# Electronic Supplementary Material (ESI) for MedChemComm.
# 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. 
# 
#######################################################################

data_mo_sj_95_0m
_audit_block_doi                 10.5517/cc13m8ll
_database_code_depnum_ccdc_archive 'CCDC 1031419'
_audit_update_record             
;
2015-06-28 deposited with the CCDC.
2015-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H F N O'
_chemical_formula_weight         62.03

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   7.8954(6)
_cell_length_b                   24.3573(18)
_cell_length_c                   12.7445(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.249(3)
_cell_angle_gamma                90.00
_cell_volume                     2444.2(3)
_cell_formula_units_Z            41
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1271
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22991
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0462
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         25.10
_reflns_number_total             4350
_reflns_number_gt                2761
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4350
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1921
_refine_ls_R_factor_gt           0.1481
_refine_ls_wR_factor_ref         0.4323
_refine_ls_wR_factor_gt          0.4093
_refine_ls_goodness_of_fit_ref   1.679
_refine_ls_restrained_S_all      1.679
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.1127(5) 0.58249(16) 0.5424(3) 0.0554(12) Uani 1 1 d . . .
F1 F 0.4316(5) 0.44054(14) 0.7573(2) 0.0600(11) Uani 1 1 d . . .
N4 N 0.2763(5) 0.47022(17) 0.3347(3) 0.0371(11) Uani 1 1 d . . .
C1 C 0.4205(7) 0.4025(2) 0.5857(4) 0.0361(13) Uani 1 1 d . . .
C2 C 0.3069(6) 0.4602(2) 0.4422(4) 0.0327(12) Uani 1 1 d . . .
C3 C 0.2949(7) 0.4910(2) 0.6212(4) 0.0408(14) Uani 1 1 d . . .
H3 H 0.2645 0.5166 0.6705 0.049 Uiso 1 1 calc R . .
C4 C 0.1640(7) 0.5485(2) 0.4777(5) 0.0420(14) Uani 1 1 d . . .
O2 O 0.5573(7) 0.17931(16) 0.8107(3) 0.0653(14) Uani 1 1 d . . .
N3 N 0.4996(6) 0.35463(17) 0.6273(3) 0.0384(12) Uani 1 1 d . . .
C5 C 0.3875(7) 0.4112(2) 0.4790(4) 0.0354(13) Uani 1 1 d . . .
H5 H 0.4184 0.3849 0.4312 0.042 Uiso 1 1 calc R . .
C6 C 0.7806(7) 0.06328(19) 0.6368(4) 0.0319(12) Uani 1 1 d . . .
H6 H 0.8490 0.0358 0.6678 0.038 Uiso 1 1 calc R . .
C7 C 0.2540(6) 0.49932(19) 0.5136(4) 0.0325(12) Uani 1 1 d . . .
C8 C 0.1358(7) 0.5537(2) 0.3682(5) 0.0440(14) Uani 1 1 d . . .
O1 O 0.7425(6) 0.01308(16) 0.4829(3) 0.0614(13) Uani 1 1 d . . .
O4 O -0.0092(6) 0.63794(17) 0.3896(4) 0.0653(13) Uani 1 1 d . . .
H4 H 0.0368 0.6314 0.4481 0.098 Uiso 1 1 calc R . .
C9 C 0.3803(7) 0.4443(2) 0.6523(4) 0.0410(14) Uani 1 1 d . . .
C10 C 0.5599(8) 0.3150(2) 0.5531(4) 0.0447(15) Uani 1 1 d . . .
H10 H 0.5335 0.3155 0.4807 0.054 Uiso 1 1 calc R . .
C11 C 0.5949(7) 0.1936(2) 0.7233(4) 0.0419(14) Uani 1 1 d . . .
C12 C 0.6469(7) 0.1509(2) 0.6486(4) 0.0417(14) Uani 1 1 d . . .
N2 N 0.5847(7) 0.24717(19) 0.6946(4) 0.0499(14) Uani 1 1 d . . .
C13 C 0.1932(7) 0.5152(2) 0.3037(5) 0.0453(14) Uani 1 1 d . . .
H13 H 0.1727 0.5207 0.2317 0.054 Uiso 1 1 calc R . .
O5 O 0.0203(8) 0.6094(2) 0.2293(5) 0.0916(19) Uani 1 1 d . . .
C14 C 0.7161(7) 0.0594(2) 0.5379(4) 0.0451(15) Uani 1 1 d . . .
C15 C 0.7426(7) 0.1087(2) 0.6901(4) 0.0435(14) Uani 1 1 d . . .
H15 H 0.7847 0.1114 0.7600 0.052 Uiso 1 1 calc R . .
C16 C 0.3308(8) 0.4308(2) 0.2555(4) 0.0475(15) Uani 1 1 d . . .
H16A H 0.3505 0.4504 0.1913 0.057 Uiso 1 1 calc R . .
H16B H 0.4371 0.4140 0.2816 0.057 Uiso 1 1 calc R . .
C17 C 0.6716(8) 0.2731(2) 0.6111(5) 0.0482(15) Uani 1 1 d . . .
H17A H 0.7045 0.2453 0.5621 0.058 Uiso 1 1 calc R . .
H17B H 0.7741 0.2909 0.6410 0.058 Uiso 1 1 calc R . .
C18 C 0.0454(8) 0.6025(2) 0.3204(6) 0.0554(18) Uani 1 1 d . . .
C19 C 0.4089(9) 0.3261(2) 0.7079(5) 0.0527(17) Uani 1 1 d . . .
H19A H 0.3126 0.3065 0.6746 0.063 Uiso 1 1 calc R . .
H19B H 0.3663 0.3529 0.7559 0.063 Uiso 1 1 calc R . .
C20 C 0.6205(10) 0.1005(3) 0.4880(5) 0.0604(19) Uani 1 1 d . . .
H20 H 0.5835 0.0973 0.4172 0.072 Uiso 1 1 calc R . .
N1 N 0.5815(9) 0.1457(3) 0.5431(5) 0.0775(19) Uani 1 1 d . . .
C21 C 0.5219(9) 0.2872(2) 0.7674(5) 0.0554(17) Uani 1 1 d . . .
H21A H 0.6165 0.3068 0.8030 0.066 Uiso 1 1 calc R . .
H21B H 0.4602 0.2687 0.8200 0.066 Uiso 1 1 calc R . .
C22 C 0.8200(11) -0.0330(3) 0.5403(6) 0.072(2) Uani 1 1 d . . .
H22A H 0.9109 -0.0200 0.5882 0.108 Uiso 1 1 calc R . .
H22B H 0.8640 -0.0584 0.4917 0.108 Uiso 1 1 calc R . .
H22C H 0.7364 -0.0510 0.5792 0.108 Uiso 1 1 calc R . .
C23 C 0.2027(10) 0.3874(3) 0.2317(6) 0.074(2) Uani 1 1 d . . .
H23A H 0.1805 0.3685 0.2954 0.112 Uiso 1 1 calc R . .
H23B H 0.2449 0.3617 0.1827 0.112 Uiso 1 1 calc R . .
H23C H 0.0996 0.4036 0.2016 0.112 Uiso 1 1 calc R . .


_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
O3 C4 1.257(7) . ?
F1 C9 1.372(6) . ?
N4 C13 1.322(7) . ?
N4 C2 1.395(6) . ?
N4 C16 1.479(7) . ?
C1 C9 1.378(7) . ?
C1 C5 1.383(7) . ?
C1 N3 1.407(6) . ?
C2 C7 1.402(7) . ?
C2 C5 1.416(7) . ?
C3 C9 1.365(7) . ?
C3 C7 1.400(7) . ?
C4 C8 1.402(8) . ?
C4 C7 1.450(7) . ?
O2 C11 1.225(6) . ?
N3 C10 1.456(7) . ?
N3 C19 1.469(7) . ?
C6 C14 1.328(7) . ?
C6 C15 1.343(7) . ?
C8 C13 1.348(8) . ?
C8 C18 1.493(8) . ?
O1 C14 1.353(6) . ?
O1 C22 1.449(8) . ?
O4 C18 1.328(8) . ?
C10 C17 1.506(8) . ?
C11 N2 1.357(7) . ?
C11 C12 1.486(8) . ?
C12 C15 1.360(8) . ?
C12 N1 1.411(8) . ?
N2 C17 1.453(7) . ?
N2 C21 1.458(8) . ?
O5 C18 1.176(8) . ?
C14 C20 1.381(8) . ?
C16 C23 1.479(9) . ?
C19 C21 1.473(8) . ?
C20 N1 1.352(8) . ?

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
C13 N4 C2 118.9(5) . . ?
C13 N4 C16 119.8(5) . . ?
C2 N4 C16 121.2(4) . . ?
C9 C1 C5 117.1(5) . . ?
C9 C1 N3 119.8(4) . . ?
C5 C1 N3 123.0(5) . . ?
N4 C2 C7 118.7(4) . . ?
N4 C2 C5 120.9(4) . . ?
C7 C2 C5 120.4(4) . . ?
C9 C3 C7 118.6(5) . . ?
O3 C4 C8 123.9(5) . . ?
O3 C4 C7 120.7(5) . . ?
C8 C4 C7 115.3(5) . . ?
C1 N3 C10 117.5(4) . . ?
C1 N3 C19 115.4(4) . . ?
C10 N3 C19 110.0(4) . . ?
C1 C5 C2 120.2(5) . . ?
C14 C6 C15 117.0(5) . . ?
C3 C7 C2 118.6(5) . . ?
C3 C7 C4 120.1(5) . . ?
C2 C7 C4 121.2(5) . . ?
C13 C8 C4 120.5(5) . . ?
C13 C8 C18 118.6(6) . . ?
C4 C8 C18 120.9(6) . . ?
C14 O1 C22 117.4(5) . . ?
C3 C9 F1 116.2(5) . . ?
C3 C9 C1 124.7(5) . . ?
F1 C9 C1 119.1(5) . . ?
N3 C10 C17 109.7(4) . . ?
O2 C11 N2 120.3(5) . . ?
O2 C11 C12 118.8(5) . . ?
N2 C11 C12 120.9(5) . . ?
C15 C12 N1 117.1(5) . . ?
C15 C12 C11 116.9(5) . . ?
N1 C12 C11 125.1(5) . . ?
C11 N2 C17 126.4(5) . . ?
C11 N2 C21 119.3(4) . . ?
C17 N2 C21 112.1(5) . . ?
N4 C13 C8 125.2(5) . . ?
C6 C14 O1 119.2(5) . . ?
C6 C14 C20 123.0(5) . . ?
O1 C14 C20 117.8(5) . . ?
C6 C15 C12 124.4(5) . . ?
C23 C16 N4 112.0(5) . . ?
N2 C17 C10 111.3(5) . . ?
O5 C18 O4 121.6(6) . . ?
O5 C18 C8 123.9(7) . . ?
O4 C18 C8 114.5(6) . . ?
N3 C19 C21 110.8(5) . . ?
N1 C20 C14 119.2(5) . . ?
C20 N1 C12 119.2(6) . . ?
N2 C21 C19 109.0(5) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         2.908
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.208
