# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_crn35
_database_code_depnum_ccdc_archive 'CCDC 2023737'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2020-08-17 deposited with the CCDC.	2021-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            'co-crystal 2'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H14 F6 I3 N O P'
_chemical_formula_weight         930.09

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'
P P 0.1023 0.0942 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.9001(6)
_cell_length_b                   13.1997(9)
_cell_length_c                   13.3554(9)
_cell_angle_alpha                99.4474(9)
_cell_angle_beta                 97.4134(10)
_cell_angle_gamma                105.2813(9)
_cell_volume                     1468.30(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      30.66

_exptl_crystal_description       plank
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.104
_exptl_crystal_F_000             874
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.192
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.102
_exptl_absorpt_coefficient_mu    3.312
_shelx_estimated_absorpt_T_min   0.569
_shelx_estimated_absorpt_T_max   0.729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6974
_exptl_absorpt_correction_T_max  0.7679
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32986
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.572
_diffrn_reflns_theta_max         31.262
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8898
_reflns_number_gt                7480
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0201P)²+0.8504P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8898
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0231
_refine_ls_wR_factor_ref         0.0514
_refine_ls_wR_factor_gt          0.0482
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.002
_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
P1 P 0.69213(7) 0.49414(4) 0.72366(4) 0.02702(11) Uani 1 1 d . . . . .
O1 O 0.6520(2) 0.58987(14) 0.77580(13) 0.0421(4) Uani 1 1 d . . . . .
C11 C 0.5375(2) 0.37074(18) 0.70139(17) 0.0304(4) Uani 1 1 d . . . . .
C12 C 0.4868(3) 0.3390(2) 0.7880(2) 0.0456(6) Uani 1 1 d . . . . .
H12 H 0.539951 0.379850 0.854495 0.055 Uiso 1 1 calc R U . . .
C13 C 0.3586(3) 0.2478(3) 0.7799(2) 0.0544(8) Uani 1 1 d . . . . .
H13 H 0.324721 0.227648 0.840267 0.065 Uiso 1 1 calc R U . . .
C14 C 0.2833(3) 0.1886(2) 0.6854(2) 0.0456(6) Uani 1 1 d . . . . .
H14 H 0.196879 0.126560 0.680334 0.055 Uiso 1 1 calc R U . . .
C15 C 0.3308(2) 0.21709(18) 0.59358(19) 0.0323(5) Uani 1 1 d . . . . .
C16 C 0.2507(3) 0.15338(18) 0.4961(2) 0.0360(5) Uani 1 1 d . . . . .
H16 H 0.164540 0.091464 0.491838 0.043 Uiso 1 1 calc R U . . .
C17 C 0.2964(3) 0.18018(19) 0.4088(2) 0.0398(6) Uani 1 1 d . . . . .
H17 H 0.242023 0.137037 0.343492 0.048 Uiso 1 1 calc R U . . .
C18 C 0.4239(3) 0.27159(18) 0.41440(18) 0.0336(5) Uani 1 1 d . . . . .
H18 H 0.453315 0.288928 0.352015 0.040 Uiso 1 1 calc R U . . .
C19 C 0.5080(2) 0.33720(15) 0.50702(16) 0.0238(4) Uani 1 1 d . . . . .
C20 C 0.4614(2) 0.31017(16) 0.60085(17) 0.0254(4) Uani 1 1 d . . . . .
C21 C 0.7327(2) 0.50285(15) 0.59692(16) 0.0240(4) Uani 1 1 d . . . . .
C22 C 0.6423(2) 0.43108(15) 0.50642(16) 0.0227(4) Uani 1 1 d . . . . .
C23 C 0.6887(3) 0.45441(18) 0.41370(17) 0.0305(4) Uani 1 1 d . . . . .
H23 H 0.632846 0.409161 0.349615 0.037 Uiso 1 1 calc R U . . .
C24 C 0.8146(3) 0.54229(19) 0.41521(18) 0.0337(5) Uani 1 1 d . . . . .
H24 H 0.841932 0.555120 0.351029 0.040 Uiso 1 1 calc R U . . .
N25 N 0.9004(2) 0.61049(15) 0.50111(16) 0.0347(4) Uani 1 1 d . . . . .
C26 C 0.8581(3) 0.58938(17) 0.58915(18) 0.0318(5) Uani 1 1 d . . . . .
H26 H 0.917474 0.636585 0.651440 0.038 Uiso 1 1 calc R U . . .
C31 C 0.8662(3) 0.47718(17) 0.79526(16) 0.0283(4) Uani 1 1 d . . . . .
C32 C 0.9790(3) 0.5681(2) 0.8563(2) 0.0451(6) Uani 1 1 d . . . . .
H32 H 0.958905 0.635889 0.862588 0.054 Uiso 1 1 calc R U . . .
C33 C 1.1193(4) 0.5608(3) 0.9076(2) 0.0604(8) Uani 1 1 d . . . . .
H33 H 1.195388 0.623216 0.948982 0.073 Uiso 1 1 calc R U . . .
C34 C 1.1486(3) 0.4624(3) 0.8986(2) 0.0575(8) Uani 1 1 d . . . . .
H34 H 1.245591 0.457334 0.933280 0.069 Uiso 1 1 calc R U . . .
C35 C 1.0372(3) 0.3711(2) 0.8392(2) 0.0484(6) Uani 1 1 d . . . . .
H35 H 1.057342 0.303378 0.834026 0.058 Uiso 1 1 calc R U . . .
C36 C 0.8967(3) 0.37832(19) 0.78753(18) 0.0351(5) Uani 1 1 d . . . . .
H36 H 0.820635 0.315607 0.746609 0.042 Uiso 1 1 calc R U . . .
I1 I 1.11919(2) 0.88081(2) 0.78413(2) 0.04393(5) Uani 1 1 d . . . . .
C41 C 1.0473(2) 0.95093(18) 0.91296(17) 0.0314(5) Uani 1 1 d . . . . .
C42 C 1.0201(3) 1.04956(19) 0.91820(18) 0.0343(5) Uani 1 1 d . . . . .
C43 C 0.9736(3) 1.09830(18) 1.00390(18) 0.0337(5) Uani 1 1 d . . . . .
F42 F 1.0361(2) 1.10020(12) 0.83921(12) 0.0510(4) Uani 1 1 d . . . . .
F43 F 0.9476(2) 1.19349(12) 1.00421(12) 0.0511(4) Uani 1 1 d . . . . .
I2 I 0.58364(2) 0.76512(2) 0.89173(2) 0.03708(4) Uani 1 1 d . . . . .
C44 C 0.5346(3) 0.90521(18) 0.95791(17) 0.0323(5) Uani 1 1 d . . . . .
C45 C 0.5876(3) 0.99951(19) 0.92340(17) 0.0330(5) Uani 1 1 d . . . . .
C46 C 0.5543(3) 1.09195(18) 0.96425(18) 0.0333(5) Uani 1 1 d . . . . .
F45 F 0.67467(17) 1.00183(12) 0.84812(11) 0.0429(3) Uani 1 1 d . . . . .
F46 F 0.61050(18) 1.18083(12) 0.92764(12) 0.0466(4) Uani 1 1 d . . . . .
I3 I 0.83868(2) 1.20984(2) 0.49915(2) 0.02557(4) Uani 1 1 d . . . . .
C47 C 0.6364(2) 1.08404(15) 0.49929(16) 0.0237(4) Uani 1 1 d . . . . .
C48 C 0.5938(3) 1.06029(17) 0.59065(17) 0.0307(5) Uani 1 1 d . . . . .
C49 C 0.4606(3) 0.97818(18) 0.59068(16) 0.0302(4) Uani 1 1 d . . . . .
F48 F 0.68248(19) 1.11741(14) 0.68113(11) 0.0602(5) Uani 1 1 d . . . . .
F49 F 0.4265(2) 0.95845(14) 0.68180(11) 0.0633(5) 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
P1 O1 1.4906(16) . ?
P1 C11 1.786(2) . ?
P1 C21 1.791(2) . ?
P1 C31 1.799(2) . ?
C11 C12 1.383(3) . ?
C11 C20 1.424(3) . ?
C12 C13 1.401(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.354(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.423(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.412(3) . ?
C15 C20 1.432(3) . ?
C16 C17 1.353(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.406(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.440(3) . ?
C19 C22 1.479(3) . ?
C21 C26 1.399(3) . ?
C21 C22 1.406(3) . ?
C22 C23 1.411(3) . ?
C23 C24 1.379(3) . ?
C23 H23 0.9500 . ?
C24 N25 1.335(3) . ?
C24 H24 0.9500 . ?
N25 C26 1.330(3) . ?
C26 H26 0.9500 . ?
C31 C36 1.391(3) . ?
C31 C32 1.395(3) . ?
C32 C33 1.380(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.380(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.385(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.383(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
I1 C41 2.074(2) . ?
C41 C42 1.378(3) . ?
C41 C43 1.384(3) 2_777 ?
C42 F42 1.342(3) . ?
C42 C43 1.384(3) . ?
C43 F43 1.335(3) . ?
I2 C44 2.093(2) . ?
C44 C45 1.385(3) . ?
C44 C46 1.387(3) 2_677 ?
C45 F45 1.346(3) . ?
C45 C46 1.374(3) . ?
C46 F46 1.344(3) . ?
I3 C47 2.1037(19) . ?
C47 C49 1.378(3) 2_676 ?
C47 C48 1.383(3) . ?
C48 F48 1.339(2) . ?
C48 C49 1.379(3) . ?
C49 F49 1.341(2) . ?

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 P1 C11 114.67(11) . . ?
O1 P1 C21 113.02(10) . . ?
C11 P1 C21 102.97(10) . . ?
O1 P1 C31 111.32(10) . . ?
C11 P1 C31 108.04(10) . . ?
C21 P1 C31 106.16(10) . . ?
C12 C11 C20 120.5(2) . . ?
C12 C11 P1 116.22(19) . . ?
C20 C11 P1 123.14(16) . . ?
C11 C12 C13 121.4(3) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 119.6(2) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 121.5(2) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 C20 120.3(2) . . ?
C14 C15 C20 119.5(2) . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.3(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C19 C18 C17 122.6(2) . . ?
C19 C18 H18 118.7 . . ?
C17 C18 H18 118.7 . . ?
C18 C19 C20 118.04(19) . . ?
C18 C19 C22 119.31(19) . . ?
C20 C19 C22 122.65(18) . . ?
C11 C20 C15 117.52(19) . . ?
C11 C20 C19 123.92(18) . . ?
C15 C20 C19 118.6(2) . . ?
C26 C21 C22 119.22(19) . . ?
C26 C21 P1 116.94(16) . . ?
C22 C21 P1 123.79(15) . . ?
C21 C22 C23 115.21(18) . . ?
C21 C22 C19 123.06(18) . . ?
C23 C22 C19 121.73(19) . . ?
C24 C23 C22 120.6(2) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
N25 C24 C23 124.2(2) . . ?
N25 C24 H24 117.9 . . ?
C23 C24 H24 117.9 . . ?
C26 N25 C24 115.87(19) . . ?
N25 C26 C21 124.9(2) . . ?
N25 C26 H26 117.5 . . ?
C21 C26 H26 117.5 . . ?
C36 C31 C32 119.0(2) . . ?
C36 C31 P1 122.63(17) . . ?
C32 C31 P1 118.29(18) . . ?
C33 C32 C31 120.8(3) . . ?
C33 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C32 C33 C34 119.7(3) . . ?
C32 C33 H33 120.2 . . ?
C34 C33 H33 120.2 . . ?
C33 C34 C35 120.3(3) . . ?
C33 C34 H34 119.8 . . ?
C35 C34 H34 119.8 . . ?
C36 C35 C34 120.0(3) . . ?
C36 C35 H35 120.0 . . ?
C34 C35 H35 120.0 . . ?
C35 C36 C31 120.2(2) . . ?
C35 C36 H36 119.9 . . ?
C31 C36 H36 119.9 . . ?
C42 C41 C43 118.0(2) . 2_777 ?
C42 C41 I1 120.26(17) . . ?
C43 C41 I1 121.78(17) 2_777 . ?
F42 C42 C41 120.5(2) . . ?
F42 C42 C43 118.2(2) . . ?
C41 C42 C43 121.2(2) . . ?
F43 C43 C41 120.6(2) . 2_777 ?
F43 C43 C42 118.5(2) . . ?
C41 C43 C42 120.8(2) 2_777 . ?
C45 C44 C46 116.9(2) . 2_677 ?
C45 C44 I2 120.73(16) . . ?
C46 C44 I2 122.32(17) 2_677 . ?
F45 C45 C46 118.5(2) . . ?
F45 C45 C44 119.7(2) . . ?
C46 C45 C44 121.8(2) . . ?
F46 C46 C45 118.7(2) . . ?
F46 C46 C44 120.1(2) . 2_677 ?
C45 C46 C44 121.2(2) . 2_677 ?
C49 C47 C48 116.67(18) 2_676 . ?
C49 C47 I3 122.14(15) 2_676 . ?
C48 C47 I3 121.19(15) . . ?
F48 C48 C49 118.87(19) . . ?
F48 C48 C47 119.97(18) . . ?
C49 C48 C47 121.16(19) . . ?
F49 C49 C47 119.52(18) . 2_676 ?
F49 C49 C48 118.30(19) . . ?
C47 C49 C48 122.17(19) 2_676 . ?

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
O1 P1 C11 C12 -60.4(2) . . . . ?
C21 P1 C11 C12 176.40(19) . . . . ?
C31 P1 C11 C12 64.4(2) . . . . ?
O1 P1 C11 C20 115.69(18) . . . . ?
C21 P1 C11 C20 -7.5(2) . . . . ?
C31 P1 C11 C20 -119.54(18) . . . . ?
C20 C11 C12 C13 -0.9(4) . . . . ?
P1 C11 C12 C13 175.3(2) . . . . ?
C11 C12 C13 C14 0.7(4) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C13 C14 C15 C16 179.6(3) . . . . ?
C13 C14 C15 C20 0.3(4) . . . . ?
C14 C15 C16 C17 -179.7(2) . . . . ?
C20 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C16 C17 C18 C19 0.3(4) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
C17 C18 C19 C22 179.1(2) . . . . ?
C12 C11 C20 C15 0.8(3) . . . . ?
P1 C11 C20 C15 -175.19(15) . . . . ?
C12 C11 C20 C19 -179.3(2) . . . . ?
P1 C11 C20 C19 4.7(3) . . . . ?
C16 C15 C20 C11 -179.74(19) . . . . ?
C14 C15 C20 C11 -0.5(3) . . . . ?
C16 C15 C20 C19 0.3(3) . . . . ?
C14 C15 C20 C19 179.6(2) . . . . ?
C18 C19 C20 C11 -179.9(2) . . . . ?
C22 C19 C20 C11 0.7(3) . . . . ?
C18 C19 C20 C15 0.0(3) . . . . ?
C22 C19 C20 C15 -179.42(17) . . . . ?
O1 P1 C21 C26 59.68(19) . . . . ?
C11 P1 C21 C26 -176.05(17) . . . . ?
C31 P1 C21 C26 -62.62(18) . . . . ?
O1 P1 C21 C22 -117.52(18) . . . . ?
C11 P1 C21 C22 6.75(19) . . . . ?
C31 P1 C21 C22 120.18(17) . . . . ?
C26 C21 C22 C23 0.0(3) . . . . ?
P1 C21 C22 C23 177.15(15) . . . . ?
C26 C21 C22 C19 179.76(18) . . . . ?
P1 C21 C22 C19 -3.1(3) . . . . ?
C18 C19 C22 C21 179.05(19) . . . . ?
C20 C19 C22 C21 -1.5(3) . . . . ?
C18 C19 C22 C23 -1.2(3) . . . . ?
C20 C19 C22 C23 178.20(19) . . . . ?
C21 C22 C23 C24 -0.1(3) . . . . ?
C19 C22 C23 C24 -179.8(2) . . . . ?
C22 C23 C24 N25 0.0(4) . . . . ?
C23 C24 N25 C26 0.1(3) . . . . ?
C24 N25 C26 C21 -0.2(3) . . . . ?
C22 C21 C26 N25 0.1(3) . . . . ?
P1 C21 C26 N25 -177.21(18) . . . . ?
O1 P1 C31 C36 155.64(19) . . . . ?
C11 P1 C31 C36 28.9(2) . . . . ?
C21 P1 C31 C36 -81.0(2) . . . . ?
O1 P1 C31 C32 -28.1(2) . . . . ?
C11 P1 C31 C32 -154.82(19) . . . . ?
C21 P1 C31 C32 95.3(2) . . . . ?
C36 C31 C32 C33 0.6(4) . . . . ?
P1 C31 C32 C33 -175.8(2) . . . . ?
C31 C32 C33 C34 0.0(5) . . . . ?
C32 C33 C34 C35 -0.7(5) . . . . ?
C33 C34 C35 C36 0.8(5) . . . . ?
C34 C35 C36 C31 -0.3(4) . . . . ?
C32 C31 C36 C35 -0.4(4) . . . . ?
P1 C31 C36 C35 175.84(19) . . . . ?
C43 C41 C42 F42 -179.0(2) 2_777 . . . ?
I1 C41 C42 F42 1.6(3) . . . . ?
C43 C41 C42 C43 0.1(4) 2_777 . . . ?
I1 C41 C42 C43 -179.35(17) . . . . ?
F42 C42 C43 F43 -0.3(3) . . . . ?
C41 C42 C43 F43 -179.4(2) . . . . ?
F42 C42 C43 C41 179.0(2) . . . 2_777 ?
C41 C42 C43 C41 -0.1(4) . . . 2_777 ?
C46 C44 C45 F45 179.86(19) 2_677 . . . ?
I2 C44 C45 F45 -1.6(3) . . . . ?
C46 C44 C45 C46 0.2(4) 2_677 . . . ?
I2 C44 C45 C46 178.73(17) . . . . ?
F45 C45 C46 F46 -0.2(3) . . . . ?
C44 C45 C46 F46 179.5(2) . . . . ?
F45 C45 C46 C44 -179.9(2) . . . 2_677 ?
C44 C45 C46 C44 -0.2(4) . . . 2_677 ?
C49 C47 C48 F48 180.0(2) 2_676 . . . ?
I3 C47 C48 F48 -0.4(3) . . . . ?
C49 C47 C48 C49 0.0(4) 2_676 . . . ?
I3 C47 C48 C49 179.63(17) . . . . ?
F48 C48 C49 F49 -0.6(3) . . . . ?
C47 C48 C49 F49 179.4(2) . . . . ?
F48 C48 C49 C47 -180.0(2) . . . 2_676 ?
C47 C48 C49 C47 0.0(4) . . . 2_676 ?

_refine_diff_density_max         0.880
_refine_diff_density_min         -0.868
_refine_diff_density_rms         0.083




#==================================================================




####################################################################### 
# 
# 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_crn23
_database_code_depnum_ccdc_archive 'CCDC 2023735'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2021-05-19 deposited with the CCDC.	2021-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            compound1
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H14 N O P'
_chemical_formula_weight         327.30

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.4617(7)
_cell_length_b                   9.0098(8)
_cell_length_c                   23.284(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1565.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    680
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      16.84

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.182
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8408
_exptl_absorpt_correction_T_max  0.9579
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10079
_diffrn_reflns_av_unetI/netI     0.1551
_diffrn_reflns_av_R_equivalents  0.1200
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.749
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.026
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2752
_reflns_number_gt                1642
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 444 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.4(2)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2752
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1325
_refine_ls_R_factor_gt           0.0714
_refine_ls_wR_factor_ref         0.1458
_refine_ls_wR_factor_gt          0.1245
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
P1 P 0.5631(3) 0.4882(2) 0.62266(8) 0.0355(5) Uani 1 1 d . . . . .
O1 O 0.3729(6) 0.4729(5) 0.6403(2) 0.0451(14) Uani 1 1 d . . . . .
C11 C 0.6103(10) 0.4198(8) 0.5515(3) 0.0345(19) Uani 1 1 d . . . . .
C12 C 0.5756(11) 0.2719(8) 0.5439(3) 0.047(2) Uani 1 1 d . . . . .
H12 H 0.541108 0.212550 0.575744 0.056 Uiso 1 1 calc R U . . .
C13 C 0.5910(11) 0.2074(9) 0.4890(4) 0.052(2) Uani 1 1 d . . . . .
H13 H 0.568245 0.104575 0.483672 0.063 Uiso 1 1 calc R U . . .
C14 C 0.6379(11) 0.2925(11) 0.4444(4) 0.057(3) Uani 1 1 d . . . . .
H14 H 0.648282 0.248194 0.407557 0.069 Uiso 1 1 calc R U . . .
C15 C 0.6729(10) 0.4473(9) 0.4503(3) 0.043(2) Uani 1 1 d . . . . .
C16 C 0.7126(11) 0.5347(11) 0.4014(4) 0.057(3) Uani 1 1 d . . . . .
H16 H 0.722588 0.489768 0.364663 0.069 Uiso 1 1 calc R U . . .
C17 C 0.7367(11) 0.6852(11) 0.4076(4) 0.054(2) Uani 1 1 d . . . . .
H17 H 0.760599 0.745299 0.374955 0.064 Uiso 1 1 calc R U . . .
C18 C 0.7259(11) 0.7489(10) 0.4617(4) 0.053(2) Uani 1 1 d . . . . .
H18 H 0.740747 0.853260 0.464884 0.064 Uiso 1 1 calc R U . . .
C19 C 0.6949(10) 0.6692(9) 0.5109(4) 0.040(2) Uani 1 1 d . . . . .
C20 C 0.6594(9) 0.5124(9) 0.5056(3) 0.0359(18) Uani 1 1 d . . . . .
C21 C 0.6443(9) 0.6765(8) 0.6189(3) 0.0346(18) Uani 1 1 d . . . . .
C22 C 0.6970(10) 0.7449(8) 0.5674(3) 0.035(2) Uani 1 1 d . . . . .
C23 C 0.7565(10) 0.8927(8) 0.5738(4) 0.043(2) Uani 1 1 d . . . . .
H23 H 0.800378 0.944844 0.541258 0.052 Uiso 1 1 calc R U . . .
C24 C 0.7522(10) 0.9621(8) 0.6259(4) 0.045(2) Uani 1 1 d . . . . .
H24 H 0.790851 1.062180 0.629483 0.054 Uiso 1 1 calc R U . . .
C25 C 0.6915(10) 0.8857(8) 0.6730(4) 0.045(2) Uani 1 1 d . . . . .
H25 H 0.686338 0.935874 0.708884 0.054 Uiso 1 1 calc R U . . .
N26 N 0.6390(8) 0.7434(7) 0.6708(3) 0.0393(17) Uani 1 1 d . . . . .
C31 C 0.7128(10) 0.3937(7) 0.6707(3) 0.0327(18) Uani 1 1 d . . . . .
C32 C 0.8972(11) 0.4096(8) 0.6661(3) 0.039(2) Uani 1 1 d . . . . .
H32 H 0.945246 0.473152 0.637456 0.047 Uiso 1 1 calc R U . . .
C33 C 1.0124(11) 0.3346(8) 0.7027(3) 0.046(2) Uani 1 1 d . . . . .
H33 H 1.138523 0.346787 0.699549 0.055 Uiso 1 1 calc R U . . .
C34 C 0.9393(12) 0.2411(8) 0.7439(3) 0.045(2) Uani 1 1 d . . . . .
H34 H 1.016169 0.187636 0.769038 0.054 Uiso 1 1 calc R U . . .
C35 C 0.7583(12) 0.2254(8) 0.7486(3) 0.046(2) Uani 1 1 d . . . . .
H35 H 0.710290 0.161035 0.777057 0.055 Uiso 1 1 calc R U . . .
C36 C 0.6438(10) 0.3018(8) 0.7126(3) 0.038(2) Uani 1 1 d . . . . .
H36 H 0.517777 0.291143 0.716699 0.045 Uiso 1 1 calc R 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
P1 O1 1.484(5) . ?
P1 C31 1.796(7) . ?
P1 C11 1.803(7) . ?
P1 C21 1.804(7) . ?
C11 C12 1.369(9) . ?
C11 C20 1.405(10) . ?
C12 C13 1.409(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.336(11) . ?
C13 H13 0.9500 . ?
C14 C15 1.426(11) . ?
C14 H14 0.9500 . ?
C15 C16 1.415(11) . ?
C15 C20 1.419(9) . ?
C16 C17 1.376(11) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(11) . ?
C17 H17 0.9500 . ?
C18 C19 1.371(10) . ?
C18 H18 0.9500 . ?
C19 C20 1.442(10) . ?
C19 C22 1.482(10) . ?
C21 N26 1.351(8) . ?
C21 C22 1.405(10) . ?
C22 C23 1.412(9) . ?
C23 C24 1.365(10) . ?
C23 H23 0.9500 . ?
C24 C25 1.373(10) . ?
C24 H24 0.9500 . ?
C25 N26 1.342(8) . ?
C25 H25 0.9500 . ?
C31 C36 1.379(10) . ?
C31 C32 1.387(10) . ?
C32 C33 1.386(9) . ?
C32 H32 0.9500 . ?
C33 C34 1.389(9) . ?
C33 H33 0.9500 . ?
C34 C35 1.362(11) . ?
C34 H34 0.9500 . ?
C35 C36 1.381(10) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?

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 P1 C31 112.2(3) . . ?
O1 P1 C11 114.2(3) . . ?
C31 P1 C11 106.8(3) . . ?
O1 P1 C21 115.0(3) . . ?
C31 P1 C21 105.5(3) . . ?
C11 P1 C21 102.2(4) . . ?
C12 C11 C20 122.0(7) . . ?
C12 C11 P1 114.5(6) . . ?
C20 C11 P1 123.2(5) . . ?
C11 C12 C13 120.2(8) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 119.3(7) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 122.3(8) . . ?
C13 C14 H14 118.8 . . ?
C15 C14 H14 118.8 . . ?
C16 C15 C20 121.0(8) . . ?
C16 C15 C14 120.4(8) . . ?
C20 C15 C14 118.6(8) . . ?
C17 C16 C15 119.5(8) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 119.7(9) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C19 C18 C17 123.5(9) . . ?
C19 C18 H18 118.2 . . ?
C17 C18 H18 118.2 . . ?
C18 C19 C20 118.2(8) . . ?
C18 C19 C22 119.9(8) . . ?
C20 C19 C22 121.9(7) . . ?
C11 C20 C15 117.6(7) . . ?
C11 C20 C19 124.4(7) . . ?
C15 C20 C19 118.0(7) . . ?
N26 C21 C22 125.2(6) . . ?
N26 C21 P1 111.5(6) . . ?
C22 C21 P1 123.2(6) . . ?
C21 C22 C23 114.3(7) . . ?
C21 C22 C19 123.6(7) . . ?
C23 C22 C19 122.1(7) . . ?
C24 C23 C22 121.3(7) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C25 119.2(7) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 H24 120.4 . . ?
N26 C25 C24 123.0(8) . . ?
N26 C25 H25 118.5 . . ?
C24 C25 H25 118.5 . . ?
C25 N26 C21 116.9(7) . . ?
C36 C31 C32 119.1(7) . . ?
C36 C31 P1 119.5(6) . . ?
C32 C31 P1 121.3(6) . . ?
C33 C32 C31 121.2(7) . . ?
C33 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
C32 C33 C34 118.5(8) . . ?
C32 C33 H33 120.8 . . ?
C34 C33 H33 120.8 . . ?
C35 C34 C33 120.5(8) . . ?
C35 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C34 C35 C36 120.8(8) . . ?
C34 C35 H35 119.6 . . ?
C36 C35 H35 119.6 . . ?
C31 C36 C35 119.8(7) . . ?
C31 C36 H36 120.1 . . ?
C35 C36 H36 120.1 . . ?

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
O1 P1 C11 C12 -60.8(7) . . . . ?
C31 P1 C11 C12 63.9(7) . . . . ?
C21 P1 C11 C12 174.4(6) . . . . ?
O1 P1 C11 C20 112.4(6) . . . . ?
C31 P1 C11 C20 -122.9(6) . . . . ?
C21 P1 C11 C20 -12.4(7) . . . . ?
C20 C11 C12 C13 0.9(12) . . . . ?
P1 C11 C12 C13 174.2(6) . . . . ?
C11 C12 C13 C14 -0.7(13) . . . . ?
C12 C13 C14 C15 -0.2(13) . . . . ?
C13 C14 C15 C16 -176.5(8) . . . . ?
C13 C14 C15 C20 0.8(12) . . . . ?
C20 C15 C16 C17 -0.7(12) . . . . ?
C14 C15 C16 C17 176.6(8) . . . . ?
C15 C16 C17 C18 1.5(13) . . . . ?
C16 C17 C18 C19 1.1(13) . . . . ?
C17 C18 C19 C20 -4.4(12) . . . . ?
C17 C18 C19 C22 176.1(7) . . . . ?
C12 C11 C20 C15 -0.2(10) . . . . ?
P1 C11 C20 C15 -172.9(5) . . . . ?
C12 C11 C20 C19 179.0(7) . . . . ?
P1 C11 C20 C19 6.3(10) . . . . ?
C16 C15 C20 C11 176.7(7) . . . . ?
C14 C15 C20 C11 -0.6(10) . . . . ?
C16 C15 C20 C19 -2.6(10) . . . . ?
C14 C15 C20 C19 -179.9(7) . . . . ?
C18 C19 C20 C11 -174.3(7) . . . . ?
C22 C19 C20 C11 5.2(11) . . . . ?
C18 C19 C20 C15 5.0(10) . . . . ?
C22 C19 C20 C15 -175.5(6) . . . . ?
O1 P1 C21 N26 62.5(6) . . . . ?
C31 P1 C21 N26 -61.7(6) . . . . ?
C11 P1 C21 N26 -173.2(5) . . . . ?
O1 P1 C21 C22 -114.4(6) . . . . ?
C31 P1 C21 C22 121.4(6) . . . . ?
C11 P1 C21 C22 9.9(7) . . . . ?
N26 C21 C22 C23 3.5(10) . . . . ?
P1 C21 C22 C23 -180.0(5) . . . . ?
N26 C21 C22 C19 -177.7(6) . . . . ?
P1 C21 C22 C19 -1.2(10) . . . . ?
C18 C19 C22 C21 171.5(7) . . . . ?
C20 C19 C22 C21 -7.9(11) . . . . ?
C18 C19 C22 C23 -9.8(11) . . . . ?
C20 C19 C22 C23 170.7(7) . . . . ?
C21 C22 C23 C24 -3.3(10) . . . . ?
C19 C22 C23 C24 177.9(7) . . . . ?
C22 C23 C24 C25 1.0(12) . . . . ?
C23 C24 C25 N26 1.5(12) . . . . ?
C24 C25 N26 C21 -1.4(11) . . . . ?
C22 C21 N26 C25 -1.3(10) . . . . ?
P1 C21 N26 C25 -178.1(5) . . . . ?
O1 P1 C31 C36 9.0(7) . . . . ?
C11 P1 C31 C36 -116.8(6) . . . . ?
C21 P1 C31 C36 135.0(6) . . . . ?
O1 P1 C31 C32 -171.8(6) . . . . ?
C11 P1 C31 C32 62.4(7) . . . . ?
C21 P1 C31 C32 -45.8(7) . . . . ?
C36 C31 C32 C33 0.3(11) . . . . ?
P1 C31 C32 C33 -178.9(5) . . . . ?
C31 C32 C33 C34 0.6(11) . . . . ?
C32 C33 C34 C35 -0.8(11) . . . . ?
C33 C34 C35 C36 0.0(12) . . . . ?
C32 C31 C36 C35 -1.1(11) . . . . ?
P1 C31 C36 C35 178.1(6) . . . . ?
C34 C35 C36 C31 1.0(12) . . . . ?

_refine_diff_density_max         0.330
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.057



####################################################################### 
# 
# 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_crn33
_database_code_depnum_ccdc_archive 'CCDC 2023736'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2020-08-17 deposited with the CCDC.	2021-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'co-crystal 1'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H14 F4 I2 N O P'
_chemical_formula_weight         729.16

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'
P P 0.1023 0.0942 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   10.2170(4)
_cell_length_b                   10.7286(4)
_cell_length_c                   13.1032(5)
_cell_angle_alpha                85.5466(9)
_cell_angle_beta                 72.5399(9)
_cell_angle_gamma                64.1678(8)
_cell_volume                     1230.85(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9891
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      31.14

_exptl_crystal_description       brick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.967
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.147
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.104
_exptl_absorpt_coefficient_mu    2.673
_shelx_estimated_absorpt_T_min   0.695
_shelx_estimated_absorpt_T_max   0.769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7025
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            57841
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.632
_diffrn_reflns_theta_max         32.430
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8497
_reflns_number_gt                6865
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0225P)²+0.4972P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8497
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0552
_refine_ls_wR_factor_gt          0.0512
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_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
P1 P 0.15317(5) 0.38039(5) 0.69460(4) 0.02021(9) Uani 1 1 d . . . . .
O1 O 0.19310(15) 0.50061(14) 0.67897(11) 0.0271(3) Uani 1 1 d . . . . .
C11 C 0.15789(19) 0.31238(18) 0.57142(14) 0.0196(3) Uani 1 1 d . . . . .
N12 N 0.30033(17) 0.24708(16) 0.50349(12) 0.0248(3) Uani 1 1 d . . . . .
C13 C 0.3150(2) 0.2035(2) 0.40692(16) 0.0288(4) Uani 1 1 d . . . . .
H13 H 0.414586 0.156550 0.358919 0.035 Uiso 1 1 calc R U . . .
C14 C 0.1916(2) 0.2233(2) 0.37289(15) 0.0281(4) Uani 1 1 d . . . . .
H14 H 0.206612 0.191663 0.302731 0.034 Uiso 1 1 calc R U . . .
C15 C 0.0474(2) 0.28944(19) 0.44219(15) 0.0242(4) Uani 1 1 d . . . . .
H15 H -0.037914 0.302644 0.420045 0.029 Uiso 1 1 calc R U . . .
C16 C 0.0248(2) 0.33797(17) 0.54595(14) 0.0197(3) Uani 1 1 d . . . . .
C21 C -0.0385(2) 0.42550(19) 0.77646(15) 0.0231(4) Uani 1 1 d . . . . .
C22 C -0.0709(2) 0.4588(2) 0.88359(16) 0.0325(4) Uani 1 1 d . . . . .
H22 H 0.010217 0.439965 0.912527 0.039 Uiso 1 1 calc R U . . .
C23 C -0.2216(3) 0.5200(3) 0.95058(17) 0.0395(5) Uani 1 1 d . . . . .
H23 H -0.242439 0.543021 1.024103 0.047 Uiso 1 1 calc R U . . .
C24 C -0.3374(2) 0.5459(2) 0.90909(17) 0.0361(5) Uani 1 1 d . . . . .
H24 H -0.439423 0.589466 0.954159 0.043 Uiso 1 1 calc R U . . .
C25 C -0.3100(2) 0.5099(2) 0.80060(16) 0.0281(4) Uani 1 1 d . . . . .
C26 C -0.4325(2) 0.5358(2) 0.76018(19) 0.0349(5) Uani 1 1 d . . . . .
H26 H -0.533953 0.576755 0.806492 0.042 Uiso 1 1 calc R U . . .
C27 C -0.4066(2) 0.5027(2) 0.65543(18) 0.0346(5) Uani 1 1 d . . . . .
H27 H -0.489765 0.521463 0.628767 0.042 Uiso 1 1 calc R U . . .
C28 C -0.2566(2) 0.4408(2) 0.58686(17) 0.0280(4) Uani 1 1 d . . . . .
H28 H -0.240743 0.419480 0.513845 0.034 Uiso 1 1 calc R U . . .
C29 C -0.13102(19) 0.40968(18) 0.62165(14) 0.0206(3) Uani 1 1 d . . . . .
C30 C -0.1567(2) 0.44679(19) 0.73120(15) 0.0228(3) Uani 1 1 d . . . . .
C31 C 0.2782(2) 0.2439(2) 0.75679(14) 0.0236(4) Uani 1 1 d . . . . .
C32 C 0.2731(2) 0.1164(2) 0.77304(17) 0.0340(4) Uani 1 1 d . . . . .
H32 H 0.202742 0.098150 0.750392 0.041 Uiso 1 1 calc R U . . .
C33 C 0.3713(3) 0.0157(3) 0.82262(19) 0.0441(6) Uani 1 1 d . . . . .
H33 H 0.369740 -0.072376 0.832537 0.053 Uiso 1 1 calc R U . . .
C34 C 0.4715(3) 0.0438(3) 0.85754(18) 0.0487(7) Uani 1 1 d . . . . .
H34 H 0.537490 -0.024756 0.892232 0.058 Uiso 1 1 calc R U . . .
C35 C 0.4760(3) 0.1699(3) 0.84237(18) 0.0455(6) Uani 1 1 d . . . . .
H35 H 0.544638 0.188394 0.866921 0.055 Uiso 1 1 calc R U . . .
C36 C 0.3802(2) 0.2711(2) 0.79106(17) 0.0328(4) Uani 1 1 d . . . . .
H36 H 0.384462 0.357899 0.779584 0.039 Uiso 1 1 calc R U . . .
I1 I 0.61767(2) 0.15592(2) 0.50259(2) 0.03057(4) Uani 1 1 d . . . . .
C41 C 0.8465(2) 0.0658(2) 0.49906(16) 0.0264(4) Uani 1 1 d . . . . .
C42 C 0.9637(2) -0.0080(2) 0.40950(16) 0.0267(4) Uani 1 1 d . . . . .
C43 C 1.1136(2) -0.0718(2) 0.40971(16) 0.0268(4) Uani 1 1 d . . . . .
F42 F 0.93367(14) -0.02132(14) 0.31877(10) 0.0373(3) Uani 1 1 d . . . . .
F43 F 1.22083(14) -0.14056(14) 0.31975(10) 0.0377(3) Uani 1 1 d . . . . .
I2 I 0.09930(2) 0.72263(2) 0.82262(2) 0.02919(4) Uani 1 1 d . . . . .
C51 C 0.0399(2) 0.88747(19) 0.92935(15) 0.0255(4) Uani 1 1 d . . . . .
C52 C 0.1332(2) 0.8840(2) 0.98802(16) 0.0273(4) Uani 1 1 d . . . . .
C53 C 0.0949(2) 0.9935(2) 1.05672(16) 0.0272(4) Uani 1 1 d . . . . .
F52 F 0.26769(14) 0.77200(13) 0.97759(11) 0.0410(3) Uani 1 1 d . . . . .
F53 F 0.19296(14) 0.98365(13) 1.10965(11) 0.0413(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
P1 O1 1.4964(14) . ?
P1 C21 1.7928(18) . ?
P1 C11 1.8016(18) . ?
P1 C31 1.8025(18) . ?
C11 N12 1.353(2) . ?
C11 C16 1.403(2) . ?
N12 C13 1.326(2) . ?
C13 C14 1.387(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.373(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.410(2) . ?
C15 H15 0.9500 . ?
C16 C29 1.488(2) . ?
C21 C22 1.380(3) . ?
C21 C30 1.425(2) . ?
C22 C23 1.403(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.360(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.415(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.413(3) . ?
C25 C30 1.434(3) . ?
C26 C27 1.362(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.406(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.386(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.435(3) . ?
C31 C32 1.389(3) . ?
C31 C36 1.391(3) . ?
C32 C33 1.391(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.385(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.370(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.394(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
I1 C41 2.0914(18) . ?
C41 C42 1.383(3) . ?
C41 C43 1.388(3) 2_756 ?
C42 F42 1.346(2) . ?
C42 C43 1.380(3) . ?
C43 F43 1.338(2) . ?
I2 C51 2.0955(18) . ?
C51 C52 1.381(3) . ?
C51 C53 1.383(3) 2_577 ?
C52 F52 1.351(2) . ?
C52 C53 1.376(3) . ?
C53 F53 1.345(2) . ?

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 P1 C21 113.22(8) . . ?
O1 P1 C11 112.78(8) . . ?
C21 P1 C11 102.58(8) . . ?
O1 P1 C31 110.62(9) . . ?
C21 P1 C31 107.60(9) . . ?
C11 P1 C31 109.66(8) . . ?
N12 C11 C16 124.24(16) . . ?
N12 C11 P1 113.22(12) . . ?
C16 C11 P1 122.26(13) . . ?
C13 N12 C11 117.86(16) . . ?
N12 C13 C14 122.94(18) . . ?
N12 C13 H13 118.5 . . ?
C14 C13 H13 118.5 . . ?
C15 C14 C13 118.94(17) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 120.64(17) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 115.38(16) . . ?
C11 C16 C29 123.57(16) . . ?
C15 C16 C29 121.05(16) . . ?
C22 C21 C30 121.01(17) . . ?
C22 C21 P1 116.49(14) . . ?
C30 C21 P1 121.82(14) . . ?
C21 C22 C23 121.18(19) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 H22 119.4 . . ?
C24 C23 C22 119.3(2) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C23 C24 C25 121.76(19) . . ?
C23 C24 H24 119.1 . . ?
C25 C24 H24 119.1 . . ?
C26 C25 C24 120.52(18) . . ?
C26 C25 C30 119.82(19) . . ?
C24 C25 C30 119.66(18) . . ?
C27 C26 C25 120.65(19) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C26 C27 C28 119.88(19) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C29 C28 C27 122.54(19) . . ?
C29 C28 H28 118.7 . . ?
C27 C28 H28 118.7 . . ?
C28 C29 C30 118.17(17) . . ?
C28 C29 C16 119.65(17) . . ?
C30 C29 C16 122.17(15) . . ?
C21 C30 C25 117.05(17) . . ?
C21 C30 C29 124.04(16) . . ?
C25 C30 C29 118.90(17) . . ?
C32 C31 C36 120.06(18) . . ?
C32 C31 P1 122.31(15) . . ?
C36 C31 P1 117.62(16) . . ?
C31 C32 C33 119.7(2) . . ?
C31 C32 H32 120.2 . . ?
C33 C32 H32 120.2 . . ?
C34 C33 C32 120.0(2) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C35 C34 C33 120.4(2) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C34 C35 C36 120.3(2) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C31 C36 C35 119.5(2) . . ?
C31 C36 H36 120.2 . . ?
C35 C36 H36 120.2 . . ?
C42 C41 C43 116.84(17) . 2_756 ?
C42 C41 I1 122.61(14) . . ?
C43 C41 I1 120.47(14) 2_756 . ?
F42 C42 C43 117.67(18) . . ?
F42 C42 C41 120.32(17) . . ?
C43 C42 C41 122.00(18) . . ?
F43 C43 C42 118.55(17) . . ?
F43 C43 C41 120.29(17) . 2_756 ?
C42 C43 C41 121.16(18) . 2_756 ?
C52 C51 C53 116.66(17) . 2_577 ?
C52 C51 I2 122.10(13) . . ?
C53 C51 I2 121.24(14) 2_577 . ?
F52 C52 C53 118.03(16) . . ?
F52 C52 C51 120.06(17) . . ?
C53 C52 C51 121.90(17) . . ?
F53 C53 C52 118.51(16) . . ?
F53 C53 C51 120.04(17) . 2_577 ?
C52 C53 C51 121.44(17) . 2_577 ?

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
O1 P1 C11 N12 69.59(15) . . . . ?
C21 P1 C11 N12 -168.28(13) . . . . ?
C31 P1 C11 N12 -54.16(15) . . . . ?
O1 P1 C11 C16 -104.47(15) . . . . ?
C21 P1 C11 C16 17.66(17) . . . . ?
C31 P1 C11 C16 131.78(15) . . . . ?
C16 C11 N12 C13 -0.6(3) . . . . ?
P1 C11 N12 C13 -174.49(15) . . . . ?
C11 N12 C13 C14 0.7(3) . . . . ?
N12 C13 C14 C15 -0.8(3) . . . . ?
C13 C14 C15 C16 0.7(3) . . . . ?
N12 C11 C16 C15 0.5(3) . . . . ?
P1 C11 C16 C15 173.88(13) . . . . ?
N12 C11 C16 C29 179.87(16) . . . . ?
P1 C11 C16 C29 -6.7(2) . . . . ?
C14 C15 C16 C11 -0.6(3) . . . . ?
C14 C15 C16 C29 -179.97(17) . . . . ?
O1 P1 C21 C22 -69.11(18) . . . . ?
C11 P1 C21 C22 169.06(16) . . . . ?
C31 P1 C21 C22 53.45(18) . . . . ?
O1 P1 C21 C30 101.53(16) . . . . ?
C11 P1 C21 C30 -20.30(17) . . . . ?
C31 P1 C21 C30 -135.91(16) . . . . ?
C30 C21 C22 C23 -2.7(3) . . . . ?
P1 C21 C22 C23 168.05(18) . . . . ?
C21 C22 C23 C24 0.4(4) . . . . ?
C22 C23 C24 C25 1.5(4) . . . . ?
C23 C24 C25 C26 178.9(2) . . . . ?
C23 C24 C25 C30 -1.3(3) . . . . ?
C24 C25 C26 C27 179.2(2) . . . . ?
C30 C25 C26 C27 -0.6(3) . . . . ?
C25 C26 C27 C28 0.7(3) . . . . ?
C26 C27 C28 C29 0.8(3) . . . . ?
C27 C28 C29 C30 -2.1(3) . . . . ?
C27 C28 C29 C16 177.06(18) . . . . ?
C11 C16 C29 C28 174.67(17) . . . . ?
C15 C16 C29 C28 -6.0(3) . . . . ?
C11 C16 C29 C30 -6.2(3) . . . . ?
C15 C16 C29 C30 173.17(17) . . . . ?
C22 C21 C30 C25 2.8(3) . . . . ?
P1 C21 C30 C25 -167.42(14) . . . . ?
C22 C21 C30 C29 -177.49(19) . . . . ?
P1 C21 C30 C29 12.3(3) . . . . ?
C26 C25 C30 C21 178.99(18) . . . . ?
C24 C25 C30 C21 -0.9(3) . . . . ?
C26 C25 C30 C29 -0.7(3) . . . . ?
C24 C25 C30 C29 179.42(19) . . . . ?
C28 C29 C30 C21 -177.64(17) . . . . ?
C16 C29 C30 C21 3.2(3) . . . . ?
C28 C29 C30 C25 2.1(3) . . . . ?
C16 C29 C30 C25 -177.10(16) . . . . ?
O1 P1 C31 C32 -175.10(16) . . . . ?
C21 P1 C31 C32 60.75(18) . . . . ?
C11 P1 C31 C32 -50.10(18) . . . . ?
O1 P1 C31 C36 6.30(18) . . . . ?
C21 P1 C31 C36 -117.84(16) . . . . ?
C11 P1 C31 C36 131.31(15) . . . . ?
C36 C31 C32 C33 -0.7(3) . . . . ?
P1 C31 C32 C33 -179.25(17) . . . . ?
C31 C32 C33 C34 1.3(3) . . . . ?
C32 C33 C34 C35 -0.8(4) . . . . ?
C33 C34 C35 C36 -0.3(4) . . . . ?
C32 C31 C36 C35 -0.5(3) . . . . ?
P1 C31 C36 C35 178.16(16) . . . . ?
C34 C35 C36 C31 1.0(3) . . . . ?
C43 C41 C42 F42 178.41(17) 2_756 . . . ?
I1 C41 C42 F42 1.8(3) . . . . ?
C43 C41 C42 C43 -0.6(3) 2_756 . . . ?
I1 C41 C42 C43 -177.23(15) . . . . ?
F42 C42 C43 F43 1.4(3) . . . . ?
C41 C42 C43 F43 -179.53(18) . . . . ?
F42 C42 C43 C41 -178.41(17) . . . 2_756 ?
C41 C42 C43 C41 0.7(3) . . . 2_756 ?
C53 C51 C52 F52 -179.11(19) 2_577 . . . ?
I2 C51 C52 F52 0.0(3) . . . . ?
C53 C51 C52 C53 -0.2(3) 2_577 . . . ?
I2 C51 C52 C53 178.91(16) . . . . ?
F52 C52 C53 F53 0.2(3) . . . . ?
C51 C52 C53 F53 -178.74(19) . . . . ?
F52 C52 C53 C51 179.15(19) . . . 2_577 ?
C51 C52 C53 C51 0.3(4) . . . 2_577 ?

_refine_diff_density_max         0.725
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.088


