# 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_tomk_jones2
_database_code_depnum_ccdc_archive 'CCDC 1064075'
_audit_update_record             
;
2015-05-08 deposited with the CCDC.
2015-10-08 downloaded from the CCDC.
;

#--------------------------------------------------------
#---------------   COMPOUND 9 ------------------------
#--------------------------------------------------------

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H27 N O'
_chemical_formula_weight         309.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 '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           trigonal
_symmetry_space_group_name_H-M   P-3


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'

_cell_length_a                   18.6953(4)
_cell_length_b                   18.6953(4)
_cell_length_c                   9.2303(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     2793.90(10)
_cell_formula_units_Z            6
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2965
_cell_measurement_theta_min      4.7250
_cell_measurement_theta_max      72.9270


_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.103
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    0.512
_exptl_absorpt_correction_T_min  0.82144
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         4.73
_diffrn_reflns_theta_max         73.12
_reflns_number_total             3634
_reflns_number_gt                3036
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       CrysalisPro
_computing_cell_refinement       CrysalisPro
_computing_data_reduction        CrysalisPro
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  SHELXL-97

_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 > 2σ(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)+(0.0765P)²+0.3499P] 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         3634
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1266
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
O1 O 0.89339(6) 0.05352(6) 0.96167(11) 0.0410(3) Uani 1 1 d . . .
N1 N 0.72839(7) 0.12146(7) 0.51261(12) 0.0318(3) Uani 1 1 d . . .
C1 C 0.75958(7) 0.10130(8) 0.64363(13) 0.0296(3) Uani 1 1 d . . .
H1 H 0.7210 0.0952 0.7238 0.036 Uiso 1 1 calc R . .
C2 C 0.76034(8) 0.01969(8) 0.63695(15) 0.0336(3) Uani 1 1 d . . .
H2A H 0.7038 -0.0262 0.6173 0.040 Uiso 1 1 calc R . .
H2B H 0.7964 0.0220 0.5564 0.040 Uiso 1 1 calc R . .
C3 C 0.79146(8) 0.00321(8) 0.77876(15) 0.0354(3) Uani 1 1 d . . .
H3A H 0.7936 -0.0484 0.7694 0.042 Uiso 1 1 calc R . .
H3B H 0.7520 -0.0048 0.8572 0.042 Uiso 1 1 calc R . .
C4 C 0.87715(8) 0.07390(8) 0.81981(14) 0.0310(3) Uani 1 1 d . . .
C5 C 0.87531(8) 0.15472(8) 0.82728(14) 0.0316(3) Uani 1 1 d . . .
H5A H 0.8389 0.1515 0.9079 0.038 Uiso 1 1 calc R . .
H5B H 0.9316 0.2008 0.8482 0.038 Uiso 1 1 calc R . .
C6 C 0.84443(8) 0.17291(8) 0.68645(15) 0.0322(3) Uani 1 1 d . . .
H6A H 0.8844 0.1829 0.6079 0.039 Uiso 1 1 calc R . .
H6B H 0.8409 0.2237 0.6986 0.039 Uiso 1 1 calc R . .
C7 C 0.94357(9) 0.08125(9) 0.71549(16) 0.0390(3) Uani 1 1 d . . .
H7A H 0.9975 0.1263 0.7467 0.058 Uiso 1 1 calc R . .
H7B H 0.9314 0.0928 0.6178 0.058 Uiso 1 1 calc R . .
H7C H 0.9446 0.0293 0.7148 0.058 Uiso 1 1 calc R . .
C8 C 0.77097(8) 0.12309(9) 0.37818(14) 0.0364(3) Uani 1 1 d . . .
H8A H 0.7481 0.0661 0.3408 0.044 Uiso 1 1 calc R . .
H8B H 0.8305 0.1456 0.3981 0.044 Uiso 1 1 calc R . .
C9 C 0.76044(8) 0.17581(10) 0.26549(16) 0.0393(3) Uani 1 1 d . . .
C10 C 0.78518(10) 0.25791(11) 0.29717(19) 0.0500(4) Uani 1 1 d . . .
H10 H 0.8095 0.2804 0.3885 0.060 Uiso 1 1 calc R . .
C11 C 0.77462(12) 0.30692(13) 0.1969(2) 0.0603(5) Uani 1 1 d . . .
H11 H 0.7922 0.3630 0.2190 0.072 Uiso 1 1 calc R . .
C12 C 0.73846(12) 0.27427(14) 0.0647(2) 0.0600(5) Uani 1 1 d . . .
H12 H 0.7308 0.3078 -0.0037 0.072 Uiso 1 1 calc R . .
C13 C 0.71338(11) 0.19296(14) 0.03151(18) 0.0571(5) Uani 1 1 d . . .
H13 H 0.6886 0.1707 -0.0596 0.068 Uiso 1 1 calc R . .
C14 C 0.72460(10) 0.14369(11) 0.13226(16) 0.0454(4) Uani 1 1 d . . .
H14 H 0.7076 0.0879 0.1093 0.054 Uiso 1 1 calc R . .
C15 C 0.63903(8) 0.06827(9) 0.49272(15) 0.0359(3) Uani 1 1 d . . .
H15A H 0.6254 0.0098 0.4914 0.043 Uiso 1 1 calc R . .
H15B H 0.6231 0.0806 0.3978 0.043 Uiso 1 1 calc R . .
C16 C 0.58972(8) 0.07961(9) 0.61004(14) 0.0346(3) Uani 1 1 d . . .
C17 C 0.58904(9) 0.15347(10) 0.62015(16) 0.0422(3) Uani 1 1 d . . .
H17 H 0.6211 0.1971 0.5546 0.051 Uiso 1 1 calc R . .
C18 C 0.54204(11) 0.16389(12) 0.72494(19) 0.0518(4) Uani 1 1 d . . .
H18 H 0.5418 0.2145 0.7305 0.062 Uiso 1 1 calc R . .
C19 C 0.49550(10) 0.10114(13) 0.82128(18) 0.0539(4) Uani 1 1 d . . .
H19 H 0.4632 0.1084 0.8928 0.065 Uiso 1 1 calc R . .
C20 C 0.49615(9) 0.02795(12) 0.81325(17) 0.0512(4) Uani 1 1 d . . .
H20 H 0.4643 -0.0153 0.8796 0.061 Uiso 1 1 calc R . .
C21 C 0.54334(9) 0.01726(10) 0.70811(15) 0.0416(3) Uani 1 1 d . . .
H21 H 0.5438 -0.0333 0.7035 0.050 Uiso 1 1 calc R . .
H1H H 0.9447(12) 0.0887(12) 0.983(2) 0.047(5) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O1 C4 1.4380(15) . ?
O1 H1H 0.87(2) . ?
N1 C8 1.4663(16) . ?
N1 C15 1.4671(17) . ?
N1 C1 1.4713(16) . ?
C1 C6 1.5300(17) . ?
C1 C2 1.5339(17) . ?
C1 H1 1.0000 . ?
C2 C3 1.5252(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5295(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C7 1.5223(18) . ?
C4 C5 1.5300(17) . ?
C5 C6 1.5281(17) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.5120(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.385(2) . ?
C9 C10 1.395(2) . ?
C10 C11 1.384(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.396(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.5044(19) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C21 1.385(2) . ?
C16 C17 1.390(2) . ?
C17 C18 1.385(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.376(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.392(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

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
C4 O1 H1H 107.6(12) . . ?
C8 N1 C15 109.30(10) . . ?
C8 N1 C1 114.85(10) . . ?
C15 N1 C1 113.08(10) . . ?
N1 C1 C6 111.00(10) . . ?
N1 C1 C2 115.07(10) . . ?
C6 C1 C2 111.08(10) . . ?
N1 C1 H1 106.4 . . ?
C6 C1 H1 106.4 . . ?
C2 C1 H1 106.4 . . ?
C3 C2 C1 111.14(11) . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C2 C3 C4 112.25(11) . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
O1 C4 C7 109.21(11) . . ?
O1 C4 C3 105.38(10) . . ?
C7 C4 C3 112.08(11) . . ?
O1 C4 C5 109.43(10) . . ?
C7 C4 C5 111.07(11) . . ?
C3 C4 C5 109.48(10) . . ?
C6 C5 C4 112.27(10) . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C5 C6 C1 111.52(10) . . ?
C5 C6 H6A 109.3 . . ?
C1 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C1 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C9 110.45(11) . . ?
N1 C8 H8A 109.6 . . ?
C9 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C14 C9 C10 119.04(15) . . ?
C14 C9 C8 121.36(14) . . ?
C10 C9 C8 119.57(14) . . ?
C11 C10 C9 120.63(17) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 119.93(19) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.25(16) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C14 119.83(17) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C9 C14 C13 120.32(17) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
N1 C15 C16 112.63(11) . . ?
N1 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
N1 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C21 C16 C17 118.63(13) . . ?
C21 C16 C15 121.44(13) . . ?
C17 C16 C15 119.93(13) . . ?
C18 C17 C16 120.55(15) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 120.35(16) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 119.70(15) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C21 120.11(16) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C16 C21 C20 120.65(16) . . ?
C16 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C6 71.79(14) . . . . ?
C15 N1 C1 C6 -161.81(11) . . . . ?
C8 N1 C1 C2 -55.43(15) . . . . ?
C15 N1 C1 C2 70.96(14) . . . . ?
N1 C1 C2 C3 -178.52(10) . . . . ?
C6 C1 C2 C3 54.29(14) . . . . ?
C1 C2 C3 C4 -56.27(15) . . . . ?
C2 C3 C4 O1 173.72(11) . . . . ?
C2 C3 C4 C7 -67.59(14) . . . . ?
C2 C3 C4 C5 56.13(15) . . . . ?
O1 C4 C5 C6 -170.55(10) . . . . ?
C7 C4 C5 C6 68.79(14) . . . . ?
C3 C4 C5 C6 -55.52(14) . . . . ?
C4 C5 C6 C1 55.35(14) . . . . ?
N1 C1 C6 C5 176.72(10) . . . . ?
C2 C1 C6 C5 -53.90(14) . . . . ?
C15 N1 C8 C9 74.59(14) . . . . ?
C1 N1 C8 C9 -157.09(11) . . . . ?
N1 C8 C9 C14 -121.70(14) . . . . ?
N1 C8 C9 C10 56.56(17) . . . . ?
C14 C9 C10 C11 -0.4(2) . . . . ?
C8 C9 C10 C11 -178.68(15) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C10 C9 C14 C13 -0.1(2) . . . . ?
C8 C9 C14 C13 178.16(13) . . . . ?
C12 C13 C14 C9 0.3(2) . . . . ?
C8 N1 C15 C16 -165.56(11) . . . . ?
C1 N1 C15 C16 65.14(14) . . . . ?
N1 C15 C16 C21 -113.13(14) . . . . ?
N1 C15 C16 C17 67.90(16) . . . . ?
C21 C16 C17 C18 -0.9(2) . . . . ?
C15 C16 C17 C18 178.12(13) . . . . ?
C16 C17 C18 C19 0.3(2) . . . . ?
C17 C18 C19 C20 0.2(2) . . . . ?
C18 C19 C20 C21 -0.2(2) . . . . ?
C17 C16 C21 C20 0.9(2) . . . . ?
C15 C16 C21 C20 -178.08(12) . . . . ?
C19 C20 C21 C16 -0.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        70.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_tomk_djones1
_database_code_depnum_ccdc_archive 'CCDC 1064076'
_audit_update_record             
;
2015-05-08 deposited with the CCDC.
2015-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H27 N O'
_chemical_formula_weight         309.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
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   Ccc2

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

_cell_length_a                   23.0565(17)
_cell_length_b                   27.3947(17)
_cell_length_c                   11.6346(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     7348.7(9)
_cell_formula_units_Z            16
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    5624
_cell_measurement_theta_min      2.9642
_cell_measurement_theta_max      28.8476


_exptl_crystal_description       'plate like fragment'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2688
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_min  0.91453
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
;
Mounted with oil in a cryoloop.
;

_diffrn_ambient_temperature      123(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  'Oxford Diffraction Xcalibur E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24970
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_sigmaI/netI    0.0653
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         27.00
_reflns_number_total             7436
_reflns_number_gt                5609
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       CrysalisPro
_computing_cell_refinement       CrysalisPro
_computing_data_reduction        CrysalisPro
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  SHELXL-97

_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 > 2σ(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)+(0.0314P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.3(12)
_refine_ls_number_reflns         7436
_refine_ls_number_parameters     429
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
O1 O 0.72080(7) 0.20693(6) 0.64554(14) 0.0399(4) Uani 1 1 d D . .
H1A H 0.716(2) 0.2083(17) 0.7200(11) 0.048 Uiso 0.50 1 d PD A 1
H1B H 0.736(2) 0.2361(8) 0.635(4) 0.048 Uiso 0.50 1 d PD B 2
O2 O 0.73480(6) 0.20041(5) -0.11882(13) 0.0315(4) Uani 1 1 d D . .
H2A H 0.7490(17) 0.2295(7) -0.108(3) 0.038 Uiso 0.50 1 d PD C 1
H2B H 0.7352(18) 0.1941(16) -0.1925(12) 0.038 Uiso 0.50 1 d PD D 2
N1 N 0.74884(7) 0.06948(6) 0.42172(16) 0.0302(4) Uani 1 1 d . . .
N2 N 0.92213(7) 0.24247(5) 0.02968(15) 0.0260(4) Uani 1 1 d . . .
C1 C 0.70886(9) 0.10891(7) 0.45393(19) 0.0313(5) Uani 1 1 d . . .
H1 H 0.6715 0.1025 0.4129 0.038 Uiso 1 1 calc R . .
C2 C 0.69586(9) 0.10640(8) 0.58174(19) 0.0327(5) Uani 1 1 d . . .
H2C H 0.7320 0.1121 0.6257 0.039 Uiso 1 1 calc R . .
H2D H 0.6814 0.0734 0.6012 0.039 Uiso 1 1 calc R . .
C3 C 0.65072(9) 0.14431(8) 0.6162(2) 0.0382(6) Uani 1 1 d . . .
H3A H 0.6134 0.1364 0.5784 0.046 Uiso 1 1 calc R . .
H3B H 0.6446 0.1428 0.7003 0.046 Uiso 1 1 calc R . .
C4 C 0.66865(10) 0.19572(8) 0.5833(2) 0.0372(6) Uani 1 1 d . . .
C5 C 0.68300(11) 0.19830(8) 0.4556(2) 0.0415(6) Uani 1 1 d . . .
H5A H 0.6977 0.2313 0.4372 0.050 Uiso 1 1 calc R . .
H5B H 0.6471 0.1930 0.4106 0.050 Uiso 1 1 calc R . .
C6 C 0.72826(10) 0.16043(7) 0.4197(2) 0.0374(6) Uani 1 1 d . . .
H6A H 0.7658 0.1680 0.4571 0.045 Uiso 1 1 calc R . .
H6B H 0.7340 0.1619 0.3354 0.045 Uiso 1 1 calc R . .
C7 C 0.62144(11) 0.23237(9) 0.6125(3) 0.0599(8) Uani 1 1 d . . .
H7A H 0.6118 0.2299 0.6943 0.090 Uiso 1 1 calc R . .
H7B H 0.5868 0.2254 0.5665 0.090 Uiso 1 1 calc R . .
H7C H 0.6352 0.2654 0.5955 0.090 Uiso 1 1 calc R . .
C8 C 0.80960(9) 0.07960(8) 0.4491(2) 0.0349(5) Uani 1 1 d . . .
H8A H 0.8115 0.1004 0.5187 0.042 Uiso 1 1 calc R . .
H8B H 0.8274 0.0980 0.3849 0.042 Uiso 1 1 calc R . .
C9 C 0.84393(9) 0.03328(8) 0.4698(2) 0.0332(5) Uani 1 1 d . . .
C10 C 0.82797(10) 0.00198(9) 0.5572(2) 0.0416(6) Uani 1 1 d . . .
H10 H 0.7940 0.0087 0.6007 0.050 Uiso 1 1 calc R . .
C11 C 0.86057(11) -0.03898(8) 0.5826(2) 0.0472(7) Uani 1 1 d . . .
H11 H 0.8488 -0.0602 0.6430 0.057 Uiso 1 1 calc R . .
C12 C 0.90967(10) -0.04909(9) 0.5212(3) 0.0519(7) Uani 1 1 d . . .
H12 H 0.9328 -0.0767 0.5396 0.062 Uiso 1 1 calc R . .
C13 C 0.92500(10) -0.01896(9) 0.4329(3) 0.0565(8) Uani 1 1 d . . .
H13 H 0.9584 -0.0263 0.3883 0.068 Uiso 1 1 calc R . .
C14 C 0.89275(10) 0.02208(8) 0.4075(2) 0.0449(6) Uani 1 1 d . . .
H14 H 0.9044 0.0428 0.3462 0.054 Uiso 1 1 calc R . .
C15 C 0.74266(9) 0.05391(8) 0.30223(19) 0.0340(5) Uani 1 1 d . . .
H15A H 0.7746 0.0312 0.2829 0.041 Uiso 1 1 calc R . .
H15B H 0.7461 0.0827 0.2514 0.041 Uiso 1 1 calc R . .
C16 C 0.68526(9) 0.02903(7) 0.27971(19) 0.0256(5) Uani 1 1 d . . .
C17 C 0.66357(9) -0.00428(8) 0.35728(19) 0.0322(5) Uani 1 1 d . . .
H17 H 0.6838 -0.0100 0.4272 0.039 Uiso 1 1 calc R . .
C18 C 0.61315(10) -0.02934(8) 0.3351(2) 0.0368(6) Uani 1 1 d . . .
H18 H 0.5993 -0.0526 0.3890 0.044 Uiso 1 1 calc R . .
C19 C 0.58259(10) -0.02095(8) 0.2356(2) 0.0355(6) Uani 1 1 d . . .
H19 H 0.5474 -0.0380 0.2211 0.043 Uiso 1 1 calc R . .
C20 C 0.60341(10) 0.01221(8) 0.1577(2) 0.0408(6) Uani 1 1 d . . .
H20 H 0.5829 0.0180 0.0882 0.049 Uiso 1 1 calc R . .
C21 C 0.65453(10) 0.03731(8) 0.18027(19) 0.0360(6) Uani 1 1 d . . .
H21 H 0.6685 0.0605 0.1262 0.043 Uiso 1 1 calc R . .
C22 C 0.87764(8) 0.20465(7) 0.01035(18) 0.0264(5) Uani 1 1 d . . .
H22 H 0.8946 0.1731 0.0377 0.032 Uiso 1 1 calc R . .
C23 C 0.82086(9) 0.21171(7) 0.07607(18) 0.0289(5) Uani 1 1 d . . .
H23A H 0.8024 0.2427 0.0518 0.035 Uiso 1 1 calc R . .
H23B H 0.8291 0.2138 0.1594 0.035 Uiso 1 1 calc R . .
C24 C 0.77939(9) 0.16915(7) 0.05318(18) 0.0320(5) Uani 1 1 d . . .
H24A H 0.7958 0.1392 0.0879 0.038 Uiso 1 1 calc R . .
H24B H 0.7420 0.1759 0.0917 0.038 Uiso 1 1 calc R . .
C25 C 0.76815(9) 0.15984(7) -0.07429(19) 0.0282(5) Uani 1 1 d . . .
C26 C 0.82510(9) 0.15545(7) -0.13895(19) 0.0296(5) Uani 1 1 d . . .
H26A H 0.8170 0.1534 -0.2224 0.036 Uiso 1 1 calc R . .
H26B H 0.8447 0.1249 -0.1156 0.036 Uiso 1 1 calc R . .
C27 C 0.86566(8) 0.19850(7) -0.11668(18) 0.0266(5) Uani 1 1 d . . .
H27A H 0.9027 0.1931 -0.1578 0.032 Uiso 1 1 calc R . .
H27B H 0.8479 0.2287 -0.1471 0.032 Uiso 1 1 calc R . .
C28 C 0.73129(10) 0.11425(7) -0.0891(2) 0.0384(6) Uani 1 1 d . . .
H28A H 0.6944 0.1185 -0.0484 0.058 Uiso 1 1 calc R . .
H28B H 0.7520 0.0860 -0.0575 0.058 Uiso 1 1 calc R . .
H28C H 0.7237 0.1089 -0.1710 0.058 Uiso 1 1 calc R . .
C29 C 0.90218(9) 0.29278(7) 0.0116(2) 0.0295(5) Uani 1 1 d . . .
H29A H 0.8854 0.3054 0.0840 0.035 Uiso 1 1 calc R . .
H29B H 0.8712 0.2928 -0.0473 0.035 Uiso 1 1 calc R . .
C30 C 0.95045(9) 0.32629(7) -0.02656(18) 0.0274(5) Uani 1 1 d . . .
C31 C 0.95901(9) 0.37157(7) 0.0235(2) 0.0313(5) Uani 1 1 d . . .
H31 H 0.9358 0.3810 0.0873 0.038 Uiso 1 1 calc R . .
C32 C 1.00065(10) 0.40331(7) -0.0177(2) 0.0364(6) Uani 1 1 d . . .
H32 H 1.0057 0.4342 0.0179 0.044 Uiso 1 1 calc R . .
C33 C 1.03462(10) 0.39064(8) -0.1091(2) 0.0357(6) Uani 1 1 d . . .
H33 H 1.0626 0.4128 -0.1386 0.043 Uiso 1 1 calc R . .
C34 C 1.02750(11) 0.34526(8) -0.1578(2) 0.0425(6) Uani 1 1 d . . .
H34 H 1.0515 0.3357 -0.2202 0.051 Uiso 1 1 calc R . .
C35 C 0.98598(10) 0.31344(8) -0.11707(19) 0.0390(6) Uani 1 1 d . . .
H35 H 0.9818 0.2823 -0.1518 0.047 Uiso 1 1 calc R . .
C36 C 0.95079(9) 0.23823(7) 0.14071(19) 0.0284(5) Uani 1 1 d . . .
H36A H 0.9214 0.2414 0.2023 0.034 Uiso 1 1 calc R . .
H36B H 0.9787 0.2654 0.1493 0.034 Uiso 1 1 calc R . .
C37 C 0.98247(9) 0.19048(7) 0.15552(19) 0.0261(5) Uani 1 1 d . . .
C38 C 0.97507(10) 0.16209(8) 0.2520(2) 0.0356(6) Uani 1 1 d . . .
H38 H 0.9484 0.1721 0.3096 0.043 Uiso 1 1 calc R . .
C39 C 1.00597(11) 0.11921(8) 0.2664(2) 0.0447(6) Uani 1 1 d . . .
H39 H 1.0007 0.1003 0.3341 0.054 Uiso 1 1 calc R . .
C40 C 1.04396(10) 0.10387(8) 0.1837(2) 0.0429(6) Uani 1 1 d . . .
H40 H 1.0652 0.0744 0.1936 0.051 Uiso 1 1 calc R . .
C41 C 1.05117(10) 0.13153(8) 0.0859(2) 0.0401(6) Uani 1 1 d . . .
H41 H 1.0772 0.1210 0.0278 0.048 Uiso 1 1 calc R . .
C42 C 1.02062(9) 0.17469(8) 0.0719(2) 0.0328(5) Uani 1 1 d . . .
H42 H 1.0260 0.1936 0.0042 0.039 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O1 C4 1.437(3) . ?
O1 H1A 0.875(10) . ?
O1 H1B 0.876(10) . ?
O2 C25 1.448(2) . ?
O2 H2A 0.870(10) . ?
O2 H2B 0.874(10) . ?
N1 C15 1.461(3) . ?
N1 C8 1.463(3) . ?
N1 C1 1.469(3) . ?
N2 C36 1.456(3) . ?
N2 C29 1.468(2) . ?
N2 C22 1.475(2) . ?
C1 C2 1.519(3) . ?
C1 C6 1.533(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.524(3) . ?
C2 H2C 0.9900 . ?
C2 H2D 0.9900 . ?
C3 C4 1.517(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C7 1.519(3) . ?
C4 C5 1.524(3) . ?
C5 C6 1.530(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.515(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.373(3) . ?
C9 C10 1.381(3) . ?
C10 C11 1.382(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.367(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.364(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.511(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C21 1.376(3) . ?
C16 C17 1.377(3) . ?
C17 C18 1.374(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.374(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.370(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.390(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C27 1.513(3) . ?
C22 C23 1.528(3) . ?
C22 H22 1.0000 . ?
C23 C24 1.531(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.527(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.518(3) . ?
C25 C28 1.521(3) . ?
C26 C27 1.527(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.509(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C35 1.380(3) . ?
C30 C31 1.384(3) . ?
C31 C32 1.381(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.366(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.376(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.378(3) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 C37 1.508(3) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.376(3) . ?
C37 C42 1.381(3) . ?
C38 C39 1.384(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.367(3) . ?
C39 H39 0.9500 . ?
C40 C41 1.377(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.386(3) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?

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
C4 O1 H1A 113(3) . . ?
C4 O1 H1B 117(3) . . ?
H1A O1 H1B 98(4) . . ?
C25 O2 H2A 117(3) . . ?
C25 O2 H2B 101(3) . . ?
H2A O2 H2B 109(4) . . ?
C15 N1 C8 110.86(17) . . ?
C15 N1 C1 113.34(17) . . ?
C8 N1 C1 113.95(16) . . ?
C36 N2 C29 110.16(16) . . ?
C36 N2 C22 113.26(16) . . ?
C29 N2 C22 114.81(15) . . ?
N1 C1 C2 109.90(17) . . ?
N1 C1 C6 115.32(17) . . ?
C2 C1 C6 110.72(18) . . ?
N1 C1 H1 106.8 . . ?
C2 C1 H1 106.8 . . ?
C6 C1 H1 106.8 . . ?
C1 C2 C3 111.19(19) . . ?
C1 C2 H2C 109.4 . . ?
C3 C2 H2C 109.4 . . ?
C1 C2 H2D 109.4 . . ?
C3 C2 H2D 109.4 . . ?
H2C C2 H2D 108.0 . . ?
C4 C3 C2 112.35(18) . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
O1 C4 C3 107.43(18) . . ?
O1 C4 C7 110.23(19) . . ?
C3 C4 C7 111.2(2) . . ?
O1 C4 C5 107.5(2) . . ?
C3 C4 C5 110.37(19) . . ?
C7 C4 C5 110.0(2) . . ?
C4 C5 C6 112.50(19) . . ?
C4 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C5 C6 C1 110.76(18) . . ?
C5 C6 H6A 109.5 . . ?
C1 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C9 112.09(17) . . ?
N1 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C14 C9 C10 117.9(2) . . ?
C14 C9 C8 122.1(2) . . ?
C10 C9 C8 119.9(2) . . ?
C9 C10 C11 121.1(2) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 119.1(2) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C12 C13 C14 121.0(2) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C9 C14 C13 120.7(2) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
N1 C15 C16 112.46(18) . . ?
N1 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
N1 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C21 C16 C17 118.25(19) . . ?
C21 C16 C15 121.5(2) . . ?
C17 C16 C15 120.20(19) . . ?
C18 C17 C16 121.0(2) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 119.2(2) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C19 C20 C21 120.0(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C20 120.9(2) . . ?
C16 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
N2 C22 C27 110.74(16) . . ?
N2 C22 C23 115.49(16) . . ?
C27 C22 C23 110.27(17) . . ?
N2 C22 H22 106.6 . . ?
C27 C22 H22 106.6 . . ?
C23 C22 H22 106.6 . . ?
C22 C23 C24 110.58(16) . . ?
C22 C23 H23A 109.5 . . ?
C24 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 108.1 . . ?
C25 C24 C23 113.71(17) . . ?
C25 C24 H24A 108.8 . . ?
C23 C24 H24A 108.8 . . ?
C25 C24 H24B 108.8 . . ?
C23 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
O2 C25 C26 110.06(16) . . ?
O2 C25 C28 107.05(16) . . ?
C26 C25 C28 111.24(17) . . ?
O2 C25 C24 108.03(17) . . ?
C26 C25 C24 110.35(17) . . ?
C28 C25 C24 110.01(17) . . ?
C25 C26 C27 112.61(17) . . ?
C25 C26 H26A 109.1 . . ?
C27 C26 H26A 109.1 . . ?
C25 C26 H26B 109.1 . . ?
C27 C26 H26B 109.1 . . ?
H26A C26 H26B 107.8 . . ?
C22 C27 C26 111.32(17) . . ?
C22 C27 H27A 109.4 . . ?
C26 C27 H27A 109.4 . . ?
C22 C27 H27B 109.4 . . ?
C26 C27 H27B 109.4 . . ?
H27A C27 H27B 108.0 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N2 C29 C30 112.47(16) . . ?
N2 C29 H29A 109.1 . . ?
C30 C29 H29A 109.1 . . ?
N2 C29 H29B 109.1 . . ?
C30 C29 H29B 109.1 . . ?
H29A C29 H29B 107.8 . . ?
C35 C30 C31 117.7(2) . . ?
C35 C30 C29 120.46(19) . . ?
C31 C30 C29 121.8(2) . . ?
C32 C31 C30 121.1(2) . . ?
C32 C31 H31 119.4 . . ?
C30 C31 H31 119.4 . . ?
C33 C32 C31 120.6(2) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C32 C33 C34 118.8(2) . . ?
C32 C33 H33 120.6 . . ?
C34 C33 H33 120.6 . . ?
C33 C34 C35 120.9(2) . . ?
C33 C34 H34 119.6 . . ?
C35 C34 H34 119.6 . . ?
C34 C35 C30 120.9(2) . . ?
C34 C35 H35 119.6 . . ?
C30 C35 H35 119.6 . . ?
N2 C36 C37 113.00(16) . . ?
N2 C36 H36A 109.0 . . ?
C37 C36 H36A 109.0 . . ?
N2 C36 H36B 109.0 . . ?
C37 C36 H36B 109.0 . . ?
H36A C36 H36B 107.8 . . ?
C38 C37 C42 118.47(19) . . ?
C38 C37 C36 121.56(19) . . ?
C42 C37 C36 119.97(19) . . ?
C37 C38 C39 121.0(2) . . ?
C37 C38 H38 119.5 . . ?
C39 C38 H38 119.5 . . ?
C40 C39 C38 120.4(2) . . ?
C40 C39 H39 119.8 . . ?
C38 C39 H39 119.8 . . ?
C39 C40 C41 119.3(2) . . ?
C39 C40 H40 120.3 . . ?
C41 C40 H40 120.3 . . ?
C40 C41 C42 120.4(2) . . ?
C40 C41 H41 119.8 . . ?
C42 C41 H41 119.8 . . ?
C37 C42 C41 120.5(2) . . ?
C37 C42 H42 119.7 . . ?
C41 C42 H42 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N1 C1 C2 152.29(18) . . . . ?
C8 N1 C1 C2 -79.7(2) . . . . ?
C15 N1 C1 C6 -81.7(2) . . . . ?
C8 N1 C1 C6 46.3(3) . . . . ?
N1 C1 C2 C3 -175.44(16) . . . . ?
C6 C1 C2 C3 56.0(2) . . . . ?
C1 C2 C3 C4 -56.2(2) . . . . ?
C2 C3 C4 O1 -62.5(2) . . . . ?
C2 C3 C4 C7 176.78(19) . . . . ?
C2 C3 C4 C5 54.3(3) . . . . ?
O1 C4 C5 C6 62.8(2) . . . . ?
C3 C4 C5 C6 -54.1(3) . . . . ?
C7 C4 C5 C6 -177.2(2) . . . . ?
C4 C5 C6 C1 55.0(3) . . . . ?
N1 C1 C6 C5 179.04(18) . . . . ?
C2 C1 C6 C5 -55.4(2) . . . . ?
C15 N1 C8 C9 -78.2(2) . . . . ?
C1 N1 C8 C9 152.49(19) . . . . ?
N1 C8 C9 C14 123.0(2) . . . . ?
N1 C8 C9 C10 -60.2(3) . . . . ?
C14 C9 C10 C11 1.0(3) . . . . ?
C8 C9 C10 C11 -176.0(2) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C10 C11 C12 C13 -1.7(4) . . . . ?
C11 C12 C13 C14 1.9(4) . . . . ?
C10 C9 C14 C13 -0.8(3) . . . . ?
C8 C9 C14 C13 176.1(2) . . . . ?
C12 C13 C14 C9 -0.7(4) . . . . ?
C8 N1 C15 C16 162.91(17) . . . . ?
C1 N1 C15 C16 -67.5(2) . . . . ?
N1 C15 C16 C21 139.9(2) . . . . ?
N1 C15 C16 C17 -42.7(3) . . . . ?
C21 C16 C17 C18 1.2(3) . . . . ?
C15 C16 C17 C18 -176.21(19) . . . . ?
C16 C17 C18 C19 -1.3(3) . . . . ?
C17 C18 C19 C20 1.0(3) . . . . ?
C18 C19 C20 C21 -0.7(3) . . . . ?
C17 C16 C21 C20 -1.0(3) . . . . ?
C15 C16 C21 C20 176.4(2) . . . . ?
C19 C20 C21 C16 0.7(3) . . . . ?
C36 N2 C22 C27 -158.79(16) . . . . ?
C29 N2 C22 C27 73.5(2) . . . . ?
C36 N2 C22 C23 75.0(2) . . . . ?
C29 N2 C22 C23 -52.8(2) . . . . ?
N2 C22 C23 C24 -177.49(17) . . . . ?
C27 C22 C23 C24 56.0(2) . . . . ?
C22 C23 C24 C25 -54.1(2) . . . . ?
C23 C24 C25 O2 -68.8(2) . . . . ?
C23 C24 C25 C26 51.6(2) . . . . ?
C23 C24 C25 C28 174.70(17) . . . . ?
O2 C25 C26 C27 67.0(2) . . . . ?
C28 C25 C26 C27 -174.52(18) . . . . ?
C24 C25 C26 C27 -52.1(2) . . . . ?
N2 C22 C27 C26 173.29(15) . . . . ?
C23 C22 C27 C26 -57.6(2) . . . . ?
C25 C26 C27 C22 56.5(2) . . . . ?
C36 N2 C29 C30 79.6(2) . . . . ?
C22 N2 C29 C30 -151.14(18) . . . . ?
N2 C29 C30 C35 50.2(3) . . . . ?
N2 C29 C30 C31 -132.9(2) . . . . ?
C35 C30 C31 C32 1.7(3) . . . . ?
C29 C30 C31 C32 -175.3(2) . . . . ?
C30 C31 C32 C33 -0.1(3) . . . . ?
C31 C32 C33 C34 -1.5(3) . . . . ?
C32 C33 C34 C35 1.5(3) . . . . ?
C33 C34 C35 C30 0.0(4) . . . . ?
C31 C30 C35 C34 -1.6(3) . . . . ?
C29 C30 C35 C34 175.4(2) . . . . ?
C29 N2 C36 C37 -168.82(17) . . . . ?
C22 N2 C36 C37 61.1(2) . . . . ?
N2 C36 C37 C38 -130.4(2) . . . . ?
N2 C36 C37 C42 50.6(2) . . . . ?
C42 C37 C38 C39 1.4(3) . . . . ?
C36 C37 C38 C39 -177.7(2) . . . . ?
C37 C38 C39 C40 -1.0(4) . . . . ?
C38 C39 C40 C41 0.0(4) . . . . ?
C39 C40 C41 C42 0.6(3) . . . . ?
C38 C37 C42 C41 -0.8(3) . . . . ?
C36 C37 C42 C41 178.25(19) . . . . ?
C40 C41 C42 C37 -0.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_tom_jones_7
_database_code_depnum_ccdc_archive 'CCDC 1064077'
_audit_update_record             
;
2015-05-08 deposited with the CCDC.
2015-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H35 N O3'
_chemical_formula_weight         373.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 '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           monoclinic
_symmetry_space_group_name_H-M   P21/n

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                   17.524(2)
_cell_length_b                   6.4455(6)
_cell_length_c                   19.9254(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.422(9)
_cell_angle_gamma                90.00
_cell_volume                     2220.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    1195
_cell_measurement_theta_min      3.6970
_cell_measurement_theta_max      71.2960


_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.572
_exptl_absorpt_correction_T_min  0.35073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7857
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_sigmaI/netI    0.0796
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.67
_diffrn_reflns_theta_max         65.00
_reflns_number_total             3772
_reflns_number_gt                2163
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       CrysalisPro
_computing_cell_refinement       CrysalisPro
_computing_data_reduction        CrysalisPro
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  SHELXL-97


_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 > 2σ(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)+(0.0911P)²+0.5843P] 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         3772
_refine_ls_number_parameters     256
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1198
_refine_ls_R_factor_gt           0.0759
_refine_ls_wR_factor_ref         0.2340
_refine_ls_wR_factor_gt          0.1942
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.002
_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
O1 O 0.79389(15) -0.3581(4) 0.60393(14) 0.0525(7) Uani 1 1 d D . .
H1H H 0.8313(16) -0.267(5) 0.604(2) 0.063 Uiso 1 1 d D . .
O2 O 0.8488(2) -0.7026(5) 0.55279(17) 0.0750(10) Uani 1 1 d D . .
H2H H 0.826(2) -0.614(6) 0.576(2) 0.090 Uiso 1 1 d D . .
O3 O 0.90402(18) -1.0557(5) 0.61209(17) 0.0700(9) Uani 1 1 d D . .
H3H H 0.888(3) -0.942(4) 0.590(2) 0.084 Uiso 1 1 d D . .
N1 N 0.63532(17) -0.1874(4) 0.42389(15) 0.0437(7) Uani 1 1 d . . .
C1 C 0.7217(2) -0.2680(6) 0.61476(19) 0.0465(9) Uani 1 1 d . . .
C2 C 0.6860(2) -0.1493(5) 0.55047(19) 0.0448(9) Uani 1 1 d . . .
H2A H 0.6392 -0.0754 0.5593 0.054 Uiso 1 1 calc R . .
H2B H 0.7234 -0.0441 0.5398 0.054 Uiso 1 1 calc R . .
C3 C 0.6644(2) -0.2914(5) 0.48937(18) 0.0425(9) Uani 1 1 d . . .
H3 H 0.7128 -0.3660 0.4831 0.051 Uiso 1 1 calc R . .
C4 C 0.6081(2) -0.4566(5) 0.5061(2) 0.0507(10) Uani 1 1 d . . .
H4A H 0.5606 -0.3891 0.5165 0.061 Uiso 1 1 calc R . .
H4B H 0.5933 -0.5482 0.4662 0.061 Uiso 1 1 calc R . .
C5 C 0.6447(2) -0.5843(5) 0.5664(2) 0.0537(10) Uani 1 1 d . . .
H5A H 0.6903 -0.6585 0.5549 0.064 Uiso 1 1 calc R . .
H5B H 0.6071 -0.6890 0.5771 0.064 Uiso 1 1 calc R . .
C6 C 0.6696(2) -0.4463(6) 0.6284(2) 0.0537(10) Uani 1 1 d . . .
H6A H 0.6228 -0.3889 0.6436 0.064 Uiso 1 1 calc R . .
H6B H 0.6972 -0.5322 0.6659 0.064 Uiso 1 1 calc R . .
C7 C 0.7365(2) -0.1236(6) 0.6763(2) 0.0580(11) Uani 1 1 d . . .
H7A H 0.7586 -0.2031 0.7167 0.087 Uiso 1 1 calc R . .
H7B H 0.6876 -0.0606 0.6835 0.087 Uiso 1 1 calc R . .
H7C H 0.7727 -0.0143 0.6680 0.087 Uiso 1 1 calc R . .
C8 C 0.5716(2) -0.0409(6) 0.42682(19) 0.0490(9) Uani 1 1 d . . .
H8A H 0.5928 0.0918 0.4468 0.059 Uiso 1 1 calc R . .
H8B H 0.5367 -0.0980 0.4566 0.059 Uiso 1 1 calc R . .
C9 C 0.5262(2) -0.0014(6) 0.35713(19) 0.0467(9) Uani 1 1 d . . .
C10 C 0.4893(2) -0.1638(6) 0.3194(2) 0.0535(10) Uani 1 1 d . . .
H10 H 0.4937 -0.3003 0.3375 0.064 Uiso 1 1 calc R . .
C11 C 0.4465(2) -0.1307(6) 0.2559(2) 0.0585(11) Uani 1 1 d . . .
H11 H 0.4218 -0.2440 0.2306 0.070 Uiso 1 1 calc R . .
C12 C 0.4393(2) 0.0675(7) 0.2291(2) 0.0578(11) Uani 1 1 d . . .
H12 H 0.4092 0.0912 0.1856 0.069 Uiso 1 1 calc R . .
C13 C 0.4762(2) 0.2308(6) 0.2659(2) 0.0547(10) Uani 1 1 d . . .
H13 H 0.4723 0.3669 0.2474 0.066 Uiso 1 1 calc R . .
C14 C 0.5189(2) 0.1958(6) 0.32975(19) 0.0516(10) Uani 1 1 d . . .
H14 H 0.5435 0.3091 0.3551 0.062 Uiso 1 1 calc R . .
C15 C 0.6962(2) -0.0921(6) 0.39304(19) 0.0492(9) Uani 1 1 d . . .
H15A H 0.7282 -0.0035 0.4273 0.059 Uiso 1 1 calc R . .
H15B H 0.6724 -0.0014 0.3552 0.059 Uiso 1 1 calc R . .
C16 C 0.7478(2) -0.2474(6) 0.36606(18) 0.0472(9) Uani 1 1 d . . .
C17 C 0.7179(2) -0.4332(6) 0.33529(19) 0.0532(10) Uani 1 1 d . . .
H17 H 0.6648 -0.4664 0.3338 0.064 Uiso 1 1 calc R . .
C18 C 0.7651(3) -0.5668(7) 0.3074(2) 0.0601(11) Uani 1 1 d . . .
H18 H 0.7441 -0.6912 0.2865 0.072 Uiso 1 1 calc R . .
C19 C 0.8418(3) -0.5242(8) 0.3090(2) 0.0658(12) Uani 1 1 d . . .
H19 H 0.8738 -0.6181 0.2895 0.079 Uiso 1 1 calc R . .
C20 C 0.8723(3) -0.3418(8) 0.3393(2) 0.0709(13) Uani 1 1 d . . .
H20 H 0.9254 -0.3102 0.3406 0.085 Uiso 1 1 calc R . .
C21 C 0.8257(2) -0.2070(7) 0.3676(2) 0.0611(11) Uani 1 1 d . . .
H21 H 0.8474 -0.0835 0.3886 0.073 Uiso 1 1 calc R . .
C22 C 0.8675(3) -0.6449(8) 0.4909(2) 0.0804(15) Uani 1 1 d . . .
H22A H 0.9074 -0.5370 0.4978 0.121 Uiso 1 1 calc R . .
H22B H 0.8213 -0.5910 0.4616 0.121 Uiso 1 1 calc R . .
H22C H 0.8871 -0.7657 0.4691 0.121 Uiso 1 1 calc R . .
C23 C 0.9731(3) -1.1094(7) 0.5900(3) 0.0787(15) Uani 1 1 d . . .
H23A H 1.0092 -0.9922 0.5973 0.118 Uiso 1 1 calc R . .
H23B H 0.9626 -1.1437 0.5415 0.118 Uiso 1 1 calc R . .
H23C H 0.9961 -1.2298 0.6158 0.118 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O1 C1 1.440(4) . ?
O1 H1H 0.879(10) . ?
O2 C22 1.378(5) . ?
O2 H2H 0.879(10) . ?
O3 C23 1.397(5) . ?
O3 H3H 0.880(10) . ?
N1 C15 1.452(5) . ?
N1 C8 1.471(4) . ?
N1 C3 1.481(4) . ?
C1 C6 1.520(5) . ?
C1 C7 1.527(5) . ?
C1 C2 1.535(5) . ?
C2 C3 1.521(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.525(5) . ?
C3 H3 1.0000 . ?
C4 C5 1.509(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.527(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.505(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.381(5) . ?
C9 C10 1.385(5) . ?
C10 C11 1.377(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.506(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C21 1.384(5) . ?
C16 C17 1.407(5) . ?
C17 C18 1.374(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.366(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.375(6) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
C1 O1 H1H 114(3) . . ?
C22 O2 H2H 120(3) . . ?
C23 O3 H3H 105(3) . . ?
C15 N1 C8 111.1(3) . . ?
C15 N1 C3 113.2(3) . . ?
C8 N1 C3 114.2(3) . . ?
O1 C1 C6 106.9(3) . . ?
O1 C1 C7 109.2(3) . . ?
C6 C1 C7 110.2(3) . . ?
O1 C1 C2 108.9(3) . . ?
C6 C1 C2 110.6(3) . . ?
C7 C1 C2 111.0(3) . . ?
C3 C2 C1 112.5(3) . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
N1 C3 C2 115.9(3) . . ?
N1 C3 C4 111.5(3) . . ?
C2 C3 C4 109.3(3) . . ?
N1 C3 H3 106.5 . . ?
C2 C3 H3 106.5 . . ?
C4 C3 H3 106.5 . . ?
C5 C4 C3 110.4(3) . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 C6 110.7(3) . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C1 C6 C5 113.3(3) . . ?
C1 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C1 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C9 111.2(3) . . ?
N1 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C14 C9 C10 118.4(4) . . ?
C14 C9 C8 121.4(3) . . ?
C10 C9 C8 120.2(3) . . ?
C11 C10 C9 121.2(4) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 119.9(4) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 119.6(4) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 119.9(4) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C9 C14 C13 120.9(4) . . ?
C9 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
N1 C15 C16 113.3(3) . . ?
N1 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
N1 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C21 C16 C17 117.7(4) . . ?
C21 C16 C15 121.0(3) . . ?
C17 C16 C15 121.2(3) . . ?
C18 C17 C16 120.2(4) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 121.3(4) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C20 119.2(4) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C21 C20 C19 120.1(4) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C16 121.4(4) . . ?
C20 C21 H21 119.3 . . ?
C16 C21 H21 119.3 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 64.5(4) . . . . ?
C6 C1 C2 C3 -52.7(4) . . . . ?
C7 C1 C2 C3 -175.3(3) . . . . ?
C15 N1 C3 C2 76.6(4) . . . . ?
C8 N1 C3 C2 -51.9(4) . . . . ?
C15 N1 C3 C4 -157.5(3) . . . . ?
C8 N1 C3 C4 74.0(4) . . . . ?
C1 C2 C3 N1 -175.3(3) . . . . ?
C1 C2 C3 C4 57.6(4) . . . . ?
N1 C3 C4 C5 170.4(3) . . . . ?
C2 C3 C4 C5 -60.0(4) . . . . ?
C3 C4 C5 C6 58.1(4) . . . . ?
O1 C1 C6 C5 -68.0(4) . . . . ?
C7 C1 C6 C5 173.5(3) . . . . ?
C2 C1 C6 C5 50.4(4) . . . . ?
C4 C5 C6 C1 -53.9(4) . . . . ?
C15 N1 C8 C9 71.3(4) . . . . ?
C3 N1 C8 C9 -159.2(3) . . . . ?
N1 C8 C9 C14 -120.9(4) . . . . ?
N1 C8 C9 C10 60.3(5) . . . . ?
C14 C9 C10 C11 0.1(6) . . . . ?
C8 C9 C10 C11 178.9(4) . . . . ?
C9 C10 C11 C12 -0.4(7) . . . . ?
C10 C11 C12 C13 0.9(7) . . . . ?
C11 C12 C13 C14 -1.1(6) . . . . ?
C10 C9 C14 C13 -0.4(6) . . . . ?
C8 C9 C14 C13 -179.2(4) . . . . ?
C12 C13 C14 C9 0.9(6) . . . . ?
C8 N1 C15 C16 -159.5(3) . . . . ?
C3 N1 C15 C16 70.5(4) . . . . ?
N1 C15 C16 C21 -146.5(4) . . . . ?
N1 C15 C16 C17 36.9(5) . . . . ?
C21 C16 C17 C18 -0.7(6) . . . . ?
C15 C16 C17 C18 176.0(3) . . . . ?
C16 C17 C18 C19 0.4(6) . . . . ?
C17 C18 C19 C20 -0.2(7) . . . . ?
C18 C19 C20 C21 0.3(7) . . . . ?
C19 C20 C21 C16 -0.6(7) . . . . ?
C17 C16 C21 C20 0.8(6) . . . . ?
C15 C16 C21 C20 -175.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        65.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_tom_jones_salt2
_database_code_depnum_ccdc_archive 'CCDC 1064078'
_audit_update_record             
;
2015-05-08 deposited with the CCDC.
2015-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H28 Cl N O'
_chemical_formula_weight         345.89

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.1484 0.1585 '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'
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   Pna21

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

_cell_length_a                   18.8610(10)
_cell_length_b                   7.1930(3)
_cell_length_c                   13.7442(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1864.64(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    11486
_cell_measurement_theta_min      3.1486
_cell_measurement_theta_max      29.9552


_exptl_crystal_description       slab
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_min  0.99094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(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  'Oxford Diffraction Xcalibur E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26232
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         30.02
_reflns_number_total             5038
_reflns_number_gt                4749
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       CrysalisPro
_computing_cell_refinement       CrysalisPro
_computing_data_reduction        CrysalisPro
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  SHELXL-97


_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 > 2σ(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)+(0.0324P)²+0.3696P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_number_reflns         5038
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0711
_refine_ls_wR_factor_gt          0.0691
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.002
_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
Cl1 Cl 1.036829(18) 0.55018(4) 0.24416(2) 0.02494(8) Uani 1 1 d . . .
O1 O 0.97038(5) 0.20677(13) -0.06544(6) 0.01896(18) Uani 1 1 d . . .
N1 N 1.00086(5) 0.16415(14) 0.15324(7) 0.01286(19) Uani 1 1 d . . .
C1 C 0.93158(6) 0.14260(16) 0.09724(8) 0.0125(2) Uani 1 1 d . . .
H1 H 0.8930 0.1779 0.1436 0.015 Uiso 1 1 calc R . .
C2 C 0.92307(7) 0.27117(16) 0.00825(8) 0.0150(2) Uani 1 1 d . . .
C3 C 0.84606(7) 0.25067(19) -0.02661(9) 0.0192(2) Uani 1 1 d . . .
H3A H 0.8139 0.2988 0.0244 0.023 Uiso 1 1 calc R . .
H3B H 0.8392 0.3275 -0.0856 0.023 Uiso 1 1 calc R . .
C4 C 0.82585(7) 0.04975(19) -0.04972(10) 0.0231(3) Uani 1 1 d . . .
H4A H 0.7749 0.0437 -0.0666 0.028 Uiso 1 1 calc R . .
H4B H 0.8534 0.0063 -0.1067 0.028 Uiso 1 1 calc R . .
C5 C 0.84047(7) -0.07723(18) 0.03665(10) 0.0223(3) Uani 1 1 d . . .
H5A H 0.8305 -0.2077 0.0182 0.027 Uiso 1 1 calc R . .
H5B H 0.8087 -0.0437 0.0912 0.027 Uiso 1 1 calc R . .
C6 C 0.91767(7) -0.05947(16) 0.06930(9) 0.0171(2) Uani 1 1 d . . .
H6A H 0.9266 -0.1416 0.1258 0.020 Uiso 1 1 calc R . .
H6B H 0.9498 -0.0971 0.0158 0.020 Uiso 1 1 calc R . .
C7 C 0.93805(8) 0.47427(18) 0.03134(10) 0.0224(3) Uani 1 1 d . . .
H7A H 0.9880 0.4887 0.0496 0.034 Uiso 1 1 calc R . .
H7B H 0.9078 0.5144 0.0854 0.034 Uiso 1 1 calc R . .
H7C H 0.9280 0.5505 -0.0261 0.034 Uiso 1 1 calc R . .
C8 C 1.06516(6) 0.11557(19) 0.09166(9) 0.0193(2) Uani 1 1 d . . .
H8A H 1.0547 -0.0002 0.0555 0.023 Uiso 1 1 calc R . .
H8B H 1.0721 0.2156 0.0431 0.023 Uiso 1 1 calc R . .
C9 C 1.13365(6) 0.08895(18) 0.14619(8) 0.0168(2) Uani 1 1 d . . .
C10 C 1.17654(7) 0.23868(19) 0.17097(9) 0.0213(3) Uani 1 1 d . . .
H10 H 1.1606 0.3621 0.1595 0.026 Uiso 1 1 calc R . .
C11 C 1.24283(7) 0.2081(2) 0.21267(10) 0.0268(3) Uani 1 1 d . . .
H11 H 1.2716 0.3109 0.2306 0.032 Uiso 1 1 calc R . .
C12 C 1.26681(7) 0.0294(2) 0.22799(9) 0.0272(3) Uani 1 1 d . . .
H12 H 1.3126 0.0092 0.2547 0.033 Uiso 1 1 calc R . .
C13 C 1.22423(7) -0.1200(2) 0.20458(10) 0.0260(3) Uani 1 1 d . . .
H13 H 1.2404 -0.2431 0.2160 0.031 Uiso 1 1 calc R . .
C14 C 1.15786(7) -0.09045(19) 0.16445(9) 0.0207(3) Uani 1 1 d . . .
H14 H 1.1285 -0.1938 0.1492 0.025 Uiso 1 1 calc R . .
C15 C 1.00167(6) 0.05625(15) 0.24842(9) 0.0149(2) Uani 1 1 d . . .
H15A H 1.0102 -0.0766 0.2336 0.018 Uiso 1 1 calc R . .
H15B H 1.0420 0.1008 0.2882 0.018 Uiso 1 1 calc R . .
C16 C 0.93481(6) 0.07149(18) 0.30822(8) 0.0165(2) Uani 1 1 d . . .
C17 C 0.91843(7) 0.23355(19) 0.35847(9) 0.0211(3) Uani 1 1 d . . .
H17 H 0.9481 0.3396 0.3525 0.025 Uiso 1 1 calc R . .
C18 C 0.85859(8) 0.2407(2) 0.41754(9) 0.0270(3) Uani 1 1 d . . .
H18 H 0.8477 0.3518 0.4519 0.032 Uiso 1 1 calc R . .
C19 C 0.81486(7) 0.0879(2) 0.42671(10) 0.0291(3) Uani 1 1 d . . .
H19 H 0.7736 0.0945 0.4661 0.035 Uiso 1 1 calc R . .
C20 C 0.83134(7) -0.0747(2) 0.37840(10) 0.0268(3) Uani 1 1 d . . .
H20 H 0.8018 -0.1808 0.3854 0.032 Uiso 1 1 calc R . .
C21 C 0.89122(7) -0.0833(2) 0.31937(9) 0.0210(3) Uani 1 1 d . . .
H21 H 0.9024 -0.1956 0.2864 0.025 Uiso 1 1 calc R . .
H1N H 1.0047(8) 0.285(2) 0.1680(12) 0.021(4) Uiso 1 1 d . . .
H2H H 0.9651(10) 0.268(3) -0.1149(15) 0.038(5) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O1 C2 1.4272(14) . ?
O1 H2H 0.82(2) . ?
N1 C8 1.5196(15) . ?
N1 C15 1.5212(15) . ?
N1 C1 1.5245(14) . ?
N1 H1N 0.894(16) . ?
C1 C6 1.5261(16) . ?
C1 C2 1.5417(16) . ?
C1 H1 1.0000 . ?
C2 C7 1.5214(18) . ?
C2 C3 1.5365(16) . ?
C3 C4 1.5280(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5230(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5290(18) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.5057(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.3894(18) . ?
C9 C14 1.3917(19) . ?
C10 C11 1.3928(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3842(19) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.5091(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.3897(18) . ?
C16 C21 1.3925(18) . ?
C17 C18 1.3914(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.380(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.3919(18) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

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
C2 O1 H2H 109.8(13) . . ?
C8 N1 C15 110.71(9) . . ?
C8 N1 C1 112.30(9) . . ?
C15 N1 C1 113.01(9) . . ?
C8 N1 H1N 106.6(10) . . ?
C15 N1 H1N 107.4(10) . . ?
C1 N1 H1N 106.4(10) . . ?
N1 C1 C6 111.80(9) . . ?
N1 C1 C2 115.39(9) . . ?
C6 C1 C2 110.72(9) . . ?
N1 C1 H1 106.1 . . ?
C6 C1 H1 106.1 . . ?
C2 C1 H1 106.1 . . ?
O1 C2 C7 110.09(10) . . ?
O1 C2 C3 109.79(9) . . ?
C7 C2 C3 109.43(10) . . ?
O1 C2 C1 107.65(9) . . ?
C7 C2 C1 113.03(9) . . ?
C3 C2 C1 106.75(9) . . ?
C4 C3 C2 113.04(10) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C3 111.10(10) . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 C6 110.55(10) . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C1 C6 C5 108.49(10) . . ?
C1 C6 H6A 110.0 . . ?
C5 C6 H6A 110.0 . . ?
C1 C6 H6B 110.0 . . ?
C5 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 N1 115.89(10) . . ?
C9 C8 H8A 108.3 . . ?
N1 C8 H8A 108.3 . . ?
C9 C8 H8B 108.3 . . ?
N1 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C10 C9 C14 118.91(12) . . ?
C10 C9 C8 121.54(12) . . ?
C14 C9 C8 119.29(11) . . ?
C9 C10 C11 120.08(13) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.30(13) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 119.97(12) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 119.99(13) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 120.73(12) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C16 C15 N1 115.02(9) . . ?
C16 C15 H15A 108.5 . . ?
N1 C15 H15A 108.5 . . ?
C16 C15 H15B 108.5 . . ?
N1 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
C17 C16 C21 118.99(12) . . ?
C17 C16 C15 121.15(11) . . ?
C21 C16 C15 119.69(11) . . ?
C16 C17 C18 120.10(13) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 120.56(13) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 119.76(13) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 120.07(13) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C16 120.50(13) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C6 65.01(12) . . . . ?
C15 N1 C1 C6 -61.11(12) . . . . ?
C8 N1 C1 C2 -62.69(12) . . . . ?
C15 N1 C1 C2 171.19(9) . . . . ?
N1 C1 C2 O1 71.40(12) . . . . ?
C6 C1 C2 O1 -56.84(12) . . . . ?
N1 C1 C2 C7 -50.41(13) . . . . ?
C6 C1 C2 C7 -178.65(11) . . . . ?
N1 C1 C2 C3 -170.77(9) . . . . ?
C6 C1 C2 C3 60.99(12) . . . . ?
O1 C2 C3 C4 60.14(13) . . . . ?
C7 C2 C3 C4 -178.92(11) . . . . ?
C1 C2 C3 C4 -56.27(12) . . . . ?
C2 C3 C4 C5 54.58(14) . . . . ?
C3 C4 C5 C6 -54.77(15) . . . . ?
N1 C1 C6 C5 166.21(9) . . . . ?
C2 C1 C6 C5 -63.63(12) . . . . ?
C4 C5 C6 C1 59.16(13) . . . . ?
C15 N1 C8 C9 -38.78(14) . . . . ?
C1 N1 C8 C9 -166.13(10) . . . . ?
N1 C8 C9 C10 -84.13(14) . . . . ?
N1 C8 C9 C14 101.85(13) . . . . ?
C14 C9 C10 C11 0.49(18) . . . . ?
C8 C9 C10 C11 -173.55(11) . . . . ?
C9 C10 C11 C12 1.17(19) . . . . ?
C10 C11 C12 C13 -1.9(2) . . . . ?
C11 C12 C13 C14 0.92(19) . . . . ?
C12 C13 C14 C9 0.76(19) . . . . ?
C10 C9 C14 C13 -1.46(18) . . . . ?
C8 C9 C14 C13 172.72(11) . . . . ?
C8 N1 C15 C16 -171.04(10) . . . . ?
C1 N1 C15 C16 -44.08(13) . . . . ?
N1 C15 C16 C17 -73.40(15) . . . . ?
N1 C15 C16 C21 111.40(12) . . . . ?
C21 C16 C17 C18 -1.10(18) . . . . ?
C15 C16 C17 C18 -176.33(12) . . . . ?
C16 C17 C18 C19 -0.2(2) . . . . ?
C17 C18 C19 C20 1.3(2) . . . . ?
C18 C19 C20 C21 -1.07(19) . . . . ?
C19 C20 C21 C16 -0.22(19) . . . . ?
C17 C16 C21 C20 1.30(18) . . . . ?
C15 C16 C21 C20 176.60(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.947
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_tom_jones_cf3
_database_code_depnum_ccdc_archive 'CCDC 1064079'
_audit_update_record             
;
2015-05-08 deposited with the CCDC.
2015-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H25 F3 N O1.50'
_chemical_formula_weight         372.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
F F 0.0171 0.0103 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c


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                   16.8197(14)
_cell_length_b                   6.2849(5)
_cell_length_c                   18.1930(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.240(7)
_cell_angle_gamma                90.00
_cell_volume                     1920.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    6392
_cell_measurement_theta_min      3.2033
_cell_measurement_theta_max      29.5053


_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05

_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             788
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_min  0.63335
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
;
Mounted in loop
;


_diffrn_ambient_temperature      123(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  'Oxford Diffraction Xcalibur E'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20222
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         27.00
_reflns_number_total             4183
_reflns_number_gt                3312
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       CrysalisPro
_computing_cell_refinement       CrysalisPro
_computing_data_reduction        CrysalisPro
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  SHELXL-97

_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 > 2σ(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)+(0.0162P)²+2.2058P] 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         4183
_refine_ls_number_parameters     256
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1176
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.144
_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
F1 F -0.04027(9) -0.1395(2) 0.86859(8) 0.0400(4) Uani 1 1 d . . .
F2 F -0.06269(8) 0.1868(3) 0.83894(8) 0.0386(4) Uani 1 1 d . . .
F3 F 0.01211(8) -0.0033(2) 0.77426(6) 0.0311(3) Uani 1 1 d . . .
O1 O 0.03330(10) 0.1584(3) 0.96230(8) 0.0252(4) Uani 1 1 d D . .
H1H H 0.017(3) 0.048(6) 0.984(3) 0.030 Uiso 0.50 1 d PD . .
H2H H 0.000(2) 0.263(6) 0.958(3) 0.030 Uiso 0.50 1 d PD . .
N1 N 0.26561(10) 0.0436(3) 0.75110(9) 0.0209(4) Uani 1 1 d . . .
C1 C 0.21620(12) 0.0760(3) 0.81487(11) 0.0204(4) Uani 1 1 d . . .
H1 H 0.2531 0.1219 0.8569 0.024 Uiso 1 1 calc R . .
C2 C 0.15795(13) 0.2589(3) 0.79943(11) 0.0211(5) Uani 1 1 d . . .
H2A H 0.1228 0.2239 0.7556 0.025 Uiso 1 1 calc R . .
H2B H 0.1881 0.3890 0.7882 0.025 Uiso 1 1 calc R . .
C3 C 0.10668(13) 0.3029(3) 0.86486(11) 0.0204(4) Uani 1 1 d . . .
H3A H 0.1408 0.3658 0.9053 0.024 Uiso 1 1 calc R . .
H3B H 0.0656 0.4094 0.8498 0.024 Uiso 1 1 calc R . .
C4 C 0.06550(12) 0.1061(3) 0.89402(11) 0.0191(4) Uani 1 1 d . . .
C5 C 0.12502(13) -0.0761(3) 0.90681(11) 0.0219(5) Uani 1 1 d . . .
H5A H 0.1621 -0.0396 0.9491 0.026 Uiso 1 1 calc R . .
H5B H 0.0957 -0.2059 0.9199 0.026 Uiso 1 1 calc R . .
C6 C 0.17337(12) -0.1244(3) 0.84031(11) 0.0206(4) Uani 1 1 d . . .
H6A H 0.1375 -0.1787 0.7995 0.025 Uiso 1 1 calc R . .
H6B H 0.2131 -0.2363 0.8534 0.025 Uiso 1 1 calc R . .
C7 C -0.00586(13) 0.0373(4) 0.84366(12) 0.0242(5) Uani 1 1 d . . .
C8 C 0.34215(12) -0.0567(4) 0.77230(12) 0.0230(5) Uani 1 1 d . . .
H8A H 0.3667 -0.1090 0.7275 0.028 Uiso 1 1 calc R . .
H8B H 0.3329 -0.1809 0.8042 0.028 Uiso 1 1 calc R . .
C9 C 0.39896(12) 0.0949(4) 0.81274(11) 0.0213(5) Uani 1 1 d . . .
C10 C 0.44566(13) 0.0301(4) 0.87415(12) 0.0274(5) Uani 1 1 d . . .
H10 H 0.4394 -0.1092 0.8933 0.033 Uiso 1 1 calc R . .
C11 C 0.50142(14) 0.1671(4) 0.90792(13) 0.0340(6) Uani 1 1 d . . .
H11 H 0.5329 0.1208 0.9499 0.041 Uiso 1 1 calc R . .
C12 C 0.51128(14) 0.3701(4) 0.88080(14) 0.0327(6) Uani 1 1 d . . .
H12 H 0.5496 0.4631 0.9038 0.039 Uiso 1 1 calc R . .
C13 C 0.46494(13) 0.4371(4) 0.81991(13) 0.0285(5) Uani 1 1 d . . .
H13 H 0.4714 0.5767 0.8011 0.034 Uiso 1 1 calc R . .
C14 C 0.40915(13) 0.3012(4) 0.78622(12) 0.0248(5) Uani 1 1 d . . .
H14 H 0.3774 0.3489 0.7446 0.030 Uiso 1 1 calc R . .
C15 C 0.22438(13) -0.0703(4) 0.68967(11) 0.0228(5) Uani 1 1 d . . .
H15A H 0.1677 -0.0269 0.6860 0.027 Uiso 1 1 calc R . .
H15B H 0.2265 -0.2251 0.6997 0.027 Uiso 1 1 calc R . .
C16 C 0.26097(12) -0.0263(4) 0.61712(11) 0.0209(5) Uani 1 1 d . . .
C17 C 0.26961(13) -0.1900(4) 0.56683(12) 0.0248(5) Uani 1 1 d . . .
H17 H 0.2544 -0.3307 0.5789 0.030 Uiso 1 1 calc R . .
C18 C 0.30041(13) -0.1488(4) 0.49880(12) 0.0273(5) Uani 1 1 d . . .
H18 H 0.3060 -0.2618 0.4648 0.033 Uiso 1 1 calc R . .
C19 C 0.32294(14) 0.0550(4) 0.48020(12) 0.0283(5) Uani 1 1 d . . .
H19 H 0.3441 0.0822 0.4338 0.034 Uiso 1 1 calc R . .
C20 C 0.31430(15) 0.2187(4) 0.52996(13) 0.0320(6) Uani 1 1 d . . .
H20 H 0.3296 0.3592 0.5177 0.038 Uiso 1 1 calc R . .
C21 C 0.28335(14) 0.1784(4) 0.59786(12) 0.0283(5) Uani 1 1 d . . .
H21 H 0.2774 0.2921 0.6315 0.034 Uiso 1 1 calc R . .
O1W O -0.0712(2) 0.4748(6) 0.9638(2) 0.0342(8) Uani 0.50 1 d PD . .
H1W H -0.1198(17) 0.475(10) 0.945(3) 0.050 Uiso 0.50 1 d PD . .
H2W H -0.065(3) 0.590(6) 0.990(3) 0.050 Uiso 0.50 1 d PD . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C7 1.344(3) . ?
F2 C7 1.340(3) . ?
F3 C7 1.339(2) . ?
O1 C4 1.422(2) . ?
O1 H1H 0.852(19) . ?
O1 H2H 0.864(19) . ?
N1 C8 1.465(3) . ?
N1 C15 1.468(3) . ?
N1 C1 1.479(3) . ?
C1 C2 1.526(3) . ?
C1 C6 1.535(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.534(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.527(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.530(3) . ?
C4 C7 1.530(3) . ?
C5 C6 1.526(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C9 1.511(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.390(3) . ?
C9 C14 1.398(3) . ?
C10 C11 1.390(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.513(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.390(3) . ?
C16 C21 1.391(3) . ?
C17 C18 1.393(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.383(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.384(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.390(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
O1W H1W 0.87(2) . ?
O1W H2W 0.87(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
C4 O1 H1H 112(4) . . ?
C4 O1 H2H 112(3) . . ?
H1H O1 H2H 116(5) . . ?
C8 N1 C15 111.16(17) . . ?
C8 N1 C1 112.14(16) . . ?
C15 N1 C1 113.72(16) . . ?
N1 C1 C2 110.03(17) . . ?
N1 C1 C6 114.69(18) . . ?
C2 C1 C6 111.47(17) . . ?
N1 C1 H1 106.7 . . ?
C2 C1 H1 106.7 . . ?
C6 C1 H1 106.7 . . ?
C1 C2 C3 112.09(17) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C2 114.16(17) . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
O1 C4 C3 108.58(17) . . ?
O1 C4 C5 108.58(16) . . ?
C3 C4 C5 110.68(17) . . ?
O1 C4 C7 105.30(17) . . ?
C3 C4 C7 112.12(17) . . ?
C5 C4 C7 111.35(18) . . ?
C6 C5 C4 113.69(17) . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C5 C6 C1 110.86(18) . . ?
C5 C6 H6A 109.5 . . ?
C1 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
F3 C7 F2 105.74(17) . . ?
F3 C7 F1 106.57(18) . . ?
F2 C7 F1 106.40(18) . . ?
F3 C7 C4 114.02(17) . . ?
F2 C7 C4 111.89(18) . . ?
F1 C7 C4 111.70(18) . . ?
N1 C8 C9 112.29(18) . . ?
N1 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C14 118.3(2) . . ?
C10 C9 C8 121.3(2) . . ?
C14 C9 C8 120.22(19) . . ?
C9 C10 C11 120.7(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 119.6(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 120.2(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 120.8(2) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
N1 C15 C16 112.16(17) . . ?
N1 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
N1 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C17 C16 C21 118.6(2) . . ?
C17 C16 C15 120.1(2) . . ?
C21 C16 C15 121.2(2) . . ?
C16 C17 C18 120.4(2) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 120.7(2) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 119.2(2) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C19 C20 C21 120.3(2) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 120.8(2) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
H1W O1W H2W 108(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 154.98(18) . . . . ?
C15 N1 C1 C2 -77.8(2) . . . . ?
C8 N1 C1 C6 -78.4(2) . . . . ?
C15 N1 C1 C6 48.8(2) . . . . ?
N1 C1 C2 C3 -178.50(17) . . . . ?
C6 C1 C2 C3 53.1(2) . . . . ?
C1 C2 C3 C4 -51.3(2) . . . . ?
C2 C3 C4 O1 168.70(17) . . . . ?
C2 C3 C4 C5 49.6(2) . . . . ?
C2 C3 C4 C7 -75.4(2) . . . . ?
O1 C4 C5 C6 -171.00(17) . . . . ?
C3 C4 C5 C6 -51.9(2) . . . . ?
C7 C4 C5 C6 73.5(2) . . . . ?
C4 C5 C6 C1 55.2(2) . . . . ?
N1 C1 C6 C5 179.19(17) . . . . ?
C2 C1 C6 C5 -54.9(2) . . . . ?
O1 C4 C7 F3 175.17(18) . . . . ?
C3 C4 C7 F3 57.3(2) . . . . ?
C5 C4 C7 F3 -67.3(2) . . . . ?
O1 C4 C7 F2 55.2(2) . . . . ?
C3 C4 C7 F2 -62.7(2) . . . . ?
C5 C4 C7 F2 172.72(17) . . . . ?
O1 C4 C7 F1 -63.9(2) . . . . ?
C3 C4 C7 F1 178.17(17) . . . . ?
C5 C4 C7 F1 53.5(2) . . . . ?
C15 N1 C8 C9 157.98(17) . . . . ?
C1 N1 C8 C9 -73.5(2) . . . . ?
N1 C8 C9 C10 138.1(2) . . . . ?
N1 C8 C9 C14 -45.8(3) . . . . ?
C14 C9 C10 C11 -0.4(3) . . . . ?
C8 C9 C10 C11 175.8(2) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C10 C11 C12 C13 0.4(4) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C9 -0.3(3) . . . . ?
C10 C9 C14 C13 0.6(3) . . . . ?
C8 C9 C14 C13 -175.6(2) . . . . ?
C8 N1 C15 C16 -75.1(2) . . . . ?
C1 N1 C15 C16 157.23(18) . . . . ?
N1 C15 C16 C17 139.6(2) . . . . ?
N1 C15 C16 C21 -43.2(3) . . . . ?
C21 C16 C17 C18 0.3(3) . . . . ?
C15 C16 C17 C18 177.5(2) . . . . ?
C16 C17 C18 C19 0.1(3) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
C18 C19 C20 C21 0.0(4) . . . . ?
C19 C20 C21 C16 0.3(4) . . . . ?
C17 C16 C21 C20 -0.5(3) . . . . ?
C15 C16 C21 C20 -177.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_tom_jones2015b
_database_code_depnum_ccdc_archive 'CCDC 1064080'
_audit_update_record             
;
2015-05-08 deposited with the CCDC.
2015-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H24 F3 N O'
_chemical_formula_weight         363.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
F F 0.0171 0.0103 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   17.8003(4)
_cell_length_b                   6.1791(2)
_cell_length_c                   17.0864(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.206(2)
_cell_angle_gamma                90.00
_cell_volume                     1843.50(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    7874
_cell_measurement_theta_min      3.2901
_cell_measurement_theta_max      29.4923


_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_min  0.96542
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(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  'Oxford Diffraction Xcalibur E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16736
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         29.56
_reflns_number_total             4716
_reflns_number_gt                3924
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       CrysalisPro
_computing_cell_refinement       CrysalisPro
_computing_data_reduction        CrysalisPro
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  SHELXL-97

_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 > 2σ(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)+(0.0399P)²+0.7252P] 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     SHELXL
_refine_ls_extinction_coef       0.0064(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4716
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.0999
_refine_ls_wR_factor_gt          0.0932
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
F1 F 0.58765(5) 0.31857(16) 0.48285(4) 0.0412(2) Uani 1 1 d . . .
F2 F 0.49857(5) 0.47249(14) 0.39806(5) 0.0392(2) Uani 1 1 d . . .
F3 F 0.48753(5) 0.14007(15) 0.42905(5) 0.0419(2) Uani 1 1 d . . .
O1 O 0.51824(5) 0.17950(18) 0.27937(5) 0.0302(2) Uani 1 1 d . . .
H1H H 0.5058(10) 0.300(3) 0.2596(10) 0.036 Uiso 1 1 d . . .
N1 N 0.75963(5) 0.06942(15) 0.21976(5) 0.01567(19) Uani 1 1 d . . .
C1 C 0.71617(6) 0.12550(17) 0.28204(6) 0.0150(2) Uani 1 1 d . . .
H1 H 0.7547 0.1526 0.3320 0.018 Uiso 1 1 calc R . .
C2 C 0.66350(7) -0.05461(18) 0.30108(7) 0.0187(2) Uani 1 1 d . . .
H2A H 0.6943 -0.1862 0.3175 0.022 Uiso 1 1 calc R . .
H2B H 0.6254 -0.0899 0.2524 0.022 Uiso 1 1 calc R . .
C3 C 0.62154(7) 0.01070(19) 0.36760(7) 0.0207(2) Uani 1 1 d . . .
H3A H 0.5856 -0.1058 0.3757 0.025 Uiso 1 1 calc R . .
H3B H 0.6591 0.0295 0.4181 0.025 Uiso 1 1 calc R . .
C4 C 0.57744(6) 0.22026(19) 0.34697(6) 0.0180(2) Uani 1 1 d . . .
C5 C 0.63061(7) 0.39957(19) 0.32971(7) 0.0213(2) Uani 1 1 d . . .
H5A H 0.6690 0.4308 0.3786 0.026 Uiso 1 1 calc R . .
H5B H 0.6005 0.5330 0.3145 0.026 Uiso 1 1 calc R . .
C6 C 0.67172(7) 0.33534(19) 0.26232(7) 0.0214(2) Uani 1 1 d . . .
H6A H 0.6336 0.3170 0.2122 0.026 Uiso 1 1 calc R . .
H6B H 0.7074 0.4522 0.2540 0.026 Uiso 1 1 calc R . .
C7 C 0.53774(7) 0.2874(2) 0.41470(7) 0.0256(3) Uani 1 1 d . . .
C8 C 0.82928(6) -0.05188(18) 0.25188(6) 0.0169(2) Uani 1 1 d . . .
H8A H 0.8477 -0.1248 0.2075 0.020 Uiso 1 1 calc R . .
H8B H 0.8173 -0.1651 0.2886 0.020 Uiso 1 1 calc R . .
C9 C 0.89212(6) 0.09237(18) 0.29621(6) 0.0166(2) Uani 1 1 d . . .
C10 C 0.90353(7) 0.29841(19) 0.26738(7) 0.0192(2) Uani 1 1 d . . .
H10 H 0.8691 0.3519 0.2219 0.023 Uiso 1 1 calc R . .
C11 C 0.96423(7) 0.4264(2) 0.30395(7) 0.0232(3) Uani 1 1 d . . .
H11 H 0.9714 0.5661 0.2833 0.028 Uiso 1 1 calc R . .
C12 C 1.01457(7) 0.3504(2) 0.37079(8) 0.0276(3) Uani 1 1 d . . .
H12 H 1.0563 0.4375 0.3960 0.033 Uiso 1 1 calc R . .
C13 C 1.00355(7) 0.1469(2) 0.40031(7) 0.0280(3) Uani 1 1 d . . .
H13 H 1.0377 0.0944 0.4461 0.034 Uiso 1 1 calc R . .
C14 C 0.94277(7) 0.0186(2) 0.36338(7) 0.0218(2) Uani 1 1 d . . .
H14 H 0.9357 -0.1209 0.3842 0.026 Uiso 1 1 calc R . .
C15 C 0.71436(7) -0.03271(19) 0.14857(6) 0.0190(2) Uani 1 1 d . . .
H15A H 0.6642 0.0409 0.1342 0.023 Uiso 1 1 calc R . .
H15B H 0.7049 -0.1862 0.1602 0.023 Uiso 1 1 calc R . .
C16 C 0.75544(6) -0.02049(19) 0.07917(6) 0.0175(2) Uani 1 1 d . . .
C17 C 0.78758(7) 0.1731(2) 0.06026(7) 0.0216(2) Uani 1 1 d . . .
H17 H 0.7832 0.2989 0.0910 0.026 Uiso 1 1 calc R . .
C18 C 0.82592(7) 0.1846(2) -0.00292(7) 0.0256(3) Uani 1 1 d . . .
H18 H 0.8478 0.3178 -0.0150 0.031 Uiso 1 1 calc R . .
C19 C 0.83243(7) 0.0027(2) -0.04852(7) 0.0267(3) Uani 1 1 d . . .
H19 H 0.8589 0.0104 -0.0917 0.032 Uiso 1 1 calc R . .
C20 C 0.80024(8) -0.1898(2) -0.03075(7) 0.0262(3) Uani 1 1 d . . .
H20 H 0.8043 -0.3149 -0.0620 0.031 Uiso 1 1 calc R . .
C21 C 0.76177(7) -0.2015(2) 0.03280(7) 0.0220(2) Uani 1 1 d . . .
H21 H 0.7397 -0.3347 0.0445 0.026 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C7 1.3343(15) . ?
F2 C7 1.3412(15) . ?
F3 C7 1.3313(15) . ?
O1 C4 1.4265(14) . ?
O1 H1H 0.831(17) . ?
N1 C8 1.4614(14) . ?
N1 C15 1.4651(14) . ?
N1 C1 1.4734(13) . ?
C1 C6 1.5222(15) . ?
C1 C2 1.5304(15) . ?
C1 H1 1.0000 . ?
C2 C3 1.5304(15) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5198(16) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5227(16) . ?
C4 C7 1.5260(15) . ?
C5 C6 1.5318(15) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C9 1.5133(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.3912(16) . ?
C9 C10 1.3941(16) . ?
C10 C11 1.3860(17) . ?
C10 H10 0.9500 . ?
C11 C12 1.3894(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3898(18) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.5112(15) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C21 1.3879(16) . ?
C16 C17 1.3907(16) . ?
C17 C18 1.3866(17) . ?
C17 H17 0.9500 . ?
C18 C19 1.3854(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.3792(19) . ?
C19 H19 0.9500 . ?
C20 C21 1.3937(16) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

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
C4 O1 H1H 105.5(12) . . ?
C8 N1 C15 112.36(9) . . ?
C8 N1 C1 112.07(8) . . ?
C15 N1 C1 114.81(8) . . ?
N1 C1 C6 111.33(9) . . ?
N1 C1 C2 114.32(9) . . ?
C6 C1 C2 110.67(9) . . ?
N1 C1 H1 106.7 . . ?
C6 C1 H1 106.7 . . ?
C2 C1 H1 106.7 . . ?
C1 C2 C3 111.94(9) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 C2 110.91(9) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.0 . . ?
O1 C4 C3 107.72(10) . . ?
O1 C4 C5 111.15(10) . . ?
C3 C4 C5 110.64(9) . . ?
O1 C4 C7 106.50(9) . . ?
C3 C4 C7 110.48(9) . . ?
C5 C4 C7 110.24(10) . . ?
C4 C5 C6 111.26(10) . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C1 C6 C5 110.98(9) . . ?
C1 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C1 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
F3 C7 F1 107.17(10) . . ?
F3 C7 F2 106.39(10) . . ?
F1 C7 F2 107.00(11) . . ?
F3 C7 C4 112.35(11) . . ?
F1 C7 C4 111.92(10) . . ?
F2 C7 C4 111.67(10) . . ?
N1 C8 C9 112.11(9) . . ?
N1 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C14 C9 C10 118.36(11) . . ?
C14 C9 C8 121.16(10) . . ?
C10 C9 C8 120.35(10) . . ?
C11 C10 C9 121.09(11) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 119.94(12) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 119.53(12) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 120.40(12) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 120.68(12) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
N1 C15 C16 110.98(9) . . ?
N1 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
N1 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C21 C16 C17 118.55(10) . . ?
C21 C16 C15 120.86(10) . . ?
C17 C16 C15 120.59(10) . . ?
C18 C17 C16 120.80(11) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C17 120.25(12) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 119.47(11) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C21 120.31(12) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 120.62(11) . . ?
C16 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C6 150.30(9) . . . . ?
C15 N1 C1 C6 -79.93(12) . . . . ?
C8 N1 C1 C2 -83.38(11) . . . . ?
C15 N1 C1 C2 46.39(13) . . . . ?
N1 C1 C2 C3 178.49(9) . . . . ?
C6 C1 C2 C3 -54.84(12) . . . . ?
C1 C2 C3 C4 55.39(13) . . . . ?
C2 C3 C4 O1 65.69(12) . . . . ?
C2 C3 C4 C5 -55.99(13) . . . . ?
C2 C3 C4 C7 -178.35(10) . . . . ?
O1 C4 C5 C6 -62.63(12) . . . . ?
C3 C4 C5 C6 57.01(13) . . . . ?
C7 C4 C5 C6 179.52(10) . . . . ?
N1 C1 C6 C5 -176.58(9) . . . . ?
C2 C1 C6 C5 55.11(13) . . . . ?
C4 C5 C6 C1 -56.79(13) . . . . ?
O1 C4 C7 F3 55.96(13) . . . . ?
C3 C4 C7 F3 -60.76(13) . . . . ?
C5 C4 C7 F3 176.65(10) . . . . ?
O1 C4 C7 F1 176.59(10) . . . . ?
C3 C4 C7 F1 59.87(14) . . . . ?
C5 C4 C7 F1 -62.73(13) . . . . ?
O1 C4 C7 F2 -63.49(13) . . . . ?
C3 C4 C7 F2 179.80(10) . . . . ?
C5 C4 C7 F2 57.20(13) . . . . ?
C15 N1 C8 C9 152.49(9) . . . . ?
C1 N1 C8 C9 -76.48(11) . . . . ?
N1 C8 C9 C14 145.01(10) . . . . ?
N1 C8 C9 C10 -39.14(13) . . . . ?
C14 C9 C10 C11 0.70(16) . . . . ?
C8 C9 C10 C11 -175.26(10) . . . . ?
C9 C10 C11 C12 -0.43(17) . . . . ?
C10 C11 C12 C13 -0.04(18) . . . . ?
C11 C12 C13 C14 0.22(18) . . . . ?
C12 C13 C14 C9 0.06(18) . . . . ?
C10 C9 C14 C13 -0.51(16) . . . . ?
C8 C9 C14 C13 175.42(10) . . . . ?
C8 N1 C15 C16 -68.21(12) . . . . ?
C1 N1 C15 C16 162.17(9) . . . . ?
N1 C15 C16 C21 132.83(11) . . . . ?
N1 C15 C16 C17 -47.36(14) . . . . ?
C21 C16 C17 C18 -0.76(18) . . . . ?
C15 C16 C17 C18 179.42(11) . . . . ?
C16 C17 C18 C19 0.31(18) . . . . ?
C17 C18 C19 C20 0.23(19) . . . . ?
C18 C19 C20 C21 -0.30(19) . . . . ?
C17 C16 C21 C20 0.69(18) . . . . ?
C15 C16 C21 C20 -179.49(11) . . . . ?
C19 C20 C21 C16 -0.17(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.913
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_tom_jones3
_database_code_depnum_ccdc_archive 'CCDC 1064081'
_audit_update_record             
;
2015-05-08 deposited with the CCDC.
2015-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H24 F3 N O'
_chemical_formula_weight         363.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
F F 0.0171 0.0103 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0335(3)
_cell_length_b                   9.8976(3)
_cell_length_c                   11.7319(3)
_cell_angle_alpha                95.431(3)
_cell_angle_beta                 101.143(3)
_cell_angle_gamma                115.147(3)
_cell_volume                     912.99(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    10119
_cell_measurement_theta_min      3.2048
_cell_measurement_theta_max      30.3927


_exptl_crystal_description       'cut block'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_min  0.90539
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(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  'Oxford Diffraction Xcalibur E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16095
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         30.46
_reflns_number_total             5061
_reflns_number_gt                4423
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       CrysalisPro
_computing_cell_refinement       CrysalisPro
_computing_data_reduction        CrysalisPro
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  SHELXL-97


_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 > 2σ(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)+(0.0465P)²+0.3110P] 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     SHELXL
_refine_ls_extinction_coef       0.034(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5061
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1005
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
F1 F 1.16072(9) 0.62670(8) 0.85896(6) 0.03159(17) Uani 1 1 d . . .
F2 F 1.32366(8) 0.51941(8) 0.88324(7) 0.03468(18) Uani 1 1 d . . .
F3 F 1.22973(8) 0.54900(7) 0.70962(6) 0.03031(16) Uani 1 1 d . . .
O1 O 0.98539(10) 0.35335(11) 0.90042(7) 0.02785(18) Uani 1 1 d . . .
N1 N 0.79466(10) 0.41914(9) 0.71040(7) 0.01544(16) Uani 1 1 d . . .
C1 C 1.03181(12) 0.35609(11) 0.79158(8) 0.01766(18) Uani 1 1 d . . .
C2 C 0.87530(11) 0.32021(10) 0.68923(8) 0.01535(17) Uani 1 1 d . . .
H2 H 0.7901 0.2171 0.6943 0.018 Uiso 1 1 calc R . .
C3 C 0.90258(13) 0.29705(11) 0.56542(8) 0.01943(19) Uani 1 1 d . . .
H3A H 0.7955 0.2671 0.5047 0.023 Uiso 1 1 calc R . .
H3B H 0.9889 0.3939 0.5534 0.023 Uiso 1 1 calc R . .
C4 C 0.96083(14) 0.17363(12) 0.55065(10) 0.0243(2) Uani 1 1 d . . .
H4A H 0.8676 0.0739 0.5511 0.029 Uiso 1 1 calc R . .
H4B H 0.9880 0.1672 0.4731 0.029 Uiso 1 1 calc R . .
C5 C 1.11648(14) 0.20694(13) 0.64958(10) 0.0257(2) Uani 1 1 d . . .
H5A H 1.1451 0.1211 0.6408 0.031 Uiso 1 1 calc R . .
H5B H 1.2140 0.2997 0.6427 0.031 Uiso 1 1 calc R . .
C6 C 1.08503(13) 0.22992(12) 0.77158(10) 0.0230(2) Uani 1 1 d . . .
H6A H 1.1897 0.2551 0.8332 0.028 Uiso 1 1 calc R . .
H6B H 0.9954 0.1332 0.7810 0.028 Uiso 1 1 calc R . .
C7 C 1.18558(13) 0.51231(12) 0.80994(9) 0.0228(2) Uani 1 1 d . . .
C8 C 0.60889(12) 0.33323(11) 0.66555(9) 0.01851(19) Uani 1 1 d . . .
H8A H 0.5808 0.2809 0.5824 0.022 Uiso 1 1 calc R . .
H8B H 0.5602 0.4059 0.6657 0.022 Uiso 1 1 calc R . .
C9 C 0.52767(11) 0.21694(11) 0.73674(8) 0.01699(18) Uani 1 1 d . . .
C10 C 0.54213(13) 0.26390(12) 0.85598(9) 0.0217(2) Uani 1 1 d . . .
H10 H 0.6093 0.3682 0.8930 0.026 Uiso 1 1 calc R . .
C11 C 0.45920(14) 0.15951(13) 0.92089(10) 0.0253(2) Uani 1 1 d . . .
H11 H 0.4701 0.1924 1.0022 0.030 Uiso 1 1 calc R . .
C12 C 0.36022(13) 0.00692(12) 0.86757(10) 0.0252(2) Uani 1 1 d . . .
H12 H 0.3023 -0.0642 0.9120 0.030 Uiso 1 1 calc R . .
C13 C 0.34623(14) -0.04109(12) 0.74968(10) 0.0247(2) Uani 1 1 d . . .
H13 H 0.2791 -0.1454 0.7130 0.030 Uiso 1 1 calc R . .
C14 C 0.43070(13) 0.06379(11) 0.68487(9) 0.02051(19) Uani 1 1 d . . .
H14 H 0.4218 0.0301 0.6042 0.025 Uiso 1 1 calc R . .
C15 C 0.85252(13) 0.55679(11) 0.65853(8) 0.01804(18) Uani 1 1 d . . .
H15A H 0.8020 0.5280 0.5718 0.022 Uiso 1 1 calc R . .
H15B H 0.9772 0.6035 0.6726 0.022 Uiso 1 1 calc R . .
C16 C 0.80322(12) 0.67183(11) 0.71181(9) 0.01803(19) Uani 1 1 d . . .
C17 C 0.70665(14) 0.72451(12) 0.63987(9) 0.0235(2) Uani 1 1 d . . .
H17 H 0.6716 0.6880 0.5566 0.028 Uiso 1 1 calc R . .
C18 C 0.66054(15) 0.83014(13) 0.68843(10) 0.0276(2) Uani 1 1 d . . .
H18 H 0.5937 0.8646 0.6383 0.033 Uiso 1 1 calc R . .
C19 C 0.71177(14) 0.88489(12) 0.80947(10) 0.0259(2) Uani 1 1 d . . .
H19 H 0.6808 0.9573 0.8427 0.031 Uiso 1 1 calc R . .
C20 C 0.80862(14) 0.83336(13) 0.88196(10) 0.0257(2) Uani 1 1 d . . .
H20 H 0.8444 0.8709 0.9651 0.031 Uiso 1 1 calc R . .
C21 C 0.85375(13) 0.72724(12) 0.83385(9) 0.0226(2) Uani 1 1 d . . .
H21 H 0.9195 0.6922 0.8844 0.027 Uiso 1 1 calc R . .
H1H H 0.917(2) 0.391(2) 0.8944(15) 0.047(5) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C7 1.3438(12) . ?
F2 C7 1.3416(12) . ?
F3 C7 1.3473(13) . ?
O1 C1 1.4181(12) . ?
O1 H1H 0.847(18) . ?
N1 C15 1.4745(12) . ?
N1 C8 1.4756(12) . ?
N1 C2 1.4769(11) . ?
C1 C6 1.5310(14) . ?
C1 C7 1.5371(14) . ?
C1 C2 1.5502(13) . ?
C2 C3 1.5318(13) . ?
C2 H2 1.0000 . ?
C3 C4 1.5299(14) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5283(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5270(16) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C9 1.5040(13) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.3879(13) . ?
C9 C10 1.3945(14) . ?
C10 C11 1.3857(14) . ?
C10 H10 0.9500 . ?
C11 C12 1.3889(15) . ?
C11 H11 0.9500 . ?
C12 C13 1.3826(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.3922(15) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.5131(13) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.3894(14) . ?
C16 C21 1.3946(14) . ?
C17 C18 1.3929(15) . ?
C17 H17 0.9500 . ?
C18 C19 1.3825(16) . ?
C18 H18 0.9500 . ?
C19 C20 1.3866(16) . ?
C19 H19 0.9500 . ?
C20 C21 1.3888(15) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

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
C1 O1 H1H 105.5(12) . . ?
C15 N1 C8 108.22(7) . . ?
C15 N1 C2 114.99(7) . . ?
C8 N1 C2 110.68(7) . . ?
O1 C1 C6 108.02(8) . . ?
O1 C1 C7 105.15(8) . . ?
C6 C1 C7 109.60(8) . . ?
O1 C1 C2 109.09(7) . . ?
C6 C1 C2 108.03(8) . . ?
C7 C1 C2 116.65(8) . . ?
N1 C2 C3 116.64(7) . . ?
N1 C2 C1 112.62(7) . . ?
C3 C2 C1 113.90(8) . . ?
N1 C2 H2 103.9 . . ?
C3 C2 H2 103.9 . . ?
C1 C2 H2 103.9 . . ?
C4 C3 C2 110.61(8) . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C3 111.60(8) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C6 C5 C4 111.25(8) . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 C1 113.32(8) . . ?
C5 C6 H6A 108.9 . . ?
C1 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
C1 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
F2 C7 F1 105.99(8) . . ?
F2 C7 F3 105.99(8) . . ?
F1 C7 F3 106.09(9) . . ?
F2 C7 C1 111.49(9) . . ?
F1 C7 C1 112.47(8) . . ?
F3 C7 C1 114.23(8) . . ?
N1 C8 C9 113.66(8) . . ?
N1 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
N1 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C14 C9 C10 118.83(9) . . ?
C14 C9 C8 121.38(9) . . ?
C10 C9 C8 119.71(9) . . ?
C11 C10 C9 120.44(9) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.23(10) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 119.80(10) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 119.87(10) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C9 C14 C13 120.81(9) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
N1 C15 C16 111.36(8) . . ?
N1 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
N1 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C17 C16 C21 118.66(9) . . ?
C17 C16 C15 120.54(9) . . ?
C21 C16 C15 120.79(9) . . ?
C16 C17 C18 120.80(10) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 120.13(10) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 119.49(10) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C19 C20 C21 120.49(10) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 120.42(10) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N1 C2 C3 -40.74(11) . . . . ?
C8 N1 C2 C3 82.25(10) . . . . ?
C15 N1 C2 C1 93.70(9) . . . . ?
C8 N1 C2 C1 -143.30(8) . . . . ?
O1 C1 C2 N1 52.67(10) . . . . ?
C6 C1 C2 N1 169.86(8) . . . . ?
C7 C1 C2 N1 -66.22(10) . . . . ?
O1 C1 C2 C3 -171.60(8) . . . . ?
C6 C1 C2 C3 -54.41(10) . . . . ?
C7 C1 C2 C3 69.52(11) . . . . ?
N1 C2 C3 C4 -171.14(8) . . . . ?
C1 C2 C3 C4 54.98(11) . . . . ?
C2 C3 C4 C5 -53.71(11) . . . . ?
C3 C4 C5 C6 54.65(12) . . . . ?
C4 C5 C6 C1 -56.45(12) . . . . ?
O1 C1 C6 C5 172.56(8) . . . . ?
C7 C1 C6 C5 -73.38(11) . . . . ?
C2 C1 C6 C5 54.68(11) . . . . ?
O1 C1 C7 F2 71.66(10) . . . . ?
C6 C1 C7 F2 -44.24(11) . . . . ?
C2 C1 C7 F2 -167.35(8) . . . . ?
O1 C1 C7 F1 -47.24(11) . . . . ?
C6 C1 C7 F1 -163.13(8) . . . . ?
C2 C1 C7 F1 73.76(11) . . . . ?
O1 C1 C7 F3 -168.23(8) . . . . ?
C6 C1 C7 F3 75.88(10) . . . . ?
C2 C1 C7 F3 -47.23(12) . . . . ?
C15 N1 C8 C9 -163.08(8) . . . . ?
C2 N1 C8 C9 70.08(10) . . . . ?
N1 C8 C9 C14 -121.76(10) . . . . ?
N1 C8 C9 C10 61.61(12) . . . . ?
C14 C9 C10 C11 -0.82(15) . . . . ?
C8 C9 C10 C11 175.90(9) . . . . ?
C9 C10 C11 C12 -0.24(16) . . . . ?
C10 C11 C12 C13 0.81(17) . . . . ?
C11 C12 C13 C14 -0.31(16) . . . . ?
C10 C9 C14 C13 1.32(14) . . . . ?
C8 C9 C14 C13 -175.35(9) . . . . ?
C12 C13 C14 C9 -0.76(16) . . . . ?
C8 N1 C15 C16 71.71(10) . . . . ?
C2 N1 C15 C16 -163.99(8) . . . . ?
N1 C15 C16 C17 -123.19(10) . . . . ?
N1 C15 C16 C21 56.87(12) . . . . ?
C21 C16 C17 C18 -0.21(16) . . . . ?
C15 C16 C17 C18 179.85(10) . . . . ?
C16 C17 C18 C19 0.48(17) . . . . ?
C17 C18 C19 C20 -0.27(17) . . . . ?
C18 C19 C20 C21 -0.19(17) . . . . ?
C19 C20 C21 C16 0.45(16) . . . . ?
C17 C16 C21 C20 -0.25(15) . . . . ?
C15 C16 C21 C20 179.69(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.913
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_tomjonesdec2014
_database_code_depnum_ccdc_archive 'CCDC 1064082'
_audit_update_record             
;
2015-05-08 deposited with the CCDC.
2015-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H12 F3 N O'
_chemical_formula_weight         183.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
F F 0.0171 0.0103 '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'
H H 0.0000 0.0000 '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 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.3916(6)
_cell_length_b                   10.5116(5)
_cell_length_c                   9.3538(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.449(6)
_cell_angle_gamma                90
_cell_volume                     808.67(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2650
_cell_measurement_theta_min      3.1386
_cell_measurement_theta_max      29.3367


_exptl_crystal_description       'cut from prism'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.146
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.57603
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   tube
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7340
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.145
_diffrn_reflns_theta_max         28.991
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2052
_reflns_number_gt                1501
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       CrysalisPro
_computing_cell_refinement       CrysalisPro
_computing_data_reduction        CrysalisPro
_computing_structure_solution    SIR92
_computing_structure_refinement  SHELXL
_computing_molecular_graphics    ?
_computing_publication_material  SHELXL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0449P)²+0.0214P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2052
_refine_ls_number_parameters     121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1093
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.91579(12) -0.25683(8) 0.17186(10) 0.0340(3) Uani 1 1 d . . . . .
F2 F 0.89080(11) -0.12138(8) -0.00383(9) 0.0279(2) Uani 1 1 d . . . . .
F3 F 1.05549(11) -0.08325(9) 0.19943(10) 0.0358(3) Uani 1 1 d . . . . .
O1 O 0.62583(12) -0.13635(8) 0.14560(12) 0.0208(3) Uani 1 1 d . . . . .
N1 N 0.47095(16) 0.11996(13) 0.15657(14) 0.0241(3) Uani 1 1 d . . . . .
C1 C 0.77080(17) -0.06709(12) 0.19901(15) 0.0177(3) Uani 1 1 d . . . . .
C2 C 0.75781(17) 0.07301(12) 0.15022(15) 0.0182(3) Uani 1 1 d . . . . .
H2A H 0.8672 0.1122 0.1736 0.022 Uiso 1 1 calc R U . . .
H2B H 0.7200 0.0765 0.0431 0.022 Uiso 1 1 calc R U . . .
C3 C 0.64138(18) 0.15079(13) 0.22281(15) 0.0203(3) Uani 1 1 d . . . . .
H3 H 0.6588 0.2424 0.2017 0.024 Uiso 1 1 calc R U . . .
C4 C 0.68103(19) 0.13482(13) 0.38864(16) 0.0232(3) Uani 1 1 d . . . . .
H4A H 0.7880 0.1740 0.4280 0.028 Uiso 1 1 calc R U . . .
H4B H 0.5982 0.1800 0.4316 0.028 Uiso 1 1 calc R U . . .
C5 C 0.6850(2) -0.00478(13) 0.43317(15) 0.0254(4) Uani 1 1 d . . . . .
H5A H 0.7152 -0.0116 0.5407 0.031 Uiso 1 1 calc R U . . .
H5B H 0.5756 -0.0425 0.4015 0.031 Uiso 1 1 calc R U . . .
C6 C 0.8069(2) -0.07771(13) 0.36475(16) 0.0237(3) Uani 1 1 d . . . . .
H6A H 0.8050 -0.1685 0.3926 0.028 Uiso 1 1 calc R U . . .
H6B H 0.9174 -0.0444 0.4034 0.028 Uiso 1 1 calc R U . . .
C7 C 0.90808(18) -0.13144(13) 0.14185(17) 0.0242(4) Uani 1 1 d . . . . .
H1N H 0.407(2) 0.1663(16) 0.1989(18) 0.031(5) Uiso 1 1 d . . . . .
H2N H 0.446(2) 0.0412(17) 0.1765(18) 0.034(5) Uiso 1 1 d . . . . .
H1H H 0.597(2) -0.1289(17) 0.050(2) 0.049(6) Uiso 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
F1 C7 1.3465(16) . ?
F2 C7 1.3456(17) . ?
F3 C7 1.3462(17) . ?
O1 C1 1.4207(16) . ?
O1 H1H 0.88(2) . ?
N1 C3 1.4773(19) . ?
N1 H1N 0.876(17) . ?
N1 H2N 0.883(18) . ?
C1 C7 1.522(2) . ?
C1 C6 1.5236(19) . ?
C1 C2 1.5392(18) . ?
C2 C3 1.5321(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5297(19) . ?
C3 H3 1.0000 . ?
C4 C5 1.5240(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.518(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?

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
C1 O1 H1H 111.0(12) . . ?
C3 N1 H1N 108.6(11) . . ?
C3 N1 H2N 111.6(11) . . ?
H1N N1 H2N 103.5(16) . . ?
O1 C1 C7 107.69(11) . . ?
O1 C1 C6 107.68(12) . . ?
C7 C1 C6 108.27(12) . . ?
O1 C1 C2 112.38(11) . . ?
C7 C1 C2 109.58(12) . . ?
C6 C1 C2 111.09(11) . . ?
C3 C2 C1 113.14(11) . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
N1 C3 C4 113.50(13) . . ?
N1 C3 C2 110.27(11) . . ?
C4 C3 C2 111.18(11) . . ?
N1 C3 H3 107.2 . . ?
C4 C3 H3 107.2 . . ?
C2 C3 H3 107.2 . . ?
C5 C4 C3 111.80(11) . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 C4 110.57(13) . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C5 C6 C1 112.18(12) . . ?
C5 C6 H6A 109.2 . . ?
C1 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C1 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
F2 C7 F3 106.34(12) . . ?
F2 C7 F1 106.20(11) . . ?
F3 C7 F1 106.42(11) . . ?
F2 C7 C1 112.58(12) . . ?
F3 C7 C1 113.07(11) . . ?
F1 C7 C1 111.74(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 69.54(15) . . . . ?
C7 C1 C2 C3 -170.78(11) . . . . ?
C6 C1 C2 C3 -51.18(16) . . . . ?
C1 C2 C3 N1 -75.50(14) . . . . ?
C1 C2 C3 C4 51.31(15) . . . . ?
N1 C3 C4 C5 70.96(16) . . . . ?
C2 C3 C4 C5 -54.05(16) . . . . ?
C3 C4 C5 C6 56.99(17) . . . . ?
C4 C5 C6 C1 -57.13(16) . . . . ?
O1 C1 C6 C5 -69.48(14) . . . . ?
C7 C1 C6 C5 174.35(12) . . . . ?
C2 C1 C6 C5 53.97(16) . . . . ?
O1 C1 C7 F2 66.90(14) . . . . ?
C6 C1 C7 F2 -176.94(11) . . . . ?
C2 C1 C7 F2 -55.62(15) . . . . ?
O1 C1 C7 F3 -172.55(11) . . . . ?
C6 C1 C7 F3 -56.38(16) . . . . ?
C2 C1 C7 F3 64.93(15) . . . . ?
O1 C1 C7 F1 -52.52(15) . . . . ?
C6 C1 C7 F1 63.65(15) . . . . ?
C2 C1 C7 F1 -175.04(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2A F1 0.99 2.50 3.4149(16) 153.3 2_755
C6 H6A F2 0.99 2.46 3.4158(16) 161.8 4_556
N1 H1N O1 0.876(17) 2.580(17) 3.3530(17) 147.7(14) 2_655
N1 H2N O1 0.883(18) 2.453(17) 3.0019(16) 120.8(14) .
O1 H1H N1 0.88(2) 1.91(2) 2.7869(17) 177.5(18) 3_655

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.055

#===END
