# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

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

data_lnl294
_database_code_depnum_ccdc_archive 'CCDC 1831850'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-05-18 downloaded from the CCDC.
;
_audit_creation_date             2017-10-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H12 F12 N4'
_chemical_formula_sum            'C22 H12 F12 N4'
_chemical_formula_weight         560.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c22 h12 n12 o4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   15.8769(2)
_cell_length_b                   17.4704(2)
_cell_length_c                   16.9020(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.4090(10)
_cell_angle_gamma                90
_cell_volume                     4595.57(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    15921
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.8250
_cell_measurement_theta_min      3.7900
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.520
_exptl_absorpt_coefficient_mu    1.506
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.18b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            33093
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.952
_diffrn_reflns_theta_min         3.677
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -107.00 -35.00   1.00    1.00    --  -17.77-178.00 -60.00   72
  2  ω    -92.00   3.00   1.00    1.00    --  -17.77 -38.00 120.00   95
  3  ω    -91.00 -36.00   1.00    1.00    --  -17.77 178.00 120.00   55
  4  ω    -91.00   4.00   1.00    1.00    --  -17.77 -57.00  60.00   95
  5  ω    -15.00  31.00   1.00    1.00    --   17.77  77.00 -60.00   46
  6  ω     62.00 104.00   1.00    1.00    --   17.77 178.00  30.00   42
  7  ω     15.00  63.00   1.00    1.00    --   17.77  77.00   0.00   48
  8  ω     39.00  94.00   1.00    1.00    --   17.77  77.00 -60.00   55
  9  ω    113.00 146.00   1.00   30.00    --  101.41 125.00 -60.00   33
 10  ω     25.00  76.00   1.00   30.00    --  101.41 -30.00 150.00   51
 11  ω     30.00 109.00   1.00   30.00    --  101.41 -94.00  60.00   79
 12  ω     59.00 120.00   1.00   30.00    --  101.41 -77.00 120.00   61
 13  ω     77.00 173.00   1.00   30.00    --  101.41  45.00  60.00   96
 14  ω     35.00 123.00   1.00   30.00    --  101.41 -45.00  30.00   88
 15  ω     72.00 104.00   1.00   30.00    --  101.41 -94.00 -30.00   32
 16  ω     95.00 173.00   1.00   30.00    --  101.41  45.00-180.00   78
 17  ω     30.00 114.00   1.00   30.00    --  101.41 -61.00 -90.00   84
 18  ω    112.00 139.00   1.00   30.00    --  101.41 125.00  60.00   27
 19  ω     28.00 121.00   1.00   30.00    --  101.41-125.00 -60.00   93
 20  ω     60.00 178.00   1.00   30.00    --  101.41  15.00 -30.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0486199000
_diffrn_orient_matrix_UB_12      -0.0583737000
_diffrn_orient_matrix_UB_13      -0.0425209000
_diffrn_orient_matrix_UB_21      -0.0266056000
_diffrn_orient_matrix_UB_22      -0.0646701000
_diffrn_orient_matrix_UB_23      0.0519936000
_diffrn_orient_matrix_UB_31      -0.0819969000
_diffrn_orient_matrix_UB_32      -0.0136570000
_diffrn_orient_matrix_UB_33      -0.0643337000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7519
_reflns_number_total             8752
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     850
_refine_ls_number_reflns         8752
_refine_ls_number_restraints     261
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0815
_refine_ls_restrained_S_all      1.093
_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)+(0.1655P)²+1.8508P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2315
_refine_ls_wR_factor_ref         0.2431
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F26) = Uanis(F22)
Uanis(F19) = Uanis(F18)
Uanis(F27) = Uanis(F24)
Uanis(F25) = Uanis(F22)
3. Rigid body (RIGU) restrains
 F40, F41, F42, C43, F43, F44, F45
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F35, F34, F36, C44, F39, F38, F37
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F24, F23, C36, F22, F26, F25, F27
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F29, F30, F28, C35, F31, F32, F33
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F17, F18, F16, C22, F21, F20, F19
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F11, F10, C21, F12, F14, F15, F13
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F4, C14, F5, F6, F7, F9, F8
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: F4(0.8) F5(0.8) F6(0.8) F7(0.2) F8(0.2) F9(0.2) F10(0.8) F11(0.8)
 F12(0.8) F13(0.2) F14(0.2) F15(0.2) F16(0.8) F17(0.8) F18(0.8) F19(0.2)
 F20(0.2) F21(0.2) F22(0.8) F23(0.8) F24(0.8) F25(0.2) F26(0.2) F27(0.2)
 F28(0.8) F29(0.8) F30(0.8) F31(0.2) F32(0.2) F33(0.2) F34(0.8) F35(0.8)
 F36(0.8) F37(0.2) F38(0.2) F39(0.2) F40(0.8) F41(0.8) F42(0.8) F43(0.2)
 F44(0.2) F45(0.2)
5.a Riding coordinates:
 N3(H3), N8(H8)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C5(H5), C8(H8A), C10(H10), C12(H12), C16(H16), C18(H18),
 C20(H20), N6(H6), C24(H24), C27(H27), C30(H30), C32(H32), C34(H34), C38(H38),
 C40(H40), C42(H42)
5.c X=CH2 refined with riding coordinates:
 N4(H4A,H4B), N7(H7A,H7B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.93435(14) 0.3277(2) 0.72563(12) 0.1182(11) Uani 1 1 d . . . . .
F2 F 1.06211(16) 0.36223(12) 0.73602(10) 0.0830(6) Uani 1 1 d . . . . .
F3 F 1.03653(17) 0.24743(11) 0.75779(10) 0.0842(6) Uani 1 1 d . . . . .
F4 F 1.0080(4) 0.06832(14) 0.54546(17) 0.0975(11) Uani 0.8 1 d . U P A 1
F5 F 1.0424(5) 0.10499(19) 0.4383(4) 0.144(2) Uani 0.8 1 d . U P A 1
F6 F 0.9129(3) 0.0996(2) 0.4497(4) 0.146(2) Uani 0.8 1 d . U P A 1
F7 F 1.0647(7) 0.0807(7) 0.5021(12) 0.097(4) Uani 0.2 1 d . U P A 2
F8 F 0.9672(13) 0.1120(5) 0.4046(6) 0.082(3) Uani 0.2 1 d . U P A 2
F9 F 0.9392(11) 0.0729(6) 0.5057(11) 0.084(4) Uani 0.2 1 d . U P A 2
F10 F 0.7255(4) 0.0759(4) 0.4056(3) 0.1322(18) Uani 0.8 1 d . U P B .
F11 F 0.7794(3) 0.0718(2) 0.3017(3) 0.1193(13) Uani 0.8 1 d . U P B 1
F12 F 0.6456(5) 0.0463(3) 0.2908(5) 0.185(4) Uani 0.8 1 d . U P B 1
F13 F 0.7541(17) 0.0841(16) 0.3853(14) 0.131(6) Uani 0.2 1 d . U P B 2
F14 F 0.7224(18) 0.0643(11) 0.2642(13) 0.127(6) Uani 0.2 1 d . U P B 2
F15 F 0.6366(16) 0.0588(11) 0.3386(14) 0.121(5) Uani 0.2 1 d . U P B 2
F16 F 0.5226(2) 0.3696(4) 0.3899(3) 0.1405(17) Uani 0.8 1 d . U P C 1
F17 F 0.4526(3) 0.3350(5) 0.2757(3) 0.150(3) Uani 0.8 1 d . U P C 1
F18 F 0.4668(3) 0.2645(4) 0.3812(4) 0.147(2) Uani 0.8 1 d . U P C 1
F19 F 0.5007(12) 0.307(2) 0.4000(15) 0.147(2) Uani 0.2 1 d . U P C 2
F20 F 0.4845(12) 0.3699(16) 0.300(2) 0.154(11) Uani 0.2 1 d . U P C 2
F21 F 0.4433(10) 0.2552(17) 0.309(2) 0.194(9) Uani 0.2 1 d . U P C 2
N1 N 1.00779(12) 0.39356(11) 0.43370(11) 0.0401(4) Uani 1 1 d . . . . .
H1 H 1.044056 0.429495 0.450160 0.048 Uiso 1 1 calc R . . . .
N2 N 0.75953(13) 0.34888(13) 0.22116(12) 0.0497(5) Uani 1 1 d . . . . .
N3 N 1.07236(13) 0.47830(12) 0.33049(13) 0.0494(5) Uani 1 1 d . . . . .
H3 H 1.096546 0.507683 0.300795 0.059 Uiso 1 1 d R . . . .
N4 N 0.82641(17) 0.42997(15) 0.11902(13) 0.0608(6) Uani 1 1 d . . . . .
H4A H 0.844865 0.457139 0.083568 0.073 Uiso 1 1 calc R . . . .
H4B H 0.778233 0.406153 0.106188 0.073 Uiso 1 1 calc R . . . .
C1 C 0.96068(13) 0.39851(11) 0.35726(12) 0.0339(4) Uani 1 1 d . . . . .
C2 C 0.88348(13) 0.36383(12) 0.33105(12) 0.0365(4) Uani 1 1 d . . . . .
H2 H 0.861257 0.332229 0.366190 0.044 Uiso 1 1 calc R . . . .
C3 C 0.83550(13) 0.37479(12) 0.25053(12) 0.0377(4) Uani 1 1 d . . . . .
C4 C 0.87310(15) 0.42471(12) 0.19488(13) 0.0408(5) Uani 1 1 d . . . . .
C5 C 0.94949(15) 0.45976(12) 0.22132(13) 0.0421(5) Uani 1 1 d . . . . .
H5 H 0.971151 0.491967 0.186330 0.051 Uiso 1 1 calc R . . . .
C6 C 0.99811(13) 0.44887(11) 0.30147(12) 0.0358(4) Uani 1 1 d . . . . .
C7 C 1.00098(13) 0.33321(12) 0.48774(12) 0.0351(4) Uani 1 1 d . . . . .
C8 C 1.00434(13) 0.34868(12) 0.56852(12) 0.0371(4) Uani 1 1 d . . . . .
H8A H 1.007242 0.398986 0.586860 0.045 Uiso 1 1 calc R . . . .
C9 C 1.00336(13) 0.28840(13) 0.62221(12) 0.0379(4) Uani 1 1 d . . . . .
C10 C 0.99743(15) 0.21348(13) 0.59606(13) 0.0426(5) Uani 1 1 d . . . . .
H10 H 0.995617 0.173565 0.632098 0.051 Uiso 1 1 calc R . . . .
C11 C 0.99423(15) 0.19897(12) 0.51507(14) 0.0426(5) Uani 1 1 d . . . . .
C12 C 0.99605(15) 0.25769(13) 0.46068(13) 0.0415(5) Uani 1 1 d . . . . .
H12 H 0.994010 0.246899 0.406450 0.050 Uiso 1 1 calc R . . . .
C13 C 1.00788(17) 0.30611(15) 0.70965(14) 0.0489(5) Uani 1 1 d . . . . .
C14 C 0.9906(2) 0.11806(15) 0.48541(18) 0.0590(6) Uani 1 1 d . U . . .
C15 C 0.71417(15) 0.29987(15) 0.26433(13) 0.0470(5) Uani 1 1 d . . . . .
C16 C 0.73715(18) 0.22404(17) 0.27913(16) 0.0559(6) Uani 1 1 d . . . . .
H16 H 0.788107 0.205661 0.267044 0.067 Uiso 1 1 calc R . . . .
C17 C 0.6844(2) 0.17573(19) 0.31185(17) 0.0632(7) Uani 1 1 d . . . . .
C18 C 0.60891(18) 0.2026(2) 0.33228(17) 0.0661(8) Uani 1 1 d . . . . .
H18 H 0.573726 0.170052 0.354818 0.079 Uiso 1 1 calc R . . . .
C19 C 0.58758(16) 0.2784(2) 0.31837(16) 0.0635(8) Uani 1 1 d . . . . .
C20 C 0.63847(16) 0.32700(18) 0.28374(15) 0.0544(6) Uani 1 1 d . . . . .
H20 H 0.622190 0.377729 0.273421 0.065 Uiso 1 1 calc R . . . .
C21 C 0.7064(3) 0.0933(2) 0.3259(3) 0.0906(11) Uani 1 1 d . U . . .
C22 C 0.5060(2) 0.3098(3) 0.3374(2) 0.0910(12) Uani 1 1 d . U . . .
F22 F 0.7892(3) 0.2731(3) 0.5161(4) 0.1472(17) Uani 0.8 1 d . U P D 1
F23 F 0.7253(2) 0.3707(3) 0.4727(2) 0.1213(14) Uani 0.8 1 d . U P D 1
F24 F 0.7850(2) 0.3683(3) 0.5945(2) 0.1299(17) Uani 0.8 1 d . U P D 1
F25 F 0.8042(10) 0.2881(12) 0.5877(16) 0.1472(17) Uani 0.2 1 d . U P D 2
F26 F 0.7470(11) 0.3122(14) 0.4723(17) 0.1472(17) Uani 0.2 1 d . U P D 2
F27 F 0.7536(10) 0.3961(15) 0.5664(11) 0.1299(17) Uani 0.2 1 d . U P D 2
F28 F 0.5995(3) 0.06714(18) 0.5950(3) 0.1088(13) Uani 0.8 1 d . U P E 1
F29 F 0.5287(3) 0.0894(2) 0.4773(2) 0.0972(12) Uani 0.8 1 d . U P E 1
F30 F 0.4662(3) 0.09184(19) 0.5751(3) 0.1095(12) Uani 0.8 1 d . U P E 1
F31 F 0.5266(14) 0.0823(8) 0.6173(8) 0.111(4) Uani 0.2 1 d . U P E 2
F32 F 0.6083(10) 0.0766(7) 0.5343(14) 0.114(5) Uani 0.2 1 d . U P E 2
F33 F 0.4854(13) 0.0983(11) 0.4978(12) 0.119(6) Uani 0.2 1 d . U P E 2
F34 F 0.3482(3) 0.1128(2) 0.4018(4) 0.1329(17) Uani 0.8 1 d . U P F 1
F35 F 0.2421(3) 0.08124(19) 0.3151(2) 0.0925(11) Uani 0.8 1 d . U P F 1
F36 F 0.2232(6) 0.1154(2) 0.4309(4) 0.152(3) Uani 0.8 1 d . U P F 1
F37 F 0.2961(16) 0.1235(9) 0.4498(9) 0.109(5) Uani 0.2 1 d . U P F 2
F38 F 0.298(3) 0.0813(14) 0.3440(17) 0.174(11) Uani 0.2 1 d . U P F 2
F39 F 0.1880(12) 0.0997(13) 0.368(2) 0.176(10) Uani 0.2 1 d . U P F 2
F40 F 0.1910(4) 0.3816(3) 0.1298(3) 0.1073(16) Uani 0.8 1 d . U P G 1
F41 F 0.2104(4) 0.2673(3) 0.10489(17) 0.1164(13) Uani 0.8 1 d . U P G 1
F42 F 0.3175(2) 0.3420(6) 0.1405(3) 0.153(3) Uani 0.8 1 d . U P G 1
F43 F 0.2910(15) 0.2757(8) 0.1235(9) 0.106(5) Uani 0.2 1 d . U P G 2
F44 F 0.2910(14) 0.3889(9) 0.1504(11) 0.105(6) Uani 0.2 1 d . U P G 2
F45 F 0.1799(8) 0.336(2) 0.1145(11) 0.154(10) Uani 0.2 1 d . U P G 2
N5 N 0.48000(14) 0.37069(14) 0.64693(13) 0.0559(5) Uani 1 1 d . . . . .
N6 N 0.23064(13) 0.40239(13) 0.43170(12) 0.0493(5) Uani 1 1 d . . . . .
H6 H 0.191189 0.435818 0.415709 0.059 Uiso 1 1 calc R . . . .
N7 N 0.41298(19) 0.45919(18) 0.74229(15) 0.0774(8) Uani 1 1 d . . . . .
H7A H 0.393598 0.487551 0.776247 0.093 Uiso 1 1 calc R . . . .
H7B H 0.463737 0.439974 0.754966 0.093 Uiso 1 1 calc R . . . .
N8 N 0.15642(13) 0.47576(12) 0.53634(13) 0.0505(5) Uani 1 1 d . . . . .
H8 H 0.129342 0.502220 0.566202 0.061 Uiso 1 1 d R . . . .
C23 C 0.40378(15) 0.39440(14) 0.61544(14) 0.0454(5) Uani 1 1 d . . . . .
C24 C 0.35701(14) 0.37986(14) 0.53512(14) 0.0434(5) Uani 1 1 d . . . . .
H24 H 0.381808 0.349489 0.500734 0.052 Uiso 1 1 calc R . . . .
C25 C 0.27720(14) 0.40950(13) 0.50809(13) 0.0401(5) Uani 1 1 d . . . . .
C26 C 0.23444(14) 0.45542(12) 0.56362(13) 0.0402(5) Uani 1 1 d . . . . .
C27 C 0.28337(17) 0.47190(14) 0.64278(15) 0.0494(6) Uani 1 1 d . . . . .
H27 H 0.258877 0.502347 0.677322 0.059 Uiso 1 1 calc R . . . .
C28 C 0.36348(17) 0.44475(15) 0.66868(14) 0.0500(5) Uani 1 1 d . . . . .
C29 C 0.52768(15) 0.32081(15) 0.60741(14) 0.0481(5) Uani 1 1 d . . . . .
C30 C 0.50561(15) 0.24387(15) 0.59456(15) 0.0492(5) Uani 1 1 d . . . . .
H30 H 0.454330 0.225555 0.606004 0.059 Uiso 1 1 calc R . . . .
C31 C 0.56037(15) 0.19495(15) 0.56471(14) 0.0475(5) Uani 1 1 d . . . . .
C32 C 0.63602(16) 0.22147(16) 0.54501(14) 0.0501(6) Uani 1 1 d . . . . .
H32 H 0.671876 0.188440 0.523885 0.060 Uiso 1 1 calc R . . . .
C33 C 0.65700(15) 0.29773(17) 0.55735(15) 0.0523(6) Uani 1 1 d . . . . .
C34 C 0.60409(17) 0.34728(16) 0.58877(16) 0.0539(6) Uani 1 1 d . . . . .
H34 H 0.619620 0.398376 0.597452 0.065 Uiso 1 1 calc R . . . .
C35 C 0.53926(19) 0.11182(17) 0.55362(18) 0.0597(6) Uani 1 1 d . U . . .
C36 C 0.7382(2) 0.3276(3) 0.5384(2) 0.0780(9) Uani 1 1 d . U . . .
C37 C 0.24208(14) 0.34445(14) 0.37675(13) 0.0431(5) Uani 1 1 d . . . . .
C38 C 0.23967(15) 0.36235(15) 0.29642(14) 0.0469(5) Uani 1 1 d . . . . .
H38 H 0.233870 0.412971 0.279182 0.056 Uiso 1 1 calc R . . . .
C39 C 0.24598(15) 0.30408(17) 0.24176(14) 0.0505(6) Uani 1 1 d . . . . .
C40 C 0.25543(16) 0.22890(17) 0.26624(16) 0.0528(6) Uani 1 1 d . . . . .
H40 H 0.260179 0.190334 0.229457 0.063 Uiso 1 1 calc R . . . .
C41 C 0.25774(16) 0.21168(15) 0.34675(16) 0.0512(6) Uani 1 1 d . . . . .
C42 C 0.25170(15) 0.26901(15) 0.40205(14) 0.0471(5) Uani 1 1 d . . . . .
H42 H 0.254104 0.256841 0.456014 0.056 Uiso 1 1 calc R . . . .
C43 C 0.2446(2) 0.3248(2) 0.15539(17) 0.0671(8) Uani 1 1 d . U . . .
C44 C 0.2658(3) 0.13088(19) 0.3751(2) 0.0747(8) Uani 1 1 d . U . . .


_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 C13 1.305(3) . ?
F2 C13 1.323(3) . ?
F3 C13 1.332(3) . ?
F10 F13 0.64(2) . ?
F10 F15 1.65(3) . ?
F10 C21 1.356(7) . ?
N1 H1 0.8600 . ?
N1 C1 1.362(3) . ?
N1 C7 1.413(3) . ?
N2 C3 1.292(3) . ?
N2 C15 1.411(3) . ?
N3 H3 0.8597 . ?
N3 C6 1.291(3) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 C4 1.351(3) . ?
C1 C2 1.360(3) . ?
C1 C6 1.496(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.435(3) . ?
C3 C4 1.491(3) . ?
C4 C5 1.353(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.433(3) . ?
C7 C8 1.382(3) . ?
C7 C12 1.394(3) . ?
C8 H8A 0.9300 . ?
C8 C9 1.392(3) . ?
C9 C10 1.379(3) . ?
C9 C13 1.498(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(3) . ?
C11 C12 1.382(3) . ?
C11 C14 1.497(3) . ?
C12 H12 0.9300 . ?
C15 C16 1.384(4) . ?
C15 C20 1.390(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.380(4) . ?
C17 C18 1.393(5) . ?
C17 C21 1.490(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.375(5) . ?
C19 C20 1.380(4) . ?
C19 C22 1.498(5) . ?
C20 H20 0.9300 . ?
N5 C23 1.290(3) . ?
N5 C29 1.407(3) . ?
N6 H6 0.8600 . ?
N6 C25 1.361(3) . ?
N6 C37 1.410(3) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N7 C28 1.357(3) . ?
N8 H8 0.8597 . ?
N8 C26 1.283(3) . ?
C23 C24 1.435(3) . ?
C23 C28 1.490(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.361(3) . ?
C25 C26 1.496(3) . ?
C26 C27 1.437(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.347(4) . ?
C29 C30 1.395(4) . ?
C29 C34 1.391(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.384(4) . ?
C31 C32 1.388(4) . ?
C31 C35 1.494(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.379(4) . ?
C33 C34 1.383(4) . ?
C33 C36 1.483(4) . ?
C34 H34 0.9300 . ?
C37 C38 1.386(3) . ?
C37 C42 1.385(4) . ?
C38 H38 0.9300 . ?
C38 C39 1.392(3) . ?
C39 C40 1.376(4) . ?
C39 C43 1.500(4) . ?
C40 H40 0.9300 . ?
C40 C41 1.387(4) . ?
C41 C42 1.386(3) . ?
C41 C44 1.488(4) . ?
C42 H42 0.9300 . ?

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
C21 F10 F15 50.7(7) . . ?
C1 N1 H1 117.9 . . ?
C1 N1 C7 124.25(17) . . ?
C7 N1 H1 117.9 . . ?
C3 N2 C15 123.2(2) . . ?
C6 N3 H3 119.7 . . ?
H4A N4 H4B 120.0 . . ?
C4 N4 H4A 120.0 . . ?
C4 N4 H4B 120.0 . . ?
N1 C1 C6 115.04(17) . . ?
C2 C1 N1 124.83(18) . . ?
C2 C1 C6 120.09(18) . . ?
C1 C2 H2 119.2 . . ?
C1 C2 C3 121.63(18) . . ?
C3 C2 H2 119.2 . . ?
N2 C3 C2 126.7(2) . . ?
N2 C3 C4 114.98(19) . . ?
C2 C3 C4 118.21(19) . . ?
N4 C4 C3 115.2(2) . . ?
N4 C4 C5 124.8(2) . . ?
C5 C4 C3 120.05(19) . . ?
C4 C5 H5 118.9 . . ?
C4 C5 C6 122.14(19) . . ?
C6 C5 H5 118.9 . . ?
N3 C6 C1 116.21(19) . . ?
N3 C6 C5 125.94(19) . . ?
C5 C6 C1 117.85(18) . . ?
C8 C7 N1 119.97(19) . . ?
C8 C7 C12 119.86(19) . . ?
C12 C7 N1 120.05(18) . . ?
C7 C8 H8A 120.2 . . ?
C7 C8 C9 119.51(19) . . ?
C9 C8 H8A 120.2 . . ?
C8 C9 C13 118.8(2) . . ?
C10 C9 C8 121.20(19) . . ?
C10 C9 C13 119.9(2) . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.5(2) . . ?
C11 C10 H10 120.7 . . ?
C10 C11 C14 119.7(2) . . ?
C12 C11 C10 121.4(2) . . ?
C12 C11 C14 118.9(2) . . ?
C7 C12 H12 120.3 . . ?
C11 C12 C7 119.5(2) . . ?
C11 C12 H12 120.3 . . ?
F1 C13 F2 105.4(3) . . ?
F1 C13 F3 107.9(2) . . ?
F1 C13 C9 113.2(2) . . ?
F2 C13 F3 104.1(2) . . ?
F2 C13 C9 112.7(2) . . ?
F3 C13 C9 112.8(2) . . ?
C16 C15 N2 122.1(2) . . ?
C16 C15 C20 119.5(2) . . ?
C20 C15 N2 117.9(2) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.9(3) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 120.9(3) . . ?
C16 C17 C21 120.9(3) . . ?
C18 C17 C21 118.2(3) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 C17 118.5(3) . . ?
C19 C18 H18 120.7 . . ?
C18 C19 C20 121.3(3) . . ?
C18 C19 C22 120.7(3) . . ?
C20 C19 C22 118.0(4) . . ?
C15 C20 H20 120.1 . . ?
C19 C20 C15 119.7(3) . . ?
C19 C20 H20 120.1 . . ?
F10 C21 F11 101.6(5) . . ?
F10 C21 C17 112.0(4) . . ?
C23 N5 C29 123.5(2) . . ?
C25 N6 H6 117.5 . . ?
C25 N6 C37 125.05(19) . . ?
C37 N6 H6 117.5 . . ?
H7A N7 H7B 120.0 . . ?
C28 N7 H7A 120.0 . . ?
C28 N7 H7B 120.0 . . ?
C26 N8 H8 119.8 . . ?
N5 C23 C24 126.9(2) . . ?
N5 C23 C28 114.8(2) . . ?
C24 C23 C28 118.2(2) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 C23 121.5(2) . . ?
C25 C24 H24 119.2 . . ?
N6 C25 C24 125.35(19) . . ?
N6 C25 C26 114.55(19) . . ?
C24 C25 C26 120.1(2) . . ?
N8 C26 C25 116.7(2) . . ?
N8 C26 C27 125.8(2) . . ?
C27 C26 C25 117.6(2) . . ?
C26 C27 H27 118.9 . . ?
C28 C27 C26 122.3(2) . . ?
C28 C27 H27 118.9 . . ?
N7 C28 C23 115.0(2) . . ?
C27 C28 N7 124.8(2) . . ?
C27 C28 C23 120.1(2) . . ?
C30 C29 N5 121.9(2) . . ?
C34 C29 N5 118.5(2) . . ?
C34 C29 C30 119.2(2) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 C29 119.7(2) . . ?
C31 C30 H30 120.2 . . ?
C30 C31 C32 121.2(2) . . ?
C30 C31 C35 120.3(2) . . ?
C32 C31 C35 118.5(2) . . ?
C31 C32 H32 120.6 . . ?
C33 C32 C31 118.7(2) . . ?
C33 C32 H32 120.6 . . ?
C32 C33 C34 121.0(2) . . ?
C32 C33 C36 120.1(3) . . ?
C34 C33 C36 118.8(3) . . ?
C29 C34 H34 119.9 . . ?
C33 C34 C29 120.1(3) . . ?
C33 C34 H34 119.9 . . ?
C38 C37 N6 120.1(2) . . ?
C42 C37 N6 120.0(2) . . ?
C42 C37 C38 119.8(2) . . ?
C37 C38 H38 120.2 . . ?
C37 C38 C39 119.6(2) . . ?
C39 C38 H38 120.2 . . ?
C38 C39 C43 118.7(3) . . ?
C40 C39 C38 121.1(2) . . ?
C40 C39 C43 120.2(2) . . ?
C39 C40 H40 120.6 . . ?
C39 C40 C41 118.8(2) . . ?
C41 C40 H40 120.6 . . ?
C40 C41 C44 120.4(3) . . ?
C42 C41 C40 120.8(3) . . ?
C42 C41 C44 118.8(3) . . ?
C37 C42 C41 119.8(2) . . ?
C37 C42 H42 120.1 . . ?
C41 C42 H42 120.1 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.687
_oxdiff_exptl_absorpt_empirical_full_min 0.429
####################################################################### 
# 
# 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_spo77
_database_code_depnum_ccdc_archive 'CCDC 1831851'
_audit_update_record             
;
2018-03-22 deposited with the CCDC.
2018-05-18 downloaded from the CCDC.
;
_audit_creation_date             2017-06-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H42 F2 N8 O8'
_chemical_formula_sum            'C34 H42 F2 N8 O8'
_chemical_formula_weight         728.75
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c34 h40 f2 n8 o8'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.0537(2)
_cell_length_b                   17.8869(4)
_cell_length_c                   22.6505(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.648(2)
_cell_angle_gamma                90
_cell_volume                     3664.16(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11633
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.5670
_cell_measurement_theta_min      4.6060
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.862
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.18b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            36478
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.155
_diffrn_reflns_theta_min         3.907
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -49.00   9.00   1.00    5.00    --  -17.77 -57.00-180.00   58
  2  ω   -105.00 -66.00   1.00    5.00    --  -17.77 178.00 -60.00   39
  3  ω    -55.00 -28.00   1.00    5.00    --  -17.77 -57.00 -60.00   27
  4  ω    -98.00 -38.00   1.00    5.00    --  -17.77 -19.00-180.00   60
  5  ω    -31.00   7.00   1.00    5.00    --  -17.77 -38.00 -60.00   38
  6  ω   -105.00 -35.00   1.00    5.00    --  -17.77 178.00-120.00   70
  7  ω    -78.00 -52.00   1.00    5.00    --  -17.77 -57.00 -90.00   26
  8  ω    -35.00  -9.00   1.00    5.00    --  -17.77 -57.00 120.00   26
  9  ω    -70.00 -44.00   1.00    5.00    --  -17.77 -38.00 -90.00   26
 10  ω    -22.00  18.00   1.00    5.00    --  -17.77 -19.00-180.00   40
 11  ω    -91.00   5.00   1.00    5.00    --  -17.77 -38.00  90.00   96
 12  ω     73.00  98.00   1.00    5.00    --   17.77  19.00  90.00   25
 13  ω     62.00  87.00   1.00    5.00    --   17.77-178.00  90.00   25
 14  ω     10.00  92.00   1.00    5.00    --   17.77  38.00   0.00   82
 15  ω     39.00  66.00   1.00    5.00    --   17.77  19.00  90.00   27
 16  ω     20.00  45.00   1.00    5.00    --   17.77  77.00 -60.00   25
 17  ω     70.00 153.00   1.00   30.00    --  101.41  77.00-150.00   83
 18  ω     76.00 102.00   1.00   30.00    --  101.41  45.00  30.00   26
 19  ω     72.00  98.00   1.00   30.00    --  101.41  61.00-120.00   26
 20  ω     76.00 102.00   1.00   30.00    --  101.41  45.00 -30.00   26
 21  ω    147.00 172.00   1.00   30.00    --  101.41  61.00 -90.00   25
 22  ω    126.00 157.00   1.00   30.00    --  101.41  77.00   0.00   31
 23  ω     69.00  96.00   1.00   30.00    --  101.41  77.00   0.00   27
 24  ω     72.00  98.00   1.00   30.00    --  101.41  61.00 -90.00   26
 25  ω     69.00  95.00   1.00   30.00    --  101.41  77.00-120.00   26
 26  ω     72.00  98.00   1.00   30.00    --  101.41  61.00 -30.00   26
 27  ω     46.00  72.00   1.00   30.00    --  101.41 -94.00-120.00   26
 28  ω     84.00 109.00   1.00   30.00    --  101.41 -94.00-120.00   25
 29  ω     72.00  98.00   1.00   30.00    --  101.41  61.00   0.00   26
 30  ω     77.00 102.00   1.00   30.00    --  101.41  45.00 -60.00   25
 31  ω     69.00  95.00   1.00   30.00    --  101.41  77.00 -60.00   26
 32  ω     74.00 108.00   1.00   30.00    --  101.41  30.00 -30.00   34
 33  ω     69.00  95.00   1.00   30.00    --  101.41  77.00 -90.00   26
 34  ω    144.00 170.00   1.00   30.00    --  101.41  61.00 -60.00   26
 35  ω    107.00 177.00   1.00   30.00    --  101.41  77.00 -30.00   70
 36  ω     73.00 100.00   1.00   30.00    --  101.41  61.00  30.00   27
 37  ω     74.00 177.00   1.00   30.00    --  101.41  30.00 -90.00  103
 38  ω     73.00 100.00   1.00   30.00    --  101.41  30.00 -60.00   27
 39  ω     73.00 100.00   1.00   30.00    --  101.41  30.00   0.00   27
 40  ω     77.00 102.00   1.00   30.00    --  101.41  45.00 -90.00   25
 41  ω     77.00 102.00   1.00   30.00    --  101.41  45.00   0.00   25
 42  ω     69.00 100.00   1.00   30.00    --  101.41  77.00 -30.00   31
 43  ω     72.00  98.00   1.00   30.00    --  101.41  61.00 -60.00   26
 44  ω     29.00 130.00   1.00   30.00    --  101.41 -61.00  60.00  101
 45  ω     70.00  95.00   1.00   30.00    --  101.41  77.00  30.00   25
 46  ω     51.00  94.00   1.00   30.00    --  101.41  15.00  30.00   43
 47  ω     25.00 134.00   1.00   30.00    --  101.41 -77.00-120.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0162381000
_diffrn_orient_matrix_UB_12      -0.0145407000
_diffrn_orient_matrix_UB_13      -0.0670322000
_diffrn_orient_matrix_UB_21      0.1674178000
_diffrn_orient_matrix_UB_22      0.0122273000
_diffrn_orient_matrix_UB_23      -0.0050707000
_diffrn_orient_matrix_UB_31      0.0271111000
_diffrn_orient_matrix_UB_32      -0.0839783000
_diffrn_orient_matrix_UB_33      0.0108557000
_diffrn_oxdiff_ac3_digest_frames 
;
0150175dc1f029244ab48b827e5605fcb00002821ea
;
_diffrn_oxdiff_ac3_digest_hkl    
;
0146668b883e479d37170ebbe83e397732f6f4
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5254
_reflns_number_total             7011
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.050
_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     478
_refine_ls_number_reflns         7011
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0727
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1125P)²+2.4762P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2032
_refine_ls_wR_factor_ref         0.2245
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C32-C35
 1.54 with sigma of 0.02
 C32-C33
 1.54 with sigma of 0.02
 C35-C36
 1.54 with sigma of 0.02
 C33-C34
 1.54 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C31 \\sim C32 \\sim C35: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C31 \\sim C32 \\sim C33: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C32 \\sim C35 \\sim C36: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04
C32 \\sim C33 \\sim C34: within 1.7A with sigma of 0.02 and sigma for terminal
atoms of 0.04
Uanis(C35) = Uanis(C33)
Uanis(C36) = Uanis(C34)
4. Others
 Fixed Sof: H32A(0.5) H32B(0.5) H32C(0.5) H32D(0.5) C33(0.5) H33A(0.5)
 H33B(0.5) C34(0.5) H34A(0.5) H34B(0.5) H34C(0.5) C35(0.5) H35A(0.5) H35B(0.5)
 C36(0.5) H36A(0.5) H36B(0.5) H36C(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,
 H17B), C18(H18A,H18B), C19(H19A,H19B), C27(H27A,H27B), C28(H28A,H28B),
 C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C32(H32C,H32D),
  C33(H33A,H33B), C35(H35A,H35B)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4), C3(H3), C6(H6), C9(H9), C12(H12), C22(H22), C25(H25)
5.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C34(H34A,H34B,H34C), C36(H36A,H36B,H36C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.1496(2) 0.44263(14) 0.82730(9) 0.0931(7) Uani 1 1 d . . . . .
F2 F 0.1775(2) 0.68303(15) 0.82061(9) 0.0959(7) Uani 1 1 d . . . . .
O1 O 0.2271(5) 0.3525(3) 0.91257(15) 0.1527(17) Uani 1 1 d . . . . .
O2 O 0.4082(4) 0.2798(2) 0.90486(13) 0.1132(11) Uani 1 1 d . . . . .
O3 O 0.6452(3) 0.25423(14) 0.72079(12) 0.0840(7) Uani 1 1 d . . . . .
O4 O 0.6763(2) 0.35853(15) 0.67568(9) 0.0721(6) Uani 1 1 d . . . . .
O5 O 0.3094(5) 0.76408(17) 0.90199(12) 0.1138(12) Uani 1 1 d . . . . .
O6 O 0.4535(3) 0.85117(18) 0.87376(11) 0.0917(9) Uani 1 1 d . . . . .
O7 O 0.6623(3) 0.84451(15) 0.68615(12) 0.0869(8) Uani 1 1 d . . . . .
O8 O 0.6615(3) 0.74073(16) 0.63985(12) 0.0899(8) Uani 1 1 d . . . . .
N1 N 0.3920(2) 0.40966(13) 0.64819(9) 0.0504(5) Uani 1 1 d . . . . .
N2 N 0.3209(2) 0.40252(13) 0.53496(9) 0.0505(5) Uani 1 1 d . . . . .
H2 H 0.337618 0.365718 0.558774 0.061 Uiso 1 1 calc R . . . .
N3 N 0.3871(3) 0.68049(14) 0.63323(9) 0.0544(6) Uani 1 1 d . . . . .
N4 N 0.3085(3) 0.66799(14) 0.52226(9) 0.0546(6) Uani 1 1 d . . . . .
H4 H 0.317627 0.708250 0.542866 0.065 Uiso 1 1 calc R . . . .
N5 N 0.3290(4) 0.3295(2) 0.88595(13) 0.0856(9) Uani 1 1 d . . . . .
N6 N 0.6093(3) 0.31854(15) 0.70901(10) 0.0565(6) Uani 1 1 d . . . . .
N7 N 0.3829(3) 0.79333(18) 0.86513(11) 0.0681(7) Uani 1 1 d . . . . .
N8 N 0.6134(3) 0.78228(15) 0.67648(11) 0.0589(6) Uani 1 1 d . . . . .
C1 C 0.3706(3) 0.47517(16) 0.62235(10) 0.0445(6) Uani 1 1 d . . . . .
C2 C 0.3347(2) 0.47023(15) 0.55674(10) 0.0435(6) Uani 1 1 d . . . . .
C3 C 0.3168(3) 0.53503(16) 0.52356(10) 0.0463(6) Uani 1 1 d . . . . .
H3 H 0.296509 0.531766 0.483018 0.056 Uiso 1 1 calc R . . . .
C4 C 0.3290(3) 0.60452(15) 0.55023(10) 0.0444(6) Uani 1 1 d . . . . .
C5 C 0.3670(3) 0.61128(16) 0.61534(10) 0.0455(6) Uani 1 1 d . . . . .
C6 C 0.3840(3) 0.54590(15) 0.64783(10) 0.0465(6) Uani 1 1 d . . . . .
H6 H 0.405346 0.549397 0.688299 0.056 Uiso 1 1 calc R . . . .
C7 C 0.3890(3) 0.40099(15) 0.70843(11) 0.0458(6) Uani 1 1 d . . . . .
C8 C 0.4838(3) 0.35028(15) 0.73873(11) 0.0475(6) Uani 1 1 d . . . . .
C9 C 0.4654(3) 0.32834(17) 0.79598(12) 0.0556(7) Uani 1 1 d . . . . .
H9 H 0.529043 0.293386 0.813833 0.067 Uiso 1 1 calc R . . . .
C10 C 0.3518(3) 0.35849(18) 0.82688(12) 0.0590(7) Uani 1 1 d . . . . .
C11 C 0.2605(3) 0.41139(19) 0.79925(13) 0.0583(7) Uani 1 1 d . . . . .
C12 C 0.2774(3) 0.43210(17) 0.74193(12) 0.0554(7) Uani 1 1 d . . . . .
H12 H 0.213821 0.467524 0.724687 0.066 Uiso 1 1 calc R . . . .
C13 C 0.2794(3) 0.38459(17) 0.47349(11) 0.0531(7) Uani 1 1 d . . . . .
H13A H 0.309731 0.333776 0.465241 0.064 Uiso 1 1 calc R . . . .
H13B H 0.331868 0.417708 0.447779 0.064 Uiso 1 1 calc R . . . .
C14 C 0.1129(3) 0.3921(2) 0.45952(14) 0.0675(9) Uani 1 1 d . . . . .
H14A H 0.062024 0.351137 0.477929 0.081 Uiso 1 1 calc R . . . .
H14B H 0.078189 0.438390 0.476338 0.081 Uiso 1 1 calc R . . . .
C15 C 0.0746(3) 0.3916(2) 0.39334(14) 0.0655(8) Uani 1 1 d . . . . .
H15A H 0.127048 0.350864 0.375378 0.079 Uiso 1 1 calc R . . . .
H15B H -0.030479 0.382257 0.387045 0.079 Uiso 1 1 calc R . . . .
C16 C 0.1117(6) 0.4620(3) 0.3635(2) 0.129(2) Uani 1 1 d . . . . .
H16A H 0.214451 0.473522 0.373762 0.155 Uiso 1 1 calc R . . . .
H16B H 0.052502 0.501582 0.379697 0.155 Uiso 1 1 calc R . . . .
C17 C 0.0909(5) 0.4647(4) 0.2976(2) 0.139(2) Uani 1 1 d . . . . .
H17A H 0.016610 0.428633 0.284344 0.167 Uiso 1 1 calc R . . . .
H17B H 0.057410 0.514081 0.285235 0.167 Uiso 1 1 calc R . . . .
C18 C 0.2307(7) 0.4478(4) 0.2714(3) 0.139(2) Uani 1 1 d . . . . .
H18A H 0.304460 0.481551 0.288768 0.167 Uiso 1 1 calc R . . . .
H18B H 0.259090 0.397606 0.283688 0.167 Uiso 1 1 calc R . . . .
C19 C 0.2400(10) 0.4515(4) 0.2092(3) 0.161(3) Uani 1 1 d . . . . .
H19A H 0.214846 0.502137 0.197047 0.193 Uiso 1 1 calc R . . . .
H19B H 0.164202 0.418955 0.191773 0.193 Uiso 1 1 calc R . . . .
C20 C 0.3796(8) 0.4322(5) 0.1831(3) 0.164(3) Uani 1 1 d . . . . .
H20A H 0.451056 0.470737 0.191899 0.246 Uiso 1 1 calc GR . . . .
H20B H 0.364229 0.427581 0.141032 0.246 Uiso 1 1 calc GR . . . .
H20C H 0.415203 0.385586 0.199211 0.246 Uiso 1 1 calc GR . . . .
C21 C 0.3948(3) 0.70098(15) 0.69139(11) 0.0481(6) Uani 1 1 d . . . . .
C22 C 0.2888(3) 0.67752(18) 0.73114(12) 0.0583(7) Uani 1 1 d . . . . .
H22 H 0.219569 0.641595 0.719070 0.070 Uiso 1 1 calc R . . . .
C23 C 0.2853(3) 0.70618(19) 0.78681(12) 0.0588(7) Uani 1 1 d . . . . .
C24 C 0.3852(3) 0.76006(17) 0.80677(11) 0.0550(7) Uani 1 1 d . . . . .
C25 C 0.4911(3) 0.78479(17) 0.76905(12) 0.0531(7) Uani 1 1 d . . . . .
H25 H 0.558824 0.821237 0.781529 0.064 Uiso 1 1 calc R . . . .
C26 C 0.4957(3) 0.75527(15) 0.71310(11) 0.0469(6) Uani 1 1 d . . . . .
C27 C 0.2714(4) 0.67653(18) 0.45908(11) 0.0609(8) Uani 1 1 d . . . . .
H27A H 0.174145 0.655747 0.449752 0.073 Uiso 1 1 calc R . . . .
H27B H 0.342538 0.649603 0.436409 0.073 Uiso 1 1 calc R . . . .
C28 C 0.2731(4) 0.7580(2) 0.44293(14) 0.0726(9) Uani 1 1 d . . . . .
H28A H 0.206600 0.784996 0.467681 0.087 Uiso 1 1 calc R . . . .
H28B H 0.237165 0.763803 0.402181 0.087 Uiso 1 1 calc R . . . .
C29 C 0.4283(5) 0.7922(2) 0.4504(2) 0.0924(12) Uani 1 1 d . . . . .
H29A H 0.470884 0.778198 0.488938 0.111 Uiso 1 1 calc R . . . .
H29B H 0.490004 0.770829 0.420835 0.111 Uiso 1 1 calc R . . . .
C30 C 0.4317(7) 0.8747(3) 0.4451(3) 0.1256(19) Uani 1 1 d . . . . .
H30A H 0.371846 0.896299 0.475146 0.151 Uiso 1 1 calc R . . . .
H30B H 0.388222 0.888939 0.406801 0.151 Uiso 1 1 calc R . . . .
C31 C 0.5887(9) 0.9068(4) 0.4518(4) 0.160(3) Uani 1 1 d . U . . .
H31A H 0.648883 0.883688 0.422556 0.192 Uiso 1 1 calc R . . . .
H31B H 0.584404 0.959966 0.443386 0.192 Uiso 1 1 calc R . . . .
C32 C 0.6638(10) 0.8956(5) 0.5125(5) 0.192(3) Uani 1 1 d D U . . .
H32A H 0.684161 0.843026 0.519580 0.230 Uiso 0.5 1 calc R . P A 1
H32B H 0.601457 0.913815 0.543107 0.230 Uiso 0.5 1 calc R . P A 1
H32C H 0.660708 0.842153 0.519619 0.230 Uiso 0.5 1 calc R . P B 2
H32D H 0.597824 0.917920 0.540096 0.230 Uiso 0.5 1 calc R . P B 2
C33 C 0.810(2) 0.9407(15) 0.5125(14) 0.205(6) Uani 0.5 1 d D U P C 1
H33A H 0.797616 0.981867 0.484786 0.246 Uiso 0.5 1 calc R . P C 1
H33B H 0.830041 0.961595 0.551483 0.246 Uiso 0.5 1 calc R . P C 1
C34 C 0.941(5) 0.892(2) 0.4953(18) 0.262(10) Uani 0.5 1 d D U P C 1
H34A H 0.918208 0.840587 0.500720 0.393 Uiso 0.5 1 calc GR . P C 1
H34B H 1.026809 0.905323 0.519944 0.393 Uiso 0.5 1 calc GR . P C 1
H34C H 0.961544 0.901299 0.454700 0.393 Uiso 0.5 1 calc GR . P C 1
C35 C 0.824(2) 0.9209(17) 0.5344(12) 0.205(6) Uani 0.5 1 d D U P C 2
H35A H 0.824749 0.971010 0.550901 0.246 Uiso 0.5 1 calc R . P C 2
H35B H 0.868675 0.886385 0.563059 0.246 Uiso 0.5 1 calc R . P C 2
C36 C 0.901(5) 0.918(3) 0.4737(15) 0.262(10) Uani 0.5 1 d D U P C 2
H36A H 0.924388 0.866867 0.464463 0.393 Uiso 0.5 1 calc GR . P C 2
H36B H 0.990880 0.946671 0.476359 0.393 Uiso 0.5 1 calc GR . P C 2
H36C H 0.836077 0.938032 0.443117 0.393 Uiso 0.5 1 calc GR . P C 2


_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 C11 1.335(3) . ?
C33a H33A 0.9700 . ?
C33a H33B 0.9700 . ?
C33a C34 1.537(19) . ?
C34a H34A 0.9600 . ?
C34a H34B 0.9600 . ?
C34a H34C 0.9600 . ?
C35b H35A 0.9700 . ?
C35b H35B 0.9700 . ?
C35b C36 1.573(19) . ?
C36b H36A 0.9600 . ?
C36b H36B 0.9600 . ?
C36b H36C 0.9600 . ?
F2 C23 1.334(3) . ?
O1 N5 1.199(4) . ?
O2 N5 1.207(4) . ?
O3 N6 1.222(3) . ?
O4 N6 1.221(3) . ?
O5 N7 1.210(4) . ?
O6 N7 1.227(4) . ?
O7 N8 1.214(3) . ?
O8 N8 1.210(3) . ?
N1 C1 1.320(4) . ?
N1 C7 1.375(3) . ?
N2 H2 0.8600 . ?
N2 C2 1.312(3) . ?
N2 C13 1.461(3) . ?
N3 C5 1.313(3) . ?
N3 C21 1.366(3) . ?
N4 H4 0.8600 . ?
N4 C4 1.309(3) . ?
N4 C27 1.463(3) . ?
N5 C10 1.458(4) . ?
N6 C8 1.461(3) . ?
N7 C24 1.451(4) . ?
N8 C26 1.462(4) . ?
C1 C2 1.509(3) . ?
C1 C6 1.394(4) . ?
C2 C3 1.387(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(4) . ?
C4 C5 1.504(3) . ?
C5 C6 1.386(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.406(4) . ?
C7 C12 1.406(4) . ?
C8 C9 1.372(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.380(4) . ?
C10 C11 1.387(5) . ?
C11 C12 1.366(4) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.532(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.523(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.475(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.498(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.454(8) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.418(9) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.461(9) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.410(4) . ?
C21 C26 1.406(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.363(4) . ?
C23 C24 1.383(4) . ?
C24 C25 1.386(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.375(4) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.503(5) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.534(6) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.481(6) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C31 1.534(9) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 C32 1.519(12) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 H32C 0.9700 . ?
C32 H32D 0.9700 . ?
C32 C33 1.546(17) . ?
C32 C35 1.579(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C7 122.1(2) . . ?
C2 N2 H2 117.4 . . ?
C34a C33a C32 112(3) . . ?
C36b C35b C32 99(2) . . ?
C2 N2 C13 125.2(2) . . ?
C13 N2 H2 117.4 . . ?
C5 N3 C21 123.4(2) . . ?
C4 N4 H4 117.1 . . ?
C34a C33a H33A 109.1 . . ?
H33Aa C33a H33B 107.9 . . ?
C34a C33a H33B 109.1 . . ?
C33a C34a H34A 109.5 . . ?
C33a C34a H34B 109.5 . . ?
C4 N4 C27 125.8(2) . . ?
C27 N4 H4 117.1 . . ?
O1 N5 O2 122.2(3) . . ?
O1 N5 C10 119.0(4) . . ?
O2 N5 C10 118.7(3) . . ?
O3 N6 C8 118.0(3) . . ?
O4 N6 O3 123.5(3) . . ?
O4 N6 C8 118.4(2) . . ?
O5 N7 O6 123.6(3) . . ?
O5 N7 C24 118.9(3) . . ?
O6 N7 C24 117.5(3) . . ?
O7 N8 C26 118.0(2) . . ?
O8 N8 O7 123.2(3) . . ?
O8 N8 C26 118.7(3) . . ?
H34Aa C34a H34B 109.5 . . ?
H34Aa C34a H34C 109.5 . . ?
H34Ba C34a H34C 109.5 . . ?
C33a C34a H34C 109.5 . . ?
C36b C35b H35A 112.0 . . ?
H35Ab C35b H35B 109.7 . . ?
C36b C35b H35B 112.0 . . ?
C35b C36b H36A 109.5 . . ?
H36Ab C36b H36B 109.5 . . ?
C35b C36b H36B 109.5 . . ?
C35b C36b H36C 109.5 . . ?
H36Ab C36b H36C 109.5 . . ?
H36Bb C36b H36C 109.5 . . ?
C33a C32 H32A 110.5 . . ?
H32Aa C32 H32B 108.7 . . ?
C33a C32 H32B 110.5 . . ?
C35b C32 H32C 105.3 . . ?
C35b C32 H32D 105.3 . . ?
H32Cb C32 H32D 106.0 . . ?
N1 C1 C2 113.9(2) . . ?
N1 C1 C6 127.9(2) . . ?
C6 C1 C2 118.2(2) . . ?
N2 C2 C1 115.9(2) . . ?
N2 C2 C3 124.1(2) . . ?
C3 C2 C1 119.9(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
N4 C4 C3 124.1(2) . . ?
N4 C4 C5 115.2(2) . . ?
C3 C4 C5 120.7(2) . . ?
N3 C5 C4 113.6(2) . . ?
N3 C5 C6 128.4(2) . . ?
C6 C5 C4 117.9(2) . . ?
C1 C6 H6 118.6 . . ?
C5 C6 C1 122.7(2) . . ?
C5 C6 H6 118.6 . . ?
N1 C7 C8 121.2(2) . . ?
N1 C7 C12 122.6(2) . . ?
C12 C7 C8 115.4(2) . . ?
C7 C8 N6 119.7(2) . . ?
C9 C8 N6 117.1(2) . . ?
C9 C8 C7 123.2(2) . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.6(3) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 N5 117.8(3) . . ?
C9 C10 C11 118.7(2) . . ?
C11 C10 N5 123.4(3) . . ?
F1 C11 C10 121.1(3) . . ?
F1 C11 C12 117.3(3) . . ?
C12 C11 C10 121.5(3) . . ?
C7 C12 H12 119.3 . . ?
C11 C12 C7 121.4(3) . . ?
C11 C12 H12 119.3 . . ?
N2 C13 H13A 109.1 . . ?
N2 C13 H13B 109.1 . . ?
N2 C13 C14 112.6(2) . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C13 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 C13 112.3(2) . . ?
C15 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C14 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 C14 113.6(3) . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C15 C16 H16A 107.9 . . ?
C15 C16 H16B 107.9 . . ?
C15 C16 C17 117.6(5) . . ?
H16A C16 H16B 107.2 . . ?
C17 C16 H16A 107.9 . . ?
C17 C16 H16B 107.9 . . ?
C16 C17 H17A 109.9 . . ?
C16 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
C18 C17 C16 109.1(5) . . ?
C18 C17 H17A 109.9 . . ?
C18 C17 H17B 109.9 . . ?
C17 C18 H18A 107.5 . . ?
C17 C18 H18B 107.5 . . ?
H18A C18 H18B 107.0 . . ?
C19 C18 C17 119.2(6) . . ?
C19 C18 H18A 107.5 . . ?
C19 C18 H18B 107.5 . . ?
C18 C19 H19A 107.6 . . ?
C18 C19 H19B 107.6 . . ?
C18 C19 C20 118.9(7) . . ?
H19A C19 H19B 107.0 . . ?
C20 C19 H19A 107.6 . . ?
C20 C19 H19B 107.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C21 C22 122.0(2) . . ?
N3 C21 C26 121.7(2) . . ?
C26 C21 C22 115.6(2) . . ?
C21 C22 H22 119.2 . . ?
C23 C22 C21 121.6(3) . . ?
C23 C22 H22 119.2 . . ?
F2 C23 C22 117.6(3) . . ?
F2 C23 C24 120.9(3) . . ?
C22 C23 C24 121.4(3) . . ?
C23 C24 N7 123.1(3) . . ?
C23 C24 C25 118.8(2) . . ?
C25 C24 N7 118.1(3) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 C24 119.8(3) . . ?
C26 C25 H25 120.1 . . ?
C21 C26 N8 120.6(2) . . ?
C25 C26 N8 116.7(2) . . ?
C25 C26 C21 122.7(2) . . ?
N4 C27 H27A 109.8 . . ?
N4 C27 H27B 109.8 . . ?
N4 C27 C28 109.6(2) . . ?
H27A C27 H27B 108.2 . . ?
C28 C27 H27A 109.8 . . ?
C28 C27 H27B 109.8 . . ?
C27 C28 H28A 109.2 . . ?
C27 C28 H28B 109.2 . . ?
C27 C28 C29 112.3(3) . . ?
H28A C28 H28B 107.9 . . ?
C29 C28 H28A 109.2 . . ?
C29 C28 H28B 109.2 . . ?
C28 C29 H29A 108.7 . . ?
C28 C29 H29B 108.7 . . ?
H29A C29 H29B 107.6 . . ?
C30 C29 C28 114.2(4) . . ?
C30 C29 H29A 108.7 . . ?
C30 C29 H29B 108.7 . . ?
C29 C30 H30A 109.0 . . ?
C29 C30 H30B 109.0 . . ?
C29 C30 C31 112.8(5) . . ?
H30A C30 H30B 107.8 . . ?
C31 C30 H30A 109.0 . . ?
C31 C30 H30B 109.0 . . ?
C30 C31 H31A 108.6 . . ?
C30 C31 H31B 108.6 . . ?
H31A C31 H31B 107.6 . . ?
C32 C33a H33A 109.1 . . ?
C32 C31 C30 114.5(6) . . ?
C32 C31 H31A 108.6 . . ?
C32 C31 H31B 108.6 . . ?
C31 C32 H32A 110.5 . . ?
C31 C32 H32B 110.5 . . ?
C31 C32 H32C 105.3 . . ?
C31 C32 H32D 105.3 . . ?
C31 C32 C33 106.1(14) . . ?
C31 C32 C35 127.8(13) . . ?
C32 C33a H33B 109.1 . . ?
C32 C35b H35A 112.0 . . ?
C32 C35b H35B 112.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C11 C12 C7 -178.6(3) . . . . ?
F2 C23 C24 N7 1.6(5) . . . . ?
F2 C23 C24 C25 -177.1(3) . . . . ?
O1 N5 C10 C9 -176.8(4) . . . . ?
O1 N5 C10 C11 -0.5(6) . . . . ?
O2 N5 C10 C9 -1.2(5) . . . . ?
O2 N5 C10 C11 175.0(4) . . . . ?
O3 N6 C8 C7 -145.5(3) . . . . ?
O3 N6 C8 C9 34.6(4) . . . . ?
O4 N6 C8 C7 37.5(4) . . . . ?
O4 N6 C8 C9 -142.4(3) . . . . ?
O5 N7 C24 C23 13.9(5) . . . . ?
O5 N7 C24 C25 -167.4(3) . . . . ?
O6 N7 C24 C23 -164.3(3) . . . . ?
O6 N7 C24 C25 14.4(4) . . . . ?
O7 N8 C26 C21 153.9(3) . . . . ?
O7 N8 C26 C25 -26.9(4) . . . . ?
O8 N8 C26 C21 -29.1(4) . . . . ?
O8 N8 C26 C25 150.1(3) . . . . ?
N1 C1 C2 N2 3.9(3) . . . . ?
N1 C1 C2 C3 -176.8(2) . . . . ?
N1 C1 C6 C5 176.1(2) . . . . ?
N1 C7 C8 N6 13.8(4) . . . . ?
N1 C7 C8 C9 -166.3(3) . . . . ?
N1 C7 C12 C11 167.4(3) . . . . ?
N2 C2 C3 C4 178.1(2) . . . . ?
N2 C13 C14 C15 166.4(3) . . . . ?
N3 C5 C6 C1 -174.7(3) . . . . ?
N3 C21 C22 C23 -170.9(3) . . . . ?
N3 C21 C26 N8 -10.7(4) . . . . ?
N3 C21 C26 C25 170.1(3) . . . . ?
N4 C4 C5 N3 -5.9(3) . . . . ?
N4 C4 C5 C6 177.4(2) . . . . ?
N4 C27 C28 C29 65.5(4) . . . . ?
N5 C10 C11 F1 4.2(5) . . . . ?
N5 C10 C11 C12 -173.9(3) . . . . ?
N6 C8 C9 C10 177.8(3) . . . . ?
N7 C24 C25 C26 -179.2(2) . . . . ?
C1 N1 C7 C8 -144.2(3) . . . . ?
C1 N1 C7 C12 46.3(4) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C2 N2 C13 C14 -78.6(3) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
C2 C3 C4 N4 -177.5(2) . . . . ?
C2 C3 C4 C5 2.1(4) . . . . ?
C3 C4 C5 N3 174.4(2) . . . . ?
C3 C4 C5 C6 -2.3(3) . . . . ?
C4 N4 C27 C28 -174.0(3) . . . . ?
C4 C5 C6 C1 1.4(4) . . . . ?
C5 N3 C21 C22 -49.0(4) . . . . ?
C5 N3 C21 C26 140.6(3) . . . . ?
C6 C1 C2 N2 -179.0(2) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
C7 N1 C1 C2 -163.4(2) . . . . ?
C7 N1 C1 C6 19.9(4) . . . . ?
C7 C8 C9 C10 -2.1(5) . . . . ?
C8 C7 C12 C11 -2.6(4) . . . . ?
C8 C9 C10 N5 175.4(3) . . . . ?
C8 C9 C10 C11 -1.1(5) . . . . ?
C9 C10 C11 F1 -179.6(3) . . . . ?
C9 C10 C11 C12 2.3(5) . . . . ?
C10 C11 C12 C7 -0.4(5) . . . . ?
C12 C7 C8 N6 -176.0(2) . . . . ?
C12 C7 C8 C9 3.9(4) . . . . ?
C13 N2 C2 C1 176.8(2) . . . . ?
C13 N2 C2 C3 -2.5(4) . . . . ?
C13 C14 C15 C16 -74.6(5) . . . . ?
C14 C15 C16 C17 174.6(4) . . . . ?
C15 C16 C17 C18 -95.3(7) . . . . ?
C16 C17 C18 C19 -176.2(6) . . . . ?
C17 C18 C19 C20 -178.2(7) . . . . ?
C21 N3 C5 C4 167.2(2) . . . . ?
C21 N3 C5 C6 -16.5(4) . . . . ?
C21 C22 C23 F2 177.3(3) . . . . ?
C21 C22 C23 C24 0.4(5) . . . . ?
C22 C21 C26 N8 178.2(3) . . . . ?
C22 C21 C26 C25 -0.9(4) . . . . ?
C22 C23 C24 N7 178.4(3) . . . . ?
C22 C23 C24 C25 -0.3(5) . . . . ?
C23 C24 C25 C26 -0.5(4) . . . . ?
C24 C25 C26 N8 -178.1(2) . . . . ?
C24 C25 C26 C21 1.1(4) . . . . ?
C26 C21 C22 C23 0.2(4) . . . . ?
C27 N4 C4 C3 -0.7(4) . . . . ?
C27 N4 C4 C5 179.7(2) . . . . ?
C27 C28 C29 C30 -170.0(4) . . . . ?
C28 C29 C30 C31 -179.1(5) . . . . ?
C29 C30 C31 C32 -64.9(8) . . . . ?
C30 C31 C32 C35b 179.6(16) . . . . ?
C30 C31 C32 C33a -172.6(13) . . . . ?
C31 C32 C33a C34a -94(3) . . . . ?
C31 C32 C35b C36b -29(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.528
_oxdiff_exptl_absorpt_empirical_full_min 0.573
