#------------------------------------------------------------------------------
#$Date: 2021-04-05 17:05:01 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263660 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/78/7127820.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_7127820
loop_
_publ_author_name
'Knight, Brian J.'
'Tolchin, Zachary A.'
'Smith, Joel M.'
_publ_section_title
;
 A predictive model for additions to N-alkyl pyridiniums.
;
_journal_issue                   21
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2693
_journal_page_last               2696
_journal_paper_doi               10.1039/d1cc00056j
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         '2(C14 H19 Br N O4), Br'
_chemical_formula_sum            'C28 H38 Br3 N2 O8'
_chemical_formula_weight         770.33
_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_block_doi                 10.5517/ccdc.csd.cc269gdd
_audit_creation_date             2019-12-05
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.10.09 svn.r3662 for Rigaku Oxford Diffraction, GUI svn.r5959)
;
_audit_update_record
;
2020-10-01 deposited with the CCDC.	2021-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                113.1790(10)
_cell_angle_beta                 99.6000(10)
_cell_angle_gamma                103.8560(10)
_cell_formula_units_Z            2
_cell_length_a                   10.89440(10)
_cell_length_b                   13.39160(10)
_cell_length_c                   14.63390(10)
_cell_measurement_reflns_used    30741
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      77.5630
_cell_measurement_theta_min      3.4170
_cell_volume                     1822.23(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00  25.00   0.50    0.10    --  -47.12  48.00 128.00  158
  2  ω   -118.00 -33.00   0.50    0.10    --  -47.12 -48.00 -19.00  170
  3  ω    -24.00  54.00   0.50    0.10    --   47.12 -48.00 -19.00  156
  4  ω     34.00 119.00   0.50    0.10    --   47.12  48.00 128.00  170
  5  ω    -54.00 -14.00   0.50    0.50    --  -86.25  48.00 128.00   80
  6  ω   -159.00 -72.00   0.50    0.50    --  -86.25 -48.00 -19.00  174
  7  ω     94.00 178.00   0.50    0.50    --  107.75  48.00 128.00  168
  8  ω   -119.00 -73.00   0.50    0.10    --  -47.12-125.00  90.00   92
  9  ω    -70.00  26.00   0.50    0.10    --  -47.12  77.00-180.00  192
 10  ω   -119.00 -73.00   0.50    0.10    --  -47.12-125.00 -90.00   92
 11  ω     34.00  95.00   0.50    0.10    --   47.12-125.00   0.00  122
 12  ω    -86.00 -13.00   0.50    0.50    --  -86.25 125.00-180.00  146
 13  ω     45.00 126.00   0.50    0.50    --  107.75-145.00-125.59  162
 14  ω     35.00  71.00   0.50    0.50    --  107.75 -61.00   0.00   72
 15  ω     35.00  71.00   0.50    0.50    --  107.75 -61.00-150.00   72
 16  ω     35.00 107.00   0.50    0.50    --  107.75-105.00 -20.45  144
 17  ω     35.00 107.00   0.50    0.50    --  107.75-102.00-130.53  144
 18  ω     35.00 106.00   0.50    0.50    --  107.75 -94.00  90.00  142
 19  ω     85.00 178.00   0.50    0.50    --  107.75  76.00  48.46  186
 20  ω     35.00 112.00   0.50    0.50    --  107.75-125.00  90.00  154
 21  ω     42.00 122.00   0.50    0.50    --  107.75-139.00 124.32  160
 22  ω     35.00 106.00   0.50    0.50    --  107.75 -77.00  90.00  142
 23  ω     95.00 178.00   0.50    0.50    --  107.75  45.00 -30.00  166
 24  ω     35.00  71.00   0.50    0.50    --  107.75 -61.00 150.00   72
 25  ω     95.00 178.00   0.50    0.50    --  107.75 125.00   0.00  166
 26  ω     95.00 178.00   0.50    0.50    --  107.75  30.00 -60.00  166
 27  ω     95.00 178.00   0.50    0.50    --  107.75  45.00   0.00  166
 28  ω     35.00 112.00   0.50    0.50    --  107.75-125.00-120.00  154
 29  ω     35.00 106.00   0.50    0.50    --  107.75 -94.00  60.00  142
 30  ω     35.00 106.00   0.50    0.50    --  107.75 -77.00 150.00  142
 31  ω     94.00 178.00   0.50    0.50    --  107.75  15.00 120.00  168
 32  ω     35.00  71.00   0.50    0.50    --  107.75 -61.00-120.00   72
 33  ω     35.00 108.00   0.50    0.50    --  107.75-111.00 -64.38  146
 34  ω     94.00 178.00   0.50    0.50    --  107.75  15.00  90.00  168
 35  ω     35.00 106.00   0.50    0.50    --  107.75 -94.00 -30.00  142
 36  ω     49.00  82.00   0.50    0.50    --  107.75-125.00 150.00   66
 37  ω     87.00 112.00   0.50    0.50    --  107.75-125.00 150.00   50
 38  ω     49.00 105.00   0.50    0.50    --  107.75 -94.00   0.00  112
 39  ω    104.00 176.00   0.50    0.50    --  107.75  45.00 -60.00  144
 40  ω     88.00 133.00   0.50    0.50    --  107.75  77.00   0.00   90
 41  ω    152.00 178.00   0.50    0.50    --  107.75  77.00   0.00   52
 42  ω     44.00  74.00   0.50    0.50    --  107.75 -77.00-150.00   60
 43  ω     39.00  65.00   0.50    0.50    --  107.75 -97.00 141.93   52
 44  ω     69.00  95.00   0.50    0.50    --  107.75 -97.00 141.93   52
 45  ω     35.00  60.00   0.50    0.50    --  107.75 -61.00 120.00   50
 46  ω     72.00 106.00   0.50    0.50    --  107.75 -94.00-120.00   68
 47  ω     59.00  99.00   0.50    0.50    --  107.75 -94.00 -60.00   80
 48  ω     59.00 102.00   0.50    0.50    --  107.75 -94.00  30.00   86
 49  ω     35.00 112.00   0.50    0.50    --  107.75-125.00 -30.00  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1209388000
_diffrn_orient_matrix_UB_12      0.0036087000
_diffrn_orient_matrix_UB_13      0.0411578000
_diffrn_orient_matrix_UB_21      0.0582668000
_diffrn_orient_matrix_UB_22      0.1326801000
_diffrn_orient_matrix_UB_23      0.0580523000
_diffrn_orient_matrix_UB_31      -0.0719431000
_diffrn_orient_matrix_UB_32      0.0066800000
_diffrn_orient_matrix_UB_33      -0.0963161000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            39990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.893
_diffrn_reflns_theta_min         3.436
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.469
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.487
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       block
_exptl_crystal_F_000             778
_exptl_crystal_size_max          0.304
_exptl_crystal_size_mid          0.202
_exptl_crystal_size_min          0.166
_refine_diff_density_max         0.844
_refine_diff_density_min         -1.135
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         7684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0422
_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)+(0.0693P)²+3.0573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1226
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7244
_reflns_number_total             7684
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc00056j2.cif
_cod_data_source_block           bk-2
_cod_depositor_comments          'Adding full bibliography for 7127820.cif.'
_cod_original_cell_volume        1822.22(3)
_cod_database_code               7127820
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C12 H20 Br N O4'
_chemical_oxdiff_usercomment     '0.8, Cu 0.1 and 0.5, 150 K'
_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   0.524
_shelx_estimated_absorpt_t_min   0.344
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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
2.a Ternary CH refined with riding coordinates:
 C11(H11), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B),
 C23(H23A,H23B), C24(H24A,H24B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C16(H16), C20(H20)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C8(H8A,H8B,H8C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.031
_oxdiff_exptl_absorpt_empirical_full_min 0.345
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
Br1 Br -0.22448(3) 0.08272(3) 0.04590(2) 0.02584(9) Uani 1 1 d . . . . .
O5 O -0.66110(19) 0.11497(18) 0.16373(15) 0.0234(4) Uani 1 1 d . . . . .
O6 O -0.45415(18) 0.16101(18) 0.27514(15) 0.0229(4) Uani 1 1 d . . . . .
O7 O 0.0732(2) 0.1019(2) 0.39449(18) 0.0366(5) Uani 1 1 d . . . . .
O8 O 0.0787(2) 0.2641(2) 0.52578(16) 0.0325(5) Uani 1 1 d . . . . .
N1 N -0.1870(2) 0.32140(19) 0.34059(18) 0.0207(4) Uani 1 1 d . . . . .
C1 C -0.1735(3) 0.1732(2) 0.1913(2) 0.0194(5) Uani 1 1 d . . . . .
C2 C -0.0861(3) 0.1487(2) 0.2526(2) 0.0214(5) Uani 1 1 d . . . . .
H2 H -0.051458 0.088882 0.222090 0.026 Uiso 1 1 calc R U . . .
C3 C -0.0502(3) 0.2137(2) 0.3596(2) 0.0212(5) Uani 1 1 d . . . . .
C4 C 0.0414(3) 0.1863(3) 0.4274(2) 0.0249(6) Uani 1 1 d . . . . .
C5 C 0.1613(4) 0.2407(4) 0.5985(3) 0.0456(9) Uani 1 1 d . . . . .
H5A H 0.116854 0.163749 0.590882 0.068 Uiso 1 1 calc R U . . .
H5B H 0.176110 0.298567 0.669730 0.068 Uiso 1 1 calc R U . . .
H5C H 0.246341 0.243947 0.583972 0.068 Uiso 1 1 calc R U . . .
C6 C -0.1007(3) 0.3006(2) 0.4022(2) 0.0200(5) Uani 1 1 d . . . . .
H6 H -0.074551 0.346169 0.475446 0.024 Uiso 1 1 calc R U . . .
C7 C -0.2271(2) 0.2596(2) 0.2352(2) 0.0191(5) Uani 1 1 d . . . . .
C8 C -0.2336(3) 0.4181(3) 0.3928(2) 0.0273(6) Uani 1 1 d . . . . .
H8A H -0.201487 0.479155 0.372936 0.041 Uiso 1 1 calc R U . . .
H8B H -0.199707 0.448633 0.468350 0.041 Uiso 1 1 calc R U . . .
H8C H -0.330461 0.390616 0.371897 0.041 Uiso 1 1 calc R U . . .
C9 C -0.3265(3) 0.2849(2) 0.1702(2) 0.0214(5) Uani 1 1 d . . . . .
H9A H -0.296088 0.286664 0.110562 0.026 Uiso 1 1 calc R U . . .
H9B H -0.329196 0.362535 0.212622 0.026 Uiso 1 1 calc R U . . .
C10 C -0.4677(3) 0.1969(3) 0.1284(2) 0.0223(5) Uani 1 1 d . . . . .
H10A H -0.523819 0.215479 0.081182 0.027 Uiso 1 1 calc R U . . .
H10B H -0.464677 0.119101 0.086928 0.027 Uiso 1 1 calc R U . . .
C11 C -0.5314(2) 0.1939(2) 0.2120(2) 0.0184(5) Uani 1 1 d . . . . .
H11 H -0.533754 0.272400 0.255184 0.022 Uiso 1 1 calc R U . . .
C12 C -0.5077(3) 0.1572(3) 0.3573(2) 0.0313(7) Uani 1 1 d . . . . .
H12A H -0.502886 0.235725 0.405006 0.038 Uiso 1 1 calc R U . . .
H12B H -0.454761 0.129373 0.397559 0.038 Uiso 1 1 calc R U . . .
C13 C -0.6502(3) 0.0775(3) 0.3132(3) 0.0303(6) Uani 1 1 d . . . . .
H13A H -0.654022 -0.003347 0.275331 0.036 Uiso 1 1 calc R U . . .
H13B H -0.690058 0.083679 0.370424 0.036 Uiso 1 1 calc R U . . .
C14 C -0.7270(3) 0.1104(3) 0.2400(2) 0.0255(6) Uani 1 1 d . . . . .
H14A H -0.817241 0.053038 0.204801 0.031 Uiso 1 1 calc R U . . .
H14B H -0.734796 0.186674 0.280001 0.031 Uiso 1 1 calc R U . . .
Br2 Br 0.77236(3) 0.08095(2) 0.53187(2) 0.02375(9) Uani 1 1 d . . . . .
O1 O 0.34751(19) 0.11589(18) 0.67320(14) 0.0230(4) Uani 1 1 d . . . . .
O2 O 0.56075(19) 0.17692(18) 0.78103(15) 0.0235(4) Uani 1 1 d . . . . .
O3 O 1.0735(2) 0.1131(2) 0.88402(17) 0.0326(5) Uani 1 1 d . . . . .
O4 O 1.0681(2) 0.27091(19) 1.01531(16) 0.0321(5) Uani 1 1 d . . . . .
N2 N 0.8204(2) 0.33466(19) 0.82124(18) 0.0202(4) Uani 1 1 d . . . . .
C15 C 0.8276(2) 0.1786(2) 0.67611(19) 0.0186(5) Uani 1 1 d . . . . .
C16 C 0.9154(3) 0.1569(2) 0.7396(2) 0.0212(5) Uani 1 1 d . . . . .
H16 H 0.949870 0.096506 0.710611 0.025 Uiso 1 1 calc R U . . .
C17 C 0.9524(3) 0.2246(2) 0.8463(2) 0.0198(5) Uani 1 1 d . . . . .
C18 C 1.0396(3) 0.1963(2) 0.9162(2) 0.0228(5) Uani 1 1 d . . . . .
C19 C 1.1478(4) 0.2474(4) 1.0895(3) 0.0450(9) Uani 1 1 d . . . . .
H19A H 1.108538 0.166948 1.075253 0.068 Uiso 1 1 calc R U . . .
H19B H 1.150717 0.298603 1.160203 0.068 Uiso 1 1 calc R U . . .
H19C H 1.237689 0.260966 1.083146 0.068 Uiso 1 1 calc R U . . .
C20 C 0.9055(3) 0.3151(2) 0.8858(2) 0.0203(5) Uani 1 1 d . . . . .
H20 H 0.932983 0.363895 0.958568 0.024 Uiso 1 1 calc R U . . .
C21 C 0.7790(3) 0.4363(2) 0.8692(2) 0.0272(6) Uani 1 1 d . . . . .
H21A H 0.809775 0.491248 0.842335 0.041 Uiso 1 1 calc R U . . .
H21B H 0.817574 0.473429 0.944792 0.041 Uiso 1 1 calc R U . . .
H21C H 0.682414 0.411492 0.852022 0.041 Uiso 1 1 calc R U . . .
C22 C 0.7746(3) 0.2660(2) 0.7171(2) 0.0189(5) Uani 1 1 d . . . . .
C23 C 0.6650(3) 0.2808(2) 0.6516(2) 0.0200(5) Uani 1 1 d . . . . .
H23A H 0.686396 0.276401 0.587268 0.024 Uiso 1 1 calc R U . . .
H23B H 0.659575 0.358348 0.690251 0.024 Uiso 1 1 calc R U . . .
C24 C 0.5296(3) 0.1891(2) 0.6221(2) 0.0213(5) Uani 1 1 d . . . . .
H24A H 0.465275 0.195888 0.570359 0.026 Uiso 1 1 calc R U . . .
H24B H 0.537528 0.111711 0.588587 0.026 Uiso 1 1 calc R U . . .
C25 C 0.4757(2) 0.1983(2) 0.71294(19) 0.0183(5) Uani 1 1 d . . . . .
H25 H 0.471339 0.277490 0.750017 0.022 Uiso 1 1 calc R U . . .
C26 C 0.5155(3) 0.1856(3) 0.8703(2) 0.0335(7) Uani 1 1 d . . . . .
H26A H 0.517674 0.265421 0.910925 0.040 Uiso 1 1 calc R U . . .
H26B H 0.574930 0.167244 0.915616 0.040 Uiso 1 1 calc R U . . .
C27 C 0.3757(3) 0.1024(3) 0.8351(2) 0.0304(6) Uani 1 1 d . . . . .
H27A H 0.375542 0.021987 0.803763 0.036 Uiso 1 1 calc R U . . .
H27B H 0.340802 0.114995 0.895459 0.036 Uiso 1 1 calc R U . . .
C28 C 0.2895(3) 0.1219(3) 0.7561(2) 0.0256(6) Uani 1 1 d . . . . .
H28A H 0.200464 0.062540 0.727251 0.031 Uiso 1 1 calc R U . . .
H28B H 0.279707 0.198515 0.790158 0.031 Uiso 1 1 calc R U . . .
Br3 Br 0.93600(4) 0.49918(3) 0.67702(3) 0.03947(11) Uani 1 1 d . . . . .
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
1 -6 -3 0.1012
-2 9 -2 0.0820
-1 7 1 0.0915
5 1 3 0.1065
5 5 -2 0.1203
-4 4 -7 0.1467
3 -1 -5 0.0960
-7 0 4 0.0964
-6 -2 6 0.0914
-5 -3 7 0.0936
2 -9 2 0.0821
2 2 -5 0.1132
0 -2 5 0.1424
2 -4 5 0.1235
-1 5 2 0.0962
-1 -5 2 0.0736
-3 5 1 0.0741
-5 5 1 0.0882
-4 5 3 0.0920
-2 -5 5 0.0837
-5 -2 -1 0.1242
7 -2 1 0.0762
-1 -5 -1 0.0911
-2 0 -8 0.1409
3 1 -5 0.0964
-5 4 -6 0.1451
-3 5 0 0.0759
3 -5 1 0.0871
3 -5 -3 0.0898
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
C11 O5 C14 110.7(2) . . ?
C11 O6 C12 111.4(2) . . ?
C4 O8 C5 115.6(3) . . ?
C6 N1 C7 122.4(2) . . ?
C6 N1 C8 116.7(2) . . ?
C7 N1 C8 121.0(2) . . ?
C2 C1 Br1 118.2(2) . . ?
C2 C1 C7 121.4(2) . . ?
C7 C1 Br1 120.38(19) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.3(2) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 119.1(2) . . ?
C6 C3 C2 119.9(2) . . ?
C6 C3 C4 121.0(2) . . ?
O7 C4 O8 125.3(3) . . ?
O7 C4 C3 122.9(3) . . ?
O8 C4 C3 111.7(2) . . ?
O8 C5 H5A 109.5 . . ?
O8 C5 H5B 109.5 . . ?
O8 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 C3 120.4(2) . . ?
N1 C6 H6 119.8 . . ?
C3 C6 H6 119.8 . . ?
N1 C7 C1 117.6(2) . . ?
N1 C7 C9 120.1(2) . . ?
C1 C7 C9 122.4(2) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 108.7 . . ?
C7 C9 H9B 108.7 . . ?
C7 C9 C10 114.2(2) . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 C9 114.2(2) . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
O5 C11 O6 111.6(2) . . ?
O5 C11 C10 108.5(2) . . ?
O5 C11 H11 109.6 . . ?
O6 C11 C10 108.0(2) . . ?
O6 C11 H11 109.6 . . ?
C10 C11 H11 109.6 . . ?
O6 C12 H12A 109.6 . . ?
O6 C12 H12B 109.6 . . ?
O6 C12 C13 110.4(2) . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C12 C13 H13A 109.8 . . ?
C12 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
C14 C13 C12 109.5(2) . . ?
C14 C13 H13A 109.8 . . ?
C14 C13 H13B 109.8 . . ?
O5 C14 C13 110.2(2) . . ?
O5 C14 H14A 109.6 . . ?
O5 C14 H14B 109.6 . . ?
C13 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C25 O1 C28 110.6(2) . . ?
C25 O2 C26 111.2(2) . . ?
C18 O4 C19 115.5(2) . . ?
C20 N2 C21 117.0(2) . . ?
C20 N2 C22 122.5(2) . . ?
C22 N2 C21 120.4(2) . . ?
C16 C15 Br2 118.2(2) . . ?
C16 C15 C22 121.5(2) . . ?
C22 C15 Br2 120.19(19) . . ?
C15 C16 H16 120.6 . . ?
C15 C16 C17 118.9(2) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 C18 119.3(2) . . ?
C20 C17 C16 119.2(2) . . ?
C20 C17 C18 121.5(2) . . ?
O3 C18 O4 125.8(3) . . ?
O3 C18 C17 122.6(3) . . ?
O4 C18 C17 111.6(2) . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C17 120.3(2) . . ?
N2 C20 H20 119.9 . . ?
C17 C20 H20 119.9 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C22 C15 117.3(2) . . ?
N2 C22 C23 120.1(2) . . ?
C15 C22 C23 122.6(2) . . ?
C22 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
C22 C23 C24 112.8(2) . . ?
H23A C23 H23B 107.8 . . ?
C24 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
C23 C24 H24A 108.7 . . ?
C23 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C25 C24 C23 114.3(2) . . ?
C25 C24 H24A 108.7 . . ?
C25 C24 H24B 108.7 . . ?
O1 C25 C24 107.9(2) . . ?
O1 C25 H25 109.8 . . ?
O2 C25 O1 111.2(2) . . ?
O2 C25 C24 108.4(2) . . ?
O2 C25 H25 109.8 . . ?
C24 C25 H25 109.8 . . ?
O2 C26 H26A 109.7 . . ?
O2 C26 H26B 109.7 . . ?
O2 C26 C27 109.9(2) . . ?
H26A C26 H26B 108.2 . . ?
C27 C26 H26A 109.7 . . ?
C27 C26 H26B 109.7 . . ?
C26 C27 H27A 109.8 . . ?
C26 C27 H27B 109.8 . . ?
H27A C27 H27B 108.3 . . ?
C28 C27 C26 109.2(3) . . ?
C28 C27 H27A 109.8 . . ?
C28 C27 H27B 109.8 . . ?
O1 C28 C27 110.1(2) . . ?
O1 C28 H28A 109.6 . . ?
O1 C28 H28B 109.6 . . ?
C27 C28 H28A 109.6 . . ?
C27 C28 H28B 109.6 . . ?
H28A C28 H28B 108.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.886(3) . ?
O5 C11 1.406(3) . ?
O5 C14 1.437(3) . ?
O6 C11 1.413(3) . ?
O6 C12 1.434(3) . ?
O7 C4 1.202(4) . ?
O8 C4 1.321(4) . ?
O8 C5 1.456(4) . ?
N1 C6 1.347(4) . ?
N1 C7 1.361(4) . ?
N1 C8 1.478(3) . ?
C1 C2 1.385(4) . ?
C1 C7 1.399(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(4) . ?
C3 C4 1.498(4) . ?
C3 C6 1.376(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6 0.9500 . ?
C7 C9 1.509(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.543(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.513(4) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.515(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.513(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
Br2 C15 1.885(3) . ?
O1 C25 1.411(3) . ?
O1 C28 1.443(3) . ?
O2 C25 1.407(3) . ?
O2 C26 1.444(3) . ?
O3 C18 1.201(4) . ?
O4 C18 1.326(4) . ?
O4 C19 1.455(4) . ?
N2 C20 1.356(3) . ?
N2 C21 1.482(3) . ?
N2 C22 1.357(3) . ?
C15 C16 1.384(4) . ?
C15 C22 1.395(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(4) . ?
C17 C18 1.500(3) . ?
C17 C20 1.381(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.505(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.540(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.514(4) . ?
C25 H25 1.0000 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.517(5) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.510(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 C3 -178.8(2) . . . . ?
Br1 C1 C7 N1 179.53(18) . . . . ?
Br1 C1 C7 C9 -0.1(3) . . . . ?
O6 C12 C13 C14 -51.6(4) . . . . ?
N1 C7 C9 C10 -103.1(3) . . . . ?
C1 C2 C3 C4 178.3(2) . . . . ?
C1 C2 C3 C6 -0.5(4) . . . . ?
C1 C7 C9 C10 76.5(3) . . . . ?
C2 C1 C7 N1 2.0(4) . . . . ?
C2 C1 C7 C9 -177.6(2) . . . . ?
C2 C3 C4 O7 -9.2(4) . . . . ?
C2 C3 C4 O8 172.2(3) . . . . ?
C2 C3 C6 N1 1.4(4) . . . . ?
C4 C3 C6 N1 -177.4(3) . . . . ?
C5 O8 C4 O7 -2.3(5) . . . . ?
C5 O8 C4 C3 176.2(3) . . . . ?
C6 N1 C7 C1 -1.1(4) . . . . ?
C6 N1 C7 C9 178.6(2) . . . . ?
C6 C3 C4 O7 169.6(3) . . . . ?
C6 C3 C4 O8 -9.0(4) . . . . ?
C7 N1 C6 C3 -0.6(4) . . . . ?
C7 C1 C2 C3 -1.2(4) . . . . ?
C7 C9 C10 C11 64.1(3) . . . . ?
C8 N1 C6 C3 -178.6(2) . . . . ?
C8 N1 C7 C1 176.8(2) . . . . ?
C8 N1 C7 C9 -3.5(4) . . . . ?
C9 C10 C11 O5 177.1(2) . . . . ?
C9 C10 C11 O6 -61.7(3) . . . . ?
C11 O5 C14 C13 -57.8(3) . . . . ?
C11 O6 C12 C13 55.9(3) . . . . ?
C12 O6 C11 O5 -61.3(3) . . . . ?
C12 O6 C11 C10 179.5(2) . . . . ?
C12 C13 C14 O5 52.6(3) . . . . ?
C14 O5 C11 O6 62.1(3) . . . . ?
C14 O5 C11 C10 -179.0(2) . . . . ?
Br2 C15 C16 C17 -177.1(2) . . . . ?
Br2 C15 C22 N2 -178.73(18) . . . . ?
Br2 C15 C22 C23 5.1(3) . . . . ?
O2 C26 C27 C28 -52.6(4) . . . . ?
N2 C22 C23 C24 -101.8(3) . . . . ?
C15 C16 C17 C18 175.5(2) . . . . ?
C15 C16 C17 C20 -3.0(4) . . . . ?
C15 C22 C23 C24 74.2(3) . . . . ?
C16 C15 C22 N2 4.9(4) . . . . ?
C16 C15 C22 C23 -171.2(2) . . . . ?
C16 C17 C18 O3 -4.1(4) . . . . ?
C16 C17 C18 O4 178.5(3) . . . . ?
C16 C17 C20 N2 2.5(4) . . . . ?
C18 C17 C20 N2 -176.0(2) . . . . ?
C19 O4 C18 O3 0.1(5) . . . . ?
C19 O4 C18 C17 177.5(3) . . . . ?
C20 N2 C22 C15 -5.6(4) . . . . ?
C20 N2 C22 C23 170.6(2) . . . . ?
C20 C17 C18 O3 174.4(3) . . . . ?
C20 C17 C18 O4 -3.0(4) . . . . ?
C21 N2 C20 C17 -177.5(3) . . . . ?
C21 N2 C22 C15 173.9(2) . . . . ?
C21 N2 C22 C23 -9.8(4) . . . . ?
C22 N2 C20 C17 2.0(4) . . . . ?
C22 C15 C16 C17 -0.7(4) . . . . ?
C22 C23 C24 C25 67.4(3) . . . . ?
C23 C24 C25 O1 175.1(2) . . . . ?
C23 C24 C25 O2 -64.4(3) . . . . ?
C25 O1 C28 C27 -58.1(3) . . . . ?
C25 O2 C26 C27 57.2(3) . . . . ?
C26 O2 C25 O1 -62.2(3) . . . . ?
C26 O2 C25 C24 179.4(2) . . . . ?
C26 C27 C28 O1 53.3(3) . . . . ?
C28 O1 C25 O2 62.4(3) . . . . ?
C28 O1 C25 C24 -178.9(2) . . . . ?
loop_
_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
0.5898 -5.9605 -3.2622 -0.2271 -0.9458 0.2319
-2.2754 8.5822 -2.3613 0.2090 0.8690 0.4485
-1.2080 7.2052 1.4935 0.2336 0.9723 -0.0088
5.0007 0.9992 2.9991 -0.4777 0.5981 -0.6420
5.0003 5.0003 -2.0003 -0.6690 0.8387 -0.1337
-4.1509 4.2857 -6.6529 0.2437 -0.0594 0.9680
3.0003 -1.0001 -4.9990 -0.5722 -0.2481 0.2590
-6.7341 -0.3990 3.6783 0.9644 -0.2318 0.1275
-5.8283 -1.8893 6.2227 0.9542 -0.2290 -0.1927
-5.1388 -2.5741 7.2744 0.9116 -0.2187 -0.3481
2.1812 -8.5229 1.9567 -0.2140 -0.8901 -0.4023
2.0000 2.0005 -4.9993 -0.4404 0.0917 0.3510
0.0002 -2.0008 4.9992 0.1985 0.0248 -0.4949
2.0006 -4.0013 4.9993 -0.0506 -0.1241 -0.6522
-1.0003 5.0008 1.9991 0.2213 0.7213 -0.0872
-0.9998 -5.0008 2.0001 0.1852 -0.6057 -0.1541
-3.0006 5.0011 0.9994 0.4221 0.5467 0.1530
-5.0009 5.0014 0.9995 0.6640 0.4302 0.2969
-4.0007 5.0011 2.9990 0.6253 0.6045 0.0324
-1.9999 -5.0010 4.9996 0.4296 -0.4898 -0.3711
-5.0006 -1.9996 -0.9994 0.5564 -0.6147 0.4427
6.7901 -1.8557 0.7359 -0.7976 0.1921 -0.5718
-0.9999 -5.0006 -0.9993 0.0618 -0.7797 0.1348
-1.6616 0.4706 -7.7352 -0.1157 -0.4834 0.8677
3.0002 1.0002 -4.9992 -0.5650 0.0173 0.2723
-4.6738 4.0570 -5.9781 0.3338 -0.0811 0.9391
-3.0006 5.0012 -0.0004 0.3809 0.4887 0.2493
3.0007 -5.0013 1.0002 -0.3398 -0.4307 -0.3456
3.0006 -5.0009 -2.9990 -0.5044 -0.6628 0.0396
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.500 0.500 -0.384 352.4 148.0 ?
