# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_ib44_m
_audit_block_doi                 10.5517/cc14nc16
_database_code_depnum_ccdc_archive 'CCDC 1062247'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-10-07 downloaded from the CCDC.
;

_audit_creation_date             2015-04-27T12:26:49-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        18b
_chemical_formula_moiety         'C22 H26 F3 N2 O4'
_chemical_formula_sum            'C21 H29 F3 N2 O5'
_chemical_formula_weight         446.46
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7878(8)
_cell_length_b                   10.2150(8)
_cell_length_c                   12.0649(10)
_cell_angle_alpha                93.455(2)
_cell_angle_beta                 95.974(2)
_cell_angle_gamma                109.227(2)
_cell_volume                     1127.05(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5308
_cell_measurement_theta_min      4
_cell_measurement_theta_max      60
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_number            26050
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_full        30.03
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             6571
_reflns_number_gt                5430
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0908P)²+0.1490P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.023(4)
_refine_ls_number_reflns         6571
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1633
_refine_ls_wR_factor_gt          0.153
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.061

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
F1 F 1.12984(15) 1.22555(13) 0.72274(18) 0.1352(7) Uani 1 1 d . . .
O2 O 0.60046(11) 0.62066(9) 0.62488(8) 0.0563(2) Uani 1 1 d . . .
F3 F 1.09316(13) 1.06001(14) 0.59907(9) 0.0954(4) Uani 1 1 d . . .
O3 O 0.50116(12) 0.91624(9) 0.36740(8) 0.0580(3) Uani 1 1 d . . .
O4 O 0.42443(11) 0.70628(9) 0.26983(7) 0.0526(2) Uani 1 1 d . . .
O5 O 0.86800(13) 1.11989(11) 0.76484(11) 0.0730(3) Uani 1 1 d . . .
O1 O 0.05995(11) 0.59719(12) 0.86687(11) 0.0674(3) Uani 1 1 d . . .
N1 N 0.52274(11) 0.79202(9) 0.56431(7) 0.0405(2) Uani 1 1 d . . .
H1 H 0.5246 0.8763 0.5775 0.049 Uiso 1 1 calc R . .
N2 N 0.84880(11) 0.89572(10) 0.71244(8) 0.0447(2) Uani 1 1 d . . .
C18 C 0.2096(2) 0.7686(2) 0.4995(2) 0.0872(6) Uani 1 1 d . . .
H18A H 0.23 0.8321 0.4429 0.131 Uiso 1 1 calc R . .
H18B H 0.255 0.8176 0.5714 0.131 Uiso 1 1 calc R . .
H18C H 0.1059 0.7301 0.4998 0.131 Uiso 1 1 calc R . .
C15 C 0.43225(19) 0.77131(16) 0.16680(10) 0.0611(4) Uani 1 1 d . . .
H15A H 0.405 0.7009 0.1044 0.092 Uiso 1 1 calc R . .
H15B H 0.5302 0.8326 0.1651 0.092 Uiso 1 1 calc R . .
H15C H 0.3668 0.8237 0.1623 0.092 Uiso 1 1 calc R . .
C13 C 0.43463(12) 0.70722(11) 0.46418(8) 0.0401(2) Uani 1 1 d . . .
H13 H 0.467 0.6272 0.4509 0.048 Uiso 1 1 calc R . .
C10 C 0.74449(17) 0.67170(18) 0.86876(13) 0.0625(4) Uani 1 1 d . . .
H10A H 0.8471 0.7093 0.8638 0.094 Uiso 1 1 calc R . .
H10B H 0.6993 0.5952 0.8119 0.094 Uiso 1 1 calc R . .
H10C H 0.7301 0.6396 0.9412 0.094 Uiso 1 1 calc R . .
C12 C 0.60147(12) 0.74021(11) 0.63666(8) 0.0396(2) Uani 1 1 d . . .
C17 C 0.2386(2) 0.5479(2) 0.56190(14) 0.0751(5) Uani 1 1 d . . .
H17A H 0.277 0.4751 0.544 0.113 Uiso 1 1 calc R . .
H17B H 0.1352 0.5083 0.5625 0.113 Uiso 1 1 calc R . .
H17C H 0.2842 0.595 0.6344 0.113 Uiso 1 1 calc R . .
C14 C 0.45963(12) 0.79122(11) 0.36428(9) 0.0407(2) Uani 1 1 d . . .
C11 C 0.69498(12) 0.84455(11) 0.73523(9) 0.0397(2) Uani 1 1 d . . .
H11 H 0.6612 0.9248 0.7365 0.048 Uiso 1 1 calc R . .
C19 C 0.91341(16) 0.79746(15) 0.66347(13) 0.0597(3) Uani 1 1 d . . .
H19A H 0.8452 0.7043 0.6583 0.09 Uiso 1 1 calc R . .
H19B H 1.0013 0.8035 0.7102 0.09 Uiso 1 1 calc R . .
H19C H 0.9358 0.8208 0.59 0.09 Uiso 1 1 calc R . .
C6 C 0.28329(15) 0.54134(13) 0.86360(11) 0.0506(3) Uani 1 1 d . . .
H6 H 0.2343 0.4465 0.8645 0.061 Uiso 1 1 calc R . .
C4 C 0.51098(13) 0.73052(12) 0.85908(9) 0.0441(2) Uani 1 1 d . . .
C8 C 0.67550(14) 0.78536(13) 0.85161(9) 0.0471(3) Uani 1 1 d . . .
C2 C 0.28345(16) 0.77506(14) 0.86795(13) 0.0573(3) Uani 1 1 d . . .
H2 H 0.234 0.8386 0.8716 0.069 Uiso 1 1 calc R . .
C1 C 0.20763(14) 0.63387(13) 0.86646(10) 0.0488(3) Uani 1 1 d . . .
C9 C 0.75189(18) 0.90565(19) 0.94427(11) 0.0677(4) Uani 1 1 d . . .
H9A H 0.7117 0.979 0.9354 0.101 Uiso 1 1 calc R . .
H9B H 0.8546 0.9407 0.9389 0.101 Uiso 1 1 calc R . .
H9C H 0.737 0.8722 1.0162 0.101 Uiso 1 1 calc R . .
C20 C 0.91845(14) 1.03418(14) 0.72935(11) 0.0525(3) Uani 1 1 d . . .
C3 C 0.43175(15) 0.82177(13) 0.86403(12) 0.0542(3) Uani 1 1 d . . .
H3 H 0.4806 0.9169 0.8647 0.065 Uiso 1 1 calc R . .
C5 C 0.43304(15) 0.59017(13) 0.85936(11) 0.0497(3) Uani 1 1 d . . .
H5 H 0.4824 0.5265 0.8566 0.06 Uiso 1 1 calc R . .
C16 C 0.26952(14) 0.65136(16) 0.47443(10) 0.0555(3) Uani 1 1 d . . .
H16 H 0.2185 0.6012 0.4021 0.067 Uiso 1 1 calc R . .
C21 C 1.07767(17) 1.09051(17) 0.70388(14) 0.0660(4) Uani 1 1 d . . .
C7 C -0.02392(19) 0.45225(19) 0.84941(19) 0.0796(5) Uani 1 1 d . . .
H7A H -0.1252 0.4401 0.8513 0.119 Uiso 1 1 calc R . .
H7B H 0.0086 0.4048 0.9074 0.119 Uiso 1 1 calc R . .
H7C H -0.0116 0.4144 0.7779 0.119 Uiso 1 1 calc R . .
F2 F 1.16612(12) 1.04052(16) 0.76638(11) 0.1003(4) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
F1 C21 1.300(2) . ?
O2 C12 1.2176(13) . ?
F3 C21 1.320(2) . ?
O3 C14 1.2027(14) . ?
O4 C14 1.3313(13) . ?
O4 C15 1.4416(15) . ?
O5 C20 1.2154(17) . ?
O1 C1 1.3693(16) . ?
O1 C7 1.427(2) . ?
N1 C12 1.3491(13) . ?
N1 C13 1.4555(13) . ?
N2 C20 1.3447(16) . ?
N2 C19 1.4767(16) . ?
N2 C11 1.4834(15) . ?
C18 C16 1.526(3) . ?
C13 C14 1.5155(15) . ?
C13 C16 1.5476(17) . ?
C10 C8 1.5371(19) . ?
C12 C11 1.5383(14) . ?
C17 C16 1.521(2) . ?
C11 C8 1.5671(16) . ?
C6 C1 1.3804(18) . ?
C6 C5 1.3918(19) . ?
C4 C5 1.3850(17) . ?
C4 C3 1.3975(17) . ?
C4 C8 1.5353(17) . ?
C8 C9 1.5407(18) . ?
C2 C3 1.378(2) . ?
C2 C1 1.3858(19) . ?
C20 C21 1.544(2) . ?
C21 F2 1.334(2) . ?

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
C14 O4 C15 116.49(10) . . ?
C1 O1 C7 117.38(12) . . ?
C12 N1 C13 120.91(9) . . ?
C20 N2 C19 123.19(11) . . ?
C20 N2 C11 116.68(10) . . ?
C19 N2 C11 119.88(10) . . ?
N1 C13 C14 109.53(9) . . ?
N1 C13 C16 113.23(9) . . ?
C14 C13 C16 109.56(9) . . ?
O2 C12 N1 123.01(10) . . ?
O2 C12 C11 122.15(10) . . ?
N1 C12 C11 114.83(9) . . ?
O3 C14 O4 123.80(10) . . ?
O3 C14 C13 126.06(10) . . ?
O4 C14 C13 110.11(9) . . ?
N2 C11 C12 108.98(9) . . ?
N2 C11 C8 113.75(9) . . ?
C12 C11 C8 113.03(9) . . ?
C1 C6 C5 119.90(12) . . ?
C5 C4 C3 116.60(12) . . ?
C5 C4 C8 122.62(11) . . ?
C3 C4 C8 120.77(11) . . ?
C4 C8 C10 111.58(11) . . ?
C4 C8 C9 109.52(11) . . ?
C10 C8 C9 107.44(12) . . ?
C4 C8 C11 107.02(9) . . ?
C10 C8 C11 112.88(10) . . ?
C9 C8 C11 108.34(11) . . ?
C3 C2 C1 120.30(12) . . ?
O1 C1 C6 124.89(12) . . ?
O1 C1 C2 116.03(12) . . ?
C6 C1 C2 119.08(12) . . ?
O5 C20 N2 125.77(13) . . ?
O5 C20 C21 116.48(12) . . ?
N2 C20 C21 117.74(12) . . ?
C2 C3 C4 121.97(12) . . ?
C4 C5 C6 122.13(11) . . ?
C17 C16 C18 111.17(14) . . ?
C17 C16 C13 110.61(12) . . ?
C18 C16 C13 112.13(13) . . ?
F1 C21 F3 106.37(16) . . ?
F1 C21 F2 107.25(15) . . ?
F3 C21 F2 105.52(15) . . ?
F1 C21 C20 110.78(14) . . ?
F3 C21 C20 113.87(12) . . ?
F2 C21 C20 112.59(14) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
