#------------------------------------------------------------------------------
#$Date: 2021-03-05 04:24:17 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262711 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/78/7157832.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_7157832
loop_
_publ_author_name
'Hsueh, Nai-Chen'
'Chen, Shin-Mei'
'Lin, Chun-Yi'
'Chang, Meng-Yang'
_publ_section_title
;
 HCl-mediated cascade cyclocondensation of oxygenated arylacetic acids
 with arylaldehydes: one-pot synthesis of 1-arylisoquinolines.
;
_journal_issue                   5
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1047
_journal_page_last               1059
_journal_paper_doi               10.1039/d0ob02431g
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C H Cl3, 2(C26 H21 N O3)'
_chemical_formula_sum            'C53 H43 Cl3 N2 O6'
_chemical_formula_weight         910.24
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-03-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-02 deposited with the CCDC.	2020-12-28 downloaded from the CCDC.
;
_cell_angle_alpha                83.0810(10)
_cell_angle_beta                 83.3180(10)
_cell_angle_gamma                79.1050(10)
_cell_formula_units_Z            2
_cell_length_a                   9.82420(10)
_cell_length_b                   13.6944(2)
_cell_length_c                   17.0549(3)
_cell_measurement_reflns_used    22767
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.8650
_cell_measurement_theta_min      1.8440
_cell_volume                     2226.41(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00 100.00   0.50   22.14    --   10.60  82.00-120.00  234
  2  ω    -17.00 100.00   0.50   22.14    --   10.60  82.00 -60.00  234
  3  ω    -15.00 100.00   0.50   22.14    --   10.60  77.00 -60.00  230
  4  ω    -79.00  38.00   0.50   22.14    --   10.60 -82.00  60.00  234
  5  ω    -15.00 100.00   0.50   22.14    --   10.60  77.00 -30.00  230
  6  ω    -16.00  29.00   0.50   22.14    --   10.60  82.00 150.00   90
  7  ω    -20.00 100.00   0.50   22.14    --   10.60  57.00-120.00  240
  8  ω    -60.00 -24.00   0.50   22.14    --   10.60 -57.00-180.00   72
  9  ω    -13.00  17.00   0.50   22.14    --   10.60  57.00 120.00   60
 10  ω     32.00  59.00   0.50   22.14    --   10.60  57.00 120.00   54
 11  ω     61.00  87.00   0.50   22.14    --   10.60  57.00 120.00   52
 12  ω    -79.00  18.00   0.50   22.14    --   10.60 -38.00 120.00  194
 13  ω    -17.00   9.00   0.50   22.14    --   10.60  82.00   0.00   52
 14  ω     38.00  92.00   0.50   22.14    --   10.60  82.00   0.00  108
 15  ω     34.00  93.00   0.50   22.14    --   10.60  77.00-120.00  118
 16  ω    -97.00 -72.00   0.50   22.14    --  -10.90 -82.00 -60.00   50
 17  ω     -8.00  17.00   0.50   22.14    --  -10.90 -82.00  90.00   50
 18  ω    -82.00   4.00   0.50   22.14    --  -10.90 -82.00   0.00  172
 19  ω    -90.00 -64.00   0.50   22.14    --  -10.90 -82.00  90.00   52
 20  ω    -31.00  17.00   0.50   22.14    --  -10.90 -82.00 -60.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0137704000
_diffrn_orient_matrix_UB_12      -0.0373826000
_diffrn_orient_matrix_UB_13      0.0309271000
_diffrn_orient_matrix_UB_21      0.0135905000
_diffrn_orient_matrix_UB_22      0.0299773000
_diffrn_orient_matrix_UB_23      0.0283183000
_diffrn_orient_matrix_UB_31      -0.0712869000
_diffrn_orient_matrix_UB_32      0.0226864000
_diffrn_orient_matrix_UB_33      0.0036115000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            49820
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.04
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
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    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.420
_refine_diff_density_min         -1.269
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     602
_refine_ls_number_reflns         8704
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0634
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0963P)²+3.0166P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1779
_refine_ls_wR_factor_ref         0.1861
_reflns_number_gt                7076
_reflns_number_total             8704
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0ob02431g2.cif
_cod_data_source_block           sh0227-1
_cod_depositor_comments
'Adding full bibliography for 7157832--7157834.cif.'
_cod_database_code               7157832
_diffrn_oxdiff_digest_frames
;
01158603f32e28b6ec1a96e8701814ca40000258219
;
_diffrn_oxdiff_digest_hkl
;
01c179d4427678c9a692e448c57aea4bfa4ca3
;
_reflns_odcompleteness_completeness 99.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2. Others
 Sof(Cl4)=Sof(Cl5)=Sof(H53A)=1-FVAR(1)
 Sof(Cl2)=Sof(Cl3)=Sof(H53)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C53(H53), C53(H53A)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C8(H8), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18),
 C20(H20), C21(H21), C22(H22), C23(H23), C28(H28), C32(H32), C34(H34), C39(H39),
  C40(H40), C41(H41), C42(H42), C44(H44), C46(H46), C47(H47), C48(H48), C49(H49)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C36(H36A,H36B,
 H36C), C51(H51A,H51B,H51C), C52(H52A,H52B,H52C)
;
_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 1.217
_oxdiff_exptl_absorpt_empirical_full_min 0.761
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 1.04081(12) 0.76062(8) 1.04936(6) 0.0600(3) Uani 1 d . . .
Cl2 Cl 0.7604(6) 0.8394(7) 1.0184(4) 0.0794(15) Uani 0.706(15) d A 1 .
Cl3 Cl 0.9989(4) 0.90340(17) 0.9142(3) 0.0599(11) Uani 0.706(15) d A 1 .
Cl4 Cl 1.0063(7) 0.9134(5) 0.9561(12) 0.076(3) Uani 0.294(15) d A 2 .
Cl5 Cl 0.7593(12) 0.8733(7) 1.0082(8) 0.0471(17) Uani 0.294(15) d A 2 .
O1 O 0.2948(2) 0.77535(13) 0.14403(11) 0.0264(4) Uani 1 d . . .
O2 O 0.85483(18) 0.41984(12) 0.36939(10) 0.0206(4) Uani 1 d . . .
O3 O 0.77138(18) 0.32788(12) 0.26907(10) 0.0212(4) Uani 1 d . . .
O4 O 0.67634(18) 0.48804(13) 0.60219(11) 0.0221(4) Uani 1 d . . .
O5 O 1.10995(19) 0.56534(14) 0.93007(11) 0.0255(4) Uani 1 d . . .
O6 O 0.8364(2) 0.32618(13) 0.63708(12) 0.0292(5) Uani 1 d . . .
N1 N 0.4405(2) 0.77750(15) 0.24105(12) 0.0189(4) Uani 1 d . . .
N2 N 0.9425(2) 0.64482(15) 0.85575(12) 0.0196(4) Uani 1 d . . .
C1 C 0.7530(2) 0.47668(18) 0.32784(14) 0.0169(5) Uani 1 d . . .
C2 C 0.6975(2) 0.57441(17) 0.33482(14) 0.0161(5) Uani 1 d . . .
H2 H 0.7284 0.6086 0.3728 0.019 Uiso 1 calc . . R
C3 C 0.5933(2) 0.62590(17) 0.28556(14) 0.0154(5) Uani 1 d . . .
C4 C 0.5360(2) 0.72838(17) 0.28773(14) 0.0165(5) Uani 1 d . . .
C5 C 0.3947(3) 0.72581(19) 0.19091(14) 0.0195(5) Uani 1 d . . .
C6 C 0.4408(3) 0.62558(18) 0.18341(14) 0.0193(5) Uani 1 d . . .
H6 H 0.4037 0.5927 0.1471 0.023 Uiso 1 calc . . R
C7 C 0.5439(2) 0.57346(17) 0.23074(14) 0.0162(5) Uani 1 d . . .
C8 C 0.6021(2) 0.47084(17) 0.22516(14) 0.0171(5) Uani 1 d . . .
H8 H 0.5689 0.4347 0.1894 0.021 Uiso 1 calc . . R
C9 C 0.7052(2) 0.42397(17) 0.27083(14) 0.0178(5) Uani 1 d . . .
C10 C 0.8986(3) 0.4634(2) 0.43199(15) 0.0238(6) Uani 1 d . . .
H10A H 0.9339 0.5244 0.4104 0.036 Uiso 1 calc . . GR
H10B H 0.9725 0.4158 0.4570 0.036 Uiso 1 calc . . GR
H10C H 0.8193 0.4798 0.4716 0.036 Uiso 1 calc . . GR
C11 C 0.5803(2) 0.78951(17) 0.34404(14) 0.0165(5) Uani 1 d . . .
C12 C 0.5132(2) 0.79254(17) 0.42132(14) 0.0174(5) Uani 1 d . . .
C13 C 0.3993(3) 0.74098(18) 0.44784(15) 0.0205(5) Uani 1 d . . .
H13 H 0.3701 0.7012 0.4133 0.025 Uiso 1 calc . . R
C14 C 0.3328(3) 0.74848(19) 0.52187(16) 0.0257(6) Uani 1 d . . .
H14 H 0.2559 0.7153 0.5379 0.031 Uiso 1 calc . . R
C15 C 0.3764(3) 0.8052(2) 0.57581(16) 0.0281(6) Uani 1 d . . .
H15 H 0.3293 0.8091 0.6276 0.034 Uiso 1 calc . . R
C16 C 0.4850(3) 0.85390(19) 0.55359(16) 0.0261(6) Uani 1 d . . .
H16 H 0.5146 0.8903 0.5905 0.031 Uiso 1 calc . . R
C17 C 0.5553(3) 0.85122(18) 0.47555(15) 0.0200(5) Uani 1 d . . .
C18 C 0.6597(3) 0.90674(18) 0.44961(15) 0.0217(5) Uani 1 d . . .
H18 H 0.6888 0.9446 0.4856 0.026 Uiso 1 calc . . R
C19 C 0.7225(3) 0.90808(18) 0.37222(15) 0.0198(5) Uani 1 d . . .
C20 C 0.8236(3) 0.97047(19) 0.34397(17) 0.0249(6) Uani 1 d . . .
H20 H 0.8491 1.0114 0.3790 0.030 Uiso 1 calc . . R
C21 C 0.8832(3) 0.97206(19) 0.26839(18) 0.0266(6) Uani 1 d . . .
H21 H 0.9495 1.0142 0.2509 0.032 Uiso 1 calc . . R
C22 C 0.8473(3) 0.91122(19) 0.21496(17) 0.0253(6) Uani 1 d . . .
H22 H 0.8903 0.9127 0.1621 0.030 Uiso 1 calc . . R
C23 C 0.7516(3) 0.85058(19) 0.23905(15) 0.0215(5) Uani 1 d . . .
H23 H 0.7293 0.8099 0.2027 0.026 Uiso 1 calc . . R
C24 C 0.6844(2) 0.84736(17) 0.31814(14) 0.0175(5) Uani 1 d . . .
C25 C 0.2648(3) 0.8824(2) 0.14260(18) 0.0309(6) Uani 1 d . . .
H25A H 0.1934 0.9098 0.1063 0.046 Uiso 1 calc . . GR
H25B H 0.3497 0.9095 0.1244 0.046 Uiso 1 calc . . GR
H25C H 0.2307 0.9008 0.1961 0.046 Uiso 1 calc . . GR
C26 C 0.7344(3) 0.27183(19) 0.21160(16) 0.0261(6) Uani 1 d . . .
H26A H 0.7517 0.3055 0.1583 0.039 Uiso 1 calc . . GR
H26B H 0.6355 0.2671 0.2220 0.039 Uiso 1 calc . . GR
H26C H 0.7907 0.2045 0.2152 0.039 Uiso 1 calc . . GR
C27 C 0.7568(2) 0.49271(18) 0.66061(15) 0.0179(5) Uani 1 d . . .
C28 C 0.7581(2) 0.57425(18) 0.69871(14) 0.0171(5) Uani 1 d . . .
H28 H 0.6979 0.6354 0.6852 0.020 Uiso 1 calc . . R
C29 C 0.8494(2) 0.56810(17) 0.75882(14) 0.0173(5) Uani 1 d . . .
C30 C 0.8565(2) 0.65022(18) 0.80008(14) 0.0176(5) Uani 1 d . . .
C31 C 1.0282(2) 0.55738(19) 0.87272(14) 0.0190(5) Uani 1 d . . .
C32 C 1.0302(3) 0.47230(18) 0.83774(15) 0.0197(5) Uani 1 d . . .
H32 H 1.0913 0.4121 0.8527 0.024 Uiso 1 calc . . R
C33 C 0.9391(2) 0.47620(18) 0.77900(14) 0.0176(5) Uani 1 d . . .
C34 C 0.9353(3) 0.39190(18) 0.73873(15) 0.0205(5) Uani 1 d . . .
H34 H 0.9940 0.3299 0.7520 0.025 Uiso 1 calc . . R
C35 C 0.8475(3) 0.39990(18) 0.68102(15) 0.0206(5) Uani 1 d . . .
C36 C 0.5884(3) 0.57898(19) 0.57595(16) 0.0239(6) Uani 1 d . . .
H36A H 0.5372 0.5672 0.5330 0.036 Uiso 1 calc . . GR
H36B H 0.6455 0.6299 0.5566 0.036 Uiso 1 calc . . GR
H36C H 0.5223 0.6021 0.6203 0.036 Uiso 1 calc . . GR
C37 C 0.7627(2) 0.74884(18) 0.78594(14) 0.0182(5) Uani 1 d . . .
C38 C 0.7987(2) 0.81984(17) 0.72369(14) 0.0173(5) Uani 1 d . . .
C39 C 0.9201(3) 0.79914(18) 0.66888(15) 0.0198(5) Uani 1 d . . .
H39 H 0.9801 0.7361 0.6745 0.024 Uiso 1 calc . . R
C40 C 0.9501(3) 0.8688(2) 0.60900(16) 0.0240(6) Uani 1 d . . .
H40 H 1.0297 0.8532 0.5724 0.029 Uiso 1 calc . . R
C41 C 0.8649(3) 0.96457(19) 0.60016(16) 0.0257(6) Uani 1 d . . .
H41 H 0.8884 1.0126 0.5582 0.031 Uiso 1 calc . . R
C42 C 0.7496(3) 0.98805(19) 0.65135(16) 0.0247(6) Uani 1 d . . .
H42 H 0.6940 1.0528 0.6453 0.030 Uiso 1 calc . . R
C43 C 0.7111(3) 0.91622(18) 0.71433(15) 0.0208(5) Uani 1 d . . .
C44 C 0.5922(3) 0.93878(19) 0.76624(16) 0.0249(6) Uani 1 d . . .
H44 H 0.5357 1.0032 0.7601 0.030 Uiso 1 calc . . R
C45 C 0.5541(3) 0.8685(2) 0.82728(16) 0.0240(6) Uani 1 d . . .
C46 C 0.4321(3) 0.8903(2) 0.88058(18) 0.0329(7) Uani 1 d . . .
H46 H 0.3746 0.9543 0.8748 0.039 Uiso 1 calc . . R
C47 C 0.3965(3) 0.8211(3) 0.93957(18) 0.0384(7) Uani 1 d . . .
H47 H 0.3151 0.8374 0.9748 0.046 Uiso 1 calc . . R
C48 C 0.4796(3) 0.7251(3) 0.94886(18) 0.0366(7) Uani 1 d . . .
H48 H 0.4535 0.6772 0.9901 0.044 Uiso 1 calc . . R
C49 C 0.5973(3) 0.7007(2) 0.89900(16) 0.0287(6) Uani 1 d . . .
H49 H 0.6515 0.6355 0.9057 0.034 Uiso 1 calc . . R
C50 C 0.6399(3) 0.77152(19) 0.83695(15) 0.0217(5) Uani 1 d . . .
C51 C 1.1980(3) 0.4772(2) 0.95923(16) 0.0279(6) Uani 1 d . . .
H51A H 1.2650 0.4519 0.9159 0.042 Uiso 1 calc . . GR
H51B H 1.1416 0.4264 0.9805 0.042 Uiso 1 calc . . GR
H51C H 1.2482 0.4924 1.0014 0.042 Uiso 1 calc . . GR
C52 C 0.9206(3) 0.2307(2) 0.6551(2) 0.0360(7) Uani 1 d . . .
H52A H 0.9006 0.2076 0.7112 0.054 Uiso 1 calc . . GR
H52B H 1.0192 0.2362 0.6445 0.054 Uiso 1 calc . . GR
H52C H 0.8997 0.1827 0.6220 0.054 Uiso 1 calc . . GR
C53 C 0.9321(4) 0.8085(3) 0.9739(2) 0.0562(10) Uani 1 d A . .
H53 H 0.9338 0.7533 0.9401 0.067 Uiso 0.706(15) calc A 1 R
H53A H 0.9382 0.7673 0.9286 0.067 Uiso 0.294(15) calc A 2 R
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'
Cl Cl 0.1484 0.1585 '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
C53 Cl1 Cl4 44.0(2) . . ?
C53 Cl4 Cl1 45.4(3) . . ?
C5 O1 C25 116.7(2) . . ?
C1 O2 C10 117.07(19) . . ?
C9 O3 C26 117.1(2) . . ?
C27 O4 C36 116.60(19) . . ?
C31 O5 C51 117.5(2) . . ?
C35 O6 C52 116.8(2) . . ?
C4 N1 C5 117.7(2) . . ?
C30 N2 C31 118.4(2) . . ?
O2 C1 C2 126.4(2) . . ?
O2 C1 C9 113.6(2) . . ?
C2 C1 C9 120.0(2) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.5(2) . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 123.1(2) . . ?
C4 C3 C7 117.3(2) . . ?
C7 C3 C2 119.6(2) . . ?
N1 C4 C3 123.5(2) . . ?
N1 C4 C11 115.3(2) . . ?
C3 C4 C11 121.2(2) . . ?
O1 C5 C6 117.4(2) . . ?
N1 C5 O1 118.0(2) . . ?
N1 C5 C6 124.6(2) . . ?
C5 C6 H6 120.8 . . ?
C5 C6 C7 118.3(2) . . ?
C7 C6 H6 120.8 . . ?
C3 C7 C8 119.0(2) . . ?
C6 C7 C3 118.5(2) . . ?
C6 C7 C8 122.5(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.5(2) . . ?
C9 C8 H8 119.8 . . ?
O3 C9 C1 113.7(2) . . ?
O3 C9 C8 125.9(2) . . ?
C8 C9 C1 120.5(2) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C4 119.7(2) . . ?
C12 C11 C24 120.3(2) . . ?
C24 C11 C4 119.9(2) . . ?
C11 C12 C13 122.0(2) . . ?
C11 C12 C17 119.9(2) . . ?
C13 C12 C17 118.1(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 119.5 . . ?
C13 C14 C15 121.0(2) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 120.9(2) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C12 119.0(2) . . ?
C18 C17 C12 119.1(2) . . ?
C18 C17 C16 121.8(2) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 C17 121.6(2) . . ?
C19 C18 H18 119.2 . . ?
C18 C19 C20 121.5(2) . . ?
C18 C19 C24 119.9(2) . . ?
C20 C19 C24 118.6(2) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.2(2) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.5(2) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 119.7 . . ?
C23 C22 C21 120.5(2) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 H23 119.5 . . ?
C22 C23 C24 121.0(2) . . ?
C24 C23 H23 119.5 . . ?
C11 C24 C19 119.1(2) . . ?
C11 C24 C23 122.7(2) . . ?
C23 C24 C19 118.2(2) . . ?
O1 C25 H25A 109.5 . . ?
O1 C25 H25B 109.5 . . ?
O1 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O3 C26 H26A 109.5 . . ?
O3 C26 H26B 109.5 . . ?
O3 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O4 C27 C28 126.4(2) . . ?
O4 C27 C35 113.4(2) . . ?
C28 C27 C35 120.1(2) . . ?
C27 C28 H28 119.9 . . ?
C27 C28 C29 120.1(2) . . ?
C29 C28 H28 119.9 . . ?
C30 C29 C28 122.9(2) . . ?
C30 C29 C33 117.4(2) . . ?
C33 C29 C28 119.7(2) . . ?
N2 C30 C29 123.0(2) . . ?
N2 C30 C37 115.2(2) . . ?
C29 C30 C37 121.8(2) . . ?
O5 C31 C32 125.1(2) . . ?
N2 C31 O5 110.7(2) . . ?
N2 C31 C32 124.2(2) . . ?
C31 C32 H32 120.9 . . ?
C31 C32 C33 118.3(2) . . ?
C33 C32 H32 120.9 . . ?
C32 C33 C29 118.7(2) . . ?
C32 C33 C34 122.2(2) . . ?
C34 C33 C29 119.1(2) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 C33 120.0(2) . . ?
C35 C34 H34 120.0 . . ?
O6 C35 C27 113.3(2) . . ?
O6 C35 C34 125.8(2) . . ?
C34 C35 C27 120.9(2) . . ?
O4 C36 H36A 109.5 . . ?
O4 C36 H36B 109.5 . . ?
O4 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C38 C37 C30 120.4(2) . . ?
C50 C37 C30 119.3(2) . . ?
C50 C37 C38 120.2(2) . . ?
C37 C38 C39 122.3(2) . . ?
C37 C38 C43 119.3(2) . . ?
C39 C38 C43 118.4(2) . . ?
C38 C39 H39 119.7 . . ?
C40 C39 C38 120.6(2) . . ?
C40 C39 H39 119.7 . . ?
C39 C40 H40 119.4 . . ?
C39 C40 C41 121.2(2) . . ?
C41 C40 H40 119.4 . . ?
C40 C41 H41 119.8 . . ?
C42 C41 C40 120.4(2) . . ?
C42 C41 H41 119.8 . . ?
C41 C42 H42 119.6 . . ?
C41 C42 C43 120.7(2) . . ?
C43 C42 H42 119.6 . . ?
C42 C43 C38 118.7(2) . . ?
C44 C43 C38 120.0(2) . . ?
C44 C43 C42 121.3(2) . . ?
C43 C44 H44 119.4 . . ?
C43 C44 C45 121.2(2) . . ?
C45 C44 H44 119.4 . . ?
C44 C45 C46 121.9(3) . . ?
C44 C45 C50 119.4(2) . . ?
C46 C45 C50 118.7(3) . . ?
C45 C46 H46 119.4 . . ?
C47 C46 C45 121.1(3) . . ?
C47 C46 H46 119.4 . . ?
C46 C47 H47 119.8 . . ?
C46 C47 C48 120.4(3) . . ?
C48 C47 H47 119.8 . . ?
C47 C48 H48 119.7 . . ?
C49 C48 C47 120.5(3) . . ?
C49 C48 H48 119.7 . . ?
C48 C49 H49 119.5 . . ?
C48 C49 C50 121.0(3) . . ?
C50 C49 H49 119.5 . . ?
C37 C50 C45 119.8(2) . . ?
C37 C50 C49 122.0(2) . . ?
C49 C50 C45 118.2(2) . . ?
O5 C51 H51A 109.5 . . ?
O5 C51 H51B 109.5 . . ?
O5 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
O6 C52 H52A 109.5 . . ?
O6 C52 H52B 109.5 . . ?
O6 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
Cl1 C53 Cl2 108.0(3) . . ?
Cl1 C53 Cl5 114.8(5) . . ?
Cl1 C53 H53 107.4 . . ?
Cl1 C53 H53A 117.0 . . ?
Cl2 C53 Cl5 15.0(4) . . ?
Cl2 C53 H53 107.4 . . ?
Cl2 C53 H53A 112.6 . . ?
Cl3 C53 Cl1 109.7(3) . . ?
Cl3 C53 Cl2 116.5(4) . . ?
Cl3 C53 Cl5 101.5(4) . . ?
Cl3 C53 H53 107.4 . . ?
Cl3 C53 H53A 92.7 . . ?
Cl4 C53 Cl1 90.7(5) . . ?
Cl4 C53 Cl2 109.5(7) . . ?
Cl4 C53 Cl3 25.4(5) . . ?
Cl4 C53 Cl5 95.5(6) . . ?
Cl4 C53 H53 130.9 . . ?
Cl4 C53 H53A 117.0 . . ?
Cl5 C53 H53 115.6 . . ?
Cl5 C53 H53A 117.0 . . ?
H53 C53 H53A 15.1 . . ?
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 Cl4 2.465(11) . ?
Cl1 C53 1.755(4) . ?
Cl2 C53 1.764(7) . ?
Cl3 C53 1.733(4) . ?
Cl4 C53 1.711(7) . ?
Cl5 C53 1.826(12) . ?
O1 C5 1.365(3) . ?
O1 C25 1.437(3) . ?
O2 C1 1.359(3) . ?
O2 C10 1.427(3) . ?
O3 C9 1.355(3) . ?
O3 C26 1.432(3) . ?
O4 C27 1.356(3) . ?
O4 C36 1.430(3) . ?
O5 C31 1.362(3) . ?
O5 C51 1.419(3) . ?
O6 C35 1.355(3) . ?
O6 C52 1.429(3) . ?
N1 C4 1.332(3) . ?
N1 C5 1.338(3) . ?
N2 C30 1.329(3) . ?
N2 C31 1.349(3) . ?
C1 C2 1.360(3) . ?
C1 C9 1.446(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.427(3) . ?
C3 C4 1.413(3) . ?
C3 C7 1.423(3) . ?
C4 C11 1.497(3) . ?
C5 C6 1.378(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.402(3) . ?
C7 C8 1.424(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.365(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.405(3) . ?
C11 C24 1.409(3) . ?
C12 C13 1.435(3) . ?
C12 C17 1.437(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.359(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.423(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.356(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.428(4) . ?
C17 C18 1.391(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.390(4) . ?
C19 C20 1.435(3) . ?
C19 C24 1.437(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.352(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.420(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.366(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.431(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.361(3) . ?
C27 C35 1.438(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.424(3) . ?
C29 C30 1.413(3) . ?
C29 C33 1.423(3) . ?
C30 C37 1.495(3) . ?
C31 C32 1.368(4) . ?
C32 H32 0.9500 . ?
C32 C33 1.409(3) . ?
C33 C34 1.421(4) . ?
C34 H34 0.9500 . ?
C34 C35 1.364(4) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C38 1.411(3) . ?
C37 C50 1.410(3) . ?
C38 C39 1.433(3) . ?
C38 C43 1.435(3) . ?
C39 H39 0.9500 . ?
C39 C40 1.357(4) . ?
C40 H40 0.9500 . ?
C40 C41 1.418(4) . ?
C41 H41 0.9500 . ?
C41 C42 1.359(4) . ?
C42 H42 0.9500 . ?
C42 C43 1.434(4) . ?
C43 C44 1.391(4) . ?
C44 H44 0.9500 . ?
C44 C45 1.398(4) . ?
C45 C46 1.425(4) . ?
C45 C50 1.434(4) . ?
C46 H46 0.9500 . ?
C46 C47 1.359(5) . ?
C47 H47 0.9500 . ?
C47 C48 1.412(5) . ?
C48 H48 0.9500 . ?
C48 C49 1.366(4) . ?
C49 H49 0.9500 . ?
C49 C50 1.428(4) . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 H53 1.0000 . ?
C53 H53A 1.0000 . ?
