# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_FuA_11
_database_code_depnum_ccdc_archive 'CCDC 1868722'
loop_
_audit_author_name
_audit_author_address
'Poulami Chakraborty'
;SRF, IACS
India
;
_audit_update_record             
;
2018-09-20 deposited with the CCDC.	2019-06-07 downloaded from the CCDC.
;
_audit_creation_date             2018-09-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        FuA_11
_chemical_formula_moiety         'C6 H4 F N2 O4, C11 H26 N'
_chemical_formula_sum            'C17 H30 F N3 O4'
_chemical_formula_weight         359.44
_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 0.0181 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'
F F 0.0727 0.0534 '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'

_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                   4.6593(2)
_cell_length_b                   10.5631(3)
_cell_length_c                   19.8391(7)
_cell_angle_alpha                97.467(2)
_cell_angle_beta                 92.052(3)
_cell_angle_gamma                91.741(2)
_cell_volume                     966.91(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2341
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.21
_cell_measurement_theta_min      4.22
_shelx_estimated_absorpt_T_max   0.912
_shelx_estimated_absorpt_T_min   0.841
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1240 before and 0.0692 after correction. The Ratio of minimum to maximum transmission is 0.7339. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.0855
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6661
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.549
_diffrn_reflns_theta_min         4.224
_diffrn_ambient_temperature      100.09
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2321
_reflns_number_total             3367
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3367
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.038
_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)+(0.0589P)²+0.1651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1493
_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, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C10(H10A,
 H10B), C13(H13A,H13B), C15(H15A,H15B), C12(H12A,H12B), C14(H14A,H14B),
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4)
2.c Idealised Me refined as rotating group:
 N3(H3A,H3B,H3C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_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 -0.2995(3) 0.57831(12) 0.18764(7) 0.0281(4) Uani 1 1 d . . . . .
O1 O 0.3524(3) 0.33893(14) -0.00276(8) 0.0228(4) Uani 1 1 d . . . . .
O3 O 0.1324(3) 0.00118(14) 0.09236(8) 0.0242(4) Uani 1 1 d . . . . .
O4 O 0.3511(4) 0.18641(15) 0.13710(8) 0.0275(4) Uani 1 1 d . . . . .
O2 O 0.1341(4) 0.70704(14) 0.12882(8) 0.0256(4) Uani 1 1 d . . . . .
N1 N 0.2335(4) 0.52071(17) 0.06366(9) 0.0194(4) Uani 1 1 d . . . . .
H1 H 0.365830 0.562537 0.043910 0.023 Uiso 1 1 calc R . . . .
N2 N -0.0097(4) 0.32866(17) 0.07131(9) 0.0187(4) Uani 1 1 d . . . . .
N3 N -0.3779(4) -0.11005(17) 0.13348(10) 0.0226(5) Uani 1 1 d . . . . .
H3A H -0.403579 -0.191656 0.112465 0.027 Uiso 1 1 calc GR . . . .
H3B H -0.216463 -0.073958 0.118442 0.027 Uiso 1 1 calc GR . . . .
H3C H -0.532517 -0.064054 0.123767 0.027 Uiso 1 1 calc GR . . . .
C1 C 0.2008(5) 0.3921(2) 0.04161(11) 0.0180(5) Uani 1 1 d . . . . .
C2 C 0.0830(5) 0.5926(2) 0.11334(12) 0.0201(5) Uani 1 1 d . . . . .
C6 C 0.1683(5) 0.1228(2) 0.09986(12) 0.0197(5) Uani 1 1 d . . . . .
C3 C -0.1316(5) 0.5158(2) 0.14101(12) 0.0203(5) Uani 1 1 d . . . . .
C4 C -0.1708(5) 0.3911(2) 0.12164(11) 0.0199(5) Uani 1 1 d . . . . .
H4 H -0.311499 0.344207 0.142674 0.024 Uiso 1 1 calc R . . . .
C5 C -0.0409(5) 0.1896(2) 0.05619(12) 0.0209(5) Uani 1 1 d . . . . .
H5A H -0.005611 0.163484 0.007518 0.025 Uiso 1 1 calc R . . . .
H5B H -0.240206 0.162229 0.064493 0.025 Uiso 1 1 calc R . . . .
C7 C -0.3469(6) -0.1108(2) 0.20817(12) 0.0264(6) Uani 1 1 d . . . . .
H7A H -0.216678 -0.179185 0.217766 0.032 Uiso 1 1 calc R . . . .
H7B H -0.536793 -0.130013 0.226052 0.032 Uiso 1 1 calc R . . . .
C8 C -0.2280(6) 0.0164(2) 0.24434(12) 0.0279(6) Uani 1 1 d . . . . .
H8A H -0.045466 0.038926 0.224015 0.033 Uiso 1 1 calc R . . . .
H8B H -0.365780 0.083730 0.237828 0.033 Uiso 1 1 calc R . . . .
C9 C -0.1750(6) 0.0118(2) 0.31987(13) 0.0323(6) Uani 1 1 d . . . . .
H9A H -0.059577 -0.063350 0.326038 0.039 Uiso 1 1 calc R . . . .
H9B H -0.361746 0.000295 0.340979 0.039 Uiso 1 1 calc R . . . .
C11 C 0.0519(7) 0.1255(3) 0.43127(13) 0.0370(7) Uani 1 1 d . . . . .
H11A H -0.129240 0.114079 0.454737 0.044 Uiso 1 1 calc R . . . .
H11B H 0.167836 0.049660 0.435355 0.044 Uiso 1 1 calc R . . . .
C10 C -0.0196(6) 0.1312(2) 0.35646(13) 0.0347(7) Uani 1 1 d . . . . .
H10A H 0.161017 0.145520 0.333322 0.042 Uiso 1 1 calc R . . . .
H10B H -0.140924 0.205389 0.352492 0.042 Uiso 1 1 calc R . . . .
C13 C 0.2965(6) 0.2352(3) 0.54109(13) 0.0370(7) Uani 1 1 d . . . . .
H13A H 0.412818 0.158938 0.543610 0.044 Uiso 1 1 calc R . . . .
H13B H 0.118752 0.223215 0.565730 0.044 Uiso 1 1 calc R . . . .
C15 C 0.5492(7) 0.3406(3) 0.65066(14) 0.0403(7) Uani 1 1 d . . . . .
H15A H 0.371830 0.330341 0.675739 0.048 Uiso 1 1 calc R . . . .
H15B H 0.658978 0.262064 0.651876 0.048 Uiso 1 1 calc R . . . .
C12 C 0.2153(7) 0.2430(3) 0.46708(13) 0.0385(7) Uani 1 1 d . . . . .
H12A H 0.392777 0.256361 0.442535 0.046 Uiso 1 1 calc R . . . .
H12B H 0.096124 0.318368 0.464556 0.046 Uiso 1 1 calc R . . . .
C14 C 0.4646(7) 0.3517(3) 0.57697(13) 0.0384(7) Uani 1 1 d . . . . .
H14A H 0.346848 0.427849 0.575563 0.046 Uiso 1 1 calc R . . . .
H14B H 0.640765 0.364935 0.551948 0.046 Uiso 1 1 calc R . . . .
C17 C 0.5745(8) 0.5778(3) 0.69608(16) 0.0531(9) Uani 1 1 d . . . . .
H17A H 0.542354 0.606396 0.651447 0.080 Uiso 1 1 calc GR . . . .
H17B H 0.692770 0.642368 0.725539 0.080 Uiso 1 1 calc GR . . . .
H17C H 0.389341 0.565703 0.716701 0.080 Uiso 1 1 calc GR . . . .
C16 C 0.7276(7) 0.4528(3) 0.68768(15) 0.0495(8) Uani 1 1 d . . . . .
H16A H 0.787184 0.432233 0.733301 0.059 Uiso 1 1 calc R . . . .
H16B H 0.903987 0.463911 0.662401 0.059 Uiso 1 1 calc R . . . .


_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 C3 1.352(3) . ?
O1 C1 1.237(3) . ?
O3 C6 1.279(3) . ?
O4 C6 1.230(3) . ?
O2 C2 1.222(3) . ?
N1 H1 0.8800 . ?
N1 C1 1.374(3) . ?
N1 C2 1.388(3) . ?
N2 C1 1.365(3) . ?
N2 C4 1.381(3) . ?
N2 C5 1.463(3) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 H3C 0.9100 . ?
N3 C7 1.485(3) . ?
C2 C3 1.437(3) . ?
C6 C5 1.529(3) . ?
C3 C4 1.329(3) . ?
C4 H4 0.9500 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.518(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.517(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.520(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.519(4) . ?
C11 C12 1.517(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C12 1.516(4) . ?
C13 C14 1.519(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C14 1.521(4) . ?
C15 C16 1.518(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 C16 1.513(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 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 N1 H1 116.1 . . ?
C1 N1 C2 127.82(19) . . ?
C2 N1 H1 116.1 . . ?
C1 N2 C4 121.13(19) . . ?
C1 N2 C5 119.50(18) . . ?
C4 N2 C5 118.89(18) . . ?
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C7 N3 H3A 109.5 . . ?
C7 N3 H3B 109.5 . . ?
C7 N3 H3C 109.5 . . ?
O1 C1 N1 121.4(2) . . ?
O1 C1 N2 122.9(2) . . ?
N2 C1 N1 115.7(2) . . ?
O2 C2 N1 121.6(2) . . ?
O2 C2 C3 126.9(2) . . ?
N1 C2 C3 111.49(19) . . ?
O3 C6 C5 113.8(2) . . ?
O4 C6 O3 126.4(2) . . ?
O4 C6 C5 119.8(2) . . ?
F1 C3 C2 116.08(19) . . ?
C4 C3 F1 120.9(2) . . ?
C4 C3 C2 123.0(2) . . ?
N2 C4 H4 119.6 . . ?
C3 C4 N2 120.9(2) . . ?
C3 C4 H4 119.6 . . ?
N2 C5 C6 111.71(18) . . ?
N2 C5 H5A 109.3 . . ?
N2 C5 H5B 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
N3 C7 H7A 109.3 . . ?
N3 C7 H7B 109.3 . . ?
N3 C7 C8 111.77(18) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 C7 111.5(2) . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C8 C9 C10 113.2(2) . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H11A C11 H11B 107.6 . . ?
C10 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
C12 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C12 C11 C10 114.1(2) . . ?
C9 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C11 C10 C9 114.2(2) . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
H13A C13 H13B 107.6 . . ?
C12 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
C12 C13 C14 114.4(2) . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H15A C15 H15B 107.5 . . ?
C14 C15 H15A 108.5 . . ?
C14 C15 H15B 108.5 . . ?
C16 C15 H15A 108.5 . . ?
C16 C15 H15B 108.5 . . ?
C16 C15 C14 115.2(2) . . ?
C11 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C13 C12 C11 114.1(2) . . ?
C13 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C13 C14 C15 113.4(2) . . ?
C13 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C15 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
C15 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
C17 C16 C15 114.4(3) . . ?
C17 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
#
_vrf_PLAT029_FuA_11              
;
PROBLEM:  _diffrn_measured_fraction_theta_full value Low .      0.955 Why?   
RESPONSE: The crystal was very poorly diffracting and the problem could 
not be resolved even after collecting fresh data set on variuos crystals.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_FuA_12
_database_code_depnum_ccdc_archive 'CCDC 1868723'
loop_
_audit_author_name
_audit_author_address
'Poulami Chakraborty'
;SRF, IACS
India
;
_audit_update_record             
;
2018-09-20 deposited with the CCDC.	2019-06-07 downloaded from the CCDC.
;
_audit_creation_date             2018-09-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        FuA_12
_chemical_formula_moiety         'C6 H3 F N2 O4, 2(C12 H28 N)'
_chemical_formula_sum            'C30 H59 F N4 O4'
_chemical_formula_weight         558.81
_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                   8.8667(6)
_cell_length_b                   9.0125(6)
_cell_length_c                   20.1479(11)
_cell_angle_alpha                89.377(2)
_cell_angle_beta                 80.718(2)
_cell_angle_gamma                88.288(2)
_cell_volume                     1588.22(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7346
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.94
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1659 before and 0.0862 after correction. The Ratio of minimum to maximum transmission is 0.7996. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0745
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            20939
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.028
_diffrn_reflns_theta_min         2.261
_diffrn_ambient_temperature      99.98
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5949
_reflns_number_total             9083
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         9083
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0576
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0684P)²+0.6225P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1432
_refine_ls_wR_factor_ref         0.1770
_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,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C19(H19A,H19B), C20(H20A,H20B), C9(H9A,H9B), C8(H8A,
 H8B), C26(H26A,H26B), C10(H10A,H10B), C22(H22A,H22B), C23(H23A,H23B), C28(H28A,
 H28B), C27(H27A,H27B), C13(H13A,H13B), C24(H24A,H24B), C11(H11A,H11B),
 C21(H21A,H21B), C25(H25A,H25B), C15(H15A,H15B), C14(H14A,H14B), C29(H29A,H29B),
  C12(H12A,H12B), C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4)
2.c Idealised Me refined as rotating group:
 N3(H3A,H3B,H3C), N4(H4A,H4B,H4C), C30(H30A,H30B,H30C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_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 0.49355(12) -0.06525(10) 0.63014(5) 0.0280(2) Uani 1 1 d . . . . .
O3 O 0.91255(13) 0.32806(12) 0.53165(6) 0.0235(2) Uani 1 1 d . . . . .
O1 O 0.63628(13) 0.35789(12) 0.44582(6) 0.0230(2) Uani 1 1 d . . . . .
O2 O 0.29459(14) 0.16706(12) 0.61507(6) 0.0263(3) Uani 1 1 d . . . . .
O4 O 1.09585(13) 0.24593(13) 0.44983(6) 0.0267(3) Uani 1 1 d . . . . .
N2 N 0.70243(15) 0.14223(13) 0.49524(6) 0.0185(3) Uani 1 1 d . . . . .
N1 N 0.46275(15) 0.26434(13) 0.52948(6) 0.0194(3) Uani 1 1 d . . . . .
N3 N 0.31734(16) 0.45412(14) 0.43175(6) 0.0193(3) Uani 1 1 d . . . . .
H3A H 0.268672 0.544105 0.439426 0.023 Uiso 1 1 calc GR . . . .
H3B H 0.400553 0.449399 0.452952 0.023 Uiso 1 1 calc GR . . . .
H3C H 0.252414 0.381060 0.447866 0.023 Uiso 1 1 calc GR . . . .
N4 N 1.14505(15) 0.42844(14) 0.59849(6) 0.0199(3) Uani 1 1 d . . . . .
H4A H 1.068126 0.412994 0.574655 0.024 Uiso 1 1 calc GR . . . .
H4B H 1.197726 0.341479 0.602560 0.024 Uiso 1 1 calc GR . . . .
H4C H 1.209354 0.496420 0.576661 0.024 Uiso 1 1 calc GR . . . .
C1 C 0.59920(18) 0.25836(15) 0.48930(8) 0.0186(3) Uani 1 1 d . . . . .
C6 C 0.96312(18) 0.24871(16) 0.48146(8) 0.0196(3) Uani 1 1 d . . . . .
C4 C 0.66678(18) 0.03547(16) 0.54380(7) 0.0188(3) Uani 1 1 d . . . . .
H4 H 0.738329 -0.042597 0.549105 0.023 Uiso 1 1 calc R . . . .
C3 C 0.53164(18) 0.04192(16) 0.58335(8) 0.0195(3) Uani 1 1 d . . . . .
C2 C 0.42174(18) 0.16022(16) 0.57740(8) 0.0192(3) Uani 1 1 d . . . . .
C5 C 0.85322(19) 0.14346(17) 0.45520(8) 0.0214(3) Uani 1 1 d . . . . .
H5A H 0.843314 0.172877 0.408580 0.026 Uiso 1 1 calc R . . . .
H5B H 0.898273 0.041482 0.453784 0.026 Uiso 1 1 calc R . . . .
C7 C 0.36691(19) 0.43421(17) 0.35833(8) 0.0206(3) Uani 1 1 d . . . . .
H7A H 0.275475 0.423372 0.336536 0.025 Uiso 1 1 calc R . . . .
H7B H 0.429788 0.341493 0.350689 0.025 Uiso 1 1 calc R . . . .
C19 C 1.07956(19) 0.48470(16) 0.66653(8) 0.0204(3) Uani 1 1 d . . . . .
H19A H 1.012826 0.573037 0.661974 0.024 Uiso 1 1 calc R . . . .
H19B H 1.163448 0.515393 0.689921 0.024 Uiso 1 1 calc R . . . .
C20 C 0.98753(19) 0.36719(17) 0.70825(8) 0.0211(3) Uani 1 1 d . . . . .
H20A H 1.052286 0.276237 0.709904 0.025 Uiso 1 1 calc R . . . .
H20B H 0.899431 0.341799 0.686409 0.025 Uiso 1 1 calc R . . . .
C9 C 0.51698(19) 0.53038(17) 0.25217(8) 0.0221(3) Uani 1 1 d . . . . .
H9A H 0.428780 0.509618 0.229540 0.027 Uiso 1 1 calc R . . . .
H9B H 0.583347 0.439611 0.249224 0.027 Uiso 1 1 calc R . . . .
C8 C 0.45828(19) 0.56223(17) 0.32570(8) 0.0213(3) Uani 1 1 d . . . . .
H8A H 0.545717 0.578672 0.349451 0.026 Uiso 1 1 calc R . . . .
H8B H 0.393044 0.653799 0.329459 0.026 Uiso 1 1 calc R . . . .
C26 C 0.53962(19) 0.16681(17) 1.05167(7) 0.0213(3) Uani 1 1 d . . . . .
H26A H 0.605536 0.076576 1.053049 0.026 Uiso 1 1 calc R . . . .
H26B H 0.452434 0.140422 1.029420 0.026 Uiso 1 1 calc R . . . .
C10 C 0.60675(19) 0.65540(17) 0.21423(8) 0.0225(3) Uani 1 1 d . . . . .
H10A H 0.539763 0.745428 0.214945 0.027 Uiso 1 1 calc R . . . .
H10B H 0.693634 0.678992 0.237208 0.027 Uiso 1 1 calc R . . . .
C22 C 0.83787(19) 0.30377(17) 0.82311(8) 0.0216(3) Uani 1 1 d . . . . .
H22A H 0.902576 0.212666 0.824376 0.026 Uiso 1 1 calc R . . . .
H22B H 0.748856 0.278141 0.801925 0.026 Uiso 1 1 calc R . . . .
C23 C 0.78089(19) 0.35416(17) 0.89497(8) 0.0216(3) Uani 1 1 d . . . . .
H23A H 0.869721 0.379755 0.916277 0.026 Uiso 1 1 calc R . . . .
H23B H 0.715814 0.445060 0.893836 0.026 Uiso 1 1 calc R . . . .
C28 C 0.3863(2) 0.09774(17) 1.16566(8) 0.0219(3) Uani 1 1 d . . . . .
H28A H 0.451794 0.007511 1.167957 0.026 Uiso 1 1 calc R . . . .
H28B H 0.299510 0.070798 1.143283 0.026 Uiso 1 1 calc R . . . .
C27 C 0.4786(2) 0.21521(17) 1.12359(8) 0.0222(3) Uani 1 1 d . . . . .
H27A H 0.565871 0.241021 1.145879 0.027 Uiso 1 1 calc R . . . .
H27B H 0.413308 0.305884 1.122156 0.027 Uiso 1 1 calc R . . . .
C13 C 0.81635(19) 0.68495(17) 0.02843(8) 0.0222(3) Uani 1 1 d . . . . .
H13A H 0.881158 0.593827 0.029410 0.027 Uiso 1 1 calc R . . . .
H13B H 0.727904 0.659851 0.006754 0.027 Uiso 1 1 calc R . . . .
C24 C 0.68975(19) 0.23689(17) 0.93774(8) 0.0216(3) Uani 1 1 d . . . . .
H24A H 0.755173 0.146237 0.938847 0.026 Uiso 1 1 calc R . . . .
H24B H 0.601495 0.210941 0.916104 0.026 Uiso 1 1 calc R . . . .
C11 C 0.66727(19) 0.61351(17) 0.14150(8) 0.0227(3) Uani 1 1 d . . . . .
H11A H 0.733274 0.522916 0.141354 0.027 Uiso 1 1 calc R . . . .
H11B H 0.579662 0.588979 0.119161 0.027 Uiso 1 1 calc R . . . .
C21 C 0.92935(19) 0.41960(17) 0.77972(8) 0.0218(3) Uani 1 1 d . . . . .
H21A H 1.017725 0.446263 0.801113 0.026 Uiso 1 1 calc R . . . .
H21B H 0.864272 0.510248 0.777810 0.026 Uiso 1 1 calc R . . . .
C25 C 0.6310(2) 0.28537(17) 1.00967(8) 0.0222(3) Uani 1 1 d . . . . .
H25A H 0.565632 0.376088 1.008709 0.027 Uiso 1 1 calc R . . . .
H25B H 0.719131 0.310798 1.031519 0.027 Uiso 1 1 calc R . . . .
C15 C 0.96642(19) 0.75074(17) -0.08579(8) 0.0226(3) Uani 1 1 d . . . . .
H15A H 1.030804 0.659549 -0.084119 0.027 Uiso 1 1 calc R . . . .
H15B H 0.877873 0.725078 -0.107278 0.027 Uiso 1 1 calc R . . . .
C14 C 0.90825(19) 0.80182(17) -0.01414(8) 0.0227(3) Uani 1 1 d . . . . .
H14A H 0.996581 0.827491 0.007490 0.027 Uiso 1 1 calc R . . . .
H14B H 0.843394 0.892747 -0.015651 0.027 Uiso 1 1 calc R . . . .
C29 C 0.3249(2) 0.14979(18) 1.23679(8) 0.0253(3) Uani 1 1 d . . . . .
H29A H 0.412040 0.177186 1.258854 0.030 Uiso 1 1 calc R . . . .
H29B H 0.259800 0.240174 1.234231 0.030 Uiso 1 1 calc R . . . .
C12 C 0.7579(2) 0.73319(17) 0.10055(8) 0.0229(3) Uani 1 1 d . . . . .
H12A H 0.845908 0.758251 0.122507 0.027 Uiso 1 1 calc R . . . .
H12B H 0.692174 0.823781 0.099879 0.027 Uiso 1 1 calc R . . . .
C16 C 1.0589(2) 0.86608(18) -0.12911(8) 0.0248(3) Uani 1 1 d . . . . .
H16A H 1.147170 0.892248 -0.107540 0.030 Uiso 1 1 calc R . . . .
H16B H 0.994359 0.957060 -0.131113 0.030 Uiso 1 1 calc R . . . .
C17 C 1.1174(2) 0.8139(2) -0.20043(8) 0.0294(4) Uani 1 1 d . . . . .
H17A H 1.182464 0.723177 -0.198545 0.035 Uiso 1 1 calc R . . . .
H17B H 1.029324 0.787495 -0.222070 0.035 Uiso 1 1 calc R . . . .
C30 C 0.2324(2) 0.0348(2) 1.28015(9) 0.0311(4) Uani 1 1 d . . . . .
H30A H 0.146121 0.006257 1.258608 0.047 Uiso 1 1 calc GR . . . .
H30B H 0.193758 0.076852 1.324501 0.047 Uiso 1 1 calc GR . . . .
H30C H 0.297553 -0.052977 1.285304 0.047 Uiso 1 1 calc GR . . . .
C18 C 1.2092(2) 0.9303(3) -0.24327(10) 0.0416(5) Uani 1 1 d . . . . .
H18A H 1.244545 0.890734 -0.288399 0.062 Uiso 1 1 calc GR . . . .
H18B H 1.297613 0.955787 -0.222533 0.062 Uiso 1 1 calc GR . . . .
H18C H 1.144592 1.019375 -0.246490 0.062 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 C3 1.3538(17) . ?
O3 C6 1.2592(18) . ?
O1 C1 1.2600(17) . ?
O2 C2 1.2537(19) . ?
O4 C6 1.2444(19) . ?
N2 C1 1.3867(18) . ?
N2 C4 1.3714(18) . ?
N2 C5 1.446(2) . ?
N1 C1 1.343(2) . ?
N1 C2 1.3536(19) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 H3C 0.9100 . ?
N3 C7 1.4849(19) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
N4 H4C 0.9100 . ?
N4 C19 1.4879(19) . ?
C6 C5 1.537(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.328(2) . ?
C3 C2 1.440(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.512(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.518(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.524(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C8 1.516(2) . ?
C9 C10 1.525(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.526(2) . ?
C26 C25 1.525(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.524(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.524(2) . ?
C22 C21 1.521(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.523(2) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C27 1.522(2) . ?
C28 C29 1.522(2) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.522(2) . ?
C13 C12 1.525(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.523(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.519(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C14 1.524(2) . ?
C15 C16 1.522(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.520(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.522(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.521(3) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
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
C1 N2 C5 119.58(12) . . ?
C4 N2 C1 119.77(13) . . ?
C4 N2 C5 120.29(12) . . ?
C1 N1 C2 121.91(13) . . ?
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C7 N3 H3A 109.5 . . ?
C7 N3 H3B 109.5 . . ?
C7 N3 H3C 109.5 . . ?
H4A N4 H4B 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C19 N4 H4A 109.5 . . ?
C19 N4 H4B 109.5 . . ?
C19 N4 H4C 109.5 . . ?
O1 C1 N2 118.75(14) . . ?
O1 C1 N1 120.91(13) . . ?
N1 C1 N2 120.34(13) . . ?
O3 C6 C5 118.38(14) . . ?
O4 C6 O3 126.49(15) . . ?
O4 C6 C5 115.13(13) . . ?
N2 C4 H4 120.2 . . ?
C3 C4 N2 119.58(13) . . ?
C3 C4 H4 120.2 . . ?
F1 C3 C2 118.35(14) . . ?
C4 C3 F1 120.06(13) . . ?
C4 C3 C2 121.58(14) . . ?
O2 C2 N1 121.58(13) . . ?
O2 C2 C3 121.63(14) . . ?
N1 C2 C3 116.79(14) . . ?
N2 C5 C6 114.00(12) . . ?
N2 C5 H5A 108.8 . . ?
N2 C5 H5B 108.8 . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
H5A C5 H5B 107.6 . . ?
N3 C7 H7A 109.0 . . ?
N3 C7 H7B 109.0 . . ?
N3 C7 C8 112.94(12) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
N4 C19 H19A 109.3 . . ?
N4 C19 H19B 109.3 . . ?
N4 C19 C20 111.41(12) . . ?
H19A C19 H19B 108.0 . . ?
C20 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C19 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
C19 C20 C21 111.93(13) . . ?
H20A C20 H20B 107.9 . . ?
C21 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H9A C9 H9B 107.6 . . ?
C8 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C8 C9 C10 114.63(13) . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C7 C8 C9 110.69(12) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
H26A C26 H26B 107.7 . . ?
C27 C26 H26A 108.9 . . ?
C27 C26 H26B 108.9 . . ?
C25 C26 H26A 108.9 . . ?
C25 C26 H26B 108.9 . . ?
C25 C26 C27 113.53(13) . . ?
C9 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 C9 111.76(13) . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H22A C22 H22B 107.7 . . ?
C23 C22 H22A 108.8 . . ?
C23 C22 H22B 108.8 . . ?
C21 C22 H22A 108.8 . . ?
C21 C22 H22B 108.8 . . ?
C21 C22 C23 113.74(13) . . ?
C22 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C24 C23 C22 113.07(13) . . ?
C24 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
H28A C28 H28B 107.8 . . ?
C27 C28 H28A 109.1 . . ?
C27 C28 H28B 109.1 . . ?
C27 C28 C29 112.68(13) . . ?
C29 C28 H28A 109.1 . . ?
C29 C28 H28B 109.1 . . ?
C26 C27 H27A 108.8 . . ?
C26 C27 H27B 108.8 . . ?
C28 C27 C26 113.80(13) . . ?
C28 C27 H27A 108.8 . . ?
C28 C27 H27B 108.8 . . ?
H27A C27 H27B 107.7 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C14 C13 C12 113.93(13) . . ?
C12 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C23 C24 H24A 108.8 . . ?
C23 C24 H24B 108.8 . . ?
C23 C24 C25 113.91(13) . . ?
H24A C24 H24B 107.7 . . ?
C25 C24 H24A 108.8 . . ?
C25 C24 H24B 108.8 . . ?
C10 C11 H11A 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C12 C11 C10 114.66(13) . . ?
C12 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C20 C21 H21A 108.9 . . ?
C20 C21 H21B 108.9 . . ?
C22 C21 C20 113.26(13) . . ?
C22 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C26 C25 H25A 108.9 . . ?
C26 C25 H25B 108.9 . . ?
C24 C25 C26 113.18(13) . . ?
C24 C25 H25A 108.9 . . ?
C24 C25 H25B 108.9 . . ?
H25A C25 H25B 107.8 . . ?
H15A C15 H15B 107.7 . . ?
C14 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C16 C15 C14 113.75(13) . . ?
C13 C14 C15 112.98(13) . . ?
C13 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C28 C29 H29A 108.8 . . ?
C28 C29 H29B 108.8 . . ?
H29A C29 H29B 107.7 . . ?
C30 C29 C28 113.96(13) . . ?
C30 C29 H29A 108.8 . . ?
C30 C29 H29B 108.8 . . ?
C13 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 C13 112.38(13) . . ?
C11 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
C15 C16 C17 113.43(14) . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C16 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 C16 112.91(16) . . ?
C18 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
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 . . ?

_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_FuA_14
_database_code_depnum_ccdc_archive 'CCDC 1868725'
loop_
_audit_author_name
_audit_author_address
'Poulami Chakraborty'
;SRF, IACS
India
;
_audit_update_record             
;
2018-09-20 deposited with the CCDC.	2019-06-07 downloaded from the CCDC.
;
_audit_creation_date             2018-09-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        FuA_14
_chemical_formula_moiety         'C6 H4 F N2 O4, C14 H32 N'
_chemical_formula_sum            'C20 H36 F N3 O4'
_chemical_formula_weight         401.52
_chemical_absolute_configuration ?
_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 0.0181 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'
F F 0.0727 0.0534 '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'

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

_cell_length_a                   4.7844(2)
_cell_length_b                   10.4899(3)
_cell_length_c                   21.3123(7)
_cell_angle_alpha                82.522(2)
_cell_angle_beta                 87.079(2)
_cell_angle_gamma                88.450(2)
_cell_volume                     1058.92(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3726
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      58.86
_cell_measurement_theta_min      4.19
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.838
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.5551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1109 before and 0.0595 after correction. The Ratio of minimum to maximum transmission is 0.7386. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_Laue_measured_fraction_full 0.939
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6122
_diffrn_reflns_point_group_measured_fraction_full 0.692
_diffrn_reflns_point_group_measured_fraction_max 0.692
_diffrn_reflns_theta_full        59.051
_diffrn_reflns_theta_max         59.051
_diffrn_reflns_theta_min         4.189
_diffrn_ambient_temperature      115.14
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.939
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.474
_reflns_Friedel_fraction_full    0.445
_reflns_Friedel_fraction_max     0.445
_reflns_number_gt                3584
_reflns_number_total             4231
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 1066 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         4231
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.032
_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)+(0.0529P)²+0.8533P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1267
_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, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C5(H5D,H5E), C34(H34A,H34B), C38(H38A,H38B), C32(H32A,H32B),
 C14(H14A,H14B), C30(H30A,H30B), C18(H18A,H18B), C36(H36A,H36B), C16(H16A,H16B),
  C20(H20A,H20B), C33(H33A,H33B), C35(H35A,H35B), C39(H39A,H39B), C28(H28A,
 H28B), C13(H13A,H13B), C19(H19A,H19B), C37(H37A,H37B), C29(H29A,H29B),
 C17(H17A,H17B), C31(H31A,H31B), C21(H21A,H21B), C15(H15A,H15B), C22(H22A,H22B),
  C24(H24A,H24B), C27(H27A,H27B), C23(H23A,H23B), C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4), C10(H10), C4(H4A)
2.c Idealised Me refined as rotating group:
 N5(H5A,H5B,H5C), N6(H6A,H6B,H6C), C40(H40A,H40B,H40C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_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
F2 F -0.2934(8) 0.5123(3) 0.33186(16) 0.0255(9) Uani 1 1 d . . . . .
F1 F 1.2940(8) 0.5032(3) 0.67468(18) 0.0311(10) Uani 1 1 d . . . . .
O1 O 0.6456(10) 0.3588(4) 0.4994(2) 0.0214(11) Uani 1 1 d . . . . .
O3 O 0.6281(10) 0.1350(4) 0.6214(2) 0.0257(11) Uani 1 1 d . . . . .
O6 O 0.1420(10) 0.3622(4) 0.3847(2) 0.0239(11) Uani 1 1 d . . . . .
O8 O 0.3624(10) 0.8866(4) 0.3762(2) 0.0251(11) Uani 1 1 d . . . . .
O4 O 0.8553(9) -0.0274(4) 0.5806(2) 0.0223(11) Uani 1 1 d . . . . .
O7 O 0.1507(10) 1.0566(4) 0.4146(2) 0.0254(12) Uani 1 1 d . . . . .
O2 O 0.8654(10) 0.6622(4) 0.6233(2) 0.0278(12) Uani 1 1 d . . . . .
N1 N 1.0020(12) 0.3121(5) 0.5665(2) 0.0187(13) Uani 1 1 d . . . . .
O5 O 0.3460(10) 0.6761(4) 0.5030(2) 0.0226(11) Uani 1 1 d . . . . .
N2 N 0.7630(12) 0.5084(5) 0.5620(2) 0.0195(13) Uani 1 1 d . . . . .
H2 H 0.631622 0.560099 0.544956 0.023 Uiso 1 1 calc R . . . .
N4 N 0.2363(12) 0.5217(5) 0.4431(2) 0.0172(13) Uani 1 1 d . . . . .
H4 H 0.367728 0.471583 0.461120 0.021 Uiso 1 1 calc R . . . .
N5 N 0.6425(12) 1.1870(5) 0.3791(3) 0.0223(13) Uani 1 1 d . . . . .
H5A H 0.498864 1.133224 0.392015 0.027 Uiso 1 1 calc GR . . . .
H5B H 0.614230 1.261876 0.396017 0.027 Uiso 1 1 calc GR . . . .
H5C H 0.806479 1.149199 0.392202 0.027 Uiso 1 1 calc GR . . . .
N3 N -0.0090(11) 0.7170(5) 0.4348(2) 0.0167(13) Uani 1 1 d . . . . .
N6 N 0.3596(12) -0.1486(5) 0.6212(2) 0.0230(13) Uani 1 1 d . . . . .
H6A H 0.233851 -0.110039 0.593765 0.028 Uiso 1 1 calc GR . . . .
H6B H 0.365074 -0.234793 0.619321 0.028 Uiso 1 1 calc GR . . . .
H6C H 0.532250 -0.115892 0.610367 0.028 Uiso 1 1 calc GR . . . .
C10 C -0.1682(14) 0.6739(6) 0.3903(3) 0.0178(15) Uani 1 1 d . . . . .
H10 H -0.310662 0.728614 0.371471 0.021 Uiso 1 1 calc R . . . .
C6 C 0.8177(15) 0.0903(6) 0.5880(3) 0.0184(15) Uani 1 1 d . . . . .
C2 C 0.9146(14) 0.5550(6) 0.6075(3) 0.0209(17) Uani 1 1 d . . . . .
C9 C -0.1272(13) 0.5572(6) 0.3732(3) 0.0169(15) Uani 1 1 d . . . . .
C7 C 0.2003(14) 0.6422(6) 0.4623(3) 0.0192(17) Uani 1 1 d . . . . .
C1 C 0.7946(14) 0.3906(5) 0.5404(3) 0.0177(16) Uani 1 1 d . . . . .
C11 C -0.0404(15) 0.8507(5) 0.4473(3) 0.0197(16) Uani 1 1 d . . . . .
H11A H -0.020282 0.854467 0.492999 0.024 Uiso 1 1 calc R . . . .
H11B H -0.230365 0.883270 0.436495 0.024 Uiso 1 1 calc R . . . .
C8 C 0.0863(14) 0.4718(6) 0.3982(3) 0.0204(16) Uani 1 1 d . . . . .
C12 C 0.1782(15) 0.9371(6) 0.4087(3) 0.0224(16) Uani 1 1 d . . . . .
C5 C 1.0327(15) 0.1796(6) 0.5511(3) 0.0194(16) Uani 1 1 d . . . . .
H5D H 1.223391 0.146377 0.560852 0.023 Uiso 1 1 calc R . . . .
H5E H 1.010900 0.179861 0.505133 0.023 Uiso 1 1 calc R . . . .
C3 C 1.1272(15) 0.4647(6) 0.6313(3) 0.0218(17) Uani 1 1 d . . . . .
C34 C 0.3946(14) 0.2355(6) 0.9933(3) 0.0243(14) Uani 1 1 d . . . . .
H34A H 0.598521 0.222234 0.997844 0.029 Uiso 1 1 calc R . . . .
H34B H 0.367181 0.309419 0.960052 0.029 Uiso 1 1 calc R . . . .
C4 C 1.1657(14) 0.3492(6) 0.6118(3) 0.0188(16) Uani 1 1 d . . . . .
H4A H 1.307511 0.292285 0.629327 0.023 Uiso 1 1 calc R . . . .
C38 C 0.3687(14) 0.5430(6) 1.1595(3) 0.0247(14) Uani 1 1 d . . . . .
H38A H 0.339860 0.614775 1.125220 0.030 Uiso 1 1 calc R . . . .
H38B H 0.572944 0.530551 1.163887 0.030 Uiso 1 1 calc R . . . .
C32 C 0.4097(14) 0.0845(6) 0.9085(3) 0.0235(14) Uani 1 1 d . . . . .
H32A H 0.614496 0.073718 0.912525 0.028 Uiso 1 1 calc R . . . .
H32B H 0.376536 0.158042 0.875471 0.028 Uiso 1 1 calc R . . . .
C14 C 0.7697(14) 1.0976(5) 0.2795(3) 0.0260(15) Uani 1 1 d . . . . .
H14A H 0.973374 1.088978 0.285678 0.031 Uiso 1 1 calc R . . . .
H14B H 0.680255 1.019662 0.302228 0.031 Uiso 1 1 calc R . . . .
C30 C 0.4212(14) -0.0656(6) 0.8235(3) 0.0273(15) Uani 1 1 d . . . . .
H30A H 0.627460 -0.072524 0.825503 0.033 Uiso 1 1 calc R . . . .
H30B H 0.376783 0.007264 0.790906 0.033 Uiso 1 1 calc R . . . .
C18 C 0.8798(14) 0.8473(6) 0.0937(3) 0.0254(15) Uani 1 1 d . . . . .
H18A H 1.085191 0.856725 0.088130 0.031 Uiso 1 1 calc R . . . .
H18B H 0.843075 0.773626 0.126838 0.031 Uiso 1 1 calc R . . . .
C36 C 0.3822(14) 0.3866(6) 1.0774(3) 0.0260(15) Uani 1 1 d . . . . .
H36A H 0.356839 0.460562 1.044111 0.031 Uiso 1 1 calc R . . . .
H36B H 0.585869 0.371855 1.081798 0.031 Uiso 1 1 calc R . . . .
C16 C 0.8498(14) 0.9880(6) 0.1824(3) 0.0243(14) Uani 1 1 d . . . . .
H16A H 0.804989 0.910105 0.212286 0.029 Uiso 1 1 calc R . . . .
H16B H 1.055805 0.996269 0.179655 0.029 Uiso 1 1 calc R . . . .
C20 C 0.8934(13) 0.6950(6) 0.0100(3) 0.0246(15) Uani 1 1 d . . . . .
H20A H 0.856603 0.622425 0.043808 0.029 Uiso 1 1 calc R . . . .
H20B H 1.098905 0.703949 0.004208 0.029 Uiso 1 1 calc R . . . .
C33 C 0.2763(14) 0.1154(6) 0.9714(3) 0.0252(15) Uani 1 1 d . . . . .
H33A H 0.305784 0.041113 1.004204 0.030 Uiso 1 1 calc R . . . .
H33B H 0.072035 0.128157 0.967065 0.030 Uiso 1 1 calc R . . . .
C35 C 0.2614(14) 0.2689(6) 1.0557(3) 0.0254(15) Uani 1 1 d . . . . .
H35A H 0.057801 0.283475 1.050988 0.031 Uiso 1 1 calc R . . . .
H35B H 0.286575 0.194656 1.088842 0.031 Uiso 1 1 calc R . . . .
C39 C 0.2377(14) 0.5807(6) 1.2210(3) 0.0284(16) Uani 1 1 d . . . . .
H39A H 0.272636 0.510735 1.255814 0.034 Uiso 1 1 calc R . . . .
H39B H 0.032658 0.590833 1.217346 0.034 Uiso 1 1 calc R . . . .
C28 C 0.4189(14) -0.2159(6) 0.7373(3) 0.0293(16) Uani 1 1 d . . . . .
H28A H 0.623879 -0.204271 0.732441 0.035 Uiso 1 1 calc R . . . .
H28B H 0.379803 -0.305833 0.731736 0.035 Uiso 1 1 calc R . . . .
C13 C 0.6554(15) 1.2146(6) 0.3085(3) 0.0249(15) Uani 1 1 d . . . . .
H13A H 0.777654 1.288767 0.294848 0.030 Uiso 1 1 calc R . . . .
H13B H 0.465772 1.237301 0.293528 0.030 Uiso 1 1 calc R . . . .
C19 C 0.7688(14) 0.8166(6) 0.0318(3) 0.0246(15) Uani 1 1 d . . . . .
H19A H 0.563096 0.808295 0.037020 0.030 Uiso 1 1 calc R . . . .
H19B H 0.808361 0.889521 -0.001658 0.030 Uiso 1 1 calc R . . . .
C37 C 0.2522(14) 0.4222(6) 1.1402(3) 0.0255(15) Uani 1 1 d . . . . .
H37A H 0.047465 0.433875 1.136498 0.031 Uiso 1 1 calc R . . . .
H37B H 0.284521 0.349892 1.173998 0.031 Uiso 1 1 calc R . . . .
C29 C 0.3135(14) -0.1896(6) 0.8034(3) 0.0268(15) Uani 1 1 d . . . . .
H29A H 0.370102 -0.262903 0.834547 0.032 Uiso 1 1 calc R . . . .
H29B H 0.106375 -0.185080 0.804759 0.032 Uiso 1 1 calc R . . . .
C40 C 0.3536(15) 0.7055(6) 1.2377(3) 0.0324(16) Uani 1 1 d . . . . .
H40A H 0.318465 0.775267 1.203543 0.049 Uiso 1 1 calc GR . . . .
H40B H 0.555540 0.695010 1.242920 0.049 Uiso 1 1 calc GR . . . .
H40C H 0.261120 0.726391 1.277270 0.049 Uiso 1 1 calc GR . . . .
C17 C 0.7529(14) 0.9688(6) 0.1168(3) 0.0248(15) Uani 1 1 d . . . . .
H17A H 0.546236 0.963624 0.118709 0.030 Uiso 1 1 calc R . . . .
H17B H 0.806162 1.044240 0.086061 0.030 Uiso 1 1 calc R . . . .
C31 C 0.2963(14) -0.0371(6) 0.8873(3) 0.0263(15) Uani 1 1 d . . . . .
H31A H 0.335790 -0.111144 0.919638 0.032 Uiso 1 1 calc R . . . .
H31B H 0.090596 -0.027590 0.884885 0.032 Uiso 1 1 calc R . . . .
C21 C 0.7803(14) 0.6623(6) -0.0514(3) 0.0247(15) Uani 1 1 d . . . . .
H21A H 0.575126 0.652580 -0.045427 0.030 Uiso 1 1 calc R . . . .
H21B H 0.815374 0.735356 -0.085057 0.030 Uiso 1 1 calc R . . . .
C15 C 0.7202(14) 1.1047(6) 0.2095(3) 0.0237(14) Uani 1 1 d . . . . .
H15A H 0.803231 1.184060 0.186631 0.028 Uiso 1 1 calc R . . . .
H15B H 0.516426 1.108776 0.203135 0.028 Uiso 1 1 calc R . . . .
C22 C 0.9066(13) 0.5413(6) -0.0737(3) 0.0260(15) Uani 1 1 d . . . . .
H22A H 0.871907 0.468507 -0.039981 0.031 Uiso 1 1 calc R . . . .
H22B H 1.111746 0.551280 -0.079690 0.031 Uiso 1 1 calc R . . . .
C24 C 0.9149(14) 0.3854(6) -0.1565(3) 0.0275(15) Uani 1 1 d . . . . .
H24A H 0.882096 0.313882 -0.121944 0.033 Uiso 1 1 calc R . . . .
H24B H 1.119830 0.394204 -0.163782 0.033 Uiso 1 1 calc R . . . .
C27 C 0.2735(15) -0.1239(6) 0.6872(3) 0.0283(16) Uani 1 1 d . . . . .
H27A H 0.068373 -0.133023 0.693796 0.034 Uiso 1 1 calc R . . . .
H27B H 0.318800 -0.034389 0.692258 0.034 Uiso 1 1 calc R . . . .
C23 C 0.7953(14) 0.5076(6) -0.1349(3) 0.0246(15) Uani 1 1 d . . . . .
H23A H 0.589439 0.499974 -0.129308 0.030 Uiso 1 1 calc R . . . .
H23B H 0.834336 0.579505 -0.168894 0.030 Uiso 1 1 calc R . . . .
C25 C 0.7943(14) 0.3502(6) -0.2163(3) 0.0273(15) Uani 1 1 d . . . . .
H25A H 0.826798 0.421353 -0.251004 0.033 Uiso 1 1 calc R . . . .
H25B H 0.589494 0.340476 -0.209100 0.033 Uiso 1 1 calc R . . . .
C26 C 0.9209(16) 0.2266(6) -0.2367(3) 0.0357(17) Uani 1 1 d . . . . .
H26A H 0.831044 0.207320 -0.274604 0.053 Uiso 1 1 calc GR . . . .
H26B H 0.890967 0.155673 -0.202435 0.053 Uiso 1 1 calc GR . . . .
H26C H 1.122128 0.237041 -0.246220 0.053 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
F2 C9 1.353(7) . ?
F1 C3 1.358(7) . ?
O1 C1 1.239(7) . ?
O3 C6 1.244(8) . ?
O6 C8 1.239(7) . ?
O8 C12 1.242(8) . ?
O4 C6 1.272(7) . ?
O7 C12 1.279(8) . ?
O2 C2 1.229(7) . ?
N1 C1 1.365(8) . ?
N1 C5 1.471(8) . ?
N1 C4 1.373(8) . ?
O5 C7 1.233(8) . ?
N2 H2 0.8800 . ?
N2 C2 1.386(8) . ?
N2 C1 1.376(8) . ?
N4 H4 0.8800 . ?
N4 C7 1.383(8) . ?
N4 C8 1.388(8) . ?
N5 H5A 0.9100 . ?
N5 H5B 0.9100 . ?
N5 H5C 0.9100 . ?
N5 C13 1.492(8) . ?
N3 C10 1.372(8) . ?
N3 C7 1.364(8) . ?
N3 C11 1.464(8) . ?
N6 H6A 0.9100 . ?
N6 H6B 0.9100 . ?
N6 H6C 0.9100 . ?
N6 C27 1.498(8) . ?
C10 H10 0.9500 . ?
C10 C9 1.329(9) . ?
C6 C5 1.528(10) . ?
C2 C3 1.436(9) . ?
C9 C8 1.418(9) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.536(10) . ?
C5 H5D 0.9900 . ?
C5 H5E 0.9900 . ?
C3 C4 1.337(9) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C34 C33 1.530(8) . ?
C34 C35 1.524(8) . ?
C4 H4A 0.9500 . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C38 C39 1.519(8) . ?
C38 C37 1.511(8) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.524(8) . ?
C32 C31 1.529(8) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.521(8) . ?
C14 C15 1.516(8) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C29 1.531(8) . ?
C30 C31 1.520(8) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.523(8) . ?
C18 C17 1.525(8) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C36 C35 1.512(8) . ?
C36 C37 1.533(8) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.534(8) . ?
C16 C15 1.524(8) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C19 1.510(8) . ?
C20 C21 1.525(8) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C39 C40 1.525(9) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.528(8) . ?
C28 C27 1.526(9) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.512(8) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.521(8) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C23 1.505(8) . ?
C24 C25 1.518(8) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.522(9) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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 N1 C5 119.5(5) . . ?
C1 N1 C4 121.6(5) . . ?
C4 N1 C5 118.6(5) . . ?
C2 N2 H2 116.3 . . ?
C1 N2 H2 116.3 . . ?
C1 N2 C2 127.4(6) . . ?
C7 N4 H4 116.7 . . ?
C7 N4 C8 126.7(6) . . ?
C8 N4 H4 116.7 . . ?
H5A N5 H5B 109.5 . . ?
H5A N5 H5C 109.5 . . ?
H5B N5 H5C 109.5 . . ?
C13 N5 H5A 109.5 . . ?
C13 N5 H5B 109.5 . . ?
C13 N5 H5C 109.5 . . ?
C10 N3 C11 119.5(5) . . ?
C7 N3 C10 121.2(5) . . ?
C7 N3 C11 118.8(5) . . ?
H6A N6 H6B 109.5 . . ?
H6A N6 H6C 109.5 . . ?
H6B N6 H6C 109.5 . . ?
C27 N6 H6A 109.5 . . ?
C27 N6 H6B 109.5 . . ?
C27 N6 H6C 109.5 . . ?
N3 C10 H10 119.3 . . ?
C9 C10 N3 121.4(6) . . ?
C9 C10 H10 119.3 . . ?
O3 C6 O4 126.1(6) . . ?
O3 C6 C5 120.1(5) . . ?
O4 C6 C5 113.8(6) . . ?
O2 C2 N2 121.4(6) . . ?
O2 C2 C3 126.6(6) . . ?
N2 C2 C3 111.9(6) . . ?
F2 C9 C8 116.3(5) . . ?
C10 C9 F2 121.3(6) . . ?
C10 C9 C8 122.3(6) . . ?
O5 C7 N4 120.9(6) . . ?
O5 C7 N3 123.5(6) . . ?
N3 C7 N4 115.6(6) . . ?
O1 C1 N1 122.4(5) . . ?
O1 C1 N2 121.8(6) . . ?
N1 C1 N2 115.7(6) . . ?
N3 C11 H11A 109.3 . . ?
N3 C11 H11B 109.3 . . ?
N3 C11 C12 111.7(5) . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
O6 C8 N4 120.1(6) . . ?
O6 C8 C9 127.0(6) . . ?
N4 C8 C9 112.8(6) . . ?
O8 C12 O7 126.5(6) . . ?
O8 C12 C11 118.8(6) . . ?
O7 C12 C11 114.7(6) . . ?
N1 C5 C6 112.1(5) . . ?
N1 C5 H5D 109.2 . . ?
N1 C5 H5E 109.2 . . ?
C6 C5 H5D 109.2 . . ?
C6 C5 H5E 109.2 . . ?
H5D C5 H5E 107.9 . . ?
F1 C3 C2 116.5(6) . . ?
C4 C3 F1 120.7(6) . . ?
C4 C3 C2 122.8(6) . . ?
H34A C34 H34B 107.7 . . ?
C33 C34 H34A 108.8 . . ?
C33 C34 H34B 108.8 . . ?
C35 C34 H34A 108.8 . . ?
C35 C34 H34B 108.8 . . ?
C35 C34 C33 114.0(5) . . ?
N1 C4 H4A 119.7 . . ?
C3 C4 N1 120.5(6) . . ?
C3 C4 H4A 119.7 . . ?
H38A C38 H38B 107.6 . . ?
C39 C38 H38A 108.7 . . ?
C39 C38 H38B 108.7 . . ?
C37 C38 H38A 108.7 . . ?
C37 C38 H38B 108.7 . . ?
C37 C38 C39 114.1(5) . . ?
H32A C32 H32B 107.7 . . ?
C33 C32 H32A 108.9 . . ?
C33 C32 H32B 108.9 . . ?
C33 C32 C31 113.3(5) . . ?
C31 C32 H32A 108.9 . . ?
C31 C32 H32B 108.9 . . ?
H14A C14 H14B 107.8 . . ?
C13 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C15 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C15 C14 C13 113.2(5) . . ?
H30A C30 H30B 107.8 . . ?
C29 C30 H30A 108.9 . . ?
C29 C30 H30B 108.9 . . ?
C31 C30 H30A 108.9 . . ?
C31 C30 H30B 108.9 . . ?
C31 C30 C29 113.2(5) . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 H18A 108.6 . . ?
C19 C18 H18B 108.6 . . ?
C19 C18 C17 114.5(5) . . ?
C17 C18 H18A 108.6 . . ?
C17 C18 H18B 108.6 . . ?
H36A C36 H36B 107.6 . . ?
C35 C36 H36A 108.6 . . ?
C35 C36 H36B 108.6 . . ?
C35 C36 C37 114.7(5) . . ?
C37 C36 H36A 108.6 . . ?
C37 C36 H36B 108.6 . . ?
H16A C16 H16B 107.5 . . ?
C17 C16 H16A 108.5 . . ?
C17 C16 H16B 108.5 . . ?
C15 C16 H16A 108.5 . . ?
C15 C16 H16B 108.5 . . ?
C15 C16 C17 114.9(5) . . ?
H20A C20 H20B 107.6 . . ?
C19 C20 H20A 108.7 . . ?
C19 C20 H20B 108.7 . . ?
C19 C20 C21 114.2(5) . . ?
C21 C20 H20A 108.7 . . ?
C21 C20 H20B 108.7 . . ?
C34 C33 H33A 108.9 . . ?
C34 C33 H33B 108.9 . . ?
C32 C33 C34 113.2(5) . . ?
C32 C33 H33A 108.9 . . ?
C32 C33 H33B 108.9 . . ?
H33A C33 H33B 107.7 . . ?
C34 C35 H35A 108.8 . . ?
C34 C35 H35B 108.8 . . ?
C36 C35 C34 113.6(5) . . ?
C36 C35 H35A 108.8 . . ?
C36 C35 H35B 108.8 . . ?
H35A C35 H35B 107.7 . . ?
C38 C39 H39A 109.1 . . ?
C38 C39 H39B 109.1 . . ?
C38 C39 C40 112.5(6) . . ?
H39A C39 H39B 107.8 . . ?
C40 C39 H39A 109.1 . . ?
C40 C39 H39B 109.1 . . ?
H28A C28 H28B 108.2 . . ?
C29 C28 H28A 109.7 . . ?
C29 C28 H28B 109.7 . . ?
C27 C28 H28A 109.7 . . ?
C27 C28 H28B 109.7 . . ?
C27 C28 C29 109.8(5) . . ?
N5 C13 C14 110.2(5) . . ?
N5 C13 H13A 109.6 . . ?
N5 C13 H13B 109.6 . . ?
C14 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C18 C19 H19A 108.8 . . ?
C18 C19 H19B 108.8 . . ?
C20 C19 C18 113.8(5) . . ?
C20 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C38 C37 C36 113.6(5) . . ?
C38 C37 H37A 108.9 . . ?
C38 C37 H37B 108.9 . . ?
C36 C37 H37A 108.9 . . ?
C36 C37 H37B 108.9 . . ?
H37A C37 H37B 107.7 . . ?
C30 C29 H29A 108.6 . . ?
C30 C29 H29B 108.6 . . ?
C28 C29 C30 114.5(5) . . ?
C28 C29 H29A 108.6 . . ?
C28 C29 H29B 108.6 . . ?
H29A C29 H29B 107.6 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C18 C17 C16 112.4(5) . . ?
C18 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C16 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.9 . . ?
C32 C31 H31A 108.9 . . ?
C32 C31 H31B 108.9 . . ?
C30 C31 C32 113.4(5) . . ?
C30 C31 H31A 108.9 . . ?
C30 C31 H31B 108.9 . . ?
H31A C31 H31B 107.7 . . ?
C20 C21 H21A 108.7 . . ?
C20 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C22 C21 C20 114.4(5) . . ?
C22 C21 H21A 108.7 . . ?
C22 C21 H21B 108.7 . . ?
C14 C15 C16 110.9(5) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.0 . . ?
C21 C22 H22A 108.5 . . ?
C21 C22 H22B 108.5 . . ?
C21 C22 C23 115.0(5) . . ?
H22A C22 H22B 107.5 . . ?
C23 C22 H22A 108.5 . . ?
C23 C22 H22B 108.5 . . ?
H24A C24 H24B 107.6 . . ?
C23 C24 H24A 108.6 . . ?
C23 C24 H24B 108.6 . . ?
C23 C24 C25 114.7(5) . . ?
C25 C24 H24A 108.6 . . ?
C25 C24 H24B 108.6 . . ?
N6 C27 C28 112.3(5) . . ?
N6 C27 H27A 109.1 . . ?
N6 C27 H27B 109.1 . . ?
C28 C27 H27A 109.1 . . ?
C28 C27 H27B 109.1 . . ?
H27A C27 H27B 107.9 . . ?
C22 C23 H23A 108.5 . . ?
C22 C23 H23B 108.5 . . ?
C24 C23 C22 115.2(5) . . ?
C24 C23 H23A 108.5 . . ?
C24 C23 H23B 108.5 . . ?
H23A C23 H23B 107.5 . . ?
C24 C25 H25A 108.9 . . ?
C24 C25 H25B 108.9 . . ?
C24 C25 C26 113.2(6) . . ?
H25A C25 H25B 107.8 . . ?
C26 C25 H25A 108.9 . . ?
C26 C25 H25B 108.9 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
#
_vrf_PLAT029_FuA_14              
;
PROBLEM:  _diffrn_measured_fraction_theta_full value Low .      0.939 Why?   
RESPONSE: The crystal was very poorly diffracting and the problem could 
not be resolved even after collecting fresh data set on variuos crystals.
;
_vrf_THETM01_FuA_14              
;
PROBLEM:  The value of sine(theta_max)/wavelength is less than 0.575
            Calculated sin(theta_max)/wavelength =    0.5563   
RESPONSE: The crystal was poorly diffracting at higher Bragg angles
and the problem could not be resolved even after collecting
fresh data set on variuos crystals.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_FuA_10
_database_code_depnum_ccdc_archive 'CCDC 1868727'
loop_
_audit_author_name
_audit_author_address
'Poulami Chakraborty'
;SRF, IACS
India
;
_audit_update_record             
;
2018-09-20 deposited with the CCDC.	2019-06-07 downloaded from the CCDC.
;
_audit_creation_date             2018-09-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        FuA_10
_chemical_formula_moiety         'C6 H3 F N2 O4, 2(C10 H24 N)'
_chemical_formula_sum            'C26 H51 F N4 O4'
_chemical_formula_weight         502.70
_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                   8.8655(11)
_cell_length_b                   9.0075(11)
_cell_length_c                   18.138(2)
_cell_angle_alpha                87.057(2)
_cell_angle_beta                 76.644(2)
_cell_angle_gamma                88.318(2)
_cell_volume                     1407.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6480
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.72
_cell_measurement_theta_min      2.26
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1678 before and 0.0508 after correction. The Ratio of minimum to maximum transmission is 0.9222. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            33446
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.846
_diffrn_reflns_theta_max         24.846
_diffrn_reflns_theta_min         2.264
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3622
_reflns_number_total             4881
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         4881
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.044
_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)+(0.0326P)²+0.5209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0919
_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 Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b), C7(H7a,H7b), C17(H17a,H17b), C8(H8a,H8b), C19(H19a,H19b),
 C21(H21a,H21b), C14(H14a,H14b), C23(H23a,H23b), C9(H9a,H9b), C18(H18a,H18b),
 C13(H13a,H13b), C10(H10a,H10b), C12(H12a,H12b), C15(H15a,H15b), C22(H22a,H22b),
  C20(H20a,H20b), C24(H24a,H24b), C11(H11a,H11b), C25(H25a,H25b)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.c Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c), C26(H26a,H26b,H26c)
;
_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 0.47183(10) -0.07665(10) 0.64686(5) 0.0263(2) Uani 1 1 d . . . . .
O2 O 0.64536(12) 0.36219(12) 0.43884(6) 0.0212(3) Uani 1 1 d . . . . .
O3 O 0.90719(12) 0.32569(12) 0.53563(6) 0.0215(3) Uani 1 1 d . . . . .
O4 O 1.10377(12) 0.25020(12) 0.44352(7) 0.0249(3) Uani 1 1 d . . . . .
O1 O 0.27550(12) 0.15725(12) 0.62949(7) 0.0243(3) Uani 1 1 d . . . . .
N4 N 0.32981(17) 0.45991(17) 0.42232(8) 0.0162(3) Uani 1 1 d . . . . .
N1 N 0.70268(14) 0.14263(14) 0.49478(7) 0.0161(3) Uani 1 1 d . . . . .
N2 N 0.45806(14) 0.26196(14) 0.53310(8) 0.0173(3) Uani 1 1 d . . . . .
N3 N 1.12908(16) 0.42000(17) 0.61058(8) 0.0179(3) Uani 1 1 d . . . . .
C4 C 0.60087(17) 0.25945(17) 0.48801(9) 0.0164(4) Uani 1 1 d . . . . .
C2 C 0.51752(18) 0.03514(17) 0.59398(9) 0.0176(4) Uani 1 1 d . . . . .
C3 C 0.65926(18) 0.03163(17) 0.54947(9) 0.0177(4) Uani 1 1 d . . . . .
H3 H 0.728305 -0.045363 0.555371 0.021 Uiso 1 1 calc R . . . .
C6 C 0.96538(18) 0.25031(17) 0.47928(9) 0.0172(4) Uani 1 1 d . . . . .
C5 C 0.86112(17) 0.14758(18) 0.44946(9) 0.0189(4) Uani 1 1 d . . . . .
H5A H 0.859174 0.180463 0.397915 0.023 Uiso 1 1 calc R . . . .
H5B H 0.905672 0.047818 0.447936 0.023 Uiso 1 1 calc R . . . .
C7 C 1.05210(18) 0.47015(18) 0.68708(9) 0.0191(4) Uani 1 1 d . . . . .
H7A H 0.987609 0.557175 0.681925 0.023 Uiso 1 1 calc R . . . .
H7B H 1.130320 0.498220 0.713085 0.023 Uiso 1 1 calc R . . . .
C1 C 0.40885(18) 0.15332(17) 0.58739(9) 0.0174(4) Uani 1 1 d . . . . .
C17 C 0.39048(18) 0.44534(18) 0.33977(9) 0.0190(4) Uani 1 1 d . . . . .
H17A H 0.304118 0.436898 0.315834 0.023 Uiso 1 1 calc R . . . .
H17B H 0.452805 0.354797 0.331430 0.023 Uiso 1 1 calc R . . . .
C8 C 0.95298(18) 0.34931(18) 0.73402(9) 0.0203(4) Uani 1 1 d . . . . .
H8A H 1.016108 0.260081 0.736110 0.024 Uiso 1 1 calc R . . . .
H8B H 0.870610 0.326064 0.709615 0.024 Uiso 1 1 calc R . . . .
C19 C 0.55924(19) 0.54990(18) 0.22008(9) 0.0208(4) Uani 1 1 d . . . . .
H19A H 0.476663 0.531250 0.194957 0.025 Uiso 1 1 calc R . . . .
H19B H 0.624430 0.461023 0.217193 0.025 Uiso 1 1 calc R . . . .
C21 C 0.72858(19) 0.64036(19) 0.09555(9) 0.0224(4) Uani 1 1 d . . . . .
H21A H 0.646598 0.617558 0.070803 0.027 Uiso 1 1 calc R . . . .
H21B H 0.792979 0.551532 0.096002 0.027 Uiso 1 1 calc R . . . .
C14 C 0.44318(19) 0.12582(18) 1.12201(9) 0.0214(4) Uani 1 1 d . . . . .
H14A H 0.361181 0.100801 1.097730 0.026 Uiso 1 1 calc R . . . .
H14B H 0.506373 0.036977 1.125073 0.026 Uiso 1 1 calc R . . . .
C23 C 0.89783(19) 0.71928(19) -0.03217(9) 0.0235(4) Uani 1 1 d . . . . .
H23A H 0.960934 0.629948 -0.030350 0.028 Uiso 1 1 calc R . . . .
H23B H 0.815001 0.695663 -0.056193 0.028 Uiso 1 1 calc R . . . .
C9 C 0.88215(18) 0.39550(18) 0.81436(9) 0.0214(4) Uani 1 1 d . . . . .
H9A H 0.964919 0.420212 0.838196 0.026 Uiso 1 1 calc R . . . .
H9B H 0.818721 0.484414 0.811942 0.026 Uiso 1 1 calc R . . . .
C18 C 0.48772(18) 0.57582(18) 0.30291(9) 0.0205(4) Uani 1 1 d . . . . .
H18A H 0.569260 0.589991 0.329356 0.025 Uiso 1 1 calc R . . . .
H18B H 0.423416 0.665371 0.306765 0.025 Uiso 1 1 calc R . . . .
C13 C 0.54312(19) 0.24506(18) 1.07310(9) 0.0218(4) Uani 1 1 d . . . . .
H13A H 0.480105 0.334366 1.071023 0.026 Uiso 1 1 calc R . . . .
H13B H 0.625771 0.268843 1.097211 0.026 Uiso 1 1 calc R . . . .
C10 C 0.78320(19) 0.27627(18) 0.86349(9) 0.0217(4) Uani 1 1 d . . . . .
H10A H 0.699971 0.252285 0.839810 0.026 Uiso 1 1 calc R . . . .
H10B H 0.846460 0.187070 0.865383 0.026 Uiso 1 1 calc R . . . .
C12 C 0.61436(19) 0.20111(18) 0.99274(9) 0.0215(4) Uani 1 1 d . . . . .
H12A H 0.531783 0.176814 0.968690 0.026 Uiso 1 1 calc R . . . .
H12B H 0.677912 0.112157 0.994779 0.026 Uiso 1 1 calc R . . . .
C15 C 0.3712(2) 0.17331(19) 1.20156(9) 0.0242(4) Uani 1 1 d . . . . .
H15A H 0.308462 0.262347 1.198253 0.029 Uiso 1 1 calc R . . . .
H15B H 0.453561 0.198643 1.225564 0.029 Uiso 1 1 calc R . . . .
C22 C 0.82676(19) 0.76244(19) 0.04849(9) 0.0238(4) Uani 1 1 d . . . . .
H22A H 0.762761 0.851260 0.047021 0.029 Uiso 1 1 calc R . . . .
H22B H 0.909124 0.785937 0.072844 0.029 Uiso 1 1 calc R . . . .
C20 C 0.65548(19) 0.67679(19) 0.17701(9) 0.0223(4) Uani 1 1 d . . . . .
H20A H 0.736562 0.698432 0.202565 0.027 Uiso 1 1 calc R . . . .
H20B H 0.590002 0.765042 0.177263 0.027 Uiso 1 1 calc R . . . .
C24 C 0.99718(19) 0.83821(19) -0.08092(10) 0.0253(4) Uani 1 1 d . . . . .
H24A H 0.934223 0.927550 -0.083030 0.030 Uiso 1 1 calc R . . . .
H24B H 1.080182 0.861984 -0.057048 0.030 Uiso 1 1 calc R . . . .
C11 C 0.71331(19) 0.32072(18) 0.94396(9) 0.0223(4) Uani 1 1 d . . . . .
H11A H 0.650044 0.409942 0.942128 0.027 Uiso 1 1 calc R . . . .
H11B H 0.796463 0.344514 0.967731 0.027 Uiso 1 1 calc R . . . .
C25 C 1.0672(2) 0.7932(2) -0.16100(10) 0.0301(4) Uani 1 1 d . . . . .
H25A H 0.984274 0.768921 -0.184817 0.036 Uiso 1 1 calc R . . . .
H25B H 1.130682 0.704184 -0.158932 0.036 Uiso 1 1 calc R . . . .
C16 C 0.2709(2) 0.0562(2) 1.25161(10) 0.0311(4) Uani 1 1 d . . . . .
H16A H 0.189358 0.029669 1.228238 0.047 Uiso 1 1 calc GR . . . .
H16B H 0.226643 0.095358 1.300288 0.047 Uiso 1 1 calc GR . . . .
H16C H 0.333337 -0.030308 1.257901 0.047 Uiso 1 1 calc GR . . . .
C26 C 1.1658(2) 0.9128(2) -0.20973(12) 0.0441(6) Uani 1 1 d . . . . .
H26A H 1.207837 0.877058 -0.259409 0.066 Uiso 1 1 calc GR . . . .
H26B H 1.249008 0.936711 -0.186896 0.066 Uiso 1 1 calc GR . . . .
H26C H 1.102973 1.000100 -0.213706 0.066 Uiso 1 1 calc GR . . . .
H3A H 1.198(2) 0.488(2) 0.5855(10) 0.027(5) Uiso 1 1 d . . . . .
H3B H 1.185(2) 0.327(2) 0.6144(11) 0.039(6) Uiso 1 1 d . . . . .
H3C H 1.051(2) 0.401(2) 0.5812(11) 0.040(6) Uiso 1 1 d . . . . .
H4A H 0.258(2) 0.389(2) 0.4398(11) 0.035(5) Uiso 1 1 d . . . . .
H4B H 0.271(2) 0.550(2) 0.4342(11) 0.038(6) Uiso 1 1 d . . . . .
H4C H 0.409(2) 0.449(2) 0.4466(11) 0.043(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 C2 1.3577(18) . ?
O2 C4 1.2576(18) . ?
O3 C6 1.2565(19) . ?
O4 C6 1.2483(18) . ?
O1 C1 1.2511(19) . ?
N4 C17 1.481(2) . ?
N4 H4A 0.91(2) . ?
N4 H4B 0.95(2) . ?
N4 H4C 0.91(2) . ?
N1 C4 1.385(2) . ?
N1 C3 1.370(2) . ?
N1 C5 1.4550(19) . ?
N2 C4 1.340(2) . ?
N2 C1 1.358(2) . ?
N3 C7 1.485(2) . ?
N3 H3A 0.910(19) . ?
N3 H3B 0.97(2) . ?
N3 H3C 0.99(2) . ?
C2 C3 1.328(2) . ?
C2 C1 1.434(2) . ?
C3 H3 0.9300 . ?
C6 C5 1.528(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.516(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.511(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.522(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C18 1.517(2) . ?
C19 C20 1.517(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.520(2) . ?
C21 C20 1.518(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.523(2) . ?
C14 C15 1.515(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C22 1.519(2) . ?
C23 C24 1.518(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.521(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.516(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.517(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.521(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.520(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.513(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.519(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
C17 N4 H4A 108.8(12) . . ?
C17 N4 H4B 112.9(11) . . ?
C17 N4 H4C 109.8(12) . . ?
H4A N4 H4B 102.5(16) . . ?
H4A N4 H4C 110.3(17) . . ?
H4B N4 H4C 112.3(17) . . ?
C4 N1 C5 119.45(13) . . ?
C3 N1 C4 119.97(13) . . ?
C3 N1 C5 120.21(13) . . ?
C4 N2 C1 121.89(14) . . ?
C7 N3 H3A 110.5(11) . . ?
C7 N3 H3B 110.7(11) . . ?
C7 N3 H3C 110.3(11) . . ?
H3A N3 H3B 108.0(15) . . ?
H3A N3 H3C 110.8(15) . . ?
H3B N3 H3C 106.5(16) . . ?
O2 C4 N1 118.66(14) . . ?
O2 C4 N2 121.05(15) . . ?
N2 C4 N1 120.29(14) . . ?
F1 C2 C1 118.34(13) . . ?
C3 C2 F1 119.73(14) . . ?
C3 C2 C1 121.92(15) . . ?
N1 C3 H3 120.4 . . ?
C2 C3 N1 119.29(15) . . ?
C2 C3 H3 120.4 . . ?
O3 C6 C5 118.96(14) . . ?
O4 C6 O3 126.26(15) . . ?
O4 C6 C5 114.78(14) . . ?
N1 C5 C6 113.78(13) . . ?
N1 C5 H5A 108.8 . . ?
N1 C5 H5B 108.8 . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
N3 C7 H7A 109.3 . . ?
N3 C7 H7B 109.3 . . ?
N3 C7 C8 111.53(13) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
O1 C1 N2 121.34(15) . . ?
O1 C1 C2 122.05(15) . . ?
N2 C1 C2 116.61(14) . . ?
N4 C17 H17A 109.1 . . ?
N4 C17 H17B 109.1 . . ?
N4 C17 C18 112.56(13) . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C7 C8 C9 112.06(13) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H19A C19 H19B 107.5 . . ?
C18 C19 H19A 108.5 . . ?
C18 C19 H19B 108.5 . . ?
C18 C19 C20 115.03(14) . . ?
C20 C19 H19A 108.5 . . ?
C20 C19 H19B 108.5 . . ?
H21A C21 H21B 107.5 . . ?
C22 C21 H21A 108.5 . . ?
C22 C21 H21B 108.5 . . ?
C20 C21 H21A 108.5 . . ?
C20 C21 H21B 108.5 . . ?
C20 C21 C22 115.20(14) . . ?
H14A C14 H14B 107.8 . . ?
C13 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C15 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C15 C14 C13 113.19(14) . . ?
H23A C23 H23B 107.6 . . ?
C22 C23 H23A 108.7 . . ?
C22 C23 H23B 108.7 . . ?
C24 C23 H23A 108.7 . . ?
C24 C23 H23B 108.7 . . ?
C24 C23 C22 114.42(14) . . ?
C8 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 C8 113.58(14) . . ?
C10 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C17 C18 C19 110.77(13) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C12 C13 C14 114.20(13) . . ?
C12 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 C9 113.98(14) . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C13 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C13 C12 C11 114.05(13) . . ?
H12A C12 H12B 107.6 . . ?
C11 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C14 C15 H15A 108.7 . . ?
C14 C15 H15B 108.7 . . ?
C14 C15 C16 114.26(14) . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C21 C22 H22A 109.0 . . ?
C21 C22 H22B 109.0 . . ?
C23 C22 C21 112.84(14) . . ?
C23 C22 H22A 109.0 . . ?
C23 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C19 C20 C21 112.02(14) . . ?
C19 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
C21 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C23 C24 H24A 108.8 . . ?
C23 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
C25 C24 C23 113.67(15) . . ?
C25 C24 H24A 108.8 . . ?
C25 C24 H24B 108.8 . . ?
C10 C11 C12 113.71(14) . . ?
C10 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C24 C25 H25A 108.9 . . ?
C24 C25 H25B 108.9 . . ?
C24 C25 C26 113.53(16) . . ?
H25A C25 H25B 107.7 . . ?
C26 C25 H25A 108.9 . . ?
C26 C25 H25B 108.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

_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_FuA_9
_database_code_depnum_ccdc_archive 'CCDC 1868726'
loop_
_audit_author_name
_audit_author_address
'Poulami Chakraborty'
;SRF, IACS
India
;
_audit_update_record             
;
2018-09-20 deposited with the CCDC.	2019-06-07 downloaded from the CCDC.
;
_audit_creation_date             2018-09-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        FuA_9
_chemical_formula_moiety         'C6 H4 F N2 O4, C9 H22 N'
_chemical_formula_sum            'C15 H26 F N3 O4'
_chemical_formula_weight         331.39
_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                   4.6735(7)
_cell_length_b                   10.5865(15)
_cell_length_c                   17.880(3)
_cell_angle_alpha                100.883(2)
_cell_angle_beta                 96.135(2)
_cell_angle_gamma                91.952(2)
_cell_volume                     862.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2502
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.90
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.1427 before and 0.0571 after correction. The Ratio of minimum to maximum transmission is 0.8745. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22159
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.114
_diffrn_reflns_theta_min         1.962
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2121
_reflns_number_total             3370
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.031(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.021
_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)+(0.0376P)²+0.6499P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1214
_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, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C10(H10A,H10B), C9(H9A,H9B), C11(H11A,
 H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4)
2.c Idealised Me refined as rotating group:
 N3(H3A,H3B,H3C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_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 0.2605(3) 0.60108(12) 0.21026(8) 0.0282(4) Uani 1 1 d . . . . .
O1 O 0.8522(3) 0.33872(14) -0.00286(9) 0.0220(4) Uani 1 1 d . . . . .
O2 O 0.6745(4) 0.72252(14) 0.14360(10) 0.0253(4) Uani 1 1 d . . . . .
O3 O 0.8971(4) 0.20381(15) 0.15334(10) 0.0270(4) Uani 1 1 d . . . . .
O4 O 0.6630(3) 0.01387(14) 0.10326(10) 0.0237(4) Uani 1 1 d . . . . .
N2 N 0.5136(4) 0.33811(17) 0.08037(11) 0.0187(5) Uani 1 1 d . . . . .
N1 N 0.7549(4) 0.52831(17) 0.07129(11) 0.0194(5) Uani 1 1 d . . . . .
H1 H 0.877615 0.566578 0.049335 0.023 Uiso 1 1 calc R . . . .
N3 N 0.1641(4) -0.09351(18) 0.14746(12) 0.0239(5) Uani 1 1 d . . . . .
H3A H 0.130300 -0.175486 0.124110 0.029 Uiso 1 1 calc GR . . . .
H3B H 0.317761 -0.060517 0.130933 0.029 Uiso 1 1 calc GR . . . .
H3C H 0.011647 -0.049095 0.136905 0.029 Uiso 1 1 calc GR . . . .
C2 C 0.6196(5) 0.6060(2) 0.12677(14) 0.0212(6) Uani 1 1 d . . . . .
C1 C 0.7152(5) 0.3973(2) 0.04744(14) 0.0198(5) Uani 1 1 d . . . . .
C3 C 0.4145(5) 0.5332(2) 0.15764(14) 0.0195(5) Uani 1 1 d . . . . .
C6 C 0.7010(5) 0.1355(2) 0.11157(14) 0.0208(5) Uani 1 1 d . . . . .
C5 C 0.4771(5) 0.1974(2) 0.06320(14) 0.0197(5) Uani 1 1 d . . . . .
H5A H 0.493897 0.166426 0.009298 0.024 Uiso 1 1 calc R . . . .
H5B H 0.285513 0.171495 0.072874 0.024 Uiso 1 1 calc R . . . .
C4 C 0.3692(5) 0.4061(2) 0.13636(14) 0.0199(5) Uani 1 1 d . . . . .
H4 H 0.238279 0.362906 0.159691 0.024 Uiso 1 1 calc R . . . .
C7 C 0.2186(6) -0.0859(2) 0.23156(14) 0.0262(6) Uani 1 1 d . . . . .
H7A H 0.349980 -0.151119 0.241942 0.031 Uiso 1 1 calc R . . . .
H7B H 0.038818 -0.103951 0.251067 0.031 Uiso 1 1 calc R . . . .
C8 C 0.3457(6) 0.0450(2) 0.27298(15) 0.0284(6) Uani 1 1 d . . . . .
H8A H 0.518069 0.065816 0.250981 0.034 Uiso 1 1 calc R . . . .
H8B H 0.208288 0.109513 0.265765 0.034 Uiso 1 1 calc R . . . .
C10 C 0.5826(6) 0.1733(2) 0.39979(15) 0.0338(7) Uani 1 1 d . . . . .
H10A H 0.461137 0.244608 0.395452 0.041 Uiso 1 1 calc R . . . .
H10B H 0.752961 0.186352 0.374982 0.041 Uiso 1 1 calc R . . . .
C9 C 0.4207(6) 0.0492(2) 0.35776(15) 0.0319(7) Uani 1 1 d . . . . .
H9A H 0.537530 -0.022693 0.364562 0.038 Uiso 1 1 calc R . . . .
H9B H 0.244427 0.038640 0.380592 0.038 Uiso 1 1 calc R . . . .
C11 C 0.6740(6) 0.1751(3) 0.48415(15) 0.0350(7) Uani 1 1 d . . . . .
H11A H 0.503021 0.165394 0.509351 0.042 Uiso 1 1 calc R . . . .
H11B H 0.789129 0.101791 0.488546 0.042 Uiso 1 1 calc R . . . .
C12 C 0.8460(6) 0.2971(3) 0.52563(16) 0.0371(7) Uani 1 1 d . . . . .
H12A H 0.729021 0.370303 0.522518 0.045 Uiso 1 1 calc R . . . .
H12B H 1.014455 0.308135 0.499685 0.045 Uiso 1 1 calc R . . . .
C13 C 0.9432(7) 0.2967(3) 0.60939(16) 0.0397(7) Uani 1 1 d . . . . .
H13A H 0.773790 0.290446 0.635711 0.048 Uiso 1 1 calc R . . . .
H13B H 1.049745 0.220452 0.612416 0.048 Uiso 1 1 calc R . . . .
C14 C 1.1298(7) 0.4138(3) 0.65113(18) 0.0497(9) Uani 1 1 d . . . . .
H14A H 1.297532 0.421021 0.624298 0.060 Uiso 1 1 calc R . . . .
H14B H 1.197298 0.400528 0.702127 0.060 Uiso 1 1 calc R . . . .
C15 C 0.9809(8) 0.5399(3) 0.65848(19) 0.0546(9) Uani 1 1 d . . . . .
H15A H 0.932725 0.559275 0.608474 0.082 Uiso 1 1 calc GR . . . .
H15B H 1.107637 0.607736 0.689272 0.082 Uiso 1 1 calc GR . . . .
H15C H 0.808236 0.532486 0.682339 0.082 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 C3 1.358(3) . ?
O1 C1 1.243(3) . ?
O2 C2 1.225(3) . ?
O3 C6 1.235(3) . ?
O4 C6 1.272(3) . ?
N2 C1 1.358(3) . ?
N2 C5 1.464(3) . ?
N2 C4 1.372(3) . ?
N1 H1 0.8600 . ?
N1 C2 1.386(3) . ?
N1 C1 1.371(3) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 H3C 0.8900 . ?
N3 C7 1.485(3) . ?
C2 C3 1.429(3) . ?
C3 C4 1.330(3) . ?
C6 C5 1.529(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C4 H4 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.511(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.511(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C9 1.517(4) . ?
C10 C11 1.519(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.518(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.519(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.514(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.516(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C1 N2 C5 119.28(19) . . ?
C1 N2 C4 121.17(19) . . ?
C4 N2 C5 119.05(19) . . ?
C2 N1 H1 116.3 . . ?
C1 N1 H1 116.3 . . ?
C1 N1 C2 127.4(2) . . ?
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C7 N3 H3A 109.5 . . ?
C7 N3 H3B 109.5 . . ?
C7 N3 H3C 109.5 . . ?
O2 C2 N1 121.4(2) . . ?
O2 C2 C3 127.0(2) . . ?
N1 C2 C3 111.5(2) . . ?
O1 C1 N2 123.0(2) . . ?
O1 C1 N1 121.0(2) . . ?
N2 C1 N1 116.0(2) . . ?
F1 C3 C2 116.33(19) . . ?
C4 C3 F1 120.5(2) . . ?
C4 C3 C2 123.1(2) . . ?
O3 C6 O4 126.3(2) . . ?
O3 C6 C5 119.6(2) . . ?
O4 C6 C5 114.1(2) . . ?
N2 C5 C6 111.93(19) . . ?
N2 C5 H5A 109.2 . . ?
N2 C5 H5B 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N2 C4 H4 119.7 . . ?
C3 C4 N2 120.7(2) . . ?
C3 C4 H4 119.7 . . ?
N3 C7 H7A 109.2 . . ?
N3 C7 H7B 109.2 . . ?
N3 C7 C8 112.06(19) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 C7 111.8(2) . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H10A C10 H10B 107.7 . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C9 C10 C11 113.8(2) . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C8 C9 C10 113.5(2) . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C10 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 C10 113.9(2) . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C11 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C11 C12 C13 113.6(2) . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C12 C13 H13A 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.5 . . ?
C14 C13 C12 114.8(3) . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C13 C14 H14A 108.6 . . ?
C13 C14 H14B 108.6 . . ?
C13 C14 C15 114.7(3) . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_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_FuA_15
_database_code_depnum_ccdc_archive 'CCDC 1868724'
loop_
_audit_author_name
_audit_author_address
'Poulami Chakraborty'
;SRF, IACS
India
;
_audit_update_record             
;
2018-09-20 deposited with the CCDC.	2019-06-07 downloaded from the CCDC.
;
_audit_creation_date             2018-09-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        FuA_15
_chemical_formula_moiety         'C6 H4 F N2 O4, C15 H34 N'
_chemical_formula_sum            'C21 H38 F N3 O4'
_chemical_formula_weight         415.54
_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                   4.7775(4)
_cell_length_b                   10.4402(9)
_cell_length_c                   45.660(3)
_cell_angle_alpha                88.427(3)
_cell_angle_beta                 88.793(2)
_cell_angle_gamma                88.556(3)
_cell_volume                     2275.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3478
_cell_measurement_temperature    106(2)
_cell_measurement_theta_max      24.48
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1037 before and 0.0541 after correction. The Ratio of minimum to maximum transmission is 0.8877. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0818
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_number            19877
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        24.543
_diffrn_reflns_theta_max         24.543
_diffrn_reflns_theta_min         2.231
_diffrn_ambient_temperature      105.94
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4227
_reflns_number_total             7568
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         7568
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1374
_refine_ls_R_factor_gt           0.0776
_refine_ls_restrained_S_all      1.160
_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)+(0.0200P)²+5.2281P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1538
_refine_ls_wR_factor_ref         0.1723
_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, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C11(H11A,H11B), C5(H5D,H5E), C18(H18A,H18B), C20(H20A,H20B),
 C22(H22A,H22B), C24(H24A,H24B), C23(H23A,H23B), C28(H28A,H28B), C39(H39A,H39B),
  C13(H13A,H13B), C35(H35A,H35B), C33(H33A,H33B), C31(H31A,H31B), C34(H34A,
 H34B), C32(H32A,H32B), C19(H19A,H19B), C25(H25A,H25B), C26(H26A,H26B),
 C29(H29A,H29B), C15(H15A,H15B), C36(H36A,H36B), C41(H41A,H41B), C21(H21A,H21B),
  C37(H37A,H37B), C17(H17A,H17B), C30(H30A,H30B), C16(H16A,H16B), C38(H38A,
 H38B), C40(H40A,H40B)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4A), N2(H2), C4(H4), C10(H10)
2.c Idealised Me refined as rotating group:
 N5(H5A,H5B,H5C), N6(H6A,H6B,H6C), C27(H27A,H27B,H27C), C42(H42A,H42B,H42C)
;
_atom_sites_solution_hydrogens   geom
_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 0.8072(5) 1.0316(2) 0.07966(6) 0.0224(6) Uani 1 1 d . . . . .
F2 F 0.2036(5) 0.4755(3) 0.41910(6) 0.0255(7) Uani 1 1 d . . . . .
O8 O 0.6218(6) 1.0269(3) 0.45941(7) 0.0168(7) Uani 1 1 d . . . . .
O1 O 0.1510(6) 0.8401(3) -0.00136(7) 0.0151(7) Uani 1 1 d . . . . .
O3 O 0.1519(6) 0.6540(3) 0.05714(7) 0.0192(8) Uani 1 1 d . . . . .
O6 O 0.6406(6) 0.3308(3) 0.44346(7) 0.0198(8) Uani 1 1 d . . . . .
O4 O 0.3509(6) 0.4751(3) 0.03893(7) 0.0180(8) Uani 1 1 d . . . . .
O2 O 0.3675(6) 1.1754(3) 0.05518(7) 0.0195(8) Uani 1 1 d . . . . .
O5 O 0.8426(6) 0.6587(3) 0.50255(7) 0.0177(8) Uani 1 1 d . . . . .
O7 O 0.8516(6) 0.8489(3) 0.44538(7) 0.0236(8) Uani 1 1 d . . . . .
N4 N 0.7322(7) 0.4973(4) 0.47256(8) 0.0137(9) Uani 1 1 d . . . . .
H4A H 0.865822 0.449878 0.480674 0.016 Uiso 1 1 calc R . . . .
N1 N 0.5150(7) 0.8106(3) 0.03014(8) 0.0122(8) Uani 1 1 d . . . . .
N3 N 0.4833(7) 0.6896(4) 0.47087(8) 0.0139(9) Uani 1 1 d . . . . .
N5 N 0.8651(8) 0.3528(4) 0.05616(8) 0.0151(9) Uani 1 1 d . . . . .
H5A H 0.873942 0.271779 0.049267 0.018 Uiso 1 1 calc GR . . . .
H5B H 1.018217 0.396148 0.049664 0.018 Uiso 1 1 calc GR . . . .
H5C H 0.707347 0.393885 0.049607 0.018 Uiso 1 1 calc GR . . . .
N6 N 0.1242(7) 1.1498(4) 0.44251(8) 0.0148(9) Uani 1 1 d . . . . .
H6A H -0.032502 1.104347 0.446646 0.018 Uiso 1 1 calc GR . . . .
H6B H 0.102634 1.229725 0.449826 0.018 Uiso 1 1 calc GR . . . .
H6C H 0.274668 1.109158 0.450811 0.018 Uiso 1 1 calc GR . . . .
N2 N 0.2676(8) 1.0044(4) 0.02734(8) 0.0157(9) Uani 1 1 d . . . . .
H2 H 0.131993 1.050732 0.019264 0.019 Uiso 1 1 calc R . . . .
C7 C 0.6953(9) 0.6199(4) 0.48296(10) 0.0117(10) Uani 1 1 d . . . . .
C2 C 0.4207(9) 1.0643(4) 0.04851(10) 0.0132(10) Uani 1 1 d . . . . .
C14 C 0.7466(9) 0.4724(4) 0.10081(9) 0.0162(11) Uani 1 1 d . . . . .
H14A H 0.541495 0.477913 0.098147 0.019 Uiso 1 1 calc R . . . .
H14B H 0.830528 0.544198 0.089358 0.019 Uiso 1 1 calc R . . . .
C8 C 0.5846(9) 0.4407(5) 0.45098(10) 0.0161(11) Uani 1 1 d . . . . .
C9 C 0.3677(9) 0.5234(4) 0.43975(10) 0.0155(10) Uani 1 1 d . . . . .
C4 C 0.6787(9) 0.8622(5) 0.05150(10) 0.0157(11) Uani 1 1 d . . . . .
H4 H 0.824213 0.811184 0.060095 0.019 Uiso 1 1 calc R . . . .
C6 C 0.3290(9) 0.5965(4) 0.04169(9) 0.0131(10) Uani 1 1 d . . . . .
C1 C 0.3037(9) 0.8822(4) 0.01768(10) 0.0156(11) Uani 1 1 d . . . . .
C11 C 0.4539(9) 0.8271(4) 0.47704(10) 0.0155(10) Uani 1 1 d . . . . .
H11A H 0.485441 0.839884 0.498112 0.019 Uiso 1 1 calc R . . . .
H11B H 0.260861 0.857464 0.472668 0.019 Uiso 1 1 calc R . . . .
C12 C 0.6616(9) 0.9057(5) 0.45880(10) 0.0155(11) Uani 1 1 d . . . . .
C10 C 0.3243(9) 0.6434(4) 0.44889(10) 0.0151(11) Uani 1 1 d . . . . .
H10 H 0.183330 0.696718 0.440156 0.018 Uiso 1 1 calc R . . . .
C5 C 0.5419(9) 0.6736(4) 0.02389(10) 0.0148(10) Uani 1 1 d . . . . .
H5D H 0.733253 0.641951 0.028613 0.018 Uiso 1 1 calc R . . . .
H5E H 0.513453 0.661255 0.002748 0.018 Uiso 1 1 calc R . . . .
C18 C 0.6708(10) 0.7753(4) 0.18527(10) 0.0194(11) Uani 1 1 d . . . . .
H18A H 0.463968 0.771388 0.186356 0.023 Uiso 1 1 calc R . . . .
H18B H 0.719951 0.842563 0.170481 0.023 Uiso 1 1 calc R . . . .
C20 C 0.6544(10) 0.9418(4) 0.22515(10) 0.0204(11) Uani 1 1 d . . . . .
H20A H 0.448275 0.935682 0.226949 0.024 Uiso 1 1 calc R . . . .
H20B H 0.695793 1.008577 0.209962 0.024 Uiso 1 1 calc R . . . .
C22 C 0.6424(10) 1.1115(4) 0.26411(10) 0.0207(11) Uani 1 1 d . . . . .
H22A H 0.436355 1.104977 0.265893 0.025 Uiso 1 1 calc R . . . .
H22B H 0.683658 1.178092 0.248887 0.025 Uiso 1 1 calc R . . . .
C24 C 0.6291(10) 1.2822(4) 0.30273(10) 0.0204(11) Uani 1 1 d . . . . .
H24A H 0.669796 1.347823 0.287260 0.025 Uiso 1 1 calc R . . . .
H24B H 0.423058 1.275341 0.304475 0.025 Uiso 1 1 calc R . . . .
C23 C 0.7537(10) 1.1537(5) 0.29317(11) 0.0205(12) Uani 1 1 d . . . . .
H23A H 0.959856 1.160011 0.291464 0.025 Uiso 1 1 calc R . . . .
H23B H 0.711418 1.087524 0.308469 0.025 Uiso 1 1 calc R . . . .
C28 C 0.1696(10) 1.1599(4) 0.41005(9) 0.0166(11) Uani 1 1 d . . . . .
H28A H 0.357378 1.194181 0.405476 0.020 Uiso 1 1 calc R . . . .
H28B H 0.027697 1.219400 0.401338 0.020 Uiso 1 1 calc R . . . .
C3 C 0.6352(9) 0.9805(5) 0.05999(10) 0.0169(11) Uani 1 1 d . . . . .
C39 C 0.1544(10) 0.2328(4) 0.19388(10) 0.0203(11) Uani 1 1 d . . . . .
H39A H 0.175333 0.166215 0.209590 0.024 Uiso 1 1 calc R . . . .
H39B H -0.048587 0.248466 0.191043 0.024 Uiso 1 1 calc R . . . .
C13 C 0.8584(10) 0.3471(5) 0.08874(10) 0.0207(12) Uani 1 1 d . . . . .
H13A H 1.049775 0.329281 0.095973 0.025 Uiso 1 1 calc R . . . .
H13B H 0.737839 0.276365 0.095764 0.025 Uiso 1 1 calc R . . . .
C35 C 0.1476(9) 0.5735(4) 0.27142(10) 0.0192(11) Uani 1 1 d . . . . .
H35A H 0.178722 0.506004 0.286743 0.023 Uiso 1 1 calc R . . . .
H35B H -0.057190 0.585148 0.269143 0.023 Uiso 1 1 calc R . . . .
C33 C 0.1470(10) 0.7381(4) 0.31138(10) 0.0205(11) Uani 1 1 d . . . . .
H33A H 0.191302 0.669225 0.326019 0.025 Uiso 1 1 calc R . . . .
H33B H -0.059427 0.745549 0.310165 0.025 Uiso 1 1 calc R . . . .
C31 C 0.1526(11) 0.8912(5) 0.35323(10) 0.0256(12) Uani 1 1 d . . . . .
H31A H 0.230589 0.823699 0.366590 0.031 Uiso 1 1 calc R . . . .
H31B H -0.053671 0.884197 0.353945 0.031 Uiso 1 1 calc R . . . .
C34 C 0.2653(10) 0.6984(5) 0.28177(10) 0.0199(12) Uani 1 1 d . . . . .
H34A H 0.471405 0.688692 0.282982 0.024 Uiso 1 1 calc R . . . .
H34B H 0.223690 0.767397 0.267075 0.024 Uiso 1 1 calc R . . . .
C32 C 0.2555(11) 0.8640(5) 0.32233(10) 0.0231(12) Uani 1 1 d . . . . .
H32A H 0.462798 0.860498 0.321845 0.028 Uiso 1 1 calc R . . . .
H32B H 0.193457 0.935032 0.308997 0.028 Uiso 1 1 calc R . . . .
C19 C 0.7754(10) 0.8144(5) 0.21498(10) 0.0203(12) Uani 1 1 d . . . . .
H19A H 0.727631 0.746937 0.229782 0.024 Uiso 1 1 calc R . . . .
H19B H 0.982011 0.819353 0.213878 0.024 Uiso 1 1 calc R . . . .
C25 C 0.7382(11) 1.3277(5) 0.33168(11) 0.0244(12) Uani 1 1 d . . . . .
H25A H 0.692852 1.263529 0.347322 0.029 Uiso 1 1 calc R . . . .
H25B H 0.944614 1.332885 0.330167 0.029 Uiso 1 1 calc R . . . .
C26 C 0.6163(10) 1.4573(5) 0.34031(10) 0.0234(11) Uani 1 1 d . . . . .
H26A H 0.410480 1.451206 0.342537 0.028 Uiso 1 1 calc R . . . .
H26B H 0.655421 1.520752 0.324322 0.028 Uiso 1 1 calc R . . . .
C29 C 0.1464(11) 1.0279(5) 0.39719(10) 0.0243(12) Uani 1 1 d . . . . .
H29A H -0.048964 0.999779 0.399959 0.029 Uiso 1 1 calc R . . . .
H29B H 0.268188 0.966883 0.408337 0.029 Uiso 1 1 calc R . . . .
C15 C 0.8071(11) 0.4881(5) 0.13296(10) 0.0212(12) Uani 1 1 d . . . . .
H15A H 1.011811 0.481301 0.135810 0.025 Uiso 1 1 calc R . . . .
H15B H 0.719054 0.417949 0.144589 0.025 Uiso 1 1 calc R . . . .
C36 C 0.2746(10) 0.5279(5) 0.24281(11) 0.0230(12) Uani 1 1 d . . . . .
H36A H 0.478866 0.514285 0.245149 0.028 Uiso 1 1 calc R . . . .
H36B H 0.246514 0.595758 0.227508 0.028 Uiso 1 1 calc R . . . .
C41 C 0.1596(10) 0.0569(5) 0.15632(10) 0.0241(11) Uani 1 1 d . . . . .
H41A H -0.043646 0.070657 0.153324 0.029 Uiso 1 1 calc R . . . .
H41B H 0.182611 -0.008356 0.172293 0.029 Uiso 1 1 calc R . . . .
C21 C 0.7657(10) 0.9839(5) 0.25421(10) 0.0191(11) Uani 1 1 d . . . . .
H21A H 0.724405 0.917307 0.269429 0.023 Uiso 1 1 calc R . . . .
H21B H 0.971769 0.990420 0.252431 0.023 Uiso 1 1 calc R . . . .
C37 C 0.1503(9) 0.4041(5) 0.23255(10) 0.0201(11) Uani 1 1 d . . . . .
H37A H -0.053305 0.418485 0.229860 0.024 Uiso 1 1 calc R . . . .
H37B H 0.174606 0.336995 0.248083 0.024 Uiso 1 1 calc R . . . .
C17 C 0.7882(10) 0.6469(5) 0.17486(11) 0.0217(12) Uani 1 1 d . . . . .
H17A H 0.995309 0.647834 0.175167 0.026 Uiso 1 1 calc R . . . .
H17B H 0.725627 0.578120 0.188666 0.026 Uiso 1 1 calc R . . . .
C30 C 0.2260(11) 1.0208(5) 0.36485(10) 0.0226(12) Uani 1 1 d . . . . .
H30A H 0.124880 1.089554 0.353712 0.027 Uiso 1 1 calc R . . . .
H30B H 0.429446 1.034074 0.362150 0.027 Uiso 1 1 calc R . . . .
C16 C 0.6973(10) 0.6162(4) 0.14410(10) 0.0226(11) Uani 1 1 d . . . . .
H16A H 0.490154 0.617016 0.143841 0.027 Uiso 1 1 calc R . . . .
H16B H 0.761534 0.685021 0.130385 0.027 Uiso 1 1 calc R . . . .
C38 C 0.2806(10) 0.3554(5) 0.20404(10) 0.0217(12) Uani 1 1 d . . . . .
H38A H 0.257328 0.422676 0.188514 0.026 Uiso 1 1 calc R . . . .
H38B H 0.483907 0.340354 0.206752 0.026 Uiso 1 1 calc R . . . .
C40 C 0.2818(10) 0.1814(5) 0.16585(10) 0.0198(12) Uani 1 1 d . . . . .
H40A H 0.485734 0.167929 0.168468 0.024 Uiso 1 1 calc R . . . .
H40B H 0.256032 0.246926 0.149975 0.024 Uiso 1 1 calc R . . . .
C27 C 0.7328(11) 1.5053(5) 0.36865(11) 0.0303(13) Uani 1 1 d . . . . .
H27A H 0.935854 1.514329 0.366440 0.045 Uiso 1 1 calc GR . . . .
H27B H 0.692036 1.443862 0.384690 0.045 Uiso 1 1 calc GR . . . .
H27C H 0.645404 1.588694 0.373079 0.045 Uiso 1 1 calc GR . . . .
C42 C 0.2926(11) 0.0048(5) 0.12837(11) 0.0299(13) Uani 1 1 d . . . . .
H42A H 0.263437 0.066994 0.112181 0.045 Uiso 1 1 calc GR . . . .
H42B H 0.206192 -0.076171 0.123796 0.045 Uiso 1 1 calc GR . . . .
H42C H 0.493861 -0.009811 0.131131 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 C3 1.358(5) . ?
F2 C9 1.353(5) . ?
O8 C12 1.275(5) . ?
O1 C1 1.242(5) . ?
O3 C6 1.243(5) . ?
O6 C8 1.228(5) . ?
O4 C6 1.279(5) . ?
O2 C2 1.227(5) . ?
O5 C7 1.233(5) . ?
O7 C12 1.233(5) . ?
N4 H4A 0.8800 . ?
N4 C7 1.383(5) . ?
N4 C8 1.378(6) . ?
N1 C4 1.391(6) . ?
N1 C1 1.366(6) . ?
N1 C5 1.468(5) . ?
N3 C7 1.351(5) . ?
N3 C11 1.473(6) . ?
N3 C10 1.376(6) . ?
N5 H5A 0.9100 . ?
N5 H5B 0.9100 . ?
N5 H5C 0.9100 . ?
N5 C13 1.487(6) . ?
N6 H6A 0.9100 . ?
N6 H6B 0.9100 . ?
N6 H6C 0.9100 . ?
N6 C28 1.495(5) . ?
N2 H2 0.8800 . ?
N2 C2 1.395(6) . ?
N2 C1 1.367(6) . ?
C2 C3 1.429(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.515(6) . ?
C14 C15 1.516(6) . ?
C8 C9 1.426(6) . ?
C9 C10 1.341(6) . ?
C4 H4 0.9500 . ?
C4 C3 1.315(6) . ?
C6 C5 1.521(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.524(6) . ?
C10 H10 0.9500 . ?
C5 H5D 0.9900 . ?
C5 H5E 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.525(6) . ?
C18 C17 1.524(6) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C19 1.518(6) . ?
C20 C21 1.520(6) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.520(6) . ?
C22 C21 1.519(6) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C23 1.526(6) . ?
C24 C25 1.523(6) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.520(6) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C39 C38 1.517(6) . ?
C39 C40 1.512(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C34 1.524(6) . ?
C35 C36 1.512(6) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.518(6) . ?
C33 C32 1.526(7) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.516(6) . ?
C31 C30 1.519(7) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.519(6) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.521(7) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.520(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.521(6) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C36 C37 1.525(7) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C41 C40 1.517(6) . ?
C41 C42 1.521(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C37 C38 1.526(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C16 1.523(7) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 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
C7 N4 H4A 116.1 . . ?
C8 N4 H4A 116.1 . . ?
C8 N4 C7 127.7(4) . . ?
C4 N1 C5 120.0(4) . . ?
C1 N1 C4 120.3(4) . . ?
C1 N1 C5 119.2(4) . . ?
C7 N3 C11 119.2(4) . . ?
C7 N3 C10 122.1(4) . . ?
C10 N3 C11 117.6(4) . . ?
H5A N5 H5B 109.5 . . ?
H5A N5 H5C 109.5 . . ?
H5B N5 H5C 109.5 . . ?
C13 N5 H5A 109.5 . . ?
C13 N5 H5B 109.5 . . ?
C13 N5 H5C 109.5 . . ?
H6A N6 H6B 109.5 . . ?
H6A N6 H6C 109.5 . . ?
H6B N6 H6C 109.5 . . ?
C28 N6 H6A 109.5 . . ?
C28 N6 H6B 109.5 . . ?
C28 N6 H6C 109.5 . . ?
C2 N2 H2 116.2 . . ?
C1 N2 H2 116.2 . . ?
C1 N2 C2 127.6(4) . . ?
O5 C7 N4 121.1(4) . . ?
O5 C7 N3 123.7(4) . . ?
N3 C7 N4 115.1(4) . . ?
O2 C2 N2 121.2(4) . . ?
O2 C2 C3 127.5(4) . . ?
N2 C2 C3 111.3(4) . . ?
H14A C14 H14B 107.7 . . ?
C13 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C13 C14 C15 113.6(4) . . ?
C15 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
O6 C8 N4 121.3(4) . . ?
O6 C8 C9 126.6(4) . . ?
N4 C8 C9 112.1(4) . . ?
F2 C9 C8 116.9(4) . . ?
C10 C9 F2 120.5(4) . . ?
C10 C9 C8 122.6(4) . . ?
N1 C4 H4 119.5 . . ?
C3 C4 N1 121.1(4) . . ?
C3 C4 H4 119.5 . . ?
O3 C6 O4 125.9(4) . . ?
O3 C6 C5 119.2(4) . . ?
O4 C6 C5 114.9(4) . . ?
O1 C1 N1 122.7(4) . . ?
O1 C1 N2 121.2(4) . . ?
N1 C1 N2 116.1(4) . . ?
N3 C11 H11A 109.4 . . ?
N3 C11 H11B 109.4 . . ?
N3 C11 C12 111.4(4) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
O8 C12 C11 115.2(4) . . ?
O7 C12 O8 126.1(4) . . ?
O7 C12 C11 118.6(4) . . ?
N3 C10 H10 119.9 . . ?
C9 C10 N3 120.2(4) . . ?
C9 C10 H10 119.9 . . ?
N1 C5 C6 111.1(3) . . ?
N1 C5 H5D 109.4 . . ?
N1 C5 H5E 109.4 . . ?
C6 C5 H5D 109.4 . . ?
C6 C5 H5E 109.4 . . ?
H5D C5 H5E 108.0 . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 H18A 108.6 . . ?
C19 C18 H18B 108.6 . . ?
C17 C18 H18A 108.6 . . ?
C17 C18 H18B 108.6 . . ?
C17 C18 C19 114.6(4) . . ?
H20A C20 H20B 107.6 . . ?
C19 C20 H20A 108.7 . . ?
C19 C20 H20B 108.7 . . ?
C19 C20 C21 114.3(4) . . ?
C21 C20 H20A 108.7 . . ?
C21 C20 H20B 108.7 . . ?
H22A C22 H22B 107.7 . . ?
C23 C22 H22A 108.8 . . ?
C23 C22 H22B 108.8 . . ?
C21 C22 H22A 108.8 . . ?
C21 C22 H22B 108.8 . . ?
C21 C22 C23 113.7(4) . . ?
H24A C24 H24B 107.6 . . ?
C23 C24 H24A 108.7 . . ?
C23 C24 H24B 108.7 . . ?
C25 C24 H24A 108.7 . . ?
C25 C24 H24B 108.7 . . ?
C25 C24 C23 114.3(4) . . ?
C22 C23 C24 113.0(4) . . ?
C22 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
C24 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
N6 C28 H28A 109.8 . . ?
N6 C28 H28B 109.8 . . ?
N6 C28 C29 109.2(4) . . ?
H28A C28 H28B 108.3 . . ?
C29 C28 H28A 109.8 . . ?
C29 C28 H28B 109.8 . . ?
F1 C3 C2 116.2(4) . . ?
C4 C3 F1 120.1(4) . . ?
C4 C3 C2 123.6(4) . . ?
H39A C39 H39B 107.5 . . ?
C38 C39 H39A 108.6 . . ?
C38 C39 H39B 108.6 . . ?
C40 C39 H39A 108.6 . . ?
C40 C39 H39B 108.6 . . ?
C40 C39 C38 114.9(4) . . ?
N5 C13 C14 110.6(4) . . ?
N5 C13 H13A 109.5 . . ?
N5 C13 H13B 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
H35A C35 H35B 107.6 . . ?
C34 C35 H35A 108.7 . . ?
C34 C35 H35B 108.7 . . ?
C36 C35 H35A 108.7 . . ?
C36 C35 H35B 108.7 . . ?
C36 C35 C34 114.2(4) . . ?
H33A C33 H33B 107.5 . . ?
C34 C33 H33A 108.5 . . ?
C34 C33 H33B 108.5 . . ?
C34 C33 C32 115.0(4) . . ?
C32 C33 H33A 108.5 . . ?
C32 C33 H33B 108.5 . . ?
H31A C31 H31B 107.4 . . ?
C32 C31 H31A 108.3 . . ?
C32 C31 H31B 108.3 . . ?
C32 C31 C30 116.0(4) . . ?
C30 C31 H31A 108.3 . . ?
C30 C31 H31B 108.3 . . ?
C35 C34 H34A 108.9 . . ?
C35 C34 H34B 108.9 . . ?
C33 C34 C35 113.2(4) . . ?
C33 C34 H34A 108.9 . . ?
C33 C34 H34B 108.9 . . ?
H34A C34 H34B 107.7 . . ?
C33 C32 H32A 109.2 . . ?
C33 C32 H32B 109.2 . . ?
C31 C32 C33 112.3(4) . . ?
C31 C32 H32A 109.2 . . ?
C31 C32 H32B 109.2 . . ?
H32A C32 H32B 107.9 . . ?
C18 C19 H19A 108.8 . . ?
C18 C19 H19B 108.8 . . ?
C20 C19 C18 113.9(4) . . ?
C20 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C24 C25 H25A 108.9 . . ?
C24 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
C26 C25 C24 113.2(4) . . ?
C26 C25 H25A 108.9 . . ?
C26 C25 H25B 108.9 . . ?
C25 C26 H26A 108.9 . . ?
C25 C26 H26B 108.9 . . ?
C25 C26 C27 113.4(4) . . ?
H26A C26 H26B 107.7 . . ?
C27 C26 H26A 108.9 . . ?
C27 C26 H26B 108.9 . . ?
C28 C29 H29A 108.6 . . ?
C28 C29 H29B 108.6 . . ?
C28 C29 C30 114.8(4) . . ?
H29A C29 H29B 107.5 . . ?
C30 C29 H29A 108.6 . . ?
C30 C29 H29B 108.6 . . ?
C14 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
C14 C15 C16 112.0(4) . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C35 C36 H36A 108.9 . . ?
C35 C36 H36B 108.9 . . ?
C35 C36 C37 113.4(4) . . ?
H36A C36 H36B 107.7 . . ?
C37 C36 H36A 108.9 . . ?
C37 C36 H36B 108.9 . . ?
H41A C41 H41B 107.6 . . ?
C40 C41 H41A 108.7 . . ?
C40 C41 H41B 108.7 . . ?
C40 C41 C42 114.0(4) . . ?
C42 C41 H41A 108.7 . . ?
C42 C41 H41B 108.7 . . ?
C20 C21 H21A 108.8 . . ?
C20 C21 H21B 108.8 . . ?
C22 C21 C20 113.6(4) . . ?
C22 C21 H21A 108.8 . . ?
C22 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C36 C37 H37A 108.7 . . ?
C36 C37 H37B 108.7 . . ?
C36 C37 C38 114.0(4) . . ?
H37A C37 H37B 107.6 . . ?
C38 C37 H37A 108.7 . . ?
C38 C37 H37B 108.7 . . ?
C18 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C16 C17 C18 113.0(4) . . ?
C16 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
C31 C30 C29 110.3(4) . . ?
C31 C30 H30A 109.6 . . ?
C31 C30 H30B 109.6 . . ?
C29 C30 H30A 109.6 . . ?
C29 C30 H30B 109.6 . . ?
H30A C30 H30B 108.1 . . ?
C15 C16 C17 114.7(4) . . ?
C15 C16 H16A 108.6 . . ?
C15 C16 H16B 108.6 . . ?
C17 C16 H16A 108.6 . . ?
C17 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C39 C38 C37 113.7(4) . . ?
C39 C38 H38A 108.8 . . ?
C39 C38 H38B 108.8 . . ?
C37 C38 H38A 108.8 . . ?
C37 C38 H38B 108.8 . . ?
H38A C38 H38B 107.7 . . ?
C39 C40 C41 114.4(4) . . ?
C39 C40 H40A 108.6 . . ?
C39 C40 H40B 108.6 . . ?
C41 C40 H40A 108.6 . . ?
C41 C40 H40B 108.6 . . ?
H40A C40 H40B 107.6 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
