#------------------------------------------------------------------------------
#$Date: 2021-10-06 17:00:29 +0300 (Wed, 06 Oct 2021) $
#$Revision: 269657 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/87/7128746.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_7128746
loop_
_publ_author_name
'Han, Tian-Jiao'
'Wang, Min-Can'
'Mei, Guang-Jian'
_publ_section_title
;
 2-Indolymethanols as 4-atom-synthons in oxa-Michael reaction cascade:
 access to tetracyclic indoles.
;
_journal_issue                   71
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8921
_journal_page_last               8924
_journal_paper_doi               10.1039/d1cc03653j
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C22 H18 Br N O3'
_chemical_formula_sum            'C22 H18 Br N O3'
_chemical_formula_weight         424.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-04-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-25 deposited with the CCDC.	2021-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.200(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1529(6)
_cell_length_b                   30.7743(11)
_cell_length_c                   8.7822(4)
_cell_measurement_reflns_used    2025
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9910
_cell_measurement_theta_min      5.4260
_cell_volume                     2194.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -11.00   1.00    1.75    --  -33.50 -77.00-180.00   91
  2  ω    -44.00 -16.00   1.00    1.75    --  -33.50 -57.00-150.00   28
  3  ω    -91.00 -65.00   1.00    1.75    --  -33.50 -57.00 120.00   26
  4  ω   -107.00 -81.00   1.00    1.75    --  -33.50 178.00   0.00   26
  5  ω     39.00  98.00   1.00    1.75    --   36.47  57.00  30.00   59
  6  ω     -3.00  74.00   1.00    1.75    --   36.47 -99.00  60.00   77
  7  ω     59.00 104.00   1.00    1.75    --   36.47  57.00  90.00   45
  8  ω     70.00  97.00   1.00   10.50    --  108.00 -94.00-150.00   27
  9  ω     79.00 177.00   1.00   10.50    --  108.00  77.00 -90.00   98
 10  ω    101.00 155.00   1.00   10.50    --  108.00 111.00 150.00   54
 11  ω    133.00 174.00   1.00   10.50    --  108.00  61.00-180.00   41
 12  ω     89.00 130.00   1.00   10.50    --  108.00  61.00-180.00   41
 13  ω    116.00 142.00   1.00   10.50    --  108.00  61.00-120.00   26
 14  ω     41.00 112.00   1.00   10.50    --  108.00-111.00 -30.00   71
 15  ω     38.00 110.00   1.00   10.50    --  108.00 -94.00-180.00   72
 16  ω    139.00 167.00   1.00   10.50    --  108.00  61.00 -60.00   28
 17  ω     41.00  67.00   1.00   10.50    --  108.00 -94.00   0.00   26
 18  ω     66.00 129.00   1.00   10.50    --  108.00 178.00   0.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1864409000
_diffrn_orient_matrix_UB_12      -0.0009990000
_diffrn_orient_matrix_UB_13      -0.0479855000
_diffrn_orient_matrix_UB_21      0.0042915000
_diffrn_orient_matrix_UB_22      -0.0500479000
_diffrn_orient_matrix_UB_23      -0.0023492000
_diffrn_orient_matrix_UB_31      -0.0346879000
_diffrn_orient_matrix_UB_32      -0.0009694000
_diffrn_orient_matrix_UB_33      0.1695000000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8408
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.062
_diffrn_reflns_theta_max         67.062
_diffrn_reflns_theta_min         5.258
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.711
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.284
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3918
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0578
_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)+(0.0810P)²+0.2436P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1529
_refine_ls_wR_factor_ref         0.1675
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2805
_reflns_number_total             3918
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc03653j2.cif
_cod_data_source_block           202104106
_cod_depositor_comments
'Adding full bibliography for 7128745--7128746.cif.'
_cod_original_cell_volume        2194.41(19)
_cod_database_code               7128746
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O5N2Br1
_chemical_oxdiff_usercomment     r
_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   0.854
_shelx_estimated_absorpt_t_min   0.703
_reflns_odcompleteness_completeness 99.85
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Br1) = Uanis(Br1A)
3. Others
 Sof(Br1A)=1-FVAR(1)
 Sof(Br1)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C11(H11)
4.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C18(H18), C19(H19), C21(H21), C22(H22), N1(H1A)
4.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
;
_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 1.364
_oxdiff_exptl_absorpt_empirical_full_min 0.807
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.3971(2) 0.46832(3) 0.7913(2) 0.1310(6) Uani 0.887(5) 1 d . . P A 1
Br1A Br 0.3414(19) 0.4625(2) 0.7217(17) 0.1310(6) Uani 0.113(5) 1 d . . P A 2
C1 C 0.0053(4) 0.65563(12) 0.6825(4) 0.0608(8) Uani 1 1 d . . . . .
H1 H -0.0066 0.6306 0.6234 0.073 Uiso 1 1 calc R . . . .
C2 C -0.1104(5) 0.66623(15) 0.7816(4) 0.0720(10) Uani 1 1 d . . . . .
H2 H -0.1990 0.6477 0.7913 0.086 Uiso 1 1 calc R . . . .
C3 C -0.0964(5) 0.70416(15) 0.8672(4) 0.0766(11) Uani 1 1 d . . . . .
H3 H -0.1776 0.7108 0.9313 0.092 Uiso 1 1 calc R . . . .
C4 C 0.0331(5) 0.73206(13) 0.8602(4) 0.0711(10) Uani 1 1 d . . . . .
H4 H 0.0415 0.7573 0.9186 0.085 Uiso 1 1 calc R . . . .
C5 C 0.1518(5) 0.72134(11) 0.7624(3) 0.0588(8) Uani 1 1 d . . . . .
C6 C 0.1410(4) 0.68310(10) 0.6721(3) 0.0520(7) Uani 1 1 d . . . . .
C7 C 0.2841(4) 0.68274(9) 0.5895(3) 0.0504(6) Uani 1 1 d . . . . .
C8 C 0.3751(4) 0.71875(10) 0.6326(3) 0.0571(7) Uani 1 1 d . . . . .
C9 C 0.5336(5) 0.73018(11) 0.5739(4) 0.0652(8) Uani 1 1 d . . . . .
H9A H 0.5414 0.7614 0.5617 0.078 Uiso 1 1 calc R . . . .
H9B H 0.6243 0.7207 0.6453 0.078 Uiso 1 1 calc R . . . .
C10 C 0.3465(4) 0.64967(9) 0.4852(3) 0.0469(6) Uani 1 1 d . . . . .
C11 C 0.5161(4) 0.66280(10) 0.4343(3) 0.0511(6) Uani 1 1 d . . . . .
H11 H 0.6064 0.6481 0.4951 0.061 Uiso 1 1 calc R . . . .
C12 C 0.5014(4) 0.64766(10) 0.2701(3) 0.0518(6) Uani 1 1 d . . . . .
C13 C 0.3393(4) 0.64265(10) 0.2262(3) 0.0525(7) Uani 1 1 d . . . . .
C14 C 0.2508(5) 0.63328(15) 0.0756(4) 0.0722(10) Uani 1 1 d . . . . .
H14A H 0.3278 0.6325 -0.0008 0.108 Uiso 1 1 calc GR . . . .
H14B H 0.1705 0.6556 0.0506 0.108 Uiso 1 1 calc GR . . . .
H14C H 0.1965 0.6057 0.0792 0.108 Uiso 1 1 calc GR . . . .
C15 C 0.6363(5) 0.64397(12) 0.1729(4) 0.0649(8) Uani 1 1 d . . . . .
C16 C 0.8085(5) 0.6511(2) 0.2465(5) 0.0946(15) Uani 1 1 d . . . . .
H16A H 0.8116 0.6772 0.3064 0.142 Uiso 1 1 calc GR . . . .
H16B H 0.8832 0.6537 0.1685 0.142 Uiso 1 1 calc GR . . . .
H16C H 0.8404 0.6268 0.3113 0.142 Uiso 1 1 calc GR . . . .
C17 C 0.3549(4) 0.60441(9) 0.5556(3) 0.0534(7) Uani 1 1 d . . . . .
C18 C 0.4310(5) 0.59934(12) 0.7021(4) 0.0638(8) Uani 1 1 d . . . . .
H18 H 0.4742 0.6236 0.7547 0.077 Uiso 1 1 calc R . . . .
C19 C 0.4442(6) 0.55919(14) 0.7717(5) 0.0794(11) Uani 1 1 d . . . . .
H19 H 0.4969 0.5562 0.8695 0.095 Uiso 1 1 calc R . . . .
C20 C 0.3779(7) 0.52374(12) 0.6931(5) 0.0910(14) Uani 1 1 d . . . . .
C21 C 0.3036(9) 0.52782(14) 0.5493(6) 0.1077(18) Uani 1 1 d . . . . .
H21 H 0.2622 0.5033 0.4969 0.129 Uiso 1 1 calc R . . . .
C22 C 0.2892(6) 0.56817(12) 0.4801(5) 0.0820(12) Uani 1 1 d . . . . .
H22 H 0.2353 0.5709 0.3827 0.098 Uiso 1 1 calc R . . . .
N1 N 0.2949(4) 0.74224(9) 0.7359(3) 0.0651(7) Uani 1 1 d . . . . .
H1A H 0.3291 0.7663 0.7775 0.078 Uiso 1 1 calc R . . . .
O1 O 0.2401(3) 0.64810(7) 0.3399(2) 0.0524(5) Uani 1 1 d . . . . .
O2 O 0.5417(3) 0.70903(7) 0.4292(2) 0.0576(5) Uani 1 1 d . . . . .
O3 O 0.6156(4) 0.63526(12) 0.0387(3) 0.0906(9) 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_
_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
C2 C1 H1 120.4 . . ?
C2 C1 C6 119.2(3) . . ?
C6 C1 H1 120.4 . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.9(4) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 122.0(3) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 121.2 . . ?
C3 C4 C5 117.6(3) . . ?
C5 C4 H4 121.2 . . ?
C4 C5 C6 122.1(4) . . ?
N1 C5 C4 130.1(3) . . ?
N1 C5 C6 107.8(3) . . ?
C1 C6 C5 118.2(3) . . ?
C1 C6 C7 135.6(3) . . ?
C5 C6 C7 106.2(3) . . ?
C6 C7 C10 131.2(3) . . ?
C8 C7 C6 107.5(3) . . ?
C8 C7 C10 121.1(3) . . ?
C7 C8 C9 124.5(3) . . ?
C7 C8 N1 109.4(3) . . ?
N1 C8 C9 126.2(3) . . ?
C8 C9 H9A 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
O2 C9 C8 108.2(3) . . ?
O2 C9 H9A 110.0 . . ?
O2 C9 H9B 110.0 . . ?
C7 C10 C11 111.4(2) . . ?
C7 C10 C17 112.4(2) . . ?
C17 C10 C11 110.4(2) . . ?
O1 C10 C7 110.3(2) . . ?
O1 C10 C11 103.3(2) . . ?
O1 C10 C17 108.8(2) . . ?
C10 C11 H11 111.7 . . ?
C12 C11 C10 101.5(2) . . ?
C12 C11 H11 111.7 . . ?
O2 C11 C10 113.8(2) . . ?
O2 C11 H11 111.7 . . ?
O2 C11 C12 105.9(2) . . ?
C13 C12 C11 107.4(3) . . ?
C13 C12 C15 126.5(3) . . ?
C15 C12 C11 125.8(3) . . ?
C12 C13 C14 131.6(3) . . ?
O1 C13 C12 114.2(3) . . ?
O1 C13 C14 114.2(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 C16 117.5(3) . . ?
O3 C15 C12 123.0(4) . . ?
O3 C15 C16 119.6(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C10 118.7(3) . . ?
C22 C17 C10 122.9(3) . . ?
C22 C17 C18 118.4(3) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 C17 121.6(4) . . ?
C19 C18 H18 119.2 . . ?
C18 C19 H19 120.7 . . ?
C20 C19 C18 118.5(4) . . ?
C20 C19 H19 120.7 . . ?
C19 C20 Br1 118.0(4) . . ?
C19 C20 Br1A 140.2(6) . . ?
C21 C20 Br1 121.0(4) . . ?
C21 C20 Br1A 98.7(6) . . ?
C21 C20 C19 121.0(4) . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.4(4) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 120.1(4) . . ?
C17 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C5 N1 C8 109.2(3) . . ?
C5 N1 H1A 125.4 . . ?
C8 N1 H1A 125.4 . . ?
C13 O1 C10 107.4(2) . . ?
C9 O2 C11 113.7(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 C20 1.911(4) . ?
Br1A C20 1.926(9) . ?
C1 H1 0.9300 . ?
C1 C2 1.379(5) . ?
C1 C6 1.402(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.366(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(5) . ?
C5 C6 1.418(4) . ?
C5 N1 1.371(5) . ?
C6 C7 1.428(5) . ?
C7 C8 1.368(5) . ?
C7 C10 1.489(4) . ?
C8 C9 1.477(5) . ?
C8 N1 1.371(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 O2 1.435(4) . ?
C10 C11 1.545(4) . ?
C10 C17 1.523(4) . ?
C10 O1 1.477(3) . ?
C11 H11 0.9800 . ?
C11 C12 1.509(4) . ?
C11 O2 1.439(4) . ?
C12 C13 1.352(5) . ?
C12 C15 1.456(5) . ?
C13 C14 1.476(4) . ?
C13 O1 1.351(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.507(6) . ?
C15 O3 1.206(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.385(5) . ?
C17 C22 1.380(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.378(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.375(7) . ?
C20 C21 1.356(8) . ?
C21 H21 0.9300 . ?
C21 C22 1.383(6) . ?
C22 H22 0.9300 . ?
N1 H1A 0.8600 . ?
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 C20 C21 C22 179.4(4) . . . . ?
Br1A C20 C21 C22 176.0(6) . . . . ?
C1 C2 C3 C4 -1.5(6) . . . . ?
C1 C6 C7 C8 -178.0(3) . . . . ?
C1 C6 C7 C10 -3.9(6) . . . . ?
C2 C1 C6 C5 -1.2(5) . . . . ?
C2 C1 C6 C7 177.9(3) . . . . ?
C2 C3 C4 C5 0.4(6) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C3 C4 C5 N1 -177.9(3) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
C4 C5 C6 C7 -179.1(3) . . . . ?
C4 C5 N1 C8 178.2(3) . . . . ?
C5 C6 C7 C8 1.2(3) . . . . ?
C5 C6 C7 C10 175.3(3) . . . . ?
C6 C1 C2 C3 1.9(6) . . . . ?
C6 C5 N1 C8 -0.1(4) . . . . ?
C6 C7 C8 C9 179.5(3) . . . . ?
C6 C7 C8 N1 -1.3(4) . . . . ?
C6 C7 C10 C11 -175.1(3) . . . . ?
C6 C7 C10 C17 -50.7(4) . . . . ?
C6 C7 C10 O1 70.8(4) . . . . ?
C7 C8 C9 O2 22.6(4) . . . . ?
C7 C8 N1 C5 0.8(4) . . . . ?
C7 C10 C11 C12 -142.4(2) . . . . ?
C7 C10 C11 O2 -29.1(3) . . . . ?
C7 C10 C17 C18 -49.5(4) . . . . ?
C7 C10 C17 C22 130.2(4) . . . . ?
C7 C10 O1 C13 141.1(2) . . . . ?
C8 C7 C10 C11 -1.7(4) . . . . ?
C8 C7 C10 C17 122.7(3) . . . . ?
C8 C7 C10 O1 -115.7(3) . . . . ?
C8 C9 O2 C11 -54.4(4) . . . . ?
C9 C8 N1 C5 -180.0(3) . . . . ?
C10 C7 C8 C9 4.7(5) . . . . ?
C10 C7 C8 N1 -176.1(3) . . . . ?
C10 C11 C12 C13 18.9(3) . . . . ?
C10 C11 C12 C15 -167.3(3) . . . . ?
C10 C11 O2 C9 60.4(3) . . . . ?
C10 C17 C18 C19 -179.3(3) . . . . ?
C10 C17 C22 C21 178.8(4) . . . . ?
C11 C10 C17 C18 75.5(3) . . . . ?
C11 C10 C17 C22 -104.9(4) . . . . ?
C11 C10 O1 C13 22.0(3) . . . . ?
C11 C12 C13 C14 172.4(4) . . . . ?
C11 C12 C13 O1 -5.9(4) . . . . ?
C11 C12 C15 C16 7.2(5) . . . . ?
C11 C12 C15 O3 -173.4(4) . . . . ?
C12 C11 O2 C9 171.0(3) . . . . ?
C12 C13 O1 C10 -10.8(3) . . . . ?
C13 C12 C15 C16 179.8(4) . . . . ?
C13 C12 C15 O3 -0.9(6) . . . . ?
C14 C13 O1 C10 170.6(3) . . . . ?
C15 C12 C13 C14 -1.3(6) . . . . ?
C15 C12 C13 O1 -179.6(3) . . . . ?
C17 C10 C11 C12 92.0(3) . . . . ?
C17 C10 C11 O2 -154.6(2) . . . . ?
C17 C10 O1 C13 -95.2(3) . . . . ?
C17 C18 C19 C20 -0.9(6) . . . . ?
C18 C17 C22 C21 -1.5(7) . . . . ?
C18 C19 C20 Br1 -180.0(3) . . . . ?
C18 C19 C20 Br1A -175.4(7) . . . . ?
C18 C19 C20 C21 1.2(8) . . . . ?
C19 C20 C21 C22 -1.8(9) . . . . ?
C20 C21 C22 C17 2.0(9) . . . . ?
C22 C17 C18 C19 1.0(6) . . . . ?
N1 C5 C6 C1 178.7(3) . . . . ?
N1 C5 C6 C7 -0.7(3) . . . . ?
N1 C8 C9 O2 -156.5(3) . . . . ?
O1 C10 C11 C12 -24.1(3) . . . . ?
O1 C10 C11 O2 89.2(3) . . . . ?
O1 C10 C17 C18 -171.9(3) . . . . ?
O1 C10 C17 C22 7.8(4) . . . . ?
O2 C11 C12 C13 -100.2(3) . . . . ?
O2 C11 C12 C15 73.6(4) . . . . ?
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 0.000 0.000 -0.671 206.1 47.7 ?
2 0.000 0.500 -0.148 206.1 47.7 ?
