#------------------------------------------------------------------------------
#$Date: 2026-03-13 00:57:40 +0100 (Fri 13 de Mar de 2026) $
#$Revision: 305066 $
#$URL: svn://www.crystallography.net/cod/cif/7/72/06/7720679.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_7720679
loop_
_publ_author_name
'Shibata, Kaname'
'Michiue, Kenji'
'Motuzis, Ignas'
'Elsegood, Mark Robert James'
'Redshaw, Carl'
_publ_section_title
;
 Vanadyl complexes supported by O,O-and N,O-chelate ligation: Structures
 and polymerization catalysis
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D6DT00387G
_journal_year                    2026
_chemical_formula_moiety         'C19 H21 Br2 N O'
_chemical_formula_sum            'C19 H21 Br2 N O'
_chemical_formula_weight         439.19
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2026-01-19 deposited with the CCDC.	2026-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                103.1633(10)
_cell_angle_beta                 93.0781(9)
_cell_angle_gamma                105.7365(11)
_cell_formula_units_Z            4
_cell_length_a                   8.27032(10)
_cell_length_b                   11.96735(15)
_cell_length_c                   19.8419(2)
_cell_measurement_reflns_used    35740
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.56
_cell_measurement_theta_min      1.83
_cell_volume                     1826.54(4)
_computing_cell_refinement       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.121a 64-bit (release 24-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
; 
Rigaku FRE+ equipped with Arc)Sec VHF Varimax confocal mirrors and an UG2 
goniometer and HyPix 6000HE detector 
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_collimation    0.2
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            138537
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.140
_diffrn_reflns_theta_min         1.827
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    4.442
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.43.121a (Rigaku Oxford Diffraction, 2024) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.664
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     580
_refine_ls_number_reflns         13940
_refine_ls_number_restraints     1131
_refine_ls_restrained_S_all      1.217
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+3.8831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0911
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10574
_reflns_number_total             13940
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6dt00387g2.cif
_cod_data_source_block           LH
_cod_database_code               7720679
_shelx_shelxl_version_number     2019/3
_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_min   0.746
_shelx_estimated_absorpt_t_max   0.808
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
O1 O 0.7028(2) 0.15501(17) 0.62042(10) 0.0206(4) Uani 1 1 d D . . . .
H1 H 0.669(4) 0.216(2) 0.6311(17) 0.024(9) Uiso 1 1 d D . . . .
C1 C 0.6962(3) 0.1241(2) 0.55059(13) 0.0176(5) Uani 1 1 d D . . . .
C2 C 0.7465(3) 0.0256(2) 0.51786(14) 0.0188(5) Uani 1 1 d D . . . .
Br1 Br 0.82587(4) -0.06277(2) 0.57304(2) 0.02474(6) Uani 1 1 d D . . . .
C3 C 0.7399(3) -0.0102(2) 0.44618(14) 0.0207(5) Uani 1 1 d D . . . .
H3 H 0.774162 -0.078313 0.425187 0.025 Uiso 1 1 calc R U . . .
C4 C 0.6829(3) 0.0542(2) 0.40529(13) 0.0210(5) Uani 1 1 d D . . . .
Br2 Br 0.67022(4) 0.00615(3) 0.30694(2) 0.03022(7) Uani 1 1 d D . . . .
C5 C 0.6335(3) 0.1539(2) 0.43564(13) 0.0198(5) Uani 1 1 d D . . . .
H5 H 0.595592 0.198122 0.407243 0.024 Uiso 1 1 calc R U . . .
C6 C 0.6394(3) 0.1895(2) 0.50820(13) 0.0171(5) Uani 1 1 d D . . . .
C7 C 0.5872(3) 0.2950(2) 0.53826(14) 0.0187(5) Uani 1 1 d D . . . .
H7 H 0.549919 0.336810 0.508139 0.022 Uiso 1 1 calc R U . . .
N1 N 0.5903(3) 0.33303(19) 0.60404(11) 0.0180(4) Uani 1 1 d D . . . .
C8 C 0.5499(3) 0.4425(2) 0.62917(13) 0.0173(5) Uani 1 1 d D . . . .
C9 C 0.4097(3) 0.4399(2) 0.66667(13) 0.0193(5) Uani 1 1 d D . . . .
C10 C 0.3670(4) 0.5460(2) 0.68912(14) 0.0224(5) Uani 1 1 d D . . . .
H10 H 0.270851 0.545446 0.713339 0.027 Uiso 1 1 calc R U . . .
C11 C 0.4622(4) 0.6524(2) 0.67673(14) 0.0227(5) Uani 1 1 d D . . . .
H11 H 0.429762 0.723653 0.691335 0.027 Uiso 1 1 calc R U . . .
C12 C 0.6049(4) 0.6544(2) 0.64294(14) 0.0223(5) Uani 1 1 d D . . . .
H12 H 0.671431 0.728238 0.635990 0.027 Uiso 1 1 calc R U . . .
C13 C 0.6535(3) 0.5508(2) 0.61883(13) 0.0190(5) Uani 1 1 d D . . . .
C14 C 0.3060(3) 0.3242(2) 0.68216(15) 0.0234(5) Uani 1 1 d D . . . .
H14 H 0.362996 0.260879 0.665703 0.028 Uiso 1 1 calc R U . . .
C15 C 0.2995(4) 0.3404(3) 0.76059(16) 0.0325(7) Uani 1 1 d D . . . .
H15A H 0.415037 0.368260 0.784864 0.049 Uiso 1 1 calc R U . . .
H15B H 0.239615 0.263529 0.769622 0.049 Uiso 1 1 calc R U . . .
H15C H 0.239773 0.399663 0.777545 0.049 Uiso 1 1 calc R U . . .
C16 C 0.1279(4) 0.2819(3) 0.64271(17) 0.0295(6) Uani 1 1 d D . . . .
H16A H 0.063784 0.207355 0.653191 0.044 Uiso 1 1 calc R U . . .
H16B H 0.134922 0.267712 0.592477 0.044 Uiso 1 1 calc R U . . .
H16C H 0.070509 0.343635 0.657153 0.044 Uiso 1 1 calc R U . . .
C17 C 0.8185(3) 0.5593(2) 0.58697(14) 0.0223(5) Uani 1 1 d D . . . .
H17 H 0.841046 0.479883 0.580997 0.027 Uiso 1 1 calc R U . . .
C18 C 0.9677(4) 0.6543(3) 0.63597(17) 0.0342(7) Uani 1 1 d D . . . .
H18A H 1.073539 0.652813 0.616339 0.051 Uiso 1 1 calc R U . . .
H18B H 0.972759 0.636689 0.681779 0.051 Uiso 1 1 calc R U . . .
H18C H 0.951785 0.733880 0.640990 0.051 Uiso 1 1 calc R U . . .
C19 C 0.8078(4) 0.5848(3) 0.51507(15) 0.0280(6) Uani 1 1 d D . . . .
H19A H 0.784843 0.662070 0.519230 0.042 Uiso 1 1 calc R U . . .
H19B H 0.716334 0.521077 0.483763 0.042 Uiso 1 1 calc R U . . .
H19C H 0.915410 0.587554 0.496097 0.042 Uiso 1 1 calc R U . . .
O2 O 0.7360(6) 0.6457(4) 0.7972(2) 0.0318(10) Uani 0.5234(17) 1 d D . P A 1
H2 H 0.690918 0.701432 0.800429 0.048 Uiso 0.5234(17) 1 calc R U P A 1
C20 C 0.7358(7) 0.6128(5) 0.8575(3) 0.0192(8) Uani 0.5234(17) 1 d D U P A 1
C21 C 0.7832(9) 0.5087(6) 0.8600(3) 0.0196(9) Uani 0.5234(17) 1 d D U P A 1
Br3 Br 0.8405(2) 0.41967(13) 0.77874(8) 0.0325(2) Uani 0.5234(17) 1 d D U P A 1
C22 C 0.7890(12) 0.4722(7) 0.9210(3) 0.0183(10) Uani 0.5234(17) 1 d D U P A 1
H22 H 0.822395 0.402685 0.922196 0.022 Uiso 0.5234(17) 1 calc R U P A 1
C23 C 0.7454(7) 0.5382(5) 0.9809(3) 0.0187(8) Uani 0.5234(17) 1 d D U P A 1
Br4 Br 0.75424(8) 0.48845(7) 1.06472(3) 0.02781(19) Uani 0.5234(17) 1 d D U P A
1
C24 C 0.6978(6) 0.6400(4) 0.9799(3) 0.0187(8) Uani 0.5234(17) 1 d D U P A 1
H24 H 0.668927 0.684546 1.021156 0.022 Uiso 0.5234(17) 1 calc R U P A 1
C25 C 0.6921(6) 0.6775(4) 0.9185(3) 0.0166(7) Uani 0.5234(17) 1 d D U P A 1
C26 C 0.6410(6) 0.7853(4) 0.9189(3) 0.0187(7) Uani 0.5234(17) 1 d D U P A 1
H26 H 0.614673 0.828041 0.961338 0.022 Uiso 0.5234(17) 1 calc R U P A 1
N2 N 0.6303(6) 0.8246(4) 0.8647(3) 0.0225(8) Uani 0.5234(17) 1 d D U P A 1
C27 C 0.5654(8) 0.9421(6) 0.8886(3) 0.0251(9) Uani 0.5234(17) 1 d D U P A 1
C28 C 0.4002(8) 0.9431(6) 0.9026(3) 0.0287(10) Uani 0.5234(17) 1 d D U P A 1
C29 C 0.3433(4) 1.0317(3) 0.88729(17) 0.0328(6) Uani 1 1 d D U . . .
H29 H 0.227025 1.026689 0.888911 0.039 Uiso 0.5234(17) 1 calc R U P A 1
H29X H 0.237855 1.034871 0.903106 0.039 Uiso 0.4766(17) 1 calc R U P A 2
C30 C 0.4485(4) 1.1289(3) 0.86940(15) 0.0285(6) Uani 1 1 d D U . . .
H30 H 0.410091 1.196160 0.867288 0.034 Uiso 1 1 calc R U . . .
C31 C 0.6097(4) 1.1283(2) 0.85457(14) 0.0252(5) Uani 1 1 d D U . . .
H31 H 0.679998 1.193989 0.840578 0.030 Uiso 0.5234(17) 1 calc R U P A 1
H31X H 0.679194 1.195173 0.841350 0.030 Uiso 0.4766(17) 1 calc R U P A 2
C32 C 0.6705(15) 1.0318(12) 0.8599(13) 0.0268(10) Uani 0.5234(17) 1 d D U P A 1
C33 C 0.2776(7) 0.8388(5) 0.9220(3) 0.0274(10) Uani 0.5234(17) 1 d D U P A 1
H33 H 0.343149 0.808621 0.953920 0.033 Uiso 0.5234(17) 1 calc R U P A 1
C34 C 0.1317(7) 0.8681(6) 0.9584(4) 0.0324(12) Uani 0.5234(17) 1 d D U P A 1
H34A H 0.059908 0.795638 0.968727 0.049 Uiso 0.5234(17) 1 calc R U P A 1
H34B H 0.176470 0.930115 1.001972 0.049 Uiso 0.5234(17) 1 calc R U P A 1
H34C H 0.064553 0.897281 0.927971 0.049 Uiso 0.5234(17) 1 calc R U P A 1
C35 C 0.2058(8) 0.7360(6) 0.8547(4) 0.0418(14) Uani 0.5234(17) 1 d D U P A 1
H35A H 0.299604 0.716956 0.831061 0.063 Uiso 0.5234(17) 1 calc R U P A 1
H35B H 0.137009 0.664702 0.867090 0.063 Uiso 0.5234(17) 1 calc R U P A 1
H35C H 0.135485 0.761720 0.823485 0.063 Uiso 0.5234(17) 1 calc R U P A 1
C36 C 0.8483(4) 1.0339(3) 0.84164(19) 0.0357(7) Uani 1 1 d D U . . .
H36 H 0.888647 0.980133 0.865972 0.043 Uiso 1 1 calc R U . A 1
C37 C 0.9760(5) 1.1601(4) 0.8660(3) 0.0594(12) Uani 1 1 d D U . . .
H37A H 1.089320 1.155444 0.856366 0.089 Uiso 1 1 calc R U . . .
H37B H 0.976959 1.191368 0.916211 0.089 Uiso 1 1 calc R U . . .
H37C H 0.942986 1.213742 0.840908 0.089 Uiso 1 1 calc R U . . .
C38 C 0.8446(5) 0.9850(4) 0.7642(2) 0.0565(11) Uani 1 1 d D U . . .
H38A H 0.771888 0.901864 0.750019 0.085 Uiso 1 1 calc R U . . .
H38B H 0.959591 0.987626 0.753386 0.085 Uiso 1 1 calc R U . . .
H38C H 0.799834 1.033777 0.738871 0.085 Uiso 1 1 calc R U . . .
O2X O 0.6732(5) 0.7380(4) 0.9998(2) 0.0231(8) Uani 0.4766(17) 1 d D U P A 2
H2X H 0.650223 0.793923 0.986028 0.035 Uiso 0.4766(17) 1 calc R U P A 2
C20X C 0.7045(7) 0.6604(5) 0.9458(3) 0.0170(8) Uani 0.4766(17) 1 d D U P A 2
C21X C 0.7492(8) 0.5605(5) 0.9577(3) 0.0186(8) Uani 0.4766(17) 1 d D U P A 2
Br3X Br 0.75348(9) 0.53705(8) 1.04845(4) 0.0271(2) Uani 0.4766(17) 1 d D U P A 2
C22X C 0.7879(14) 0.4796(8) 0.9040(4) 0.0189(11) Uani 0.4766(17) 1 d D U P A 2
H22X H 0.818528 0.412827 0.912810 0.023 Uiso 0.4766(17) 1 calc R U P A 2
C23X C 0.7817(10) 0.4967(6) 0.8374(3) 0.0192(10) Uani 0.4766(17) 1 d D U P A 2
Br4X Br 0.8416(2) 0.38832(13) 0.76441(8) 0.0263(2) Uani 0.4766(17) 1 d D U P A 2
C24X C 0.7333(7) 0.5913(5) 0.8235(3) 0.0189(9) Uani 0.4766(17) 1 d D U P A 2
H24X H 0.725047 0.600012 0.777175 0.023 Uiso 0.4766(17) 1 calc R U P A 2
C25X C 0.6966(6) 0.6741(5) 0.8773(3) 0.0160(7) Uani 0.4766(17) 1 d D U P A 2
C26X C 0.6458(7) 0.7751(5) 0.8615(3) 0.0180(8) Uani 0.4766(17) 1 d D U P A 2
H26X H 0.634897 0.780355 0.814480 0.022 Uiso 0.4766(17) 1 calc R U P A 2
N2X N 0.6164(6) 0.8547(4) 0.9089(3) 0.0196(8) Uani 0.4766(17) 1 d D U P A 2
C27X C 0.5628(9) 0.9301(6) 0.8681(4) 0.0254(10) Uani 0.4766(17) 1 d D U P A 2
C28X C 0.3972(9) 0.9250(6) 0.8814(4) 0.0296(11) Uani 0.4766(17) 1 d D U P A 2
C32X C 0.6736(16) 1.0343(13) 0.8582(14) 0.0264(11) Uani 0.4766(17) 1 d D U P A 2
C33X C 0.2751(8) 0.8033(7) 0.8846(4) 0.0327(11) Uani 0.4766(17) 1 d D U P A 2
H33X H 0.341999 0.745506 0.886063 0.039 Uiso 0.4766(17) 1 calc R U P A 2
C34X C 0.1863(12) 0.8163(8) 0.9477(4) 0.0528(19) Uani 0.4766(17) 1 d D U P A 2
H34D H 0.269747 0.847182 0.989458 0.079 Uiso 0.4766(17) 1 calc R U P A 2
H34E H 0.119735 0.872456 0.946605 0.079 Uiso 0.4766(17) 1 calc R U P A 2
H34F H 0.110865 0.738037 0.948668 0.079 Uiso 0.4766(17) 1 calc R U P A 2
C35X C 0.1486(10) 0.7552(7) 0.8181(4) 0.0472(18) Uani 0.4766(17) 1 d D U P A 2
H35D H 0.210078 0.747348 0.777272 0.071 Uiso 0.4766(17) 1 calc R U P A 2
H35E H 0.072968 0.676527 0.818351 0.071 Uiso 0.4766(17) 1 calc R U P A 2
H35F H 0.081838 0.810946 0.816287 0.071 Uiso 0.4766(17) 1 calc R U 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 0.0033 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'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 107(2) . . ?
O1 C1 C2 120.2(2) . . ?
O1 C1 C6 121.9(2) . . ?
C2 C1 C6 117.8(2) . . ?
C3 C2 C1 122.1(2) . . ?
C3 C2 Br1 118.89(19) . . ?
C1 C2 Br1 119.00(19) . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 Br2 120.3(2) . . ?
C5 C4 Br2 119.2(2) . . ?
C4 C5 C6 119.9(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.2(2) . . ?
C5 C6 C7 118.4(2) . . ?
C1 C6 C7 121.4(2) . . ?
N1 C7 C6 121.8(2) . . ?
N1 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 N1 C8 117.9(2) . . ?
C9 C8 C13 121.5(2) . . ?
C9 C8 N1 118.3(2) . . ?
C13 C8 N1 120.1(2) . . ?
C10 C9 C8 118.3(2) . . ?
C10 C9 C14 120.5(2) . . ?
C8 C9 C14 121.2(2) . . ?
C11 C10 C9 121.1(2) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C12 C11 C10 119.7(2) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 121.8(2) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C12 C13 C8 117.4(2) . . ?
C12 C13 C17 119.7(2) . . ?
C8 C13 C17 122.8(2) . . ?
C9 C14 C16 110.8(2) . . ?
C9 C14 C15 110.9(2) . . ?
C16 C14 C15 110.9(2) . . ?
C9 C14 H14 108.0 . . ?
C16 C14 H14 108.0 . . ?
C15 C14 H14 108.0 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 C19 112.2(2) . . ?
C13 C17 C18 111.1(2) . . ?
C19 C17 C18 110.5(2) . . ?
C13 C17 H17 107.6 . . ?
C19 C17 H17 107.6 . . ?
C18 C17 H17 107.6 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 O2 H2 109.5 . . ?
O2 C20 C25 123.1(5) . . ?
O2 C20 C21 118.6(5) . . ?
C25 C20 C21 118.3(5) . . ?
C22 C21 C20 121.1(6) . . ?
C22 C21 Br3 119.8(5) . . ?
C20 C21 Br3 119.1(4) . . ?
C21 C22 C23 119.5(6) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C24 C23 C22 120.7(5) . . ?
C24 C23 Br4 119.9(4) . . ?
C22 C23 Br4 119.4(4) . . ?
C23 C24 C25 120.1(5) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C20 120.3(5) . . ?
C24 C25 C26 119.0(5) . . ?
C20 C25 C26 120.7(5) . . ?
N2 C26 C25 122.9(5) . . ?
N2 C26 H26 118.6 . . ?
C25 C26 H26 118.6 . . ?
C26 N2 C27 105.9(5) . . ?
C28 C27 C32 121.5(6) . . ?
C28 C27 N2 126.4(5) . . ?
C32 C27 N2 105.7(6) . . ?
C29 C28 C27 117.5(5) . . ?
C29 C28 C33 119.6(5) . . ?
C27 C28 C33 122.1(6) . . ?
C28 C29 C30 122.3(4) . . ?
C30 C29 C28X 118.5(4) . . ?
C28 C29 H29 118.8 . . ?
C30 C29 H29 118.8 . . ?
C30 C29 H29X 120.7 . . ?
C28X C29 H29X 120.7 . . ?
C31 C30 C29 119.9(3) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C32X C31 C30 122.6(4) . . ?
C30 C31 C32 120.7(4) . . ?
C30 C31 H31 119.6 . . ?
C32 C31 H31 119.6 . . ?
C32X C31 H31X 118.7 . . ?
C30 C31 H31X 118.7 . . ?
C31 C32 C27 116.7(6) . . ?
C31 C32 C36 118.9(6) . . ?
C27 C32 C36 124.2(7) . . ?
C34 C33 C28 115.4(5) . . ?
C34 C33 C35 109.3(5) . . ?
C28 C33 C35 108.6(5) . . ?
C34 C33 H33 107.8 . . ?
C28 C33 H33 107.8 . . ?
C35 C33 H33 107.8 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C32X C36 C38 109.8(11) . . ?
C38 C36 C32 110.6(10) . . ?
C32X C36 C37 112.0(7) . . ?
C38 C36 C37 110.0(3) . . ?
C32 C36 C37 112.8(7) . . ?
C38 C36 H36 107.7 . . ?
C32 C36 H36 107.7 . . ?
C37 C36 H36 107.7 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C20X O2X H2X 109.5 . . ?
O2X C20X C25X 123.2(5) . . ?
O2X C20X C21X 118.8(5) . . ?
C25X C20X C21X 118.0(5) . . ?
C22X C21X C20X 121.1(6) . . ?
C22X C21X Br3X 120.0(5) . . ?
C20X C21X Br3X 118.9(4) . . ?
C21X C22X C23X 119.5(6) . . ?
C21X C22X H22X 120.3 . . ?
C23X C22X H22X 120.3 . . ?
C24X C23X C22X 120.9(6) . . ?
C24X C23X Br4X 119.7(5) . . ?
C22X C23X Br4X 119.4(5) . . ?
C23X C24X C25X 120.0(6) . . ?
C23X C24X H24X 120.0 . . ?
C25X C24X H24X 120.0 . . ?
C24X C25X C20X 120.4(5) . . ?
C24X C25X C26X 119.2(5) . . ?
C20X C25X C26X 120.4(5) . . ?
N2X C26X C25X 121.6(5) . . ?
N2X C26X H26X 119.2 . . ?
C25X C26X H26X 119.2 . . ?
C26X N2X C27X 101.6(5) . . ?
C32X C27X C28X 121.2(7) . . ?
C32X C27X N2X 122.7(9) . . ?
C28X C27X N2X 105.5(5) . . ?
C27X C28X C29 118.8(5) . . ?
C27X C28X C33X 118.7(6) . . ?
C29 C28X C33X 122.4(6) . . ?
C31 C32X C27X 117.9(7) . . ?
C31 C32X C36 122.3(6) . . ?
C27X C32X C36 119.2(7) . . ?
C34X C33X C35X 111.0(6) . . ?
C34X C33X C28X 111.1(7) . . ?
C35X C33X C28X 108.3(6) . . ?
C34X C33X H33X 108.8 . . ?
C35X C33X H33X 108.8 . . ?
C28X C33X H33X 108.8 . . ?
C33X C34X H34D 109.5 . . ?
C33X C34X H34E 109.5 . . ?
H34D C34X H34E 109.5 . . ?
C33X C34X H34F 109.5 . . ?
H34D C34X H34F 109.5 . . ?
H34E C34X H34F 109.5 . . ?
C33X C35X H35D 109.5 . . ?
C33X C35X H35E 109.5 . . ?
H35D C35X H35E 109.5 . . ?
C33X C35X H35F 109.5 . . ?
H35D C35X H35F 109.5 . . ?
H35E C35X H35F 109.5 . . ?
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
O1 C1 1.344(3) . ?
O1 H1 0.837(18) . ?
C1 C2 1.390(4) . ?
C1 C6 1.413(3) . ?
C2 C3 1.382(4) . ?
C2 Br1 1.891(3) . ?
C3 C4 1.384(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(4) . ?
C4 Br2 1.893(3) . ?
C5 C6 1.399(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.455(3) . ?
C7 N1 1.277(3) . ?
C7 H7 0.9500 . ?
N1 C8 1.427(3) . ?
C8 C9 1.408(3) . ?
C8 C13 1.412(3) . ?
C9 C10 1.392(4) . ?
C9 C14 1.526(3) . ?
C10 C11 1.386(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.396(4) . ?
C12 H12 0.9500 . ?
C13 C17 1.523(4) . ?
C14 C16 1.527(4) . ?
C14 C15 1.529(4) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C19 1.528(4) . ?
C17 C18 1.539(4) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
O2 C20 1.342(6) . ?
O2 H2 0.8400 . ?
C20 C25 1.403(7) . ?
C20 C21 1.415(8) . ?
C21 C22 1.380(7) . ?
C21 Br3 1.879(6) . ?
C22 C23 1.392(8) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(7) . ?
C23 Br4 1.894(5) . ?
C24 C25 1.394(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.462(6) . ?
C26 N2 1.274(6) . ?
C26 H26 0.9500 . ?
N2 C27 1.620(8) . ?
C27 C28 1.412(8) . ?
C27 C32 1.434(9) . ?
C28 C29 1.356(7) . ?
C28 C33 1.519(7) . ?
C29 C30 1.382(4) . ?
C29 C28X 1.445(8) . ?
C29 H29 0.9500 . ?
C29 H29X 0.9500 . ?
C30 C31 1.382(4) . ?
C30 H30 0.9500 . ?
C31 C32X 1.380(9) . ?
C31 C32 1.401(8) . ?
C31 H31 0.9500 . ?
C31 H31X 0.9500 . ?
C32 C36 1.529(8) . ?
C33 C34 1.519(8) . ?
C33 C35 1.555(9) . ?
C33 H33 1.0000 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 C32X 1.500(8) . ?
C36 C38 1.510(5) . ?
C36 C37 1.542(5) . ?
C36 H36 1.0000 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
O2X C20X 1.336(6) . ?
O2X H2X 0.8400 . ?
C20X C25X 1.404(7) . ?
C20X C21X 1.408(7) . ?
C21X C22X 1.381(9) . ?
C21X Br3X 1.885(6) . ?
C22X C23X 1.383(8) . ?
C22X H22X 0.9500 . ?
C23X C24X 1.376(8) . ?
C23X Br4X 1.896(6) . ?
C24X C25X 1.389(7) . ?
C24X H24X 0.9500 . ?
C25X C26X 1.473(7) . ?
C26X N2X 1.263(7) . ?
C26X H26X 0.9500 . ?
N2X C27X 1.474(7) . ?
C27X C32X 1.395(10) . ?
C27X C28X 1.396(9) . ?
C28X C33X 1.548(8) . ?
C33X C34X 1.485(10) . ?
C33X C35X 1.530(9) . ?
C33X H33X 1.0000 . ?
C34X H34D 0.9800 . ?
C34X H34E 0.9800 . ?
C34X H34F 0.9800 . ?
C35X H35D 0.9800 . ?
C35X H35E 0.9800 . ?
C35X H35F 0.9800 . ?
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
_geom_hbond_publ_flag
O1 H1 N1 0.837(18) 1.86(2) 2.621(3) 150(3) . yes
O1 H1 Br4X 0.837(18) 2.97(3) 3.399(2) 115(3) . yes
O2 H2 N2 0.84 1.91 2.642(7) 144.2 . yes
O2X H2X N2X 0.84 1.88 2.615(6) 145.9 . yes
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
O1 C1 C2 C3 179.2(2) . . . . ?
C6 C1 C2 C3 -1.0(4) . . . . ?
O1 C1 C2 Br1 -0.6(3) . . . . ?
C6 C1 C2 Br1 179.23(18) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
Br1 C2 C3 C4 -179.65(19) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C2 C3 C4 Br2 -179.31(19) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
Br2 C4 C5 C6 178.94(19) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C4 C5 C6 C7 179.7(2) . . . . ?
O1 C1 C6 C5 -179.6(2) . . . . ?
C2 C1 C6 C5 0.6(4) . . . . ?
O1 C1 C6 C7 0.9(4) . . . . ?
C2 C1 C6 C7 -178.9(2) . . . . ?
C5 C6 C7 N1 -179.6(2) . . . . ?
C1 C6 C7 N1 -0.1(4) . . . . ?
C6 C7 N1 C8 175.1(2) . . . . ?
C7 N1 C8 C9 119.3(3) . . . . ?
C7 N1 C8 C13 -63.4(3) . . . . ?
C13 C8 C9 C10 4.9(4) . . . . ?
N1 C8 C9 C10 -177.8(2) . . . . ?
C13 C8 C9 C14 -175.5(2) . . . . ?
N1 C8 C9 C14 1.8(4) . . . . ?
C8 C9 C10 C11 -1.8(4) . . . . ?
C14 C9 C10 C11 178.6(3) . . . . ?
C9 C10 C11 C12 -1.6(4) . . . . ?
C10 C11 C12 C13 2.0(4) . . . . ?
C11 C12 C13 C8 1.0(4) . . . . ?
C11 C12 C13 C17 -175.4(3) . . . . ?
C9 C8 C13 C12 -4.4(4) . . . . ?
N1 C8 C13 C12 178.3(2) . . . . ?
C9 C8 C13 C17 171.8(2) . . . . ?
N1 C8 C13 C17 -5.5(4) . . . . ?
C10 C9 C14 C16 66.9(3) . . . . ?
C8 C9 C14 C16 -112.7(3) . . . . ?
C10 C9 C14 C15 -56.7(3) . . . . ?
C8 C9 C14 C15 123.7(3) . . . . ?
C12 C13 C17 C19 -71.8(3) . . . . ?
C8 C13 C17 C19 112.1(3) . . . . ?
C12 C13 C17 C18 52.4(3) . . . . ?
C8 C13 C17 C18 -123.7(3) . . . . ?
O2 C20 C21 C22 178.5(6) . . . . ?
C25 C20 C21 C22 -0.9(9) . . . . ?
O2 C20 C21 Br3 -1.0(8) . . . . ?
C25 C20 C21 Br3 179.5(4) . . . . ?
C20 C21 C22 C23 0.8(11) . . . . ?
Br3 C21 C22 C23 -179.6(6) . . . . ?
C21 C22 C23 C24 -0.5(11) . . . . ?
C21 C22 C23 Br4 -179.7(6) . . . . ?
C22 C23 C24 C25 0.3(9) . . . . ?
Br4 C23 C24 C25 179.6(4) . . . . ?
C23 C24 C25 C20 -0.5(8) . . . . ?
C23 C24 C25 C26 179.9(5) . . . . ?
O2 C20 C25 C24 -178.7(5) . . . . ?
C21 C20 C25 C24 0.8(8) . . . . ?
O2 C20 C25 C26 0.9(8) . . . . ?
C21 C20 C25 C26 -179.6(5) . . . . ?
C24 C25 C26 N2 -179.0(5) . . . . ?
C20 C25 C26 N2 1.4(8) . . . . ?
C25 C26 N2 C27 178.5(5) . . . . ?
C26 N2 C27 C28 -73.5(7) . . . . ?
C26 N2 C27 C32 134.6(11) . . . . ?
C32 C27 C28 C29 0.7(14) . . . . ?
N2 C27 C28 C29 -147.1(5) . . . . ?
C32 C27 C28 C33 170.1(13) . . . . ?
N2 C27 C28 C33 22.3(9) . . . . ?
C27 C28 C29 C30 -10.4(8) . . . . ?
C33 C28 C29 C30 179.9(5) . . . . ?
C28 C29 C30 C31 11.5(6) . . . . ?
C28X C29 C30 C31 -7.8(5) . . . . ?
C29 C30 C31 C32X -1.4(14) . . . . ?
C29 C30 C31 C32 -2.4(13) . . . . ?
C30 C31 C32 C27 -7(2) . . . . ?
C30 C31 C32 C36 178.8(11) . . . . ?
C28 C27 C32 C31 8(2) . . . . ?
N2 C27 C32 C31 161.2(14) . . . . ?
C28 C27 C32 C36 -178.2(13) . . . . ?
N2 C27 C32 C36 -25(2) . . . . ?
C29 C28 C33 C34 -30.5(8) . . . . ?
C27 C28 C33 C34 160.3(6) . . . . ?
C29 C28 C33 C35 92.6(7) . . . . ?
C27 C28 C33 C35 -76.6(7) . . . . ?
C31 C32 C36 C38 -85.3(18) . . . . ?
C27 C32 C36 C38 100.6(19) . . . . ?
C31 C32 C36 C37 38(2) . . . . ?
C27 C32 C36 C37 -135.7(16) . . . . ?
O2X C20X C21X C22X -178.0(7) . . . . ?
C25X C20X C21X C22X 1.4(9) . . . . ?
O2X C20X C21X Br3X 2.7(8) . . . . ?
C25X C20X C21X Br3X -177.9(4) . . . . ?
C20X C21X C22X C23X -0.3(12) . . . . ?
Br3X C21X C22X C23X 178.9(6) . . . . ?
C21X C22X C23X C24X -1.7(12) . . . . ?
C21X C22X C23X Br4X 178.1(7) . . . . ?
C22X C23X C24X C25X 2.6(10) . . . . ?
Br4X C23X C24X C25X -177.1(5) . . . . ?
C23X C24X C25X C20X -1.6(9) . . . . ?
C23X C24X C25X C26X 179.7(6) . . . . ?
O2X C20X C25X C24X 178.9(5) . . . . ?
C21X C20X C25X C24X -0.4(8) . . . . ?
O2X C20X C25X C26X -2.4(8) . . . . ?
C21X C20X C25X C26X 178.3(5) . . . . ?
C24X C25X C26X N2X -177.7(5) . . . . ?
C20X C25X C26X N2X 3.6(8) . . . . ?
C25X C26X N2X C27X -177.1(5) . . . . ?
C26X N2X C27X C32X -96.4(12) . . . . ?
C26X N2X C27X C28X 119.0(6) . . . . ?
C32X C27X C28X C29 -2.2(16) . . . . ?
N2X C27X C28X C29 143.1(6) . . . . ?
C32X C27X C28X C33X 173.9(14) . . . . ?
N2X C27X C28X C33X -40.8(8) . . . . ?
C30 C29 C28X C27X 9.5(8) . . . . ?
C30 C29 C28X C33X -166.5(5) . . . . ?
C30 C31 C32X C27X 9(3) . . . . ?
C30 C31 C32X C36 179.6(13) . . . . ?
C28X C27X C32X C31 -7(3) . . . . ?
N2X C27X C32X C31 -146.0(14) . . . . ?
C28X C27X C32X C36 -177.9(13) . . . . ?
N2X C27X C32X C36 43(2) . . . . ?
C38 C36 C32X C31 -86(2) . . . . ?
C37 C36 C32X C31 36(2) . . . . ?
C38 C36 C32X C27X 84.7(19) . . . . ?
C37 C36 C32X C27X -152.8(16) . . . . ?
C27X C28X C33X C34X 131.5(8) . . . . ?
C29 C28X C33X C34X -52.6(9) . . . . ?
C27X C28X C33X C35X -106.4(8) . . . . ?
C29 C28X C33X C35X 69.6(9) . . . . ?
