# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_3

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            3
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 Br2 F5 N5 O3'
_chemical_formula_weight         685.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_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.
;

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                   14.052(3)
_cell_length_b                   10.029(3)
_cell_length_c                   18.994(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.069(3)
_cell_angle_gamma                90
_cell_volume                     2627.0(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1045
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      15.85

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.733
_exptl_crystal_F_000             1368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    3.159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5486
_exptl_absorpt_correction_T_max  0.8234
_exptl_absorpt_process_details   SADABS
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25093
_diffrn_reflns_av_unetI/netI     0.1510
_diffrn_reflns_av_R_equivalents  0.1865
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.477
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4628
_reflns_number_gt                1910
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0784P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4628
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1993
_refine_ls_R_factor_gt           0.0693
_refine_ls_wR_factor_ref         0.1801
_refine_ls_wR_factor_gt          0.1480
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_restrained_S_all      0.925
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.64559(7) 0.70244(12) 0.06211(5) 0.0703(4) Uani 1 1 d . . . . .
Br2 Br 0.92780(7) -0.19929(10) 0.51380(6) 0.0681(4) Uani 1 1 d . . . . .
F1 F 0.8322(4) 0.0384(5) 0.5629(3) 0.0683(16) Uani 1 1 d . . . . .
F2 F 0.9175(4) -0.1402(5) 0.3554(3) 0.0704(16) Uani 1 1 d . . . . .
F3 F 0.8267(4) 0.0601(5) 0.2762(3) 0.0784(18) Uani 1 1 d . . . . .
F4 F 0.5012(3) 0.4945(5) 0.0891(2) 0.0615(15) Uani 1 1 d . . . . .
F5 F 0.8145(4) 0.6519(5) 0.1810(3) 0.0609(15) Uani 1 1 d . . . . .
O1 O 0.3146(5) 0.2831(8) 0.1969(4) 0.094(3) Uani 1 1 d . . . . .
O2 O 0.6370(5) 0.4514(7) 0.5510(5) 0.099(3) Uani 1 1 d . . . . .
O3 O 1.0192(6) 0.4674(8) 0.3884(5) 0.112(3) Uani 1 1 d . . . . .
N1 N 0.6939(5) 0.2602(7) 0.2808(4) 0.055(2) Uani 1 1 d . . . . .
N2 N 0.7416(5) 0.2751(7) 0.3443(4) 0.058(2) Uani 1 1 d . . . . .
N3 N 0.5169(6) 0.2986(8) 0.1970(4) 0.060(2) Uani 1 1 d . . . . .
N4 N 0.8440(5) 0.4584(7) 0.2884(4) 0.052(2) Uani 1 1 d . . . . .
N5 N 0.7376(5) 0.2572(8) 0.4854(4) 0.058(2) Uani 1 1 d . . . . .
C1 C 0.6605(7) 0.5677(9) 0.1315(4) 0.049(2) Uani 1 1 d . . . . .
C2 C 0.5864(7) 0.4836(9) 0.1359(5) 0.048(2) Uani 1 1 d . . . . .
C3 C 0.5903(7) 0.3868(10) 0.1897(5) 0.052(3) Uani 1 1 d . . . . .
C4 C 0.6799(7) 0.3794(9) 0.2395(5) 0.051(3) Uani 1 1 d . . . . .
C5 C 0.7571(6) 0.4692(9) 0.2390(4) 0.047(2) Uani 1 1 d . . . . .
C6 C 0.7445(6) 0.5608(9) 0.1845(5) 0.049(2) Uani 1 1 d . . . . .
C7 C 0.7785(6) 0.1565(8) 0.3811(5) 0.048(3) Uani 1 1 d . . . . .
C8 C 0.7824(6) 0.1526(9) 0.4537(5) 0.049(2) Uani 1 1 d . . . . .
C9 C 0.8289(6) 0.0474(9) 0.4909(5) 0.048(3) Uani 1 1 d . . . . .
C10 C 0.8719(6) -0.0518(8) 0.4587(5) 0.047(2) Uani 1 1 d . . . . .
C11 C 0.8724(7) -0.0470(9) 0.3877(5) 0.052(3) Uani 1 1 d . . . . .
C12 C 0.8228(7) 0.0573(10) 0.3481(5) 0.059(3) Uani 1 1 d . . . . .
C13 C 0.4770(7) 0.2970(11) 0.2647(6) 0.081(4) Uani 1 1 d . . . . .
H13A H 0.5201 0.3487 0.3024 0.097 Uiso 1 1 calc R U . . .
H13B H 0.4742 0.2041 0.2818 0.097 Uiso 1 1 calc R U . . .
C14 C 0.3755(8) 0.3579(13) 0.2507(6) 0.098(4) Uani 1 1 d . . . . .
H14A H 0.3490 0.3571 0.2954 0.117 Uiso 1 1 calc R U . . .
H14B H 0.3785 0.4516 0.2348 0.117 Uiso 1 1 calc R U . . .
C15 C 0.3494(7) 0.2921(12) 0.1305(6) 0.085(4) Uani 1 1 d . . . . .
H15A H 0.3499 0.3866 0.1155 0.102 Uiso 1 1 calc R U . . .
H15B H 0.3051 0.2425 0.0926 0.102 Uiso 1 1 calc R U . . .
C16 C 0.4524(8) 0.2340(11) 0.1390(6) 0.090(4) Uani 1 1 d . . . . .
H16A H 0.4506 0.1371 0.1488 0.108 Uiso 1 1 calc R U . . .
H16B H 0.4767 0.2464 0.0939 0.108 Uiso 1 1 calc R U . . .
C17 C 0.7752(8) 0.3034(11) 0.5598(6) 0.082(4) Uani 1 1 d . . . . .
H17A H 0.8469 0.3034 0.5691 0.098 Uiso 1 1 calc R U . . .
H17B H 0.7538 0.2411 0.5942 0.098 Uiso 1 1 calc R U . . .
C18 C 0.7394(7) 0.4408(11) 0.5713(6) 0.089(4) Uani 1 1 d . . . . .
H18A H 0.7593 0.4648 0.6226 0.106 Uiso 1 1 calc R U . . .
H18B H 0.7700 0.5051 0.5429 0.106 Uiso 1 1 calc R U . . .
C19 C 0.6028(7) 0.4098(12) 0.4770(6) 0.092(4) Uani 1 1 d . . . . .
H19A H 0.6308 0.4687 0.4444 0.111 Uiso 1 1 calc R U . . .
H19B H 0.5313 0.4178 0.4647 0.111 Uiso 1 1 calc R U . . .
C20 C 0.6321(7) 0.2667(9) 0.4667(6) 0.068(3) Uani 1 1 d . . . . .
H20A H 0.6023 0.2067 0.4977 0.082 Uiso 1 1 calc R U . . .
H20B H 0.6093 0.2394 0.4162 0.082 Uiso 1 1 calc R U . . .
C21 C 0.8480(7) 0.5285(9) 0.3562(6) 0.081(4) Uani 1 1 d . . . . .
H21A H 0.7848 0.5208 0.3717 0.098 Uiso 1 1 calc R U . . .
H21B H 0.8617 0.6242 0.3502 0.098 Uiso 1 1 calc R U . . .
C22 C 0.9277(8) 0.4669(10) 0.4125(6) 0.084(4) Uani 1 1 d . . . . .
H22A H 0.9342 0.5179 0.4578 0.101 Uiso 1 1 calc R U . . .
H22B H 0.9100 0.3740 0.4221 0.101 Uiso 1 1 calc R U . . .
C23 C 0.9361(7) 0.4614(12) 0.2649(5) 0.082(4) Uani 1 1 d . . . . .
H23A H 0.9545 0.5547 0.2573 0.099 Uiso 1 1 calc R U . . .
H23B H 0.9307 0.4128 0.2190 0.099 Uiso 1 1 calc R U . . .
C24 C 1.0137(8) 0.3957(12) 0.3224(6) 0.088(4) Uani 1 1 d . . . . .
H24A H 0.9965 0.3014 0.3289 0.106 Uiso 1 1 calc R U . . .
H24B H 1.0773 0.3980 0.3072 0.106 Uiso 1 1 calc R 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
Br1 C1 1.870(9) . ?
Br2 C10 1.893(8) . ?
F1 C9 1.362(10) . ?
F2 C11 1.342(10) . ?
F3 C12 1.378(10) . ?
F4 C2 1.351(9) . ?
F5 C6 1.354(9) . ?
O1 C14 1.415(12) . ?
O1 C15 1.441(12) . ?
O2 C18 1.421(10) . ?
O2 C19 1.457(11) . ?
O3 C24 1.436(13) . ?
O3 C22 1.444(14) . ?
N1 N2 1.271(9) . ?
N1 C4 1.422(10) . ?
N2 C7 1.425(10) . ?
N3 C3 1.384(11) . ?
N3 C16 1.439(12) . ?
N3 C13 1.499(13) . ?
N4 C5 1.393(9) . ?
N4 C23 1.447(11) . ?
N4 C21 1.459(11) . ?
N5 C8 1.416(11) . ?
N5 C20 1.460(11) . ?
N5 C17 1.486(11) . ?
C1 C2 1.356(12) . ?
C1 C6 1.399(11) . ?
C2 C3 1.403(12) . ?
C3 C4 1.425(11) . ?
C4 C5 1.411(12) . ?
C5 C6 1.370(11) . ?
C7 C8 1.370(12) . ?
C7 C12 1.386(12) . ?
C8 C9 1.364(11) . ?
C9 C10 1.368(12) . ?
C10 C11 1.351(12) . ?
C11 C12 1.396(12) . ?
C13 C14 1.528(14) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.540(14) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.497(13) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.516(13) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.523(11) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.535(12) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

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
C14 O1 C15 109.8(8) . . ?
C18 O2 C19 111.6(9) . . ?
C24 O3 C22 111.9(8) . . ?
N2 N1 C4 114.6(7) . . ?
N1 N2 C7 116.3(7) . . ?
C3 N3 C16 125.7(9) . . ?
C3 N3 C13 120.0(8) . . ?
C16 N3 C13 111.5(8) . . ?
C5 N4 C23 120.7(8) . . ?
C5 N4 C21 115.9(7) . . ?
C23 N4 C21 112.2(8) . . ?
C8 N5 C20 117.3(7) . . ?
C8 N5 C17 122.0(7) . . ?
C20 N5 C17 111.7(8) . . ?
C2 C1 C6 118.4(8) . . ?
C2 C1 Br1 120.7(6) . . ?
C6 C1 Br1 120.6(7) . . ?
F4 C2 C1 120.1(8) . . ?
F4 C2 C3 116.2(8) . . ?
C1 C2 C3 123.6(8) . . ?
N3 C3 C2 126.1(8) . . ?
N3 C3 C4 118.7(8) . . ?
C2 C3 C4 115.2(9) . . ?
C5 C4 N1 121.0(7) . . ?
C5 C4 C3 123.0(8) . . ?
N1 C4 C3 114.9(8) . . ?
C6 C5 N4 122.0(9) . . ?
C6 C5 C4 116.4(7) . . ?
N4 C5 C4 121.4(8) . . ?
F5 C6 C5 120.0(8) . . ?
F5 C6 C1 116.9(8) . . ?
C5 C6 C1 123.2(8) . . ?
C8 C7 C12 120.0(8) . . ?
C8 C7 N2 117.3(8) . . ?
C12 C7 N2 122.0(9) . . ?
C9 C8 C7 117.8(9) . . ?
C9 C8 N5 124.1(9) . . ?
C7 C8 N5 118.1(8) . . ?
F1 C9 C8 119.5(9) . . ?
F1 C9 C10 117.9(8) . . ?
C8 C9 C10 122.7(9) . . ?
C11 C10 C9 120.5(8) . . ?
C11 C10 Br2 119.9(8) . . ?
C9 C10 Br2 119.6(7) . . ?
F2 C11 C10 121.7(9) . . ?
F2 C11 C12 120.4(9) . . ?
C10 C11 C12 117.9(10) . . ?
F3 C12 C7 122.7(9) . . ?
F3 C12 C11 116.1(10) . . ?
C7 C12 C11 121.0(9) . . ?
N3 C13 C14 109.7(8) . . ?
N3 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
N3 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
O1 C14 C13 109.2(10) . . ?
O1 C14 H14A 109.8 . . ?
C13 C14 H14A 109.8 . . ?
O1 C14 H14B 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
O1 C15 C16 110.7(9) . . ?
O1 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
N3 C16 C15 110.6(10) . . ?
N3 C16 H16A 109.5 . . ?
C15 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
N5 C17 C18 110.9(9) . . ?
N5 C17 H17A 109.5 . . ?
C18 C17 H17A 109.5 . . ?
N5 C17 H17B 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 108.0 . . ?
O2 C18 C17 112.4(8) . . ?
O2 C18 H18A 109.1 . . ?
C17 C18 H18A 109.1 . . ?
O2 C18 H18B 109.1 . . ?
C17 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?
O2 C19 C20 110.4(8) . . ?
O2 C19 H19A 109.6 . . ?
C20 C19 H19A 109.6 . . ?
O2 C19 H19B 109.6 . . ?
C20 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
N5 C20 C19 108.5(8) . . ?
N5 C20 H20A 110.0 . . ?
C19 C20 H20A 110.0 . . ?
N5 C20 H20B 110.0 . . ?
C19 C20 H20B 110.0 . . ?
H20A C20 H20B 108.4 . . ?
N4 C21 C22 108.8(8) . . ?
N4 C21 H21A 109.9 . . ?
C22 C21 H21A 109.9 . . ?
N4 C21 H21B 109.9 . . ?
C22 C21 H21B 109.9 . . ?
H21A C21 H21B 108.3 . . ?
O3 C22 C21 110.9(10) . . ?
O3 C22 H22A 109.5 . . ?
C21 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
N4 C23 C24 109.2(8) . . ?
N4 C23 H23A 109.8 . . ?
C24 C23 H23A 109.8 . . ?
N4 C23 H23B 109.8 . . ?
C24 C23 H23B 109.8 . . ?
H23A C23 H23B 108.3 . . ?
O3 C24 C23 108.5(9) . . ?
O3 C24 H24A 110.0 . . ?
C23 C24 H24A 110.0 . . ?
O3 C24 H24B 110.0 . . ?
C23 C24 H24B 110.0 . . ?
H24A C24 H24B 108.4 . . ?

_refine_diff_density_max         0.606
_refine_diff_density_min         -0.569
_refine_diff_density_rms         0.106

_shelxl_version_number           2014-3

_vrf_RINTA01_3                   
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: the crystal diffracted poorly at higher angles
and attempts to obatin a better quality one were not
successful.
;
_database_code_depnum_ccdc_archive 'CCDC 1007719'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_4-morpholine

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '4:morpholine 1/1 solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H41 Br2 F4 N7 O5'
_chemical_formula_weight         839.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   19.4138(15)
_cell_length_b                   17.3697(14)
_cell_length_c                   10.4512(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3524.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    457
_cell_measurement_theta_min      2.242
_cell_measurement_theta_max      24.33

_exptl_crystal_description       needle
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.022
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_F_000             1712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    2.372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6480
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39250
_diffrn_reflns_av_unetI/netI     0.0902
_diffrn_reflns_av_R_equivalents  0.0859
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.573
_diffrn_reflns_theta_max         28.139
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8163
_reflns_number_gt                5730
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_max     0.926
_reflns_Friedel_fraction_full    0.995

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0377P)²+0.8773P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2184 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.024(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8163
_refine_ls_number_parameters     452
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1009
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

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 0.17700(4) 0.70780(4) 0.75236(8) 0.0364(2) Uani 1 1 d . . . . .
Br2 Br 0.20897(4) 0.24618(4) -0.17400(8) 0.03377(18) Uani 1 1 d . . . . .
F1 F 0.0572(2) 0.6959(2) 0.5746(4) 0.0335(10) Uani 1 1 d . . . . .
F2 F 0.26212(19) 0.5700(2) 0.6803(4) 0.0328(10) Uani 1 1 d . . . . .
F3 F 0.1332(2) 0.19081(19) 0.0595(4) 0.0332(10) Uani 1 1 d . . . . .
F4 F 0.2304(2) 0.4140(2) -0.1147(4) 0.0322(10) Uani 1 1 d . . . . .
O1 O 0.2543(3) 0.6504(3) 0.1064(5) 0.0312(12) Uani 1 1 d . . . . .
O2 O 0.0210(3) 0.1724(3) 0.4511(5) 0.0396(13) Uani 1 1 d . . . . .
O3 O -0.0830(3) 0.6046(4) 0.2114(6) 0.0628(19) Uani 1 1 d . . . . .
O4 O 0.3400(2) 0.3375(3) 0.4841(5) 0.0336(12) Uani 1 1 d . . . . .
O5 O 0.0478(8) 0.9028(10) 0.4786(12) 0.223(8) Uani 1 1 d . . . . .
N1 N 0.1282(2) 0.4865(3) 0.3152(5) 0.0173(11) Uani 1 1 d . . . . .
N2 N 0.1440(2) 0.4156(3) 0.3180(5) 0.0169(11) Uani 1 1 d . . . . .
N3 N 0.2059(3) 0.4978(3) 0.1067(5) 0.0177(12) Uani 1 1 d . . . . .
N4 N 0.2439(3) 0.4590(3) 0.4866(5) 0.0177(11) Uani 1 1 d . . . . .
N5 N 0.0338(3) 0.5935(3) 0.3678(5) 0.0227(13) Uani 1 1 d . . . . .
N6 N 0.0965(3) 0.2635(3) 0.2791(5) 0.0251(13) Uani 1 1 d . . . . .
N7 N 0.0253(7) 0.9077(13) 0.2278(13) 0.196(9) Uani 1 1 d . . . . .
H7N H 0.0038 0.8890 0.1565 0.250 Uiso 1 1 d . U . . .
C1 C 0.1501(3) 0.3828(4) 0.1941(6) 0.0188(14) Uani 1 1 d . . . . .
C2 C 0.1320(3) 0.3043(3) 0.1847(6) 0.0191(14) Uani 1 1 d . . . . .
C3 C 0.1510(3) 0.2655(4) 0.0730(7) 0.0244(15) Uani 1 1 d . . . . .
C4 C 0.1855(3) 0.3011(4) -0.0269(6) 0.0242(15) Uani 1 1 d . . . . .
C5 C 0.1998(3) 0.3783(4) -0.0141(6) 0.0209(15) Uani 1 1 d . . . . .
C6 C 0.1835(3) 0.4208(4) 0.0928(6) 0.0176(13) Uani 1 1 d . . . . .
C7 C 0.1375(3) 0.5271(3) 0.4321(6) 0.0167(14) Uani 1 1 d . . . . .
C8 C 0.1969(3) 0.5197(3) 0.5089(6) 0.0165(14) Uani 1 1 d . . . . .
C9 C 0.2074(3) 0.5764(4) 0.6016(6) 0.0206(14) Uani 1 1 d . . . . .
C10 C 0.1625(3) 0.6364(4) 0.6203(6) 0.0216(15) Uani 1 1 d . . . . .
C11 C 0.1038(3) 0.6405(3) 0.5466(6) 0.0192(14) Uani 1 1 d . . . . .
C12 C 0.0901(3) 0.5885(4) 0.4497(6) 0.0184(14) Uani 1 1 d . . . . .
C13 C 0.2781(4) 0.5149(4) 0.0738(7) 0.0305(17) Uani 1 1 d . . . . .
H13A H 0.2831 0.5220 -0.0197 0.037 Uiso 1 1 calc R U . . .
H13B H 0.3084 0.4720 0.1009 0.037 Uiso 1 1 calc R U . . .
C14 C 0.1603(4) 0.5601(4) 0.0677(7) 0.0283(17) Uani 1 1 d . . . . .
H14A H 0.1123 0.5479 0.0923 0.034 Uiso 1 1 calc R U . . .
H14B H 0.1621 0.5664 -0.0264 0.034 Uiso 1 1 calc R U . . .
C15 C 0.1831(4) 0.6334(4) 0.1321(7) 0.0295(16) Uani 1 1 d . . . . .
H15A H 0.1541 0.6766 0.1016 0.035 Uiso 1 1 calc R U . . .
H15B H 0.1763 0.6285 0.2257 0.035 Uiso 1 1 calc R U . . .
C16 C 0.2974(4) 0.5877(4) 0.1432(8) 0.0333(18) Uani 1 1 d . . . . .
H16A H 0.2932 0.5792 0.2366 0.040 Uiso 1 1 calc R U . . .
H16B H 0.3460 0.6006 0.1242 0.040 Uiso 1 1 calc R U . . .
C17 C 0.1273(3) 0.1953(3) 0.3366(8) 0.0272(15) Uani 1 1 d . . . . .
H17A H 0.1523 0.2098 0.4157 0.033 Uiso 1 1 calc R U . . .
H17B H 0.1608 0.1721 0.2764 0.033 Uiso 1 1 calc R U . . .
C18 C 0.0715(4) 0.1380(4) 0.3678(8) 0.037(2) Uani 1 1 d . . . . .
H18A H 0.0490 0.1206 0.2879 0.045 Uiso 1 1 calc R U . . .
H18B H 0.0920 0.0924 0.4101 0.045 Uiso 1 1 calc R U . . .
C19 C 0.0433(3) 0.2977(4) 0.3568(6) 0.0275(17) Uani 1 1 d . . . . .
H19A H 0.0212 0.3406 0.3098 0.033 Uiso 1 1 calc R U . . .
H19B H 0.0635 0.3185 0.4366 0.033 Uiso 1 1 calc R U . . .
C20 C -0.0098(4) 0.2362(4) 0.3884(8) 0.0329(18) Uani 1 1 d . . . . .
H20A H -0.0459 0.2585 0.4442 0.040 Uiso 1 1 calc R U . . .
H20B H -0.0322 0.2185 0.3085 0.040 Uiso 1 1 calc R U . . .
C21 C -0.0549(4) 0.5324(5) 0.2446(9) 0.051(2) Uani 1 1 d . . . . .
H21A H -0.0218 0.5164 0.1777 0.061 Uiso 1 1 calc R U . . .
H21B H -0.0923 0.4937 0.2473 0.061 Uiso 1 1 calc R U . . .
C22 C -0.0189(4) 0.5338(4) 0.3720(7) 0.0317(17) Uani 1 1 d . . . . .
H22A H -0.0523 0.5450 0.4411 0.038 Uiso 1 1 calc R U . . .
H22B H 0.0026 0.4832 0.3894 0.038 Uiso 1 1 calc R U . . .
C23 C 0.0033(4) 0.6671(4) 0.3418(7) 0.0331(17) Uani 1 1 d . . . . .
H23A H 0.0391 0.7077 0.3422 0.040 Uiso 1 1 calc DR U . . .
H23B H -0.0314 0.6797 0.4079 0.040 Uiso 1 1 calc R U . . .
C24 C -0.0311(4) 0.6625(5) 0.2090(7) 0.048(2) Uani 1 1 d . . . . .
H24A H -0.0519 0.7129 0.1870 0.058 Uiso 1 1 calc R U . . .
H24B H 0.0038 0.6499 0.1432 0.058 Uiso 1 1 calc R U . . .
C25 C 0.2288(3) 0.3862(3) 0.5508(6) 0.0203(15) Uani 1 1 d . . . . .
H25A H 0.1786 0.3760 0.5489 0.024 Uiso 1 1 calc R U . . .
H25B H 0.2438 0.3886 0.6412 0.024 Uiso 1 1 calc R U . . .
C26 C 0.2666(3) 0.3239(4) 0.4821(7) 0.0279(16) Uani 1 1 d . . . . .
H26A H 0.2566 0.2738 0.5231 0.033 Uiso 1 1 calc R U . . .
H26B H 0.2505 0.3214 0.3923 0.033 Uiso 1 1 calc R U . . .
C27 C 0.3552(4) 0.4098(4) 0.4263(7) 0.0334(18) Uani 1 1 d . . . . .
H27A H 0.3410 0.4086 0.3353 0.040 Uiso 1 1 calc R U . . .
H27B H 0.4055 0.4188 0.4293 0.040 Uiso 1 1 calc R U . . .
C28 C 0.3182(3) 0.4752(4) 0.4941(7) 0.0280(16) Uani 1 1 d . . . . .
H28A H 0.3331 0.4782 0.5845 0.034 Uiso 1 1 calc R U . . .
H28B H 0.3288 0.5249 0.4520 0.034 Uiso 1 1 calc R U . . .
C29 C 0.0717(6) 0.8622(5) 0.2563(12) 0.079(4) Uani 1 1 d . . . . .
H29A H 0.1099 0.8687 0.1944 0.095 Uiso 1 1 calc R U . . .
H29B H 0.0538 0.8092 0.2465 0.095 Uiso 1 1 calc DR U . . .
C30 C 0.0999(6) 0.8703(8) 0.3865(17) 0.103(5) Uani 1 1 d . . . . .
H30A H 0.1406 0.9046 0.3839 0.123 Uiso 1 1 calc R U . . .
H30B H 0.1152 0.8193 0.4176 0.123 Uiso 1 1 calc R U . . .
C31 C -0.0015(5) 0.9443(6) 0.4353(9) 0.053(2) Uani 1 1 d . . . . .
H31A H 0.0149 0.9982 0.4309 0.064 Uiso 1 1 calc R U . . .
H31B H -0.0396 0.9428 0.4984 0.064 Uiso 1 1 calc R U . . .
C32 C -0.0278(5) 0.9256(7) 0.3200(13) 0.087(3) Uani 1 1 d . . . . .
H32A H -0.0557 0.9692 0.2877 0.105 Uiso 1 1 calc R U . . .
H32B H -0.0586 0.8806 0.3295 0.105 Uiso 1 1 calc R 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
Br1 C10 1.877(6) . ?
Br2 C4 1.866(6) . ?
F1 C11 1.354(7) . ?
F2 C9 1.348(7) . ?
F3 C3 1.350(7) . ?
F4 C5 1.357(7) . ?
O1 C16 1.427(8) . ?
O1 C15 1.440(8) . ?
O2 C20 1.419(8) . ?
O2 C18 1.442(9) . ?
O3 C21 1.411(9) . ?
O3 C24 1.425(10) . ?
O4 C27 1.424(8) . ?
O4 C26 1.443(8) . ?
O5 C31 1.281(15) . ?
O5 C30 1.506(17) . ?
N1 N2 1.269(6) . ?
N1 C7 1.422(7) . ?
N2 C1 1.420(8) . ?
N3 C6 1.414(8) . ?
N3 C14 1.455(8) . ?
N3 C13 1.474(8) . ?
N4 C8 1.414(8) . ?
N4 C25 1.460(8) . ?
N4 C28 1.473(8) . ?
N5 C12 1.391(8) . ?
N5 C23 1.434(8) . ?
N5 C22 1.457(9) . ?
N6 C2 1.396(8) . ?
N6 C19 1.442(8) . ?
N6 C17 1.457(8) . ?
N7 C29 1.235(16) . ?
N7 C32 1.444(15) . ?
C1 C6 1.408(9) . ?
C1 C2 1.411(9) . ?
C2 C3 1.397(9) . ?
C3 C4 1.387(9) . ?
C4 C5 1.376(9) . ?
C5 C6 1.376(8) . ?
C7 C8 1.411(9) . ?
C7 C12 1.422(8) . ?
C8 C9 1.396(9) . ?
C9 C10 1.374(9) . ?
C10 C11 1.378(9) . ?
C11 C12 1.382(8) . ?
C13 C16 1.504(10) . ?
C14 C15 1.507(9) . ?
C17 C18 1.508(9) . ?
C19 C20 1.522(9) . ?
C21 C22 1.505(10) . ?
C23 C24 1.542(10) . ?
C25 C26 1.492(9) . ?
C27 C28 1.520(9) . ?
C29 C30 1.474(18) . ?
C31 C32 1.348(14) . ?

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
C16 O1 C15 110.9(5) . . ?
C20 O2 C18 109.4(5) . . ?
C21 O3 C24 111.0(6) . . ?
C27 O4 C26 110.1(5) . . ?
C31 O5 C30 119.2(12) . . ?
N2 N1 C7 115.5(5) . . ?
N1 N2 C1 112.9(5) . . ?
C6 N3 C14 119.2(5) . . ?
C6 N3 C13 117.3(5) . . ?
C14 N3 C13 111.3(5) . . ?
C8 N4 C25 116.1(5) . . ?
C8 N4 C28 118.7(5) . . ?
C25 N4 C28 109.7(5) . . ?
C12 N5 C23 119.8(5) . . ?
C12 N5 C22 119.2(5) . . ?
C23 N5 C22 110.5(5) . . ?
C2 N6 C19 122.8(5) . . ?
C2 N6 C17 120.1(6) . . ?
C19 N6 C17 113.4(5) . . ?
C29 N7 C32 119.8(16) . . ?
C6 C1 C2 121.1(6) . . ?
C6 C1 N2 122.4(5) . . ?
C2 C1 N2 115.6(5) . . ?
N6 C2 C3 118.4(5) . . ?
N6 C2 C1 124.3(6) . . ?
C3 C2 C1 117.3(6) . . ?
F3 C3 C4 118.2(6) . . ?
F3 C3 C2 119.0(6) . . ?
C4 C3 C2 122.8(6) . . ?
C5 C4 C3 117.3(6) . . ?
C5 C4 Br2 122.0(5) . . ?
C3 C4 Br2 120.7(5) . . ?
F4 C5 C6 119.0(5) . . ?
F4 C5 C4 117.3(6) . . ?
C6 C5 C4 123.7(6) . . ?
C5 C6 C1 117.7(6) . . ?
C5 C6 N3 121.4(6) . . ?
C1 C6 N3 120.6(5) . . ?
C8 C7 N1 123.2(5) . . ?
C8 C7 C12 121.6(5) . . ?
N1 C7 C12 113.6(5) . . ?
C9 C8 C7 116.8(6) . . ?
C9 C8 N4 123.1(6) . . ?
C7 C8 N4 120.1(6) . . ?
F2 C9 C10 118.4(6) . . ?
F2 C9 C8 118.8(5) . . ?
C10 C9 C8 122.8(6) . . ?
C9 C10 C11 119.0(6) . . ?
C9 C10 Br1 120.7(5) . . ?
C11 C10 Br1 120.1(5) . . ?
F1 C11 C10 117.9(5) . . ?
F1 C11 C12 119.7(6) . . ?
C10 C11 C12 122.4(6) . . ?
C11 C12 N5 124.2(6) . . ?
C11 C12 C7 117.4(6) . . ?
N5 C12 C7 118.4(5) . . ?
N3 C13 C16 107.1(6) . . ?
N3 C14 C15 109.0(6) . . ?
O1 C15 C14 111.8(6) . . ?
O1 C16 C13 111.5(6) . . ?
N6 C17 C18 109.4(6) . . ?
O2 C18 C17 110.2(6) . . ?
N6 C19 C20 108.6(5) . . ?
O2 C20 C19 111.2(6) . . ?
O3 C21 C22 112.5(7) . . ?
N5 C22 C21 108.1(6) . . ?
N5 C23 C24 107.6(6) . . ?
O3 C24 C23 109.1(6) . . ?
N4 C25 C26 107.9(5) . . ?
O4 C26 C25 111.1(5) . . ?
O4 C27 C28 111.3(6) . . ?
N4 C28 C27 107.1(6) . . ?
N7 C29 C30 115.6(12) . . ?
C29 C30 O5 112.1(10) . . ?
O5 C31 C32 117.6(10) . . ?
C31 C32 N7 112.2(10) . . ?

_refine_diff_density_max         0.537
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.086

_shelxl_version_number           2014-3

_vrf_PLAT431_4-morpholine        
;
PROBLEM: Short Inter HL..A  Contact Br2 ..  O1 ..2.92 Ang.  
RESPONSE: The short contact corresponds to one of the 
halogen bonds described in the manuscript.
;
_database_code_depnum_ccdc_archive 'CCDC 1007720'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_5-morpholine

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '5:morpholine 1/1 solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H41 F4 I2 N7 O5'
_chemical_formula_weight         933.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   19.6801(13)
_cell_length_b                   17.4108(11)
_cell_length_c                   10.6952(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3664.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7160
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      22.41

_exptl_crystal_description       Needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_F_000             1856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    1.786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5642
_exptl_absorpt_correction_T_max  0.9066
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40162
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.562
_diffrn_reflns_theta_max         27.118
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8076
_reflns_number_gt                6845
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.892
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.999

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0240P)²+4.5427P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2826 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8076
_refine_ls_number_parameters     451
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0739
_refine_ls_wR_factor_gt          0.0690
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001

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
I1 I 0.19943(3) 0.72800(2) 0.23938(5) 0.02524(11) Uani 1 1 d . . . . .
I2 I 0.17200(2) 1.20757(3) 1.17399(5) 0.02704(12) Uani 1 1 d . . . . .
N1 N 0.1255(3) 0.9772(3) 0.7324(6) 0.0148(11) Uani 1 1 d . . . . .
N2 N 0.1408(3) 0.9061(3) 0.7386(6) 0.0158(11) Uani 1 1 d . . . . .
C1 C 0.1455(4) 0.8719(4) 0.6178(7) 0.0162(15) Uani 1 1 d . . . . .
C2 C 0.1269(3) 0.7933(4) 0.6111(6) 0.0164(14) Uani 1 1 d . . . . .
C3 C 0.1429(4) 0.7549(4) 0.5002(6) 0.0189(16) Uani 1 1 d . . . . .
C4 C 0.1749(4) 0.7895(4) 0.4004(6) 0.0203(15) Uani 1 1 d . . . . .
C5 C 0.1905(4) 0.8663(4) 0.4107(7) 0.0183(16) Uani 1 1 d . . . . .
C6 C 0.1777(4) 0.9092(4) 0.5166(7) 0.0185(15) Uani 1 1 d . . . . .
C7 C 0.1344(3) 1.0196(4) 0.8450(6) 0.0148(15) Uani 1 1 d . . . . .
C8 C 0.1929(4) 1.0120(4) 0.9220(7) 0.0172(16) Uani 1 1 d . . . . .
C9 C 0.2036(3) 1.0695(4) 1.0104(6) 0.0156(15) Uani 1 1 d . . . . .
C10 C 0.1589(4) 1.1298(4) 1.0284(7) 0.0184(16) Uani 1 1 d . . . . .
C11 C 0.1014(3) 1.1332(4) 0.9541(7) 0.0181(15) Uani 1 1 d . . . . .
C12 C 0.0886(3) 1.0801(4) 0.8592(6) 0.0160(15) Uani 1 1 d . . . . .
F1 F 0.1246(2) 0.6802(2) 0.4889(4) 0.0263(10) Uani 1 1 d . . . . .
F2 F 0.2199(2) 0.9010(2) 0.3110(4) 0.0273(10) Uani 1 1 d . . . . .
F3 F 0.0560(2) 1.1893(2) 0.9781(4) 0.0276(10) Uani 1 1 d . . . . .
F4 F 0.2574(2) 1.0631(2) 1.0885(4) 0.0251(10) Uani 1 1 d . . . . .
N3 N 0.2036(3) 0.9849(3) 0.5292(6) 0.0170(13) Uani 1 1 d . . . . .
C13 C 0.1619(4) 1.0490(4) 0.4901(7) 0.0233(17) Uani 1 1 d . . . . .
H13A H 0.1140 1.0399 0.5139 0.028 Uiso 1 1 calc R U . . .
H13B H 0.1641 1.0549 0.3981 0.028 Uiso 1 1 calc R U . . .
C15 C 0.2985(4) 1.0680(4) 0.5607(8) 0.0257(18) Uani 1 1 d . . . . .
H15A H 0.2950 1.0592 0.6519 0.031 Uiso 1 1 calc R U . . .
H15B H 0.3468 1.0776 0.5403 0.031 Uiso 1 1 calc R U . . .
C16 C 0.2740(4) 0.9972(4) 0.4912(7) 0.0251(17) Uani 1 1 d . . . . .
H16A H 0.2768 1.0054 0.3997 0.030 Uiso 1 1 calc R U . . .
H16B H 0.3022 0.9521 0.5133 0.030 Uiso 1 1 calc R U . . .
C14 C 0.1880(4) 1.1211(4) 0.5530(7) 0.0246(17) Uani 1 1 d . . . . .
H14A H 0.1614 1.1658 0.5234 0.030 Uiso 1 1 calc R U . . .
H14B H 0.1813 1.1167 0.6445 0.030 Uiso 1 1 calc R U . . .
O1 O 0.2588(3) 1.1335(3) 0.5270(5) 0.0251(12) Uani 1 1 d . . . . .
N4 N 0.0950(3) 0.7534(3) 0.7069(5) 0.0187(15) Uani 1 1 d . . . . .
N5 N 0.2385(3) 0.9511(3) 0.9038(5) 0.0170(13) Uani 1 1 d . . . . .
N6 N 0.0337(3) 1.0864(3) 0.7775(5) 0.0206(14) Uani 1 1 d . . . . .
C20 C 0.3456(4) 0.8987(4) 0.8385(8) 0.0281(19) Uani 1 1 d . . . . .
H20A H 0.3305 0.8981 0.7502 0.034 Uiso 1 1 calc R U . . .
H20B H 0.3954 0.9065 0.8395 0.034 Uiso 1 1 calc R U . . .
C18 C 0.2578(4) 0.8146(4) 0.9013(7) 0.0231(17) Uani 1 1 d . . . . .
H18A H 0.2485 0.7655 0.9448 0.028 Uiso 1 1 calc R U . . .
H18B H 0.2393 0.8106 0.8155 0.028 Uiso 1 1 calc R U . . .
C19 C 0.3115(4) 0.9649(4) 0.9058(8) 0.0235(17) Uani 1 1 d . . . . .
H19A H 0.3279 0.9680 0.9931 0.028 Uiso 1 1 calc R U . . .
H19B H 0.3221 1.0140 0.8633 0.028 Uiso 1 1 calc R U . . .
C17 C 0.2224(4) 0.8788(4) 0.9692(7) 0.0191(16) Uani 1 1 d . . . . .
H17A H 0.1727 0.8700 0.9693 0.023 Uiso 1 1 calc R U . . .
H17B H 0.2383 0.8813 1.0569 0.023 Uiso 1 1 calc R U . . .
O2 O 0.3300(3) 0.8264(3) 0.8948(5) 0.0290(13) Uani 1 1 d . . . . .
C23 C 0.1242(4) 0.6834(4) 0.7579(9) 0.037(2) Uani 1 1 d . . . . .
H23A H 0.1534 0.6591 0.6936 0.045 Uiso 1 1 calc R U . . .
H23B H 0.1533 0.6966 0.8302 0.045 Uiso 1 1 calc R U . . .
C22 C -0.0059(4) 0.7286(5) 0.8281(9) 0.041(2) Uani 1 1 d . . . . .
H22A H -0.0363 0.7524 0.8908 0.049 Uiso 1 1 calc R U . . .
H22B H -0.0342 0.7130 0.7560 0.049 Uiso 1 1 calc R U . . .
C24 C 0.0732(5) 0.6289(5) 0.7974(10) 0.047(2) Uani 1 1 d . . . . .
H24A H 0.0957 0.5853 0.8401 0.056 Uiso 1 1 calc R U . . .
H24B H 0.0496 0.6084 0.7228 0.056 Uiso 1 1 calc R U . . .
C21 C 0.0425(5) 0.7860(5) 0.7861(8) 0.041(2) Uani 1 1 d . . . . .
H21A H 0.0181 0.8265 0.7392 0.049 Uiso 1 1 calc R U . . .
H21B H 0.0641 0.8103 0.8599 0.049 Uiso 1 1 calc R U . . .
O3 O 0.0235(3) 0.6624(3) 0.8810(5) 0.0363(14) Uani 1 1 d . . . . .
C25 C 0.0063(4) 1.1630(4) 0.7423(9) 0.0328(18) Uani 1 1 d . . . . .
H25A H -0.0256 1.1814 0.8073 0.039 Uiso 1 1 calc R U . . .
H25B H 0.0439 1.2005 0.7350 0.039 Uiso 1 1 calc R U . . .
C27 C -0.0202(4) 1.0295(5) 0.7842(8) 0.034(2) Uani 1 1 d . . . . .
H27A H -0.0519 1.0426 0.8529 0.041 Uiso 1 1 calc R U . . .
H27B H -0.0005 0.9783 0.8016 0.041 Uiso 1 1 calc R U . . .
C26 C -0.0292(5) 1.1557(6) 0.6218(9) 0.053(3) Uani 1 1 d . . . . .
H26A H -0.0481 1.2063 0.5979 0.064 Uiso 1 1 calc R U . . .
H26B H 0.0038 1.1402 0.5566 0.064 Uiso 1 1 calc R U . . .
C28 C -0.0574(5) 1.0279(6) 0.6632(11) 0.068(3) Uani 1 1 d . . . . .
H28A H -0.0269 1.0077 0.5974 0.081 Uiso 1 1 calc R U . . .
H28B H -0.0965 0.9925 0.6705 0.081 Uiso 1 1 calc R U . . .
O4 O -0.0815(3) 1.1021(4) 0.6262(7) 0.063(2) Uani 1 1 d . . . . .
O5 O 0.4232(4) 0.9323(5) 0.3699(8) 0.078(3) Uani 1 1 d . . . . .
C32 C 0.3934(6) 0.8724(8) 0.2845(14) 0.086(5) Uani 1 1 d . . . . .
H32A H 0.3445 0.8832 0.2710 0.104 Uiso 1 1 calc R U . . .
H32B H 0.3975 0.8211 0.3237 0.104 Uiso 1 1 calc R U . . .
C33 C 0.4299(5) 0.8728(8) 0.1614(13) 0.082(4) Uani 1 1 d . . . . .
H33A H 0.4114 0.8318 0.1072 0.098 Uiso 1 1 calc R U . . .
H33B H 0.4224 0.9227 0.1190 0.098 Uiso 1 1 calc R U . . .
C34 C 0.4879(6) 0.9207(8) 0.3776(11) 0.076(4) Uani 1 1 d . . . . .
H34A H 0.4952 0.8711 0.4209 0.091 Uiso 1 1 calc R U . . .
H34B H 0.5076 0.9614 0.4311 0.091 Uiso 1 1 calc R U . . .
N7 N 0.4980(5) 0.8615(6) 0.1786(10) 0.076(3) Uani 1 1 d . . . . .
H7N H 0.5196 0.8643 0.1033 0.100 Uiso 1 1 d . U . . .
C31 C 0.5254(6) 0.9190(6) 0.2622(11) 0.066(3) Uani 1 1 d . . . . .
H31A H 0.5737 0.9073 0.2798 0.079 Uiso 1 1 calc R U . . .
H31B H 0.5232 0.9700 0.2217 0.079 Uiso 1 1 calc R 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
I1 C4 2.084(7) . ?
I2 C10 2.080(7) . ?
N1 N2 1.275(7) . ?
N1 C7 1.423(8) . ?
N2 C1 1.426(9) . ?
C1 C6 1.413(10) . ?
C1 C2 1.418(9) . ?
C2 N4 1.388(8) . ?
C2 C3 1.399(10) . ?
C3 F1 1.355(7) . ?
C3 C4 1.377(10) . ?
C4 C5 1.377(9) . ?
C5 F2 1.355(8) . ?
C5 C6 1.379(10) . ?
C6 N3 1.419(9) . ?
C7 C12 1.396(9) . ?
C7 C8 1.421(10) . ?
C8 C9 1.393(10) . ?
C8 N5 1.402(9) . ?
C9 F4 1.353(7) . ?
C9 C10 1.382(9) . ?
C10 C11 1.384(10) . ?
C11 F3 1.349(7) . ?
C11 C12 1.396(9) . ?
C12 N6 1.394(8) . ?
N3 C13 1.448(9) . ?
N3 C16 1.459(9) . ?
C13 C14 1.513(10) . ?
C15 O1 1.428(9) . ?
C15 C16 1.518(10) . ?
C14 O1 1.439(9) . ?
N4 C21 1.452(9) . ?
N4 C23 1.454(9) . ?
N5 C19 1.456(9) . ?
N5 C17 1.475(8) . ?
N6 C27 1.453(9) . ?
N6 C25 1.486(9) . ?
C20 O2 1.428(9) . ?
C20 C19 1.516(10) . ?
C18 O2 1.437(9) . ?
C18 C17 1.504(9) . ?
C23 C24 1.445(12) . ?
C22 O3 1.409(10) . ?
C22 C21 1.452(11) . ?
C24 O3 1.447(11) . ?
C25 C26 1.472(12) . ?
C27 C28 1.487(12) . ?
C26 O4 1.390(12) . ?
C28 O4 1.431(11) . ?
O5 C34 1.291(13) . ?
O5 C32 1.505(14) . ?
C32 C33 1.500(17) . ?
C33 N7 1.367(13) . ?
C34 C31 1.438(15) . ?
N7 C31 1.446(13) . ?

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 N1 C7 115.5(6) . . ?
N1 N2 C1 111.9(6) . . ?
C6 C1 C2 121.4(6) . . ?
C6 C1 N2 122.1(6) . . ?
C2 C1 N2 115.6(6) . . ?
N4 C2 C3 119.2(6) . . ?
N4 C2 C1 124.3(6) . . ?
C3 C2 C1 116.5(6) . . ?
F1 C3 C4 118.2(6) . . ?
F1 C3 C2 118.3(6) . . ?
C4 C3 C2 123.5(6) . . ?
C5 C4 C3 117.7(6) . . ?
C5 C4 I1 120.9(5) . . ?
C3 C4 I1 121.4(5) . . ?
F2 C5 C4 117.7(6) . . ?
F2 C5 C6 118.8(6) . . ?
C4 C5 C6 123.5(7) . . ?
C5 C6 C1 117.5(6) . . ?
C5 C6 N3 121.0(6) . . ?
C1 C6 N3 121.0(6) . . ?
C12 C7 C8 122.1(6) . . ?
C12 C7 N1 113.8(6) . . ?
C8 C7 N1 122.8(6) . . ?
C9 C8 N5 122.7(6) . . ?
C9 C8 C7 116.6(7) . . ?
N5 C8 C7 120.6(7) . . ?
F4 C9 C10 118.3(6) . . ?
F4 C9 C8 118.5(6) . . ?
C10 C9 C8 123.0(6) . . ?
C9 C10 C11 118.2(6) . . ?
C9 C10 I2 121.3(5) . . ?
C11 C10 I2 120.2(5) . . ?
F3 C11 C10 117.6(6) . . ?
F3 C11 C12 119.9(6) . . ?
C10 C11 C12 122.5(6) . . ?
C11 C12 N6 123.0(6) . . ?
C11 C12 C7 117.5(6) . . ?
N6 C12 C7 119.5(6) . . ?
C6 N3 C13 119.0(6) . . ?
C6 N3 C16 116.8(6) . . ?
C13 N3 C16 110.2(6) . . ?
N3 C13 C14 108.6(6) . . ?
O1 C15 C16 110.5(6) . . ?
N3 C16 C15 106.5(6) . . ?
O1 C14 C13 111.5(6) . . ?
C15 O1 C14 111.2(5) . . ?
C2 N4 C21 123.7(6) . . ?
C2 N4 C23 121.2(6) . . ?
C21 N4 C23 113.0(6) . . ?
C8 N5 C19 120.3(6) . . ?
C8 N5 C17 116.3(6) . . ?
C19 N5 C17 110.2(6) . . ?
C12 N6 C27 118.7(6) . . ?
C12 N6 C25 120.7(6) . . ?
C27 N6 C25 111.1(6) . . ?
O2 C20 C19 112.1(6) . . ?
O2 C18 C17 112.0(6) . . ?
N5 C19 C20 107.7(6) . . ?
N5 C17 C18 107.9(6) . . ?
C20 O2 C18 111.0(5) . . ?
C24 C23 N4 112.6(7) . . ?
O3 C22 C21 114.7(7) . . ?
C23 C24 O3 112.7(8) . . ?
N4 C21 C22 112.2(7) . . ?
C22 O3 C24 111.0(6) . . ?
C26 C25 N6 108.4(7) . . ?
N6 C27 C28 109.2(7) . . ?
O4 C26 C25 112.3(8) . . ?
O4 C28 C27 112.8(8) . . ?
C26 O4 C28 111.7(7) . . ?
C34 O5 C32 108.3(9) . . ?
O5 C32 C33 110.0(10) . . ?
N7 C33 C32 110.5(11) . . ?
O5 C34 C31 117.0(11) . . ?
C33 N7 C31 110.5(10) . . ?
C34 C31 N7 110.7(9) . . ?

_refine_diff_density_max         1.069
_refine_diff_density_min         -0.819
_refine_diff_density_rms         0.103

_shelxl_version_number           2014-3

_vrf_PLAT431_5-morpholine        
;
PROBLEM: Short Inter HL..A  Contact I1 .. O1 .. 2.92 Ang.  
RESPONSE: This short contact corresponds to one of the
halogen bonds described in the manuscript.
;
_database_code_depnum_ccdc_archive 'CCDC 1007721'
