# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_Marek135
_database_code_depnum_ccdc_archive 'CCDC 1574441'
_audit_update_record             
;
2017-09-14 deposited with the CCDC.
2018-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'Marek135 (Jian Qiang Huang)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 Br F N O4'
_chemical_formula_sum            'C16 H13 Br F N O4'
_chemical_formula_weight         382.18
_chemical_absolute_configuration unk

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'

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

_cell_length_a                   29.8490(2)
_cell_length_b                   7.0020(2)
_cell_length_c                   7.6880(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1606.81(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1455
_cell_measurement_theta_min      0.68
_cell_measurement_theta_max      24.38

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    2.587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4623
_exptl_absorpt_correction_T_max  0.6531
_exptl_absorpt_process_details   
;  
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'   
;
_exptl_special_details           
;   
 ?   
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi- and omega-scans'
_diffrn_detector_area_resol_mean 95
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            1551
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         24.38
_reflns_number_total             1551
_reflns_number_gt                1417
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius, 2006)'
_computing_cell_refinement       'DENZO HKL2000 (Otwinowski & Minor 1997)'
_computing_data_reduction        'DENZO HKL2000 (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury 3.7'
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1011P)²+0.7687P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         1551
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1449
_refine_ls_wR_factor_gt          0.1317
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.44614(3) 0.22375(13) 0.71509(11) 0.0603(3) Uani 1 1 d . . .
F1 F 0.61465(12) 0.8037(7) 0.0396(5) 0.0535(11) Uani 1 1 d . . .
O1 O 0.6230(2) 0.3545(12) 0.5714(8) 0.078(2) Uani 1 1 d . . .
O2 O 0.63112(18) 0.1486(10) 0.3692(9) 0.0698(18) Uani 1 1 d . . .
O3 O 0.57207(19) 0.2222(9) -0.0430(6) 0.0577(14) Uani 1 1 d . . .
O4 O 0.60447(18) 0.4340(8) 0.1346(6) 0.0537(14) Uani 1 1 d . . .
N1 N 0.60825(18) 0.2554(10) 0.4562(7) 0.0455(15) Uani 1 1 d . . .
C1 C 0.4861(2) 0.2396(10) 0.5260(9) 0.0410(15) Uani 1 1 d . . .
C2 C 0.4696(2) 0.2360(10) 0.3580(10) 0.0479(16) Uani 1 1 d . . .
H2 H 0.4389 0.2260 0.3383 0.057 Uiso 1 1 calc R . .
C3 C 0.4993(2) 0.2476(10) 0.2184(8) 0.0449(15) Uani 1 1 d . . .
H3 H 0.4883 0.2452 0.1052 0.054 Uiso 1 1 calc R . .
C4 C 0.5450(2) 0.2627(9) 0.2468(8) 0.0366(13) Uani 1 1 d . . .
C5 C 0.5598(2) 0.2598(10) 0.4193(8) 0.0361(14) Uani 1 1 d . . .
C6 C 0.5314(2) 0.2511(10) 0.5588(8) 0.0411(15) Uani 1 1 d . . .
H6 H 0.5423 0.2530 0.6721 0.049 Uiso 1 1 calc R . .
C7 C 0.5754(2) 0.2975(11) 0.0965(9) 0.0408(16) Uani 1 1 d . . .
C8 C 0.6367(2) 0.4861(12) 0.0040(8) 0.0488(19) Uani 1 1 d . . .
H8A H 0.6230 0.4846 -0.1104 0.059 Uiso 1 1 calc R . .
H8B H 0.6616 0.3970 0.0044 0.059 Uiso 1 1 calc R . .
C9 C 0.6529(2) 0.6845(10) 0.0480(9) 0.0387(16) Uani 1 1 d . . .
C10 C 0.6709(2) 0.7068(11) 0.2329(8) 0.0456(16) Uani 1 1 d . . .
H10A H 0.6788 0.8379 0.2529 0.068 Uiso 1 1 calc R . .
H10B H 0.6970 0.6279 0.2471 0.068 Uiso 1 1 calc R . .
H10C H 0.6484 0.6685 0.3147 0.068 Uiso 1 1 calc R . .
C11 C 0.6861(2) 0.7486(11) -0.0898(8) 0.0402(15) Uani 1 1 d . . .
C12 C 0.6765(3) 0.9000(11) -0.2011(9) 0.0505(18) Uani 1 1 d . . .
H12 H 0.6499 0.9678 -0.1877 0.061 Uiso 1 1 calc R . .
C13 C 0.7060(3) 0.9500(14) -0.3308(10) 0.059(2) Uani 1 1 d . . .
H13 H 0.6994 1.0520 -0.4040 0.071 Uiso 1 1 calc R . .
C14 C 0.7450(3) 0.8502(15) -0.3524(11) 0.063(2) Uani 1 1 d . . .
H14 H 0.7641 0.8805 -0.4437 0.076 Uiso 1 1 calc R . .
C15 C 0.7559(3) 0.7073(13) -0.2411(11) 0.060(2) Uani 1 1 d . . .
H15 H 0.7832 0.6451 -0.2531 0.072 Uiso 1 1 calc R . .
C16 C 0.7270(3) 0.6534(11) -0.1109(11) 0.0513(19) Uani 1 1 d . . .
H16 H 0.7347 0.5537 -0.0367 0.062 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0538(5) 0.0639(5) 0.0633(5) -0.0001(4) 0.0261(3) 0.0017(4)
F1 0.040(2) 0.070(3) 0.050(2) 0.006(2) 0.0021(17) 0.011(2)
O1 0.059(3) 0.125(6) 0.049(3) -0.032(4) -0.007(3) -0.019(4)
O2 0.043(3) 0.092(5) 0.074(4) -0.022(4) 0.002(3) 0.017(3)
O3 0.073(3) 0.063(4) 0.037(3) -0.008(3) 0.006(2) -0.019(3)
O4 0.070(3) 0.063(3) 0.028(2) -0.011(3) 0.015(2) -0.026(3)
N1 0.041(3) 0.063(4) 0.032(3) -0.005(3) 0.002(2) 0.000(3)
C1 0.040(3) 0.037(4) 0.046(3) -0.003(4) 0.013(3) 0.004(3)
C2 0.039(3) 0.042(4) 0.063(4) 0.003(4) 0.003(3) -0.001(3)
C3 0.049(4) 0.047(4) 0.039(3) 0.008(4) -0.006(3) 0.000(3)
C4 0.048(3) 0.030(3) 0.031(3) 0.002(3) 0.000(3) -0.002(3)
C5 0.034(3) 0.037(3) 0.038(3) -0.006(3) -0.001(2) 0.002(3)
C6 0.052(4) 0.036(4) 0.035(3) -0.004(3) 0.002(3) 0.000(3)
C7 0.046(4) 0.042(4) 0.035(4) -0.001(3) -0.003(3) -0.007(3)
C8 0.055(5) 0.056(4) 0.036(4) -0.007(4) 0.015(3) -0.019(4)
C9 0.037(3) 0.043(4) 0.036(3) 0.003(3) 0.002(3) 0.004(3)
C10 0.047(4) 0.054(4) 0.036(3) 0.001(4) -0.006(3) 0.002(3)
C11 0.037(3) 0.050(4) 0.033(3) 0.004(3) -0.004(2) -0.006(3)
C12 0.045(4) 0.056(4) 0.050(4) 0.012(4) -0.005(3) -0.008(3)
C13 0.054(5) 0.073(5) 0.051(4) 0.016(4) -0.004(4) -0.016(4)
C14 0.065(5) 0.075(6) 0.049(4) -0.004(5) 0.015(4) -0.032(5)
C15 0.051(4) 0.060(5) 0.068(5) -0.011(5) 0.020(4) -0.004(4)
C16 0.052(4) 0.043(4) 0.060(5) 0.000(4) 0.008(4) 0.005(3)

_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 1.884(6) . ?
F1 C9 1.415(8) . ?
O1 N1 1.208(8) . ?
O2 N1 1.213(8) . ?
O3 C7 1.199(9) . ?
O4 C7 1.324(8) . ?
O4 C8 1.439(8) . ?
N1 C5 1.474(8) . ?
C1 C6 1.377(9) . ?
C1 C2 1.383(10) . ?
C2 C3 1.394(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.398(9) . ?
C4 C7 1.488(9) . ?
C5 C6 1.369(9) . ?
C6 H6 0.9300 . ?
C8 C9 1.509(11) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C11 1.518(9) . ?
C9 C10 1.528(9) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.392(10) . ?
C11 C16 1.402(10) . ?
C12 C13 1.375(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(13) . ?
C13 H13 0.9300 . ?
C14 C15 1.355(13) . ?
C14 H14 0.9300 . ?
C15 C16 1.373(11) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O4 C8 117.9(5) . . ?
O1 N1 O2 123.6(6) . . ?
O1 N1 C5 119.1(6) . . ?
O2 N1 C5 117.3(6) . . ?
C6 C1 C2 121.5(6) . . ?
C6 C1 Br1 118.9(5) . . ?
C2 C1 Br1 119.6(5) . . ?
C1 C2 C3 119.4(6) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 120.7(6) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 117.3(6) . . ?
C3 C4 C7 119.3(6) . . ?
C5 C4 C7 123.2(6) . . ?
C6 C5 C4 123.3(6) . . ?
C6 C5 N1 117.1(5) . . ?
C4 C5 N1 119.5(5) . . ?
C5 C6 C1 117.8(6) . . ?
C5 C6 H6 121.1 . . ?
C1 C6 H6 121.1 . . ?
O3 C7 O4 124.7(7) . . ?
O3 C7 C4 124.9(6) . . ?
O4 C7 C4 110.2(6) . . ?
O4 C8 C9 106.9(6) . . ?
O4 C8 H8A 110.3 . . ?
C9 C8 H8A 110.3 . . ?
O4 C8 H8B 110.3 . . ?
C9 C8 H8B 110.3 . . ?
H8A C8 H8B 108.6 . . ?
F1 C9 C8 106.0(6) . . ?
F1 C9 C11 108.7(6) . . ?
C8 C9 C11 108.9(6) . . ?
F1 C9 C10 105.5(5) . . ?
C8 C9 C10 114.5(6) . . ?
C11 C9 C10 112.9(6) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 118.0(6) . . ?
C12 C11 C9 121.3(6) . . ?
C16 C11 C9 120.6(6) . . ?
C13 C12 C11 120.5(8) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 120.2(8) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 120.3(7) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.8(8) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C11 120.1(8) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        24.38
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.249
_refine_diff_density_min         -0.792
_refine_diff_density_rms         0.135
