#------------------------------------------------------------------------------
#$Date: 2019-11-04 10:16:30 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222455 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/38/4033882.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_4033882
loop_
_publ_author_name
'Galenko, Ekaterina E.'
'Linnik, Stanislav A.'
'Khoroshilova, Olesya V.'
'Novikov, Mikhail S.'
'Khlebnikov, Alexander F.'
_publ_section_title
;
 Isoxazole Strategy for the Synthesis of α-Aminopyrrole Derivatives.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11275
_journal_page_last               11285
_journal_paper_doi               10.1021/acs.joc.9b01634
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C24 H18 Br N O2, C2 H3 N'
_chemical_formula_sum            'C26 H21 Br N2 O2'
_chemical_formula_weight         473.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                93.9200(10)
_cell_angle_beta                 95.1410(10)
_cell_angle_gamma                106.4740(10)
_cell_formula_units_Z            4
_cell_length_a                   10.11970(10)
_cell_length_b                   10.50710(10)
_cell_length_c                   21.9497(2)
_cell_measurement_reflns_used    15645
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.5530
_cell_measurement_theta_min      2.0200
_cell_volume                     2218.30(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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_temperature      100(2)
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -22.00  41.00   0.50    0.20    --   38.82 -90.00-173.00  126
  2  ω     81.00 108.00   0.50    0.42    --  107.00  90.00 -59.00   54
  3  ω    117.00 143.00   0.50    0.42    --  107.00  90.00 -59.00   52
  4  ω     98.00 130.00   0.50    0.42    --  107.00 -90.00-173.00   64
  5  ω    -21.00  17.00   0.50    0.20    --  -38.82 104.00   0.00   76
  6  ω    -63.00 -20.00   0.50    0.20    --  -38.82 104.00-180.00   86
  7  ω     -8.00  27.00   0.50    0.20    --  -38.82  43.00 120.00   70
  8  ω    -51.00  30.00   0.50    0.20    --  -38.82  32.00 -90.00  162
  9  ω    -59.00 -16.00   0.50    0.20    --  -38.82  77.00 -30.00   86
 10  ω    -69.00 -32.00   0.50    0.20    --  -38.82  90.00 -59.00   74
 11  ω    -66.00 -28.00   0.50    0.20    --  -38.82 104.00   0.00   76
 12  ω    -97.00 -52.00   0.50    0.20    --  -38.82 138.00  60.00   90
 13  ω    -10.00  15.00   0.50    0.20    --  -38.82 104.00-180.00   50
 14  ω    -53.00 -27.00   0.50    0.20    --  -38.82  43.00 120.00   52
 15  ω     -1.00  28.00   0.50    0.20    --  -38.82  77.00 -30.00   58
 16  ω     23.00  62.00   0.50    0.20    --   38.82  43.00   0.00   78
 17  ω     19.00  60.00   0.50    0.20    --   38.82  65.00 120.00   82
 18  ω     20.00  54.00   0.50    0.20    --   38.82 -65.00  90.00   68
 19  ω     25.00 103.00   0.50    0.20    --   38.82  65.00 -90.00  156
 20  ω     20.00 102.00   0.50    0.20    --   38.82  54.00  60.00  164
 21  ω     26.00  51.00   0.50    0.20    --   38.82  54.00 -60.00   50
 22  ω     36.00  61.00   0.50    0.20    --   38.82-104.00-180.00   50
 23  ω    -16.00  19.00   0.50    0.20    --   38.82-104.00-180.00   70
 24  ω     58.00 103.00   0.50    0.20    --   38.82  54.00 -60.00   90
 25  ω    -28.00  19.00   0.50    0.20    --   38.82 -77.00   0.00   94
 26  ω     40.00  66.00   0.50    0.20    --   38.82 -77.00   0.00   52
 27  ω     66.00 104.00   0.50    0.20    --   38.82  43.00   0.00   76
 28  ω     12.00  39.00   0.50    0.20    --   38.82 -32.00-180.00   54
 29  ω     17.00  42.00   0.50    0.20    --   38.82 -32.00 -60.00   50
 30  ω    -30.00  11.00   0.50    0.20    --   38.82 -32.00-180.00   82
 31  ω     71.00  96.00   0.50    0.20    --   38.82  32.00 -60.00   50
 32  ω     65.00  91.00   0.50    0.20    --   38.82  65.00 120.00   52
 33  ω     72.00  97.00   0.50    0.20    --   38.82-138.00  60.00   50
 34  ω    -26.00  15.00   0.50    0.20    --   38.82 -65.00  90.00   82
 35  ω    -23.00   2.00   0.50    0.20    --   38.82 -32.00 -60.00   50
 36  ω     98.00 137.00   0.50    0.42    --  107.00 111.00 -30.00   78
 37  ω     44.00  77.00   0.50    0.42    --  107.00-133.00 120.00   66
 38  ω    119.00 157.00   0.50    0.42    --  107.00  30.00 -30.00   76
 39  ω     43.00 123.00   0.50    0.42    --  107.00-133.00-120.00  160
 40  ω    125.00 151.00   0.50    0.42    --  107.00  93.00 -90.00   52
 41  ω     93.00 156.00   0.50    0.42    --  107.00  30.00-150.00  126
 42  ω     93.00 153.00   0.50    0.42    --  107.00  22.00 -90.00  120
 43  ω     97.00 123.00   0.50    0.42    --  107.00  93.00 -90.00   52
 44  ω    100.00 152.00   0.50    0.42    --  107.00  22.00  60.00  104
 45  ω     38.00 118.00   0.50    0.42    --  107.00 -30.00   0.00  160
 46  ω     87.00 123.00   0.50    0.42    --  107.00-133.00-180.00   72
 47  ω     39.00  77.00   0.50    0.42    --  107.00 -30.00 150.00   76
 48  ω     81.00 157.00   0.50    0.42    --  107.00  93.00 120.00  152
 49  ω     67.00  93.00   0.50    0.42    --  107.00 -93.00 120.00   52
 50  ω     42.00 129.00   0.50    0.42    --  107.00 -61.00-180.00  174
 51  ω     33.00  60.00   0.50    0.42    --  107.00 -93.00 120.00   54
 52  ω     53.00  91.00   0.50    0.42    --  107.00 -37.00-180.00   76
 53  ω     43.00 109.00   0.50    0.42    --  107.00-133.00  30.00  132
 54  ω     49.00 123.00   0.50    0.42    --  107.00-133.00  90.00  148
 55  ω     41.00  86.00   0.50    0.42    --  107.00 -69.00  60.00   90
 56  ω     85.00 153.00   0.50    0.42    --  107.00  69.00 150.00  136
 57  ω     59.00  85.00   0.50    0.42    --  107.00-133.00-180.00   52
 58  ω     47.00 123.00   0.50    0.42    --  107.00-133.00   0.00  152
 59  ω     34.00  68.00   0.50    0.42    --  107.00 -93.00-180.00   68
 60  ω     78.00 106.00   0.50    0.42    --  107.00 -93.00-180.00   56
 61  ω     77.00 120.00   0.50    0.42    --  107.00 -30.00 -90.00   86
 62  ω     98.00 147.00   0.50    0.42    --  107.00  15.00 120.00   98
 63  ω     94.00 156.00   0.50    0.42    --  107.00  45.00 -60.00  124
 64  ω     43.00 124.00   0.50    0.42    --  107.00 -77.00 120.00  162
 65  ω     82.00 108.00   0.50    0.42    --  107.00-133.00 120.00   52
 66  ω     60.00  99.00   0.50    0.42    --  107.00 -93.00  60.00   78
 67  ω     47.00  85.00   0.50    0.42    --  107.00 -93.00   0.00   76
 68  ω     96.00 121.00   0.50    0.42    --  107.00 -30.00 150.00   50
 69  ω     43.00  98.00   0.50    0.42    --  107.00 -53.00 -30.00  110
 70  ω    113.00 155.00   0.50    0.42    --  107.00  90.00 -59.00   84
 71  ω    -46.00 -15.00   0.50    0.20    --    0.00 124.00 -50.15   62
 72  ω    -19.00   6.00   0.50    0.20    --   24.00 113.00 172.24   50
 73  ω    -10.00  15.00   0.50    0.20    --   28.00 104.00  75.69   50
 74  ω     -8.00  17.00   0.50    0.20    --   28.00 100.00 -92.32   50
 75  ω     -1.00  24.00   0.50    0.20    --   32.00  93.00  12.94   50
 76  ω      6.00  31.00   0.50    0.20    --   36.00  87.00-163.59   50
 77  ω      5.00  30.00   0.50    0.20    --   36.00  88.00 -79.91   50
 78  ω      6.00  31.00   0.50    0.20    --   36.00  87.00  28.74   50
 79  ω      5.00  30.00   0.50    0.20    --   36.00  88.00  96.13   50
 80  ω      5.00  30.00   0.50    0.20    --   36.00  89.00 141.51   50
 81  ω    -26.00  23.00   0.50    0.20    --  -38.82  54.00 -60.00   98
 82  ω    -53.00 -27.00   0.50    0.20    --  -38.82  54.00 -60.00   52
 83  ω    -63.00 -37.00   0.50    0.20    --  -38.82 138.00  30.00   52
 84  ω     12.00  37.00   0.50    0.20    --   40.00  82.00 -31.94   50
 85  ω     11.00  36.00   0.50    0.20    --   40.00  84.00-110.96   50
 86  ω     16.00  41.00   0.50    0.20    --   44.00  82.00  40.95   50
 87  ω     16.00  41.00   0.50    0.20    --   44.00  81.00-178.90   50
 88  ω     16.00  41.00   0.50    0.20    --   44.00  82.00  82.88   50
 89  ω     16.00  41.00   0.50    0.20    --   44.00  82.00 122.10   50
 90  ω     16.00  41.00   0.50    0.20    --   44.00  81.00  -1.61   50
 91  ω     16.00  41.00   0.50    0.20    --   44.00  81.00-133.60   50
 92  ω     33.00  59.00   0.50    0.20    --   52.00  77.00-123.68   52
 93  ω     25.00  51.00   0.50    0.20    --   52.00  77.00-165.54   52
 94  ω     28.00  54.00   0.50    0.20    --   52.00  74.00 -66.33   52
 95  ω     26.00  52.00   0.50    0.20    --   52.00  77.00  41.82   52
 96  ω     26.00  52.00   0.50    0.20    --   52.00  75.00 -31.28   52
 97  ω     33.00  59.00   0.50    0.20    --   56.00  74.00 -90.80   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            26883
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.029
_diffrn_reflns_theta_min         2.031
_exptl_absorpt_coefficient_mu    2.724
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.417
_exptl_crystal_description       prism
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.595
_refine_diff_density_min         -0.970
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.00026(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     583
_refine_ls_number_reflns         8919
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0399
_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)+(0.0597P)²+0.3596P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1148
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7972
_reflns_number_total             8919
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b01634_si_005.cif
_cod_data_source_block           10681-12188_cat8-151
_cod_database_code               4033882
_shelx_shelxl_version_number     2014/7
_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   0.467
_shelx_estimated_absorpt_t_min   0.401
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Others
 Sof(H3SD)=Sof(H3SE)=Sof(H3SF)=Sof(N1SS)=Sof(C2SS)=1-FVAR(1)
 Sof(N1S)=Sof(H3SA)=Sof(H3SB)=Sof(H3SC)=Sof(C2S)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N1B(H1B), C17B(H17B), C15(H15), C14(H14), C10B(H10B), C18B(H18B),
 C18(H18), C17(H17), C14B(H14B), C24(H24), C20(H20), C15B(H15B), C22(H22),
 C23(H23), C9B(H9B), C6(H6), C6B(H6B), C10(H10), C24B(H24B), C8(H8), C9(H9),
 C20B(H20B), C23B(H23B), C7(H7), C21(H21), C8B(H8B), C21B(H21B), C7B(H7B),
 C22B(H22B)
3.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C12B(H12D,H12E,H12F), C3SB(H3SG,H3SH,H3SI), C3S(H3SA,
 H3SB,H3SC), C3S(H3SD,H3SE,H3SF)
;
_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
;
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.35419(2) 0.87159(2) 0.54061(2) 0.02596(9) Uani 1 1 d . . . .
Br1B Br -0.64437(2) -0.06270(2) 0.05250(2) 0.02804(9) Uani 1 1 d . . . .
O2 O -0.07106(15) 0.28140(15) 0.28506(7) 0.0201(3) Uani 1 1 d . . . .
O1B O -0.49676(17) 0.24319(15) 0.31669(7) 0.0247(3) Uani 1 1 d . . . .
O2B O -0.46996(16) 0.43539(15) 0.37516(7) 0.0217(3) Uani 1 1 d . . . .
O1 O 0.09689(17) 0.31106(19) 0.36257(7) 0.0316(4) Uani 1 1 d . . . .
N1 N 0.26353(18) 0.47769(17) 0.19117(8) 0.0169(3) Uani 1 1 d . . . .
H1 H 0.2898 0.4791 0.1540 0.020 Uiso 1 1 calc R . . .
N1B N -0.15425(18) 0.60766(18) 0.27506(8) 0.0176(4) Uani 1 1 d . . . .
H1B H -0.0850 0.6817 0.2791 0.021 Uiso 1 1 calc R . . .
N1SB N 0.0578(2) 0.8792(2) 0.29166(10) 0.0328(5) Uani 1 1 d . . . .
C16B C -0.5369(2) 0.0874(2) 0.10703(10) 0.0219(4) Uani 1 1 d . . . .
C17B C -0.3936(2) 0.1213(2) 0.11336(10) 0.0197(4) Uani 1 1 d . . . .
H17B H -0.3471 0.0723 0.0896 0.024 Uiso 1 1 calc R . . .
C1 C 0.1599(2) 0.3775(2) 0.20956(10) 0.0163(4) Uani 1 1 d . . . .
C15 C 0.4370(2) 0.7541(2) 0.43494(10) 0.0203(4) Uani 1 1 d . . . .
H15 H 0.5290 0.7971 0.4534 0.024 Uiso 1 1 calc R . . .
C5 C 0.0881(2) 0.2574(2) 0.16820(10) 0.0177(4) Uani 1 1 d . . . .
C4B C -0.1959(2) 0.5215(2) 0.22213(10) 0.0170(4) Uani 1 1 d . . . .
C3B C -0.3064(2) 0.4173(2) 0.23389(10) 0.0164(4) Uani 1 1 d . . . .
C2B C -0.3313(2) 0.4440(2) 0.29609(10) 0.0175(4) Uani 1 1 d . . . .
C14 C 0.4134(2) 0.6793(2) 0.37818(10) 0.0183(4) Uani 1 1 d . . . .
H14 H 0.4902 0.6715 0.3579 0.022 Uiso 1 1 calc R . . .
C10B C -0.1900(2) 0.5721(2) 0.43461(10) 0.0213(4) Uani 1 1 d . . . .
H10B H -0.2039 0.4785 0.4307 0.026 Uiso 1 1 calc R . . .
C2 C 0.1514(2) 0.4121(2) 0.27065(10) 0.0177(4) Uani 1 1 d . . . .
C11 C 0.0600(2) 0.3307(2) 0.31126(10) 0.0188(4) Uani 1 1 d . . . .
C16 C 0.3243(2) 0.7648(2) 0.46414(10) 0.0200(4) Uani 1 1 d . . . .
C13 C 0.2789(2) 0.6156(2) 0.35044(9) 0.0175(4) Uani 1 1 d . . . .
C18B C -0.3194(2) 0.2281(2) 0.15497(10) 0.0196(4) Uani 1 1 d . . . .
H18B H -0.2209 0.2516 0.1600 0.023 Uiso 1 1 calc R . . .
C3 C 0.2535(2) 0.5375(2) 0.28953(10) 0.0178(4) Uani 1 1 d . . . .
C18 C 0.1676(2) 0.6277(2) 0.38165(10) 0.0209(4) Uani 1 1 d . . . .
H18 H 0.0755 0.5842 0.3636 0.025 Uiso 1 1 calc R . . .
C13B C -0.3859(2) 0.3020(2) 0.18966(9) 0.0177(4) Uani 1 1 d . . . .
C1B C -0.2343(2) 0.5633(2) 0.32040(10) 0.0183(4) Uani 1 1 d . . . .
C11B C -0.4399(2) 0.3620(2) 0.32889(10) 0.0182(4) Uani 1 1 d . . . .
C19 C 0.4341(2) 0.6952(2) 0.23035(9) 0.0177(4) Uani 1 1 d . . . .
C5B C -0.2036(2) 0.6375(2) 0.38191(10) 0.0188(4) Uani 1 1 d . . . .
C17 C 0.1889(2) 0.7020(2) 0.43837(10) 0.0213(4) Uani 1 1 d . . . .
H17 H 0.1126 0.7096 0.4591 0.026 Uiso 1 1 calc R . . .
C4 C 0.3206(2) 0.5754(2) 0.23860(10) 0.0171(4) Uani 1 1 d . . . .
C14B C -0.5310(2) 0.2654(2) 0.18157(10) 0.0212(4) Uani 1 1 d . . . .
H14B H -0.5781 0.3146 0.2048 0.025 Uiso 1 1 calc R . . .
C24 C 0.5535(2) 0.6817(2) 0.20726(10) 0.0219(4) Uani 1 1 d . . . .
H24 H 0.5604 0.5954 0.1954 0.026 Uiso 1 1 calc R . . .
C20 C 0.4235(2) 0.8227(2) 0.24580(10) 0.0215(4) Uani 1 1 d . . . .
H20 H 0.3411 0.8329 0.2604 0.026 Uiso 1 1 calc R . . .
C15B C -0.6070(2) 0.1587(2) 0.14030(10) 0.0222(4) Uani 1 1 d . . . .
H15B H -0.7055 0.1349 0.1349 0.027 Uiso 1 1 calc R . . .
C22 C 0.6531(2) 0.9201(2) 0.21834(11) 0.0244(5) Uani 1 1 d . . . .
H22 H 0.7286 0.9964 0.2151 0.029 Uiso 1 1 calc R . . .
C23 C 0.6630(2) 0.7938(2) 0.20145(11) 0.0245(5) Uani 1 1 d . . . .
H23 H 0.7445 0.7838 0.1859 0.029 Uiso 1 1 calc R . . .
C9B C -0.1566(2) 0.6425(3) 0.49252(10) 0.0262(5) Uani 1 1 d . . . .
H9B H -0.1483 0.5970 0.5280 0.031 Uiso 1 1 calc R . . .
C6 C 0.0508(2) 0.2656(2) 0.10569(10) 0.0228(4) Uani 1 1 d . . . .
H6 H 0.0686 0.3502 0.0901 0.027 Uiso 1 1 calc R . . .
C6B C -0.1826(2) 0.7752(2) 0.38857(11) 0.0230(5) Uani 1 1 d . . . .
H6B H -0.1918 0.8212 0.3534 0.028 Uiso 1 1 calc R . . .
C10 C 0.0589(2) 0.1311(2) 0.19007(10) 0.0210(4) Uani 1 1 d . . . .
H10 H 0.0823 0.1242 0.2324 0.025 Uiso 1 1 calc R . . .
C2SB C 0.1516(2) 0.9362(2) 0.32495(11) 0.0253(5) Uani 1 1 d . . . .
C19B C -0.1256(2) 0.5558(2) 0.16714(10) 0.0176(4) Uani 1 1 d . . . .
C12 C -0.1642(2) 0.2013(2) 0.32337(11) 0.0254(5) Uani 1 1 d . . . .
H12A H -0.2596 0.1781 0.3033 0.038 Uiso 1 1 calc GR . . .
H12B H -0.1577 0.2520 0.3632 0.038 Uiso 1 1 calc GR . . .
H12C H -0.1385 0.1195 0.3295 0.038 Uiso 1 1 calc GR . . .
C24B C 0.0163(2) 0.6252(2) 0.17404(10) 0.0207(4) Uani 1 1 d . . . .
H24B H 0.0660 0.6470 0.2140 0.025 Uiso 1 1 calc R . . .
C8 C -0.0392(2) 0.0261(2) 0.08900(12) 0.0292(5) Uani 1 1 d . . . .
H8 H -0.0821 -0.0523 0.0620 0.035 Uiso 1 1 calc R . . .
C9 C -0.0036(2) 0.0162(2) 0.15080(11) 0.0265(5) Uani 1 1 d . . . .
H9 H -0.0221 -0.0688 0.1661 0.032 Uiso 1 1 calc R . . .
C20B C -0.1959(2) 0.5242(2) 0.10784(10) 0.0224(4) Uani 1 1 d . . . .
H20B H -0.2922 0.4783 0.1022 0.027 Uiso 1 1 calc R . . .
C23B C 0.0845(2) 0.6624(2) 0.12329(11) 0.0237(5) Uani 1 1 d . . . .
H23B H 0.1801 0.7112 0.1288 0.028 Uiso 1 1 calc R . . .
C7 C -0.0121(3) 0.1502(3) 0.06665(11) 0.0286(5) Uani 1 1 d . . . .
H7 H -0.0367 0.1563 0.0244 0.034 Uiso 1 1 calc R . . .
C21 C 0.5330(2) 0.9354(2) 0.24003(11) 0.0245(5) Uani 1 1 d . . . .
H21 H 0.5255 1.0220 0.2508 0.029 Uiso 1 1 calc R . . .
C8B C -0.1351(2) 0.7795(3) 0.49850(11) 0.0292(5) Uani 1 1 d . . . .
H8B H -0.1116 0.8279 0.5380 0.035 Uiso 1 1 calc R . . .
C21B C -0.1262(2) 0.5595(2) 0.05688(11) 0.0260(5) Uani 1 1 d . . . .
H21B H -0.1748 0.5360 0.0168 0.031 Uiso 1 1 calc R . . .
C7B C -0.1479(2) 0.8455(2) 0.44698(12) 0.0288(5) Uani 1 1 d . . . .
H7B H -0.1330 0.9392 0.4513 0.035 Uiso 1 1 calc R . . .
C12B C -0.5705(2) 0.3663(2) 0.41348(10) 0.0237(5) Uani 1 1 d . . . .
H12D H -0.6617 0.3325 0.3893 0.036 Uiso 1 1 calc GR . . .
H12E H -0.5756 0.4280 0.4482 0.036 Uiso 1 1 calc GR . . .
H12F H -0.5424 0.2915 0.4290 0.036 Uiso 1 1 calc GR . . .
C22B C 0.0146(3) 0.6290(2) 0.06436(11) 0.0268(5) Uani 1 1 d . . . .
H22B H 0.0622 0.6532 0.0296 0.032 Uiso 1 1 calc R . . .
C3SB C 0.2739(3) 1.0072(3) 0.36743(12) 0.0355(6) Uani 1 1 d . . . .
H3SG H 0.3276 1.0854 0.3492 0.053 Uiso 1 1 calc GR . . .
H3SH H 0.3314 0.9479 0.3755 0.053 Uiso 1 1 calc GR . . .
H3SI H 0.2448 1.0361 0.4061 0.053 Uiso 1 1 calc GR . . .
N1S N 0.3923(3) 0.5425(3) 0.06920(12) 0.0337(8) Uani 0.811(5) 1 d . P A 1
C3S C 0.5905(3) 0.7247(3) 0.02794(15) 0.0419(7) Uani 1 1 d . . . .
H3SA H 0.5619 0.7357 -0.0147 0.063 Uiso 0.811(5) 1 calc GR P A 1
H3SB H 0.6747 0.6959 0.0298 0.063 Uiso 0.811(5) 1 calc GR P A 1
H3SC H 0.6092 0.8098 0.0532 0.063 Uiso 0.811(5) 1 calc GR P A 1
H3SD H 0.5474 0.7916 0.0139 0.063 Uiso 0.189(5) 1 calc GR P A 2
H3SE H 0.6822 0.7695 0.0502 0.063 Uiso 0.189(5) 1 calc GR P A 2
H3SF H 0.5321 0.6698 0.0553 0.063 Uiso 0.189(5) 1 calc GR P A 2
C2S C 0.4782(3) 0.6228(3) 0.05145(14) 0.0291(7) Uani 0.811(5) 1 d . P A 1
N1SS N 0.3793(13) 0.4447(14) 0.0684(5) 0.034(3) Uani 0.189(5) 1 d . P A 2
C2SS C 0.6066(14) 0.6318(15) -0.0301(7) 0.034(4) Uani 0.189(5) 1 d . 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 0.0181 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
C11 O2 C12 114.27(17) .
C11B O2B C12B 117.15(17) .
C1 N1 H1 124.6 .
C1 N1 C4 110.72(17) .
C4 N1 H1 124.6 .
C4B N1B H1B 124.4 .
C1B N1B H1B 124.4 .
C1B N1B C4B 111.17(17) .
C17B C16B Br1B 120.34(17) .
C17B C16B C15B 121.7(2) .
C15B C16B Br1B 117.90(16) .
C16B C17B H17B 120.7 .
C16B C17B C18B 118.6(2) .
C18B C17B H17B 120.7 .
N1 C1 C5 121.25(18) .
N1 C1 C2 106.79(18) .
C2 C1 C5 131.81(19) .
C14 C15 H15 120.6 .
C16 C15 H15 120.6 .
C16 C15 C14 118.9(2) .
C6 C5 C1 121.01(19) .
C10 C5 C1 120.37(19) .
C10 C5 C6 118.6(2) .
N1B C4B C3B 107.32(18) .
N1B C4B C19B 119.07(18) .
C3B C4B C19B 133.6(2) .
C4B C3B C2B 106.95(18) .
C4B C3B C13B 126.18(19) .
C2B C3B C13B 126.86(18) .
C3B C2B C11B 126.78(19) .
C1B C2B C3B 107.77(18) .
C1B C2B C11B 125.45(19) .
C15 C14 H14 119.4 .
C15 C14 C13 121.25(19) .
C13 C14 H14 119.4 .
C5B C10B H10B 119.6 .
C9B C10B H10B 119.6 .
C9B C10B C5B 120.8(2) .
C1 C2 C11 126.43(19) .
C1 C2 C3 108.23(18) .
C3 C2 C11 125.22(19) .
O2 C11 C2 112.46(18) .
O1 C11 O2 122.84(19) .
O1 C11 C2 124.7(2) .
C15 C16 Br1 119.59(17) .
C15 C16 C17 121.7(2) .
C17 C16 Br1 118.71(16) .
C14 C13 C3 121.35(19) .
C14 C13 C18 118.2(2) .
C18 C13 C3 120.46(19) .
C17B C18B H18B 119.3 .
C17B C18B C13B 121.43(19) .
C13B C18B H18B 119.3 .
C2 C3 C13 127.35(18) .
C4 C3 C2 106.45(18) .
C4 C3 C13 126.14(19) .
C13 C18 H18 119.3 .
C17 C18 C13 121.5(2) .
C17 C18 H18 119.3 .
C18B C13B C3B 121.49(19) .
C18B C13B C14B 118.26(19) .
C14B C13B C3B 120.25(19) .
N1B C1B C2B 106.80(18) .
N1B C1B C5B 120.18(19) .
C2B C1B C5B 132.95(19) .
O1B C11B O2B 123.30(19) .
O1B C11B C2B 125.67(19) .
O2B C11B C2B 111.03(18) .
C24 C19 C4 120.0(2) .
C24 C19 C20 119.2(2) .
C20 C19 C4 120.77(19) .
C10B C5B C1B 120.64(19) .
C6B C5B C10B 118.8(2) .
C6B C5B C1B 120.5(2) .
C16 C17 H17 120.7 .
C18 C17 C16 118.5(2) .
C18 C17 H17 120.7 .
N1 C4 C3 107.80(18) .
N1 C4 C19 121.27(18) .
C3 C4 C19 130.9(2) .
C13B C14B H14B 119.4 .
C15B C14B C13B 121.2(2) .
C15B C14B H14B 119.4 .
C19 C24 H24 119.8 .
C19 C24 C23 120.5(2) .
C23 C24 H24 119.8 .
C19 C20 H20 119.7 .
C19 C20 C21 120.5(2) .
C21 C20 H20 119.7 .
C16B C15B H15B 120.6 .
C14B C15B C16B 118.8(2) .
C14B C15B H15B 120.6 .
C23 C22 H22 119.9 .
C23 C22 C21 120.2(2) .
C21 C22 H22 119.9 .
C24 C23 H23 120.0 .
C22 C23 C24 120.0(2) .
C22 C23 H23 120.0 .
C10B C9B H9B 120.1 .
C8B C9B C10B 119.9(2) .
C8B C9B H9B 120.1 .
C5 C6 H6 119.9 .
C7 C6 C5 120.2(2) .
C7 C6 H6 119.9 .
C5B C6B H6B 120.0 .
C5B C6B C7B 120.1(2) .
C7B C6B H6B 120.0 .
C5 C10 H10 119.5 .
C9 C10 C5 121.0(2) .
C9 C10 H10 119.5 .
N1SB C2SB C3SB 178.6(3) .
C24B C19B C4B 119.32(19) .
C20B C19B C4B 122.26(19) .
C20B C19B C24B 118.40(19) .
O2 C12 H12A 109.5 .
O2 C12 H12B 109.5 .
O2 C12 H12C 109.5 .
H12A C12 H12B 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
C19B C24B H24B 119.7 .
C23B C24B C19B 120.7(2) .
C23B C24B H24B 119.7 .
C9 C8 H8 119.9 .
C7 C8 H8 119.9 .
C7 C8 C9 120.2(2) .
C10 C9 C8 119.7(2) .
C10 C9 H9 120.2 .
C8 C9 H9 120.2 .
C19B C20B H20B 119.7 .
C21B C20B C19B 120.7(2) .
C21B C20B H20B 119.7 .
C24B C23B H23B 119.7 .
C24B C23B C22B 120.7(2) .
C22B C23B H23B 119.7 .
C6 C7 H7 119.8 .
C8 C7 C6 120.4(2) .
C8 C7 H7 119.8 .
C20 C21 H21 120.2 .
C22 C21 C20 119.5(2) .
C22 C21 H21 120.2 .
C9B C8B H8B 120.0 .
C7B C8B C9B 120.0(2) .
C7B C8B H8B 120.0 .
C20B C21B H21B 119.8 .
C20B C21B C22B 120.4(2) .
C22B C21B H21B 119.8 .
C6B C7B H7B 119.8 .
C8B C7B C6B 120.4(2) .
C8B C7B H7B 119.8 .
O2B C12B H12D 109.5 .
O2B C12B H12E 109.5 .
O2B C12B H12F 109.5 .
H12D C12B H12E 109.5 .
H12D C12B H12F 109.5 .
H12E C12B H12F 109.5 .
C23B C22B C21B 119.2(2) .
C23B C22B H22B 120.4 .
C21B C22B H22B 120.4 .
C2SB C3SB H3SG 109.5 .
C2SB C3SB H3SH 109.5 .
C2SB C3SB H3SI 109.5 .
H3SG C3SB H3SH 109.5 .
H3SG C3SB H3SI 109.5 .
H3SH C3SB H3SI 109.5 .
H3SA C3S H3SB 109.5 .
H3SA C3S H3SC 109.5 .
H3SB C3S H3SC 109.5 .
H3SD C3S H3SE 109.5 .
H3SD C3S H3SF 109.5 .
H3SE C3S H3SF 109.5 .
C2S C3S H3SA 109.5 .
C2S C3S H3SB 109.5 .
C2S C3S H3SC 109.5 .
C2SS C3S H3SD 109.5 .
C2SS C3S H3SE 109.5 .
C2SS C3S H3SF 109.5 .
N1S C2S C3S 178.8(4) .
N1SS C2SS C3S 173.3(13) 2_665
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C16 1.904(2) .
Br1B C16B 1.908(2) .
O2 C11 1.338(3) .
O2 C12 1.447(2) .
O1B C11B 1.216(3) .
O2B C11B 1.342(3) .
O2B C12B 1.445(2) .
O1 C11 1.204(3) .
N1 H1 0.8800 .
N1 C1 1.370(3) .
N1 C4 1.372(3) .
N1B H1B 0.8800 .
N1B C4B 1.378(3) .
N1B C1B 1.363(3) .
N1SB C2SB 1.134(3) .
C16B C17B 1.384(3) .
C16B C15B 1.385(3) .
C17B H17B 0.9500 .
C17B C18B 1.384(3) .
C1 C5 1.466(3) .
C1 C2 1.382(3) .
C15 H15 0.9500 .
C15 C14 1.390(3) .
C15 C16 1.385(3) .
C5 C6 1.405(3) .
C5 C10 1.403(3) .
C4B C3B 1.382(3) .
C4B C19B 1.470(3) .
C3B C2B 1.434(3) .
C3B C13B 1.485(3) .
C2B C1B 1.391(3) .
C2B C11B 1.469(3) .
C14 H14 0.9500 .
C14 C13 1.396(3) .
C10B H10B 0.9500 .
C10B C5B 1.401(3) .
C10B C9B 1.389(3) .
C2 C11 1.478(3) .
C2 C3 1.432(3) .
C16 C17 1.389(3) .
C13 C3 1.482(3) .
C13 C18 1.401(3) .
C18B H18B 0.9500 .
C18B C13B 1.394(3) .
C3 C4 1.384(3) .
C18 H18 0.9500 .
C18 C17 1.389(3) .
C13B C14B 1.399(3) .
C1B C5B 1.473(3) .
C19 C4 1.478(3) .
C19 C24 1.391(3) .
C19 C20 1.395(3) .
C5B C6B 1.397(3) .
C17 H17 0.9500 .
C14B H14B 0.9500 .
C14B C15B 1.384(3) .
C24 H24 0.9500 .
C24 C23 1.392(3) .
C20 H20 0.9500 .
C20 C21 1.395(3) .
C15B H15B 0.9500 .
C22 H22 0.9500 .
C22 C23 1.387(3) .
C22 C21 1.390(3) .
C23 H23 0.9500 .
C9B H9B 0.9500 .
C9B C8B 1.389(4) .
C6 H6 0.9500 .
C6 C7 1.390(3) .
C6B H6B 0.9500 .
C6B C7B 1.398(3) .
C10 H10 0.9500 .
C10 C9 1.389(3) .
C2SB C3SB 1.461(3) .
C19B C24B 1.403(3) .
C19B C20B 1.397(3) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C24B H24B 0.9500 .
C24B C23B 1.384(3) .
C8 H8 0.9500 .
C8 C9 1.391(3) .
C8 C7 1.387(4) .
C9 H9 0.9500 .
C20B H20B 0.9500 .
C20B C21B 1.391(3) .
C23B H23B 0.9500 .
C23B C22B 1.389(3) .
C7 H7 0.9500 .
C21 H21 0.9500 .
C8B H8B 0.9500 .
C8B C7B 1.381(4) .
C21B H21B 0.9500 .
C21B C22B 1.393(3) .
C7B H7B 0.9500 .
C12B H12D 0.9800 .
C12B H12E 0.9800 .
C12B H12F 0.9800 .
C22B H22B 0.9500 .
C3SB H3SG 0.9800 .
C3SB H3SH 0.9800 .
C3SB H3SI 0.9800 .
N1S C2S 1.144(4) .
C3S H3SA 0.9800 .
C3S H3SB 0.9800 .
C3S H3SC 0.9800 .
C3S H3SD 0.9800 .
C3S H3SE 0.9800 .
C3S H3SF 0.9800 .
C3S C2S 1.481(4) .
C3S C2SS 1.599(16) .
N1SS C2SS 1.17(2) 2_665
C2SS N1SS 1.17(2) 2_665
