# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_1x1
_database_code_depnum_ccdc_archive 'CCDC 1957428'
loop_
_audit_author_name
_audit_author_address
'Arshad Mehmood'
;Texas Christian University
United States of America
;
_audit_update_record             
;
2019-10-03 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;
_audit_creation_date             2019-09-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H34 N16 O4, 2(C2 F3 O2), 2(H2 O)'
_chemical_formula_sum            'C26 H38 F6 N16 O10'
_chemical_formula_weight         848.72
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.5858(3)
_cell_length_b                   18.8852(6)
_cell_length_c                   10.9389(4)
_cell_angle_alpha                90
_cell_angle_beta                 115.1840(10)
_cell_angle_gamma                90
_cell_volume                     1792.03(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5480
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.98
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0476 before and 0.0404 after correction. The Ratio of minimum to maximum transmission is 0.8361. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.382
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.152
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12645
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.293
_diffrn_reflns_theta_min         2.981
_diffrn_ambient_temperature      99.96
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_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                3504
_reflns_number_total             4393
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4393
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.017
_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)+(0.0471P)²+1.5900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1179
_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
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C4(H4A,H4B), C7(H7A,H7B), C9(H9A,H9B), C6(H6A,H6B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 N5(H5), C8(H8A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.03218(13) 0.59040(7) 0.01005(12) 0.0182(3) Uani 1 1 d . . . . .
O3 O 0.52588(14) 0.58728(7) 0.46216(12) 0.0208(3) Uani 1 1 d . . . . .
O5 O 0.72551(16) 0.55685(8) -0.02954(14) 0.0240(3) Uani 1 1 d . . . . .
F3 F 0.56462(15) 0.72442(6) 0.63316(17) 0.0482(4) Uani 1 1 d . . . . .
O4 O 0.63239(15) 0.57354(7) 0.68697(13) 0.0235(3) Uani 1 1 d . . . . .
F2 F 0.34589(16) 0.68880(8) 0.48368(15) 0.0559(5) Uani 1 1 d . . . . .
F1 F 0.41325(18) 0.66388(7) 0.68863(17) 0.0522(4) Uani 1 1 d . . . . .
N1 N 0.72953(16) 0.48986(8) 0.41623(14) 0.0142(3) Uani 1 1 d . . . . .
N2 N 0.94508(15) 0.41634(7) 0.53281(14) 0.0141(3) Uani 1 1 d . . . . .
N6 N 0.66374(16) 0.51926(8) 0.19247(15) 0.0174(3) Uani 1 1 d . . . . .
N5 N 0.82071(15) 0.47324(7) 0.64588(14) 0.0143(3) Uani 1 1 d . . . . .
H5 H 0.738043 0.495917 0.640370 0.017 Uiso 1 1 calc R . . . .
O1 O 1.1008(2) 0.21338(7) 0.37106(15) 0.0370(4) Uani 1 1 d . . . . .
N8 N 0.26855(16) 0.60567(8) 0.18261(16) 0.0186(3) Uani 1 1 d . . . . .
N7 N 0.54211(16) 0.55669(8) 0.19746(15) 0.0172(3) Uani 1 1 d . . . . .
N3 N 0.85328(16) 0.43725(7) 0.29353(14) 0.0154(3) Uani 1 1 d . . . . .
N4 N 1.04609(16) 0.35705(8) 0.40441(14) 0.0165(3) Uani 1 1 d . . . . .
C1 C 0.83509(17) 0.45873(8) 0.53279(16) 0.0130(3) Uani 1 1 d . . . . .
C10 C 0.12260(18) 0.58288(8) 0.12990(17) 0.0140(3) Uani 1 1 d . . . . .
C3 C 0.75079(18) 0.48101(9) 0.30172(16) 0.0147(3) Uani 1 1 d . . . . .
C2 C 0.94492(18) 0.40427(8) 0.41061(17) 0.0142(3) Uani 1 1 d . . . . .
C12 C 0.54831(18) 0.60274(9) 0.57900(17) 0.0165(3) Uani 1 1 d . . . . .
C8 C 0.47142(19) 0.59938(9) 0.10139(18) 0.0194(4) Uani 1 1 d . . . . .
H8A H 0.506373 0.607190 0.033231 0.023 Uiso 1 1 calc R . . . .
C11 C 0.93692(18) 0.45290(9) 0.77817(16) 0.0148(3) Uani 1 1 d . . . . .
H11A H 0.994420 0.495887 0.824189 0.018 Uiso 1 1 calc R . . . .
H11B H 1.010998 0.420590 0.765444 0.018 Uiso 1 1 calc R . . . .
C4 C 1.0371(2) 0.33049(9) 0.27526(18) 0.0194(4) Uani 1 1 d . . . . .
H4A H 1.138476 0.335032 0.272301 0.023 Uiso 1 1 calc R . . . .
H4B H 0.960295 0.358004 0.199435 0.023 Uiso 1 1 calc R . . . .
C7 C 1.15127(19) 0.31597(9) 0.52037(18) 0.0179(3) Uani 1 1 d . . . . .
H7A H 1.144141 0.332425 0.603449 0.022 Uiso 1 1 calc R . . . .
H7B H 1.258659 0.322870 0.532193 0.022 Uiso 1 1 calc R . . . .
C9 C 0.3326(2) 0.63718(11) 0.0968(2) 0.0281(4) Uani 1 1 d . . . . .
H9A H 0.360654 0.686967 0.124812 0.034 Uiso 1 1 calc R . . . .
H9B H 0.252523 0.637537 0.002459 0.034 Uiso 1 1 calc R . . . .
C13 C 0.4667(2) 0.67064(10) 0.5951(2) 0.0241(4) Uani 1 1 d . . . . .
C6 C 1.1090(3) 0.23790(10) 0.4974(2) 0.0308(5) Uani 1 1 d . . . . .
H6A H 1.187031 0.209820 0.571394 0.037 Uiso 1 1 calc R . . . .
H6B H 1.008101 0.230391 0.500004 0.037 Uiso 1 1 calc R . . . .
C5 C 0.9895(3) 0.25328(10) 0.2639(2) 0.0289(4) Uani 1 1 d . . . . .
H5A H 0.888110 0.249312 0.267014 0.035 Uiso 1 1 calc R . . . .
H5B H 0.979232 0.234026 0.176266 0.035 Uiso 1 1 calc R . . . .
H5C H 0.679(3) 0.5581(14) -0.112(3) 0.042(7) Uiso 1 1 d . . . . .
H5D H 0.822(4) 0.5706(16) -0.018(3) 0.055(8) Uiso 1 1 d . . . . .
H1 H 0.661(3) 0.5171(13) 0.420(2) 0.030(6) Uiso 1 1 d . . . . .
H6 H 0.689(2) 0.5230(12) 0.123(2) 0.023(5) Uiso 1 1 d . . . . .
H8 H 0.324(2) 0.5995(11) 0.267(2) 0.019(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C10 1.234(2) . ?
O3 C12 1.237(2) . ?
F3 C13 1.324(2) . ?
O4 C12 1.240(2) . ?
F2 C13 1.320(2) . ?
F1 C13 1.331(2) . ?
N1 C1 1.377(2) . ?
N1 C3 1.362(2) . ?
N2 C1 1.324(2) . ?
N2 C2 1.355(2) . ?
N6 N7 1.384(2) . ?
N6 C3 1.341(2) . ?
N5 C1 1.330(2) . ?
N5 C11 1.453(2) . ?
O1 C6 1.428(2) . ?
O1 C5 1.420(3) . ?
N8 C10 1.337(2) . ?
N8 C9 1.450(2) . ?
N7 C8 1.268(2) . ?
N3 C3 1.316(2) . ?
N3 C2 1.357(2) . ?
N4 C2 1.340(2) . ?
N4 C4 1.467(2) . ?
N4 C7 1.463(2) . ?
C10 C11 1.511(2) 3_666 ?
C12 C13 1.551(2) . ?
C8 C9 1.492(2) . ?
C4 C5 1.517(3) . ?
C7 C6 1.521(3) . ?

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
C3 N1 C1 117.41(14) . . ?
C1 N2 C2 115.78(14) . . ?
C3 N6 N7 117.07(14) . . ?
C1 N5 C11 122.20(13) . . ?
C5 O1 C6 109.88(15) . . ?
C10 N8 C9 120.43(16) . . ?
C8 N7 N6 117.01(14) . . ?
C3 N3 C2 115.22(14) . . ?
C2 N4 C4 121.94(14) . . ?
C2 N4 C7 123.76(14) . . ?
C7 N4 C4 112.97(13) . . ?
N2 C1 N1 121.97(15) . . ?
N2 C1 N5 121.48(15) . . ?
N5 C1 N1 116.55(14) . . ?
O2 C10 N8 123.64(15) . . ?
O2 C10 C11 117.72(14) . 3_666 ?
N8 C10 C11 118.63(15) . 3_666 ?
N6 C3 N1 118.27(15) . . ?
N3 C3 N1 123.22(15) . . ?
N3 C3 N6 118.50(15) . . ?
N2 C2 N3 125.60(15) . . ?
N4 C2 N2 117.69(14) . . ?
N4 C2 N3 116.69(14) . . ?
O3 C12 O4 129.46(16) . . ?
O3 C12 C13 115.99(15) . . ?
O4 C12 C13 114.47(15) . . ?
N7 C8 C9 119.12(16) . . ?
N5 C11 C10 115.77(13) . 3_666 ?
N4 C4 C5 107.47(14) . . ?
N4 C7 C6 109.53(15) . . ?
N8 C9 C8 113.52(15) . . ?
F3 C13 F1 106.57(17) . . ?
F3 C13 C12 110.22(14) . . ?
F2 C13 F3 108.47(17) . . ?
F2 C13 F1 105.15(17) . . ?
F2 C13 C12 113.37(16) . . ?
F1 C13 C12 112.70(16) . . ?
O1 C6 C7 112.04(15) . . ?
O1 C5 C4 110.39(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H5 O4 0.88 1.97 2.7820(18) 153.2 . yes
C8 H8A O5 0.95 2.65 3.405(2) 137.0 . yes
C11 H11A O2 0.99 2.61 3.470(2) 145.0 1_656 yes
C11 H11A N3 0.99 2.64 3.210(2) 116.6 3_766 yes
C4 H4B O2 0.99 2.52 3.263(2) 131.8 3_665 yes
C7 H7B O3 0.99 2.65 3.528(2) 147.5 3_766 yes
C9 H9A F3 0.99 2.55 3.344(2) 137.6 4_575 yes
O5 H5C O4 0.82(3) 2.07(3) 2.8560(19) 161(3) 1_554 yes
O5 H5D O2 0.92(3) 1.94(3) 2.8544(18) 175(3) 1_655 yes
N1 H1 O3 0.85(2) 2.04(3) 2.8779(19) 170(2) . yes
N6 H6 O5 0.89(2) 1.96(2) 2.824(2) 165(2) . yes
N8 H8 O3 0.85(2) 2.20(2) 3.0227(19) 161.5(19) . yes

_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_3x3
_database_code_depnum_ccdc_archive 'CCDC 1957430'
loop_
_audit_author_name
_audit_author_address
'Arshad Mehmood'
;Texas Christian University
United States of America
;
_audit_update_record             
;
2019-10-03 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;
_audit_creation_date             2019-09-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C24 H38 N16 O4), C2 F3 O2, 2(C H4 O)'
_chemical_formula_sum            'C16 H27 F3 N8 O6'
_chemical_formula_weight         484.45
_chemical_absolute_configuration syn
_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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   24.515(10)
_cell_length_b                   8.492(4)
_cell_length_c                   25.298(10)
_cell_angle_alpha                90
_cell_angle_beta                 119.248(12)
_cell_angle_gamma                90
_cell_volume                     4595(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      3.23
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0526 before and 0.0477 after correction. The Ratio of minimum to maximum transmission is 0.9095. 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    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.565
_exptl_crystal_size_mid          0.482
_exptl_crystal_size_min          0.386
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            25354
_diffrn_reflns_point_group_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.088
_diffrn_reflns_theta_min         2.889
_diffrn_ambient_temperature      100.13
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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         0.855
_reflns_Friedel_fraction_full    0.880
_reflns_Friedel_fraction_max     0.852
_reflns_number_gt                7912
_reflns_number_total             9347
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 3064 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     603
_refine_ls_number_reflns         9347
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0536
_refine_ls_restrained_S_all      1.049
_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)+(0.0750P)²+4.9482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1421
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C21(H21A,H21B), C12(H12A,H12B), C23(H23A,H23B), C4(H4A,H4B),
 C16(H16A,H16B), C2(H2A,H2B), C24(H24A,H24B), C11(H11A,H11B), C19(H19A,H19B),
 C3(H3A,H3B), C17(H17A,H17B), C1(H1A,H1B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N14(H14), N9(H9), N5(H5), N8(H8), N6(H6), N16(H16), N13(H13),
 C20(H20), C8(H8A)
2.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C30(H30A,H30B,
 H30C)
2.d Idealised tetrahedral OH refined as rotating group:
 O12(H12), O10(H10), O9(H9C), O11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.40486(15) 0.2353(3) 0.28889(14) 0.0308(7) Uani 1 1 d . . . . .
O8 O 0.32586(14) 0.8606(4) 0.41770(14) 0.0326(7) Uani 1 1 d . . . . .
O2 O 0.53316(16) 1.0535(4) 0.68897(14) 0.0327(7) Uani 1 1 d . . . . .
F2 F 0.41585(17) 0.5973(4) 0.65288(15) 0.0534(9) Uani 1 1 d . . . . .
O7 O 0.38487(14) 0.7304(4) 0.38709(14) 0.0332(7) Uani 1 1 d . . . . .
N11 N 0.60873(16) 0.3980(4) 0.50219(15) 0.0234(7) Uani 1 1 d . . . . .
N1 N 0.50096(16) 0.8503(4) 0.47609(14) 0.0200(7) Uani 1 1 d . . . . .
H1 H 0.469051 0.794654 0.449451 0.024 Uiso 1 1 calc R . . . .
N14 N 0.41186(17) 0.4863(4) 0.32084(15) 0.0241(7) Uani 1 1 d . . . . .
H14 H 0.397914 0.559723 0.335775 0.029 Uiso 1 1 calc R . . . .
N7 N 0.58712(16) 0.6348(4) 0.60561(15) 0.0211(7) Uani 1 1 d . . . . .
N9 N 0.51964(16) 0.4457(4) 0.51277(15) 0.0207(7) Uani 1 1 d . . . . .
H9 H 0.502403 0.494983 0.531523 0.025 Uiso 1 1 calc R . . . .
O5 O 0.45328(15) 0.5543(4) 0.57129(15) 0.0364(8) Uani 1 1 d . . . . .
O12 O 0.65718(16) 1.2385(4) 0.90193(16) 0.0378(8) Uani 1 1 d . . . . .
H12 H 0.640612 1.239458 0.863980 0.057 Uiso 1 1 calc GR . . . .
N2 N 0.60672(16) 0.9252(4) 0.51734(15) 0.0221(7) Uani 1 1 d . . . . .
N5 N 0.44006(16) 0.9521(4) 0.51444(14) 0.0209(7) Uani 1 1 d . . . . .
H5 H 0.409481 0.895075 0.486710 0.025 Uiso 1 1 calc R . . . .
N8 N 0.61528(16) 0.5619(4) 0.57636(15) 0.0210(7) Uani 1 1 d . . . . .
H8 H 0.655155 0.577188 0.588382 0.025 Uiso 1 1 calc R . . . .
N6 N 0.53031(17) 0.8040(4) 0.65670(16) 0.0251(8) Uani 1 1 d . . . . .
H6 H 0.506859 0.723156 0.636665 0.030 Uiso 1 1 calc R . . . .
N10 N 0.51036(16) 0.2703(4) 0.43612(14) 0.0214(7) Uani 1 1 d . . . . .
N16 N 0.56259(16) 0.7585(4) 0.43630(15) 0.0210(7) Uani 1 1 d . . . . .
H16 H 0.597873 0.754438 0.435168 0.025 Uiso 1 1 calc R . . . .
N15 N 0.51045(16) 0.6740(4) 0.39544(15) 0.0219(7) Uani 1 1 d . . . . .
N3 N 0.54397(15) 1.0258(4) 0.55929(14) 0.0196(7) Uani 1 1 d . . . . .
O6 O 0.36568(15) 0.4207(4) 0.51181(17) 0.0418(9) Uani 1 1 d . . . . .
N13 N 0.42604(16) 0.3206(4) 0.45050(16) 0.0235(7) Uani 1 1 d . . . . .
H13 H 0.411152 0.370665 0.471178 0.028 Uiso 1 1 calc R . . . .
F4 F 0.23733(18) 0.8837(6) 0.30166(16) 0.0780(13) Uani 1 1 d . . . . .
O1 O 0.75675(16) 1.1859(6) 0.70596(16) 0.0518(11) Uani 1 1 d . . . . .
N4 N 0.64845(16) 1.0856(4) 0.60225(15) 0.0245(7) Uani 1 1 d . . . . .
O4 O 0.63920(18) 0.1857(5) 0.34014(16) 0.0483(10) Uani 1 1 d . . . . .
O10 O 0.24057(17) -0.0957(5) 0.11840(17) 0.0500(10) Uani 1 1 d . . . . .
H10 H 0.268460 -0.045257 0.147726 0.075 Uiso 1 1 calc GR . . . .
N12 N 0.59682(18) 0.2381(4) 0.42391(16) 0.0280(8) Uani 1 1 d . . . . .
F5 F 0.24494(18) 0.6402(6) 0.3184(2) 0.0946(17) Uani 1 1 d . . . . .
C15 C 0.58072(18) 0.4676(5) 0.52938(17) 0.0198(8) Uani 1 1 d . . . . .
F3 F 0.3254(2) 0.6175(7) 0.5767(2) 0.0953(16) Uani 1 1 d . . . . .
C10 C 0.3901(2) 0.3382(5) 0.31392(18) 0.0262(9) Uani 1 1 d . . . . .
C5 C 0.59806(19) 1.0095(5) 0.55828(17) 0.0191(8) Uani 1 1 d . . . . .
C7 C 0.49597(19) 0.9444(4) 0.51782(16) 0.0187(8) Uani 1 1 d . . . . .
C14 C 0.57092(19) 0.3031(5) 0.45482(17) 0.0205(8) Uani 1 1 d . . . . .
O9 O 0.3477(2) 0.0081(5) 0.2066(2) 0.0797(17) Uani 1 1 d . . . . .
H9C H 0.355630 0.087005 0.229212 0.120 Uiso 1 1 calc GR . . . .
F6 F 0.29130(18) 0.7306(8) 0.27489(16) 0.104(2) Uani 1 1 d . . . . .
C22 C 0.5035(2) 0.9416(5) 0.65586(18) 0.0235(8) Uani 1 1 d . . . . .
C13 C 0.48515(18) 0.3430(4) 0.46522(17) 0.0191(8) Uani 1 1 d . . . . .
C6 C 0.55731(19) 0.8469(5) 0.47767(17) 0.0200(8) Uani 1 1 d . . . . .
C25 C 0.3357(2) 0.7912(5) 0.3807(2) 0.0279(9) Uani 1 1 d . . . . .
O11 O 0.5992(3) 1.2593(5) 0.77776(19) 0.0673(14) Uani 1 1 d . . . . .
H11 H 0.587890 1.182120 0.753971 0.101 Uiso 1 1 calc GR . . . .
C20 C 0.6238(2) 0.7024(5) 0.65579(18) 0.0254(9) Uani 1 1 d . . . . .
H20 H 0.667718 0.698889 0.671039 0.030 Uiso 1 1 calc R . . . .
C9 C 0.4589(2) 0.5240(5) 0.3033(2) 0.0286(9) Uani 1 1 d . . . . .
H9A H 0.438964 0.585183 0.265108 0.034 Uiso 1 1 calc R . . . .
H9B H 0.474799 0.424671 0.295255 0.034 Uiso 1 1 calc R . . . .
C21 C 0.5981(2) 0.7867(5) 0.69052(18) 0.0270(9) Uani 1 1 d . . . . .
H21A H 0.609714 0.728178 0.728412 0.032 Uiso 1 1 calc R . . . .
H21B H 0.617418 0.892432 0.701810 0.032 Uiso 1 1 calc R . . . .
C12 C 0.3843(2) 0.2160(5) 0.40131(18) 0.0246(9) Uani 1 1 d . . . . .
H12A H 0.354032 0.168020 0.411779 0.029 Uiso 1 1 calc R . . . .
H12B H 0.409257 0.129946 0.397229 0.029 Uiso 1 1 calc R . . . .
C8 C 0.5129(2) 0.6159(5) 0.3501(2) 0.0268(9) Uani 1 1 d . . . . .
H8A H 0.549103 0.631128 0.346137 0.032 Uiso 1 1 calc R . . . .
C23 C 0.4352(2) 0.9610(5) 0.6106(2) 0.0278(9) Uani 1 1 d . . . . .
H23A H 0.414313 1.019795 0.629493 0.033 Uiso 1 1 calc R . . . .
H23B H 0.415326 0.856085 0.598486 0.033 Uiso 1 1 calc R . . . .
C4 C 0.6438(2) 1.1869(5) 0.64647(19) 0.0263(9) Uani 1 1 d . . . . .
H4A H 0.605116 1.161879 0.648008 0.032 Uiso 1 1 calc R . . . .
H4B H 0.641706 1.298558 0.634358 0.032 Uiso 1 1 calc R . . . .
C16 C 0.5622(2) 0.1307(5) 0.3729(2) 0.0301(10) Uani 1 1 d . . . . .
H16A H 0.516968 0.136786 0.359311 0.036 Uiso 1 1 calc R . . . .
H16B H 0.576243 0.021042 0.385523 0.036 Uiso 1 1 calc R . . . .
C28 C 0.4012(2) 0.4979(5) 0.5570(2) 0.0323(10) Uani 1 1 d . . . . .
F1 F 0.3607(4) 0.3937(6) 0.6178(3) 0.135(3) Uani 1 1 d . . . . .
C2 C 0.7080(2) 1.0971(6) 0.6018(2) 0.0310(10) Uani 1 1 d . . . . .
H2A H 0.711589 1.201693 0.586469 0.037 Uiso 1 1 calc R . . . .
H2B H 0.709911 1.015528 0.574756 0.037 Uiso 1 1 calc R . . . .
C24 C 0.4268(2) 1.0500(5) 0.55428(19) 0.0257(9) Uani 1 1 d . . . . .
H24A H 0.383259 1.089046 0.531364 0.031 Uiso 1 1 calc R . . . .
H24B H 0.454951 1.142483 0.567276 0.031 Uiso 1 1 calc R . . . .
C11 C 0.3486(2) 0.3014(5) 0.3407(2) 0.0306(10) Uani 1 1 d . . . . .
H11A H 0.313315 0.234723 0.312077 0.037 Uiso 1 1 calc R . . . .
H11B H 0.331016 0.400561 0.346614 0.037 Uiso 1 1 calc R . . . .
C19 C 0.6632(2) 0.2503(7) 0.4426(2) 0.0369(11) Uani 1 1 d . . . . .
H19A H 0.684041 0.148156 0.459128 0.044 Uiso 1 1 calc R . . . .
H19B H 0.683059 0.330851 0.474825 0.044 Uiso 1 1 calc R . . . .
C3 C 0.7004(2) 1.1615(7) 0.7084(2) 0.0370(11) Uani 1 1 d . . . . .
H3A H 0.698807 1.235477 0.737889 0.044 Uiso 1 1 calc R . . . .
H3B H 0.699743 1.052855 0.722344 0.044 Uiso 1 1 calc R . . . .
C26 C 0.2780(3) 0.7697(10) 0.3173(3) 0.0582(18) Uani 1 1 d . . . . .
C17 C 0.5739(2) 0.1768(6) 0.3215(2) 0.0358(11) Uani 1 1 d . . . . .
H17A H 0.553872 0.098597 0.288489 0.043 Uiso 1 1 calc R . . . .
H17B H 0.554332 0.280368 0.305381 0.043 Uiso 1 1 calc R . . . .
C29 C 0.3922(3) -0.1100(7) 0.2374(3) 0.0563(16) Uani 1 1 d . . . . .
H29A H 0.377157 -0.210334 0.215964 0.084 Uiso 1 1 calc GR . . . .
H29B H 0.398805 -0.120269 0.278679 0.084 Uiso 1 1 calc GR . . . .
H29C H 0.431773 -0.081814 0.238988 0.084 Uiso 1 1 calc GR . . . .
C1 C 0.7614(2) 1.0737(8) 0.6662(2) 0.0443(13) Uani 1 1 d . . . . .
H1A H 0.759650 0.965690 0.680067 0.053 Uiso 1 1 calc R . . . .
H1B H 0.801937 1.086493 0.667005 0.053 Uiso 1 1 calc R . . . .
C18 C 0.6705(3) 0.2961(8) 0.3881(2) 0.0465(13) Uani 1 1 d . . . . .
H18A H 0.652754 0.402488 0.373931 0.056 Uiso 1 1 calc R . . . .
H18B H 0.715395 0.299438 0.400046 0.056 Uiso 1 1 calc R . . . .
C27 C 0.3765(3) 0.5238(8) 0.6024(3) 0.0503(15) Uani 1 1 d . . . . .
C31 C 0.5846(4) 1.4019(7) 0.7438(3) 0.0601(18) Uani 1 1 d . . . . .
H31A H 0.598651 1.394309 0.713682 0.090 Uiso 1 1 calc GR . . . .
H31B H 0.605841 1.490102 0.771223 0.090 Uiso 1 1 calc GR . . . .
H31C H 0.539326 1.419211 0.723220 0.090 Uiso 1 1 calc GR . . . .
C32 C 0.7210(3) 1.1893(9) 0.9277(3) 0.0618(17) Uani 1 1 d . . . . .
H32A H 0.724275 1.106147 0.902529 0.093 Uiso 1 1 calc GR . . . .
H32B H 0.735438 1.148975 0.968691 0.093 Uiso 1 1 calc GR . . . .
H32C H 0.746894 1.279183 0.929423 0.093 Uiso 1 1 calc GR . . . .
C30 C 0.2543(3) -0.0972(10) 0.0696(3) 0.070(2) Uani 1 1 d . . . . .
H30A H 0.220548 -0.150569 0.034551 0.105 Uiso 1 1 calc GR . . . .
H30B H 0.293752 -0.153251 0.082250 0.105 Uiso 1 1 calc GR . . . .
H30C H 0.258171 0.011265 0.058570 0.105 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
O3 C10 1.233(5) . ?
O8 C25 1.226(5) . ?
O2 C22 1.240(5) . ?
F2 C27 1.321(7) . ?
O7 C25 1.248(5) . ?
N11 C15 1.325(5) . ?
N11 C14 1.364(5) . ?
N1 H1 0.8800 . ?
N1 C7 1.376(5) . ?
N1 C6 1.362(5) . ?
N14 H14 0.8800 . ?
N14 C10 1.344(6) . ?
N14 C9 1.461(6) . ?
N7 N8 1.381(5) . ?
N7 C20 1.278(5) . ?
N9 H9 0.8800 . ?
N9 C15 1.356(5) . ?
N9 C13 1.389(5) . ?
O5 C28 1.240(6) . ?
O12 H12 0.8400 . ?
O12 C32 1.432(7) . ?
N2 C5 1.358(5) . ?
N2 C6 1.315(5) . ?
N5 H5 0.8800 . ?
N5 C7 1.333(5) . ?
N5 C24 1.461(5) . ?
N8 H8 0.8800 . ?
N8 C15 1.337(5) . ?
N6 H6 0.8800 . ?
N6 C22 1.336(6) . ?
N6 C21 1.458(6) . ?
N10 C14 1.349(5) . ?
N10 C13 1.323(5) . ?
N16 H16 0.8800 . ?
N16 N15 1.388(5) . ?
N16 C6 1.344(5) . ?
N15 C8 1.276(5) . ?
N3 C5 1.346(5) . ?
N3 C7 1.326(5) . ?
O6 C28 1.234(6) . ?
N13 H13 0.8800 . ?
N13 C13 1.322(5) . ?
N13 C12 1.462(5) . ?
F4 C26 1.304(8) . ?
O1 C3 1.429(6) . ?
O1 C1 1.430(7) . ?
N4 C5 1.355(5) . ?
N4 C4 1.460(6) . ?
N4 C2 1.469(5) . ?
O4 C17 1.432(6) . ?
O4 C18 1.424(7) . ?
O10 H10 0.8400 . ?
O10 C30 1.430(8) . ?
N12 C14 1.343(5) . ?
N12 C16 1.466(6) . ?
N12 C19 1.459(6) . ?
F5 C26 1.374(9) . ?
F3 C27 1.353(8) . ?
C10 C11 1.506(7) . ?
O9 H9C 0.8400 . ?
O9 C29 1.405(7) . ?
F6 C26 1.308(6) . ?
C22 C23 1.506(6) . ?
C25 C26 1.545(7) . ?
O11 H11 0.8400 . ?
O11 C31 1.425(8) . ?
C20 H20 0.9500 . ?
C20 C21 1.491(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C8 1.493(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.527(6) . ?
C8 H8A 0.9500 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.535(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.518(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.511(6) . ?
C28 C27 1.553(7) . ?
F1 C27 1.293(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.525(7) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C18 1.527(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 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
C15 N11 C14 114.7(3) . . ?
C7 N1 H1 121.3 . . ?
C6 N1 H1 121.3 . . ?
C6 N1 C7 117.3(3) . . ?
C10 N14 H14 120.4 . . ?
C10 N14 C9 119.2(4) . . ?
C9 N14 H14 120.4 . . ?
C20 N7 N8 116.1(4) . . ?
C15 N9 H9 121.1 . . ?
C15 N9 C13 117.8(3) . . ?
C13 N9 H9 121.1 . . ?
C32 O12 H12 109.5 . . ?
C6 N2 C5 114.8(3) . . ?
C7 N5 H5 118.2 . . ?
C7 N5 C24 123.5(3) . . ?
C24 N5 H5 118.2 . . ?
N7 N8 H8 120.7 . . ?
C15 N8 N7 118.6(3) . . ?
C15 N8 H8 120.7 . . ?
C22 N6 H6 119.7 . . ?
C22 N6 C21 120.6(4) . . ?
C21 N6 H6 119.7 . . ?
C13 N10 C14 116.2(3) . . ?
N15 N16 H16 121.2 . . ?
C6 N16 H16 121.2 . . ?
C6 N16 N15 117.7(3) . . ?
C8 N15 N16 116.0(4) . . ?
C7 N3 C5 115.7(3) . . ?
C13 N13 H13 118.6 . . ?
C13 N13 C12 122.8(4) . . ?
C12 N13 H13 118.6 . . ?
C3 O1 C1 110.2(4) . . ?
C5 N4 C4 121.9(4) . . ?
C5 N4 C2 122.4(3) . . ?
C4 N4 C2 114.7(3) . . ?
C18 O4 C17 111.4(4) . . ?
C30 O10 H10 109.5 . . ?
C14 N12 C16 122.3(4) . . ?
C14 N12 C19 123.4(4) . . ?
C19 N12 C16 113.8(4) . . ?
N11 C15 N9 123.5(4) . . ?
N11 C15 N8 117.7(3) . . ?
N8 C15 N9 118.8(3) . . ?
O3 C10 N14 122.2(4) . . ?
O3 C10 C11 121.1(4) . . ?
N14 C10 C11 116.7(4) . . ?
N3 C5 N2 126.2(4) . . ?
N3 C5 N4 116.5(3) . . ?
N4 C5 N2 117.2(4) . . ?
N5 C7 N1 117.0(3) . . ?
N3 C7 N1 122.2(4) . . ?
N3 C7 N5 120.8(4) . . ?
N10 C14 N11 126.1(4) . . ?
N12 C14 N11 116.3(4) . . ?
N12 C14 N10 117.6(4) . . ?
C29 O9 H9C 109.5 . . ?
O2 C22 N6 122.5(4) . . ?
O2 C22 C23 119.8(4) . . ?
N6 C22 C23 117.6(4) . . ?
N10 C13 N9 121.5(4) . . ?
N13 C13 N9 117.0(4) . . ?
N13 C13 N10 121.4(4) . . ?
N2 C6 N1 123.7(4) . . ?
N2 C6 N16 118.2(4) . . ?
N16 C6 N1 118.1(4) . . ?
O8 C25 O7 129.6(4) . . ?
O8 C25 C26 115.3(4) . . ?
O7 C25 C26 115.0(4) . . ?
C31 O11 H11 109.5 . . ?
N7 C20 H20 119.8 . . ?
N7 C20 C21 120.4(4) . . ?
C21 C20 H20 119.8 . . ?
N14 C9 H9A 108.9 . . ?
N14 C9 H9B 108.9 . . ?
N14 C9 C8 113.4(3) . . ?
H9A C9 H9B 107.7 . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
N6 C21 C20 113.0(3) . . ?
N6 C21 H21A 109.0 . . ?
N6 C21 H21B 109.0 . . ?
C20 C21 H21A 109.0 . . ?
C20 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
N13 C12 H12A 109.1 . . ?
N13 C12 H12B 109.1 . . ?
N13 C12 C11 112.7(3) . . ?
H12A C12 H12B 107.8 . . ?
C11 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
N15 C8 C9 120.2(4) . . ?
N15 C8 H8A 119.9 . . ?
C9 C8 H8A 119.9 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 C24 110.8(4) . . ?
H23A C23 H23B 108.1 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
N4 C4 H4A 109.8 . . ?
N4 C4 H4B 109.8 . . ?
N4 C4 C3 109.4(4) . . ?
H4A C4 H4B 108.2 . . ?
C3 C4 H4A 109.8 . . ?
C3 C4 H4B 109.8 . . ?
N12 C16 H16A 109.9 . . ?
N12 C16 H16B 109.9 . . ?
N12 C16 C17 108.9(4) . . ?
H16A C16 H16B 108.3 . . ?
C17 C16 H16A 109.9 . . ?
C17 C16 H16B 109.9 . . ?
O5 C28 C27 116.5(4) . . ?
O6 C28 O5 129.5(4) . . ?
O6 C28 C27 114.0(4) . . ?
N4 C2 H2A 110.0 . . ?
N4 C2 H2B 110.0 . . ?
N4 C2 C1 108.7(4) . . ?
H2A C2 H2B 108.3 . . ?
C1 C2 H2A 110.0 . . ?
C1 C2 H2B 110.0 . . ?
N5 C24 C23 112.7(3) . . ?
N5 C24 H24A 109.1 . . ?
N5 C24 H24B 109.1 . . ?
C23 C24 H24A 109.1 . . ?
C23 C24 H24B 109.1 . . ?
H24A C24 H24B 107.8 . . ?
C10 C11 C12 111.6(4) . . ?
C10 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
N12 C19 H19A 109.8 . . ?
N12 C19 H19B 109.8 . . ?
N12 C19 C18 109.2(4) . . ?
H19A C19 H19B 108.3 . . ?
C18 C19 H19A 109.8 . . ?
C18 C19 H19B 109.8 . . ?
O1 C3 C4 110.5(4) . . ?
O1 C3 H3A 109.6 . . ?
O1 C3 H3B 109.6 . . ?
C4 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
F4 C26 F5 103.2(5) . . ?
F4 C26 F6 113.5(6) . . ?
F4 C26 C25 113.8(5) . . ?
F5 C26 C25 108.9(6) . . ?
F6 C26 F5 101.5(6) . . ?
F6 C26 C25 114.4(4) . . ?
O4 C17 C16 112.5(4) . . ?
O4 C17 H17A 109.1 . . ?
O4 C17 H17B 109.1 . . ?
C16 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
O9 C29 H29A 109.5 . . ?
O9 C29 H29B 109.5 . . ?
O9 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O1 C1 C2 110.1(5) . . ?
O1 C1 H1A 109.7 . . ?
O1 C1 H1B 109.6 . . ?
C2 C1 H1A 109.7 . . ?
C2 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
O4 C18 C19 110.5(5) . . ?
O4 C18 H18A 109.6 . . ?
O4 C18 H18B 109.6 . . ?
C19 C18 H18A 109.6 . . ?
C19 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
F2 C27 F3 104.7(5) . . ?
F2 C27 C28 114.7(4) . . ?
F3 C27 C28 109.4(5) . . ?
F1 C27 F2 107.2(5) . . ?
F1 C27 F3 107.6(6) . . ?
F1 C27 C28 112.6(5) . . ?
O11 C31 H31A 109.5 . . ?
O11 C31 H31B 109.5 . . ?
O11 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O12 C32 H32A 109.5 . . ?
O12 C32 H32B 109.5 . . ?
O12 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O10 C30 H30A 109.5 . . ?
O10 C30 H30B 109.5 . . ?
O10 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O7 0.88 1.97 2.818(5) 162.8 . yes
N14 H14 O7 0.88 2.07 2.937(5) 167.3 . yes
N9 H9 O5 0.88 1.97 2.836(5) 165.6 . yes
O12 H12 O11 0.84 1.91 2.749(5) 174.7 . yes
N5 H5 O8 0.88 1.96 2.781(5) 154.9 . yes
N8 H8 O10 0.88 1.85 2.730(5) 175.1 4 yes
N6 H6 O5 0.88 2.10 2.957(5) 165.8 . yes
N16 H16 O12 0.88 2.00 2.847(5) 159.8 2_574 yes
N13 H13 O6 0.88 1.90 2.750(5) 162.6 . yes
O10 H10 O9 0.84 1.84 2.632(6) 157.6 . yes
O9 H9C O3 0.84 1.88 2.677(5) 157.6 . yes
O11 H11 O2 0.84 1.88 2.677(5) 157.5 . yes
C21 H21A O4 0.99 2.65 3.416(6) 133.8 2_565 yes
C8 H8A O12 0.95 2.57 3.351(6) 140.2 2_574 yes
C23 H23B F2 0.99 2.59 3.378(6) 136.5 . yes
C4 H4A O2 0.99 2.61 3.555(6) 159.4 . yes
C4 H4B N8 0.99 2.58 3.544(6) 165.4 1_565 yes
C16 H16A O3 0.99 2.58 3.490(6) 153.2 . yes
C16 H16B N16 0.99 2.67 3.543(6) 146.6 1_545 yes
C11 H11A O1 0.99 2.44 3.033(6) 118.1 4_464 yes
C17 H17A O2 0.99 2.65 3.577(6) 156.2 2_564 yes
C1 H1B F3 0.99 2.63 3.347(7) 129.6 3 yes
C18 H18B O8 0.99 2.57 3.547(6) 168.0 3_545 yes
C30 H30B F1 0.98 2.50 3.394(8) 152.2 2_554 yes

_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_2x2
_database_code_depnum_ccdc_archive 'CCDC 1957429'
loop_
_audit_author_name
_audit_author_address
'Arshad Mehmood'
;Texas Christian University
United States of America
;
_audit_update_record             
;
2019-10-03 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_THETM01_2x2                 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Crystals diffracted poorly at room temperature and at
100K. Best ones show reflections at a maximum resolution of ~1.15 Ang. 
;
# end Validation Reply Form

_audit_creation_date             2019-02-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 F3 O2, C12 H19 N8 O2, 2(H2 O)'
_chemical_formula_sum            'C14 H23 F3 N8 O6'
_chemical_formula_weight         456.40
_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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.754(3)
_cell_length_b                   13.7241(16)
_cell_length_c                   15.904(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.156(3)
_cell_angle_gamma                90
_cell_volume                     4673.7(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9047
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.823
_cell_measurement_theta_min      2.969
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.7446
_exptl_absorpt_correction_T_min  0.6800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0777 before and 0.0718 after correction. The Ratio of minimum to maximum transmission is 0.9132. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.462
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.222
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            49604
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        20.868
_diffrn_reflns_theta_max         20.868
_diffrn_reflns_theta_min         2.940
_diffrn_ambient_temperature      100.02
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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                2035
_reflns_number_total             2444
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.936
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         2444
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0841
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1297P)²+46.0410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2230
_refine_ls_wR_factor_ref         0.2405
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O5(H5C,H5D), O6(H6C,H6D)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,
 H10B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N5(H5), N7(H7), N8(H8), C8(H8A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.5995(2) 0.9635(3) 0.3079(3) 0.0743(14) Uani 1 1 d . . . . .
F2 F 0.6174(2) 0.8678(3) 0.2110(3) 0.0629(12) Uani 1 1 d . . . . .
F3 F 0.6704(2) 0.8567(3) 0.3364(3) 0.0776(14) Uani 1 1 d . . . . .
O3 O 0.5246(2) 0.8295(3) 0.3518(3) 0.0381(11) Uani 1 1 d . . . . .
O4 O 0.57921(19) 0.7114(3) 0.3032(3) 0.0391(11) Uani 1 1 d . . . . .
C13 C 0.5673(3) 0.7983(5) 0.3180(4) 0.0358(16) Uani 1 1 d . . . . .
C14 C 0.6139(3) 0.8722(4) 0.2932(4) 0.0386(16) Uani 1 1 d . . . . .
O1 O 0.7010(3) 0.6660(6) 0.0734(4) 0.106(3) Uani 1 1 d . . . . .
O2 O 0.3164(2) 0.2108(3) 0.4423(3) 0.0483(12) Uani 1 1 d . . . . .
N1 N 0.4999(2) 0.3837(3) 0.3803(3) 0.0264(12) Uani 1 1 d . . . . .
N2 N 0.5209(2) 0.5491(3) 0.3586(3) 0.0246(11) Uani 1 1 d . . . . .
H2 H 0.543416 0.593589 0.338232 0.029 Uiso 1 1 calc R . . . .
N3 N 0.4351(2) 0.5082(3) 0.4231(3) 0.0285(12) Uani 1 1 d . . . . .
N4 N 0.4126(2) 0.3466(3) 0.4369(3) 0.0324(12) Uani 1 1 d . . . . .
N5 N 0.5866(2) 0.4254(3) 0.3273(3) 0.0302(12) Uani 1 1 d . . . . .
H5 H 0.595335 0.362975 0.324468 0.036 Uiso 1 1 calc R . . . .
N6 N 0.6261(2) 0.4931(3) 0.3020(3) 0.0326(12) Uani 1 1 d . . . . .
N7 N 0.6619(2) 0.6522(4) 0.1948(3) 0.0440(14) Uani 1 1 d . . . . .
H7 H 0.627711 0.659558 0.216653 0.053 Uiso 1 1 calc R . . . .
N8 N 0.4573(2) 0.6680(3) 0.3995(3) 0.0318(12) Uani 1 1 d . . . . .
H8 H 0.480952 0.711419 0.379752 0.038 Uiso 1 1 calc R . . . .
C1 C 0.4498(3) 0.4145(4) 0.4123(3) 0.0271(14) Uani 1 1 d . . . . .
C2 C 0.5349(3) 0.4529(4) 0.3562(3) 0.0261(14) Uani 1 1 d . . . . .
C3 C 0.4702(2) 0.5740(4) 0.3942(3) 0.0266(14) Uani 1 1 d . . . . .
C4 C 0.3595(3) 0.3711(4) 0.4784(4) 0.0367(15) Uani 1 1 d . . . . .
H4A H 0.349703 0.441392 0.471022 0.044 Uiso 1 1 calc R . . . .
H4B H 0.370074 0.357173 0.540329 0.044 Uiso 1 1 calc R . . . .
C5 C 0.3037(3) 0.3115(5) 0.4388(4) 0.0444(17) Uani 1 1 d . . . . .
H5A H 0.268577 0.324987 0.469182 0.053 Uiso 1 1 calc R . . . .
H5B H 0.290592 0.331279 0.378468 0.053 Uiso 1 1 calc R . . . .
C6 C 0.3648(3) 0.1889(5) 0.3965(4) 0.0427(17) Uani 1 1 d . . . . .
H6A H 0.351494 0.207518 0.335862 0.051 Uiso 1 1 calc R . . . .
H6B H 0.372540 0.117740 0.398616 0.051 Uiso 1 1 calc R . . . .
C7 C 0.4246(3) 0.2414(4) 0.4322(4) 0.0355(15) Uani 1 1 d . . . . .
H7A H 0.441562 0.216123 0.489964 0.043 Uiso 1 1 calc R . . . .
H7B H 0.456010 0.229662 0.395189 0.043 Uiso 1 1 calc R . . . .
C8 C 0.6756(3) 0.4592(5) 0.2809(4) 0.0394(16) Uani 1 1 d . . . . .
H8A H 0.681494 0.390599 0.283619 0.047 Uiso 1 1 calc R . . . .
C9 C 0.7244(3) 0.5185(5) 0.2525(5) 0.0552(19) Uani 1 1 d . . . . .
H9A H 0.764681 0.503062 0.289845 0.066 Uiso 1 1 calc R . . . .
H9B H 0.727934 0.497631 0.193961 0.066 Uiso 1 1 calc R . . . .
C10 C 0.7165(3) 0.6247(6) 0.2517(5) 0.059(2) Uani 1 1 d . . . . .
H10A H 0.713811 0.647558 0.310020 0.071 Uiso 1 1 calc R . . . .
H10B H 0.753272 0.655965 0.234233 0.071 Uiso 1 1 calc R . . . .
C11 C 0.6569(3) 0.6681(6) 0.1115(5) 0.055(2) Uani 1 1 d . . . . .
C12 C 0.4055(3) 0.6997(5) 0.4369(4) 0.0423(17) Uani 1 1 d . . . . .
H12A H 0.406187 0.771695 0.440502 0.051 Uiso 1 1 calc R . . . .
H12B H 0.410485 0.673933 0.495849 0.051 Uiso 1 1 calc R . . . .
O5 O 0.8165(3) 0.6624(6) 0.0412(5) 0.100(2) Uani 1 1 d . . . . .
H5C H 0.796364 0.715674 0.048101 0.151 Uiso 1 1 d G . . . .
H5D H 0.809808 0.646457 -0.012547 0.151 Uiso 1 1 d G . . . .
O6 O 0.6106(2) 0.2324(3) 0.3076(3) 0.0525(13) Uani 1 1 d . . . . .
H6C H 0.638880 0.206165 0.346450 0.079 Uiso 1 1 d G . . . .
H6D H 0.577311 0.195980 0.299499 0.079 Uiso 1 1 d G . . . .


_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 C14 1.323(7) . ?
F2 C14 1.323(7) . ?
F3 C14 1.314(7) . ?
O3 C13 1.230(7) . ?
O4 C13 1.252(7) . ?
C13 C14 1.533(9) . ?
O1 C11 1.223(8) . ?
O2 C5 1.408(8) . ?
O2 C6 1.415(8) . ?
N1 C1 1.349(7) . ?
N1 C2 1.315(7) . ?
N2 H2 0.8800 . ?
N2 C2 1.357(7) . ?
N2 C3 1.369(7) . ?
N3 C1 1.344(7) . ?
N3 C3 1.316(7) . ?
N4 C1 1.337(7) . ?
N4 C4 1.467(7) . ?
N4 C7 1.472(8) . ?
N5 H5 0.8800 . ?
N5 N6 1.374(6) . ?
N5 C2 1.344(7) . ?
N6 C8 1.271(7) . ?
N7 H7 0.8800 . ?
N7 C10 1.413(9) . ?
N7 C11 1.327(8) . ?
N8 H8 0.8800 . ?
N8 C3 1.325(7) . ?
N8 C12 1.433(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.507(9) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.508(9) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9500 . ?
C8 C9 1.471(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.467(11) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.501(10) 2_655 ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
O5 H5C 0.8696 . ?
O5 H5D 0.8697 . ?
O6 H6C 0.8700 . ?
O6 H6D 0.8699 . ?

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
O3 C13 O4 127.6(6) . . ?
O3 C13 C14 117.9(6) . . ?
O4 C13 C14 114.4(6) . . ?
F1 C14 F2 105.9(5) . . ?
F1 C14 C13 113.1(6) . . ?
F2 C14 C13 112.3(5) . . ?
F3 C14 F1 106.8(5) . . ?
F3 C14 F2 107.4(5) . . ?
F3 C14 C13 110.9(5) . . ?
C5 O2 C6 110.4(4) . . ?
C2 N1 C1 115.5(5) . . ?
C2 N2 H2 121.5 . . ?
C2 N2 C3 117.1(5) . . ?
C3 N2 H2 121.5 . . ?
C3 N3 C1 116.5(5) . . ?
C1 N4 C4 122.5(5) . . ?
C1 N4 C7 123.1(5) . . ?
C4 N4 C7 114.2(4) . . ?
N6 N5 H5 119.5 . . ?
C2 N5 H5 119.5 . . ?
C2 N5 N6 121.1(5) . . ?
C8 N6 N5 115.6(5) . . ?
C10 N7 H7 116.8 . . ?
C11 N7 H7 116.8 . . ?
C11 N7 C10 126.5(6) . . ?
C3 N8 H8 119.6 . . ?
C3 N8 C12 120.8(5) . . ?
C12 N8 H8 119.6 . . ?
N3 C1 N1 125.0(5) . . ?
N4 C1 N1 117.6(5) . . ?
N4 C1 N3 117.4(5) . . ?
N1 C2 N2 123.4(5) . . ?
N1 C2 N5 117.3(5) . . ?
N5 C2 N2 119.3(5) . . ?
N3 C3 N2 122.2(5) . . ?
N3 C3 N8 120.3(5) . . ?
N8 C3 N2 117.6(5) . . ?
N4 C4 H4A 109.9 . . ?
N4 C4 H4B 109.9 . . ?
N4 C4 C5 109.1(5) . . ?
H4A C4 H4B 108.3 . . ?
C5 C4 H4A 109.9 . . ?
C5 C4 H4B 109.9 . . ?
O2 C5 C4 112.2(5) . . ?
O2 C5 H5A 109.2 . . ?
O2 C5 H5B 109.2 . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
O2 C6 H6A 109.2 . . ?
O2 C6 H6B 109.2 . . ?
O2 C6 C7 112.0(5) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
N4 C7 C6 109.8(5) . . ?
N4 C7 H7A 109.7 . . ?
N4 C7 H7B 109.7 . . ?
C6 C7 H7A 109.7 . . ?
C6 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
N6 C8 H8A 117.6 . . ?
N6 C8 C9 124.7(6) . . ?
C9 C8 H8A 117.6 . . ?
C8 C9 H9A 107.9 . . ?
C8 C9 H9B 107.9 . . ?
H9A C9 H9B 107.2 . . ?
C10 C9 C8 117.5(6) . . ?
C10 C9 H9A 107.9 . . ?
C10 C9 H9B 107.9 . . ?
N7 C10 C9 110.8(6) . . ?
N7 C10 H10A 109.5 . . ?
N7 C10 H10B 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
O1 C11 N7 123.9(7) . . ?
O1 C11 C12 118.0(6) . 2_655 ?
N7 C11 C12 117.8(6) . 2_655 ?
N8 C12 C11 114.0(5) . 2_655 ?
N8 C12 H12A 108.8 . . ?
N8 C12 H12B 108.8 . . ?
C11 C12 H12A 108.8 2_655 . ?
C11 C12 H12B 108.8 2_655 . ?
H12A C12 H12B 107.7 . . ?
H5C O5 H5D 109.5 . . ?
H6C O6 H6D 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O4 0.88 1.92 2.783(6) 166.5 . yes
N5 H5 O6 0.88 1.85 2.728(6) 174.5 . yes
N7 H7 O4 0.88 2.01 2.821(7) 153.5 . yes
N8 H8 O3 0.88 1.97 2.832(6) 166.7 . yes
N8 H8 O4 0.88 2.64 3.341(6) 137.3 . yes
C5 H5A O2 0.99 2.56 3.497(7) 157.7 7_556 yes
C5 H5B F3 0.99 2.61 3.128(8) 112.9 3_445 yes
C6 H6A O6 0.99 2.58 3.433(8) 144.1 2_655 yes
C7 H7A O3 0.99 2.57 3.554(7) 171.3 5_666 yes
C12 H12B N1 0.99 2.64 3.449(8) 139.3 5_666 yes

_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_4x4
_database_code_depnum_ccdc_archive 'CCDC 1957431'
loop_
_audit_author_name
_audit_author_address
'Arshad Mehmood'
;Texas Christian University
United States of America
;
_audit_update_record             
;
2019-10-03 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;
_audit_creation_date             2019-09-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C2 F3 O2), C26 H42 N16 O4, 3(C H4 O)'
_chemical_formula_sum            'C33 H54 F6 N16 O11'
_chemical_formula_weight         964.92
_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                   8.3279(4)
_cell_length_b                   15.8912(9)
_cell_length_c                   16.9567(9)
_cell_angle_alpha                98.047(2)
_cell_angle_beta                 96.401(2)
_cell_angle_gamma                98.061(2)
_cell_volume                     2180.2(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9606
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.23
_cell_measurement_theta_min      2.95
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.922
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0663 before and 0.0593 after correction. The Ratio of minimum to maximum transmission is 0.9226. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1012
_exptl_crystal_size_max          0.649
_exptl_crystal_size_mid          0.526
_exptl_crystal_size_min          0.276
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            84848
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.265
_diffrn_reflns_theta_min         2.920
_diffrn_ambient_temperature      100.05
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.988
_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                8226
_reflns_number_total             9663
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.190
_refine_diff_density_min         -0.900
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     629
_refine_ls_number_reflns         9663
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0822
_refine_ls_restrained_S_all      1.079
_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)+(0.1002P)²+5.1165P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2209
_refine_ls_wR_factor_ref         0.2303
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F1A) = Uanis(F1B)
Uanis(F2A) = Uanis(F2B)
Uanis(F3A) = Uanis(F3B)
Uanis(F4A) = Uanis(F4B)
Uanis(F5A) = Uanis(F5B)
Uanis(F6A) = Uanis(F6B)
Uanis(O11A) = Uanis(O11B)
Uanis(O12A) = Uanis(O12B)
Uanis(C30A) = Uanis(C30B)
3. Others
 Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(F4B)=Sof(F5B)=Sof(F6B)=Sof(O11B)=Sof(O12B)=
 Sof(C30B)=1-FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=Sof(O11A)=Sof(O12A)=
 Sof(C30A)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C8(H8A,H8B), C10(H10A,
 H10B), C11(H11A,H11B), C12(H12A,H12B), C16(H16A,H16B), C17(H17A,H17B),
 C18(H18A,H18B), C19(H19A,H19B), C21(H21A,H21B), C23(H23A,H23B), C24(H24A,H24B),
  C25(H25A,H25B)
4.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N5(H5), N7(H7), N8(H8), N9(H9), N13(H13), N15(H15), N16(H16),
 C13(H13A), C26(H26)
4.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C)
4.d Idealised tetrahedral OH refined as rotating group:
 O5(H5A), O6(H6), O7(H7A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
F1A F 1.2497(10) 0.7311(6) -0.0269(4) 0.0358(12) Uani 0.781(6) 1 d . . P A 1
F2A F 1.3430(6) 0.8010(5) 0.0940(5) 0.0471(13) Uani 0.781(6) 1 d . . P A 1
F3A F 1.0823(10) 0.7718(3) 0.0535(5) 0.0512(15) Uani 0.781(6) 1 d . . P A 1
F4A F 0.1050(7) 0.1010(3) 0.7008(4) 0.0748(17) Uani 0.781(6) 1 d . . P A 1
F5A F 0.0880(17) 0.0234(6) 0.8027(6) 0.109(3) Uani 0.781(6) 1 d . . P A 1
F6A F -0.0915(19) 0.0935(8) 0.7659(5) 0.079(2) Uani 0.781(6) 1 d . . P A 1
O11A O -0.1649(8) -0.0854(5) 0.6991(5) 0.076(2) Uani 0.781(6) 1 d . . P A 1
O12A O 0.0277(6) -0.0647(3) 0.6285(3) 0.0590(11) Uani 0.781(6) 1 d . . P A 1
C30A C -0.0481(7) -0.0408(4) 0.6818(3) 0.0384(11) Uani 0.781(6) 1 d . . P A 1
F1B F 1.278(4) 0.742(3) -0.015(2) 0.0358(12) Uani 0.219(6) 1 d . . P A 2
F2B F 1.297(3) 0.800(2) 0.096(2) 0.0471(13) Uani 0.219(6) 1 d . . P A 2
F3B F 1.061(4) 0.7473(15) 0.040(2) 0.0512(15) Uani 0.219(6) 1 d . . P A 2
F4B F 0.158(3) 0.0775(11) 0.7210(15) 0.0748(17) Uani 0.219(6) 1 d . . P A 2
F5B F 0.050(7) 0.035(3) 0.804(3) 0.109(3) Uani 0.219(6) 1 d . . P A 2
F6B F -0.095(8) 0.087(4) 0.743(2) 0.079(2) Uani 0.219(6) 1 d . . P A 2
O11B O -0.119(3) -0.084(2) 0.676(2) 0.076(2) Uani 0.219(6) 1 d . . P A 2
O12B O -0.022(2) -0.0166(9) 0.5966(9) 0.0590(11) Uani 0.219(6) 1 d . . P A 2
C30B C -0.095(3) -0.0189(14) 0.6703(14) 0.0384(11) Uani 0.219(6) 1 d . . P A 2
O8 O 1.1502(3) 0.65178(15) 0.14615(13) 0.0301(5) Uani 1 1 d . . . . .
O9 O 1.2907(3) 0.59882(15) 0.05132(13) 0.0302(5) Uani 1 1 d . . . . .
C32 C 1.2204(3) 0.65377(19) 0.08538(17) 0.0222(6) Uani 1 1 d . . . . .
C33 C 1.2208(4) 0.7391(2) 0.05039(19) 0.0290(6) Uani 1 1 d . . . . .
C31 C 0.0167(5) 0.0457(2) 0.7369(2) 0.0388(8) Uani 1 1 d . . . . .
O1 O 0.7453(3) 1.00677(14) 1.01005(13) 0.0286(5) Uani 1 1 d . . . . .
O2 O 0.6231(3) 0.08429(15) 0.21017(17) 0.0416(6) Uani 1 1 d . . . . .
O3 O 0.5574(3) 0.47706(13) 0.66898(12) 0.0236(4) Uani 1 1 d . . . . .
O4 O 0.8234(2) 0.61369(13) 0.55904(11) 0.0218(4) Uani 1 1 d . . . . .
N1 N 0.5864(3) 0.60638(15) 0.81498(14) 0.0197(5) Uani 1 1 d . . . . .
H1 H 0.543641 0.557274 0.784220 0.024 Uiso 1 1 calc R . . . .
N2 N 0.7542(3) 0.74124(15) 0.83213(14) 0.0207(5) Uani 1 1 d . . . . .
N3 N 0.6077(3) 0.69888(16) 0.93849(14) 0.0217(5) Uani 1 1 d . . . . .
N4 N 0.7571(3) 0.83395(16) 0.94865(14) 0.0224(5) Uani 1 1 d . . . . .
N5 N 0.4446(3) 0.56782(16) 0.91835(14) 0.0235(5) Uani 1 1 d . . . . .
H5 H 0.413236 0.578523 0.966113 0.028 Uiso 1 1 calc R . . . .
N6 N 0.3891(3) 0.49019(16) 0.86807(14) 0.0216(5) Uani 1 1 d . . . . .
N7 N 0.5015(3) 0.33365(15) 0.67425(14) 0.0220(5) Uani 1 1 d . . . . .
H7 H 0.495771 0.281744 0.646931 0.026 Uiso 1 1 calc R . . . .
N8 N 0.6531(3) 0.43987(14) 0.51822(13) 0.0182(4) Uani 1 1 d . . . . .
H8 H 0.688084 0.490451 0.548044 0.022 Uiso 1 1 calc R . . . .
N9 N 0.8117(3) 0.48301(14) 0.42303(13) 0.0174(4) Uani 1 1 d . . . . .
H9 H 0.847609 0.532752 0.454136 0.021 Uiso 1 1 calc R . . . .
N10 N 0.6452(3) 0.34699(14) 0.40064(13) 0.0192(5) Uani 1 1 d . . . . .
N11 N 0.8138(3) 0.39007(15) 0.30186(13) 0.0192(5) Uani 1 1 d . . . . .
N12 N 0.6529(3) 0.25697(15) 0.28340(14) 0.0218(5) Uani 1 1 d . . . . .
N13 N 0.9701(3) 0.52346(15) 0.32631(14) 0.0208(5) Uani 1 1 d . . . . .
H13 H 1.011718 0.512475 0.281208 0.025 Uiso 1 1 calc R . . . .
N14 N 1.0121(3) 0.60248(15) 0.37495(14) 0.0203(5) Uani 1 1 d . . . . .
N15 N 0.8672(3) 0.75871(16) 0.56068(15) 0.0250(5) Uani 1 1 d . . . . .
H15 H 0.862015 0.808842 0.589018 0.030 Uiso 1 1 calc R . . . .
N16 N 0.7322(3) 0.64694(15) 0.71458(14) 0.0212(5) Uani 1 1 d . . . . .
H16 H 0.687566 0.598155 0.683796 0.025 Uiso 1 1 calc R . . . .
C1 C 0.6435(4) 0.93879(19) 1.03606(18) 0.0252(6) Uani 1 1 d . . . . .
H1A H 0.535795 0.926693 1.002014 0.030 Uiso 1 1 calc R . . . .
H1B H 0.625375 0.957086 1.092187 0.030 Uiso 1 1 calc R . . . .
C2 C 0.7205(4) 0.85738(19) 1.03122(17) 0.0251(6) Uani 1 1 d . . . . .
H2A H 0.822560 0.867147 1.069549 0.030 Uiso 1 1 calc R . . . .
H2B H 0.644367 0.810014 1.045579 0.030 Uiso 1 1 calc R . . . .
C3 C 0.8529(4) 0.90401(19) 0.91810(18) 0.0264(6) Uani 1 1 d . . . . .
H3A H 0.861444 0.886384 0.860562 0.032 Uiso 1 1 calc R . . . .
H3B H 0.964777 0.917412 0.948038 0.032 Uiso 1 1 calc R . . . .
C4 C 0.7693(4) 0.9827(2) 0.92838(19) 0.0291(6) Uani 1 1 d . . . . .
H4A H 0.836845 1.031167 0.910714 0.035 Uiso 1 1 calc R . . . .
H4B H 0.662056 0.970564 0.893921 0.035 Uiso 1 1 calc R . . . .
C5 C 0.7049(3) 0.75614(18) 0.90607(16) 0.0209(5) Uani 1 1 d . . . . .
C6 C 0.5479(3) 0.62567(18) 0.89112(16) 0.0206(5) Uani 1 1 d . . . . .
C7 C 0.6931(3) 0.66577(18) 0.78837(16) 0.0198(5) Uani 1 1 d . . . . .
C8 C 0.8493(3) 0.70774(19) 0.68560(16) 0.0230(6) Uani 1 1 d . . . . .
H8A H 0.960819 0.705196 0.711348 0.028 Uiso 1 1 calc R . . . .
H8B H 0.825744 0.766716 0.701118 0.028 Uiso 1 1 calc R . . . .
C9 C 0.8433(3) 0.68907(18) 0.59554(16) 0.0198(5) Uani 1 1 d . . . . .
C10 C 0.9013(4) 0.75677(18) 0.47819(17) 0.0237(6) Uani 1 1 d . . . . .
H10A H 0.862855 0.806079 0.456285 0.028 Uiso 1 1 calc R . . . .
H10B H 0.841945 0.703053 0.444618 0.028 Uiso 1 1 calc R . . . .
C11 C 1.0854(4) 0.7614(2) 0.47535(18) 0.0271(6) Uani 1 1 d . . . . .
H11A H 1.142722 0.817295 0.505675 0.033 Uiso 1 1 calc R . . . .
H11B H 1.124529 0.715283 0.502341 0.033 Uiso 1 1 calc R . . . .
C12 C 1.1301(4) 0.75190(19) 0.39012(19) 0.0266(6) Uani 1 1 d . . . . .
H12A H 1.075073 0.791634 0.360474 0.032 Uiso 1 1 calc R . . . .
H12B H 1.249614 0.769813 0.392918 0.032 Uiso 1 1 calc R . . . .
C13 C 1.0847(3) 0.66265(19) 0.34350(17) 0.0228(6) Uani 1 1 d . . . . .
H13A H 1.110278 0.651011 0.290239 0.027 Uiso 1 1 calc R . . . .
C14 C 0.8641(3) 0.46432(17) 0.35006(15) 0.0180(5) Uani 1 1 d . . . . .
C15 C 0.7054(3) 0.33356(17) 0.32997(16) 0.0184(5) Uani 1 1 d . . . . .
C16 C 0.6997(4) 0.23524(18) 0.20288(16) 0.0227(6) Uani 1 1 d . . . . .
H16A H 0.791820 0.278547 0.195021 0.027 Uiso 1 1 calc R . . . .
H16B H 0.606213 0.235997 0.161584 0.027 Uiso 1 1 calc R . . . .
C17 C 0.7501(4) 0.14670(19) 0.1936(2) 0.0301(7) Uani 1 1 d . . . . .
H17A H 0.774121 0.130673 0.138060 0.036 Uiso 1 1 calc R . . . .
H17B H 0.850862 0.147820 0.230925 0.036 Uiso 1 1 calc R . . . .
C18 C 0.5894(5) 0.1046(2) 0.2907(2) 0.0375(8) Uani 1 1 d . . . . .
H18A H 0.689754 0.105733 0.328399 0.045 Uiso 1 1 calc R . . . .
H18B H 0.504387 0.059205 0.301715 0.045 Uiso 1 1 calc R . . . .
C19 C 0.5314(4) 0.19074(18) 0.30493(18) 0.0260(6) Uani 1 1 d . . . . .
H19A H 0.424576 0.188124 0.271792 0.031 Uiso 1 1 calc R . . . .
H19B H 0.516929 0.205256 0.362151 0.031 Uiso 1 1 calc R . . . .
C20 C 0.7013(3) 0.42201(16) 0.44644(15) 0.0167(5) Uani 1 1 d . . . . .
C21 C 0.5427(3) 0.37588(18) 0.54724(16) 0.0206(5) Uani 1 1 d . . . . .
H21A H 0.579793 0.319296 0.537188 0.025 Uiso 1 1 calc R . . . .
H21B H 0.431566 0.370613 0.517475 0.025 Uiso 1 1 calc R . . . .
C22 C 0.5364(3) 0.40038(18) 0.63673(16) 0.0199(5) Uani 1 1 d . . . . .
C23 C 0.4718(4) 0.34086(19) 0.75843(16) 0.0228(6) Uani 1 1 d . . . . .
H23A H 0.532545 0.395948 0.788911 0.027 Uiso 1 1 calc R . . . .
H23B H 0.512392 0.293339 0.782621 0.027 Uiso 1 1 calc R . . . .
C24 C 0.2902(4) 0.33706(19) 0.76425(17) 0.0235(6) Uani 1 1 d . . . . .
H24A H 0.230459 0.281929 0.733402 0.028 Uiso 1 1 calc R . . . .
H24B H 0.250398 0.384273 0.739237 0.028 Uiso 1 1 calc R . . . .
C25 C 0.2510(4) 0.34468(19) 0.85089(18) 0.0255(6) Uani 1 1 d . . . . .
H25A H 0.131085 0.330704 0.849850 0.031 Uiso 1 1 calc R . . . .
H25B H 0.301853 0.301602 0.877702 0.031 Uiso 1 1 calc R . . . .
C26 C 0.3094(4) 0.43190(19) 0.89944(17) 0.0237(6) Uani 1 1 d . . . . .
H26 H 0.287281 0.443775 0.953299 0.028 Uiso 1 1 calc R . . . .
O5 O 0.2388(6) 0.0353(3) 0.5469(2) 0.0797(12) Uani 1 1 d . . . . .
H5A H 0.153756 0.010807 0.561740 0.120 Uiso 1 1 calc GR . . . .
C28 C 0.2686(10) -0.0107(5) 0.4788(4) 0.093(2) Uani 1 1 d . . . . .
H28A H 0.165154 -0.041692 0.448566 0.140 Uiso 1 1 calc GR . . . .
H28B H 0.340346 -0.051985 0.492110 0.140 Uiso 1 1 calc GR . . . .
H28C H 0.322054 0.028238 0.446176 0.140 Uiso 1 1 calc GR . . . .
O6 O 0.4730(4) 0.15913(18) 0.6244(2) 0.0625(9) Uani 1 1 d . . . . .
H6 H 0.392319 0.123199 0.600822 0.094 Uiso 1 1 calc GR . . . .
C27 C 0.5498(8) 0.1256(3) 0.6936(4) 0.0714(16) Uani 1 1 d . . . . .
H27A H 0.606975 0.078503 0.674267 0.107 Uiso 1 1 calc GR . . . .
H27B H 0.465190 0.104186 0.724901 0.107 Uiso 1 1 calc GR . . . .
H27C H 0.628147 0.171770 0.727579 0.107 Uiso 1 1 calc GR . . . .
O7 O 1.1039(3) 0.49377(14) 0.18653(12) 0.0274(5) Uani 1 1 d . . . . .
H7A H 1.137271 0.540811 0.171967 0.041 Uiso 1 1 calc GR . . . .
C29 C 1.0209(4) 0.4348(2) 0.1190(2) 0.0339(7) Uani 1 1 d . . . . .
H29A H 1.091128 0.431295 0.076377 0.051 Uiso 1 1 calc GR . . . .
H29B H 0.919651 0.454557 0.099443 0.051 Uiso 1 1 calc GR . . . .
H29C H 0.994534 0.377905 0.134581 0.051 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
F1A C33 1.350(9) . ?
F2A C33 1.378(8) . ?
F3A C33 1.334(8) . ?
F4A C31 1.326(6) . ?
F5A C31 1.322(9) . ?
F6A C31 1.347(12) . ?
O11A C30A 1.210(8) . ?
O12A C30A 1.207(7) . ?
C30A C31 1.541(7) . ?
F1B C33 1.25(4) . ?
F2B C33 1.20(3) . ?
F3B C33 1.35(3) . ?
F4B C31 1.29(2) . ?
F5B C31 1.17(4) . ?
F6B C31 1.22(5) . ?
O11B C30B 1.04(4) . ?
O12B C30B 1.45(3) . ?
C30B C31 1.54(2) . ?
O8 C32 1.242(4) . ?
O9 C32 1.232(4) . ?
C32 C33 1.554(4) . ?
O1 C1 1.428(4) . ?
O1 C4 1.428(4) . ?
O2 C17 1.425(4) . ?
O2 C18 1.427(4) . ?
O3 C22 1.244(3) . ?
O4 C9 1.249(3) . ?
N1 H1 0.8800 . ?
N1 C6 1.369(3) . ?
N1 C7 1.363(4) . ?
N2 C5 1.362(3) . ?
N2 C7 1.320(4) . ?
N3 C5 1.348(4) . ?
N3 C6 1.317(4) . ?
N4 C2 1.474(3) . ?
N4 C3 1.466(4) . ?
N4 C5 1.330(4) . ?
N5 H5 0.8800 . ?
N5 N6 1.386(3) . ?
N5 C6 1.335(4) . ?
N6 C26 1.275(4) . ?
N7 H7 0.8800 . ?
N7 C22 1.326(4) . ?
N7 C23 1.467(3) . ?
N8 H8 0.8800 . ?
N8 C20 1.330(3) . ?
N8 C21 1.449(3) . ?
N9 H9 0.8800 . ?
N9 C14 1.365(3) . ?
N9 C20 1.371(3) . ?
N10 C15 1.351(3) . ?
N10 C20 1.322(3) . ?
N11 C14 1.323(3) . ?
N11 C15 1.355(4) . ?
N12 C15 1.342(3) . ?
N12 C16 1.470(3) . ?
N12 C19 1.469(4) . ?
N13 H13 0.8800 . ?
N13 N14 1.379(3) . ?
N13 C14 1.333(4) . ?
N14 C13 1.272(4) . ?
N15 H15 0.8800 . ?
N15 C9 1.327(4) . ?
N15 C10 1.455(4) . ?
N16 H16 0.8800 . ?
N16 C7 1.332(3) . ?
N16 C8 1.449(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.519(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.513(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.508(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.531(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.525(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.499(4) . ?
C13 H13A 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.516(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.512(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.521(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.520(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.532(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.496(4) . ?
C26 H26 0.9500 . ?
O5 H5A 0.8400 . ?
O5 C28 1.344(8) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
O6 H6 0.8400 . ?
O6 C27 1.474(7) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
O7 H7A 0.8400 . ?
O7 C29 1.417(4) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 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
O11A C30A C31 117.6(6) . . ?
O12A C30A O11A 122.8(7) . . ?
O12A C30A C31 119.2(5) . . ?
O11B C30B O12B 105(3) . . ?
O11B C30B C31 121(3) . . ?
O12B C30B C31 107.8(15) . . ?
O8 C32 C33 113.9(3) . . ?
O9 C32 O8 128.9(3) . . ?
O9 C32 C33 117.2(3) . . ?
F1A C33 F2A 106.9(5) . . ?
F1A C33 C32 112.9(5) . . ?
F2A C33 C32 109.5(4) . . ?
F3A C33 F1A 106.9(6) . . ?
F3A C33 F2A 106.1(4) . . ?
F3A C33 C32 114.1(4) . . ?
F1B C33 F3B 110(2) . . ?
F1B C33 C32 117(2) . . ?
F2B C33 F1B 105(2) . . ?
F2B C33 F3B 109.8(18) . . ?
F2B C33 C32 112.3(18) . . ?
F3B C33 C32 103.5(12) . . ?
F4A C31 F6A 101.7(7) . . ?
F4A C31 C30A 112.6(4) . . ?
F5A C31 F4A 117.7(8) . . ?
F5A C31 F6A 102.3(7) . . ?
F5A C31 C30A 103.9(5) . . ?
F6A C31 C30A 118.9(7) . . ?
F4B C31 C30B 117.3(14) . . ?
F5B C31 F4B 101(4) . . ?
F5B C31 F6B 102(3) . . ?
F5B C31 C30B 126(3) . . ?
F6B C31 F4B 123(3) . . ?
F6B C31 C30B 89(3) . . ?
C1 O1 C4 110.3(2) . . ?
C17 O2 C18 110.6(2) . . ?
C6 N1 H1 121.1 . . ?
C7 N1 H1 121.1 . . ?
C7 N1 C6 117.8(2) . . ?
C7 N2 C5 115.9(2) . . ?
C6 N3 C5 115.7(2) . . ?
C3 N4 C2 114.1(2) . . ?
C5 N4 C2 122.3(3) . . ?
C5 N4 C3 123.7(2) . . ?
N6 N5 H5 121.5 . . ?
C6 N5 H5 121.5 . . ?
C6 N5 N6 117.1(2) . . ?
C26 N6 N5 115.7(2) . . ?
C22 N7 H7 117.9 . . ?
C22 N7 C23 124.2(2) . . ?
C23 N7 H7 117.9 . . ?
C20 N8 H8 120.1 . . ?
C20 N8 C21 119.9(2) . . ?
C21 N8 H8 120.1 . . ?
C14 N9 H9 121.0 . . ?
C14 N9 C20 118.1(2) . . ?
C20 N9 H9 121.0 . . ?
C20 N10 C15 115.8(2) . . ?
C14 N11 C15 115.1(2) . . ?
C15 N12 C16 122.9(2) . . ?
C15 N12 C19 123.0(2) . . ?
C19 N12 C16 113.9(2) . . ?
N14 N13 H13 121.2 . . ?
C14 N13 H13 121.2 . . ?
C14 N13 N14 117.6(2) . . ?
C13 N14 N13 116.0(2) . . ?
C9 N15 H15 118.2 . . ?
C9 N15 C10 123.6(2) . . ?
C10 N15 H15 118.2 . . ?
C7 N16 H16 120.4 . . ?
C7 N16 C8 119.2(2) . . ?
C8 N16 H16 120.4 . . ?
O1 C1 H1A 109.4 . . ?
O1 C1 H1B 109.4 . . ?
O1 C1 C2 111.3(2) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
N4 C2 C1 108.9(2) . . ?
N4 C2 H2A 109.9 . . ?
N4 C2 H2B 109.9 . . ?
C1 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
N4 C3 H3A 109.9 . . ?
N4 C3 H3B 109.9 . . ?
N4 C3 C4 109.0(2) . . ?
H3A C3 H3B 108.3 . . ?
C4 C3 H3A 109.9 . . ?
C4 C3 H3B 109.9 . . ?
O1 C4 C3 111.5(3) . . ?
O1 C4 H4A 109.3 . . ?
O1 C4 H4B 109.3 . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
N3 C5 N2 125.3(2) . . ?
N4 C5 N2 116.5(3) . . ?
N4 C5 N3 118.2(2) . . ?
N3 C6 N1 122.8(3) . . ?
N3 C6 N5 118.7(2) . . ?
N5 C6 N1 118.5(2) . . ?
N2 C7 N1 122.3(2) . . ?
N2 C7 N16 119.6(3) . . ?
N16 C7 N1 118.0(2) . . ?
N16 C8 H8A 109.3 . . ?
N16 C8 H8B 109.3 . . ?
N16 C8 C9 111.8(2) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
O4 C9 N15 124.3(3) . . ?
O4 C9 C8 121.4(3) . . ?
N15 C9 C8 114.3(2) . . ?
N15 C10 H10A 109.7 . . ?
N15 C10 H10B 109.7 . . ?
N15 C10 C11 109.9(2) . . ?
H10A C10 H10B 108.2 . . ?
C11 C10 H10A 109.7 . . ?
C11 C10 H10B 109.7 . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 C10 113.2(2) . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C11 C12 H12A 108.6 . . ?
C11 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C13 C12 C11 114.5(2) . . ?
C13 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
N14 C13 C12 120.3(3) . . ?
N14 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
N11 C14 N9 122.8(2) . . ?
N11 C14 N13 118.6(2) . . ?
N13 C14 N9 118.6(2) . . ?
N10 C15 N11 126.1(2) . . ?
N12 C15 N10 116.8(2) . . ?
N12 C15 N11 117.1(2) . . ?
N12 C16 H16A 109.7 . . ?
N12 C16 H16B 109.7 . . ?
N12 C16 C17 109.8(2) . . ?
H16A C16 H16B 108.2 . . ?
C17 C16 H16A 109.7 . . ?
C17 C16 H16B 109.7 . . ?
O2 C17 C16 110.6(3) . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
O2 C18 H18A 109.3 . . ?
O2 C18 H18B 109.3 . . ?
O2 C18 C19 111.5(3) . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
N12 C19 C18 109.1(3) . . ?
N12 C19 H19A 109.9 . . ?
N12 C19 H19B 109.9 . . ?
C18 C19 H19A 109.9 . . ?
C18 C19 H19B 109.9 . . ?
H19A C19 H19B 108.3 . . ?
N8 C20 N9 117.8(2) . . ?
N10 C20 N8 120.1(2) . . ?
N10 C20 N9 122.0(2) . . ?
N8 C21 H21A 109.4 . . ?
N8 C21 H21B 109.4 . . ?
N8 C21 C22 111.0(2) . . ?
H21A C21 H21B 108.0 . . ?
C22 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
O3 C22 N7 124.8(3) . . ?
O3 C22 C21 121.2(2) . . ?
N7 C22 C21 114.0(2) . . ?
N7 C23 H23A 109.5 . . ?
N7 C23 H23B 109.5 . . ?
N7 C23 C24 110.6(2) . . ?
H23A C23 H23B 108.1 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
C23 C24 H24A 108.9 . . ?
C23 C24 H24B 108.9 . . ?
C23 C24 C25 113.2(2) . . ?
H24A C24 H24B 107.8 . . ?
C25 C24 H24A 108.9 . . ?
C25 C24 H24B 108.9 . . ?
C24 C25 H25A 108.8 . . ?
C24 C25 H25B 108.8 . . ?
H25A C25 H25B 107.7 . . ?
C26 C25 C24 113.8(2) . . ?
C26 C25 H25A 108.8 . . ?
C26 C25 H25B 108.8 . . ?
N6 C26 C25 119.6(3) . . ?
N6 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C28 O5 H5A 109.5 . . ?
O5 C28 H28A 109.5 . . ?
O5 C28 H28B 109.5 . . ?
O5 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 O6 H6 109.5 . . ?
O6 C27 H27A 109.5 . . ?
O6 C27 H27B 109.5 . . ?
O6 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 O7 H7A 109.5 . . ?
O7 C29 H29A 109.5 . . ?
O7 C29 H29B 109.5 . . ?
O7 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O3 0.88 2.20 2.952(3) 142.8 . yes
N5 H5 O9 0.88 1.88 2.735(3) 164.4 1_456 yes
N7 H7 O6 0.88 1.91 2.753(4) 159.6 . yes
N8 H8 O4 0.88 2.09 2.875(3) 148.0 . yes
N9 H9 O4 0.88 2.09 2.862(3) 145.9 . yes
N13 H13 O7 0.88 1.86 2.740(3) 177.7 . yes
N15 H15 O11A 0.88 2.38 3.228(10) 160.8 1_665 yes
N15 H15 O12A 0.88 2.24 2.948(5) 136.9 1_665 yes
N15 H15 O11B 0.88 2.06 2.93(4) 167.0 1_665 yes
N16 H16 O3 0.88 2.04 2.840(3) 150.8 . yes
C1 H1B O2 0.99 2.64 3.522(4) 148.2 1_566 yes
C2 H2A F5A 0.99 2.55 3.274(10) 130.0 2_667 yes
C2 H2A F5B 0.99 2.50 3.31(4) 138.8 2_667 yes
C3 H3B O1 0.99 2.52 3.460(4) 158.5 2_777 yes
C8 H8A N11 0.99 2.58 3.393(4) 139.3 2_766 yes
C8 H8B O11A 0.99 2.35 3.283(8) 157.7 1_665 yes
C8 H8B O11B 0.99 2.46 3.31(3) 144.1 1_665 yes
C10 H10B N14 0.99 2.54 3.117(4) 117.3 . yes
C12 H12B O6 0.99 2.49 3.458(4) 164.9 2_766 yes
C13 H13A O8 0.95 2.50 3.435(4) 166.5 . yes
C18 H18A O12A 0.99 2.58 3.504(6) 154.7 2_656 yes
C19 H19A O11A 0.99 2.66 3.257(6) 119.3 2_556 yes
C19 H19A N2 0.99 2.65 3.524(4) 147.4 2_666 yes
C21 H21B O4 0.99 2.42 3.401(3) 168.8 2_666 yes
C23 H23A N6 0.99 2.40 3.012(4) 119.2 . yes
C25 H25A O8 0.99 2.40 3.355(4) 160.8 2_666 yes
O5 H5A O12A 0.84 2.03 2.811(6) 154.7 . yes
O5 H5A O12B 0.84 1.66 2.491(18) 168.0 . yes
C28 H28A O12B 0.98 1.78 2.421(18) 119.7 2_556 yes
O6 H6 O5 0.84 1.82 2.652(5) 171.8 . yes
C27 H27A F6B 0.98 2.60 3.15(6) 115.7 1_655 yes
C27 H27B F4B 0.98 2.52 3.34(2) 140.9 . yes
O7 H7A O8 0.84 1.87 2.682(3) 162.9 . yes

_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_6x6
_database_code_depnum_ccdc_archive 'CCDC 1957432'
loop_
_audit_author_name
_audit_author_address
'Arshad Mehmood'
;Texas Christian University
United States of America
;
_audit_update_record             
;
2019-10-03 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;
_audit_creation_date             2019-09-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H46 N16 O4, 2(C2 F3 O2), 2(C H4 O), H2 O'
_chemical_formula_sum            'C34 H56 F6 N16 O11'
_chemical_formula_weight         978.94
_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                   10.0220(3)
_cell_length_b                   13.0296(4)
_cell_length_c                   18.2777(5)
_cell_angle_alpha                102.8940(10)
_cell_angle_beta                 95.7540(10)
_cell_angle_gamma                103.8890(10)
_cell_volume                     2228.50(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      2.88
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0497 before and 0.0474 after correction. The Ratio of minimum to maximum transmission is 0.9611. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1028
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            84991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.128
_diffrn_reflns_theta_min         2.876
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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                8016
_reflns_number_total             9843
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.649
_refine_diff_density_min         -1.410
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     614
_refine_ls_number_reflns         9843
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0793
_refine_ls_restrained_S_all      1.034
_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)+(0.1153P)²+5.5261P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2154
_refine_ls_wR_factor_ref         0.2318
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O11(H11C,H11D)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C11(H11A,H11B), C13(H13A,H13B), C2(H2A,H2B), C28(H28A,H28B),
 C18(H18A,H18B), C1(H1A,H1B), C25(H25A,H25B), C23(H23A,H23B), C9(H9A,H9B),
 C27(H27A,H27B), C10(H10A,H10B), C4(H4A,H4B), C21(H21A,H21B), C3(H3A,H3B),
 C24(H24A,H24B), C20(H20A,H20B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 N9(H9), N1(H1), N5(H5), N8(H8), N16(H16), N15(H15), N13(H13), N7(H7), C8(H8A),
  C22(H22)
2.d Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C33(H33A,H33B,H33C)
2.e Idealised tetrahedral OH refined as rotating group:
 O9(H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.76404(19) 0.68827(15) 0.84988(11) 0.0200(4) Uani 1 1 d . . . . .
O2 O 0.5031(2) 0.41028(16) 0.66373(12) 0.0259(4) Uani 1 1 d . . . . .
O1 O 0.3589(2) 0.07560(16) 1.02426(13) 0.0279(5) Uani 1 1 d . . . . .
O4 O 1.1433(2) 0.90311(18) 0.50208(13) 0.0310(5) Uani 1 1 d . . . . .
N9 N 0.6457(2) 0.52021(18) 0.56813(12) 0.0173(4) Uani 1 1 d . . . . .
H9 H 0.599220 0.463773 0.582600 0.021 Uiso 1 1 calc R . . . .
N11 N 0.7454(2) 0.71017(18) 0.59391(13) 0.0177(4) Uani 1 1 d . . . . .
N1 N 0.7170(2) 0.53036(17) 0.93878(12) 0.0163(4) Uani 1 1 d . . . . .
H1 H 0.769847 0.582651 0.922922 0.020 Uiso 1 1 calc R . . . .
O8 O 0.8779(2) 0.05109(18) 0.23535(15) 0.0354(5) Uani 1 1 d . . . . .
N5 N 0.8903(2) 0.56019(18) 1.03997(13) 0.0189(5) Uani 1 1 d . . . . .
H5 H 0.930119 0.542008 1.078474 0.023 Uiso 1 1 calc R . . . .
N8 N 0.6145(2) 0.63558(18) 0.67587(12) 0.0175(4) Uani 1 1 d . . . . .
H8 H 0.574856 0.575973 0.689087 0.021 Uiso 1 1 calc R . . . .
N2 N 0.6929(2) 0.41814(17) 1.02384(13) 0.0173(4) Uani 1 1 d . . . . .
N3 N 0.5051(2) 0.39545(17) 0.92252(13) 0.0168(4) Uani 1 1 d . . . . .
O9 O 1.0497(3) 0.5328(2) 0.16635(14) 0.0376(6) Uani 1 1 d . . . . .
H9C H 0.986193 0.507745 0.189441 0.056 Uiso 1 1 calc GR . . . .
N10 N 0.7683(2) 0.58782(19) 0.47807(13) 0.0200(5) Uani 1 1 d . . . . .
O6 O 0.7328(3) 0.3637(2) 0.31174(13) 0.0382(6) Uani 1 1 d . . . . .
N14 N 0.5925(2) 0.32016(18) 0.48296(13) 0.0194(5) Uani 1 1 d . . . . .
N16 N 0.5416(2) 0.51009(17) 0.84185(13) 0.0171(4) Uani 1 1 d . . . . .
H16 H 0.602975 0.556987 0.825776 0.020 Uiso 1 1 calc R . . . .
F6 F 0.9099(3) -0.21143(19) 0.18976(19) 0.0654(8) Uani 1 1 d . . . . .
N6 N 0.9547(2) 0.65096(18) 1.01657(13) 0.0185(4) Uani 1 1 d . . . . .
N15 N 0.4600(3) 0.23566(19) 0.67350(14) 0.0242(5) Uani 1 1 d . . . . .
H15 H 0.424202 0.189305 0.699361 0.029 Uiso 1 1 calc R . . . .
N13 N 0.6689(2) 0.40437(19) 0.45726(13) 0.0209(5) Uani 1 1 d . . . . .
H13 H 0.699483 0.391339 0.413540 0.025 Uiso 1 1 calc R . . . .
N7 N 0.9668(2) 0.7988(2) 0.83664(14) 0.0226(5) Uani 1 1 d . . . . .
H7 H 1.006969 0.845827 0.812325 0.027 Uiso 1 1 calc R . . . .
N12 N 0.8807(2) 0.77132(19) 0.50988(13) 0.0205(5) Uani 1 1 d . . . . .
O7 O 0.7320(3) -0.10124(19) 0.24733(17) 0.0442(7) Uani 1 1 d . . . . .
N4 N 0.4879(2) 0.28262(18) 1.00330(13) 0.0190(5) Uani 1 1 d . . . . .
F3 F 1.0725(3) 0.3974(3) 0.31208(15) 0.0628(8) Uani 1 1 d . . . . .
C7 C 0.5846(3) 0.4763(2) 0.90076(14) 0.0152(5) Uani 1 1 d . . . . .
C15 C 0.6704(3) 0.6248(2) 0.61279(15) 0.0167(5) Uani 1 1 d . . . . .
C6 C 0.7648(3) 0.5014(2) 1.00146(14) 0.0163(5) Uani 1 1 d . . . . .
C12 C 0.8296(3) 0.7593(2) 0.82133(14) 0.0178(5) Uani 1 1 d . . . . .
C17 C 0.7960(3) 0.6872(2) 0.52783(15) 0.0182(5) Uani 1 1 d . . . . .
C16 C 0.6949(3) 0.5062(2) 0.50092(15) 0.0180(5) Uani 1 1 d . . . . .
O11 O 0.6521(3) 0.1357(3) 0.24196(19) 0.0522(7) Uani 1 1 d . . . . .
H11C H 0.720400 0.105208 0.242321 0.078 Uiso 1 1 d G . . . .
H11D H 0.691500 0.204829 0.262407 0.078 Uiso 1 1 d G . . . .
C5 C 0.5645(3) 0.3679(2) 0.98282(15) 0.0160(5) Uani 1 1 d . . . . .
C14 C 0.6154(3) 0.7413(2) 0.72460(15) 0.0195(5) Uani 1 1 d . . . . .
H14A H 0.551604 0.728481 0.761605 0.023 Uiso 1 1 calc R . . . .
H14B H 0.578066 0.783455 0.692654 0.023 Uiso 1 1 calc R . . . .
F4 F 1.0407(3) -0.0676(2) 0.1781(2) 0.0899(12) Uani 1 1 d . . . . .
C11 C 1.0543(3) 0.7680(2) 0.89183(16) 0.0236(6) Uani 1 1 d . . . . .
H11A H 1.147956 0.774746 0.877332 0.028 Uiso 1 1 calc R . . . .
H11B H 1.013567 0.690567 0.891214 0.028 Uiso 1 1 calc R . . . .
C13 C 0.7574(3) 0.8104(2) 0.76820(16) 0.0214(5) Uani 1 1 d . . . . .
H13A H 0.818834 0.827987 0.730987 0.026 Uiso 1 1 calc R . . . .
H13B H 0.746488 0.880260 0.798338 0.026 Uiso 1 1 calc R . . . .
C2 C 0.5287(3) 0.2528(2) 1.07351(16) 0.0207(5) Uani 1 1 d . . . . .
H2A H 0.475172 0.279243 1.112904 0.025 Uiso 1 1 calc R . . . .
H2B H 0.628994 0.287958 1.092814 0.025 Uiso 1 1 calc R . . . .
C26 C 0.4466(3) 0.3370(2) 0.69288(15) 0.0210(5) Uani 1 1 d . . . . .
C8 C 1.0761(3) 0.7041(2) 1.05183(16) 0.0211(5) Uani 1 1 d . . . . .
H8A H 1.118925 0.679464 1.090844 0.025 Uiso 1 1 calc R . . . .
C28 C 0.3982(3) 0.4742(2) 0.80193(15) 0.0190(5) Uani 1 1 d . . . . .
H28A H 0.386045 0.523732 0.769370 0.023 Uiso 1 1 calc R . . . .
H28B H 0.334809 0.480807 0.839891 0.023 Uiso 1 1 calc R . . . .
C22 C 0.5841(3) 0.2233(2) 0.44484(16) 0.0211(5) Uani 1 1 d . . . . .
H22 H 0.630345 0.212720 0.401995 0.025 Uiso 1 1 calc R . . . .
C18 C 0.9350(3) 0.8803(2) 0.56193(17) 0.0243(6) Uani 1 1 d . . . . .
H18A H 0.902745 0.880737 0.611421 0.029 Uiso 1 1 calc R . . . .
H18B H 0.900962 0.934453 0.540478 0.029 Uiso 1 1 calc R . . . .
O10 O 0.4535(4) -0.0121(3) 0.28555(18) 0.0616(8) Uani 1 1 d . . . . .
C1 C 0.5005(3) 0.1294(2) 1.05777(18) 0.0244(6) Uani 1 1 d . . . . .
H1A H 0.562646 0.104407 1.023066 0.029 Uiso 1 1 calc R . . . .
H1B H 0.521494 0.109410 1.105997 0.029 Uiso 1 1 calc R . . . .
C25 C 0.5310(3) 0.1983(2) 0.61162(16) 0.0233(6) Uani 1 1 d . . . . .
H25A H 0.571164 0.139722 0.622152 0.028 Uiso 1 1 calc R . . . .
H25B H 0.608310 0.259655 0.608032 0.028 Uiso 1 1 calc R . . . .
C23 C 0.5019(3) 0.1266(2) 0.46715(17) 0.0252(6) Uani 1 1 d . . . . .
H23A H 0.564956 0.082080 0.478324 0.030 Uiso 1 1 calc R . . . .
H23B H 0.429995 0.081031 0.423339 0.030 Uiso 1 1 calc R . . . .
C9 C 1.1515(3) 0.8052(2) 1.03197(17) 0.0248(6) Uani 1 1 d . . . . .
H9A H 1.237558 0.793436 1.013483 0.030 Uiso 1 1 calc R . . . .
H9B H 1.179714 0.865962 1.078772 0.030 Uiso 1 1 calc R . . . .
C27 C 0.3560(3) 0.3577(2) 0.75287(16) 0.0226(6) Uani 1 1 d . . . . .
H27A H 0.359876 0.307503 0.786030 0.027 Uiso 1 1 calc R . . . .
H27B H 0.258302 0.340244 0.727522 0.027 Uiso 1 1 calc R . . . .
C10 C 1.0678(3) 0.8397(2) 0.97179(17) 0.0237(6) Uani 1 1 d . . . . .
H10A H 0.973501 0.836575 0.984648 0.028 Uiso 1 1 calc R . . . .
H10B H 1.113506 0.916414 0.972789 0.028 Uiso 1 1 calc R . . . .
C4 C 0.3293(3) 0.1012(2) 0.95359(18) 0.0276(6) Uani 1 1 d . . . . .
H4A H 0.232553 0.060530 0.929269 0.033 Uiso 1 1 calc R . . . .
H4B H 0.392717 0.077514 0.919273 0.033 Uiso 1 1 calc R . . . .
C21 C 0.9343(3) 0.7604(2) 0.43754(16) 0.0232(6) Uani 1 1 d . . . . .
H21A H 0.900293 0.807099 0.408290 0.028 Uiso 1 1 calc R . . . .
H21B H 0.900710 0.683587 0.406838 0.028 Uiso 1 1 calc R . . . .
C3 C 0.3467(3) 0.2228(2) 0.96442(17) 0.0230(6) Uani 1 1 d . . . . .
H3A H 0.330291 0.238969 0.914372 0.028 Uiso 1 1 calc R . . . .
H3B H 0.277906 0.245955 0.995026 0.028 Uiso 1 1 calc R . . . .
C24 C 0.4306(3) 0.1548(2) 0.53595(16) 0.0226(6) Uani 1 1 d . . . . .
H24A H 0.359555 0.088536 0.538111 0.027 Uiso 1 1 calc R . . . .
H24B H 0.381766 0.210514 0.529150 0.027 Uiso 1 1 calc R . . . .
C20 C 1.0915(3) 0.7947(3) 0.45351(18) 0.0283(6) Uani 1 1 d . . . . .
H20A H 1.124940 0.742987 0.478034 0.034 Uiso 1 1 calc R . . . .
H20B H 1.127996 0.791725 0.404949 0.034 Uiso 1 1 calc R . . . .
F1 F 0.9590(4) 0.3852(4) 0.4054(2) 0.1089(15) Uani 1 1 d . . . . .
C19 C 1.0930(3) 0.9098(3) 0.57300(18) 0.0291(6) Uani 1 1 d . . . . .
H19A H 1.131071 0.985108 0.605863 0.035 Uiso 1 1 calc R . . . .
H19B H 1.126208 0.859549 0.599103 0.035 Uiso 1 1 calc R . . . .
C30 C 0.8429(3) -0.0460(2) 0.23637(17) 0.0274(6) Uani 1 1 d . . . . .
F5 F 1.0377(5) -0.0944(4) 0.2869(2) 0.130(2) Uani 1 1 d . . . . .
F2 F 1.0377(4) 0.5381(3) 0.3775(3) 0.1247(19) Uani 1 1 d . . . . .
C29 C 0.9581(4) -0.1059(3) 0.2235(2) 0.0339(7) Uani 1 1 d . . . . .
O5 O 0.8589(4) 0.4447(7) 0.2357(3) 0.156(3) Uani 1 1 d . . . . .
C34 C 0.3917(4) -0.0833(4) 0.2166(2) 0.0472(9) Uani 1 1 d . . . . .
H34A H 0.379973 -0.041985 0.178797 0.071 Uiso 1 1 calc GR . . . .
H34B H 0.300418 -0.127419 0.221266 0.071 Uiso 1 1 calc GR . . . .
H34C H 0.450638 -0.131481 0.200302 0.071 Uiso 1 1 calc GR . . . .
C32 C 0.9766(4) 0.4304(4) 0.3493(2) 0.0443(9) Uani 1 1 d . . . . .
C31 C 0.8407(4) 0.4102(4) 0.2945(3) 0.0538(11) Uani 1 1 d . . . . .
C33 C 1.1711(4) 0.6016(4) 0.2215(2) 0.0494(10) Uani 1 1 d . . . . .
H33A H 1.240917 0.637847 0.194866 0.074 Uiso 1 1 calc GR . . . .
H33B H 1.210929 0.556262 0.248695 0.074 Uiso 1 1 calc GR . . . .
H33C H 1.143156 0.656894 0.257824 0.074 Uiso 1 1 calc GR . . . .
H10 H 0.544(4) 0.036(3) 0.275(2) 0.027(9) 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
O3 C12 1.246(3) . ?
O2 C26 1.243(3) . ?
O1 C1 1.427(4) . ?
O1 C4 1.425(4) . ?
O4 C20 1.431(4) . ?
O4 C19 1.430(4) . ?
N9 H9 0.8800 . ?
N9 C15 1.374(3) . ?
N9 C16 1.361(3) . ?
N11 C15 1.320(3) . ?
N11 C17 1.357(3) . ?
N1 H1 0.8800 . ?
N1 C7 1.374(3) . ?
N1 C6 1.361(3) . ?
O8 C30 1.234(4) . ?
N5 H5 0.8800 . ?
N5 N6 1.383(3) . ?
N5 C6 1.335(3) . ?
N8 H8 0.8800 . ?
N8 C15 1.326(3) . ?
N8 C14 1.462(3) . ?
N2 C6 1.322(3) . ?
N2 C5 1.353(3) . ?
N3 C7 1.322(3) . ?
N3 C5 1.358(3) . ?
O9 H9C 0.8400 . ?
O9 C33 1.458(5) . ?
N10 C17 1.354(4) . ?
N10 C16 1.315(3) . ?
O6 C31 1.215(5) . ?
N14 N13 1.382(3) . ?
N14 C22 1.276(4) . ?
N16 H16 0.8800 . ?
N16 C7 1.323(3) . ?
N16 C28 1.460(3) . ?
F6 C29 1.322(4) . ?
N6 C8 1.270(4) . ?
N15 H15 0.8800 . ?
N15 C26 1.331(4) . ?
N15 C25 1.450(4) . ?
N13 H13 0.8800 . ?
N13 C16 1.336(4) . ?
N7 H7 0.8800 . ?
N7 C12 1.324(4) . ?
N7 C11 1.456(4) . ?
N12 C17 1.341(3) . ?
N12 C18 1.463(4) . ?
N12 C21 1.467(4) . ?
O7 C30 1.232(4) . ?
N4 C5 1.341(3) . ?
N4 C2 1.469(3) . ?
N4 C3 1.462(4) . ?
F3 C32 1.331(5) . ?
C12 C13 1.513(4) . ?
O11 H11C 0.8701 . ?
O11 H11D 0.8698 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.519(4) . ?
F4 C29 1.321(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.522(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.520(4) . ?
C26 C27 1.512(4) . ?
C8 H8A 0.9500 . ?
C8 C9 1.493(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C27 1.516(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.494(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.518(4) . ?
O10 C34 1.371(5) . ?
O10 H10 1.03(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C24 1.531(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.526(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.527(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.518(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C20 1.509(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
F1 C32 1.299(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C30 C29 1.550(5) . ?
F5 C29 1.296(5) . ?
F2 C32 1.346(6) . ?
O5 C31 1.266(6) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C32 C31 1.538(6) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 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
C4 O1 C1 109.7(2) . . ?
C19 O4 C20 110.7(2) . . ?
C15 N9 H9 120.9 . . ?
C16 N9 H9 120.9 . . ?
C16 N9 C15 118.2(2) . . ?
C15 N11 C17 115.4(2) . . ?
C7 N1 H1 120.7 . . ?
C6 N1 H1 120.7 . . ?
C6 N1 C7 118.7(2) . . ?
N6 N5 H5 121.5 . . ?
C6 N5 H5 121.5 . . ?
C6 N5 N6 116.9(2) . . ?
C15 N8 H8 118.3 . . ?
C15 N8 C14 123.4(2) . . ?
C14 N8 H8 118.3 . . ?
C6 N2 C5 115.1(2) . . ?
C7 N3 C5 115.7(2) . . ?
C33 O9 H9C 109.5 . . ?
C16 N10 C17 115.0(2) . . ?
C22 N14 N13 116.2(2) . . ?
C7 N16 H16 118.1 . . ?
C7 N16 C28 123.9(2) . . ?
C28 N16 H16 118.1 . . ?
C8 N6 N5 116.5(2) . . ?
C26 N15 H15 118.6 . . ?
C26 N15 C25 122.9(2) . . ?
C25 N15 H15 118.6 . . ?
N14 N13 H13 121.1 . . ?
C16 N13 N14 117.9(2) . . ?
C16 N13 H13 121.1 . . ?
C12 N7 H7 118.5 . . ?
C12 N7 C11 123.0(2) . . ?
C11 N7 H7 118.5 . . ?
C17 N12 C18 123.5(2) . . ?
C17 N12 C21 122.8(2) . . ?
C18 N12 C21 113.7(2) . . ?
C5 N4 C2 122.9(2) . . ?
C5 N4 C3 122.5(2) . . ?
C3 N4 C2 113.9(2) . . ?
N3 C7 N1 121.5(2) . . ?
N3 C7 N16 122.3(2) . . ?
N16 C7 N1 116.2(2) . . ?
N11 C15 N9 121.9(2) . . ?
N11 C15 N8 121.7(2) . . ?
N8 C15 N9 116.4(2) . . ?
N5 C6 N1 117.2(2) . . ?
N2 C6 N1 122.5(2) . . ?
N2 C6 N5 120.3(2) . . ?
O3 C12 N7 123.2(2) . . ?
O3 C12 C13 122.3(2) . . ?
N7 C12 C13 114.5(2) . . ?
N10 C17 N11 126.2(2) . . ?
N12 C17 N11 116.8(2) . . ?
N12 C17 N10 117.0(2) . . ?
N10 C16 N9 123.0(2) . . ?
N10 C16 N13 119.1(2) . . ?
N13 C16 N9 117.9(2) . . ?
H11C O11 H11D 104.5 . . ?
N2 C5 N3 126.3(2) . . ?
N4 C5 N2 117.2(2) . . ?
N4 C5 N3 116.5(2) . . ?
N8 C14 H14A 108.5 . . ?
N8 C14 H14B 108.5 . . ?
N8 C14 C13 115.0(2) . . ?
H14A C14 H14B 107.5 . . ?
C13 C14 H14A 108.5 . . ?
C13 C14 H14B 108.5 . . ?
N7 C11 H11A 109.3 . . ?
N7 C11 H11B 109.3 . . ?
N7 C11 C10 111.5(2) . . ?
H11A C11 H11B 108.0 . . ?
C10 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
C12 C13 C14 115.9(2) . . ?
C12 C13 H13A 108.3 . . ?
C12 C13 H13B 108.3 . . ?
C14 C13 H13A 108.3 . . ?
C14 C13 H13B 108.3 . . ?
H13A C13 H13B 107.4 . . ?
N4 C2 H2A 109.7 . . ?
N4 C2 H2B 109.7 . . ?
N4 C2 C1 109.8(2) . . ?
H2A C2 H2B 108.2 . . ?
C1 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
O2 C26 N15 123.0(3) . . ?
O2 C26 C27 121.5(3) . . ?
N15 C26 C27 115.4(2) . . ?
N6 C8 H8A 120.0 . . ?
N6 C8 C9 120.0(2) . . ?
C9 C8 H8A 120.0 . . ?
N16 C28 H28A 108.8 . . ?
N16 C28 H28B 108.8 . . ?
N16 C28 C27 114.0(2) . . ?
H28A C28 H28B 107.6 . . ?
C27 C28 H28A 108.8 . . ?
C27 C28 H28B 108.8 . . ?
N14 C22 H22 119.8 . . ?
N14 C22 C23 120.4(3) . . ?
C23 C22 H22 119.8 . . ?
N12 C18 H18A 110.0 . . ?
N12 C18 H18B 110.0 . . ?
N12 C18 C19 108.5(2) . . ?
H18A C18 H18B 108.4 . . ?
C19 C18 H18A 110.0 . . ?
C19 C18 H18B 110.0 . . ?
C34 O10 H10 105(2) . . ?
O1 C1 C2 111.2(2) . . ?
O1 C1 H1A 109.4 . . ?
O1 C1 H1B 109.4 . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
N15 C25 H25A 109.4 . . ?
N15 C25 H25B 109.4 . . ?
N15 C25 C24 111.0(2) . . ?
H25A C25 H25B 108.0 . . ?
C24 C25 H25A 109.4 . . ?
C24 C25 H25B 109.4 . . ?
C22 C23 H23A 108.6 . . ?
C22 C23 H23B 108.6 . . ?
C22 C23 C24 114.6(2) . . ?
H23A C23 H23B 107.6 . . ?
C24 C23 H23A 108.6 . . ?
C24 C23 H23B 108.6 . . ?
C8 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C8 C9 C10 114.7(2) . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C26 C27 C28 113.7(2) . . ?
C26 C27 H27A 108.8 . . ?
C26 C27 H27B 108.8 . . ?
C28 C27 H27A 108.8 . . ?
C28 C27 H27B 108.8 . . ?
H27A C27 H27B 107.7 . . ?
C11 C10 C9 113.0(2) . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
O1 C4 H4A 109.3 . . ?
O1 C4 H4B 109.3 . . ?
O1 C4 C3 111.4(2) . . ?
H4A C4 H4B 108.0 . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
N12 C21 H21A 109.8 . . ?
N12 C21 H21B 109.8 . . ?
N12 C21 C20 109.2(2) . . ?
H21A C21 H21B 108.3 . . ?
C20 C21 H21A 109.8 . . ?
C20 C21 H21B 109.8 . . ?
N4 C3 C4 109.1(2) . . ?
N4 C3 H3A 109.9 . . ?
N4 C3 H3B 109.9 . . ?
C4 C3 H3A 109.9 . . ?
C4 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
C25 C24 H24A 108.8 . . ?
C25 C24 H24B 108.8 . . ?
C23 C24 C25 113.6(2) . . ?
C23 C24 H24A 108.8 . . ?
C23 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
O4 C20 C21 111.2(2) . . ?
O4 C20 H20A 109.4 . . ?
O4 C20 H20B 109.4 . . ?
C21 C20 H20A 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
O4 C19 C18 111.6(3) . . ?
O4 C19 H19A 109.3 . . ?
O4 C19 H19B 109.3 . . ?
C18 C19 H19A 109.3 . . ?
C18 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
O8 C30 C29 114.4(3) . . ?
O7 C30 O8 129.9(3) . . ?
O7 C30 C29 115.7(3) . . ?
F6 C29 C30 113.9(3) . . ?
F4 C29 F6 103.9(3) . . ?
F4 C29 C30 112.2(3) . . ?
F5 C29 F6 108.5(4) . . ?
F5 C29 F4 106.4(4) . . ?
F5 C29 C30 111.4(3) . . ?
O10 C34 H34A 109.5 . . ?
O10 C34 H34B 109.5 . . ?
O10 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
F3 C32 F2 102.0(4) . . ?
F3 C32 C31 110.8(3) . . ?
F1 C32 F3 110.3(4) . . ?
F1 C32 F2 108.9(5) . . ?
F1 C32 C31 113.2(4) . . ?
F2 C32 C31 111.1(4) . . ?
O6 C31 O5 128.8(4) . . ?
O6 C31 C32 117.6(4) . . ?
O5 C31 C32 113.5(4) . . ?
O9 C33 H33A 109.5 . . ?
O9 C33 H33B 109.5 . . ?
O9 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N9 H9 O2 0.88 2.01 2.789(3) 147.1 . yes
N1 H1 O3 0.88 2.13 2.877(3) 142.7 . yes
N5 H5 O9 0.88 1.95 2.814(3) 167.1 1_556 yes
N8 H8 O2 0.88 2.03 2.828(3) 149.7 . yes
O9 H9C O5 0.84 1.74 2.581(5) 174.8 . yes
N16 H16 O3 0.88 1.98 2.771(3) 148.9 . yes
N15 H15 O7 0.88 2.16 2.989(3) 157.2 2_656 yes
N13 H13 O6 0.88 1.89 2.764(3) 169.6 . yes
N13 H13 F1 0.88 2.64 3.194(4) 122.1 . yes
N7 H7 O8 0.88 1.97 2.842(3) 171.8 2_766 yes
C11 H11B N6 0.99 2.55 3.130(4) 117.0 . yes
C13 H13A N11 0.99 2.56 3.140(4) 117.4 . yes
C2 H2A O3 0.99 2.66 3.547(3) 149.3 2_667 yes
C8 H8A O9 0.95 2.60 3.368(4) 138.0 1_556 yes
C28 H28A O5 0.99 2.58 3.083(5) 111.4 2_666 yes
C28 H28B N2 0.99 2.62 3.485(3) 146.0 2_667 yes
C18 H18B O4 0.99 2.53 3.507(4) 169.4 2_776 yes
C1 H1A O1 0.99 2.64 3.436(4) 137.3 2_657 yes
C1 H1B O11 0.99 2.60 3.527(5) 155.9 1_556 yes
C25 H25A O10 0.99 2.61 3.406(5) 137.5 2_656 yes
C25 H25B N14 0.99 2.58 3.149(4) 116.4 . yes
C23 H23B O10 0.99 2.60 3.331(4) 130.6 . yes
C9 H9B F4 0.99 2.52 3.259(4) 130.8 1_566 yes
C27 H27A N3 0.99 2.62 3.182(4) 116.3 . yes
C27 H27A O7 0.99 2.53 3.243(4) 128.6 2_656 yes
C21 H21B F2 0.99 2.59 3.304(5) 129.0 . yes
O10 H10 O11 1.03(4) 1.74(4) 2.732(5) 159(3) . yes

_olex2_submission_special_instructions 'No special instructions were received'
