# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_9st229
_database_code_depnum_ccdc_archive 'CCDC 2023472'
_audit_update_record             
;
2020-08-15 deposited with the CCDC.	2021-03-17 downloaded from the CCDC.
;
_audit_creation_date             2019-09-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H17 Br N2 O3'
_chemical_formula_sum            'C19 H17 Br N2 O3'
_chemical_formula_weight         401.25
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.4819(3)
_cell_length_b                   5.4926(2)
_cell_length_c                   25.2518(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.834(3)
_cell_angle_gamma                90
_cell_volume                     1694.42(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3261
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3840
_cell_measurement_theta_min      3.5600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.488
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            5983
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.578
_diffrn_reflns_theta_min         3.577
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     70.00 119.00   1.00    1.00    --   40.98  19.00 120.00   49
  2  ω    124.00 164.00   1.00    1.00    --  106.95 125.00   0.00   40
  3  ω    105.00 168.00   1.00    1.00    --  106.95 125.00 120.00   63
  4  ω     81.00 178.00   1.00    1.00    --  106.95  45.00 -90.00   97
  5  ω    138.00 165.00   1.00    1.00    --  106.95 125.00-120.00   27
  6  ω     36.00 130.00   1.00    1.00    --  106.95 -61.00 120.00   94
  7  ω     25.00  96.00   1.00    1.00    --   40.98-125.00 150.00   71
  8  ω     28.00 104.00   1.00    1.00    --  106.95 -94.00  60.00   76
  9  ω      6.00  35.00   1.00    1.00    --   40.98 -99.00-180.00   29
 10  ω    -24.00  65.00   1.00    1.00    --   40.98 -57.00-150.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1089999000
_diffrn_orient_matrix_UB_12      0.1398479000
_diffrn_orient_matrix_UB_13      0.0148480000
_diffrn_orient_matrix_UB_21      0.0163343000
_diffrn_orient_matrix_UB_22      -0.0282852000
_diffrn_orient_matrix_UB_23      -0.0585140000
_diffrn_orient_matrix_UB_31      -0.0612858000
_diffrn_orient_matrix_UB_32      0.2415083000
_diffrn_orient_matrix_UB_33      -0.0154983000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2860
_reflns_number_total             3295
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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)'
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0308
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0376P)²+0.2301P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0817
_refine_special_details          ?
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C5(H5), C6(H6), C3(H3A), C14(H14), C10(H10), C13(H13),
 C12(H12), C11(H11)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 1.00809(2) 0.83291(5) 0.25228(2) 0.02924(10) Uani 1 1 d . . . . .
O2 O 0.99036(12) 0.8322(3) 0.55393(6) 0.0235(3) Uani 1 1 d . . . . .
O1 O 0.63445(12) 1.0823(3) 0.50763(6) 0.0237(3) Uani 1 1 d . . . . .
O3 O 0.86220(12) 0.4584(3) 0.48426(6) 0.0227(3) Uani 1 1 d . . . . .
H3 H 0.912011 0.407255 0.470603 0.034 Uiso 1 1 calc GR . . . .
N2 N 0.81941(14) 1.0021(4) 0.53883(6) 0.0182(4) Uani 1 1 d . . . . .
N1 N 0.54474(15) 0.7778(4) 0.41969(7) 0.0237(4) Uani 1 1 d . . . . .
H1 H 0.533799 0.912690 0.435023 0.028 Uiso 1 1 calc R . . . .
C1 C 0.75382(16) 0.5817(4) 0.35388(7) 0.0182(4) Uani 1 1 d . . . . .
C16 C 0.71723(16) 0.9726(4) 0.50275(8) 0.0180(4) Uani 1 1 d . . . . .
C2 C 0.73923(17) 0.7977(4) 0.32478(8) 0.0202(4) Uani 1 1 d . . . . .
H2 H 0.678406 0.894003 0.325815 0.024 Uiso 1 1 calc R . . . .
C4 C 0.90445(17) 0.7272(5) 0.29327(8) 0.0212(5) Uani 1 1 d . . . . .
C9 C 0.45150(17) 0.6510(4) 0.38956(8) 0.0194(4) Uani 1 1 d . . . . .
C17 C 0.89738(17) 0.8517(4) 0.52679(8) 0.0188(4) Uani 1 1 d . . . . .
C18 C 0.84979(17) 0.7121(4) 0.47493(8) 0.0187(4) Uani 1 1 d . . . . .
H18 H 0.885433 0.762199 0.445532 0.022 Uiso 1 1 calc R . . . .
C15 C 0.73248(17) 0.7919(4) 0.46363(8) 0.0180(4) Uani 1 1 d . . . . .
C8 C 0.64910(17) 0.6973(4) 0.42540(8) 0.0181(4) Uani 1 1 d . . . . .
C5 C 0.92105(17) 0.5102(4) 0.32135(8) 0.0219(5) Uani 1 1 d . . . . .
H5 H 0.981905 0.414356 0.320113 0.026 Uiso 1 1 calc R . . . .
C7 C 0.67184(17) 0.5008(4) 0.38722(8) 0.0197(4) Uani 1 1 d . . . . .
H7A H 0.603838 0.455950 0.363055 0.024 Uiso 1 1 calc R . . . .
H7B H 0.699876 0.357594 0.408001 0.024 Uiso 1 1 calc R . . . .
C6 C 0.84490(17) 0.4374(4) 0.35161(8) 0.0201(4) Uani 1 1 d . . . . .
H6 H 0.854891 0.291070 0.370503 0.024 Uiso 1 1 calc R . . . .
C3 C 0.81369(18) 0.8728(4) 0.29415(8) 0.0222(5) Uani 1 1 d . . . . .
H3A H 0.803097 1.017397 0.274619 0.027 Uiso 1 1 calc R . . . .
C19 C 0.83902(18) 1.1719(4) 0.58418(8) 0.0223(5) Uani 1 1 d . . . . .
H19A H 0.774497 1.267941 0.583556 0.033 Uiso 1 1 calc GR . . . .
H19B H 0.899025 1.277021 0.581322 0.033 Uiso 1 1 calc GR . . . .
H19C H 0.856429 1.082661 0.617529 0.033 Uiso 1 1 calc GR . . . .
C14 C 0.39469(17) 0.7459(5) 0.34109(8) 0.0224(5) Uani 1 1 d . . . . .
H14 H 0.417426 0.890471 0.327684 0.027 Uiso 1 1 calc R . . . .
C10 C 0.41886(18) 0.4332(4) 0.40924(8) 0.0241(5) Uani 1 1 d . . . . .
H10 H 0.457317 0.370179 0.441819 0.029 Uiso 1 1 calc R . . . .
C13 C 0.30301(18) 0.6229(5) 0.31253(8) 0.0280(5) Uani 1 1 d . . . . .
H13 H 0.263734 0.687163 0.280267 0.034 Uiso 1 1 calc R . . . .
C12 C 0.27041(19) 0.4062(5) 0.33199(9) 0.0298(6) Uani 1 1 d . . . . .
H12 H 0.209373 0.324348 0.312861 0.036 Uiso 1 1 calc R . . . .
C11 C 0.3293(2) 0.3106(5) 0.38037(10) 0.0285(5) Uani 1 1 d . . . . .
H11 H 0.308050 0.163421 0.393263 0.034 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C4 1.906(2) . ?
O2 C17 1.226(3) . ?
O1 C16 1.224(3) . ?
O3 H3 0.8200 . ?
O3 C18 1.417(3) . ?
N2 C16 1.416(2) . ?
N2 C17 1.357(3) . ?
N2 C19 1.458(3) . ?
N1 H1 0.8600 . ?
N1 C9 1.433(3) . ?
N1 C8 1.355(3) . ?
C1 C2 1.388(3) . ?
C1 C7 1.519(3) . ?
C1 C6 1.396(3) . ?
C16 C15 1.440(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(3) . ?
C4 C5 1.380(3) . ?
C4 C3 1.390(3) . ?
C9 C14 1.384(3) . ?
C9 C10 1.388(3) . ?
C17 C18 1.529(3) . ?
C18 H18 0.9800 . ?
C18 C15 1.499(3) . ?
C15 C8 1.369(3) . ?
C8 C7 1.512(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.395(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C6 H6 0.9300 . ?
C3 H3A 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C14 H14 0.9300 . ?
C14 C13 1.396(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.380(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.393(3) . ?
C11 H11 0.9300 . ?

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
C18 O3 H3 109.5 . . ?
C16 N2 C19 124.20(18) . . ?
C17 N2 C16 112.26(17) . . ?
C17 N2 C19 123.54(17) . . ?
C9 N1 H1 118.1 . . ?
C8 N1 H1 118.1 . . ?
C8 N1 C9 123.79(19) . . ?
C2 C1 C7 120.9(2) . . ?
C2 C1 C6 118.9(2) . . ?
C6 C1 C7 120.2(2) . . ?
O1 C16 N2 123.11(19) . . ?
O1 C16 C15 129.90(19) . . ?
N2 C16 C15 106.96(17) . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.3(2) . . ?
C3 C2 H2 119.4 . . ?
C5 C4 Br1 119.66(17) . . ?
C5 C4 C3 121.7(2) . . ?
C3 C4 Br1 118.65(18) . . ?
C14 C9 N1 119.9(2) . . ?
C14 C9 C10 120.4(2) . . ?
C10 C9 N1 119.64(19) . . ?
O2 C17 N2 124.63(19) . . ?
O2 C17 C18 126.3(2) . . ?
N2 C17 C18 109.06(17) . . ?
O3 C18 C17 109.94(16) . . ?
O3 C18 H18 110.6 . . ?
O3 C18 C15 112.87(18) . . ?
C17 C18 H18 110.6 . . ?
C15 C18 C17 102.08(17) . . ?
C15 C18 H18 110.6 . . ?
C16 C15 C18 109.41(17) . . ?
C8 C15 C16 123.86(19) . . ?
C8 C15 C18 126.52(19) . . ?
N1 C8 C15 121.8(2) . . ?
N1 C8 C7 117.83(18) . . ?
C15 C8 C7 120.38(19) . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.8(2) . . ?
C6 C5 H5 120.6 . . ?
C1 C7 H7A 109.1 . . ?
C1 C7 H7B 109.1 . . ?
C8 C7 C1 112.35(18) . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.8(2) . . ?
C5 C6 H6 119.6 . . ?
C2 C3 C4 118.6(2) . . ?
C2 C3 H3A 120.7 . . ?
C4 C3 H3A 120.7 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C9 C14 H14 120.3 . . ?
C9 C14 C13 119.4(2) . . ?
C13 C14 H14 120.3 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.8(2) . . ?
C11 C10 H10 120.1 . . ?
C14 C13 H13 119.9 . . ?
C12 C13 C14 120.3(2) . . ?
C12 C13 H13 119.9 . . ?
C13 C12 H12 120.1 . . ?
C13 C12 C11 119.8(2) . . ?
C11 C12 H12 120.1 . . ?
C10 C11 C12 120.3(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?

_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 1.752
_oxdiff_exptl_absorpt_empirical_full_min 0.649
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_yst-i
_database_code_depnum_ccdc_archive 'CCDC 2023473'
_audit_update_record             
;
2020-08-15 deposited with the CCDC.	2021-03-17 downloaded from the CCDC.
;
_audit_creation_date             2019-05-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 I N2 O3'
_chemical_formula_sum            'C19 H15 I N2 O3'
_chemical_formula_weight         446.23
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   20.0555(10)
_cell_length_b                   7.4291(5)
_cell_length_c                   23.0509(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3434.5(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4260
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.8250
_cell_measurement_theta_min      2.9270
_shelx_estimated_absorpt_T_max   0.849
_shelx_estimated_absorpt_T_min   0.805
_exptl_absorpt_coefficient_mu    1.885
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9747
_diffrn_reflns_point_group_measured_fraction_full 0.848
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.215
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_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    -18.00  16.00   1.00    5.00    --   11.74 -99.00-150.00   34
  2  ω    -12.00  24.00   1.00    5.00    --   11.74  37.00-180.00   36
  3  ω    -53.00  14.00   1.00    5.00    --   11.74 -77.00   0.00   67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0083538000
_diffrn_orient_matrix_UB_12      0.0551143000
_diffrn_orient_matrix_UB_13      0.0240319000
_diffrn_orient_matrix_UB_21      0.0304437000
_diffrn_orient_matrix_UB_22      -0.0238719000
_diffrn_orient_matrix_UB_23      0.0136585000
_diffrn_orient_matrix_UB_31      0.0159865000
_diffrn_orient_matrix_UB_32      0.0742167000
_diffrn_orient_matrix_UB_33      -0.0134507000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.651
_reflns_Friedel_fraction_full    0.688
_reflns_Friedel_fraction_max     0.688
_reflns_number_gt                4555
_reflns_number_total             5136
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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)'
_refine_diff_density_max         0.768
_refine_diff_density_min         -0.712
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details 
;
 Flack x determined using 1561 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.26(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         5136
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.025
_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)+(0.0241P)²+2.1151P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0678
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C18B) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C14B) \\sim Ueq, Uanis(C17B) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
3.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C9B(H9B), C11B(H11B)
3.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C16(H16), C18(H18), C16B(H16B), C3(H3), C15(H15), C17B(H17B),
 C6B(H6B), C18B(H18B), C19B(H19B), C15B(H15B), C6(H6), C5B(H5B), C2B(H2B),
 C19(H19), C4(H4), C3B(H3B), C2(H2), C5(H5), C4B(H4B)
3.c Idealised Me refined as rotating group:
 C13(H13D,H13E,H13F), C13B(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
I1B I 0.42869(2) -0.10869(7) 0.29433(2) 0.02085(15) Uani 1 1 d . . . . .
I1 I 0.68281(2) 0.60668(8) 0.70857(2) 0.02152(15) Uani 1 1 d . . . . .
O1B O 0.3966(4) 0.5396(10) 0.4371(4) 0.0235(19) Uani 1 1 d . . . . .
O2B O 0.6211(4) 0.4877(8) 0.4657(5) 0.015(2) Uani 1 1 d . . . . .
O3B O 0.5689(3) 0.1384(7) 0.4163(2) 0.0129(12) Uani 1 1 d . . . . .
O1 O 0.8246(3) 0.3615(7) 0.5858(2) 0.0114(12) Uani 1 1 d . . . . .
N2 N 0.7637(4) -0.0515(11) 0.5532(3) 0.0109(16) Uani 1 1 d . . . . .
N1B N 0.5270(3) 0.1481(9) 0.3645(3) 0.0111(16) Uani 1 1 d . . . . .
O2 O 0.8751(4) 0.0090(8) 0.5354(5) 0.018(2) Uani 1 1 d . . . . .
O3 O 0.6500(4) -0.0309(9) 0.5649(4) 0.0220(19) Uani 1 1 d . . . . .
C17 C 0.8444(5) -0.0381(13) 0.7588(4) 0.018(2) Uani 1 1 d . . . . .
H17 H 0.858364 -0.118097 0.787328 0.021 Uiso 1 1 calc R . . . .
N2B N 0.5112(4) 0.5523(12) 0.4473(3) 0.0152(17) Uani 1 1 d . . . . .
C16 C 0.7792(6) 0.0142(11) 0.7557(5) 0.018(3) Uani 1 1 d . . . . .
H16 H 0.748903 -0.033877 0.781964 0.021 Uiso 1 1 calc R . . . .
C7 C 0.6650(4) 0.4321(12) 0.6378(4) 0.0104(18) Uani 1 1 d . . . . .
C18 C 0.8892(5) 0.0299(13) 0.7188(6) 0.017(2) Uani 1 1 d . . . . .
H18 H 0.933204 -0.009303 0.719435 0.021 Uiso 1 1 calc R . . . .
N1 N 0.7825(3) 0.3518(10) 0.6371(3) 0.0116(16) Uani 1 1 d . . . . .
C16B C 0.6343(5) 0.4728(12) 0.2830(6) 0.016(3) Uani 1 1 d . . . . .
H16B H 0.678560 0.510078 0.281695 0.020 Uiso 1 1 calc R . . . .
C8B C 0.4606(4) 0.1582(11) 0.3871(3) 0.0096(17) Uani 1 1 d . . . . .
C3 C 0.4930(4) 0.2428(13) 0.6092(3) 0.017(2) Uani 1 1 d . . . . .
H3 H 0.470762 0.133252 0.612161 0.021 Uiso 1 1 calc R . . . .
C10B C 0.4495(5) 0.4646(13) 0.4418(5) 0.010(2) Uani 1 1 d . . . . .
C15 C 0.7565(4) 0.1372(10) 0.7144(4) 0.0135(18) Uani 1 1 d . . . . .
H15 H 0.711804 0.169809 0.712797 0.016 Uiso 1 1 calc R . . . .
C17B C 0.5887(5) 0.5427(14) 0.2436(4) 0.017(2) Uani 1 1 d . U . . .
H17B H 0.602396 0.626142 0.215989 0.020 Uiso 1 1 calc R . . . .
C1B C 0.3389(4) 0.0809(12) 0.3824(4) 0.011(2) Uani 1 1 d . . . . .
C6B C 0.3058(4) 0.2452(13) 0.3820(4) 0.018(2) Uani 1 1 d . . . . .
H6B H 0.328385 0.348603 0.370516 0.021 Uiso 1 1 calc R . . . .
C7B C 0.4095(4) 0.0678(13) 0.3645(4) 0.0109(18) Uani 1 1 d . . . . .
C1 C 0.5940(4) 0.4179(12) 0.6197(4) 0.014(2) Uani 1 1 d . . . . .
C12 C 0.7046(5) 0.0405(15) 0.5594(5) 0.017(2) Uani 1 1 d . . . . .
C18B C 0.5220(5) 0.4870(11) 0.2455(6) 0.013(3) Uani 1 1 d . U . . .
H18B H 0.491417 0.532409 0.218961 0.016 Uiso 1 1 calc R . . . .
C14B C 0.5474(4) 0.2935(10) 0.3269(3) 0.0092(17) Uani 1 1 d . U . . .
C9 C 0.7179(4) 0.2440(11) 0.5567(3) 0.0092(18) Uani 1 1 d . . . . .
H9 H 0.690413 0.303695 0.527285 0.011 Uiso 1 1 calc R . . . .
C19B C 0.5017(4) 0.3646(11) 0.2870(4) 0.0146(19) Uani 1 1 d . . . . .
H19B H 0.457246 0.329015 0.288488 0.017 Uiso 1 1 calc R . . . .
C15B C 0.6142(4) 0.3462(11) 0.3248(4) 0.0143(19) Uani 1 1 d . . . . .
H15B H 0.644965 0.298271 0.350734 0.017 Uiso 1 1 calc R . . . .
C6 C 0.5592(5) 0.5724(15) 0.6008(4) 0.017(2) Uani 1 1 d . . . . .
H6 H 0.580719 0.683054 0.598330 0.020 Uiso 1 1 calc R . . . .
C13 C 0.7685(5) -0.2473(13) 0.5549(5) 0.023(3) Uani 1 1 d . . . . .
H13D H 0.783812 -0.284551 0.592526 0.034 Uiso 1 1 calc GR . . . .
H13E H 0.799360 -0.287477 0.525882 0.034 Uiso 1 1 calc GR . . . .
H13F H 0.725391 -0.298673 0.547572 0.034 Uiso 1 1 calc GR . . . .
C12B C 0.5637(5) 0.4399(14) 0.4583(4) 0.0132(18) Uani 1 1 d . . . . .
C5B C 0.2398(4) 0.2565(13) 0.3983(3) 0.020(2) Uani 1 1 d . . . . .
H5B H 0.218551 0.367714 0.398659 0.024 Uiso 1 1 calc R . . . .
C10 C 0.7931(4) 0.2524(12) 0.5418(4) 0.011(2) Uani 1 1 d . . . . .
H10 H 0.799836 0.305529 0.503313 0.013 Uiso 1 1 calc R . . . .
C2B C 0.3038(5) -0.0731(15) 0.3976(4) 0.018(2) Uani 1 1 d . . . . .
H2B H 0.324896 -0.184538 0.396857 0.022 Uiso 1 1 calc R . . . .
C8 C 0.7160(4) 0.3419(11) 0.6141(3) 0.0106(18) Uani 1 1 d . . . . .
C13B C 0.5169(5) 0.7495(13) 0.4466(4) 0.021(2) Uani 1 1 d . . . . .
H13A H 0.527824 0.788991 0.408083 0.031 Uiso 1 1 calc GR . . . .
H13B H 0.551415 0.786388 0.472916 0.031 Uiso 1 1 calc GR . . . .
H13C H 0.475298 0.801931 0.458276 0.031 Uiso 1 1 calc GR . . . .
C19 C 0.8695(4) 0.1547(12) 0.6781(4) 0.0145(19) Uani 1 1 d . . . . .
H19 H 0.900335 0.202483 0.652220 0.017 Uiso 1 1 calc R . . . .
C4 C 0.4591(4) 0.3946(13) 0.5908(4) 0.015(2) Uani 1 1 d . . . . .
H4 H 0.414050 0.387086 0.581636 0.018 Uiso 1 1 calc R . . . .
C9B C 0.4628(4) 0.2597(11) 0.4448(4) 0.0111(19) Uani 1 1 d . . . . .
H9B H 0.434755 0.201596 0.474115 0.013 Uiso 1 1 calc R . . . .
C11B C 0.5373(4) 0.2456(13) 0.4604(4) 0.010(2) Uani 1 1 d . . . . .
H11B H 0.543480 0.192567 0.498976 0.012 Uiso 1 1 calc R . . . .
C11 C 0.8183(5) 0.0597(14) 0.5430(4) 0.0131(18) Uani 1 1 d . . . . .
C3B C 0.2370(4) -0.0614(17) 0.4140(4) 0.020(2) Uani 1 1 d . . . . .
H3B H 0.214005 -0.164699 0.424943 0.024 Uiso 1 1 calc R . . . .
C2 C 0.5610(4) 0.2544(13) 0.6235(4) 0.014(2) Uani 1 1 d . . . . .
H2 H 0.583843 0.152172 0.635564 0.017 Uiso 1 1 calc R . . . .
C5 C 0.4918(5) 0.5565(16) 0.5860(4) 0.020(2) Uani 1 1 d . . . . .
H5 H 0.468800 0.657045 0.572675 0.024 Uiso 1 1 calc R . . . .
C4B C 0.2050(4) 0.1032(15) 0.4141(4) 0.026(2) Uani 1 1 d . . . . .
H4B H 0.160377 0.111058 0.424745 0.031 Uiso 1 1 calc R . . . .
C14 C 0.8022(4) 0.2093(11) 0.6762(3) 0.0108(18) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
I1B C7B 2.118(9) . ?
I1 C7 2.115(9) . ?
O1B C10B 1.203(13) . ?
O2B C12B 1.216(12) . ?
O3B N1B 1.462(8) . ?
O3B C11B 1.438(11) . ?
O1 N1 1.454(8) . ?
O1 C10 1.444(10) . ?
N2 C12 1.375(14) . ?
N2 C13 1.458(12) . ?
N2 C11 1.391(13) . ?
N1B C8B 1.432(10) . ?
N1B C14B 1.444(10) . ?
O2 C11 1.213(12) . ?
O3 C12 1.223(13) . ?
C17 H17 0.9300 . ?
C17 C16 1.365(15) . ?
C17 C18 1.383(15) . ?
N2B C10B 1.405(13) . ?
N2B C12B 1.368(13) . ?
N2B C13B 1.469(13) . ?
C16 H16 0.9300 . ?
C16 C15 1.395(14) . ?
C7 C1 1.486(12) . ?
C7 C8 1.340(12) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(14) . ?
N1 C8 1.437(9) . ?
N1 C14 1.444(10) . ?
C16B H16B 0.9300 . ?
C16B C17B 1.390(16) . ?
C16B C15B 1.405(15) . ?
C8B C7B 1.331(12) . ?
C8B C9B 1.530(11) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(13) . ?
C3 C2 1.406(11) . ?
C10B C9B 1.547(13) . ?
C15 H15 0.9300 . ?
C15 C14 1.380(11) . ?
C17B H17B 0.9300 . ?
C17B C18B 1.401(13) . ?
C1B C6B 1.390(12) . ?
C1B C7B 1.477(11) . ?
C1B C2B 1.389(14) . ?
C6B H6B 0.9300 . ?
C6B C5B 1.378(12) . ?
C1 C6 1.412(14) . ?
C1 C2 1.387(13) . ?
C12 C9 1.537(14) . ?
C18B H18B 0.9300 . ?
C18B C19B 1.381(14) . ?
C14B C19B 1.401(11) . ?
C14B C15B 1.398(11) . ?
C9 H9 0.9800 . ?
C9 C10 1.550(10) . ?
C9 C8 1.510(11) . ?
C19B H19B 0.9300 . ?
C15B H15B 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.399(13) . ?
C13 H13D 0.9600 . ?
C13 H13E 0.9600 . ?
C13 H13F 0.9600 . ?
C12B C11B 1.539(13) . ?
C5B H5B 0.9300 . ?
C5B C4B 1.385(13) . ?
C10 H10 0.9800 . ?
C10 C11 1.518(14) . ?
C2B H2B 0.9300 . ?
C2B C3B 1.394(13) . ?
C13B H13A 0.9600 . ?
C13B H13B 0.9600 . ?
C13B H13C 0.9600 . ?
C19 H19 0.9300 . ?
C19 C14 1.411(11) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(14) . ?
C9B H9B 0.9800 . ?
C9B C11B 1.540(11) . ?
C11B H11B 0.9800 . ?
C3B H3B 0.9300 . ?
C3B C4B 1.382(15) . ?
C2 H2 0.9300 . ?
C5 H5 0.9300 . ?
C4B H4B 0.9300 . ?

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
C11B O3B N1B 107.3(5) . . ?
C10 O1 N1 106.9(5) . . ?
C12 N2 C13 123.3(9) . . ?
C12 N2 C11 113.6(9) . . ?
C11 N2 C13 123.1(8) . . ?
C8B N1B O3B 103.9(5) . . ?
C8B N1B C14B 116.2(6) . . ?
C14B N1B O3B 111.4(6) . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C18 118.9(10) . . ?
C18 C17 H17 120.6 . . ?
C10B N2B C13B 122.0(8) . . ?
C12B N2B C10B 114.3(9) . . ?
C12B N2B C13B 123.4(8) . . ?
C17 C16 H16 118.8 . . ?
C17 C16 C15 122.3(10) . . ?
C15 C16 H16 118.8 . . ?
C1 C7 I1 114.9(6) . . ?
C8 C7 I1 119.4(6) . . ?
C8 C7 C1 125.6(8) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 120.9(9) . . ?
C19 C18 H18 119.5 . . ?
C8 N1 O1 104.0(5) . . ?
C8 N1 C14 116.5(6) . . ?
C14 N1 O1 112.6(6) . . ?
C17B C16B H16B 119.7 . . ?
C17B C16B C15B 120.6(8) . . ?
C15B C16B H16B 119.7 . . ?
N1B C8B C9B 108.4(6) . . ?
C7B C8B N1B 123.2(7) . . ?
C7B C8B C9B 127.7(7) . . ?
C4 C3 H3 120.1 . . ?
C4 C3 C2 119.9(8) . . ?
C2 C3 H3 120.1 . . ?
O1B C10B N2B 124.8(9) . . ?
O1B C10B C9B 127.7(9) . . ?
N2B C10B C9B 107.5(8) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 C16 118.3(8) . . ?
C14 C15 H15 120.9 . . ?
C16B C17B H17B 120.1 . . ?
C16B C17B C18B 119.8(10) . . ?
C18B C17B H17B 120.1 . . ?
C6B C1B C7B 120.9(8) . . ?
C2B C1B C6B 118.9(9) . . ?
C2B C1B C7B 120.2(9) . . ?
C1B C6B H6B 119.7 . . ?
C5B C6B C1B 120.7(9) . . ?
C5B C6B H6B 119.7 . . ?
C8B C7B I1B 118.1(6) . . ?
C8B C7B C1B 126.5(8) . . ?
C1B C7B I1B 115.4(6) . . ?
C6 C1 C7 120.1(9) . . ?
C2 C1 C7 120.1(8) . . ?
C2 C1 C6 119.7(9) . . ?
N2 C12 C9 109.6(8) . . ?
O3 C12 N2 124.5(10) . . ?
O3 C12 C9 125.8(10) . . ?
C17B C18B H18B 120.1 . . ?
C19B C18B C17B 119.9(10) . . ?
C19B C18B H18B 120.1 . . ?
C19B C14B N1B 119.4(7) . . ?
C15B C14B N1B 120.1(7) . . ?
C15B C14B C19B 119.9(7) . . ?
C12 C9 H9 112.0 . . ?
C12 C9 C10 102.5(7) . . ?
C10 C9 H9 112.0 . . ?
C8 C9 C12 115.8(7) . . ?
C8 C9 H9 112.0 . . ?
C8 C9 C10 101.5(7) . . ?
C18B C19B C14B 120.6(8) . . ?
C18B C19B H19B 119.7 . . ?
C14B C19B H19B 119.7 . . ?
C16B C15B H15B 120.4 . . ?
C14B C15B C16B 119.1(8) . . ?
C14B C15B H15B 120.4 . . ?
C1 C6 H6 120.5 . . ?
C5 C6 C1 119.0(10) . . ?
C5 C6 H6 120.5 . . ?
N2 C13 H13D 109.5 . . ?
N2 C13 H13E 109.5 . . ?
N2 C13 H13F 109.5 . . ?
H13D C13 H13E 109.5 . . ?
H13D C13 H13F 109.5 . . ?
H13E C13 H13F 109.5 . . ?
O2B C12B N2B 125.2(10) . . ?
O2B C12B C11B 126.6(9) . . ?
N2B C12B C11B 108.3(8) . . ?
C6B C5B H5B 119.8 . . ?
C6B C5B C4B 120.4(9) . . ?
C4B C5B H5B 119.8 . . ?
O1 C10 C9 107.0(6) . . ?
O1 C10 H10 110.5 . . ?
O1 C10 C11 111.8(7) . . ?
C9 C10 H10 110.5 . . ?
C11 C10 C9 106.4(7) . . ?
C11 C10 H10 110.5 . . ?
C1B C2B H2B 119.8 . . ?
C1B C2B C3B 120.3(10) . . ?
C3B C2B H2B 119.8 . . ?
C7 C8 N1 122.2(7) . . ?
C7 C8 C9 128.0(7) . . ?
N1 C8 C9 109.0(6) . . ?
N2B C13B H13A 109.5 . . ?
N2B C13B H13B 109.5 . . ?
N2B C13B H13C 109.5 . . ?
H13A C13B H13B 109.5 . . ?
H13A C13B H13C 109.5 . . ?
H13B C13B H13C 109.5 . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C14 119.3(8) . . ?
C14 C19 H19 120.3 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.3(8) . . ?
C5 C4 H4 119.9 . . ?
C8B C9B C10B 116.2(7) . . ?
C8B C9B H9B 111.4 . . ?
C8B C9B C11B 101.4(6) . . ?
C10B C9B H9B 111.4 . . ?
C11B C9B C10B 104.2(7) . . ?
C11B C9B H9B 111.4 . . ?
O3B C11B C12B 110.2(7) . . ?
O3B C11B C9B 107.4(7) . . ?
O3B C11B H11B 111.3 . . ?
C12B C11B H11B 111.3 . . ?
C9B C11B C12B 105.2(7) . . ?
C9B C11B H11B 111.3 . . ?
N2 C11 C10 107.6(8) . . ?
O2 C11 N2 125.4(10) . . ?
O2 C11 C10 127.1(9) . . ?
C2B C3B H3B 119.9 . . ?
C4B C3B C2B 120.1(11) . . ?
C4B C3B H3B 119.9 . . ?
C3 C2 H2 119.9 . . ?
C1 C2 C3 120.2(9) . . ?
C1 C2 H2 119.9 . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.0(10) . . ?
C4 C5 H5 119.5 . . ?
C5B C4B H4B 120.2 . . ?
C3B C4B C5B 119.6(9) . . ?
C3B C4B H4B 120.2 . . ?
C15 C14 N1 120.1(7) . . ?
C15 C14 C19 120.2(8) . . ?
C19 C14 N1 119.5(7) . . ?

_olex2_date_sample_data_collection 2019-05-03
_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 1.632
_oxdiff_exptl_absorpt_empirical_full_min 0.650
