# 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_snm-p2-cn-5-f
_database_code_depnum_ccdc_archive 'CCDC 1831432'
_audit_update_record             
;
2018-03-21 deposited with the CCDC.
2018-07-10 downloaded from the CCDC.
;
_audit_creation_date             2018-01-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_chemical_name_common            ?
_chemical_name_systematic        Unknown
_chemical_formula_moiety         'C22 H21 F N3 O3, C H4 O'
_chemical_formula_sum            'C23 H25 F N3 O4'
_chemical_formula_weight         426.46
_chemical_absolute_configuration ?
_chemical_compound_source        Synthesis
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H22 O3 N3 F1'
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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_symmetry_int_tables_number      14
_cell_length_a                   11.8968(11)
_cell_length_b                   18.4254(17)
_cell_length_c                   10.7033(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.556(8)
_cell_angle_gamma                90.00
_cell_volume                     2280.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1792
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.2250
_cell_measurement_theta_min      3.6640
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64395
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             900
_exptl_crystal_recrystallization_method 'Dichloromethane and methanol solvents'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8912
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.95
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2760
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  21.00   1.00    8.93    --  -17.33 -99.00  60.00   30
  2  ω    -48.00  16.00   1.00    8.93    --   20.84 -57.00 150.00   64
  3  ω    -86.00   1.00   1.00    8.93    --  -17.33 -57.00   0.00   87
  4  ω    -75.00 -21.00   1.00    8.93    --  -17.33 -57.00 -90.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0274521000
_diffrn_orient_matrix_UB_12      -0.0343828000
_diffrn_orient_matrix_UB_13      0.0047099000
_diffrn_orient_matrix_UB_21      -0.0546782000
_diffrn_orient_matrix_UB_22      -0.0170430000
_diffrn_orient_matrix_UB_23      -0.0210059000
_diffrn_orient_matrix_UB_31      0.0046135000
_diffrn_orient_matrix_UB_32      0.0030264000
_diffrn_orient_matrix_UB_33      -0.0646507000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2551
_reflns_number_total             4015
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4015
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0567
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0491P)²+0.6800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1468
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H24), C5(H5), C2(H2), C17(H17), C3(H3), C13(H13), C16(H16), C15(H15),
 C14(H14)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C20(H20A,H20B,H20C), C23(H23A,H23B,H23C), C21(H21A,H21B,
 H21C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O2 O 0.50752(14) 0.56035(11) 0.20378(16) 0.0468(5) Uani 1 d . . .
F1 F 1.02588(16) 0.58134(11) -0.03895(16) 0.0779(6) Uani 1 d . . .
O1 O 0.66731(17) 0.66901(10) 0.44002(17) 0.0527(5) Uani 1 d . . .
O3 O 0.41917(15) 0.53817(11) 0.36596(17) 0.0541(6) Uani 1 d . . .
N3 N 0.60594(16) 0.50796(11) 0.38424(18) 0.0366(5) Uani 1 d . . .
H24 H 0.6067 0.4881 0.4571 0.044 Uiso 1 calc . . R
N1 N 0.73623(19) 0.67347(11) 0.2617(2) 0.0428(6) Uani 1 d . . .
C11 C 0.7144(2) 0.50689(13) 0.3440(2) 0.0329(6) Uani 1 d . . .
H11 H 0.6963 0.5153 0.2510 0.040 Uiso 1 calc . . R
C9 C 0.7277(2) 0.64276(14) 0.3733(2) 0.0380(6) Uani 1 d . . .
C18 C 0.5040(2) 0.53654(14) 0.3205(2) 0.0376(6) Uani 1 d . . .
C8 C 0.7949(2) 0.57140(13) 0.4102(2) 0.0348(6) Uani 1 d . . .
C6 C 0.8970(2) 0.59840(14) 0.2339(2) 0.0377(6) Uani 1 d . . .
N2 N 0.8377(2) 0.55536(15) 0.6593(2) 0.0633(7) Uani 1 d . . .
C12 C 0.7741(2) 0.43312(14) 0.3690(2) 0.0379(6) Uani 1 d . . .
C1 C 0.8086(2) 0.64677(14) 0.1832(2) 0.0397(6) Uani 1 d . . .
C7 C 0.9124(2) 0.57482(15) 0.3714(2) 0.0403(7) Uani 1 d . . .
H7A H 0.9631 0.6087 0.4272 0.048 Uiso 1 calc . . R
H7B H 0.9486 0.5273 0.3828 0.048 Uiso 1 calc . . R
C10 C 0.8176(2) 0.56284(15) 0.5509(3) 0.0412(7) Uani 1 d . . .
C5 C 0.9702(2) 0.57595(15) 0.1574(3) 0.0463(7) Uani 1 d . . .
H5 H 1.0302 0.5437 0.1891 0.056 Uiso 1 calc . . R
O4 O 0.6206(3) 0.70138(14) 0.6713(3) 0.1169(12) Uani 1 d . . .
H4 H 0.6377 0.6822 0.6091 0.175 Uiso 1 calc . . GR
C2 C 0.7914(3) 0.67124(15) 0.0579(3) 0.0497(7) Uani 1 d . . .
H2 H 0.7307 0.7027 0.0246 0.060 Uiso 1 calc . . R
C17 C 0.7678(2) 0.39092(15) 0.4742(3) 0.0491(7) Uani 1 d . . .
H17 H 0.7278 0.4078 0.5333 0.059 Uiso 1 calc . . R
C4 C 0.9522(3) 0.60228(17) 0.0345(3) 0.0507(8) Uani 1 d . . .
C3 C 0.8646(3) 0.64886(16) -0.0180(3) 0.0536(8) Uani 1 d . . .
H3 H 0.8544 0.6651 -0.1022 0.064 Uiso 1 calc . . R
C13 C 0.8355(2) 0.40682(15) 0.2838(3) 0.0499(7) Uani 1 d . . .
H13 H 0.8407 0.4346 0.2129 0.060 Uiso 1 calc . . R
C16 C 0.8211(3) 0.32362(17) 0.4915(3) 0.0638(9) Uani 1 d . . .
H16 H 0.8159 0.2954 0.5619 0.077 Uiso 1 calc . . R
C19 C 0.4024(3) 0.5929(2) 0.1203(3) 0.0641(10) Uani 1 d . . .
C15 C 0.8815(3) 0.29813(17) 0.4059(4) 0.0699(10) Uani 1 d . . .
H15 H 0.9168 0.2528 0.4180 0.084 Uiso 1 calc . . R
C14 C 0.8892(3) 0.34002(18) 0.3024(4) 0.0683(10) Uani 1 d . . .
H14 H 0.9307 0.3234 0.2445 0.082 Uiso 1 calc . . R
C22 C 0.4463(3) 0.6152(2) 0.0035(3) 0.0909(13) Uani 1 d . . .
H22A H 0.5049 0.6517 0.0279 0.136 Uiso 1 calc . . GR
H22B H 0.3833 0.6343 -0.0612 0.136 Uiso 1 calc . . GR
H22C H 0.4782 0.5737 -0.0300 0.136 Uiso 1 calc . . GR
C20 C 0.3083(3) 0.5355(3) 0.0844(3) 0.1044(16) Uani 1 d . . .
H20A H 0.3372 0.4949 0.0452 0.157 Uiso 1 calc . . GR
H20B H 0.2426 0.5557 0.0250 0.157 Uiso 1 calc . . GR
H20C H 0.2857 0.5196 0.1604 0.157 Uiso 1 calc . . GR
C23 C 0.5543(4) 0.6560(2) 0.7207(4) 0.1109(16) Uani 1 d . . .
H23A H 0.5915 0.6096 0.7362 0.166 Uiso 1 calc . . GR
H23B H 0.4807 0.6506 0.6612 0.166 Uiso 1 calc . . GR
H23C H 0.5432 0.6755 0.8002 0.166 Uiso 1 calc . . GR
C21 C 0.3658(4) 0.6584(2) 0.1854(4) 0.1147(18) Uani 1 d . . .
H21A H 0.3297 0.6429 0.2522 0.172 Uiso 1 calc . . GR
H21B H 0.3120 0.6867 0.1235 0.172 Uiso 1 calc . . GR
H21C H 0.4325 0.6874 0.2220 0.172 Uiso 1 calc . . GR


_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
O2 C18 1.334(3) . ?
O2 C19 1.482(3) . ?
F1 C4 1.363(3) . ?
O1 C9 1.226(3) . ?
O3 C18 1.219(3) . ?
N3 H24 0.8600 . ?
N3 C11 1.453(3) . ?
N3 C18 1.352(3) . ?
N1 C9 1.347(3) . ?
N1 C1 1.424(3) . ?
C11 H11 0.9800 . ?
C11 C8 1.586(3) . ?
C11 C12 1.528(3) . ?
C9 C8 1.541(3) . ?
C8 C7 1.550(3) . ?
C8 C10 1.475(3) . ?
C6 C1 1.388(4) . ?
C6 C7 1.504(3) . ?
C6 C5 1.390(3) . ?
N2 C10 1.136(3) . ?
C12 C17 1.384(3) . ?
C12 C13 1.384(3) . ?
C1 C2 1.385(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C4 1.371(4) . ?
O4 H4 0.8200 . ?
O4 C23 1.340(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(3) . ?
C17 H17 0.9300 . ?
C17 C16 1.385(4) . ?
C4 C3 1.365(4) . ?
C3 H3 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.379(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.372(4) . ?
C19 C22 1.519(4) . ?
C19 C20 1.523(5) . ?
C19 C21 1.509(5) . ?
C15 H15 0.9300 . ?
C15 C14 1.371(4) . ?
C14 H14 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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
C18 O2 C19 119.36(19) . . ?
C11 N3 H24 116.2 . . ?
C18 N3 H24 116.2 . . ?
C18 N3 C11 127.6(2) . . ?
C9 N1 C1 124.0(2) . . ?
N3 C11 H11 107.5 . . ?
N3 C11 C8 110.06(18) . . ?
N3 C11 C12 111.64(19) . . ?
C8 C11 H11 107.5 . . ?
C12 C11 H11 107.5 . . ?
C12 C11 C8 112.40(19) . . ?
O1 C9 N1 121.8(2) . . ?
O1 C9 C8 121.8(2) . . ?
N1 C9 C8 116.3(2) . . ?
O2 C18 N3 112.3(2) . . ?
O3 C18 O2 125.2(2) . . ?
O3 C18 N3 122.5(2) . . ?
C9 C8 C11 107.59(19) . . ?
C9 C8 C7 110.0(2) . . ?
C7 C8 C11 113.52(19) . . ?
C10 C8 C11 108.8(2) . . ?
C10 C8 C9 108.3(2) . . ?
C10 C8 C7 108.5(2) . . ?
C1 C6 C7 118.4(2) . . ?
C1 C6 C5 118.9(2) . . ?
C5 C6 C7 122.7(2) . . ?
C17 C12 C11 122.1(2) . . ?
C13 C12 C11 119.5(2) . . ?
C13 C12 C17 118.5(3) . . ?
C6 C1 N1 119.9(2) . . ?
C2 C1 N1 119.1(2) . . ?
C2 C1 C6 120.9(2) . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C6 C7 C8 111.3(2) . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N2 C10 C8 178.2(3) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 C6 118.8(3) . . ?
C4 C5 H5 120.6 . . ?
C23 O4 H4 109.5 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C12 C17 H17 119.9 . . ?
C12 C17 C16 120.1(3) . . ?
C16 C17 H17 119.9 . . ?
F1 C4 C5 118.5(3) . . ?
F1 C4 C3 118.2(2) . . ?
C3 C4 C5 123.3(3) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 C2 118.0(3) . . ?
C4 C3 H3 121.0 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.1(3) . . ?
C14 C13 H13 119.5 . . ?
C17 C16 H16 119.6 . . ?
C15 C16 C17 120.8(3) . . ?
C15 C16 H16 119.6 . . ?
O2 C19 C22 101.7(2) . . ?
O2 C19 C20 109.7(3) . . ?
O2 C19 C21 109.8(3) . . ?
C22 C19 C20 110.8(3) . . ?
C21 C19 C22 110.8(3) . . ?
C21 C19 C20 113.4(3) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 C16 119.4(3) . . ?
C14 C15 H15 120.3 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 119.9 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.636
_oxdiff_exptl_absorpt_empirical_full_min 0.720
