# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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. 
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data_RMH3_258_0m
_database_code_depnum_ccdc_archive 'CCDC 2414370'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2025-01-03 deposited with the CCDC.	2025-10-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H40 F2 N2 O5, 0.25(C6 H14)'
_chemical_formula_sum            'C43.50 H43.50 F2 N2 O5'
_chemical_formula_weight         712.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   43.884(9)
_cell_length_b                   5.5853(12)
_cell_length_c                   15.050(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.925(12)
_cell_angle_gamma                90
_cell_volume                     3684.0(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7389
_cell_measurement_theta_min      2.9401
_cell_measurement_theta_max      79.1913

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             1506
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.738
_shelx_estimated_absorpt_T_min   0.732
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5559
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S 3.0 microsource X-ray tube'
_diffrn_source_current           '1.1 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'HELIOS multilayer Montel optics'
_diffrn_measurement_device       'four circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_detector_type            
'PhotonIII_C14 charge-integrating and photon counting pixel array'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            18691
_diffrn_reflns_av_unetI/netI     0.0844
_diffrn_reflns_av_R_equivalents  0.0867
_diffrn_reflns_limit_h_min       -55
_diffrn_reflns_limit_h_max       55
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.016
_diffrn_reflns_theta_max         80.214
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             7038
_reflns_number_gt                4584
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.661
_reflns_Friedel_fraction_max     0.778
_reflns_Friedel_fraction_full    0.907

_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       'Apex5 v2023.9-2 (Bruker, 2023)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015b)'
_computing_structure_refinement  
;  
SHELXL-2019/2 (Sheldrick, 2015a, 2019), 
SHELXLE Rev1613 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
One of the phenyl rings was refined as disordered. The ipso C-atom 
was excluded from the disorder. The two disordered moieties were 
restrained to have similar geometries. Uij components of ADPs for 
disordered atoms closer to each other than 2.0 Angstrom were 
restrained to be similar. Subject to these conditions the occupancy 
ratio refined to 0.533(19) to 0.467(19).

A hexane molecule is incommensurate with the crystal unit cell 
and stretches over the length of two lengths of the cell along 
the b-axis direction. No satellite reflections indicating a 
doubling of the unit cell are observed and the hexane molecule 
was thus refined as disordered. The molecule is also aligned along 
a two-fold axis, thus leading to quarter occupancy for the 
independent hexane molecule atoms. Bond distances and angles 
were restrained to expected target values (1.53(2) and 2.50(2) A
for bond distances and 1,3 distances respectively), Uij components 
of ADPs for disordered atoms closer to each other than 2.0 
Angstrom were restrained to be similar and atoms to be close to 
isotropic. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0549P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_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 1376 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.23(16)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7038
_refine_ls_number_parameters     560
_refine_ls_number_restraints     292
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1338
_refine_ls_wR_factor_gt          0.1190
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.968
_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
F1 F 0.29406(6) 0.0934(5) 0.26760(15) 0.0664(7) Uani 1 1 d . . . . .
F2 F 0.29453(5) 0.4128(4) 0.34886(14) 0.0540(6) Uani 1 1 d . . . . .
O1 O 0.32655(7) 0.4225(5) 0.15908(16) 0.0549(7) Uani 1 1 d . . . . .
O2 O 0.40854(8) 0.1461(6) 0.5018(2) 0.0711(9) Uani 1 1 d . . . . .
O3 O 0.42805(7) 0.5454(6) 0.2845(2) 0.0613(8) Uani 1 1 d . . . . .
O4 O 0.35979(6) 0.3198(5) 0.38243(15) 0.0460(7) Uani 1 1 d . . . . .
O6 O 0.38000(7) 0.7220(5) 0.16674(17) 0.0593(8) Uani 1 1 d . . . . .
N1 N 0.31017(8) 0.0706(6) 0.4130(2) 0.0456(8) Uani 1 1 d . . . . .
N2 N 0.32795(8) -0.1308(6) 0.4146(2) 0.0524(8) Uani 1 1 d . . . . .
C1 C 0.40801(11) 0.3696(9) 0.4565(3) 0.0630(12) Uani 1 1 d . . . . .
H1A H 0.429107 0.425461 0.448536 0.076 Uiso 1 1 calc R U . . .
H1B H 0.397441 0.491047 0.491613 0.076 Uiso 1 1 calc R U . . .
C2 C 0.39167(10) 0.3377(8) 0.3683(3) 0.0521(11) Uani 1 1 d . . . . .
H2 H 0.398773 0.186757 0.340162 0.062 Uiso 1 1 calc R U . . .
C3 C 0.39655(10) 0.5482(8) 0.3059(3) 0.0510(10) Uani 1 1 d . . . . .
H3 H 0.391624 0.702109 0.335917 0.061 Uiso 1 1 calc R U . . .
C4 C 0.37670(10) 0.5191(8) 0.2214(3) 0.0516(10) Uani 1 1 d . . . . .
H4 H 0.384169 0.376329 0.188875 0.062 Uiso 1 1 calc R U . . .
C5 C 0.34352(10) 0.4765(7) 0.2403(2) 0.0480(10) Uani 1 1 d . . . . .
H5 H 0.334904 0.622688 0.268082 0.058 Uiso 1 1 calc R U . . .
C6 C 0.34207(10) 0.2646(8) 0.3047(2) 0.0475(9) Uani 1 1 d . . . . .
H6 H 0.350634 0.119078 0.276356 0.057 Uiso 1 1 calc R U . . .
C7 C 0.31034(10) 0.2094(7) 0.3339(3) 0.0492(10) Uani 1 1 d . . . . .
C8 C 0.32499(10) -0.2281(8) 0.4930(3) 0.0510(10) Uani 1 1 d . . . . .
H8 H 0.334727 -0.372277 0.512176 0.061 Uiso 1 1 calc R U . . .
C9 C 0.30548(9) -0.0916(7) 0.5455(2) 0.0437(9) Uani 1 1 d . . . . .
C10 C 0.29465(9) -0.1159(8) 0.6312(2) 0.0469(9) Uani 1 1 d . . . . .
H10 H 0.300691 -0.247789 0.667874 0.056 Uiso 1 1 calc R U . . .
C11 C 0.27512(9) 0.0554(8) 0.6609(2) 0.0483(10) Uani 1 1 d . . . . .
H11 H 0.267536 0.042173 0.718657 0.058 Uiso 1 1 calc R U . . .
C12 C 0.26632(9) 0.2495(8) 0.6065(2) 0.0490(10) Uani 1 1 d . . . . .
H12 H 0.252915 0.365968 0.628789 0.059 Uiso 1 1 calc R U . . .
C13 C 0.27632(9) 0.2781(7) 0.5221(2) 0.0441(9) Uani 1 1 d . . . . .
H13 H 0.270112 0.410167 0.485715 0.053 Uiso 1 1 calc R U . . .
C14 C 0.29605(8) 0.1031(7) 0.4926(2) 0.0412(9) Uani 1 1 d . . . . .
C15 C 0.42047(12) 0.1638(11) 0.5916(3) 0.0774(15) Uani 1 1 d . . . . .
H15A H 0.441143 0.234975 0.592322 0.093 Uiso 1 1 calc R U . . .
H15B H 0.422294 0.001373 0.617662 0.093 Uiso 1 1 calc R U . . .
C16 C 0.40035(12) 0.3153(9) 0.6475(3) 0.0642(13) Uani 1 1 d . . . . .
C17 C 0.36946(12) 0.2621(10) 0.6511(3) 0.0672(13) Uani 1 1 d . . . . .
H17 H 0.361224 0.127409 0.619721 0.081 Uiso 1 1 calc R U . . .
C18 C 0.35095(12) 0.4018(11) 0.6993(3) 0.0705(13) Uani 1 1 d . . . . .
H18 H 0.329903 0.363322 0.701170 0.085 Uiso 1 1 calc R U . . .
C19 C 0.36234(13) 0.5978(10) 0.7453(3) 0.0736(14) Uani 1 1 d . . . . .
H19 H 0.349308 0.694842 0.778678 0.088 Uiso 1 1 calc R U . . .
C20 C 0.39291(14) 0.6515(10) 0.7423(4) 0.0783(15) Uani 1 1 d . . . . .
H20 H 0.401071 0.785498 0.774258 0.094 Uiso 1 1 calc R U . . .
C21 C 0.41167(13) 0.5121(11) 0.6933(4) 0.0759(15) Uani 1 1 d . . . . .
H21 H 0.432663 0.552020 0.691029 0.091 Uiso 1 1 calc R U . . .
C22 C 0.44232(12) 0.7728(9) 0.2875(3) 0.0663(13) Uani 1 1 d . . . . .
H22A H 0.446033 0.823268 0.350214 0.080 Uiso 1 1 calc R U . A 1
H22B H 0.428793 0.892576 0.257239 0.080 Uiso 1 1 calc R U . A 1
C23 C 0.47197(11) 0.7609(9) 0.2427(3) 0.0621(11) Uani 0.533(19) 1 d D U P B 1
C24 C 0.4957(3) 0.927(2) 0.2661(10) 0.073(3) Uani 0.533(19) 1 d D U P B 1
H24 H 0.493244 1.036658 0.313371 0.088 Uiso 0.533(19) 1 calc R U P B 1
C25 C 0.5223(3) 0.929(3) 0.2201(10) 0.080(3) Uani 0.533(19) 1 d D U P B 1
H25 H 0.538738 1.030207 0.238968 0.096 Uiso 0.533(19) 1 calc R U P B 1
C26 C 0.5248(5) 0.782(4) 0.1470(16) 0.082(3) Uani 0.533(19) 1 d D U P B 1
H26 H 0.541271 0.802437 0.108954 0.099 Uiso 0.533(19) 1 calc R U P B 1
C27 C 0.5033(4) 0.607(3) 0.1297(10) 0.082(3) Uani 0.533(19) 1 d D U P B 1
H27 H 0.506249 0.490638 0.084821 0.098 Uiso 0.533(19) 1 calc R U P B 1
C28 C 0.4771(4) 0.601(3) 0.1787(9) 0.069(3) Uani 0.533(19) 1 d D U P B 1
H28 H 0.462374 0.479630 0.166203 0.083 Uiso 0.533(19) 1 calc R U P B 1
C23B C 0.47197(11) 0.7609(9) 0.2427(3) 0.0621(11) Uani 0.467(19) 1 d D U P B 2
C24B C 0.4878(3) 0.972(2) 0.2312(11) 0.071(3) Uani 0.467(19) 1 d D U P B 2
H24B H 0.479853 1.118929 0.252096 0.086 Uiso 0.467(19) 1 calc R U P B 2
C25B C 0.5151(4) 0.970(3) 0.1893(12) 0.080(3) Uani 0.467(19) 1 d D U P B 2
H25B H 0.526035 1.114810 0.182311 0.096 Uiso 0.467(19) 1 calc R U P B 2
C26B C 0.5266(6) 0.760(4) 0.1577(19) 0.082(3) Uani 0.467(19) 1 d D U P B 2
H26B H 0.546581 0.754341 0.136448 0.098 Uiso 0.467(19) 1 calc R U P B 2
C27B C 0.5087(4) 0.558(3) 0.1572(12) 0.079(3) Uani 0.467(19) 1 d D U P B 2
H27B H 0.515069 0.417693 0.127585 0.094 Uiso 0.467(19) 1 calc R U P B 2
C28B C 0.4810(4) 0.558(3) 0.2003(11) 0.069(3) Uani 0.467(19) 1 d D U P B 2
H28B H 0.468683 0.418045 0.199950 0.082 Uiso 0.467(19) 1 calc R U P B 2
C29 C 0.38703(17) 0.6600(11) 0.0785(3) 0.0903(19) Uani 1 1 d . . . . .
H29A H 0.369044 0.584103 0.047677 0.108 Uiso 1 1 calc R U . . .
H29B H 0.404018 0.543122 0.080163 0.108 Uiso 1 1 calc R U . . .
C30 C 0.39597(12) 0.8799(9) 0.0281(3) 0.0627(12) Uani 1 1 d . . . . .
C31 C 0.37792(14) 0.9748(11) -0.0382(3) 0.0774(15) Uani 1 1 d . . . . .
H31 H 0.358028 0.911946 -0.050387 0.093 Uiso 1 1 calc R U . . .
C32 C 0.3881(2) 1.1609(12) -0.0878(4) 0.099(2) Uani 1 1 d . . . . .
H32 H 0.375387 1.222684 -0.135448 0.119 Uiso 1 1 calc R U . . .
C33 C 0.4161(2) 1.2583(12) -0.0699(4) 0.093(2) Uani 1 1 d . . . . .
H33 H 0.422594 1.390250 -0.103894 0.112 Uiso 1 1 calc R U . . .
C34 C 0.43438(15) 1.1695(11) -0.0047(4) 0.0860(17) Uani 1 1 d . . . . .
H34 H 0.453942 1.237917 0.007867 0.103 Uiso 1 1 calc R U . . .
C35 C 0.42480(14) 0.9776(11) 0.0444(3) 0.0823(17) Uani 1 1 d . . . . .
H35 H 0.438085 0.911561 0.089801 0.099 Uiso 1 1 calc R U . . .
C36 C 0.30770(11) 0.6140(8) 0.1266(3) 0.0586(11) Uani 1 1 d . . . . .
H36A H 0.319147 0.766528 0.131580 0.070 Uiso 1 1 calc R U . . .
H36B H 0.289578 0.627399 0.162897 0.070 Uiso 1 1 calc R U . . .
C37 C 0.29774(10) 0.5692(8) 0.0312(2) 0.0514(10) Uani 1 1 d D . . . .
C38 C 0.27851(12) 0.7340(8) -0.0122(3) 0.0612(12) Uani 1 1 d D . . . .
H38 H 0.271898 0.870466 0.019193 0.073 Uiso 1 1 calc R U . . .
C39 C 0.26890(12) 0.7030(9) -0.0997(3) 0.0650(13) Uani 1 1 d D . . . .
H39 H 0.255658 0.817158 -0.128192 0.078 Uiso 1 1 calc R U . . .
C40 C 0.27839(12) 0.5074(9) -0.1461(3) 0.0617(12) Uani 1 1 d D . . . .
H40 H 0.272013 0.486815 -0.206862 0.074 Uiso 1 1 calc R U . . .
C41 C 0.29721(12) 0.3415(8) -0.1039(3) 0.0654(13) Uani 1 1 d D . . . .
H41 H 0.303540 0.204721 -0.135599 0.078 Uiso 1 1 calc R U . . .
C42 C 0.30700(11) 0.3713(8) -0.0160(3) 0.0599(12) Uani 1 1 d D . . . .
H42 H 0.320127 0.255839 0.012232 0.072 Uiso 1 1 calc R U . . .
C43 C 0.5013(15) 0.540(6) 0.477(3) 0.125(11) Uani 0.25 1 d D U P C -1
H43A H 0.506483 0.675891 0.515933 0.188 Uiso 0.25 1 calc R U P C -1
H43B H 0.515442 0.535447 0.428328 0.188 Uiso 0.25 1 calc R U P C -1
H43C H 0.480388 0.559298 0.451550 0.188 Uiso 0.25 1 calc R U P C -1
C44 C 0.5039(10) 0.296(6) 0.532(2) 0.118(8) Uani 0.25 1 d D U P C -1
H44A H 0.524930 0.273783 0.558105 0.142 Uiso 0.25 1 calc R U P C -1
H44B H 0.489692 0.297760 0.581449 0.142 Uiso 0.25 1 calc R U P C -1
C45 C 0.4956(8) 0.098(6) 0.4675(16) 0.120(7) Uani 0.25 1 d D U P C -1
H45A H 0.511703 0.076935 0.424389 0.144 Uiso 0.25 1 calc R U P C -1
H45B H 0.476045 0.132791 0.434468 0.144 Uiso 0.25 1 calc R U P C -1
C46 C 0.4928(7) -0.135(5) 0.5274(18) 0.114(7) Uani 0.25 1 d D U P C -1
H46A H 0.501580 -0.105920 0.588221 0.137 Uiso 0.25 1 calc R U P C -1
H46B H 0.471066 -0.181106 0.531303 0.137 Uiso 0.25 1 calc R U P C -1
C47 C 0.5100(8) -0.330(7) 0.483(2) 0.123(8) Uani 0.25 1 d D U P C -1
H47A H 0.532310 -0.302526 0.489472 0.148 Uiso 0.25 1 calc R U P C -1
H47B H 0.503768 -0.342960 0.419129 0.148 Uiso 0.25 1 calc R U P C -1
C48 C 0.5001(11) -0.568(7) 0.538(3) 0.135(11) Uani 0.25 1 d D U P C -1
H48A H 0.510235 -0.708660 0.514235 0.202 Uiso 0.25 1 calc R U P C -1
H48B H 0.506249 -0.548293 0.600995 0.202 Uiso 0.25 1 calc R U P C -1
H48C H 0.477951 -0.588382 0.531251 0.202 Uiso 0.25 1 calc R U P C -1


_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 C7 1.361(5) . ?
F2 C7 1.356(5) . ?
O1 C36 1.423(5) . ?
O1 C5 1.431(5) . ?
O2 C1 1.422(6) . ?
O2 C15 1.428(6) . ?
O3 C22 1.416(6) . ?
O3 C3 1.435(5) . ?
O4 C6 1.405(5) . ?
O4 C2 1.430(5) . ?
O6 C4 1.412(5) . ?
O6 C29 1.422(5) . ?
N1 N2 1.369(5) . ?
N1 C14 1.390(5) . ?
N1 C7 1.421(5) . ?
N2 C8 1.311(5) . ?
C1 C2 1.486(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.527(6) . ?
C2 H2 1.0000 . ?
C3 C4 1.512(6) . ?
C3 H3 1.0000 . ?
C4 C5 1.516(6) . ?
C4 H4 1.0000 . ?
C5 C6 1.533(5) . ?
C5 H5 1.0000 . ?
C6 C7 1.513(6) . ?
C6 H6 1.0000 . ?
C8 C9 1.417(6) . ?
C8 H8 0.9500 . ?
C9 C14 1.398(5) . ?
C9 C10 1.404(5) . ?
C10 C11 1.374(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.401(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(6) . ?
C13 H13 0.9500 . ?
C15 C16 1.510(8) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C21 1.377(7) . ?
C16 C17 1.391(7) . ?
C17 C18 1.362(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.376(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.378(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.374(8) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23B 1.497(7) . ?
C22 C23 1.497(7) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C28 1.340(12) . ?
C23 C24 1.423(11) . ?
C24 C25 1.388(12) . ?
C24 H24 0.9500 . ?
C25 C26 1.380(17) . ?
C25 H25 0.9500 . ?
C26 C27 1.376(15) . ?
C26 H26 0.9500 . ?
C27 C28 1.399(13) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C23B C28B 1.371(14) . ?
C23B C24B 1.384(12) . ?
C24B C25B 1.384(14) . ?
C24B H24B 0.9500 . ?
C25B C26B 1.369(18) . ?
C25B H25B 0.9500 . ?
C26B C27B 1.375(16) . ?
C26B H26B 0.9500 . ?
C27B C28B 1.406(14) . ?
C27B H27B 0.9500 . ?
C28B H28B 0.9500 . ?
C29 C30 1.506(7) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.350(7) . ?
C30 C35 1.388(8) . ?
C31 C32 1.368(8) . ?
C31 H31 0.9500 . ?
C32 C33 1.358(10) . ?
C32 H32 0.9500 . ?
C33 C34 1.331(9) . ?
C33 H33 0.9500 . ?
C34 C35 1.380(8) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 C37 1.500(6) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C42 1.386(6) . ?
C37 C38 1.389(6) . ?
C38 C39 1.373(6) . ?
C38 H38 0.9500 . ?
C39 C40 1.373(6) . ?
C39 H39 0.9500 . ?
C40 C41 1.375(6) . ?
C40 H40 0.9500 . ?
C41 C42 1.380(6) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 C44 1.60(2) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 C45 1.51(2) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C46 1.59(2) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 C47 1.50(2) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C48 1.63(2) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C36 O1 C5 113.7(3) . . ?
C1 O2 C15 112.9(4) . . ?
C22 O3 C3 114.4(3) . . ?
C6 O4 C2 113.3(3) . . ?
C4 O6 C29 112.5(4) . . ?
N2 N1 C14 111.8(3) . . ?
N2 N1 C7 115.8(3) . . ?
C14 N1 C7 132.3(3) . . ?
C8 N2 N1 105.9(3) . . ?
O2 C1 C2 108.5(4) . . ?
O2 C1 H1A 110.0 . . ?
C2 C1 H1A 110.0 . . ?
O2 C1 H1B 110.0 . . ?
C2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
O4 C2 C1 107.8(3) . . ?
O4 C2 C3 108.3(3) . . ?
C1 C2 C3 112.4(4) . . ?
O4 C2 H2 109.4 . . ?
C1 C2 H2 109.4 . . ?
C3 C2 H2 109.4 . . ?
O3 C3 C4 109.3(3) . . ?
O3 C3 C2 107.3(3) . . ?
C4 C3 C2 110.0(4) . . ?
O3 C3 H3 110.1 . . ?
C4 C3 H3 110.1 . . ?
C2 C3 H3 110.1 . . ?
O6 C4 C3 109.4(4) . . ?
O6 C4 C5 111.3(4) . . ?
C3 C4 C5 112.1(3) . . ?
O6 C4 H4 108.0 . . ?
C3 C4 H4 108.0 . . ?
C5 C4 H4 108.0 . . ?
O1 C5 C4 109.6(3) . . ?
O1 C5 C6 109.9(3) . . ?
C4 C5 C6 108.1(3) . . ?
O1 C5 H5 109.7 . . ?
C4 C5 H5 109.7 . . ?
C6 C5 H5 109.7 . . ?
O4 C6 C7 106.3(3) . . ?
O4 C6 C5 108.5(3) . . ?
C7 C6 C5 114.2(3) . . ?
O4 C6 H6 109.2 . . ?
C7 C6 H6 109.2 . . ?
C5 C6 H6 109.2 . . ?
F2 C7 F1 105.5(3) . . ?
F2 C7 N1 107.1(3) . . ?
F1 C7 N1 109.2(3) . . ?
F2 C7 C6 111.3(3) . . ?
F1 C7 C6 109.9(3) . . ?
N1 C7 C6 113.5(3) . . ?
N2 C8 C9 111.7(4) . . ?
N2 C8 H8 124.2 . . ?
C9 C8 H8 124.2 . . ?
C14 C9 C10 119.6(4) . . ?
C14 C9 C8 105.7(3) . . ?
C10 C9 C8 134.7(4) . . ?
C11 C10 C9 118.5(4) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C10 C11 C12 120.5(4) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 122.6(4) . . ?
C13 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
C12 C13 C14 116.4(4) . . ?
C12 C13 H13 121.8 . . ?
C14 C13 H13 121.8 . . ?
N1 C14 C13 132.7(4) . . ?
N1 C14 C9 104.9(3) . . ?
C13 C14 C9 122.4(3) . . ?
O2 C15 C16 111.7(4) . . ?
O2 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
O2 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
C21 C16 C17 118.5(5) . . ?
C21 C16 C15 121.3(5) . . ?
C17 C16 C15 120.1(5) . . ?
C18 C17 C16 120.5(5) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 120.8(5) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C18 C19 C20 119.1(6) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C21 C20 C19 120.4(6) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C16 120.7(5) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
O3 C22 C23B 109.8(4) . . ?
O3 C22 C23 109.8(4) . . ?
O3 C22 H22A 109.7 . . ?
C23 C22 H22A 109.7 . . ?
O3 C22 H22B 109.7 . . ?
C23 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C28 C23 C24 117.6(9) . . ?
C28 C23 C22 122.3(8) . . ?
C24 C23 C22 120.0(6) . . ?
C25 C24 C23 120.3(10) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C26 C25 C24 119.8(13) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C27 C26 C25 119.3(14) . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C26 C27 C28 119.4(13) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.3 . . ?
C23 C28 C27 122.5(12) . . ?
C23 C28 H28 118.7 . . ?
C27 C28 H28 118.7 . . ?
C28B C23B C24B 119.2(9) . . ?
C28B C23B C22 121.7(9) . . ?
C24B C23B C22 118.1(7) . . ?
C23B C24B C25B 120.0(11) . . ?
C23B C24B H24B 120.0 . . ?
C25B C24B H24B 120.0 . . ?
C26B C25B C24B 120.6(14) . . ?
C26B C25B H25B 119.7 . . ?
C24B C25B H25B 119.7 . . ?
C25B C26B C27B 119.0(16) . . ?
C25B C26B H26B 120.5 . . ?
C27B C26B H26B 120.5 . . ?
C26B C27B C28B 120.3(14) . . ?
C26B C27B H27B 119.9 . . ?
C28B C27B H27B 119.9 . . ?
C23B C28B C27B 119.5(13) . . ?
C23B C28B H28B 120.2 . . ?
C27B C28B H28B 120.2 . . ?
O6 C29 C30 110.2(4) . . ?
O6 C29 H29A 109.6 . . ?
C30 C29 H29A 109.6 . . ?
O6 C29 H29B 109.6 . . ?
C30 C29 H29B 109.6 . . ?
H29A C29 H29B 108.1 . . ?
C31 C30 C35 118.1(5) . . ?
C31 C30 C29 122.3(5) . . ?
C35 C30 C29 119.4(5) . . ?
C30 C31 C32 120.4(6) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C33 C32 C31 120.8(6) . . ?
C33 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C34 C33 C32 120.2(6) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C33 C34 C35 119.7(6) . . ?
C33 C34 H34 120.2 . . ?
C35 C34 H34 120.2 . . ?
C34 C35 C30 120.7(5) . . ?
C34 C35 H35 119.6 . . ?
C30 C35 H35 119.6 . . ?
O1 C36 C37 109.8(3) . . ?
O1 C36 H36A 109.7 . . ?
C37 C36 H36A 109.7 . . ?
O1 C36 H36B 109.7 . . ?
C37 C36 H36B 109.7 . . ?
H36A C36 H36B 108.2 . . ?
C42 C37 C38 118.3(4) . . ?
C42 C37 C36 123.0(4) . . ?
C38 C37 C36 118.7(4) . . ?
C39 C38 C37 121.1(4) . . ?
C39 C38 H38 119.4 . . ?
C37 C38 H38 119.4 . . ?
C40 C39 C38 120.1(4) . . ?
C40 C39 H39 119.9 . . ?
C38 C39 H39 119.9 . . ?
C39 C40 C41 119.5(4) . . ?
C39 C40 H40 120.3 . . ?
C41 C40 H40 120.3 . . ?
C40 C41 C42 120.8(4) . . ?
C40 C41 H41 119.6 . . ?
C42 C41 H41 119.6 . . ?
C41 C42 C37 120.1(4) . . ?
C41 C42 H42 119.9 . . ?
C37 C42 H42 119.9 . . ?
C44 C43 H43A 109.5 . . ?
C44 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C44 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C45 C44 C43 106.1(18) . . ?
C45 C44 H44A 110.5 . . ?
C43 C44 H44A 110.5 . . ?
C45 C44 H44B 110.5 . . ?
C43 C44 H44B 110.5 . . ?
H44A C44 H44B 108.7 . . ?
C44 C45 C46 104.9(16) . . ?
C44 C45 H45A 110.8 . . ?
C46 C45 H45A 110.8 . . ?
C44 C45 H45B 110.8 . . ?
C46 C45 H45B 110.8 . . ?
H45A C45 H45B 108.8 . . ?
C47 C46 C45 106.6(17) . . ?
C47 C46 H46A 110.4 . . ?
C45 C46 H46A 110.4 . . ?
C47 C46 H46B 110.4 . . ?
C45 C46 H46B 110.4 . . ?
H46A C46 H46B 108.6 . . ?
C46 C47 C48 102.2(19) . . ?
C46 C47 H47A 111.3 . . ?
C48 C47 H47A 111.3 . . ?
C46 C47 H47B 111.3 . . ?
C48 C47 H47B 111.3 . . ?
H47A C47 H47B 109.2 . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?

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
C14 N1 N2 C8 1.0(4) . . . . ?
C7 N1 N2 C8 178.8(3) . . . . ?
C15 O2 C1 C2 -172.8(4) . . . . ?
C6 O4 C2 C1 -173.9(3) . . . . ?
C6 O4 C2 C3 64.3(4) . . . . ?
O2 C1 C2 O4 74.7(4) . . . . ?
O2 C1 C2 C3 -166.0(4) . . . . ?
C22 O3 C3 C4 105.0(4) . . . . ?
C22 O3 C3 C2 -135.9(4) . . . . ?
O4 C2 C3 O3 -173.4(3) . . . . ?
C1 C2 C3 O3 67.6(4) . . . . ?
O4 C2 C3 C4 -54.7(4) . . . . ?
C1 C2 C3 C4 -173.7(4) . . . . ?
C29 O6 C4 C3 128.4(4) . . . . ?
C29 O6 C4 C5 -107.2(5) . . . . ?
O3 C3 C4 O6 -66.1(4) . . . . ?
C2 C3 C4 O6 176.4(3) . . . . ?
O3 C3 C4 C5 169.9(3) . . . . ?
C2 C3 C4 C5 52.4(4) . . . . ?
C36 O1 C5 C4 -105.4(4) . . . . ?
C36 O1 C5 C6 135.9(4) . . . . ?
O6 C4 C5 O1 63.9(4) . . . . ?
C3 C4 C5 O1 -173.2(3) . . . . ?
O6 C4 C5 C6 -176.3(3) . . . . ?
C3 C4 C5 C6 -53.4(4) . . . . ?
C2 O4 C6 C7 170.2(3) . . . . ?
C2 O4 C6 C5 -66.6(4) . . . . ?
O1 C5 C6 O4 178.0(3) . . . . ?
C4 C5 C6 O4 58.4(4) . . . . ?
O1 C5 C6 C7 -63.6(4) . . . . ?
C4 C5 C6 C7 176.8(3) . . . . ?
N2 N1 C7 F2 -173.0(3) . . . . ?
C14 N1 C7 F2 4.3(6) . . . . ?
N2 N1 C7 F1 73.3(4) . . . . ?
C14 N1 C7 F1 -109.5(4) . . . . ?
N2 N1 C7 C6 -49.7(5) . . . . ?
C14 N1 C7 C6 127.5(4) . . . . ?
O4 C6 C7 F2 79.8(4) . . . . ?
C5 C6 C7 F2 -39.8(4) . . . . ?
O4 C6 C7 F1 -163.7(3) . . . . ?
C5 C6 C7 F1 76.7(4) . . . . ?
O4 C6 C7 N1 -41.1(4) . . . . ?
C5 C6 C7 N1 -160.7(3) . . . . ?
N1 N2 C8 C9 -0.8(5) . . . . ?
N2 C8 C9 C14 0.3(5) . . . . ?
N2 C8 C9 C10 179.1(4) . . . . ?
C14 C9 C10 C11 -0.5(6) . . . . ?
C8 C9 C10 C11 -179.2(4) . . . . ?
C9 C10 C11 C12 0.0(6) . . . . ?
C10 C11 C12 C13 0.4(6) . . . . ?
C11 C12 C13 C14 -0.3(6) . . . . ?
N2 N1 C14 C13 179.9(4) . . . . ?
C7 N1 C14 C13 2.6(7) . . . . ?
N2 N1 C14 C9 -0.8(4) . . . . ?
C7 N1 C14 C9 -178.1(4) . . . . ?
C12 C13 C14 N1 179.0(4) . . . . ?
C12 C13 C14 C9 -0.3(6) . . . . ?
C10 C9 C14 N1 -178.8(3) . . . . ?
C8 C9 C14 N1 0.3(4) . . . . ?
C10 C9 C14 C13 0.7(6) . . . . ?
C8 C9 C14 C13 179.7(3) . . . . ?
C1 O2 C15 C16 64.8(5) . . . . ?
O2 C15 C16 C21 -123.9(5) . . . . ?
O2 C15 C16 C17 53.9(6) . . . . ?
C21 C16 C17 C18 -0.2(6) . . . . ?
C15 C16 C17 C18 -178.1(4) . . . . ?
C16 C17 C18 C19 0.0(7) . . . . ?
C17 C18 C19 C20 -0.2(7) . . . . ?
C18 C19 C20 C21 0.6(7) . . . . ?
C19 C20 C21 C16 -0.9(7) . . . . ?
C17 C16 C21 C20 0.7(7) . . . . ?
C15 C16 C21 C20 178.5(4) . . . . ?
C3 O3 C22 C23B -165.8(4) . . . . ?
C3 O3 C22 C23 -165.8(4) . . . . ?
O3 C22 C23 C28 26.5(10) . . . . ?
O3 C22 C23 C24 -155.1(9) . . . . ?
C28 C23 C24 C25 3.4(15) . . . . ?
C22 C23 C24 C25 -175.1(9) . . . . ?
C23 C24 C25 C26 5(2) . . . . ?
C24 C25 C26 C27 -11(3) . . . . ?
C25 C26 C27 C28 9(3) . . . . ?
C24 C23 C28 C27 -5.9(16) . . . . ?
C22 C23 C28 C27 172.5(9) . . . . ?
C26 C27 C28 C23 0(2) . . . . ?
O3 C22 C23B C28B 4.9(11) . . . . ?
O3 C22 C23B C24B 173.6(10) . . . . ?
C28B C23B C24B C25B -10.3(18) . . . . ?
C22 C23B C24B C25B -179.3(10) . . . . ?
C23B C24B C25B C26B 1(3) . . . . ?
C24B C25B C26B C27B 9(4) . . . . ?
C25B C26B C27B C28B -9(3) . . . . ?
C24B C23B C28B C27B 9.7(18) . . . . ?
C22 C23B C28B C27B 178.3(10) . . . . ?
C26B C27B C28B C23B 0(2) . . . . ?
C4 O6 C29 C30 -169.6(5) . . . . ?
O6 C29 C30 C31 -109.4(6) . . . . ?
O6 C29 C30 C35 76.5(7) . . . . ?
C35 C30 C31 C32 0.4(8) . . . . ?
C29 C30 C31 C32 -173.8(5) . . . . ?
C30 C31 C32 C33 -2.0(10) . . . . ?
C31 C32 C33 C34 1.7(10) . . . . ?
C32 C33 C34 C35 0.1(10) . . . . ?
C33 C34 C35 C30 -1.7(9) . . . . ?
C31 C30 C35 C34 1.4(8) . . . . ?
C29 C30 C35 C34 175.7(5) . . . . ?
C5 O1 C36 C37 164.5(3) . . . . ?
O1 C36 C37 C42 -1.8(6) . . . . ?
O1 C36 C37 C38 178.6(4) . . . . ?
C42 C37 C38 C39 -0.2(7) . . . . ?
C36 C37 C38 C39 179.4(5) . . . . ?
C37 C38 C39 C40 -0.4(8) . . . . ?
C38 C39 C40 C41 0.9(8) . . . . ?
C39 C40 C41 C42 -1.0(8) . . . . ?
C40 C41 C42 C37 0.5(7) . . . . ?
C38 C37 C42 C41 0.1(7) . . . . ?
C36 C37 C42 C41 -179.5(5) . . . . ?
C43 C44 C45 C46 -170(4) . . . . ?
C44 C45 C46 C47 -133(3) . . . . ?
C45 C46 C47 C48 -169(3) . . . . ?

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_MK_216_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2414405'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2025-01-03 deposited with the CCDC.	2025-10-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 F2 N2 O3'
_chemical_formula_weight         348.34

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'
F F 0.0171 0.0103 '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'

_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                   5.4907(3)
_cell_length_b                   11.8432(8)
_cell_length_c                   25.3093(16)
_cell_angle_alpha                90
_cell_angle_beta                 93.479(3)
_cell_angle_gamma                90
_cell_volume                     1642.77(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9080
_cell_measurement_theta_min      2.9698
_cell_measurement_theta_max      33.1579

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6999
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device       'three circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_detector_type            
'PhotonII charge-integrating pixel array (CPAD)'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            53511
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.357
_diffrn_reflns_theta_max         33.137
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6253
_reflns_number_gt                4781
_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       'Apex4 v2022.10-0 (Bruker, 2022)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015b)'
_computing_structure_refinement  
;  
SHELXL-2019/2 (Sheldrick, 2015a, 2019), 
SHELXLE Rev1541 (Hübschle et al., 2011)
;
_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)+(0.0483P)²+0.5289P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6253
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1125
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
F1 F 0.76634(12) 0.27581(7) 0.53374(3) 0.03327(17) Uani 1 1 d . . . . .
F2 F 0.46065(14) 0.37122(6) 0.49996(3) 0.03135(16) Uani 1 1 d . . . . .
O1 O 0.74192(14) 0.44514(7) 0.73164(3) 0.02519(16) Uani 1 1 d . . . . .
O2 O 0.41955(14) 0.61607(6) 0.71658(3) 0.02275(15) Uani 1 1 d . . . . .
O3 O 0.09617(14) 0.61952(7) 0.63371(3) 0.02486(16) Uani 1 1 d . . . . .
N1 N 0.47863(15) 0.18370(7) 0.48257(3) 0.02007(16) Uani 1 1 d . . . . .
N2 N 0.27287(15) 0.11990(8) 0.48315(3) 0.02077(16) Uani 1 1 d . . . . .
C1 C 0.60405(19) 0.17084(10) 0.43831(4) 0.0252(2) Uani 1 1 d . . . . .
H1 H 0.750589 0.208080 0.430323 0.030 Uiso 1 1 calc R U . . .
C2 C 0.47464(19) 0.09228(9) 0.40717(4) 0.02197(19) Uani 1 1 d . . . . .
C3 C 0.4985(2) 0.04355(10) 0.35628(4) 0.0285(2) Uani 1 1 d . . . . .
H3 H 0.633351 0.061426 0.336012 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3217(2) -0.02953(10) 0.33757(4) 0.0297(2) Uani 1 1 d . . . . .
H4 H 0.332773 -0.061663 0.303402 0.036 Uiso 1 1 calc R U . . .
C5 C 0.1206(2) -0.05900(10) 0.36799(5) 0.0291(2) Uani 1 1 d . . . . .
H5 H 0.001893 -0.110465 0.353452 0.035 Uiso 1 1 calc R U . . .
C6 C 0.0929(2) -0.01560(10) 0.41741(4) 0.0254(2) Uani 1 1 d . . . . .
H6 H -0.039665 -0.037133 0.437643 0.030 Uiso 1 1 calc R U . . .
C7 C 0.27148(18) 0.06309(8) 0.43704(4) 0.01963(17) Uani 1 1 d . . . . .
C8 C 0.52113(17) 0.26970(9) 0.52262(4) 0.02073(18) Uani 1 1 d . . . . .
C9 C 0.38381(18) 0.24960(9) 0.57167(4) 0.02074(18) Uani 1 1 d . . . . .
H9A H 0.449702 0.181169 0.589886 0.025 Uiso 1 1 calc R U . . .
H9B H 0.210017 0.235314 0.561068 0.025 Uiso 1 1 calc R U . . .
C10 C 0.40060(17) 0.34782(8) 0.60991(4) 0.01942(17) Uani 1 1 d . . . . .
C11 C 0.57547(18) 0.34825(8) 0.65222(4) 0.02003(18) Uani 1 1 d . . . . .
H11 H 0.688267 0.287686 0.656728 0.024 Uiso 1 1 calc R U . . .
C12 C 0.58380(17) 0.43841(8) 0.68798(4) 0.01883(17) Uani 1 1 d . . . . .
C13 C 0.42128(17) 0.52900(8) 0.68066(4) 0.01836(17) Uani 1 1 d . . . . .
C14 C 0.24774(17) 0.52783(8) 0.63783(4) 0.01898(17) Uani 1 1 d . . . . .
C15 C 0.23571(17) 0.43685(9) 0.60290(4) 0.02075(18) Uani 1 1 d . . . . .
H15 H 0.115254 0.435467 0.574331 0.025 Uiso 1 1 calc R U . . .
C16 C 0.92285(19) 0.35878(10) 0.73867(4) 0.0266(2) Uani 1 1 d . . . . .
H16A H 0.843039 0.285998 0.744002 0.040 Uiso 1 1 calc R U . . .
H16B H 1.031841 0.376394 0.769669 0.040 Uiso 1 1 calc R U . . .
H16C H 1.017700 0.354731 0.707145 0.040 Uiso 1 1 calc R U . . .
C17 C 0.6228(2) 0.69074(11) 0.71597(6) 0.0345(3) Uani 1 1 d . . . . .
H17A H 0.618933 0.730612 0.682003 0.052 Uiso 1 1 calc R U . . .
H17B H 0.774459 0.647323 0.720725 0.052 Uiso 1 1 calc R U . . .
H17C H 0.614729 0.745664 0.744779 0.052 Uiso 1 1 calc R U . . .
C18 C -0.08790(19) 0.61841(10) 0.59118(5) 0.0266(2) Uani 1 1 d . . . . .
H18A H -0.010513 0.613035 0.557380 0.040 Uiso 1 1 calc R U . . .
H18B H -0.183747 0.688140 0.591920 0.040 Uiso 1 1 calc R U . . .
H18C H -0.195480 0.553311 0.595105 0.040 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
F1 C8 1.3606(11) . ?
F2 C8 1.3644(12) . ?
O1 C12 1.3655(11) . ?
O1 C16 1.4294(13) . ?
O2 C13 1.3751(12) . ?
O2 C17 1.4246(14) . ?
O3 C14 1.3683(12) . ?
O3 C18 1.4313(13) . ?
N1 C1 1.3585(13) . ?
N1 N2 1.3600(12) . ?
N1 C8 1.4458(13) . ?
N2 C7 1.3466(13) . ?
C1 C2 1.3870(15) . ?
C1 H1 0.9500 . ?
C2 C3 1.4246(15) . ?
C2 C7 1.4274(14) . ?
C3 C4 1.3636(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.4275(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3692(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.4204(15) . ?
C6 H6 0.9500 . ?
C8 C9 1.5100(15) . ?
C9 C10 1.5124(14) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.3941(13) . ?
C10 C15 1.3941(14) . ?
C11 C12 1.3987(14) . ?
C11 H11 0.9500 . ?
C12 C13 1.4006(13) . ?
C13 C14 1.3993(13) . ?
C14 C15 1.3926(14) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O1 C16 117.51(8) . . ?
C13 O2 C17 114.93(8) . . ?
C14 O3 C18 116.64(8) . . ?
C1 N1 N2 114.18(9) . . ?
C1 N1 C8 126.06(9) . . ?
N2 N1 C8 118.86(8) . . ?
C7 N2 N1 103.26(8) . . ?
N1 C1 C2 106.01(9) . . ?
N1 C1 H1 127.0 . . ?
C2 C1 H1 127.0 . . ?
C1 C2 C3 135.52(10) . . ?
C1 C2 C7 104.56(9) . . ?
C3 C2 C7 119.89(10) . . ?
C4 C3 C2 117.95(10) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C3 C4 C5 121.69(10) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 122.23(11) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C7 116.96(10) . . ?
C5 C6 H6 121.5 . . ?
C7 C6 H6 121.5 . . ?
N2 C7 C6 126.76(9) . . ?
N2 C7 C2 111.98(9) . . ?
C6 C7 C2 121.25(9) . . ?
F1 C8 F2 104.63(8) . . ?
F1 C8 N1 107.34(8) . . ?
F2 C8 N1 107.54(8) . . ?
F1 C8 C9 112.06(8) . . ?
F2 C8 C9 111.31(8) . . ?
N1 C8 C9 113.45(8) . . ?
C8 C9 C10 113.01(8) . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C15 120.44(9) . . ?
C11 C10 C9 120.45(9) . . ?
C15 C10 C9 119.10(9) . . ?
C10 C11 C12 119.59(9) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
O1 C12 C11 124.22(9) . . ?
O1 C12 C13 115.53(9) . . ?
C11 C12 C13 120.24(9) . . ?
O2 C13 C14 119.21(9) . . ?
O2 C13 C12 121.12(8) . . ?
C14 C13 C12 119.56(9) . . ?
O3 C14 C15 124.09(9) . . ?
O3 C14 C13 115.69(9) . . ?
C15 C14 C13 120.22(9) . . ?
C14 C15 C10 119.93(9) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
C1 N1 N2 C7 0.77(12) . . . . ?
C8 N1 N2 C7 170.58(8) . . . . ?
N2 N1 C1 C2 -0.49(12) . . . . ?
C8 N1 C1 C2 -169.43(9) . . . . ?
N1 C1 C2 C3 177.74(12) . . . . ?
N1 C1 C2 C7 -0.01(11) . . . . ?
C1 C2 C3 C4 -176.85(12) . . . . ?
C7 C2 C3 C4 0.64(16) . . . . ?
C2 C3 C4 C5 -1.29(17) . . . . ?
C3 C4 C5 C6 0.21(18) . . . . ?
C4 C5 C6 C7 1.48(17) . . . . ?
N1 N2 C7 C6 -179.43(10) . . . . ?
N1 N2 C7 C2 -0.76(11) . . . . ?
C5 C6 C7 N2 176.46(11) . . . . ?
C5 C6 C7 C2 -2.09(16) . . . . ?
C1 C2 C7 N2 0.50(12) . . . . ?
C3 C2 C7 N2 -177.68(9) . . . . ?
C1 C2 C7 C6 179.25(10) . . . . ?
C3 C2 C7 C6 1.07(15) . . . . ?
C1 N1 C8 F1 -45.20(13) . . . . ?
N2 N1 C8 F1 146.32(9) . . . . ?
C1 N1 C8 F2 66.90(12) . . . . ?
N2 N1 C8 F2 -101.58(10) . . . . ?
C1 N1 C8 C9 -169.55(10) . . . . ?
N2 N1 C8 C9 21.97(12) . . . . ?
F1 C8 C9 C10 66.42(11) . . . . ?
F2 C8 C9 C10 -50.36(11) . . . . ?
N1 C8 C9 C10 -171.82(8) . . . . ?
C8 C9 C10 C11 -95.63(11) . . . . ?
C8 C9 C10 C15 85.65(11) . . . . ?
C15 C10 C11 C12 0.44(15) . . . . ?
C9 C10 C11 C12 -178.27(9) . . . . ?
C16 O1 C12 C11 5.27(15) . . . . ?
C16 O1 C12 C13 -175.55(9) . . . . ?
C10 C11 C12 O1 177.65(9) . . . . ?
C10 C11 C12 C13 -1.49(15) . . . . ?
C17 O2 C13 C14 -111.43(11) . . . . ?
C17 O2 C13 C12 72.45(13) . . . . ?
O1 C12 C13 O2 -2.03(14) . . . . ?
C11 C12 C13 O2 177.19(9) . . . . ?
O1 C12 C13 C14 -178.14(9) . . . . ?
C11 C12 C13 C14 1.08(14) . . . . ?
C18 O3 C14 C15 1.43(14) . . . . ?
C18 O3 C14 C13 -178.05(9) . . . . ?
O2 C13 C14 O3 3.72(13) . . . . ?
C12 C13 C14 O3 179.90(9) . . . . ?
O2 C13 C14 C15 -175.78(9) . . . . ?
C12 C13 C14 C15 0.40(14) . . . . ?
O3 C14 C15 C10 179.09(9) . . . . ?
C13 C14 C15 C10 -1.46(15) . . . . ?
C11 C10 C15 C14 1.04(15) . . . . ?
C9 C10 C15 C14 179.76(9) . . . . ?

_refine_diff_density_max         0.394
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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 
# 
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# Please retain this information to preserve the provenance of 
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data_RMH3_611_0m
_database_code_depnum_ccdc_archive 'CCDC 2492669'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2025-10-01 deposited with the CCDC.	2025-10-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2025/1
_shelx_SHELXL_version_number     2025/1
_chemical_name_systematic        
3-bromo-7-(1,1-difluoro-2-(3,4,5-trimethoxyphenyl)ethyl)-7H-pyrrolo[2,3-b]pyridine
_chemical_name_common            ?
_chemical_melting_point          452
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 Br F2 N2 O3'
_chemical_formula_weight         427.24

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

_cell_length_a                   25.4790(12)
_cell_length_b                   5.0337(2)
_cell_length_c                   13.4427(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.449(2)
_cell_angle_gamma                90
_cell_volume                     1683.54(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8746
_cell_measurement_theta_min      3.1029
_cell_measurement_theta_max      33.1527

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.485
_shelx_estimated_absorpt_T_min   0.376
_shelx_estimated_absorpt_T_max   0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4815
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device       'three circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_detector_type            
'PhotonII charge-integrating pixel array (CPAD)'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            15420
_diffrn_reflns_av_unetI/netI     0.0789
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.104
_diffrn_reflns_theta_max         33.219
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             5499
_reflns_number_gt                4688
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_max     0.735
_reflns_Friedel_fraction_full    0.957

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Apex6 v2024.9-1 (Bruker, 2025)'
_computing_cell_refinement       'SAINT V8.41 (Bruker, 2025)'
_computing_data_reduction        'SAINT V8.41 (Bruker, 2025)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015b)'
_computing_structure_refinement  
;  
SHELXL-2025/1 (Sheldrick, 2015a, 2025), 
SHELXLE Rev1737 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+0.5231P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.029(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5499
_refine_ls_number_parameters     239
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.0926
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.088
_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
Br1 Br 0.68543(2) -0.11719(8) 0.88259(3) 0.03268(12) Uani 1 1 d . . . . .
F1 F 0.56251(9) 0.5924(5) 0.39177(19) 0.0267(5) Uani 1 1 d . . . . .
F2 F 0.54052(8) 0.1949(5) 0.42848(17) 0.0252(4) Uani 1 1 d . . . . .
O1 O 0.39319(10) 0.8962(5) 0.1787(2) 0.0241(5) Uani 1 1 d . . . . .
O2 O 0.31035(9) 0.5864(5) 0.1965(2) 0.0215(5) Uani 1 1 d . . . . .
O3 O 0.31867(10) 0.2393(6) 0.3506(2) 0.0255(6) Uani 1 1 d . . . . .
N1 N 0.59999(11) 0.4270(6) 0.5491(2) 0.0190(6) Uani 1 1 d . . . . .
N2 N 0.56419(11) 0.0780(6) 0.6380(2) 0.0215(6) Uani 1 1 d . . . . .
C1 C 0.64268(14) 0.5906(7) 0.5475(3) 0.0237(7) Uani 1 1 d . . . . .
H1 H 0.639915 0.720802 0.495455 0.028 Uiso 1 1 calc R U . . .
C2 C 0.68962(14) 0.5689(8) 0.6204(4) 0.0273(8) Uani 1 1 d . . . . .
H2 H 0.718869 0.683186 0.617170 0.033 Uiso 1 1 calc R U . . .
C3 C 0.69516(15) 0.3834(7) 0.6986(3) 0.0248(7) Uani 1 1 d . . . . .
H3 H 0.727916 0.367706 0.747831 0.030 Uiso 1 1 calc R U . . .
C4 C 0.65166(13) 0.2221(7) 0.7029(3) 0.0213(6) Uani 1 1 d . . . . .
C5 C 0.60268(12) 0.2451(7) 0.6256(2) 0.0188(6) Uani 1 1 d . . . . .
C6 C 0.63890(14) 0.0181(8) 0.7657(3) 0.0235(7) Uani 1 1 d . . . . .
C7 C 0.58751(15) -0.0607(8) 0.7254(3) 0.0247(7) Uani 1 1 d . . . . .
H7 H 0.569577 -0.196467 0.754261 0.030 Uiso 1 1 calc R U . . .
C8 C 0.55061(13) 0.4439(7) 0.4679(3) 0.0200(6) Uani 1 1 d . . . . .
C9 C 0.50287(13) 0.5528(8) 0.5034(3) 0.0204(6) Uani 1 1 d . . . . .
H9A H 0.511137 0.735583 0.529248 0.024 Uiso 1 1 calc R U . . .
H9B H 0.496409 0.442873 0.560655 0.024 Uiso 1 1 calc R U . . .
C10 C 0.45220(12) 0.5582(7) 0.4204(3) 0.0192(6) Uani 1 1 d . . . . .
C11 C 0.44756(13) 0.7344(7) 0.3385(3) 0.0196(6) Uani 1 1 d . . . . .
H11 H 0.476167 0.852486 0.334891 0.024 Uiso 1 1 calc R U . . .
C12 C 0.40087(12) 0.7362(7) 0.2625(3) 0.0193(6) Uani 1 1 d . . . . .
C13 C 0.35782(13) 0.5690(7) 0.2687(3) 0.0196(6) Uani 1 1 d . . . . .
C14 C 0.36253(13) 0.3943(7) 0.3511(3) 0.0191(6) Uani 1 1 d . . . . .
C15 C 0.40956(13) 0.3875(7) 0.4267(3) 0.0190(6) Uani 1 1 d . . . . .
H15 H 0.412683 0.267782 0.482317 0.023 Uiso 1 1 calc R U . . .
C16 C 0.43608(14) 1.0735(8) 0.1711(3) 0.0252(7) Uani 1 1 d . . . . .
H16A H 0.425467 1.182500 0.109603 0.038 Uiso 1 1 calc R U . . .
H16B H 0.468215 0.970496 0.167205 0.038 Uiso 1 1 calc R U . . .
H16C H 0.443904 1.188888 0.231165 0.038 Uiso 1 1 calc R U . . .
C17 C 0.30610(15) 0.3887(8) 0.1181(3) 0.0269(8) Uani 1 1 d . . . . .
H17A H 0.271517 0.407726 0.069781 0.040 Uiso 1 1 calc R U . . .
H17B H 0.308471 0.211412 0.148840 0.040 Uiso 1 1 calc R U . . .
H17C H 0.335404 0.412167 0.082150 0.040 Uiso 1 1 calc R U . . .
C18 C 0.32208(15) 0.0509(8) 0.4312(3) 0.0274(8) Uani 1 1 d . . . . .
H18A H 0.288999 -0.054565 0.420037 0.041 Uiso 1 1 calc R U . . .
H18B H 0.326745 0.144936 0.496381 0.041 Uiso 1 1 calc R U . . .
H18C H 0.352855 -0.066898 0.432584 0.041 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
Br1 C6 1.880(3) . ?
F1 C8 1.353(4) . ?
F2 C8 1.363(4) . ?
O1 C12 1.364(4) . ?
O1 C16 1.431(4) . ?
O2 C13 1.381(4) . ?
O2 C17 1.436(5) . ?
O3 C14 1.362(4) . ?
O3 C18 1.429(5) . ?
N1 C1 1.368(4) . ?
N1 C5 1.369(5) . ?
N1 C8 1.480(4) . ?
N2 C5 1.329(4) . ?
N2 C7 1.386(5) . ?
C1 C2 1.378(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.390(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(5) . ?
C3 H3 0.9500 . ?
C4 C6 1.411(6) . ?
C4 C5 1.446(4) . ?
C6 C7 1.364(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.503(5) . ?
C9 C10 1.514(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.398(5) . ?
C10 C15 1.402(5) . ?
C11 C12 1.391(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.399(5) . ?
C13 C14 1.399(5) . ?
C14 C15 1.395(5) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O1 C16 116.8(3) . . ?
C13 O2 C17 112.8(3) . . ?
C14 O3 C18 117.4(3) . . ?
C1 N1 C5 120.2(3) . . ?
C1 N1 C8 120.4(3) . . ?
C5 N1 C8 119.3(3) . . ?
C5 N2 C7 103.4(3) . . ?
N1 C1 C2 120.8(3) . . ?
N1 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C1 C2 C3 121.5(3) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 118.3(4) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C6 137.8(3) . . ?
C3 C4 C5 119.8(3) . . ?
C6 C4 C5 102.3(3) . . ?
N2 C5 N1 126.8(3) . . ?
N2 C5 C4 113.9(3) . . ?
N1 C5 C4 119.3(3) . . ?
C7 C6 C4 107.4(3) . . ?
C7 C6 Br1 127.2(3) . . ?
C4 C6 Br1 125.4(3) . . ?
C6 C7 N2 112.9(3) . . ?
C6 C7 H7 123.5 . . ?
N2 C7 H7 123.5 . . ?
F1 C8 F2 105.6(3) . . ?
F1 C8 N1 107.2(3) . . ?
F2 C8 N1 107.0(3) . . ?
F1 C8 C9 111.6(3) . . ?
F2 C8 C9 111.2(3) . . ?
N1 C8 C9 113.8(3) . . ?
C8 C9 C10 113.1(3) . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C11 C10 C15 120.1(3) . . ?
C11 C10 C9 120.4(3) . . ?
C15 C10 C9 119.5(3) . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
O1 C12 C11 123.9(3) . . ?
O1 C12 C13 115.4(3) . . ?
C11 C12 C13 120.6(3) . . ?
O2 C13 C14 120.6(3) . . ?
O2 C13 C12 119.9(3) . . ?
C14 C13 C12 119.4(3) . . ?
O3 C14 C15 124.4(3) . . ?
O3 C14 C13 115.2(3) . . ?
C15 C14 C13 120.4(3) . . ?
C14 C15 C10 119.7(3) . . ?
C14 C15 H15 120.1 . . ?
C10 C15 H15 120.1 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
C5 N1 C1 C2 2.4(5) . . . . ?
C8 N1 C1 C2 -177.3(3) . . . . ?
N1 C1 C2 C3 -0.8(6) . . . . ?
C1 C2 C3 C4 -1.2(6) . . . . ?
C2 C3 C4 C6 -179.1(4) . . . . ?
C2 C3 C4 C5 1.6(5) . . . . ?
C7 N2 C5 N1 179.6(3) . . . . ?
C7 N2 C5 C4 0.1(4) . . . . ?
C1 N1 C5 N2 178.6(3) . . . . ?
C8 N1 C5 N2 -1.7(5) . . . . ?
C1 N1 C5 C4 -2.0(5) . . . . ?
C8 N1 C5 C4 177.8(3) . . . . ?
C3 C4 C5 N2 179.5(3) . . . . ?
C6 C4 C5 N2 0.0(4) . . . . ?
C3 C4 C5 N1 0.0(5) . . . . ?
C6 C4 C5 N1 -179.6(3) . . . . ?
C3 C4 C6 C7 -179.5(4) . . . . ?
C5 C4 C6 C7 0.0(4) . . . . ?
C3 C4 C6 Br1 0.1(7) . . . . ?
C5 C4 C6 Br1 179.6(3) . . . . ?
C4 C6 C7 N2 0.1(4) . . . . ?
Br1 C6 C7 N2 -179.5(3) . . . . ?
C5 N2 C7 C6 -0.1(4) . . . . ?
C1 N1 C8 F1 13.0(4) . . . . ?
C5 N1 C8 F1 -166.7(3) . . . . ?
C1 N1 C8 F2 125.9(3) . . . . ?
C5 N1 C8 F2 -53.8(4) . . . . ?
C1 N1 C8 C9 -110.9(4) . . . . ?
C5 N1 C8 C9 69.4(4) . . . . ?
F1 C8 C9 C10 60.8(4) . . . . ?
F2 C8 C9 C10 -56.7(4) . . . . ?
N1 C8 C9 C10 -177.7(3) . . . . ?
C8 C9 C10 C11 -69.3(4) . . . . ?
C8 C9 C10 C15 111.5(4) . . . . ?
C15 C10 C11 C12 -1.2(5) . . . . ?
C9 C10 C11 C12 179.6(3) . . . . ?
C16 O1 C12 C11 -0.9(5) . . . . ?
C16 O1 C12 C13 178.8(3) . . . . ?
C10 C11 C12 O1 -178.4(3) . . . . ?
C10 C11 C12 C13 2.0(5) . . . . ?
C17 O2 C13 C14 -84.8(4) . . . . ?
C17 O2 C13 C12 98.3(4) . . . . ?
O1 C12 C13 O2 -4.3(5) . . . . ?
C11 C12 C13 O2 175.4(3) . . . . ?
O1 C12 C13 C14 178.8(3) . . . . ?
C11 C12 C13 C14 -1.6(5) . . . . ?
C18 O3 C14 C15 -2.4(5) . . . . ?
C18 O3 C14 C13 177.9(3) . . . . ?
O2 C13 C14 O3 3.1(5) . . . . ?
C12 C13 C14 O3 -179.9(3) . . . . ?
O2 C13 C14 C15 -176.6(3) . . . . ?
C12 C13 C14 C15 0.4(5) . . . . ?
O3 C14 C15 C10 -179.3(3) . . . . ?
C13 C14 C15 C10 0.4(5) . . . . ?
C11 C10 C15 C14 0.0(5) . . . . ?
C9 C10 C15 C14 179.2(3) . . . . ?

_refine_diff_density_max         0.453
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.097


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexanes and ethyl acetate (2:3 hexanes:ethyl acetate)'
####################################################################### 
# 
# 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_X_RCL_MAEK_5482_0m
_database_code_depnum_ccdc_archive 'CCDC 2414406'
loop_
_audit_author_name
_audit_author_address
'Denver R. Hopkins'
;Purdue University
United States of America
;
_audit_update_record             
;
2025-01-03 deposited with the CCDC.	2025-10-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
1-(1,1-difluoro-2-(3,4,5-trimethoxyphenyl)ethyl)-1H-benzo[d][1,2,3]triazole
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 F2 N3 O3'
_chemical_formula_sum            'C17 H17 F2 N3 O3'
_chemical_formula_weight         349.33

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'

_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                   13.662(5)
_cell_length_b                   5.521(2)
_cell_length_c                   21.611(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.246(10)
_cell_angle_gamma                90
_cell_volume                     1617.1(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      2.5671
_cell_measurement_theta_max      33.1716

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.668
_exptl_crystal_size_mid          0.425
_exptl_crystal_size_min          0.258
_exptl_absorpt_coefficient_mu    0.115
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6368
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D. (2015). J. Appl. Cryst. 48, 3-10.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device       'three circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_detector_type            
'PhotonII charge-integrating pixel array (CPAD)'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            33368
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.006
_diffrn_reflns_theta_max         33.194
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6182
_reflns_number_gt                4691
_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       ' Apex4 v2022.1-1 (Bruker, 2022) '
_computing_cell_refinement       ' SAINT V8.40B (Bruker, 2020)'
_computing_data_reduction        ' SAINT V8.40B (Bruker, 2020)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015a, 2018), 
SHELXLE Rev1428 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Hydrogens placed automatically with HFIX.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0515P)²+0.4244P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6182
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1168
_refine_ls_wR_factor_gt          0.1047
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
F1 F 0.44673(5) 0.43240(13) 0.36459(4) 0.0395(2) Uani 1 1 d . . . . .
F2 F 0.49964(5) 0.74724(17) 0.41774(3) 0.0395(2) Uani 1 1 d . . . . .
O1 O 0.18051(6) 1.17767(15) 0.45304(4) 0.02594(16) Uani 1 1 d . . . . .
O2 O 0.03480(5) 0.88581(14) 0.40333(4) 0.02400(16) Uani 1 1 d . . . . .
O3 O 0.06732(5) 0.53468(15) 0.32249(4) 0.02415(16) Uani 1 1 d . . . . .
N1 N 0.57627(6) 0.63137(16) 0.33578(4) 0.02088(16) Uani 1 1 d . . . . .
N2 N 0.60657(6) 0.79700(17) 0.29473(4) 0.02387(18) Uani 1 1 d . . . . .
N3 N 0.69740(6) 0.75139(18) 0.28791(5) 0.02648(19) Uani 1 1 d . . . . .
C1 C 0.48243(7) 0.65904(19) 0.35830(5) 0.02178(19) Uani 1 1 d . . . . .
C2 C 0.41003(7) 0.8156(2) 0.31812(5) 0.02181(19) Uani 1 1 d . . . . .
H2A H 0.400355 0.749324 0.275215 0.026 Uiso 1 1 calc R U . . .
H2B H 0.437572 0.980888 0.316156 0.026 Uiso 1 1 calc R U . . .
C3 C 0.31120(7) 0.82957(19) 0.34278(5) 0.01980(18) Uani 1 1 d . . . . .
C4 C 0.29563(7) 1.00127(19) 0.38785(5) 0.02114(18) Uani 1 1 d . . . . .
H4 H 0.347278 1.107999 0.403797 0.025 Uiso 1 1 calc R U . . .
C5 C 0.20362(7) 1.01528(18) 0.40938(5) 0.01950(17) Uani 1 1 d . . . . .
C6 C 0.12744(7) 0.85882(18) 0.38551(4) 0.01891(17) Uani 1 1 d . . . . .
C7 C 0.14488(7) 0.68389(18) 0.34161(4) 0.01877(17) Uani 1 1 d . . . . .
C8 C 0.23667(7) 0.66961(19) 0.31969(5) 0.02020(18) Uani 1 1 d . . . . .
H8 H 0.248089 0.551917 0.289342 0.024 Uiso 1 1 calc R U . . .
C9 C 0.65210(7) 0.47552(18) 0.35636(5) 0.02020(18) Uani 1 1 d . . . . .
C10 C 0.72940(7) 0.5561(2) 0.32519(5) 0.02272(19) Uani 1 1 d . . . . .
C11 C 0.82219(8) 0.4425(2) 0.33444(6) 0.0294(2) Uani 1 1 d . . . . .
H11 H 0.875571 0.497714 0.313936 0.035 Uiso 1 1 calc R U . . .
C12 C 0.83226(8) 0.2481(2) 0.37446(6) 0.0306(2) Uani 1 1 d . . . . .
H12 H 0.893874 0.166527 0.381644 0.037 Uiso 1 1 calc R U . . .
C13 C 0.75309(9) 0.1672(2) 0.40505(6) 0.0301(2) Uani 1 1 d . . . . .
H13 H 0.763013 0.031525 0.432163 0.036 Uiso 1 1 calc R U . . .
C14 C 0.66157(8) 0.2777(2) 0.39711(5) 0.0260(2) Uani 1 1 d . . . . .
H14 H 0.608540 0.222848 0.417986 0.031 Uiso 1 1 calc R U . . .
C15 C 0.25509(9) 1.3457(2) 0.47674(6) 0.0292(2) Uani 1 1 d . . . . .
H15A H 0.273511 1.445174 0.442469 0.044 Uiso 1 1 calc R U . . .
H15B H 0.313128 1.257290 0.496249 0.044 Uiso 1 1 calc R U . . .
H15C H 0.229947 1.450298 0.507812 0.044 Uiso 1 1 calc R U . . .
C16 C 0.01688(8) 0.7256(2) 0.45281(6) 0.0299(2) Uani 1 1 d . . . . .
H16A H -0.050334 0.750472 0.462928 0.045 Uiso 1 1 calc R U . . .
H16B H 0.064276 0.759300 0.489743 0.045 Uiso 1 1 calc R U . . .
H16C H 0.024435 0.557571 0.439626 0.045 Uiso 1 1 calc R U . . .
C17 C 0.08356(8) 0.3530(2) 0.27774(6) 0.0280(2) Uani 1 1 d . . . . .
H17A H 0.024037 0.253761 0.268578 0.042 Uiso 1 1 calc R U . . .
H17B H 0.138990 0.250047 0.294649 0.042 Uiso 1 1 calc R U . . .
H17C H 0.098799 0.430796 0.239327 0.042 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
F1 C1 1.3561(13) . ?
F2 C1 1.3661(13) . ?
O1 C5 1.3672(13) . ?
O1 C15 1.4247(14) . ?
O2 C6 1.3767(12) . ?
O2 C16 1.4322(14) . ?
O3 C7 1.3644(12) . ?
O3 C17 1.4298(14) . ?
N1 N2 1.3739(12) . ?
N1 C9 1.3766(13) . ?
N1 C1 1.4356(13) . ?
N2 N3 1.2927(12) . ?
N3 C10 1.3833(15) . ?
C1 C2 1.5043(15) . ?
C2 C3 1.5148(14) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C8 1.3919(14) . ?
C3 C4 1.3945(15) . ?
C4 C5 1.3965(14) . ?
C4 H4 0.9500 . ?
C5 C6 1.4000(14) . ?
C6 C7 1.3953(14) . ?
C7 C8 1.3975(13) . ?
C8 H8 0.9500 . ?
C9 C10 1.3952(14) . ?
C9 C14 1.3987(15) . ?
C10 C11 1.4059(15) . ?
C11 C12 1.3744(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.4096(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.3825(16) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C15 117.27(8) . . ?
C6 O2 C16 113.06(8) . . ?
C7 O3 C17 116.58(8) . . ?
N2 N1 C9 110.42(8) . . ?
N2 N1 C1 120.18(8) . . ?
C9 N1 C1 128.67(9) . . ?
N3 N2 N1 108.40(8) . . ?
N2 N3 C10 108.84(9) . . ?
F1 C1 F2 104.84(9) . . ?
F1 C1 N1 106.47(8) . . ?
F2 C1 N1 107.55(8) . . ?
F1 C1 C2 111.68(9) . . ?
F2 C1 C2 111.14(9) . . ?
N1 C1 C2 114.57(8) . . ?
C1 C2 C3 112.12(8) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C8 C3 C4 120.84(9) . . ?
C8 C3 C2 119.06(9) . . ?
C4 C3 C2 120.10(9) . . ?
C3 C4 C5 119.56(9) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
O1 C5 C4 124.21(9) . . ?
O1 C5 C6 115.67(8) . . ?
C4 C5 C6 120.12(9) . . ?
O2 C6 C7 120.46(9) . . ?
O2 C6 C5 119.82(9) . . ?
C7 C6 C5 119.65(9) . . ?
O3 C7 C6 115.54(8) . . ?
O3 C7 C8 123.99(9) . . ?
C6 C7 C8 120.47(9) . . ?
C3 C8 C7 119.33(9) . . ?
C3 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
N1 C9 C10 103.25(9) . . ?
N1 C9 C14 134.23(9) . . ?
C10 C9 C14 122.51(9) . . ?
N3 C10 C9 109.08(9) . . ?
N3 C10 C11 130.06(10) . . ?
C9 C10 C11 120.86(10) . . ?
C12 C11 C10 117.05(10) . . ?
C12 C11 H11 121.5 . . ?
C10 C11 H11 121.5 . . ?
C11 C12 C13 121.39(10) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 122.50(11) . . ?
C14 C13 H13 118.7 . . ?
C12 C13 H13 118.7 . . ?
C13 C14 C9 115.67(10) . . ?
C13 C14 H14 122.2 . . ?
C9 C14 H14 122.2 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_refine_diff_density_max         0.391
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_MK_220M_0m
_database_code_depnum_ccdc_archive 'CCDC 2414748'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2025-01-03 deposited with the CCDC.	2025-10-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 F2 N3 O5'
_chemical_formula_weight         393.34

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'

_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                   8.3337(3)
_cell_length_b                   8.3855(3)
_cell_length_c                   14.3817(5)
_cell_angle_alpha                78.462(2)
_cell_angle_beta                 74.211(2)
_cell_angle_gamma                63.5570(10)
_cell_volume                     862.29(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9830
_cell_measurement_theta_min      2.7912
_cell_measurement_theta_max      33.2246

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.360
_exptl_absorpt_coefficient_mu    0.126
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6918
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device       'three circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_detector_type            
'PhotonII charge-integrating pixel array (CPAD)'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            33476
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.791
_diffrn_reflns_theta_max         33.247
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6596
_reflns_number_gt                5687
_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       'Apex4 v2022.10-0 (Bruker, 2022)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015b)'
_computing_structure_refinement  
;  
SHELXL-2019/2 (Sheldrick, 2015a, 2019), 
SHELXLE Rev1506 (Hübschle et al., 2011)
;
_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)+(0.0588P)²+0.1562P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6596
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.1045
_refine_ls_wR_factor_gt          0.0994
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
F1 F 0.64974(8) 0.74626(7) 0.70396(4) 0.02571(11) Uani 1 1 d . . . . .
F2 F 0.80548(8) 0.64700(7) 0.56289(3) 0.02452(11) Uani 1 1 d . . . . .
O1 O 0.75412(9) 0.47051(8) 1.05937(4) 0.02207(12) Uani 1 1 d . . . . .
O2 O 0.65198(7) 0.20253(7) 1.08281(4) 0.01855(11) Uani 1 1 d . . . . .
O3 O 0.68012(8) 0.04469(8) 0.92968(4) 0.01996(11) Uani 1 1 d . . . . .
O4 O 1.02390(10) 0.13514(11) 0.37375(6) 0.03692(17) Uani 1 1 d . . . . .
O5 O 0.86464(12) -0.00547(12) 0.36741(6) 0.0423(2) Uani 1 1 d . . . . .
N1 N 0.60943(9) 0.53070(9) 0.65568(4) 0.01704(11) Uani 1 1 d . . . . .
N2 N 0.36614(10) 0.46220(11) 0.71250(5) 0.02388(14) Uani 1 1 d . . . . .
N3 N 0.88797(11) 0.10317(10) 0.40239(6) 0.02535(14) Uani 1 1 d . . . . .
C1 C 0.44907(11) 0.55603(11) 0.72356(5) 0.02127(14) Uani 1 1 d . . . . .
H1 H 0.403307 0.633869 0.773427 0.026 Uiso 1 1 calc R U . . .
C2 C 0.48030(10) 0.36328(11) 0.63516(5) 0.01922(13) Uani 1 1 d . . . . .
C3 C 0.46060(12) 0.23700(13) 0.59412(6) 0.02536(16) Uani 1 1 d . . . . .
H3 H 0.357044 0.209281 0.618215 0.030 Uiso 1 1 calc R U . . .
C4 C 0.59625(12) 0.15380(12) 0.51752(6) 0.02528(16) Uani 1 1 d . . . . .
H4 H 0.586943 0.067263 0.488095 0.030 Uiso 1 1 calc R U . . .
C5 C 0.74722(11) 0.19685(10) 0.48325(5) 0.01940(13) Uani 1 1 d . . . . .
C6 C 0.77298(10) 0.32100(10) 0.52149(5) 0.01748(13) Uani 1 1 d . . . . .
H6 H 0.876815 0.348147 0.496829 0.021 Uiso 1 1 calc R U . . .
C7 C 0.63507(10) 0.40252(10) 0.59866(5) 0.01605(12) Uani 1 1 d . . . . .
C8 C 0.74235(11) 0.59605(10) 0.65693(5) 0.01800(13) Uani 1 1 d . . . . .
C9 C 0.90274(10) 0.46318(10) 0.70164(5) 0.01838(13) Uani 1 1 d . . . . .
H9A H 0.976631 0.362267 0.660687 0.022 Uiso 1 1 calc R U . . .
H9B H 0.981822 0.522009 0.703178 0.022 Uiso 1 1 calc R U . . .
C10 C 0.84064(10) 0.39177(10) 0.80343(5) 0.01606(12) Uani 1 1 d . . . . .
C11 C 0.82506(10) 0.47308(10) 0.88294(5) 0.01726(13) Uani 1 1 d . . . . .
H11 H 0.854780 0.572978 0.873509 0.021 Uiso 1 1 calc R U . . .
C12 C 0.76547(10) 0.40687(10) 0.97664(5) 0.01623(12) Uani 1 1 d . . . . .
C13 C 0.71721(9) 0.26264(9) 0.99040(5) 0.01513(12) Uani 1 1 d . . . . .
C14 C 0.73078(9) 0.18369(9) 0.90976(5) 0.01553(12) Uani 1 1 d . . . . .
C15 C 0.79459(10) 0.24682(10) 0.81641(5) 0.01646(12) Uani 1 1 d . . . . .
H15 H 0.806641 0.191375 0.761888 0.020 Uiso 1 1 calc R U . . .
C16 C 0.75670(11) 0.64265(10) 1.04977(6) 0.02080(14) Uani 1 1 d . . . . .
H16A H 0.872176 0.639268 1.007530 0.031 Uiso 1 1 calc R U . . .
H16B H 0.745904 0.674416 1.113860 0.031 Uiso 1 1 calc R U . . .
H16C H 0.653789 0.732094 1.021349 0.031 Uiso 1 1 calc R U . . .
C17 C 0.79198(13) 0.05326(12) 1.12382(6) 0.02775(17) Uani 1 1 d . . . . .
H17A H 0.847954 -0.044787 1.081921 0.042 Uiso 1 1 calc R U . . .
H17B H 0.737834 0.013381 1.188414 0.042 Uiso 1 1 calc R U . . .
H17C H 0.885884 0.089129 1.129174 0.042 Uiso 1 1 calc R U . . .
C18 C 0.66319(13) -0.01734(12) 0.84858(6) 0.02473(16) Uani 1 1 d . . . . .
H18A H 0.588383 0.084718 0.809475 0.037 Uiso 1 1 calc R U . . .
H18B H 0.604473 -0.100579 0.871946 0.037 Uiso 1 1 calc R U . . .
H18C H 0.785121 -0.078647 0.808777 0.037 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
F1 C8 1.3530(9) . ?
F2 C8 1.3676(8) . ?
O1 C12 1.3627(9) . ?
O1 C16 1.4316(9) . ?
O2 C13 1.3780(8) . ?
O2 C17 1.4333(10) . ?
O3 C14 1.3630(9) . ?
O3 C18 1.4313(10) . ?
O4 N3 1.2236(11) . ?
O5 N3 1.2309(10) . ?
N1 C1 1.3800(10) . ?
N1 C7 1.3878(9) . ?
N1 C8 1.4433(10) . ?
N2 C1 1.3100(11) . ?
N2 C2 1.3860(10) . ?
N3 C5 1.4655(10) . ?
C1 H1 0.9500 . ?
C2 C3 1.3979(11) . ?
C2 C7 1.4099(10) . ?
C3 C4 1.3805(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.3971(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.3874(10) . ?
C6 C7 1.3891(10) . ?
C6 H6 0.9500 . ?
C8 C9 1.5154(11) . ?
C9 C10 1.5107(10) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.3935(10) . ?
C10 C15 1.3947(10) . ?
C11 C12 1.3974(10) . ?
C11 H11 0.9500 . ?
C12 C13 1.3993(10) . ?
C13 C14 1.4018(10) . ?
C14 C15 1.3940(10) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O1 C16 117.06(6) . . ?
C13 O2 C17 112.76(6) . . ?
C14 O3 C18 116.42(6) . . ?
C1 N1 C7 106.51(6) . . ?
C1 N1 C8 126.05(6) . . ?
C7 N1 C8 126.27(6) . . ?
C1 N2 C2 104.79(6) . . ?
O4 N3 O5 123.22(8) . . ?
O4 N3 C5 118.42(7) . . ?
O5 N3 C5 118.36(8) . . ?
N2 C1 N1 113.40(7) . . ?
N2 C1 H1 123.3 . . ?
N1 C1 H1 123.3 . . ?
N2 C2 C3 129.07(7) . . ?
N2 C2 C7 110.63(7) . . ?
C3 C2 C7 120.29(7) . . ?
C4 C3 C2 117.95(7) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C3 C4 C5 120.02(7) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 124.19(7) . . ?
C6 C5 N3 118.11(7) . . ?
C4 C5 N3 117.70(7) . . ?
C5 C6 C7 114.76(7) . . ?
C5 C6 H6 122.6 . . ?
C7 C6 H6 122.6 . . ?
N1 C7 C6 132.60(7) . . ?
N1 C7 C2 104.60(6) . . ?
C6 C7 C2 122.80(7) . . ?
F1 C8 F2 106.85(6) . . ?
F1 C8 N1 106.64(6) . . ?
F2 C8 N1 107.09(6) . . ?
F1 C8 C9 111.31(6) . . ?
F2 C8 C9 109.53(6) . . ?
N1 C8 C9 115.02(6) . . ?
C10 C9 C8 111.95(6) . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C15 120.63(6) . . ?
C11 C10 C9 120.24(6) . . ?
C15 C10 C9 119.10(6) . . ?
C10 C11 C12 119.63(6) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
O1 C12 C11 124.39(6) . . ?
O1 C12 C13 115.42(6) . . ?
C11 C12 C13 120.17(6) . . ?
O2 C13 C12 119.79(6) . . ?
O2 C13 C14 120.52(6) . . ?
C12 C13 C14 119.66(6) . . ?
O3 C14 C15 124.01(6) . . ?
O3 C14 C13 115.81(6) . . ?
C15 C14 C13 120.18(6) . . ?
C14 C15 C10 119.69(6) . . ?
C14 C15 H15 120.2 . . ?
C10 C15 H15 120.2 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
C2 N2 C1 N1 2.25(10) . . . . ?
C7 N1 C1 N2 -2.86(9) . . . . ?
C8 N1 C1 N2 -171.11(7) . . . . ?
C1 N2 C2 C3 178.13(9) . . . . ?
C1 N2 C2 C7 -0.80(9) . . . . ?
N2 C2 C3 C4 -179.00(8) . . . . ?
C7 C2 C3 C4 -0.15(13) . . . . ?
C2 C3 C4 C5 -0.06(14) . . . . ?
C3 C4 C5 C6 0.08(14) . . . . ?
C3 C4 C5 N3 179.42(8) . . . . ?
O4 N3 C5 C6 1.78(12) . . . . ?
O5 N3 C5 C6 -179.10(8) . . . . ?
O4 N3 C5 C4 -177.60(9) . . . . ?
O5 N3 C5 C4 1.53(12) . . . . ?
C4 C5 C6 C7 0.11(12) . . . . ?
N3 C5 C6 C7 -179.22(7) . . . . ?
C1 N1 C7 C6 -178.21(8) . . . . ?
C8 N1 C7 C6 -9.99(13) . . . . ?
C1 N1 C7 C2 2.10(8) . . . . ?
C8 N1 C7 C2 170.32(7) . . . . ?
C5 C6 C7 N1 -179.98(8) . . . . ?
C5 C6 C7 C2 -0.33(11) . . . . ?
N2 C2 C7 N1 -0.85(9) . . . . ?
C3 C2 C7 N1 -179.90(7) . . . . ?
N2 C2 C7 C6 179.41(7) . . . . ?
C3 C2 C7 C6 0.37(12) . . . . ?
C1 N1 C8 F1 -28.16(10) . . . . ?
C7 N1 C8 F1 165.86(6) . . . . ?
C1 N1 C8 F2 -142.27(7) . . . . ?
C7 N1 C8 F2 51.75(9) . . . . ?
C1 N1 C8 C9 95.77(9) . . . . ?
C7 N1 C8 C9 -70.21(9) . . . . ?
F1 C8 C9 C10 66.17(8) . . . . ?
F2 C8 C9 C10 -175.89(6) . . . . ?
N1 C8 C9 C10 -55.26(8) . . . . ?
C8 C9 C10 C11 -93.42(8) . . . . ?
C8 C9 C10 C15 84.87(8) . . . . ?
C15 C10 C11 C12 1.02(11) . . . . ?
C9 C10 C11 C12 179.28(7) . . . . ?
C16 O1 C12 C11 17.01(11) . . . . ?
C16 O1 C12 C13 -164.68(7) . . . . ?
C10 C11 C12 O1 176.59(7) . . . . ?
C10 C11 C12 C13 -1.64(11) . . . . ?
C17 O2 C13 C12 -96.35(8) . . . . ?
C17 O2 C13 C14 85.44(8) . . . . ?
O1 C12 C13 O2 4.07(10) . . . . ?
C11 C12 C13 O2 -177.54(6) . . . . ?
O1 C12 C13 C14 -177.71(6) . . . . ?
C11 C12 C13 C14 0.67(11) . . . . ?
C18 O3 C14 C15 -10.92(11) . . . . ?
C18 O3 C14 C13 169.70(7) . . . . ?
O2 C13 C14 O3 -1.45(10) . . . . ?
C12 C13 C14 O3 -179.66(6) . . . . ?
O2 C13 C14 C15 179.14(6) . . . . ?
C12 C13 C14 C15 0.94(10) . . . . ?
O3 C14 C15 C10 179.08(7) . . . . ?
C13 C14 C15 C10 -1.56(10) . . . . ?
C11 C10 C15 C14 0.58(11) . . . . ?
C9 C10 C15 C14 -177.70(6) . . . . ?

_refine_diff_density_max         0.472
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.054

