# 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. 
# 
#######################################################################

data_mo_nj_zyq_45_0m
_database_code_depnum_ccdc_archive 'CCDC 1412248'
_audit_update_record             
;
2015-07-13 deposited with the CCDC.
2015-08-20 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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.5592(4)
_cell_length_b                   16.6240(8)
_cell_length_c                   14.1389(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.372(2)
_cell_angle_gamma                90.00
_cell_volume                     1999.37(16)
_cell_formula_units_Z            33
_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    1.700
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1023
_exptl_absorpt_coefficient_mu    0.191
_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            20400
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         27.55
_reflns_number_total             4599
_reflns_number_gt                3175
_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)+(0.0643P)²+0.6003P] 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         4599
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1338
_refine_ls_wR_factor_gt          0.1167
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
N1 N 0.73996(19) 0.22262(10) 1.02616(10) 0.0414(4) Uani 1 1 d . . .
O1 O 0.55479(18) -0.13014(8) 0.86507(11) 0.0545(4) Uani 1 1 d . . .
F2 F 0.67628(16) 0.15563(10) 0.43027(8) 0.0737(4) Uani 1 1 d . . .
C7 C 0.7155(2) 0.18854(11) 0.94275(12) 0.0359(4) Uani 1 1 d . . .
C20 C 0.6659(2) 0.24171(11) 0.60401(12) 0.0404(4) Uani 1 1 d . . .
H20 H 0.5990 0.2654 0.5556 0.048 Uiso 1 1 calc R . .
O2 O 0.42067(18) -0.03307(8) 0.77271(10) 0.0553(4) Uani 1 1 d . . .
C15 C 0.74628(19) 0.22427(10) 0.77331(11) 0.0325(4) Uani 1 1 d . . .
N3 N 0.5110(2) 0.30505(11) 0.71691(11) 0.0479(4) Uani 1 1 d . . .
N2 N 0.72449(17) 0.24329(8) 0.86857(9) 0.0338(3) Uani 1 1 d . . .
C16 C 0.6468(2) 0.25583(11) 0.69782(12) 0.0353(4) Uani 1 1 d . . .
C9 C 0.5597(2) 0.08267(11) 0.85093(12) 0.0400(4) Uani 1 1 d . . .
H9 H 0.5062 0.1214 0.8125 0.048 Uiso 1 1 calc R . .
C5 C 0.7599(2) 0.31810(10) 0.91122(12) 0.0350(4) Uani 1 1 d . . .
C8 C 0.6772(2) 0.10381(11) 0.92442(12) 0.0365(4) Uani 1 1 d . . .
C17 C 0.8674(2) 0.17532(11) 0.74826(12) 0.0399(4) Uani 1 1 d . . .
C19 C 0.7856(2) 0.19196(12) 0.58287(12) 0.0407(4) Uani 1 1 d . . .
O4 O 1.02426(18) 0.17951(11) 0.89171(11) 0.0706(5) Uani 1 1 d . . .
O5 O 0.41205(19) 0.27290(12) 0.75857(11) 0.0721(5) Uani 1 1 d . . .
C11 C 0.6076(2) -0.05529(11) 0.89473(13) 0.0405(4) Uani 1 1 d . . .
C10 C 0.5281(2) 0.00272(11) 0.83877(12) 0.0387(4) Uani 1 1 d . . .
O6 O 0.5049(2) 0.37321(10) 0.68514(14) 0.0788(5) Uani 1 1 d . . .
F1 F 0.8559(2) 0.24506(11) 0.44172(9) 0.0920(5) Uani 1 1 d . . .
F3 F 0.91358(18) 0.12186(11) 0.46960(9) 0.0878(5) Uani 1 1 d . . .
C6 C 0.7682(2) 0.30310(11) 1.00874(12) 0.0388(4) Uani 1 1 d . . .
C13 C 0.7549(2) 0.04478(12) 0.98094(13) 0.0446(5) Uani 1 1 d . . .
H13 H 0.8315 0.0599 1.0295 0.054 Uiso 1 1 calc R . .
C18 C 0.8859(2) 0.15776(12) 0.65463(13) 0.0440(4) Uani 1 1 d . . .
H18 H 0.9654 0.1232 0.6402 0.053 Uiso 1 1 calc R . .
C4 C 0.7837(2) 0.39333(12) 0.87428(15) 0.0463(5) Uani 1 1 d . . .
H4 H 0.7797 0.4022 0.8091 0.056 Uiso 1 1 calc R . .
N4 N 0.9856(2) 0.14135(13) 0.82074(12) 0.0590(5) Uani 1 1 d . . .
C2 C 0.8200(3) 0.44133(14) 1.03685(17) 0.0603(6) Uani 1 1 d . . .
H2 H 0.8393 0.4844 1.0784 0.072 Uiso 1 1 calc R . .
C21 C 0.8085(3) 0.17824(15) 0.48078(14) 0.0542(5) Uani 1 1 d . . .
C1 C 0.7982(2) 0.36660(13) 1.07276(14) 0.0502(5) Uani 1 1 d . . .
H1 H 0.8032 0.3582 1.1380 0.060 Uiso 1 1 calc R . .
C12 C 0.7211(2) -0.03627(12) 0.96679(14) 0.0486(5) Uani 1 1 d . . .
H12 H 0.7733 -0.0758 1.0047 0.058 Uiso 1 1 calc R . .
C14 C 0.4181(3) -0.11584(12) 0.80046(15) 0.0525(5) Uani 1 1 d . . .
H14A H 0.3243 -0.1271 0.8308 0.063 Uiso 1 1 calc R . .
H14B H 0.4181 -0.1503 0.7451 0.063 Uiso 1 1 calc R . .
C3 C 0.8138(3) 0.45461(13) 0.93918(17) 0.0592(6) Uani 1 1 d . . .
H3 H 0.8305 0.5063 0.9173 0.071 Uiso 1 1 calc R . .
O3 O 1.0355(3) 0.07512(15) 0.80527(15) 0.1272(11) Uani 1 1 d . . .


_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
N1 C7 1.304(2) . ?
N1 C6 1.386(2) . ?
O1 C11 1.373(2) . ?
O1 C14 1.422(3) . ?
F2 C21 1.324(2) . ?
C7 N2 1.397(2) . ?
C7 C8 1.463(3) . ?
C20 C16 1.375(2) . ?
C20 C19 1.375(3) . ?
O2 C10 1.371(2) . ?
O2 C14 1.432(2) . ?
C15 C16 1.392(2) . ?
C15 C17 1.394(2) . ?
C15 N2 1.416(2) . ?
N3 O5 1.208(2) . ?
N3 O6 1.218(2) . ?
N3 C16 1.471(2) . ?
N2 C5 1.401(2) . ?
C9 C10 1.364(3) . ?
C9 C8 1.408(2) . ?
C5 C4 1.379(3) . ?
C5 C6 1.395(2) . ?
C8 C13 1.388(3) . ?
C17 C18 1.382(2) . ?
C17 N4 1.471(2) . ?
C19 C18 1.377(3) . ?
C19 C21 1.496(3) . ?
O4 N4 1.202(2) . ?
C11 C12 1.364(3) . ?
C11 C10 1.378(3) . ?
F1 C21 1.324(3) . ?
F3 C21 1.320(3) . ?
C6 C1 1.396(3) . ?
C13 C12 1.388(3) . ?
C4 C3 1.376(3) . ?
N4 O3 1.210(3) . ?
C2 C1 1.363(3) . ?
C2 C3 1.394(3) . ?

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 N1 C6 105.79(14) . . ?
C11 O1 C14 105.32(14) . . ?
N1 C7 N2 112.28(16) . . ?
N1 C7 C8 126.08(15) . . ?
N2 C7 C8 121.61(15) . . ?
C16 C20 C19 118.92(16) . . ?
C10 O2 C14 105.06(14) . . ?
C16 C15 C17 115.71(15) . . ?
C16 C15 N2 120.76(15) . . ?
C17 C15 N2 123.52(15) . . ?
O5 N3 O6 126.03(19) . . ?
O5 N3 C16 117.02(17) . . ?
O6 N3 C16 116.85(18) . . ?
C7 N2 C5 106.41(13) . . ?
C7 N2 C15 126.35(14) . . ?
C5 N2 C15 124.25(14) . . ?
C20 C16 C15 123.20(16) . . ?
C20 C16 N3 116.94(15) . . ?
C15 C16 N3 119.83(15) . . ?
C10 C9 C8 116.86(16) . . ?
C4 C5 C6 122.88(16) . . ?
C4 C5 N2 132.55(16) . . ?
C6 C5 N2 104.57(14) . . ?
C13 C8 C9 120.39(17) . . ?
C13 C8 C7 119.70(16) . . ?
C9 C8 C7 119.91(16) . . ?
C18 C17 C15 122.31(16) . . ?
C18 C17 N4 116.30(16) . . ?
C15 C17 N4 121.36(15) . . ?
C20 C19 C18 120.45(16) . . ?
C20 C19 C21 118.83(17) . . ?
C18 C19 C21 120.68(18) . . ?
C12 C11 O1 128.39(17) . . ?
C12 C11 C10 122.12(17) . . ?
O1 C11 C10 109.49(16) . . ?
C9 C10 O2 128.13(16) . . ?
C9 C10 C11 122.08(16) . . ?
O2 C10 C11 109.78(16) . . ?
N1 C6 C5 110.94(15) . . ?
N1 C6 C1 129.62(17) . . ?
C5 C6 C1 119.42(18) . . ?
C8 C13 C12 121.64(17) . . ?
C19 C18 C17 119.34(18) . . ?
C3 C4 C5 116.32(19) . . ?
O4 N4 O3 124.14(19) . . ?
O4 N4 C17 118.91(18) . . ?
O3 N4 C17 116.93(18) . . ?
C1 C2 C3 121.5(2) . . ?
F3 C21 F1 107.56(18) . . ?
F3 C21 F2 106.66(18) . . ?
F1 C21 F2 107.22(19) . . ?
F3 C21 C19 112.82(18) . . ?
F1 C21 C19 110.71(18) . . ?
F2 C21 C19 111.59(17) . . ?
C2 C1 C6 118.09(19) . . ?
C11 C12 C13 116.90(17) . . ?
O1 C14 O2 107.47(15) . . ?
C4 C3 C2 121.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.071
