#------------------------------------------------------------------------------
#$Date: 2020-12-01 03:54:03 +0200 (Tue, 01 Dec 2020) $
#$Revision: 259370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/74/7127463.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_7127463
loop_
_publ_author_name
'Xiang, Min'
'Li, Chen-Yi'
'Song, Xiang-Jia'
'Zou, Ying'
'Huang, Zhi-Cheng'
'Li, Xia'
'Tian, Fang'
'Wang, Li-Xin'
_publ_section_title
;
 Organocatalytic and enantioselective [4+2] cyclization between
 hydroxymaleimides and ortho-hydroxyphenyl para-quinone
 methide-selective preparation of chiral hemiketals.
;
_journal_issue                   94
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              14825
_journal_page_last               14828
_journal_paper_doi               10.1039/d0cc06777f
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety
'C33 H37 N O5, C0.7 H0.7 Cl1.55, C0.3 H0.3 Cl1.45'
_chemical_formula_sum            'C34 H38 Cl3 N O5'
_chemical_formula_weight         647.00
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-03-18 deposited with the CCDC.	2020-10-29 downloaded from the CCDC.
;
_cell_angle_alpha                98.879(6)
_cell_angle_beta                 105.364(6)
_cell_angle_gamma                95.484(6)
_cell_formula_units_Z            2
_cell_length_a                   10.5380(6)
_cell_length_b                   12.9179(10)
_cell_length_c                   13.0658(9)
_cell_measurement_reflns_used    2830
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6750
_cell_measurement_theta_min      4.4870
_cell_volume                     1677.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -32.00   1.00    1.00    --  -33.50 178.00 150.00   76
  2  ω    -62.00  36.00   1.00    1.00    --  -33.50  77.00 120.00   98
  3  ω    -46.00   0.00   1.00    1.00    --  -33.50 -19.00  90.00   46
  4  ω    -86.00 -60.00   1.00    1.00    --  -33.50 -57.00  30.00   26
  5  ω     57.00 109.00   1.00    1.00    --   36.47 178.00  30.00   52
  6  ω     57.00 109.00   1.00    1.00    --   36.47 178.00 120.00   52
  7  ω     18.00 107.00   1.00    1.00    --   36.47  37.00-120.00   89
  8  ω    -33.00  18.00   1.00    1.00    --   36.47 -77.00 -30.00   51
  9  ω     36.00  65.00   1.00    1.00    --   36.47 -77.00 -30.00   29
 10  ω    -34.00  47.00   1.00    1.00    --   36.47 -37.00  60.00   81
 11  ω     58.00  91.00   1.00    1.00    --   36.47 178.00  90.00   33
 12  ω     68.00  94.00   1.00    1.00    --   36.47 178.00   0.00   26
 13  ω     40.00 100.00   1.00    1.00    --   36.47-140.00-122.00   60
 14  ω    103.00 128.00   1.00    5.50    --  108.00 -45.00 150.00   25
 15  ω     39.00  90.00   1.00    5.50    --  108.00 -45.00 150.00   51
 16  ω     46.00  72.00   1.00    5.50    --  108.00 -61.00 120.00   26
 17  ω     39.00 114.00   1.00    5.50    --  108.00 -45.00 -30.00   75
 18  ω     64.00 169.00   1.00    5.50    --  108.00  15.00-150.00  105
 19  ω     38.00 120.00   1.00    5.50    --  108.00 -45.00  60.00   82
 20  ω     64.00 111.00   1.00    5.50    --  108.00-111.00-150.00   47
 21  ω    120.00 176.00   1.00    5.50    --  108.00  61.00  90.00   56
 22  ω     37.00 111.00   1.00    5.50    --  108.00-111.00 -30.00   74
 23  ω     88.00 121.00   1.00    5.50    --  108.00  45.00   0.00   33
 24  ω    116.00 165.00   1.00    5.50    --  108.00  61.00  30.00   49
 25  ω     46.00 110.00   1.00    5.50    --  108.00 -94.00  90.00   64
 26  ω     61.00 103.00   1.00    5.50    --  108.00-111.00  60.00   42
 27  ω     96.00 153.00   1.00    5.50    --  108.00  45.00 120.00   57
 28  ω     97.00 126.00   1.00    5.50    --  108.00  45.00  90.00   29
 29  ω     69.00 140.00   1.00    5.50    --  108.00 178.00   0.00   71
 30  ω     41.00  85.00   1.00    5.50    --  108.00 -61.00 -60.00   44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0669125000
_diffrn_orient_matrix_UB_12      -0.0073482000
_diffrn_orient_matrix_UB_13      -0.1214847000
_diffrn_orient_matrix_UB_21      -0.0235141000
_diffrn_orient_matrix_UB_22      -0.1216385000
_diffrn_orient_matrix_UB_23      -0.0151017000
_diffrn_orient_matrix_UB_31      -0.1357816000
_diffrn_orient_matrix_UB_32      0.0049762000
_diffrn_orient_matrix_UB_33      0.0225429000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11890
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.062
_diffrn_reflns_theta_max         67.062
_diffrn_reflns_theta_min         3.571
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.802
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81539
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.281
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     411
_refine_ls_number_reflns         6004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0716
_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)+(0.1136P)²+0.4778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1933
_refine_ls_wR_factor_ref         0.2204
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4283
_reflns_number_total             6004
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc06777f2.cif
_cod_data_source_block           201909219
_cod_database_code               7127463
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20O4b
_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   0.767
_shelx_estimated_absorpt_t_min   0.578
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Uiso/Uaniso restraints and constraints
Uanis(Cl2) = Uanis(Cl2A)
Uanis(C34) = Uanis(C34A)
Uanis(Cl1) = Uanis(Cl1A)
Uanis(Cl3) = Uanis(Cl3A)
3. Others
 Sof(C34A)=Sof(H34A)=Sof(Cl1A)=Sof(Cl2A)=1-FVAR(1)
 Sof(C34)=Sof(H34)=Sof(Cl1)=Sof(Cl2)=FVAR(1)
 Sof(Cl3A)=1-FVAR(2)
 Sof(Cl3)=FVAR(2)
4.a Riding coordinates:
 O5(H5a)
4.b Ternary CH refined with riding coordinates:
 C5(H5), C34(H34), C34A(H34A)
4.c Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b)
4.d Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C21(H21), C25(H25)
4.e Idealised Me refined as rotating group:
 C13(H13a,H13b,H13c), C27(H27a,H27b,H27c), C28(H28a,H28b,H28c), C29(H29a,H29b,
 H29c), C31(H31a,H31b,H31c), C32(H32a,H32b,H32c), C33(H33a,H33b,H33c)
4.f 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 1.256
_oxdiff_exptl_absorpt_empirical_full_min 0.847
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
C1 C 0.5626(3) 0.9253(2) 0.3508(2) 0.0410(6) Uani 1 1 d . . . . .
C2 C 0.4421(3) 0.8568(2) 0.3641(2) 0.0397(6) Uani 1 1 d . . . . .
C3 C 0.4013(3) 0.7663(2) 0.2637(2) 0.0391(6) Uani 1 1 d . . . . .
C4 C 0.4749(3) 0.8068(2) 0.1889(2) 0.0426(6) Uani 1 1 d . . . . .
C5 C 0.4553(3) 0.6630(2) 0.2946(2) 0.0438(6) Uani 1 1 d . . . . .
H5 H 0.4073 0.6048 0.2353 0.053 Uiso 1 1 calc R . . . .
C6 C 0.4131(3) 0.6434(3) 0.3925(3) 0.0527(7) Uani 1 1 d . . . . .
C7 C 0.4277(3) 0.7289(3) 0.4741(3) 0.0536(7) Uani 1 1 d . . . . .
C8 C 0.3925(4) 0.7196(4) 0.5681(3) 0.0777(12) Uani 1 1 d . . . . .
H8 H 0.4027 0.7786 0.6220 0.093 Uiso 1 1 calc R . . . .
C9 C 0.3423(5) 0.6215(6) 0.5794(5) 0.1015(19) Uani 1 1 d . . . . .
H9 H 0.3206 0.6134 0.6425 0.122 Uiso 1 1 calc R . . . .
C10 C 0.3236(4) 0.5351(5) 0.4987(6) 0.1003(19) Uani 1 1 d . . . . .
H10 H 0.2876 0.4693 0.5068 0.120 Uiso 1 1 calc R . . . .
C11 C 0.3584(4) 0.5455(3) 0.4046(4) 0.0767(12) Uani 1 1 d . . . . .
H11 H 0.3450 0.4868 0.3498 0.092 Uiso 1 1 calc R . . . .
C12 C 0.2503(3) 0.7400(2) 0.2085(2) 0.0471(6) Uani 1 1 d . . . . .
H12A H 0.2335 0.6710 0.1619 0.057 Uiso 1 1 calc R . . . .
H12B H 0.2063 0.7338 0.2642 0.057 Uiso 1 1 calc R . . . .
C13 C 0.1851(4) 0.8173(3) 0.1417(3) 0.0700(10) Uani 1 1 d . . . . .
H13A H 0.2221 0.8203 0.0824 0.105 Uiso 1 1 calc GR . . . .
H13B H 0.2009 0.8863 0.1862 0.105 Uiso 1 1 calc GR . . . .
H13C H 0.0911 0.7939 0.1144 0.105 Uiso 1 1 calc GR . . . .
C14 C 0.6613(3) 0.9471(2) 0.2022(2) 0.0462(6) Uani 1 1 d . . . . .
C15 C 0.7786(4) 0.9098(3) 0.2061(4) 0.0722(10) Uani 1 1 d . . . . .
H15 H 0.7982 0.8509 0.2369 0.087 Uiso 1 1 calc R . . . .
C16 C 0.8689(4) 0.9614(5) 0.1632(4) 0.0955(15) Uani 1 1 d . . . . .
H16 H 0.9503 0.9376 0.1668 0.115 Uiso 1 1 calc R . . . .
C17 C 0.8398(5) 1.0452(4) 0.1166(4) 0.0907(14) Uani 1 1 d . . . . .
H17 H 0.8998 1.0778 0.0864 0.109 Uiso 1 1 calc R . . . .
C18 C 0.7232(6) 1.0821(5) 0.1135(5) 0.1080(18) Uani 1 1 d . . . . .
H18 H 0.7044 1.1412 0.0827 0.130 Uiso 1 1 calc R . . . .
C19 C 0.6323(5) 1.0330(4) 0.1555(4) 0.0857(13) Uani 1 1 d . . . . .
H19 H 0.5517 1.0580 0.1522 0.103 Uiso 1 1 calc R . . . .
C20 C 0.6040(3) 0.6600(2) 0.3083(2) 0.0409(6) Uani 1 1 d . . . . .
C21 C 0.6404(3) 0.5988(2) 0.2264(2) 0.0441(6) Uani 1 1 d . . . . .
H21 H 0.5740 0.5640 0.1650 0.053 Uiso 1 1 calc R . . . .
C22 C 0.7718(3) 0.5874(2) 0.2322(2) 0.0438(6) Uani 1 1 d . . . . .
C23 C 0.8688(3) 0.6403(2) 0.3265(2) 0.0473(6) Uani 1 1 d . . . . .
C24 C 0.8379(3) 0.7069(2) 0.4095(2) 0.0439(6) Uani 1 1 d . . . . .
C25 C 0.7038(3) 0.7140(2) 0.3988(2) 0.0427(6) Uani 1 1 d . . . . .
H25 H 0.6805 0.7560 0.4536 0.051 Uiso 1 1 calc R . . . .
C26 C 0.8076(3) 0.5210(3) 0.1388(3) 0.0560(8) Uani 1 1 d . . . . .
C27 C 0.6844(4) 0.4801(4) 0.0421(4) 0.0866(14) Uani 1 1 d . . . . .
H27A H 0.6202 0.4376 0.0641 0.130 Uiso 1 1 calc GR . . . .
H27B H 0.7096 0.4381 -0.0146 0.130 Uiso 1 1 calc GR . . . .
H27C H 0.6462 0.5391 0.0162 0.130 Uiso 1 1 calc GR . . . .
C28 C 0.8704(6) 0.4261(4) 0.1744(4) 0.1004(16) Uani 1 1 d . . . . .
H28A H 0.9464 0.4502 0.2362 0.151 Uiso 1 1 calc GR . . . .
H28B H 0.8978 0.3884 0.1165 0.151 Uiso 1 1 calc GR . . . .
H28C H 0.8067 0.3799 0.1930 0.151 Uiso 1 1 calc GR . . . .
C29 C 0.9019(4) 0.5897(4) 0.0975(3) 0.0844(13) Uani 1 1 d . . . . .
H29A H 0.8574 0.6446 0.0683 0.127 Uiso 1 1 calc GR . . . .
H29B H 0.9285 0.5468 0.0422 0.127 Uiso 1 1 calc GR . . . .
H29C H 0.9790 0.6209 0.1561 0.127 Uiso 1 1 calc GR . . . .
C30 C 0.9458(3) 0.7703(3) 0.5101(3) 0.0621(8) Uani 1 1 d . . . . .
C31 C 1.0133(5) 0.6947(5) 0.5800(3) 0.0887(13) Uani 1 1 d . . . . .
H31A H 0.9476 0.6529 0.6011 0.133 Uiso 1 1 calc GR . . . .
H31B H 1.0781 0.7350 0.6434 0.133 Uiso 1 1 calc GR . . . .
H31C H 1.0564 0.6489 0.5393 0.133 Uiso 1 1 calc GR . . . .
C32 C 1.0492(4) 0.8412(4) 0.4780(4) 0.0929(14) Uani 1 1 d . . . . .
H32A H 1.1037 0.7979 0.4471 0.139 Uiso 1 1 calc GR . . . .
H32B H 1.1040 0.8897 0.5409 0.139 Uiso 1 1 calc GR . . . .
H32C H 1.0043 0.8803 0.4260 0.139 Uiso 1 1 calc GR . . . .
C33 C 0.8848(4) 0.8448(4) 0.5812(4) 0.0936(16) Uani 1 1 d . . . . .
H33A H 0.8377 0.8912 0.5391 0.140 Uiso 1 1 calc GR . . . .
H33B H 0.9542 0.8860 0.6408 0.140 Uiso 1 1 calc GR . . . .
H33C H 0.8243 0.8038 0.6080 0.140 Uiso 1 1 calc GR . . . .
N1 N 0.5671(2) 0.89608(18) 0.24641(18) 0.0412(5) Uani 1 1 d . . . . .
O1 O 0.6381(2) 0.99371(18) 0.41844(18) 0.0581(6) Uani 1 1 d . . . . .
O2 O 0.3405(2) 0.91829(17) 0.36527(17) 0.0513(5) Uani 1 1 d . . . . .
H2 H 0.3573 0.9571 0.4245 0.077 Uiso 1 1 calc GR . . . .
O3 O 0.4860(2) 0.82707(17) 0.46603(15) 0.0482(5) Uani 1 1 d . . . . .
O4 O 0.4619(2) 0.76915(19) 0.09662(17) 0.0601(6) Uani 1 1 d . . . . .
O5 O 0.9983(2) 0.6243(2) 0.3340(2) 0.0719(7) Uani 1 1 d . . . . .
H5A H 1.0628 0.6402 0.3294 0.48(11) Uiso 1 1 d R . . . .
C34 C 0.3139(11) 0.2362(8) 0.1836(10) 0.116(3) Uani 0.698(4) 1 d . . P A 1
H34 H 0.3713 0.2587 0.2579 0.140 Uiso 0.698(4) 1 calc R . P A 1
C34A C 0.262(3) 0.201(2) 0.110(2) 0.116(3) Uani 0.302(4) 1 d . . P A 2
H34A H 0.2462 0.1632 0.0357 0.140 Uiso 0.302(4) 1 calc R . P A 2
Cl1 Cl 0.1665(4) 0.2945(3) 0.1660(3) 0.1212(10) Uani 0.698(4) 1 d . . P A 1
Cl1A Cl 0.1530(10) 0.2565(8) 0.1247(7) 0.1212(10) Uani 0.302(4) 1 d . . P A 2
Cl2 Cl 0.4024(3) 0.2474(3) 0.0937(3) 0.1387(13) Uani 0.698(4) 1 d . . P A 1
Cl2A Cl 0.4227(9) 0.3037(7) 0.1580(8) 0.1387(13) Uani 0.302(4) 1 d . . P A 2
Cl3 Cl 0.253(2) 0.1086(12) 0.161(2) 0.1211(12) Uani 0.157(12) 1 d . . P A 1
Cl3A Cl 0.3035(5) 0.11016(18) 0.2136(5) 0.1211(12) Uani 0.843(12) 1 d . . P A 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'
Cl Cl 0.3639 0.7018 '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
N1 C1 C2 107.7(2) . . ?
O1 C1 C2 126.7(2) . . ?
O1 C1 N1 125.7(3) . . ?
C1 C2 C3 104.6(2) . . ?
O2 C2 C1 109.1(2) . . ?
O2 C2 C3 111.2(2) . . ?
O2 C2 O3 109.0(2) . . ?
O3 C2 C1 105.8(2) . . ?
O3 C2 C3 116.7(2) . . ?
C2 C3 C5 110.2(2) . . ?
C4 C3 C2 103.1(2) . . ?
C4 C3 C5 108.3(2) . . ?
C4 C3 C12 111.5(2) . . ?
C12 C3 C2 114.7(2) . . ?
C12 C3 C5 108.7(2) . . ?
N1 C4 C3 109.1(2) . . ?
O4 C4 C3 127.1(3) . . ?
O4 C4 N1 123.7(3) . . ?
C3 C5 H5 106.6 . . ?
C6 C5 C3 107.1(2) . . ?
C6 C5 H5 106.6 . . ?
C6 C5 C20 113.3(2) . . ?
C20 C5 C3 116.2(2) . . ?
C20 C5 H5 106.6 . . ?
C7 C6 C5 117.6(3) . . ?
C7 C6 C11 118.1(3) . . ?
C11 C6 C5 124.3(4) . . ?
C6 C7 C8 122.3(4) . . ?
C6 C7 O3 119.5(3) . . ?
O3 C7 C8 118.1(4) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 C7 118.4(5) . . ?
C9 C8 H8 120.8 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.8(4) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.3(4) . . ?
C11 C10 H10 119.9 . . ?
C6 C11 C10 120.0(5) . . ?
C6 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C3 C12 H12A 108.0 . . ?
C3 C12 H12B 108.0 . . ?
H12A C12 H12B 107.2 . . ?
C13 C12 C3 117.4(3) . . ?
C13 C12 H12A 108.0 . . ?
C13 C12 H12B 108.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 120.3(3) . . ?
C15 C14 N1 120.1(3) . . ?
C19 C14 N1 119.7(3) . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 118.9(4) . . ?
C16 C15 H15 120.5 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.7(4) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.1(4) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.5(5) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 119.5(4) . . ?
C14 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C21 C20 C5 118.0(2) . . ?
C21 C20 C25 118.5(2) . . ?
C25 C20 C5 123.5(2) . . ?
C20 C21 H21 118.6 . . ?
C22 C21 C20 122.8(3) . . ?
C22 C21 H21 118.6 . . ?
C21 C22 C23 116.8(3) . . ?
C21 C22 C26 121.0(3) . . ?
C23 C22 C26 122.2(2) . . ?
C22 C23 C24 122.6(3) . . ?
O5 C23 C22 116.5(3) . . ?
O5 C23 C24 121.0(3) . . ?
C23 C24 C30 122.5(3) . . ?
C25 C24 C23 117.5(3) . . ?
C25 C24 C30 120.0(3) . . ?
C20 C25 C24 121.7(3) . . ?
C20 C25 H25 119.2 . . ?
C24 C25 H25 119.2 . . ?
C22 C26 C27 111.4(3) . . ?
C28 C26 C22 110.8(3) . . ?
C28 C26 C27 108.4(4) . . ?
C28 C26 C29 110.5(4) . . ?
C29 C26 C22 109.7(3) . . ?
C29 C26 C27 105.9(3) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C24 110.2(3) . . ?
C31 C30 C32 110.8(4) . . ?
C31 C30 C33 107.0(4) . . ?
C32 C30 C24 111.3(3) . . ?
C33 C30 C24 111.1(3) . . ?
C33 C30 C32 106.2(4) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C1 N1 C4 113.1(2) . . ?
C1 N1 C14 123.7(2) . . ?
C4 N1 C14 123.1(2) . . ?
C2 O2 H2 109.5 . . ?
C7 O3 C2 115.6(2) . . ?
C23 O5 H5A 151.8 . . ?
Cl1 C34 H34 110.7 . . ?
Cl2 C34 H34 110.7 . . ?
Cl2 C34 Cl1 117.8(6) . . ?
Cl3 C34 H34 110.7 . . ?
Cl3 C34 Cl1 100.9(10) . . ?
Cl3 C34 Cl2 105.4(9) . . ?
Cl1A C34A H34A 112.6 . . ?
Cl1A C34A Cl2A 107.4(16) . . ?
Cl1A C34A Cl3A 110.4(15) . . ?
Cl2A C34A H34A 112.6 . . ?
Cl3A C34A H34A 112.6 . . ?
Cl3A C34A Cl2A 100.6(13) . . ?
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
C1 C2 1.542(4) . ?
C1 N1 1.373(4) . ?
C1 O1 1.202(4) . ?
C2 C3 1.551(4) . ?
C2 O2 1.394(3) . ?
C2 O3 1.414(3) . ?
C3 C4 1.520(4) . ?
C3 C5 1.568(4) . ?
C3 C12 1.542(4) . ?
C4 N1 1.404(4) . ?
C4 O4 1.195(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.510(4) . ?
C5 C20 1.535(4) . ?
C6 C7 1.377(5) . ?
C6 C11 1.388(5) . ?
C7 C8 1.393(5) . ?
C7 O3 1.387(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.371(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.372(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.395(7) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.521(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.361(5) . ?
C14 C19 1.368(5) . ?
C14 N1 1.431(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.393(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.343(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.353(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.390(4) . ?
C20 C25 1.392(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.390(4) . ?
C22 C23 1.404(4) . ?
C22 C26 1.533(4) . ?
C23 C24 1.405(4) . ?
C23 O5 1.379(4) . ?
C24 C25 1.396(4) . ?
C24 C30 1.546(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.535(5) . ?
C26 C28 1.525(6) . ?
C26 C29 1.526(5) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.536(6) . ?
C30 C32 1.540(6) . ?
C30 C33 1.536(5) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
O2 H2 0.8200 . ?
O5 H5A 0.7115 . ?
C34 H34 0.9800 . ?
C34 Cl1 1.766(10) . ?
C34 Cl2 1.697(10) . ?
C34 Cl3 1.662(19) . ?
C34A H34A 0.9800 . ?
C34A Cl1A 1.45(3) . ?
C34A Cl2A 1.94(3) . ?
C34A Cl3A 1.91(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.82 2.04 2.820(3) 159.0 2_676
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
C1 C2 C3 C4 -14.9(3) . . . . ?
C1 C2 C3 C5 100.6(2) . . . . ?
C1 C2 C3 C12 -136.3(2) . . . . ?
C1 C2 O3 C7 -148.1(2) . . . . ?
C2 C1 N1 C4 -7.5(3) . . . . ?
C2 C1 N1 C14 176.0(2) . . . . ?
C2 C3 C4 N1 11.3(3) . . . . ?
C2 C3 C4 O4 -170.8(3) . . . . ?
C2 C3 C5 C6 51.1(3) . . . . ?
C2 C3 C5 C20 -76.6(3) . . . . ?
C2 C3 C12 C13 74.5(3) . . . . ?
C3 C2 O3 C7 -32.2(3) . . . . ?
C3 C4 N1 C1 -2.6(3) . . . . ?
C3 C4 N1 C14 173.9(2) . . . . ?
C3 C5 C6 C7 -44.0(3) . . . . ?
C3 C5 C6 C11 134.7(3) . . . . ?
C3 C5 C20 C21 -104.4(3) . . . . ?
C3 C5 C20 C25 76.4(3) . . . . ?
C4 C3 C5 C6 163.2(2) . . . . ?
C4 C3 C5 C20 35.5(3) . . . . ?
C4 C3 C12 C13 -42.3(4) . . . . ?
C5 C3 C4 N1 -105.5(2) . . . . ?
C5 C3 C4 O4 72.4(4) . . . . ?
C5 C3 C12 C13 -161.6(3) . . . . ?
C5 C6 C7 C8 -179.8(3) . . . . ?
C5 C6 C7 O3 -3.3(4) . . . . ?
C5 C6 C11 C10 179.4(3) . . . . ?
C5 C20 C21 C22 -177.7(3) . . . . ?
C5 C20 C25 C24 178.3(3) . . . . ?
C6 C5 C20 C21 131.0(3) . . . . ?
C6 C5 C20 C25 -48.2(4) . . . . ?
C6 C7 C8 C9 0.4(5) . . . . ?
C6 C7 O3 C2 44.6(4) . . . . ?
C7 C6 C11 C10 -1.9(5) . . . . ?
C7 C8 C9 C10 -1.9(7) . . . . ?
C8 C7 O3 C2 -138.7(3) . . . . ?
C8 C9 C10 C11 1.4(7) . . . . ?
C9 C10 C11 C6 0.5(7) . . . . ?
C11 C6 C7 C8 1.4(5) . . . . ?
C11 C6 C7 O3 177.9(3) . . . . ?
C12 C3 C4 N1 134.9(2) . . . . ?
C12 C3 C4 O4 -47.1(4) . . . . ?
C12 C3 C5 C6 -75.4(3) . . . . ?
C12 C3 C5 C20 156.8(2) . . . . ?
C14 C15 C16 C17 -1.4(8) . . . . ?
C15 C14 C19 C18 -0.6(7) . . . . ?
C15 C14 N1 C1 91.9(4) . . . . ?
C15 C14 N1 C4 -84.2(4) . . . . ?
C15 C16 C17 C18 1.8(9) . . . . ?
C16 C17 C18 C19 -1.6(9) . . . . ?
C17 C18 C19 C14 1.0(9) . . . . ?
C19 C14 C15 C16 0.8(6) . . . . ?
C19 C14 N1 C1 -88.4(4) . . . . ?
C19 C14 N1 C4 95.5(4) . . . . ?
C20 C5 C6 C7 85.4(3) . . . . ?
C20 C5 C6 C11 -95.9(4) . . . . ?
C20 C21 C22 C23 0.7(4) . . . . ?
C20 C21 C22 C26 -178.7(3) . . . . ?
C21 C20 C25 C24 -0.9(4) . . . . ?
C21 C22 C23 C24 -3.7(4) . . . . ?
C21 C22 C23 O5 176.9(3) . . . . ?
C21 C22 C26 C27 4.3(5) . . . . ?
C21 C22 C26 C28 -116.5(4) . . . . ?
C21 C22 C26 C29 121.2(3) . . . . ?
C22 C23 C24 C25 4.3(4) . . . . ?
C22 C23 C24 C30 -176.2(3) . . . . ?
C23 C22 C26 C27 -175.1(3) . . . . ?
C23 C22 C26 C28 64.2(4) . . . . ?
C23 C22 C26 C29 -58.2(4) . . . . ?
C23 C24 C25 C20 -1.9(4) . . . . ?
C23 C24 C30 C31 -67.4(4) . . . . ?
C23 C24 C30 C32 55.9(5) . . . . ?
C23 C24 C30 C33 174.1(4) . . . . ?
C25 C20 C21 C22 1.5(4) . . . . ?
C25 C24 C30 C31 112.1(3) . . . . ?
C25 C24 C30 C32 -124.5(4) . . . . ?
C25 C24 C30 C33 -6.3(5) . . . . ?
C26 C22 C23 C24 175.7(3) . . . . ?
C26 C22 C23 O5 -3.8(4) . . . . ?
C30 C24 C25 C20 178.6(3) . . . . ?
N1 C1 C2 C3 14.2(3) . . . . ?
N1 C1 C2 O2 -104.9(2) . . . . ?
N1 C1 C2 O3 138.0(2) . . . . ?
N1 C14 C15 C16 -179.5(4) . . . . ?
N1 C14 C19 C18 179.7(5) . . . . ?
O1 C1 C2 C3 -167.3(3) . . . . ?
O1 C1 C2 O2 73.7(4) . . . . ?
O1 C1 C2 O3 -43.4(4) . . . . ?
O1 C1 N1 C4 173.9(3) . . . . ?
O1 C1 N1 C14 -2.6(5) . . . . ?
O2 C2 C3 C4 102.7(2) . . . . ?
O2 C2 C3 C5 -141.8(2) . . . . ?
O2 C2 C3 C12 -18.8(3) . . . . ?
O2 C2 O3 C7 94.8(3) . . . . ?
O3 C2 C3 C4 -131.4(2) . . . . ?
O3 C2 C3 C5 -16.0(3) . . . . ?
O3 C2 C3 C12 107.1(3) . . . . ?
O3 C7 C8 C9 -176.1(3) . . . . ?
O4 C4 N1 C1 179.3(3) . . . . ?
O4 C4 N1 C14 -4.2(5) . . . . ?
O5 C23 C24 C25 -176.3(3) . . . . ?
O5 C23 C24 C30 3.3(5) . . . . ?
