# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_130726-230K-1
_database_code_depnum_ccdc_archive 'CCDC 1451796'
_audit_update_record             
;
2016-02-04 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C18 H15 Br F3 N O'
_chemical_formula_moiety         'C18 H15 Br F3 N O'
_chemical_formula_weight         398.22
_chemical_melting_point          ?
_chemical_absolute_configuration unk

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_Int_Tables_number      1
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
#------------------------------------------------------------------------------
_cell_length_a                   5.0171(14)
_cell_length_b                   8.347(2)
_cell_length_c                   10.439(3)
_cell_angle_alpha                101.211(5)
_cell_angle_beta                 102.192(7)
_cell_angle_gamma                91.033(8)
_cell_volume                     418.4(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2022
_cell_measurement_theta_min      4.33
_cell_measurement_theta_max      27.47
_cell_measurement_temperature    233
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             200.00
_exptl_absorpt_coefficient_mu    2.498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.422
_exptl_absorpt_correction_T_max  0.607

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      233
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            8770
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using reflections with F² > 2.0 sigma(F²).
    The weighted     R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3667
_reflns_number_gt                2890
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0242
_refine_ls_wR_factor_ref         0.0288
_refine_ls_number_restraints     ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2890
_refine_ls_number_parameters     232
_refine_ls_goodness_of_fit_ref   0.818
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w = 1/[1.0000σ(Fo²)]/(4Fo²)'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.466
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.33559(9) -0.03986(5) -0.03663(4) 0.05192(9) Uani 1.0 1 d . . .
F1 F 0.5515(3) 0.68555(18) 0.51540(13) 0.0726(6) Uani 1.0 1 d . . .
F2 F 0.7111(4) 0.84704(18) 0.70256(16) 0.0723(6) Uani 1.0 1 d . . .
F3 F 0.2905(4) 0.76643(19) 0.64662(14) 0.0717(6) Uani 1.0 1 d . . .
O1 O 0.9900(3) 0.20490(19) 0.63273(15) 0.0390(6) Uani 1.0 1 d . . .
N1 N 0.5289(4) 0.15514(19) 0.56841(15) 0.0262(6) Uani 1.0 1 d . . .
C1 C 0.7631(5) 0.2062(3) 0.6611(2) 0.0263(7) Uani 1.0 1 d . . .
C2 C 0.7285(5) 0.2648(3) 0.8011(2) 0.0288(7) Uani 1.0 1 d . . .
C3 C 0.8952(6) 0.4273(3) 0.8684(3) 0.0287(8) Uani 1.0 1 d . . .
C4 C 0.8120(5) 0.5678(3) 0.8004(3) 0.0353(7) Uani 1.0 1 d . . .
C5 C 0.6002(5) 0.5748(3) 0.7074(3) 0.0390(8) Uani 1.0 1 d . . .
C6 C 0.5416(6) 0.7160(3) 0.6446(3) 0.0434(9) Uani 1.0 1 d . . .
C7 C 0.9063(5) 0.4715(3) 1.0171(2) 0.0277(7) Uani 1.0 1 d . . .
C8 C 1.1028(5) 0.4096(3) 1.1064(3) 0.0337(7) Uani 1.0 1 d . . .
C9 C 1.1174(5) 0.4477(4) 1.2422(3) 0.0399(8) Uani 1.0 1 d . . .
C10 C 0.9383(5) 0.5523(3) 1.2921(3) 0.0400(8) Uani 1.0 1 d . . .
C11 C 0.7388(6) 0.6150(3) 1.2065(3) 0.0402(8) Uani 1.0 1 d . . .
C12 C 0.7242(6) 0.5723(4) 1.0692(3) 0.0366(8) Uani 1.0 1 d . . .
C13 C 0.4989(4) 0.1035(3) 0.4281(2) 0.0240(7) Uani 1.0 1 d . . .
C14 C 0.2857(5) -0.0065(3) 0.3586(2) 0.0329(7) Uani 1.0 1 d . . .
C15 C 0.2373(5) -0.0516(3) 0.2205(3) 0.0362(8) Uani 1.0 1 d . . .
C16 C 0.4033(5) 0.0150(3) 0.1535(2) 0.0303(7) Uani 1.0 1 d . . .
C17 C 0.6173(5) 0.1262(3) 0.2215(3) 0.0336(8) Uani 1.0 1 d . . .
C18 C 0.6646(5) 0.1703(3) 0.3586(2) 0.0333(7) Uani 1.0 1 d . . .
H1 H 0.3807 0.1546 0.5987 0.0323 Uiso 1.0 1 calc R . .
H2 H 0.5345 0.2778 0.8003 0.0348 Uiso 1.0 1 calc R . .
H3 H 0.7916 0.1831 0.8537 0.0357 Uiso 1.0 1 calc R . .
H4 H 1.0861 0.4092 0.8611 0.0336 Uiso 1.0 1 calc R . .
H5 H 0.9273 0.6626 0.8349 0.0407 Uiso 1.0 1 calc R . .
H6 H 0.4800 0.4820 0.6725 0.0454 Uiso 1.0 1 calc R . .
H7 H 1.2277 0.3399 1.0735 0.0402 Uiso 1.0 1 calc R . .
H8 H 1.2500 0.4025 1.3003 0.0477 Uiso 1.0 1 calc R . .
H9 H 0.9527 0.5811 1.3846 0.0474 Uiso 1.0 1 calc R . .
H10 H 0.6146 0.6845 1.2402 0.0495 Uiso 1.0 1 calc R . .
H11 H 0.5886 0.6160 1.0115 0.0447 Uiso 1.0 1 calc R . .
H12 H 0.1724 -0.0517 0.4045 0.0404 Uiso 1.0 1 calc R . .
H13 H 0.0917 -0.1266 0.1730 0.0419 Uiso 1.0 1 calc R . .
H14 H 0.7289 0.1711 0.1747 0.0422 Uiso 1.0 1 calc R . .
H15 H 0.8107 0.2451 0.4057 0.0398 Uiso 1.0 1 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Br1 C16 1.903(3) yes . .
F1 C6 1.335(3) yes . .
F2 C6 1.333(3) yes . .
F3 C6 1.339(4) yes . .
O1 C1 1.236(3) yes . .
N1 C1 1.356(3) yes . .
N1 C13 1.418(3) yes . .
C1 C2 1.495(3) yes . .
C2 C3 1.540(3) yes . .
C3 C4 1.507(4) yes . .
C3 C7 1.513(4) yes . .
C4 C5 1.290(4) yes . .
C5 C6 1.462(4) yes . .
C7 C8 1.388(3) yes . .
C7 C12 1.378(4) yes . .
C8 C9 1.377(4) yes . .
C9 C10 1.375(4) yes . .
C10 C11 1.377(4) yes . .
C11 C12 1.393(4) yes . .
C13 C14 1.375(3) yes . .
C13 C18 1.388(4) yes . .
C14 C15 1.385(3) yes . .
C15 C16 1.368(4) yes . .
C16 C17 1.380(3) yes . .
C17 C18 1.374(3) yes . .
N1 H1 0.867 no . .
C2 H2 0.980 no . .
C2 H3 0.973 no . .
C3 H4 0.989 no . .
C4 H5 0.936 no . .
C5 H6 0.936 no . .
C8 H7 0.936 no . .
C9 H8 0.938 no . .
C10 H9 0.935 no . .
C11 H10 0.936 no . .
C12 H11 0.938 no . .
C14 H12 0.934 no . .
C15 H13 0.938 no . .
C17 H14 0.934 no . .
C18 H15 0.938 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 N1 C13 127.49(19) yes . . .
O1 C1 N1 122.7(2) yes . . .
O1 C1 C2 121.92(18) yes . . .
N1 C1 C2 115.4(2) yes . . .
C1 C2 C3 111.9(2) yes . . .
C2 C3 C4 114.13(19) yes . . .
C2 C3 C7 112.5(3) yes . . .
C4 C3 C7 111.8(2) yes . . .
C3 C4 C5 128.5(3) yes . . .
C4 C5 C6 124.3(3) yes . . .
F1 C6 F2 106.2(3) yes . . .
F1 C6 F3 104.66(19) yes . . .
F1 C6 C5 113.2(2) yes . . .
F2 C6 F3 105.5(2) yes . . .
F2 C6 C5 113.8(2) yes . . .
F3 C6 C5 112.8(3) yes . . .
C3 C7 C8 120.3(3) yes . . .
C3 C7 C12 122.2(3) yes . . .
C8 C7 C12 117.5(3) yes . . .
C7 C8 C9 121.5(3) yes . . .
C8 C9 C10 119.8(3) yes . . .
C9 C10 C11 120.3(3) yes . . .
C10 C11 C12 119.0(3) yes . . .
C7 C12 C11 121.9(3) yes . . .
N1 C13 C14 118.6(2) yes . . .
N1 C13 C18 121.81(17) yes . . .
C14 C13 C18 119.4(2) yes . . .
C13 C14 C15 120.5(3) yes . . .
C14 C15 C16 119.28(19) yes . . .
Br1 C16 C15 120.24(15) yes . . .
Br1 C16 C17 118.73(19) yes . . .
C15 C16 C17 121.0(2) yes . . .
C16 C17 C18 119.5(3) yes . . .
C13 C18 C17 120.30(19) yes . . .
C1 N1 H1 115.985 no . . .
C13 N1 H1 116.525 no . . .
C1 C2 H2 109.500 no . . .
C1 C2 H3 108.939 no . . .
C3 C2 H2 110.031 no . . .
C3 C2 H3 108.148 no . . .
H2 C2 H3 108.259 no . . .
C2 C3 H4 106.536 no . . .
C4 C3 H4 105.999 no . . .
C7 C3 H4 105.076 no . . .
C3 C4 H5 113.876 no . . .
C5 C4 H5 117.583 no . . .
C4 C5 H6 119.128 no . . .
C6 C5 H6 116.417 no . . .
C7 C8 H7 119.174 no . . .
C9 C8 H7 119.278 no . . .
C8 C9 H8 119.868 no . . .
C10 C9 H8 120.297 no . . .
C9 C10 H9 119.724 no . . .
C11 C10 H9 120.020 no . . .
C10 C11 H10 120.321 no . . .
C12 C11 H10 120.719 no . . .
C7 C12 H11 119.636 no . . .
C11 C12 H11 118.487 no . . .
C13 C14 H12 120.046 no . . .
C15 C14 H12 119.412 no . . .
C14 C15 H13 120.554 no . . .
C16 C15 H13 120.169 no . . .
C16 C17 H14 120.243 no . . .
C18 C17 H14 120.295 no . . .
C13 C18 H15 119.684 no . . .
C17 C18 H15 120.016 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N1 C13 C14 152.02(19) no . . . .
C1 N1 C13 C18 -33.1(3) no . . . .
C13 N1 C1 O1 -4.2(4) no . . . .
C13 N1 C1 C2 175.74(17) no . . . .
O1 C1 C2 C3 46.1(3) no . . . .
N1 C1 C2 C3 -133.83(18) no . . . .
C1 C2 C3 C4 62.2(3) no . . . .
C1 C2 C3 C7 -169.01(17) no . . . .
C2 C3 C4 C5 10.7(4) no . . . .
C2 C3 C7 C8 85.4(3) no . . . .
C2 C3 C7 C12 -94.1(3) no . . . .
C4 C3 C7 C8 -144.6(2) no . . . .
C4 C3 C7 C12 35.9(3) no . . . .
C7 C3 C4 C5 -118.4(3) no . . . .
C3 C4 C5 C6 -178.0(3) no . . . .
C4 C5 C6 F1 113.9(3) no . . . .
C4 C5 C6 F2 -7.4(4) no . . . .
C4 C5 C6 F3 -127.5(3) no . . . .
C3 C7 C8 C9 -179.92(19) no . . . .
C3 C7 C12 C11 -178.8(2) no . . . .
C8 C7 C12 C11 1.7(4) no . . . .
C12 C7 C8 C9 -0.4(4) no . . . .
C7 C8 C9 C10 -1.5(4) no . . . .
C8 C9 C10 C11 2.0(4) no . . . .
C9 C10 C11 C12 -0.8(4) no . . . .
C10 C11 C12 C7 -1.1(4) no . . . .
N1 C13 C14 C15 175.49(16) no . . . .
N1 C13 C18 C17 -175.23(17) no . . . .
C14 C13 C18 C17 -0.4(3) no . . . .
C18 C13 C14 C15 0.5(3) no . . . .
C13 C14 C15 C16 -0.3(4) no . . . .
C14 C15 C16 Br1 -178.22(17) no . . . .
C14 C15 C16 C17 -0.1(4) no . . . .
Br1 C16 C17 C18 178.34(14) no . . . .
C15 C16 C17 C18 0.2(4) no . . . .
C16 C17 C18 C13 0.1(4) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
F1 C4 3.327(3) no . .
F2 C4 2.736(3) no . .
F3 C4 3.404(3) no . .
O1 C3 2.911(3) no . .
O1 C4 3.425(3) no . .
O1 C13 2.890(3) no . .
O1 C18 2.937(3) no . .
N1 C5 3.502(3) no . .
C1 C4 3.066(3) no . .
C1 C5 3.170(4) no . .
C1 C18 3.046(4) no . .
C2 C5 2.974(4) no . .
C2 C8 3.323(3) no . .
C2 C12 3.414(4) no . .
C4 C12 2.925(4) no . .
C5 C7 3.548(4) no . .
C7 C10 2.787(4) no . .
C8 C11 2.754(4) no . .
C9 C12 2.745(4) no . .
C13 C16 2.753(3) no . .
C14 C17 2.757(4) no . .
C15 C18 2.761(3) no . .
Br1 F3 3.3454(17) no . 1_544
F1 C9 3.441(3) no . 1_454
F1 C10 3.461(3) no . 1_454
F1 C10 3.379(3) no . 1_554
F1 C11 3.492(4) no . 1_554
F1 C14 3.450(3) no . 1_565
F2 F3 3.143(3) no . 1_655
F2 O1 3.541(3) no . 1_565
F2 N1 3.218(3) no . 1_565
F2 C1 3.125(3) no . 1_565
F2 C2 3.433(3) no . 1_565
F3 Br1 3.3454(17) no . 1_566
F3 F2 3.143(3) no . 1_455
O1 F2 3.541(3) no . 1_545
O1 N1 2.938(3) no . 1_655
N1 F2 3.218(3) no . 1_545
N1 O1 2.938(3) no . 1_455
C1 F2 3.125(3) no . 1_545
C2 F2 3.433(3) no . 1_545
C8 C11 3.452(4) no . 1_655
C8 C12 3.504(4) no . 1_655
C9 F1 3.441(3) no . 1_656
C9 C11 3.514(4) no . 1_655
C9 C17 3.584(4) no . 1_556
C10 F1 3.379(3) no . 1_556
C10 F1 3.461(3) no . 1_656
C11 F1 3.492(4) no . 1_556
C11 C8 3.452(4) no . 1_455
C11 C9 3.514(4) no . 1_455
C12 C8 3.504(4) no . 1_455
C14 F1 3.450(3) no . 1_545
C14 C18 3.472(4) no . 1_455
C15 C17 3.472(4) no . 1_455
C17 C9 3.584(4) no . 1_554
C17 C15 3.472(4) no . 1_655
C18 C14 3.472(4) no . 1_655
Br1 H13 2.9196 no . .
Br1 H14 2.8961 no . .
F1 H5 3.5099 no . .
F1 H6 2.6484 no . .
F2 H5 2.3895 no . .
F2 H6 3.1736 no . .
F3 H5 3.5961 no . .
F3 H6 2.6144 no . .
O1 H1 3.0140 no . .
O1 H2 3.1588 no . .
O1 H3 2.7334 no . .
O1 H4 2.5939 no . .
O1 H6 3.5157 no . .
O1 H15 2.4411 no . .
N1 H2 2.4321 no . .
N1 H3 2.9532 no . .
N1 H6 2.7697 no . .
N1 H12 2.5604 no . .
N1 H15 2.6308 no . .
C1 H4 2.6369 no . .
C1 H6 2.7233 no . .
C1 H15 2.8065 no . .
C2 H1 2.4461 no . .
C2 H5 3.3797 no . .
C2 H6 2.6390 no . .
C2 H7 3.3157 no . .
C2 H11 3.4836 no . .
C3 H6 2.7072 no . .
C3 H7 2.6528 no . .
C3 H11 2.6877 no . .
C4 H2 2.7700 no . .
C4 H3 3.3674 no . .
C4 H11 2.6443 no . .
C5 H1 3.5477 no . .
C5 H2 2.8694 no . .
C5 H4 3.1242 no . .
C5 H11 3.1398 no . .
C6 H5 2.5770 no . .
C7 H2 2.8109 no . .
C7 H3 2.6415 no . .
C7 H5 2.7262 no . .
C7 H8 3.2543 no . .
C7 H10 3.2632 no . .
C8 H3 3.0309 no . .
C8 H4 2.5435 no . .
C8 H9 3.2243 no . .
C8 H11 3.2171 no . .
C9 H10 3.2320 no . .
C10 H7 3.2217 no . .
C10 H11 3.2259 no . .
C11 H8 3.2344 no . .
C12 H2 3.3066 no . .
C12 H4 3.2367 no . .
C12 H5 3.0552 no . .
C12 H7 3.2106 no . .
C12 H9 3.2350 no . .
C13 H13 3.2447 no . .
C13 H14 3.2401 no . .
C14 H1 2.5455 no . .
C14 H15 3.2316 no . .
C15 H14 3.2323 no . .
C16 H12 3.2160 no . .
C16 H15 3.2276 no . .
C17 H13 3.2375 no . .
C18 H1 3.1554 no . .
C18 H12 3.2315 no . .
H1 H2 2.1276 no . .
H1 H3 2.9683 no . .
H1 H6 2.6987 no . .
H1 H12 2.4189 no . .
H1 H15 3.4135 no . .
H2 H4 2.8533 no . .
H2 H6 2.3468 no . .
H2 H11 3.1945 no . .
H3 H4 2.3547 no . .
H3 H7 2.8936 no . .
H4 H5 2.3194 no . .
H4 H6 3.3907 no . .
H4 H7 2.3663 no . .
H4 H11 3.5264 no . .
H5 H6 2.7309 no . .
H5 H11 2.8320 no . .
H6 H11 3.4204 no . .
H7 H8 2.3018 no . .
H8 H9 2.3123 no . .
H9 H10 2.3178 no . .
H10 H11 2.3185 no . .
H12 H13 2.3206 no . .
H14 H15 2.3149 no . .
Br1 H3 3.4518 no . 1_454
Br1 H3 3.4336 no . 1_554
Br1 H5 3.0862 no . 1_444
Br1 H7 3.2514 no . 1_454
Br1 H11 3.2465 no . 1_544
F1 H8 3.0476 no . 1_454
F1 H9 3.0599 no . 1_454
F1 H9 2.7270 no . 1_554
F1 H10 2.9544 no . 1_554
F1 H12 3.1584 no . 1_565
F2 H1 3.3152 no . 1_565
F2 H3 2.9136 no . 1_565
F3 H1 3.4100 no . 1_565
F3 H5 3.1704 no . 1_455
F3 H9 3.0085 no . 1_454
F3 H12 3.1523 no . 1_565
O1 H1 2.1002 no . 1_655
O1 H2 2.8983 no . 1_655
O1 H6 3.2494 no . 1_655
O1 H12 3.1798 no . 1_655
C1 H1 3.3175 no . 1_655
C2 H4 3.5959 no . 1_455
C6 H9 3.5595 no . 1_454
C7 H13 3.4487 no . 1_666
C7 H14 3.4537 no . 1_556
C8 H10 3.2917 no . 1_655
C8 H11 3.3795 no . 1_655
C8 H14 2.9951 no . 1_556
C9 H10 3.1604 no . 1_655
C9 H14 2.8724 no . 1_556
C9 H15 3.2060 no . 1_556
C10 H12 3.3842 no . 1_666
C10 H13 3.3092 no . 1_666
C10 H14 3.2476 no . 1_556
C10 H15 3.1361 no . 1_556
C11 H7 3.2895 no . 1_455
C11 H8 3.4141 no . 1_455
C11 H12 3.5202 no . 1_666
C11 H13 2.8856 no . 1_666
C12 H4 3.5465 no . 1_455
C12 H7 3.1425 no . 1_455
C12 H13 2.9702 no . 1_666
C13 H8 3.2053 no . 1_454
C14 H8 3.5836 no . 1_454
C14 H10 3.2679 no . 1_544
C14 H14 3.5610 no . 1_455
C14 H15 3.2567 no . 1_455
C15 H10 2.9394 no . 1_544
C15 H14 3.1928 no . 1_455
C16 H7 3.0801 no . 1_454
C16 H8 3.4730 no . 1_454
C16 H10 3.1980 no . 1_544
C16 H11 3.5955 no . 1_544
C17 H7 3.0518 no . 1_454
C17 H8 3.0736 no . 1_454
C17 H12 3.5522 no . 1_655
C17 H13 3.2632 no . 1_655
C18 H8 2.9193 no . 1_454
C18 H12 3.1871 no . 1_655
H1 F2 3.3152 no . 1_545
H1 F3 3.4100 no . 1_545
H1 O1 2.1002 no . 1_455
H1 C1 3.3175 no . 1_455
H1 H15 3.3233 no . 1_455
H2 O1 2.8983 no . 1_455
H2 H4 2.6623 no . 1_455
H2 H7 3.4754 no . 1_455
H3 Br1 3.4336 no . 1_556
H3 Br1 3.4518 no . 1_656
H3 F2 2.9136 no . 1_545
H3 H14 3.4515 no . 1_556
H4 C2 3.5959 no . 1_655
H4 C12 3.5465 no . 1_655
H4 H2 2.6623 no . 1_655
H4 H6 3.1968 no . 1_655
H4 H11 2.9864 no . 1_655
H5 Br1 3.0862 no . 1_666
H5 F3 3.1704 no . 1_655
H5 H11 3.5072 no . 1_655
H5 H13 3.5408 no . 1_666
H6 O1 3.2494 no . 1_455
H6 H4 3.1968 no . 1_455
H7 Br1 3.2514 no . 1_656
H7 C11 3.2895 no . 1_655
H7 C12 3.1425 no . 1_655
H7 C16 3.0801 no . 1_656
H7 C17 3.0518 no . 1_656
H7 H2 3.4754 no . 1_655
H7 H10 3.3902 no . 1_655
H7 H11 3.1510 no . 1_655
H7 H14 3.3066 no . 1_556
H7 H14 3.0015 no . 1_656
H8 F1 3.0476 no . 1_656
H8 C11 3.4141 no . 1_655
H8 C13 3.2053 no . 1_656
H8 C14 3.5836 no . 1_656
H8 C16 3.4730 no . 1_656
H8 C17 3.0736 no . 1_656
H8 C18 2.9193 no . 1_656
H8 H10 3.1912 no . 1_655
H8 H14 3.1095 no . 1_556
H8 H14 3.4256 no . 1_656
H8 H15 3.0455 no . 1_556
H8 H15 3.1999 no . 1_656
H9 F1 2.7270 no . 1_556
H9 F1 3.0599 no . 1_656
H9 F3 3.0085 no . 1_656
H9 C6 3.5595 no . 1_656
H9 H12 3.1916 no . 1_666
H9 H15 2.9424 no . 1_556
H10 F1 2.9544 no . 1_556
H10 C8 3.2917 no . 1_455
H10 C9 3.1604 no . 1_455
H10 C14 3.2679 no . 1_566
H10 C15 2.9394 no . 1_566
H10 C16 3.1980 no . 1_566
H10 H7 3.3902 no . 1_455
H10 H8 3.1912 no . 1_455
H10 H12 3.4506 no . 1_666
H10 H13 3.1088 no . 1_566
H10 H13 3.1168 no . 1_666
H11 Br1 3.2465 no . 1_566
H11 C8 3.3795 no . 1_455
H11 C16 3.5955 no . 1_566
H11 H4 2.9864 no . 1_455
H11 H5 3.5072 no . 1_455
H11 H7 3.1510 no . 1_455
H11 H13 3.2294 no . 1_666
H12 F1 3.1584 no . 1_545
H12 F3 3.1523 no . 1_545
H12 O1 3.1798 no . 1_455
H12 C10 3.3842 no . 1_444
H12 C11 3.5202 no . 1_444
H12 C17 3.5522 no . 1_455
H12 C18 3.1871 no . 1_455
H12 H9 3.1916 no . 1_444
H12 H10 3.4506 no . 1_444
H12 H15 3.0972 no . 1_455
H13 C7 3.4487 no . 1_444
H13 C10 3.3092 no . 1_444
H13 C11 2.8856 no . 1_444
H13 C12 2.9702 no . 1_444
H13 C17 3.2632 no . 1_455
H13 H5 3.5408 no . 1_444
H13 H10 3.1168 no . 1_444
H13 H10 3.1088 no . 1_544
H13 H11 3.2294 no . 1_444
H13 H14 3.1062 no . 1_455
H14 C7 3.4537 no . 1_554
H14 C8 2.9951 no . 1_554
H14 C9 2.8724 no . 1_554
H14 C10 3.2476 no . 1_554
H14 C14 3.5610 no . 1_655
H14 C15 3.1928 no . 1_655
H14 H3 3.4515 no . 1_554
H14 H7 3.0015 no . 1_454
H14 H7 3.3066 no . 1_554
H14 H8 3.4256 no . 1_454
H14 H8 3.1095 no . 1_554
H14 H13 3.1062 no . 1_655
H15 C9 3.2060 no . 1_554
H15 C10 3.1361 no . 1_554
H15 C14 3.2567 no . 1_655
H15 H1 3.3233 no . 1_655
H15 H8 3.1999 no . 1_454
H15 H8 3.0455 no . 1_554
H15 H9 2.9424 no . 1_554
H15 H12 3.0972 no . 1_655

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O1 . . 1_455 2.938(3) 0.867 2.100 162.2 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================


