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

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1515627'
_audit_update_record             
;
2017-10-05 deposited with the CCDC.
2018-11-13 downloaded from the CCDC.
;
_audit_creation_date             2017-10-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C24 H25 F7 N2 O3)'
_chemical_formula_sum            'C20.50 H0 F20.50 N20.50 O20.50'
_chemical_formula_weight         1250.8177
_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'
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'
F F 0.0171 0.0103 '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'

_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                   9.207(5)
_cell_length_b                   14.125(5)
_cell_length_c                   18.327(5)
_cell_angle_alpha                96.941(5)
_cell_angle_beta                 90.055(5)
_cell_angle_gamma                90.101(5)
_cell_volume                     2365.9(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1945
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1414
_cell_measurement_theta_min      3.0317
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.944
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.9518
_exptl_absorpt_correction_T_min  0.9444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1230
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14346
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         28.264
_diffrn_reflns_theta_min         1.452
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7432
_reflns_number_total             10536
_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       'SHELXL-2013 (Sheldrick, 2013)'
_computing_data_collection       
'CrysAlisPro(1.171.35.21) (Agilent Tech., 2012)'
_computing_data_reduction        
'CrysAlisPro(1.171.35.21) (Agilent Tech., 2012)'
_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    'SHELXL-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     651
_refine_ls_number_reflns         10536
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0744
_refine_ls_restrained_S_all      1.065
_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)+(0.1186P)²+0.9815P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1932
_refine_ls_wR_factor_ref         0.2220
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B), C44(H44A,
 H44B), C46(H46A,H46B), C47(H47A,H47B), C48(H48A,H48B), C14(H14A,H14B),
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C22(H22A,H22B),
  C23(H23A,H23B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39), N4(H4), C8(H8),
 C9(H9), C10(H10), C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.4419(4) 0.2130(2) -0.02751(13) 0.0975(11) Uani 1 1 d . . . . .
F2 F 0.3399(3) 0.09500(16) 0.01301(13) 0.0621(6) Uani 1 1 d . . . . .
F3 F 0.5690(3) 0.1149(2) 0.02399(18) 0.0925(10) Uani 1 1 d . . . . .
F4 F 0.2952(2) 0.26696(14) 0.09472(13) 0.0501(5) Uani 1 1 d . . . . .
F5 F 0.3973(2) 0.15869(15) 0.15042(11) 0.0491(5) Uani 1 1 d . . . . .
F6 F 0.65779(19) 0.23352(14) 0.14065(10) 0.0429(5) Uani 1 1 d . . . . .
F7 F 0.5806(2) 0.33722(14) 0.07140(9) 0.0418(5) Uani 1 1 d . . . . .
O1 O 0.3097(2) 0.28127(15) 0.29135(11) 0.0330(5) Uani 1 1 d . . . . .
O2 O 0.7563(2) 0.32385(18) 0.34855(12) 0.0438(6) Uani 1 1 d . . . . .
O3 O 0.7738(2) 0.38681(17) 0.24321(11) 0.0359(5) Uani 1 1 d . . . . .
N1 N 0.4842(3) 0.58270(17) 0.28035(14) 0.0305(5) Uani 1 1 d . . . . .
N2 N 0.3122(3) 0.47188(18) 0.30678(14) 0.0317(5) Uani 1 1 d . . . . .
H2 H 0.2621 0.4221 0.2910 0.038 Uiso 1 1 calc R . . . .
C25 C 0.4448(5) 0.1600(3) 0.0261(2) 0.0497(9) Uani 1 1 d . . . . .
C26 C 0.4195(3) 0.2198(2) 0.10085(16) 0.0328(6) Uani 1 1 d . . . . .
C27 C 0.5426(3) 0.2895(2) 0.12861(15) 0.0282(6) Uani 1 1 d . . . . .
C28 C 0.5075(3) 0.35708(19) 0.19728(14) 0.0233(5) Uani 1 1 d . . . . .
C29 C 0.5510(3) 0.32264(19) 0.26844(15) 0.0255(6) Uani 1 1 d . . . . .
C30 C 0.6981(3) 0.3408(2) 0.29276(15) 0.0261(6) Uani 1 1 d . . . . .
C31 C 0.9241(3) 0.4081(3) 0.25958(18) 0.0374(7) Uani 1 1 d . . . . .
H31A H 0.9773 0.3499 0.2640 0.045 Uiso 1 1 calc R . . . .
H31B H 0.9326 0.4497 0.3055 0.045 Uiso 1 1 calc R . . . .
C32 C 0.9834(4) 0.4559(4) 0.1982(2) 0.0713(14) Uani 1 1 d . . . . .
H32A H 0.9826 0.4121 0.1539 0.107 Uiso 1 1 calc GR . . . .
H32B H 1.0812 0.4763 0.2095 0.107 Uiso 1 1 calc GR . . . .
H32C H 0.9246 0.5103 0.1915 0.107 Uiso 1 1 calc GR . . . .
C33 C 0.4441(3) 0.2792(2) 0.30774(15) 0.0265(6) Uani 1 1 d . . . . .
C34 C 0.4813(3) 0.2298(2) 0.37426(15) 0.0278(6) Uani 1 1 d . . . . .
C35 C 0.5843(3) 0.1589(2) 0.37346(18) 0.0347(7) Uani 1 1 d . . . . .
H35 H 0.6429 0.1445 0.3323 0.042 Uiso 1 1 calc R . . . .
C36 C 0.6010(4) 0.1089(3) 0.4337(2) 0.0472(9) Uani 1 1 d . . . . .
H36 H 0.6695 0.0604 0.4325 0.057 Uiso 1 1 calc R . . . .
C37 C 0.5153(4) 0.1313(3) 0.4957(2) 0.0507(10) Uani 1 1 d . . . . .
H37 H 0.5279 0.0990 0.5365 0.061 Uiso 1 1 calc R . . . .
C38 C 0.4119(4) 0.2013(3) 0.49638(17) 0.0460(9) Uani 1 1 d . . . . .
H38 H 0.3544 0.2163 0.5378 0.055 Uiso 1 1 calc R . . . .
C39 C 0.3928(4) 0.2497(2) 0.43589(16) 0.0366(7) Uani 1 1 d . . . . .
H39 H 0.3206 0.2957 0.4363 0.044 Uiso 1 1 calc R . . . .
C40 C 0.4421(3) 0.4401(2) 0.19275(15) 0.0267(6) Uani 1 1 d . . . . .
C41 C 0.3868(3) 0.4842(2) 0.12611(17) 0.0320(6) Uani 1 1 d . . . . .
H41A H 0.2931 0.5135 0.1378 0.038 Uiso 1 1 calc R . . . .
H41B H 0.3729 0.4341 0.0856 0.038 Uiso 1 1 calc R . . . .
C42 C 0.4914(4) 0.5603(2) 0.10135(18) 0.0401(8) Uani 1 1 d . . . . .
H42A H 0.5845 0.5307 0.0888 0.048 Uiso 1 1 calc R . . . .
H42B H 0.4526 0.5829 0.0574 0.048 Uiso 1 1 calc R . . . .
C43 C 0.5148(4) 0.6451(2) 0.15937(19) 0.0395(8) Uani 1 1 d . . . . .
H43A H 0.4217 0.6741 0.1727 0.047 Uiso 1 1 calc R . . . .
H43B H 0.5741 0.6922 0.1389 0.047 Uiso 1 1 calc R . . . .
C44 C 0.5887(3) 0.6174(2) 0.22837(19) 0.0373(7) Uani 1 1 d . . . . .
H44A H 0.6596 0.5679 0.2142 0.045 Uiso 1 1 calc R . . . .
H44B H 0.6400 0.6723 0.2528 0.045 Uiso 1 1 calc R . . . .
C45 C 0.4145(3) 0.5011(2) 0.26414(16) 0.0280(6) Uani 1 1 d . . . . .
C46 C 0.2814(4) 0.5211(3) 0.37972(19) 0.0446(8) Uani 1 1 d . . . . .
H46A H 0.2598 0.4748 0.4132 0.054 Uiso 1 1 calc R . . . .
H46B H 0.1971 0.5618 0.3775 0.054 Uiso 1 1 calc R . . . .
C47 C 0.4115(4) 0.5808(3) 0.40767(19) 0.0447(8) Uani 1 1 d . . . . .
H47A H 0.3867 0.6204 0.4529 0.054 Uiso 1 1 calc R . . . .
H47B H 0.4914 0.5396 0.4177 0.054 Uiso 1 1 calc R . . . .
C48 C 0.4554(4) 0.6423(2) 0.35034(19) 0.0425(8) Uani 1 1 d . . . . .
H48A H 0.3785 0.6873 0.3436 0.051 Uiso 1 1 calc R . . . .
H48B H 0.5420 0.6782 0.3663 0.051 Uiso 1 1 calc R . . . .
F8 F 1.0558(4) -0.2862(2) -0.02732(13) 0.0960(11) Uani 1 1 d . . . . .
F9 F 0.9301(3) -0.3852(2) 0.02384(17) 0.0896(10) Uani 1 1 d . . . . .
F10 F 1.1581(3) -0.40385(16) 0.01304(12) 0.0615(6) Uani 1 1 d . . . . .
F11 F 1.1009(2) -0.34107(14) 0.15057(11) 0.0466(5) Uani 1 1 d . . . . .
F12 F 1.2030(2) -0.23163(14) 0.09532(12) 0.0484(5) Uani 1 1 d . . . . .
F13 F 0.84068(19) -0.26666(14) 0.14063(10) 0.0415(5) Uani 1 1 d . . . . .
F14 F 0.9170(2) -0.16292(13) 0.07151(9) 0.0393(4) Uani 1 1 d . . . . .
O4 O 1.1882(2) -0.21842(14) 0.29165(11) 0.0304(4) Uani 1 1 d . . . . .
O5 O 0.7420(2) -0.17689(18) 0.34891(12) 0.0436(6) Uani 1 1 d . . . . .
O6 O 0.7240(2) -0.11408(16) 0.24346(11) 0.0332(5) Uani 1 1 d . . . . .
N3 N 1.0121(3) 0.08204(17) 0.28106(14) 0.0310(5) Uani 1 1 d . . . . .
N4 N 1.1855(3) -0.02693(18) 0.30739(13) 0.0302(5) Uani 1 1 d . . . . .
H4 H 1.2361 -0.0762 0.2914 0.036 Uiso 1 1 calc R . . . .
C1 C 1.0528(5) -0.3405(3) 0.02632(19) 0.0483(9) Uani 1 1 d . . . . .
C2 C 1.0787(3) -0.2799(2) 0.10114(16) 0.0314(6) Uani 1 1 d . . . . .
C3 C 0.9552(3) -0.2104(2) 0.12874(15) 0.0279(6) Uani 1 1 d . . . . .
C4 C 0.9911(3) -0.14303(19) 0.19756(14) 0.0223(5) Uani 1 1 d . . . . .
C5 C 0.9470(3) -0.17732(19) 0.26836(14) 0.0234(5) Uani 1 1 d . . . . .
C6 C 1.0545(3) -0.22034(19) 0.30818(14) 0.0241(5) Uani 1 1 d . . . . .
C7 C 1.0193(3) -0.27063(19) 0.37414(14) 0.0251(6) Uani 1 1 d . . . . .
C8 C 0.9154(3) -0.3414(2) 0.37363(18) 0.0360(7) Uani 1 1 d . . . . .
H8 H 0.8565 -0.3559 0.3325 0.043 Uiso 1 1 calc R . . . .
C9 C 0.8982(4) -0.3909(3) 0.4338(2) 0.0497(9) Uani 1 1 d . . . . .
H9 H 0.8283 -0.4387 0.4329 0.060 Uiso 1 1 calc R . . . .
C10 C 0.9849(5) -0.3693(3) 0.49529(19) 0.0519(10) Uani 1 1 d . . . . .
H10 H 0.9728 -0.4021 0.5359 0.062 Uiso 1 1 calc R . . . .
C11 C 1.0890(5) -0.2993(3) 0.49629(17) 0.0473(9) Uani 1 1 d . . . . .
H11 H 1.1472 -0.2848 0.5376 0.057 Uiso 1 1 calc R . . . .
C12 C 1.1074(4) -0.2505(2) 0.43622(16) 0.0356(7) Uani 1 1 d . . . . .
H12 H 1.1790 -0.2038 0.4370 0.043 Uiso 1 1 calc R . . . .
C13 C 0.8002(3) -0.1593(2) 0.29288(15) 0.0260(6) Uani 1 1 d . . . . .
C14 C 0.5749(3) -0.0932(2) 0.26010(18) 0.0359(7) Uani 1 1 d . . . . .
H14A H 0.5671 -0.0513 0.3060 0.043 Uiso 1 1 calc R . . . .
H14B H 0.5218 -0.1514 0.2649 0.043 Uiso 1 1 calc R . . . .
C15 C 0.5143(4) -0.0455(4) 0.1981(2) 0.0680(14) Uani 1 1 d . . . . .
H15A H 0.5172 -0.0890 0.1536 0.102 Uiso 1 1 calc GR . . . .
H15B H 0.5711 0.0100 0.1921 0.102 Uiso 1 1 calc GR . . . .
H15C H 0.4156 -0.0270 0.2089 0.102 Uiso 1 1 calc GR . . . .
C16 C 1.0559(3) -0.05942(19) 0.19312(14) 0.0233(5) Uani 1 1 d . . . . .
C17 C 1.1104(3) -0.0154(2) 0.12654(16) 0.0302(6) Uani 1 1 d . . . . .
H17A H 1.1227 -0.0655 0.0859 0.036 Uiso 1 1 calc R . . . .
H17B H 1.2048 0.0132 0.1379 0.036 Uiso 1 1 calc R . . . .
C18 C 1.0078(4) 0.0611(2) 0.10218(18) 0.0387(7) Uani 1 1 d . . . . .
H18A H 1.0480 0.0843 0.0588 0.046 Uiso 1 1 calc R . . . .
H18B H 0.9149 0.0316 0.0885 0.046 Uiso 1 1 calc R . . . .
C19 C 0.9824(4) 0.1452(2) 0.16001(19) 0.0392(7) Uani 1 1 d . . . . .
H19A H 0.9223 0.1916 0.1393 0.047 Uiso 1 1 calc R . . . .
H19B H 1.0749 0.1753 0.1736 0.047 Uiso 1 1 calc R . . . .
C20 C 0.9092(3) 0.1171(2) 0.22881(18) 0.0357(7) Uani 1 1 d . . . . .
H20A H 0.8583 0.1721 0.2533 0.043 Uiso 1 1 calc R . . . .
H20B H 0.8378 0.0678 0.2144 0.043 Uiso 1 1 calc R . . . .
C21 C 1.0838(3) 0.00149(19) 0.26463(15) 0.0261(6) Uani 1 1 d . . . . .
C22 C 1.2166(4) 0.0215(2) 0.38086(19) 0.0414(8) Uani 1 1 d . . . . .
H22A H 1.3010 0.0623 0.3791 0.050 Uiso 1 1 calc R . . . .
H22B H 1.2376 -0.0253 0.4141 0.050 Uiso 1 1 calc R . . . .
C23 C 1.0870(4) 0.0804(3) 0.40835(19) 0.0458(8) Uani 1 1 d . . . . .
H23A H 1.0074 0.0387 0.4183 0.055 Uiso 1 1 calc R . . . .
H23B H 1.1117 0.1198 0.4537 0.055 Uiso 1 1 calc R . . . .
C24 C 1.0415(4) 0.1425(2) 0.35137(18) 0.0407(8) Uani 1 1 d . . . . .
H24A H 0.9547 0.1778 0.3676 0.049 Uiso 1 1 calc R . . . .
H24B H 1.1179 0.1880 0.3445 0.049 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C25 1.305(5) . ?
F2 C25 1.333(4) . ?
F3 C25 1.309(5) . ?
F4 C26 1.337(4) . ?
F5 C26 1.342(3) . ?
F6 C27 1.357(3) . ?
F7 C27 1.359(3) . ?
O1 C33 1.274(3) . ?
O2 C30 1.203(3) . ?
O3 C30 1.370(3) . ?
O3 C31 1.439(4) . ?
N1 C44 1.478(4) . ?
N1 C45 1.320(4) . ?
N1 C48 1.471(4) . ?
N2 H2 0.8600 . ?
N2 C45 1.322(4) . ?
N2 C46 1.459(4) . ?
C25 C26 1.538(5) . ?
C26 C27 1.546(4) . ?
C27 C28 1.520(4) . ?
C28 C29 1.500(4) . ?
C28 C40 1.331(4) . ?
C29 C30 1.438(4) . ?
C29 C33 1.404(4) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 C32 1.484(5) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.516(4) . ?
C34 C35 1.379(4) . ?
C34 C39 1.394(4) . ?
C35 H35 0.9300 . ?
C35 C36 1.389(4) . ?
C36 H36 0.9300 . ?
C36 C37 1.389(6) . ?
C37 H37 0.9300 . ?
C37 C38 1.373(6) . ?
C38 H38 0.9300 . ?
C38 C39 1.382(5) . ?
C39 H39 0.9300 . ?
C40 C41 1.524(4) . ?
C40 C45 1.499(4) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C41 C42 1.551(4) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C42 C43 1.517(5) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C43 C44 1.528(4) . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C46 C47 1.517(5) . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C47 C48 1.497(5) . ?
C48 H48A 0.9700 . ?
C48 H48B 0.9700 . ?
F8 C1 1.319(4) . ?
F9 C1 1.291(5) . ?
F10 C1 1.322(4) . ?
F11 C2 1.341(3) . ?
F12 C2 1.342(4) . ?
F13 C3 1.352(3) . ?
F14 C3 1.358(3) . ?
O4 C6 1.269(3) . ?
O5 C13 1.211(3) . ?
O6 C13 1.364(3) . ?
O6 C14 1.430(3) . ?
N3 C20 1.475(4) . ?
N3 C21 1.320(4) . ?
N3 C24 1.482(4) . ?
N4 H4 0.8600 . ?
N4 C21 1.314(4) . ?
N4 C22 1.462(4) . ?
C1 C2 1.544(4) . ?
C2 C3 1.548(4) . ?
C3 C4 1.521(4) . ?
C4 C5 1.495(4) . ?
C4 C16 1.333(4) . ?
C5 C6 1.411(4) . ?
C5 C13 1.438(4) . ?
C6 C7 1.509(4) . ?
C7 C8 1.382(4) . ?
C7 C12 1.398(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.384(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.374(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.378(5) . ?
C12 H12 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.496(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.520(4) . ?
C16 C21 1.500(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.542(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.512(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.524(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.508(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.503(5) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?

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
C30 O3 C31 117.1(2) . . ?
C45 N1 C44 121.2(3) . . ?
C45 N1 C48 120.0(3) . . ?
C48 N1 C44 118.7(3) . . ?
C45 N2 H2 118.9 . . ?
C45 N2 C46 122.2(3) . . ?
C46 N2 H2 118.9 . . ?
F1 C25 F2 107.2(3) . . ?
F1 C25 F3 108.5(4) . . ?
F1 C25 C26 111.4(3) . . ?
F2 C25 C26 109.9(3) . . ?
F3 C25 F2 107.7(3) . . ?
F3 C25 C26 111.9(3) . . ?
F4 C26 F5 107.2(3) . . ?
F4 C26 C25 106.4(3) . . ?
F4 C26 C27 110.5(2) . . ?
F5 C26 C25 107.3(3) . . ?
F5 C26 C27 108.9(2) . . ?
C25 C26 C27 116.1(3) . . ?
F6 C27 F7 106.1(2) . . ?
F6 C27 C26 105.4(2) . . ?
F6 C27 C28 110.7(2) . . ?
F7 C27 C26 106.9(2) . . ?
F7 C27 C28 111.9(2) . . ?
C28 C27 C26 115.3(2) . . ?
C29 C28 C27 115.2(2) . . ?
C40 C28 C27 121.1(2) . . ?
C40 C28 C29 123.8(3) . . ?
C30 C29 C28 117.1(2) . . ?
C33 C29 C28 117.8(2) . . ?
C33 C29 C30 125.0(2) . . ?
O2 C30 O3 119.7(3) . . ?
O2 C30 C29 129.5(3) . . ?
O3 C30 C29 110.8(2) . . ?
O3 C31 H31A 110.2 . . ?
O3 C31 H31B 110.2 . . ?
O3 C31 C32 107.3(3) . . ?
H31A C31 H31B 108.5 . . ?
C32 C31 H31A 110.2 . . ?
C32 C31 H31B 110.2 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O1 C33 C29 122.4(2) . . ?
O1 C33 C34 115.8(2) . . ?
C29 C33 C34 121.8(2) . . ?
C35 C34 C33 123.5(3) . . ?
C35 C34 C39 119.2(3) . . ?
C39 C34 C33 116.8(3) . . ?
C34 C35 H35 119.8 . . ?
C34 C35 C36 120.4(3) . . ?
C36 C35 H35 119.8 . . ?
C35 C36 H36 120.0 . . ?
C37 C36 C35 120.0(3) . . ?
C37 C36 H36 120.0 . . ?
C36 C37 H37 120.1 . . ?
C38 C37 C36 119.7(3) . . ?
C38 C37 H37 120.1 . . ?
C37 C38 H38 119.8 . . ?
C37 C38 C39 120.4(3) . . ?
C39 C38 H38 119.8 . . ?
C34 C39 H39 119.9 . . ?
C38 C39 C34 120.3(3) . . ?
C38 C39 H39 119.9 . . ?
C28 C40 C41 130.6(3) . . ?
C28 C40 C45 116.2(2) . . ?
C45 C40 C41 113.2(2) . . ?
C40 C41 H41A 109.0 . . ?
C40 C41 H41B 109.0 . . ?
C40 C41 C42 113.1(2) . . ?
H41A C41 H41B 107.8 . . ?
C42 C41 H41A 109.0 . . ?
C42 C41 H41B 109.0 . . ?
C41 C42 H42A 108.9 . . ?
C41 C42 H42B 108.9 . . ?
H42A C42 H42B 107.7 . . ?
C43 C42 C41 113.5(3) . . ?
C43 C42 H42A 108.9 . . ?
C43 C42 H42B 108.9 . . ?
C42 C43 H43A 109.1 . . ?
C42 C43 H43B 109.1 . . ?
C42 C43 C44 112.5(3) . . ?
H43A C43 H43B 107.8 . . ?
C44 C43 H43A 109.1 . . ?
C44 C43 H43B 109.1 . . ?
N1 C44 C43 112.5(2) . . ?
N1 C44 H44A 109.1 . . ?
N1 C44 H44B 109.1 . . ?
C43 C44 H44A 109.1 . . ?
C43 C44 H44B 109.1 . . ?
H44A C44 H44B 107.8 . . ?
N1 C45 N2 122.6(3) . . ?
N1 C45 C40 120.5(3) . . ?
N2 C45 C40 116.8(3) . . ?
N2 C46 H46A 109.7 . . ?
N2 C46 H46B 109.7 . . ?
N2 C46 C47 109.8(3) . . ?
H46A C46 H46B 108.2 . . ?
C47 C46 H46A 109.7 . . ?
C47 C46 H46B 109.7 . . ?
C46 C47 H47A 109.9 . . ?
C46 C47 H47B 109.9 . . ?
H47A C47 H47B 108.3 . . ?
C48 C47 C46 108.8(3) . . ?
C48 C47 H47A 109.9 . . ?
C48 C47 H47B 109.9 . . ?
N1 C48 C47 110.0(3) . . ?
N1 C48 H48A 109.7 . . ?
N1 C48 H48B 109.7 . . ?
C47 C48 H48A 109.7 . . ?
C47 C48 H48B 109.7 . . ?
H48A C48 H48B 108.2 . . ?
C13 O6 C14 117.0(2) . . ?
C20 N3 C24 118.5(3) . . ?
C21 N3 C20 121.5(3) . . ?
C21 N3 C24 119.9(3) . . ?
C21 N4 H4 118.5 . . ?
C21 N4 C22 123.0(3) . . ?
C22 N4 H4 118.5 . . ?
F8 C1 F10 106.8(3) . . ?
F8 C1 C2 110.4(3) . . ?
F9 C1 F8 108.5(4) . . ?
F9 C1 F10 108.6(3) . . ?
F9 C1 C2 112.4(3) . . ?
F10 C1 C2 110.0(3) . . ?
F11 C2 F12 107.4(2) . . ?
F11 C2 C1 106.9(3) . . ?
F11 C2 C3 109.1(2) . . ?
F12 C2 C1 107.0(3) . . ?
F12 C2 C3 110.2(2) . . ?
C1 C2 C3 116.1(3) . . ?
F13 C3 F14 106.1(2) . . ?
F13 C3 C2 105.3(2) . . ?
F13 C3 C4 110.8(2) . . ?
F14 C3 C2 106.9(2) . . ?
F14 C3 C4 112.2(2) . . ?
C4 C3 C2 114.9(2) . . ?
C5 C4 C3 115.2(2) . . ?
C16 C4 C3 121.0(2) . . ?
C16 C4 C5 123.8(2) . . ?
C6 C5 C4 117.6(2) . . ?
C6 C5 C13 124.7(2) . . ?
C13 C5 C4 117.6(2) . . ?
O4 C6 C5 122.3(2) . . ?
O4 C6 C7 115.2(2) . . ?
C5 C6 C7 122.5(2) . . ?
C8 C7 C6 123.6(3) . . ?
C8 C7 C12 118.8(3) . . ?
C12 C7 C6 117.3(3) . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.0(4) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.4(3) . . ?
C11 C12 H12 119.8 . . ?
O5 C13 O6 119.7(3) . . ?
O5 C13 C5 129.4(3) . . ?
O6 C13 C5 110.9(2) . . ?
O6 C14 H14A 110.3 . . ?
O6 C14 H14B 110.3 . . ?
O6 C14 C15 107.3(3) . . ?
H14A C14 H14B 108.5 . . ?
C15 C14 H14A 110.3 . . ?
C15 C14 H14B 110.3 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C16 C17 130.3(3) . . ?
C4 C16 C21 116.2(2) . . ?
C21 C16 C17 113.5(2) . . ?
C16 C17 H17A 108.9 . . ?
C16 C17 H17B 108.9 . . ?
C16 C17 C18 113.5(2) . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
C17 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 C17 114.3(3) . . ?
C19 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C18 C19 H19A 109.0 . . ?
C18 C19 H19B 109.0 . . ?
C18 C19 C20 112.9(3) . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
N3 C20 C19 113.2(2) . . ?
N3 C20 H20A 108.9 . . ?
N3 C20 H20B 108.9 . . ?
C19 C20 H20A 108.9 . . ?
C19 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
N3 C21 C16 120.1(2) . . ?
N4 C21 N3 122.6(3) . . ?
N4 C21 C16 117.2(2) . . ?
N4 C22 H22A 109.8 . . ?
N4 C22 H22B 109.8 . . ?
N4 C22 C23 109.4(3) . . ?
H22A C22 H22B 108.3 . . ?
C23 C22 H22A 109.8 . . ?
C23 C22 H22B 109.8 . . ?
C22 C23 H23A 109.8 . . ?
C22 C23 H23B 109.8 . . ?
H23A C23 H23B 108.2 . . ?
C24 C23 C22 109.5(3) . . ?
C24 C23 H23A 109.8 . . ?
C24 C23 H23B 109.8 . . ?
N3 C24 C23 109.3(3) . . ?
N3 C24 H24A 109.8 . . ?
N3 C24 H24B 109.8 . . ?
C23 C24 H24A 109.8 . . ?
C23 C24 H24B 109.8 . . ?
H24A C24 H24B 108.3 . . ?

_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_1
_database_code_depnum_ccdc_archive 'CCDC 1578234'
_audit_update_record             
;
2017-10-05 deposited with the CCDC.
2018-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H F N O'
_chemical_formula_weight         62.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   12.9920(4)
_cell_length_b                   9.8081(3)
_cell_length_c                   18.9141(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.2446(14)
_cell_angle_gamma                90
_cell_volume                     2390.92(13)
_cell_formula_units_Z            40
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_F_000             1240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.783
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19607
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.713
_diffrn_reflns_theta_max         54.305
_diffrn_reflns_theta_full        54.305
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2926
_reflns_number_gt                2505
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.006(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2926
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1494
_refine_ls_R_factor_gt           0.1397
_refine_ls_wR_factor_ref         0.4300
_refine_ls_wR_factor_gt          0.4216
_refine_ls_goodness_of_fit_ref   3.804
_refine_ls_restrained_S_all      3.804
_refine_ls_shift/su_max          7.508
_refine_ls_shift/su_mean         0.102

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
C1 C -0.2709(6) 0.3361(8) 0.2550(4) 0.034(2) Uani 1 1 d . . . . .
C2 C -0.2638(6) 0.3400(8) 0.1791(4) 0.039(2) Uani 1 1 d . . . . .
C3 C -0.2643(7) 0.4657(9) 0.1429(5) 0.049(2) Uani 1 1 d . . . . .
H3A H -0.2694 0.5479 0.1688 0.058 Uiso 1 1 calc R U . . .
C4 C -0.2576(8) 0.4719(11) 0.0720(5) 0.062(3) Uani 1 1 d . . . . .
H4A H -0.2551 0.5580 0.0491 0.074 Uiso 1 1 calc R U . . .
C5 C -0.2544(8) 0.3524(11) 0.0325(5) 0.062(3) Uani 1 1 d . . . . .
H5A H -0.2545 0.3567 -0.0176 0.075 Uiso 1 1 calc R U . . .
C6 C -0.2512(7) 0.2274(11) 0.0666(5) 0.058(3) Uani 1 1 d . . . . .
H6A H -0.2444 0.1462 0.0401 0.070 Uiso 1 1 calc R U . . .
C7 C -0.2579(6) 0.2199(9) 0.1388(4) 0.045(2) Uani 1 1 d . . . . .
H7A H -0.2585 0.1334 0.1614 0.054 Uiso 1 1 calc R U . . .
C8 C -0.3609(6) 0.1359(7) 0.2938(4) 0.035(2) Uani 1 1 d . . . . .
C9 C -0.2739(6) -0.0484(7) 0.3610(4) 0.031(2) Uani 1 1 d . . . . .
C10 C -0.1772(6) 0.0153(8) 0.3640(4) 0.034(2) Uani 1 1 d . . . . .
C11 C -0.1745(6) 0.1418(7) 0.3286(4) 0.031(2) Uani 1 1 d . . . . .
C12 C -0.2635(6) 0.2030(7) 0.2938(4) 0.0306(19) Uani 1 1 d . . . . .
C13 C -0.4655(7) -0.0418(9) 0.3382(5) 0.048(2) Uani 1 1 d . . . . .
H13A H -0.4854 -0.1059 0.2984 0.058 Uiso 1 1 calc R U . . .
H13B H -0.5184 0.0312 0.3360 0.058 Uiso 1 1 calc R U . . .
C14 C -0.4608(7) -0.1155(9) 0.4076(5) 0.051(2) Uani 1 1 d . . . . .
H14A H -0.4413 -0.0515 0.4476 0.061 Uiso 1 1 calc R U . . .
H14B H -0.5297 -0.1545 0.4131 0.061 Uiso 1 1 calc R U . . .
C15 C -0.3828(8) -0.2258(9) 0.4089(6) 0.060(3) Uani 1 1 d . . . . .
H15A H -0.3704 -0.2649 0.4575 0.072 Uiso 1 1 calc R U . . .
H15B H -0.4104 -0.2992 0.3759 0.072 Uiso 1 1 calc R U . . .
C16 C -0.2140(8) -0.2904(8) 0.3822(5) 0.058(3) Uani 1 1 d . . . . .
H16A H -0.2541 -0.3711 0.3633 0.070 Uiso 1 1 calc R U . . .
H16B H -0.1797 -0.3139 0.4304 0.070 Uiso 1 1 calc R U . . .
C17 C -0.1280(8) -0.2608(10) 0.3331(5) 0.057(3) Uani 1 1 d . . . . .
H17A H -0.0973 -0.3481 0.3199 0.068 Uiso 1 1 calc R U . . .
H17B H -0.1600 -0.2163 0.2888 0.068 Uiso 1 1 calc R U . . .
C18 C -0.0438(7) -0.1708(9) 0.3692(4) 0.047(2) Uani 1 1 d . . . . .
H18A H 0.0028 -0.2254 0.4038 0.057 Uiso 1 1 calc R U . . .
H18B H -0.0021 -0.1340 0.3332 0.057 Uiso 1 1 calc R U . . .
C19 C -0.0876(6) -0.0555(8) 0.4073(4) 0.038(2) Uani 1 1 d . . . . .
H19A H -0.0319 0.0119 0.4209 0.045 Uiso 1 1 calc R U . . .
H19B H -0.1109 -0.0906 0.4517 0.045 Uiso 1 1 calc R U . . .
C20 C -0.0738(6) 0.2152(8) 0.3295(4) 0.035(2) Uani 1 1 d . . . . .
C21 C -0.0427(6) 0.3112(8) 0.3944(4) 0.039(2) Uani 1 1 d . . . . .
C22 C 0.0630(7) 0.3799(10) 0.3980(5) 0.054(3) Uani 1 1 d . . . . .
N1 N -0.3641(5) 0.0175(6) 0.3314(3) 0.0342(17) Uani 1 1 d . . . . .
N2 N -0.2864(6) -0.1781(6) 0.3887(3) 0.046(2) Uani 1 1 d . . . . .
O1 O -0.4446(4) 0.1842(6) 0.2612(3) 0.0465(17) Uani 1 1 d . . . . .
O2 O -0.2918(5) 0.4397(6) 0.2871(3) 0.0499(18) Uani 1 1 d . . . . .
F1 F 0.0765(5) 0.4674(6) 0.4518(3) 0.0760(19) Uani 1 1 d . . . . .
F2 F 0.0764(5) 0.4424(7) 0.3402(3) 0.093(2) Uani 1 1 d . . . . .
F3 F 0.1383(5) 0.2874(7) 0.4128(4) 0.094(2) Uani 1 1 d . . . . .
F4 F -0.1130(4) 0.4093(5) 0.3938(3) 0.0584(16) Uani 1 1 d . . . . .
F5 F -0.0445(4) 0.2422(5) 0.4559(2) 0.0553(16) Uani 1 1 d . . . . .
F6 F -0.0771(3) 0.2988(5) 0.2717(2) 0.0505(16) Uani 1 1 d . . . . .
F7 F 0.0068(3) 0.1310(5) 0.3251(2) 0.0480(15) Uani 1 1 d . . . . .
O3W O 0.3504(3) 0.3528(4) 0.3399(3) 0.0210(14) Uani 1 1 d . . . . .
O2W O -0.4583(4) 0.1580(6) -0.0622(2) 0.0477(18) Uani 1 1 d . . . . .
O1W O -0.5259(7) 0.4125(11) 0.3606(5) 0.121(3) Uani 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
C1 O2 1.231(9) . ?
C1 C2 1.451(11) . ?
C1 C12 1.495(10) . ?
C2 C7 1.411(11) . ?
C2 C3 1.410(11) . ?
C3 C4 1.357(13) . ?
C4 C5 1.393(14) . ?
C5 C6 1.383(12) . ?
C6 C7 1.382(12) . ?
C8 O1 1.273(9) . ?
C8 N1 1.365(9) . ?
C8 C12 1.427(11) . ?
C9 C10 1.398(11) . ?
C9 N2 1.394(10) . ?
C9 N1 1.392(10) . ?
C10 C11 1.413(10) . ?
C10 C19 1.506(11) . ?
C11 C12 1.391(10) . ?
C11 C20 1.492(10) . ?
C13 N1 1.460(10) . ?
C13 C14 1.493(12) . ?
C14 C15 1.481(13) . ?
C15 N2 1.433(12) . ?
C16 N2 1.463(11) . ?
C16 C17 1.567(14) . ?
C17 C18 1.502(13) . ?
C18 C19 1.491(11) . ?
C20 F7 1.344(9) . ?
C20 F6 1.364(8) . ?
C20 C21 1.559(11) . ?
C21 F4 1.326(9) . ?
C21 F5 1.348(9) . ?
C21 C22 1.523(12) . ?
C22 F2 1.284(11) . ?
C22 F1 1.326(11) . ?
C22 F3 1.338(11) . ?
O3W O1W 1.709(11) 1_655 ?
O2W O1W 1.750(10) 4_565 ?
O1W O3W 1.709(11) 1_455 ?
O1W O2W 1.750(10) 4_566 ?

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
O2 C1 C2 120.8(7) . . ?
O2 C1 C12 118.9(7) . . ?
C2 C1 C12 120.0(7) . . ?
C7 C2 C3 117.7(7) . . ?
C7 C2 C1 121.8(7) . . ?
C3 C2 C1 120.4(7) . . ?
C4 C3 C2 121.5(9) . . ?
C3 C4 C5 120.1(9) . . ?
C6 C5 C4 119.9(9) . . ?
C5 C6 C7 120.4(9) . . ?
C6 C7 C2 120.3(8) . . ?
O1 C8 N1 119.3(7) . . ?
O1 C8 C12 122.1(7) . . ?
N1 C8 C12 118.6(6) . . ?
C10 C9 N2 122.6(7) . . ?
C10 C9 N1 121.0(6) . . ?
N2 C9 N1 116.3(6) . . ?
C9 C10 C11 116.7(7) . . ?
C9 C10 C19 116.5(7) . . ?
C11 C10 C19 126.8(7) . . ?
C12 C11 C10 122.3(7) . . ?
C12 C11 C20 118.2(6) . . ?
C10 C11 C20 119.5(7) . . ?
C11 C12 C8 119.0(7) . . ?
C11 C12 C1 127.4(7) . . ?
C8 C12 C1 113.6(6) . . ?
N1 C13 C14 109.5(7) . . ?
C15 C14 C13 108.6(8) . . ?
N2 C15 C14 112.2(7) . . ?
N2 C16 C17 115.1(7) . . ?
C18 C17 C16 111.9(7) . . ?
C19 C18 C17 111.4(7) . . ?
C18 C19 C10 113.8(6) . . ?
F7 C20 F6 105.4(5) . . ?
F7 C20 C11 113.1(6) . . ?
F6 C20 C11 110.0(6) . . ?
F7 C20 C21 107.1(6) . . ?
F6 C20 C21 104.3(6) . . ?
C11 C20 C21 116.2(6) . . ?
F4 C21 F5 106.6(7) . . ?
F4 C21 C22 107.2(7) . . ?
F5 C21 C22 107.4(6) . . ?
F4 C21 C20 108.7(6) . . ?
F5 C21 C20 110.2(6) . . ?
C22 C21 C20 116.4(7) . . ?
F2 C22 F1 109.0(8) . . ?
F2 C22 F3 109.1(9) . . ?
F1 C22 F3 104.8(7) . . ?
F2 C22 C21 113.1(7) . . ?
F1 C22 C21 110.6(8) . . ?
F3 C22 C21 109.9(8) . . ?
C8 N1 C9 121.6(6) . . ?
C8 N1 C13 118.2(6) . . ?
C9 N1 C13 120.2(6) . . ?
C9 N2 C15 123.0(7) . . ?
C9 N2 C16 123.3(7) . . ?
C15 N2 C16 111.7(7) . . ?
O3W O1W O2W 114.4(6) 1_455 4_566 ?

_refine_diff_density_max         3.133
_refine_diff_density_min         -0.662
_refine_diff_density_rms         0.171

####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1578180'
_audit_update_record             
;
2017-10-05 deposited with the CCDC.
2018-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          195-196
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3.83 H3.30 F1.04 I0.17 N0.35 O0.35'
_chemical_formula_weight         101.1624

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   10.7013(10)
_cell_length_b                   10.5720(9)
_cell_length_c                   19.8575(18)
_cell_angle_alpha                90
_cell_angle_beta                 103.499(3)
_cell_angle_gamma                90
_cell_volume                     2184.5(3)
_cell_formula_units_Z            23
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1945
_cell_measurement_theta_min      3.0317
_cell_measurement_theta_max      29.1414

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    1.540
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85293
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   
;
 CrysAlis (Oxford Diffraction, 2006)
;
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            31028
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.102
_diffrn_reflns_theta_max         28.323
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             5323
_reflns_number_gt                4067
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
'CrysAlisPro(1.171.35.21) (Agilent Tech., 2012)'
_computing_cell_refinement       
'CrysAlisPro(1.171.35.21) (Agilent Tech., 2012)'
_computing_data_reduction        
'CrysAlisPro(1.171.35.21) (Agilent Tech., 2012)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1648P)²+19.9184P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.012(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5323
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1559
_refine_ls_R_factor_gt           0.1291
_refine_ls_wR_factor_ref         0.3637
_refine_ls_wR_factor_gt          0.3365
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
I1 I 0.90761(8) 0.70676(8) 0.05475(5) 0.0853(5) Uani 1 1 d . . . . .
F1 F 1.0334(5) 0.4041(6) 0.2527(3) 0.0628(14) Uani 1 1 d . . . . .
F2 F 1.1470(6) 0.3366(7) 0.1844(4) 0.0806(19) Uani 1 1 d . . . . .
F4 F 1.1270(11) 0.6671(9) 0.1939(6) 0.152(6) Uani 1 1 d . . . . .
F6 F 0.8992(11) 0.4514(8) 0.1133(5) 0.122(3) Uani 1 1 d . . . . .
C1 C 1.1173(8) 0.5032(8) 0.3686(4) 0.0462(17) Uani 1 1 d . . . . .
C2 C 1.1021(7) 0.3896(8) 0.4109(4) 0.0415(15) Uani 1 1 d . . . . .
C3 C 1.1921(9) 0.2919(7) 0.4228(4) 0.0464(17) Uani 1 1 d . . . . .
H3A H 1.2633 0.2958 0.4034 0.056 Uiso 1 1 calc R U . . .
C4 C 1.1761(12) 0.1892(9) 0.4632(5) 0.063(2) Uani 1 1 d . . . . .
H4A H 1.2355 0.1235 0.4703 0.075 Uiso 1 1 calc R U . . .
C5 C 1.0720(16) 0.1846(12) 0.4927(6) 0.082(4) Uani 1 1 d . . . . .
H5A H 1.0631 0.1172 0.5214 0.099 Uiso 1 1 calc R U . . .
C6 C 0.9809(13) 0.2790(15) 0.4802(6) 0.082(4) Uani 1 1 d . . . . .
H6A H 0.9088 0.2735 0.4987 0.099 Uiso 1 1 calc R U . . .
C7 C 0.9964(9) 0.3812(12) 0.4406(5) 0.062(2) Uani 1 1 d . . . . .
H7A H 0.9356 0.4457 0.4333 0.075 Uiso 1 1 calc R U . . .
C8 C 1.3445(7) 0.5574(7) 0.3907(4) 0.0403(15) Uani 1 1 d . . . . .
C9 C 1.2367(7) 0.5109(7) 0.3406(4) 0.0396(14) Uani 1 1 d . . . . .
C10 C 1.2499(7) 0.4777(7) 0.2745(4) 0.0417(15) Uani 1 1 d . . . . .
C11 C 1.3681(8) 0.4878(8) 0.2546(4) 0.0453(16) Uani 1 1 d . . . . .
C12 C 1.3967(11) 0.4210(11) 0.1906(6) 0.066(3) Uani 1 1 d . . . . .
H12A H 1.3663 0.4748 0.1506 0.079 Uiso 1 1 calc R U . . .
H12B H 1.3471 0.3434 0.1828 0.079 Uiso 1 1 calc R U . . .
C13 C 1.5398(11) 0.3878(11) 0.1947(6) 0.069(3) Uani 1 1 d . . . . .
H13A H 1.5791 0.3568 0.2407 0.082 Uiso 1 1 calc R U . . .
H13B H 1.5439 0.3206 0.1620 0.082 Uiso 1 1 calc R U . . .
C14 C 1.6141(13) 0.4997(13) 0.1789(6) 0.077(3) Uani 1 1 d . . . . .
H14A H 1.7054 0.4843 0.1959 0.093 Uiso 1 1 calc R U . . .
H14B H 1.5971 0.5119 0.1292 0.093 Uiso 1 1 calc R U . . .
C15 C 1.5769(11) 0.6165(11) 0.2122(5) 0.066(2) Uani 1 1 d . . . . .
H15A H 1.6365 0.6841 0.2091 0.080 Uiso 1 1 calc R U . . .
H15B H 1.4917 0.6431 0.1876 0.080 Uiso 1 1 calc R U . . .
C16 C 1.4680(7) 0.5494(7) 0.3024(4) 0.0414(15) Uani 1 1 d . . . . .
C17 C 1.5679(8) 0.6234(9) 0.4192(4) 0.0520(19) Uani 1 1 d . . . . .
H17A H 1.5623 0.5991 0.4655 0.062 Uiso 1 1 calc R U . . .
H17B H 1.5670 0.7150 0.4167 0.062 Uiso 1 1 calc R U . . .
C18 C 1.6901(9) 0.5753(10) 0.4056(5) 0.059(2) Uani 1 1 d . . . . .
H18A H 1.7628 0.6081 0.4399 0.071 Uiso 1 1 calc R U . . .
H18B H 1.6922 0.4836 0.4079 0.071 Uiso 1 1 calc R U . . .
C19 C 1.6957(11) 0.6182(13) 0.3359(6) 0.072(3) Uani 1 1 d . . . . .
H19A H 1.7134 0.7083 0.3373 0.087 Uiso 1 1 calc R U . . .
H19B H 1.7657 0.5754 0.3220 0.087 Uiso 1 1 calc R U . . .
C20 C 1.1298(8) 0.4372(9) 0.2215(4) 0.0486(18) Uani 1 1 d . . . . .
C21 C 1.0729(13) 0.5545(16) 0.1716(6) 0.093(4) Uani 1 1 d . . . . .
N1 N 1.4574(6) 0.5729(6) 0.3687(3) 0.0395(13) Uani 1 1 d . . . . .
N2 N 1.5774(7) 0.5939(8) 0.2852(4) 0.0525(16) Uani 1 1 d . . . . .
O1 O 1.0385(7) 0.5876(7) 0.3600(4) 0.072(2) Uani 1 1 d . . . . .
O2 O 1.3389(6) 0.5877(6) 0.4503(3) 0.0547(15) Uani 1 1 d . . . . .
F3 F 1.1478(13) 0.5319(13) 0.1156(7) 0.141(4) Uiso 1 1 d . . . . .
C22 C 0.956(2) 0.556(2) 0.1246(11) 0.127(6) Uiso 1 1 d . . . . .
F5 F 0.9191(15) 0.6169(14) 0.1992(7) 0.158(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
I1 C22 2.10(2) . ?
F1 C20 1.366(10) . ?
F2 C20 1.331(11) . ?
F4 C21 1.352(18) . ?
F6 C22 1.26(2) . ?
C1 O1 1.211(10) . ?
C1 C2 1.496(11) . ?
C1 C9 1.510(11) . ?
C2 C3 1.394(12) . ?
C2 C7 1.395(11) . ?
C3 C4 1.385(12) . ?
C4 C5 1.376(18) . ?
C5 C6 1.38(2) . ?
C6 C7 1.369(17) . ?
C8 O2 1.241(9) . ?
C8 N1 1.387(10) . ?
C8 C9 1.424(10) . ?
C9 C10 1.397(11) . ?
C10 C11 1.414(12) . ?
C10 C20 1.521(10) . ?
C11 C16 1.413(10) . ?
C11 C12 1.545(13) . ?
C12 C13 1.555(16) . ?
C13 C14 1.499(18) . ?
C14 C15 1.498(17) . ?
C15 N2 1.467(12) . ?
C16 N1 1.371(9) . ?
C16 N2 1.377(10) . ?
C17 N1 1.461(10) . ?
C17 C18 1.484(13) . ?
C18 C19 1.471(15) . ?
C19 N2 1.445(13) . ?
C20 C21 1.615(15) . ?
C21 C22 1.38(2) . ?
C21 F3 1.535(19) . ?
C22 F5 1.74(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
O1 C1 C2 120.5(8) . . ?
O1 C1 C9 121.9(8) . . ?
C2 C1 C9 117.5(7) . . ?
C3 C2 C7 118.5(8) . . ?
C3 C2 C1 121.9(7) . . ?
C7 C2 C1 119.6(8) . . ?
C4 C3 C2 120.3(9) . . ?
C5 C4 C3 119.8(11) . . ?
C4 C5 C6 120.5(10) . . ?
C7 C6 C5 120.0(10) . . ?
C6 C7 C2 120.8(11) . . ?
O2 C8 N1 120.6(6) . . ?
O2 C8 C9 123.0(7) . . ?
N1 C8 C9 116.4(6) . . ?
C10 C9 C8 120.0(7) . . ?
C10 C9 C1 127.8(7) . . ?
C8 C9 C1 112.2(6) . . ?
C9 C10 C11 122.5(7) . . ?
C9 C10 C20 117.8(7) . . ?
C11 C10 C20 119.6(7) . . ?
C16 C11 C10 115.7(7) . . ?
C16 C11 C12 119.9(8) . . ?
C10 C11 C12 123.8(7) . . ?
C11 C12 C13 116.3(8) . . ?
C14 C13 C12 112.0(10) . . ?
C15 C14 C13 110.4(9) . . ?
N2 C15 C14 111.3(9) . . ?
N1 C16 N2 116.3(7) . . ?
N1 C16 C11 120.7(7) . . ?
N2 C16 C11 123.0(7) . . ?
N1 C17 C18 110.9(7) . . ?
C19 C18 C17 107.2(9) . . ?
N2 C19 C18 112.3(8) . . ?
F2 C20 F1 105.2(7) . . ?
F2 C20 C10 113.8(7) . . ?
F1 C20 C10 111.4(6) . . ?
F2 C20 C21 110.8(8) . . ?
F1 C20 C21 105.0(8) . . ?
C10 C20 C21 110.2(8) . . ?
F4 C21 C22 117.6(15) . . ?
F4 C21 F3 96.7(12) . . ?
C22 C21 F3 93.3(13) . . ?
F4 C21 C20 113.8(8) . . ?
C22 C21 C20 125.3(14) . . ?
F3 C21 C20 98.0(11) . . ?
C16 N1 C8 123.7(6) . . ?
C16 N1 C17 119.3(7) . . ?
C8 N1 C17 116.9(6) . . ?
C16 N2 C19 123.0(7) . . ?
C16 N2 C15 119.6(7) . . ?
C19 N2 C15 117.4(8) . . ?
F6 C22 C21 115.7(19) . . ?
F6 C22 F5 106.4(16) . . ?
C21 C22 F5 77.2(14) . . ?
F6 C22 I1 121.2(15) . . ?
C21 C22 I1 120.1(15) . . ?
F5 C22 I1 102.3(12) . . ?

_refine_diff_density_max         3.499
_refine_diff_density_min         -3.102
_refine_diff_density_rms         0.177

