# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_pf17_02_a
_database_code_depnum_ccdc_archive 'CCDC 1401263'
_audit_update_record             
;
2015-05-16 deposited with the CCDC.
2015-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'(Z)-1-((4-bromothiophen-2-yl)methylene)-6-methylfuro[3,4-c]pyridine-3,4(1H,5H)-dione , 1-methylpyrrolidin-2-one'
_chemical_name_common            pf17
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H8 Br N O3 S, C5 H9 N O'
_chemical_formula_sum            'C18 H17 Br N2 O4 S'
_chemical_formula_weight         437.30

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'
S S 0.1246 0.1234 '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                   7.4930(4)
_cell_length_b                   32.9156(16)
_cell_length_c                   7.6917(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.704(2)
_cell_angle_gamma                90
_cell_volume                     1834.93(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      26.38

_exptl_crystal_description       Plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.586
_exptl_crystal_size_mid          0.334
_exptl_crystal_size_min          0.238
_exptl_absorpt_coefficient_mu    2.380
_shelx_estimated_absorpt_T_min   0.336
_shelx_estimated_absorpt_T_max   0.601
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.342
_exptl_absorpt_correction_T_max  0.525
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36491
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.475
_diffrn_reflns_theta_max         26.409
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3761
_reflns_number_gt                3147
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0517P)²+1.8641P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0148(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3761
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1194
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.002
_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 1.26253(6) 0.77263(2) 0.77867(6) 0.0716(2) Uani 1 1 d . . . . .
S1 S 0.72200(10) 0.71395(2) 0.64861(11) 0.0431(2) Uani 1 1 d . . . . .
O1 O 0.5294(3) 0.63657(6) 0.5186(3) 0.0404(5) Uani 1 1 d . . . . .
O3 O 0.2203(3) 0.52609(7) 0.2946(4) 0.0550(6) Uani 1 1 d . . . . .
O2 O 0.2365(3) 0.61496(8) 0.4778(4) 0.0622(7) Uani 1 1 d . . . . .
N1 N 0.5099(3) 0.50924(7) 0.2756(3) 0.0380(5) Uani 1 1 d . . . . .
H1N H 0.4676 0.4863 0.2296 0.046 Uiso 1 1 calc R U . . .
O4 O 0.4344(4) 0.43053(8) 0.1313(4) 0.0716(8) Uani 1 1 d . . . . .
C3 C 0.8883(4) 0.68118(8) 0.6075(3) 0.0325(6) Uani 1 1 d . . . . .
C7 C 0.6543(3) 0.58005(8) 0.4175(3) 0.0312(5) Uani 1 1 d . . . . .
C5 C 0.8515(4) 0.64079(8) 0.5367(4) 0.0327(6) Uani 1 1 d . . . . .
H5 H 0.9528 0.6269 0.5172 0.039 Uiso 1 1 calc R U . . .
N2 N 0.2814(4) 0.37380(8) 0.0096(4) 0.0512(7) Uani 1 1 d . . . . .
C8 C 0.4687(3) 0.57293(8) 0.3962(4) 0.0345(6) Uani 1 1 d . . . . .
C4 C 1.0583(4) 0.69928(9) 0.6485(4) 0.0378(6) Uani 1 1 d . . . . .
H4 H 1.1652 0.6867 0.6355 0.045 Uiso 1 1 calc R U . . .
C10 C 0.7717(3) 0.55188(8) 0.3678(4) 0.0352(6) Uani 1 1 d . . . . .
H10 H 0.8965 0.5572 0.3820 0.042 Uiso 1 1 calc R U . . .
C6 C 0.6927(3) 0.62035(8) 0.4951(4) 0.0329(6) Uani 1 1 d . . . . .
C12 C 0.3831(4) 0.53586(9) 0.3206(4) 0.0373(6) Uani 1 1 d . . . . .
C11 C 0.6933(4) 0.51597(8) 0.2972(4) 0.0363(6) Uani 1 1 d . . . . .
C9 C 0.3880(4) 0.60759(9) 0.4638(4) 0.0412(7) Uani 1 1 d . . . . .
C1 C 1.0524(4) 0.73917(9) 0.7126(4) 0.0438(7) Uani 1 1 d . . . . .
C14 C 0.2926(5) 0.41131(10) 0.0735(4) 0.0493(8) Uani 1 1 d . . . . .
C2 C 0.8830(5) 0.75112(9) 0.7216(4) 0.0491(8) Uani 1 1 d . . . . .
H2 H 0.8568 0.7765 0.7625 0.059 Uiso 1 1 calc R U . . .
C13 C 0.8019(4) 0.48271(9) 0.2402(5) 0.0504(8) Uani 1 1 d . . . . .
H13A H 0.7876 0.4581 0.3025 0.076 Uiso 1 1 calc R U . . .
H13B H 0.9299 0.4902 0.2686 0.076 Uiso 1 1 calc R U . . .
H13C H 0.7579 0.4785 0.1130 0.076 Uiso 1 1 calc R U . . .
C17 C 0.0977(5) 0.35796(11) -0.0551(5) 0.0587(9) Uani 1 1 d . . . . .
H17A H 0.0844 0.3322 0.0014 0.070 Uiso 1 1 calc R U . . .
H17B H 0.0664 0.3544 -0.1845 0.070 Uiso 1 1 calc R U . . .
C15 C 0.1011(5) 0.42614(12) 0.0620(5) 0.0611(9) Uani 1 1 d . . . . .
H15A H 0.0906 0.4354 0.1788 0.073 Uiso 1 1 calc R U . . .
H15B H 0.0701 0.4485 -0.0224 0.073 Uiso 1 1 calc R U . . .
C18 C 0.4414(6) 0.35061(12) -0.0038(6) 0.0674(10) Uani 1 1 d . . . . .
H18A H 0.4403 0.3473 -0.1280 0.101 Uiso 1 1 calc R U . . .
H18B H 0.4386 0.3244 0.0503 0.101 Uiso 1 1 calc R U . . .
H18C H 0.5515 0.3647 0.0575 0.101 Uiso 1 1 calc R U . . .
C16 C -0.0236(5) 0.39107(14) -0.0001(6) 0.0723(11) Uani 1 1 d . . . . .
H16A H -0.1238 0.3987 -0.1018 0.087 Uiso 1 1 calc R U . . .
H16B H -0.0754 0.3814 0.0956 0.087 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 1.883(3) . ?
S1 C2 1.710(3) . ?
S1 C3 1.737(3) . ?
O1 C6 1.389(3) . ?
O1 C9 1.408(3) . ?
O3 C12 1.228(3) . ?
O2 C9 1.192(4) . ?
N1 C11 1.360(4) . ?
N1 C12 1.399(4) . ?
N1 H1N 0.8600 . ?
O4 C14 1.219(4) . ?
C3 C4 1.368(4) . ?
C3 C5 1.436(4) . ?
C7 C8 1.379(4) . ?
C7 C10 1.397(4) . ?
C7 C6 1.453(4) . ?
C5 C6 1.333(4) . ?
C5 H5 0.9300 . ?
N2 C14 1.324(4) . ?
N2 C17 1.437(4) . ?
N2 C18 1.447(4) . ?
C8 C12 1.431(4) . ?
C8 C9 1.448(4) . ?
C4 C1 1.407(4) . ?
C4 H4 0.9300 . ?
C10 C11 1.369(4) . ?
C10 H10 0.9300 . ?
C11 C13 1.494(4) . ?
C1 C2 1.347(5) . ?
C14 C15 1.497(5) . ?
C2 H2 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C17 C16 1.545(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C15 C16 1.486(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C16 H16A 0.9700 . ?
C16 H16B 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
C2 S1 C3 91.45(15) . . ?
C6 O1 C9 108.7(2) . . ?
C11 N1 C12 126.6(2) . . ?
C11 N1 H1N 116.7 . . ?
C12 N1 H1N 116.7 . . ?
C4 C3 C5 124.6(2) . . ?
C4 C3 S1 110.9(2) . . ?
C5 C3 S1 124.5(2) . . ?
C8 C7 C10 122.7(2) . . ?
C8 C7 C6 107.0(2) . . ?
C10 C7 C6 130.2(2) . . ?
C6 C5 C3 129.2(2) . . ?
C6 C5 H5 115.4 . . ?
C3 C5 H5 115.4 . . ?
C14 N2 C17 115.6(3) . . ?
C14 N2 C18 122.9(3) . . ?
C17 N2 C18 121.5(3) . . ?
C7 C8 C12 121.9(2) . . ?
C7 C8 C9 108.9(2) . . ?
C12 C8 C9 129.2(2) . . ?
C3 C4 C1 112.2(3) . . ?
C3 C4 H4 123.9 . . ?
C1 C4 H4 123.9 . . ?
C11 C10 C7 116.4(2) . . ?
C11 C10 H10 121.8 . . ?
C7 C10 H10 121.8 . . ?
C5 C6 O1 122.5(2) . . ?
C5 C6 C7 129.1(2) . . ?
O1 C6 C7 108.4(2) . . ?
O3 C12 N1 120.3(3) . . ?
O3 C12 C8 127.8(3) . . ?
N1 C12 C8 111.8(2) . . ?
N1 C11 C10 120.5(3) . . ?
N1 C11 C13 117.0(3) . . ?
C10 C11 C13 122.5(3) . . ?
O2 C9 O1 119.7(3) . . ?
O2 C9 C8 133.4(3) . . ?
O1 C9 C8 106.9(2) . . ?
C2 C1 C4 113.8(3) . . ?
C2 C1 Br1 123.3(2) . . ?
C4 C1 Br1 122.8(2) . . ?
O4 C14 N2 125.9(3) . . ?
O4 C14 C15 125.9(3) . . ?
N2 C14 C15 108.2(3) . . ?
C1 C2 S1 111.7(2) . . ?
C1 C2 H2 124.2 . . ?
S1 C2 H2 124.2 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C17 C16 103.1(3) . . ?
N2 C17 H17A 111.1 . . ?
C16 C17 H17A 111.1 . . ?
N2 C17 H17B 111.1 . . ?
C16 C17 H17B 111.1 . . ?
H17A C17 H17B 109.1 . . ?
C16 C15 C14 106.3(3) . . ?
C16 C15 H15A 110.5 . . ?
C14 C15 H15A 110.5 . . ?
C16 C15 H15B 110.5 . . ?
C14 C15 H15B 110.5 . . ?
H15A C15 H15B 108.7 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C16 C17 105.7(3) . . ?
C15 C16 H16A 110.6 . . ?
C17 C16 H16A 110.6 . . ?
C15 C16 H16B 110.6 . . ?
C17 C16 H16B 110.6 . . ?
H16A C16 H16B 108.7 . . ?

_refine_diff_density_max         0.596
_refine_diff_density_min         -0.861
_refine_diff_density_rms         0.062



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent:  1-methylpyrrolidin-2-one, n-hexane'
