#------------------------------------------------------------------------------
#$Date: 2021-10-01 01:19:38 +0300 (Fri, 01 Oct 2021) $
#$Revision: 269408 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/47/1564786.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_1564786
loop_
_publ_author_name
'Qiu, Shaotong'
'Gao, Xiang'
'Zhu, Shifa'
_publ_section_title
;
 Dirhodium(II)-Catalysed Cycloisomerization of Azaenyne: Rapid Assembly of
 Centrally and Axially Chiral Isoindazoles Frameworks
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC04961E
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H18 Br N3 O'
_chemical_formula_sum            'C28 H18 Br N3 O'
_chemical_formula_weight         492.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-08-27 deposited with the CCDC.	2021-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.590(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.2119(12)
_cell_length_b                   7.9865(4)
_cell_length_c                   28.5833(19)
_cell_measurement_reflns_used    9690
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      73.3830
_cell_measurement_theta_min      2.4450
_cell_volume                     4549.5(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_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 -35.00   1.00    1.00    --  -41.11  57.00  60.00   27
  2  ω   -111.00 -17.00   1.00    1.00    --  -41.11 -57.00  30.00   94
  3  ω   -102.00 -15.00   1.00    1.00    --  -41.11 -57.00 120.00   87
  4  ω     57.00  86.00   1.00    1.00    --   41.11-125.00-180.00   29
  5  ω     67.00 121.00   1.00    1.30    --  106.95-125.00-150.00   54
  6  ω     44.00 125.00   1.00    1.30    --  106.95 -77.00  30.00   81
  7  ω     82.00 177.00   1.00    1.30    --  106.95  30.00 -90.00   95
  8  ω     79.00 172.00   1.00    1.30    --  106.95  30.00-180.00   93
  9  ω     35.00 113.00   1.00    1.30    --  106.95-125.00  60.00   78
 10  ω     -9.00  16.00   1.00    1.00    --   34.00 102.00 101.79   25
 11  ω     -6.00  19.00   1.00    1.00    --   34.00  97.00-133.84   25
 12  ω   -116.00 -17.00   1.00    1.00    --  -41.23 -38.00-150.00   99
 13  ω    -61.00  33.00   1.00    1.00    --  -41.23  38.00-180.00   94
 14  ω     24.00  90.00   1.00    1.00    --   41.23-125.00 -60.00   66
 15  ω     24.00  66.00   1.00    1.00    --   41.23-125.00  60.00   42
 16  ω     16.00  41.00   1.00    1.00    --   50.00  82.00 -26.47   25
 17  ω     20.00  45.00   1.00    2.00    --   54.00  81.00 117.36   25
 18  ω     20.00  45.00   1.00    2.00    --   54.00  81.00 165.56   25
 19  ω     21.00  46.00   1.00    2.00    --   54.00  78.00  67.35   25
 20  ω     20.00  45.00   1.00    2.00    --   54.00  81.00 -66.58   25
 21  ω     25.00  50.00   1.00    2.00    --   58.00  77.00-159.05   25
 22  ω     90.00 116.00   1.00    2.00    --   58.00  77.00-159.05   26
 23  ω     30.00  56.00   1.00    2.00    --   62.00  76.00  14.49   26
 24  ω     81.00 113.00   1.00    2.00    --   62.00  76.00  14.49   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0222141000
_diffrn_orient_matrix_UB_12      -0.0552057000
_diffrn_orient_matrix_UB_13      -0.0466961000
_diffrn_orient_matrix_UB_21      0.0737976000
_diffrn_orient_matrix_UB_22      0.0306374000
_diffrn_orient_matrix_UB_23      0.0222216000
_diffrn_orient_matrix_UB_31      0.0056720000
_diffrn_orient_matrix_UB_32      -0.1822485000
_diffrn_orient_matrix_UB_33      0.0177836000
_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  0.0537
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            14962
_diffrn_reflns_point_group_measured_fraction_full 0.815
_diffrn_reflns_point_group_measured_fraction_max 0.775
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.598
_diffrn_reflns_theta_min         2.493
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       block
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.193
_refine_diff_density_min         -0.802
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
;
 Flack x determined using 2133 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     595
_refine_ls_number_reflns         7084
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0745P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1160
_reflns_Friedel_coverage         0.479
_reflns_Friedel_fraction_full    0.600
_reflns_Friedel_fraction_max     0.544
_reflns_number_gt                6865
_reflns_number_total             7084
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc04961e2.cif
_cod_data_source_block           9st-147
_cod_database_code               1564786
_shelx_shelxl_version_number     2018/3
_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   0.776
_shelx_estimated_absorpt_t_min   0.723
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C15(H15), C35(H35), C36(H36)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14),
 C17(H17), C18(H18), C20(H20), C21(H21), C24(H24), C25(H25), C27(H27), C28(H28),
  C30(H30), C31(H31), C32(H32), C33(H33), C38(H38), C39(H39), C41(H41),
 C42(H42), C47(H47), C48(H48), C49(H49), C50(H50), C52(H52), C53(H53), C55(H55),
  C56(H56)
;
_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 1.613
_oxdiff_exptl_absorpt_empirical_full_min 0.642
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, 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_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
Br1 Br -0.11888(3) 1.07404(7) 0.67509(2) 0.03892(17) Uani 1 1 d . . . . .
O1 O 0.17829(17) 0.4065(4) 0.55051(12) 0.0290(8) Uani 1 1 d . . . . .
N1 N 0.0753(2) 0.4936(5) 0.68179(14) 0.0227(9) Uani 1 1 d . . . . .
N2 N 0.0805(2) 0.3983(6) 0.72150(15) 0.0286(9) Uani 1 1 d . . . . .
N3 N -0.0548(2) -0.3166(6) 0.54774(16) 0.0315(10) Uani 1 1 d . . . . .
C1 C 0.1605(2) 0.3270(6) 0.67660(16) 0.0209(9) Uani 1 1 d . . . . .
C2 C 0.2171(2) 0.2347(6) 0.66832(17) 0.0240(10) Uani 1 1 d . . . . .
H2 H 0.236178 0.253410 0.641335 0.029 Uiso 1 1 calc R U . . .
C3 C 0.2431(3) 0.1171(6) 0.70109(18) 0.0283(11) Uani 1 1 d . . . . .
H3 H 0.280460 0.055810 0.696119 0.034 Uiso 1 1 calc R U . . .
C4 C 0.2147(3) 0.0859(7) 0.74251(19) 0.0327(12) Uani 1 1 d . . . . .
H4 H 0.233991 0.005379 0.764068 0.039 Uiso 1 1 calc R U . . .
C5 C 0.1592(3) 0.1724(7) 0.75137(19) 0.0329(12) Uani 1 1 d . . . . .
H5 H 0.139941 0.149730 0.778060 0.040 Uiso 1 1 calc R U . . .
C6 C 0.1327(2) 0.2962(6) 0.71858(16) 0.0238(10) Uani 1 1 d . . . . .
C7 C 0.1222(2) 0.4571(6) 0.65350(15) 0.0190(9) Uani 1 1 d . . . . .
C8 C 0.1219(2) 0.5475(6) 0.60722(15) 0.0198(9) Uani 1 1 d . . . . .
H8 H 0.087094 0.634233 0.603607 0.024 Uiso 1 1 calc R U . . .
C9 C 0.1887(2) 0.6271(6) 0.60299(15) 0.0205(9) Uani 1 1 d . . . . .
C10 C 0.2173(2) 0.5398(6) 0.56989(17) 0.0223(10) Uani 1 1 d . . . . .
C11 C 0.2799(2) 0.5779(8) 0.55878(18) 0.0310(11) Uani 1 1 d . . . . .
H11 H 0.298924 0.515294 0.537023 0.037 Uiso 1 1 calc R U . . .
C12 C 0.3122(3) 0.7144(7) 0.58195(18) 0.0303(12) Uani 1 1 d . . . . .
H12 H 0.354041 0.744790 0.575267 0.036 Uiso 1 1 calc R U . . .
C13 C 0.2845(3) 0.8077(7) 0.61481(19) 0.0311(12) Uani 1 1 d . . . . .
H13 H 0.307692 0.899254 0.629507 0.037 Uiso 1 1 calc R U . . .
C14 C 0.2217(2) 0.7641(7) 0.62591(18) 0.0273(11) Uani 1 1 d . . . . .
H14 H 0.202706 0.825343 0.647973 0.033 Uiso 1 1 calc R U . . .
C15 C 0.1117(2) 0.4342(7) 0.56201(16) 0.0239(10) Uani 1 1 d . . . . .
H15 H 0.086020 0.498785 0.536002 0.029 Uiso 1 1 calc R U . . .
C16 C 0.0771(2) 0.2682(6) 0.56414(16) 0.0223(10) Uani 1 1 d . . . . .
C17 C 0.0087(2) 0.2663(7) 0.56711(17) 0.0255(10) Uani 1 1 d . . . . .
H17 H -0.013584 0.366464 0.570264 0.031 Uiso 1 1 calc R U . . .
C18 C -0.0257(3) 0.1174(6) 0.56540(17) 0.0265(11) Uani 1 1 d . . . . .
H18 H -0.070919 0.116875 0.567980 0.032 Uiso 1 1 calc R U . . .
C19 C 0.0073(2) -0.0329(6) 0.55980(16) 0.0242(10) Uani 1 1 d . . . . .
C20 C 0.0761(2) -0.0319(7) 0.55750(16) 0.0245(10) Uani 1 1 d . . . . .
H20 H 0.098501 -0.131810 0.554208 0.029 Uiso 1 1 calc R U . . .
C21 C 0.1102(2) 0.1174(6) 0.56012(16) 0.0238(10) Uani 1 1 d . . . . .
H21 H 0.155957 0.117830 0.559195 0.029 Uiso 1 1 calc R U . . .
C22 C -0.0276(3) -0.1896(7) 0.55394(17) 0.0252(11) Uani 1 1 d . . . . .
C23 C 0.0293(2) 0.6303(6) 0.67739(16) 0.0238(10) Uani 1 1 d . . . . .
C24 C 0.0533(3) 0.7923(7) 0.68463(18) 0.0277(11) Uani 1 1 d . . . . .
H24 H 0.099307 0.811315 0.690265 0.033 Uiso 1 1 calc R U . . .
C25 C 0.0099(3) 0.9254(7) 0.68359(17) 0.0284(11) Uani 1 1 d . . . . .
H25 H 0.025776 1.034386 0.688229 0.034 Uiso 1 1 calc R U . . .
C26 C -0.0589(3) 0.8915(7) 0.67535(17) 0.0285(11) Uani 1 1 d . . . . .
C27 C -0.0838(2) 0.7317(8) 0.66762(17) 0.0310(12) Uani 1 1 d . . . . .
H27 H -0.129838 0.713242 0.661794 0.037 Uiso 1 1 calc R U . . .
C28 C -0.0399(2) 0.5991(7) 0.66857(16) 0.0262(11) Uani 1 1 d . . . . .
H28 H -0.056030 0.490474 0.663438 0.031 Uiso 1 1 calc R U . . .
Br2 Br 0.79409(3) -0.05616(7) 0.53344(2) 0.03622(17) Uani 1 1 d . . . . .
O2 O 0.46326(15) 0.5816(5) 0.60466(12) 0.0278(7) Uani 1 1 d . . . . .
N4 N 0.7381(2) 0.6386(5) 0.66357(15) 0.0283(9) Uani 1 1 d . . . . .
N5 N 0.69449(19) 0.5278(5) 0.63896(14) 0.0219(9) Uani 1 1 d . . . . .
N6 N 0.6049(2) 1.3204(6) 0.49747(17) 0.0334(10) Uani 1 1 d . . . . .
C29 C 0.5247(2) 0.3709(6) 0.64631(17) 0.0236(10) Uani 1 1 d . . . . .
C30 C 0.5318(3) 0.2383(7) 0.67798(18) 0.0309(11) Uani 1 1 d . . . . .
H30 H 0.572398 0.181556 0.684959 0.037 Uiso 1 1 calc R U . . .
C31 C 0.4781(3) 0.1912(8) 0.69906(19) 0.0357(13) Uani 1 1 d . . . . .
H31 H 0.482731 0.102595 0.720455 0.043 Uiso 1 1 calc R U . . .
C32 C 0.4174(3) 0.2749(7) 0.68865(18) 0.0314(12) Uani 1 1 d . . . . .
H32 H 0.381580 0.240586 0.702982 0.038 Uiso 1 1 calc R U . . .
C33 C 0.4089(2) 0.4090(7) 0.65723(18) 0.0288(11) Uani 1 1 d . . . . .
H33 H 0.368416 0.466672 0.650539 0.035 Uiso 1 1 calc R U . . .
C34 C 0.4635(2) 0.4525(7) 0.63640(17) 0.0251(10) Uani 1 1 d . . . . .
C35 C 0.5729(2) 0.4505(6) 0.61730(15) 0.0206(9) Uani 1 1 d . . . . .
H35 H 0.591546 0.363350 0.599181 0.025 Uiso 1 1 calc R U . . .
C36 C 0.5218(2) 0.5601(6) 0.58238(16) 0.0219(9) Uani 1 1 d . . . . .
H36 H 0.508149 0.494730 0.553367 0.026 Uiso 1 1 calc R U . . .
C37 C 0.5450(2) 0.7272(6) 0.56809(16) 0.0213(10) Uani 1 1 d . . . . .
C38 C 0.5908(2) 0.7360(7) 0.53610(17) 0.0256(11) Uani 1 1 d . . . . .
H38 H 0.608958 0.637749 0.526169 0.031 Uiso 1 1 calc R U . . .
C39 C 0.6092(3) 0.8866(6) 0.51938(17) 0.0270(11) Uani 1 1 d . . . . .
H39 H 0.639983 0.890729 0.498619 0.032 Uiso 1 1 calc R U . . .
C40 C 0.5812(2) 1.0344(6) 0.53373(16) 0.0242(10) Uani 1 1 d . . . . .
C41 C 0.5372(2) 1.0293(6) 0.56652(17) 0.0234(10) Uani 1 1 d . . . . .
H41 H 0.519553 1.127645 0.576817 0.028 Uiso 1 1 calc R U . . .
C42 C 0.5202(2) 0.8754(7) 0.58346(17) 0.0248(10) Uani 1 1 d . . . . .
H42 H 0.491392 0.871441 0.605673 0.030 Uiso 1 1 calc R U . . .
C43 C 0.5959(3) 1.1929(7) 0.51372(18) 0.0282(11) Uani 1 1 d . . . . .
C44 C 0.6289(2) 0.5462(6) 0.64582(15) 0.0208(9) Uani 1 1 d . . . . .
C45 C 0.6302(2) 0.6770(6) 0.67815(17) 0.0233(10) Uani 1 1 d . . . . .
C46 C 0.6987(3) 0.7300(6) 0.68786(17) 0.0273(11) Uani 1 1 d . . . . .
C47 C 0.7182(3) 0.8606(7) 0.7204(2) 0.0369(13) Uani 1 1 d . . . . .
H47 H 0.762541 0.896834 0.726818 0.044 Uiso 1 1 calc R U . . .
C48 C 0.6707(3) 0.9318(7) 0.74223(19) 0.0382(13) Uani 1 1 d . . . . .
H48 H 0.682865 1.017866 0.763858 0.046 Uiso 1 1 calc R U . . .
C49 C 0.6024(3) 0.8784(7) 0.73294(18) 0.0338(12) Uani 1 1 d . . . . .
H49 H 0.571432 0.929562 0.748976 0.041 Uiso 1 1 calc R U . . .
C50 C 0.5813(3) 0.7544(6) 0.70120(17) 0.0283(11) Uani 1 1 d . . . . .
H50 H 0.536562 0.721777 0.694884 0.034 Uiso 1 1 calc R U . . .
C51 C 0.7202(2) 0.3921(6) 0.61436(16) 0.0236(10) Uani 1 1 d . . . . .
C52 C 0.7568(2) 0.4239(7) 0.57845(17) 0.0271(10) Uani 1 1 d . . . . .
H52 H 0.766074 0.533282 0.570430 0.033 Uiso 1 1 calc R U . . .
C53 C 0.7796(2) 0.2891(7) 0.55454(19) 0.0291(11) Uani 1 1 d . . . . .
H53 H 0.804840 0.307652 0.530633 0.035 Uiso 1 1 calc R U . . .
C54 C 0.7646(2) 0.1295(7) 0.56648(18) 0.0268(11) Uani 1 1 d . . . . .
C55 C 0.7292(2) 0.0958(6) 0.60327(17) 0.0246(10) Uani 1 1 d . . . . .
H55 H 0.720403 -0.013946 0.611245 0.030 Uiso 1 1 calc R U . . .
C56 C 0.7075(2) 0.2288(6) 0.62765(17) 0.0242(10) Uani 1 1 d . . . . .
H56 H 0.684611 0.209526 0.652781 0.029 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'
Br Br -0.6763 1.2805 '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
C10 O1 C15 106.2(3) . . ?
N2 N1 C7 114.1(4) . . ?
N2 N1 C23 117.5(4) . . ?
C7 N1 C23 127.8(4) . . ?
C6 N2 N1 103.9(4) . . ?
C2 C1 C6 119.5(4) . . ?
C7 C1 C2 135.2(4) . . ?
C7 C1 C6 105.2(4) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.2(5) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.9(5) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.3(5) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 121.2 . . ?
C4 C5 C6 117.5(5) . . ?
C6 C5 H5 121.2 . . ?
N2 C6 C1 111.7(4) . . ?
N2 C6 C5 126.9(5) . . ?
C5 C6 C1 121.4(5) . . ?
N1 C7 C1 105.2(4) . . ?
N1 C7 C8 120.8(4) . . ?
C1 C7 C8 133.9(4) . . ?
C7 C8 H8 109.2 . . ?
C7 C8 C9 113.4(4) . . ?
C7 C8 C15 115.4(4) . . ?
C9 C8 H8 109.2 . . ?
C9 C8 C15 99.9(3) . . ?
C15 C8 H8 109.2 . . ?
C10 C9 C8 108.9(4) . . ?
C10 C9 C14 120.0(4) . . ?
C14 C9 C8 131.1(4) . . ?
O1 C10 C11 123.8(5) . . ?
C9 C10 O1 112.9(4) . . ?
C9 C10 C11 123.2(5) . . ?
C10 C11 H11 122.0 . . ?
C12 C11 C10 116.1(5) . . ?
C12 C11 H11 122.0 . . ?
C11 C12 H12 118.8 . . ?
C11 C12 C13 122.5(5) . . ?
C13 C12 H12 118.8 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.1(5) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 118.1(5) . . ?
C9 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
O1 C15 C8 106.0(4) . . ?
O1 C15 H15 107.6 . . ?
O1 C15 C16 109.3(4) . . ?
C8 C15 H15 107.6 . . ?
C16 C15 C8 118.3(4) . . ?
C16 C15 H15 107.6 . . ?
C17 C16 C15 118.9(4) . . ?
C21 C16 C15 121.7(4) . . ?
C21 C16 C17 119.3(5) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.4(5) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.1(5) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C20 119.7(5) . . ?
C18 C19 C22 122.1(4) . . ?
C20 C19 C22 118.1(5) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.6(5) . . ?
C21 C20 H20 120.2 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.8(4) . . ?
C20 C21 H21 119.6 . . ?
N3 C22 C19 177.6(6) . . ?
C24 C23 N1 119.7(4) . . ?
C24 C23 C28 120.4(5) . . ?
C28 C23 N1 119.8(5) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.9(5) . . ?
C25 C24 H24 119.6 . . ?
C24 C25 H25 121.1 . . ?
C24 C25 C26 117.9(5) . . ?
C26 C25 H25 121.1 . . ?
C25 C26 Br1 118.0(4) . . ?
C27 C26 Br1 119.7(4) . . ?
C27 C26 C25 122.2(5) . . ?
C26 C27 H27 120.2 . . ?
C26 C27 C28 119.5(5) . . ?
C28 C27 H27 120.2 . . ?
C23 C28 H28 120.4 . . ?
C27 C28 C23 119.1(5) . . ?
C27 C28 H28 120.4 . . ?
C34 O2 C36 106.8(3) . . ?
C46 N4 N5 103.4(4) . . ?
N4 N5 C44 114.4(4) . . ?
N4 N5 C51 119.3(4) . . ?
C44 N5 C51 125.8(4) . . ?
C30 C29 C34 119.1(5) . . ?
C30 C29 C35 132.1(5) . . ?
C34 C29 C35 108.9(4) . . ?
C29 C30 H30 120.3 . . ?
C31 C30 C29 119.4(5) . . ?
C31 C30 H30 120.3 . . ?
C30 C31 H31 119.7 . . ?
C30 C31 C32 120.6(5) . . ?
C32 C31 H31 119.7 . . ?
C31 C32 H32 119.3 . . ?
C31 C32 C33 121.3(5) . . ?
C33 C32 H32 119.3 . . ?
C32 C33 H33 121.6 . . ?
C34 C33 C32 116.8(5) . . ?
C34 C33 H33 121.6 . . ?
O2 C34 C29 113.2(4) . . ?
O2 C34 C33 123.9(5) . . ?
C33 C34 C29 122.9(5) . . ?
C29 C35 H35 109.2 . . ?
C29 C35 C36 99.5(3) . . ?
C36 C35 H35 109.2 . . ?
C44 C35 C29 114.4(4) . . ?
C44 C35 H35 109.2 . . ?
C44 C35 C36 114.8(4) . . ?
O2 C36 C35 106.6(3) . . ?
O2 C36 H36 107.6 . . ?
O2 C36 C37 109.4(4) . . ?
C35 C36 H36 107.6 . . ?
C37 C36 C35 117.8(4) . . ?
C37 C36 H36 107.6 . . ?
C38 C37 C36 119.5(4) . . ?
C42 C37 C36 122.0(4) . . ?
C42 C37 C38 118.4(4) . . ?
C37 C38 H38 119.5 . . ?
C39 C38 C37 121.1(5) . . ?
C39 C38 H38 119.5 . . ?
C38 C39 H39 120.2 . . ?
C38 C39 C40 119.6(5) . . ?
C40 C39 H39 120.2 . . ?
C39 C40 C43 120.4(4) . . ?
C41 C40 C39 120.4(5) . . ?
C41 C40 C43 119.2(4) . . ?
C40 C41 H41 120.5 . . ?
C42 C41 C40 118.9(4) . . ?
C42 C41 H41 120.5 . . ?
C37 C42 C41 121.5(4) . . ?
C37 C42 H42 119.2 . . ?
C41 C42 H42 119.2 . . ?
N6 C43 C40 177.3(6) . . ?
N5 C44 C35 121.9(4) . . ?
N5 C44 C45 105.1(4) . . ?
C45 C44 C35 132.6(4) . . ?
C44 C45 C46 105.2(4) . . ?
C44 C45 C50 134.2(5) . . ?
C50 C45 C46 120.6(5) . . ?
N4 C46 C45 111.9(4) . . ?
N4 C46 C47 127.9(5) . . ?
C47 C46 C45 120.1(5) . . ?
C46 C47 H47 120.9 . . ?
C48 C47 C46 118.2(6) . . ?
C48 C47 H47 120.9 . . ?
C47 C48 H48 119.1 . . ?
C47 C48 C49 121.8(5) . . ?
C49 C48 H48 119.1 . . ?
C48 C49 H49 119.1 . . ?
C50 C49 C48 121.8(5) . . ?
C50 C49 H49 119.1 . . ?
C45 C50 H50 121.3 . . ?
C49 C50 C45 117.5(5) . . ?
C49 C50 H50 121.3 . . ?
C52 C51 N5 120.4(5) . . ?
C52 C51 C56 121.2(5) . . ?
C56 C51 N5 118.4(4) . . ?
C51 C52 H52 120.6 . . ?
C51 C52 C53 118.9(5) . . ?
C53 C52 H52 120.6 . . ?
C52 C53 H53 120.2 . . ?
C54 C53 C52 119.5(4) . . ?
C54 C53 H53 120.2 . . ?
C53 C54 Br2 120.1(4) . . ?
C53 C54 C55 122.1(5) . . ?
C55 C54 Br2 117.8(4) . . ?
C54 C55 H55 120.7 . . ?
C56 C55 C54 118.6(5) . . ?
C56 C55 H55 120.7 . . ?
C51 C56 H56 120.2 . . ?
C55 C56 C51 119.6(4) . . ?
C55 C56 H56 120.2 . . ?
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
Br1 C26 1.895(5) . ?
O1 C10 1.384(6) . ?
O1 C15 1.454(5) . ?
N1 N2 1.356(6) . ?
N1 C7 1.376(6) . ?
N1 C23 1.425(6) . ?
N2 C6 1.347(6) . ?
N3 C22 1.153(7) . ?
C1 C2 1.415(7) . ?
C1 C6 1.429(6) . ?
C1 C7 1.394(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.422(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.406(7) . ?
C7 C8 1.506(6) . ?
C8 H8 0.9800 . ?
C8 C9 1.516(6) . ?
C8 C15 1.563(7) . ?
C9 C10 1.377(6) . ?
C9 C14 1.388(7) . ?
C10 C11 1.389(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.387(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.403(7) . ?
C14 H14 0.9300 . ?
C15 H15 0.9800 . ?
C15 C16 1.506(7) . ?
C16 C17 1.398(7) . ?
C16 C21 1.391(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.374(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.394(7) . ?
C19 C20 1.404(7) . ?
C19 C22 1.432(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.373(7) . ?
C21 H21 0.9300 . ?
C23 C24 1.385(8) . ?
C23 C28 1.402(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.376(7) . ?
C25 H25 0.9300 . ?
C25 C26 1.396(7) . ?
C26 C27 1.377(8) . ?
C27 H27 0.9300 . ?
C27 C28 1.378(7) . ?
C28 H28 0.9300 . ?
Br2 C54 1.906(5) . ?
O2 C34 1.373(6) . ?
O2 C36 1.444(5) . ?
N4 N5 1.360(6) . ?
N4 C46 1.353(7) . ?
N5 C44 1.380(6) . ?
N5 C51 1.435(6) . ?
N6 C43 1.146(7) . ?
C29 C30 1.385(7) . ?
C29 C34 1.385(7) . ?
C29 C35 1.520(6) . ?
C30 H30 0.9300 . ?
C30 C31 1.377(7) . ?
C31 H31 0.9300 . ?
C31 C32 1.386(8) . ?
C32 H32 0.9300 . ?
C32 C33 1.390(8) . ?
C33 H33 0.9300 . ?
C33 C34 1.383(7) . ?
C35 H35 0.9800 . ?
C35 C36 1.577(6) . ?
C35 C44 1.490(6) . ?
C36 H36 0.9800 . ?
C36 C37 1.494(7) . ?
C37 C38 1.408(7) . ?
C37 C42 1.385(7) . ?
C38 H38 0.9300 . ?
C38 C39 1.368(7) . ?
C39 H39 0.9300 . ?
C39 C40 1.399(7) . ?
C40 C41 1.397(7) . ?
C40 C43 1.440(7) . ?
C41 H41 0.9300 . ?
C41 C42 1.386(7) . ?
C42 H42 0.9300 . ?
C44 C45 1.392(7) . ?
C45 C46 1.430(7) . ?
C45 C50 1.418(7) . ?
C46 C47 1.410(7) . ?
C47 H47 0.9300 . ?
C47 C48 1.354(8) . ?
C48 H48 0.9300 . ?
C48 C49 1.426(8) . ?
C49 H49 0.9300 . ?
C49 C50 1.362(7) . ?
C50 H50 0.9300 . ?
C51 C52 1.386(7) . ?
C51 C56 1.394(7) . ?
C52 H52 0.9300 . ?
C52 C53 1.394(8) . ?
C53 H53 0.9300 . ?
C53 C54 1.367(8) . ?
C54 C55 1.393(7) . ?
C55 H55 0.9300 . ?
C55 C56 1.382(7) . ?
C56 H56 0.9300 . ?
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
Br1 C26 C27 C28 -179.0(4) . . . . ?
O1 C10 C11 C12 -179.2(4) . . . . ?
O1 C15 C16 C17 -169.8(4) . . . . ?
O1 C15 C16 C21 6.0(6) . . . . ?
N1 N2 C6 C1 -0.2(6) . . . . ?
N1 N2 C6 C5 179.7(5) . . . . ?
N1 C7 C8 C9 126.2(4) . . . . ?
N1 C7 C8 C15 -119.4(5) . . . . ?
N1 C23 C24 C25 -175.8(4) . . . . ?
N1 C23 C28 C27 175.6(4) . . . . ?
N2 N1 C7 C1 0.5(5) . . . . ?
N2 N1 C7 C8 177.9(4) . . . . ?
N2 N1 C23 C24 104.6(5) . . . . ?
N2 N1 C23 C28 -71.6(6) . . . . ?
C1 C2 C3 C4 0.2(7) . . . . ?
C1 C7 C8 C9 -57.2(7) . . . . ?
C1 C7 C8 C15 57.2(7) . . . . ?
C2 C1 C6 N2 178.0(4) . . . . ?
C2 C1 C6 C5 -1.9(7) . . . . ?
C2 C1 C7 N1 -177.5(5) . . . . ?
C2 C1 C7 C8 5.5(9) . . . . ?
C2 C3 C4 C5 0.4(8) . . . . ?
C3 C4 C5 C6 -1.7(8) . . . . ?
C4 C5 C6 N2 -177.5(5) . . . . ?
C4 C5 C6 C1 2.4(8) . . . . ?
C6 C1 C2 C3 0.5(7) . . . . ?
C6 C1 C7 N1 -0.5(5) . . . . ?
C6 C1 C7 C8 -177.5(5) . . . . ?
C7 N1 N2 C6 -0.2(5) . . . . ?
C7 N1 C23 C24 -66.3(7) . . . . ?
C7 N1 C23 C28 117.6(5) . . . . ?
C7 C1 C2 C3 177.2(5) . . . . ?
C7 C1 C6 N2 0.5(6) . . . . ?
C7 C1 C6 C5 -179.5(5) . . . . ?
C7 C8 C9 C10 109.6(4) . . . . ?
C7 C8 C9 C14 -70.7(6) . . . . ?
C7 C8 C15 O1 -99.2(4) . . . . ?
C7 C8 C15 C16 23.8(6) . . . . ?
C8 C9 C10 O1 -0.5(5) . . . . ?
C8 C9 C10 C11 -177.9(4) . . . . ?
C8 C9 C14 C13 179.3(5) . . . . ?
C8 C15 C16 C17 68.8(6) . . . . ?
C8 C15 C16 C21 -115.4(5) . . . . ?
C9 C8 C15 O1 22.8(5) . . . . ?
C9 C8 C15 C16 145.8(4) . . . . ?
C9 C10 C11 C12 -2.0(7) . . . . ?
C10 O1 C15 C8 -24.3(5) . . . . ?
C10 O1 C15 C16 -152.9(4) . . . . ?
C10 C9 C14 C13 -1.0(7) . . . . ?
C10 C11 C12 C13 0.6(8) . . . . ?
C11 C12 C13 C14 0.5(8) . . . . ?
C12 C13 C14 C9 -0.3(8) . . . . ?
C14 C9 C10 O1 179.7(4) . . . . ?
C14 C9 C10 C11 2.3(7) . . . . ?
C15 O1 C10 C9 16.1(5) . . . . ?
C15 O1 C10 C11 -166.5(5) . . . . ?
C15 C8 C9 C10 -13.8(5) . . . . ?
C15 C8 C9 C14 165.9(5) . . . . ?
C15 C16 C17 C18 174.9(4) . . . . ?
C15 C16 C21 C20 -173.6(4) . . . . ?
C16 C17 C18 C19 -1.2(7) . . . . ?
C17 C16 C21 C20 2.1(7) . . . . ?
C17 C18 C19 C20 2.1(7) . . . . ?
C17 C18 C19 C22 -174.8(5) . . . . ?
C18 C19 C20 C21 -0.9(7) . . . . ?
C19 C20 C21 C16 -1.2(7) . . . . ?
C21 C16 C17 C18 -0.9(7) . . . . ?
C22 C19 C20 C21 176.1(4) . . . . ?
C23 N1 N2 C6 -172.3(4) . . . . ?
C23 N1 C7 C1 171.6(4) . . . . ?
C23 N1 C7 C8 -11.0(7) . . . . ?
C23 C24 C25 C26 0.4(7) . . . . ?
C24 C23 C28 C27 -0.5(7) . . . . ?
C24 C25 C26 Br1 178.8(4) . . . . ?
C24 C25 C26 C27 -1.1(8) . . . . ?
C25 C26 C27 C28 0.9(8) . . . . ?
C26 C27 C28 C23 -0.1(7) . . . . ?
C28 C23 C24 C25 0.4(7) . . . . ?
Br2 C54 C55 C56 179.9(4) . . . . ?
O2 C36 C37 C38 -165.1(4) . . . . ?
O2 C36 C37 C42 11.6(6) . . . . ?
N4 N5 C44 C35 172.2(4) . . . . ?
N4 N5 C44 C45 -1.3(5) . . . . ?
N4 N5 C51 C52 -61.1(6) . . . . ?
N4 N5 C51 C56 118.7(5) . . . . ?
N4 C46 C47 C48 -177.6(5) . . . . ?
N5 N4 C46 C45 -0.4(5) . . . . ?
N5 N4 C46 C47 177.9(5) . . . . ?
N5 C44 C45 C46 0.9(5) . . . . ?
N5 C44 C45 C50 -177.4(5) . . . . ?
N5 C51 C52 C53 -178.4(4) . . . . ?
N5 C51 C56 C55 177.3(4) . . . . ?
C29 C30 C31 C32 0.3(9) . . . . ?
C29 C35 C36 O2 20.6(5) . . . . ?
C29 C35 C36 C37 143.9(4) . . . . ?
C29 C35 C44 N5 133.6(5) . . . . ?
C29 C35 C44 C45 -55.0(7) . . . . ?
C30 C29 C34 O2 179.8(4) . . . . ?
C30 C29 C34 C33 0.8(8) . . . . ?
C30 C29 C35 C36 167.0(5) . . . . ?
C30 C29 C35 C44 -70.1(7) . . . . ?
C30 C31 C32 C33 -0.7(9) . . . . ?
C31 C32 C33 C34 1.1(8) . . . . ?
C32 C33 C34 O2 180.0(5) . . . . ?
C32 C33 C34 C29 -1.2(8) . . . . ?
C34 O2 C36 C35 -22.5(5) . . . . ?
C34 O2 C36 C37 -150.9(4) . . . . ?
C34 C29 C30 C31 -0.3(8) . . . . ?
C34 C29 C35 C36 -12.0(5) . . . . ?
C34 C29 C35 C44 110.9(5) . . . . ?
C35 C29 C30 C31 -179.2(5) . . . . ?
C35 C29 C34 O2 -1.1(6) . . . . ?
C35 C29 C34 C33 179.9(5) . . . . ?
C35 C36 C37 C38 73.1(6) . . . . ?
C35 C36 C37 C42 -110.3(5) . . . . ?
C35 C44 C45 C46 -171.6(5) . . . . ?
C35 C44 C45 C50 10.1(9) . . . . ?
C36 O2 C34 C29 15.3(5) . . . . ?
C36 O2 C34 C33 -165.7(5) . . . . ?
C36 C35 C44 N5 -112.2(5) . . . . ?
C36 C35 C44 C45 59.2(6) . . . . ?
C36 C37 C38 C39 174.9(4) . . . . ?
C36 C37 C42 C41 -173.8(5) . . . . ?
C37 C38 C39 C40 -0.9(7) . . . . ?
C38 C37 C42 C41 2.8(7) . . . . ?
C38 C39 C40 C41 2.8(7) . . . . ?
C38 C39 C40 C43 -175.2(5) . . . . ?
C39 C40 C41 C42 -1.9(7) . . . . ?
C40 C41 C42 C37 -1.0(7) . . . . ?
C42 C37 C38 C39 -1.9(7) . . . . ?
C43 C40 C41 C42 176.2(5) . . . . ?
C44 N5 C51 C52 128.4(5) . . . . ?
C44 N5 C51 C56 -51.8(6) . . . . ?
C44 C35 C36 O2 -102.0(4) . . . . ?
C44 C35 C36 C37 21.2(6) . . . . ?
C44 C45 C46 N4 -0.3(5) . . . . ?
C44 C45 C46 C47 -178.8(4) . . . . ?
C44 C45 C50 C49 177.4(5) . . . . ?
C45 C46 C47 C48 0.6(8) . . . . ?
C46 N4 N5 C44 1.0(5) . . . . ?
C46 N4 N5 C51 -170.5(4) . . . . ?
C46 C45 C50 C49 -0.7(7) . . . . ?
C46 C47 C48 C49 -0.1(8) . . . . ?
C47 C48 C49 C50 -0.9(8) . . . . ?
C48 C49 C50 C45 1.2(8) . . . . ?
C50 C45 C46 N4 178.3(4) . . . . ?
C50 C45 C46 C47 -0.2(7) . . . . ?
C51 N5 C44 C35 -16.8(7) . . . . ?
C51 N5 C44 C45 169.7(4) . . . . ?
C51 C52 C53 C54 0.9(7) . . . . ?
C52 C51 C56 C55 -2.9(7) . . . . ?
C52 C53 C54 Br2 179.0(4) . . . . ?
C52 C53 C54 C55 -2.5(8) . . . . ?
C53 C54 C55 C56 1.4(7) . . . . ?
C54 C55 C56 C51 1.3(7) . . . . ?
C56 C51 C52 C53 1.8(7) . . . . ?
