# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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. 
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data_2018_01_25_dt_bbcl2thf_n
_database_code_depnum_ccdc_archive 'CCDC 1995127'
loop_
_audit_author_name
_audit_author_address
'Damian Trzybinski'
;Biological and Chemical Research Centre University of Warsaw
Poland
;
_audit_update_record             
;
2020-04-06 deposited with the CCDC.	2020-07-10 downloaded from the CCDC.
;
_audit_creation_date             2020-03-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 Cl2 N2 O2, C4 H8 O'
_chemical_formula_sum            'C18 H16 Cl2 N2 O3'
_chemical_formula_weight         379.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         ?
_chemical_oxdiff_usercomment     ?
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'
Cl Cl 0.3639 0.7018 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.6078(5)
_cell_length_b                   10.7273(4)
_cell_length_c                   31.0150(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3529.3(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2392
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.2210
_cell_measurement_theta_min      5.6910
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.483
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.544
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7516
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.074
_diffrn_reflns_theta_max         67.074
_diffrn_reflns_theta_min         2.850
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4391
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      ?
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0631265000
_diffrn_orient_matrix_UB_12      0.0953869000
_diffrn_orient_matrix_UB_13      -0.0301431000
_diffrn_orient_matrix_UB_21      -0.1145100000
_diffrn_orient_matrix_UB_22      -0.0871269000
_diffrn_orient_matrix_UB_23      -0.0048016000
_diffrn_orient_matrix_UB_31      -0.0628285000
_diffrn_orient_matrix_UB_32      0.0627840000
_diffrn_orient_matrix_UB_33      0.0392452000
_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                2558
_reflns_number_total             3152
_reflns_odcompleteness_completeness 99.83
_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 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.462
_refine_diff_density_min         -0.956
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3152
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0617
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0916P)²+8.3758P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1646
_refine_ls_wR_factor_ref         0.1764
_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
2. Restrained distances
 C16-C17
 1.54 with sigma of 0.02
 N1-H1
 0.87 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C17) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
4. Rigid body (RIGU) restrains
 C17, C18, O3, C15, C16
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B)
5.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.6600(3) 0.1696(3) 0.40382(11) 0.0163(7) Uani 1 1 d . . . . .
C2 C 0.5491(3) 0.2272(3) 0.42596(10) 0.0155(7) Uani 1 1 d . . . . .
C3 C 0.5200(3) 0.3539(3) 0.42232(10) 0.0150(7) Uani 1 1 d . . . . .
C4 C 0.5909(3) 0.4311(3) 0.35180(10) 0.0154(7) Uani 1 1 d . . . . .
C5 C 0.5242(3) 0.3277(3) 0.32907(10) 0.0162(7) Uani 1 1 d . . . . .
C6 C 0.5621(3) 0.2029(3) 0.33197(10) 0.0157(7) Uani 1 1 d . . . . .
C7 C 0.4800(3) 0.1523(3) 0.45407(10) 0.0185(7) Uani 1 1 d . . . . .
H7 H 0.4986 0.0680 0.4567 0.022 Uiso 1 1 calc R . . . .
C8 C 0.3837(3) 0.2045(3) 0.47793(11) 0.0191(7) Uani 1 1 d . . . . .
C9 C 0.3562(4) 0.3303(3) 0.47600(11) 0.0217(8) Uani 1 1 d . . . . .
H9 H 0.2931 0.3643 0.4932 0.026 Uiso 1 1 calc R . . . .
C10 C 0.4250(3) 0.4052(3) 0.44782(11) 0.0194(7) Uani 1 1 d . . . . .
H10 H 0.4074 0.4900 0.4460 0.023 Uiso 1 1 calc R . . . .
C11 C 0.4334(3) 0.3618(3) 0.29860(11) 0.0191(7) Uani 1 1 d . . . . .
H11 H 0.4073 0.4443 0.2964 0.023 Uiso 1 1 calc R . . . .
C12 C 0.3826(3) 0.2720(4) 0.27171(11) 0.0221(8) Uani 1 1 d . . . . .
C13 C 0.4213(4) 0.1488(4) 0.27378(11) 0.0253(8) Uani 1 1 d . . . . .
H13 H 0.3873 0.0895 0.2552 0.030 Uiso 1 1 calc R . . . .
C14 C 0.5116(3) 0.1153(3) 0.30398(11) 0.0212(7) Uani 1 1 d . . . . .
H14 H 0.5386 0.0329 0.3055 0.025 Uiso 1 1 calc R . . . .
Cl1 Cl 0.29840(9) 0.10905(8) 0.51269(3) 0.0262(3) Uani 1 1 d . . . . .
Cl2 Cl 0.27108(10) 0.31894(10) 0.23425(3) 0.0355(3) Uani 1 1 d . . . . .
N1 N 0.5925(3) 0.4333(3) 0.39502(9) 0.0162(6) Uani 1 1 d D . . . .
H1 H 0.634(3) 0.491(3) 0.4081(11) 0.019 Uiso 1 1 d DR . . . .
N2 N 0.6613(3) 0.1664(3) 0.36006(9) 0.0164(6) Uani 1 1 d . . . . .
H2 H 0.722(4) 0.123(4) 0.3481(14) 0.021(11) Uiso 1 1 d . . . . .
O1 O 0.7441(2) 0.1221(2) 0.42554(7) 0.0180(5) Uani 1 1 d . . . . .
O2 O 0.6425(2) 0.5126(2) 0.32965(7) 0.0202(5) Uani 1 1 d . . . . .
C15 C 0.0489(5) 0.2692(5) 0.41827(18) 0.0511(11) Uani 1 1 d . U . . .
H15A H 0.0869 0.3287 0.4379 0.061 Uiso 1 1 calc R . . . .
H15B H -0.0229 0.2313 0.4325 0.061 Uiso 1 1 calc R . . . .
C16 C 0.0081(7) 0.3328(6) 0.37817(18) 0.0665(16) Uani 1 1 d D U . . .
H16A H -0.0790 0.3126 0.3716 0.080 Uiso 1 1 calc R . . . .
H16B H 0.0156 0.4225 0.3812 0.080 Uiso 1 1 calc R . . . .
C17 C 0.0911(7) 0.2875(7) 0.3444(2) 0.0779(15) Uani 1 1 d D U . . .
H17A H 0.1317 0.3566 0.3297 0.093 Uiso 1 1 calc R . . . .
H17B H 0.0442 0.2392 0.3234 0.093 Uiso 1 1 calc R . . . .
C18 C 0.1869(6) 0.2077(6) 0.3667(2) 0.0637(14) Uani 1 1 d . U . . .
H18A H 0.2030 0.1327 0.3502 0.076 Uiso 1 1 calc R . . . .
H18B H 0.2655 0.2527 0.3701 0.076 Uiso 1 1 calc R . . . .
O3 O 0.1368(4) 0.1777(4) 0.40665(14) 0.0622(10) Uani 1 1 d . U . . .


_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
C1 C2 1.495(5) . ?
C1 N2 1.358(4) . ?
C1 O1 1.229(4) . ?
C2 C3 1.399(5) . ?
C2 C7 1.394(5) . ?
C3 C10 1.394(5) . ?
C3 N1 1.427(4) . ?
C4 C5 1.493(4) . ?
C4 N1 1.341(4) . ?
C4 O2 1.239(4) . ?
C5 C6 1.402(5) . ?
C5 C11 1.398(5) . ?
C6 C14 1.387(5) . ?
C6 N2 1.421(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.380(5) . ?
C8 C9 1.382(5) . ?
C8 Cl1 1.740(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.394(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.384(5) . ?
C12 C13 1.385(5) . ?
C12 Cl2 1.733(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(5) . ?
C14 H14 0.9300 . ?
N1 H1 0.867(10) . ?
N2 H2 0.88(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.483(7) . ?
C15 O3 1.401(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.453(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.499(9) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 O3 1.385(7) . ?

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
N2 C1 C2 118.5(3) . . ?
O1 C1 C2 119.4(3) . . ?
O1 C1 N2 122.0(3) . . ?
C3 C2 C1 122.6(3) . . ?
C7 C2 C1 117.6(3) . . ?
C7 C2 C3 119.6(3) . . ?
C2 C3 N1 120.6(3) . . ?
C10 C3 C2 119.9(3) . . ?
C10 C3 N1 119.4(3) . . ?
N1 C4 C5 119.4(3) . . ?
O2 C4 C5 118.1(3) . . ?
O2 C4 N1 122.4(3) . . ?
C6 C5 C4 123.0(3) . . ?
C11 C5 C4 116.9(3) . . ?
C11 C5 C6 119.4(3) . . ?
C5 C6 N2 121.0(3) . . ?
C14 C6 C5 119.8(3) . . ?
C14 C6 N2 118.9(3) . . ?
C2 C7 H7 120.3 . . ?
C8 C7 C2 119.5(3) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 C9 121.9(3) . . ?
C7 C8 Cl1 118.6(3) . . ?
C9 C8 Cl1 119.4(3) . . ?
C8 C9 H9 120.6 . . ?
C8 C9 C10 118.7(3) . . ?
C10 C9 H9 120.6 . . ?
C3 C10 H10 119.8 . . ?
C9 C10 C3 120.4(3) . . ?
C9 C10 H10 119.8 . . ?
C5 C11 H11 120.2 . . ?
C12 C11 C5 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 121.4(3) . . ?
C11 C12 Cl2 117.9(3) . . ?
C13 C12 Cl2 120.7(3) . . ?
C12 C13 H13 120.5 . . ?
C12 C13 C14 118.9(3) . . ?
C14 C13 H13 120.6 . . ?
C6 C14 C13 120.9(3) . . ?
C6 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C3 N1 H1 115(3) . . ?
C4 N1 C3 125.2(3) . . ?
C4 N1 H1 119(3) . . ?
C1 N2 C6 126.7(3) . . ?
C1 N2 H2 116(3) . . ?
C6 N2 H2 116(3) . . ?
H15A C15 H15B 108.5 . . ?
C16 C15 H15A 110.2 . . ?
C16 C15 H15B 110.2 . . ?
O3 C15 H15A 110.2 . . ?
O3 C15 H15B 110.2 . . ?
O3 C15 C16 107.5(5) . . ?
C15 C16 H16A 110.5 . . ?
C15 C16 H16B 110.5 . . ?
H16A C16 H16B 108.7 . . ?
C17 C16 C15 105.9(5) . . ?
C17 C16 H16A 110.5 . . ?
C17 C16 H16B 110.5 . . ?
C16 C17 H17A 110.6 . . ?
C16 C17 H17B 110.6 . . ?
C16 C17 C18 105.5(5) . . ?
H17A C17 H17B 108.8 . . ?
C18 C17 H17A 110.6 . . ?
C18 C17 H17B 110.6 . . ?
C17 C18 H18A 110.4 . . ?
C17 C18 H18B 110.4 . . ?
H18A C18 H18B 108.6 . . ?
O3 C18 C17 106.6(5) . . ?
O3 C18 H18A 110.4 . . ?
O3 C18 H18B 110.4 . . ?
C18 O3 C15 108.8(4) . . ?

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
C1 C2 C3 C10 -172.1(3) . . . . ?
C1 C2 C3 N1 3.3(5) . . . . ?
C1 C2 C7 C8 174.5(3) . . . . ?
C2 C1 N2 C6 -5.9(5) . . . . ?
C2 C3 C10 C9 -2.0(5) . . . . ?
C2 C3 N1 C4 71.2(4) . . . . ?
C2 C7 C8 C9 -2.3(5) . . . . ?
C2 C7 C8 Cl1 179.8(3) . . . . ?
C3 C2 C7 C8 0.0(5) . . . . ?
C4 C5 C6 C14 -167.9(3) . . . . ?
C4 C5 C6 N2 5.4(5) . . . . ?
C4 C5 C11 C12 169.9(3) . . . . ?
C5 C4 N1 C3 -9.5(5) . . . . ?
C5 C6 C14 C13 -1.7(5) . . . . ?
C5 C6 N2 C1 66.8(5) . . . . ?
C5 C11 C12 C13 -1.1(5) . . . . ?
C5 C11 C12 Cl2 -179.6(3) . . . . ?
C6 C5 C11 C12 -0.2(5) . . . . ?
C7 C2 C3 C10 2.1(5) . . . . ?
C7 C2 C3 N1 177.6(3) . . . . ?
C7 C8 C9 C10 2.5(6) . . . . ?
C8 C9 C10 C3 -0.3(5) . . . . ?
C10 C3 N1 C4 -113.3(4) . . . . ?
C11 C5 C6 C14 1.6(5) . . . . ?
C11 C5 C6 N2 174.8(3) . . . . ?
C11 C12 C13 C14 1.0(6) . . . . ?
C12 C13 C14 C6 0.5(5) . . . . ?
C14 C6 N2 C1 -119.9(4) . . . . ?
Cl1 C8 C9 C10 -179.7(3) . . . . ?
Cl2 C12 C13 C14 179.4(3) . . . . ?
N1 C3 C10 C9 -177.5(3) . . . . ?
N1 C4 C5 C6 -64.2(5) . . . . ?
N1 C4 C5 C11 126.1(3) . . . . ?
N2 C1 C2 C3 -65.2(4) . . . . ?
N2 C1 C2 C7 120.5(3) . . . . ?
N2 C6 C14 C13 -175.1(3) . . . . ?
O1 C1 C2 C3 117.9(4) . . . . ?
O1 C1 C2 C7 -56.4(4) . . . . ?
O1 C1 N2 C6 170.9(3) . . . . ?
O2 C4 C5 C6 116.2(4) . . . . ?
O2 C4 C5 C11 -53.5(4) . . . . ?
O2 C4 N1 C3 170.1(3) . . . . ?
C15 C16 C17 C18 -5.4(8) . . . . ?
C16 C15 O3 C18 21.2(7) . . . . ?
C16 C17 C18 O3 18.2(8) . . . . ?
C17 C18 O3 C15 -24.6(7) . . . . ?
O3 C15 C16 C17 -9.0(7) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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 1.517
_oxdiff_exptl_absorpt_empirical_full_min 0.634
####################################################################### 
# 
# 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_2018_01_25_dt_bbi2thf_n
_database_code_depnum_ccdc_archive 'CCDC 1995128'
loop_
_audit_author_name
_audit_author_address
'Damian Trzybinski'
;Biological and Chemical Research Centre University of Warsaw
Poland
;
_audit_update_record             
;
2020-04-06 deposited with the CCDC.	2020-07-10 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT431_2018_01_25_dt_bbi2thf_n 
;
PROBLEM: Short Inter HL..A Contact  I1       ..O3       .       2.93 Ang.
RESPONSE: This alert results from the presence of the I...O halogen bond.
;
# Added during the CSD deposition process: Monday 06 April 2020 12:25 PM
# end Validation Reply Form

_audit_creation_date             2018-02-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 I2 N2 O2, 2(C4 H8 O)'
_chemical_formula_sum            'C22 H24 I2 N2 O4'
_chemical_formula_weight         634.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         ?
_chemical_oxdiff_usercomment     ?
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'
I I -0.3257 6.8362 '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 21/c'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   20.3062(6)
_cell_length_b                   10.4583(3)
_cell_length_c                   11.1201(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.196(3)
_cell_angle_gamma                90
_cell_volume                     2308.25(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3939
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.4370
_cell_measurement_theta_min      4.1660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    21.654
_exptl_absorpt_correction_T_max  0.318
_exptl_absorpt_correction_T_min  0.019
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.825
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8500
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         2.226
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4391
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      ?
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0466776000
_diffrn_orient_matrix_UB_12      0.1016216000
_diffrn_orient_matrix_UB_13      0.0739911000
_diffrn_orient_matrix_UB_21      0.0337533000
_diffrn_orient_matrix_UB_22      -0.1039361000
_diffrn_orient_matrix_UB_23      0.0904898000
_diffrn_orient_matrix_UB_31      0.0520415000
_diffrn_orient_matrix_UB_32      -0.0237949000
_diffrn_orient_matrix_UB_33      -0.0801958000
_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                3538
_reflns_number_total             4122
_reflns_odcompleteness_completeness 99.91
_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 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.514
_refine_diff_density_min         -1.730
_refine_diff_density_rms         0.203
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4122
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.046
_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)+(0.0868P)²+3.2071P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1363
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N1-H1
 0.87 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C15) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4. Rigid body (RIGU) restrains
 O3, C15, C16, C17, C18
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C18(H18A,H18B), C19(H19A,H19B), C22(H22A,H22B), C17(H17B,
 H17A), C21(H21A,H21B), C16(H16A,H16B), C15(H15A,H15B)
5.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C11(H11), C7(H7), C10(H10), C9(H9), C13(H13)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
I2 I 0.49396(2) 0.68264(3) 0.52875(4) 0.02191(15) Uani 1 1 d . . . . .
I1 I 0.93585(2) 0.80842(4) 0.49771(4) 0.02382(16) Uani 1 1 d . . . . .
O4 O 0.7211(2) 0.5250(5) 0.7254(4) 0.0315(10) Uani 1 1 d . . . . .
N1 N 0.7214(2) 1.1106(5) 0.7201(4) 0.0167(9) Uani 1 1 d D . . . .
O1 O 0.76711(18) 1.2462(4) 0.4292(4) 0.0189(8) Uani 1 1 d . . . . .
O2 O 0.61700(19) 1.1553(4) 0.7473(4) 0.0207(9) Uani 1 1 d . . . . .
O3 O 0.9763(3) 1.3265(5) 0.6384(6) 0.0392(12) Uani 1 1 d . U . . .
N2 N 0.6670(2) 1.1568(5) 0.4364(5) 0.0158(9) Uani 1 1 d . . . . .
C14 C 0.5902(3) 0.9828(6) 0.3616(5) 0.0208(12) Uani 1 1 d . . . . .
H14 H 0.5915 1.0071 0.2817 0.025 Uiso 1 1 calc R . . . .
C11 C 0.5833(3) 0.9156(5) 0.5990(5) 0.0165(11) Uani 1 1 d . . . . .
H11 H 0.5800 0.8929 0.6784 0.020 Uiso 1 1 calc R . . . .
C7 C 0.8205(3) 0.9892(6) 0.4986(5) 0.0187(11) Uani 1 1 d . . . . .
H7 H 0.8224 0.9974 0.4161 0.022 Uiso 1 1 calc R . . . .
C1 C 0.7348(3) 1.1608(5) 0.4656(5) 0.0162(11) Uani 1 1 d . . . . .
C4 C 0.6533(3) 1.1003(5) 0.6883(5) 0.0163(11) Uani 1 1 d . . . . .
C3 C 0.7685(3) 1.0405(5) 0.6688(5) 0.0143(10) Uani 1 1 d . . . . .
C10 C 0.8155(3) 0.9620(6) 0.7440(5) 0.0192(11) Uani 1 1 d . . . . .
H10 H 0.8143 0.9528 0.8267 0.023 Uiso 1 1 calc R . . . .
C20 C 0.7255(4) 0.6768(7) 0.5716(7) 0.0355(17) Uani 1 1 d . . . . .
H20A H 0.7038 0.7551 0.5372 0.043 Uiso 1 1 calc R . . . .
H20B H 0.7721 0.6771 0.5632 0.043 Uiso 1 1 calc R . . . .
C12 C 0.5494(3) 0.8464(6) 0.5007(5) 0.0173(11) Uani 1 1 d . . . . .
C6 C 0.6277(2) 1.0505(5) 0.4608(5) 0.0162(11) Uani 1 1 d . . . . .
C5 C 0.6228(2) 1.0195(5) 0.5807(5) 0.0137(10) Uani 1 1 d . . . . .
C9 C 0.8641(3) 0.8974(6) 0.6967(6) 0.0216(12) Uani 1 1 d . . . . .
H9 H 0.8957 0.8463 0.7477 0.026 Uiso 1 1 calc R . . . .
C2 C 0.7728(2) 1.0573(5) 0.5461(5) 0.0160(11) Uani 1 1 d . . . . .
C13 C 0.5512(3) 0.8800(6) 0.3808(5) 0.0207(12) Uani 1 1 d . . . . .
H13 H 0.5266 0.8341 0.3148 0.025 Uiso 1 1 calc R . . . .
C8 C 0.8653(3) 0.9092(6) 0.5752(6) 0.0205(12) Uani 1 1 d . . . . .
C18 C 0.9270(4) 1.2484(8) 0.6774(8) 0.0410(16) Uani 1 1 d . U . . .
H18A H 0.9486 1.1864 0.7379 0.049 Uiso 1 1 calc R . . . .
H18B H 0.9003 1.2029 0.6080 0.049 Uiso 1 1 calc R . . . .
C19 C 0.7202(4) 0.6594(7) 0.7050(7) 0.0351(16) Uani 1 1 d . . . . .
H19A H 0.7579 0.7001 0.7598 0.042 Uiso 1 1 calc R . . . .
H19B H 0.6787 0.6966 0.7190 0.042 Uiso 1 1 calc R . . . .
C22 C 0.6965(4) 0.4613(7) 0.6125(7) 0.0374(17) Uani 1 1 d . . . . .
H22A H 0.6536 0.4210 0.6131 0.045 Uiso 1 1 calc R . . . .
H22B H 0.7281 0.3957 0.5994 0.045 Uiso 1 1 calc R . . . .
C17 C 0.8831(4) 1.3373(8) 0.7329(9) 0.0464(18) Uani 1 1 d . U . . .
H17B H 0.8369 1.3074 0.7177 0.056 Uiso 1 1 calc R . . . .
H17A H 0.8999 1.3469 0.8208 0.056 Uiso 1 1 calc R . . . .
C21 C 0.6884(4) 0.5601(9) 0.5118(8) 0.047(2) Uani 1 1 d . . . . .
H21A H 0.6412 0.5793 0.4804 0.056 Uiso 1 1 calc R . . . .
H21B H 0.7079 0.5302 0.4444 0.056 Uiso 1 1 calc R . . . .
C16 C 0.8889(5) 1.4597(9) 0.6662(10) 0.053(2) Uani 1 1 d . U . . .
H16A H 0.8536 1.4662 0.5926 0.064 Uiso 1 1 calc R . . . .
H16B H 0.8862 1.5329 0.7185 0.064 Uiso 1 1 calc R . . . .
C15 C 0.9546(5) 1.4525(9) 0.6353(10) 0.0560(18) Uani 1 1 d . U . . .
H15A H 0.9521 1.4875 0.5536 0.067 Uiso 1 1 calc R . . . .
H15B H 0.9866 1.5030 0.6933 0.067 Uiso 1 1 calc R . . . .
H2 H 0.650(3) 1.206(6) 0.380(7) 0.011(16) Uiso 1 1 d . . . . .
H1 H 0.742(4) 1.158(6) 0.780(5) 0.04(2) Uiso 1 1 d 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
I2 C12 2.109(6) . ?
I1 C8 2.104(6) . ?
O4 C19 1.423(8) . ?
O4 C22 1.416(8) . ?
N1 C4 1.358(7) . ?
N1 C3 1.418(7) . ?
N1 H1 0.86(2) . ?
O1 C1 1.227(7) . ?
O2 C4 1.228(7) . ?
O3 C18 1.429(9) . ?
O3 C15 1.387(11) . ?
N2 C1 1.345(7) . ?
N2 C6 1.428(7) . ?
N2 H2 0.82(7) . ?
C14 H14 0.9300 . ?
C14 C6 1.394(8) . ?
C14 C13 1.378(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.369(8) . ?
C11 C5 1.390(8) . ?
C7 H7 0.9300 . ?
C7 C2 1.393(8) . ?
C7 C8 1.388(8) . ?
C1 C2 1.509(8) . ?
C4 C5 1.488(8) . ?
C3 C10 1.396(8) . ?
C3 C2 1.396(8) . ?
C10 H10 0.9300 . ?
C10 C9 1.387(8) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C19 1.521(11) . ?
C20 C21 1.512(11) . ?
C12 C13 1.386(8) . ?
C6 C5 1.397(8) . ?
C9 H9 0.9300 . ?
C9 C8 1.362(9) . ?
C13 H13 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C17 1.507(10) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C21 1.507(11) . ?
C17 H17B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 C16 1.496(12) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C15 1.447(12) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?

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
C22 O4 C19 109.5(6) . . ?
C4 N1 C3 126.2(5) . . ?
C4 N1 H1 124(6) . . ?
C3 N1 H1 110(6) . . ?
C15 O3 C18 108.1(6) . . ?
C1 N2 C6 124.3(5) . . ?
C1 N2 H2 114(5) . . ?
C6 N2 H2 118(5) . . ?
C6 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C6 120.6(5) . . ?
C12 C11 H11 119.9 . . ?
C12 C11 C5 120.3(5) . . ?
C5 C11 H11 119.9 . . ?
C2 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C8 C7 C2 119.6(5) . . ?
O1 C1 N2 122.3(5) . . ?
O1 C1 C2 118.4(5) . . ?
N2 C1 C2 119.3(5) . . ?
N1 C4 C5 118.9(5) . . ?
O2 C4 N1 121.1(5) . . ?
O2 C4 C5 120.0(5) . . ?
C10 C3 N1 119.8(5) . . ?
C10 C3 C2 118.9(5) . . ?
C2 C3 N1 121.0(5) . . ?
C3 C10 H10 119.7 . . ?
C9 C10 C3 120.7(5) . . ?
C9 C10 H10 119.7 . . ?
H20A C20 H20B 109.3 . . ?
C19 C20 H20A 111.4 . . ?
C19 C20 H20B 111.4 . . ?
C21 C20 H20A 111.4 . . ?
C21 C20 H20B 111.4 . . ?
C21 C20 C19 101.6(6) . . ?
C11 C12 I2 120.3(4) . . ?
C11 C12 C13 121.5(5) . . ?
C13 C12 I2 118.1(4) . . ?
C14 C6 N2 118.7(5) . . ?
C14 C6 C5 120.0(5) . . ?
C5 C6 N2 121.2(5) . . ?
C11 C5 C4 118.8(5) . . ?
C11 C5 C6 118.8(5) . . ?
C6 C5 C4 122.3(5) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 C10 119.7(5) . . ?
C8 C9 H9 120.2 . . ?
C7 C2 C1 116.8(5) . . ?
C7 C2 C3 119.9(5) . . ?
C3 C2 C1 122.7(5) . . ?
C14 C13 C12 118.6(5) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
C7 C8 I1 117.7(4) . . ?
C9 C8 I1 121.2(4) . . ?
C9 C8 C7 121.1(5) . . ?
O3 C18 H18A 110.4 . . ?
O3 C18 H18B 110.4 . . ?
O3 C18 C17 106.5(6) . . ?
H18A C18 H18B 108.6 . . ?
C17 C18 H18A 110.4 . . ?
C17 C18 H18B 110.4 . . ?
O4 C19 C20 105.8(6) . . ?
O4 C19 H19A 110.6 . . ?
O4 C19 H19B 110.6 . . ?
C20 C19 H19A 110.6 . . ?
C20 C19 H19B 110.6 . . ?
H19A C19 H19B 108.7 . . ?
O4 C22 H22A 110.2 . . ?
O4 C22 H22B 110.2 . . ?
O4 C22 C21 107.4(6) . . ?
H22A C22 H22B 108.5 . . ?
C21 C22 H22A 110.2 . . ?
C21 C22 H22B 110.2 . . ?
C18 C17 H17B 111.3 . . ?
C18 C17 H17A 111.3 . . ?
H17B C17 H17A 109.2 . . ?
C16 C17 C18 102.1(7) . . ?
C16 C17 H17B 111.3 . . ?
C16 C17 H17A 111.3 . . ?
C20 C21 H21A 110.7 . . ?
C20 C21 H21B 110.7 . . ?
C22 C21 C20 105.1(6) . . ?
C22 C21 H21A 110.7 . . ?
C22 C21 H21B 110.7 . . ?
H21A C21 H21B 108.8 . . ?
C17 C16 H16A 110.9 . . ?
C17 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
C15 C16 C17 104.2(8) . . ?
C15 C16 H16A 110.9 . . ?
C15 C16 H16B 110.9 . . ?
O3 C15 C16 110.4(8) . . ?
O3 C15 H15A 109.6 . . ?
O3 C15 H15B 109.6 . . ?
C16 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?

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
I2 C12 C13 C14 -176.6(4) . . . . ?
O4 C22 C21 C20 13.3(8) . . . . ?
N1 C4 C5 C11 119.5(6) . . . . ?
N1 C4 C5 C6 -65.9(7) . . . . ?
N1 C3 C10 C9 -176.9(5) . . . . ?
N1 C3 C2 C7 178.6(5) . . . . ?
N1 C3 C2 C1 7.9(8) . . . . ?
O1 C1 C2 C7 -56.6(7) . . . . ?
O1 C1 C2 C3 114.4(6) . . . . ?
O2 C4 C5 C11 -59.8(7) . . . . ?
O2 C4 C5 C6 114.7(6) . . . . ?
O3 C18 C17 C16 27.4(9) . . . . ?
N2 C1 C2 C7 123.4(6) . . . . ?
N2 C1 C2 C3 -65.5(8) . . . . ?
N2 C6 C5 C11 179.5(5) . . . . ?
N2 C6 C5 C4 5.0(8) . . . . ?
C14 C6 C5 C11 3.9(8) . . . . ?
C14 C6 C5 C4 -170.6(5) . . . . ?
C11 C12 C13 C14 2.4(9) . . . . ?
C1 N2 C6 C14 -114.1(7) . . . . ?
C1 N2 C6 C5 70.2(8) . . . . ?
C4 N1 C3 C10 -119.6(6) . . . . ?
C4 N1 C3 C2 66.3(8) . . . . ?
C3 N1 C4 O2 172.1(5) . . . . ?
C3 N1 C4 C5 -7.3(9) . . . . ?
C3 C10 C9 C8 -1.0(9) . . . . ?
C10 C3 C2 C7 4.4(8) . . . . ?
C10 C3 C2 C1 -166.4(5) . . . . ?
C10 C9 C8 I1 -177.9(4) . . . . ?
C10 C9 C8 C7 2.8(9) . . . . ?
C12 C11 C5 C4 173.9(5) . . . . ?
C12 C11 C5 C6 -0.8(8) . . . . ?
C6 N2 C1 O1 170.2(5) . . . . ?
C6 N2 C1 C2 -9.8(9) . . . . ?
C6 C14 C13 C12 0.8(9) . . . . ?
C5 C11 C12 I2 176.6(4) . . . . ?
C5 C11 C12 C13 -2.4(8) . . . . ?
C2 C7 C8 I1 179.7(4) . . . . ?
C2 C7 C8 C9 -1.0(9) . . . . ?
C2 C3 C10 C9 -2.6(8) . . . . ?
C13 C14 C6 N2 -179.7(5) . . . . ?
C13 C14 C6 C5 -3.9(9) . . . . ?
C8 C7 C2 C1 168.6(5) . . . . ?
C8 C7 C2 C3 -2.6(8) . . . . ?
C18 O3 C15 C16 -2.8(11) . . . . ?
C18 C17 C16 C15 -28.2(10) . . . . ?
C19 O4 C22 C21 7.9(8) . . . . ?
C19 C20 C21 C22 -27.4(8) . . . . ?
C22 O4 C19 C20 -25.9(8) . . . . ?
C17 C16 C15 O3 20.3(11) . . . . ?
C21 C20 C19 O4 32.7(7) . . . . ?
C15 O3 C18 C17 -15.9(9) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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 1.818
_oxdiff_exptl_absorpt_empirical_full_min 0.580
####################################################################### 
# 
# 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_2018_03_27_dt_bbf2-thf_n
_database_code_depnum_ccdc_archive 'CCDC 1995129'
loop_
_audit_author_name
_audit_author_address
'Damian Trzybinski'
;Biological and Chemical Research Centre University of Warsaw
Poland
;
_audit_update_record             
;
2020-04-06 deposited with the CCDC.	2020-07-10 downloaded from the CCDC.
;
_audit_creation_date             2020-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 F2 N2 O2, C4 H8 O'
_chemical_formula_sum            'C18 H16 F2 N2 O3'
_chemical_formula_weight         346.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         ?
_chemical_oxdiff_usercomment     ?
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'
F F 0.0727 0.0534 '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 21/n'
_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                   10.6612(3)
_cell_length_b                   20.5090(5)
_cell_length_c                   14.3063(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.046(2)
_cell_angle_gamma                90
_cell_volume                     3128.08(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    11270
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.1850
_cell_measurement_theta_min      4.6590
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.993
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (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    1.471
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            42020
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.062
_diffrn_reflns_theta_max         67.062
_diffrn_reflns_theta_min         3.767
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      ?
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0281840000
_diffrn_orient_matrix_UB_12      0.0581351000
_diffrn_orient_matrix_UB_13      -0.0648767000
_diffrn_orient_matrix_UB_21      -0.0778260000
_diffrn_orient_matrix_UB_22      0.0449174000
_diffrn_orient_matrix_UB_23      0.0638840000
_diffrn_orient_matrix_UB_31      0.1184323000
_diffrn_orient_matrix_UB_32      0.0156845000
_diffrn_orient_matrix_UB_33      0.0574975000
_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                4030
_reflns_number_total             5600
_reflns_odcompleteness_completeness 99.98
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         5600
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0962P)²+1.0125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1642
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 N2A-H2A
 0.87 with sigma of 0.01
 N1A-H1A
 0.87 with sigma of 0.01
 N1B-H1B
 0.87 with sigma of 0.01
 N2B-H2B
 0.87 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C15A(H15A,H15B), C16A(H16A,H16B), C17A(H17A,H17B), C18A(H18A,H18B), C15B(H15C,
 H15D), C16B(H16C,H16D), C17B(H17C,H17D), C18B(H18C,H18D)
3.b Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C9A(H9A), C10A(H10A), C11A(H11A), C13A(H13A), C14A(H14A), C7B(H7B),
 C9B(H9B), C10B(H10B), C11B(H11B), C13B(H13B), C14B(H14B)
;
_atom_sites_solution_hydrogens   mixed
_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
C1A C 0.37198(17) 0.55966(9) 0.30189(12) 0.0141(4) Uani 1 1 d . . . . .
C2A C 0.29246(17) 0.50906(9) 0.34949(12) 0.0129(4) Uani 1 1 d . . . . .
C3A C 0.16244(17) 0.50887(8) 0.34083(11) 0.0125(4) Uani 1 1 d . . . . .
C4A C 0.10469(17) 0.55358(9) 0.18679(12) 0.0134(4) Uani 1 1 d . . . . .
C5A C 0.19152(18) 0.50591(9) 0.14047(12) 0.0142(4) Uani 1 1 d . . . . .
C6A C 0.32152(17) 0.51166(8) 0.14908(11) 0.0126(4) Uani 1 1 d . . . . .
C7A C 0.35192(19) 0.46550(9) 0.40961(12) 0.0154(4) Uani 1 1 d . . . . .
H7A H 0.4388 0.4651 0.4156 0.018 Uiso 1 1 calc R . . . .
C8A C 0.27768(19) 0.42288(9) 0.46006(12) 0.0165(4) Uani 1 1 d . . . . .
C9A C 0.14856(19) 0.42306(9) 0.45610(12) 0.0183(4) Uani 1 1 d . . . . .
H9A H 0.1015 0.3948 0.4929 0.022 Uiso 1 1 calc R . . . .
C10A C 0.09075(18) 0.46651(9) 0.39582(12) 0.0153(4) Uani 1 1 d . . . . .
H10A H 0.0037 0.4675 0.3918 0.018 Uiso 1 1 calc R . . . .
C11A C 0.14046(18) 0.45815(9) 0.08231(12) 0.0160(4) Uani 1 1 d . . . . .
H11A H 0.0541 0.4540 0.0754 0.019 Uiso 1 1 calc R . . . .
C12A C 0.22195(19) 0.41714(9) 0.03521(12) 0.0176(4) Uani 1 1 d . . . . .
C13A C 0.35069(18) 0.42351(9) 0.03963(12) 0.0176(4) Uani 1 1 d . . . . .
H13A H 0.4027 0.3963 0.0050 0.021 Uiso 1 1 calc R . . . .
C14A C 0.40045(18) 0.47141(9) 0.09690(12) 0.0151(4) Uani 1 1 d . . . . .
H14A H 0.4869 0.4768 0.1006 0.018 Uiso 1 1 calc R . . . .
F1A F 0.33585(11) 0.37867(6) 0.51591(8) 0.0241(3) Uani 1 1 d . . . . .
F2A F 0.17281(11) 0.36861(6) -0.01754(8) 0.0263(3) Uani 1 1 d . . . . .
N1A N 0.10033(15) 0.55416(7) 0.28106(10) 0.0139(3) Uani 1 1 d D . . . .
N2A N 0.37515(14) 0.56063(7) 0.20781(10) 0.0137(3) Uani 1 1 d D . . . .
O1A O 0.43117(13) 0.59876(6) 0.35036(9) 0.0174(3) Uani 1 1 d . . . . .
O2A O 0.03949(12) 0.59010(6) 0.13854(8) 0.0166(3) Uani 1 1 d . . . . .
C1B C 0.62669(18) 0.19037(9) 0.19368(12) 0.0140(4) Uani 1 1 d . . . . .
C2B C 0.70826(18) 0.23877(8) 0.14372(12) 0.0131(4) Uani 1 1 d . . . . .
C3B C 0.83839(18) 0.23722(9) 0.15335(12) 0.0136(4) Uani 1 1 d . . . . .
C4B C 0.89383(17) 0.19627(9) 0.30942(12) 0.0142(4) Uani 1 1 d . . . . .
C5B C 0.80897(18) 0.24634(9) 0.35273(12) 0.0132(4) Uani 1 1 d . . . . .
C6B C 0.67875(18) 0.24211(9) 0.34422(12) 0.0131(4) Uani 1 1 d . . . . .
C7B C 0.65254(19) 0.28185(9) 0.08082(12) 0.0158(4) Uani 1 1 d . . . . .
H7B H 0.5659 0.2833 0.0736 0.019 Uiso 1 1 calc R . . . .
C8B C 0.72980(19) 0.32241(9) 0.02941(12) 0.0177(4) Uani 1 1 d . . . . .
C9B C 0.85888(18) 0.32068(9) 0.03525(12) 0.0174(4) Uani 1 1 d . . . . .
H9B H 0.9081 0.3477 -0.0019 0.021 Uiso 1 1 calc R . . . .
C10B C 0.91322(18) 0.27773(9) 0.09774(12) 0.0156(4) Uani 1 1 d . . . . .
H10B H 1.0001 0.2757 0.1029 0.019 Uiso 1 1 calc R . . . .
C11B C 0.86251(18) 0.29462(9) 0.40816(12) 0.0159(4) Uani 1 1 d . . . . .
H11B H 0.9491 0.2981 0.4141 0.019 Uiso 1 1 calc R . . . .
C12B C 0.78332(19) 0.33734(9) 0.45415(12) 0.0168(4) Uani 1 1 d . . . . .
C13B C 0.65440(18) 0.33252(9) 0.45076(12) 0.0169(4) Uani 1 1 d . . . . .
H13B H 0.6039 0.3608 0.4848 0.020 Uiso 1 1 calc R . . . .
C14B C 0.60240(18) 0.28428(9) 0.39519(12) 0.0144(4) Uani 1 1 d . . . . .
H14B H 0.5157 0.2800 0.3918 0.017 Uiso 1 1 calc R . . . .
F1B F 0.67597(11) 0.36665(6) -0.02834(8) 0.0258(3) Uani 1 1 d . . . . .
F2B F 0.83589(11) 0.38549(6) 0.50594(8) 0.0247(3) Uani 1 1 d . . . . .
N1B N 0.89738(15) 0.19245(7) 0.21542(11) 0.0148(3) Uani 1 1 d D . . . .
N2B N 0.62282(15) 0.19242(7) 0.28817(10) 0.0140(3) Uani 1 1 d D . . . .
O1B O 0.56545(13) 0.15050(6) 0.14800(9) 0.0175(3) Uani 1 1 d . . . . .
O2B O 0.95749(12) 0.16065(6) 0.36007(8) 0.0173(3) Uani 1 1 d . . . . .
C15A C 0.3013(2) 0.24061(12) 0.17140(16) 0.0339(6) Uani 1 1 d . . . . .
H15A H 0.3449 0.2037 0.1442 0.041 Uiso 1 1 calc R . . . .
H15B H 0.2334 0.2534 0.1301 0.041 Uiso 1 1 calc R . . . .
C16A C 0.2526(2) 0.22422(11) 0.26712(17) 0.0337(6) Uani 1 1 d . . . . .
H16A H 0.3117 0.1973 0.3013 0.040 Uiso 1 1 calc R . . . .
H16B H 0.1726 0.2018 0.2635 0.040 Uiso 1 1 calc R . . . .
C17A C 0.2385(2) 0.29113(11) 0.31228(16) 0.0318(5) Uani 1 1 d . . . . .
H17A H 0.2637 0.2900 0.3774 0.038 Uiso 1 1 calc R . . . .
H17B H 0.1525 0.3063 0.3083 0.038 Uiso 1 1 calc R . . . .
C18A C 0.3263(2) 0.33483(10) 0.25494(14) 0.0271(5) Uani 1 1 d . . . . .
H18A H 0.2790 0.3691 0.2243 0.032 Uiso 1 1 calc R . . . .
H18B H 0.3888 0.3547 0.2951 0.032 Uiso 1 1 calc R . . . .
O3A O 0.38530(16) 0.29373(8) 0.18692(11) 0.0357(4) Uani 1 1 d . . . . .
C15B C 0.7004(2) 0.50947(12) 0.31260(16) 0.0324(5) Uani 1 1 d . . . . .
H15C H 0.7692 0.4972 0.3534 0.039 Uiso 1 1 calc R . . . .
H15D H 0.6565 0.5463 0.3399 0.039 Uiso 1 1 calc R . . . .
C16B C 0.7476(2) 0.52585(11) 0.21604(17) 0.0317(5) Uani 1 1 d . . . . .
H16C H 0.8270 0.5489 0.2187 0.038 Uiso 1 1 calc R . . . .
H16D H 0.6872 0.5520 0.1819 0.038 Uiso 1 1 calc R . . . .
C17B C 0.7628(2) 0.45862(11) 0.17206(16) 0.0327(5) Uani 1 1 d . . . . .
H17C H 0.8490 0.4438 0.1764 0.039 Uiso 1 1 calc R . . . .
H17D H 0.7377 0.4591 0.1069 0.039 Uiso 1 1 calc R . . . .
H1A H 0.0464(19) 0.5804(10) 0.3075(17) 0.039 Uiso 1 1 d DR . . . .
H2A H 0.423(2) 0.5890(10) 0.1797(16) 0.039 Uiso 1 1 d DR . . . .
H1B H 0.9519(19) 0.1652(10) 0.1917(17) 0.039 Uiso 1 1 d DR . . . .
H2B H 0.574(2) 0.1650(10) 0.3162(16) 0.039 Uiso 1 1 d DR . . . .
C18B C 0.6753(2) 0.41496(10) 0.23010(14) 0.0266(5) Uani 1 1 d . . . . .
H18C H 0.6122 0.3951 0.1903 0.032 Uiso 1 1 calc R . . . .
H18D H 0.7228 0.3806 0.2604 0.032 Uiso 1 1 calc R . . . .
O3B O 0.61740(16) 0.45608(8) 0.29836(11) 0.0358(4) 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
C1A C2A 1.503(2) . ?
C1A N2A 1.347(2) . ?
C1A O1A 1.233(2) . ?
C2A C3A 1.392(3) . ?
C2A C7A 1.393(3) . ?
C3A C10A 1.400(2) . ?
C3A N1A 1.425(2) . ?
C4A C5A 1.501(2) . ?
C4A N1A 1.349(2) . ?
C4A O2A 1.233(2) . ?
C5A C6A 1.396(3) . ?
C5A C11A 1.395(3) . ?
C6A C14A 1.396(2) . ?
C6A N2A 1.428(2) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.383(3) . ?
C8A C9A 1.378(3) . ?
C8A F1A 1.358(2) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.384(3) . ?
C10A H10A 0.9300 . ?
C11A H11A 0.9300 . ?
C11A C12A 1.385(3) . ?
C12A C13A 1.380(3) . ?
C12A F2A 1.354(2) . ?
C13A H13A 0.9300 . ?
C13A C14A 1.385(3) . ?
C14A H14A 0.9300 . ?
N1A H1A 0.874(10) . ?
N2A H2A 0.870(10) . ?
C1B C2B 1.501(2) . ?
C1B N2B 1.353(2) . ?
C1B O1B 1.233(2) . ?
C2B C3B 1.394(3) . ?
C2B C7B 1.394(3) . ?
C3B C10B 1.400(3) . ?
C3B N1B 1.423(2) . ?
C4B C5B 1.503(2) . ?
C4B N1B 1.348(2) . ?
C4B O2B 1.232(2) . ?
C5B C6B 1.396(3) . ?
C5B C11B 1.391(3) . ?
C6B C14B 1.394(3) . ?
C6B N2B 1.427(2) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.383(3) . ?
C8B C9B 1.379(3) . ?
C8B F1B 1.354(2) . ?
C9B H9B 0.9300 . ?
C9B C10B 1.382(3) . ?
C10B H10B 0.9300 . ?
C11B H11B 0.9300 . ?
C11B C12B 1.384(3) . ?
C12B C13B 1.379(3) . ?
C12B F2B 1.355(2) . ?
C13B H13B 0.9300 . ?
C13B C14B 1.385(3) . ?
C14B H14B 0.9300 . ?
N1B H1B 0.875(10) . ?
N2B H2B 0.869(10) . ?
C15A H15A 0.9700 . ?
C15A H15B 0.9700 . ?
C15A C16A 1.503(3) . ?
C15A O3A 1.428(3) . ?
C16A H16A 0.9700 . ?
C16A H16B 0.9700 . ?
C16A C17A 1.524(3) . ?
C17A H17A 0.9700 . ?
C17A H17B 0.9700 . ?
C17A C18A 1.534(3) . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C18A O3A 1.433(2) . ?
C15B H15C 0.9700 . ?
C15B H15D 0.9700 . ?
C15B C16B 1.508(3) . ?
C15B O3B 1.423(3) . ?
C16B H16C 0.9700 . ?
C16B H16D 0.9700 . ?
C16B C17B 1.524(3) . ?
C17B H17C 0.9700 . ?
C17B H17D 0.9700 . ?
C17B C18B 1.537(3) . ?
C18B H18C 0.9700 . ?
C18B H18D 0.9700 . ?
C18B O3B 1.431(2) . ?

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
N2A C1A C2A 118.52(16) . . ?
O1A C1A C2A 118.85(15) . . ?
O1A C1A N2A 122.63(16) . . ?
C3A C2A C1A 121.58(16) . . ?
C3A C2A C7A 120.40(17) . . ?
C7A C2A C1A 117.78(17) . . ?
C2A C3A C10A 119.74(17) . . ?
C2A C3A N1A 120.92(16) . . ?
C10A C3A N1A 119.22(17) . . ?
N1A C4A C5A 117.95(15) . . ?
O2A C4A C5A 119.75(16) . . ?
O2A C4A N1A 122.30(16) . . ?
C6A C5A C4A 121.23(16) . . ?
C11A C5A C4A 118.69(17) . . ?
C11A C5A C6A 119.91(17) . . ?
C5A C6A N2A 120.53(16) . . ?
C14A C6A C5A 120.11(17) . . ?
C14A C6A N2A 119.29(17) . . ?
C2A C7A H7A 121.1 . . ?
C8A C7A C2A 117.87(18) . . ?
C8A C7A H7A 121.1 . . ?
C9A C8A C7A 123.31(18) . . ?
F1A C8A C7A 117.89(17) . . ?
F1A C8A C9A 118.80(16) . . ?
C8A C9A H9A 120.9 . . ?
C8A C9A C10A 118.14(17) . . ?
C10A C9A H9A 120.9 . . ?
C3A C10A H10A 119.8 . . ?
C9A C10A C3A 120.44(18) . . ?
C9A C10A H10A 119.8 . . ?
C5A C11A H11A 120.9 . . ?
C12A C11A C5A 118.16(18) . . ?
C12A C11A H11A 120.9 . . ?
C13A C12A C11A 122.99(18) . . ?
F2A C12A C11A 118.36(17) . . ?
F2A C12A C13A 118.65(17) . . ?
C12A C13A H13A 120.8 . . ?
C12A C13A C14A 118.35(17) . . ?
C14A C13A H13A 120.8 . . ?
C6A C14A H14A 119.8 . . ?
C13A C14A C6A 120.35(18) . . ?
C13A C14A H14A 119.8 . . ?
C3A N1A H1A 116.5(17) . . ?
C4A N1A C3A 125.27(15) . . ?
C4A N1A H1A 117.5(18) . . ?
C1A N2A C6A 124.56(15) . . ?
C1A N2A H2A 119.1(17) . . ?
C6A N2A H2A 115.6(17) . . ?
N2B C1B C2B 118.24(16) . . ?
O1B C1B C2B 119.52(16) . . ?
O1B C1B N2B 122.24(16) . . ?
C3B C2B C1B 120.97(16) . . ?
C7B C2B C1B 118.68(17) . . ?
C7B C2B C3B 120.11(17) . . ?
C2B C3B C10B 119.85(17) . . ?
C2B C3B N1B 121.02(16) . . ?
C10B C3B N1B 119.05(17) . . ?
N1B C4B C5B 117.94(16) . . ?
O2B C4B C5B 119.62(16) . . ?
O2B C4B N1B 122.45(16) . . ?
C6B C5B C4B 121.38(16) . . ?
C11B C5B C4B 118.34(17) . . ?
C11B C5B C6B 120.10(17) . . ?
C5B C6B N2B 120.55(16) . . ?
C14B C6B C5B 119.79(17) . . ?
C14B C6B N2B 119.55(17) . . ?
C2B C7B H7B 121.0 . . ?
C8B C7B C2B 118.10(18) . . ?
C8B C7B H7B 121.0 . . ?
C9B C8B C7B 123.17(18) . . ?
F1B C8B C7B 118.37(18) . . ?
F1B C8B C9B 118.46(17) . . ?
C8B C9B H9B 120.9 . . ?
C8B C9B C10B 118.25(17) . . ?
C10B C9B H9B 120.9 . . ?
C3B C10B H10B 119.8 . . ?
C9B C10B C3B 120.46(18) . . ?
C9B C10B H10B 119.8 . . ?
C5B C11B H11B 120.9 . . ?
C12B C11B C5B 118.14(18) . . ?
C12B C11B H11B 120.9 . . ?
C13B C12B C11B 123.13(18) . . ?
F2B C12B C11B 117.97(17) . . ?
F2B C12B C13B 118.89(17) . . ?
C12B C13B H13B 121.0 . . ?
C12B C13B C14B 118.04(17) . . ?
C14B C13B H13B 121.0 . . ?
C6B C14B H14B 119.7 . . ?
C13B C14B C6B 120.66(17) . . ?
C13B C14B H14B 119.7 . . ?
C3B N1B H1B 117.6(17) . . ?
C4B N1B C3B 124.92(15) . . ?
C4B N1B H1B 116.3(17) . . ?
C1B N2B C6B 124.78(15) . . ?
C1B N2B H2B 117.4(17) . . ?
C6B N2B H2B 117.1(17) . . ?
H15A C15A H15B 108.9 . . ?
C16A C15A H15A 110.9 . . ?
C16A C15A H15B 110.9 . . ?
O3A C15A H15A 110.9 . . ?
O3A C15A H15B 110.9 . . ?
O3A C15A C16A 104.25(17) . . ?
C15A C16A H16A 111.2 . . ?
C15A C16A H16B 111.2 . . ?
C15A C16A C17A 102.66(18) . . ?
H16A C16A H16B 109.1 . . ?
C17A C16A H16A 111.2 . . ?
C17A C16A H16B 111.2 . . ?
C16A C17A H17A 111.0 . . ?
C16A C17A H17B 111.0 . . ?
C16A C17A C18A 103.82(17) . . ?
H17A C17A H17B 109.0 . . ?
C18A C17A H17A 111.0 . . ?
C18A C17A H17B 111.0 . . ?
C17A C18A H18A 110.4 . . ?
C17A C18A H18B 110.4 . . ?
H18A C18A H18B 108.6 . . ?
O3A C18A C17A 106.72(17) . . ?
O3A C18A H18A 110.4 . . ?
O3A C18A H18B 110.4 . . ?
C15A O3A C18A 106.17(16) . . ?
H15C C15B H15D 108.9 . . ?
C16B C15B H15C 110.9 . . ?
C16B C15B H15D 110.9 . . ?
O3B C15B H15C 110.9 . . ?
O3B C15B H15D 110.9 . . ?
O3B C15B C16B 104.37(17) . . ?
C15B C16B H16C 111.3 . . ?
C15B C16B H16D 111.3 . . ?
C15B C16B C17B 102.25(18) . . ?
H16C C16B H16D 109.2 . . ?
C17B C16B H16C 111.3 . . ?
C17B C16B H16D 111.3 . . ?
C16B C17B H17C 111.0 . . ?
C16B C17B H17D 111.0 . . ?
C16B C17B C18B 103.84(17) . . ?
H17C C17B H17D 109.0 . . ?
C18B C17B H17C 111.0 . . ?
C18B C17B H17D 111.0 . . ?
C17B C18B H18C 110.4 . . ?
C17B C18B H18D 110.4 . . ?
H18C C18B H18D 108.6 . . ?
O3B C18B C17B 106.72(17) . . ?
O3B C18B H18C 110.4 . . ?
O3B C18B H18D 110.4 . . ?
C15B O3B C18B 106.43(16) . . ?

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
C1A C2A C3A C10A -171.56(16) . . . . ?
C1A C2A C3A N1A 4.4(2) . . . . ?
C1A C2A C7A C8A 174.12(16) . . . . ?
C2A C1A N2A C6A -8.7(3) . . . . ?
C2A C3A C10A C9A -2.5(3) . . . . ?
C2A C3A N1A C4A 69.7(2) . . . . ?
C2A C7A C8A C9A -2.3(3) . . . . ?
C2A C7A C8A F1A 177.45(15) . . . . ?
C3A C2A C7A C8A -0.4(3) . . . . ?
C4A C5A C6A C14A -172.66(16) . . . . ?
C4A C5A C6A N2A 4.4(2) . . . . ?
C4A C5A C11A C12A 175.88(16) . . . . ?
C5A C4A N1A C3A -6.4(3) . . . . ?
C5A C6A C14A C13A -3.0(3) . . . . ?
C5A C6A N2A C1A 71.3(2) . . . . ?
C5A C11A C12A C13A -3.3(3) . . . . ?
C5A C11A C12A F2A 176.68(15) . . . . ?
C6A C5A C11A C12A 0.6(3) . . . . ?
C7A C2A C3A C10A 2.7(3) . . . . ?
C7A C2A C3A N1A 178.63(15) . . . . ?
C7A C8A C9A C10A 2.5(3) . . . . ?
C8A C9A C10A C3A -0.1(3) . . . . ?
C10A C3A N1A C4A -114.3(2) . . . . ?
C11A C5A C6A C14A 2.5(3) . . . . ?
C11A C5A C6A N2A 179.53(15) . . . . ?
C11A C12A C13A C14A 2.8(3) . . . . ?
C12A C13A C14A C6A 0.5(3) . . . . ?
C14A C6A N2A C1A -111.6(2) . . . . ?
F1A C8A C9A C10A -177.25(16) . . . . ?
F2A C12A C13A C14A -177.22(16) . . . . ?
N1A C3A C10A C9A -178.50(16) . . . . ?
N1A C4A C5A C6A -66.9(2) . . . . ?
N1A C4A C5A C11A 117.96(19) . . . . ?
N2A C1A C2A C3A -65.3(2) . . . . ?
N2A C1A C2A C7A 120.32(18) . . . . ?
N2A C6A C14A C13A 179.86(16) . . . . ?
O1A C1A C2A C3A 114.4(2) . . . . ?
O1A C1A C2A C7A -60.0(2) . . . . ?
O1A C1A N2A C6A 171.64(17) . . . . ?
O2A C4A C5A C6A 113.8(2) . . . . ?
O2A C4A C5A C11A -61.4(2) . . . . ?
O2A C4A N1A C3A 172.86(17) . . . . ?
C1B C2B C3B C10B 172.48(16) . . . . ?
C1B C2B C3B N1B -4.1(2) . . . . ?
C1B C2B C7B C8B -174.61(16) . . . . ?
C2B C1B N2B C6B 7.9(3) . . . . ?
C2B C3B C10B C9B 1.9(3) . . . . ?
C2B C3B N1B C4B -71.2(2) . . . . ?
C2B C7B C8B C9B 2.2(3) . . . . ?
C2B C7B C8B F1B -176.72(15) . . . . ?
C3B C2B C7B C8B -0.2(3) . . . . ?
C4B C5B C6B C14B 171.63(16) . . . . ?
C4B C5B C6B N2B -4.5(2) . . . . ?
C4B C5B C11B C12B -174.73(16) . . . . ?
C5B C4B N1B C3B 7.9(3) . . . . ?
C5B C6B C14B C13B 3.2(3) . . . . ?
C5B C6B N2B C1B -70.9(2) . . . . ?
C5B C11B C12B C13B 2.9(3) . . . . ?
C5B C11B C12B F2B -178.13(15) . . . . ?
C6B C5B C11B C12B 0.3(3) . . . . ?
C7B C2B C3B C10B -1.8(3) . . . . ?
C7B C2B C3B N1B -178.38(15) . . . . ?
C7B C8B C9B C10B -2.1(3) . . . . ?
C8B C9B C10B C3B 0.0(3) . . . . ?
C10B C3B N1B C4B 112.2(2) . . . . ?
C11B C5B C6B C14B -3.3(3) . . . . ?
C11B C5B C6B N2B -179.46(15) . . . . ?
C11B C12B C13B C14B -3.0(3) . . . . ?
C12B C13B C14B C6B -0.1(3) . . . . ?
C14B C6B N2B C1B 113.0(2) . . . . ?
F1B C8B C9B C10B 176.80(16) . . . . ?
F2B C12B C13B C14B 178.04(15) . . . . ?
N1B C3B C10B C9B 178.54(16) . . . . ?
N1B C4B C5B C6B 66.1(2) . . . . ?
N1B C4B C5B C11B -118.92(19) . . . . ?
N2B C1B C2B C3B 65.7(2) . . . . ?
N2B C1B C2B C7B -119.87(19) . . . . ?
N2B C6B C14B C13B 179.41(16) . . . . ?
O1B C1B C2B C3B -114.5(2) . . . . ?
O1B C1B C2B C7B 59.9(2) . . . . ?
O1B C1B N2B C6B -171.82(17) . . . . ?
O2B C4B C5B C6B -114.2(2) . . . . ?
O2B C4B C5B C11B 60.8(2) . . . . ?
O2B C4B N1B C3B -171.84(17) . . . . ?
C15A C16A C17A C18A -21.5(2) . . . . ?
C16A C15A O3A C18A -40.5(2) . . . . ?
C16A C17A C18A O3A -1.8(2) . . . . ?
C17A C18A O3A C15A 26.1(2) . . . . ?
O3A C15A C16A C17A 38.1(2) . . . . ?
C15B C16B C17B C18B 22.3(2) . . . . ?
C16B C15B O3B C18B 40.3(2) . . . . ?
C16B C17B C18B O3B 0.7(2) . . . . ?
C17B C18B O3B C15B -25.3(2) . . . . ?
O3B C15B C16B C17B -38.4(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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 1.173
_oxdiff_exptl_absorpt_empirical_full_min 0.826
####################################################################### 
# 
# 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_2018_01_25_dt_bbbr2thf_n
_database_code_depnum_ccdc_archive 'CCDC 1995130'
loop_
_audit_author_name
_audit_author_address
'Damian Trzybinski'
;Biological and Chemical Research Centre University of Warsaw
Poland
;
_audit_update_record             
;
2020-04-06 deposited with the CCDC.	2020-07-10 downloaded from the CCDC.
;
_audit_creation_date             2020-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 Br2 N2 O2, C4 H8 O'
_chemical_formula_sum            'C18 H16 Br2 N2 O3'
_chemical_formula_weight         468.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         ?
_chemical_oxdiff_usercomment     ?
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.77295(12)
_cell_length_b                   10.79851(9)
_cell_length_c                   31.7818(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3697.23(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    40453
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.4050
_cell_measurement_theta_min      2.7600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.731
_exptl_absorpt_correction_T_max  0.763
_exptl_absorpt_correction_T_min  0.246
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.682
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0731
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            115169
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.037
_diffrn_reflns_theta_max         67.037
_diffrn_reflns_theta_min         2.781
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4391
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      ?
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0767724000
_diffrn_orient_matrix_UB_12      0.1011736000
_diffrn_orient_matrix_UB_13      0.0221643000
_diffrn_orient_matrix_UB_21      -0.0780515000
_diffrn_orient_matrix_UB_22      -0.1005849000
_diffrn_orient_matrix_UB_23      0.0219542000
_diffrn_orient_matrix_UB_31      0.0920353000
_diffrn_orient_matrix_UB_32      -0.0009533000
_diffrn_orient_matrix_UB_33      0.0370875000
_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                3037
_reflns_number_total             3289
_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 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         3.419
_refine_diff_density_min         -1.313
_refine_diff_density_rms         0.145
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3289
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0576
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0787P)²+28.4993P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1538
_refine_ls_wR_factor_ref         0.1575
_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
2. Uiso/Uaniso restraints and constraints
Uanis(C18) \\sim Ueq, Uanis(C17) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 C15, C16, C17, C18, O3
 with sigma for 1-2 distances of 0.0025 and sigma for 1-3 distances of 0.0025
4.a Free rotating group:
 O3(C15,C16,C17,C18)
4.b Secondary CH2 refined with riding coordinates:
 C15(H15a,H15b), C16(H16a,H16b), C17(H17a,H17b), C18(H18b,H18a)
4.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), N1(H1), N2(H2)
;
_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 -0.69802(6) -0.89213(5) -0.48558(2) 0.0301(2) Uani 1 1 d . . . . .
Br2 Br -0.73446(6) -0.66743(6) -0.76345(2) 0.0344(2) Uani 1 1 d . . . . .
C1 C -0.3401(5) -0.8290(4) -0.59648(15) 0.0169(10) Uani 1 1 d . . . . .
C2 C -0.4469(4) -0.7683(4) -0.57452(14) 0.0174(10) Uani 1 1 d . . . . .
C3 C -0.4732(4) -0.6425(4) -0.57749(14) 0.0159(9) Uani 1 1 d . . . . .
C4 C -0.4031(4) -0.5684(4) -0.64678(15) 0.0160(9) Uani 1 1 d . . . . .
C5 C -0.4729(5) -0.6700(4) -0.66867(15) 0.0166(10) Uani 1 1 d . . . . .
C6 C -0.4378(4) -0.7944(5) -0.66584(15) 0.0177(10) Uani 1 1 d . . . . .
C7 C -0.5153(5) -0.8429(4) -0.54695(15) 0.0206(10) Uani 1 1 d . . . . .
H7 H -0.4993 -0.9273 -0.5450 0.025 Uiso 1 1 calc R . . . .
C8 C -0.6066(5) -0.7895(5) -0.52277(16) 0.0223(11) Uani 1 1 d . . . . .
C9 C -0.6313(5) -0.6635(5) -0.52421(16) 0.0228(11) Uani 1 1 d . . . . .
H9 H -0.6919 -0.6289 -0.5070 0.027 Uiso 1 1 calc R . . . .
C10 C -0.5640(5) -0.5900(5) -0.55181(16) 0.0227(11) Uani 1 1 d . . . . .
H10 H -0.5795 -0.5054 -0.5532 0.027 Uiso 1 1 calc R . . . .
C11 C -0.5635(5) -0.6343(5) -0.69766(15) 0.0193(10) Uani 1 1 d . . . . .
H11 H -0.5884 -0.5521 -0.6994 0.023 Uiso 1 1 calc R . . . .
C12 C -0.6156(5) -0.7222(5) -0.72362(16) 0.0242(11) Uani 1 1 d . . . . .
C13 C -0.5801(5) -0.8455(5) -0.72189(17) 0.0258(11) Uani 1 1 d . . . . .
H13 H -0.6158 -0.9034 -0.7399 0.031 Uiso 1 1 calc R . . . .
C14 C -0.4907(5) -0.8813(5) -0.69294(16) 0.0224(11) Uani 1 1 d . . . . .
H14 H -0.4659 -0.9637 -0.6916 0.027 Uiso 1 1 calc R . . . .
N1 N -0.4020(4) -0.5643(4) -0.60477(12) 0.0175(8) Uani 1 1 d . . . . .
H1 H -0.3546 -0.5102 -0.5931 0.021 Uiso 1 1 calc R . . . .
N2 N -0.3396(4) -0.8331(4) -0.63883(13) 0.0185(9) Uani 1 1 d . . . . .
H2 H -0.2739 -0.8618 -0.6507 0.022 Uiso 1 1 calc R . . . .
O1 O -0.2562(3) -0.8758(3) -0.57522(10) 0.0199(7) Uani 1 1 d . . . . .
O2 O -0.3503(3) -0.4902(3) -0.66879(10) 0.0213(8) Uani 1 1 d . . . . .
O3 O -0.8442(9) -0.8203(7) -0.5979(3) 0.144(4) Uani 1 1 d . U . A -1
C15 C -0.9165(10) -0.7168(8) -0.58351(19) 0.118(5) Uani 1 1 d G U . A -1
H15A H -0.8628 -0.6489 -0.5753 0.142 Uiso 1 1 calc R . . A -1
H15B H -0.9670 -0.7403 -0.5595 0.142 Uiso 1 1 calc R . . A -1
C16 C -0.9990(8) -0.6786(8) -0.6205(2) 0.082(3) Uani 1 1 d G U . A -1
H16A H -1.0162 -0.5904 -0.6201 0.099 Uiso 1 1 calc R . . A -1
H16B H -1.0767 -0.7239 -0.6206 0.099 Uiso 1 1 calc R . . A -1
C17 C -0.9178(10) -0.7141(10) -0.65837(19) 0.136(5) Uani 1 1 d G U . A -1
H17A H -0.9676 -0.7295 -0.6832 0.164 Uiso 1 1 calc R . . A -1
H17B H -0.8570 -0.6504 -0.6645 0.164 Uiso 1 1 calc R . . A -1
C18 C -0.8555(10) -0.8330(9) -0.6426(3) 0.130(4) Uani 1 1 d G U . A -1
H18B H -0.9057 -0.9047 -0.6496 0.155 Uiso 1 1 calc R . . A -1
H18A H -0.7743 -0.8428 -0.6554 0.155 Uiso 1 1 calc R . . A -1


_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 C8 1.896(5) . ?
Br2 C12 1.896(5) . ?
C1 C2 1.497(7) . ?
C1 N2 1.347(6) . ?
C1 O1 1.236(6) . ?
C2 C3 1.391(7) . ?
C2 C7 1.400(7) . ?
C3 C10 1.394(7) . ?
C3 N1 1.432(6) . ?
C4 C5 1.501(7) . ?
C4 N1 1.336(6) . ?
C4 O2 1.236(6) . ?
C5 C6 1.399(7) . ?
C5 C11 1.396(7) . ?
C6 C14 1.395(7) . ?
C6 N2 1.424(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.375(7) . ?
C8 C9 1.388(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.388(7) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.377(7) . ?
C12 C13 1.386(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(8) . ?
C14 H14 0.9300 . ?
N1 H1 0.8600 . ?
N2 H2 0.8600 . ?
O3 C15 1.4367 . ?
O3 C18 1.4352 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.5314 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.5356 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.5322 . ?
C18 H18B 0.9700 . ?
C18 H18A 0.9700 . ?

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
N2 C1 C2 118.9(4) . . ?
O1 C1 C2 119.1(4) . . ?
O1 C1 N2 122.0(5) . . ?
C3 C2 C1 123.5(4) . . ?
C3 C2 C7 119.8(5) . . ?
C7 C2 C1 116.4(4) . . ?
C2 C3 C10 120.0(4) . . ?
C2 C3 N1 120.5(4) . . ?
C10 C3 N1 119.3(4) . . ?
N1 C4 C5 119.5(4) . . ?
O2 C4 C5 117.9(4) . . ?
O2 C4 N1 122.6(4) . . ?
C6 C5 C4 122.5(4) . . ?
C11 C5 C4 117.0(4) . . ?
C11 C5 C6 119.8(5) . . ?
C5 C6 N2 121.4(4) . . ?
C14 C6 C5 119.7(5) . . ?
C14 C6 N2 118.6(4) . . ?
C2 C7 H7 120.5 . . ?
C8 C7 C2 119.0(5) . . ?
C8 C7 H7 120.5 . . ?
C7 C8 Br1 118.4(4) . . ?
C7 C8 C9 122.0(5) . . ?
C9 C8 Br1 119.6(4) . . ?
C8 C9 H9 120.6 . . ?
C8 C9 C10 118.8(5) . . ?
C10 C9 H9 120.6 . . ?
C3 C10 H10 119.9 . . ?
C9 C10 C3 120.3(5) . . ?
C9 C10 H10 119.9 . . ?
C5 C11 H11 120.3 . . ?
C12 C11 C5 119.3(5) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 Br2 117.4(4) . . ?
C11 C12 C13 121.8(5) . . ?
C13 C12 Br2 120.8(4) . . ?
C12 C13 H13 120.5 . . ?
C12 C13 C14 119.0(5) . . ?
C14 C13 H13 120.5 . . ?
C6 C14 H14 119.8 . . ?
C13 C14 C6 120.4(5) . . ?
C13 C14 H14 119.8 . . ?
C3 N1 H1 117.3 . . ?
C4 N1 C3 125.5(4) . . ?
C4 N1 H1 117.3 . . ?
C1 N2 C6 126.2(4) . . ?
C1 N2 H2 116.9 . . ?
C6 N2 H2 116.9 . . ?
C18 O3 C15 110.1 . . ?
O3 C15 H15A 110.5 . . ?
O3 C15 H15B 110.5 . . ?
O3 C15 C16 106.3 . . ?
H15A C15 H15B 108.7 . . ?
C16 C15 H15A 110.5 . . ?
C16 C15 H15B 110.5 . . ?
C15 C16 H16A 111.4 . . ?
C15 C16 H16B 111.4 . . ?
C15 C16 C17 101.8 . . ?
H16A C16 H16B 109.3 . . ?
C17 C16 H16A 111.4 . . ?
C17 C16 H16B 111.4 . . ?
C16 C17 H17A 111.4 . . ?
C16 C17 H17B 111.4 . . ?
H17A C17 H17B 109.3 . . ?
C18 C17 C16 101.8 . . ?
C18 C17 H17A 111.4 . . ?
C18 C17 H17B 111.4 . . ?
O3 C18 C17 106.3 . . ?
O3 C18 H18B 110.5 . . ?
O3 C18 H18A 110.5 . . ?
C17 C18 H18B 110.5 . . ?
C17 C18 H18A 110.5 . . ?
H18B C18 H18A 108.7 . . ?

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 C8 C9 C10 -179.6(4) . . . . ?
Br2 C12 C13 C14 178.5(4) . . . . ?
C1 C2 C3 C10 -171.5(5) . . . . ?
C1 C2 C3 N1 4.3(7) . . . . ?
C1 C2 C7 C8 173.6(5) . . . . ?
C2 C1 N2 C6 -6.0(7) . . . . ?
C2 C3 C10 C9 -2.1(8) . . . . ?
C2 C3 N1 C4 68.5(7) . . . . ?
C2 C7 C8 Br1 -179.9(4) . . . . ?
C2 C7 C8 C9 -1.3(8) . . . . ?
C3 C2 C7 C8 -0.9(7) . . . . ?
C4 C5 C6 C14 -167.8(4) . . . . ?
C4 C5 C6 N2 5.7(7) . . . . ?
C4 C5 C11 C12 169.3(5) . . . . ?
C5 C4 N1 C3 -6.8(7) . . . . ?
C5 C6 C14 C13 -1.6(8) . . . . ?
C5 C6 N2 C1 66.4(7) . . . . ?
C5 C11 C12 Br2 -178.2(4) . . . . ?
C5 C11 C12 C13 -0.3(8) . . . . ?
C6 C5 C11 C12 -1.1(7) . . . . ?
C7 C2 C3 C10 2.6(7) . . . . ?
C7 C2 C3 N1 178.4(4) . . . . ?
C7 C8 C9 C10 1.8(8) . . . . ?
C8 C9 C10 C3 -0.1(8) . . . . ?
C10 C3 N1 C4 -115.7(6) . . . . ?
C11 C5 C6 C14 2.0(7) . . . . ?
C11 C5 C6 N2 175.5(4) . . . . ?
C11 C12 C13 C14 0.7(8) . . . . ?
C12 C13 C14 C6 0.3(8) . . . . ?
C14 C6 N2 C1 -120.1(5) . . . . ?
N1 C3 C10 C9 -178.0(5) . . . . ?
N1 C4 C5 C6 -66.0(7) . . . . ?
N1 C4 C5 C11 123.9(5) . . . . ?
N2 C1 C2 C3 -65.6(7) . . . . ?
N2 C1 C2 C7 120.1(5) . . . . ?
N2 C6 C14 C13 -175.3(5) . . . . ?
O1 C1 C2 C3 115.7(5) . . . . ?
O1 C1 C2 C7 -58.6(6) . . . . ?
O1 C1 N2 C6 172.6(5) . . . . ?
O2 C4 C5 C6 115.2(5) . . . . ?
O2 C4 C5 C11 -54.9(6) . . . . ?
O2 C4 N1 C3 172.0(4) . . . . ?
O3 C15 C16 C17 -30.6 . . . . ?
C15 O3 C18 C17 12.0 . . . . ?
C15 C16 C17 C18 36.3 . . . . ?
C16 C17 C18 O3 -30.6 . . . . ?
C18 O3 C15 C16 12.0 . . . . ?

_shelx_SHELXL_version_number     2014/7
_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 1.736
_oxdiff_exptl_absorpt_empirical_full_min 0.543
