#------------------------------------------------------------------------------
#$Date: 2017-06-16 03:46:17 +0200 (vie 16 de jun de 2017) $
#$Revision: 197869 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/84/7228485.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_7228485
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(C11 H9 N O), C3 H6 O'
_chemical_formula_sum            'C72 H69 Br4 N3 O12'
_chemical_formula_weight         1487.94
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 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                 114.269(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   19.2354(5)
_cell_length_b                   7.84234(14)
_cell_length_c                   22.8722(6)
_cell_measurement_reflns_used    7405
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      73.1800
_cell_measurement_theta_min      3.8720
_cell_volume                     3145.37(15)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(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 -115.00  -19.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  -37.0000   30.0000 96

#__ type_ start__ end____ width___ exp.time_
  2 omega  -72.00   29.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   77.0000 -150.0000 101

#__ type_ start__ end____ width___ exp.time_
  3 omega   77.00  173.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   61.0000  120.0000 96

#__ type_ start__ end____ width___ exp.time_
  4 omega   82.00  175.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   61.0000 -180.0000 93

#__ type_ start__ end____ width___ exp.time_
  5 omega   50.00   94.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -45.0000 -180.0000 44

#__ type_ start__ end____ width___ exp.time_
  6 omega   33.00  135.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -61.0000   30.0000 102

#__ type_ start__ end____ width___ exp.time_
  7 omega   39.00   90.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000  -60.0000 51

#__ type_ start__ end____ width___ exp.time_
  8 omega  -23.00   19.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6176   37.0000  150.0000 42

#__ type_ start__ end____ width___ exp.time_
  9 omega  -64.00   33.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.6176   77.0000  -30.0000 97

#__ type_ start__ end____ width___ exp.time_
 10 omega  118.00  178.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   45.0000   60.0000 60

#__ type_ start__ end____ width___ exp.time_
 11 omega   85.00  111.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   45.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   25.00   51.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   72.00  109.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000  120.0000 37

#__ type_ start__ end____ width___ exp.time_
 14 omega   24.00  109.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154  -94.0000    0.0000 85

#__ type_ start__ end____ width___ exp.time_
 15 omega  128.00  154.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154   45.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   34.00   76.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      105.6154 -125.0000  -90.0000 42
;
_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      0.0050365000
_diffrn_orient_matrix_UB_12      -0.0070742000
_diffrn_orient_matrix_UB_13      0.0689557000
_diffrn_orient_matrix_UB_21      -0.0386546000
_diffrn_orient_matrix_UB_22      0.1760782000
_diffrn_orient_matrix_UB_23      -0.0094667000
_diffrn_orient_matrix_UB_31      -0.0787209000
_diffrn_orient_matrix_UB_32      -0.0867675000
_diffrn_orient_matrix_UB_33      -0.0248337000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            17556
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.736
_diffrn_reflns_theta_max         66.736
_diffrn_reflns_theta_min         3.904
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.681
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89626
_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_density_diffrn    1.571
_exptl_crystal_F_000             1516
_exptl_crystal_size_max          0.0696
_exptl_crystal_size_mid          0.0559
_exptl_crystal_size_min          0.0277
_refine_diff_density_max         1.435
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     450
_refine_ls_number_reflns         5578
_refine_ls_number_restraints     41
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0451
_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)+(0.0696P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1147
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4769
_reflns_number_total             5578
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce00975e2.cif
_cod_data_source_block           acetone_BrC2_7
_cod_original_cell_volume        3145.36(14)
_cod_database_code               7228485
_chemical_oxdiff_formula         'C20 H20 N1 O9'
_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 99.87
_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. Restrained distances
 H4-O4
 0.85 with sigma of 0.02
 O7-N2
 1.34 with sigma of 0.02
 O3-H3
 0.85 with sigma of 0.02
 O2-H2
 0.85 with sigma of 0.02
 H5-O5
 0.85 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C32) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C30)
\\sim Ueq, Uanis(N2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms
of 0.02
Uanis(C37) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: O7(0.5) C30(0.5) H30(0.5) C31(0.5) H31(0.5) C32(0.5) C33(0.5)
 H33(0.5) C34(0.5) H34(0.5) N2(0.5) C38(0.5) H38(0.5) C37(0.5) H37(0.5)
 C36(0.5) H36(0.5) C35(0.5) C40(0.5) H40(0.5) C39(0.5) H39(0.5)
 Fixed U11: O7(0.104627) C34(0.078601) C37(0.086901)
 Fixed U22: C37(0.0962)
 Fixed U33: C39(0.09185)
5.a Riding coordinates:
 O2(H2), O3(H3), O5(H5)
5.b Ternary CH refined with riding coordinates:
 C7(H7), C16(H16)
5.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C17(H17A,H17B)
5.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C10(H10), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26),
 C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C33(H33), C34(H34), C38(H38),
  C37(H37), C36(H36), C40(H40), C39(H39)
5.e Fitted hexagon refined as free rotating group:
 C30(C31,C32,C33,C34,N2), C38(C37,C36,C35,C40,C39)
5.f Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C18(H18A,H18B,H18C), C41(H41A,H41B,H41C)
;
_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+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, 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 0.26906(2) 0.36485(4) 0.46788(2) 0.02347(12) Uani 1 1 d . . . . .
Br2 Br -0.08747(2) 0.46720(4) 0.14589(2) 0.02283(12) Uani 1 1 d . . . . .
O2 O 0.00061(13) 0.6241(3) 0.28023(11) 0.0229(5) Uani 1 1 d D . . . .
H2 H -0.0426 0.6563 0.2779 0.12(3) Uiso 1 1 d DR . . A 1
O3 O 0.13106(13) 0.5584(3) 0.38561(12) 0.0254(5) Uani 1 1 d D . . . .
H3 H 0.0918 0.5859 0.3524 0.051(15) Uiso 1 1 d DR . . . .
O4 O 0.39860(13) 0.5714(3) 0.46689(11) 0.0221(5) Uani 1 1 d D . . . .
H4 H 0.435(2) 0.604(6) 0.460(3) 0.038(13) Uiso 1 1 d D . . . .
O5 O -0.01971(13) 0.6543(3) 0.06290(11) 0.0234(5) Uani 1 1 d D . . . .
H5 H -0.0487 0.5958 0.0318 0.035 Uiso 1 1 d DR . . . .
C1 C 0.10223(17) 0.8796(4) 0.20742(16) 0.0185(6) Uani 1 1 d . . . . .
H1 H 0.1416 0.9590 0.2199 0.022 Uiso 1 1 calc R . . . .
C2 C 0.07058(17) 0.8255(4) 0.14407(15) 0.0180(6) Uani 1 1 d . . . . .
C3 C 0.01187(18) 0.7048(4) 0.12596(15) 0.0199(6) Uani 1 1 d . . . . .
C4 C -0.01140(17) 0.6388(4) 0.17140(16) 0.0195(6) Uani 1 1 d . . . . .
C5 C 0.02066(18) 0.6958(4) 0.23470(16) 0.0204(6) Uani 1 1 d . . . . .
C6 C 0.07766(17) 0.8204(4) 0.25305(15) 0.0169(6) Uani 1 1 d . . . . .
C7 C 0.11230(17) 0.8873(4) 0.32184(15) 0.0187(6) Uani 1 1 d . . . . .
H7 H 0.0787 0.8502 0.3420 0.022 Uiso 1 1 calc R . . . .
C8 C 0.11465(19) 1.0827(4) 0.32464(16) 0.0217(6) Uani 1 1 d . . . . .
H8A H 0.1406 1.1189 0.3689 0.026 Uiso 1 1 calc R . . . .
H8B H 0.1435 1.1247 0.3014 0.026 Uiso 1 1 calc R . . . .
C9 C 0.0345(2) 1.1602(5) 0.2957(2) 0.0330(8) Uani 1 1 d . . . . .
H9A H 0.0099 1.1305 0.2511 0.050 Uiso 1 1 calc GR . . . .
H9B H 0.0381 1.2820 0.3000 0.050 Uiso 1 1 calc GR . . . .
H9C H 0.0054 1.1167 0.3178 0.050 Uiso 1 1 calc GR . . . .
C10 C 0.25745(19) 0.8795(4) 0.36448(15) 0.0189(6) Uani 1 1 d . . . . .
H10 H 0.2550 0.9825 0.3436 0.023 Uiso 1 1 calc R . . . .
C11 C 0.18955(18) 0.8046(4) 0.35908(14) 0.0186(6) Uani 1 1 d . . . . .
C12 C 0.19340(18) 0.6454(4) 0.38900(15) 0.0183(6) Uani 1 1 d . . . . .
C13 C 0.26466(18) 0.5736(4) 0.42468(15) 0.0199(6) Uani 1 1 d . . . . .
C14 C 0.33154(18) 0.6517(4) 0.43029(15) 0.0191(6) Uani 1 1 d . . . . .
C15 C 0.32947(18) 0.8078(4) 0.39986(14) 0.0173(6) Uani 1 1 d . . . . .
C16 C 0.40283(18) 0.8960(4) 0.40551(15) 0.0187(6) Uani 1 1 d . . . . .
H16 H 0.4422 0.8661 0.4478 0.022 Uiso 1 1 calc R . . . .
C17 C 0.39708(19) 1.0914(4) 0.40321(16) 0.0219(6) Uani 1 1 d . . . . .
H17A H 0.3558 1.1254 0.3632 0.026 Uiso 1 1 calc R . . . .
H17B H 0.3848 1.1306 0.4381 0.026 Uiso 1 1 calc R . . . .
C18 C 0.4705(2) 1.1776(4) 0.40849(17) 0.0260(7) Uani 1 1 d . . . . .
H18A H 0.4777 1.1576 0.3699 0.039 Uiso 1 1 calc GR . . . .
H18B H 0.5129 1.1313 0.4445 0.039 Uiso 1 1 calc GR . . . .
H18C H 0.4671 1.2980 0.4144 0.039 Uiso 1 1 calc GR . . . .
O6 O -0.12666(19) 0.7058(4) 0.27508(17) 0.0475(8) Uani 1 1 d . . . . .
N1 N -0.15061(18) 0.5822(5) 0.30340(17) 0.0352(7) Uani 1 1 d . . . . .
C19 C -0.1376(2) 0.4172(6) 0.2967(2) 0.0370(9) Uani 1 1 d . . . . .
H19 H -0.1086 0.3866 0.2743 0.044 Uiso 1 1 calc R . . . .
C20 C -0.1667(2) 0.2928(6) 0.3225(2) 0.0370(9) Uani 1 1 d . . . . .
H20 H -0.1574 0.1787 0.3172 0.044 Uiso 1 1 calc R . . . .
C21 C -0.2101(2) 0.3353(5) 0.35665(19) 0.0312(8) Uani 1 1 d . . . . .
C22 C -0.2187(2) 0.5082(5) 0.36521(19) 0.0331(8) Uani 1 1 d . . . . .
H22 H -0.2445 0.5423 0.3898 0.040 Uiso 1 1 calc R . . . .
C23 C -0.1899(2) 0.6296(5) 0.3381(2) 0.0373(9) Uani 1 1 d . . . . .
H23 H -0.1973 0.7446 0.3436 0.045 Uiso 1 1 calc R . . . .
C24 C -0.2488(2) 0.2037(5) 0.37886(18) 0.0279(7) Uani 1 1 d . . . . .
C25 C -0.2531(2) 0.2180(5) 0.43835(18) 0.0313(8) Uani 1 1 d . . . . .
H25 H -0.2292 0.3084 0.4655 0.038 Uiso 1 1 calc R . . . .
C26 C -0.2927(2) 0.0979(5) 0.45664(19) 0.0337(8) Uani 1 1 d . . . . .
H26 H -0.2943 0.1068 0.4966 0.040 Uiso 1 1 calc R . . . .
C27 C -0.3301(2) -0.0356(5) 0.41648(19) 0.0317(8) Uani 1 1 d . . . . .
H27 H -0.3578 -0.1138 0.4289 0.038 Uiso 1 1 calc R . . . .
C28 C -0.3261(2) -0.0520(5) 0.3577(2) 0.0370(9) Uani 1 1 d . . . . .
H28 H -0.3506 -0.1421 0.3306 0.044 Uiso 1 1 calc R . . . .
C29 C -0.2853(3) 0.0664(5) 0.33916(19) 0.0360(8) Uani 1 1 d . . . . .
H29 H -0.2822 0.0541 0.2998 0.043 Uiso 1 1 calc R . . . .
O7 O 0.0939(9) -0.0091(18) 0.5781(7) 0.095(4) Uani 0.5 1 d D . . B -1
C30 C 0.0880(5) 0.2128(11) 0.5075(4) 0.063(4) Uani 0.5 1 d . U . B -1
H30 H 0.1229 0.1633 0.4940 0.075 Uiso 0.5 1 calc R . . B -1
C31 C 0.0583(6) 0.3733(11) 0.4850(4) 0.070(4) Uani 0.5 1 d G U . B -1
H31 H 0.0732 0.4311 0.4566 0.083 Uiso 0.5 1 calc R . . B -1
C32 C 0.0061(6) 0.4473(9) 0.5051(5) 0.064(4) Uani 0.5 1 d G U . B -1
C33 C -0.0163(6) 0.3610(12) 0.5476(5) 0.076(4) Uani 0.5 1 d G . . B -1
H33 H -0.0512 0.4105 0.5610 0.091 Uiso 0.5 1 calc R . . B -1
C34 C 0.0134(6) 0.2005(12) 0.5700(5) 0.088(4) Uani 0.5 1 d G U . B -1
H34 H -0.0016 0.1428 0.5984 0.106 Uiso 0.5 1 calc R . . B -1
N2 N 0.0656(5) 0.1265(9) 0.5499(4) 0.060(3) Uani 0.5 1 d DG U . B -1
C38 C -0.0863(6) 0.9603(11) 0.4428(5) 0.068(5) Uani 0.5 1 d . . . B -1
H38 H -0.1062 1.0678 0.4281 0.081 Uiso 0.5 1 calc R . . B -1
C37 C -0.0359(7) 0.8850(12) 0.4210(5) 0.090(3) Uani 0.5 1 d G U . B -1
H37 H -0.0222 0.9421 0.3917 0.108 Uiso 0.5 1 calc R . . B -1
C36 C -0.0062(6) 0.7243(12) 0.4430(5) 0.063(4) Uani 0.5 1 d G . . B -1
H36 H 0.0275 0.6739 0.4284 0.076 Uiso 0.5 1 calc R . . B -1
C35 C -0.0267(6) 0.6389(11) 0.4867(5) 0.074(4) Uani 0.5 1 d G . . B -1
C40 C -0.0771(6) 0.7142(14) 0.5085(5) 0.077(5) Uani 0.5 1 d G . . B -1
H40 H -0.0908 0.6571 0.5378 0.092 Uiso 0.5 1 calc R . . B -1
C39 C -0.1069(6) 0.8749(15) 0.4865(5) 0.090(5) Uani 0.5 1 d G . . B -1
H39 H -0.1405 0.9253 0.5011 0.108 Uiso 0.5 1 calc R . . B -1
O1 O 0.2500 0.1934(4) 0.2500 0.0263(7) Uani 1 2 d S T P . .
C41 C 0.1778(3) 0.4476(6) 0.2304(3) 0.0553(13) Uani 1 1 d . . . . .
H41A H 0.1356 0.3709 0.2201 0.083 Uiso 1 1 calc GR . . . .
H41B H 0.1708 0.5155 0.1934 0.083 Uiso 1 1 calc GR . . . .
H41C H 0.1808 0.5208 0.2649 0.083 Uiso 1 1 calc GR . . . .
C42 C 0.2500 0.3476(6) 0.2500 0.0286(11) Uani 1 2 d S T P . .
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_
_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
-12 1 2 0.0118 -12.0066 0.9966 2.0089 0.0710 0.6206 0.8088
12 0 -2 0.0228 12.0035 0.0032 -2.0094 -0.0781 -0.4444 -0.8953
-1 5 2 0.0235 -1.0138 4.9997 1.9975 0.0973 0.9006 -0.4036
0 -5 -2 0.0374 0.0134 -5.0000 -1.9966 -0.1022 -0.8620 0.4824
3 1 12 0.0059 3.0108 1.0059 11.9922 0.8350 -0.0528 -0.6221
-6 -1 -8 0.0141 -6.0080 -1.0052 -7.9912 -0.5742 0.1309 0.7586
-10 -2 10 0.0244 -9.9881 -1.9988 10.0056 0.6538 -0.0606 0.7112
9 2 -12 0.0305 8.9856 1.9976 -12.0039 -0.7966 0.1180 -0.5826
1 -5 5 0.0283 1.0211 -4.9967 4.9998 0.3853 -0.9666 0.2290
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
C5 O2 H2 113.8 . .
C12 O3 H3 111.4 . .
C14 O4 H4 114(4) . .
C3 O5 H5 154.5 . .
C2 C1 H1 118.6 . .
C2 C1 C6 122.9(3) . .
C6 C1 H1 118.6 . .
C1 C2 C3 118.0(3) . .
C1 C2 C16 121.9(3) . 2
C3 C2 C16 120.1(3) . 2
O5 C3 C2 117.4(3) . .
O5 C3 C4 122.6(3) . .
C4 C3 C2 120.0(3) . .
C3 C4 Br2 118.7(2) . .
C3 C4 C5 121.1(3) . .
C5 C4 Br2 120.2(2) . .
O2 C5 C4 121.0(3) . .
O2 C5 C6 119.3(3) . .
C4 C5 C6 119.6(3) . .
C1 C6 C5 118.3(3) . .
C1 C6 C7 121.3(3) . .
C5 C6 C7 120.4(3) . .
C6 C7 H7 106.9 . .
C6 C7 C8 112.3(3) . .
C8 C7 H7 106.9 . .
C11 C7 C6 110.0(2) . .
C11 C7 H7 106.9 . .
C11 C7 C8 113.4(3) . .
C7 C8 H8A 109.3 . .
C7 C8 H8B 109.3 . .
H8A C8 H8B 107.9 . .
C9 C8 C7 111.8(3) . .
C9 C8 H8A 109.3 . .
C9 C8 H8B 109.3 . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9B 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C11 C10 H10 118.3 . .
C11 C10 C15 123.4(3) . .
C15 C10 H10 118.3 . .
C10 C11 C7 122.4(3) . .
C10 C11 C12 118.1(3) . .
C12 C11 C7 119.6(3) . .
O3 C12 C11 123.3(3) . .
O3 C12 C13 117.7(3) . .
C13 C12 C11 119.0(3) . .
C12 C13 Br1 118.5(2) . .
C14 C13 Br1 119.6(2) . .
C14 C13 C12 121.9(3) . .
O4 C14 C13 117.4(3) . .
O4 C14 C15 122.2(3) . .
C13 C14 C15 120.4(3) . .
C10 C15 C16 121.7(3) . .
C14 C15 C10 117.2(3) . .
C14 C15 C16 121.1(3) . .
C2 C16 C15 110.7(2) 2 .
C2 C16 H16 106.7 2 .
C2 C16 C17 112.1(3) 2 .
C15 C16 H16 106.7 . .
C15 C16 C17 113.4(3) . .
C17 C16 H16 106.7 . .
C16 C17 H17A 109.0 . .
C16 C17 H17B 109.0 . .
H17A C17 H17B 107.8 . .
C18 C17 C16 112.8(3) . .
C18 C17 H17A 109.0 . .
C18 C17 H17B 109.0 . .
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 . .
O6 N1 C23 117.9(4) . .
C19 N1 O6 121.5(3) . .
C19 N1 C23 120.6(4) . .
N1 C19 H19 119.7 . .
N1 C19 C20 120.6(4) . .
C20 C19 H19 119.7 . .
C19 C20 H20 119.5 . .
C19 C20 C21 120.9(4) . .
C21 C20 H20 119.5 . .
C20 C21 C24 121.7(4) . .
C22 C21 C20 116.3(4) . .
C22 C21 C24 121.8(3) . .
C21 C22 H22 119.3 . .
C23 C22 C21 121.4(4) . .
C23 C22 H22 119.3 . .
N1 C23 C22 120.1(4) . .
N1 C23 H23 120.0 . .
C22 C23 H23 120.0 . .
C25 C24 C21 121.1(3) . .
C29 C24 C21 120.3(3) . .
C29 C24 C25 118.6(3) . .
C24 C25 H25 120.0 . .
C26 C25 C24 120.0(4) . .
C26 C25 H25 120.0 . .
C25 C26 H26 119.4 . .
C25 C26 C27 121.1(4) . .
C27 C26 H26 119.4 . .
C26 C27 H27 120.2 . .
C26 C27 C28 119.6(4) . .
C28 C27 H27 120.2 . .
C27 C28 H28 120.1 . .
C27 C28 C29 119.9(4) . .
C29 C28 H28 120.1 . .
C24 C29 H29 119.6 . .
C28 C29 C24 120.9(4) . .
C28 C29 H29 119.6 . .
C31 C30 H30 120.0 . .
C31 C30 N2 120.0 . .
N2 C30 H30 120.0 . .
C30 C31 H31 120.0 . .
C30 C31 C32 120.0 . .
C32 C31 H31 120.0 . .
C31 C32 C35 124.1(7) . .
C33 C32 C31 120.0 . .
C33 C32 C35 115.7(7) . .
C32 C33 H33 120.0 . .
C32 C33 C34 120.0 . .
C34 C33 H33 120.0 . .
C33 C34 H34 120.0 . .
N2 C34 C33 120.0 . .
N2 C34 H34 120.0 . .
O7 N2 C30 125.6(8) . .
O7 N2 C34 114.0(8) . .
C34 N2 C30 120.0 . .
C37 C38 H38 120.0 . .
C37 C38 C39 120.0 . .
C39 C38 H38 120.0 . .
C38 C37 H37 120.0 . .
C36 C37 C38 120.0 . .
C36 C37 H37 120.0 . .
C37 C36 H36 120.0 . .
C35 C36 C37 120.0 . .
C35 C36 H36 120.0 . .
C36 C35 C32 116.0(7) . .
C36 C35 C40 120.0 . .
C40 C35 C32 123.8(7) . .
C35 C40 H40 120.0 . .
C35 C40 C39 120.0 . .
C39 C40 H40 120.0 . .
C38 C39 H39 120.0 . .
C40 C39 C38 120.0 . .
C40 C39 H39 120.0 . .
H41A C41 H41B 109.5 . .
H41A C41 H41C 109.5 . .
H41B C41 H41C 109.5 . .
C42 C41 H41A 109.5 . .
C42 C41 H41B 109.5 . .
C42 C41 H41C 109.5 . .
O1 C42 C41 121.7(3) . .
O1 C42 C41 121.7(3) . 2
C41 C42 C41 116.7(6) 2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C13 1.896(3) .
Br2 C4 1.895(3) .
O2 H2 0.8484 .
O2 C5 1.371(4) .
O3 H3 0.8501 .
O3 C12 1.354(4) .
O4 H4 0.82(2) .
O4 C14 1.369(4) .
O5 H5 0.8384 .
O5 C3 1.373(4) .
C1 H1 0.9300 .
C1 C2 1.387(5) .
C1 C6 1.391(5) .
C2 C3 1.400(5) .
C2 C16 1.526(4) 2
C3 C4 1.389(5) .
C4 C5 1.394(5) .
C5 C6 1.398(5) .
C6 C7 1.527(4) .
C7 H7 0.9800 .
C7 C8 1.534(4) .
C7 C11 1.521(4) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C8 C9 1.531(5) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C10 H10 0.9300 .
C10 C11 1.391(5) .
C10 C15 1.403(5) .
C11 C12 1.411(4) .
C12 C13 1.394(5) .
C13 C14 1.382(5) .
C14 C15 1.401(4) .
C15 C16 1.529(4) .
C16 C2 1.526(4) 2
C16 H16 0.9800 .
C16 C17 1.536(4) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C17 C18 1.525(5) .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
O6 N1 1.347(5) .
N1 C19 1.339(6) .
N1 C23 1.353(6) .
C19 H19 0.9300 .
C19 C20 1.373(6) .
C20 H20 0.9300 .
C20 C21 1.399(6) .
C21 C22 1.389(6) .
C21 C24 1.479(5) .
C22 H22 0.9300 .
C22 C23 1.372(6) .
C23 H23 0.9300 .
C24 C25 1.401(5) .
C24 C29 1.398(6) .
C25 H25 0.9300 .
C25 C26 1.380(6) .
C26 H26 0.9300 .
C26 C27 1.383(6) .
C27 H27 0.9300 .
C27 C28 1.385(6) .
C28 H28 0.9300 .
C28 C29 1.389(6) .
C29 H29 0.9300 .
O7 N2 1.247(11) .
C30 H30 0.9300 .
C30 C31 1.3900 .
C30 N2 1.3900 .
C31 H31 0.9300 .
C31 C32 1.3900 .
C32 C33 1.3900 .
C32 C35 1.617(13) .
C33 H33 0.9300 .
C33 C34 1.3900 .
C34 H34 0.9300 .
C34 N2 1.3900 .
C38 H38 0.9300 .
C38 C37 1.3900 .
C38 C39 1.3900 .
C37 H37 0.9300 .
C37 C36 1.3900 .
C36 H36 0.9300 .
C36 C35 1.3900 .
C35 C40 1.3900 .
C40 H40 0.9300 .
C40 C39 1.3900 .
C39 H39 0.9300 .
O1 C42 1.209(6) .
C41 H41A 0.9600 .
C41 H41B 0.9600 .
C41 H41C 0.9600 .
C41 C42 1.494(6) .
C42 C41 1.494(6) 2
