# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_aa581_cu
_database_code_depnum_ccdc_archive 'CCDC 1577645'
_audit_update_record             
;
2017-10-02 deposited with the CCDC.
2018-04-05 downloaded from the CCDC.
;
_audit_creation_date             2015-06-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H29 F N2 O4'
_chemical_formula_sum            'C22 H29 F N2 O4'
_chemical_formula_weight         404.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H29 F1 N2 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_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                   10.7014(2)
_cell_length_b                   14.4421(3)
_cell_length_c                   14.1016(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.984(3)
_cell_angle_gamma                90
_cell_volume                     2084.35(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7487
_cell_measurement_temperature    119.99(17)
_cell_measurement_theta_max      74.3060
_cell_measurement_theta_min      4.4620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_T_max  0.943
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14166
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.387
_diffrn_reflns_theta_min         4.320
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119.99(17)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -33.00   22.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000 -150.0000 55

#__ type_ start__ end____ width___ exp.time_
  2 omega  -48.00   -1.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   37.0000 -180.0000 47

#__ type_ start__ end____ width___ exp.time_
  3 omega  -80.00   37.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000    0.0000  -60.0000 117

#__ type_ start__ end____ width___ exp.time_
  4 omega   77.00  135.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   15.0000 -150.0000 58

#__ type_ start__ end____ width___ exp.time_
  5 omega   99.00  125.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   45.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   85.00  175.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   45.0000 -150.0000 90

#__ type_ start__ end____ width___ exp.time_
  7 omega  139.00  165.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega  150.00  176.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   45.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega  119.00  168.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   61.0000   90.0000 49

#__ type_ start__ end____ width___ exp.time_
 10 omega  108.00  145.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   61.0000  -30.0000 37

#__ type_ start__ end____ width___ exp.time_
 11 omega  102.00  127.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   30.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 12 omega   84.00  136.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   45.0000   30.0000 52

#__ type_ start__ end____ width___ exp.time_
 13 omega   93.00  118.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000   61.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 14 omega   64.00   90.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega  104.00  129.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 16 omega   56.00  131.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000   30.0000 75

#__ type_ start__ end____ width___ exp.time_
 17 omega   59.00  124.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -64.0000  108.4734 65

#__ type_ start__ end____ width___ exp.time_
 18 omega   55.00   80.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -45.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 19 omega   42.00   80.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000   30.0000 38

#__ type_ start__ end____ width___ exp.time_
 20 omega   54.00  122.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000  -90.0000 68

#__ type_ start__ end____ width___ exp.time_
 21 omega   52.00   98.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -61.0000 -180.0000 46

#__ type_ start__ end____ width___ exp.time_
 22 omega   40.00   79.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      106.0000  -30.0000 -180.0000 39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0763796000
_diffrn_orient_matrix_UB_12      -0.0911254000
_diffrn_orient_matrix_UB_13      0.0049040000
_diffrn_orient_matrix_UB_21      0.0856812000
_diffrn_orient_matrix_UB_22      0.0252244000
_diffrn_orient_matrix_UB_23      0.1050605000
_diffrn_orient_matrix_UB_31      -0.0973922000
_diffrn_orient_matrix_UB_32      -0.0493166000
_diffrn_orient_matrix_UB_33      0.0446542000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3739
_reflns_number_total             4241
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0420P)²+0.6121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0988
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C14(H14A,H14B), C16(H16A,H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 -0.00783(8) 0.13304(6) 0.03131(7) 0.0344(2) Uani 1 1 d . . . . .
O1 O 0.57219(9) 0.13662(6) 0.01388(7) 0.0228(2) Uani 1 1 d . . . . .
N1 N 0.48677(9) 0.24527(7) -0.10522(7) 0.0173(2) Uani 1 1 d . . . . .
C1 C 0.10949(12) 0.14444(10) 0.01405(9) 0.0242(3) Uani 1 1 d . . . . .
O2 O 0.68540(9) 0.12126(6) -0.14014(8) 0.0265(2) Uani 1 1 d . . . . .
N2 N 0.70253(10) 0.40422(7) -0.01672(8) 0.0216(2) Uani 1 1 d . . . . .
C2 C 0.18730(13) 0.06778(9) 0.01631(10) 0.0248(3) Uani 1 1 d . . . . .
H2A H 0.1604 0.0092 0.0296 0.030 Uiso 1 1 calc R . . . .
O3 O 0.77131(10) 0.54184(6) 0.05677(8) 0.0338(3) Uani 1 1 d . . . . .
C3 C 0.30699(12) 0.08062(9) -0.00178(9) 0.0214(3) Uani 1 1 d . . . . .
H3 H 0.3618 0.0303 0.0000 0.026 Uiso 1 1 calc R . . . .
O4 O 0.88327(8) 0.40777(6) 0.10969(6) 0.02004(19) Uani 1 1 d . . . . .
C4 C 0.34524(12) 0.16894(8) -0.02258(8) 0.0188(2) Uani 1 1 d . . . . .
C5 C 0.26409(12) 0.24479(8) -0.02378(9) 0.0201(2) Uani 1 1 d . . . . .
H5 H 0.2900 0.3036 -0.0373 0.024 Uiso 1 1 calc R . . . .
C6 C 0.14500(12) 0.23285(9) -0.00491(9) 0.0224(3) Uani 1 1 d . . . . .
H6 H 0.0905 0.2830 -0.0050 0.027 Uiso 1 1 calc R . . . .
C7 C 0.47737(12) 0.18101(8) -0.03724(9) 0.0185(2) Uani 1 1 d . . . . .
C8 C 0.38504(11) 0.25930(9) -0.20133(9) 0.0196(2) Uani 1 1 d . . . . .
H8 H 0.2970 0.2551 -0.1939 0.024 Uiso 1 1 calc R . . . .
C9 C 0.40819(12) 0.18408(9) -0.27094(9) 0.0231(3) Uani 1 1 d . . . . .
H9A H 0.4018 0.1235 -0.2429 0.028 Uiso 1 1 calc R . . . .
H9B H 0.3414 0.1882 -0.3344 0.028 Uiso 1 1 calc R . . . .
C10 C 0.54322(12) 0.19521(9) -0.28636(9) 0.0235(3) Uani 1 1 d . . . . .
H10A H 0.5413 0.2481 -0.3292 0.028 Uiso 1 1 calc R . . . .
H10B H 0.5618 0.1407 -0.3201 0.028 Uiso 1 1 calc R . . . .
C11 C 0.65464(12) 0.20877(9) -0.18959(9) 0.0206(2) Uani 1 1 d . . . . .
C12 C 0.61058(11) 0.27840(8) -0.12194(9) 0.0175(2) Uani 1 1 d . . . . .
C13 C 0.56129(11) 0.37175(8) -0.17489(9) 0.0184(2) Uani 1 1 d . . . . .
H13 H 0.6102 0.3881 -0.2214 0.022 Uiso 1 1 calc R . . . .
C14 C 0.41492(11) 0.35759(9) -0.22996(9) 0.0214(3) Uani 1 1 d . . . . .
H14A H 0.3617 0.4029 -0.2088 0.026 Uiso 1 1 calc R . . . .
H14B H 0.3989 0.3628 -0.3011 0.026 Uiso 1 1 calc R . . . .
C15 C 0.77646(13) 0.23983(10) -0.21603(11) 0.0274(3) Uani 1 1 d . . . . .
C16 C 0.71474(11) 0.30383(8) -0.02457(9) 0.0193(2) Uani 1 1 d . . . . .
H16A H 0.6979 0.2726 0.0314 0.023 Uiso 1 1 calc R . . . .
H16B H 0.8014 0.2871 -0.0273 0.023 Uiso 1 1 calc R . . . .
C17 C 0.58731(12) 0.44125(8) -0.08972(10) 0.0220(3) Uani 1 1 d . . . . .
H17A H 0.6044 0.5025 -0.1114 0.026 Uiso 1 1 calc R . . . .
H17B H 0.5137 0.4447 -0.0628 0.026 Uiso 1 1 calc R . . . .
C18 C 0.78477(12) 0.45844(8) 0.05105(9) 0.0210(2) Uani 1 1 d . . . . .
C19 C 0.98998(12) 0.45257(9) 0.18673(9) 0.0226(3) Uani 1 1 d . . . . .
C20 C 1.07321(12) 0.37031(10) 0.23425(10) 0.0253(3) Uani 1 1 d . . . . .
H20A H 1.0230 0.3300 0.2631 0.038 Uiso 1 1 calc GR . . . .
H20B H 1.1487 0.3918 0.2849 0.038 Uiso 1 1 calc GR . . . .
H20C H 1.1006 0.3372 0.1847 0.038 Uiso 1 1 calc GR . . . .
C21 C 0.93781(14) 0.50294(11) 0.26194(11) 0.0334(3) Uani 1 1 d . . . . .
H21A H 0.8926 0.5579 0.2323 0.050 Uiso 1 1 calc GR . . . .
H21B H 1.0092 0.5195 0.3185 0.050 Uiso 1 1 calc GR . . . .
H21C H 0.8787 0.4632 0.2825 0.050 Uiso 1 1 calc GR . . . .
C22 C 1.06763(15) 0.51535(12) 0.13834(12) 0.0374(4) Uani 1 1 d . . . . .
H22A H 1.0963 0.4807 0.0905 0.056 Uiso 1 1 calc GR . . . .
H22B H 1.1422 0.5392 0.1881 0.056 Uiso 1 1 calc GR . . . .
H22C H 1.0134 0.5658 0.1059 0.056 Uiso 1 1 calc GR . . . .
H15A H 0.8555(19) 0.2418(13) -0.1562(15) 0.036(5) Uiso 1 1 d . . . . .
H15B H 0.7954(18) 0.1964(13) -0.2621(14) 0.034(4) Uiso 1 1 d . . . . .
H15C H 0.7635(18) 0.2981(14) -0.2499(14) 0.035(5) Uiso 1 1 d . . . . .
H2 H 0.658(2) 0.1211(14) -0.0871(17) 0.041(5) 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 C1 1.3569(15) . ?
O1 C7 1.2381(15) . ?
N1 C7 1.3589(16) . ?
N1 C8 1.4837(14) . ?
N1 C12 1.4908(15) . ?
C1 C2 1.380(2) . ?
C1 C6 1.3803(19) . ?
O2 C11 1.4345(15) . ?
O2 H2 0.88(2) . ?
N2 C16 1.4629(15) . ?
N2 C17 1.4577(15) . ?
N2 C18 1.3452(17) . ?
C2 H2A 0.9300 . ?
C2 C3 1.3895(19) . ?
O3 C18 1.2185(16) . ?
C3 H3 0.9300 . ?
C3 C4 1.3967(17) . ?
O4 C18 1.3495(15) . ?
O4 C19 1.4759(14) . ?
C4 C5 1.3950(17) . ?
C4 C7 1.4977(17) . ?
C5 H5 0.9300 . ?
C5 C6 1.3868(18) . ?
C6 H6 0.9300 . ?
C8 H8 0.9800 . ?
C8 C9 1.5320(18) . ?
C8 C14 1.5348(17) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.5312(17) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.5400(17) . ?
C11 C12 1.5514(17) . ?
C11 C15 1.5243(18) . ?
C12 C13 1.5566(16) . ?
C12 C16 1.5389(15) . ?
C13 H13 0.9800 . ?
C13 C14 1.5452(16) . ?
C13 C17 1.5271(17) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 1.01(2) . ?
C15 H15B 0.97(2) . ?
C15 H15C 0.96(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C19 C20 1.5183(18) . ?
C19 C21 1.5204(19) . ?
C19 C22 1.5197(19) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C8 123.50(10) . . ?
C7 N1 C12 125.67(10) . . ?
C8 N1 C12 105.10(9) . . ?
F1 C1 C2 118.82(12) . . ?
F1 C1 C6 117.94(12) . . ?
C2 C1 C6 123.24(12) . . ?
C11 O2 H2 109.3(14) . . ?
C17 N2 C16 112.70(10) . . ?
C18 N2 C16 125.20(10) . . ?
C18 N2 C17 122.08(10) . . ?
C1 C2 H2A 121.0 . . ?
C1 C2 C3 118.10(12) . . ?
C3 C2 H2A 121.0 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.19(12) . . ?
C4 C3 H3 119.9 . . ?
C18 O4 C19 120.74(9) . . ?
C3 C4 C7 118.79(11) . . ?
C5 C4 C3 120.01(11) . . ?
C5 C4 C7 121.09(11) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.25(11) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.21(12) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
O1 C7 N1 123.19(11) . . ?
O1 C7 C4 120.37(11) . . ?
N1 C7 C4 116.37(10) . . ?
N1 C8 H8 111.4 . . ?
N1 C8 C9 106.00(9) . . ?
N1 C8 C14 102.29(9) . . ?
C9 C8 H8 111.4 . . ?
C9 C8 C14 113.71(10) . . ?
C14 C8 H8 111.4 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 C8 110.64(10) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C9 C10 C11 113.96(10) . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
O2 C11 C10 109.09(10) . . ?
O2 C11 C12 109.87(10) . . ?
O2 C11 C15 106.68(10) . . ?
C10 C11 C12 109.36(10) . . ?
C15 C11 C10 108.47(11) . . ?
C15 C11 C12 113.26(10) . . ?
N1 C12 C11 109.45(9) . . ?
N1 C12 C13 99.30(9) . . ?
N1 C12 C16 112.40(9) . . ?
C11 C12 C13 112.81(10) . . ?
C16 C12 C11 115.61(9) . . ?
C16 C12 C13 106.08(9) . . ?
C12 C13 H13 110.9 . . ?
C14 C13 C12 106.15(9) . . ?
C14 C13 H13 110.9 . . ?
C17 C13 C12 103.51(9) . . ?
C17 C13 H13 110.9 . . ?
C17 C13 C14 114.04(10) . . ?
C8 C14 C13 104.40(9) . . ?
C8 C14 H14A 110.9 . . ?
C8 C14 H14B 110.9 . . ?
C13 C14 H14A 110.9 . . ?
C13 C14 H14B 110.9 . . ?
H14A C14 H14B 108.9 . . ?
C11 C15 H15A 111.9(11) . . ?
C11 C15 H15B 109.6(11) . . ?
C11 C15 H15C 111.8(11) . . ?
H15A C15 H15B 107.0(15) . . ?
H15A C15 H15C 110.9(16) . . ?
H15B C15 H15C 105.3(16) . . ?
N2 C16 C12 104.28(9) . . ?
N2 C16 H16A 110.9 . . ?
N2 C16 H16B 110.9 . . ?
C12 C16 H16A 110.9 . . ?
C12 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
N2 C17 C13 103.69(9) . . ?
N2 C17 H17A 111.0 . . ?
N2 C17 H17B 111.0 . . ?
C13 C17 H17A 111.0 . . ?
C13 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?
N2 C18 O4 110.57(10) . . ?
O3 C18 N2 123.85(12) . . ?
O3 C18 O4 125.58(11) . . ?
O4 C19 C20 102.11(10) . . ?
O4 C19 C21 111.13(10) . . ?
O4 C19 C22 109.76(11) . . ?
C20 C19 C21 110.74(11) . . ?
C20 C19 C22 109.74(12) . . ?
C22 C19 C21 112.84(12) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
F1 C1 C2 C3 179.84(11) . . . . ?
F1 C1 C6 C5 -179.24(11) . . . . ?
N1 C8 C9 C10 -61.87(13) . . . . ?
N1 C8 C14 C13 24.74(12) . . . . ?
N1 C12 C13 C14 -29.47(11) . . . . ?
N1 C12 C13 C17 90.90(10) . . . . ?
N1 C12 C16 N2 -96.99(11) . . . . ?
C1 C2 C3 C4 -0.68(18) . . . . ?
O2 C11 C12 N1 -64.30(12) . . . . ?
O2 C11 C12 C13 -173.84(9) . . . . ?
O2 C11 C12 C16 63.83(13) . . . . ?
C2 C1 C6 C5 0.82(19) . . . . ?
C2 C3 C4 C5 0.96(18) . . . . ?
C2 C3 C4 C7 177.31(11) . . . . ?
C3 C4 C5 C6 -0.35(18) . . . . ?
C3 C4 C7 O1 -37.72(16) . . . . ?
C3 C4 C7 N1 145.17(11) . . . . ?
C4 C5 C6 C1 -0.52(18) . . . . ?
C5 C4 C7 O1 138.58(12) . . . . ?
C5 C4 C7 N1 -38.53(16) . . . . ?
C6 C1 C2 C3 -0.23(19) . . . . ?
C7 N1 C8 C9 -81.01(13) . . . . ?
C7 N1 C8 C14 159.61(11) . . . . ?
C7 N1 C12 C11 82.15(13) . . . . ?
C7 N1 C12 C13 -159.53(11) . . . . ?
C7 N1 C12 C16 -47.74(15) . . . . ?
C7 C4 C5 C6 -176.61(11) . . . . ?
C8 N1 C7 O1 143.14(12) . . . . ?
C8 N1 C7 C4 -39.85(16) . . . . ?
C8 N1 C12 C11 -71.67(11) . . . . ?
C8 N1 C12 C13 46.65(11) . . . . ?
C8 N1 C12 C16 158.44(9) . . . . ?
C8 C9 C10 C11 47.95(15) . . . . ?
C9 C8 C14 C13 -89.09(12) . . . . ?
C9 C10 C11 O2 76.45(13) . . . . ?
C9 C10 C11 C12 -43.74(14) . . . . ?
C9 C10 C11 C15 -167.71(11) . . . . ?
C10 C11 C12 N1 55.42(12) . . . . ?
C10 C11 C12 C13 -54.13(13) . . . . ?
C10 C11 C12 C16 -176.46(10) . . . . ?
C11 C12 C13 C14 86.31(11) . . . . ?
C11 C12 C13 C17 -153.31(10) . . . . ?
C11 C12 C16 N2 136.36(11) . . . . ?
C12 N1 C7 O1 -6.14(18) . . . . ?
C12 N1 C7 C4 170.87(10) . . . . ?
C12 N1 C8 C9 73.53(11) . . . . ?
C12 N1 C8 C14 -45.85(11) . . . . ?
C12 C13 C14 C8 3.20(12) . . . . ?
C12 C13 C17 N2 30.98(12) . . . . ?
C13 C12 C16 N2 10.51(12) . . . . ?
C14 C8 C9 C10 49.72(13) . . . . ?
C14 C13 C17 N2 145.83(10) . . . . ?
C15 C11 C12 N1 176.52(10) . . . . ?
C15 C11 C12 C13 66.98(13) . . . . ?
C15 C11 C12 C16 -55.35(14) . . . . ?
C16 N2 C17 C13 -26.44(14) . . . . ?
C16 N2 C18 O3 -178.98(13) . . . . ?
C16 N2 C18 O4 1.80(18) . . . . ?
C16 C12 C13 C14 -146.16(10) . . . . ?
C16 C12 C13 C17 -25.78(12) . . . . ?
C17 N2 C16 C12 9.93(14) . . . . ?
C17 N2 C18 O3 -0.7(2) . . . . ?
C17 N2 C18 O4 -179.96(11) . . . . ?
C17 C13 C14 C8 -110.09(11) . . . . ?
C18 N2 C16 C12 -171.68(12) . . . . ?
C18 N2 C17 C13 155.11(12) . . . . ?
C18 O4 C19 C20 178.47(10) . . . . ?
C18 O4 C19 C21 60.35(15) . . . . ?
C18 O4 C19 C22 -65.16(15) . . . . ?
C19 O4 C18 N2 176.89(10) . . . . ?
C19 O4 C18 O3 -2.3(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2 5 -8 0.0523 2.0000 5.0081 -8.0084 -0.3429 -0.5437 -0.7994
4 7 2 0.0406 3.9972 7.0122 1.9870 -0.3239 0.7281 -0.6464
-2 -1 -8 0.0512 -1.9974 -1.0028 -7.9965 -0.1004 -1.0365 -0.1131
-4 -8 3 0.0749 -3.9980 -8.0135 3.0143 0.4396 -0.2280 0.9192
0 -2 9 0.0632 -0.0015 -2.0026 9.0025 0.2265 0.8952 0.5009
0 9 0 0.0382 0.0012 9.0117 -0.0103 -0.8212 0.2263 -0.4450
7 0 -2 0.0414 6.9943 0.0054 -2.0089 0.5239 0.3884 -0.7712
0 -9 0 0.0734 -0.0012 -9.0117 0.0103 0.8212 -0.2263 0.4450
2 2 8 0.0527 1.9975 2.0041 7.9953 0.0092 1.0617 0.0636
4 -1 -9 0.0473 3.9977 -0.9982 -9.0041 0.3521 -0.6286 -0.7422
-7 -1 2 0.0682 -6.9944 -1.0067 2.0101 -0.4326 -0.4135 0.8206
-6 -2 -2 0.0571 -5.9949 -2.0072 -1.9901 -0.2847 -0.7734 0.5940
-3 8 0 0.0362 -2.9964 8.0081 -0.0053 -0.9586 -0.0553 -0.1033
4 -8 -1 0.0640 3.9957 -8.0073 -0.9959 1.0300 0.0357 -0.0387
-3 -5 8 0.0775 -2.9992 -5.0088 8.0097 0.2666 0.4582 0.8968
6 2 0 0.0361 5.9952 2.0072 -0.0099 0.2750 0.5633 -0.6833
-6 1 -2 0.0484 -5.9945 0.9967 -1.9936 -0.5585 -0.6979 0.4456
6 -1 2 0.0484 5.9945 -0.9967 1.9936 0.5585 0.6979 -0.4456
-1 9 3 0.0390 -0.9984 9.0109 2.9910 -0.8827 0.4560 -0.2136

_olex2_date_sample_data_collection 2015-06-16
_olex2_submission_special_instructions 'No special instructions were received'
