# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_sbc8
_database_code_depnum_ccdc_archive 'CCDC 1522198'
_audit_update_record             
;
2016-12-12 deposited with the CCDC.
2017-05-14 downloaded from the CCDC.
;
_audit_creation_date             2016-12-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H28 N O4'
_chemical_formula_sum            'C23 H28 N O4'
_chemical_formula_weight         382.46
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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 21/c'
_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                   11.1904(16)
_cell_length_b                   13.7744(17)
_cell_length_c                   14.105(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.815(6)
_cell_angle_gamma                90
_cell_volume                     2120.0(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3200
_cell_measurement_temperature    293
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.9
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             820
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.0831
_diffrn_reflns_Laue_measured_fraction_full 0.997
_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       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11343
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.032
_diffrn_reflns_theta_max         25.032
_diffrn_reflns_theta_min         1.866
_diffrn_ambient_temperature      293
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 240.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 533
	           Slice: -69.0000 - 90.9000
	     Image width: 0.3000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 49.8600
	          2theta: 29.8900
;
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.009753
_diffrn_orient_matrix_UB_12      -0.083149
_diffrn_orient_matrix_UB_13      -0.037281
_diffrn_orient_matrix_UB_21      0.062434
_diffrn_orient_matrix_UB_22      0.008811
_diffrn_orient_matrix_UB_23      -0.035985
_diffrn_orient_matrix_UB_31      0.033668
_diffrn_orient_matrix_UB_32      -0.043174
_diffrn_orient_matrix_UB_33      0.047842
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2193
_reflns_number_total             3748
_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       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3737
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1220
_refine_ls_R_factor_gt           0.0756
_refine_ls_restrained_S_all      1.071
_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)+(0.1297P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1928
_refine_ls_wR_factor_ref         0.2453
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00L(H00K,H00L), C00M(H00M,H00N), C00N(H00O,H00P), C00O(H00Q,H00R), C00P(H00S,
 H00T), C00Q(H00U,H00V), C00R(H00W,H00X)
2.b Aromatic/amide H refined with riding coordinates:
 N004(H004), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J)
2.c Idealised Me refined as rotating group:
 C00K(H00A,H00B,H00C), C00S(H00Y,H,HA)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O001 O 0.27702(19) 0.59723(14) 0.39253(15) 0.0654(6) Uani 1 1 d . . . . .
O002 O 0.16742(19) 0.23991(14) -0.31309(14) 0.0663(7) Uani 1 1 d . . . . .
O003 O 0.1782(2) 0.41546(13) 0.09853(14) 0.0670(7) Uani 1 1 d . . . . .
N004 N 0.13268(19) 0.50868(15) -0.06134(15) 0.0486(6) Uani 1 1 d . . . . .
H004 H 0.1427 0.4552 -0.0291 0.058 Uiso 1 1 calc R . . . .
O005 O 0.0109(2) 0.28368(16) -0.42985(16) 0.0837(8) Uani 1 1 d . . . . .
C006 C 0.1062(2) 0.40431(17) -0.20029(19) 0.0430(6) Uani 1 1 d . . . . .
C007 C 0.1052(2) 0.49844(18) -0.16303(19) 0.0447(7) Uani 1 1 d . . . . .
C008 C 0.0799(2) 0.39441(18) -0.30141(19) 0.0459(7) Uani 1 1 d . . . . .
C009 C 0.1765(2) 0.58656(17) 0.09263(19) 0.0470(7) Uani 1 1 d . . . . .
C00A C 0.1941(3) 0.49676(19) 0.1455(2) 0.0508(7) Uani 1 1 d . . . . .
C00B C 0.0821(3) 0.3000(2) -0.3539(2) 0.0545(7) Uani 1 1 d . . . . .
C00C C 0.2432(3) 0.5873(2) 0.2950(2) 0.0532(7) Uani 1 1 d . . . . .
C00D C 0.1453(2) 0.58786(18) -0.0085(2) 0.0506(7) Uani 1 1 d . . . . .
H00D H 0.1328 0.6475 -0.0401 0.061 Uiso 1 1 calc R . . . .
C00E C 0.0780(3) 0.57908(18) -0.2232(2) 0.0529(7) Uani 1 1 d . . . . .
H00E H 0.0782 0.6408 -0.1965 0.063 Uiso 1 1 calc R . . . .
C00F C 0.2248(3) 0.6759(2) 0.2431(2) 0.0582(8) Uani 1 1 d . . . . .
H00F H 0.2350 0.7346 0.2764 0.070 Uiso 1 1 calc R . . . .
C00G C 0.2287(3) 0.5004(2) 0.24702(19) 0.0536(7) Uani 1 1 d . . . . .
H00G H 0.2420 0.4429 0.2823 0.064 Uiso 1 1 calc R . . . .
C00H C 0.0510(3) 0.4762(2) -0.3606(2) 0.0560(8) Uani 1 1 d . . . . .
H00H H 0.0315 0.4684 -0.4278 0.067 Uiso 1 1 calc R . . . .
C00I C 0.1925(3) 0.6750(2) 0.1455(2) 0.0548(8) Uani 1 1 d . . . . .
H00I H 0.1803 0.7336 0.1119 0.066 Uiso 1 1 calc R . . . .
C00J C 0.0508(3) 0.56704(19) -0.3223(2) 0.0563(8) Uani 1 1 d . . . . .
H00J H 0.0322 0.6206 -0.3631 0.068 Uiso 1 1 calc R . . . .
C00K C 0.1315(3) 0.31962(18) -0.13189(19) 0.0542(7) Uani 1 1 d . . . . .
H00A H 0.2161 0.3202 -0.0985 0.081 Uiso 1 1 calc GR . . . .
H00B H 0.1137 0.2603 -0.1680 0.081 Uiso 1 1 calc GR . . . .
H00C H 0.0807 0.3241 -0.0854 0.081 Uiso 1 1 calc GR . . . .
C00L C 0.3015(3) 0.5102(2) 0.4504(2) 0.0645(8) Uani 1 1 d . . . . .
H00K H 0.3653 0.4728 0.4308 0.077 Uiso 1 1 calc R . . . .
H00L H 0.2281 0.4705 0.4407 0.077 Uiso 1 1 calc R . . . .
C00M C 0.3412(3) 0.5378(2) 0.5547(2) 0.0666(9) Uani 1 1 d . . . . .
H00M H 0.2746 0.5710 0.5750 0.080 Uiso 1 1 calc R . . . .
H00N H 0.4100 0.5821 0.5628 0.080 Uiso 1 1 calc R . . . .
C00N C 0.3780(3) 0.4495(2) 0.6181(2) 0.0679(9) Uani 1 1 d . . . . .
H00O H 0.4479 0.4192 0.5998 0.081 Uiso 1 1 calc R . . . .
H00P H 0.3110 0.4032 0.6051 0.081 Uiso 1 1 calc R . . . .
C00O C 0.4454(3) 0.3799(3) 0.7874(2) 0.0723(9) Uani 1 1 d . . . . .
H00Q H 0.3789 0.3334 0.7706 0.087 Uiso 1 1 calc R . . . .
H00R H 0.5170 0.3510 0.7706 0.087 Uiso 1 1 calc R . . . .
C00P C 0.4109(3) 0.4704(2) 0.7262(2) 0.0677(9) Uani 1 1 d . . . . .
H00S H 0.3416 0.5013 0.7448 0.081 Uiso 1 1 calc R . . . .
H00T H 0.4790 0.5156 0.7398 0.081 Uiso 1 1 calc R . . . .
C00Q C 0.4724(3) 0.3965(2) 0.8953(2) 0.0708(9) Uani 1 1 d . . . . .
H00U H 0.4016 0.4268 0.9121 0.085 Uiso 1 1 calc R . . . .
H00V H 0.5405 0.4414 0.9126 0.085 Uiso 1 1 calc R . . . .
C00R C 0.5032(3) 0.3051(3) 0.9548(3) 0.0828(11) Uani 1 1 d . . . . .
H00W H 0.5771 0.2769 0.9412 0.099 Uiso 1 1 calc R . . . .
H00X H 0.4374 0.2586 0.9348 0.099 Uiso 1 1 calc R . . . .
C00S C 0.5226(4) 0.3219(3) 1.0633(3) 0.1170(16) Uani 1 1 d . . . . .
H00Y H 0.4496 0.3493 1.0775 0.175 Uiso 1 1 calc GR . . . .
H H 0.5898 0.3659 1.0842 0.175 Uiso 1 1 calc GR . . . .
HA H 0.5405 0.2613 1.0969 0.175 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00C 1.350(3) . ?
O001 C00L 1.442(3) . ?
O002 C00B 1.298(3) . ?
O003 C00A 1.293(3) . ?
N004 H004 0.8600 . ?
N004 C007 1.406(3) . ?
N004 C00D 1.311(3) . ?
O005 C00B 1.205(3) . ?
C006 C007 1.400(3) . ?
C006 C008 1.398(4) . ?
C006 C00K 1.500(3) . ?
C007 C00E 1.390(3) . ?
C008 C00B 1.499(4) . ?
C008 C00H 1.396(4) . ?
C009 C00A 1.435(4) . ?
C009 C00D 1.392(4) . ?
C009 C00I 1.419(4) . ?
C00A C00G 1.399(4) . ?
C00C C00F 1.414(4) . ?
C00C C00G 1.368(4) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
C00E C00J 1.373(4) . ?
C00F H00F 0.9300 . ?
C00F C00I 1.344(4) . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9300 . ?
C00H C00J 1.364(4) . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00K H00A 0.9600 . ?
C00K H00B 0.9600 . ?
C00K H00C 0.9600 . ?
C00L H00K 0.9700 . ?
C00L H00L 0.9700 . ?
C00L C00M 1.489(4) . ?
C00M H00M 0.9700 . ?
C00M H00N 0.9700 . ?
C00M C00N 1.511(4) . ?
C00N H00O 0.9700 . ?
C00N H00P 0.9700 . ?
C00N C00P 1.516(4) . ?
C00O H00Q 0.9700 . ?
C00O H00R 0.9700 . ?
C00O C00P 1.516(4) . ?
C00O C00Q 1.503(4) . ?
C00P H00S 0.9700 . ?
C00P H00T 0.9700 . ?
C00Q H00U 0.9700 . ?
C00Q H00V 0.9700 . ?
C00Q C00R 1.510(4) . ?
C00R H00W 0.9700 . ?
C00R H00X 0.9700 . ?
C00R C00S 1.515(5) . ?
C00S H00Y 0.9600 . ?
C00S H 0.9600 . ?
C00S HA 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
C00C O001 C00L 117.9(2) . . ?
C007 N004 H004 115.3 . . ?
C00D N004 H004 115.3 . . ?
C00D N004 C007 129.4(2) . . ?
C007 C006 C00K 119.7(2) . . ?
C008 C006 C007 117.1(2) . . ?
C008 C006 C00K 123.2(2) . . ?
C006 C007 N004 117.2(2) . . ?
C00E C007 N004 120.8(2) . . ?
C00E C007 C006 122.0(2) . . ?
C006 C008 C00B 124.5(2) . . ?
C00H C008 C006 120.0(2) . . ?
C00H C008 C00B 115.5(2) . . ?
C00D C009 C00A 121.2(2) . . ?
C00D C009 C00I 120.1(2) . . ?
C00I C009 C00A 118.7(3) . . ?
O003 C00A C009 119.6(3) . . ?
O003 C00A C00G 122.0(3) . . ?
C00G C00A C009 118.4(2) . . ?
O002 C00B C008 115.1(2) . . ?
O005 C00B O002 123.5(3) . . ?
O005 C00B C008 121.4(3) . . ?
O001 C00C C00F 114.6(2) . . ?
O001 C00C C00G 124.6(3) . . ?
C00G C00C C00F 120.7(3) . . ?
N004 C00D C009 122.9(2) . . ?
N004 C00D H00D 118.6 . . ?
C009 C00D H00D 118.6 . . ?
C007 C00E H00E 120.2 . . ?
C00J C00E C007 119.6(2) . . ?
C00J C00E H00E 120.2 . . ?
C00C C00F H00F 120.1 . . ?
C00I C00F C00C 119.9(3) . . ?
C00I C00F H00F 120.1 . . ?
C00A C00G H00G 119.6 . . ?
C00C C00G C00A 120.9(3) . . ?
C00C C00G H00G 119.6 . . ?
C008 C00H H00H 119.2 . . ?
C00J C00H C008 121.6(3) . . ?
C00J C00H H00H 119.2 . . ?
C009 C00I H00I 119.3 . . ?
C00F C00I C009 121.3(3) . . ?
C00F C00I H00I 119.3 . . ?
C00E C00J H00J 120.2 . . ?
C00H C00J C00E 119.7(2) . . ?
C00H C00J H00J 120.2 . . ?
C006 C00K H00A 109.5 . . ?
C006 C00K H00B 109.5 . . ?
C006 C00K H00C 109.5 . . ?
H00A C00K H00B 109.5 . . ?
H00A C00K H00C 109.5 . . ?
H00B C00K H00C 109.5 . . ?
O001 C00L H00K 109.9 . . ?
O001 C00L H00L 109.9 . . ?
O001 C00L C00M 109.0(3) . . ?
H00K C00L H00L 108.3 . . ?
C00M C00L H00K 109.9 . . ?
C00M C00L H00L 109.9 . . ?
C00L C00M H00M 109.4 . . ?
C00L C00M H00N 109.4 . . ?
C00L C00M C00N 111.2(3) . . ?
H00M C00M H00N 108.0 . . ?
C00N C00M H00M 109.4 . . ?
C00N C00M H00N 109.4 . . ?
C00M C00N H00O 108.6 . . ?
C00M C00N H00P 108.6 . . ?
C00M C00N C00P 114.6(3) . . ?
H00O C00N H00P 107.6 . . ?
C00P C00N H00O 108.6 . . ?
C00P C00N H00P 108.6 . . ?
H00Q C00O H00R 107.5 . . ?
C00P C00O H00Q 108.6 . . ?
C00P C00O H00R 108.6 . . ?
C00Q C00O H00Q 108.6 . . ?
C00Q C00O H00R 108.6 . . ?
C00Q C00O C00P 114.8(3) . . ?
C00N C00P C00O 113.0(3) . . ?
C00N C00P H00S 109.0 . . ?
C00N C00P H00T 109.0 . . ?
C00O C00P H00S 109.0 . . ?
C00O C00P H00T 109.0 . . ?
H00S C00P H00T 107.8 . . ?
C00O C00Q H00U 108.8 . . ?
C00O C00Q H00V 108.8 . . ?
C00O C00Q C00R 113.9(3) . . ?
H00U C00Q H00V 107.7 . . ?
C00R C00Q H00U 108.8 . . ?
C00R C00Q H00V 108.8 . . ?
C00Q C00R H00W 108.9 . . ?
C00Q C00R H00X 108.9 . . ?
C00Q C00R C00S 113.4(3) . . ?
H00W C00R H00X 107.7 . . ?
C00S C00R H00W 108.9 . . ?
C00S C00R H00X 108.9 . . ?
C00R C00S H00Y 109.5 . . ?
C00R C00S H 109.5 . . ?
C00R C00S HA 109.5 . . ?
H00Y C00S H 109.5 . . ?
H00Y C00S HA 109.5 . . ?
H C00S HA 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
O001 C00C C00F C00I 179.1(3) . . . . ?
O001 C00C C00G C00A -179.6(3) . . . . ?
O001 C00L C00M C00N -175.4(3) . . . . ?
O003 C00A C00G C00C -179.1(3) . . . . ?
N004 C007 C00E C00J -179.6(2) . . . . ?
C006 C007 C00E C00J 0.2(4) . . . . ?
C006 C008 C00B O002 -36.6(4) . . . . ?
C006 C008 C00B O005 145.2(3) . . . . ?
C006 C008 C00H C00J 1.7(4) . . . . ?
C007 N004 C00D C009 -178.0(2) . . . . ?
C007 C006 C008 C00B 177.3(2) . . . . ?
C007 C006 C008 C00H -1.6(4) . . . . ?
C007 C00E C00J C00H -0.2(4) . . . . ?
C008 C006 C007 N004 -179.5(2) . . . . ?
C008 C006 C007 C00E 0.7(4) . . . . ?
C008 C00H C00J C00E -0.8(4) . . . . ?
C009 C00A C00G C00C 1.2(4) . . . . ?
C00A C009 C00D N004 -1.5(4) . . . . ?
C00A C009 C00I C00F 0.8(4) . . . . ?
C00B C008 C00H C00J -177.3(3) . . . . ?
C00C O001 C00L C00M 178.0(2) . . . . ?
C00C C00F C00I C009 -0.2(5) . . . . ?
C00D N004 C007 C006 175.3(3) . . . . ?
C00D N004 C007 C00E -4.8(4) . . . . ?
C00D C009 C00A O003 -1.4(4) . . . . ?
C00D C009 C00A C00G 178.3(2) . . . . ?
C00D C009 C00I C00F -178.8(3) . . . . ?
C00F C00C C00G C00A -0.7(4) . . . . ?
C00G C00C C00F C00I 0.1(5) . . . . ?
C00H C008 C00B O002 142.3(3) . . . . ?
C00H C008 C00B O005 -35.8(4) . . . . ?
C00I C009 C00A O003 179.0(3) . . . . ?
C00I C009 C00A C00G -1.3(4) . . . . ?
C00I C009 C00D N004 178.0(3) . . . . ?
C00K C006 C007 N004 2.2(4) . . . . ?
C00K C006 C007 C00E -177.6(2) . . . . ?
C00K C006 C008 C00B -4.5(4) . . . . ?
C00K C006 C008 C00H 176.6(3) . . . . ?
C00L O001 C00C C00F -178.0(2) . . . . ?
C00L O001 C00C C00G 1.0(4) . . . . ?
C00L C00M C00N C00P -175.7(3) . . . . ?
C00M C00N C00P C00O 179.1(3) . . . . ?
C00O C00Q C00R C00S -176.5(3) . . . . ?
C00P C00O C00Q C00R 178.5(3) . . . . ?
C00Q C00O C00P C00N -177.0(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_spc4f
_database_code_depnum_ccdc_archive 'CCDC 1520913'
_audit_update_record             
;
2016-12-06 deposited with the CCDC.
2017-05-14 downloaded from the CCDC.
;
_audit_creation_date             2015-12-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H24 F N O4'
_chemical_formula_sum            'C25 H24 F N O4'
_chemical_formula_weight         421.45
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.431(7)
_cell_length_b                   9.940(3)
_cell_length_c                   13.486(15)
_cell_angle_alpha                108.84(7)
_cell_angle_beta                 98.46(18)
_cell_angle_gamma                96.64(16)
_cell_volume                     1041.8(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2959
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing 1995'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1427
_diffrn_reflns_av_unetI/netI     0.1259
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11272
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.628
_diffrn_reflns_theta_min         3.015
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 240.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 120.0000
	             XTD: 49.8600
	          2theta: 29.8900
;
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.097742
_diffrn_orient_matrix_UB_12      -0.044094
_diffrn_orient_matrix_UB_13      0.057705
_diffrn_orient_matrix_UB_21      0.035348
_diffrn_orient_matrix_UB_22      0.049791
_diffrn_orient_matrix_UB_23      0.091317
_diffrn_orient_matrix_UB_31      -0.033850
_diffrn_orient_matrix_UB_32      0.050624
_diffrn_orient_matrix_UB_33      -0.051732
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           12.0
_diffrn_source_power             0.6
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3338
_reflns_number_total             4824
_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       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4747
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0562
_refine_ls_restrained_S_all      0.974
_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)+(0.0608P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1794
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C8(H8), C25(H25), C5(H5), C14(H14), C4(H4), C24(H24),
 C6(H6), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C18(H18A,H18B,H18C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 -0.39848(15) -0.33161(12) -0.12329(10) 0.0324(3) Uani 1 1 d . . . . .
O4 O 0.82160(15) 1.21172(13) 0.75440(11) 0.0221(3) Uani 1 1 d . . . . .
O3 O 0.51034(15) 0.74111(13) 0.57225(11) 0.0216(3) Uani 1 1 d . . . . .
H3 H 0.4145 0.7010 0.5410 0.032 Uiso 1 1 calc GR . . . .
O1 O -0.00723(16) 0.18524(14) 0.24881(11) 0.0262(4) Uani 1 1 d . . . . .
O2 O -0.24396(16) 0.21620(13) 0.16510(11) 0.0246(3) Uani 1 1 d . . . . .
N1 N 0.20654(19) 0.72229(16) 0.49227(13) 0.0196(4) Uani 1 1 d . . . . .
C12 C 0.6805(2) 1.11899(19) 0.70330(15) 0.0177(4) Uani 1 1 d . . . . .
C2 C 0.0543(2) 0.50176(18) 0.36073(15) 0.0171(4) Uani 1 1 d . . . . .
C11 C 0.6679(2) 0.97026(19) 0.66490(14) 0.0176(4) Uani 1 1 d . . . . .
H11 H 0.7603 0.9269 0.6764 0.021 Uiso 1 1 calc R . . . .
C7 C 0.0535(2) 0.63545(19) 0.43818(15) 0.0179(4) Uani 1 1 d . . . . .
C10 C 0.5184(2) 0.88535(19) 0.60928(14) 0.0170(4) Uani 1 1 d . . . . .
C3 C -0.0971(2) 0.41160(19) 0.31265(15) 0.0170(4) Uani 1 1 d . . . . .
C13 C 0.5429(2) 1.18285(19) 0.68972(15) 0.0203(4) Uani 1 1 d . . . . .
H13 H 0.5509 1.2846 0.7194 0.024 Uiso 1 1 calc R . . . .
C9 C 0.3793(2) 0.94746(19) 0.59158(15) 0.0186(4) Uani 1 1 d . . . . .
C1 C 0.2106(2) 0.4633(2) 0.32965(16) 0.0211(4) Uani 1 1 d . . . . .
H1A H 0.2886 0.5517 0.3442 0.032 Uiso 1 1 calc GR . . . .
H1B H 0.1904 0.4061 0.2533 0.032 Uiso 1 1 calc GR . . . .
H1C H 0.2554 0.4067 0.3711 0.032 Uiso 1 1 calc GR . . . .
C8 C 0.2249(2) 0.86030(19) 0.53125(15) 0.0200(4) Uani 1 1 d . . . . .
H8 H 0.1346 0.9063 0.5201 0.024 Uiso 1 1 calc R . . . .
C25 C -0.3826(2) -0.0262(2) 0.11295(15) 0.0217(4) Uani 1 1 d . . . . .
H25 H -0.4281 0.0000 0.1755 0.026 Uiso 1 1 calc R . . . .
C5 C -0.2382(2) 0.5865(2) 0.41326(15) 0.0205(4) Uani 1 1 d . . . . .
H5 H -0.3368 0.6166 0.4303 0.025 Uiso 1 1 calc R . . . .
C14 C 0.3972(2) 1.09785(19) 0.63353(15) 0.0199(4) Uani 1 1 d . . . . .
H14 H 0.3055 1.1423 0.6227 0.024 Uiso 1 1 calc R . . . .
C4 C -0.2423(2) 0.45496(19) 0.33653(15) 0.0192(4) Uani 1 1 d . . . . .
H4 H -0.3436 0.3940 0.3000 0.023 Uiso 1 1 calc R . . . .
C24 C -0.4252(2) -0.1645(2) 0.03862(16) 0.0225(4) Uani 1 1 d . . . . .
H24 H -0.5010 -0.2352 0.0486 0.027 Uiso 1 1 calc R . . . .
C23 C -0.3552(2) -0.19674(19) -0.04997(16) 0.0222(4) Uani 1 1 d . . . . .
C20 C -0.2727(2) 0.07289(19) 0.09468(15) 0.0215(4) Uani 1 1 d . . . . .
C6 C -0.0911(2) 0.67491(19) 0.46553(15) 0.0198(4) Uani 1 1 d . . . . .
H6 H -0.0887 0.7638 0.5209 0.024 Uiso 1 1 calc R . . . .
C19 C -0.1051(2) 0.26143(19) 0.24125(15) 0.0180(4) Uani 1 1 d . . . . .
C15 C 0.9692(2) 1.1540(2) 0.76326(16) 0.0222(4) Uani 1 1 d . . . . .
H15A H 0.9797 1.0889 0.6923 0.027 Uiso 1 1 calc R . . . .
H15B H 0.9680 1.0981 0.8121 0.027 Uiso 1 1 calc R . . . .
C16 C 1.1099(2) 1.2787(2) 0.80641(16) 0.0220(4) Uani 1 1 d . . . . .
H16A H 1.1109 1.3312 0.7553 0.026 Uiso 1 1 calc R . . . .
H16B H 1.2128 1.2401 0.8111 0.026 Uiso 1 1 calc R . . . .
C21 C -0.2021(2) 0.0392(2) 0.00650(17) 0.0250(5) Uani 1 1 d . . . . .
H21 H -0.1259 0.1095 -0.0034 0.030 Uiso 1 1 calc R . . . .
C22 C -0.2441(2) -0.0995(2) -0.06798(17) 0.0263(5) Uani 1 1 d . . . . .
H22 H -0.1971 -0.1264 -0.1299 0.032 Uiso 1 1 calc R . . . .
C17 C 1.1049(2) 1.3843(2) 0.91504(17) 0.0262(5) Uani 1 1 d . . . . .
H17A H 1.0999 1.3318 0.9659 0.031 Uiso 1 1 calc R . . . .
H17B H 1.0047 1.4268 0.9101 0.031 Uiso 1 1 calc R . . . .
C18 C 1.2520(3) 1.5048(2) 0.95774(18) 0.0300(5) Uani 1 1 d . . . . .
H18A H 1.2558 1.5591 0.9087 0.045 Uiso 1 1 calc GR . . . .
H18B H 1.3515 1.4635 0.9637 0.045 Uiso 1 1 calc GR . . . .
H18C H 1.2438 1.5698 1.0283 0.045 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C23 1.354(3) . ?
O4 C12 1.355(4) . ?
O4 C15 1.434(3) . ?
O3 H3 0.8400 . ?
O3 C10 1.347(2) . ?
O1 C19 1.198(3) . ?
O2 C20 1.403(3) . ?
O2 C19 1.361(4) . ?
N1 C7 1.414(4) . ?
N1 C8 1.282(2) . ?
C12 C11 1.385(3) . ?
C12 C13 1.401(3) . ?
C2 C7 1.401(3) . ?
C2 C3 1.403(4) . ?
C2 C1 1.496(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.389(4) . ?
C7 C6 1.388(3) . ?
C10 C9 1.412(3) . ?
C3 C4 1.392(3) . ?
C3 C19 1.480(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.368(4) . ?
C9 C8 1.442(4) . ?
C9 C14 1.398(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C8 H8 0.9500 . ?
C25 H25 0.9500 . ?
C25 C24 1.383(3) . ?
C25 C20 1.379(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.374(3) . ?
C5 C6 1.377(4) . ?
C14 H14 0.9500 . ?
C4 H4 0.9500 . ?
C24 H24 0.9500 . ?
C24 C23 1.372(3) . ?
C23 C22 1.371(4) . ?
C20 C21 1.370(4) . ?
C6 H6 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.508(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.511(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.386(3) . ?
C22 H22 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.519(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C12 O4 C15 118.44(16) . . ?
C10 O3 H3 109.5 . . ?
C19 O2 C20 117.6(2) . . ?
C8 N1 C7 122.0(2) . . ?
O4 C12 C11 123.9(2) . . ?
O4 C12 C13 115.65(17) . . ?
C11 C12 C13 120.5(2) . . ?
C7 C2 C3 116.9(2) . . ?
C7 C2 C1 120.1(2) . . ?
C3 C2 C1 122.97(17) . . ?
C12 C11 H11 120.4 . . ?
C12 C11 C10 119.1(2) . . ?
C10 C11 H11 120.4 . . ?
C2 C7 N1 117.1(2) . . ?
C6 C7 N1 121.88(18) . . ?
C6 C7 C2 120.9(2) . . ?
O3 C10 C11 117.8(2) . . ?
O3 C10 C9 120.8(2) . . ?
C11 C10 C9 121.41(18) . . ?
C2 C3 C19 120.2(2) . . ?
C4 C3 C2 121.88(18) . . ?
C4 C3 C19 117.7(2) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.62(18) . . ?
C14 C13 H13 120.2 . . ?
C10 C9 C8 121.72(18) . . ?
C14 C9 C10 117.4(2) . . ?
C14 C9 C8 120.9(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C8 C9 121.6(2) . . ?
N1 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C24 C25 H25 120.6 . . ?
C20 C25 H25 120.6 . . ?
C20 C25 C24 118.8(2) . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C13 C14 C9 121.9(2) . . ?
C13 C14 H14 119.0 . . ?
C9 C14 H14 119.0 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 H4 120.2 . . ?
C25 C24 H24 120.9 . . ?
C23 C24 C25 118.2(2) . . ?
C23 C24 H24 120.9 . . ?
F1 C23 C24 118.1(2) . . ?
F1 C23 C22 118.5(2) . . ?
C22 C23 C24 123.4(2) . . ?
C25 C20 O2 117.9(2) . . ?
C21 C20 O2 119.3(2) . . ?
C21 C20 C25 122.6(2) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 C7 120.65(18) . . ?
C5 C6 H6 119.7 . . ?
O1 C19 O2 122.83(18) . . ?
O1 C19 C3 126.1(2) . . ?
O2 C19 C3 111.0(2) . . ?
O4 C15 H15A 110.1 . . ?
O4 C15 H15B 110.1 . . ?
O4 C15 C16 107.97(17) . . ?
H15A C15 H15B 108.4 . . ?
C16 C15 H15A 110.1 . . ?
C16 C15 H15B 110.1 . . ?
C15 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
C15 C16 C17 114.1(2) . . ?
H16A C16 H16B 107.6 . . ?
C17 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C20 C21 H21 120.6 . . ?
C20 C21 C22 118.8(2) . . ?
C22 C21 H21 120.6 . . ?
C23 C22 C21 118.2(2) . . ?
C23 C22 H22 120.9 . . ?
C21 C22 H22 120.9 . . ?
C16 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
C16 C17 C18 112.5(2) . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 C23 C22 C21 178.99(16) . . . . ?
O4 C12 C11 C10 -177.05(16) . . . . ?
O4 C12 C13 C14 176.19(16) . . . . ?
O4 C15 C16 C17 60.0(2) . . . . ?
O3 C10 C9 C8 -1.6(3) . . . . ?
O3 C10 C9 C14 179.33(16) . . . . ?
O2 C20 C21 C22 -173.67(17) . . . . ?
N1 C7 C6 C5 -178.38(17) . . . . ?
C12 O4 C15 C16 170.88(16) . . . . ?
C12 C11 C10 O3 179.53(16) . . . . ?
C12 C11 C10 C9 -0.3(3) . . . . ?
C12 C13 C14 C9 2.1(3) . . . . ?
C2 C7 C6 C5 -3.3(3) . . . . ?
C2 C3 C4 C5 -3.4(3) . . . . ?
C2 C3 C19 O1 32.0(3) . . . . ?
C2 C3 C19 O2 -149.97(18) . . . . ?
C11 C12 C13 C14 -3.2(3) . . . . ?
C11 C10 C9 C8 178.15(17) . . . . ?
C11 C10 C9 C14 -0.9(3) . . . . ?
C7 N1 C8 C9 176.37(16) . . . . ?
C7 C2 C3 C4 3.0(3) . . . . ?
C7 C2 C3 C19 -171.68(16) . . . . ?
C10 C9 C8 N1 1.0(3) . . . . ?
C10 C9 C14 C13 0.0(3) . . . . ?
C3 C2 C7 N1 175.62(16) . . . . ?
C3 C2 C7 C6 0.3(3) . . . . ?
C13 C12 C11 C10 2.3(3) . . . . ?
C1 C2 C7 N1 -6.8(3) . . . . ?
C1 C2 C7 C6 177.91(17) . . . . ?
C1 C2 C3 C4 -174.48(18) . . . . ?
C1 C2 C3 C19 10.8(3) . . . . ?
C8 N1 C7 C2 152.50(19) . . . . ?
C8 N1 C7 C6 -32.2(3) . . . . ?
C8 C9 C14 C13 -179.07(17) . . . . ?
C25 C24 C23 F1 -179.25(16) . . . . ?
C25 C24 C23 C22 0.7(3) . . . . ?
C25 C20 C21 C22 0.8(3) . . . . ?
C14 C9 C8 N1 -179.99(18) . . . . ?
C4 C3 C19 O1 -142.9(2) . . . . ?
C4 C3 C19 O2 35.1(2) . . . . ?
C4 C5 C6 C7 3.0(3) . . . . ?
C24 C25 C20 O2 173.49(16) . . . . ?
C24 C25 C20 C21 -1.0(3) . . . . ?
C24 C23 C22 C21 -0.9(3) . . . . ?
C20 O2 C19 O1 1.3(3) . . . . ?
C20 O2 C19 C3 -176.78(16) . . . . ?
C20 C25 C24 C23 0.3(3) . . . . ?
C20 C21 C22 C23 0.2(3) . . . . ?
C6 C5 C4 C3 0.4(3) . . . . ?
C19 O2 C20 C25 101.7(2) . . . . ?
C19 O2 C20 C21 -83.6(2) . . . . ?
C19 C3 C4 C5 171.40(17) . . . . ?
C15 O4 C12 C11 4.4(3) . . . . ?
C15 O4 C12 C13 -175.03(16) . . . . ?
C15 C16 C17 C18 177.65(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
