#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:52:37 +0200 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/7/22/84/7228479.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_7228479
loop_
_publ_author_name
'Puttreddy, Rakesh'
'Beyeh, Ngong Kodiah'
'Ras, Robin H.A.'
'Trant, John'
'Rissanen, Kari'
_publ_section_title
;
 Endo-/Exo- and Halogen Bonded Complexes of Conformationally Rigid
 Cethyl-2-bromoresorcinarene and aromatic N-oxides
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE00975E
_journal_year                    2017
_chemical_formula_moiety         'C36 H36 Br4 O8, 3(C10 H8 N2 O2), 3(C3 H6 O)'
_chemical_formula_sum            'C75 H78 Br4 N6 O17'
_chemical_formula_weight         1655.07
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2017-05-22 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 120.42(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   37.615(8)
_cell_length_b                   7.8003(16)
_cell_length_c                   27.830(6)
_cell_measurement_reflns_used    10353
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      73.1380
_cell_measurement_theta_min      3.6550
_cell_volume                     7041(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -46.00   33.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   37.0000  -90.0000 79

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00   -4.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   37.0000 -120.0000 45

#__ type_ start__ end____ width___ exp.time_
  3 omega  -96.00   -7.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  125.0000  -30.0000 89

#__ type_ start__ end____ width___ exp.time_
  4 omega -114.00  -25.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  -37.0000   90.0000 89

#__ type_ start__ end____ width___ exp.time_
  5 omega   33.00   91.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000  -60.0000 58

#__ type_ start__ end____ width___ exp.time_
  6 omega   53.00  121.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   15.0000  -60.0000 68

#__ type_ start__ end____ width___ exp.time_
  7 omega   61.00  173.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   15.0000 -180.0000 112

#__ type_ start__ end____ width___ exp.time_
  8 omega   98.00  173.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  125.0000 -150.0000 75

#__ type_ start__ end____ width___ exp.time_
  9 omega   41.00   99.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -45.0000  120.0000 58

#__ type_ start__ end____ width___ exp.time_
 10 omega   32.00  122.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154 -125.0000   90.0000 90

#__ type_ start__ end____ width___ exp.time_
 11 omega   26.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000  150.0000 83

#__ type_ start__ end____ width___ exp.time_
 12 omega   30.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -30.0000 -120.0000 59

#__ type_ start__ end____ width___ exp.time_
 13 omega   31.00  136.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -73.0000 -122.0000 105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0201194000
_diffrn_orient_matrix_UB_12      -0.1232074000
_diffrn_orient_matrix_UB_13      -0.0099238000
_diffrn_orient_matrix_UB_21      -0.0327794000
_diffrn_orient_matrix_UB_22      -0.1366391000
_diffrn_orient_matrix_UB_23      -0.0314106000
_diffrn_orient_matrix_UB_31      -0.0278506000
_diffrn_orient_matrix_UB_32      0.0718906000
_diffrn_orient_matrix_UB_33      -0.0766715000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            21198
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_min         1.516
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.362
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85341
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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    1.561
_exptl_crystal_description       needle
_exptl_crystal_F_000             3384
_exptl_crystal_size_max          0.1712
_exptl_crystal_size_mid          0.0805
_exptl_crystal_size_min          0.0549
_refine_diff_density_max         3.166
_refine_diff_density_min         -0.787
_refine_diff_density_rms         0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     466
_refine_ls_number_reflns         6382
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0566
_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)+(0.0993P)²+33.2637P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1499
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5827
_reflns_number_total             6382
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce00975e2.cif
_cod_data_source_block           acetone_BrC2_10
_cod_original_cell_volume        7042(3)
_cod_database_code               7228479
_chemical_oxdiff_formula         'C10 H20 N4 O4 Br1'
_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.
;
_reflns_odcompleteness_completeness 99.88
_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.a Riding coordinates:
 O1(H1), O2(H2), O3(H3), O4(H4)
2.b Ternary CH refined with riding coordinates:
 C13(H13), C16(H16)
2.c Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C17(H17A,H17B)
2.d Aromatic/amide H refined with riding coordinates:
 C6(H6), C12(H12), C19(H19), C20(H20), C21(H21), C22(H22), C25(H25), C26(H26),
 C27(H27), C28(H28), C29(H29), C30(H30), C32(H32), C33(H33)
2.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C35(H35A,H35B,H35C), C36(H36A,H36B,
 H36C), C38(H38A,H38B,H38C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'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
Br1 Br 0.66976(2) 0.60542(5) 0.77296(2) 0.02083(14) Uani 1 1 d . . .
Br2 Br 0.44013(2) 0.74056(5) 0.56495(2) 0.01793(14) Uani 1 1 d . . .
O1 O 0.66213(8) 0.4381(3) 0.86616(10) 0.0161(5) Uani 1 1 d . . .
H1 H 0.6806 0.3670 0.8852 0.024 Uiso 1 1 d R . .
O2 O 0.60006(8) 0.4570(4) 0.66837(11) 0.0191(5) Uani 1 1 d . . .
H2 H 0.5751 0.4772 0.6478 0.029 Uiso 1 1 d R . .
O3 O 0.51581(7) 0.5153(3) 0.59985(11) 0.0171(5) Uani 1 1 d . . .
H3 H 0.5163 0.5926 0.5780 0.026 Uiso 1 1 d R . .
O4 O 0.38615(8) 0.5283(3) 0.59106(11) 0.0190(6) Uani 1 1 d . . .
H4 H 0.3712 0.4994 0.6036 0.029 Uiso 1 1 d R . .
O5 O 0.72011(8) 0.2226(4) 0.92343(12) 0.0231(6) Uani 1 1 d . . .
O6 O 0.99620(8) 0.2353(3) 0.98148(12) 0.0195(6) Uani 1 1 d . . .
O7 O 0.33102(9) 0.7819(4) 0.40952(13) 0.0254(6) Uani 1 1 d . . .
O8 O 0.72760(13) 0.9285(5) 0.78529(14) 0.0445(9) Uani 1 1 d . . .
O9 O 0.5000 0.8927(5) 0.7500 0.0244(9) Uani 1 2 d S T P
N1 N 0.75779(10) 0.2256(4) 0.93082(14) 0.0178(7) Uani 1 1 d . . .
N2 N 0.95873(10) 0.2330(4) 0.97470(13) 0.0160(6) Uani 1 1 d . . .
N3 N 0.30877(10) 0.7706(4) 0.43317(14) 0.0184(7) Uani 1 1 d . . .
C1 C 0.57049(11) 0.2675(5) 0.70820(15) 0.0136(7) Uani 1 1 d . . .
C2 C 0.59959(11) 0.3895(5) 0.71327(15) 0.0152(7) Uani 1 1 d . . .
C3 C 0.63041(11) 0.4422(5) 0.76646(15) 0.0150(7) Uani 1 1 d . . .
C4 C 0.63200(11) 0.3776(5) 0.81416(15) 0.0144(7) Uani 1 1 d . . .
C5 C 0.60220(11) 0.2613(4) 0.80957(15) 0.0135(7) Uani 1 1 d . . .
C6 C 0.57178(10) 0.2121(5) 0.75639(15) 0.0120(7) Uani 1 1 d . . .
H6 H 0.5512 0.1381 0.7530 0.014 Uiso 1 1 calc R . .
C7 C 0.42890(11) 0.2729(5) 0.62848(15) 0.0155(7) Uani 1 1 d . . .
C8 C 0.42115(11) 0.4375(5) 0.60524(14) 0.0148(7) Uani 1 1 d . . .
C9 C 0.45007(11) 0.5171(5) 0.59507(14) 0.0149(7) Uani 1 1 d . . .
C10 C 0.48695(11) 0.4375(5) 0.60839(14) 0.0147(7) Uani 1 1 d . . .
C11 C 0.49602(11) 0.2744(5) 0.63338(15) 0.0151(7) Uani 1 1 d . . .
C12 C 0.46677(11) 0.1979(5) 0.64260(14) 0.0136(7) Uani 1 1 d . . .
H12 H 0.4727 0.0902 0.6592 0.016 Uiso 1 1 calc R . .
C13 C 0.53798(10) 0.1979(5) 0.65131(14) 0.0128(7) Uani 1 1 d . . .
H13 H 0.5457 0.2371 0.6244 0.015 Uiso 1 1 calc R . .
C14 C 0.53824(11) 0.0007(5) 0.65022(15) 0.0185(7) Uani 1 1 d . . .
H14A H 0.5308 -0.0427 0.6766 0.022 Uiso 1 1 calc R . .
H14B H 0.5176 -0.0386 0.6134 0.022 Uiso 1 1 calc R . .
C15 C 0.58012(13) -0.0722(5) 0.66455(18) 0.0248(8) Uani 1 1 d . . .
H15A H 0.5886 -0.0231 0.6403 0.037 Uiso 1 1 calc GR . .
H15B H 0.5781 -0.1945 0.6599 0.037 Uiso 1 1 calc GR . .
H15C H 0.6001 -0.0450 0.7025 0.037 Uiso 1 1 calc GR . .
C16 C 0.39670(11) 0.1902(5) 0.63863(14) 0.0141(7) Uani 1 1 d . . .
H16 H 0.3698 0.2214 0.6068 0.017 Uiso 1 1 calc R . .
C17 C 0.39831(11) -0.0070(5) 0.64042(15) 0.0157(7) Uani 1 1 d . . .
H17A H 0.3956 -0.0495 0.6059 0.019 Uiso 1 1 calc R . .
H17B H 0.4250 -0.0434 0.6707 0.019 Uiso 1 1 calc R . .
C18 C 0.36428(13) -0.0865(5) 0.64844(17) 0.0226(8) Uani 1 1 d . . .
H18A H 0.3380 -0.0405 0.6211 0.034 Uiso 1 1 calc GR . .
H18B H 0.3694 -0.0600 0.6851 0.034 Uiso 1 1 calc GR . .
H18C H 0.3641 -0.2086 0.6441 0.034 Uiso 1 1 calc GR . .
C19 C 0.76639(12) 0.1300(5) 0.89729(16) 0.0210(8) Uani 1 1 d . . .
H19 H 0.7456 0.0655 0.8688 0.025 Uiso 1 1 calc R . .
C20 C 0.80556(12) 0.1274(5) 0.90512(16) 0.0192(8) Uani 1 1 d . . .
H20 H 0.8112 0.0592 0.8824 0.023 Uiso 1 1 calc R . .
C21 C 0.78772(12) 0.3194(5) 0.97298(16) 0.0204(8) Uani 1 1 d . . .
H21 H 0.7817 0.3820 0.9964 0.024 Uiso 1 1 calc R . .
C22 C 0.82682(11) 0.3221(5) 0.98109(15) 0.0173(7) Uani 1 1 d . . .
H22 H 0.8470 0.3884 1.0097 0.021 Uiso 1 1 calc R . .
C23 C 0.83699(12) 0.2267(5) 0.94707(16) 0.0157(7) Uani 1 1 d . . .
C24 C 0.87922(12) 0.2290(5) 0.95628(16) 0.0165(7) Uani 1 1 d . . .
C25 C 0.90215(12) 0.3807(5) 0.97000(16) 0.0185(8) Uani 1 1 d . . .
H25 H 0.8906 0.4824 0.9732 0.022 Uiso 1 1 calc R . .
C26 C 0.94153(12) 0.3807(5) 0.97879(15) 0.0186(8) Uani 1 1 d . . .
H26 H 0.9564 0.4825 0.9876 0.022 Uiso 1 1 calc R . .
C27 C 0.93765(11) 0.0824(5) 0.96237(15) 0.0166(7) Uani 1 1 d . . .
H27 H 0.9501 -0.0186 0.9607 0.020 Uiso 1 1 calc R . .
C28 C 0.89772(11) 0.0792(5) 0.95232(15) 0.0164(7) Uani 1 1 d . . .
H28 H 0.8831 -0.0234 0.9429 0.020 Uiso 1 1 calc R . .
C29 C 0.32652(12) 0.7239(5) 0.48750(17) 0.0200(8) Uani 1 1 d . . .
H29 H 0.3545 0.6978 0.5073 0.024 Uiso 1 1 calc R . .
C30 C 0.30415(12) 0.7147(5) 0.51350(16) 0.0206(8) Uani 1 1 d . . .
H30 H 0.3173 0.6824 0.5508 0.025 Uiso 1 1 calc R . .
C31 C 0.26193(12) 0.7522(4) 0.48572(16) 0.0154(7) Uani 1 1 d . . .
C32 C 0.24414(12) 0.7946(5) 0.42900(16) 0.0200(8) Uani 1 1 d . . .
H32 H 0.2160 0.8169 0.4081 0.024 Uiso 1 1 calc R . .
C33 C 0.26763(12) 0.8035(5) 0.40389(16) 0.0203(8) Uani 1 1 d . . .
H33 H 0.2551 0.8324 0.3664 0.024 Uiso 1 1 calc R . .
C34 C 0.5000 0.7369(7) 0.7500 0.0246(13) Uani 1 2 d S T P
C35 C 0.5341(2) 0.6395(8) 0.7509(2) 0.0582(18) Uani 1 1 d . . .
H35A H 0.5531 0.7179 0.7490 0.087 Uiso 1 1 calc GR . .
H35B H 0.5232 0.5633 0.7195 0.087 Uiso 1 1 calc GR . .
H35C H 0.5483 0.5742 0.7847 0.087 Uiso 1 1 calc GR . .
C36 C 0.69387(19) 0.8910(7) 0.6878(2) 0.0401(12) Uani 1 1 d . . .
H36A H 0.7101 0.7883 0.6970 0.060 Uiso 1 1 calc GR . .
H36B H 0.6978 0.9575 0.6618 0.060 Uiso 1 1 calc GR . .
H36C H 0.6653 0.8614 0.6713 0.060 Uiso 1 1 calc GR . .
C37 C 0.70705(14) 0.9941(6) 0.73965(19) 0.0299(9) Uani 1 1 d . . .
C38 C 0.69367(18) 1.1767(7) 0.7322(2) 0.0450(13) Uani 1 1 d . . .
H38A H 0.6981 1.2215 0.7669 0.068 Uiso 1 1 calc GR . .
H38B H 0.6649 1.1841 0.7046 0.068 Uiso 1 1 calc GR . .
H38C H 0.7094 1.2422 0.7202 0.068 Uiso 1 1 calc GR . .
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'
Br Br -0.2901 2.4595 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 -12 0.0345 -0.0038 0.0001 -11.9989 0.1190 0.3770 0.9201
0 0 12 0.0323 0.0038 -0.0001 11.9989 -0.1190 -0.3770 -0.9201
-11 -5 5 0.0726 -10.9993 -5.0000 4.9997 0.3451 0.8867 -0.4365
12 5 -5 0.1096 11.9994 5.0000 -4.9998 -0.3250 -0.9195 0.4086
28 -1 -18 0.0355 27.9969 -0.9999 -17.9993 0.8651 -0.2157 0.5284
-27 0 18 0.0282 -26.9968 -0.0001 17.9992 -0.7218 0.3196 -0.6282
28 1 -6 0.0441 28.0006 0.9999 -6.0003 0.4997 -0.8660 -0.2479
-24 0 2 0.0132 -24.0015 0.0001 2.0006 -0.5028 0.7239 0.5151
-30 -2 14 0.0088 -29.9983 -2.0000 13.9996 -0.4961 0.8169 -0.3817
19 2 -16 0.0647 18.9967 2.0001 -15.9991 0.2945 -0.3934 0.8414
-11 -4 9 0.0464 -10.9981 -4.0000 8.9994 0.1823 0.6244 -0.6713
-6 5 1 0.0931 -6.0003 5.0000 1.0003 -0.7467 -0.5179 0.4499
29 -1 -8 0.0306 29.0001 -1.0000 -8.0002 0.7861 -0.5627 -0.2662
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
C4 O1 H1 114.4 . .
C2 O2 H2 99.9 . .
C10 O3 H3 137.3 . .
C8 O4 H4 119.8 . .
O5 N1 C19 119.5(3) . .
O5 N1 C21 119.8(3) . .
C19 N1 C21 120.6(3) . .
O6 N2 C26 119.7(3) . .
O6 N2 C27 119.3(3) . .
C26 N2 C27 120.9(3) . .
O7 N3 C29 120.1(3) . .
O7 N3 C33 120.8(3) . .
C29 N3 C33 119.1(3) . .
C2 C1 C13 121.3(3) . .
C6 C1 C2 118.1(3) . .
C6 C1 C13 120.6(3) . .
O2 C2 C1 122.7(3) . .
O2 C2 C3 117.8(3) . .
C3 C2 C1 119.4(3) . .
C2 C3 Br1 119.1(3) . .
C4 C3 Br1 119.9(3) . .
C4 C3 C2 120.9(3) . .
O1 C4 C5 120.5(3) . .
C3 C4 O1 119.2(3) . .
C3 C4 C5 120.2(3) . .
C4 C5 C16 120.9(3) . 2_656
C6 C5 C4 117.8(3) . .
C6 C5 C16 121.3(3) . 2_656
C1 C6 C5 123.4(3) . .
C1 C6 H6 118.3 . .
C5 C6 H6 118.3 . .
C8 C7 C16 118.4(3) . .
C12 C7 C8 117.2(3) . .
C12 C7 C16 124.3(3) . .
O4 C8 C7 123.7(3) . .
O4 C8 C9 116.5(3) . .
C9 C8 C7 119.9(3) . .
C8 C9 Br2 120.0(3) . .
C10 C9 Br2 118.5(3) . .
C10 C9 C8 121.4(3) . .
O3 C10 C9 122.0(3) . .
O3 C10 C11 118.2(3) . .
C9 C10 C11 119.7(3) . .
C10 C11 C13 118.0(3) . .
C12 C11 C10 117.7(3) . .
C12 C11 C13 124.2(3) . .
C7 C12 H12 118.0 . .
C11 C12 C7 124.0(4) . .
C11 C12 H12 118.0 . .
C1 C13 H13 106.8 . .
C1 C13 C14 111.4(3) . .
C11 C13 C1 110.8(3) . .
C11 C13 H13 106.8 . .
C11 C13 C14 113.8(3) . .
C14 C13 H13 106.8 . .
C13 C14 H14A 109.1 . .
C13 C14 H14B 109.1 . .
H14A C14 H14B 107.8 . .
C15 C14 C13 112.6(3) . .
C15 C14 H14A 109.1 . .
C15 C14 H14B 109.1 . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C5 C16 H16 106.5 2_656 .
C5 C16 C17 110.6(3) 2_656 .
C7 C16 C5 112.2(3) . 2_656
C7 C16 H16 106.5 . .
C7 C16 C17 114.1(3) . .
C17 C16 H16 106.5 . .
C16 C17 H17A 109.1 . .
C16 C17 H17B 109.1 . .
H17A C17 H17B 107.8 . .
C18 C17 C16 112.7(3) . .
C18 C17 H17A 109.1 . .
C18 C17 H17B 109.1 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18B 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
N1 C19 H19 119.7 . .
N1 C19 C20 120.6(4) . .
C20 C19 H19 119.7 . .
C19 C20 H20 119.7 . .
C19 C20 C23 120.5(4) . .
C23 C20 H20 119.7 . .
N1 C21 H21 119.9 . .
N1 C21 C22 120.1(4) . .
C22 C21 H21 119.9 . .
C21 C22 H22 119.4 . .
C21 C22 C23 121.2(4) . .
C23 C22 H22 119.4 . .
C20 C23 C22 116.9(3) . .
C20 C23 C24 122.1(3) . .
C22 C23 C24 120.9(3) . .
C25 C24 C23 121.2(3) . .
C28 C24 C23 120.9(3) . .
C28 C24 C25 117.9(4) . .
C24 C25 H25 119.7 . .
C26 C25 C24 120.6(4) . .
C26 C25 H25 119.7 . .
N2 C26 C25 120.2(4) . .
N2 C26 H26 119.9 . .
C25 C26 H26 119.9 . .
N2 C27 H27 120.0 . .
N2 C27 C28 120.1(3) . .
C28 C27 H27 120.0 . .
C24 C28 H28 119.9 . .
C27 C28 C24 120.3(4) . .
C27 C28 H28 119.9 . .
N3 C29 H29 119.4 . .
N3 C29 C30 121.2(4) . .
C30 C29 H29 119.4 . .
C29 C30 H30 119.0 . .
C29 C30 C31 121.9(4) . .
C31 C30 H30 119.0 . .
C30 C31 C31 121.9(4) . 7_566
C30 C31 C32 115.5(4) . .
C32 C31 C31 122.6(4) . 7_566
C31 C32 H32 119.4 . .
C33 C32 C31 121.2(4) . .
C33 C32 H32 119.4 . .
N3 C33 C32 120.9(4) . .
N3 C33 H33 119.5 . .
C32 C33 H33 119.5 . .
O9 C34 C35 120.8(4) . .
O9 C34 C35 120.8(4) . 2_656
C35 C34 C35 118.3(7) . 2_656
C34 C35 H35A 109.5 . .
C34 C35 H35B 109.5 . .
C34 C35 H35C 109.5 . .
H35A C35 H35B 109.5 . .
H35A C35 H35C 109.5 . .
H35B C35 H35C 109.5 . .
H36A C36 H36B 109.5 . .
H36A C36 H36C 109.5 . .
H36B C36 H36C 109.5 . .
C37 C36 H36A 109.5 . .
C37 C36 H36B 109.5 . .
C37 C36 H36C 109.5 . .
O8 C37 C36 120.4(5) . .
O8 C37 C38 122.6(4) . .
C38 C37 C36 117.0(4) . .
C37 C38 H38A 109.5 . .
C37 C38 H38B 109.5 . .
C37 C38 H38C 109.5 . .
H38A C38 H38B 109.5 . .
H38A C38 H38C 109.5 . .
H38B C38 H38C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C3 1.891(4) .
Br2 C9 1.888(4) .
O1 H1 0.8366 .
O1 C4 1.393(4) .
O2 H2 0.8294 .
O2 C2 1.364(4) .
O3 H3 0.8621 .
O3 C10 1.365(4) .
O4 H4 0.8277 .
O4 C8 1.365(4) .
O5 N1 1.325(4) .
O6 N2 1.324(4) .
O7 N3 1.304(5) .
O8 C37 1.216(6) .
O9 C34 1.215(7) .
N1 C19 1.355(5) .
N1 C21 1.357(5) .
N2 C26 1.354(5) .
N2 C27 1.361(5) .
N3 C29 1.357(5) .
N3 C33 1.359(5) .
C1 C2 1.403(5) .
C1 C6 1.386(5) .
C1 C13 1.528(5) .
C2 C3 1.402(5) .
C3 C4 1.393(5) .
C4 C5 1.397(5) .
C5 C6 1.390(5) .
C5 C16 1.526(5) 2_656
C6 H6 0.9300 .
C7 C8 1.400(5) .
C7 C12 1.400(5) .
C7 C16 1.520(5) .
C8 C9 1.400(5) .
C9 C10 1.388(5) .
C10 C11 1.407(5) .
C11 C12 1.385(5) .
C11 C13 1.516(5) .
C12 H12 0.9300 .
C13 H13 0.9800 .
C13 C14 1.539(5) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C14 C15 1.526(5) .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C16 C5 1.526(5) 2_656
C16 H16 0.9800 .
C16 C17 1.539(5) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C17 C18 1.537(5) .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 H19 0.9300 .
C19 C20 1.376(5) .
C20 H20 0.9300 .
C20 C23 1.401(6) .
C21 H21 0.9300 .
C21 C22 1.371(5) .
C22 H22 0.9300 .
C22 C23 1.401(5) .
C23 C24 1.476(5) .
C24 C25 1.398(5) .
C24 C28 1.393(5) .
C25 H25 0.9300 .
C25 C26 1.374(5) .
C26 H26 0.9300 .
C27 H27 0.9300 .
C27 C28 1.382(5) .
C28 H28 0.9300 .
C29 H29 0.9300 .
C29 C30 1.362(6) .
C30 H30 0.9300 .
C30 C31 1.401(6) .
C31 C31 1.470(8) 7_566
C31 C32 1.407(5) .
C32 H32 0.9300 .
C32 C33 1.378(6) .
C33 H33 0.9300 .
C34 C35 1.482(6) 2_656
C34 C35 1.482(6) .
C35 H35A 0.9600 .
C35 H35B 0.9600 .
C35 H35C 0.9600 .
C36 H36A 0.9600 .
C36 H36B 0.9600 .
C36 H36C 0.9600 .
C36 C37 1.501(6) .
C37 C38 1.490(7) .
C38 H38A 0.9600 .
C38 H38B 0.9600 .
C38 H38C 0.9600 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139203600
