#------------------------------------------------------------------------------
#$Date: 2024-10-06 08:37:40 +0300 (Sun, 06 Oct 2024) $
#$Revision: 295121 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/36/7133614.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_7133614
loop_
_publ_author_name
'Dong, Yujie'
'Liu, Jun'
'Ning, Rongjin'
'Yang, Fazhou'
'Zhang, Cheng'
'Guo, Hongchao'
_publ_section_title
;
 Pd-catalyzed sequential intramolecular annulation/intermolecular [3+2]
 cycloaddition of 5-allenyloxazolidine-2,4-diones with dipoles: synthesis
 of spiroheterocycles.
;
_journal_issue                   76
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10516
_journal_page_last               10519
_journal_paper_doi               10.1039/d4cc03551h
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C33 H26 Cl N3 O2'
_chemical_formula_sum            'C33 H26 Cl N3 O2'
_chemical_formula_weight         532.046
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-09-08 deposited with the CCDC.	2024-08-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.387(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1281(2)
_cell_length_b                   17.8377(2)
_cell_length_c                   13.6750(2)
_cell_measurement_reflns_used    9845
_cell_measurement_temperature    173
_cell_measurement_theta_max      75.7000
_cell_measurement_theta_min      4.1010
_cell_volume                     2651.29(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9969
_diffrn_measured_fraction_theta_max 0.9786
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00  28.00   1.00    2.22    --  -41.81  57.00   0.00   90
  2  ω   -114.00 -14.00   1.00    2.22    --  -41.81 -57.00-150.00  100
  3  ω     20.00 108.00   1.00    2.22    --   41.81  38.00 150.00   88
  4  ω      9.00  68.00   1.00    2.22    --   41.81 -99.00  60.00   59
  5  ω     34.00  92.00   1.00    2.22    --   41.81-125.00-120.00   58
  6  ω     27.00 173.00   1.00    8.70    --  110.95   0.00-150.00  146
  7  ω     48.00 100.00   1.00    8.70    --  110.95 -77.00-150.00   52
  8  ω    118.00 169.00   1.00    8.70    --  110.95  77.00  30.00   51
  9  ω    121.00 147.00   1.00    8.70    --  110.95 125.00-120.00   26
 10  ω     54.00 139.00   1.00    8.70    --  110.95 -30.00 -30.00   85
 11  ω     47.00 105.00   1.00    8.70    --  110.95 -95.00  90.00   58
 12  ω     81.00 108.00   1.00    8.70    --  110.95-107.00 -71.00   27
 13  ω     41.00 131.00   1.00    8.70    --  110.95 -45.00  90.00   90
 14  ω     80.00 106.00   1.00    8.70    --  110.95-125.00   0.00   26
 15  ω     38.00 123.00   1.00    8.70    --  110.95 -45.00-120.00   85
 16  ω     67.00 106.00   1.00    8.70    --  110.95 -95.00 150.00   39
 17  ω     32.00 108.00   1.00    8.70    --  110.95-105.00  43.92   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0611381000
_diffrn_orient_matrix_UB_12      0.0774620000
_diffrn_orient_matrix_UB_13      0.0005928000
_diffrn_orient_matrix_UB_21      -0.1213882000
_diffrn_orient_matrix_UB_22      -0.0320907000
_diffrn_orient_matrix_UB_23      -0.0616074000
_diffrn_orient_matrix_UB_31      -0.0402640000
_diffrn_orient_matrix_UB_32      -0.0207286000
_diffrn_orient_matrix_UB_33      0.0975008000
_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  0.0397
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.9969
_diffrn_reflns_Laue_measured_fraction_max 0.9786
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18334
_diffrn_reflns_point_group_measured_fraction_full 0.9969
_diffrn_reflns_point_group_measured_fraction_max 0.9786
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         75.82
_diffrn_reflns_theta_min         4.07
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.562
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
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    1.333
_exptl_crystal_description       prism
_exptl_crystal_F_000             1116.697
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.3971
_refine_diff_density_min         -0.4884
_refine_diff_density_rms         0.0690
_refine_ls_d_res_high            0.7951
_refine_ls_d_res_low             10.8690
_refine_ls_goodness_of_fit_ref   1.0494
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    49
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5394
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0494
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0350P)²+1.1727P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0951
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                4809
_reflns_number_total             5394
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4cc03551h2.cif
_cod_data_source_block           20230425ZengYuan-4_auto
_cod_depositor_comments
'Adding full bibliography for 7133612--7133614.cif.'
_cod_database_code               7133614
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17a,H17b), C26(H26a,H26b), C25(H25a,H25b)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C5(H5), C6(H6), C29(H29), C33(H33), C20(H20), C30(H30), C14(H14),
 C22(H22), C3(H3), C23(H23), C32(H32), C31(H31), C21(H21), C10(H10), C2(H2),
 C13(H13), C12(H12), C11(H11)
;
_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 1.289
_oxdiff_exptl_absorpt_empirical_full_min 0.449
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2
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_refinement_flags_posn
Cl1 Cl 0.25658(4) 0.20788(2) 0.77609(4) 0.04352(12) Uani 1.000000 .
O2 O 0.86853(11) 0.34066(6) 0.69385(8) 0.0324(2) Uani 1.000000 .
O1 O 0.59190(11) 0.33920(7) 0.45575(8) 0.0399(3) Uani 1.000000 .
N1 N 0.61237(11) 0.38990(7) 0.61225(8) 0.0256(2) Uani 1.000000 .
N2 N 0.73313(11) 0.45365(6) 0.85496(8) 0.0226(2) Uani 1.000000 .
N3 N 0.75871(11) 0.42008(6) 0.76719(8) 0.0230(2) Uani 1.000000 .
C4 C 0.52589(13) 0.34381(8) 0.64770(10) 0.0234(3) Uani 1.000000 .
C27 C 0.83989(13) 0.36249(7) 0.77086(10) 0.0233(3) Uani 1.000000 .
C19 C 0.57133(14) 0.54053(8) 0.88786(10) 0.0260(3) Uani 1.000000 .
C28 C 0.89318(13) 0.32565(7) 0.86895(10) 0.0240(3) Uani 1.000000 .
C7 C 0.63978(13) 0.38355(8) 0.51978(10) 0.0262(3) Uani 1.000000 .
C8 C 0.73501(13) 0.44216(8) 0.51454(10) 0.0251(3) Uani 1.000000 .
C15 C 0.75614(13) 0.47979(8) 0.60090(10) 0.0255(3) Uani 1.000000 .
H15 H 0.81157(13) 0.52079(8) 0.61566(10) 0.0306(3) Uiso 1.000000 R
C18 C 0.60639(12) 0.48126(8) 0.82039(10) 0.0232(3) Uani 1.000000 .
H18 H 0.54885(12) 0.43791(8) 0.81798(10) 0.0278(3) Uiso 1.000000 R
C16 C 0.68203(13) 0.44975(7) 0.67209(10) 0.0230(3) Uani 1.000000 .
C17 C 0.60195(13) 0.50751(8) 0.71205(10) 0.0255(3) Uani 1.000000 .
H17a H 0.51658(13) 0.50711(8) 0.67193(10) 0.0306(3) Uiso 1.000000 R
H17b H 0.63621(13) 0.55866(8) 0.71110(10) 0.0306(3) Uiso 1.000000 R
C9 C 0.79617(13) 0.45072(9) 0.42978(11) 0.0298(3) Uani 1.000000 .
C5 C 0.56494(13) 0.28020(8) 0.70337(11) 0.0282(3) Uani 1.000000 .
H5 H 0.64893(13) 0.26567(8) 0.71471(11) 0.0339(4) Uiso 1.000000 R
C26 C 0.82179(13) 0.51400(8) 0.89133(11) 0.0289(3) Uani 1.000000 .
H26a H 0.90664(13) 0.49381(8) 0.90672(11) 0.0347(4) Uiso 1.000000 R
H26b H 0.81658(13) 0.55340(8) 0.83961(11) 0.0347(4) Uiso 1.000000 R
C6 C 0.48243(14) 0.23736(8) 0.74284(11) 0.0288(3) Uani 1.000000 .
H6 H 0.50917(14) 0.19380(8) 0.78138(11) 0.0346(4) Uiso 1.000000 R
C24 C 0.65826(15) 0.57314(8) 0.96430(11) 0.0312(3) Uani 1.000000 .
C1 C 0.36158(14) 0.25931(8) 0.72498(11) 0.0284(3) Uani 1.000000 .
C29 C 0.82560(15) 0.31173(9) 0.94155(12) 0.0316(3) Uani 1.000000 .
H29 H 0.74374(15) 0.32991(9) 0.93288(12) 0.0379(4) Uiso 1.000000 R
C33 C 1.01182(14) 0.29764(9) 0.88126(12) 0.0326(3) Uani 1.000000 .
H33 H 1.05700(14) 0.30526(9) 0.83051(12) 0.0391(4) Uiso 1.000000 R
C20 C 0.44863(15) 0.56247(9) 0.87199(12) 0.0328(3) Uani 1.000000 .
H20 H 0.38909(15) 0.53927(9) 0.82073(12) 0.0394(4) Uiso 1.000000 R
C30 C 0.87779(16) 0.27134(10) 1.02648(12) 0.0381(4) Uani 1.000000 .
H30 H 0.83119(16) 0.26119(10) 1.07561(12) 0.0458(4) Uiso 1.000000 R
C14 C 0.85859(15) 0.51681(10) 0.41815(13) 0.0384(4) Uani 1.000000 .
H14 H 0.85863(15) 0.55708(10) 0.46363(13) 0.0460(5) Uiso 1.000000 R
C22 C 0.49930(18) 0.65232(9) 1.00513(13) 0.0415(4) Uani 1.000000 .
H22 H 0.47529(18) 0.69132(9) 1.04423(13) 0.0499(5) Uiso 1.000000 R
C25 C 0.78970(15) 0.54638(10) 0.98515(12) 0.0377(4) Uani 1.000000 .
H25a H 0.80175(15) 0.50760(10) 1.03816(12) 0.0453(4) Uiso 1.000000 R
H25b H 0.84537(15) 0.58883(10) 1.00965(12) 0.0453(4) Uiso 1.000000 R
C3 C 0.40333(15) 0.36400(9) 0.62928(14) 0.0404(4) Uani 1.000000 .
H3 H 0.37573(15) 0.40683(9) 0.58948(14) 0.0485(5) Uiso 1.000000 R
C23 C 0.62049(17) 0.62951(9) 1.02222(13) 0.0392(4) Uani 1.000000 .
H23 H 0.67933(17) 0.65247(9) 1.07423(13) 0.0471(5) Uiso 1.000000 R
C32 C 1.06457(16) 0.25855(11) 0.96741(14) 0.0431(4) Uani 1.000000 .
H32 H 1.14661(16) 0.24060(11) 0.97658(14) 0.0517(5) Uiso 1.000000 R
C31 C 0.99734(17) 0.24575(11) 1.04006(13) 0.0420(4) Uani 1.000000 .
H31 H 1.03354(17) 0.21930(11) 1.09937(13) 0.0504(5) Uiso 1.000000 R
C21 C 0.41302(17) 0.61803(10) 0.93070(13) 0.0399(4) Uani 1.000000 .
H21 H 0.32909(17) 0.63261(10) 0.91979(13) 0.0478(5) Uiso 1.000000 R
C10 C 0.79885(16) 0.39162(11) 0.36304(12) 0.0418(4) Uani 1.000000 .
H10 H 0.75678(16) 0.34621(11) 0.36986(12) 0.0502(5) Uiso 1.000000 R
C2 C 0.32042(15) 0.32179(10) 0.66884(16) 0.0449(4) Uani 1.000000 .
H2 H 0.23623(15) 0.33589(10) 0.65729(16) 0.0539(5) Uiso 1.000000 R
C13 C 0.92056(17) 0.52437(13) 0.34095(15) 0.0521(5) Uani 1.000000 .
H13 H 0.96208(17) 0.56982(13) 0.33327(15) 0.0625(6) Uiso 1.000000 R
C12 C 0.92190(17) 0.46558(15) 0.27500(14) 0.0566(6) Uani 1.000000 .
H12 H 0.96351(17) 0.47098(15) 0.22157(14) 0.0679(7) Uiso 1.000000 R
C11 C 0.86285(18) 0.39912(14) 0.28678(13) 0.0548(5) Uani 1.000000 .
H11 H 0.86600(18) 0.35841(14) 0.24261(13) 0.0657(6) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
C7 N1 C4 124.52(12) . . ?
C16 N1 C4 123.07(11) . . ?
C16 N1 C7 112.41(11) . . ?
C18 N2 N3 102.76(10) . . ?
C26 N2 N3 110.59(10) . . ?
C26 N2 C18 112.96(11) . . ?
C27 N3 N2 122.50(11) . . ?
C16 N3 N2 113.92(10) . . ?
C16 N3 C27 123.43(11) . . ?
C5 C4 N1 120.28(13) . . ?
C3 C4 N1 119.97(13) . . ?
C3 C4 C5 119.72(13) . . ?
N3 C27 O2 120.01(13) . . ?
C28 C27 O2 120.24(12) . . ?
C28 C27 N3 119.75(11) . . ?
C24 C19 C18 121.57(13) . . ?
C20 C19 C18 118.39(13) . . ?
C20 C19 C24 120.03(13) . . ?
C29 C28 C27 123.17(13) . . ?
C33 C28 C27 116.77(12) . . ?
C33 C28 C29 119.69(13) . . ?
N1 C7 O1 124.74(14) . . ?
C8 C7 O1 128.61(13) . . ?
C8 C7 N1 106.63(12) . . ?
C15 C8 C7 107.47(12) . . ?
C9 C8 C7 124.05(13) . . ?
C9 C8 C15 128.38(14) . . ?
H15 C15 C8 123.94(8) . . ?
C16 C15 C8 112.13(12) . . ?
C16 C15 H15 123.94(7) . . ?
C19 C18 N2 113.17(11) . . ?
H18 C18 N2 108.32(7) . . ?
H18 C18 C19 108.32(7) . . ?
C17 C18 N2 103.92(10) . . ?
C17 C18 C19 114.52(11) . . ?
C17 C18 H18 108.32(7) . . ?
N3 C16 N1 111.37(11) . . ?
C15 C16 N1 101.34(11) . . ?
C15 C16 N3 113.61(11) . . ?
C17 C16 N1 114.21(11) . . ?
C17 C16 N3 101.23(10) . . ?
C17 C16 C15 115.58(11) . . ?
C16 C17 C18 103.67(11) . . ?
H17a C17 C18 111.03(7) . . ?
H17a C17 C16 111.03(7) . . ?
H17b C17 C18 111.03(7) . . ?
H17b C17 C16 111.03(7) . . ?
H17b C17 H17a 109.0 . . ?
C14 C9 C8 120.20(15) . . ?
C10 C9 C8 120.90(15) . . ?
C10 C9 C14 118.80(15) . . ?
H5 C5 C4 119.70(8) . . ?
C6 C5 C4 120.60(13) . . ?
C6 C5 H5 119.70(8) . . ?
H26a C26 N2 110.20(7) . . ?
H26b C26 N2 110.20(7) . . ?
H26b C26 H26a 108.5 . . ?
C25 C26 N2 107.56(12) . . ?
C25 C26 H26a 110.20(8) . . ?
C25 C26 H26b 110.20(9) . . ?
H6 C6 C5 120.72(8) . . ?
C1 C6 C5 118.57(13) . . ?
C1 C6 H6 120.72(9) . . ?
C25 C24 C19 120.03(13) . . ?
C23 C24 C19 118.77(15) . . ?
C23 C24 C25 121.19(15) . . ?
C6 C1 Cl1 119.59(12) . . ?
C2 C1 Cl1 118.57(12) . . ?
C2 C1 C6 121.83(14) . . ?
H29 C29 C28 120.06(9) . . ?
C30 C29 C28 119.88(14) . . ?
C30 C29 H29 120.06(9) . . ?
H33 C33 C28 119.92(8) . . ?
C32 C33 C28 120.17(14) . . ?
C32 C33 H33 119.92(9) . . ?
H20 C20 C19 119.88(9) . . ?
C21 C20 C19 120.25(16) . . ?
C21 C20 H20 119.88(11) . . ?
H30 C30 C29 119.88(9) . . ?
C31 C30 C29 120.24(15) . . ?
C31 C30 H30 119.88(9) . . ?
H14 C14 C9 119.65(10) . . ?
C13 C14 C9 120.69(18) . . ?
C13 C14 H14 119.65(13) . . ?
C23 C22 H22 120.22(10) . . ?
C21 C22 H22 120.22(9) . . ?
C21 C22 C23 119.55(15) . . ?
C24 C25 C26 110.82(13) . . ?
H25a C25 C26 109.48(9) . . ?
H25a C25 C24 109.48(9) . . ?
H25b C25 C26 109.48(9) . . ?
H25b C25 C24 109.48(9) . . ?
H25b C25 H25a 108.1 . . ?
H3 C3 C4 119.97(9) . . ?
C2 C3 C4 120.06(14) . . ?
C2 C3 H3 119.97(10) . . ?
C22 C23 C24 121.16(16) . . ?
H23 C23 C24 119.42(10) . . ?
H23 C23 C22 119.42(10) . . ?
H32 C32 C33 120.10(9) . . ?
C31 C32 C33 119.81(15) . . ?
C31 C32 H32 120.10(10) . . ?
C32 C31 C30 120.15(15) . . ?
H31 C31 C30 119.93(9) . . ?
H31 C31 C32 119.93(10) . . ?
C22 C21 C20 120.20(16) . . ?
H21 C21 C20 119.90(11) . . ?
H21 C21 C22 119.90(9) . . ?
H10 C10 C9 119.90(10) . . ?
C11 C10 C9 120.20(19) . . ?
C11 C10 H10 119.90(13) . . ?
C3 C2 C1 119.20(15) . . ?
H2 C2 C1 120.40(9) . . ?
H2 C2 C3 120.40(10) . . ?
H13 C13 C14 120.03(13) . . ?
C12 C13 C14 119.93(19) . . ?
C12 C13 H13 120.03(11) . . ?
H12 C12 C13 119.94(11) . . ?
C11 C12 C13 120.12(16) . . ?
C11 C12 H12 119.94(11) . . ?
C12 C11 C10 120.2(2) . . ?
H11 C11 C10 119.89(13) . . ?
H11 C11 C12 119.89(11) . . ?
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
Cl1 C1 1.7452(15) . ?
O2 C27 1.2273(17) . ?
O1 C7 1.2150(18) . ?
N1 C4 1.4272(17) . ?
N1 C7 1.3677(18) . ?
N1 C16 1.4623(17) . ?
N2 N3 1.4237(15) . ?
N2 C18 1.4728(17) . ?
N2 C26 1.4727(18) . ?
N3 C27 1.3617(17) . ?
N3 C16 1.4911(17) . ?
C4 C5 1.383(2) . ?
C4 C3 1.381(2) . ?
C27 C28 1.4972(19) . ?
C19 C18 1.5085(18) . ?
C19 C24 1.390(2) . ?
C19 C20 1.392(2) . ?
C28 C29 1.390(2) . ?
C28 C33 1.388(2) . ?
C7 C8 1.501(2) . ?
C8 C15 1.335(2) . ?
C8 C9 1.4725(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.5031(18) . ?
C18 H18 1.0000 . ?
C18 C17 1.5443(18) . ?
C16 C17 1.5372(18) . ?
C17 H17a 0.9900 . ?
C17 H17b 0.9900 . ?
C9 C14 1.395(2) . ?
C9 C10 1.399(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(2) . ?
C26 H26a 0.9900 . ?
C26 H26b 0.9900 . ?
C26 C25 1.518(2) . ?
C6 H6 0.9500 . ?
C6 C1 1.371(2) . ?
C24 C25 1.507(2) . ?
C24 C23 1.399(2) . ?
C1 C2 1.375(2) . ?
C29 H29 0.9500 . ?
C29 C30 1.384(2) . ?
C33 H33 0.9500 . ?
C33 C32 1.386(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.386(2) . ?
C30 H30 0.9500 . ?
C30 C31 1.381(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.386(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.380(3) . ?
C22 C21 1.383(3) . ?
C25 H25a 0.9900 . ?
C25 H25b 0.9900 . ?
C3 H3 0.9500 . ?
C3 C2 1.387(2) . ?
C23 H23 0.9500 . ?
C32 H32 0.9500 . ?
C32 C31 1.385(2) . ?
C31 H31 0.9500 . ?
C21 H21 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.390(2) . ?
C2 H2 0.9500 . ?
C13 H13 0.9500 . ?
C13 C12 1.385(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.382(3) . ?
C11 H11 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
Cl1 C1 C6 C5 -178.48(12) . . . . ?
Cl1 C1 C2 C3 178.82(15) . . . . ?
O2 C27 N3 N2 -172.36(12) . . . . ?
O2 C27 N3 C16 12.39(17) . . . . ?
O2 C27 C28 C29 -140.78(14) . . . . ?
O2 C27 C28 C33 32.23(16) . . . . ?
O1 C7 N1 C4 1.82(19) . . . . ?
O1 C7 N1 C16 -178.22(15) . . . . ?
O1 C7 C8 C15 177.30(17) . . . . ?
O1 C7 C8 C9 -6.05(19) . . . . ?
N1 C4 C5 C6 176.40(13) . . . . ?
N1 C4 C3 C2 -176.07(16) . . . . ?
N1 C7 C8 C15 -1.20(13) . . . . ?
N1 C7 C8 C9 175.44(11) . . . . ?
N1 C16 N3 N2 -122.17(11) . . . . ?
N1 C16 N3 C27 53.44(13) . . . . ?
N1 C16 C15 C8 -1.32(12) . . . . ?
N1 C16 C17 C18 97.95(12) . . . . ?
N2 N3 C27 C28 8.10(14) . . . . ?
N2 N3 C16 C15 124.16(11) . . . . ?
N2 N3 C16 C17 -0.40(11) . . . . ?
N2 C18 C19 C24 9.98(14) . . . . ?
N2 C18 C19 C20 -170.12(12) . . . . ?
N2 C18 C17 C16 36.82(11) . . . . ?
N2 C26 C25 C24 -56.45(13) . . . . ?
N3 C27 C28 C29 38.76(16) . . . . ?
N3 C27 C28 C33 -148.23(14) . . . . ?
N3 C16 C15 C8 118.23(12) . . . . ?
N3 C16 C17 C18 -21.82(11) . . . . ?
C4 C5 C6 C1 0.33(17) . . . . ?
C4 C3 C2 C1 -1.0(2) . . . . ?
C27 C28 C29 C30 174.09(15) . . . . ?
C27 C28 C33 C32 -175.88(15) . . . . ?
C19 C18 C17 C16 160.78(13) . . . . ?
C19 C24 C25 C26 27.04(16) . . . . ?
C19 C24 C23 C22 0.59(18) . . . . ?
C19 C20 C21 C22 0.33(18) . . . . ?
C28 C29 C30 C31 0.94(19) . . . . ?
C28 C33 C32 C31 1.7(2) . . . . ?
C7 C8 C15 C16 1.58(12) . . . . ?
C7 C8 C9 C14 163.45(14) . . . . ?
C7 C8 C9 C10 -20.21(17) . . . . ?
C8 C15 C16 C17 -125.35(12) . . . . ?
C8 C9 C14 C13 177.44(15) . . . . ?
C8 C9 C10 C11 -176.36(16) . . . . ?
C15 C16 C17 C18 -145.04(13) . . . . ?
C9 C14 C13 C12 -0.65(19) . . . . ?
C9 C10 C11 C12 -1.5(2) . . . . ?
C5 C6 C1 C2 0.49(19) . . . . ?
C26 C25 C24 C23 -154.48(14) . . . . ?
C6 C1 C2 C3 -0.15(19) . . . . ?
C24 C23 C22 C21 1.2(2) . . . . ?
C29 C30 C31 C32 -1.8(2) . . . . ?
C33 C32 C31 C30 0.5(2) . . . . ?
C20 C21 C22 C23 -1.7(2) . . . . ?
C14 C13 C12 C11 -0.8(2) . . . . ?
C10 C11 C12 C13 1.9(2) . . . . ?
