22 C21 C19 C10 -68.8(2) . . . . ?
C22 C21 C19 C20 61.3(2) . . . . ?
C22 C23 C24 C25 0.4(3) . . . . ?
C14 C13 C18 C17 1.3(2) . . . . ?
C14 C13 C12 C11 -107.47(17) . . . . ?
C14 C15 C16 C17 1.2(3) . . . . ?
C33 C28 C29 C30 -0.4(2) . . . . ?
C33 C28 C27 N1 -2.8(2) . . . . ?
C29 C28 C33 C32 -0.6(2) . . . . ?
C29 C28 C27 N1 176.90(13) . . . . ?
C29 C30 C31 C32 -0.1(2) . . . . ?
C27 N1 C34 O1 2.8(2) . . . . ?
C27 N1 C34 C19 -176.48(13) . . . . ?
C27 N1 C26 C21 177.31(14) . . . . ?
C27 N1 C26 C25 -0.9(3) . . . . ?
C27 C28 C33 C32 179.10(15) . . . . ?
C27 C28 C29 C30 179.90(15) . . . . ?
C18 C13 C14 C15 -1.0(2) . . . . ?
C18 C13 C12 C11 67.3(2) . . . . ?
C15 C16 C17 C18 -0.9(3) . . . . ?
C12 C13 C14 C15 173.87(15) . . . . ?
C12 C13 C18 C17 -173.67(15) . . . . ?
C30 C31 C32 C33 -0.9(3) . . . . ?
